HERBICIDAL PYRIDINESULFONYLUREAS

Abstract: Herbicidal pyridinesulfonylureas which are highly active as preemergence and postemergence herbicides.

Description: HERBICIDAL PYRIDINESULFONYLUREAS Background of the Invention Pyridinesulfonylureas of the instant appli¬ cation show high activity as preemergence and post¬ emergence herbicides. In particular, safety to corn is demonstrated by many of the herbicides. EP-A-13,480 discloses herbicidal sulfonamides of the formula wherein R 1 is H, Cl, Br. F. C -C. alkyl. C.-C alkoxy. C χ -C 4 alkylthio. NO or CO R U.S. 4,435,206, issued March 6. 1984 and U.S. 4,522,645, issued June 11, 1985, disclose 2- pyridinesulfonylureas substituted in the 3-position by R_ . wherein R. is H, Cl, Br. F. C -C„ alkyl. C,-C_ 1 1 1 4 1 4 alkoxy. C 1 -C 4 alkylthio. NO,,. CF 3 . C0 2 R 5 or SO.NR R ? . U.S. 4.339,267 discloses herbicidal sulfonamides of the formula wherein R 4 is H. Cl, Br. F. C 1 -C 4 alkyl. C -C alkoxy, N0 2 , C0 2 R 6 or S 13 EP-A-30,433 discloses herbicidal sulfonamides of the formula wherein X is H; is H, F. Cl, Br. CH OCH. NO, C °2 R 11 ° C S 0) n R 12 U_S. 4.456.469 discloses herbicidal sulfonamides of the formula wherein R is C. 1-C6- alkyl, C,3-C6, alkenyl, C2_-C4 Λ alkoxy- CF CH , HGLCCF or HCF ; and Z is H. F. Cl. Br, CH , OCH or SCH . U.S. 4.487,626 discloses herbicidal sulfonamides of the formula wherein R is H, F, Cl. Br, ^-^ alkyl. C^C^ alkoxy. 0 2 . C0 2 15 . S(0> m R 16 . S0 2 NR 18 R 19 or S0 2 N(OCH 3 )CH 3 . U.S. 4.421,550 discloses herbicidal sulfonamides of the formula wherein R is H, C -C alkyl. C ]L -C 4 alkoxy. F, Cl, Br. CF 3 . C0 2 R 20 . SO 2 NR 10 R I;L . S0 2 N(OCH 3 )CH 3 or S(0) n H 13 . U.S. 4,496,392 discloses herbicidal sulfonamides of the formula wherein R_ is Cl, S0 2 CH 3 or S0_2,N(CH3)_2, EP-A-84.224 discloses herbicidal sulfonamides of the formula wherein is H. C 1 -C 4 alkyl, C χ 4 alkoxy. F, Cl, Br. CF 3 . C0 2 9 . S0 2 R 10 R 11 . S0 2 N(0CH 3 )CH 3 or S(0) n R 13 . EP-A-125.846 discloses herbicidal sulfonamides of the formula where 3 is Cl. S0 2 CH 3 . S0 2 (CH 3 ) 2 , OCH 3 . NO ∑ or N(CH 3 ) 2 . EP-A-155,767 discloses herbicidal sulfonamides of the formula wherein R is H. CH 3 . Cl. Br. C0 2 R 15 . C(0)NR 16 1? , S0 2 R 16 I7 . S0 2 N(0CH 3 )CH 3 . S0 2 R 18 or 0 2 . EP-A-161,905 discloses herbicidal sulfonamides of the formula wherein R 4 is CH 3 . CH 2 CH 3 . OCH 3 . OCH 2 CH 3 . F. Cl. Br. S0 2 N 16 R 17 . S0 2 N(OCH 3 )CH 3 . S(0) n H 19 . C 3 -C 4 alkenyloxy or C -C alkynyloxy. EP-A-164,269 discloses herbicidal sulfonamides of the formula wherein R is CH . CH CH . OCH . OCH 2 CH 3 . F. Cl, Br. S0 2 NR 1 1 R 1 2' S0 2 N ( OCH 3 ) CH 3 or 3 ( 0 ) ^. EP-A-171,286 discloses herbicidal sulfonamides of the formula 0 wherein R4 Λ is CH,3. CH2,CH,3, OCH,3. OCH2_CH,3. F. Cl. Br. S °2 NR 18 R 19' S0 2 < 0CH 3> CH 3' S{0) n R 21 * C 3~°4 alkenyloxy. CH 2 OCH 3 or CH 2 OCH 2 CH 3 . South, African Patent Application 83/4305, 5 published December 14, 1983, discloses herbicidal sulfonamides of the formula wherein _ R is H, C -C alkyl, C,-C haloalkyl, halogen, 0 2 . C 1 -C 3 alkoxy. CζW.Rg. SO^R^. S(0) Q - C- L -0 2 alkyl or C(0)R ; R is H. halogen, C -C alkyl. OCH , NO or CF.; R_b is H, NO2,. F. Cl. Br, CH,3. CF_3. S(O)nC.1-C,3 0 alkyl. C(0)C -C alkoxy or C,-C alkoxy; Y is o or S. 5 South African Patent Application 83/6639. published March 8. 1984. discloses herbicidal sulfonamides of the formula wherein A is a C -C_ alkynyl radical, a C.-C, alkyl rad- 3 6 1 6 ical which is substituted by halogen, C. 1-C4 Λ alkoxy. C.-C alkylthio, 0 -C alkylsulfinyl. C 1 -C 4 alkylsulfonyl, C.-C haloalkoxy. τ- 4 haloalkylthio. C.-C haloalkylsulfinyl or C.-C. haloalkylsulfonyl. or is a C 2 ~C 4 alkenyl radical which is unsubstituted or substituted as for C 1.-C6, alkyl, or is a phenyl radical which is unsubstituted or sub¬ stituted by halogen, cyano. nitro, C.-C alkyl, C,-C haloalkyl. an -X-C,-C. alkyl. C.-C alkoxycarbonyl, amino, mono- or di(C -C alkyl)amino, carba oyl, mono- or di-.C.-C alkyl)carbamoyl, sulfamoyl, mono- or di-(C -C alkyl)sulfamoyl radical; is hydrogen, halogen. C,-C alkyl, C.-C alkoxy, C.-C haloalkyl, C,-C haloalkoxy, C2_-C_b alkoxyalkoxy, C_l-Cb_ alkylthio, C.l-Cb,. alkylsulfinyl or C.-C.b alkylsulfonyl; and X is 0. S. SO or SO . U.S. 4,518,776 discloses a process for the preparation of herbicidal sulfonamides of the formula wherein R , in part, is s CO) n C 1 ~C 4 alkyl, S0 2 di-C 1 -C 4 alkyl- amino or CO -C -C alkyl; and is H. halogen. CF 3 , 0 2 C χ -C 4 alkyl or ' C -C alkoxy. This patent generically discloses some, but does not claim any. compounds of the instant invention. EP-A-101.670. published February 29, 1984, discloses a process for the preparation of herbicidal sulfonamides of the formula wherein R,1 is Q-C,1-C4 A alkyl. alkylamino or CO -C -C 4 alkyl; Q is S or S(O) ; and R is H. halogen. CF . NO , C -C alkyl or C,-C. alkoxy. This application generically discloses some of the compounds of the instant invention. U.S. 4,521.597 discloses a process for the preparation of herbicidal sulfonamides of the formula wherein R 3 is H, F . Cl , Br . N0 2 . OCH 3 or CF 3 ; 10 R 5 is alkyl. or COR_; and R6, is H. F. CH,3 or OCH,3. This patent generically discloses some, but does not claim any, compounds of the instant invention. 15 EP-A-184,385, published June 11, 1986, discloses the following compound for selective weed control in tomatoes and turf. 20 U.S.S.N. 874,307 discloses herbicidal _-alkylcar- bonyl-pyridinesulfonylureas. _. U.S.S.N. 943,137 discloses herbicidal p_-substi- tuted-pyridinesulfonylureas. 5 SUMMARY OF THE INVENTION This application pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. W JSO,NHCNA R wherein J-4 ιl___i R i s H or CH 3 ; W is 0 or S ; R, is R. or R : 1 f <3 R f is H, C.-C 3 alkyl. C 1 -C 3 haloalkyl. halogen, NO , C,-C, alkoxy, C.-C alkylthio or CN; R is C -C 3 haloalkyl. C,-C 3 alkyl. cyσlopropyl, C,-C, alkyl substituted by C.-C alkoxy. OH, C -C- alkylthio or CN, CN, R , amino, c ι" C 3 alkylamino or C,-C 3 dialkylamino; R2„ is C,1-C4„ alkylsulfinyl, C1.-C4. alkylsulfonyl, C -C 5 cycloalkylthio, -C cycloalkylsulfinyl, C 3 -C 5 cycloalkylsulfonyl. S0 2 NH 2 . S0 2 N d R e , S0 2 NR 7 R 8 . S0 2 NR 7 R 8 . OS0 2 R 8 , S0 2 OR 8 . N 3 . P(W 1 )(OC 1 -C 2 alkyl) 2 , CN, C0 2 R 9 . C0 2 R . CH 2 F. CF 2 H. CH 2 C1. CC1 2 H or C 2 -C 4 haloalkyl; R. is C1.-C4. alkylsulfinyl, C3. -Cb c cycloalkylthio. C 3.-Cb- cycloalkylsulfinyl. C3,-C4. cycloalkylsul- fonyl. S0 2 NH 2 . S0 2 NR d R e . S0 2 NR 7 R 8 , S0 2 NR^R 8 , 0S0 2 R s* S0 2 OE 8 ' N 3 ' p(w 1 )( ° c 1 " 2 alkyl ) 2 . C N. C0 Rg, C0 2 R' or C1-C haloalkyl; R 4. is C.-C. alkylsulfinyl, C3,-C_b cycloalkylthio, C 3,-C_b cycloalkylsulfinyl, C3_-C4 Λ cycloalkylsul- fonyl. S0 2 H 2 . S02_NRα,Re Ω , S0 2 R 7 R 8 OS0 2 R 8 . S0 2 OR 8 . N 3 . P(W 1 )(OC 1 -C 2 alkyl) 2 . CN. C0 2 R g or C,-C. haloalkyl; R is C -C alkylsulfinyl, C 1 ~C 4 alkylsulfonyl. o -C ^ cycloalkylthio. C,-C_ cycloalkylsulfinyl. 3 5 3 b C 3 -C cycloalkylsulfonyl. S0 2 H 2# S0 2 NR d R g . S0 2 NR ? R 8 . OS0 2 R g . S0 2 O g, Ng, P.W^COC^^ . alkyl) 2 . CN, C0 2 R g or C χ -C 4 haloalkyl; R 6 is C L -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C L -C 4 haloalkylthio, .-C 4 haloalkylsulfinyl. C. -C haloalkylsulfonyl, 3 ~C alkenylthio, C 3 ~C. alkenylsulfinyl, Cg-C alkenylsulfonyl, Cg- 4 alkynylthio, C -C alkynylsulfinyl, Cg- 4 alkynylsulfonyl, C 3 ~ c 5 cycloalkylthio, 3 -C 8 cycloalkylsulfinyl, G 3 - C E cycloalkylsulfonyl, S0 2 R d R e . S0 2 NR ? 8 . . S0 2 ORg. 3 , P W 1 )(OC 1 -C 2 alkyl) 2 . CN, C0 2 g or C χ -C 4 halo¬ alkyl; R ? is H, C 2 -C 3 cyanoalkyl, C -C alkenyl or C 3 - 4 alkynyl; R' is C x -C 4 alkyl; is C -C 4 alkyl, C 1 -C 4 haloalkyl. C 3 -C 4 alkenyl, C -C alkynyl, C_-C alkoxyalkyl or cyclo- propyl; or 7 and R8 may be taken together as -(CH2)3-, -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 0CH 2 CH 2 - -R g is CH 2 CH 2 R 10 . CH 2 CF 3 . C 3 -C 4 haloalkyl, C 3 -C alkynyl. C -C 4 alkylthioalkyl, C 3 -Cς cycloalkyl or C -C cycloalkylalkyl; R' is C 1 -C alkyl. C 3 -C 4 alkenyl. CH 2 CH 2 C1, CH 2 CH 2 B . CH 2 CH 2 0CH 3 or CH 2 CH 2 OC 2 H 5 ; R 10 is OH. F. CN, OS0 2 (C 1 -C 3 alkyl) or OSO^C^C, haloalkyl); R 1L is C 1 -C 3 alkyl. C 1 -C 3 haloalkyl. C -C alkenyl or C, 3-C4. al< ■ kynyl; W is O or S; W is 0 or S; A-l A-2 A-3 A-4 A-5 A-6 A-7 X is H, C.-C 4 alkyl, C.-C 4 alkoxy, C_-C 4 halo¬ alkoxy, C.-C 4 haloalkyl. C 2 "" 4 haloalkylthio, C 1.-C. alkylthio, halogen, C2--Cb- alkoxyalkyl, C 2_-C_b alkoxyalkoxy, amino. C.1-C3, alkylamino or diCC j^ -C alkyl)amino; Y is H. C 1 -C 4 alkyl. C -C 4 alkoxy. C 2 -C 4 halo¬ alkoxy. C 2 -C 4 haloalkylthio. C.-C alkylthio. C -C_ alkoxyalkyl, C_-C alkoxyalkoxy, amino, C.-C. alkylamino. di(C.-C 3 alkyl)amino, C 3 -C alkenyloxy, C 3 -C alkynyloxy, C_-C ς alkylthio- alkyl. 2 ~C alkylsulfinylalkyl. C -C 5 alkyl¬ sulfonylalkyl, C,-C. haloalkyl. C -C 4 alkynyl, C.-C- cycloalkyl, azido, N(OCH 3 )CH 3 ; m is 2 or 3; Q. and Q- are independently O or S; Ra is H or C,-C alkyl_ R b and Rc <are independently C,-G alkyl R, α iβ H or C L -C 2 alkyl; R e is Ci-C: alkoxy; , CC1 or CBr * • or OCF H:r F,3; . SC H , CHg or CH 2 CH 3 ; *4 is CHg. OCHg. OC 2 H 5 . CH 2 0CHg or Cl; Y 4 is CHg. OCHg. OC 2 H 5 or Clϊ and their agriculturally suitable salts; provided that 1) when X is halogen, then Z is CH and Y is OCH 3 . OC j H j . NH 2 . NHCHg. (CHg> 2 or N(OCHg)CHg; 2) when is S, then R is H. A is A-l. Z iβ CH or N. and Y is CHg, OCHg. OC 2 Hg. CH^CHg, C 2 H 5 . CFg. SCHg. OCH 2 CK»CH 2 . OCH 2 C≡CH. OCH 2 CH 2 OCHg. - 3) when the total number of carbon atoms of X and Y iβ greater than four, then the combined number of carbons of R. 1, R2_, R_3. R,. R c b or R6. is less than or equal to six; 4) when J is J-l and R 2 is C^C^ alkylsulfonyl. S0 2 NR d R e . S0 2 NR 7 R 8 or C0 2 R1. or when J is J-2 and R 3 is CF 3 . S0 2 NR d R e . S0 2 NR 7 R 8 or C0 R*. then Y is other than C -Cs alkylthioalkyl. C 2 ~C_ *l*Υl β}i iε iRγlalkγl C -C_ alkylsulfonylalkyl. 5) when J is J-2 or J-3 and Rg or R 4 is C.-C 4 alkyl¬ sulfinyl. then X and Y are other than H 2 or NHCH 6) when J is J-2 and Rg is C^-C. alkylsulfinyl or SO.2NRd.Re, or R_7 is H. then X and Y are other than C 2 ~ C 4 naloal * oχ Yi 7) when J is J-5. then R ? is other than H and R g is other than SO 2-NRd.Re: 8) when J is J-2 and R, 3 is SOZ-NHZ, or SO2,NRα,Rβ. or R_ is H. then X is other than iodine; 9) when J is J-2 and R_ 7 iβ H or R,3 iβ SO.2NRα.Re. then Y i β other than C 2 ~ C 4 allς Y n Y 1 i 10) X. and Y 4 are not simultaneously Cl; 11) when J iβ J-1. J-2. J-3. J-4 and A iβ A-5. then R f iβ other than H; 12) when J iβ J-1 or J-2. then A is other than A-6; 13) when J iβ J-1 and A iβ A-7. then R 2 is other than C.-C alkylsulfonyl; 14) when R or R3 is C0 R* or S0 2 NR'Rβ. then R 1, is R„g and when R_z or R_3 is other than C0 R' or S0 2 NR'R 8 . then R^ is Rf; and 15) when J is J-2 and R_ is adjacent to the sulfonylure bridge, then is ^-Cg haloalkyl. C 2 -Cg alkyl. cyclopropyl, CN. W 2 R,.. amino, C j -Cg alkylamino or c ι" c 3 dialkylamino. In the above definitions, the term "alXyl", used either alone or in compound words such as "alkylthio" or "haloalkyl". denotes straight chain or branched alkyl. e.g. methyl, ethyl, n-propyl. isopropyl or the different butyl isomers. Alkoxy denotes methoxy, ethoxy. n-propyloxy or isopropyloxy. Alkenyl denotes straight chain or branched alkenes. e.g. 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. Alkynyl denotes straight chain or branched allcynes. e.g. ethynyl. 1-ρropynyl, 2-propynyl and the different butynyl isomers. Alkylsulfonyl denotes methylsulfonyl. ethyl- sulfonyl and the different propylsulfonyl and butylsulfonyl isomers. Cycloalkyl denotes eyclopropyl* cyclobutyl and cyclopentyl. The term "halogen", either alone or in compound words such as "haloalkyl". denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially halogenated or fully substituted with halogen atoms which may be the same or different. Examples of halo¬ alkyl include CH CH F. CF CF and CH CHFCl. Similarly. this definition applies to haloalkoxy and haloalkylthio. The total number of carbon atoms in a substituent group .is indicated by the C.-C. prefix where i and j are numbers from 1 to 5. For example, C -C alkylsul- fonyl would designate methylsulfonyl through propylsul- fonyl, C Ct alkoxyalkoxy would designate OCH £*OCH 3, C & cyanoalkyl would designate CH CN and C cyanoalkyl would •__ • designate CH •toCH-SCN and CH(CN)CH <J. Preferred Compounds Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are: 1. Compounds of Formula I where X is C -C alkyl, C -C alkoxy. Cl. F. Br. I. CH 2 F « CF 3« OCH 2 CH 2 F. OCH 2 CHF 2 . OCH 2 CF 3 . CH 2 C1 or CH Br; and. Y is H. C -C alkyl. C -C alkoxy. CH 2 OCH 3 . CH 2 OCH 2 CH 3 . NHCH 3 . N(OCH 3 )CH 3 . N(CH 3 2 « CF 3 . SCH 3 , OCH 2 CH=CH 2 . OCH 2 C=CH. OCH 2 CH 2 OCH 3< CH SCH . cyclopropyl. C≡CH or C≡CCH ; Ra is H or CH ; and z is CH or N. Compounds of Preferred 1 where W is 0; R f is H. CH . C haloalkyl. halogen or OCH ; R is C. ^ -^ haloalkyl. ethyl. 2 R l;L . CH 2 OCH 3# g CH SCH., CH 2 CN. C 1 -C 2 alkylamino or (CH 3 > 2 ; C. alkylsulfonyl. R 2 is c λ -C alkylsulfinyl. C,- S0 2 NH . S0 2 NR d R e . S0 2 NR 7 R 8 , S0 2 NR^R 8 . oso 2 R 8 . so 2 O 8 . Ng. P(W._) (OC 1 -C 2 alkyl) 2 . CN. C0 2 R 9 . C0 2 R' CHF 2 . CF 2 H. CH 2 C1. CC1 H or C 2 -C 4 haloalkyl; R. is C -C 4 alkylsulfinyl. S0 2 NH 2 . S0 2 NR d R e , S0 2 R 7 R 8 . S0 2 NR^R 8 . OS0 2 R 8 . S0 2 OR 8 . N 3 . P(W I )(OC 1 -C 2 alkyl) 2 . CN. C0 2 R 9 . C0 2 R or C1.-C4, haloalkyl; R4„ is C,1-C4 Λ alkylsulfiny ■ 'l,' SO2NH„2, SO_2N(OCH„3)CH3 S0 2 NR ? R 8 . OS0 2 R 8 . S0 2 OR 8 . N... P(W χ ) (OC^^ alkyl) . CN. CO R or C -C haloalkyl; is C -C alkylsulfinyl. C,-C alkylsulfonyl. S0 2 NH 2 . S0 2 N(OCH 3 )CH 3 . S0 2 NR 7 R 8 . OSO^. S0 2 OR 8 . Ng. P( 1 ) (OC 1 -C 2 alkyl) 2 . CN. C0 2 9 or C -C haloalkyl; R, is C,-C„ alkylthio, C,-C. alkylsulfinyl. 6 1 4 1 4 C„-C „ haloalkylthio, C.-C. haloalkylsul- 1 4 1 4 finyl. C -C haloalkylsulfonyl, C 3 -C 4 alkenylthio, C -C alkenylsulfinyl, C -C 4 alkenylsulfonyl, C--C alkynylthio, Cg-C alkynylsulfinyl. C -C alkynylsulfonyl. S0 2 N(OCH 3 )CH 3 , S0 2 NR ? R 8 , . S0 2 OR 8 , 3 . P(W 1 )(OC 1 -C 2 allcyl) 2 . CN. CO^ or C^C^ haloalkyl; R is H, C--C 3 cyanoalkyl, C -C alkenyl or C -C 4 alkynyl; R is C 1 -C 4 alkyl, C χ -C 4 haloalkyl. Cg-C 4 alkenyl, c 3 - c 4 alkynyl. C 2 ~ C Λ alkoxyalkyl or cyclopropyl; and R is C -C alkyl, C -C haloalkyl, allyl or propargyl. 3. Compounds of Preferred 2 where J is J-1. 4. Compounds of Preferred 2 where J is J-2. 5. Compounds of Preferred 2 where J is J-3. 6. Compounds of Preferred 2 where J is J-4. 7. Compounds of Preferred 2 where J is J-5. 8. Compounds of Preferred 3 where R is H. -C cyanoalkyl, allyl or propargyl; R^ is ^-03 alkyl; R is C.-C alkyl, allyl, propargyl or cyclo¬ propyl; R 9 is CH 2 CH 2 R L0 . CH 2 CH 2 SCH 3 , propargyl or cyclopropylmethyl; R 9 is C x -C 3 alkyl. allyl, CH 2 CH 2 OCH 3 or R 9. C where A is A-l; X is CH 3 . OCH 3 , OCH CH . Cl or OCH CF ; and Y is CH 3 . OCH 3 . CH 2 CH 3 . CH 2 OCH 3 . NHCH 3 or CH(OCH 3 ) 2 . 10. Compounds of Preferred 9 where Z is CH. 11. Compounds of Preferred 9 where Z is N. 12. Compounds of Preferred 4 where is H, C 2 -C cyanoalkyl. allyl or propargyl; and R g is C.-C alkyl, allyl, propargyl or cyclo- propyl. 13. Compounds of Preferred 12 where A is A-l; X is CH 3 . OCH 3 . OCH 2 CH 3 . Cl or OCH 2 CF 3 ; and Y is CH 3, . OCH3, . CH2-CH3- , CH2.OCH3, . NHCH3, or CH(OCH 3 ) 2 . 14. Compounds of Preferred 13 where Z is CH. 15. Compounds of Preferred 13 where Z is N. 16. Compounds of Preferred 5 where R_ is H, C,-C- cyanoalkyl. allyl or propargyl; and R_ is C.-C, alkyl, allyl. propargyl or cyclo- propyl. 17. Compounds of Preferred 16 where A is A-l; X is CH3,. OCH3. OCH2CH3, Cl or OCH2_,CF3_,; and Y is CH . OCH . CH CH., CH 2 OCH , NHCH or CH(OCH 3 ) 2 - 18. Compounds of Preferred 17 where Z is CH. 19. Compounds of Preferred 17 where Z is N. 20. Compounds of Preferred 6 where R is H. C -C cyanoalkyl, allyl or propargyl; and R Q is C - C alkyl, allyl, propargyl or cyclo- propyl. 21. Compounds of Preferred 20 where A is A-l; X is CH 3 . OCH 3 . OCH 2 CH 3 , Cl or OCH 2 CF 3 ; and Y is CH 3 . OCH 3 , CH 2 CH 3 . CH 2 OCH 3 . HCH 3 or CH(OCH 3 ) 2 . 22. Compounds of Preferred 21 where Z is CH. 23. Compounds of Preferred 21 where Z is N. 24. Compounds of Preferred 7 where R is χ -C 2 alkylthio, C 1 ~C 2 alkylsulfinyl, C L -C 2 haloalkylthio, C--C 2 haloalkylsul- finyl. C λ -C 2 haloalkylsul onyl, S0 2 N(OCH 3 )CH 3 or S0 2 R ? 8 R is H, 2 -C 3 cyanoalkyl, allyl or propargyl; is C.-C 3 alkyl, allyl, propargyl or cyclo- propyl. 25. Compounds of Preferred 24 where A is A-l; X is CH, 3. OCH,3. OCH2.CH,3. Cl or OCH2-CF,; and Y is CH 3,, OCH3,. CH2„CH3,, CH2-OCH3-. NHCH3, or CH(OCH 3 ) 2 . 26. Compounds of Preferred 25 where Z is CH. 27. Compounds of Preferred 25 where Z is N. 28. Compounds of Preferred 1 where J is J-1; A is A-l; Z is CH; W is O; R 2_ is C.1-C4. alkylsulfinyl or C.1-C4., alkylsulfonyl; and R f is H, C 1 -C 2 alkyl. C. haloalkyl, C.-C 2 alkoxy or C.-C thioalkyl. 29. Compounds of Preferred 28 where R is H; R 2 is C -C alkylsulfonyl; Specifically Preferred for reasons of greateβt ease of βyntheβiβ and/or greateβt herbicidal efficacy are: • N-[(4.6-dimethoxypyrimidin-2-yl)arainocarbonyl]- 3-(l-propylβulfonyl)-2-pyridineβulfonamide; • N-C(4,6-dimethoxypyriraidin-2- 1)arainocarbony1]- 3-(l-propylsulfinyl)-2-pyridinesulfona ide; • N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 3-(ethylsulfonyl)-2-pyridinesulfonamide; • N2-C(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- N3-ethyl-2,3-pyridinedisulfonamide; • N-[(4.6-dimethoxypyriraidin-2-yl)arainocarbonyl]- 3-(methylsulfonyloxy)-2-pyridinesulfonamide; and • N2-[(4.6-dimethoxypyrimidin-2-yl)- aminocarbonyl]-N3-methyl-2.3- pyridinedisulfonamide. This invention alβo pertainβ to novel compoundβ of the following formulas wherein X fl iβ Cl. NH 2 . HNC(CHg)g and NHCOCgH 5 which are useful as intermediates to herbicidal sulfonylureas. Specifically preferred are: 3-ethylsulfonyl-2-pyridinesulfonamide and N3-methy1-2.3-pyridinedisulfonamide. DETAILED DESCRIPTION OF THE INVENTION Synthesis Compounds of Formula I can be synthesized either by one or more of the methods described in U.S. 4,456,469, or by the reaction of sulfonamides II with the phenyl ester of the appropriate carbamic acid III in the presence of an equimolar quantity of a tertiary amine base such as l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as shown in Equation 1. Equation 1 JSO II III wherein J, R, and A are as previously defined. The reaction shown in Equation 1 is best carried out at 25°C in a solvent such as dioxane or acetonitrile for 1-2 hours under an inert atmosphere as described in European Patent Application TJo. 70.804 (published January 26, 1983). The desired products of Formula I can be conveniently isolated by acidifying the reaction solution with aqueous hydrochloric acid. Alternatively, the aqueous layer can be extracted with a solvent such, as methylene chloride or ethyl acetate. Drying and evaporation of the solvent affords the desired products. The phenyl carbamates can be synthesized by treatment of the corresponding heterocyclic amines of Formula A-NHR with diphenyl carbonate or phenyl chloroformate in the presence of a base such as sodium hydride, pyridine, or potassium carbonate with a catalytic amount of 4-dimethylamino- pyridine. The mixture is stirred at temperatures between 25° and 65°C in a suitable solvent such as tetrahydrofuran for 12-36 hours. The required sulfonamides of Formula II can be synthesized by either one of the methods shown below in Equations 2 and 3. Equation 2 depicts the reaction of sulfonyl chlorides of Formula IV with ammonia to give sulfonamides of Formula II. Equation 2 JS0 2 C1 NH. JS0 2 NH 2 IV II wherein J is as previously defined. The a ination of Equation 2 is conveniently effected by adding at least two molar equivalents of either anhydrous ammonia or concentrated ammonium hydroxide to a solution of the sulfonyl chloride IV in a suitable solvent such as diethyl ether, tetrahydro- furan or methylene chloride at temperatures between -30° and 25°C. The desired sulfonamides of Formula II are isolated either by filtration, in which case the by-product ammonium chloride is removed by washing with water, or extraction into a suitable organic solvent such as methylene chloride or ethyl acetate. Drying and evaporation of the solvent then affords the products II which are usually sufficiently pure to be carried directly on to the next step. Sulfonamides of Formula II can also be prepared as shown in Equation 3 by treatment of the corre¬ sponding N-t.-butylsulfonamides VI with an appropriate acid such as trifluoroacetic (TFA). polyphosphoric (PPA), or £-toluenesulfonic acid (p_-TSA) . Equation 3 JSO NH- -BU TFA. PPA JS0 2 NH or 7 VI P.-TSA I_I wherein J is as previously defined. The reaction of Equation 3 is conveniently carried out by stirring a solution of the compound of Formula VI in excess trifluoroacetic acid (approximately 0.3M) at about 25 β C for 1-72 hours. The desired sulfonamides of Formula II are then isolated by removal of the volatiles in vacuo and crystallization from a suitable solvent such as diethyl ether, 1-chlorobutane, or ethyl acetate. Alternatively, the N-t_-butylsulfonamides of Formula VI can be treated with a catalytic amount of p_-toluene- sulfonic acid monohydrate in a solvent such as toluene or xylenes at reflux temperature for 1-6 hours. The desired products are then isolated in a manner analogous to the one described above. For use of polyphosphoric acid in the deprotection of N-t_-butyl- sulfonamides, see J. G. Lombardino, J. Orq. Chem., 36. 1843 (1971); for use of trifluoroacetic acid, see J. D. Catt and W. L. Matier. J. Pro. Chem.. 38. 1974 (1973). Sulfonamides of Formula VI can be prepared by the reaction of sulfonyl chlorides of Formula IV with excess t.-butyl amine as shown in Equation 4. Equation 4 JS0 2 C1 ~ ~BUNH 2 > JS0 2 NH-;t-BU IV VI wherein J is as previously defined. Sulfonyl chlorides of Formula IV can be prepared according to the procedures described in U.S. 4.456.469. Alternatively, the procedures of South African Patent Application 84/8844 may be utilized which describe the conversion of mercapto or aryl ethylthio compounds to sulfonyl chlorides via treatment with hypochlorite solution. Sulfonyl chlorides of Formula IVa may also be prepared via metallation of 2-fluoropyridine derivatives with lithium diisopropyl amide (LDA) according to the procedure of T. Gungor. F. Marsais and G. Queguiner, J. Orqanomet. Chem.. 1981. 215, 139-150. followed by treatment with sulfur dioxide and N-chlorosuccinimide (NCS) as shown in Equation 5. Equation 5 IVa wherein R is as previously defined. Sulfonyl chlorides of Formula IVb can be prepared from compounds of Formula VII as shown in Equation 6 and described in U.S. 4.420,325. Equation 6 JCH 3 2) [hiourea - CH a 80 2 C l 3) Cl. VII * IVb wherein J is as previously defined; and [X] is a suitable halogenating reagent which would be obvious to one skilled in the art. The sulfides of Formula VIII can be prepared by the reaction of a halo pyridine compound of Formula IX with an appropriate mercaptan in the presence of a base as described in U.S. 4,456,469 and shown in Equation 7. Equation 7 IX VIII wherein X' is F, Cl, or Br; and R' is C -C alkyl or benzyl. The sulfides of Formula Villa can be prepared by metallation of the pyridine compound of Formula X with two equivalents of a strong base such as ri-butyllithium or lithium diisopropylamide (LDA) as described by P. Breant, F. Marsais. and G. Queguiner. Synthesis. 1983. 822-824, followed by treatment with the appropriate disulfide as shown in Equation 8. Equation 8 wherein R' is C -C. alkyl. C. -C c cycloalkyl or 1 3 b benzyl; and R is as previously defined. In an analogous manner, sulfides of Formula VHIb can be prepared as shown in Equation 9. Equation 9 VHIb wherein R' is C1 ' -C4 Λ alkyl, C3_-C5_ cycloalkyl. or benzyl; and is as previously defined. Sulfides of Formula VIIIc can be prepared by the metallation of a 2-fluoropyridine derivative as described previously and again followed by treatment with an appropriate disulfide as shown in Equation 10. Equation 10 1 VIIIc wherein R* is C -C alkyl. C -C cycloalkyl. or benzyl; and is as previously defined. The sulfones and sulfoxides of General Formula XI can be prepared from the corresponding sulfides of Formula VIIId by any one of the numerous oxidation reagents [O] known in the art such as hydrogen peroxide or peracids. as shown in Equation 11. Equation 11 R'-S S0 2 NH-t-Bu Vllld XI wherein R_, is as previously defined; is C,1-C4 Λ alkyl or C3-C P 5 cycloalkyl; and n is 1 or 2. The chloropyridine of Formula IXa can be prepared by diazotization of 3-amino-2-chloropyridine followed by displacement with cuprous cyanide as shown in Equation 12. The diazoniu group can also be replaced by other groups such as SO Cl and N by those skilled in the art via methods known in the literature. Equation 12 IXa wherein R is as previously defined, The sulfides of General Formula Vlllf can be prepared as shown in Equation 13. Alkylation of a 3-hydroxy-2-mercaptopyridine derivative with alkyl halides utilizing a variety of bases such as potassium carbonate or potassium Jt-butoxide afforded the sul¬ fides of Formula Vllle which were then treated with the appropriate sulfonyl chlorides in the presence of an acid acceptor such as triethylamine to afford sul¬ fides of Formula Vlllf. Equation 13 Vllle Vllle Vlllf Wherein R' is C. -C alkyl or benzyl: X' is Cl. Br. or I; and and are as previously defined, 1 8 The esters of Formula Vlllg. Vlllh. and VIIIj can be prepared by either of the two methods shown in Equa- tion 14. The first method involves metallation of a 2- fluoropyridine derivative as previously described in Equation 5, followed by treatment with ethyl or methyl chloroformate which afforded esters of Formula XIII. Mercaptide displacement as described in Equation 7 resulted in esters of Formula Vlllg. Acid catalyzed transesterification using the appropriate alcohol as the solvent afforded esters of Formula Vlllh. The second method involves the alkylation of a 2-mercaptonicotinic acid derivative Vllli with alkyl halides utilizing a variety of bases such as potassium carbonate or potassium t:-butoxide, followed by conver¬ sion to the acid halides by any number of standard reagents such as thionyl chloride, phosphorous tri¬ chloride or pentachloride, or oxalyl chloride. The acid chlorides were then treated with the appropriate alcohols in the presence of an acid acceptor such as triethylamine, to afford esters of Formula Vlllh. Conversion of the sulfides Vlllh to the sulfonamides VIIIj was carried out as previously described. Equation 14 A. XIII Vlllg Vlllh a. Vlllh VIIIj wherein R' is C -C alkyl or benzyl; R„ can also be R' ; and 9 9 X', R'. R . R and R 1 are as previously defined. The sulfonamides of General Formula XIla can be prepared as shown in Equation 15. However, for the preparation of primary or unhindered secondary sulfonamides. a protective group is needed for a later stage in the synthetic sequence. A representative example is shown in Equation 16 where a t,-butyl protective group is utilized for the synthesis of sulfonamide Ila. Equation 15 IVa XIla wherein t∑>] is *dΛe R 7 R 8' R 7_-_R8« * or H 2_ and R,1, Rdj. R Ree-' R_7, R8 β and R 1 are as previously defined. Equation 16 4) TFA Ila wherein R χ is as previously defined, The difluoro compounds of Formula XlVa in Equa¬ tion 17 can be prepared using the reactions previously described. Treatment with one equivalent of various R nucleophiles (those that are available in the art) results in a mixture of products which can be separated. An example of the use of sodium ethoxide as the reactive nucleophile is shown. Intermediates XlVb and XIVc can be separated and further derivatized as previously described. Equation 17 XIVc wherein R is as previously defined. An alternative method to prepare esters of Formula XVd is shown in Equation 18. ercaptide d isplacement of a 2,6-dihalopyridine can be achieved followed by conversion to the sulfonamide XVa as pre- viously described. Treatment with two equivalents of a strong base such as n-butyllithium in a similar manner to that described by P. Breant. F. Marsalis, an d G . Queguiner. Synthesis, 1983. 822-824, followed by treatment with carbon dioxide affords the acids of Formula XVb. The acids can then be treated with various R. nucleophiles such as alkoxides. mercap- ti d es or amines to afford the acids of Formula XVc ( using sodium methoxide as an example) which can then be esterified with the appropriate alcohols utilizing stan d ard 1,3-dicyclohexylcarbodiimide (DCC) coupling con d itions to afford esters of Formula XVd. Equation 18 XVa XVb £_£ XVd wherein R can also be R -* 9 is F or Cl; and R 1 and R' are as previously defined. In an analogous manner, sulfonamides of General Formula XVIb can be prepared as shown in Equation 19. Treatment of XVa with strong base followed by an ap¬ propriate disulfide affords sulfides of Formula XVIa. Further elaboration utilizing chemistry previously described affords sulfonamides of Formula XVIb. Equation 19 X XVIb whe ein X' is F or Cl; and R* and [D] are as previously defined. A choice by one skilled in the art of the appro¬ priate methods for preparing compounds of Formula I must take into account the nature of the substituents R through R,, « and Rd through Rg. and their chemical compatibility with the reaction conditions of Equations 1 through 19. The heterocyclic amines of Formula A-NHR in Equation 1 above can be prepared by methods known in the literature, or simple modifications thereof, by those skilled in the art. For instance, EP-A No. 84,224 (published July 27, 1983) and . Braker et al.. J. Chem. Soc. 69. 3072 (1947) describes methods for preparing aminopyridines and triazines substituted by acetal groups such as dialkoxymethyl- or 1,3-dioxolan- 2-yl, among other groups. Also, for example. South African patent application Nos. 82/5045 and 82/5671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as 0CH 2CH2_,F, OCH2.CF,3. SCF2H., or OCF2„H. among other groups. South African patent application No. 83/7434 (published October 5, 1983) describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkyl- amino or alkoxyalkyl. The 5,6-dihydrofuro[2.3-d]pyrimidine-2-amines. the cyclopenta[d]pyrimidine-2-amines (A is A-2) and the 6,7-dihydro-5H-pyrano[2.3-d]pyrimidin-2-amines (A is A-3) can be prepared as described in EP-A No. 15,683. The furo[2.3-d]pyrimidin-2-amines (A is A-4) are described in EP-A No. 46,677. Compounds o Formula A-NHR where A is A-5 are described in EP-A-73.562. Compounds where A is A-6 are described in EP-A-94.260. In addition, general methods for preparing aminopyrimidines and triazines have been reviewed in the following publications: • The Chemistry of Heterocyclic Compounds". a series published by Interscience Publishers, Inc., New York and London; • "Pyri idines". Vol. 16 of the same series by D. J. Brown: • "s.-Triazines and Derivatives", Vol. 13 of the same series by E. . S olin and L. Rappoport; and • F. C. Schaefer, U.S. Patent 3.154.547 and K. R. Huffman and F. C. Schaefer. J. Orq. Chem.. 28. 1812 (1963). which describes the synthesis of triazines. Preparation in view of the above would be obvious to one skilled in the art. Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide. carbonate or hydroxide). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I can also be pre- pared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g.. alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g.. a potassium, sodium or calcium salt. Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid. e.g.. p_-toluenesulfonic acid, trichloroacetic acid or the like. The preparation of the compounds of this invention is further illustrated by the following specific examples. Temperatures are reported in degrees Celsius; abbreviations for nuclear magnetic resonance (NMR) are: s = singlet, d = doublet, t = triplet, m = multiplet, and peak- positions are reported as parts per million downfield from internal tetramethylsilane. Infrared (IR) peak positions are given in reciprocal centimeters (cm~ ) . Example 1 Preparation of 2-Fluoro-3-(propylthio)pyridine To a stirred solution of 59 ml (0.113 ol) of; 1.9 molar lithium diisopropyl amide (in hexanes) in 150 mis dry tetrahydrofuran cooled to -70° under nitrogen was added dropwise a solution of 10.0 g of 2-fluoropyridine (0.103 mol) in 30 mis dry tetrahydrofuran such that the temperature was maintained below -65°. The solution was stirred at -70° for 4 hours and a solution 17 g of n-propyldisulfide (0.113 mol) in 45 mis dry tetrahydrofuran was added dropwise while maintaining the temperature below -65°. After stirring another hour at -70°, the solu- tion was poured into water and extracted with ether. The combined organic phases were washed with brine, dried over magnesium sulfate. and evaporated to afford 14.5 g (82%) of a red oil: NMR (CDC1 . 200 MHz). 1.0 (3H. m), 1.7 (2H. m). 2.9 (2H. m). 7.1 (1H. m). 7.7 (1H. m). 8.0 (1H. m); IR (neat) 1585, 1560. 1410. 1245 cm "1 . Example 2 Preparation of 2-(Phenylmethylthio)-3-(propylthio)- yridine To a stirred suspension of 0.62 g (0.013 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes, in 20 mis dry dimethylformamide cooled to -5° under nitrogen was added dropwise 1.6 g (0.013 mol) benzyl mercaptan such that the temperature was maintained below 5 β . The suspension was stirred at room temperature for 1 hour, cooled to 0°. and a solution of 2.0 g (0.012 mol) of the product from Example 1 was added dropwise while maintaining the temperature between 0° and 5°. After warming to room temperature, the solution was poured into water and extracted with ether. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, and evaporated to an oil which was purified by flash chromatography to afford 0.9 g (27%> Oil: NMR (CDC1 . 200 MHz). 1.02 (3H. t. J=7 Hz). 1.6 (2H. m). 2.9 (2H. t. J=7 Hz) . 4.45 (2H. S). 6.9-7.6 (7H. m). 8.3 (1H. m); IR (neat) 1560. 1370 cm "1 . Example 3 Preparation of N-(l,l-Dimethylethyl)-2-(propyl- sulfinyl)-2- yridinesulfonamide To a vigorously stirred mixture of 0.5 g (0.0018 mol) of the product from Example 2 in 9 is methylene chloride and 4 mis water cooled to 0° was added 0.7 mis (0.008 mol) concentrated hydrochloric acid followed by the dropwise addition of 8.9 mis (0.006 mol) of a 5% sodium hypochlorite solution such that the temperature was maintained between 0 β and 5 β . After the mixture was stirred for an additional 30 minutes at 0° the reaction was poured into water and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate, and filtered. The filtrate was stirred and cooled to -70° under nitrogen and 0.53 g (0.0072 mol) of t.-butyl amine was added dropwise and the mixture was allowed to warm to room temperature. The reaction was poured into water and extracted with methylene chloride. The organic layers were combined and washed with brine, dried over magnesium sulfate. and evaporated to a mixture which was purified by flash chromatography to afford 0.4 g (69%) white solid: m.t. 138-140°; NMR (CDCl . 200 MHZ) 1.09 (3H, m), 1.7 (1H, m). 2.0 (1H, m), 2.8 (1H. m), 3.3 (1H. ra), 5.2 (NH), 7.7 (1H. m), 8.6 (1H, m), 8.8 (1H. m); IR (nujol) 3400, 1375, 1325. 1160, 1065. 1015 cm "1 . Example 4 Preparation of 3-(PropyIsulfonyl)-2-pyridinesulfonamide To a stirred solution of 8.8 g (0.029 mol) of the product from Example 3 in 400 mis methylene chloride cooled to -5°, under nitrogen, was added 6.6 g (0.038 mol) of 3-chloroperbenzoic acid and stirred at room temperature for 20 hours. The reaction mixture was poured into water and extracted with methylene chloride. The organic layers were combined and washed with saturated sodium bisulfite and brine, dried over magnesium sulfate, and evaporated to a solid mixture which was washed with hexanes to afford a white solid. The solid was dissolved and stirred in 150 mis trifluoroacetic acid for 72 hours. The solution was evaporated and triturated with ether to afford 5.3 g (46%) white solid: m.p. 153-157°; NMR (CDCl , 200 MHZ) 1.06 (3H. t. J=7 Hz), 1.8 (2H. m), 3.7 (2H. m) 5.8 (NH ). 7.8 (IH. m). 8.6 (IH. m). 8.95 (IH. m); IR (nujol) 3390. 3180. 1360, 1310, 1175, 1150 cm "1 . Example 5 Preparation of N-[(4,6-Dimethoxypyrimidin-2-yl)amino- carbonyl,-3-(propylsulfonyl)-2-pyri inesulfonamide To a stirred suspension of 0.4 g (0.0015 mol) of the product from Example 4 and 0.63 g (0.0023 mol) of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate in 4 mis acetonitrile was added 0.35 g (0.0023 mol) of 1,8- diazabicy lo[5.4.0]undec-7-ene and stirred for 30 minutes. The solution was diluted with water and acidified with 1 normal hydrochloric acid. The resulting precipitate was collected and washed with water and ether to afford 0.45 g (67%) white solid: m.p. 168-170°; NMR (CDCl , 200 MHZ), 1.07 (3H, t. J=7 Hz). 1.85 (2H. m). 3.7 (2H. m). 3.97 (6H. S)» 5.8 ( H. s). 7.26 (NH). 7.8 (IH. m). 8.6 (IH. m), 8.9 (IH, m). 12.9 (NH); IR (nujol) 3320. 1740. 1610, 1580. 1375. 1195. 1170 cm "1 . Example 6 Preparation of 3-ethylthio-2-fluoropyridine Using the procedure of Example 1, 40.0 g of 2-fluoropyridine (0.412 mol) was converted to 46.5 g (72%) of the title compound as an oil: NMR(CDC1 . 200 MHz) 1.3 (3H. t. J = 7 Hz), 2.95 (2H. q. J = 7 Hz). 7.1 (IH. m), 7.7 (IH. m) . 8.0 (IH. m) ; IR (neat) 1585. 1565. 1410. 1230 cm "1 . Example 7 Preparation of 3-ethylthio-2-(phenylmethylthio)- pyridine Using the procedure of Example 2, 25.0 g (0.160 mol) of the product from Example 6 was converted to 44.8 g (100%) of the title compound as a yellow liquid: NMR (CDClg. 200 MHz) 1.28 (3H, t, J * 7 HZ), 2.9 (2H, q. J = 7 Hz). 4.45 (2H, S). 7.0-7.6 (7H, m). 8.35 (IH, m); IR (neat) 1610. 1405 cm "1 . Example 8 Preparation of N-(1.1-Dimethylethyl)-3-ethylsulfinyl- 2-pyridines Ifonamide Using the procedure of Example 3, 35.0 g (0.134 mol) of the product from Example 7 was converted to 21.2 g (56%) of the title compound: m.p. 129-131°; NMR (CDCl . 200 MHZ) 1.23 (9H. S), 1.28 (3H, t. J _> 7 HZ), 2.9 (IH, m). 3.3 (IH, m), 5.2 (NH) , 7.7 (IH, m). 8.55 (IH, m), 8.75 (IH, m) ; IR (nujol) 3100, 1320, -1 1155 cm Example 9 Preparation of N-(l,l-Dimethylethyl)-3-ethylsulfonyl- 2-pyridinesuIfonamide t Using the first half of the procedure of Example 4 (i.e.. the 3-chloropetbenzoic acid reaction). 9.0 g (0.033 mol) of the product from Example 9 was converted to 10.1 g (100%) of the title compound: m.p. 58-63°; NMR (CDCl . 200 MHz) 1.2 (3H, t, J = 7 HZ), 1.2 (9H. S), 3.7 (2H. q, J = 7 Hz). 6.1 (NH). 7.7 (IH, m), 8.55 (IH, m). 8.95 (IH. m); IR (nujol) 3300. 1560. 1350. 1300. 1170. 1140 cm "1 . Example 10 Preparation of 3-ethylsulfonyl-2-pyridinesυlfonamide Using the second half of the procedure of Example 4 (i.e., the trifluoroacetic acid reaction), 9.0 g (0.029 mol) of the product from Example 9 was converted to 4.2 g (58%) of the title compound: m.p. 211-212.5°; NMR (DMSO-d 6,. 200 MHZ) 1.15 (3H. t. J - 7 HZ). 3.4 (NH 2 ). 3.7 (2H. q. J = 7 Hz). 7.9 (IH. m). 8.5 (IH. m). 8.95 (IH. m); IR (nujol) 3370. 3190. 1350. 1310. 1180 cm "1 . Example 11 Preparation of N-[(4.6-dimethoxypyrimidin-2-yl)- aminocarbony11-3-ethylsulfonyl-2-pyridinesulfonamide Using the procedure of Example 5, 0.60 g (0.0024 mol) of the product from Example 10 was converted to 0.70 g (70%) of the title compound: m.p. 160-162°; NMR (CDC1 3 . 200 MHz) 1.35 (3H. t. J = 7 Hz). 3.7 (2H, q. J = 7 Hz). 3.97 (6H. S). 5.8 (IH. s). 7.3 (NH), 7.75 (IH. m). 8.6 (IH, m). 8.9 (IH. m). 12.95 (NH); IR (nujol) 3260. 1740, 1610. 1360. 1195. 1175 Example 12 Preparation of 2.6-Difluoro-3-pyridinecarboxylic acid, methyl ester To a stirred solution of 91 ml (0.182 mol) of 2.0 molar lithium diisopropylamide (in hexanes) in 200 mL dry tetrahydrofuran cooled to -70° under nitrogen was added dropwise a solution of 20.0 g of 2,6-difluoro- pyridine (0.174 mol) in 75 mL dry tetrahydrofuran such that the temperature was maintained below -60°. The solution was stirred at -70° for 3 hours and was then added via a cannula to a solution 21.7 g (0.230 mol) of methyl chloroformate in 100 mL dry tetrahydrofuran cooled to -70° under nitrogen. After stirring another hour at -70°. the mixture was poured into water and extracted with ether. The combined organic layers were washed with brine, dried over magnesium sulfate. and evaporated to a semisolid which was purified by flash chromatography to afford 13.0 g (43%) orange Oil: NMR (CDClg. 200 MHZ) 3.95 (3H, S), 6.9 (IH. m), 8.5 (IH. m); IR (neat) 1745. 1730. 1610. 1415. 1290 cm " . Example 13 Preparation of 2-Fluoro-6-Methoχy-3-Pyridinecarboχylic Acid. Methyl Ester To a stirred solution of 15.0 g (0.0867 mol) of the product from Example 12 in 240 mL dry tetrahydro¬ furan cooled to -78° was added dropwise 22.7 mL (0.0993 mol) of 25% sodium methoxide in methanol solution over 45 minutes. After warming to -20°, the mixture was poured into ice water, acidified with 1 normal hydro¬ chloric acid and extracted with ether. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to a semisolid which was purified by flash chromatography to afford 3.2 g (17%) light yellow solid: m.p. 81-82°; NMR (CDCl . 200 MHZ) 3.9 (3H. S). 3.98 (3H. S). 6.67 (IH. d. J=9 Hz). 8.25 (IH, m); IR (nujol) 1715, 1615, 1290 cm "1 . Example 14 Preparation of 6-Methoxy-2-(Phenylmethylthio)-3- Pyridinecarboxylic Acid, Methyl Ester To a stirred mixture of 0.8 g (0.0161 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes. in 20 mL dry dimethylformamide cooled to -5° under nitrogen was added dropwise 1.9 mL (0.0161 mol) benzyl mercaptan The suspension was stirred at room temperature for 1 hour, cooled to 0°, and a solution of 3.2 g (0.0147 mol) of the product of Example 13 in 20 mL dry dimethylformamide was add¬ ed dropwise. After warming to room temperature, the solution was poured into water and extracted with ether. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, and evaporated to an oil which was purified by flash chromatography to afford 3.0 g (64%) of a yellow solid: m.p. 67-71°; NMR (CDCl , 200 MHz) 3.88 (3H. S). 3.96 (3H. S), 4.46 (2H. S). 6.44 (IH. d. J=9HZ). 7.2-7.5 (5H. m). 8.1 (IH. d. J=9Hz); IR (nujol) 1700. 1580, 1305, 1255 cm "1 . Example 15 Preparation of 2-[l.l-Dimethylethyl)Aminosulfonyl]-6- Methoxy-3-Pyridinecarboxylic Acid. Methyl Ester To a vigorously stirred mixture of 3.7 g (0.0129 mol) of the product from Example 14 in 79 mL methylene chloride and 41 L water cooled to 0° was added 6.3 mL (0.0759 mol) concentrated hydrochloric acid followed by the dropwise addition of 79 mL (0.053 mol) of a 5% sodium hypochlorite solution such that the temperature was maintained below 5°. After the mixture was stir¬ red for an additional 30 minutes at 0° the reaction was poured into water and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate, and filter- ed. The filtrate was stirred and cooled to -70° under nitrogen, and 4.7 (0.0645 mol) of t-butyl amine was added dropwise. The reaction mixture was allowed to warm to -20°, poured into water, acidified with 1 normal hydrochloric acid, and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate, and evapor¬ ated to a semisolid which was purified by flash chromatography to afford 3.0 g (77%) yellow solid: m.p. 128-130°; NMR (CDClg, 200 MHz) 1.27 (9H. s), 3.94 (3H. S), 4.05 (3H, s) 5.75 (NH) , 6.9 (IH. d, J=9 HZ), 7.95 (IH, d. J=9 HZ); IR (nujol) 3260, 1740, 1605, 1325, 1125 cm "1 . Example 16 Preparation of 2-(Aminosulfonyl)-6-Methoxy-3-Pyridine- Carboxylic Acid. Methyl Ester A solution of 2.9 g (0.0096 mol) of the product from Example 15 was stirred in 50 mL trifluoroacetic acid at room temperature for 20 hours. The solution was evaporated to afford 2.4 g (100%) white solid: m.p. 142.5-144.5°; NMR (CDCl, 200 MHz) 3.97 (3H. S), 4.1 (3H. S), 5.6 (NH 2 ). 6.9 (IH, d. J=9Hz), 8.1 (IH. d. J=9HZ); IR (nujol) 3305. 3205, 1715. 1590. 1355, 1320, 1175 cm "1 . Example 17 Preparation of 2-T[ (4.6-Dimethoxypyrimidin-2-yl) aminocarbonyl1aminosulfonyl1-6-Methoxy-3-Pyridine- carboxylic Acid, Methyl Ester To a stirred suspension of 0.4 g (0.0016 mol) of the product from Example 16 and 0.54 g (0.002 mol) of phenyl(4, 6-dimethoxypyrimidin-2-yl) carbamate in 4 L acetonitrile was added dropwise 0.30 g (0.002 mol) of l,8-diazobicyclo[5.4.0]undec-7-ene and stirred for 30 minutes. The solution was diluted with water and acidified with 1 normal hydrochloric acid. The resulting precipitate was collected and washed with water and with ether to afford 0.57 g (84%) white SOlid: m.p. 194-196°; NMR (CDClg. 200 MHZ). 3.83 (3H. S), 3.95 (9H. s), 5.8 (IH. s). 6.95 (IH, d. J=9 HZ). 7.4 (NH). 8.1 (IH. d. J=9 Hz). 12.8 (NH); IR (nujol) 3140. 1740. 1720. 1640. 1360. 1195. 1140 cm " . Example 18 Preparation of N-(l.l-Dimethylethyl)-2-Fluoro-3- Pyridinesulfonamide To a stirred solution of 396 mL (0.740 mol) of 1.9 molar lithium diisopropylamide (in hexanes) in 1.5 L dry tetrahydrofuran cooled to -70° under nitrogen was added dropwise a solution of 65 g (0.670 mol) of 2-fluoropyridine in 150 L dry tetrahydrofuran such that the temperature was maintained below -65°. The suspension was stirred at -70° for another 3.5 hours and 86 g (1.34 mol) of sulfur dioxide was added while maintaining the temperature below -65°. After stirring another 15 minutes at -70°, the reaction was allowed to warm to 0° and evaporated to half the original volume and diluted with ether. The white precipitate was collected under nitrogen, washed with ether, and dried. The solid was dissolved in 800 mL acetic acid and cooled to 10-20°. To this stirred solution was added portionwise 99.4 g (0.740 mol) of N-chlorosuccinimide while maintaining the temperature below 20°. After stirring another 30 minutes, the suspension was evaporated, diluted with water and extracted with methylene chloride. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution until no more gas evolution, washed with brine, dried over magnesium sulfate. and filtered. The filtrate was cooled to -70° under nitrogen and to this stirred solution was added dropwise 199 g (2.7 mol) of -butylamine. The suspension was poured into ice water, acidified with concentrated hydrochloric acid, and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to an oil which was purified by flash chromatography to afford 29.1 g (19%) of a brown solid which was further washed with cold n-butylchloride to afford 22.4 g (14.5%) of a white solid: m.p. 95-97°; NMR (CDC1 3 . 200 MHz) 1.25 (9H. S). 4.9 (NH). 7.35 (IH. m). 8.3-8.5 (2H, m). Example 19 Preparation of N-(l.l-Dimethylethyl)-2-Fluoro-N-Methyl- 3-Py idinesulfonamide To a stirred suspension of 3.4 g (0.071 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes, in 120 mL dry dimethyldormamide cooled to 0° under nitrogen was added dropwise a solution of 15.Q g (0.065 mol) of the product from Example 18 in 120 mL dry dimethylformamide. After stirring at room temperature for 1 hour, the mixture was cooled to 0° and 12.2 g (0.086 mol) of methyl iodide was added dropwise. After warming to room temperature the reaction was poured into ice water and extracted with ether. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to 15.9 g (99%) oil; NMR (CDCl . 200 MHz), 1.32 (9H. S). 3.1 (3H, s). 7.3 (IH, m) . 8.3-8.4 (2H, m); IR (neat) 1590. 1570. 1335. 1155 cm "1 . 49 Example 20 5 Preparation of N-(l.l-Dimethylethyl)-N-Methyl-2- (Phenylmethylthio)-3-Pyri inesulfonamide Using the same procedure as in Example 14, 15.9 g (0.065 mol) of the product from Example 19 was 10 converted to 19.5 g (86%) yellow solid: m.p. 92-94°; NMR (CDCl ). 200 MHz) 1.26 (9H. s), 3.1 (3H. s). 4.5 (2H. s). 7.0-7.5 (6H. m) . 8.2 (IH. m) ; IR (nujol) 1570. 1385. 1315. 1150. 1120 cm "1 . 15 Example 21 Preparation of N2. N3-Bis(l.1-Dimethylethyl)-N3-Methyl- 2,3-Pyridinedisulfonamide Using the same procedure as in Example 15, 19.5 g (0.056 mol) of the product from Example 20 was converted 20 to a tan solid which was washed with n-butylchloride to afford 13.1 g (66%) white solid: m.p. 155-156.5°; NMR (CDCl . 200 MHz) 1.23 (9H. s). 1.33 (9H. S). 3.1 (3H. s), 6.0 (NH). IH. m) . 8.5 (IH. m). 8.8 (IH. m); IR (nujol) 3320. 1340. 1325. 1160, 1120 cm "1 . 25 Example 22 Preparation of N3-Methyl-2,3-Pyridinedisulfonamide A stirred solution of 13.1 g (0.036 mol) of the product from Example 21 in 150 mL trifluoroacetic acid 30 was refluxed for 5 hours. After cooling to room temperature, the solution was evaporated to a solid which was washed with ether to afford 9.6 g (100%) white solid: m.p. 220-223°; NMR (DMSO-d . 200 MHz). 2.5 (3H. d), 6.9 (NH) . 7.65 (NH ) , 7.85 (IH. m) . 35 8.45 (IH. m). 8.9 (IH. m) ; IR (nujol) 3380, 3320. 3180, 1355, 1170 cm "1 . Example 23 Preparation of N2-f(4.6-Dimethoxyρyrimidin-2-yl)amino- carbonyl_- 3-Methyl-2.3-Pyridinedisulfonamide To a stirred suspension of 4.15 g (0.0165 mol) of the product from Example 22 and 5.0 g (0.018 mol) of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate in 50 mL acetonitrile was added dropwise 2.8 g (0.018 mol) of 1,8-diazabicyclo [5.4.0] undee-4-ene and stirred for 30 minutes. The solution was diluted with water and acidified with 1 normal hydrochloric acid. The resulting precipitate was collected and washed with water and with ether to afford 6.4 g (82%) white solid: m.p. 147-148.5°; NMR (CDCl , 200 MHz) 2.7 (3H. d. J=7 Hz), 3.97 (6H, s). 5.8 (IH, s), 6.15 (IH. m), 7.3 (NH). 7.7 (IH. m). 8.55 (IH. ' m). 8.8 (IH, ). 13.1 (NH); IR (nujol) 3310. 1740, 1610, 1340, 1190, 1165 cm " . By applying the procedures of Examples 1 through 23 and Equations 1 through 19, the compounds in Tables I through X can be prepared by one skilled in the art. General Formulas For Tables General Formula 1 General Formula 2 General Formula 3 General Formula 5 General Formulas For Tables ( continued ) General Formula 6 General Formula 7 General Formula 8 General Formula 9 General Formula 10 53 Table I General Formul .a 1 H S0CH 3 H 0CH 3 OCH 3 CH 170-174 H SOCH H 0CH 3 CH 3 CH 138-140 H S0CH 3 H Cl OCH 3 CH 124-126 H SOCH H CH 3 CH 3 CH 126-127.5 H SOCH H 0CH 3 0CH 3 N H SOCHg H 0CH 3 CH 3 N 165-167 H SOCH H OCH CH 3 NHCH N H SOCH CH 3 0CH 3 CH 3 N 133-137 4- ■ CHg ' SOCH 3 H 0CH 3 0CH 3 CH 4- ■0CH 3 SOCH H 0CH 3 0CH 3 CH 6- CH 3 SOCH H 0CH 3 OCH 3 CH 6- •0CH 3 SOCH H 0CH 3 0CH 3 CH 6- •F SOCH H CH 3 0CH 3 CH 6- •Cl SOCH H OCH 3 OCH 3 CH H SO„CH H OCH 3 0CH 3 CH 170-172 2 3 H S0 2 CH 3 H OCH, CH 3 CH 158-160 3 H S0 2 CH 3 H Cl OCH 3 CH 158-160 H 0 2 CH 3 H CH 3 CH 3 CH 162-164 H S0 2 CH 3 H OCH 3 0CH 3 N 180-184 H S0 2 CH 3 H OCH 3 CH 3 N 154-156.5 H S0 2 CH 3 H OCH 2 CH 3 NHCH N H S0 2 CH 3 CH 3 OCH 3 CH 3 N 4- -CH 3 S0 2 CH 3 H OCH 3 0CH 3 CH 4- -0CH 3 S0 2 CH 3 H OCH 3 0CH 3 CH 6- -CH 3 S0 2 CH 3 H OCH 3 0CH 3 CH 6- -0CH 3 S0 2 CH 3 H 0CH 3 0CH 3 CH 6- -F S0 2 CH 3 H OCH 3 0CH 3 CH 6- -Cl 0 2 CH 3 H OCH 3 0CH 3 CH Table I (continued) m. p . ( °C) H SOCH 2 CH 3 H OCH 3 OCH 3 CH 132-136 H SOCH Λ CH„ H OCH 3 CH 3 CH 141-144 2 3 H S0CH n CH H Cl OCH 3 CH 105-107.5 2 3 H SOCH„CH„ H CH 3 CH 3 CH 153-156.5 2 3 H SQCH„CH„ H 0CH 3 OCH 3 N 154-158 2 3 H S0CH„CH o H 0CH 3 CH 3 N 172-174 2 3 H S0CH„CH., H OCH^CH, NHCH N 2 3 2 3 H SOCH fl CH. GH 3 OCH 3 CH 3 N 2 3 4-CH 3 S0CH 2 CH 3 H OCH 3 OCH 3 CH 4-OCH 3 S0CH 2 CH 3 H OCH 3 OCH 3 CH 6-CH 3 SOCH CH H OCH 3 OCH 3 CH 6-OCH SOCH CH H OCH 3 0CH 3 CH 2 3 6-F SOCH CH„ H OCH 3 OCH 2 3 3 CH 6-C1 S0CK Λ CH Λ H OCH„ OCH CH 2 3 3 3 H S0 2 CH 2 CH 3 H OCH3 CH 3 CH 160-162 H S0 2 CH 2 CH 3 H OCH CH 3 3 CH 160-162 H S0 Λ CH Λ CH H Cl OCH 3 CH 163-164.5 2 2 3 H SO CH CH H CH 3 CH 3 CH 167-169 2 2 3 H H OC R , S0 2 CK 2 CH 3 3 OCH3„ N 155-158 H 0 2 CH 2 CH 3 H 0CH 3 CH 3 N 165.5-168 H 0 2 CH 2 CH 3 H OCH 2 CH 3 NHCH N H SO,CH„CH_, CH 3 OCH 3 CH 3 N 137-138 2 2 3 4-CH, SO„CH„CH,, H OCH 3 OCH 3 CH 3 2 2 3 4-OCH S0 CH„CH H OCH 3 OCH 3 CH 2 2 3 6-CH 3 S0„CH„CH H 0CH 3 OCH 3 CH 178-180 2 2 3 6-CH 3 S0 2 CH 2 CH 3 H 0CH 3 CH 3 CH 169.5-172 6-CH 3 S0 2 CH 2 CH 3 H CH 3 CH 3 CH 172-173.5 6-CH 3 0 2 CH 2 CH 3 CH 3 0CH 3 CH 3 N 133-135 6-OCH S0_.CH,CH_, H 0CH_, OCH„ 2 2 3 CH 3 210-213 3 6-F SO CH CH H OCH 2 2 3 3 OCH 3 CH 157-160 6-F SO CH CH H CH 3 CH 3 CH 176-177 2 2 3 55 Ta b le I (continued) R X Y Z m. .rc !a 89 6-1 .1 S0 2 CH 2 CH 3 H OCH OCH CH 187-1 3 171-174 6-1Cl SO CH CH H Cl OCH 3 CH 2 2 3 6-ι Cl SO,CH,CH, H CH 3 CH 3 CH 181-182 2 2 3 6- S0,CH,CH, H OCH 3 OCH 3 CH SCH 3 2 2 3 6- SCH, SO,CH,CH, H Cl OCH 3 CH 3 2 2 3 CH 159-160 5-CH 3 S0,CH,CH„ H 0CH 3 OCH 3 2 2 3 S0 2 CH 2 CH 3 OCH 3 CH 176-177 5- CH_ H Cl 3 S0 2 CH 2 CH 3 3 OCH 3 N 155-156 5-CH_ H OCH 3 61 5-CH_ S0,CH„CH, H OCH 3 N 159-1 3 2 2 3 CH 3 H SOCH CH CH H OCH 3 OCH 3 CH 111-115 H S0CH,CH,CH, H OCH 3 CH 3 CH 141-145 2 2 3 H S0CH 2 CH 2 CH 3 H Cl OCH 3 CH 111-113 H H CH 3 CH 3 CH 173-175 H H OCH 3 OCH 3 N 186-189 2 2 3 N 164-166 H SOCH CH CH, H OCH 3 CH 3 2 2 3 H SOCH CH CH, H OCH,CH, NHCH, N 121-123 2 2 3 2 3 3 H SOCH CH CH CH 3 OCH, N 2 2 3 3 CH 3 CH 4- -CH 3 SOCH CH CH, H OCH, 0CH 3 2 2 3 3 4- -OCH SOCH CH CH, H OCH 0CH 3 CH 3 2 2 3 3 6- -CH 3 SOCH CH CH H OCH, OCH, CH 2 2 3 3 3 6- -OCH SOCH CH CH H OCH OCH, CH 3, 2 2 3 3 3 OCH, CH 6- -F SOCH CH CH, H OCH, 2 2 3 3 3 6- -Cl SOCH CH CH, H OCH 3 OCH, CH 2 2 3 3 S0,CH,CH,CH, OCH 3 CH 168-170 H H OCH, 2 2 2 3 SO,CH„CH,CH, CH 157-159 H H OCH 3 CH 3 2 2 2 3 S0,CH,CH,C H Cl OCH 3 CH 165-167 H H, 2 2 2 3 CH 3 CH 158-160 H S0,CH,CH,CH, H CH 3 2 2 2 3 H SO,CH,CH,CH, H OCH 3 OCH 3 N 164-166 2 2 2 3 65-168 H SO,CH,CH,CH, H 0CH 3 CH 3 N 1 2 2 2 3 CH N 148-152 H S0,CH,CH CH„ H OCH,CH, NH 2 2 2 3 2 3 H S0,CH,CH,CH, CH 3 OCH 3 CH 3 N 2 2 2 3 -CH 3 SO CH CH CH, H OCH 3 OCH 3 CH 2 2 2 3 Table I (continued) 5 ι R X y Z m.o.( β C) -OCH S0 2 CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 6-CH, S0 2 CH 2 CH 2 CH 3 H CH 3 OCH 3 CH 3 6-OCH S0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-F S0 2 CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 10 yj 6-< :ι S0 2 CH 2 CH 2 CH 3 H OCH 3 0CH 3 CH H SOCH CH 3 ) 2 H OCH 3 OCH 3 CH 144-147 H SOCH(CH 3 > 2 H OCH 3 CH 3 CH 143-145.5 H S0CH(CH 3 > 2 H Cl OCH 3 CH 133-135 CH 150-153 K 155-159 N 150-153 N N 4- CH 3 SOCH CH 3 ) 2 H OCH OCH 3 CH 20 4- OCH 3 SOCH(CH 3 ) 2 H OCH 3 0CH 3 CH 6- •CH 3 S0CH(CH 3 ) 2 H OCH 3 OCH 3 CH 6- •OCH 3 S0CH(CH 3 > 2 H 0CH 3 0CH 3 CH 6- •F SOCHCCH 3 ) 2 H OCH 3 OCH 3 CH 6- -Cl S0CH(CH 3 > 2 H OCH 3 OCH 3 CH 25 H S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH 140-146 H 0 2 CH CH 3 ) 2 H OCH, CH 3 CH 159-160.5 3 H S0 2 CH(CH 3 ) 2 H Cl OCH 3 CH 164-165.5 H S0 2 CH(CH 3 ) 2 H CH 3 CH 3 CH 161-163 H S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 N 164-166 30 H S0 2 CH(CH 3 ) 2 H 0CH 3 CH 3 N 165-167 H S0 2 CH(CH 3 ) 2 H 0CH 2 CH 3 NHCH N H S 2 CH(CH 3 ) 2 CH 3 0CH 3 CH 3 N 145-149 4- -CH 3 S0 2 CH(CH 3 ) 2 H OCH 3 0CH 3 CH 4- -OCH 3 S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH 35 6 -CH 3 S0 2 CH(CH 3 ) 2 H 0CH 3 OCH 3 CH Table I ( continued) 6-OCH 3 S0 2 CH(CH 3 2 H 0CH 3 OCH 3 CH ' 6-F S0 2 CH( CH 3 ) 2 H OCH 3 OCH CH 6-C1 S0,CH(CH, ) „ H OCH 3 OCH 3 CH 2 3 2 H S0CH,CH,CH,CH, H OCH, OCH 3 CH 2 2 2 3 3 H SOCH CH CH CH, H OCH, CH 3 CH 2 2 2 3 3 H SOCH CH CH CH, H Cl OCH, CH 2 2 2 3 3 H SOCH CH CH CH H CH 3 CH 3 CH H S CH 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 N H SOCH 2 CH 2 CH 2 CH 3 H OCH 3 CH 3 N H SOCH 2 CH 2 CH 2 CH 3 H OCH,CH, NHCH, N 2 3 H SOCH 2 CH 2 CH 2 CH 3 CH, OCH 3 CH 3 " N 4-CH 3 SOCH 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 4-OCH, SOCH,CH,CH,CH, H 0CH 3 OCH 3 CH 3 2 2 2 3 6-CH, SOCH,CH,CH,CH_ H OCH 3 OCH 3 3 2 2 2 3 CH 6-OCH, SOCK,CH,CH,CH, H OCH 3 OCH 3 3 2 2 2 3 CH 6-F SOCH,CH,CH,CH, H OCH 3 OCH, 2 2 2 3 CH 3 6-C1 SOCH,CH,CH,CH, H OCH 3 OCH 2 2 2 3 CH H SO,CH,CH,CH,CH, H OCH, OCH 3 2 2 2 2 3 3 CH 155-157 H SO,CH,CH,CH,CH, H OCH, CH 3 CH 142-144 2 2 2 2 3 3 H SO„CH,CH,CH,CH, H Cl OCH, CH 151-153 2 2 2 2 3 3 H SO CH CH CH CH, H CH 3 CH 3 CH 142-143 2 2 2 2 3 H SO CH CH CH,CH, H OCH 3 OCH 3 N 153.5-155 2 2 2 2 3 H SO„CH,CH,CH,CH, H OCH, CH 3 N 142.5-145.5 2 2 2 2 3 3 H SO„CH„CH„CH,CH, H OCH,CH, NHCH, N 2 2 2 2 3 2 3 3 H SO,CH,CH,CH,CH, CH, OCH CH 3 2 2 2 2 3 3 N H SO,CH,CH,CH,CH, CH, 0CH 3 OCH 3 2 2 2 2 3 3 N 133-136 4-CH, SO,CH,CH,CH,CH, H OCH 3 OCH CH 3 2 2 2 2 3 4-OCH, SO,CH,CH,CH,CH, H 0CH 3 OCH 3 3 2 2 2 2 3 CH 6-CH, SO,CH,CH,CH,CH, H OCH 3 OCH 3 3 2 2 2 2 3 CH 6-OCH SO,CH,CH,CH,CH, H OCH_ OCH 3 2 2 2 2 3 CH Table X (continued) R X Y Z m.p.CC) 6-F SO,CH,CH,CH,CH H OCH 3 0CH 3 CH 2 2 2 2 3 6-C1 SO,CH,CH,CH,CH, H OCH 3 CH 2 2 2 2 3 0CH 3 H S-cyclopropyl H OCH 3 0CH 3 CH H S-cyclopropyl H OCH, CH 3 CH 3 H S-cyclo rop 1 H Cl 0CH 3 CH H S-cyclopropyl H H 3 CH 3 CH H S-cyclopropyl H OCH, OCH N 3 3 H S-cyclopropyl H 0CH 3 CH 3 N H S-cyclopropyl H OCH„CH„ NHCH, N 2 3 3 H S-cyclopropyl CH CH 3 N 3 ° CH 3 -CH 3 S-cyclopropyl H OCHg CH 3 CH -OCH, S-cyclopropyl H 0CH 3 0CH 3 CH 3 6-CH 3 S-cyclopropyl H 0CH 3 OCH 3 CH 6-OCH, S-cyclopropyl H 0CH 3 0CH 3 CH 3 6-F S-cyclopropyl H OCH 0CH 3 CH 6-C1 S-cyclopropyl H 0CH 3 OCH CH Table I (continued) _1 R Z m.p.(°C) H SO-cyclopropyl H 0CH 3 OCH, CH H SO-cyclopropyl H OCH 3 CH 3 " CH H SO-cyclopropyl H Cl 0CH 3 CH H SO-cyclopropyl H CH 3 CH 3 CH H SO-cyclopropyl H OCH 3 0CH 3 N H SO -cyclopropyl H 0CH 3 CH 3 N H SO-cyclopropyl H 0CH,CH, NHCH N 2 3 H SO-cyclopropyl CH OCH, CH 3 N •3 3 4-CH 3 SO-cyclopropyl H 0CH_ OCH, CH 3 4-0CH, SO-cyclopropyl H OCH. OCH. CH 6-CH, SO-cyclopropyl H 0CH 3 OCH CH 3 6 -OCH, SO-cyclopropyl H OCH„ OCH 3 CH 6-F SO-cyclopropyl H OCH. OCH. CH 6-C1 SO-cyclopropyl H 0CH 3 OCH 3 CH H SO -cyclopropyl H OCH, 0CH 3 CH 3 H SO -cyclopropyl H OCH, CH 3 CH 3 H SO -cyclopropyl H Cl OCH 3 CH H SO -cyclopropyl H CH 3 CH 3 CH H SO -cyclopropyl H 0CH 3 0CH 3 N H SO -cyclopropyl H OCH 3 CH 3 N H SO -cyclopropyl H 0CH,CH, NHCH N 2 3 H SO -cyclopropyl CH 0CH 3 CH 3 N 4-CH 3 SO -cyclopropyl H OCH, 0CH 3 CH 3 4 -OCH, SO -cyclopropyl H 3 OCH, 0CH 3 CH -CH 3 SO -cyclopropyl H OCHg 0CH 3 CH 6 -OCH SO -cyclopropyl H OCH, OCH, CH 3 3 6-F SO -cyclopropyl H OCH. OCH. CH -C1 SO -cyclopropyl H OCH, OCH, 3 3 CH Table I (continued) ι R X y Z m.p.CC) H OS0 2 CH 3 H OCH 3 OCH 3 CH 169-171 H 0S0 2 CH 3 H OCH 3 CH 3 CH 172-173.5 H OS0 2 CH 3 H Cl OCH 3 CH 171-173 H OSO,CH„ H CH 3 CH 3 CH 161.5-165 2 3 H OSO-CH, H OCH 3 0CH 3 N 2 3 H 0S0 2 CH 3 H OCH 3 CH 3 N 155-158 H H 0CH,CH, NHCH, N 0S0 2 CH 3 2 3 3 H OSO,CH, CH 3 0CH 3 CH 3 N 2 3 4-CH 3 3, 0S0,CH, H 0CH OCH 3 CH 2 3 -OCH H 3 3, OSO,CH, H OC OCH 3 - CH 2 3 6-OCH 0S0 2 CH 3 H OCH 3 OCH 3 CH 6-F OSO,CH, H 0CH 3 OCH, 2 3 3 CH 6-C1 00 2 CH 3 H OCH 3 OCH 3 CH H OS0 2 CH 2 CH 3 H OCH OCH 3 CH 162-163.5 H 0S0,CH,CH, H OCH 3 CH 2 2 3 160-162 CH 3 H OSO,CH„CH, H Cl OCH 3 CH 2 2 3 139-143 H OSO,CH,CH, H CH 3 CH 3 CH 2 2 3 132-138 H OSO CH CH H 0CH 3 2 2 3 OCH 3 N 171.5-173 H OSO,CH,CH, H 0CH 2 2 3 CH 3 N 147-149 H 0S0 2 CH 2 CH 3 H OCH 2 CH 3 NHCH N H " OS0 2 CH 2 CH 3 CH 3 0CH 3 CH 3 N 4-CH 3 OSO,CH,CH, H 0CH 3 OCH 3 2 2 3 CH 4-OCH, OSO,CH,CH, H 0CH 3 3 OCH 2 2 3 3, CH 6-CH, OSO,CH,CH, H 3 OCH, OCH, 2 2 3 CH 3 3 6-OCH, OSO,CH,CH, H 3 OCH, 2 2 3 OCH 3 3, CH 6-F 0S0,CH,CH, H OCH, OCH, 2 2 3 CH 3 3 6-C1 OSO,CH CH, H OCH, OCH, 2 2 3 CH Table I (continued) R X Y Z m. ■ c) H OSO,CH,CH,CH, H OCH 3 OCH 3 CH 156- -157 2 2 2 3 H OS0 2 CH 2 CH 2 CH 3 H OCH, CH 3 CH 3 131- -133 H OS0 2 CH 2 CH 2 CH 3 H Cl OCH 3 CH 127- -132 H OSO,CH,CH„CH, H CH 3 CH 3 CH 152- -153 2 2 2 3 H OS0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 N 154- ■155 H OS0 2 CH 2 CH 2 CH 3 H OCH 3 CH 3 N H OSO_CH,CH,CH, H OCH 2 CH 3 NHCH N 2 2 2 3 H OSO,CH,CH,CH, CH 3 OCH 3 N 2 2 2 3 CH 3 4-CH 3 OSO,CH,CH,CH, H OCH 3 OCH 3 CH 2 2 2 3 4-OCH 3 OSO,CH,CH,CH, H OCH 3 OCH 3 CH 2 2 2 3 6-CH 3 OSO,CH,CH,CH, H OCH 3 OCH 3 CH 2 2 2 3 6-OCH OSO„CH,GH,CH, H OCH 3 OCH 3 CH 2 2 2 3 6-F OSO,CH,CH,CH, H OCH OCH 3 CH 2 2 2 3 6-C1 OS0 2 CH 2 CH 2 CH 3 H OCH3, OCH 3 CH H 0S0 2 CH(CH 3 > 2 H OCH3, OCH3, CH H OS0 2 CH(CH 3 2 H OCH 3 CH 3 CH H 0S0 2 CH(CH 3 ) 2 H Cl OCH 3 CH H 0S0 2 CH CH 3 2 H CH 3 CH 3 CH H O 0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 H OS0 2 CH(CH 3 ) 2 H OCH 3 CH 3 N H OS0 2 CH(CH 3 ) 2 H OCH,CH, NHCH N 2 3 H 0S0 2 CH(CH 3 2 CH 3 OCH 3 CH 3 N 4-CH, OS0 2 CH(CH 3 2 H OCH 3 OCH 3 CH 3 -OCH 0S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH 6-CH 3 OS0 2 CH CH 3 2 H OCH 3 0CH 3 CH 6-OCH OS0 2 CH(CH 3 ) 2 H OCH, OCH 3 CH 3 -F 0S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH -C1 OS0 2 CH(CH 3 2 H OCH 3 OCH 3 CH Table I (continued) 2 m.P . CO H 0S0,CH,CH,CH,CH. H OCH 3 OCH 3 CH 2 2 2 2 3 H 0S0,CH CH^CH.CH, H 0CH 3 CH 2 2 2 2 3 CH 3 H 0S0,CH,CH^H^CH, H 2 2 2 2 3 Cl 0CH 3 CH H 0S0,CH,CH,CH,CH, H CH 3 CH 3 CH 2 2 2 2 3 H 0S0,CH CH,CH,CH 0 H 0CH 3 0CH 3 N 2 2 2 2 3 H 0S0,CH„CH,CH,CH, H 0CH 3 CH 3 N 2 2 2 2 3 H 0S0,CH,CH,CH,CH_ H 0CH 2 CH 3 NHCH N 2 2 2 2 3 H 0S0,CH CH,CH„CH, CH 3 0CH 3 CH 3 N 2 2 2 2 3 4- -CH 3 0S0,CH„CH,CH„CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 4- -0CH 3 0S0,CH,CH,CH,CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 6- -CH 3 0S0,CH,CH,CH,CH, H 0CH 3 OCH 3 CH 2 2 2 2 3 6- ■OCH, 0S0,CH,CH,CH,CH, H 0CH 3 OCH 3 CH 2 2 2 2 3 6- -F 0S0,CH,CH,CH„CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 6- -Cl 0S0,CH,CH,CH,CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 H 0S0„CF, H 0CH 3 0CH 3 CH 1 0- -142 2 3 H 0S0 CF, H 0CH 3 CH 2 3 3, CH H 0S0,CF, H Cl OCH 2 3 3, CH 154- -156 H 0S0,CF, H CH 3 CH 3 CH 157- 2 3 -160 H 0S0„CF, H 0CH 3 2 3 0CH 3 N 164- -166 H OS0,CF, H CH 3 CH 3 2 3 N 157- -159 H 0S0,CF, H 2 3 * 0CH,CH, NHCH, N 2 3 3 H 0S0,CF, CH 3 OCH, CH 3 2 3 N 3 4- •CH 3 0S0,CF, H 0CH 3 2 3 0CH 3 CH 4- ■0CH 3 0S0,CF, H 0CH 3 2 3 0CH 3 CH 6- CH 3 0S0,CF, H 2 3 0CH 3 0CH 3 CH 6- 0CH 3 0S0,CF, H 2 3 OCH 3 0CH 3 CH 6- F 0S0,CF, 2 3 H 0CH 3 0CH 3 CH 6- Cl 0S0,CF, H 2 3 0CH 3 OCH CH Table I (continued) R X y Z m.P.( β C > H OSO.CCl, H 0CH 3 0CH 3 CH 2 3 H 0S0,CC1, H 0CH 3 CH 3 CH 2 3 H 0S0,CC1, H Cl OCH 3 CH 2 3 H oso 2 ccι 3 H CH 3 CH 3 CH H oso 2 ccι 3 H OCH 3 0CH 3 N H oso 2 ccι 3 H 0CH,CH, NHCH N 2 3 H oso 2 ccι 3 CH 3 0CH 3 CH 3 N 4-CH 3 oso 2 ccι 3 H 0CH 3 OCH 3 CH -OCH oso 2 ccι 3 H OCH 3 OCH 3 CH 6-CH 3 oso 2 ccι 3 H OCH 3 OCH 3 CH 6-OCH oso,ccι, H 0CH 3 OCH, CH 2 3 3 6-F oso 2,ccι, H OCH 3 OCH, CH 3 3 6-C1 oso 2,ccι3, H OCH 3 OCH3, CH H 0S0,CH,CH,CH,C1 H OCH 3 OCH 2 2 2 2 3, CH H OSO,CH,CH,CH,Cl H OCH 2 2 2 2 3, CH 3 CH H 0S0,CH,CH,CH,C1 H Cl OCH 3 CH 2 2 2 2 H 0S0,CH,CH„CH,C1 H CH 3 CH 3 CH 2 2 2 2 H 0S0,CH„CH,CH,C1 H 0CH 3 OCH 3 N 2 2 2 2 H 0S0,CH,CH,CH,C1 H OCH 3 CH 3 N 2 2 2 2 H 0S0,CH,CH,CH,C1 H OCH,CH, NHCH N 2 2 2 2 2 3 H 0S0,CH,CH,CH,C1 CH 3 OCH 3 CH 3 N 2 2 2 2 4-CH 3 OSO,CH,CH,CH,Cl H OCH 3 OCH 3 CH 2 2 2 2 4-OCH, OSO,CH,CH,CH,Cl H OCH 3 OCH 3 CH 3 2 2 2 2 6-CH, 0S0,CH,CH,CH,C1 H OCH OCH 3 CH 3 2 2 2 2 3, 6-OCH, 0S0,CH,CH,CH,C1 H OCH 3 OCH 3 CH 3 2 2 2 2 6-F 0S0,CH,CH,CH,C1 H 0CH 3 OCH 3 CH 2 2 2 2 6-C1 OSO,CH,CH,CH,Cl H OCH, OCH 3 CH 2 2 2 2 3 X X X Nl o o υ o , ϊC * 33 3-} 33 33 ? 33 3, 33 a a a υ υ o o υ o o o o a a a a vO CO Pl Pl tO Pl tO tO PI PI PI fO tO CO P) fo fo of fo fo fo fo fo ix, fo fo fo fo o o o o o o o o o o o o o o CM CM CM CM CM CM CM CM CM CM CM CM CM CM PI Pl Pl CO CO tO tO t X X X X X X X X X X X X X X X X X X X X X X O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O CM CM CM CM CM CM cM CM CM lM tM CM cM cM cM CM CM fM CM CM CM t .Ml O O O O O O O P O O O O O O O O O O O O O O tύ O CO CO C CO CO CO CO CO CO CO CO CO CO CO CO IO CO CO C CO CO 65 Table I (continued) R. R __ Y m.p. CO OCH 3 CH H H OCH 3 S0 2° CH 2 CH 3 CH 3 CH H SO OCH 2 CH 3 H OCH 3 OCH 3 CH H SO OCH 2 CH 3 H Cl H S0 2 0CH 2 CH 3 H CH 3 CH 3 CH H S0 2 OCH 2 CH 3 H OCH, OCH, N N H S0 2 0CH 2 CH 3 H OCH, CH. * 3 " 3 H H OCH CH, NHCH N S0 2° CH 2 CH 3 2 - " 3 " — ■ 3 H S0 2 OCH 2 CH 3 CH 3 0CH 3 CH. N 3 4-CH 3 S0 2 0CH 2 CH 3 H OCH 3 OCH 3 CH 4-OCH, SO,OCH,CH H 0CH 3 0CH 3 CH 3 "2 " ~ " 2 "" 3 CH 6-CH, SO OCH CH, H OCH 3 OCH 3 3 2 2 3 6-OCH SO OCH 2 CH 3 H OCH 3 OCH 3 CH 6-F H 0CH 3 OCH 3 CH S0 2° CH 2 CH 3 6-C1 S0,0CH,CH, H OCH 3 OCH 3 CH H H OCH 3 OCH 3 CH H N, H 0CH 3 CH 3 CH H H Cl OCH, CH H H CH 3 CH 3 " CH H H OCH.. OCH^ N H H OCH, CH. N 3 H H OCH CH NHCH N <3 2 3 J H CH OCH CH 3 N 4-CH, . N.,. H OCH 3 OCH 3 CH 3 3 4-OCH, N, H 0CH 3 OCH, CH 3 3 6-CH, N„ H 0CH 3 OCH, CH " 3 " 3 6-OCH 3 N 3 H OCH, OCH, CH • 3 3 6-F N, H OCH, . OCH CH 6-Cl H_ H OCH, OCH, CH Table I (continued) H ?2 R X Y Z .o.CC) CN H OCH 3 OCH 3 CH H H CN H 0CH 3 CH, CH 3 H CN H Cl OCH 3 CH H CN H CH 3 CH 3 CH H CN H OCH 3 OCH 3 N H CN H OCH 3 CH 3 N H CN H OCH 2 CH 3 NHCH N -H CN CH 3 OCH 3 CH 3 N 4- CH 3 CN H OCH 3 OCH 3 CH 4- 0CH 3 CN H OCH 3 OCH 3 CH 6- CH 3 CN H OCH, OCH 3 " CH 6- 0CH 3 CN H OCH OCH 3 CH 6- F CN H OCH 3 OCH 3 CH 6- ■Cl CN H OCH 3 OCH 3 CH H P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH H P(0)(0CH 3 ) 2 H OCH 3 CH CH 3 H P(0)(OCH 3 ) 2 H Cl OCH 3 CH H P(0)(OCH 3 ) 2 H CH 3 CH 3 CH H P(0)(OCH 3 ) 2 H OCH 3 OCH 3 N H P(0)(OCH 3 ) 2 H OCH 3 N CH 3 H P(0)(OCH 3 ) 2 H OCH 2 CH 3 NHCH N H P(0)(OCH 3 ) 2 CH 3 OCH 3 CH 3 N 4- -CH 3 P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH 4- -0CH 3 P 0) 0CH 3 ) 2 H OCH 3 OCH 3 CH 6- -CH 3 P(0)(OCH 3 ) 2 H OCH 3 OCH, CH 3 6- -0CH 3 P 0)COCH 3 ) 2 H OCH 3 OCH 3 CH 6- -F P(0)(OCH 3 ) 2 H OCH 3 OCH, CH 3 6- -Cl P(0)(OCH 3 ) 2 H OCH 3 . OCH 3 CH 67 Table I (continued) !ι R X Y Z m.p. CO H P(0 OCH 2 CH 3 2 H 0CH 3 OCH 3 CH 108-111 H P 0)(0CH 2 CH 3 ) 2 H 0CH 3 CH 3 CH H P(0) OCH 2 CH 3 ) 2 H Cl OCH 3 CH H P(0 (OCH 2 CH 3 ) 2 H CH 3 CH 3 CH 110-114 H P(0 (OCH 2 CH 3 ) 2 H OCH 3 OCH 3 N H P(0 (0CH 2 CH 3 ) 2 H 0CH 3 CH 3 N H P 0 OCH 2 CH 3 ) 2 H OCH,CH, NHCH N 2 3 H P 0) OCH 2 CH 3 ) 2 CH 3 OCH 3 CH 3 N 4-CH 3 P(0)(0CH,CH,), H OCH 3 OCH 3 CH 4b J Δ 4-0CH, P 0 (OCH 2 CH 3 ) 2 H OCH 3 OCH 3 - CH 6-CH OCH 3 CH , J *_! P(0 OCH 2 CH 3 ) 2 H 0CH 3 6-OCH P(0 (OCH 2 CH 3 ) 2 H 0CH 3 OCH 3 CH 6-F P(0 (OCH 2 CH 3 ) 2 H OCH 3 OCH 3 CH 6-C1 P(0 OCH 2 CH 3 ) 2 H 0CH 3 OCH 3 CH H P(S)(OCH 3 ) 2 H OCH 3 OCH 3 CH H P(S (OCH 3 2 H OCH 3 CH 3 CH H P(S)(OCH 3 ) 2 H Cl OCH 3 CH H P(S)(OCH 3 ) 2 H CH 3 CH 3 CH H P(S)(0CH 3 ) 2 H 0CH 3 OCH 3 N H P(S)(OCH 3 ) 2 H OCH 3 CH 3 N H P(S)(OCH 3 ) 2 H OCH,CH, NHCH 2 3 i N H P(S)(0CH 3 ) 2 CH 3 0CH 3 CH 3 N 4-CH P(S)(0CH 3 2 H 0CH 3 OCH, CH 3 4-0CH ; P(S)(0CH 3 ) 2 H OCH, OCH, CH 3 3 6-CH P(S)(OCH 3 ) 2 H OCH, OCH 3 CH 3 6-0CH, . P(S OCH 3 ) 2 H OCH, OCH 3 CH 3 6-F P(S)(0CH 3 ) 2 H OCH, OCH, CH 3 3 6-C1 P(S)(0CH 3 ) 2 H OCH, OCH, CH 3 3 Table I (continued) R X Y Z m.p. CO H P S) OCH 2 CH 3 ) 2 H OCH 3 OCH 3 CH H P S) OCH 2 CH 3 ) 2 H OCH 3 CH 3 CH H PCSXOCH CH ) H Cl OCH 3 CH H P S) OCH 2 CH 3 2 H CH 3 - CH 3 CH H P(S)(OCH CH H OCH 3 OCH3, N H P(S)(OCH CH ) H OCH 3 CH 3 N H PCS) (OCH CH ) H OCH,CH, NHCH _£ b 2 3 3, N H PCS)COCH 2 CH ) CH 3 OCH3, CH 3 N 4 " CH 3 p C )(OCH 2 CH 3 ) 2 H OCH 3 OCH 3 CH 4 -OCH PCS)COCH CH ) H OCH 3 OCH 3 - CH 6-CH 3 P(S)(0CH 2 CH 3 ) 2 H OCH3, OCH 3 CH 6-OCH PCS)COCH CH ) H OCH 3 OCH 3 CH 6-F PCS COCH 2 CH 3 2 H OCH 3 OCH 3 CH 6-C1 CS)COCH 2 CH 3 ) 2 H OCH 3 OCH 3 CH H CH F H OCH 3 OCH 3 CH H CH,F H OCH 3 CH 3 CH 2 H CH F H Cl OCH 3 CH H CH F H CH 3 CH 3 CH H 0CH 3 OCH 3 N K CH 2 F H CH,F H OCH 3 CH 3 N 2 H CH,F H OCH,CH, NHCH 2 2 3 3, N H CH,F CH 3 OCH, CH 3 N 2 3 -OCH, CH,F H OCH, OCH, 3 2 3 3 CH 6-OCH, CH,F H OCH, O 3 2 3 CH, CH 3 6-F CH F H OCH, OCH, 2 3 3 CH 6-C1 CH,F H OCH, OCH, CH 2 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X ^ ^ ^ ^ f q ", » *i , *J to to io to to to to to to to to to to to to to to to to io to to Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X Ω X X X X X X 33 33 3« 33 33 X X ω ω O O O O O O O Ω Ω Ω Ω Ω Ω Ω X X X X X X X ω ω ω ω ω ω ω O O O O O O Ω Ω O O O O O Q O O O O O O a Ω Ω Ω Ω Ω Ω X X Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X X X X X X X ω Ω CO ω x ω x x x x x x x ω Ω ω ω ω ω ω ω x ω ω ω ω ω ω ω ω ω X ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X a a a a Ω Ω Ω Ω Ω Ω X X X X X X X X X X a a Table I (continued) R- X m.p . CO H CC Λ _ti H OCH 3 OCH 3 CH 2 H CC1 H H OCH 3 CH 3 CH H CC1 2 H H Cl OCH 3 CH H CC1 2 H H CH 3 CH 3 CH H H OCH 3 OCH 3 N CC1 2 H H CC1 2 H H OCH 3 CH 3 N H CC1 H H OCH 2 CH 3 NHCH . N H CC1 H CH 3 OCH, CH 3 N 3 4-CH 3 CC1 2 H H OCH 3 OCH 3 CH 4-OCH, CC1 H H 3 ° CH 3 OCH, CH 3 6-CH 3 CC1,H H CH 3 CH 2 0CH 3 6-OCH3, CC1 H H 0CH 3 OCH, CH 2 3 6-C1 CC1 2 H H OCH, OCH, 3 3 CH H CH,CH,C1 H OCH 3 OCH, 2 2 3 CH H CH,CH,C1 H 0CH 3 CH 3 . CH 2 2 H CH,CH,C1 H Cl OCH 3 CH 2 2 H CH,CH,C1 H CH 3 CH 3 . CH ' 2 • 2 H CH,CH,C1 H OCH 3 OCH 3 N 2 2 H CH,CH,C1 H 0CH 3 CH 3 N 2 2 H CH,CH,C1 H 0CH,CH, NHCH N 2 2 2 3 H CH,CH,C1 CH 3 OCH 3 CH 3 N 2 2 4-CH 3 CH,CH,C1 H 0CH 3 OCH 3 CH 2 2 4-OCH, CH,CH,C1 H OCH, OCH 3 CH 3 2 2 3 6-CH, CH,CH,C1 H 0CH 3 OCH, 3 2 2 3 CH 6-OCH CH CH Cl 3 H OCH, OCH 3 2 2 3 CH 6-F CH,CH,C1 H OCH, OCH, CH 2 2 3 3 6-C1 CH CH Cl H OCH, OCH, CH 2 2 3 3 71 Table I (continued) ?1 R X Y z m.p.CO OCH 3 CH H H OCH 3 CH 2 CH 2 Br H CH 2 CH 2 Br H OCH 3 CH 3 CH 3 CH H H Cl OCH CH 2 CH 2 BΓ H H H CH 3 CH 3 C CH 2 CH 2 BΓ H CH 2 CH 2 Br H OCH 3 OCH 3 N H H OCH 3 CH 3 N CH 2 CH 2 BΓ H H OCH 2 CH 3 NHCH 3 N CH 2 CH 2 BΓ H CH 3 0CH 3 CH 3 N CH 2 CH 2 BΓ 4- CH 3 H OCH 3 OCH 3 CH CH 2 CH 2 BΓ 4- 0CH 3 CH,CH_Br H OCH 3 OCH 3 . CH 2 2 6- CH 3 CH 2 CH 2 BΓ H OCH 3 OCH 3 CH OCH 3 CH 6- •0CH 3 CH 2 CH 2 BΓ H OCH 3 6- •F CH,CH,BΓ H OCH 3 OCH 3 CH 2 2 6- ■Cl CH,CH,BΓ H OCH 3 OCH 3 CH 2 2 H CHFCH H OCH 3 0CH 3 CH H CHFCH H OCH 3 CH 3 CH H CHFCH H Cl OCH 3 CH H CHFCH H CH, CH 3 CH 3 - H CHFCH 3 H OCH 3 OCH 3 N H CHFCH 3 H OCH 3 CH 3 N H CHFCH H OCH 2 CH 3 NHCH N H CHFCH 3 CH 3 OCH 3 CH 3 N 4- -CH 3 CHFCH H 0CH 3 OCH 3 CH 4- -0CH 3 CHFCH 3 H OCH 3 OCH 3 CH 6- -CH 3 CHFCH 3 H OCH 3 OCH 3 CH 6- -0CH 3 CHFCH H OCH 3 OCH 3 CH 6- -F CHFCH 3 H OCH 3 OCH 3 CH 6- -Cl CHFCH. H OCH OCH CH Table I (continued) H CHC1CH H OCH 3 OCH 3 CH H GHC1CH H OCH 3 CH 3 CH H CHC1CH H Cl OCH 3 CH H CHC1CH H CH 3 CH 3 CH H CHC1CH H OCH 3 OCH 3 H CHC1CH K OCH 3 CH 3 N H CHC1CH H OCH,CH„ NHCH N 2 3 H CHC1CH CH 3 OCH 3 CH 3 N 4-CH, CHC1CH H OCH 3 OCH 3 CH 4-OCH, CHC1CH, H OCH 3 OCH 3 CH 3 3 6-CH, CHC1CH, H OCH 3 OCH 3 CH 3 3 6 -OCH. CHC1CH. H OCH 3 OCH 3 CH 6-F CHC1CH H OCH s OCH 3 CH 6-C1 CHC1CH, H OCH 3 OCH 3 CH 3 H CF,CF,H H OCH 3 CH 2 2 0CH 3 H CF,CF,H H OCH, CH 2 2 3 CH 3 H CF,CF,H H Cl OCH 3 CH 2 2 H CF,CF,H H CH 3 CH 3 CH 2 2 H CF,CF,H H OCH 3 OCH 3 N 2 2 H CF,CF,H H OCH 3 CH 3 2 2 N H CF„CF,H H OCH,CH, NHCH 2 2 2 3 3, N H CF,CF,H OCH 3 CH 3 N 2 2 CH, 4-CH 3 CF,CF_H H OCH 3 OCH 3 CH 2 2 4-OCH CF 2 CF 2 H H OCH 3 OCH 3 CH 6-CH 3 CF 2 CF 2 H H OCH 3 OCH 3 CH 6-OCH CF,CF,H H OCH 3 OCH 3 2 2 CH 6-F CF,CF,H H OCH 3 OCH 3 2 2 CH 6-C1 CF,CF,H H OCH, OCH, 2 2 CH υ υ Xυ a a a a Xυ Xυ Xυ υ a a a a to to PI PI X co PI PI X X PI X PI X PI υ PI X PI X PI x PI o to ,υ x υ X υ X υ x υ X υ xl o υ o υ o υ a u o υ o υ o X υ X X Q) a υ 3 C to •H X X X υ u υ C PI PI PI CO PI PI P) CM P) X X PI x X X X PI x co o X X X υ ,υ O rH X υ υ υ υ o O rH x υ υ υ υ KIO o υ υ o o o o o o υ υ o o o o Table I C continued) R 2 R X y Z πup. ( β C) 6-OCH,CH, S0 2 CH 3 ) 2 H OCH 3 OCH 3 CH 2 3 6-0CH,CH, S0 2 CCH 3 ) 2 H 0CH 3 CH 2 3 GH 3 6-0CH 2 CH 3 SO,NCCH,)_, H Cl OCH 3 CH 2 3 2 6-OCH,CH, SO,NCCH,), H CH 3 CH 3 CH 2 3 2 3 2 6-0CH,CH, S0 2 NCCH 3 ) 2 H OCH 3 OCH 3 N 2 3 6-OCH,CH, S0 2 NCCH 3 2 H OCH 3 CH 3 N 2 3 6-0CH,CH, S0 2 NCCH 3 2 H OCH,CH, NHCH N 2 3 2 3 6-OCH CH, S0 2 NCCH 3 2 OCH 3 CH 3 N 2 3 CH 3 6-SCH,CH, S0 2 NCCH 3 ) 2 H OCH 3 OCH 3 CH 2 3 6-SCH CH, S0 2 CCH 3 ) 2 H OCH 3 CH 2 3 CH 3 6-SCH CH, S0 2 N CH 3 2 H Cl OCH 3 ' CH 2 3 6-SCH CH, S0 2 CCH 3 ) 2 H CH 3 CH 2 3 CH 3 - 6-SCH CH, S0 2 CCH 3 ) 2 H OCH 3 OCH, 2 3 3 N 6-SCH CH, S0 2 NCCH 3 ) 2 H OCH 3 N 2 3 CH 3 6-SCH CH, S0 2 N(CH 3 ) 2 H OCH,CH, NHCH, 2 3 2 3 3 N 6-SCH,CH, 0 2 N CH 3 ) 2 CH 3 OCH, CH 3 N 2 3 3 6-SCH, 3 S0 2 N CH 3 ) 2 H OCH 3 OCH 3 CH 6-SCH, S0 2 NCCH 3 ) 2 H OCH 3 CH 3 CH 3 6-SCH, S0 2 NCCH 3 ) 2 H Cl OCH 3 - CH 3 6-SCH S0 2 N CH 3 ) 2 H CH 3 CH 3 CH 6-SCH, 0 2 CH 3 ) 2 H OCH 3 OCH 3 3 N 6-SCH S0 2 NCCH 3 ) 2 H 0CH 3 CH 3 N 6-SCH S0 2 CH 3 ) 2 H OCH,CH, NHCH N 2 3 6-SCH S0 2 CCH 3 ) 2 CH 3 OCH 3 CH 3 N 6- CCH 3 ) 2 S0 2 CH 3 ) 2 H OCH 3 OCH 3 CH 6-NCCH 3 ) 2 S0 2 CH 3 ) 2 H 0CH 3 CH 3 CH 6- (CH 3 2 S0 2 N CH 3 2 H Cl OCH, CH 3 6-NCCH S0 2 NCCH 3 ) 2 H CH 3 CH 3 CH 3 2 6-NCCH ) S0 2 NCCH 3 ) 2 H OCH, OCH, 3 2 N 3 3 6-NCCH ) S0 2 N CH 3 ) 2 H OCH, CH 3 3 2 N 3 6-N(CH 3 2 S0 2 CCH 3 2 H OCH CH NHCH, N 2 3 3 • 6-NCCH 3 2 S0 2 CH 3 2 CH 3 OCH CH 3 N 3 Table I (continued) _i -2 S X 5 y Z m.p. CO 6 -NHCH SO N(CH H 0OCCHH 3 , OCH 3 CH 6 -NHCH SO M(CH ) H OOCCHH 3 , CH 3 CH 6-NHCH SO NCCH ) H CCll OCH 3 CH 6-NHCH 3 S0 2 N(CH 3 2 H CCHH 33 CH 3 CH 6 -NHCH, S0 2 (CH 3 2 H CH 3 CH 3 N j 6 -NHCH Λ . S0 2 (CH 3 2 H OCH 3 CH 3 N 6-NHCH 3 S 0 2 N(CH 3 ) 2 H 0CH„CH, NHCH N 2 3 6-NHCH 3 S0 2 NCCH 3 ) 2 CH 3 OOCCHH 3a CH 3 N 6-OCH 3 S0 2 NCCH 2 CH 3 ) 2 H OCH 3 OCH 3 CH 6 -OCH. S0 2 NCCH 2 CH 3 ) 2 H OCH 3 CH 3 CH 6 -OCH, SO,N(CH,CH,), H Cl OCH, CH j 2 2 3 2 3 6 -OCH, S0,N(CH,CH,), H CH, CH, CH -3 2 2 3 2 3 3 6 -OCH, S0,NCCH,CH,), H OCH, OCH, N 3 2 2 3 2 3 3 6-OCH 3 S0 2 NCCH 2 CH 3 2 H OCH 3 CHg N 6 -OCH S0 2 NCCH 2 CH 3 ) 2 H OCH,CH, NHCH, N 2 3 3 6 -OCH. S0,NCCH,CH,), CH, OCH, CH, N o 2 2 3 2 3 3 3 6-SCH, SO CCH CH ), H OCH, OCH, CH 3 2 2 3 2 3 Ξ 6-SCH, SO,NCCH,CH,), H OCH, CH, CH 3 2 2 3 2 3 3 6-SCH SO NCCH CH H Cl OCH CH 6-SCH, CH S0 2 N(CH 2 CH 3 ) 2 H CH 3 CH 3 6-SCH. S0 2 CCH 2 CH 3 ) 2 H OCH 3 OCH 3 N 6-SCH 3 S0 2 N CH 2 CH 3 2 H OCH 3 CH 3 N 6-SCH, SO,N(CH,CH,), H OCH,CH, NHCH, N 3 2 2 3 2 2 3 3 6-SCH 3 S0 2 NCCH 2 CH 3 ) 2 CH 3 OCH 3 CH N 6-N(CH 3 2 S0 2 NCCH 2 CH 3 ) 2 H OCH., OCH, CH 6-NCCH 3 2 S0 2 NCCH 2 CH 3 2 H OCHg CH 3 CH 6-NCCH 3 2 S0 2 NCCH 2 CH 3 ) 2 H Cl OCH CH 6- (CH 3 ) 2 S0 2 CCH 2 CH 3 2 H CH.. CH 3 CH 6-NCCH 3 2 S0 2 NCCH 2 CH 3 ) 2 H OCH OCH N 6- (CH 3 ) 2 S0 2 N(CH 2 CH 3 2 H OCH 3 CH 3 N 6-N(CH 3 ) 2 S0 2 N CH 2 CH 3 ) 2 H OCH CH, NHCH, N 2 3 3 6-N(CH 3 ) 2 S0 2 (CH 2 CH 3 ) 2 CH 3 OCH 3 CH N Table I (continued) _1 R X Y Z m- - CO 6-SCH SO,NHOCH, H OCH OCH 3 CH 2 3 6-SCH SO,NHOCH, H OCH 3 CH 3 CH 2 3 6-SCH SO NHOCH H Cl OCH 3 CH 6-SCH SO,NHOCH. H CH 3 CH 3 CH 2 3 6-SCH SO NH0CH 3 H OCH 3 OCH 3 N 6-SCH. SO,NHOCH, H OCH 3 CH 3 N 2 3 6-SCH 3 SO NHOCH H OCH 2 CH 3 NHCH N 6-SCH SO,NHOCH, CH 3 OCH 3 2 3 CH 3 N 6-SCH,CH„ SO NHOCH H OCH 3 OCH 3 CH 2 3 6-SCH,CH, SO,NHOCH, H OCH 3 CH 3 CH 2 3 2 3 6-SCH„CH. SO,NHOCH, H Cl OCH 3 CH 2 3 2 3 6-SCH,CH. SO,NHOCH„ H CH 3 CH 2 3 2 3 CH 3 6-SCH,CH, SO,NHOCH, H OCH 3 OCH 3 N 2 3 2 3 6-SCH,CH, SO,NHOCH, H OCH 3 CH 3 N 2 3 2 3 6-SCH,CH, SO,NHOCH, H 0CH 2 CH 3 NHCH N 2 3 2 3 6-SCH,CH SO,NHOCH, CH 3 cH 3 CH 3 N 2 3 2 3 6- CCH 3 ) 2 SO,NHOCH, H OCH 3 OCH 3 CH 2 3 6-NCCH 3 2 SO,NHOCH, H OCH 3 CH 3 CH 2 3 6-NCCH 3 ) 2 SO,NHOCH, H Cl OCH 3 CH 2 3 6-NCCH 3 ) 2 SO,NHOCH, H CH 3 CH 3 CH 2 3 6-NCCH 3 ) 2 SO,NHOCH, H OCH 3 OCH, N 2 3 3 6-NCCH 3 ) 2 SO, HOCH, H OCH 3 CH 3 N 2 3 6-NCCH 3 ) 2 SO,NHOCH, H OCH 2 CH 3 NHCH, N 2 3 6-NCCH 3 ) 2 SO,NHOCH, CH 3 OCH 3 CH 3 " N 2 3 6-OCH SO.NHOCH, H OCH 3 OCH 3 CH 2 3 6-OCH SO NHOCH H OCH 3 CH 3 CH 6-OCH SO,NHOCH, H Cl OCH 3 CH 2 3 6-OCH SO NHOCH H CH 3 CH 3 CH 6-OCH SO,NHOCH, H OCH 3 OCH 3 2 3 N 6-OCH. SO,NHOCH, H OCH. CH. N 2 3 Table I (continued) ι !_2 R X Y Z m.p. < β C> 6-OCH, SO,NHOCH, H 3 OCH CH, NHCH N 2 3 2 3 6-OCH, SO,NHOCH, CH 3 OCH 3 3 CH 3 N 2 3 6-OCH SO,NHCH, H OCH 3 OCH 3 CH 2 3 6-OCH SO,NHCH, H OCH 3 CH 3 CH 2 3 6-OCH S0 2 NHCH 3 H Cl OCH 3 CH 6-OCH S0 2 NHCH 3 H CH 3 CH 3 CH 6-OCH SO,NHCH, H OCH 3 OCH 3 N 2 3 6-OCH SO.NHCH- II OCH 3 CH 3 N 2 3 6-OCH SO,NHCH, H 0CH 2 CH 3 NHCH N 2 3 6-OCH SO,NHCH, CH 3 OCH 3 CH 3 N 2 3 6-SCH S0,NHCH, H OCH 3 OCH 3 CH 2 3 6-SCH S0 2 NHCH 3 H - OCH 3 CH 3 CH 6-SCH SO,NHCH, H Cl OCH 3 CH 2 3 6-SCH, SO,NHCH, H CH 3 CH 3 3 CH 2 3 •6-SCH SO,NHCH, H OCH 3 OCH 3 N 2 3 6-SCH S0,NHCH, H 0CH 3 CH 3 N 2 3 6-SCH, S0,NHCH, H 0CH,CH, NHCH, 3 2 3 2 3 3 N 6-SCH S0,NHCH, 0CH 3 CH 3 N 2 3 CH 3 H S0,NHCH, H OCH 3 OCH, CH 2 3 3 147-148.5 H S0,NHCH, H OCH, CH 3 CH 2 3 3 H SO,NHCH, H 2 3 Cl 0CH 3 CH 155-157 H SO,NHCH, H CH 3 CH 3 2 3 CH 150-152 H SO,NHCH, H OCH 3 2 3 OCH 3 N H SO,NHCH, H 0CH 3 CH 3 2 3 N 153.5-155 H SO,NHCH, H 0CH 2 CH 3 2 3 NHCH N H SO,NHCH, CH 3 0CH 3 CH 3 2 3 N 4-CH 3 S0 2 NHCH 3 H OCH 3 OCH 3 CH 4-OCH SO,NHCH, H OCH 3 OCH 3 2 3 CH 6-CH, SO NHCH, H OCH 3 3 OCH 3 2 3 CH 6-F SO,NHCH, H OCH 3 OCH 3 2 3 CH Table I (continued) R 2 R X Y Z m.p. CO 6-C1 SO NHCH, H OCH, OCH, CH 2 3 3 3 H SO NHCH CK, H OCH. OCH 3 CH 163-165.5 2 2 3 3 H SOJSHCH„CH, H OCH 2 2 3 3, CH CH 3 H SO NHCH CK H Cl OCH 3 CH 158.5-161 H S0,NHCH,CH. H CH 3 CH 3 CH 118-121.5 2 2 3 K S0 2 NHCH 2 CH 3 H 0CH 3 OCH 3 N 162-164 H S0 2 NHCH 2 CH 3 H OCH 3 CH 3 N 158-160 H S0,NHCH,CH, H OCH 2 CH 3 NHCH N 2 2 3 H S0,NHCH,CH_ CH 3 OCH 3 CH 3 N 122-125.5 2 2 3 4-CH 3 S0 2 NHCH 2 CH 3 H OCH 3 OCH CH 4-OCH 3 SO NHCH CH H OCH OCH CH 6-CH 3 SO,NHCH,CH, H OCH 3 0CH 3 CH 2 2 3 6-OCH S0,NHCH,CH, H OCH 3 OCH CH 2 2 3 6-F SO,NHCH,CH, H OCH 3 0CH 3 CH 2 2 3 6-C1 SO,NHCH,CH, H OCH, 2 2 3 0CH 3 3 CH H SO,NHCH,CH,CH, H OCH 3 OCH 2 2 2 3 3, CH 138.5-141 H SO,NHCH,CH,CH, H OCH 3 CH 3 CH 117-120 2 2 2 3 H SO NHCH CH CH, H Cl OCH, CH 125-129 2 2 2 3 3 H SO,NHCH,CH CH, H CH 3 CH 3 CH 2 2 2 3 H SO,NHCH,CH,CH, H 0CH 3 OCH, 2 2 2 3 3 N 132-135 H SO,NHCH,CH,CH, H OCH, CH 3 2 2 2 3 3 N H SO,NHCH,CH,CH, H OCH,CH, NHCH 2 2 2 3 2 3 3, N H SO,NHCH,CH,CH, CH 3 0CH 3 CH 3 N 2 2 2 3 4-CH 3 SO,NHCH,CH,CH, H 0CH 3 OCH 3 CH 2 2 2 3 -OCH, SO,NHCH,CH,CH, H OCH 3 0CH 3 CH 3 2 2 2 3 6-CH 3 SO,NHCH,CH,CH, H OCH 3 0CH 3 CH 2 2 2 3 6-OCH SO,NHCH,CH,CH, H 0CH 3 OCH, CH 2 2 2 3 3 Table I (continued) " 1 ___ R X Y z m.p . O 6-F SO,NHCH,CH,CH, H OCH 3 OCH 3 CH 2 2 2 3 6-C1 S0 2 NHCH 2 CH 2 CH 3 H OCH 3 OCH 3 CH H S0 2 NHCH CH 3 ) 2 H 0CH 3 OCH 3 CH 164- -166 H S0 2 NHCH(CH 3 ) 2 H OCH 3 CH 3 CH 3 H S0 2 NHCH CH 3 2 H Cl OCH 3 CH 153, .5-156 H S0 2 NHCH(CH 3 ) 2 H CH 3 CH 3 CH H S0 2 NHCHCCH 3 ) 2 H OCH 3 OCH 3 N 14 - -152 H S0 2 HCH CH 3 ) 2 H 0CH 3 OCH N 149- -151 H S0 2 NHCH(CH 3 ) 2 H OCH.CH, NHCH, N 2 3 3 H S0 2 HCH(CH 3 2 CH 3 0CH 3 CH 3 N 141- -143 4-CH 3 S0 2 RHCHCCH 3 2 H OCH 3 OCH 3 CH 4-OCH , S0 2 HHCH CH 3 ) 2 H OCH 3 OCH 3 CH 6-CH 3 S0 2 NHCHCCH 3 2 H 0CH 3 OCH 3 CH 6-OCH S0 2 NHCHCCH 3 ) 2 H 0CH 3 OCH 3 CH 6-F SO OTfCH(CH H OCH 3 OCH 3 CH 6-C1 SO NHCHCCH H OCH 3 OCH 3 CH H SO NHcyclopropyl H OCH 3 OCH 3 CH H SO JTricyclopropyl H OCH, CH 3 CH 3 H SO NHcyclopropyl H Cl OCH, CH 3 H SO NHcyclopropyl H CH 3 CH 3 CH H SO NHcyclopropyl H OCH, OCH 3 N 3 H SO NHcyclopropyl H OCH, CH 3 N 3 H SO NHcyclopropyl H OCH,CH, NHCH N 2 3 H SO NHcyclopropyl CH 3 OCH 3 CH 3 N -CH 3 " SO NHcyclopropyl H OCH 3 OCH 3 CH 4-OCH, SO NHcyclopropyl H OCH 3 OCH 3 CH 3 6-CH 3 SO NHcyclopropyl H OCH 3 OCH 3 CH 6-OCH SO NHcyclopropyl H OCH 3 OCH 3 CH 6-F SO NHcyclopropyl H OCH 3 OCH 3 CH 6-C1 SO NHcyclopropyl H OCH 3 OCH 3 CH H SO,NHCH,CH=CH, H 0CH 3 0CH 3 CH 2 2 2 Table I (continued) R X 1 z m.p.CO H S0,NHCH,CH=CH, H 0CH 3 CH 2 2 2 CH 3 H S0„NHCH CH=CH H CL OCH, CH 2 2 2 3 H S0,NHCH CH=CH, H CH 3 CH 3 CH 2 2 2 H SO,NHCH,CH=CH, H OCH, 2 2 2 3 OCH 3 N H SO,NHCH,CH=CH, H OCH, CH 3 N 2 2 2 3 H SO,NHCH,CH=CH^ H OCH 2 CH 3 NHCH N 2 2 2 H S0,NHCH,CH=CH_, CH 3 OCH 3 CH 3 N 2 2 2 4-CH, S0,NHCH,CH=CH, H OCH 3 0CH 3 CH 3 2 2 2 4 -OCH, SO,NHCR,CH=CH, K OCH 3 OCR 3 CH 3 2 2 2 6-CH, SO,NHCH,CH=CH, H OCH 3 3 2 2 2 OCH 3 CH 6-OCH, SO,NHCH,CH=CH, H OCH 3 OCH 3 CH 3 2 2 2 6-F SO,NHCH,CH=CH, H OCH 3 2 2 2 OCH 3 CH 6-C1 SO,NHCH,CH=CH, H OCH 3 OCH 3 2 2 2 CH H SO,NHCH,C=CH H OCH 3 OCH 3 CH 2 2 H SO,NHCH,C=CH H OCH 3 CH 3 2 2 CH H SO,NHCH,C≡CH H Cl OCH 3 CH 2 2 H SO,NHCH,C≡CH H CH 3 CH 3 2 2 CH H SO,NHCH,C≡CH H OCH 3 OCH 2 2 3, N H SO,NHCH,C=CH H OCH 3 CH 3 2 2 N H SO HCH C≡CH H OCH,CH, NHCH, 2 2 N 2 3 3 H S0,NHCH C≡CH CH 3 OCH 3 CH 3 2 2 N 4-CH, SO,NHCH.C≡CH H OCH, . 3 2 2 OCH 3 3, CH -OCH, SO,NHCH,C=CH H OCH, 3 2 2 OCH 3 CH 3 6-CH, SO,NHCH,C=CH H OCH, • 3 2 2 OCH 3 CH 3 6 -OCH SO NHCH C≡CH H OCH, OCH 3 3, CH 6-F SO.NHCH C≡CH H 2 2 OCH, 0CH 3 CH 3 6-C1 SO,NHCH,C≡CH H 2 2 OCH 3 OCH 3 CH H SO,NHCH,OCH, H 2 2 3 OCH 3 0CH 3 CH H SO NHCH OCH H OCH 3 CH 3 CH H SO NHCH OCH H CL OCH, CH CO * NΛ ivj o P> in in o in Ω O Ω O O O O O O O Ω Ω O Ω O Ω O O O O O O O Ω Z Ω O ΩIK X Ω X Ω Ω Ω Ω Ω Ω Ω X X Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X X Ω X ω x ω x x x x x x xω Ωω X ω x ω x x x x x x xω Ω xω ω ω ω ω ω ω ω ω x ω ω ω ω ω ω ω ω ω x ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω β a a a ΩIN X X X X X X X X X X a a a a Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X Table I (continued) R X Y Z m.p,CO H SO,NHCH,CN H OCH 3 0CH 3 N 2 2 H SO,NHCH,CN H OCH, CH 3 N 2 2 3 H S0,NHCH,CN H OCH CH, NHCH, N 2 2 2 3 3 H SO NHCH,CN CH 3 OCH, CH 3 N 2 2 3 4-CH, SO NHCH CN H OCH 3 OCH, CH 3 2 2 3 -OCH S0,NHCH,CN H 0CH 3 0CH 3 CH 2 2 6-CH 3 S0,NHCH,CN H 0CH 3 OCH 3 CH 2 2 6-OCH S0,NHCH,CN H 0CH 3 0CH 3 CH 2 2 6-F S0,NHCH,CN H OCH 3 0CH a CH 2 2 6-C1 SO NHCH CN H OCH 0CH 3 CH H SO,NCCH,CH=CH,), H OCH 3 OCH 3 CH 2 2 2 2 H SO,NCCH,CH=CH,), H OCH 3 CH 3 CH 2 2 2 2 H SO,NCCH,CH=CH,), K Cl 0CH 3 CH 2 2 2 2 H SO,NCCH,CH=CH,)„ H CH 3 CH 2 2 22 CH 3 H S0 2 NCCH 2 CH=CH 2 ) 2 H OCH 3 0CH 3 N H S0 2 NCCH 2 CH=CH 2 ) 2 H OCH 3 CH 3 N H S0 2 CH 2 CH=CH 2 ) 2 H OCH 2 CH 3 NHCH N H OCH 3 CH 3 N S0 2 NCGH 2 CH=CH 2 } 2 CH 3 4-OCH, SO NCCH CH=CH )„ H 0CH 3 0CH 3 CH 3 2 2 2 2 6-C1 SO -pyrrolidino H OCH, OCH, CH 3 3 H SO -pyrrolidino H 0CH 3 OCH, CH 3 H SO -pyrrolidino H OCH 3 CH 3 CH H SO -pyrrolidino H CL OCH 3 CH H SO -pyrrolidino H CH 3 CH CH 3 H SO -pyrrolidino H OCH 3 OCH 3 N H SO -pyrrolidino H OCH 3 CH 3 N 83 Table I Ccontinued) ι κ 2_. «R X y Δ_ m -P: H SO -pyrrolidino H 0CH,CH, NHCH N 2 3 H SO -pyrrolidino CH OCH, CH 3 N 3 4-CH, SO -pyrrolidino H OCH, 0CH 3 CH 3 3 -OCH, SO.-pyrrolidino H OCH, OCH, CH 3 2 3 3 6-CH. SO -pyrrolidino H OCH, OCH, CH 3 3 3 CH 6-OCH, SO -pyrrolidino H OCH, OCH, 3 3 3 6-F SO -pyrrolidino H OCH 3 OCH 3 CH 6-C1 SO -pyrrolidino H OCH 3 OCH 3 CH S0,NHCH,CH,0CH, H OCH 3 CH H OCH 3 2 2 2 3 S0,NHCH,CH,0CH_ CH H H OCH 3 CH 3 2 2 2 3 H S0,NHCH,CH,0CH, H Cl OCH 3 CH 2 2 2 3 H S0,NHCH,CH,0CH, H CH 3 CH 3 CH 2 2 2 3 H SO,NHCH,CH,OCH, H OCH 3 OCH 3 N 2 2 2 3 H SO,NHCH,CH,OCH, H 0CH 3 CH 3 N 2 2 2 3 H SO,NHCH,CH,OCH, H 0CH,CH, NHCH N 2 2 2 3 2 3 H S0,NHCH,CH,0CH, CH, 0CH 3 CH 3 N 2 2 2 3 3 4-CH 3 SO,NHCH,CH,OCH, H OCH 3 OCH 3 CH 2 2 2 3 -OCH. SO,NHCH,CH,OCH, H OCH 3 0CH 3 CH 3 2 2 2 3 6-CH 3 SO,NHCH,CH,OCH, H OCH, OCH, CH 2 2 2 3 3 3 SO,NHCH,CH,0CH, H OCH, OCH, CH 6-OCH3, 2 2 2 3 3 3 6-F S0,NHCH,CH,0CH, H OCH, OCH, CH 2 2 2 3 3 3 6-C1 S0,NHCH,CH,0CH, H OCH, 0CH 3 CH 2 2 2 3 3 H SO -pyrrolidino H 0CH 3 0CH 3 CH 146-149 SO -pyrrolidin H CH 3 CH 3 CH 169-171 H o 6-CH,CH. C0,CH, H OCH 3 OCH 3 CH 2 3 2 3 6-CH,CH, C0,CH, H 0CH 3 CH 3 CH 2 3 2 3 6-CH CH, CO,CH, H Cl 0CH 3 CH 2 3 2 3 6-CH,CH, CO,CH, H CH 3 CH 3 CH 2 3 2 3 6-CH.CH, C0,CH, H OCH 3 0CH 3 N 2 3 2 3 6-CH,CH, CO,CH, H 0CH 3 CH 3 N 2 3 2 3 6-CH,CH, CO,CH, H 0CH,CH, NHCH, N 2 3i 2 3 2 3 3 6-CH.CH. , CO CH CH * 0 2 31 2 3 3 CH o CH 3 N 3 Table I (continued) ^ ^ R X Y Z m.p. CO 6-OCH, CO,CH, H 0CH 3 OCH 3 CH 194-196 3 2 3 6 -OCH, CO,CH H OCH 3 3 2 3 CH 3 CH 165-167 6-OCH, CO,CH_ K Gl 0CH 3 CH 173-175 3 2 3 6-OCH, CO„CH„ H CH 3 CH 138.5-145 3 2 3 GH 3 6-OCH, CO-CH. H OCH 3 OCH 3 N 173-176 3 2 3 6-OCH 3 C0 2 CH 3 H OCH 3 CH 3 N 158-161 6-OCH 3 0 2 CH 3 H OCH 2 CH 3 NHCH 3 N 6-0CH 3 G 0 2 CH 3 CH 3 0CH 3 CH 3 N 6-OCH 2 CH 3 C0 2 CH 3 H 0CH 3 OCH 3 CH 154-157 6-OCH 2 CH 3 C0 2 CH 3 H 0CH 3 CH 3 CH 160-162 6 -OCH CH CO CH 3 H Cl OCH 3 CH 130-132 6-OCH,CH, CO,CH_ H CH 3 2 3 2 3 CH 3 CH 140-141 6-0CH,CH, C0,CH, H OCH OCH N 160-162 2 3 2 3 6-OCH,CH, CO,CH, 2 3 2 3 H OCH 3 CH 3 N 152-153 6-OCH,CH, CO,CH, 2 3 2 3 H OCH CH 3 NHCH N 6-OCH.CH, CO.CH, CH 3 OCH 3 2 3 2 3 CH 3 N 6-OCF, C0,CH, H OCH 3 OCH 3 3 2 3 CH 6-OCF, C0,CH, H 0CH 3 3 2 3 CH 3 CH 6-OCF, CO,CH, H Cl 0CH 3 3 2 3 CH 6-OCF, C0,CH, 3 2 3 H CH 3 CH 3 CH 6-OCF 3 C0 2 CH 3 H OCH OCH 3 N 6-OCF, CO,CH, 3 2 3 H 0CH 3 CH 3 N 6-OCH,CF, CO,CH, H OCH, OCH 3 2 3 2 3 3 CH 158-162 6-OCH,CF, CO,CH, H 0CH 3 2 3 2 3 CH 3 CH 168-170 6-OCH,CF, CO,CH, 2 3 2 3 H Cl OCH 3 CH 149-150 6-OCH 2 CF 3 C0 2 CH 3 H CH 3 CH 3 CH 150-152 6-OCH 2 CF 3 C0 2 CH 3 H 0CH 3 OCH 3 N 6-OCH,CF, C0,CH, 2 3 2 3 H OCH 3 CH 3 N 6-OCH 2 CF 3 C0 2 CH 3 H OCH CH NHCH N 6-0CH 2 CF 3 C0 2 CH CH 3 0CH 3 CH 3 N x x x X X X X Ni a a υ x u X X x x x x υ υ a a a a υ υ υ υ a a a a x x υ υ υ υ a υ υ υ υ co co pi co pi pi pi co co co co co to to pi to to to to pi to co fo to pi to pi co co co X X X X X X X X X X X X X X X X X X X X X X X X X X X X X υ cMυCMucgucgυcgυcgυcMυCMυcMυc_υCMυcMυegυcgυcMυCMυcMυcgυcMυCMυcMυpgυcgυcv!υCMυCMυcMυCMυCMυcM tn o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ υ to cM X *~-. ,- ._ ■ _. ^_, υ co co co co X o υ υ co a a a a Table I (continued) ι R X Y Z m.p. < β C 6- CCH 3 2 C0 2 CH 3 H OCH 3 OCH, N 171- -172 3 6- CCH 3 ) 2 C0 2 CH 3 H OCH 3 CH 3 N 132- -134 6- CCH 3 ) 2 •C0,CH, H 0CH 2 CH 3 NHCH N 152- -155 2 3 6-N CH 3 ) 2 CO,CH, CH 3 OCH 3 CH 3 N 2 3 6-NHCH CO,CH, H OCH 3 OCH 3 CH 2 3 6-NHCH CO,CH, H OCH 3 CH 3 CH 2 3 6-NHCH CO,CH, H Cl OCH 3 CH 2 3 6-NHCH C0 2 CH 3 H CH 3 CH 3 CH 6-NHCH C0 2 CH 3 H ' OCH 3 0CH 3 N 6-NHCH 3 CO,CH, H * OCH CH 3 . N 2 3 6-NHCH CO„CH, H OCH,CH, NHCH N -2 3 2 3 6-NHCH C0 2 CH 3 CH 3 0CH 3 CH 3 N 6-CH,CH, C0 2 CH 2 CH 3 H OCH 3 0CH 3 CH 2 3 6-CH,CH, C0 2 CH 2 CH 3 H 0CH 3 CH 2 3 CH 3 6-CH 2 CH 3 CO,CH,CH, H Cl OCH, CH 2 2 3 3 6-CH 2 CH 3 CO,CH,CH, H CH 3 CH 2 2 3 CH 3 6-CH 2 CH 3 C0 2 CH 2 CH 3 H OCH 3 0CH 3 N 6-CH 2 CH 3 C0 2 CH 2 CH 3 H OCH 3 CH 3 N 6-CH,CH, C0 2 CH 2 CH 3 H 0CH 2 CH 3 NHCH N 2 3 6-CH,CH, C0,CH,CH, CH, 0CH 3 N 2 3 2 2 3 3 CH 3 6-OCH CO,CH,CK, K OCH 3 OCH 3 CH 158- -161 2 2 3 6-OCH C0,CH,CH, H OCH 3 CH 3 CH 147- -149 2 2 3 6-OCH, CO,CH,CH, H Cl 0CH 3 CH 124- -127 3 2 2 3 6-OCH CO,CH,CH, H CH 3 CH 3 CH 149- -151 2 2 3 6-OCH CO,CH,CH, H OCH,* OCH 3 N 164- -165 2 2 3 3 6-OCH, C0,CH,CH, H OCH 3 CH 3 3 N 131- -132 2 2 3 6-OCH C0,CH,CH, H 0CH 2 CH 3 NHCH N 2 2 3 6-OCH CO,CH,CH, CH 3 OCH 3 CH 3 N 2 2 3 6-0CH,CH, C0,CH,CH, H OCH 3 OCH, 2 3 CH 2 2 3 152- -154 3 6-OCH,CH, CO,CH,CH, H OCH 3 2 3 2 2 3 CH, CH 134- -135 ) io to M H H in o in O in O in σ σv σv σv σv σv O σ σv σv σv σv αv σv σv σv σv σv tjv Ov σv σv σ σv σv σv » 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 o o o o O O o o o o o o o o o o o O O o o o O O O O O O O n n o Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω o Ω Ω Ω Ω Ω Ω Ω Ω Ω 11 "1 *t Ml •_! Ω Ω "1 X X X X X X X X X X X X X X to to to to to to to to ω ω ω ω to to to to to to to to to to to to to to Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O •>l r <- , q r 4 ni > 4 *4 r 4 X X X X X ω ω ω ω ω ω ω ω ω ω ω ω ω ω a a Ω Ω Ω Ω Ω X X X X a a a 65 8 Ω Ω X X X a a a a Ω Ω Ω Ω Ω X X X X a a a a X a N Table I (continued) R Y Z m.p . CO 6-SCH, CO,CH,CH, H OCH OCH 3 CH 3 2 2 3 6 -SCH CO,CH,CH_ H OCH 3 CH 3 CH 2 2 3 6-SCH, CO,CH,CH, H Cl OCH CH 3 2 2 3 6-SCH, CO,CH,CH, H CH 3 CH 3 2 2 3 CH 3 6 -SCH, CO,CH,CH, H OCH 3 0CH 3 N 3 2 2 3 6-SCH, CO,CH,CH, H OCH, CH 3 N 3 2 2 3 3 6 -SCH, CO,CH,CH, H OCH,CH, NHCH, N 3 2 2 3 2 3 6 -SCH CO,CH CH, CH 3 OCH 3 GH 3 ' N 2 2 3 6-SCH CH, CO,CH,CH, H OCH 3 OCH 3 CH 2 3 2 2 3 6-SCH CH, CO,CH,CH, H OCH 3 CH 2 3 2 2 3 GH 3 6-SCH 2 CH 3 CO CH CH H Cl OCH CH 2 2 3 6-SCH,CH, CO CH CH H CH 3 CH, CH 2 3 2 2 3 6-SCH,CH, C0 2 CH 2 CH 3 H OCH 3 0CH 3 N 2 3 6-SCH,CH, C0 2 CH 2 CH 3 H OCH 3 CH 3 N 2 3 C0 2 CH 2 CH 3 H OCH 2 CH 3 NHCH, N 2 3 6-SCH 2 CH 3 CO,CH,CH, CH 3 OCH, CH 3 N 2 2 3 3 6-NCCH 3 ) 2 CO,CH,CH, H 0CH 3 OCH 3 CH 147-149 2 2 3 6- CCH 3 ) 2 CO,CH,CH, H OCH, CH 3 CH 149-150 2 2 3 3 6-NCCH 3 2 CO,CH,CH, H Cl OCH 3 CH 150-151 2 2 3 6-NCCH 3 ) 2 CO,CH,CH, H CH 3 CH 3 CH 172-175 2 2 3 6-N CH 3 ) 2 CO,CH,CH, H OCH 3 OCH, N 152-153 2 2 3 3 6-NCCH 3 ) 2 CO,CH,CH, H 0CH 3 CH 3 N 148-150 2 2 3 6-NCCH 3 ) 2 CO.CH.CH_ H OCH CH, NHCH, N 2 2 3 2 3 3 6- NCCH 3 ) 2 CO,CH,CH, CH 3 OCH, CH 3 N 2 2 3 3 6 -NHCH. CO,CH,CH H OCH, OCH 3 CH 2 2 3 3 6 -NHCH 3 CO.CH.CH, H OCH, CH 3 CH 2 2 3 3 6 -NHCH 2 CO,CH, CH, H Cl OCH 3 CH 2 2 3 6 -NHCH. C0 2 CH 2 CH 3 H CH 3 CH 3 CH 3 6 -NHCH, C0 2 CH 2 CH 3 H OCH 3 0CH 3 N 3 6 -NHCH, CO,CH,CH, H OCH 3 CH 3 N 2 2 3 6 -NHCH, CO,CH,CH, H OCH 2 CH 3 NHCH, N 2 2 3 _«. 6 -NHCH CO,CH,CH, CH. OCH. CH. N 2 2 3 Table I Ccontinued) R X Y Z m.p. CO H C0 2 CH 2 CH 2 OH H 0CH 3 OCH 3 CH H C0,CH,CH,0H H 0CH 3 CH 3 CH 2 2 2 H C0,CH,CH,0H H Cl OCH 3 CH 2 2 2 H CO,CH,CH,OH H CH 3 CH 3 CH 2 2 2 H CO,CH,CH,OH H OCH 3 OCH 3 N 2 2 2 H C0,CH,CH,0H H 0CH 3 CH 3 N 2 2 2 H CO,CH,CH,OH H OCH,CH, NHCH N 2 2 2 2 3 H CO„CH,CH,OH CH 3 OCH 3 CH 3 N 2 2 2 4-CH, C0,CH,CH,0H H 0CH 3 OCH 3 CH 3 2 2 2 4-OCH, C0,CH,CH,0H H 0CH 3 OCH 3 CH 3 2 2 2 6-CH 3 CO,CH,CH,OH H OCH 3 OCH 3 2 2 2 CH 6-OCH C0 2 CH 2 CH 2 0H H 0CH 3 OCH 3 CH 6-F C0 2 CH 2 CH 2 OH H OCH 3 OCH 3 CH 6-C1 C0 2 CH 2 CH 2 OH H 0CH 3 0CH 3 CH H C0 2 CH 2 CH 2 CN H 0CH 3 0CH 3 CH H C0 2 CH 2 CH 2 CN H 0CH 3 CH 3 CH H C0 2 CH 2 CH 2 CN H Cl 0CH 3 CH H C0 2 CH 2 CH 2 CN H CH 3 CH 3 CH H C0 2 CH 2 CH 2 CN H 0CH 3 0CH 3 N H CO,CH,CH,CN H OCH 3 CH 3 2 2 2 N H C0,CH,CH,CN H OCH,CH, NHCH N 2 2 2 2 3 H CO,CH CH,CN CH 3 OCH, CH 3 N 2 2 2 3 4-CH 3 C0,CH,CH,CN H OCH 3 0CH 3 2 2 2 CH -OCH, C0,CH,CH,CN H 0CH 3 3 0CH 3 2 2 2 CH 6-CH, C0,CH,CH,CN H CH 3 OCH, 3 2 2 2 CH 3 6-OCH, C0,CH,CH,CN H OCH 3 3 OCH, 2 2 2 CH 3 6-F C0,CH,CH.CN H 0CH 3 OCH 2 2 2 3, CH 6-C1 CO,CH,CH,CN H OCH, OCH, CH 2 2 2 3 3 Table I (continued) R Z m. p . CO H C0,CH,CH,0S0,CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 H CO,CH,CH,OSO,CH, H 0CH 3 CH 3 CH 2 2 2 2 3 H C0,CH,CH,0S0,CH. H Cl OCH CH 2 2 2 2 3 . _ H C0,CH,CH,0S0,CH, H CH 3 CH 3 CH 10 2 2 2 2 3 H C0,CH,CH,0S0,CH, H 0CH 3 OCH 3 N 2 2 2 2 3 H C0,CH,CH ,0SQ,CH, H OCH, CH 3 N 2 2 2 2 3 3 H C0,CH,CH,0S0,CH, H 0CH,CH, NHCH N 2 2 2 2 3 2 3 H C0,CH,CH,0S0,CH, CH 3 0CH 3 CH, N 2 2 2 2 3 3 ., ,. 4-CH, C0,CH,CH,0S0,CH, H 0CH 3 OCH, CH 15 3 2 2 2 2 3 4-0CH, C0,CH,CH,0S0,CH, H 0CH 3 OCH 3 2 2 2 2 3 3, . CH 6-CH, C0,CH,CH,0S0,CH, H 0CH 3 0CH 3 CH 3 2 2 2 2 3 6-0CH, C0,CH,CH,0S0,CH, H 0CH 3 0CH 3 CH 3 2 2 2 2 3 6-F C0,CH,CH,OS0,CH, H 0CH 3 0CH 3 CH 2 2 2 2 3 _ Λ 6-C1 C0,CH,CH,0S0,CH, H 0CH 3 0CH 3 CH 20 2 2 2 2 3 H C0 2 CH 2 CH 2 0S0 2 C 3 H OCH 0CH 3 CH H C0,CH,CH,0S0,CF, H 0CH 3 CH 3 2 2 2 2 3 CH H C0,CH,CH,0S0,CF, H 2 2 2 2 3 Cl OCH 3 CH H C0,CH,CH,0S0,CF, H CH 3 CH 3 2 2 2 2 3 CH H C0,CH,CH,0S0,CF, H 0CH 3 0CH 3 25 2 2 2 2 3 N H C0,CH.CH,0S0,CF, H 0CH 3 2 2 2 2 3 CH 3 N H C0,CH,CH,0S0,CF, H 2 2 2 2 3 0CH 2 CH 3 NHCH N H C0,CH,CH,0S0,CF, CH 3 0CH 3 2 2 2 2 3 CH 3 N 4-CH, C0,CH,CH,0S0,CF, H 0CH 3 0CH 3 3 2 2 2 2 3 CH , _ 4-0CH, C0,CH,CH,0S0,CF, H OCH, 30 3 2 2 2 2 3 3 0CH 3 CH 6-CH, C0,CH,CH,0S0,CF, H OCH, 3 2 2 2 2 3 3 0CH 3 CH 6-0CH, C0,CH,CH,0S0,CF, H OCH, 3 2 2 2 2 3 3 OCH, CH 3 6-F C0,CH,CH,0S0,CF, H OCH, 2 2 2 2 3 3 0CH 3 CH 6-C1 C0,CH,CH,0S0,CF, H OCH 3 OCH, 2 2 2 2 3 CH 3 35 O O O O O O O O O O O Ω O O O O O O O O O O O O Ω Ω O O IX Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X t- Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X P' Ω Ω o vO X X X X X X X X X X ω X X X X X X X X X X X X ω x x o ω ω ω ω ω ω ω to ω ω ω ω ω ω ω ω ω ω ω to ω ω ω ω 3 Ω Ω rt- X ω X P- ω 3 C (D O O O O O O Ω Ω O Ω O Ω O O O O O O O Ω Ω O Ω O Ω O IK P. Ω Ω Ω Ω Ω Ω X X Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X Ω X Ω X Ω X X X X X Xω Ωω Xω x ω x x x x x x xω Ω ω X ω x ω x ω ω ω ω ω ω x ω ω ω ω ω ω ω ω ω x LO CO IO ω ω Ω Ω Ω Ω Ω Ω a a Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IN X X X X X X X X X X X X X X X X a a a a Ω Ω X X X X Table I (continued) R- l R Z m. p . CO H C0,CH,CH,CH,C1 H 0CH 3 OCH CH 2 2 2 2 H C0„CH,CH,CH,C1 H 0CH 3 CH 2 2 2 2 CH 3 H C0,CH,CH,CH,C1 H Cl 0CH 3 CH 2 2 2 2 H C0,CH,CH,CH,C1 H CH 3 CH 3 CH 2 2 2 2 H C0,CH,CH,CH,C1 H 0CH 3 0CH 3 N 2 2 2 2 H C0,CH,CH,CH,C1 H 0CH 3 CH 3 N 2 2 2 2 H CO CH CH CH Cl H 0CH 2 CH 3 NHCH N 2 2 2 2 H C0,CH,CH,CH,C1 CH 3 0CH 3 CH 3 N 2 2 2 2 4-CH, C0,CH,CH,CH,C1 H 0CH 3 0CH 3 CH 3 2 2 2 2 4-OCH 3 C0,CH,CH CH,C1 H 0CH 3 OCH 3 - CH 2 2 2 2 6-CH, C0,CH,CH,CH,C1 H OCH3, CH 3 2 2 2 2 0CH 3 6 -OCH, C0,CH,CH,CH,C1 H 0CH 3 OCH, CH 3 2 2 2 2 3 6-F C0,CH,CH,CH,C1 H 0CH 3 OCH 2 2 2 2 3, CH 6-C1 C0,CH,CH,CH,C1 H OCH, OCH 2 2 2 2 3 3, CH H CO,CH,CH,SCH, H 0CH 3 0CH 3 CH 2 2 2 3 H CO CH CH SCH, H OCH CH CH 2 2 2 3 3 3 H CO,CH,CH,SCH, H Cl 0CH 3 CH 2 2 2 3 H CO,CH,CH,SCH, H CH 3 CH 3 CH 2 2 2 3 H CO,CH,CH,SCH, H 0CH 3 0CH 3 N 2 2 2 3 H CO,CH,CH,SCH, H OCH 3 N 2 2 2 3 GH 3 H H 0CH,CH, NHCH, C0 2 CH 2 CH 2 SCH 3 N 2 3 H CH 3 0CH 3 CH 3 N C °2 CH 2 CH 2 S H 3 4-CH 3 CO,CH,CH,SCH, H 0CH 3 2 2 2 3 OCH 3 CH 4-OCH CO,CH,CH,SCH, H 0CH 3 2 2 2 3 OCH 3 CH 6-CH 3 CO,CH,CH,SCH, H 0CH 3 2 2 2 3 OCH 3 CH 6 -OCH, CO,CH,CH,SCH, H 0CH 3 3 OCH 3 2 2 2 3 CH 6-F CO,CH,CH,SCH, H 0CH 3 0CH 3 2 2 2 3 CH 6-C1 CO,CH,CH,SCH, H 0CH 3 OCH, CH 2 2 2 3 3 H CO CH -cyclopropyl H OCH, OCH 3 3, CH 143-145 H CO CH -cyclopropyl H Cl OCH, CH 124-128 3 - H CO CH -cyclopropyl H CH 3 CH 3 CH 134-138 H CO CH -cyclopropyl H OCH, OCH, 3 N 154-161 3 CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO O O O O O O O O O O O O O O O O O O O O Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω .—. Λ _C __. X iΕ X X X X X X X X X X X X X X lo to to to to to to io io -O to to to ω ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω ' Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X X X ω ω ω ω ω ω ω ω ω ω ω ω ω X X X X X X O O O O O O Ω Ω Ω Ω Ω Ω X X X X X X ω ω ω ω ω ω 0 0 0 0 O O Ω Ω Ω Ω Ω Ω X X X X X X ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω X X X X X X a a a Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X a Table II (continued) ι h R X Y Z m.p.( β C) H S0CH 2 CH 2 CH 3 H 0CH 3 0CH 3 CH - H SOCH CH CH H 0CH 3 CH 3 CH H S0CH,CH,CH, H Cl 0CH 3 CH 2 2 3 H S0CH,CH,CH, H CH 3 CH 3 CH 2 2 3 H S0CH 2 CH 2 CH 3 H OCH 3 OCH 3 N H SOCH 2 CH 2 CH 3 H 0CH 3 CH 3 N H S0CH 2 CH 2 CH 3 CH 3 0CH 3 CH 3 N 4-CH 3 S0CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 4-C1 S0CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-CH 3 S0CH 2 CH 2 CH 3 H OCH 0CH 3 ' CH 6-OCH S0CH 2 CH 2 CH 3 H 0CH 3 0CH 3 CH 6-F S0CH,CH,CH, H OCH 3 OCH 3 CH 2 2 3 6-C1 SOCH,CH,CH, H 0CH 3 0CH 3 CH 2 2 3 H S0CH,CH,CH CR, H OCH, 0CH 3 CH 2 2 2 3 3 H SOCH,CH,CH,CH, H OCH 2 2 2 3 3, CH 3 CH H SOCH CH CH CH, H Cl OCH, 2 2 2 3 3 CH H SOCH,CH,CH,CH, H CH 3 CH 3 CH 2 2 2 3 H SOCH,CH,CH,CH, ' H OCH 3 OCH 3 N 2 2 2 3 H SOCH,CH,CH,CH, H 0CH 3 CH 3 N 2 2 2 3 H SOCH,CH,CH,CH, CH 3 OCH 3 CH 3 N 2 2 2 3 4-CH 3 SOCH,CH,CH,CH, H 0CH 3 0CH 3 CH 2 2 2 3 4-C1 SOCH,CH,CH ^ CH, H 0CH 3 OCH 3 CH 2 2 2 3 6-CH 3 SOCH,CH,CH,CH, H 0CH 3 0CH 3 CH 2 2 2 3 6-OCH SOCH,CH,CH,CH, H 0CH 3 OCH 3 CH 2 2 2 3 6-F SOCH_CH,CH,CH, H 0CH 3 0CH 3 CH 2 2 2 3 6-C1 SOCH,CH,CH,CH, H OCH 3 0CH 3 CH 2 2 2 3 CO w to o H on o in αv σ |v _ts X X X X X X X X σv σv αv σ is is 1 ■ X 1 1 1 Ω •*! O Ω Ω Ω Ω o Ω Ω Ω P 1 Ω X P X P- Ω X P« X X ω ω X ω ω ω ω co 1 1 1 1 I 1 J 1 1 1 1 o O o O O O o O r> o o o n o o r» o o o o o Ω Ω Ω Ω Ω Ω Ω » » j » « • » « « «< « < « v< « < X X X X X X X o o o o o o o o o o o o o o .-. P" _-• P" P- P* P« P" P» P" P» _- ■ I- 1 P- * Ω Ω Ω Ω Ω Ω Ω o o o o o o o o o o o o o o X X X X X X X TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ ω ω ω ω ω ω ω 1 1 n π 1 n n 1 π n 1 n n v<» «___» «___» o o o o o o o o o o o o o o to to to to to to to TJ TJ TJ TJ TJ TJ TJ J TJ TJ TJ TJ TJ TJ J * *< *< » " « *< « < « « «< •< « < 33 33 33 33 33 33 Ω 33 33 33 33 33 33 33 33 33 33 33 X 55 G ω X ω o o o o o o o o o o o Ω O O O O O O O O O Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X P' Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X ω x x x x x x x x x ω ω ω ω ω ω io to ω ω ω ω ω ω ω ω ω ω ω Ω X ω o o o o o o Ω Ω O Ω O Ω O O O O O O O Ω Ω Ω Ω Ω Ω Ω X Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X X X X X X ω Ωω Xω xω x x x x x x xω > to ω ω ω ω x ω ω ω ω ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X a a a a Ω X X X a Table II (continued) ι ι R X Y Z m.p. ,( β C) H SO-cyclopropyl H OCH, OCH, CH 3 3 H SO-cyclopropyl H OCH, CH 3 CH 3 H SO-cyclopropyl H Cl OCH, CH 3 H SO-cyclopropyl H CH 3 CH 3 CH H SO-cyclopropyl H OCH 3 OCH 3 N H SO-cyclopropyl H OCH 3 CH 3 N H SO-cyclopropyl H OCH„CH NHCH N 2 3 H SO-cyclopropyl CH 3 OCH 3 CH 3 N 4-CH 3 SO-cyclopropyl H OCH 3 0CH 3 CH 4-C1 SO-cycloprop 1 H OCH OCH CH 6-CH 3 SO-cyclopropyl H OCH OCH 3 CH 6-OCH SO-cyclopropy1 H OCH 3 OCH 3 CH 6-F SO-cyclopropyl H OCH 3 OCH 3 CH 6-Cl SO-cyclopropyl H OCH 3 OCH 3 CH H SO -cyclopropyl H OCH 3 OCH 3 CH H SO -cyclopropyl H OCH 3 CH 3 CH H SO -cyclopropyl H Cl OCH 3 CH H SO -cyclopropyl H CH 3 CH 3 CH H SO -cyclopropyl H OCH 3 OCH, N 3 H SO -cyclopropyl H OCH, N 3 CH 3 H SO -cyclopropyl H OCH,CH, NHCH, N 2 3 3 H SO -cyclopropyl CH 3 OCH, CH 3 N 3 4-CH 3 SO -cyclopropyl H OCH 3 OCH 3 CH 4-C1 SO -cyclopropyl H OCH 3 OCH 3 CH 6-CH 3 SO -cyclopropyl H OCH 3 OCH 3 CH 6-OCH. SO -cyclopropyl H OCH 3 0CH 3 CH 6-F SO -cyclopropyl H OCH 3 OCH 3 CH 6-Cl SO -cyclopropyl H OCH 3 OCH 3 CH O O O O O O O O O O O O O O O O O O O O O O O O O O O O V0 CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO CO tl CO CO CO CO CO CO CO CO O O O O O O O O O O O O O O O O O O O O O O O O O O O O to to to to to to to to to to to to to to io to to to to io to to to to to to io to Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X X X X X X X X X X X X X X X X X X to to to to to io io to to to to to to to ω ω ω ω ω ω ω ω ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X X X X ω ω ω ω ω ω ω ω ω ω ω ω ω X X X O O O O O O Ω Ω Ω Ω Ω Ω v X X X X X X ω ω ω ω ω ω o o o o o o Ω Ω Ω Ω Ω Ω X X X X X X to to ω ω ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IN X X X X X X a a a Ω Ω Ω Ω Ω Ω Ω 33 33 33 33 33 33 33 33 33 33 a a a a Ω Ω Ω X X X X Table II (continued) R, R Z m.p . CO H 0S0.CF, H 0CH 3 0CH 3 CH 2 3 H 0S0,CF, H 0CH 3 CH 3 CH 2 3 H 0S0,CF, H Cl OCH 3 CH 2 3 H 0S0,CF, H CH 3 CH 3 CH 2 3 H 0S0,CF, H OCH, OCH 2 3 3 3, N H OSO,CF, H 0CH 3 CH 3 N 2 3 H 0S0,CF, H OCH CH, NHCH N 2 3 2 3 H 0S0,CF, CH 3 OCH 3 CH 3 N 2 3 4-CH 3 0S0.CF, H OCH 3 0CH 3 CH 2 3 4-C1 OSO„CF, H 0CH 3 0CH 3 - CH 2 3 6-CH 3 0S0,CF, H OCH 3 0CH 3 CH 2 3 6-OCH OSO.CF, H OCH 3 OCH 3 CH 2 3 6-F 0S0,CF, H 0CH 3 OCH 3 CH 2 3 6-Cl 0S0,CF, H 2 3 oco 3 OCH 3 CH H 0S0,CC1, H 0CH 3 0CH 3 CH 2 3 H 0S0,CC1, H 0CH 3 CH 3 CH 2 3 H 0S0,CC1, H Cl OCH 3 CH 2 3 H 0S0,CC1, H CH 3 CH 3 CH 2 3 H OSO,CCl H 0CH 3 OCH,3 N 2 3 H OSO CCl H OCH 3 CH 3 N 2 3 H 0S0,CC1, H 0CH,CH, NHCH, 2 3 2 3 3 N H 0S0 CC1, 0H 3 OCH, CH N 2 3 3 3 4-CH, OSO CCl, H OCH, 3 2 3 3 OCH 3 CH 4-C1 OSO CCl, H OCH 3 0CH 3 CH 2 3 6-CH 3 0S0,CC1, H 0CH 3 OCH 3 2 3 CH 6-OCH 0S0,CC1, H OCH 3 2 3 OCH 3 CH 6-F 0S0,CC1, H 2 3 0CH 3 OCH 3 CH 6-Cl 0S0,CC1, H OCH, 2 3 OCH, CH CO CO CO CO CO CO C CO CO CO CO CO CO CO O O O O O O O O O O O O O O O O O O O O O O CO CO CO CO CO CO CO CO to to to to to to to to to to to to to to O O O O O O O O O O O O O O O O O O O O O O N to to to io lo to io Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X X X X X X X X X X X X to to to to to to to to io io to to to to to to to to to to N io i Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω MJ Mtj nj »^j i»] nj »j n] jj tjj Bxj q -^ » T j x x x x x x ω ω ω ω ω ω ω ω ω ω ω ω ω ω to to to to to io to io Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X ω ω ω ω ω ω ω ω X X X Ω X X X X X X X X X X X X X Ω X X ω ω o o o' O Ω O Ω O O O O O O O Ω Ω Ωo oΩ Ωo Ω Ω Xo aX ΩX Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X X X X Xω Ωω x ω x ω x x x x x x xω Ω ω ω ω ω ω ω x ω ω ω ω ω ω ω ω ω x ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X a a a a Ω Ω Ω Ω .>_-3 33 33 33 33 33 33 33 33 8 a a Table II (continued) ι R X y Z m.p.CO H P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH H P(0)(0CH 3 ) 2 H OCH 3 CH 3 CH H P(0)(OCH 3 ) 2 H Cl OCH CH H P(0)(OCH 3 ) 2 H CH 3 CH 3 CH H P(0)(0CH 3 ) 2 H OCH 3 OCH 3 N H P(0)(0CH 3 ) 2 H OCH 3 CH 3 N H P(0)(0CH 3 ) 2 H OCH,CH„ NHCH N 2 3 H P(0)(0CH 3 ) 2 CH 3 OCH 3 CH 3 N 4-CH 3 P 0 OCH 3 2 H OCH 3 OCH 3 CH 4-C1 P(0)(0CH 3 ) 2 H OCH 3 OCH 3 . CH 6-CH 3 P(0)(OCH 3 ) 2 H 0CH 3 OCH 3 CH 6-OCH P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH 6-F P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH 6-Cl P(0)(0CH 3 ) 2 H oco 3 OCH 3 CH H CN H OCH 3 OCH 3 CH H CN H OCH 3 CH 3 CH H CN H Cl OCH 3 CH H CN H CH 3 CH 3 CH H CN H OCH 3 OCH 3 N H CN H OCH 3 N GH 3 H CN H OCH 2 CH 3 NHCH N H cm CH 3 0CH 3 CH 3 N 4-CH 3 CN H OCH 3 OCH 3 CH 4-C1 CN H OCH 3 OCH 3 CH 6-CH 3 CN H OCH 3 OCH 3 CH 6-OCH CN H OCH 3 OCH, CH 3 6-F CN H OCH, OCH 3 CH 3 6-Cl CN H OCH, OCH. CH Ω >τj Ω»»j Ω'ri Ω_] Ω__i Ω(_ 1 Ωχ Ω Ωχ Ωχ Ωχ Ωχ Ω w to to to to to to to to to io io to to X X X X X X '-l , ». , ?l »5d *i. »»l , »J Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IN 33 33 33 M 33 33 a a a a Ω X X X X X X a a a a X X X X Table II (continued) _1 -3 R I y Z m.p.CC) H SO NHCH 3 H OCH 3 OCH 3 CH H SO NHCH 3 H OCH CH 3 CH H S0 2 NHCH 3 H Cl 0CH 3 CH H S0 2 NHCH 3 H CH 3 CH 3 CH H S0,NHCH, H 0CH 3 0CH 3 N 2 3 H S0,NHCH, H 0CH 3 N 2 3 CH 3 H S0,NHCH„ H 0CH„CH„ NHCH N 2 3 2 3 H S0,NHCH„ CH 3 0CH 3 CH 3 N 2 3 4-CH 3 SO NHCH H OCH, - CH 0CH 3 3 4-C1 SO„NHCH, H OCH 3 CH 3 CH 2 3 6-CH 3 SO,NHCH, H OCH 3 0CH 3 CH 2 3 6-OCH, S0,NHCH, H OCH 3 OCH, CH 3 2 3 3 6-F SO,NHCH, H OCH 3 OCH 3 CH 2 3 6-Cl SO NHCH H OCH 0CH 3 CH H S0 2 NHCH 2 CH 3 H OCH 3 OCH 3 CH H S0,NHCH,CH, H 0CH 3 CH 3 CH 2 2 3 H S0,NHCH,CH, H Cl 0CH 3 CH 2 2 3 H S0,NHCH,CH, H CH 3 CH 2 2 3 CH 3 H SO NHCH CH H CH 3 0CH 3 N H SO,NHCH,CH, H 0CH 3 CH 3 N 2 2 3 H S0 2 NHCH 2 CH 3 H 0CH 2 CH 3 NHCH N H S0,NHCH,CH, CH 3 0CH 3 CH 3 N 2 2 3 4-CH 3 S0,NHCH,CH, H 0CH 3 OCH 3 CH 2 2 3 4-C1 SO,NHCH,CH, H 0CH 3 0CH 3 CH 2 2 3 6-CH 3 SO,NHCH,CH, H OCH 3 CH 2 2 3 0CH 3 6-OCH, 3 SO,NHCH,CH, H OCH 2 2 3 3, OCH 3 CH 6-F SO,NHCH,CH, H OCH, OCH, CH 2 2 3 3 3 6-Cl SO,NHCH,CH, H OCH 3 OCH, CH 2 2 3 3 O O O O O O O Ω Ω Ω Ω Ω Ω Ω X X X X X X X ω ω ω ω ω ω ω O O O O O O Ω Ω Ω Ω Ω Ω Ω X X X X X X X ω ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X a a a Ω Ω Ω Ω Ω X X X 33 33 33 33 33 33 a a a a Ω Ω Ω Ω IN X X E |Ω Table II (continued) i R X y Z m.p. <*c? H SO NH-cyclopropyl H 0CH 3 0CH 3 CH H SO NH-cyelopropyl H 0CH 3 CH CH 3 H SO NH-cyclopropyl H Cl OCH 3 CH H SO NH-cyclopropyl H CH 3 CH 3 CH H SO NH-cyclopropyl H 0CH 3 0CH 3 N H SO NH-cyclopropyl H 0CH 3 CH 3 N H SO,NH-cyclopropyl H OCH 2 CH 3 NHCH N H SO NH-cyclopropyl CH 3 OCH 3 CH 3 N -CH 3 SO NH-cyclopropyl H OCH 3 0CH 3 CH * 4-C1 S0 2 NH-cyclopropyl H OCH, OCH CH 3 6-CH 3 SO NH-cyclopropyl H OCH OCH CH . 6 -OCH SO NH-cyclopropyl H 0CH 3 OCH CH 6-F SO.NH-cyclopropyl H 0CH 3 0CH 3 CH 6-Cl SO NH-cyclopropyl H OCH 3 OCH 3 CH H SO,NHCH,CH=CH, H 0CH 3 OCH 3 CH 2 2 2 H SO,NHCH CHs-CH, H OCH 3 CH 3 CH 2 2 2 H SO,NHCH,CH=CH, H Cl 0CH 3 CH 2 2 2 H SO,NHCH,CH=CH, H CH 3 CH 3 CH - 2 2 2 H SO,NHCH,CH=GH, H 0CH 3 0CH 3 N 2 2 2 H S0„NHCH CH-sCH H 0CH 3 CH 3 N 2 2 2 H SO,NHCH,CH=CH, H 0CH,CH, NHCH, N 2 2 2 2 3 3 H SO,NHCH,CH=CH, CH 3 OCH 2 2 2 3, CH 3 N 4-CH 3 SO NHCH CH=CH H 0CH 3 OCH 3 CH 4-C1 S ,NHCH,CH=CH, H 0CH 3 OCH 3 CH 2 2 2 6-CH 3 SO,NHCH,CH=CH, H OCH 3 0CH 3 CH 2 2 2 6 -OCH, SO,NHCH,CH=CH, H OCH 3 OCH 3 CH 3 2 2 2 6-F SO,NHCH,CH=CH, H 0CH 3 0CH 3 CH 2 2 2 . 6-Cl SO,NHCH,CH=CH, H 0CH 3 0CH 3 CH 2 2 2 co co co co co co co co co co co co co co co co co co co co O O O O O O O O O O O O O O O O O O O O to to to to to to to to to to to to to to to lo to to to to Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X X X X X X X X X X to to to to to to to to io to to to to to to to to to to to Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω a a a a a a a a a a a a a a ω , »j ω'-ιω ,: - ω , »ιω , *j ω , *ι 33 • 33 323 33 33 Ω X 33 33 33 33 33 33 33 33 33 33 33 33 Ω X X ω o o o o o o o o o o o O O O O O O O O O O Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω X X X X X X X X X X ω X X X X X X X X X X ω ω ω ω ω ω ω io ω ω ω ω ω ω ω ω ω ω ω to Ω X ω ω o o o o o o Ω Ω O Ω O Ω O O O O O O O Ω Ω Ω Ω Ω Ω Ω X .X Ω X Ω X Ω Ω Ω Ω Ω Ω Ω X X X X X X X ω Ωω x ω x ω x x x x x x x ω to ω ω ω ω ω x ω ω ω ω ω ω ω ω ω ω ω Ω Ω Ω Ω Ω Ω a a a a Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω a X X X X X X 33 33 33 33 33 33 33 33 33 33 Table II (continued) R 5 Z m.p.CC) H S0 2 CH 2 CH=CH 2 ) 2 H OCH 3 OCH CH H 0 2 N CH 2 CH=CH 2 ) 2 H OCH, CH, CH 3 3 H S0 2 N(CH 2 CH=CH 2 2 H Cl OCH, CH 3 H SO,N(CH,CH=CH,), H CH 3 CH_ 2 2 2 2 CH H S0 2 N CH 2 CH=CH 2 ) 2 H OCH OCH, N 3 H S0 2 N(CH 2 CH=CH 2 2 H OCH 3 CH. N H S0 2 N(CH 2 CH=CH 2 ) 2 H OCH,CH, NHCH N 2 3 H S0 2 N(CH 2 CH=CH 2 2 CH, OCH, CH_ N 3 3 4-CH 3 S0 2 N CH 2 CH=CH 2 2 H OCH 3 OCH CH 4-C1 S0 2 N CH 2 CH=CH 2 2 H OCH OCH CH 6-CH 3 SO,N(CH,CH=CH,), 2 2 22 H OCH 3 OCH CH 6 -OCH, SO,N(CH,CH=CH,), H OCH 3 2 2 22 OCH, CH 3 6-F S0 2 N CH 2 CH=CH 2 ) 2 H OCH 3 OCH CH 6-Ci S0 2 N CH 2 CH=CH 2 ) 2 H OCH 3 OCH CH H SO -pyrrolidino H OCH, OCH 3 CH 3 H SO -pyrrolidino H OCH, CH CH 3 H SO -pyrrolidino H Cl OCH CH H SO -pyrrolidino H CH 3 CH, CH 3 H SO,-ρyrrolidino H OCH, OCH, N 3 3 H SO -pyrrolidino H OCH, CH_ N 3 H S -pyrrolidino H OCH CH, NHCH, N 2 3 3 H SO -pyrrolidino CH, OCH, CH N 3 3 4-CH, 3 SO -pyrrolidino H OCH_ OCH CH 4-C1 SO -pyrrolidino H. OCH„ OCH CH 6-CH 3 SO -pyrrolidino H OCH 3 OCH CH 6 -OCH SO -pyrrolidino H OCH OCH, CH 3 6-F SO -pyrrolidino H OCH 3 OCH CH 6-Cl SO -pyrrolidino Η OCH, OCH CH t 33 33 33 33 tM υ3 3υ3 3υ3 Nl υ υ υ υ a a a a υ υ 3υ3 3υ-3 3 3υ3 3υ3 υ 33 a a a x a υ to to Pl to CO X CO Pl Pl tO Pl tO tO Pl Pl X X to X CO x PI υ PI X X X X X X X PI X PI X Pl U Pl u x υ x υ X X o υ o υ o υ E xυ υo υo υo υo υo υo υo xυ υo xυ υo xυ x υ υ o Φ Pl to 3 X C υ x •H PI CO Pl tO CM Pl Pl Pl tO Pl Pl Pl tO PI υ *J X Xυ rH x Pl Xυ υX υX υX Xυ Xυ Xυ Xυ Xυ xυ xυ xυ -H CO PlxPlxCMxCOx c υ XI o o υ υ o o o o o o o o o o o o υ xυ υo υo υo υo υo σv αv σv σv is is σv σ |v σv pa I I I X X X X X X X X σv is is X X X X B 1 B Ω «1 o Ω Ω Ω Ω •v. Ω Ω P" Ω o X P" X P Ω 8 P 1 X X ω ω ω X ω ω ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω |N X X X X X X a a a a Ω Ω X X X X X 8 Ω X a a a a x Table II (continued) !ι h. & X Y Z m.p.CC) H C0,CH,CH,0S0,CH, H OCH 3 OCH 3 2 2 2 2 3 CH H CO,CH,CH,OSO,CH, H OCH 3 CH 3 2 2 2 2 3 CH H CO,CH,CH,OSO,CH, H Cl OCH 3 2 2 2 2 3 CH H CO,CH,CH,0S0,CH, H CH 3 CH 3 2 2 2 2 3 CH H C0,CH,CH,0S0,CH, H 0CH 3 OCH 2 2 2 2 3 3, N H CO,CH,CH,OSO,CH, H OCH 3 CH 3 N 2 2 2 2 3 H CO,CH,CH,OSO,CH, H OCH 2 CH 3 NHCH 2 2 2 2 3 N H CO,CH,CH,OSO,CH, CH 2 2 2 2 3 , °CH, CH 3 N 3 3 4-CH, 3 CO,CH,CH,OSO,CH, H " OCH 3 OCH 3 2 2 2 2 3 CH 4-C1 CO,CH,CH,OSO,CH, H ' OCH 3 OCH 2 2 2 2 3 3 - CH 6-CH, CO,CH,CH,OSO,CH, H 0CH 3 OCH, CH 3 2 2 -2 2 3 3 6-OCH, CO,CH,CH,OSO,CH, H 0CH 3 OCH 3 3 2 2 2 2 3 CH 6-F CO,CH,CH,OSO,CH, H OCH 3 OCH 3 2 2 2 2 3 CH 6-Cl C0 2 CH 2 CH 2 OS0 2 CH 3 H oco 3 0CH 3 CH H C0 2 CH 2 CF 3 H OCH 3 0CH 3 CH H C0 2 CH 2 CF 3 H 0CH 3 CH 3 CH H C0 2 CH 2 CF 3 H Cl OCH 3 CH H C0 2 CH 2 CF 3 H CH 3 CH 3 CH H C0 2 CH 2 CF 3 H 0CH 3 OCH 3 N H C0 2 CH 2 CF 3 H OCH 3 CH 3 N H C0 2 CH 2 CF 3 H OCH 2 CH 3 NHCH N H C0 2 CH 2 CF 3 CH 3 OCH 3 CH 3 N 4-CH, CO,CH,CF, H 0CH 3 3 2 2 3 OCH 3 CH Table III General Formula 3 R. R Y n.P.C'C) H S0CH 3 H OCH 3 OCH 3 CH H SOCH 3 H OCH 3 CH 3 CH H S0CH 3 H Cl OCH 3 CH H S0CH 3 H CH 3 CH, CH H S0CH 3 H OCH 3 OCH 3 N 2-F SOCH H 0CH 3 CH 3 6-CH 3 SOCH3, K OCH 3 OCH 3 CH 6-OCH SOCH H OCH 3 OCH 3 CH 6-F SOCH H 0CH 3 0CH 3 CH 6-Cl SOCH 3 H Owii * 0CH 3 CH H SOC 2 A Clf3 M H 0CH 3 0CH 3 CH H SOCH„CH„ H OCH 2 3 αr 3 CH H SOCH 2 CH 3 H Cl 0CH 3 CH H SCOTCH H 0CH 3 OCH 3 X H SOCH CH, H OCH 3 N ^3 H SOCH 2 CH 3 CH 3 0CH 3 CH 3 H 2-C1 SOCH 2 CH 3 H OCH 3 OCH 3 CH 2-F SOCH2.CH3, H OCH 3 0CH 3 CH 6-CH 3 S0CH 2 CH 3 H OCHj OCH 3 CH 6-OCH SOCH2.CH3, H OCH 3 OCH 3 CH 6-Cl SOCH2.CH-3 H OCH 3 OCH 3 CH Table III (continued) f !i R X Y z m.p.CC) H SOCH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH H S0CH,CH_CH, 2 2 3 H 0CH 3 CH 3 CH H SOCH.CH.CH, 2 2 3 H Cl OCH 3 CH H SOCH 2 CH 2 CH 3 H CH 3 CH 3 CH H SOCH_,CH.CH- 2 2 3 H OCH 3 OCH 3 __. H SOCH CH CH H 0CH 3 CH 3 ir H SOCH 2 CH 2 CH 3 CH 3 OCH 3 CH 3 H 2-C1 SOCH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 2-F S0CH 2 CH 2 CH 3 H OCH 3 0CH 3 CH 6-CH 3 S0CH 2 CH 2 CH 3 H OCH 3 0CH 3 CH 6-OCH SOCH 2 CH 2 CH 3 H 0CH 3 0CH 3 CH 6-F SOCH.CH.CH, 2 2 3 H OCH 3 OCH 3 CH 6-Cl SOCH.CH.CH, 2 2 3 H OCH 3 OCH 3 CH H SOCH.CH.CH.CH, 2 2 2 3 H OCH 3 0CH 3 CH H SOCH.CH.CH.CH, 2 2 2 3 H OCH 3 CH 3 CH H SOCH.CH.CH.CH, 2 2 2 3 H Cl OCH 3 CH H SOCH.CH.CH.CH, 2 2 2 3 H CH 3 CH 3 CH H SOCH,CH,CH,CH, OCH 3 OCH 2 2 2 3 H 3 M H SOCH 2 CH-CH 2 CH 3 H OCH 3 CH 3 H H SOCH.CH.CH.CH, 2 2 2 3 CH 3 OCH 3 CH 3 2-C1 SOCH.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 CH 2-F SOCH.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 CH 6-CH 3 SOCH.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 CH 6-OCH SOCH,CH,CH„CH, 2 2 2 3 H 0CH 3 OCH 3 CH 6-F SOCH.CH.CH.CH, 2 2 2 3 H 0CH 3 OCH 3 CH 6-Cl SOCH.CH.CH.CH, 0CH 3 2 2 2 3 H OCH 3 CH Table III (continued) i R X y z m.p.CC) H OCH(CH 3 2 H 0CH 3 OCH 3 CH H S0CH(CH 3 ) 2 H 0CH 3 CH 3 CH H S0CH(CH 3 ) 2 H Cl 0CH 3 CH H S0CH(CH 3 ) 2 H CH 3 CH 3 CH H SOCH(CH 3 ) 2 H 0CH 3 0CH 3 N H S0CH(CH 3 ) 2 H 0CH 3 CH 3 y H S0CH(CH 3 ) 2 CH 3 0CH 3 IT CH 3 2-C1 S0CH(CH 3 ) 2 H OCH. 0CH 3 CH 3 2-F SOCH(CH ) H 0CH 3 OGH A 3 - CH 6-CH 3 SOCH(CH 3 > 2 H 0CH 3 OCH CH 6-0CH S0CH(CH 3 ) 2 H 0CH 3 OCH CH 6-F SOCHCCH 3 ) 2 H 0CH 3 0CH 3 CH 6-Cl S0CHCCH 3 ) 2 H 0CH 3 0CH 3 CH H S-cyclopropyl H OCH OGH.. CH H S-cyclopropyl H 0CH 3 CH 3 CH H S-cyclopropyl H Cl 0CH 3 CH H S-cyclopropyl H CH 3 CH 3 CH H S-cyclopropyl H 0CH 3 0CH 3 U H S-cyclopropyl H 0CH 3 CH 3 U H S-cyclopropyl H H S-cyclopcopyl CH 3 0CH 3 CH 3 X 2-C1 S-cyclopcopyl H 0CH 3 0CH 3 CH 2-F S-cyclopropyl H 0CH 3 0CH 3 CH 6-CH 3 S-cyclopropyl H 0CH 3 0CH 3 CH 6-0CH S-cyclopropyl H 0CH 3 0CH 3 CH 6-F S-cyclopropyl H 0CH 3 OCH 3 CH 6-Cl S-cyclopropyl H 0CH 3 0CH 3 CH Table III (continued) . __ R X Y z m.p.CC) H SO-cyclopropyl H 0CH 3 0CH 3 CH H SO-cyclopropyl H 0CH 3 CH 3 CH H SO-cyclopropyl H Cl 0CH 3 CH H SO-cyclopropyl H CH 3 CH 3 CH H SO-cyclopropyl H 0CH 3 0CH 3 N H SO-cyclopropyl H 0CH 3 CH 3 N H SO-cyclopropyl H OCH.CH, NHCH 2 3 H H SO-cyclopropyl CH, 0CH 3 CH 3 N 2-C1 SO-cyclopropyl H 0CH 3 0CH 3 CH 2-F SO-cyclopropyl H 0CH 3 OCH 3 CH 6-CH 3 SO-cyclopropyl H 0CH 3 0CH 3 CH 6-OCH SO-cyclopropyl H OCH 3 0CH 3 CH 6-F SO-cyclopropyl H 0CH 3 0CH 3 CH 6-Cl SO-cyclopropyl H 0CH 3 OCH 3 CH H SO -cyclopropyl H 0CH 3 0CH 3 CH H SO -cyclopropyl H 0CH 3 CH 3 CH H SO -cyclopropyl H Cl 0CH 3 CH H SO -cyclopropyl H CH 3 CH 3 CH H SO -cyclopropyl H OCH 3 OCH 3 H H SO ? -cyclopropyl H OCH 3 CH 3 H SO.-cyclopropyl H OCH 2 CH 3 NHCH 3 H SO.-cyclopropyl CH, OCH 3 CH 3 2-C1 SO.-cyclopropyl H 0CH 3 0CH 3 CH 2-F SO.-cyclopropyl H 0CH 3 OCH 3 CH 6-CH 3 SO.-cyclopropyl H 0CH 3 0CH 3 CH 6-OCH SO.-cyclopropyl H 0CH 3 OCH 3 CH 6-F SO.-cyclopropyl H 0CH 3 0CH 3 CH -Cl SO.-cyclopropyl H OCH, OCH, CH Table III (continued) R. R Z m.p. CC) H OSO.CH, H 0CH 3 2 3 CH 3 CH H OSO.CH, H Cl OCH 3 CH 2 3 H OSO Λ CH, H CH 3 CH 3 CH 2 3 H 0S0„CH, H OCH 3 0CH 3 IT 2 3 H 0S0 Λ CH, H OCH 3 2 3 CH 3 N H OSO CH H OCH2.CH3, NHCH X H OSO.CH, CH 3 OCH 3 2 3 CH 3 X 2-C1 0S0 2 CH 3 K OCH 3 0CH 3 CH 2-F OSO CH H 0CH 3 0CH 3 CH 6-CH 3 OSO2.CH3. H 0CH 3 0CH 3 CH 6-OCH 3 OSO.2CH3, H 0CH 3 OCH 3 CH 6-F OSO2.CH3, H 0CH 3 OCH 3 CH 6-Cl OSO.CH. H 2 3 0CH 3 OCH 3 CH H OSO2.CH2.CH3. H 0CH 3 0CH 3 CH H OS0 2 CH 2 CH 3 H OCH 3 CH 3 CH H 0S0 2 CH 2 CH 3 H Cl OCH 3 CH H OSO2.CH2.CH3, H CH 3 CH 3 CH H OSOgCH CH 3 H OCH 3 OCH 3 X H OSO CH CH H 0CH 3 CH 3 X H OSO OCH 2.CH2.CH3, H 2.CH3, NHCH 3 X H OSO_2,CH,2CH3. CH 3 OCH 3 CH 3 X 2-C1 OSO Λ CH,CH, H OCH 3 0CH 3 CH 2 2 3 2-F OSO„2CH2.,CH3, H OCH 3 OCH 3 CH 6-CH 3 OS0 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-OCH OS0 2 CH 2 CH 3 H 0CH 3 0CH 3 CH 6-F OS0 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-Cl OSO CH CH 3 H OCH 3 OCH 3 CH Table III (continued) . i R X Y Z m. p .CC ) H OSO-CH,CH.CH, 2 2 2 3 H 0CH 3 OCH 3 CH H OSO,CH,CH,CH, 2 2 2 3 H 0CH 3 CH 3 CH H 0S0,CH,CH.CH, 2 2 2 3 H Cl 0CH 3 CH H OSO.CH.CH.CH, 2 2 2 3 H CH 3 CH 3 CH H OSO.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 X H OSO.CH.CH.CH, 2 2 2 3 H 0CH 3 CH 3 X H OSO_CH,CH,CH, 2 2 2 3 H OCH.CH, HHCH 2 3 X H OSO.CH.CH.CH, 2 2 2 3 CH 3 OCH 3 CH 3 X 2-C1 OSO.CH.CH.CH, 2 2 2 3 H OCH 3 0CH 3 CH 2-F OSO.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 CH 6-CH 3 OSO.CH.CH.CH, 2 2 2 3 H OCH 3 OCH 3 CH 6-OCH OSO.CH.CH.CH, 2 2 2 3 H OCH 3 0CH 3 CH 6-F OS0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-Cl OS0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH H 0S0 2 CF 3 H OCH 3 OCH 3 CH H OSO„CF, 2 3 H OCH 3 CH 3 CH H OS0 2 CF 3 H Cl OCH 3 CH H 0S0 2 CF 3 H CH 3 CH 3 CH H 0S0 2 CF 3 H OCH 3 OCH 3 X H OSO.CF, 2 3 H OCH 3 CH 3 X H 0S0 2 C 3 H 0CH 2 CH 3 NHCH 3 X H OS0 2 CF 3 CH 3 OCH 3 CH 3 X 2-C1 OS0 2 CF 3 H OCH 3 OCH 3 CH 2-F OS0 2 CF 3 H OCH 3 OCH 3 CH 6-CH 3 OS0 2 CF 3 H OCH 3 OCH 3 CH 6-OCH OSO,CF, 2 3 H OCH 3 OCH 3 CH 6-F OSO„CF, 2 3 H 0CH 3 0CH 3 CH 6-Cl OSO,CF, 2 3 H 0CH 3 0CH 3 CH Table III (continued) R. R X __ Z Z m.p . CC) H OSO.CCl, H 2 3 OCH OCH 3 CH H 0S0„CC1, H OCH 3 2 3 CH 3 CH H 0S0„CC1- H Cl OCH 3 2 3 CH H OSO.CCl, H 2 3 CH 3 CH 3 CH H OSO.CCl, H OCH 3 OCH 3 2 3 If H oso 2 ccι 3 H 0CH 3 CH 3 X H oso 2 ccι 3 H OCH 2 CH 3 HHCH 3 X H OSO.CCl, CH 3 OCH 3 2 3 CH 3 X 2-C1 OSO.CCl, 2 3 H 0CH 3 0CH 3 CH 2-F oso 2 ccι 3 H 0CH 3 0CH 3 CH 6-CH 3 oso 2 ccι 3 H 0CH 3 0CH 3 CH 6-OCH 3 oso 2 ccι 3 H 0CH 3 OCH 3 CH 6-F oso 2 ccι 3 H 0CH 3 0CH 3 CH 6-Cl OSO-CCl. 2 3 H 0CH 3 0CH 3 CH H *3 H OCH 3 OCH 3 CH H H 3 H OCH 3 CH 3 CH H H 3 H Cl OCH 3 CH H H »3 CH 3 CH 3 CH H H 3 H OCH 3 OCH 3 X H H OCH 3 CH 3 X H 3 H *3 H OCH.CH, NHCH X 2 3 H CH 3 H 3 OCH 3 CH 3 X 2-C1 H OCH 3 OCH 3 CH »3 2-F H. H OCH 3 OCH 3 CH 6-CH 3 H- H OCH 3 OCH 3 CH 6-OCH 3 H OCH 3 OCH 3 CH 6-F ■ 3 H 0CH 3 OCH 3 CH 6-Cl H OCH, OCH, CH Table III (continued) ϋ± R X Y Z m.p.CC) H P(0)(OCH 3 ) 2 H 0CH 3 OCH 3 CH H P(0)(OCH 3 ) 2 H OCH 3 CH 3 CH H P(0)(OCH 3 ) 2 H Cl OCH 3 CH H P(0)(OCH 3 ) 2 H CH 3 CH 3 CH H P(0)(OCH 3 ) 2 H OCH 3 OCH 3 H H P(0)(0CH 3 ) 2 H 0CH 3 CH 3 X H P(0)(0CH 3 ) 2 H OCH CH, HHCH X 2 3 H P(0)(OCH 3 ) 2 CH 3 OCH 3 CH 3 X 2-C1 P(0)(0CH 3 ) 2 H OCH 3 0CH 3 CH 2-F P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH 6-CH P(0)(OCH 3 > 2 H OCH 3 OCH 3 CH 6-OCH P(0)(0CH 3 ) 2 H OCH 3 OCH 3 CH 6-F P(0)(OCH 3 ) 2 H OCH 3 OCH 3 CH 6-Cl P(0)(0CH 3 ) 2 H 0CH 3 OCH 3 CH H CM H OCH 3 OCH 3 CH H CH H OCH 3 CH 3 CH H CH H Cl OCH 3 CH H CH H CH 3 CH 3 CH H CH H OCH 3 OCH 3 CH H CH H 0CH 3 CH 3 CH H CH H OCH 2 CH 3 NHCH 3 CH H CH CH 3 OCH 3 CH 3 CH 2-C1 CH H OCH 3 OCH 3 CH 2-F CH H OCH 3 OCH 3 CH 6-CH 3 CH H OCH 3 OCH 3 CH 6-OCH CH H OCH 3 OCH 3 CH 6-F CH H OCH 3 OCH 3 CH -Cl CH H OCH, OCH„ CH Table III (continued) R, R. Z m.p . CC) H CH 2 F H 0CH 3 0CH 3 CH H CH 2 F H 0CH 3 CH 3 CH H CH 2 F H Cl 0CH 3 CH H CH 2 F H CH 3 CH 3 CH H CH 2 F H 0CH 3 0CH 3 H H CH 2 F H 0CH 3 CH 3 H H CH 2 F H 0CH.CH. NHCH 3 2 3 H H CH 2 F CH 3 0CH 3 CH 3 H 2-C1 CH 2 F H 0CH 3 0CH 3 CH 2-F CH 2 F H 0CH 3 0CH 3 CH 6-CH 3 CH 2 F H 0CH 3 0CH 3 CH 6-OCH CH 2 F H 0CH 3 0CH 3 CH 6-F H 0CH 3 CH 2 F ∞*3 CH 6-Cl CH 2 F H 0CH 3 0CH 3 CH H CF 2 H H 0CH 3 0CH 3 CH H CF 2 H H 0CH 3 CH 3 CH H CF 2 H H Cl 0CH 3 CH H CF 2 H H CH 3 CH 3 CH H CF 2 H H 0CH 3 OCH X H CF 2 H H 0CH 3 CH 3 ¥ H CF 2 H H 0CH 3 OCH 3 X H CF 2 H CH 3 0CH 3 CH 3 X 2-C1 CF 2 H H 0CH 3 0CH 3 CH 2-F C 2 H H 0CH 3 0CH 3 CH 6-CH 3 CF 2 H H 0CH 3 OCH 3 CH 6-OCH 3 CF 2 H H 0CH 3 0CH 3 CH 6-F CF 2 H H 0CH 3 0CH 3 CH 6-Cl CF 2 H H 0CH 3 0CH 3 CH 119 Table III (continued) R X Y Z Z m.p . CC) H S0 2 H 0CH 3 )CH 3 H OCH 3 OCH 3 CH H S0 2 H(OCH 3 CH 3 H 0CH 3 CH 3 CH H S0 2 H OCH 3 )CH 3 H Cl OCH 3 CH H S0 2 H 0CH 3 )CH 3 H CH 3 CH 3 CH H S0 2 H 0CH 3 )CH 3 H 0CH 3 0CH 3 H H S0 2 H 0CH 3 CH 3 H 0CH 3 CH 3 X H SO H(0CH )CH H OCH 2 CH 3 HHCH X H SO H(0CH 3 )CH 3 CH 3 0CH 3 X CH 3 2-C1 SO H(0CH )CH H 0CH 3 OCH 3 CH 2-F S0 2 H OCH 3 )CH 3 H OCH 3 OCH 3 CH 6-CH SO H(0CH 3 )CH 3 H OCH 3 0CH 3 CH 6-OCH SO H OCH 3 )CH 3 H OCH 3 OCH 3 CH 6-F S0 2 H(OCH H 0CH 3 0CH 3 CH 6-Cl S0 2 H(OCH H OCH 3 OCH 3 CH H S0 2 HHCH 3 H OCH 3 OCH 3 CH H S0 2 HHCH 3 H OCH 3 CH 3 CH H S0 2 HHCH 3 H Cl OCH 3 CH H S0 2 HHCH 3 H CH 3 CH 3 CH H SO,HHCH, H OCH 3 OCH 3 H 2 3 H SO,NHCH, H OCH 3 CH 3 H 2 3 H S0,HHCH, H OCH 2 CH 3 HHCH H 2 3 H SO,NHCH, CH 3 OCH 3 CH 3 H 2 3 2-C1 S0,NHCH, H 0CH 3 0CH 3 CH 2 3 2-F SO,NHCH, H OCH 3 OCH 3 CH 2 3 6-CH 3 S0 2 NHCH 3 H OCH 3 OCH 3 CH 6-OCH S0 2 NHCH 3 H OCH 3 OCH 3 CH 6-F S0 2 NHCH 3 H OCH 3 OCH 3 CH 6-Cl SO,NHCH, H OCH, OCH, CH 2 3 Table III (continued) Y Α m.p.CC) H SO HHCH CH 3 H Cl OCH 3 CH H S0 2 HHCH 2 CH 3 H CH 3 CH 3 CH H S0 2 HHCH 2 CH 3 H OCH 3 OCH 3 H H S0 2 HHCH 2 CH 3 H 0CH 3 CH 3 H H S0„NHCH.GH, H 2 2 3 0CH 2 CH 3 NHCH N 2-C1 SO HHCH CH 3 H 0CH 3 OCH 3 CH 2-F S0„2NHCH Λ 2CH3, H OCH OCH 3 CH 6-CH 3 SO„2NHCH2_CH3, H OCH 3 OCH 3 CH 6-OCH S0 2 HHCH 2 CH 3 H OCH 3 OCH CH 6-F SO„NHCH„CH. 2 2 3 H OCH 3 OCH 3 CH 6-Cl SO HHCH CH H 0CH 3 0CH 3 CH H S0 2 HHCH 2 CH 2 0CH 3 H OCH 3 0CH 3 CH ft SO2.NHCH2.CH2.OCH3, H OCH 3 CH 3 CH H SO2.NHCH2.CH2.OCH3, H Cl 0CH 3 CH H SO2.NHCH2.CH.2OCH3, H CH 3 CH 3 CH H SO„NHCH.CH.OCH, 2 2 2 3 H OCH 3 OCH 3 H H SO HHCH CH 2 0CH 3 H OCH 3 CH 3 H H SO,2HHCH2,CH,2OCH3, H OCH2.CH3, NHCH N H SO2.NHCH2.CH2.OCH3, CH 3 OCH 3 CH 3 H 2-C1 SO,HHCH,CH,OCH, 2 2 2 3 H 0CH 3 OCH 3 CH 2-F SO NHCH CH 0CH 3 H OCH 3 OCH 3 CH 6-CH 3 SO2.NHCH2,CH2-OCH3, H OCH 3 OCH 3 CH 6-OCH 3 SO2.NHCH,2CH2.OCH3, H 0CH 3 0CH 3 CH 6-F S0 2 NHCH 2 CH 2 OCH 3 H 0CH 3 OCH 3 CH 6-Cl S02.NHCH„2CH,20CH3, H OCH 3 OCH. CH Table III (continued) Z m.p.CC) H C0,CH,CH,0H H 0CH 3 OCH 3 CH 2 2 2 H C0,CH,CH,0H H 0CH 3 CH 3 CH 2 2 2 H C0,CH,CH,0H H Cl OCH 3 CH 2 2 2 H C0,CH.CH,0H H CH 3 CH 3 CH 2 2 2 H C0,CH,CH,0H H 0CH 3 0CH 3 H 2 2 2 H CO.CH.CH.OH 2 2 2 H OCH 3 CH 3 X H CO,CH,CH,OH H OCH.CH, NHCH 2 2 2 X 2 3 H C0,CH„CH,0H CH 3 0CH 3 CH 3 X 2 2 2 2-C1 C0 2 CH 2 CH 2 OH H OCH 3 0CH 3 CH 2-F C0 2 CH 2 CH 2 0H H 0CH 3 OCH 3 CH 6-CH 3 C0,CH,CH,0H OCH 3 CH 2 2 2 H OCH 3 6-OCH 3 C0 2 CH 2 CH 2 OH H OCH 3 OCH 3 CH 6-F C0„CH,CH.0H OCH 3 CH 2 2 2 H OCH 3 6-Cl C0 2 CH 2 CH 2 0H H OCH 3 OCH 3 CH H CO.CH.CH.CN OCH 3 OCH 3 CH 2 2 2 H H C0 2 CH 2 CH 2 CH H OCH 3 CH 3 CH H C0,CH_CH.CN 2 2 2 H Cl OCH 3 CH H CO,CH,CH,CH H CH 3 CH 3 CH 2 2 2 H C0,CH,CH,CN H OCH 3 OCH 3 H 2 2 2 H CO,CH,CH,CN H OCH 3 CH 3 H 2 2 2 H C0,CH.CH,CN OCH 3 0CH 3 N 2 2 2 H H C0,CH,CH,CH CH 3 H 2 2 2 CH 3 OCH 3 2-C1 CO,CH,CH,CN H OCH 3 OCH 3 CH 2 2 2 2-F C0 2 CH 2 CH 2 CH H 0CH 3 0CH 3 CH 6-CH 3 CO.CH.CH.CN H OCH 3 OCH 3 CH 2 2 2 6-OCH 3 C0 2 CH 2 CH 2 CN H OCH 3 OCH 3 CH 6-F C0 2 CH 2 CH 2 CH H 0CH 3 OCH 3 CH 6-Cl C0 2 CH 2 CH 2 CN H OCH 3 OCH, CH CJ ω N ts) P» Ul O Ul O ui O Ul v σv to IO σv σv σ |s> M 1 a w x x x x X X X X X X X X 1 » Ω Ω Ω P" H * k Ω k 1 P» ω a ω . X ω* 6 F- Ωo Ωo Ωo Ωo Ωo Ω oo Ωo Ω Ω Ω Ω Ω Ω Ω Ω Ω 6 OCH- t - tO t SOo otootOotOotOo Ω Ω Ω Ω fOo Ω Ω O O O O O Q Ω O Ω O Ω O Ω Q O O O O O Q Ω Ω O Ω O Ω O IK Ω XΩ ΩX ΩX Ω Ω ΩX ωa aΩ ωa Ω a Ω a Ω Ω Ω ΩX ΩX ΩX ΩX ωa Ω ω a a Ω a Ω ω ω ω ω ω ω ω ω ω ω X w X X X ω ω ω ω ω ω ω ω x ω ω X ω x ω a a Ω Ω a a Ω a Ω x Ω Ω x a as a a Ωx Ωx Ωx Ωx Ωx Ωx Ωx xΩ Ox Ωx 85 85 B5 85 Ωa Ωa Oa Ωa IN Table IV General Formula 4 i m.P.CO H SOCH H OCH 3 OCH 3 CH H SOCH H OCH 3 CH 3 CH H S0CH 3 H Cl OCH 3 CH H SOCH H CH 3 CH 3 CH H SOCH 3 H OCH 3 OCH 3 N H SOCH 3 H OCH 3 CH 3 N H S0CH 3 H 0CH 2 CH 3 NHCH 3 M H SOCH CH 3 OCH 3 CH 3 H 5-CH. SOCH, H OCH 3 OCH 3 CH 5-OCH_, SOCH. H OCH 3 OCH 3 CH 6-CH, SOCH„ H OCH 3 OCH 3 CH 6-OCH_, SOCH. H OCH 3 OCH 3 CH 6-F SOCH H OCH 3 OCH 3 CH 6-Cl SOCH H OCH 3 OCH 3 CH H S0 2 CH 3 H OCH 3 OCH 3 CH H S0 2 CH 3 H OCH 3 CH 3 CH H S0 2 CH 3 H Cl OCH 3 CH H S0 2 CH 3 H CH 3 CH 3 CH H SO.CH, 2 3 H OCH 3 OCH 3 N H S0 2 CH 3 H OCH 3 CH 3 N H S0 2 CH 3 H OCH.CH, NHCH 2 3 N H S0 2 CH 3 CH 3 OCH 3 CH 3 H 5-CH 3 S0 2 CH 3 H OCH 3 OCH 3 CH 5-OCH 3 S0 2 CH 3 H OCH 3 OCH 3 CH 6-CH 3 S0 2 CH 3 H OCH 3 0CH 3 CH 6-OCH 3 S0 2 CH 3 H OCH 3 0CH 3 CH 6-F S0 2 CH 3 H OCH 3 OCH 3 CH 6-Cl S0 2 CH 3 H OCH, OCH, CH 124 Table IV (continued) R« R- m.p. CC) H S0CH,CH, 2 3 H 0CH 3 OCH 3 CH H SOCH CH H 0CH 3 CH 3 CH H S0CH Λ CH, H Cl OCH 3 CH 2 3 H S0CH,CH, H CH 3 CH 3 CH 2 3 H S0CH,CH, H 0CH 3 OCH 3 2 3 N H S0CH„CH, H 0CH 3 2.3 CH 3 H H S0CH„CH, H OCH CH, NHCH N 2 3 2 3 H S0CH,CH, CH 3 0CH 3 CH 3 N 2 3 5-CH 3 SOCH.CH, 2 3 H 0CH 3 OCH 3 CH 5-0CH SOCH 2 CH 3 H 0CH 3 0CH 3 CH 6-CH 3 S0CH 2 CH 3 H OCH 3 0CH 3 CH 6-OCH 3 S0CH 2 CH 3 H 0CH 3 OCH 3 CH 6-F SOCH.CH, 2 3 H 0CH 3 OCH 3 CH 6-Cl S0CH„CH, 2 3 H OCH 0CH 3 CH H S0 2 CH 2 CH 3 H 0CH 3 OCH 3 CH H S0 2 CH 2 CH 3 H 0CH 3 CH 3 CH H S0 2 CH 2 CH 3 H Cl OCH 3 CH H S0_CH,CH, 2 2 3 H CH 3 CH 3 CH H SO CH CH 2 2 3 H OCH 3 OCH 3 H H SO,CH,CH, H OCH 3 2 2 3 CH 3 N H SO,CH„CH, H OCH,CH, NHCH N 2 2 3 2 3 H S0 Λ CH,CH, CH 3 OCH 3 CH 3 N 2 2 3 5-CH 3 S0„CH„CH, H 0CH 3 0CH 3 CH 2 2 3 5-OCH, S0,CH,CH, 3 2 2 3 H OCH 3 0CH 3 CH 6-CH 3 SO.CH.CH, 2 2 3 H OCH 3 OCH 3 CH 6-OCH SO,CH,CH, H OCH 3 0CH 3 2 2 3 CH 6-F SO.CH.CH, 2 2 3 H OCH 3 0CH 3 CH 6-Cl S0,CH,CH, 2 2 3 H 0CH 3 0CH 3 CH Table IV (continued) !t . R X y Z m.p.CC) H SOCH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH H SOCH 2 CH 2 CH 3 H OCH 3 CH 3 CH H SOCH 2 CH 2 CH 3 H Cl OCH 3 CH H S0CH 2 CH 2 CH 3 H CH 3 CH 3 CH H SOCH 2 CH 2 CH 3 H OCH 3 OCH 3 N H S0CH 2 CH 2 CH 3 H OCH 3 CH, N H SOCH.CH.CH, 2 2 3 H OCH 2 CH 3 NHCH N H S0CH 2 CH 2 CH 3 CH 3 OCH 3 CH 3 N 5-CH 3 S0CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 5-0CH SOCH-CH„CH, H 0CH 3 OCH 3 CH 2 2 3 6-CH 3 SOCH„CH„CH, 2 2 3 H OCH 3 OCH 3 CH 6-0CH SOCH,CH,CH, H OCH 3 OCH 3 CH 2 2 3 6-F SOCH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-Cl SOCH_CH,CH, 2 2 3 H 0CH 3 OCH 3 CH H S0,CH,CH,CH. 2 2 2 3 H 0CH 3 OCH 3 CH H S0,CH,CH,CH, OCH 3 2 2 2 3 H CH 3 CH H S0 2 CH 2 CH 2 CH 3 H Cl OCH 3 CH H S0 2 CH 2 CH 2 CH 3 H CH 3 CH 3 CH H S0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 N H S0 2 CH 2 CH 2 CH 3 H 0CH 3 CH 3 N H S0 2 CH 2 CH 2 CH 3 H 0CH 2 CH 3 NHCH 3 N H S0.CH,CH-CH, 2 2 2 3 CH, OCH 3 CH 3 N 5-CH 3 S0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 5-OCH 3 S0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-CH 3 S0 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-OCH S0,CH,CH,CH, OCH 3 2 2 2 3 H OCH 3 CH 6-F SO,CH,CH,CH, OCH 3 2 2 2 3 H OCH 3 CH -Cl SO„CH,CH,CH, H OCH 3 OCH 3 CH 2 2 2 3 Table IV (continued) Y Z m.p.CC) H SOCH,CH,CH,CH, H 2 2 2 3 0CH 3 OCH 3 CH H SOCH,CH,CH,CH, H 2 2 2 3 OCH 3 CH 3 CH ft SOCH,CH,CH,CH, H 2 2 2 3 Cl OCH 3 CH H SOCH,CH,CH,CH, H 2 2 2 3 CH 3 CH 3 CH H SOCH,CH,CH,CH, H 2 2 2 3 OCH 3 OCH 3 N H SOCH CH 2 CH CH 3 H OCH 3 CH 3 H H S0CH 2 CH 2 CH CH 3 H OCH2.CH3, HHCH N H SOCH 2 CH 2 CH 2 CH 3 CH 3 0CH 3 CH 3 N 5-CH SOCH 2 CH 2 CH 2 CH 3 H OCH 3 0CH 3 CH 5-OCH 3 SOCH 2 CH 2 CH 2 CH H 0CH 3 OCH 3 CH 6-CH SOCH CH 2 CH 2 CH H OCH 3 OCH CH 6-OCH 3 S0CH 2 CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 6-F SOCH,CH,CH,CH, H 2 2 2 3 0CH 3 OCH 3 CH 6-Cl SOCH.CH-CH.CH, H 2 2 2 3 OCH 3 OCH 3 CH H SO,CH.CH,CH„CH, H 2 2 2 2 3 OCH 3 OCH 3 CH H SO.CH.CH.CH.CH, H OCH 3 CH 3 CH 2 2 2 2 3 H SO,CH,CH,CH,CH, H 2 2 2 2 3 Cl OCH 3 CH H SO,CH,CH,CH,CH, H 2 2 2 2 3 CH 3 CH CH H SO,CH,CH,CH,CH, H OCH 3 OCH 3 N 2 2 2 2 3 H SO,CH,CH,CH,CH, H 0CH 3 CH 3 N 2 2 2 2 3 H SO.CH.CH.CH.CH, H 2 2 2 2 3 0CH 2 CH 3 NHCH N H SO-CH-CH,CH.CH, CH, 2 2 2 2 3 3 OCH 3 CH 3 N 5-CH, SO,CH.CH,CH,CH, H 3 2 2 2 2 3 0CH 3 OCH 3 CH 5-OCH 3 S0 2 CH 2 CH 2 CH 2 CH 3 H 0CH 3 OCH 3 CH 6-CH 3 S0 2 CH 2 CH 2 CH 2 CH 3 H 0CH 3 0CH 3 CH 6-OCH 3 S0 2 CH 2 CH 2 CH CH H OCH 3 OCH 3 CH 6-F S0 2 CH 2 CH 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-C1 S0 2 CH 2 CH 2 CH 2 CH 3 H 0CH« OCH, CH Table IV (continued) R _f __ R X y z m.p.CC) H SOCH(CH 3 ) 2 H 0CH 3 0CH 3 CH H SOCH(CH 3 ) 2 H OCH 3 CH 3 CH H SOCH(CH 3 ) 2 H Cl OCH 3 CH H SOCH(CH 3 ) 2 H CH 3 CH 3 CH H SOCH(CH 3 ) 2 H OCH 3 OCH 3 N H SOCH(CH 3 ) 2 H 0CH 3 CH 3 N H SOCHCCH H OCH 2 CH 3 NHCH N H SOCH(CH 3 ) 2 CH 3 OCH 3 CH 3 X 5-CH 3 SOCH(CH 3 ) 2 H 0CH 3 OCH 3 CH 5-0CH SOCH(CH 3 ) 2 H OCH 3 OCH 3 CH 6-CH 3 SOCH(CH 3 ) 2 H 0CH 3 0CH 3 CH 6-OCH SOCH(CH 3 ) 2 H OCH 3 OCH 3 CH 6-F S0CH(CH 3 ) 2 H 0CH 3 OCH 3 CH 6-Cl SOCH(CH 3 ) 2 H OCH 3 OCH 3 CH H S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH H S0 2 CH(CH 3 ) 2 H OCH 3 CH, CH H S0 2 CH(CH 3 ) 2 H Cl OCH 3 CH H S0 2 CH CH 3 ) 2 H CH 3 CH, CH H S0 2 CH CH 3 ) 2 H OCH 3 OCH 3 N H S0 2 CH(CH 3 ) 2 H OCH 3 CH 3 N H S0 2 CH(CH 3 ) 2 H OCH.CH, NHCH 3 2 3 N H S0 2 CH(CH 3 2 CH 3 OCH 3 CH 3 N 5-CH 3 S0 2 CH(CH 3 ) 2 H 0CH 3 OCH 3 CH 5-OCH S0 2 CH CH 3 ) 2 H OCH 3 OCH 3 CH 6-CH 3 S0 2 CH(CH 3 ) 2 H OCH 3 OCH 3 CH 6-OCH S0 2 CH CH 3 ) 2 H OCH 3 OCH 3 CH 6-F S0 2 CH CH 3 ) 2 H OCH 3 OCH 3 CH 6-Cl S0 2 CH CH 3 2 H 0CH 3 0CH 3 CH Table IV (continued) R, R Z m.p. CC) H S-cyclopropyl H 0CH 3 0CH 3 CH H S-cyclopcopyl H 0CH 3 CH 3 CH H S-cyclopropyl H Cl 0CH 3 CH H S-cyclopropyl H CH 3 CH 3 CH H S-cyclopropyl H OCH 3 0CH 3 H H S-cyclopropyl H OCH 3 CH 3 H H S-cyclopropyl H 0CH,CH, NHCH 2 3 N H S-cyclopropyl CH 3 0CH 3 CH 3 N 5-CH 3 S-cyclopropyl H 0CH 3 0CH 3 CH 5-OCH 3 S-cyclopcopyl H 0CH 3 OCH 3 CH 6-CH 3 S-cyclopcopyl H 0CH 3 ^ OCH 3 CH 6-OCH S-cyclopcopyl H OCH 3 0CH 3 CH 6-F S-cyclopcopyl H OCH 3 0CH 3 CH 6-Cl S-cyclopcopyl H 0CH 3 OCH CH ft SO-cyclopcopyl H OCH 0CH 3 CH H SO-cyclopcopyl H OCH 3 CH 3 CH H SO-cyclopcopyl H Cl OCH 3 CH H SO-cyclopcopyl H CH 3 CH 3 CH H SO-cyclopcopyl H 0CH 3 0CH 3 H H SO-cyclopcopyl H OCH 3 CH 3 N H SO-cyclopcopyl H OCH.CH, NHCH 3 N 2 3 H SO-cyclopcopyl CH 3 0CH 3 CH 3 N 5-CH 3 SO-cyclopcopyl H OCH 3 0CH 3 CH 5-OCH 3 SO-cyclopcopyl H OCH 3 OCH 3 CH 6-CH 3 SO-cyclopcopyl H OCH 3 0CH 3 CH 6-OCH 3 SO-cyclopcopyl H OCH 3 ocκ 3 CH 6-F SO-cyclopcopyl H 0CH 3 OCH 3 CH 6-Cl SO-cyclo opyl H OCH, OCH. CH Table IV (continued) i __ X Y Z m.p. CC) H SO -cyclopropyl H OCH 3 0CH 3 CH H SO -cyclopcopyl H OCH 3 CH 3 CH H SO -cyclopcopyl H Cl 0CH 3 CH H SO -cyclopropyl H CH 3 CH 3 CH H SO -cyclopropyl H OCH 3 OCH 3 N H SO -cyclopropyl H OCH 3 CH 3 X H SO -cyclopropyl H OCH.CH, NHCH X 2 3 H SO.-cyclopropyl CH. OCH 3 CH, X 5-CH 3 SO.-cyclopropyl H OCH 3 OCH 3 CH 5-OCH 3 SO.-cyclopropyl H O βi OCH 3 CH 6-CH 3 SO.-cyclopropyl H OCH 3 OCH 3 CH 6-OCH 3 SO.-cyclopropyl H OCH 3 OCH 3 CH 6-F SO -cyclopropyl H OCH 3 OCH 3 CH 6-Cl SO.-cyclopropyl H OCH, OCH, CH Nl δ δ δ δ a a a a δ δ δ δ δ δ δ δ δ δ a a a a δ δ δ δ δ δ a Pla COa PI .alaOa toa to 888888 o x x x x x x a PlalaPlaPlaPlaOaPlaOaPlaPIaPlaPlaPlaPlfaPlfaPIfaPlfaPI υ CMυ CMυ CMυ CMυCMυCMυcMυCMυCMυCMbCMυCMυCMbCMcjCMυCMυCMυCM O O O O O O O O O O O O O O O O O O to to to to co to -. to co to co to to to co to to co OSm O O O O O O O O O O O O O O O O O O Table IV (continued) i i R X Y Z m.p.CC) H OS0 2 CH 2 CH 3 H 0CH 3 OCH 3 CH H OSO,CH,CH, 2 2 3 H 0CH 3 CH 3 CH H 0S0 2 CH 2 CH 3 H Cl OCH 3 CH H OS0 2 CH 2 CH 3 H CH 3 CH 3 CH H OS0 2 CH 2 CH 3 H OCH 3 OCH 3 N H 0S0 2 CH 2 CH 3 H OCH 3 CH 3 N H 0S0 2 CH 2 CH 3 H OCH.CH, NHCH 3 X 2 3 H OS0 2 CH 2 CH 3 CH 3 OCH 3 CH 3 X 5-CH 3 OS0 2 CH 2 CH 3 H OCH 3 OCH 3 CH 5-OCH 0S0 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-CH 3 0S0 2 CH 2 CH 3 H OCH 3 OCH 3 CH 6-OCH 3 0S0 2 CH 2 CH 3 H OCH 3 0CH 3 CH 6-F OS0 2 CH 2 CH 3 H OCH 3 0CH 3 CH 6-Cl OS0 2 CH 2 CH 3 H 0CH 3 OCH 3 CH H H OCH 3 OCH 3 CH tf 3 H N H OCH 3 CH 3 CH 3 H H 3 H Cl OCH 3 CH H H 3 H CH 3 CH CH 3 H M 3 H 0CH 3 OCH 3 N H H 3 H OCH 3 CH 3 N H H 3 H OCH 2 CH 3 NHCH N H H 3 CH 3 OCH 3 CH 3 N 5-CH 3 S 3 H OCH 3 OCH 3 CH 5-OCH 3 H CH H 3 OCH 3 OCH 3 6-CH 3 M 3 H 0CH 3 0CH 3 CH 6-OCH 3 H 3 H 0CH 3 0CH 3 CH 6-F H 3 H OCH 3 0CH 3 CH 6-Cl H, H OCH, OCH, CH 132 Table IV (continued) R Z m.p. CC) H CN H OCH OCH 3 CH H CN H OCH 3 CH 3 CH H CH H Cl OCH 3 CH H CN H CH 3 CH 3 CH H CN H OCH 3 OCH 3 N H CN H OCH 3 CH 3 N H CN H OCH CH, NHCH H H CN CH 3 OCH 3 CH 3 N 5-CH 3 CH H OCH OCH 3 CH 5-OCH 3 CN i OCH 3 OCH 3 CH 6-CH 3 CN H OCH 3 OCH 3 CH 6-OCH 3 CH H OCH 3 OCH 3 CH 6-F CN H OCH 3 OCH 3 CH 6-Cl CH ft OCH, OCH, CH Nl a υ aυ aυ aυ ^ a_ _a u a ^ a_ aυ aυ aυ aυ aυ aυ aυ« aυ aυ aυ _a_ u a _a _a aυ aυ aυ aυs aυ Bυ a co a co a to a co a to a to υo υo υo υo υo υo aPIaPIaPIaPIaPIaP l 888888 2 a a a a a a ■ * -*f__^ . . fa .JN fa __?• fa —N ,fa .J^ .fa . ^ ,fa ___**» „ fa __P* fa CM faCM faCM faCM fa fa a a a a a a aCM aCM aCM aCM aCM aCM aCM a a a a a a a a a a a CMaCM CM CM CM CM CM CM CM « I υ υ υ υ υ υ u υ υ υ aυ aυ au υ faυ faυ faυ faυ faυ fau faυ faυ faυ faυ faυ faυ faυ faυ 33 33 33 Nl υ υ a a a aυ aυ aυ aυs aυ» aυ ab__ aυ aυ aυ a._ _a ,a_ .a_ aυ3 aυ aυ4 a x as υ - o υ co PI a Pl . Pl CO CO Pl O PI a coυ, coa a a a a υ a a a υ υ υ υ υ υ υ o u S υ o o o o o o a" PI Pl CM Pl Pl Pl PI Pl Pl Pl s Pl Xy Xy Xc yX yX X X X X X υ δ δ δ δ δ o b o bo o b υδ O 33 33 35 33 0 35 35 35 33 .35 35 to co co co to π co co co co to co co co a a a a a a a a a x a a a a υ υ υ υ υ υ υ υ υ υ υ υ υ υ CO Pl PI Pl Pl CO SO O O Pl Pl Pl Pl xυ xυ υx xo xυ xb xu xυ xυ aυ xυ xυ xb xυ JwO JxO JxOx COxOxO JxOxOx PIx . Plx Plxl .x Plx to sa δa δa δa δa δa δa S M a w CM a 8 CM a δ CM a 8 CM aCM.δa w CM a i CM aCM.iSCM.§a _ CM aCM.sa s CM aCM a_ CM._ _ _ _ _ _ _ CM CM pg CM CM CM C cM. cM. CM HCM aCM aCM aCM O O O O O O O O O O O O O O O O O O O O O O O O O O O O as OT C CO CO CO CO tO CO CO C CO tO tO CO tO CO CO CO CO CO CO CO CO tO CO CO CO CO Ωx Ωx Ωx Ω Ωa Ωa a a Ωa aΩ Ωa Ω Ωa Ωa Ωa Ωa Ω x Ωx Ωx Ωx a Ωa a a a Ωa Ωa Ωa Ωa IN σv σv ov in lπ X X X X X X X X σv , in a a a a I » Ω »* O Ω O Ω Ω «a P Ω H Ω a Ω a Ω Ω O X ω a Ω x ω a ω X ω ω a ω ω ω O Ω OΩ OΩ OΩ pΩ OΩ Ωa a Ωa pΩ Ωa OΩ Ωa O OΩ OΩ pΩ p aΩ P xΩ O Ω w a Ωa ι ωaωaωaωaωaωaω ω a _»» a ω a a a a ωa w w ω ω ω ω ω ω ω ω w Ωx xΩ Ωx Ωa Ωa aΩ a a a E in' Table V General Formula 5 f R X Y z m.p.CC) H SCH 3 H OCH 3 OCH 3 CH H SCH 3 H OCH 3 CH 3 CH H SCH 3 H Cl OCH 3 CH H SCH 3 H CH 3 CH 3 CH H SCH 3 H OCH 3 OCH 3 N H SCH 3 H OCH 3 CH 3 N H SCH, 3 H OCH,CH, NHCH N 2 3 3 H SCH 3 CH 3 OCH 3 CH 3 N 4-CH 3 SCH 3 H OCH 3 OCH 3 CH 4-OCH 3 SCH 3 H OCH 3 OCH 3 CH 6-CH 3 SCH 3 H OCH 3 OCH 3 CH 6-OCH SCH 3 H OCH 3 OCH 3 CH 6-F SCH 3 H OCH 3 OCH 3 CH 6-Cl SCH 3 H OCH 3 OCH 3 CH H SOCH H OCH 3 OCH 3 CH H SOCH H OCH 3 CH 3 CH H SOCH H Cl OCH 3 CH H SOCH H CH 3 CH 3 CH H SOCH H OCH 3 OCH 3 N H SOCH H OCH 3 CH 3 N H SOCH H OCH,CH, NHCH N 2 3 H SOCH 3 CH 3 OCH 3 CH 3 N 4-CH 3 SOCH . H OCH 3 OCH 3 CH 4-OCH 3 SOCH H OCH 3 OCH 3 CH 6-CH 3 SOCH H OCH 3 OCH 3 CH 6-0CH SOCH H OCH 3 OCH 3 CH 6-F SOCH, H OCH 3 0CH 3 CH 3 6-Cl SOCH Λ H OCH,. OCH CH 138 Table V (continued) m.p. R X Y Z CO H SO-cyclopropyl H OCH 3 0CH 3 CH H SO-cyclopropyl H 0CH 3 CH 3 CH H SO-cyclopropyl H Cl 0CH 3 CH H SO-cyclopropyl H CH 3 CH 3 CH H SO-cyclopropyl H OCH 3 0CH 3 N H SO-cyclopropyl H OCH 3 CH 3 X K SO-cyclopropyl H 0CH„CH, NHCH. X 2 3 H SO-cyclopropyl CH 3 OCH 3 CH 3 X 4-CH 3 SO-cyclopropyl H 0CH 3 OCH 3 CH 4-OCH 3 SO-cyclopropyl H 0CH 3 0CH 3 CH 6-CH 3 SO-cyclopropyl H 0CH 3 OCH 3 CH 6-OCH SO-cyclopropyl H 0CH 3 CH 3 CH 6-F SO-cyclopropyl H 0CH 3 0CH 3 CH 6-Cl SO-cyclopropyl H OCH 3 OCH 3 CH H SO -cyclopropyl H OCH, OCH, CH 3 3 H SO -cyclopropyl H OCH 3 CH CH 3 H SO.-cyclopropyl H Cl 0CH 3 CH H SO -cyclopropyl H CH 3 CH 3 CH H SO.-cyclopropyl H 0CH 3 0CH 3 N H SO.-cyclopropyl H OCH 3 CH 3 N H SO.-cyclopropyl H 0CH,CH, NHCH N 2 3 H SO -cyclopropyl CH 3 OCH 3 CH 3 N 4-CH 3 SO.-cyclopropyl H 0CH 3 0CH 3 CH 4-OCH SO ? -cyclopropyl H 0CH 3 0CH 3 CH 6-CH 3 SO.-cyclopropyl H 0CH 3 0CH 3 CH 6-0CH SO -cyclopropyl H 0CH 3 OCH 3 CH 6-F SO -cyclopropyl H 0CH 3 0CH 3 CH 6-Cl SO -cyclopropyl H OCH, 0CH 3 CH 3 Table V (continued) t ! R X ϊ Z m.p . CC) H 0S0,CH, CH 3 OCH 3 2 3 H O CH H 0S0,CH, H OCH 3 2 3 CH 3 CH H 0S0,CH, H Cl OCH 3 CH 2 3 H OS0 2 CH 3 H CH 3 CH 3 CH H OS0 2 CH 3 H OCH 3 OCH 3 N H OS0 2 CH 3 H OCH 3 CH, N H 0S0,CH, 2 3 H OCH,CH, NHCH, 2 3 3 N H OSO.CH, CH 3 OCH 3 CH 3 2 3 N 4-CH 3 0S0,CH, H OCH 3 OCH 3 2 3 CH 4-0CH, , 0S0,CH, H OCH 3 OCH 3 CH I 2 3 6-CH 3 " OSO,CH, H OCH 3 OCH 3 CH 2 3 6-OCH , 0S0,CH, H OCH 3 OCH 3 1 2 3 CH 6-F OSO.CH, H OCH 3 OCH 3 2 3 CH 6-Cl 0S0,CH, H OCH 3 OCH 3 CH 2 3 H CN H OCH 3 OCH 3 CH H CN H OCH 3 CH 3 CH H CN H Cl OCH 3 CH H CN • H CH 3 CH 3 CH H CN H OCH 3 OCH 3 N H CN H OCH 3 CH 3 N H CN H OCH,CH, NHCH N 2 3 H CN CH 3 OCH 3 CH 3 N 4-CH 3 CN H OCH 3 OCH 3 CH 4-OCH 3 CN H OCH 3 OCH 3 CH 6-CH 3 CN H 0CH 3 OCH 3 CH 6-OCH CN H 0CH 3 OCH 3 CH 6-F CN H OCH 3 OCH 3 CH 6-Cl CN H OCH 3 OCH 3 CH 7 140 Table V ( continued ) H CH 2 F H 0CH 3 0CH 3 CH H CH 2 F H 0CH 3 CH 3 CH H CH 2 F H Cl 0CH 3 CH ft H 0CH 3 0CH 3 N CH 2 F H CH 2 H 0CH 3 CH 3 H H CH 2 F H 0CH,CH, NHCH, 2 3 3 , H CH 3 0CH 3 X CH 2 F ^3 4-CH 3 CH 2 ft 0CH 3 OCH 3 CH 4-0CH 3 CH 2 F H 0CH 3 0CH 3 CH 6-CH 3 CH 2 F H 0CH 3 OCH 3 CH 6-OCH CH 2 F H 0CH 3 OCH 3 CH 6-F CH 2 H 0CH 3 0CH 3 CH 6-Cl CH 2 H 0CH 3 OCH 3 CH Table V (continued) X Z m.p.CC) H S0 2 N(0CH 3 )CH 3 H OCH 3 OCH 3 CH H SO N(0CH )CH H OCH, CH 3 CH 3 H SO N(0CH )CH H Cl OCH 3 CH H SO N(0CH )CH H CH 3 CH 3 CH H SO N(OCH )CH H OCH OCH 3 N H SO N(OCH )CH H OCH 3 CH 3 N H SO„N(OCH,)CH, H OCH,CH, NHCH N 2 3 3 2 3 H S0 2 N(OCH 3 )CH 3 CH, OCH. CH 3 N 4-CH 3 SO N(OCH )CH H OCH 3 OCH 3 CH 4-OCH 3 SO N(OCH )CH H OCH OCH 3 CH 6-CH 3 S0 2 N(OCH 3 CH 3 H OCH 3 OCH 3 CH 6-OCH S0 2 N OCH 3 )CH 3 H OCH 3 CH 3 CH 6-F S0 2 N OCH 3 )CH 3 H OCH 3 OCH 3 CH 6-Cl S0 2 N(OCH 3 )CH 3 H OCH 3 OCH 3 CH H CO,CH,CH,OH H OCH 3 OCH 3 CH 2 2 2 H CO,CH,CH,OH H OCH CH 3 CH 2 2 2 H CO,CH,CH,OH H Cl OCH 3 CH 2 2 2 H CO,CH,CH,OH H CH 3 CH 3 CH 2 2 2 H CO 2 CH 2 CH 2 0H H OCH 3 OCH 3 N H C0,CH,CH,0H H OCH 3 CH 3 N 2 2 2 H CO,CH,CH OH H OCH,CH, NHCH N 2 2 2 2 3 H CO,CH,CH,OH CH 3 OCH CH 3 N 2 2 2 4-CH 3 CO,CH CH,OH H OCH 3 OCH 3 CH 2 2 2 4-OCH 3 CO,CH,CH,OH H OCH 3 OCH 3 CH 2 2 2 6-CH 3 CO,CH,CH„OH H OCH 3 OCH 3 CH 2 2 2 6-OCH CO,CH„CH„OH H OCH. OCH 3 CH 2 2 2 6-F CO,CH,CH,OH H OCH„ OCH_ CH 2 2 2 7 142 Table V (continued) i R Έ, ϊ z Z m.p. CC) 6-Cl C0 2 CH 2 CH 2 0H H OCH 3 OCH 3 CH H C0 2 CH 2 CH 2 CN H OCH 3 OCH 3 CH H CO,CH,CH„CN H OCH 3 CH 2 2 2 CH 3 H C0 2 CH 2 CH 2 CN H Cl OCH 3 CH H C0 2 CH 2 CH 2 CN H CH 3 CH 3 CH H C0 2 CH 2 CH 2 CN H OCH 3 OCH 3 N H C0,CH,CH,CN H OCH,CH, NHCH, 2 2 2 2 3 3 N H C0 2 CH 2 CH 2 CH CH 3 OCH 3 CH 3 N 4-CH 3 C0,CH,CH,CH H OCH 3 OCH 3 CH 2 2 2 4-OCH CO,CH,CH,CN H OCH 3 OCH 3 CH 2 2 2 6-CH C0 2 CH 2 CH 2 CN H CH 3 OCH CH 6-OCH C0,CH,CH,CH 2 2 2 H OCH 3 OCH 3 CH 6-F CO,CH„CH,CH H OCH 3 OCH 3 CH 2 2 2 6-Cl C0,CH,CH,CN 2 2 2 H OCH 3 OCH 3 CH H CΘ 2 CH 2 C 3 H OCH 3 OCH 3 CH H C0 2 CH 2 CF 3 H OCH 3 CH CH 3 H C0,CH,CF, H Cl 2 2 3 ocκ 3 CH H C0 2 CH 2 CF 3 H CH 3 CH 3 CH H C0 2 CH 2 CF 3 H OCH 3 OCH 3 N H C0,CH,CF, 2 2 3 H OCH 3 CH 3 N H C0,CH,CF, CH, NHCH 2 2 3 H OCH, N 2 3 H C0,CH,CF, 2 2 3 CH 3 OCH 3 CH 3 N 4-CH 3 CO,CH,CF, 2 2 3 H •0CH 3 OCH 3 CH 4-OCH 3 C0„CH,CF, ft 0CH 3 OCH 3 CH 2 2 3 6-CH 3 CO CH CF H OCH 2 2 3 3, OCH 3 CH 6-OCH C0 2 CH 2 C 3 H OCH 3 OCH 3 CH 6-F C0 2 CH 2 CF 3 H OCH 3 OCH 3 CH 6-Cl C0 2 CH 2 CF 3 H OCH 3 OCH 3 CH 143 Table VI General Formula 6 i ι R X Y Z m.p.CC) H SCH 3 H OCH 3 OCH 3 CH H SCH 3 H 0CH 3 CH 3 CH H SCH 3 H Cl OCH 3 CH H SCH 3 H CH 3 CH 3 CH H SCH 3 H OCH 3 OCH 3 N H SCH 3 H 0CH 3 CH 3 N H SCH 3 H OCH 2 CH 3 NHCH N H SCH 3 CH 3 OCH 3 CH 3 N 4-CH 3 SCH 3 H OCH 3 0CH 3 CH 4-C1 SCH 3 H 0CH 3 OCH 3 CH 6-CH 3 SCH 3 H OCH 3 0CH 3 CH 6-OCH SCH 3 H OCH 3 OCH 3 CH 6-F SCH 3 H OCH 3 0CH 3 CH 6-Cl SCH 3 H OCH 3 OCH 3 CH H SOCH H OCH 3 OCH 3 CH H SOCH H 0CH 3 CH 3 CH H SOCH, H Cl OCH 3 CH 3 H SOCH H CH 3 CH 3 CH H SOCH H 0CH 3 OCH 3 N H SOCH H 0CH 3 CH 3 N H SOCH H OCH 2 CH 3 NHCH 3 N H SOCH CH 3 0CH 3 CH 3 N 4-CH 3 SOCH H OCH 3 OCH 3 CH 4-C1 SOCH H 0CH 3 0CH 3 CH 6-CH 3 SOCH H OCH 3 0CH 3 CH 6-OCH SOCH3, H OCH 3 0CH 3 CH 6-F SOCH H OCH 3 0CH 3 CH 6-Cl SOCH H 0CH„ OCH, CH 144 Table VI (continued) m.p. R, R CO H SO-cyclopropyl H 0CH 3 0CH 3 CH H SO-cyclopropyl H 0CH 3 CH 3 CH H SO-cyclopropyl H Cl OCH 3 CH H SO-cyclopropyl H CH 3 CH 3 CH H SO-cyclopropyl H 0CH 3 0CH 3 N H SO-cyclopropyl H 0CH 3 CH 3 N H SO-cyclopropyl H OCH 2 CH 3 NHCH N H SO-cyclopropyl CH 3 0CH 3 CH 3 N 4-CH 3 SO-cyclopropyl H 0CH 3 0CH 3 CH 4-C1 SO-cyclopropyl H 0CH 3 0CH 3 CH 6-CH 3 SO-cyclopropyl H 0CH 3 0CH 3 CH 6-OCH SO-cyelopropyl H ocft 3 OCH 3 CH 6-F SO-cyclopropyl H OCH 3 OCH 3 CH 6-Cl SO-cyclopropyl H 0CH 3 OCH 3 CH H SO -cyclopropyl H OCH 3 OCH 3 CH H SO.-cyclopropyl H OCH 3 CH 3 CH ft SO.-cyclopropyl H Cl 0CH 3 CH ft SO.-cyclopropyl H CH 3 CH 3 CH H SO.-cyclopropyl H 0CH 3 0CH 3 N H SO -cyclopropyl H 0CH 3 CH 3 N H SO.-cyclopropyl H 0CH 2 CH 3 NHCH N H SO.-cyclopropyl CH 3 0CH 3 CH 3 N 4-CH 3 SO -cyclopropyl H 0CH 3 OCH 3 CH 4-C1 SO -cyclopropyl H 0CH 3 0CH 3 CH 6-CH, SO.-cyclopropyl H 0CH 3 0CH 3 CH 3 6-OCH SO -cyclopropyl H OCH 0CH 3 CH 6-F SO -cyclopropyl H OCH 0CH 3 CH 6-Cl SO -cyclopropyl H OCH OCH, CH Table VI (continued]► m.p. R X Y Z ( • C) H 0S0,CH, H 0CH 3 OCH 3 CH 2 3 H 0S0,CH, H 0CH 3 CH 3 CH 2 3 H 0S0,CH, H Cl 0CH 3 CH 2 3 H 0S0„CH, H CH 3 2 3 CH 3 CH H 0S0,CH, H OCH 3 0CH 3 N 2 3 H 0S0,CH, H OCH 3 CH 3 N 2 3 H 0S0,CH, H OCH,CH, NHCH, N 2 3 2 3 3 H 0S0,CH, CH. CH 3 N 2 3 3 0CH 3 4-CH 3 0S0,CH, H OCH 3 0CH 3 CH 2 3 4-C1 0S0,CH, H 0CH 3 0CH 3 CH 2 3 6-CH 3 0S0,CH, H OCH 3 OCH 3 2 3 CH 6-0CH OSO.CH, H OCH 3 OCH 3 2 3 CH 6-F OSO.CH, 2 3 H OCH 3 OCH 3 CH 6-Cl OSO,CH, 2 3 H 0CH 3 0CH 3 CH 146 Table VI (continued) m.p. !f R ϊ Y z CO H CN H 0CH 3 OCH 3 CH H CN H OCH 3 CH 3 CH H CN H Cl OCH 3 CH H CN H CH 3 CH 3 CH H CN H OCH OCH 3 N H CN H OCH 3 CH 3 N H CN H OCH.CH, NHCH N 2 3 H CN CH 3 OCH 3 CH 3 N 4-CH 3 CN H OCH OCH 3 CH 4-C1 CN H OCH 3 OCH 3 CH 6-CH 3 CN H OCH_ OCH 3 CH 6-0CH CN H OCH 3 OCH 3 CH 6-F CN H OCH. OCH 3 3 CH 6-Cl CN H OCH 3 OCH 3 CH Table VI (continued) R. R -1 _i R X Y Z Z m.p . CC) H S0 2 N(OCH 3 )CH 3 H 0CH 3 OCH 3 CH H S0 2 N(0CH 3 )CH 3 H 0CH 3 CH 3 CH H S0 2 N(0CH 3 )CH 3 H Cl OCH 3 CH H S0 2 N OCH 3 )CH 3 H CH 3 CH 3 CH H S0 2 N(OCH 3 )CH 3 H 0CH 3 OCH 3 N H S0 2 N(0CH 3 )CH 3 H 0CH 3 CH 3 N H S0 2 N(OCH 3 )CH 3 H OCH,CH, NHCH N 2 3 H S0 2 N(0CH 3 )CH 3 CH 3 OCH 3 CH 3 N 4-CH 3 S0 2 N(OCH 3 )CH 3 H 0CH 3 OCH 3 CH 4-C1 S0 2 N OCH 3 CH 3 H OCH 3 OCH 3 CH 6-CH 3 SO N(0CH )CH H OCH 3 OCH 3 CH 6-OCH, SO N(0CH )CH H OCH 3 OCH 3 3 CH 6-F SO N(0CH )CH H 0CH 3 OCH 3 CH 6-Cl S0 2 N OCH 3 )CH 3 H OCH, OCH 3 CH 3 H C0,CH,CH,0H H OCH 2 2 2 3, OCH 3 CH H C0,CH,CH,0H H OCH, CH 3 CH 2 2 2 3 H CO,CH,CH,OH H Cl OCH 3 CH 2 2 2 H C0,CH,CH,0H H CH 3 CH 3 CH 2 2 2 H CO,CH,CH,OH H OCH 3 OCH 3 N 2 2 2 H C0,CH,CH,0H H OCH 3 N 2 2 2 CH 3 H C0,CH,CH,OH H 2 2 2 OCH,CH, NHCHg N 2 3 H C0,CH,CH,0H CH 3 OCH 3 CH 3 2 2 2 N 4-CH 3 C0,CH,CH,0H H OCH 3 2 2 2 OCH 3 CH 4-C1 CO,CH,CH,OH H OCH 3 2 2 2 OCH 3 CH 6-CH 3 CO,CH,CH,OH H OCH 3 2 2 2 OCH 3 CH 6-OCH C0,CH,CH,0H H OCH 3 2 2 2 OCH 3 CH 6-F C0,CH,CH,0H 2 2 2 H OCH 3 OCH 3 CH 6-Cl C0,CH,CH,0H H OCH, 2 2 2 3 0CH 3 CH H C0,CH,CH,CN 2 2 2 H OCH, OCH 3 CH 3 aa a ^ ^ a a a ,N x x x a a a a a a a a.a a a a a a a a a a a a a a a a a a a a pa w W CO in W oo CO CO O CO O O CO W CO CO CO CO CO CO to co co co co co co co co co co pa o o o o o o o to o o o o o o o o o o o o o o o o o o o o o o o o o > t Ω Ω Ω Ω to to to to Ω Ω o O to to to to Ω Ω Ω O tO to to to Ω Ω Ω Ω o n n X X X X Ω Ω Ω Ω X X X X Ω Ω Ω Ω X X X X Ω Ω Ω Ω X X X X X X X <*-\ X X X X to to to to X X X X to to to co X X X X ω ω ω ω _--. Ω Ω Ω Ω to to to to Ω Ω Ω Ω to to to tO Ω Ω Ω Ω ω ω ω ω Ω Ω Ω X X X X Ω Ω Ω Ω X X X X O Ω O X X X X X X X ω ω ω ω X X X X to to to to x x x x ω ω ω ω ω ω v - » to to to to Ω Ω Ω Ω ω ω ω ω S to N to to Ω Ω Ω Ω X X X X X X X X ω ω ω ω ω ω ω ω > 1 > > > > > > > > > > > > > T > •__ •__ > •__» •_- > > > • •» I I I I I I I I I I I I I I ω ω t ω ω to A- ω ω to A- ω ω to A- ω ω io A- ω ω to A- ω ω to A- ω ω to <n > 3 X CD X ><i X X X X X X X X X X X ixi X X X X H ω t- 4 H 4 I- 4 ω I- 4 I- 4 ω _-• _-* ω H H> ω ι-» M ω ι-» ι-' i-* ω ι-» ι- i i-* n rt II II II II II II II II II II II II II II II II II II li II II II II II II II II II II II II 01 Dl o Ω Ω O o Ω Ω O o Ω Ω o o Ω Ω o o Ω Ω O O Ω Ω O O Ω Ω O O Ω Ω _-• cr Ω X X Ω Ω X X Ω Ω X X Ω Ω X X Ω Ω X X Ω Ω X X Ω Ω X X Ω Ω X X X ι_> . ω X X ω ω X X ω ω X X ω ω X X ω ω X X ω ω x x ω ω x x ω ω •n (D ω i ω ω ω ω ω ω ω ω ω ω ω ω ω ω o 3 < H K K K K IK c H t-> I- 4 r-« II II II II II II II II 01 Ω Ω Ω Ω Ω Ω Ω Ω -H X X X X X X X X to to to to to to E |Ω Table VII (continued) __1 __2 A X ϊ m. p .CC) H S0 2 CH CH 3 ) 2 A-4 3 =OCH 3 H SOCH,Cft,CH,CH, A-3 X,=CH, 2 2 2 3 1 3 H SOCH CH Cft CH 3 A-3 Ε =QCR 3 H SOCH CH CH CH 3 A-4 X 3 =0CH 3 H SO CH CH Λ CH,CH, A-2 X =CH, Y =CH, 2 2 2 2 3 1 3 1 2 H SO„CH„CH„CH.CH_ A-3 X ,=CH, 2 2 2 2 3 1 3 H SO CH CH CH CH A-3 X =0CH H SO CH CH CH, CH, A-4 X,=OCH, 2 2 2 2 3 3 3 H S-cyclopropyl A-2 X^GH Y ι =CH 2 H S-cyclopropyl A-3 X =GH H S-cyclopropyl A-3 X =OCH H S-cyclopropyl A-4 X =OCH H SO -cyclopropyl A-2 X.,=CH Y τ . =CH 2 H SO -cyclopropyl A-3 X,=CH H SO -cyclopropyl A-3 X 0CH, H SO -cyclopropyl A-4 X =0CH Table VII (continued) m.p. (*C> H 0S0,CH, A-3 2 3 X 1 =CH 3 H OSO„CH, A-4 X =OCH, 2 3 3 3 H OSO„CH_. A- 7 X =OCH„ Y =OCH 2 3 4 3 H OSO,CH,CH, A-3 X 1= CH 3 2 2 3 H OSO ,CH,CH, A-4 X 3 =OCH 3 2 2 3 H OS0 2 CF 3 A-3 lS OCH 3 H 0S0,CF, A-4 X 3 =OCH 3 2 3 H oso 2 ccι 3 A-2 X 1 =CH 3 Y 1 =CH 2 H oso 2 cci 3 A-3 X 1 =0CH 3 H oso 2 ccι 3 A-4 X 3 =OCH 3 H CN A- 2 Y 1= CH 2 X l βCH 3 H CN A-3 X 1= CH 3 H CN A-3 X. =0CH 3 H CN A-4 X,=0CH, 3 3 H CH 2 F A-2 X 1= CH 3 Y 1= CH 2 H CH 2 F A-3 X 1 =CH 3 H CH 2 F A-3 x^oc^ H CH 2 F A-4 X 3 β ° CH 3 H CF 2 H A- 2 X 1 =CH 3 Y 1 =CH 2 H CF Λ H A-3 X χ =CH 3 2 H CF 2 H A- 3 X aOCH, 1 3 H CF 2 H A-4 X,=0CH, 3 3 Table VII (continued) R, m. .CC) 6- (CH 3 ) 2 S0 2 N CH 3 ) 2 A-2 X 1 =CH 3 Y 1 =CH 2 6-N CH 3 ) 2 S0 2 N(CH 3 ) 2 A-3 X 1= CH 3 6-N(CH 3 ) 2 S0 2 N CH 3 ) 2 A-3 x^oc^ 6-N(CH 3 ) 2 S0 2 N(CH 3 2 A-4 X 3 =OCH 3 6-NHCH 3 S0 2 N CH 3 ) 2 A-2 X 1 =CH 3 Y 1 =CH 2 6-NHCH 3 S0 2 N(CH 3 ) 2 A-3 X 1= CH 3 . 6-NHCH S0 2 CH 3 ) 2 A-3 X 1= 0CH 3 6-NHCH S0 2 N(CH 3 ) 2 A-4 X 3 = OCH 3 6-OCH C0 2 CH 3 A-3 X 1= CH 3 6-OCH C0 2 CH 3 A-3 X 1 -OCH 3 6-OCH C0_,CH, A-4 X 3 =OCH 3 2 3 6-SCH, C0 Λ CH, A-2 3 2 3 X 1 =CH 3 Y 1 =CH 2 6-SCH C0,CH, A-3 2 3 X 1= CH 3 6-SCH CO,CH, A-3 X 1= OCH 3 2 3 6-SCH CO„CH„ A-4 X =OCH, 2 3 3 3 6-N CH 3 ) 2 CO,CH, A-3 1 =OCH 3 2 3 6-N(CH 3 2 CO,CH, A-4 X =OCH, 2 3 3 3 Table VII (continued) ι R. X m.p.CC) 6 -NHCH 0 2 N CH 3 2 A-2 . 6 -NHCH S0 2 N(CH 3 ) 2 A-3 x CH 3 6 -NHCH, S0 2 N CH 3 2 A-3 3 X 1= 0CH 3 6 -NHCH, S0 2 N(CH 3 ) 2 A-4 X 3 =OCH 3 3 6 -OCH, S0 2 N CH 3 ) 2 A-2 3 X 1= CH 3 Y 1= CH 2 6-OCH, S0 2 N(CH 3 ) 2 A-3 3 X 1 =CH 3 6 -OCH S0 2 CH 3 ) 2 A-3 ^OCH 3 6 -OCH S0 2 N(CH 3 ) 2 A-4 3 =OCH 3 6-SCH 0 2 N(CH 3 2 A-3 X. =CH ε l 3 6 -SCH 2 N(CH 3 ) 2 A-3 ε ι OCH„ 6 -SCH S0 2 N CH 3 ) 2 A-4 X,=OCH„ 3 3 6-N CH 3 ) 2 S0 2 N CH 3 ) 2 A-2 X 1= CH 3 Y 1 =CH 2 S0 2 N(CH 3 ) 2 A-3 X =CH 6 -* C V 2 3 6- CH 3 2 0 2 CH 3 2 A-3 OCH 3 6-N CH 3 2 S0 2 N CH 3 ) 2 A-4 X-- OCH. 6 -NHCH CO,CH, A-3 2 3 X 1= CH 3 6-NHCH, C0 2 CH 3 A-3 X 1 =OCH, 3 6-NHCH C0 2 CH 3 A-4 X =OCH„ 3 2 6 -O 6 -OCH, SO,NHOCH, A-3 3 2 3 X 1= CH 3 6 -OC 6 -OCH, SO„NHOCH, A-4 X,=OCH 3 2 3 3 2 6 -SC 6-SCH, SO,NHOCH, A-3 X. =CH_ 3 2 3 3 6-SCH, SO,NHOCH, A-3 X =' OCH. 3 2 3 6-SCH SO, NHOCH, A-4 X =OCH. 2 3 > I I I > I > > ^. f t> > > > > > > > I I > I I I I I I I I I I I I A- ω ω to A- ω ω to A- ω ω io A- ω ω to A- k x x X X X X X X X X M X k I- 1 h» ft ω M ι-» t A- , &- 4 _-* ω ι-« II II II II II II II II II II II II II II II II II I o o Ω Ω O O Ω Ω O O Ω Ω O O Ω Ω O Ω Ω X X Ω Ω X X Ω Ω X X Ω Ω X X Ω X X ω ω X X ω ω X X ω ω X X ω ω x ω ω ω ω ω ω ω ω ω ω II II II II Ω Ω Ω Ω X X X X ιo to to to Table VIII General Formula 8 _3 A X Y m.p.CC) H SOCH A-3 1 3 H SOCH A-3 X 1 =0CH 3 H SOCH A-4 X 3 =OCH 3 H SOCH CH, A-3 2 3 X 1 =CH 3 H SOCH„CH, A-3 2 3 ∑ 1 =0CH 3 H SOCH,CH, A-4 X 3 =OCH 3 2 3 H SOCH CH CH A-3 £ * £• __» ∑ 1= CH 3 H SOCH CH,CH, . A-3 X 1= 0CH 3 2 2 3 H SOCH 2 CH 2 CH 3 A-4 3= OCH 3 H S-cyclopropyl A-2 H S-cyclopropyl A-3 1= CH 3 H S-cyclopropyl A-3 X 1 =0CH 3 H S-cyclopropyl A-4 3 =OCH 3 H SO -cyclopropyl A-2 X 1= CH 3 Y 1 =CH 2 H SO -cyclopropyl A-3 H S0 2 -cyclopropyl A-3 H S0 2 -cyclopropyl A-4 X 3 =OCH 3 Table VIII (continued) _1 h. A X Y m. .( β C) H 0S0 2 CH 3 A-2 X 1= CH 3 Y 1 =CH 2 H 0S0 2 CH 3 A-3 1 =CH 3 H 0S0 2 CH 3 A-3 Xl =OCH 3 H 0S0 2 CH 3 A-4 X 3 =0CH 3 H 0S0 2 CH 2 CH 3 A-2 X 1 =CH 3 Y 1 =CH 2 H 0S0 2 CH 2 CH 3 A-3 X 1= CH 3 H 0S0,CH,CH, A-3 ∑ 1= 0CH 3 2 2 3 H OSO CH,CH, A-4 3 =0CH 3 2 2 3 H OSO,CF, A-2 2 3 X 1= CH 3 Y 1= CH 2 H 0S0,CF, A-3 X 1 =OCH 3 2 3 H OS0 2 CF 3 A-4 X 3 =OCH 3 H 0S0,CC1, A-3 2 3 X 1= CH 3 H 0S0,CC1, A-3 - 2 3 X 1= 0CH 3 H CH 2 F A-3 1= CH 3 H CH 2 F A-4 3 =OCH 3 Table VIII (continued) ι h. A X Y m.p.CC) H S0,NHCH, A-2 X 1 =CH 3 Y X =CH 2 2 3 H S0,NHCH, A-3 X^-^CH^ 2 3 H S0,NHCH, A-3 χ =0CH 3 2 3 H S0,NHCH, A-4 X 3 =OCH 3 2 3 H C0,CH,CH,0H A-2 2 2 2 X 1= CH 3 Y 1 =CH 2 H C0 2 CH 2 CH 2 0H A-3 1= CH 3 H C0 2 CH 2 CH 2 OH A-3 X 1 =0CH 3 H C0 2 CH 2 CH 2 OH A-4 X 3 =OCH 3 H C0 2 CH 2 CH 2 CN A-2 X 1 =GH 3 Y 1= CH 2 _ H CO CH CHgCN A-3 X 1 =CH 3 H C0 2 CH 2 CH 2 CN A-3 X 1= OCH 3 H C0 2 CH 2 CH 2 CN A-4 X 3 =OCH 3 H C0 2 CH 2 C 3 A-2 X 1= CH 3 Y 1 =CH 2 H C0 2 CH 2 CF 3 A-3 X 1= CH 3 H C0 2 CH 2 CF 3 A-3 X 1 =0CH 3 H C0 2 CH 2 CF 3 A-4 X =OCH, 3 3 159 . Table IX General Formula , 9 ι A X Y m. p . ( *C) H SOCH A-3 X l βCH 3 H SOCH A-3 ∑ 1^ oca 3 H SOCH A-4 ∑ 3 -^CH 3 H SOCH,CH, A-2 2 3 ∞ s Y l βCH 2 H SOCH,CH, A-3 X, ^CH, 2 3 1 3 H SOCH,CH, A-4 3 -OCH 3 2 3 H SOCH 2 CH 2 CH 3 A-2 ∞a * ™! H S0CH,CH,CH, A-3 2 2 3 ∑ l βCH 3 H SOCH 2 CH 2 CH 3 A-3 X χ -OCH 3 H SOCH,CH,CH, A-4 X 3 = CH 3 2 2 3 H S-cyclopropyl A-2 Xl =CH 3 Y l βCH 2 H S-cyclopropyl A-3 ∞s H S-cyclopropyl A-3 X^CH 3 H S-cyclopropyl A-4 X 3 =OCH 3 H SO-cyclopropyl A-2 X lβ CH 3 V CT 2 H SO-cyclopropyl A-3 X 1= CH 3 H SO-cy c lopropy 1 A-3 H SO-cyclopropyl A-4 X 3 =OCH 3 H SO.-cyclopropyl A-2 X 1= CH 3 jr CE 2 H SO.-cyclopropyl A-3 X 1 =CH 3 H SO.-cyclopropyl A-3 ∑^C^ H SO -cyclopropyl A-4 X 3 =OCH 3 160 Table IX (continued) i X Y m.p. CC) H OS0 2 CH 3 A-2 ^s ^ H OS0 2 CH 3 A-3 X l βCH 3 H 0S0,CH, A-3 X «OCH 2 3 H 0S0,CH, A-4 ∑ 3 «OCH 3 2 3 H 0S0,CH„CH, A-3 X 1 -CH 3 2 2 3 H 0S0,CH.CH. A-3 ∑1 -OCH 3 2 2 3 H OSO.CH-CH. A-4 2 2 3 r 3 -ocH 3 - H OS0 2 CF 3 A-3 h m( z - H 0 2 CF 3 Λ? 80 *-* X^-OCH K OS0 2 CF 3 A-4 X,»0CH, 3 3 H CH 2 F A-2 ∑1 ^ 3 Y 1- CH 2 H CH F A-3 X 1 »CH 3 H CH 2 A-3 Xl -0CH 3 H CH 2 A-4 3 3 H CN A-2 ∞s -™ 2 H CN A-3 X 1 -CH 3 H CN A-3 ^-OC^ H CN A-4 X 3 « CH 3 161 Table IX (continued) R. m.p. CC) H S0 2 N(OCH 3 )CH 3 A-2 X t 'C 3 Y 1 =CH 2 H SO,N(OCH, )CH, A-3 2 3 3 X 1 =CH 3 H SO N(0CH )CH A-3 _^-0CH 3 H SO N(0CH )CH A-4 X 3 -OCH 3 H SO NHCH A-3 X l βCH 3 H SO,NHCH, A-3 X lβ OCH 3 2 3 H S0 2 NHCH 3 A-4 X 3 -OCH 3 H C0 2 CH 2 CH 2 0H A-2 -cκ 3 Y l aCH 2 H C0 2 CH 2 CH 2 OH A-3 CH 3 H C0 2 CH 2 CH 2 0H A-3 x^c^ H C0 2 CH 2 CH 2 OH A-4 X 3 ^CH 3 H C0 2 CH 2 CH 2 CN A-2 Xl -CH 3 V CT 2 H C0,CH,CH,CN A-3 2 2 2 ∑ 1 SCH 3 H CO,CH,CH,CN A-3 X 1 = CH 3 2 2 2 H C0 2 CH 2 CH 2 CN A-4 X,=OCH, 3 3 H C0,CH,CF, A-2 2 2 3 X 1= CH 3 Y 1 =CH 2 H CO,CH,CF, A-3 2 2 3 X 1 =CH 3 H C0,CH,CF, A-3 X =OCH 2 2 3 1 3 H CO,CH,CF, A-4 X,=0CH, 2 2 3 3 3 Table X General Formula 10 e A X ϊ m.p. CC) H SOCH A-2 X 1 -CH 3 Y^O^ H SOCH A-3 X l eCH 3 H SOCH A-3 ∑ lβ OCH 3 H SOCH, A-4 X 3 -0CH 3 3 H S0CH,CH, A-2 2 3 h-∞z H S0CH 2 CH 3 A-4 ∑ 3 - CH 3 H SOCH CH CH A-2 ∑ Λ ™* H SOCH 2 CH 2 CH 3 A-3 V*s H SOCH CH,CH, A-3 X «0CH 2 2 3 H SOCH,CH,CH, A-4 X 3 »0CH 3 2 2 3 H SO.CH, A-2 2 3 "** Y 1 =CH 2 H S0 2 CH 3 A-3 ∑, * H 3 H SO,CH, A-3 2 3 *^ H SO,CH,CH, A-2 ∑1 ^H 3 1= CH 2 2 2 3 H S0 2 CH 2 CH 3 A-3 X 1 =CH 3 H 0 2 CH 2 CH 3 A-3 X lβ OCH 3 H 0 2 CH 2 CH 3 A-4 ∑ 3 =OCH 3 H SO,CH,CH,CH, A-3 2 2 2 3 X 1 S0H 3 H SO,CH,CH,CH, A-3 X lS OCH 3 2 2 2 3 H SO,CH,CH,CH, A-4 X 3 =OCH 3 2 2 2 3 H S-cyclopropyl A-2 H S-cyclopropyl A-3 A βCH 3 H S-cyclopropyl A-3 Σ , =OCH, 1 3 H S-cyclopropyl A-4 X 3 =,0CH 3 H SO-cyclopropyl A-2 CH 3 V CH 2 H SO-cyclopropyl A-3 X l βCH 3 H SO-cyclopropyl A-3 X. «OCH, Table X (continued) i h. A X Y m.p.CC) H SO-cyc lopropy 1 A-4 ∑ 3 -OCH 3 H SO -cyclopropyl A-2 Xl -CH 3 Y 1- CT 2 H SO -cyclopropyl A-3 Σ »CH 1 3 H SO -cyclopropyl A-3 Xl -OCH 3 H SO -cyclopropyl A-4 ∑ 3 -OCH 3 H 0S0,CH, A-2 ∑1 -CH 3 Y χ -CH 2 2 3 H OSO,CH, A-3 2 3 ° H OSO,CH, A-3 Σ χ ^CH 3 2 3 H OSO,CH, A-4 Σ,-OCH, 2 3 3 3 H CH 2 F A-2 Σ «CH 1 3 H CH 2 F A-3 Σ χ -CH 3 W H CH 2 F A-3 Xl «0CH 3 H CH 2 F A-4 ∑ 3 -OCH 3 H CN A-4 ∑ 3 - CH 3 Table Σ (continued) R_- R, . .CO H S0 2 N OCH 3 )CH 3 A-2 1 3 Y l sCH 2 H SO N(0CH )CH A-3 ^s H SO N(0CH )CH A-3 X l"° CH 3 H SO N(0CH )CH A-4 ∑ 3 «0CH 3 H S0,NHCH, A-2 ∑1 ^H 3 2 3 H S0,NHCH, A-3 V ∑ 1 -CH 3 2 3 H S0 2 NHCH 3 A-3 ∑1 ^CH 3 H S0,NHCH, A-4 Σ,-0CH, 2 3 3 3 H SO NHCH CH A-2 "^^ V*z H S0,NHCH,CH, A-4 ∑ 3 »0CH 3 2 2 3 H C0,CH Λ CH,0H A-3 2 2 2 h m<m z H CO.OT CH.OH A-3 ∑1 »0CH 3 2 2 2 H C0 2 CH 2 CH 2 CN A-2 Σ χ »CH 3 H C0,CH,CH,CN A-3 2 2 2 X l βCH 3 H C0,CH,CH CN A-3 X lS OCH 3 2 2 2 H C0,CH,CH,CN A-4 ∑ 3 =0CH 3 2 2 2 H C0,CH,CF, A-3 ∑ 1 =CH 3 2 2 3 H C0,CH,CF, A-3 Σ, =0CH, 2 2 3 1 3 H C0,CH,CF, A-4 Σ,=OCH, 2 2 3 3 3 Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Weight Percent* Active Ingredient Diluent(s) Surfactant(s). Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can, of course, be present.depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are some- times desirable, and are achieved by incorporation into the formulation or by tank mixing. Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufac¬ tured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide." 2nd Ed.. Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp.. Ridgewood. New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York. 1964. list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example. Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering. December 4, 1967, pp. " 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. LOUX. U.S. Patent 3,235,361. February 15, 1966, Col. 6, line 16 through Col. 7. line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3.309.192. March 14. 1967, Col. 5, line 43 through Col. 7. line 62 and Examples 8. 12. 15, 39. 41. 52. 53. 58. 132, 138-140, 162-164. 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855. June 23, 1959. Col. 3. line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.. New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications. Oxford. 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 24 High Strength Concentrate N2-[ (4,6-Dimethoxypyrimidin-2-y1)aminocarbonyl]- N3-methyl-2.3-pyridinedisulfonamide 99% trimethylnonyl polyethylene glycol ether 1% The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U. S. S. no. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use. Example 25 Wettable Powder 2-[[(4.6-Dimethoxypy imidin-2-yl)aminocarbonyl - aminosulfonyl]-3-pyridinecarboxylic acid, methyl ester 65% dodecylphenol polyethylene glycol ether 2% sodium ligninsulfonate 4% sodium silicoaluminate 6% montmorillonite (calcined) 23% The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example 26 Agueous Suspension N2-[( .6-Dime hoxypyrimidin-2-yl) minoca bonyl1- N3-methyl-2,3-pyridinedisulfonamide 50.0% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodiu phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. Example 27 Oil Suspension N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl3-3-(1- propylsulfonyl)-2-pyridinesulfonamide methyl ester 35% blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates 6% xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water. Example 28 Oil Suspension N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl3- 3-(1-methylsulfonyloxy)-2-pyridinesulfonamide methyl ester 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 29 Aqueous Suspension N-[ (4,6-dimethoxyρyrimidin-2-yl)aminocarbonyl3- 3-(l-ethylsulfonyl)-2-pyridinesulfonamide methyl ester 25% hydrated attapulgite 3% crude calcium ligninsulfonate 10% sodium dihydrogen phosphate 0.5% water 61.5% The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns. Example 29 Wettable Powder N2-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl3- N3-methyl-2,3-pyridinedisulfonamide 40.0% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3% low viscosity methyl cellulose 1.5% attapulgite 54% The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging. All compounds of the invention may be formulated in the same manner. Example 30 Granule wettable powder of Example 29 15% gypsum 69% potassium sulfate 16% The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S.#18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient. Example 31 Wettable Powder N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl- 3-(ethylsulfonyl)-2-pyridinesulfonamide methyl ester 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammer- milled and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging. Example 32 Extruded Pellet N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl- 3-(ethylsulfonyl)-2-pyridinesulfonamide 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. Example 33 Wettable Powder N-[ (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl3- 3-(1-ethylsulfonyl)-2-pyridinesuIfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended and then ground in a hammer ill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged. Example 34 High Strength Concentrate N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl3- 3-(l-ethylsulfonyl)-2-pyridinesulfonamide 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer mill to produce a high strength concentrate ' essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways. Example 35 Wettable Powder 2-[[ (4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl3- aminosulfonyl3-3-pyridinecarboxylic acid, methyl ester 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended and then ground in a ha mermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged. Example 36 High Strength Concentrate N2-[ (4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl - N3-methyl-2,3-pyridinedisulfonamide 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways. Utility Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulantε. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in plantation crops. Solanaceae family-crops such as tomatoes, potatoes and peppers, other crops such as wheat, barley, corn, cotton or soybeans, and their fallow land. In particular, some of the compounds of this invention control weeds in corn (maize) both pre- and postemergence without significant crop damage. Some of the compounds of this invention also control weeds in potato (Solanum tuberosum) and tomato (Lvcopersicon esculentum) without significant crop damage. They are particularly useful to control such problem weeds as the foxtail (Setaria spp.). fall panicu (Panicum dichotomiflorum). barnyardgrass (Echinochloa crusσalli). seedling johnsongrass (Sorghum halepense) and shattercane (Sorghum bicolor) . They can be used preeme-rgence or postemergence and are most effective when applied postemergence to young weeds. They are also effective on certain broadleaf weeds such as lambsquarters (Chenopodium album) . pigweed (Amaranthus spp.) and velvet leaf (Abutilon theophrasti) . Alternatively, the subject compounds are useful to modify plant growth. The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formu¬ lations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.001 5 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required. 10 The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole. imidazolinone, uracil. urea, amide, diphenylether, cineole, carbamate and bipyridylium types. They are 15 particularly useful in combination with the following herbicides. Common Name Chemical Name alachlor 2-chloro-2' ,6 '-diethyl-N-(methoxymethyl)' 20 acetanilide atrazme 2-chloro-4-(ethylamino)-δ-(isopropyl- amino)-s_-triazine butylate s-ethyl- iisobutylthiocarbamate Δ __b cyanazine 2-[ [4-chloro-6-(ethylamino)-s_-triazin-2- yl3amino]-2-methylpropionitrile dicamba 3, 6-dichloro-_-anisic acid EPTC S-ethyl dipropylthiocarbamate linuron 3-(3,4-dichlorophenyl)-l-methoxy-l- 0 methylurea metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N- (2-methoxy-l-methylethyl)acetamide metribuzin 4-amino-6-.ter_t-butyl-3-(methylthio)-as- triaziήe-5(4H)-one 5 4297 176 Common Name Chemical Name tridiphane 2-(3,5-dichlorophenyl)-2-(2.2.2-tri- chloroethyl)oxirane 2.4-D (2,4-dichlorophenoxy)acetic acid bromoxynil 3,5-dibromo-4-hydroxyphenylcyanide paraquat l,l , -dimethyl-4.4-bipyridinium ion glyphosate N-(phosphononeth 1)glycine DCPA dimethyl tetrachloroterephthalate dalapon 2,2-dichloropropionic acid dinoseb 2-(l-methylpropyl)-4.6-dinitrophenol diphena id N.N-dimethyl-2.2-diphenylacetamide pendimethalin N-(l-ethylptopyl)-3.4-diraethyl-2.6- dinitrobenamine oryzalin 3,5-dinitro-N,N-dipropylsulfanilamide trifluralin α.α.α-trifluoro-2.6-dinitro-N.N- dipropyl-p-toluidine chloramben 3-amino-2.5-dichlorobenzoic acid naproparaide 2-(α-naphthoxy)-N.N-diβthylpropion- a ide pebulate S-propyl butylethylth 0iocarbamate chlorpropham isopropyl m-chlorocarbanilate bensulide S-(0.0-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl)benzene- sulfonamide Trade Name Chemical Name Harmony TM 3-CC(4-methoxy-6-methyl-l.3.5-triazin- 2-yl)aminocarbonyl]aminosulfonyl3-2- thiophenecarboxylic acid, methyl ester Cinch® l-methyl-4-(l-methylethyl)-2-exo-[(2- methylphenyl)-methoxy -7-oxabicyclo- [2.2.13heptane 2-ethoxy-N-[[4-(2.2.2-trifluoroethoxy)- 6-methoxy-l.3,5-triazin-2-yl3amino- carbonyljbenzenesulfonamide Compounds Compound _2 R -1 X Y 2 1 S0,CH,CH,CH, H H 0CH 3 OCH 3 CH 2 2 2 3 2 S0,CH,CH,CH, H H CH 3 OCH 3 CH 2 2 2 3 3 S0,CH CH,CH, H H Cl OCH, 3 CH 2 2 2 3 4 S0„CH CH„CH„ H H CH 3 CH 2 2 2 3 CH 3 5 S0,CH CH CH H H OCH 3 OCH 2 2 2 3 3, N 6 SO CH„CH,,CH H H CH 3 OCH 3 N 2 2 2 3 7 S0„CH CH,CH, H H OCH CH NHCH 2 2 2 3 2 3 3, N 9 S(0)CH CH CH„ H ■ H CH 3 OCH 2 2 3 3 CH 10 S(0)CH CH CH H H Cl OCH 2 2 3 3 CH 11 S(0)CH CH CH H H CH 3 CH 3 CH 12 S(0)CH CH CH H H OCH3, OCH,3 N 13 S(0)CH CH CH H H CH 3 OCH, N 3 14 S(0)CH CH Λ CH, H H OCH CH., NHCH 2 2 3 2 3 3 N 15 S(0)CH CH H H 0CH 3 OCH 3 . CH 16 S(0)CH CH H H OCH 3 CH 3 CH 17 S(0)CH CH CH H H Cl OCH 3 CH 18 S(0)CH CH H H CH 3 CH 3 CH 19 S(0 CH 2 CH 3 H H OCH OCH 3 N 20 S(0)CH CH H H OCH 3 CH 3 N 21 S0,CH,CH, H H OCH 3 OCH 3 CH 2 2 3 22 SO,CH,CH, H H 0CH 3 CH 3 CH 2 2 3 23 SO,CH CH, H H Cl OCH 3 CH 2 2 3 Compound!5 (continued) Compound R ϋ X Y Z .24 S0 2 CH 2 CH 3 H H CH 3 CH 3 CH 25 . S0,CH,CH, H H 0CH 3 OCH 3 N 2 2 3 26 S0,CH,CH, H H 0CH 3 CH 3 N 2 2 3 27 S0,CH,CH, CH 3 H 0CH 3 CH 3 N 2 2 3 28 S(0)CH 3 H H 0CH 3 0CH 3 CH 29 S(0)CH 3 H H 0CH 3 CH 3 CH 30 S(0)CH 3 H H Cl 0CH 3 CH 31 S(0)CH 3 H H CH 3 CH 3 CH 32 S(0)CH 3 H H 0CH 3 CH 3 N ~ 33 S(0)CH CH 3 H 0CH 3 CH 3 N 34 S0,CH, H H OCH 0CH 3 CH 2 3 35 S0,CH, H H 0CH 3 CH 2 3 - CH 3 36 S0„CH, H H Cl 0CH 3 CH 2 3 37 S0,CH, H H CH 3 CH 3 CH 2 3 38 S0,CH, H H 0CH 3 0CH 3 N 2 3 39 S0,CH, H H 0CH 3 CH 3 N 2 3 40 S(0)CH(CH 3 ) 2 H H 0CH 3 0CH 3 CH 41 S(0)CH(CH 3 ) 2 H H 0CH 3 CH CH 3 42 S(0)CH(CH 3 ) 2 H H Cl 0CH 3 CH 43 S(0)CH(CH 3 ) 2 H H CH 3 CH 3 CH 44 S(0)CH(CH 3 ) 2 H H 0CH 3 OCH 3 N 45 S(0)CH(CH 3 ) 2 H H 0CH 3 CH, N 3 46 S0 2 CH(CH 3 ) 2 H H OCH 3 0CH 3 CH 47 S0 2 CH CH 3 ) 2 H H OCH, CH 3 CH 3 48 S0 2 CH CH 3 2 CH 3 H Cl 0CH 3 CH 49 S0 2 CH CH 3 ) 2 H H CH 3 CH CH 3 50 S0 2 CH CH 3 ) 2 H H 0CH 3 0CH 3 N 51 S0 2 CH CH 3 ) 2 H H 0CH 3 CH 3 N 52 S0 2 CH CH 3 ) 2 CH 3 H 0CH 3 CH 3 N 53 S0 2 CH 2 ) 3 CH 3 " H H 0CH 3 CH 0CH 3 54 S0 2 CH 2 3 CH 3 H H 0CH 3 CH 3 CH 55 S0 2 CH 2 ) 3 CH 3 H H Cl 0CH 3 CH Compounds (continued) Compound Hi R ι X Y Z 56 S0 2 (CH 2 ) 3 CH 3 H H CH 3 CH CH 3 57 S0 2 CH 2 ) 3 CH 3 H H OCH 3 OCH 3 N 58 S0 2 CH 2 ) 3 CH 3 H H OCH, 3 CH 3 N 59 S0 2 (CH 2 ) 3 CH 3 CH 3 H OCH, CH 3 N 3 60 S0,CH,CH, H CH 3 2 2 3 OCH, OCH CH 3 61 SO,CH,CH, H CH 3 2 2 3 OCH 3 CH 3 CH 62 S0,CH,CH, H CH 3 CH 3 2 2 3 CH 3 CH 63 S0,CH,CH, H 2 2 3 OCH, CH 3 N CH 3 3 64 SO,CH,CH, H OCH, 2 2 3 OCH 3 OCH, 3 CH 3 65 OSO,CH, H H 2 3 0CH 3 OCH 3 CH 66 OSO,CH, H H 2 3 QCH 3 CH 3 CH 67 0S0,CH, H 2 3 H Cl 0CH 3 CH 68 0S0,CH, H 2 3 H CH 3 CH 3 CH 69 0S0,CH, H 2 3 H 0CH 3 CH 3 N 70 0S0,C,H. H 2 25 H 0CH 3 OCH 3 CH 71 0S0 2 C 2 H 5 H H CH 3 OCH 3 CH 72 OS0 2 C 2 H 5 H H Cl OCH 3 CH 73 0S0.C,H. H 2 2 5 H CH 3 CH 3 CH 74 OSO C H, H 2 2 5 H OCH 3 OCH 3 N Compounds (continued) Compound R. R R- X Y Z 88 CH 2 C1 H H CH 3 OCH, N 89 P (0) (OCH 2 CH 3 ) 2 H H OCH, OCH, CH 90 PCO) OCH 2 CH 3 ) 2 H H OCH " 3 CH CH 3 " 91 P(0) (0CH 2 CH 3 ) 2 H H CH. CH. CH R Compound _2 R _1 X Y Z 92 SO,NHCH, H H OCH 3 OCH 3 CH 2 3 93 SO,NHCH, H H Cl OCH 3 CH 2 3 94 SO,NHCH, H H CH 3 CH 3 CH 2 3 95 SO,NHCH, H H OCH, CH 3 N 2 3 3 96 SO N(OCH )CH H H OCH 3 OCH 3 CH 97 S0 2 N(OCH 3 CH 3 H H OCH 3 CH 3 CH 98 SO N(OCH )CH H H OCH 3 CH 3 N 99 SO N(0CH )CH CH 3 H OCH 3 CH 3 N 100 SO,NHCH,CH, H H OCH 3 OCH 3 CH 2 2 3 101 SO,NHCH,CH, H H Cl OCH 3 CH 2 2 3 102 SO,NHCH,CH, H H CH 3 CH 3 CH 2 2 3 103 SO NHCH,CH H H OCH 2 2 3 3, OCH 3 N 104 SO,NHCH,CH, H H OCH, CH 3 N 2 2 3 3 105 SO NHCH CH H H OCH, 2 2 3 3 CH 3 N 106 SO NHCH CH CH H H OCH, OCH 2 2 2 3 3 3 CH 107 SO NHCH CH CH H H CH 3 OCH 2 2 2 3 3 CH 108 SO NHCH CH CH H H Cl OCH 2 2 2 3 3, CH 109 SO,NHCH,CH,CH, H H OCH, OCH, N 2 2 2 3 3 3 Compounds 1[continued) Compound *2 R ϋ X Y Z 110 S ° 2 P" 2 H H 0CH 3 0CH 3 CH 111 SO 2 NICH 2 ) 4 H H CH 3 CH 3 CH 112 CO CH cyclopropyl H H 0CH 3 0CH 3 CH 113 CO CH cyclopropyl H H Cl 0CH 3 CH 114 CO CH cyclopropyl H H CH 3 CH 3 CH 115 CO CH cyclopropyl H H OCH 3 0CH 3 N 116 CO,CH, H CH 3 OCH 3 0CH 3 CH 2 3 117 CO,CH, H OCH 3 CH 3 OCH 3 CH 2 3 118 CO,CH, H 0CH 3 Cl OCH 3 CH 2 3 119 CO,CH, H OCH 3 CH 3 CH 3 CH 2 3 120 CO,CH, H 0CH 3 0CH 3 OCH 3 N 2 3 121 C0,CH, H OCH 3 CH 3 OCH 3 N 2 3 Test A Seeds of large crabgrass (Digitaria sanguinalis), bamyardgrass (Echinochloa crus-galli), giant foxtail (Sβtaria faberi), wild oats (Avena fatua), cheatgrass (Broπtus secalinus), velvetleaf (Abutilon theophrasti) , cultivated morningglory (Ipomoea coeeinea. variety Scarlet O'Hara), cocklebur (Xanthium pensylvanicum), G522 sorghum (Sorghum vulgare. variety Funk ' G522), G4646 corn (Zea mays, variety Funk G4646), Williams soybeans (Glycine max. variety Williams), USH11 sugarbeet (Beta vulgaris. variety Union Sugarbeet Co. USH11), Cόker cotton (Gossypium hirsu um. variety Coker 315), dry seeded rice (Oryjza sativa. variety California Rice Coop. H101), Era wheat (Triticum aestivum. variety Era spring), lages barley (Hordeum vulgare. variety Klages spring) and purple nutsedg (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis; B = burn; D = defoliation; E = emergence inhibition; G = growth retardation; H = formative effect; U = unusual pigmentation; X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers. "P0S0L" and "PRSO " in Table A denote post- and preemergence treatments, respectively. TABLE A CMPD CMPD RATE=KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 9C 4C, 9H 0 0 CULT MORNINGLRY 10C 10C IH 0 COCKLEBUR 10C 9C IH 0 PURPLE NUTSEDGE 9C 4C,9G 0 0 LARGE CRABGRASS 2C, 8G 5G 0 0 BARNYARDGRASS 9C 9C 2H 0 WILD OATS 4C, 9G 9G 0 0 ERA WHEAT 9C 4C, 9G 2G 0 G4646 CORN 2H 0 0 0 WILLMS SOYBEANS 4C, 9H 2C,4G 0 0 RICE DRY SEEDED 6C, 9G 9C 0 0 G522 SORGHUM 9C 9C 3G 0 CHEAT GRASS 10C 9C 2G 0 USH11 SUGARBEET 9C 9C 0 0 VELVETLEAF 10C 5C, 9G 0 0 GIANT FOXTAIL 9C 6C, 9G 2G 0 KLAGES BARLEY 5C, 9G 2C, 8G 0 0 CMPD 3 CMP 'D . _ RATE=KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 2G 0 0 0 CULT MORNINGLRY 9C 4C.8G IH 0 COCKLEBUR 5C,9G 3C,8G 2H, 5G 0 PURPLE NUTSEDGE 3C,8G 2C 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 3C,8H 3C,7H IH 0 WILD OATS 3C,8G 0 0 0 ERA WHEAT 6G 0 2G 0 G4646 CORN 0 0 0 0. WILLMS SOYBEANS 1C 0 0 0 RICE DRY SEEDED 9C 5G 2G 0 G522 SORGHUM 9C 9C 2C, , 5G 2C, 2G CHEAT GRASS 5C,9G 7G 0 0 USH11 SUGARBEET 9C 3C, 7H 0 0 VELVETLEAF 7G 0 0 0 GIANT FOXTAIL 2C,4G 2G 0 0 KLAGES BARLEY 2C.6G 0 0 0 TABLE A (continued) CMPD 1 CMPD 2 RATE-KG/HA 0.05 0.01 0.05 0.01 RSOL COKER COTTON 8G 5G 0 0 CULT MORNINGLRY 9G 8H 0 0 COCKLEBUR 9H 9H 0 0 PURPLE NUTSEDGE 10E 3C, 7G 0 0 LARGE CRABGRASS 9G - 9G 0 BARNYARDGRASS 9H 9H 0 0 WILD OATS 4C.8G 1C 0 0 ERA WHEAT 10E 8G 0 0 G4646 CORN 5G 0 0 0 WILLMS SOYBEANS 3G 0 0 0 RICE DRY SEEDED 10E 4C, 9H 0 0 G522 SORGHUM 1ΘE 10H 0 0 CHEAT GRASS 9H 8G - 0 0 USH11 SUGARBEET 9G 6G 6G 0 VELVETLEAF 8H 3H 0 0 GIANT FOXTAIL 9H 3C, 8G 0 0 KLAGES BARLEY 8G 7G 0 0 CMP D CMPD RΛTE*KG/HΛ 0.05 0.01 0.05 0. PRSOL COKER COTTON 2G 0 2G 0 CULT MORNINGLRY 5H IH 1C 0 COCKLEBUR 3G 1C 0 0 PURPLE NUTSEDGE 9G 8G 0 0 LARGE CRABGRASS 9G 5G 8G - BARNYARDGRASS 3C, 7G 2G 2G 0 WILD OATS 0 4G 2G 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 2G 2G 0 WILLMS SOYBEANS 3G 0 5G 0 RICE DRY SEEDED 3C, 8G 6G 2C.5G 0 G522 SORGHUM 2C, 9G 3C,8G 2C 0 CHEAT GRASS 7G 2G 5G 0 USH11 SUGARBEET 7G 4H 8G 4G VELVETLEAF 2G 0 0 0 GIANT FOXTAIL 2C 0 2G 0 KLAGES BARLEY 6G 0 0 0 TABLE A ( cont inued ; CMPD CMPD RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 2G 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 2G 0 0 0 0 0 BARNYARDGRASS 4C.8H 0 WILD OATS 9G 0 0 0 ERA WHEAT 9G 0 0 0 G4646 CORN 3C,9G 0 0 0 0 WILLMS SOYBEANS 0 0 0 RICE DRY SEEDED 8G 0 0 0 G522 SORGHUM 3C,8H 0 0 0 CHEAT GRASS 3C,8G 0 0 0 USH11 SUGARBEET 3C,7G 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 2C.5G 0 0 0 KLAGES BARLEY 3C,7G 0 0 0 TABLE A CMPD 5 CMPD 6 RATE=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 - 0 0 LARGE CRABGRASS 2G - - 2G 0 0 BARNYARDGRASS 0 WILD OATS • 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USH11 SUGARBEET 0 - 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 2G 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A (continued ) CMPD CMPD RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 4C.9H 2C,5G CULT MORNINGLRY 0 0 10C 4C,9G COCKLEBUR 0 0 10C 10C PURPLE NUTSEDGE 0 0 6C,9G 2C,9G LARGE CRABGRASS 0 0 2G 0 BARNYARDGRASS 0 0 9C 4C,9H WILD OATS 0 0 9G 9G ERA WHEAT 0 0 2C.9G 9G G4646 CORN 0 0 4C.9G 3C,7H WILLMS SOYBEANS 0 0 4C.9G 2C.7H RICE DRY SEEDED 0 0 9C 9C G522 SORGHUM 0 0 9C 9C CHEAT GRASS 0 0 9C 4C,8G USH11 SUGARBEET 0 .0 10C 9C VELVETLEAF 0 0 10C 4C.9H GIANT FOXTAIL 0 0 4C,9G 4C,8G KLAGES BARLEY - 0 0 9G 7G CMPD CMPD RATE=KG/HA 0. i 05 0.01 0.05 O.ftl PRSOL COKER COTTON 0 0 4G 3G CULT MORNINGLRY 0 0 9G 8H COCKLEBUR 0 0 8H 3C. 5H PURPLE NUTSEDGE 10E 0 9G 3C, 9G LARGE CRABGRASS — 6G 2C BARNYARDGRASS 0 0 9H 3C, 8H WILD OATS 0 0 3C, 8H 6G„ ERA WHEAT 0 0 8H 6G G4646 CORN 0 0 3C, 7H 0 WILLMS SOYBEANS 0 0 3G 5G RICE DRY SEEDED 0 0 10E 3C, ,9H G522 SORGHUM 0 0 5C, 9H 3C, ,9H CHEAT GRASS 0 0 9H 9G USH11 SUGARBEET 0 0 4C, 9G 3C, , 8G VELVETLEAF 0 0 8H 2C, , 2G GIANT FOXTAIL 0 0 9H 7G KLAGES BARLEY 0 0 2C, ,9G 6G TABLE A ( continued ) CMPD 9 CMPD 10 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C.9G 9H 3C.5H 2C.3G CULT MORNINGLRY 9C 5C,9G 4C,9H 3C,5H COCKLEBUR IOC 9C 4C,9H 3C.7H PURPLE NUTSEDGE 4C,8G 2C, 5G 2C.4G 0 LARGE CRABGRASS 3G 0 0 0 BARNYARDGRASS 3C,9H 3C,7H 3C.6H 5H WILD OATS 3C.9G 8G 2C.6G 0 ERA WHEAT 9C 7G 4G 0 G4646 CORN 3C,8H IH 0 0 WILLMS SOYBEANS 4C,8H 3H 1C,1H 0 RICE DRY SEEDED 9C 5C,9G 9G 5G G522 SORGHUM 5C,9G 4C,9G 4C,9G 4C,9G CHEAT GRASS 4C,9G 3C,7G 8G 3G USH11 SUGARBEET 9C 4C,8G 3C.8H 6G VELVETLEAF 9C 4C,9H 2C.3G 0 GIANT FOXTAIL 3C.5G 2G 1C 0 KLAGES BARLEY 2C,8G 4G 0 0 TABLE A CMPD CMPD 10 RATE=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON IH 0 0 0 CULT MORNINGLRY 2C, 8H 1C 3H 0 COCKLEBUR - - 0 0 PURPLE NUTSEDGE 3G 0 0 0 LARGE CRABGRASS 0 - 0 0 BARNYARDGRASS 3C,8H 2C 3G 0 WILD- OATS 4C, 9G 4G 2C,4G , . 0 ERA WHEAT 4C,8G 0 0 0 G4646 CORN 2G 0 0 0 WILLMS SOYBEANS 3G IH 0 0 RICE DRY SEEDED 4C, 9H 3G 5G 2G G522 SORGHUM 5C, 9H 3C,8H 3C, 8H 3C 7H CHEAT GRASS 9G 5G 7G 0 USH11 SUGARBEET 4C, 9G 8H 3C, 3H 0 VELVETLEAF 2C, 3H 1C 0 0 GIANT FOXTAIL 2C, 3G 0 0 0 KLAGES BARLEY - 4C, 9G 0 0 0 TABLE A ( continued) CMPD 11 CMPD 12 RATE-KG/HΛ 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C.8H 2G 0 0 CULT MORNINGLRY 3C.7H 2C,2H 0 0 COCKLEBUR 3C, 9H 2C,3H 4C,8H 2H PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 5H 3H 2H 0 WILD OATS 2C,8G 5G 2G 0 ERA WHEAT 7G 5G 3G 0 G4646 CORN 0 0 5H 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 3C.5G 2C.5G 2G 0 G522 SORGHUM 9C 3C,7H 2C,5G 0 CHEAT GRASS 5G 3G 3G 0 USHll SUGARBEET 4C.8G 3C,3H 2H 0 VELVETLEAF 3C,7H 2C 5G 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 3G 0 2G 0 CMPD 11 CMPD 12 RATE=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 2G 0 5G 0 CULT MORNINGLRY IH 0 0 0 COCKLEBUR 4H 0 IH 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 θ 0 BARNYARDGRASS 2G 0 0 0 WILD OATS 7G 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 2G 0 2G 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 2G 0 0 0 G522 SORGHUM 3C r 5G 4G 0 0 CHEAT GRASS 4G 0 0 0 USHll SUGARBEET 5H 0 3H 0 VELVETLEAF IH 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY • 2G 0 0 0 TABLE A (continued) CMPD 13 CMPD 14 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL : COKER COTTON 0 0. 0 0 CULT MORNINGLRY ic, ,3G 0 0 0 COCKLEBUR 3C ( ,9G 3H 2C.5G 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 5H 0 7H 0 WILD OATS 0 0 7G 0 ERA WHEAT 6G 0 8G 2G G4646 CORN 3H 0 6H 0 WILLMS SOYBEANS 0 0 0 0 RICE- DRY SEEDED 2G 0 2C.5G 0 G522 SORGHUM 8G 0 3C,8H 0 CHEAT GRASS 7G 0 2C,8G 0 USHll SUGARBEET 3H 0 3H 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 2G 0 KLAGES BARLEY 0 0 2C,8G 4G TABLE A CMPD 13 CMPD 14 RATE=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT TOXTAIL 0 0 0 0 KLAGES BARLEY. 0 0 0 0 TABLE A (continued) CMPD 15 CMPD 16 RATE*KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 10C 3C,9H 3C,9H 3C, 8H CULT MORNINGLRY 10C 10C 6C.9G 6C.9H COCKLEBUR 10C 10C 9C 4C, 9H PURPLE NUTSEDGE 4C.9G 9G 9G 6G LARGE CRABGRASS 9G 2C,5G 7G 2G BARNYARDGRASS 10C IOC 9C 3C, 9H WILD OATS 3C,9G 3C,9G 4C.9G 3C, 8G ERA WHEAT 4C,9G 8& 9G 9G G4646 CO N 3C,8H 2G 3G 2G WILLMS SOYBEANS 9C 3C.8G 5C.9G 4C f 9G RICE DRY SEEDED 9C 9C 9C 9C G522 SORGHUM 10C 9C 3C,9G 3C,9G CHEAT GRASS 10C 9C IOC 4C,9G USHll SUGARBEET 9C 9C 9C 4C r 9H VELVETLEAF 10C 5C r 9H IOC 5C,9H GIANT FOXTAIL 10C 9C 9C 3C.9G KLAGES BARLEY 9C 3C, 8G 2C,8G 6G CMPD 15 CMPD 16 RATE=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 3C, 9G 8G 5G 0 CULT MORNINGLRY 9G 2C, 9H 3C, 7H 0 COCKLEBUR 8H 2H 1C, 2G 0 PURPLE NUTSEDGE 10E 9C 3G 0 LARGE CRABGRASS 9H 2G 2G 0 BARNYARDGRASS 9H 4C,8H 3G 0 WILD OATS 3C, 7G 6G 2C, 6G 6G. ERA WHEAT 3C, 9H 6G 7G 4G G4646 CORN 4G 4G 3G 0 WILLMS SOYBEANS 8H 3C, ,6H 3C, ,7H 0 RICE DRY SEEDED 10H 10H 10R ' 2C.4G G522 SORGHUM 10H 4C,9H 9H 4C, 9H CHEAT GRASS 9H 3C.9G 3C, ,8H 2C.7H USHll SUGARBEET 3C, 9 9GG 3C.9G 3C, ,8H 2C, 3G VELVETLEAF 3C, ,88GG 3C, 6H 2C, .5G 0 GIANT FOXTAIL 5C.9H 2C r 8H 2C 0 KLAGES BARLEY 3C.8G 7G 2C, ,7G 2G TABLE A (continued) CMPD 17 CMPD 18 RATE*KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 4C.8H 0 3C r 8H 2C CULT MORNINGLRY 5C r 9G 2C, ,7H 4C.8H 3G COCKLEBUR 4C,8H H 3C.8H 3C,5G PURPLE NUTSEDGE 3C,5G 0 2G 2G LARGE CRABGRASS 0 0 2G 0 BARNYARDGRASS 5C,9H 3C, ,7H 3C.8H 3C,6H WILD OATS 9G 4G 2C,9G 9G ERA WHEAT 7G 3G 9G 8G G4646 CORN 0 0 IH 0 WILLMS SOYBEANS 3C.6H 2G 3C, 8G 3C,3H RICE DRY SEEDED 5C.9G 2G 5C, 9G 5C,9G G522 SORGHUM 5C.9G 4C, 9G 3C.9G 4C,9G CHEAT GRASS 9G 9G - 9C 9G USHll SUGARBEET 4C,8H 3C, 6G 3C, 7H 3C,5G VELVETLEAF 4C,8H 5G 3C,7G 3C,6G GIANT FOXTAIL 9C 3C, 7G 3C,9G 3C,6G KLAGES BARLEY 4G 0 2C,8G 6G TABLE A CMPD 17 CMPD 18 RATE*KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2C,3H 0 0 0 COCKLEBUR 0 0 - 0 PURPLE NUTSEDGE 8G 0 8G 0 LARGE CRABGRASS 3G 0 0 0 BARNYARDGRASS 7G 0 2C 0 WILD OATS 4G 0 7G 2G ERA WHEAT 2G 0 6G 2G G4646 CORN 0 2G 0 0 WILLMS SOYBEANS 2C, 2H 0 0 0 RICE DRY SEEDED 9H 2G 8H 2G G522 SORGHUM 9H 3C, 8H 4C, 9H 2C 7G CHEAT GRASS 7G 0 7G 2G USHll SUGARBEET 8G 5H 5H 0 VELVETLEAF 3G 0 0 0 GIANT FOXTAIL 2G 0 0 0 KLAGES BARLEY 5G 0 3G 1C TABLE A ( continued ) CMPD 19 CMPD 20 RATE»KG/HA 0.05 0.01 0.05 - 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 θ θ 0 COCKLEBUR 2H 0 2H 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 2G 0 WILD OATS 2G 0 0 0 ERA WHEAT 5G 0 3G 0 G4 46 CORN 0 0 0 0 WILLMS SOYBEANS 2C, 2H 0 3C 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 3C, 3G 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 1C 0 2H 0 VELVETLEAF 3G 0 0 0 GIANT FOXTAIL 2G θ 0 0 KLAGES BARLEY 2G 0 0 0 CMPD 19 CMPD 20 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 - 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 - BARNYARDGRASS 2G 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 2G 0 0 0 WILLMS SOYBEANS 2G 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 2G 0 0 0 USHll SUGARBEET 2H 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES .BARLEY 0 0 0 0 TABLE A (continued) CMPD 2 1 CMPD 22 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON IOC 9C 2C.5G 0 CULT MORNINGLRY IOC IOC 2C.7G 0 COCKLEBUR IOC IOC 5G 0 PURPLE NUTSEDGE IOC 9G 0 0 LARGE CRABGRASS 5C, ,9G 8G 3G 0 BARNYARDGRASS 9C 9C 2C,5H 2G WILD OATS 3C, 9G 3C, 9G 0 0 ERA WHEAT 5C. 9G IOC 0 0 G4646 CORN 1C. 4H 2G 0 0 WILLMS SOYBEANS 9C 5C, 9G 3C, 4H 1C,1H RICE DRY SEEDED 9C 9C 3G 0 G522 SORGHUM 9C 9C 3C,8G 3G CHEAT GRASS 9C 9C 5G 0 USHll. SUGARBEET IOC IOC 2C.5G 2G VELVETLEAF IOC IOC 2G 0 GIANT FOXTAIL IOC IOC 6G 0 KLAGES BARLEY 5C, 9G 4C, 9G 0 0 TABLE A CMPD 21 CMPD 22 RATE*KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 9G 8G 0 0 CULT MORNINGLRY 9G 8G 2G 0 COCKLEBUR 9H 8G 0 0 PURPLE NUTSEDGE 10E 5G 0 0 LARGE CRABGRASS 9H 0 0 0 BARNYARDGRASS 9H 9H 0 0 WILD OATS 3C,7H 6G 0 0 ERA WHEAT 5C, 9H 8H 0 0 G4646 CORN 1C,4G 2G 0 0 WILLMS SOYBEANS 9H 3C 6H 0 0 RICE DRY SEEDED 10E 10H 0 0 G522 SORGHUM 10E 9H 3G 0 CHEAT GRASS 9H 9H 0 0 USHll SUGARBEET 9G 9G 3G VELVETLEAF 7H 2G 2G 0 GΣANT FOXTAIL 9H 9H 0 0 KLAGES BARLEY 9G 8G 0 0 TABLE A ( continued) CMPD 23 CMPD 24 RATE-KG/HA 0.05 0.01 0.05 0.01 OSOL COKER COTTON IOC 2C,6G 2G 0 CULT MORNINGLRY IOC 4C,9G 2C f 5H 0 COCKLEBUR IOC 7H 4G 0 PURPLE NUTSEDGE 3C,8G 7G 0 0 LARGE CRABGRASS 7G 2G 2G 0 BARNYARDGRASS 9C 5C,9H 2C.5G 0 WILD OATS 8G 6G 2G 0 ERA WHEAT 8G 4G 6G 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 3C,8H 3C,4G 3C.5H IK RICE DRY SEEDED 9C 5C.9G 3G 0 G522 SORGHUM 9C 9C 3C.7G 2G CHEAT GRASS 5C.9G 9G 3G 0 USHll SUGARBEET 9C 5C.9G 3G 2G VELVETLEAF 9C 8G 3C.7G 3H GIANT FOXTAIL 1ΘC 4C.9G 2C.7G 5G KLAGES BARLEY 3C,9G 3G 0 0 CMPD 23 CMPD 24 RATE*KG/HA 0.05 0.01 0.05 0.01 PRSOL % s COKER COTTON 6G 3G 0 0 CULT MORNINGLRY 9G 2G 1C 0 COCKLEBUR 8G 0 5G 0 PURPLE NUTSEDGE ' 10E 7G 0 0 LARGE CRABGRASS 6G 0 0 0 BARNYARDGRASS 9H 3C f 8H 0 0 WILD OATS 4G 0 0 0 ERA WHEAT SG " 0 0 o" G4646 CORN 2G 0 0 0 WILLMS SOYBEANS 2G 0 0 0 RICE DRY SEEDED 10E 9H 0 0 G522 SORGHUM 10E 10H 3G 0 CHEAT GRASS 9H 7H 0 0 USHll SUGARBEET 8G 3H 0 0 VELVETLEAF 2G 0 0 0 GIANT FOXTAIL 7H 3G 0 0 KLAGES BARLEY 4C.9G 2G 0 0 TABLE A ( cont inued ; CMPD 25 CMPD 26 0.01 0.05 0.01 RATE-KG/HA 0.05 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 2C 0 0 0 0 COCKLEBUR IH PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 3G 0 0 0 0 0 0 WILD OATS 8G 0 3G 0 ERA WHEAT 9G G4646 CORN 3G 0 0 0 0 0 0 WILLMS SOYBEANS 2C.2H RICE DRY SEEDED 4G 0 0 0 G522 SORGHUM 2G 0 0 0 0 2G 0 CHEAT GRASS 8G USHll SUGARBEET 2H 0 0 0 VELVETLEAF 0 0 2G 0 GIANT FOXTAIL 0 0 2G 0 KLAGES BARLEY 7G 0 0 0 TABLE A CMPD 25 CMPD 26 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 1C,1H 0 0 0 0 0 0 COCKLEBUR PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 G4646 CORN WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 2G 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 5G 0 0 VELVETLEAF 2G 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A (continued) CMPD 27 CMPD 28 RATE-KG/HA 0.05 0.01. 0.05 0.01 POSOL COKER COTTON 5C,9G 4C,8G 3C,9G 4C.9G CULT MORNINGLRY 5C,9G 2C,7G 1ΘC ?C g 7(i COCKLEBUR 10C 2C,8G 10C 4C.9H PURPLE NUTSEDGE 0 0 2C r 9G 9G LARGE CRABGRASS 0 0 4C,9G 2C,8G BARNYARDGRASS 3C,7G 4G 9C 9C WILD OATS 3C.6G 0 6C,9G 9G ERA WHEAT 4C.9G 0 6C.9G 9G G4646 CORN 2H 0 2U,9G 9G WILLMS SOYBEANS 4C.9G 3C.8G 9C 9C RICE DRY SEEDED SG 2G 9C 9C G522 SORGHUM 4C,9G " 3C.8G 9C 5C.9G CHEAT GRASS 7G 3G 9C 9C USHll SUGARBEET 6C,9G 3C,6G 9C 9C VELVETLEAF 6C,9G 3C,7G 9C 4C r 8R GIANT FOXTAIL 4C,8G SG 9C 9C KLAGES BARLEY 2G 0 5C,9G 4C.9G CMPD 27 CMPD 28 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 8G 6G CULT MORNINGLRY 0 0 7H 7H COCKLEBUR 0 - IH - PURPLE NUTSEDGE 0 0 loε 3G LARGE CRABGRASS 0 0 2C.8G 8G BARNYARDGRASS 0 0 9H 2C.6G WILD OATS 0 0 3C.8G 3 ..7G ERA WHEAT 0 0 3C f 9G 3C, 8G G4646 CORN 0 0 2C, SG 3C.7G WILLMS SOYBEANS 0 0 3C,7H 3C.7H RICE DRY SEEDED 0 0 9H 9H G522 SORGHUM 2C 0 5C,9H 5C.9H CHEAT GRASS 0 0 2C.8G 8G USHll SUGARBEET 3H 0 4C.9G 1C VELVETLEAF 0 0 7G 3G GIANT FOXTAIL 0 0 9H 7G KLAGES BARLEY 0 0 2C.7G 8G TABLE A ( cont inued ) CMPD 29 CMPD 30 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 4C,8H 3G 0 0 CULT MORNINGLRY 4C,9G 3C,7H 3C.6G .0 COCKLEBUR 4C,9H 2C,6H 2H 0 PURPLE NUTSEDGE 2C.8G 5G 0 0 LARGE CRABGRASS 3C,7G 2C.5G 2C,4G 0 BARNYARDGRASS 9C 4C, 8H 4C.9H 3C, 6H WILD OATS 4C, 9G 2C,9G 9G 3G ERA WHEAT 4C,9G 2C,9G 7G 4G G4646 CORN 2C,9G 2C, 5H 2C,5G 0 WILLMS SOYBEANS 5C.9G 4C, 8H 3C,3H 1C RICE DRY SEEDED 9C 5C, 9G 8G 0 G522 SORGHUM 4C,9G 3C.7G 3C,8H 3C. 3H CHEAT GRASS 5C,9G 4C, 9G 3C.9G 7G USHll SUGARBEET 5 ' C, 9G 2C.4G 3C.4H 2C VELVETLEAF 4C.9H 3C, 6H 5G 0 GIANT FOXTAIL SC,9G 3C.7G 4C,9G 2C. 5G KLAGES BARLEY 4C, 9G 3C.7G 2C.5G 3G TABLE 4 \ CMPD 29 CMPD 30 RATE=KG/HA 0.05 0.01 0.1 D5 0.01 >RSOL COKER COTTON 5G 3G 0 0 CULT MORNINGLRY 3G 0 3C ,7G 2G COCKLEBUR 0 0 2C ι 3H 0 PURPLE NUTSEDGE 4G 0 0 0 LARGE CRABGRASS - - - - BARNYARDGRASS 2G 0 0 0 WILD OATS 3G 0 0 0 ERA WHEAT 2G 0 0 0 G4646 CORN 2C, 4G 0 2C 0 WILLMS SOYBEANS 3C, 3H 2G 2C, ,2H 2H RICE DRY SEEDED 3C, 6G 2C, 3G 2G 2G G522 SORGHUM 4C. 5G 2G 2C 0 CHEAT GRASS 3G 2G 0 0 USHll SUGARBEET 7G 5H 7G 2H VELVETLEAF 2G 0 4G 0 GIANT FOXTAIL 8G 0 5G 5G KLAGES BARLEY 2C. 6G 0 2C 0 TABLE A (on inued) CMPD 31 CMPD 32 RATE-KG/HA 6.65 0.01 0.05 0.01 POSOL COKER COTTON CULT MORNINGLRY COCKLEBUR PURPLE NUTSEDGE LARGE CRABGRASS BARNYARDGRASS WILD OATS ERA WHEAT G4646 CORN WILLMS SOYBEANS RICE DRY SEEDED G522 SORGHUM CHEAT GRASS USHll SUGARBEET VELVETLEAF GIANT FOXTAIL KLAGES BARLEY CMPD 31 CMPD 32 RATE=KG/HA 0.05 0.01 0.05 0_01 PRSOL COKER COTTON 2G 0 4G 0 CULT MORNINGLRY 2G 0 2G 0 COCKLEBUR 7G 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS β 0 Q 0 BARNYARDGRASS 0 0 0 0 WILD OATS 2G 0 5G 0 ERA WHEAT 4G 0 2G 0 G4646 CORN 3G 0 0 0 WILLMS SOYBEANS 4G 0 2G 0 RICE DRY SEEDED 2G 0 0 0 G522 SORGHUM 2G 0 0 0 CHEAT GRASS 0 0 2G 0 USHll SUGARBEET 2H 0 2H 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 2G 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A ( continued ) CMPD 33 CMPD : 34 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 2C, ,4H 0 9C 4C,8G CULT MORNINGLRY 2C 0 6C,9G 4C,9G COCKLEBUR 1C 0 10C 4C,9H PURPLE NUTSEDGE 0 0 3C,9G 2C,9G LARGE CRABGRASS 0 0 5C,9G 9G BARNYARDGRASS 0 0 9C 4C,9G WILD OATS 0 0 2C,9G 9G ERA WHEAT 0 0 4C.9G 2C,9G G4646 CORN 0 0 4C,9G 2C,8G WILLMS SOYBEANS 2C, 5H 0 9C 5C.9G RICE DRY SEEDED 1C 0 5C, 9G 4C.9G G522 SORGHUM 0 0 9C 6C.9G CHEAT GRASS 0 0 9C 4C,9G USHll SUGARBEET 2C 0 4C,9H 2C,6H VELVETLEAF 1C 0 10C 10C GIANT FOXTAIL 0 0 9C 9C KLAGES BARLEY 0 0 4C,9G 3C.8G TABLE A CMPD 33 CMPD 34 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 8G 8G CULT MORNINGLRY 0 0 9G 8G COCKLEBUR - 0 8H - PURPLE NUTSEDGE 0 0 10E 9G LARGE CRABGRASS 0 0 4C, ,9H 10E BARNYARDGRASS 0 0 9H 3C.8H WILD OATS 0 0 * 3C, ,8H 6G ERA WHEAT 0 0 4C, ,9H 8G G4646 CORN 0 0 9G 2C.4G WILLMS SOYBEANS 0 0 9G 3C, 6G RICE DRY SEEDED 0 0 10H 10H G522 SORGHUM 0 0 9G 9G CHEAT GRASS 0 0 9H 6G USHll SUGARBEET 5H 3G 9G 7G VELVETLEAF 3G 0 3C, 8G 2C,βG GIANT FOXTAIL 0 0 9H 9H KLAGES BARLEY 0 0 3C. 8G 8G TABLE A ( continued ) CMPD 35 CMPD 36 RATE-KG/HA 0.Θ5 0.01 COS 0.01 POSOL COKER COTTON 0 0 6G 2G CULT MORNINGLRY 3G 0 5C,9H 3C.7H COCKLEBUR 2C,4G 0 4C,9H 4C,6H PURPLE NUTSEDGE 0 0 3G 0 LARGE CRABGRASS 0 0 2C,8G 5G BARNYARDGRASS 2C.8H 0 9C 2C, 8H WILD OATS 8G 0 9G 3G ERA WHEAT 9G 0 9G 0 G4646 CORN 0 0 o- 0 WILLMS SOYBEANS 1C,5H 2C 4C,8G 2C,4H RICE DRY SEEDED 7G 0 4C.9G 2C,6G G522 SORGHUM 2G 0 3C,9G 3C,9G CHEAT GRASS 8G 4G 3C f 9G 9G USHll SUGARBEET 2G 0 4C,iH 2C,7G VεLVETLEAF 5G 0 7G 0 GIANT FOXTAIL 7G 0 4C,9G 3C,9G KLAGES BARLEY 4G 0 3C,8G 2C.7G CMPD 35 CMPD 36 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 4G _ 8G - 4G CULT MORNINGLRY 0 2C 7G 0 COCKLEBUR 0 0 2G 0 PURPLE NUTSEDGE 0 0 9G 0 LARGE CRABGRASS 0 0 10E 8G BARNYARDGRASS 0 0 9H 2G WILD OATS 0 0 0 4G ERA WHEAT 0 0 2G 3G * G4646 CORN 0 0 0 0 WILLMS SOYBEANS 2G 2C 2C, 4G 0 RICE DRY SEEDED 3G 0 10E 2C,5G G522 SORGHUM 2G 0 10E 3C r 6H CHEAT GRASS 0 0 7G 2G USHll SUGARBEET 0 — 7G 4G VELVETLEAF 0 0 1C, 3G 2C GIANT FOXTAIL 0 0 9H 4G KLAGES BARLEY 0 0 2G 0 TABLE A ( continued) CMPD 37 CMPD 38 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 2H 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A CMPD 37 CMPD 38 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 - BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 . 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 - - KLAGES BARLEY . 0 0 0 0 TABLE A (continued) CMPD 39 CMPD 40 RATE-KG/HA 0.05 0.01 8.05 0.01 POSOL COKER COTTON 0 0 4C,9G 9K CULT MORNINGLRY 0 0 10C 4C, 8H COCKLEBUR 0 0 10C 4C,9G PURPLE NUTSEDGE 0 0 9G 8G LARGE CRABGRASS 0 0 3G 0 BARNYARDGRASS 0 0 9C 3C,9H WILD OATS 0 0 3C,9G 8G ERA WHEAT 0 0 9G 8G G4646 CORN 0 0 4C„9H 2G WILLMS SOYBEANS 0 0 4C,9G 4C,9G RICE DRY SEEDED 0 0 5C,9G • 5C.9G G522 SORGHUM 0 0 4C,9G 4C, 9G CHEAT GRASS 0 0 - 9C • 6G USHll SUGARBEET 0 0 9C 9C VELVETLEAF 4G & 4C,9H 4C.7H GIANT " FOXTAIL 0 0 4C,9G 3C,7G KLAGES BARLEY 0 0 8G 7G CMPD 39 CMPD 40 RATE-KG/HA 0.05 0.01 0.05 0.01 RSOL COKER COTTON 0 0 2C,5G 2G CULT MORNINGLRY 0 0 9H 7H COCKLEBUR 0 0 8H 3H PURPLE NUTSEDGE 0 0 7G 7G LARGE CRABGRASS - - 9G 4G BARNYARDGRASS 0 0 5G 4G WILD OATS 0 0 3C.7G 3G. ERA WHEAT 0 0 8G 3G G4646 CORN 0 0 3C,3G 3G WILLMS SOYBEANS 0 0 3C,3H 2H RICE DRY SEEDED 0 0 9H 5G G522 SORGHUM 0' 0 5C,9G 3C. 7.H CHEAT GRASS 0 0 8G 5G USHll SUGARBEET - 0 3C,8G 6H VELVETLEAF 0 0 7H 1C GIANT FOXTAIL ' 0 0 9H 0 KLAGES BARLEY 0 0 2C,8G 7G TABLE A ( continued ) CMPD 41 CMPD 42 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C.9G 3C,8H 3C,5H 0 CULT MORNINGLRY 9C 3C.8H 3C,3H 0 COCKLEBUR 9C 3C,9G 3C,6H 2C.2H PURPLE NUTSEDGE 3G 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 4C.9G 4C, SH 3C, 4G 0 WILD OATS 3C, 9G 3C, 8G 5G 0 ERA WHEAT 9G 9G 2G 0 G4646 CORN 7G 0 0 0 WILLMS SOYBEANS 4C,7G 3C,3H 0 0 RICE DRY SEEDED 5C,9G 3C, 7G 3G 0 G522 SORGHUM 4C,9G 4C,9G 3C, 9G 0 CHEAT GRASS 5C.9G 4C.8G 6G 0 USHll SUGARBEET 4C, 8H 3C,7G 3C.6H 0 VELVETLEAF 3C,8H 3C, 6H 0 0 GIANT FOXTAIL 3C,7G 3G 0 0 KLAGES BARLEY 8G 5G 0 0 TABLE A CMPD 41 CMPD 42 RATE-KG/HA 0.05 0.01 0.( 35 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2C.7H 2C.5H 0 0 COCKLEBUR 2C, 4H 3G 0 0 PURPLE NUTSEDGE 0 0 4G 0 LARGE CRABGRASS 3G - 4G - BARNYARDGRASS 7G 0 0 0 WILD OATS 2C.6G 0 0 0 ERA WHEAT 2C.7G 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 2C, 2G 0 2G 0 RICE DRY SEEDED 3C,5G 0 0 0 G522 SORGHUM 3C.5G 2C 3C, ,3G 0 CHEAT GRASS 7G 0 0 0 USHll SUGARBEET 3C.5G 3G 0 0 VELVETLEAF 7G 0 0 0 GIANT FOXTAIL 9H 5G 3G 0 KLAGES BARLEY • 7G 2G 3G 0 TABLE A (continued ) CMPD 43 CMPD 44 RATE-KG/HA 0.05 0.01 0.05 0.01 OSOL COKER COTTON 2C,3G 0 0 0 CULT MORNINGLRY 3C,6G IH 0 0 COCKLEBUR 3C.6G 1C,1H 2C.2H IH PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 2G 0 0 0 BARNYARDGRASS 3C,7G IH 0 0 WILD OATS 9G 2G 0 0 EKΛ WHEAT 9G 2G 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 1C 0 0 0 RICE DRY SEEDED 4C, 9G 0 0 0 GS22 SORGHUM 4C.8H 4G 0 0 CHEAT GRASS 3C 9G 8G 0 0 USHll SUGARBEET 3C.6G 0 " 0 0 VELVETLEAF 2C,2G 0 0 0 GIANT FOXTAIL 3C r 7G 4G 0 0 KLAGES BARLEY 7G 4G 0 0 CMPD 43 CMPD 44 RATE-KG/HA 0 . 05 0 . 01 0 . 05 0 . 01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAΓ 0 0 0 0 GIANT FOXTAIL - 2G 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A ( cont inued ) CMPD 45 CMPD 46 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 3C,8G 3C,7H CULT MORNINGLRY 0 0 10C 9C COCKLEBUR 2C,2H 0 3C, 9H 2C,8G PURPLE NUTSEDGE 0 0 9G 2C,9G LARGE CRABGRASS 0 0 6G 4G BARNYARDGRASS 0 0 9C 9C WILD OATS 0 0 SG 2G ERA WHEAT 0 0 8G 8G G4646 CORN 0 0 3G 0 WILLMS SOYBEANS 0 0 4C.9G 3C,7H RICE DRY SEEDED o - 0 9C 4C.9G G522 SORGHUM 0 0 4C.9G 4C.9G CHEAT GRASS 0 0 5C, 8G 5G USHll SUGARBEET 0 0 6C, 8G 3C.7G VELVETLEAF 0 0 " 4C,9H 2C.7H GIANT FOXTAIL 0 0 4C,9G 2C,8G KLAGES BARLEY 0 0 9C 7G TABLE A CMPD 45 CMPD 46 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 3C, 5H 2C,4G CULT MORNINGLRY 0 0 9H 1C COCKLEBUR 0 0 9H 0 PURPLE NUTSEDGE 0 0 10E 10E LARGE CRABGRASS 0 0 9H 0 BARNYARDGRASS 0 0 2C, 9H 3C,7H WILD OATS 0 0 2C,4G 4G ERA WHEAT 0 0 9H 7G G4646 CORN 0 0 5G 0 WILLMS SOYBEANS 0 0 3C, 9H 1C,2H RICE DRY SEEDED 0 0 9H 4C.8H G522 SORGHUM 0 0 9H 3C.9H CHEAT GRASS 0 0 9H 7G USHll SUGARBEET 0 0 4C, 8G 3H VELVETLEAF 0 0 3C, 8G 1C.4H GIANT FOXTAIL 0 0 3C.9H 8G KLAGES BARLEY .0 0 2C, 9H 2C, 9H TABLE A (cont inued ) CMPD 47 CMPD 48 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2G 0 3C,8H 3C 6H COCKLEBUR 0 6 3C, 8H 2C PURPLE NUTSEDGE 0 θ 5G 3G LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 2G 0 7H 4H WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 2C,7G 2G G522 SORGHUM 4G 0 3C,9G 3C 7H CHEAT GRASS 4G 0 5G 3G USHll SUGARBEET 3H 0 2C,4G IH VELVETLEAF 0 0 - 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 2G 0 4G 0 CMPD 47 CMPD 48 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 1C 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 IH - PURPLE NUTSEDGE 4G 0 0 - LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0. ERA WHEAT 0 0 0 0 G4646 CORN 0 0 2G 0 WILLMS SOYBEANS 0 0 2G 0 RICE DRY SEEDED 0 0 3C, 9H 2C,3G G522 SORGHUM 0 0 2C, 8H 2C.4G CHEAT GRASS 0 0 2G 0 USHll SUGARBEET 4H 0 2C. 4H 2H VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 3G 0 KLAGES BARLEY 0 0 5G 0 TABLE A ( cont i nued ) CMPD 49 CMPD 50 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2H 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 - LARGE CRABGRASS 2G 0 0 0 BARNYARDGRASS 2G 0 2G 0 WILD OATS 0 0 4G 0 ERA WHEAT 0 0 7G 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 2C 0 G522 SORGHUM 0 0 3G 0 CHEAT GRASS 0 0 4G 0 USHll SUGARBEET 0 0 IH 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 2C,7G 0 0 0 KLAGES BARLEY 0 0 5G 0 TABLE A CMPD 49 CMPD 50 RATE-KG/HA 0 . 0 5 0 . 0 1 0 . 0 5 0 . 0 1 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 - 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAΓ 0 0 0 0 GIANT FOXTAIL 0 0 3G 0 KLAGES BARLEY 0 0 0 0 TABLE A ( continued) CMPD 51 CMPD 52 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 2G 0 3C, 5H 3G CULT MORNINGLRY 2C f 7H 0 2C.6H 2C, 2H COCKLEBUR 2C; 6H 0 1C,4G 0 PURPLE NUTSEDGE 0 = 0 0 LARGE CRABGRASS 3G 0 2G 0 BARNYARDGRASS 4G 0 4G 2G WILD OATS 2G 0 0 0 ERA WHEAT 4G 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 1C 0 2C, 2G 0 G522 SORGHUM 3G 0 4H 0 CHEAT GRASS 2G 0 2G 0 USHll SUGARBEET 0 0 2C, 5G 0 VELVETLEAF 2G 0 6G 5G GIANT FOXTAIL 3G 0 5G 2G KLAGES BARLEY 3G 0 0 0 CMPD 51 CMPD 52 RATE-KG/HA 0.05 0.01 0.05 0.01 RSOL COKER COTTON 0 - 2G 0 CULT MORNINGLRY IH 0 IH IH COCKLEBUR 0 0 - 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 2H 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 . 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 2G 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 IH 0 VELVETLEAF 0 0 IH 0 GIANT FOXTAIL 0 0 2G 0 KLAGES BARLEY 0 0 0 0 TABLE A ( cont inued ) CMPD 53 CMPD 54 RATE-KG/HA 0.05 0.01 0.05 0. POSOL COKER COTTON 5G 0 0 0 CULT MORNINGLRY 3C,7G 3C,5H 0 0 COCKLEBUR 3C,5G 3G 0 0 PURPLE NUTSEDGE 3C,8G - 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 3C, 8H 4H 0 0 WILD OATS 2C.9G 0 0 0 ERA WHEAT 7G 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 9G 5G . 0 0 G522 SORGHUM 3C.9H 7G 0 0 CHEAT GRASS 9G 0 0 0 USHll SUGARBEET 3C,7G 4H 0 0 VELVETLEAF 2C,5G 0 0 0 GIANT FOXTAIL 2C f 5G 3G 0 0 KLAGES BARLEY 7G 0 0 0 TABLE A CMPD 53 CMPD 54 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 4H 0 0 0 COCKLEBUR 2H 0 4G 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 4G 0 0 0 WILD OATS 6G 0 0 0 ERA WHEAT 5G 0 0 0 G4646 CORN 2G 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 6G 0 0 0 G522 SORGHUM 2C.6G 0 0 0 CHEAT GRASS 7G 0 0 0 USHll SUGARBEET 6G 0 0 0 VELVETLEAF 0 0 2G 0 GIANT FOXTAIL 3G 0 0 0 KLAGES BARLEY 8G 0 0 0 TABLE A (continued ) CMPD 55 CMPD 56 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY H 0 0 0 COCKLEBUR I H 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 2 H 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 CMPD 55 CMPD 56 RATE-KG/HA 0 . 0 S 0 , 01 0 . 05 0 . 01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 — 0 0 COCKLEBUR 0 0 3 G 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 Q RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAΓ 0 0 3 G 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A ( cont i nued ) CMPD 57 CMPD 58 RATE-KG/HA 0.05 0.01 0.05 0. POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 .0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 , 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A CMPD 57 CMPD 58 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 - LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A ( cont inued ) CMPD 59 CMPD 60 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 9C 3C,9G CULT MORNINGLRY 0 0 10C 3C,9G COCKLEBUR 0 0 10C 9C PURPLE NUTSEDGE 0 4C,9G 8G LARGE CRABGRASS 0 0 4C.7G 2G BARNYARDGRASS 0 0 10C 9C WILD OATS 0 0 5C,9G 7G ERA WHEAT 0 0 9C 9G G4646 CORN 0 0 3C,7H 0 WILLMS SOYBEANS 0 0 5C.9G 5C.9G RICE DRY SEEDED 0 0 9C 9C G522 SORGHUM 0 0 9C 5C.9G CHEAT GRASS 0 0 9C 4C,9G USHll SUGARBEET 0 0 10C 4C, 8G VELVETLEAF 0 0 10C 10C GIANT FOXTAIL 0 0 4C,9G 7G KLAGES BARLEY 0 0 5C.9G 6G CMPD 59 CMPD 60 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 9G 2G CULT MORNINGLRY 0 0 9G 5G COCKLEBUR 0 0 9H 3C,6G PURPLE NUTSEDGE 0 - 10E 0 LARGE CRABGRASS 0 0 3C, 7G 0 BARNYARDGRASS 0 0 9H 3C f 6G WILD OATS 0 0 2C, 8G 3C„7G ERA WHEAT 0 0 9H * 2C,9H G4646 CORN 0 0 2C f 4G 0 WILLMS SOYBEANS 0 0 9H 3C.6G RICE DRY SEEDED 0 0 10E 8H G522 SORGHUM 0 0 10H 3C.8H CHEAT GRASS 0 0 9G 6G USHll SUGARBEET 0 0 9G 8G VELVETLεAF 0 0 4C, 8G 0 GIANT FOXTAIL 0 0 3C, 7G 3G KLAGES BARLEY 0 0 9G 8G TABLE A ( cont inued ) CMPD 61 CMPD 62 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 4G 2G 2G 0 CULT MORNINGLRY IH 0 0 0 COCKLEBUR 2H 0 0 0 PURPLE NUTSEDGE 3G 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 1C, 4H 0 0 0 WILLMS SOYBEANS 2C.8G 0 3H 0 RICE DRY SEEDED 4G 0 2G 0 G522 SORGHUM 2G 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 5C,9G 3C,7G 3C.7H 0 VELVETLεAF 3C.7G 3G 3G 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A CMPD 61 CMPD 62 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY IH 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 . 0 0 0 G4646 CORN 2C,2G 0 0 0 WILLMS SOYBEANS 2C, 2H 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 4G 0 0 0 VELVETLEAF 3H 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 , . TABLE A (continued) CMPD 63 CMPD 64 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C,8H 3C,6G 5C,9G 9C CULT MORNINGLRY 3C,7G 3C,3B 10C IOC COCKLEBUR _SC,7G 2 ( 2ιi IOC 10C PURPLE NUTSEDGE 2<S - §C.9G SC,9G LARGE CRABGRASS 6 0 €Q 4G BARNYARDGRASS 3G 0 9C 3C.9H WILD OATS 0 0 8G 2C.3G ERA WHEAT 0 0 7G SG G4646 CORN 0 0 3C,6G 3G WILLMS SOYBEANS 3C,7G 2C.3H 5C,9G 9C RICE DRY SEEDED 6G 0 9C 5C,9G G522 SORGHUM 7G 0 3C,9G 4C, 9G CHEAT GRASS 0 0 3C.8G 4C,9G USHll SUGARBEET 3C,8H 3C,8G 9G 3C,SG VELVETLEAF 3C 7G 3G 9C 5C.9G GIANT FOXTAIL 0 0 7G 3G KLAGES BARLEY 0 0 3C . 7G 2C, 6G CMPD 63 CMPD 64 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 9G 8G CULT MORNINGLRY 0 0 9G 9G COCKLEBUR 0 — 9H 9H PURPLE NUTSEDGE 4G — 10E 5G LARGE CRABGRASS 0 ό 3C, 8G 3G BARNYARDGRASS 0 0 9H 3C,66 WILD OATS 0 0 3C„ 7G 2C te 4G ERA WHEAT 0 0 3C„ 7G θ G4646 CORN 0 0 3C f 9H 2C.4G WILLMS SOYBEANS 0 0 9H 3C,8H RICE DRY SEEDED 2G 0 10E 9H G522 SORGHUM 0 0 9H 3C r 8G CHEAT GRASS 0 0 8G 2G USHll SUGARBEET 2H 0 9G - 9G VELVETLEAF 4G IH 4C, ,9G 3C.6G GIANT FOXTAIL 0 0 6G 0 KLAGES BARLEY 0 0 9G 4G TABLE A 2 (1c5ontinued ) CMPD 6 5 CMPD 66 RATE-KG/HA 0.05 0.01 0.05 0.01 >OSOL COKER COTTON 9C 9C 9C 4C,8G CULT MORNINGLRY IOC 10C IOC IOC COCKLEBUR 9C 10C IOC IOC PURPLE NUTSEDGE 9C 5C,9G 5C,9G 3C,7G LARGE CRABGRASS 6C, ,9G 4C,9G 9C 3C,8G BARNYARDGRASS 9C 9C 9C 9C WILD OATS IOC 9C 9C 5C.9G ERA WHEAT 6C, 9G 6C, 9G 9C 9G G4646 CORN 7U, 9C 7U, 9C 6U,9G 3U,9G WILLMS SOYBEANS 9C 9C 9C 5C.9G RICE DRY SEEDED 9C 9C 9C 9C G522 SORGHUM 9C 9C 6C, 9G 4C,9G CHEAT GRASS 9C 9C 9C 9C USHll SUGARBEET 9C 9C IOC IOC VELVETLEAF 9C 9C IOC 9C GIANT FOXTAIL 9C 10C 9C 9C KLAGES BARLEY 9C 6C,9G 6C,9G 4C.9G TABLE A CMPD 65 CMPD 66 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 9G 9G 8G 2G CULT MORNINGLRY 9H 9H 9G 9G COCKLEBUR 9H 9H 9G 8G PURPLE NUTSEDGE 10E 9G 10E 4C,9G LARGE CRABGRASS 5C.9G 3C,8G 6C, 9H 3C,6G BARNYARDGRASS 9H 9H 9H 6G WILD OATS 4C, 8G 8G 3C, 7G 2C.6G ERA WHEAT 4C,9G 9G 3C, 9G 0 G4646 CORN 3C,9H 3C,9G 3C, 9G 3C,9H WILLMS SOYBEANS 9H 9H 9H 7G RICE DRY SEEDED 10E 9H 10E 9H G522 SORGHUM 10H 3C,9H 9H 5G CHEAT GRASS 9H 10E 9H 8G USHll SUGARBEET 9G 3C,9G 8G 8G VELVETLEAF 9G 9G 7G 7G GIANT FOXTAIL 9H 9H 10H 3C.9H KLAGES BARLEY 5C,9G 3C,9G 5C, 9H 3G TABLE A (continued) CMPD 67 CMPD 68 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON IOC 9C 9C 4C.9G CULT MORNINGLRY IOC 4C,9G 10C 4C, 9H COCKLEBUR IOC 9C 10C 8G PURPLE NUTSEDGE 5C,9G 3C,9G 5C.9G 3C,9G LARGE CRABGRASS 5C,9G 8G 6C,9G 4C,8G BARNYARDGRASS 9C 9C 9C 9C WILD OATS 6C,9G 9G 9C 9C ERA WHEAT 9G 5G 4C f 9G 5C„ 9G G4646 CORN 5U.9G 9H 2C,9G 3C,7G WILLMS SOYBEANS 5C,9G 5C,9G 5C,9H 9C RICE DRY SEEDED 5C r 9G 9C 9C 9C G522 SORGHUM 9C 9C 9C 6C,9G CHEAT GRASS 9C 9C 9C 6C,9G USHll SUGARBEET 9C 9C 10C 9C VELVETLEAF IOC 3C,9G 10C 4C f 9H GIANT FOXTAIL 6C,9G 8G 10C 5C f 9G KLAGES BARLEY 3C,8G 5G 6C.9G 5C, 9G CMPD 67 CMPD 68 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 8G 9G 9G 5G CULT MORNINGLRY 9G 9H 9G 7G COCKLEBUR 8G 4G 8H 4G PURPLE NUTSEDGE 10E 10E 10E 9G LARGE CRABGRASS 5C, 9H 5C, 9G 9C 3C, 8G BARNYARDGRASS 9H 9H 9H 5G WILD OATS 4C, 8G 3C f 7G 4C, 9G 3C r 6G ERA WHEAT 9H 3C. 9G 9H 3C.7G G4646 CORN 9H 3C, 9H 3C, 9G 3C, 8G WILLMS SOYBEANS 9H 3C, 8G 9H 9H RICE DRY SEEDED 10E 10E 10E 9H G522 SORGHUM 10C 4C, 9H 10E 3C, 9H CHEAT GRASS 10E 8G 10E 9H USHll SUGARBEET 9G 9G 5C, 9G 7H VELVETLEAF 4C, 8G 5G 9G 2G GIANT FOXTAIL 9H 6G 10H 3C, 8G KLAGES BARLEY 3C, 9H 3C, 9G 5C, 9G 4C.9G SUBSTITUTE SHEET TABLE A ( cont inued ) CMPD 69 CMPD 70 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C.5G 3C,4G 9C 9C CULT MORNINGLRY 3C.6G 3G 10C IOC COCKLEBUR 3G 2G 10C IOC PURPLE NUTSEDGE 5G 0 10C 9C LARGE CRABGRASS 6G 4G 5C, 9G 4G BARNYARDGRASS 9C 2C,2H 9C 9C WILD OATS 5C.9G 1C 5C, 9G 9G ERA WHEAT 5C.9G 8G 9G 7G G4646 CORN 4U,9G 9G 9C 9C WILLMS SOYBEANS 4C,8H 2C, 5G 9C 9C RICE DRY SEEDED 9C 5C.9G 9C 9C G522 SORGHUM 3C.7G 3C.3G 9C 9C CHEAT GRASS 5C,9G 9G IOC 5C, 9G USHll SUGARBEET 3C,5G 5H 9C 9C VELVETLEAF 2H 3G IOC IOC GIANT FOXTAIL 3C,9G 2G IOC 9C KLAGES BARLEY 5C,9G 3C,6G 3C, 9G 6G TABLE A CMPD 69 CMPD 70 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 7G 2G 9G 8G CULT MORNINGLRY 6G 4G 9G 7G COCKLEBUR 2H 4G 9H 3C,6H PURPLE NUTSEDGE 0 0 10E 9G LARGE CRABGRASS 3C, ,7G 0 4C.8G 5G BARNYARDGRASS 5G 0 9H 8H WJ.LD OATS 2C, ,6G 6G 3C.7G SG ERA WHEAT 8G 6G 8H 4G G4646 CORN 3C, ,8G 5G 9H 9G WILLMS SOYBEANS 8G 7G 9H 3C.7H RICE DRY SEEDED 8G 4G 10E 8G G522 SORGHUM 6G 3G 9H 2C,9G CHEAT GRASS 8G 3G 4C.9G 5G USHll SUGARBEET 3H 4G 4C.9G 9G VELVETLEAF 2G 0 5C.9G 5C.9G GIANT FOXTAIL 9H 3G 9K 3C.7G KLAGES BARLEY 3C, 9G 2G 9G 2C.4G TABLE A ( continued ) CMPD 71 CMPD 72 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 9C 9C 9C 9C CULT MORNINGLRY 9C IΘC IΘC IΘC COCKLEBUR IOC IOC IOC IOC PURPLE NUTSEDGE 9C 9G - 3C,9G LARGE CRABGRASS 8G 5G 2C, 7G - BARNYARDGRASS 9C 9C 9C 9C WILD OATS 4C. 9G 9G 9G 8G ERA WHEAT 9G 8G 9G 5G G4646 CORN 3C, 9G 3C,8H 3C, 9H 2C.7G WILLMS SOYBEANS 9C 9C 9C 3C, 8H RICε DRY SEEDED 9C 3C,8G 9C 8G G522 SORGHUM 9C 9G 9C 9C CHEAT GRASS 9C 4C,9G 9C 9G USHll SUGARBEET IOC 9C- IOC 9C VELVETLEAF 9C 9C 9C 8G GIANT FOXTAIL 9C 3C,8G 4C t 9G 2C.7G KLAGES BARLEY 4C f 9G 7G 2C, 9G 4G CMPD 71 CMPD 72 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 2C,9G 3G 2C,7H 2C, 6G CULT MORNINGLRY 9G 4G 2C.9G 9H COCKLEBUR 8H 3C,6H 3C,9H 3H PURPLE NUTSEDGε 10E 0 10E 10E LARGE CRABGRASS 2C.8G 4G 2C.7G 2G BARNYARDGRASS 9H 9H 9H 8H WILD OATS 4C, 8G 2G 3C.8G 2G ^ ERA WHEAT 9H 0 8G 3G G4646 CORN 2C,9H 2C.4G 9G 3C. ,7H WILLMS SOYBEANS 9H 3C.7H 3C.8H 3C, 5G RICE DRY SEEDED 10E 2C.5G 10E 9H G522 SORGHUM 9H 9H 4C, 9H 3C, ,9H CHEAT GRASS 9H 2C,7G 9H 7G USHll SUGARBEET 3C,9G 3C.9G 4C,9G 3C. ,8H VELV8TL8AF 3C,6G 2G 3C r 7H 3G GIANT FOXTAIL 9H 2C,7G 3C, 8H 3G KLAGES BARLEY 3C,7G 2C.4G 2C.9G 2G TABLE A ( cont inued ) CMPD 73 CMPD 74 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKεR COTTON 5C,9G 3C,8G 2C.5G 1C CULT MORNINGLRY 10C 9C 3C,8H 2C,3H COCKLEBUR 10C 10C 3C,5H IH PURPLE NUTSEDGE 4C,9G 4C, 8G 5G 0 LARGE CRABGRASS 5C,9G 3C, 7G 7G 2G BARNYARDGRASS 10C 9C 9C 3C,7H WILD OATS 5C,9G 3C, 9G 5C,9G 4C,9G ERA WHEAT 2C, 9G 9G 9G 6G G4646 CORN 3C,9H 2C, 5G 5C,9G 2C,9G WILLMS SOYBEANS 9C 9C 4C.8H 5G RICE DRY SEEDED 9C 9C 9C 9C G522 SORGHUM 9C 9C 5C,9G 4C, 9G CHEAT GRASS 9C 5C,9G 4C, 9G 9G USHll SUGARBEET 10C 9C 4C,9H 3C,6H VELVETLEAF 4C,9G 8G 3C.6H 0 GIANT FOXTAIL 9C 2C.9G 9C 3C,7G KLAGES BARLEY 3C,9G 7G 9C 9G TABLE A CMPD 73 CMPD 74 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 3C.7H 2C, 2G 2G 0 CULT MORNINGLRY 9G 8H 0 0 COCKLEBUR 3C,8H 3C,2H 0 0 PURPLE NUTSEDGE 10E 3C.9G 0 0 LARGE CRABGRASS 4C, 9G 3C.5G 7G 0 BARNYARDGRASS 9H 9H 3G 0 WILD OATS 3C, 8H 3C.8H 6G 0 ERA WHEAT 3C r 9H 2C,9H • 7G 0 G4646 CORN 3C, 9H 3C,7H 3C, 7G 2C.5G WILLMS SOYBEANS 3C, 9H 3C, 5H 2G 0 RICE DRY SEEDED ιoε 9H 7G 0 G522 SORGHUM 9H 3C,9G 3C. 8H 2C.6G CHEAT GRASS 3C,9H 9H 7G 0 USHll SUGARBEET 4C, 9G 3C, 7H 2H 0 VELVETLEAF 3C,8H 5G 0 0 GIANT FOXTAIL 9H 3C, 7H 7G 2G KLAGES BARLEY 9G 3C, 8H 3C, 7G 0 TABLE A ( co 2n2t0inued ) CMPD 75 CMPD 76 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C,5G 2C,5G 0 θ CULT MORNINGLRY 3C,7H 1C,1H θ 0 COCKLEBUR 2C.6H 9C 2H 0 PURPLE NUTSEDGE 3G 0 0 0 LARGE CRABGRASS 3C,7G 3G 0 0 BARNYARDGRASS 9C 9C 0 0 WILD OATS 9C 9C 0 0 ERA WHEAT 2C.9G 2C.9G 0 0 G4646 CORN 5C.9G 5C,9G 0 0 WILLMS SOYBEANS 4C.9G 7H 0 0 RICE DRY SEEDED 9C 9C 0 0 G522 SORGHUM 9C 5C,9G 0 0 CHEAT GRASS 5C, 9G 3C, 9G 0 0 USHll SUGARBEET 3C,6G 5C.9G. 0 0 VELVETLEAF 0 7G 0 0 GIANT FOXTAIL 9C 3C,8G 0 0 KLAGES BARLEY 9C 9C 0 0 CMPD 75 CMPD 76 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 9H 2G 0 0 BARNYARDGRASS 3C,5G 2G 0 0 WILD OATS 7G 2G 0 0 ERA WHEAT SG 3G 0 0 G4646 CORN 9G 6G 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 8G 7G 0 0 G522 SORGHUM 3C.9G 3C, 8H 0 0 CHEAT GRASS 8G 3G 0 0 USHll SUGARBEET 0 2H 0 0 VELVETLEAF 4G 0 0 0 GIANT FOXTAIL 3C.8H 3G 0 0 KLAGES BARLEY 9G 2G 0 0 TABLE A ( cont i nued ) CMPD 77 CMPD 78 RATE-KG/HA 0.05 0.01 0.05 0 . 01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE - 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM ό 0 ~ 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 .0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A CMPD 77 CMPD 78 RATE-KG/HA 0.05 0.01 0.05 0 . 01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A ( cont inued ) CMPD 79 CMPD 80 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKεR COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE — 0 0 0 LARGE CRABGRASS ic, ,3G 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 2C, ,6G 3G 0 0 VELVETLEAF 0 0 3G 0 GIANT FOXTAIL 3G 0 0 0 KLAGES BARLEY 0 0 0 0 CMPD 79 CMPD 80 RATE-KG/HA 0.05 0.01 0.05 0. RSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 - 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 - 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A 2Z Tcontinued ) CMPD 81 CMPD 82 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 4C,9G 0 2G 0 CULT MORNINGLRY 4C,9G 3C,6G 2G 0 COCKLEBUR 10C 10C 5C,9G 4C,9G PURPLE NUTSEDGE - 5C,9G 10C - LARGE CRABGRASS 3C.8G - 5G 0 BARNYARDGRASS 10C 3C, 9H 3C,8H 2C,5G WILD OATS 2C,5G 0 2G 0 ERA WHEAT 2G 0 2G 0 G4646 CORN 9C 9G 3C, 9H 3G WILLMS SOYBEANS 3C,8G 4G IH 0 RICE DRY SEEDED 9C 5C, 9G 3C, 8G 8G G522 SORGHUM 9C 4C,9G 5C,9H 2C,8G CHEAT GRASS 2C,6G 2G 2C, 5G 0 USHll SUGARBEET 10C 9C 9C 2C, 4H VELVETLEAF 10C 9C 5G 0 GIANT FOXTAIL 9C 4C,8G 0 0 KLAGES BARLEY SG 7G 4G 0 TABLE A CMPD 81 CMPD 82 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 8G 0 2G 0 CULT MORNINGLRY 9G 5G 5G 0 COCKLEBUR 9H 3C, 9H 3C, 3G 0 PURPLE NUTSEDGE 10E 0 10E 0 LARGE CRABGRASS 5G 2G 3G 0 BARNYARDGRASS 9H 8H 7G 0 WILD OATS 2G 0 0 0 ERA WHEAT 2G 0 0 0 G4646 CORN 5C, 9H 7G 6G 2G WILLMS SOYBEANS SG 2C,2H 2C, 3G 0 RICE DRY SEEDED 10E 9H 10H 4C,9H G522 SORGHUM 5C, 9H 3C.9H 9H 4C.9G CHEAT GRASS 5G 0 3G 0 USHll SUGARBEET 9G 8G 7G 5G VELVETLEAF 5H 3C.5G 3G 0 GIANT FOXTAIL 8G 7G 3G 0 KLAGES BARLEY 2C. 9G 3C.8G 7G 2G TABLE A (continued) CMPD 83 CMPD 84 P.ATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2C,2G 0 3C.7G 0 COCKLEBUR 5C.9G 3C,8H 4C.9H 2H PURPLE NUTSEDGE SG 0 0 0 LARGE CRABGRASS 5G 0 3C.7G 0 BARNYARDGRASS 3C,8H 3G 4C,9G 3C, 6G WILD OATS 2C, 6G 0 0 0 £RA WHEAT 0 0 0 0 G4646 CORN 3C,7H 0 4C, 9G 4C.8G WILLMS SOYBEANS 0 0 3C.3H 0 RICE DRY SEEDED 9C 7G 5C.9G 8G G522 SORGHUK 4C, 9G 2C.8G 5C,9G 3C r 8G CHEAT GRASS 4G 0 0 0 USHll SUGARBEE 3C,5H 4G 2H 0 VELVETLEAF - 0 — 0 GIANT FOXTAIL 2C.5G 0 4C.9G 3C.8G KLAGES BARLEY 2C r SG 0 0 0 CMPD 83 CMPD 84 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 - 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR C,8H 0 1C 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 - 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 3C,7G 0 3C. 9G 2G WILLMS SOYBEANS IH 0 2G 0 RICE DRY SEEDED lOH 7H 9H 4G G522 SORGHUM 10H 5G 2C, 9G 6G CHEAT GRASS 0 0 0 0 USHll SUGARBEεT 6G 2G 3G 2H VεLVεTLEAF IH 0 0 0 GIANT FOXTAIL 3G 0 3G 0 KLAGES BARLEY 2C,7G 0 3G 0 TABLE A ( cont inued ) CMPD 85 CMPD 1 86 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 9C 4G CULT MORNINGLRY 3C, 4H 0 4C, 8G 3C,3G COCKLEBUR 4C,9H 2H 5C,9G 1C PURPLE NUTSEDGE - 0 10C 10C LARGE CRABGRASS 5G - 9C 3C.6G BARNYARDGRASS 9C 3C,8G 9C 3C, 8H WILD OATS 0 0 3C,5G 0 ERA WHEAT 0 0 3C,5G 2G G4646 CORN 5C,9G 9G 4C,9G 3C.7G WILLMS SOYBEANS 3G 0 9C 4C,9G RICE DRY SEEDED 9C 3C,8G 9C 3C,8G G522 SORGHUM 5C,9G 3C.9G 3C.9G 3C.7G CHEAT GRASS 0 0 - . - USHll SUGARBEET 3C, 6G 2H 10C 10C VELVETLEAF 3C,7G 0 9C 10C GIANT FOXTAIL 5C.9G 3C,7G 9C 2G KLAGES BARLEY 3G 0 2C,5G 0 DOWNY BROME - - 5C,9G 5C,9G TABLE A CMPD 85 CMPD 86 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 2C, ,6G 0 COCKLEBUR 0 0 3G 2G PURPLE NUTSEDGε 0 0 5G 0 LARGE CRABGRASS 0 0 3C, ,7G 0 BARNYARDGRASS 7G 0 9H 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 2G 0 G4646 CORN 3C, ,9G 2G 3C, ,6G 0 WILLMS SOYBEANS 0 0 3C, ,5H 0 RICE DRY SEEDED 9H 4G 8G 0 G522 SORGHUM 9H 5G 9G 2C CHEAT GRASS 0 0 - - USHll SUGARBEET 3G 2G 9G 5G VELVETLEAF 2G 0 7G 5G GIANT FOXTAIL 7G 2G 5G 0 KLAGES BARLEY 2G 0 0 0 DOWNY BROME - - 7G 0 TABLE A (continued ) CMPD 87 CMPD 88 RATE-KG/HA 0.05 0. 0 . 0 5 0 . 0 1 OSOL COKER COTTON 0 0 0 CULT MORNINGLRY 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE - 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 2G 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 2C.6G 0 0 0 CHEAT GRASS - - USHll SUGARBEET 3G 0 0 VELVETLEAF 0 0 0 GIANT FOXTAIL 0 0 0 KLAGES BARLEY 0 0 0 DOWNY BROME 0 0 0 CMPD 87 CMPD 88 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COK8R COTTON 0 0 0 0 CULT " MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGε 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 . WILD OATS 0 ■ 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS - - - - USHll SUGARBEET 0 0 0 0 VELVεTLεAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 DOWNY BROME 0 0 0 0 TABLE A ( continued) CMPD 89 CMPD 90 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON IH 0 0 0 CULT MORNINGLRY 3C,4G 0 0 0 COCKLEBUR 3C.6G 2G 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 4C,9H 2G 0 0 WILD OATS 2C,5G 0 0 0 BRA WHEAT 3C, 5G 0 0 0 G4646 CORN 3C,8H 0 0 0 WILLMS SOYBEANS 3C,7G IH 3H 0 RICE DRY SEEDED 6G 0 0 0 G522 SORGHUM 3C,9H 2C.4G 0 0 CHEAT GRASS USHll SUGARBEET 10C 4G 3G 0 VELV8TL8AF 3C,6G 0 0 0 GIANT FOXTAIL 2C,5G 0 0 0 KLAGES BARLEY 3C,8G 0 0 0 DOWNY BROME 4C,7G 0 0 0 TABLE A CMPD 89 CMPD 90 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR IH 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHελT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICB DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS - - - - USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 DOWNY BROME 0 0 0 0 TABLE A (continued) CMPD 91 CMPD 92 RATE»KG/HA 0.05 0.01 0.05 ? 0.0I OSOL COK8R COTTON 0 0 IOC OC CULT MORNINGLRY 0 0 10C IOC COCKLεBUR 0 0 IΘC IOC PURPLE NUTSEDGE 0 0 9C 5C,9G LARGE CRABGRASS 0 0 8G 5G BARNYARDGRASS 0 0 9C 9C WILD OATS 0 0 5C, 9G 3C, 8G ERA WHEAT 0 0 6C f 9G 9G G4646 CORN 0 0 6G 3G WILLMS SOYBEANS 0 0 9C 9C RICE DRY SEEDED 0 0 9C 6C r 9G G522 SORGHUM 0 0 9C 5C,9G CHEAT GRASS - — 9C 9C USHll SUGARBEET 0 Q 9C 9C VELVBTLεAF θ 0 IOC IOC GIANT FOXTAIL 0 0 SC 9C KLAGES BARLEY 0 0 5C, 9G 2C.8G DOWNY BROME 0 0 - - CMPD 91 CMPD 92 RATB-KG/HA 0.05 0.01 0.05 0,01 PRSOL COKER COTTON 0 0 8G 8G CULT MORNINGLRY 0 0 9G 7G COCKLEBUR 0 0 — 5G PURPLE NUTSEDGE 0 0 10E 9G LARGE CRABGRASS 0 0 3C,8G 2G BARNYARDGRASS 0 0 9H 3C,8H WILD OATS 0 0 2C,7G 5G ERA WHEAT 0 0 3C,9H 3C.8H G4646 CORN 0 0 2C,6G 3G WILLMS SOYBEANS 0 0 3C.9H 3C.7H RICE DRY SEEDED 0 0 10E ιoε G522 SORGHUM 0 0 10H 6C,9H CHEAT GRASS - 9G 9G USHll SUGARBEET 0 0 5C, 9G 9G VELVETL8AF 0 0 3C,8G 4G GIANT FOXTAIL 0 0 9H 2C,8G KLAGES BARLEY 0 0 8G 7G DOWNY BROME 0 0 ___, — TABLE A ( continued ) CMPD 93 CMPD 94 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 6C,9G 4C,9G 2C,5G 2G CULT MORNINGLRY 9C 4C,9G IH 0 COCKLEBUR IOC 3C,8H 2G 0 PURPLE NUTSEDGE 2C,9G 2C,6G 0 0 LARGE CRABGRASS 5G 0 0 0 BARNYARDGRASS 3C,9H 3C,7H IH 0 WILD OATS 5G 3G 0 0 ERA WHEAT 8G 3G 0 0 G4646 CORN 3G 0 0 0 WILLMS SOYBEANS 3C,7G 2C,6H 3C,4H 2H RICE DRY SEEDED 6C,9G 5C,9G 0 0 G522 SORGHUM 9C 9C 2G 0 CHEAT GRASS 2C,9G 8G 0 0 USHll SUGARBEET 9C 9C 0 0 VELVETLEAF 4C,9H 5H 2C,7G 0 GIANT FOXTAIL 3C,8G 3C,6G 2G 0 KLAGES BARLEY 2C.5G 0 0 0 TABLE A CMPD 93 CMPD 94 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 3G 1C 0 0 CULT MORNINGLRY 2C,5H 1C 0 0 COCKLEBUR 3C,8H 2H 0 0 PURPLE NUTSEDGE ιoε ιoε 0 0 LARGE CRABGRASS 3C,5G 0 0 0 BARNYARDGRASS 3C, 8H 2C.7G 0 0 WILD OATS 5G 0 0 0 ERA WHEAT 5G 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 3G 2H 0 0 RICE DRY SEEDED ιoε 9H 0 0 G522 SORGHUM 7C, 9H 9H 0 0 CHEAT GRASS 9H 6G 0 0 USHll SUGARBEET 4C, 8H 6H 2G 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 3C.5G 0 0 0 KLAGES BARLEY 7G 0 0 0 TABLE A ( continued: CMPD 95 CMPD 96 RATE-KG/HA 0.05 0.01 0.05 0.01 OSOL - COKER COTTON 0 0 4C, 8G SG CULT MORNINGLRY 2C 0 IΘC IOC COCKLEBUR 0 0 10C 4C,9H PURPLE NUTSEDGE 0 0 9G 2C,5G LARGE CRABGRASS 0 0 10C 9G BARNYARDGRASS 0 0 10C 9C WILD OATS 0 0 3C, 9G 9G ERA WHEAT 0 0 3C, 9G 9G G4646 CORN 0 0 3C, 9H 5G WILLMS SOYBEANS 0 0 5C, 9H 6C,9G RICB DRY S EDεD 0 0 5C, 9G 5C, 9G G522 SORGHUM 0 0 9C 3C,9G CHEAT GRASS 0 0 9C 9G USHll SUGARBEET 0 0 10C 3C,7G VELVETLEAF 0 0 10C 9G GIANT FOXTAIL 0 0 - 10C 5C,9G KLAGES BARLEY 0 0 6C, ,9G 8G CMPD 95 CMPD 96 RATE-KG/HA 0.05 0.05 0.01 PRSOL COKER COTTON 0 0 2C f 8G 5G CULT MORNINGLRY 0 0 9G 0 COCKLEBUR 0 — 8H 2C,6H PURPLE NUTSEDGE 0 0 9G 8G LARGE CRABGRASS 0 0 loε 3C r 6G BARNYARDGRASS 0 0 4C,9H 4G WILD OATS 0 0 7G 2G _ ERA WHEAT 0 0 9H 7G G4646 CORN 0 0 2C.7G 3G WILLMS SOYBEANS 0 0 9H 8G RICE DRY" SEEDED 0 0 4C t 9H 3C,8H G522 SORGHUM 0 0 9H 9H CHEAT GRASS 0 0 8G 2G USHll SUGARBEET 0 0 5G 5G VELVεTLEAF 0 0 3C,8G 2G GIANT FOXTAIL 0 0 9H 2C.9G KLAGES BARLEY 0 0 8G 2C,2G TABLE A ( continued ) CMPD 97 CMPD 98 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 2C,7G 0 2G 0 COCKLEBUR 2C 0 0 0 PURPLE NUTSEDGE 5G 0 4G 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 2G 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 2H 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 4G 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 8G 4G 7G 0 VELV8TL8AF 0 0 3G 0 GIANT FOXTAIL 0 0 2C 0 KLAGES BARLEY 0 0 0 0 TABLE A CMPD 97 CMPD 98 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR - 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A (c 2o3n2tinued) CMPD 99 CMPD100 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 4C,9G 3C,9H 5C.9G 5C.9G CULT MORNINGLRY 3C.8G 2C. SH §C SC COCKLEBUR 4C,9H 3C.8H IΘC 9C PURPLE NUTSEDGE 0 θ 4C.9G 2C,9G LARGE CRABGRASS 0 0 3C,7G 3C.7G BARNYARDGRASS 0 0 9C 9C WILD OATS 0 0 5C,9G 3C, 9G ERA WHEAT 0 0 9G 9G G4646 CORN 2C,6G 0 3C, 9H 1C WILLMS SOYBEANS 4C,8H 3C f 6H 5C,9G 4C.,9H RICE DRY SBEDED 26 0 9C 9C G522 SORGHUM 3C.7H 6G 9C 9C CHEAT GRASS 5G 0 9C 9G USHll SUGARBEET 10C 6H 9C 9C VELVETLEAF 9G 7G 9C 9C GIANT FOXTAIL 0 0 . 9C 5C,9G KLAGES BARLEY 0 0 5C,9G 4C,9G CMPD 99 CMPD100 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 2G 0 8H 2C.6G CULT MORNINGLRY 2C 0 9G 9G COCKLEBUR 2G 0 9H 3C.7H PURPLE NUTSEDGE 10E 0 ιoε 9G LARGE CRABGRASS 0 0 6G 4G BARNYARDGRASS 0 0 9H 5H WILD OATS 0 0 3C, 8H 66. ERA WHEAT 0 0 9H 9H G4646 CORN 0 0 2G 2G WILLMS SOYBEANS 0 0 3C, 8H 3C.6H RICE DRY SEEDED 0 0 ιoε ιoε G522 SORGHUM 2C.3G 0 9H 9H CHEAT GRASS 0 0 8H 7H USHll SUGARBEET 8G 0 9G 9G VELVεTLεAF 3G 0 3C, 8H 3C.5H GIANT FOXTAIL 2G 0 9H 9H KLAGES BARLEY 0 0 9G 8G TABLE A c^f&inued) CMPD101 CMPD102 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 5C, 9G 3C,6H 3C.3H 0 CULT MORNINGLRY 5C,96 3C,8H 2C.3H IH COCKLEBUR 9G 2C.8H ' 2H 2G PURPLE NUTSEDGE 9G 4G 0 - LARGE CRABGRASS 2C, 46 0 4G 0 BARNYARDGRASS 3C,9H 2C,6G 2H 0 WILD OATS 2C,7G 1C 2C,8G 0 ERA WHEAT 2C,56 3G 2C,8G 3G G4646 CORN 0 0 0 0 WILLMS SOYBEANS 3C,7G 0 3C,4H 0 RICE DRY SEEDED 4C,9G 2C.86 4G 0 G522 SORGHUM 5C f 96 4C.96 0 0 CHEAT GRASS 3C, 9G 2C,9G 5G 0 USHll SUGARBEET 5C, 9H 5C,9H 3C,5G 0 VELVETLEAF 3C, 7H IH 3C,5G IH GIANT FOXTAIL 3C.7G 2C 5G 0 KLAGES BARLEY 2C,56 3G 4G 0 TABLE A CMPD101 CMPD102 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON SG 2C,36 26 0 CULT MORNINGLRY 86 7H 1C 0 COCKLEBUR - 2C IH 0 PURPLE NUTSEDGε oε 56 0 0 LARGE CRABGRASS 2C.56 2C 0 0 BARNYARDGRASS 9H 66 0 0 WILD OATS 56 0 0 0 ERA WHEAT 76 0 0 0 G4646 CORN 26 0 0 0 WILLMS SOYBEANS 46 ' 2H 26 0 RICE DRY SEEDED 9H 8H 0 0 G522 SORGHUM 9H 4C.9H 0 0 CHEAT GRASS 86 56 0 0 USHll SUGARBEET 96 5G 56 0 VELVETLελF 46 0 26 0 GIANT FOXTAIL 3C.8H 5G 0 0 KLAGES BARLEY 96 76 0 0 TABLE A (continued) CMPD103 CMPD104 RATE-K6/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 θ 0 COCKLEBUR 36 0 6 0 PURPLE NUTSEDGE 46 0 «. θ LARGE CRABGRASS θ θ 0 θ BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 6522 SΘR6KUM 0 0 0 0 CHEAT GRASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 CMPD103 CMPD104 RATE * KG/HΛ 0.05 0.01 0.05 0.01 PRSOL COKεR COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSED6E 0 0 0 LAR6E CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 0 0 0 0 G4646 CORN θ 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 6522 SORGHUM 0 0 0 0 CHEAT 6RASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLεAF 0 0 0 " 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 0 0 0 0 TABLE A (continued) CMPD105 CMPD106 RATε-K6/HA 0.05 0.01 0.05 0.01 POSOL COKεR COTTON 3C,9H 3C ( ,7H 3C, ,6G 2C,46 CULT M0RNIN6LRY 2C,4H 26 9C 3C,8B COCKLEBUR 3C,9H 3C, 9H 5C. ,96 2C,8H PURPLE NUTSED6E 0 - 2C, ,76 2C,2G LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 9C 5C,96 WILD OATS 0 0 9C 9C ERA WHEAT 0 0 96 96 64646 CORN 0 0 2C, 26 2C WILLMS SOYBEANS 2C,6H 4H 3C, 9G 0 RICE DRY SEEDED 0 0 9C 3C,8H 6522 SORGHUM 0 0 5C, 9G 4C.96 CHEAT 6RASS 0 0 9C 96 USHll SUGARBEET 3C,9H 3C, 8H 9C 66 VELVETLEAF 3C,96 56 9C 2C,66 GIANT FOXTAIL 0 0 9C 3C,86 KLAGES BARLEY 0 0 2C f 96 2C,86 TABLE A CMPD105 CMPD106 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 2G 0 CULT MORNINGLRY 0 0 1C 0 COCKLEBUR 0 0 26 0 PURPLE NUTSEDGE 0 0 10E 0 LARGE CRABGRASS 0 0 36 0 BARNYARDGRASS 0 0 7H 0 WILD OATS 0 0 2C.3G 0 .ERA WHEAT 0 0 66 0 G4646 CORN 0 0 . 2C,46 0 WILLMS SOYBEANS 0 0 1C 0 RICE DRY SEEDED 0 0 8H 0 G522 SORGHUM 0 0 2C,8H 0 CHEAT GRASS 0 0 46 0 USHll SUGARBEET 3H 0 2G 0 VELVETLEAF 0 0 66 0 GIANT FOXTAIL 0 0 9H 0 KLAGES BARLEY 0 0 56 0 TABLE A ( continued) CMPD107 CMPD108 RATE-K6/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 6 0 26 0 CULT MORNINGLRY θ 0 2.C.4G 0 COCKLEBUR θ 0 1C 0 PURPLE NUTSEDOE 0 θ 6 0 LAR6E CRABGRASS θ 0 26 0 BARNYARDGRASS 0 0 4G 0 WILD OATS 0 0 36 0 ERA WHEAT 0 0 26 0 G4646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 G522 SORGHUM 0 0 2C,86 0 CHEAT GRASS 0 0 56 0 USHll SUGARBEET θ 0 0 0 VELVETLEAF SG 0 46 0 GIANT FOXTAIL 0 0 2G 0 KLAGES BARLEY 0 0 36 0 CMPD107 CMPD108 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 0 0 CULT MORNINGLRY 0 0 0 0 COCKLEBUR 0 0 0 0 PURPLE NUTSEDGE 0 0 0 0 LAR6E CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS θ 0 0 0 ERA WHEAT 0 0 0 0 64646 CORN 0 0 0 0 WILLMS SOYBEANS 0 0 0 0 RICE DRY SEEDED 0 0 0 0 6522 S0R6HUM 0 0 0 0 CHEAT 6RASS 0 0 0 0 USHll SUGARBEET 0 0 0 0 VELVETLεAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 KLA6ES BARLEY 0 0 0 0 TABLE A ( continued ) CMPD109 CMPD110 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 4C.9G 4C,8H CULT MORNINGLRY 1C 6C,9G 3C,8G COCKLEBUR 0 0 5C f 96 3C,9G PURPLE NUTSEDGE 0 0 46 36 LARGE CRABGRASS 2G 0 9C 26 BARNYARDGRASS 0 0 9C 3C.8H WILD OATS 0 0 2C,76 46 ERA WHEAT 0 0 3C.96 56 64646 CORN 0 0 3C.8H 2C,46 WILLMS SOYBEANS 0 0 3C.7H 2H RICE DRY SEEDED 0 0 3C,96 46 G522 SORGHUM 0 0 9C 96 CHEAT GRASS 0 0 _2C,86 56 USHll SUGARBEET 0 0 10C 9C VELVETL8AF 3G 0 5C.96 3C,86 6IANT FOXTAIL 26 0 4C,9H 3C,76 KLAGES BARLEY 0 0 3C,86 2C,56 DOWNY BROME TABLE A CMPD109 CMPD110 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 IH 0 CULT MORNINGLRY 0 0 36 0 COCKLEBUR 0 0 2C 0 PURPLE NUTSEDGE 0 0 ιoε 0 LAR6E CRAB6RASS 0 0 76 46 BARNYARDGRASS 0 0 3C, 56 3G WILD OATS 0 0 0 0 ERA WHEAT 0 0 56 0 G4646 CORN 0 0 3C, 76 2C,56 WILLMS SOYBEANS 0 0 IH 0 RICE DRY SEEDED 0 0 66 26 G522 SORGHUM 0 0 10H 3C,36 CHEAT GRASS 0 0 46 0 USHll SUGARBEET 0 0 66 4H VBLVεTLEAF 36 0 IH 0 GIANT FOXTAIL 0 0 2C, 86 46 KLAGES BARLEY 0 0 3C, 76 26 DOWNY BROME TABLE A ( continued) CMPD111 CMPD112 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 0 0 4C,8H 3C,8H CULT MORNINGLRY θ 0 IΘC 10C COCKLEBUR 0 0 IΘC IΘC PURPLE NUTSEDGE 0 0 9C 5C,96 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 9C WILD OATS 0 0 4C,9G 36 ERA WHEAT 0 0 3C,S6 36 64646 CORN 0 0 SU,9C 3C,9G WILLMS SOYBEANS 0 0 9C 4C, 96 RΣCE DRY SEEDED 0 0 5C.96 2C, 86 6522 SORGHUH 0 0 3C,96 3C,9H CHEAT GRASS 0 0 USHll SUGARBEET 0 0 10C 9C VELVETLEAF 0 0 IΘC 5C r 96 GIANT FOXTAIL 0 0 4C,96 0 KLAGES BARLEY 0 0 76 36 DOWNY BROME — "• 9C 9C CMPD111 CMPD112 RATE-KG/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 7G 26 CULT MORNINGLRY 0 0 96 3C, 46 COCKLEBUR 0 0 8H 8H PURPLE NUTSEDGE 0 0 10E 10E LARGE .CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 8H 7H . WILD OATS 0 0 26 o" ERA WHEAT 0 0 36 36 G4646 CORN 0 0 96 86 WILLMS SOYBEANS 0 0 3C,76 1C, IH RICE DRY SEEDED 0 0 9H 8H G522 SORGHUM 0 0 9H 7H CHEAT GRASS 0 0 - • USHll SUGARBEET 0 0 96 2K VELVETLEAF 0 0 7H SH 6ΣANT FOXTAIL 0 0 46 θ KLAGES BARLEY 0 0 76 2C,36 DOWNY BROME __. — 9H 76 TABLE A (continued) CMPD113 CMPD114 RATE-K6/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 3C,9H 3C.76 66 0 CULT MORNINGLRY 10C 3C,86 0 0 COCKLEBUR 9C 4C,9G 3C,7G 7G PURPLE NUTSEDGE 9C 2C,86 36 0 LARGE CRAB6RASS 0 0 0 0 BARNYARD6RASS 3C,9G 3C,7G 3C,3G 0 WILD OATS 0 0 36 0 ERA WHEAT 0 0 36 0 64646 CORN 3C,7H 3C,7H 3C,76 2C,66 WILLMS SOYBEANS 2H 0 3C,76 2H RICE DRY SEEDED 76 2C f 56 26 0 G522 SORGHUM 3C,96 3C,9G 36 3G CHEAT GRASS - — - — USHll SUGARBEET 9C 3C, 7H 56 0 VELVETL8AF 9C 2C,7G 3C,86 2C,76 GIANT FOXTAIL 0 0 46 0 KLAGES BARLEY 2G 0 36 0 DOWNY BROME 3C,9G 3G 2C,56 26 TABLE A CMPD113 CMPD114 RATE-K6/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 8G 4G 0 0 CULT M0RNIN6LRY 2C,2H 0 0 0 COCKLEBUR 5H- 1C 2G 0 PURPLE NUTSEDGE 96 0 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 8H 0 0 0 WILD OATS 0 0 0 0 ERA WHEAT 2G 0 0 0 G4646 CORN 2C,7G 0 0 0 WILLMS SOYBEANS 1C 0 0 0 RICE DRY SE1DBD 86 6G 0 0 G522 SORGHUM 86 86 0 0 CHEAT GRASS USHll SUGARBEET 86 4H 36 0 VELVETLEAF 3H 0 0 0 GIANT FOXTAIL 0 0 0 0 KLAGES BARLEY 2C,56 0 0 0 DOWNY BROME ioc 3G 0 0 TABLE A (continued) CMPD115 CMPD116 RATE-K6/HA o.os 0.01 0.05 0.01 POSOL COKER COTTON 2C, 26 θ 10C 9C CULT MORNINGLRY 1C 0 9C 9C COCKLEBUR 3C.86 2H IΘC 10C PURPLE NUTSEDGE 0 θ 10C IΘC LARGE CRABGRASS 0 0 3C, 5G 2G BARNYARDGRASS 3C.9K 3C.76 9C 9C WILD OATS 3C,76 2G 5C, 96 2C.7G ERA WHEAT 3C,66 2G 5C, 96 9G G4646 CORN 5C,96 2C,7H 7U, 9C 5U,9C WILLMS SOYBEANS 2H 0 9C 9C RICE DRY SEEDED 5C,96 4C,96 9C 9C GS22 SORGHUM 3C.9G 3C,86 5C, 96 9G CHEAT GRASS -. — 9C 9C USHll SUGARBEεi 4C,9H 3C,7H 10C 9C VELVεTLEAF 0 0 IQC 10C GIANT FOXTAIL 3C.76 2G 9C 4C,9G KLAGES BARLEY 3€ 3G 2C, 96 7G DOWNY BROME 9C 2C,5G - - CMPD115 CMPD116 RATE-K6/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 0 0 96 86 CULT M0RNIN6LRY 0 - 0 96 96 COCKLEBUR 26 36 9H 9H PURPLE NUTSEDGE 0 0 96 96 LAR6E CRAB6RASS 76 0 56 2G BARNYARD6RASS 0 0 9H 4H WILD OATS 0 0 76 2G * ERA WHEAT 0 0 4C.96 5G 64646 CORN 2C,56 0 3C,9G 3C,76 WILLMS SOYBEANS 0 0 4C,8H 3C.8G RICE DRY SEEDED 7G 0 ιoε 3C,8G 6522 S0R6HUM 76 0 9H 3C,7G CHEAT 6RASS - - 4C,86 7G USHll SUGARBEET 36 0 5C,96 96 VELVETLEAF 0 0 3C,96 96 6IANT FOXTAIL SG 0 3C,7H 2H KLAGES BARLEY 7G 0 2C,9G 2C,6G DOWNY BROME SG 0 — — TABLE A (continued) CMPD117 CMPD118 RATE-KG/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 5C,96 9C 9C 9C CULT M0RNIN6LRY 10C 10C 10C IOC COCKLEBUR IOC IOC IOC IOC PURPLE NUTSED6E IOC 9C IOC LARGE CRABGRASS 3C,9G 36 76 66 BARNYARD6RASS 9C 5C,96 IOC 5C.9H WILD OATS 3C,9G 96 96 76 ERA WHEAT 2C, 96 96 2C,96 86 64646 CORN 4C,96 96 5C,96 2C, ,7H WILLMS SOYBEANS 9C 6C, 96 5C,9G 3C, 8H RICE DRY SEEDED 6C.9G 5C, 96 SC.9G 4C, 96 G522 SORGHUM 4C,9G 96 6C,96 9H CHEAT GRASS 5C,9G 96 9G 76 USHll SUGARBEET IOC IOC IOC 9C VELVETLEAF IOC 9C 9C 96 GIANT FOXTAIL IOC 2C, 96 4C,96 3C, 86 KLA6ES BARLEY 5C,96 9G 96 56 TABLE A CMPD117 CMPD118 RATE-K6/HA 0.05 0.01 0.05 0.01 PRSOL COKER COTTON 96 2C.66 96 96 CULT MORNINOLRY 96 96 96 96 COCKLEBUR 8H 3C,7H 8H - PURPLE NUTSEDGE 5C, 96 96 ιoε 76 LARGE CRABGRASS 2C.76 66 76 46 BARNYARD6RASS 9H 2C.56 9H 2C, ,7H WILD OATS 2C,76 26 26 0 ERA WHEAT 3C,9H 76 2C, 8H 86 64646 CORN 96 3C.8H 96 3C, ,8G WILLMS SOYBEANS 4C.9H 3C.66 2C, 9H 3C, 7H RICE DRY SEEDED 10H 4C,8H 10H 9H G522 SORGHUM 3C,9H 3C.9H 9H 9H CHEAT GRASS 3C,8H 8G 86 86 USHll SUGARBEET 4C,96 3C,96 4C, 96 4C, 9G VELVETLEAF 4C, 9G 4C,9G 4C, 96 3C # 76 GIANT FOXTAIL 9H 3C,8H 8G 3C, 7H KLAGES BARLEY 86 66 86 8G TABLE A ( continued) CMPD119 CMPD120 RATE * K6/HA 0.05 0.01 0.05 0.01 POSOL COKER COTTON 9C 6C r 9G 9C C * 8n CULT MORNIN6LRY 4C, 8H 2C r 6G IOC 4C,96 COCKLEBUR 10C IOC IΘC 5C,96 PURPLE NUTSEDGE 9C 9C 76 0 LAR6E CRABGRASS 4C.9G 2C,7G 2C,76 SG BARNYARDGRASS 10C 9C 9C 4C,8H WILD OATS 3C r 9G 2C,96 3C.9G 3C,9G ERA WHEAT 3C,96 96 76 5G G4646 CORN 6C.9G 3C,9G 9C 3C r 9G WILLMS SOYBEANS 6C.9G 5C,96 4C.96 5C,96 RICE DRY SEEDED 9C 5C, 96 9C 5C,96 G522 SORGHUM 5C,9G 4C,96 96 3C,8H CHEAT GRASS 6C,9G 3C,96 5C,96 3C,96 USHll SUGARBEET 10C 9C IOC 9C VELVETLεAF 10C IOC 96 4C f 9H GIANT FOXTAIL IOC 3C f 96 - 4C,9G 3C.66 KLAGES BARLEY 6C,96 3C.96 66 36 CMPD119 CMPD120 RATB=KG/HA 0.05 0.01 0.05 0.01 PRSOL COKεR COTTON 96 86 4C,8G 56 CULT MORNINGLRY 86 86 9G 2C.56 COCKLEBUR IOC 9H 8H 3C,6H PURPLE NUTSEDGE 10E 10E 56 2G LARGE CRABGRASS 3C.9H 96 4C, 96 2C,4G BARNYARDGRASS 9H 3C, 8H 5C r 9H 2G WILD OATS 3C t 86 66 56 o. ERA WHEAT 5C,9H 86 76 0 G4646 CORN 96 3C,9H 2C,96 2C,6G WILLMS SOYBEANS 9K 9H ' 9H 4C,8H RICE DRY SEEDED loε 10H 10H 3C, 7H G522 SORGHUM 5C.9H 4C.9H 4C f 8H 3C.6H CHEAT 6RASS 9H 8H 3C.8G 0 USHll SUGARBEET 5C.9G 76 5C,9G 2C, 4G VELVETLEAF 4C.96 3C.96 9C 2G 61ANT FOXTAIL 9H 86 7G 0 KLAGES BARLEY - 96 96 2C.86 5G TABLE A (continued. CMPD121 RATE-K6/HA 0.( )5 0.( )1 POSOL COKER COTTON 5C, ,96 4C, ,86 CULT MORNIN6LRY IOC 4C, ,9H COCKLEBUR IOC 4C, ,9H PURPLE NUTSEDGE 66 0 LARGE CRABGRASS 3C. ,86 26 BARNYARDGRASS 9C 9C WILD OATS 3C, 96 4C, ,96 ERA WHEAT 4C, 9G 96 G4646 CORN 6U, 9G 6U, 96 WILLMS SOYBEANS 6C, 96 5C, 96 RICE DRY SEEDED 9C 5C, 96 G522 SORGHUM 3C, 96 96 CHEAT GRASS 9C 96 USHll SUGARBEET IOC 4C, 8H VELVETLEAF IOC 5C, 9H GIANT FOXTAIL IOC 4C, 96 KLAGES BARLEY 4C, 96 46 TABLE A CMPD121 RATE=K6/HA 0.05 0.01 PRSOL COKER COTTON 9G 2C.66 CULT M0RNIN6LRY 96 9G COCKLEBUR 9H 9H PURPLE NUTSEDGE 76 7G LAR6E CRABGRASS 4C.86 2C.5G BARNYARDGRASS 4C.9H 3C.7H WILD OATS 4C,SG 26 ERA WHEAT 3C.9H 46 64646 CORN 96 3C,7H WILLMS SOYBEANS 9H 4C.8H RICE DRY SEEDED 1ΘH 4C,8H G522 SORGHUM 3C,9H 5C.8H CHEAT GRASS 4C.8H 3C,8H USHll SUGARBEET 5C.96 4C.96 VELVETLEAF 4C, 86 3C.36 GIANT FOXTAIL 9H 7G KLAGES BARLEY 96 7G It is noted that a few compounds such as compounds 6. 19. 20. 26. 32, 37-39, 44, 49. 54-59. 76-78 and 88 show little or no herbicidal activity at the rate tested. It is thought they would show more herbicidal activity at higher rates. Test B 244 Postemergence Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, large crabgrass (Digltaria sanguinalis) » sicklepod (Cassia obtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album) , dry seeded rice (Oryza sativa. variety California Rice Coop. M101) and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis), cocklebur (Xanthium pensylvanieum). cultivated morningglory (Ipomoβa coceinea, variety Scarlet O'Hara), Coker cotton (Gossypium hirsutum. variety Coker 315), johnsongrass (Sorghum halepense), bamyardgrass (Echinochloa erus-galli), 64646 corn (Zea mays, variety Funk G4646), Williams soybeans (Glycine max. variety Williams) and giant oxtail (Setaria faberi). The third pot was planted with Era wheat (Triticum aestivum. variety Era spring), Klages barley (Hordeum vulgare. variety Klages spring) r wild buckwheat (Polgonum convolvulus)» eheatgrass (Bromus seealinus) , USHll sugarbeet (Beta vulgaris. variety Union Sugarbeet Co. USHll), wild oats (Avena fatua), viola (Viola arvensis), blackgrass (Alopecurus myosuroides), and Altex rape (Brassica napus. variety Altex). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a-non-phy otoxic solvent. . Preemergence Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice and teaweed. The second pot was planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass, bamyardgrass, corn, soybean and giant foxtail. The third pot was planted with wheat, barley, wild buck¬ wheat, cheatgrass, sugarbeet, wild oat, viola, black- grass and rape. The three pans were sprayed preemer¬ gence with the chemicals dissolved in a non-phytotoxic solvent. Treated plants and controls were maintained in the greenhouse for 24 days, then all rated plants were compared to controls and visually rated for plant response. Response ratings are based on a scale of 0 to 100 where 0 = no effect and 100 » complete control. A dash (-) response means no test. Response ratings are contained in Table B. SUBSTITUTESHEET TABLE B CMPD 1 RATE»G/HA 0001 0004 0016 0062 02 RE 6IANT FOXTAIL 20 20 80 85 90 VELVETLEAF 0 20 30 40 70 USHll SUGARBEET 20 60 70 80 90 LARGE CRABGRASS 0 0 40 50 75 PRICKLY SI A - - 30 80 80 JIMSONWEED - 0 — 50 - RICE DRY SEEDED 20 85 90 95 100 COCKLEBUR 0 0 30 85 90 COKER COTTON 0 10 85 85 90 WILLMS SOYBEANS 0 0 0 10 30 BARNYARDGRASS 0 20 • 100 95 95 WILD OATS 10 20 30 60 70 IVY MORNINGLORY 0 0 20 80 95 BRA WHEAT 0 20 30 80 90 SICKLEPOD - 0 - - - J0HNS0N6RASS 60 85 90 100 100 PURPLE NUTSEDGE 20 30 80 ' 90 95 G4646 CORN 0 0 0 0 10 WILD BUCKWHEAT 0 50 70 80 90 BLACK6RASS 0 20 80 85 100 ALTEX RAPE 0 50 80 90 95 KLAGES BARLEY 20 30 80 80 90 GREEN FOXTAIL 20 90 95 100 99 CHEAT GRASS 30 70 90 100 100 LAMB QUAR ER 0 0 SO 70 80 CMPD RATB-6/HA 0.25 0001 0004 0016 POST 6IANT FOXTAIL 40 70 100 100 VELVεTLEAF 0 0 50 90 USHll SUGARBEET 0 20 40 70 LAR6E CRAB6RASS 0 0 0 70 PRICKLY SIDA 0 — — — IMSONWEED 0 0 20 SO RICE DRY SEEDED 0 40 90 100 COCKLEBUR 0 0 40 80 COKER COTTON 0 30 60 80 WILLMS SOYBEANS 40 50 80 90 BARNYARD6RASS 50 80 95 100 WILD OATS 0 20 70 80 IVY M0RNIN6L0RY 0 20 95 95 ERA WHEAT 50 60 60 100 SICKLEPOD 0 30 90 100 JOHNSONGRASS 70 80 100 100 PURPLE NUTSEDGE 0 30 40 70 G4646 CORN 0 0 0 0 WILD BUCKWHEAT 20 20 50 60 BLAC GRASS 0 50 80 — ALTEX RAPE 50 80 100 - KLAGES BARLEY 20 20 60 70 GREEN FOXTAIL 60 90 100 100 CHEAT GRASS 20 30 50 90 FIELD VIOLET 0 30 40 - LAMBSQUARTER 0 — 0 — TABLE B (con fc ti. nued) CMPD 2 1 RATEaG/HA 0001 0004 0016 0062 PRE 6IANT FOXTAIL 30 70 90 100 VELVETLEAF 30 50 70 90 USHll SU6ARBEET 30 60 90 100 LARGE CRABGRASS 30 50 70 90 PRICKLY SIDA 30 50 70 90 IMSONWEED 60 70 80 90 RICE DRY SEEDED 60 100 100 100 COCKLEBUR 0 30 50 70 COKBR COTTON 0 30 50 80 WILLMS SOYBEANS 0 0 30 90 BARNYARDGRASS 30 60 90 100 WILD OATS 0 0 30 80 IVY MORNINGLORY 0 30 60 90 ERA WHEAT 0 30 60 90 JOHNSONGRASS 50 70 80 90 PURPLE NUTSEDGε 0 30 80 100 G4646 CORN 0 0 .0 0 WILD BUCKWHEAT 70 80 90 90 BLACKGRASS 60 70 80 90 ALTEX RAPE 70 90 100 100 KLAGES BARLEY 30 50 80 90 -3REEN FOXTAIL 30 70 100 100 CHEAT GRASS 30 70 100 100 FIELD VIOLET 30 50 70 90 LAMBSQUARTER 50 60 70 90 CMPD 21 RATB-G/HA 0001 0004 0016 0062 POST GIANT FOXTAIL 30 50 80 90 VELVETLEAF 30 60 80 100 USHll SUGARBEET - 50 70 90 LARGE CRABGRASS 0 0 30 50 PRICKLY SIDA 0 20 40 60 JIMSONWEED 0 0 30 60 RICE DRY SEEDED 30 50 70 90 COCKLEBUR 30 40 50 60 COKER COTTON 0 30 50 60 WILLMS SOYBEANS 0 30 60 90 BARNYARDGRASS 50 70 80 90 WILD OATS - 0 30 60 IVY MORNINGLORY 30 50 70 80 ERA WHEAT - 50 80 100 SICKLEPOD 0 30 60 90 JOHNSONGRASS 30 60 90 100 PURPLE NUTSEDGE 0 30 60 90 G4646 CORN - 0 0 0 WILD BUCKWHEAT - 50 70 90 BLACKGRASS - 50 70 100 ALTEX RAPE 90 100 100 KLAGES BARLEY - 50 60 70 GREEN FOXTAIL 30 50 70 80 CHEAT GRASS 50 70 90 LAMBSQUARTER 0 0 30 50 CHICKWEED SPP. SO 70 90 TABLE B (continued) CMPD 46 RATE*G/HA 0004 0016 0062 0250 PRE GIANT FOXTAIL 50 80 90 100 VELVETLEAF 30 60 90 1Θ0 USHII SUGARBEET 70 90 100 - LARGE CRABGRASS θ 30 50 70 PRICKLY SIDA 0 30 50 80 IMSONWEED 0 30 60 90 RICE DRY SEEDED 80 §0 100 100 COCKLEBUR 0 30 50 70 COKER COTTON 0 30 40 60 WILLMS SOYBEANS 0 0 70 - BARNYARDGRASS 60 90 100 100 WILD OATS 0 30 40 60 IVY MORNINGLORY 30 50 70 90 ERA WHEAT 30 50 70 80 SICKLEPOD 30 60 90 100 JOHNSONGRASS 50 70 80 90 PURPLE NUTSEDGE 30 60 90 100 G4646 CORN 0 0 0 30 WILD BUCKWHEAT 30 50 70 90 B ACKGRA S 50 70 80 90 ALTS 2vλF£ 50 70 90 100 KLAGES BARLEY 20 40 60 80 GREEN FOXTAIL 30 50 80 100 CHEAT GRASS 60 70 80 90 LAMBSQUARTER 30 50 80. 90 CHICKWEED SPP. 30 §0 70 90 CMPD 46 RATE * 6/HA 0001 0004 0016 0062 POST 6IANT FOXTAIL 20 20 80 90 VELVETLEAF 70 80 100 100 USHll SU6ARBEET — 60 80 100 LARGE CRABGRASS 0 0 30 40 PRICKLY SIDA 20 30 40 60 JIMSONWEED 20 30 40 60 RICE DRY SEEDED 60 60 90 100 COCKLEBUR 50 100 100 100 COKBR COTTON 20 30 90 100 WILLMS SOYBEANS 60 80 90 100 BARNYARDGRASS 60 100 100 100 WILD OATS 0 40 60 80 IVY MORNINGLORY — 60 60 80 ERA WHEAT 0 30 60 100 SICKLEPOD 30- 60 90 100 JOHNSONGRASS 20 90 100 100 PURPLE NUTSEDGε 20 30 80 90 64646 CORN - 20 50 70 WILD BUCKWHEAT 70 70 80 90 BLACK6RASS 60 100 100 100 ALTEX RAPE 80 100 100 100 KLA6ES BARLEY 0 40 60 90 GREEN FOXTAIL 30 50 80 90 CHEAT 6RASS 40 60 80 100 LAMBSQUARTER 0 50 50 90 CHICKWEED SPP. 30 60 90 100 TABLE B (continued) CMPD 60 RATE-6/HΛ 0004 00 0062 0250 PRE VELVεTLEAF 30 40 80 100 USHll SUGARBEET - 90 90 90 LARGE CRABGRASS 60 60 70 80 PRICKLY SIDA 50 70 90 90 JIMSONWEED 0 50 70 80 RICE DRY SEEDED 90 90 100 100 COCKLEBUR 0 50 60 90 COKBR COTTON 0 50 90 90 WILLMS SOYBEANS 30 60 90 100 BARNYARDGRASS 20 100 100 100 WILD OATS - 30 50 70 IVY M0RNIN6L0RY 20 80 90 100 ERA WHEAT 30 40 60 90 SICKLEPOD 50 80 90 90 JOHNSONGRASS 70 80 100 100 PURPLE NUTSEDGε 0 80 90 100 G4646 CORN 0 20 30 40 WILD BUCKWHEAT 50 70 80 90 BLACKGRASS - 80 100 100 ALTEX RAPE - 90 90 100 KLAGES BARLEY 20 30 30 90 GREEN FOXTAIL 0 70 100 100 CHEAT GRASS 30 70 100 100 LAMBSQUARTBR 30 50 90 100 CHICKWEED SPP. - 100 100 100 CMPD 60 RATE=G/HA 0001 0004 0016 0062 POST GIANT FOXTAIL - 30 50 80 VELVETLEAF 70 80 100 100 USHll SUGARBEET - 70 90 100 LARGE CRABGRASS 0 0 30 50 PRICKLY SIDA 50 60 70 80 JIMSONWEED 0 30 60 90 RICE DRY SEEDED 30 50 70 90 COCKLEBUR 70 80 90 100 COKER COTTON 30 50 70 90 WILLMS SOYBEANS - 90 100 100 BARNYARDGRASS 30 50 80 100 WILD OATS - 0 30 60 IVY M0RNIN6L0RY 50 70 90 100 ERA WHEAT - 30 50 70 SICKLEPOD 50 70 100 100 J0HNS0N6RASS 30 50 70 90 PURPLE NUTSEDGE 70 100 100 100 G4646 CORN - 0 20 60 WILD BUCKWHEAT - 60 80 90 BLACKGRASS - 50 70 90 ALTEX RAPE - 100 100 100 KLAGES BARLEY - 30 50 70 GREEN FOXTAIL 0 30 50 70 CHEAT GRASS - 30 50 70 LAMBSQUARTER 60 70 80 90 CHICKWEED SPP. - 50 70 90 CMPD 64 RATE»6/HA 0004 0016 0062 0250 PRE 6IANT FOXTAIL 0 50 70 90 VELV8TL8AF 50 70 90 100 USHll SU6ARBEET 80 90 100 100 LAR6E CRABGRASS 0 30 50 70 PRICKLY SIDA 30 50 70 90 JIMSONWEED 30 50 70 90 RICE DRY SEEDED 50 70 100 100 COCKLEBUR 50 70 80 90 COKER COTTON 30 50 70 90 WILLMS SOYBEANS 30 60 80 90 BARNYARDGRASS 30 50 70 90 WILD OATS 0 30 50 70 IVY MORNINGLORY 50 80 90 100 ERA WHEAT 30 50 70 90 SICKLEPOD 30 50 70 90 JOHNSONGRASS 30 50 70 90 PURPLE NUTSEDGE 80 90 100 100 64646 CORN 0 30 60 90 WILD BUCKWHEAT 70 80 90 95 B ACKGRASS 30 70 80 90 ALTEX RAPE 80 100 100 100 KLAGES BARLEY 0 30 60 90 GRE8N FOXTAIL 30 SO 70 90 CHEAT GRASS 50 70 80 90 LAMBSQUARTER 30 50 70 90 CHICKWEED SPP. 30 50 70 90 CMPD 64 RATEaβ/HA 0.25 0001 0004 0016 POST 6IANT FOXTAIL — 100 100 100 VELVETLEAF 60 100 100 100 USHll SUGARBEET — 100 100 100 LARGE CRABGRASS 30 60 90 100 PRICKLY SIDA 0 60 100 100 JIMSONWEED 0 20 80 100 RICE DRY SEEDED 30 100 100 100 COCKLEBUR 50 80 100 100 COKBR COTTON 0 20 30 100 WILLMS SOYBEANS - 100 100 100 BARNYARDGRASS 60 100 100 100 WILD OATS - 90 100 100 IVY MORNINGLORY 40 90 100 100 ERA WHEAT - 90 100 100 SICKLEPOD 50 90 100 100 JOHNSONGRASS 60 100 100 100 PURPLE NUTSεDGε 30 80 100 100 64646 CORN ___. 100 100 100 WILD BUCKWHBAT _ 80 100 100 BLACK6RASS - 60 80 90 ALTEX RAPE - 100 100 100 KLA6ES BARLEY - 70 100 100 GREEN FOXTAIL 70 100 100 100 CHEAT GRASS - 90 90 100 LAMBSQUARTER 80 100 100 100 CHICKWEED SPP. - 90 100 100 ( 2 c 5 • TABLE B o 1 ntinued) CMPD 65 RATE-6/HA 0001 0004 0016 0062 PRE 6IANT FOXTAIL 0 20 100 100 VELVETLεAF 0 20 80 90 USHll SUGARBEET 70 90 100 100 LARGE CRABGRASS 20 60 90 90 PRICKLY SIDA 20 50 100 100 IMSONWEED 0 30 100 100 RICε DRY SEEDED 0 20 100 100 COCKLEBUR 0 20 90 100 COKER COTTON 0 20 80 100 WILLMS SOYBEANS 0 0 30 50 BARNYARDGRASS 0 30 40 50 WILD OATS 20 40 80 100 IVY MORNINGLORY 0 30 100 100 ERA WHEAT 0 60 80 100 SICKLEPOD 0 50 90 100 JOHNSONGRASS 0 30 90 90 PURPLE NUTSEDGE 0 30 90 90 G4646 CORN 0 0 90 90 WILD BUCKWHEAT 80 100 100 100 BLACKGRASS 40 50 90 100 ALTEX RAPE 70 100 100 100 KLAGES BARLEY 20 40 80 100 GREEN FOXTAIL 0 20 100 100 CHEAT GRASS 70 80 100 100 LAMBSQUARTER 20 40 100 100 CHICKWEED SPP. 70 90 100 100 CMPD 65 RATE=G/HA 0 . 25 000 1 0004 0016 POST GIANT FOXTAIL - 50 100 100 VELVETLEAF 20 70 90 100 USHll SUGARBEET - 50 100 100 LARGE CRABGRASS 0 40 . 60 100 PRICKLY SIDA 0 30 70 90 JIMSONWEED 0 60 90 100 RICE DRY SEEDED 20 40 90 100 COCKLEBUR 0 30 90 100 COKER COTTON 0 0 30 40 WILLMS SOYBEANS - 80 100 100 BARNYARDGRASS 30 80 100 100 WILD OATS - 80 90 100 IVY MORNINGLORY 20 40 90 100 ERA WHEAT - 80 90 100 SICKLEPOD 0 30 90 100 JOHNSONGRASS 40 60 80 100 PURPLE NUTSEDGE 0 20 40 100 G4646 CORN _ 50 90 100 WILD BUCKWHEAT - 30 50 80 BLACKGRASS - 30 40 90 ALTEX RAPE - 90 100 100 KLAGES BARLEY - 40 80 100 GREEN FOXTAIL 0 50 90 100 CHEAT GRASS - 60 90 90 LAMBSQUARTER 50 60 90 100 CHICKWEED SPP. - 50 90 100 TABLE B (continued) CMPD 66 RATE * 6/HΛ 0001 0004 0016 0062 PRE GIANT FOXTAIL 20 40 70 90 VELVETLEAF 0 0 40 60 USHll SUGARBEET 40 60 100 100 LARGE CRABGRASS 20 70 100 100 PRICKLY SIDA 20 30 90 90 JIMSONWEED 20 20 40 80 RICE DRY SEEDED 0 20 60 100 COCKLEBUR 0 0 .20 80 COKER COTTON 0 0 0 0 WILLMS SOYBEANS 0 0 30 80 BARNYARDGRASS 0 0 20 30 WILD OATS 20 30 40 90 IVY MORNINGLORY 0 20 90 90 ERA WHEAT 0 30 90 100 SICKLEPOD 20 40 80 100 JOHNSONGRASS 0 0 30 70 PURPLE NUTSEDGε 0 20 40 80 G4646 CORN 0 0 SO 70 WILD BUCKWHBAT 0 40 1Θ0 100 BLACK6RASS 30 50 90 100 ALTBX RAPε 40 60 90 100 KLAGES BARLEY 0 30 60 90 GREEN FOXTAIL 0 20 90 100 CHEAT. GRASS 60 70 100 100 LAMBSQUARTER 0 0 20 80 CHICKWEED SPP. 70 80 90 100 CMPD 66 RATEsG/HA 0001 0004 0016 00 POST GIANT FOXTAIL 0 30 100 100 VELVETLEAF 50 80 90 100 USK11 SU6ARBEET - 100 100 100 LARGE CRABGRASS 30 40 80 100 PRICKLY SIDA 30 70 90 100 JIMSONWEED 70 100 100 100 RICE DRY SEEDED 30 80 100 100 COCKLEBUR 40 60 100 100 COKER COTTON 0 40 80 100 WILLMS SOYBEANS - 90 100 100 BARNYARDGRASS 90 100 100 100 WILD OATS - 30 80 90 IVY MORNINGLORY 60 90 100 100 ε__.A jiEAT ___> 30 40 70 SICKLEPOD 30 100 100 100 JOHNSONGRASS 80 100 100 100 PURPLE NUTSEDGE 30 80 90 100 64646 CORN - 80 100 100 WILD BUCKWHEAT - 60 80 100 BLACK6RASS - 80 90 90 ALTEX RAPE - 100 100 100 KLA6ES BARLEY - 40 . 80 90 6REEN FOXTAIL 20 40 70 90 CHEAT 6RASS - 80 90 100 LAMBSQUARTER 80 100 100 100 CHICKWEED SPP. - 60 90 100 TABLE B ( continued ) CMPD 67 RATE-6/HA 0001 0004 0016 0062 PRE GIANT FOXTAIL 20 40 100 100 VELV8TL8AF 0 30 70 100 USHll SUGARBEET 60 70 100 100 LARGE CRABGRASS 30 70 100 100 PRICKLY SIDA 0 20 70 80 JIMSONWEED 0 40 100 100 RICE DRY SEEDED 20 50 100 100 COCKLEBUR 0 20 70 80 COKBR COTTON — 0 20 90 WILLMS SOYBEANS 0 0 40 80 BARNYARDGRASS 0 20 100 100 WILD OATS 0 20 30 40 IVY MORNINGLORY 0 20 30 100 £KA WHEAT 0 20 50 90 SICKLEPOD 0 20 30 40 JOHNSONGRASS 0 30 100 100 PURPLE NUTSEDGE 20 60 100 100 G4646 CORN 0 20 80 100 WILD BUCKWHEAT 60 90 100 100 BLACKGRASS 30 50 80 90 ALTEX RAPE 30 70 100 100 KLAGES BARLEY 0 20 70 100 GREEN FOXTAIL 0 20 90 100 CHEAT GRASS 30 70 80 100 LAMBSQUARTER 0 30 90 100 CHicKwεεD SPP. 30 70 80 90 CMPD 67 RATE=G/HA 0001 0004 0016 00 POST GIANT FOXTAIL - 90 100 100 VELVETLEAF 40 90 100 100 USHll SUGARBEET - 100 100 100 LARGE CRAB6RASS 30 70 90 100 PRICKLY SIDA 20 80 90 90 JIMSONWEED 70 100 100 100 RICE DRY SEEDED 50 90 100 100 COCKLEBUR 40 80 100 100 COK8R COTTON 0 30 80 100 WILLMS SOYBEANS - 100 100 100 BARNYARD6RASS 60 100 100 100 WILD OATS - 90 100 100 IVY MORNINOLORY 30 80 100 100 ERA WHEAT - 90 100 100 SICKLEPOD 30 90 100 100 JOHNSON6RASS 70 90 100 100 PURPLE NUTSEDGE 20 70 80 100 G4646 CORN - 20 90 100 WILD BUCKWHEAT - 70 90 100 BLACKGRASS - 80 100 100 ALTEX RAPE - 100 100 100 KLAGES BARLEY - 90 100 100 GREEN FOXTAIL 40 80 100 100 CHEAT GRASS - 90 100 100 LAMBSQUARTER 70 90 100 100 CHICKWEED SPP. - 70 90 100 7 Continued) CMPD 68 RATE-G/HA 0001 0004 0016 0062 PRE GIANT FOXTAIL 20 40 90 100 VELVεTLEAF 0 30 80 90 USHll SUGARBEET 30 40 100 100 LARGE CRABGRASS 0 40 100 1ΘΘ PRICKLY SΣBA * 0 30 80 60 JIMSONWEED 0 30 70 90 RICE DRY SEEDED 0 30 100 100 COCKLEBUR 0 20 30 40 COKER COTTON 0 0 20 40 WILLMS SOYBEANS 0 0 30 70 BARNYARDGRASS 20 30 60 80 WILD OATS 40 50 80 100 IVY MORNINGLORY 0 30 50 80 ERA WHEAT 0 30 60 100 SICKLEPOD 0 30 80 90 JOHNSONGRASS 20 30 90 90 PURPLB NUTSEDOε 0 30 100 100 64646 CORN 0 0 0 40 WILD BUCKWHEAT 40 70 90 " 90 B A K6RASS 30 50 80 90 ALTEX RAPE 30 70 100 100 KLAGES BARLEY 0 40 80 90 GREEN FOXTAIL 0 30 90 100 CHEAT 6RASS 30 40 100 100 LAMBSQUARTER 0 30 70 90 CHICKWEED SPP. 40 60 70 80 CMPD 68 RATE * 6/HA 0004 0016 POST 6IANT FOXTAIL 90 90 VεLVETLελF 70 70 USHll SUGARBEBT 100 100 LARGE CRABGRASS 0 60 PRICKLY SIDA 20 60 JIMSONWEED 50 50 RICE DRY SEEDED 60 100 COCKLEBUR 80 100 COKER COTTON 90 90 WILLMS SOYBEANS 70 100 BARNYARD6RASS 60 90 WILD OATS 60 80 IVY MORNΣNOLORY 70 100 ERA WHEAT 90 90 SICKLEPOD 90 100 JOHNSON6RASS 100 100 PURPLE NUTSEDGE 0 60 G4646 CORN 0 0 WILD BUCKWHEAT 70 80 BLACK6RASS 90 90 ALTEX RAPE 100 100 KLA6ES BARLEY 70 80 6REEN FOXTAIL 70 80 CHEAT GRASS 90 100 LAMBSQUARTER 80 90 CHICKWEED SPP. 70 90 TABLE B ( continued) CMPD 92 RATE-G/HA 0016 0062 PRE VELVETLελF 50 60 USHll SUGARBEET 80 90 LARGE CRABGRASS 60 70 PRICKLY SIDA - 90 JIMSONWEED 70 90 RICE DRY SEED8D 100 100 COCKLEBUR 30 50 COKER COTTON 50 90 WILLMS SOYBEANS 70 100 BARNYARDGRASS 100 100 WILD OATS 30 50 IVY MORNINGLORY 70 90 ERA WHEAT 40 70 SICKLEPOD 60 80 JOHNSONGRASS 90 100 PURPLE NUTSEDGE 80 90 G4646 CORN 0 40 WILD BUCKWHEAT 80 80 BLACKGRASS 70 100 ALTEX RAPE 90 100 KLAGES BARLEY 40 70 GREEN FOXTAIL 90 100 CHEAT GRASS 70 90 LAMBSQUARTER 90 100 CHICKWEED SPP. 50 80 CMPD 92 RATE=G/HA 0001 0004 0016 0062 POST 6IANT FOXTAIL - 0 20 60 V8LV8TLEAF 0 0 20 70 USHll SUGARBEET - 30 80 - LARGE CRABGRASS 0 0 0 20 PRICKLY SIDA 0 0 0 50 JIMSONWEED 60 80 90 100 RICE DRY SEEDED 0 0 60 80 COCKLEBUR 60 60 70 90 COKER COTTON - 40 50 70 WILLMS SOYBEANS - 0 10 50 BARNYARDGRASS 30 40 60 70 WILD OATS 0 0 0 — IVY MORNINGLORY 70 70 80 80 ERA WHEAT 0 0 10 40 SICKLEPOD 0 0 40 70 JOHNSONGRASS 90 90 100 100 PURPLE NUTSEDGE 0 0 30 40 G4646 CORN 0 0 0 10 WILD BUCKWHEAT 0 0 30 30 BLACKGRASS 50 50 70 - ALTEX RAPE 00 100 100 - KLAGES BARLEY 0 0 0 10 GREEN FOXTAIL - 40 50 90 CHEAT GRASS 0 0 30 - FIELD VIOLET 0 0 0 - LAMBSQUARTER - 50 60 70 TABLE B (continued) CMPD 93 RAT8»6/HA 0001 0004 0016 0062 PRE 6IANT FOXTAIL 30 50 70 80 VELVETLEAF 0 30 50 70 USHll SUGARBEET 30 50 80 90 LAR6E CRABGRASS 0 20 30 60 PRICKLY SIDA 30 50 70 90 JIMSONWEED 0 30 60 90 RICE DRY SEEDED 30 50 90 100 COCKLEBUR 0 0 30 40 COKER COTTON 0 0 0 20 WILLMS SOYBBANS 0 0 0 0 BARNYARD6RASS 0 30 50 70 WILD OATS 0 0 30 50 IVY MORNIN6LORY 0 20 30 50 ERA WHEAT 0 0 20 40 SICKLEPOD 0 20 30 50 JOHNSONGRASS 70 80 90 100 PURPLE NUTSEDGE 0 0 30 70 64646 CORN 0 0 0 0 WILD BUCKWHEAT 0 30 50- 70 BLACKGRASS 30 50 70 100 ALTEX RAPE 50 70 80 90 KLAGES BARLEY 0 20 40 60 GREEN FOXTAIL 0 0 30 60 CHEAT GRASS 0 30 50 70 FIELD VIOLET 20 30 60 80 LAMBSQUARTER 0 30 60 90 CMPD 93 RATE=G/HA 0.25 0001 0004 0016 POST GIANT FOXTAIL 0 - 40 100 VεLVETLEAF 0 0 20 60 USHll SUGARBEET _ 20 30 60 LARGE CRABGRASS 0 0 40 80 PRICKLY SIDA 0 0 20 70 jiMsoN εεD 0 30 50 60 RICε DRY SEEDED 0 0 50 90 COCKLEBUR 0 0 30 70 COKER COTTON 0 0 0 20 WILLMS SOYBEANS 30 40 90 90 BARNYARDGRASS 30 40 90 100 WILD OATS - 30 50 70 IVY MORNINGLORY 0 0 30 60 ERA WHEAT — 40 50 60 SICKLEPOD 0. 0 40 80 JOHNSONGRASS 0 70 90 1Q0 PURPLE NUTSEDGE 0 20 30 60 64646 CORN — 0 20 80 WILD BUCKWHEAT - 0 — 80 BLACKGRASS — 0 70 ■" 80 ALTEX RAPE - 30 90 100 KLAGES BARLEY - 20 40 90 GREEN FOXTAIL 0 40 70 90 CHEAT GRASS - 0 70 70 LAMBSQUARTER 0 0 0 40 CHICKWEED SPP. — 0 40 60 TABLE B ( continued) CMPD 96 RATε»6/HA 0001 0004 0016 0062 PRE 6IANT FOXTAIL 0 20 90 100 vεLvεTLεAF 0 30 30 40 USHll SUGARBEET 0 0 60 80 LARGE CRABGRASS 0 0 40 100 PRICKLY SIDA 0 0 30 30 JIMSONWEED 0 60 80 90 RICB DRY SEEDED 0 so 90 90 COCKLEBUR 0 30 50 60 COKBR COTTON 0 0 40 70 WILLMS SOYBEANS 0 20 50 60 BARNYARDGRASS 0 20 80 80 WILD OATS 0 30 40 40 IVY MORNINGLORY 0 0 30 60 ERA WHEAT 0 0 30 60 SICKLEPOD 0 0 40 80 J0HNSON6RASS 0 40 70 90 PURPLE NUTSEDGE 0 20 40 60 G4646 CORN 0 0 0 0 WILD BUCKWHEAT 0 0 50 90 BLACK6RASS 0 50 50 70 ALTEX RAPE 0 70 70 90 KLAGES BARLEY 0 20 30 80 GREEN FOXTAIL 0 70 100 100 CHEAT GRASS 0 30 50 80 LAMBSQUARTER 0 20 30 70 CHICKWEED SPP. 0 0 40 40 CMPD 96 RATE=G/HA 0001 0004 0016 0062 POST 6IANT FOXTAIL - 50 90 100 VELVETLEAF 30 80 90 100 USHll SUGARBEET - 100 100 100 LARGE CRABGRASS 0 0 50 60 PRICKLY SIDA 0 30 50 70 JIMSONWEED 0 0 20 40 RICE DRY SEEDED 50 90 100 100 COCKLEBUR 70 100 100 100 COKER COTTON 50 80 90 90 WILLMS SOYBEANS - 80 100 100 BARNYARDGRASS 30 40 80 100 WILD OATS - 70 100 100 IVY MORNINGLORY 60 90 100 100 ERA WHEAT — 70 100 100 SICKLEPOD 50 70 100 100 JOHNSONGRASS 70 100 100 100 PURPLE NUTSEDGE 0 30 60 100 G4646 CORN - 0 20 40 WILD BUCKWHEAT - 60 90 100 BLACKGRASS - 90 100 100 ALTEX RAPE - 100 100 100 KLAGES BARLEY - 70 100 100 GREEN FOXTAIL 30 50 80 90 CHEAT GRASS - 80 100 100 LAMBSQUARTER 50 70 100 100 CHICKWEED SPP. 70 90 100 TABLE B (continued) CMPD 100 RATE-6/HA 0001 0004 0016 0062 PRE 6IANT FOXTAIL 70 90 100 100 VELVETLEAF 30 60 90 95 USHll SU6ARBEET 70 90 100 100 LARGE CRABGRASS 0 30 SO 80 PRICKLY SIDA 0 30 50 70 JIMSONWEED 0 30 50 80 RICE DRY SEEDED 30 60 80 90 COCKLEBUR 0 30 60 90 COKER COTTON 0 30 50 60 WILLMS SOYBEANS 0 30 40 60 BARNYARDGRASS 30 50 80 100 WILD OATS 0 0 30 50 IVY MORNINGLORY 0 30 50 80 ERA WHEAT 0 30 60 90 SICKLEPOD 30 SO 70 90 JOHNSONGRASS 50 70 80 90 PURPLE NUTSEDGE 0 30 60 90 G4646 CORN 0 0 0 _ 0 WILD BUCKWHEAT 0 30 60 90 BLACKGRASS 50 60 70 90 ALTEX RAPE 70 100 100 100 KLAGES BARLEY 30 50 70 90 6RE8N FOXTAIL 50 70 90 100 CHEAT 6RASS 50 70 80 90 LAMBSQUARTER 70 100 100 100 CHICKWEED SPP. 30 50 70 90 CMPD 100 RATE=6/HA 0001 0004 0016 OOi POST 6IANT FOXTAIL 0 20 40 90 VELVETLEAF 0 30 70 90 USHll SU6ARBEET 40 70 80 90 LAR6E CRAB6RASS 0 0 0 0 PRICKLY SIDA 0 0 20 30 JiMsoNwεεD 0 0 20 40 RICε DRY SEEDED 0 30 70 100 COCKLEBUR 0 50 70 100 COKER COTTON 0 0 10 20 WILLMS SOYBEANS 0 40 50 90 BARNYARDGRASS 30 . 60 90 100 WILD OATS 0 60 90 100 IVY MORNINGLORY 0 50 90 90 ERA WHEAT 0 40 80 100 SICKLEPOD — 20 -> SO JOHNSONGRASS SO 50 70 90 PURPLE NUTSEDGE 0 0 20 30 G4646 CORN 0 0 0 20 WILD BUCKWHEAT 0 0 SO 70 BLACK6RASS 50 70 90 90 ALTEX RAPE 70 100 100 100 KLA6ES BARLEY 0 30 SO 90 6R8EN FOXTAIL 20 40 80 90 CHEAT 6RASS 0 30 70 90 LAMBSQUARTER 40 60 80 90 CHICKWEεD SPP. 0 0 30 70 TABLE B ( continued) CMPD 106 PRE 6IANT FOXTAIL 40 90 100 VELVETLEAF 0 20 60 USHll SUGARBEET 30 80 100 LARGE CRABGRASS 40 80 80 PRICKLY SIDA 30 50 70 JIMSONWEED 0 - 20 RICE DRY SEEDED 80 100 100 COCKLEBUR 0 40 80 COKER COTTON 0 10 20 WILLMS SOYBEANS 0 0 20 BARNYARDGRASS 20 40 100 WILD OATS 20 60 80 IVY MORNINGLORY 20 40 50 BRA WHEAT 20 40 60 SICKLEPOD 0 20 60 JOHNSONGRASS 70 90 100 PURPLE NUTSEDGε 40 50 70 G4646 CORN 0 0 10 WILD BUCKWHEAT 30 60 80 BLACKGRASS 80 100 100 ALTEX RAPE 80 90 100 KLAGES BARLEY 50 80 90 GREEN FOXTAIL 40 90 100 CHEAT GRASS 70 100 100 LAMBSQUARTER 80 90 100 CHICKWEED SPP. 0 10 20 CMPD 106 RATE=G/HA 0001 0004 0016 0062 POST GIANT FOXTAIL 0 20 40 90 VELVETLεAF 0 30 70 90 USHll SUGARBEET 40 70 80 90 LARGE CRABGRASS 0 0 0 0 PRICKLY SIDA 0 0 20 30 JIMSONWEED 0 0 20 40 Ricε DRY sεεDED 0 30 70 100 COCKLEBUR 0 50 70 100 COKER COTTON 0 0 10 20 WILLMS SOYBEANS 0 40 50 90 BARNYARDGRASS 30 60 90 100 WILD OATS 0 60 90 100 IVY MORNINGLORY 0 50 90 90 ERA WHEAT 0 40 80 100 SICKLEPOD - 20 - 50 JOHNSONGRASS 50 50 70 90 PURPLE NUTSEDGE 0 0 20 30 G4646 CORN 0 0 0 20 WILD BUCKWHEAT 0 0 50 70 BLACKGRASS 50 70 90 90 ALTEX RAPE 70 100 100 100 KLA6ES BARLEY 0 30 50 90 GREEN FOXTAIL 20 40 80 90 CHEAT GRASS 0 30 70 90 LAMBSQUARTER 40 60 80 90 CHICKWEED SPP. 0 0 30 70 Test C Postemergence Six round pots (17 cm diameter by 15 cm deep) were used to grow plants to the treatment βtage. Four were planted with seeds or tubers of four species each and another with soybeans using Sassafras sandy loam as the growing media.. The sixth pot was planted to corn using a Tama silt loam. During spraying, the soil of this pot was temporarily covered with perlite then later removed so any effects noted would be from foliar uptake only. A separate pot of corn (25.5 cm diameter by 19.5 cm deep) grown in Sassafras sandy loam was also included to determine foliar/soil treatment effects on plant growth. Plants were grown 10 to 20 days and were in the 2 to 5 leaf stage when sprayed postemergence with compounds of the invention. Species included were as follows: G4646 Corn [maize] (Zea mays, variety Funk G4646). Williams Soybeans (Glycine max. variety Williams). Green foxtail (Setaria viridis). Giant foxtail CSetaria faberi)« Fall Panicum (Panicum dichotomiflorum)_ Crabgrass (Diαitaria sanquinalis)« Bamyardgrass (Echinochloa crus-galli). Johnsongrass (Sorghum halepense). G522 Sorghum (Sorghum vulgare. variety Funk G522). Nutsedge (Cvperus rotundus). Velvetleaf (Abυtilon theophxasti). Cocklebur (Xanthium pensylvanicum). Smartweed (Polygonum persicaria. Lambsquarter (Chenopodium album), Pigweed (Amaranthus retroflexus), Ivy Morningglory (Ipomoea hederacea), Jimsonweed (Datura stramonium). Ragweed (Ambrosia artemisiifolia). Preemergence Plantings were made as above except all in Ta a silt loam. Compounds were sprayed preemergence the day after planting then all pots were watered to simulate rainfall. After treatment all plantings were maintained in a greenhouse about 20 days then visually rated for plant response. Ratings are based on a scale of 0 to 100 where 0 = no effect and 100 » complete control. Response ratings are shown in Table C. SUBSTITUTESHEET TABLE C CMPD RATE GM/HA 0004 0008 0016 0032 0064 01 OST • SOIL TYPE SAS SAS SAS SAS SAS SAS G4646 CORN 0 0 0 0 25 40 WILLMS SOYBEANS 0 20 35 50 65 βs GRE8N FOXTAIL 50 65 80 90 95 100 6IANT FOXTAIL 40 65 70 90 95 100 FALL PANICUM 70 90 95 100 100 100 LARGE CRABGRASS 0 0 0 30 70 80 BARNYARDGRASS 90 100 10Θ 100 100 100 JOHNSONGRASS 100 100 100 100 100 100 G522 SORGHUM 100 100 1Θ0 100 100 100 PURPLE NUTSEDGE 30 SO 75 90 100 100 VELVETLEAF 20 45 75 85 95 100 COCKLEBUR SO 8S 160 100 100 100 LADY SMARTWEED 0 0 0 ' 25 50 70 LAMBSQUARTER 0 0 0 0 35 so REDRΘOT PIGWEED 70 85 100 100 100 100 IVY MORNINGLORY 50 85 100 100 100 100 JIMSONWEED 0 0 0 0 0 35 PERLITE CORN 0 0 0 0 20 30 BSTITUTE SHEET TABLE C (continued ) CMPD 21 RATE GM/HA 0002 0004 0008 0016 POST SOIL TYPE SAS SAS SAS SAS G4646 CORN 0 0 0 0 WILLMS SOYBEANS 95 98 100 100 GREEN FOXTAIL 80 90 90 100 GIANT FOXTAIL 70 90 90 95 FALL PANICUM 80 95 98 100 LARGE CRABGRASS 0 0 0 30 00 BARNYARDGRASS 100 100 100 1 100 JOHNSONGRASS 100 100 100 100 6522 S0R6HUM 100 100 100 60 VELVETLEAF 40 60 60 90 COCKLEBUR 40 40 40 0 0 30 LADY S ART EED 0 30 30 60 LAMBSQUARTER 30 100 100 100 REDROOT PI6WEED 90 20 0 0 IVY M0RNIN6L0RY 0 30 JIMSONWEED 0 20 20 10 P8RLIT8 CORN 0 0 0 RATE GM/HA 0032 0064 0125 POST SOIL TYPE SAS SAS SAS G4646 CORN 10 20 70 WILLMS SOYBEANS 100 100 100 GREEN FOXTAIL 100 100 100 GIANT FOXTAIL 100 100 100 PALL PANICUM 100 100 100 LARGE CRABGRASS 40 60 70 BARNYARDGRASS 100 100 100 JOHNSONGRASS 100 100 100 G522 SORGHUM 100 100 100 VELVETLEAF 90 100 100 COCKLEBUR 100 100 100 LADY S ART EED 50 80 80 40 50 70 LAMBSQUARTER REDROOT PIGWEED 100 100 100 IVY MORNINGLORY 30 40 70 JIMSONWEED 40 40 50 PERLITE CORN 10 20 60 SUBSTITUTE SHEET TABLE C ( continued) CMPD 46 RATE GM/HA 0002 0004 0008 POST SOIL TYPE SAS SAS SAS G4646 CORN 0 0 0 WILLMS SOYBEANS 25 45 75 GREEN FOXTAIL 0 30 60 GIANT FOXTAIL 0 30 60 FALL PANICUM 0 35 70 LARGE CRAB6RASS 0 0 0 BARNYARD6RASS 45 90 100 JOHNSONGRASS 60 80 95 6522 S0R6HUM 75 90 100 PURPLE NUTSEDGE 0 35 45 VELV8TL8AF 0 0 35 COCKLEBUR 0 30 40 LADY SMARTWEED 0 30 75 LAMBSQUARTER . 0 0 0 REDROOT PIGWEED 35 70 100 IVY MORNINGLORY 0 0 20 JIMSONWEED 0 0 0 PERLITE CORN 0 o • 0 RATE GM/HA 0016 0032 0064 0125 POST SOIL TYPE SAS SAS SAS SAS 64646 CORN 0 0 0 30 WILLMS SOYBEANS 90 100 100 100 GREEN FOXTAIL 75 85 90 100 GIANT FOXTAIL 75 85 90 100 FALL PANICUM 90 100 100 100 LARGE CRABGRASS 0 25 35 45 BARNYARDGRASS 100 100 100 100 JOHNSONGRASS 100 100 100 100 G522 SOR6HUM 100 100 100 100 PURPLE NUTSED6E 60 80 95 100 VELVETLEAF 70 70 85 95 COCKLEBUR 60 75 95 95 LADY SMARTWEED 85 95 100 100 LAMBSQUARTER 30 40 55 65 REDROOT PIGWEED 100 100 100 100 IVY MORNINGLORY 40 60 70 80 JIMSONWEED 0 25 40 60 PERLITE CORN 0 0 0 ' 25 TABLE C (continued) CMPD 60 RATE 6M/HA 0002 0004 00 POST SOIL TYPE SAS SAS SAS 64646 CORN 0 0 0 WILLMS SOYBEANS 100 100 100 6REEN FOXTAIL 20 35 45 OIANT FOXTAIL 0 25 40 FALL PANICUM 60 75 90 LARGE CRABGRASS 0 0 0 BARNYARDGRASS 80 95 100 JOHNSONGRASS 95 100 100 G522 S0R6HUM 100 100 100 PURPLE NUTSEDGE 30 50 65 VELVεTLεAF 20 35 55 COCKLEBUR 35 40 60 LADY SMARTWEED 20 30 40 LAMBSQUARTER 0 0 0 REDROOT PIGWEED 60 75 100 IVY MORNINGLORY 0 0 20 JIMSONWEED 0 0 0 PERLITE CORN 0 0 0 RATE GM/HA 0016 0032 0064 0125 POST SOIL TYPE SAS SAS SAS SAS 64646 CORN 0 30 60 85 WILLMS SOYBEANS 100 100 100 100 6REEN FOXTAIL 65 75 85 95 OIANT FOXTAIL 60 75 90 100 FALL PANICUM 95 100 100 100 LARCE CRAB6RASS 30 40 60 80 BARNYARDGRASS 100 100 100 100 JOHNSONGRASS 100 100 100 100 6522 SOR6HUM 100 100 100 100 PURPLE NUTSEDGE 75 100 100 100 VELV8TL8AF 85 100 100 100 COCKLEBUR 70 85 100 100 LADY SMARTWEED 60 80 100 100 LAMBSQUARTER 35 60 90 95 REDROOT PIGWEED 100 100 100 100 IVY MORNINOLORY 40 65 80 95 JIMSONWEED 20 40 65 85 PERLITE CORN 0 25 50 70 SUBSTΓΓUTE SHEET TABLE C (continued) CMPD 60 RATE GM/HA 0016 0032 0064 0125 PRE SOIL TYPE TAM TAM TAM TAM G4646 CORN 0 0 0 0 WILLMS SOYBEANS 30 40 60 βs GREEN FOXTAIL 20 25 35 60 GIANT FOXTAIL 20 20 30 40 FALL PANICUM 70 80 95 100 LARGE CRABGRASS 0 0 20 — BARNYARD6RASS 65 70 90 100 J0HNS0N6RASS 70 90 100 100 6522 S0R6HUM 75 100 100 100 PURPLE NUTSEDGE 35 60 80 - VELVETLEAF 0 0 0 — COCKLEBUR 0 0 0 - LADY SMARTWEED 50 65 sr _» LAMBSQUARTER 25 40 60 — REDROOT PI6WEED 50 60 90 — IVY MORNINOLORY 0 0 0 — JIMSONWEED 0 0 0 — TABLE C (continued _ . CMPD 92 RATE GM/HA 0016 0032 0064 0125 PRE SOIL TYPE TAM TAM TAM TAM G4646 CORN o 0 0 0 WILLMS SOYBEANS o 25 SO •0 GREEN FOXTAIL o 35 70 100 GIANT FOXTAIL o 30 70 95 5 FALL PANICUM 20 45 15 9 40 LARGE CRABGRASS o 20 70 BARNYARDGRASS 25 45 •5 100 JOHNSONGRASS 50 65 100 100 G522 SORGHUM 45 55 90 100 PURPLE NUTSEDGE o 25 «5 10 VELVETLEAF o 0 O 30 COCKLEBUR o 0 0 20 100 LADY SMARTWEED 30 60 95 LAMBSQUARTER 20 40 90 100 REDROOT PIGWEED 50 70 100 100 IVY MORNINGLORY o O 0 25 JIMSONWEED 0 0 0 35 TABLE C (continued) CMPD 92 RATE GM/HA 0002 0004 0001 POST SOIL TYPE SAS SAS SAS G4646 CORN 0 0 0 WILLMS SOYBEANS 65 •5 100 GREEN FOXTAIL 40 50 to GIANT FOXTAIL 40 65 to FALL PANICUM 0 40 to LARGE CRABGRASS 0 0 0 BARNYARDGRASS 0 30 50 JOHNSONGRASS to ss 100 G522 SORGHUM •s 95 100 PURPLE NUTSEDGE 0 35 60 VELVETLEAF 0 25 40 COCKLEBUR 35 60 to LADY SMARTWEED 25 40 50 LAMBSQUARTER 40 65 85 REDROOT PIGWEED 75 95 100 IVY MORNINGLORY 0 30 55 JIMSONWEED 0 0 20 PERLITE CORN 0 0 0 RATE GM/HA 0016 0032 0064 0125 POST SOIL TYPE SAS SAS SAS SAS G464 CORN 0 20 35 60 WILLMS SOYBEANS 100 100 100 100 GREEN FOXTAIL 90 95 100 100 GIANT FOXTAIL 100 100 100 100 FALL PANICUM 95 100 100 100 LARGE CRABGRASS 25 40 50 to BARNYARDGRASS 70 100 100 100 JOHNSONGRASS 100 100 100 100 G522 SORGHUM 100 100 100 100 PURPLE NUTSEDGE 90 100 100 100 VBLVETLEAr 65 85 95 100 COCKLEBUR 100 100 100 100 LADY SMARTWEED 60 70 •5 95 LAMBSQUARTER 95 100 100 100 REDROOT PIGWEED 100 100 100 100 IVY MORNINGLORY 70 15 95 100 JIMSONWEED 40 60 70 85 PERLITE CORN 0 0 20 40 SUBSTITUTE SHEET TABLE C ( continued ) CMPD 96 RATE GM/HA 0016 0032 0064 0125 0>S0 PRE SOIL TYPE rAM TAM TAM TAM TAM 64646 CORN 0 0 0 0 0 WILLMS SOYBEANS 0 0 0 20 45 GREEN FOXTAIL 0 15 20 35 50 GIANT FOXTAIL 0 15 20 35 50 FALL PANICUM 0 0 0 0 15 LARGE CRABGRASS 0 0 0 0 15 BARNYARDGRASS 0 15 30 70 •5 JOHNSONGRASS 0 20 45 55 75 G522 SORGHUM 20 35 55 75 95 PURPLE NUTSEDGE 0 0 0 0 0 VELVETLEAF 0 0 20 30 40 COCKLEBUR 0 10 20 35 50 LADY SMARTWEED 15 35 50 60 75 LAMBSQUARTER 0 0 0 15 25 REDROOT PIGWEED 0 25 45 65 15 IVY MORNINGLORY 0 0 0 0 0 JIMSONWEED 0 0 0 15 20 TABLE C (continued) CMPD 96 RATE CM/HA 0002 0004 OΘOt 0016 0032 0064 5 POST SOIL TYPE SAS SAS SAS SAS SAS SAS G4646 CORK 0 20 50 60 to 90 WILLMS SOYBEANS 90 90 91 98 100 100 GREEN FOXTAIL 50 60 70 70 90 98 . GIANT FOXTAIL 40 50 60 70 9t 100 LAR6E CRABGRASS 0 0 θ 20 40 50 BARNYARDGRASS 70 9t 100 100 100 100 θ JOHNSONGRASS 60 9t 100 100 100 • 100 6522 SORGHUM to 90 9t 100 100 100 PURPLE NUTSEDGE 0 0 0 0 30 70 ELVETLEAF 0 0 30 SO 60 90 COCKLEBUR 30 70 to 90 100 100 LADY SMARTWEED 20 30 30 50 70 9t LAMBSQUARTER 0 0 30 30 30 30 REDROOT PIGWEED 0 0 40 40 to 90 5 IVY MORNINGLORY 0 30 30 30 40 50 JIMSONWEED 40 60 60 60 100 100 PERLITE CORN 20 20 30 60 60 to 0 5 0 5 SUBSTITUTE SHEET TABLE C (continued) CMPD 100 RATE GM/HA 0016 0012 0064 012S 02! PRE SOIL TYPE TAM TAM TAM TAM TAM G 4646 CORN 0 0 0 0 20 W ILLMS SOYBEANS 0 25 40 70 to G REEN FOXTAIL 25 45 85 95 100 95 100 GIANT FOXTAIL 0 35 70 FALL PANICUM 40 15 100 100 100 65 LA RGE CRABGRASS 0 20 35 50 100 B A RNYARDGRASS 35 60 100 100 100 JOHNSONGRASS 70 90 100 100 100 6 522 SORGHUM 75 95 100 100 PU RPLE NUTSEDGE 30 SO 70 90 100 VELVETLEAF 0 0 0 0 25 COCKLEBUR 0 0 20 35 SO LADY SMARTWEED 40 70 95 100 100 LA MBSQUARTER 25 40 65 95 100 100 100 R EDROOT PIGWEED 30 65 90 0 35 I V Y MORNIN6LORY 0 0 0 JIMSONWEED 0 0 30 45 70 TABLE C (continued) CMPD 100 RATE GM/HA 0002 0004 00 FOS* SOIL TYPE SAS SAS SAS G4646 CORN 0 0 e WILLMS SOYBEANS 65 75 90 GREEN FOXTAIL 50 65 to GIANT FOXTAIL 45 60 to FALL PANICUM SO 65 to LARGE CRABGRASS 0 0 0 BARNYARDGRASS 50 60 70 JOHNSONGRASS 95 100 100 G522 SORGHUM 100 100 100 PURPLE NUTSEDGE 0 20 40 VELVETLEAF 0 40 70 COCKLEBUR 45 95 100 LADY SMARTWEED 0 20 45 LAMBSQUARTER 30 40 60 REDROOT PIGWEED 65 90 100 IVY MORNINGLORY 30 70 15 JIMSONWEE 0 0 0 PERLITE CORN 0 0 0 RATE GH/SA 0016 0032 0064 0125 POST SOIL TYPE SAS SAS SAS SAS 64646 CORN 0 θ 0 30 WILLMS SOYBEANS 100 100 100 100 GREEN FOXTAIL 95 100 100 100 GIANT FOXTAIL 90 9S 100 100 FALL PANICUM 95 9S 100 100 LARGE CRABGRASS- 30 40 50 to BARNYARDGRASS to 100 100 100 JOHNSONGRASS 100 100 100 100 G522 SORGHUM 100 100 100 100 PURPLE NUTSEDGE 65 15 90 95 VELVETLEAr 10 90 100 100 COCKLEBUR 100 100 100 100 LADY SMARTWEED 60 70 95 100 LAMBSQUARTER to 90 100 100 REDROOT PIGWEED 100 100 100 100 IVY M0RNIN6L0RY 100 100 100 100 JIMSONWEED 0 25 45 70 PERLITE CORN 0 © 0 20 Test D 273 Potatoes (Solanum tuberosum. cult. 'Green Mountain') were grown in Metro 350 medium in 20 cm plastic pots. Potatoes were 17 days old at time of spraying. Bamyardgrass (Echinochloa crus-qalli)_ johnsongrass (Sorghum halepense). giant foxtail (Setaria faberii). crabgrass (Diqitaria sanquinalis), purple nutsedge (Cvperus rotundus). ji sonweed (Datura stramonium), velvetleaf (Abutilon theophrasti) . cocklebur (Xanthium pensylvanicum). and morningglory (Ipomoea hederacea) were grown in Sassafras sandy loam (pH 6.5, 1% organic matter) in plastic-lined 25 cm pots. These plants were 9 days old at the time of spraying. Compounds were sprayed at 62, 16, 4, and 1 g/ha. Compounds were sprayed at each rate on one pot containing potato plants and at the same time on one pot containing the remaining species. Compounds were dissolved in a non-phytotoxic solvent. 4.0\ and was sprayed at 374 1/ha. Plants were maintained in a greenhouse and were evaluated 11 days after spraying. All sprayed plants were evaluated for injury as compared to control plants. Injury was measured visually using a 0 to 100% scale where 0 = no effect and 100 = complete control. Results are shown in Table D. SUBSTITUTESHEET TABLE D Compound 21 Rate (g/ha) Species 62 16 potato 0 0 0 0 bamyardgrass 100 100 70 30 johnsongrass 100 100 100 60 giant foxtail 100 100 90 60 crabgrass - 90 85 60 50 purple nutsedge 90 90 80 30 jimsonweed 80 60 40 20 velvetleaf 100 95 50 20 cocklebur 90 50 30 0 morningglory 90 70 40 20 Test E Tomatoes (Lvcopersicon esculentum cult. 'Rutgers') and peppers (Capsicum rutescens cult. •Yolo*) were grown in Metro 350 medium in 10 cm plastic pots. Tomatoes and peppers were 19 days old at time of spraying. Purple nutsedge (Cvperus rotundus). crabgrass (Diqitaria san uinalis)_ sicklepod (Cassia tora). prickley sida (Sida spinosa). jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti). lambsquarter (Chenopodium album), green foxtail (Setaria viridis). cocklebur (Xanthium pensylvanicum). morningglory (Ipomoea hederacea). johnsongrass (Sorghum halepense). bamyardgrass (Echinochloa crus-qalli). giant foxtail (Setaria faberii) . wild buckwheat (Polyqonum convolvulus), downy brome (Bromus tectorum). wild oat (Avena fatua), chickweed (Stellaria spp.). and blackgrass (Alopecurus myosuroides) . were grown in sassafras sandy loam (pH 6.5. 1% organic matter) in plastic-lined 25 cm pots. These plants were 7 to 11 days old at the time of spraying. Compounds were sprayed at 62, 16, 4, and 1 g/ha. Compounds were sprayed at each rate on one pot containing tomatoes, one pot containing peppers, and on three pots containing the remaining species. Compounds were dissolved in a non-phytotoxic solvent, and were sprayed at 374 1/ha. Plants were maintained in a greenhouse and were evaluated 16 days after spraying. All sprayed plants were evaluated for injury as compared to control plants. Injury was measured visually using a 0 to 100% scale where 0 - no effect and 100 » complete control. Results are shown in Table E. SUBSTITUTE SHEET TABLE E Compound 21 Rate (g/ha) Species 62 16 tomatoes 10 0 0 0 peppers 80 70 50 30 nutsedge 100 100 30 0 crabgrass 90 80 50 30 sicklepod 100 100 90 40 prickley sida 100 100 50 20 jimsonweed 100 50 10 0 velvetleaf 100 100 70 50 lambsquarter 60 50 40 0 green foxtail 100 100 100 50 cocklebur 100 80 50 20 morningglory 90 85 50 20 johnsongrass 100 100 100 50 ba yardgrass 100 100 100 40 giant foxtail 100 100 90 40 wild buckwheat 100 90 90 40 downy brome 100 100 80 20 wild oats 100 70 30 20 chickweed 100 100 90 90 blackgrass 100 100 100 70

Claims: WHAT IS CLAIMED: 1. A compound selected from w JSC-NHCNA ** I R wherein J-4 J-5 W is O or S; R. is R. or R : - 1 f g R. is H. C.-C, alkyl, C.-C, haloalkyl, halogen. NO , C. -C. alkoxy, C.-C. alkylthio or CN; is C. -C- haloalkyl, C -C, alkyl, cyclopropyl. C.-C. alkyl substituted by C.-C alkoxy, OH, C.-C. alkylthio or CN. CN, W_R.., amino, C.-C. alkylamino or C.-C 3 dialkylamino; R. is C.-C. alkylsulfinyl, C.-C alkylsulfonyl, C -C cycloalkylthio, C -C cycloalkylsulfinyl, C3-C,5_ cycloalkyl r sulfonyl, SO2_NH2„. S0 2 NR^R 8 , S0 2 NR 7 R 8 , OS0 2 R 8 . S0 2 OR 8 . N 3 , P(W 1 )(OC 1 -C 2 alkyl) 2 , CN. C0 2 R 9 . C0 2 R^. CH 2 F. CF 2 H. CH 2 C1, CC1 2 H or C 2 -C 4 haloalkyl; R„ is C.-C. alkylsulfinyl, C_-C_ cycloalkylthio. 3 4 3 9 C -C cycloalkylsulfinyl, C -C cycloalkylsul- fonyl, S0 2 NH 2 , S0 2 NR d R e . S0 2 NR 7 R 8 . S0 2 NR ? R 8 . OS0 2 R 8 . S0 2 OR 8 . N 3 . alkyl> 2 . CN. C0 2 R 9 . C0 2 R' or C-L-C4 haloalkyl; R. is C -C_ alkylsulfinyl. C -C_ cycloalkylthio. 4 1 3 b C -C cycloalkylsulfinyl, C -C cycloalkylsul- fonyl. S0 2 NH 2 . S0 2 R d R e , S0 2 OR g . N 3 . P(W 1 )(OC 1 -C 2 alkyl) 2 . CN, CO^ or , 1 c 5 c,1-C4„ haloalkyl; R is C.-C. alkylsulfinyl, C.-C. alkylsulfonyl, C 3--C_D cycloalkylthio, C3,-C_b_cycloalkylsulfinyl, C_-C 5 cycloalkylsulfonyl, S0 2 H 2 , S0 2 NR d e , S0 2 R 7 g. OS0 2 Rg, S0 2 ORg. N 3 . P.W^ (OC.^^ 20 alkyl) 2 , CN. C0 2 R g or C χ -C 4 haloalkyl; R. is C.-C 4 alkylthio, C.-C alkylsulfinyl, C.-C haloalkylthio, C -C haloalkylsulfinyl, C -C haloalkylsul onyl, C -C alkenylthio, C -C alkenylsulfinyl, C -C alkenylsulfonyl, C -C alkynylthio, C -C alkynylsulfinyl, C -C alkynylsul onyl. C -C cycloalkylthio, C -C cycloalkylsulfinyl, C -C cycloalkylsulfonyl, S0 2 R d R e , S0 2 R 7 Rg, S0 2 ORg. N 3 , P(W )(OC -C alkyl) 2 . CN. C0 2 R or C -C 4 halo- 30 alkyl; R is H, C 2 -C cyanoalkyl, C -C alkenyl or C -C alkynyl; R' is C1-C alkyl; Rg is C.-C alkyl. C.-C haloalkyl. C_-C alkenyl, 35 C 3 ~ C al}ε Y n YΪ» C 2 -C 4 alfcoxyaikyl ©∑ cyclo- propyl; or R. and R 8 may be taken together as -(CH.),-. -(CH 2 ) 4 -. -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -; R. is CH_CH_R... CH_CF_. C.-C. haloalkyl. 2 2 10 2 3 3 4 C -C alkynyl. C -C 4 alkylthioalkyl, C -C. cycloalkyl or C -C_ cycloalkylalkyl; R. is CX-C4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 C1, CH ^ CH ^ Br, CH_CH_OCH- or CH CH_0C_H_; 2 2 2 2 3 2 2 2 5 R is OH, F. CN. OS0 2 (C 1 -C 3 alkyl) or OS0 2 «_—-C, haloalkyl); R is C -C 3 alkyl. C -C 3 haloalkyl. C -C alkenyl or C -C alkynyl; W is O or S; W is O or S; A-l A-2 A-3 A-4 A-5 A-6 A-7 X is H. C.1-C4. alkyl, C.1-C4. alkoxy. C2--C4. halo- alkoxy, C -C haloalkyl, C -C haloalkylthio, C -C alkylthio. halogen. C -C alkoxyalkyl, C 2_-C_b alkoxyalkoxy, amino. C.1-C,3 alkylamino or di(C -C alkyl)amino; SUBSTITUTE SHEET Y is H. C χ -C 4 alkyl. C χ -C 4 alkoxy, C 2 ~C 4 halo¬ alkoxy, C -C haloalkylthio, C -C 4 alkylthio, C 2~ C 5 alkoχ Y allζ Y 1 * C 2 " C 5 alkoxyalkoxy' amino, C.-C 3 alkylamino. di(C.-C 3 alkyl)amino, C 3 ~C 4 alkenyloxy, C -C 4 alkynyloxy, C 2 ~C alkylthio- alkyl, C -C alkylsulfinylalkyl, C -C alkyl¬ sulfonylalkyl. C χ -C 4 haloalkyl, C 2 ~C 4 alkynyl, C -C_ cycloalkyl, azido. N(OCH 3 )CH 3 . « m is 2 or 3; Q and 0 are independently O or S; Ra is H or C.-C3. alkyl; R. D and RC are independently C,1-C_3 alkyl; R a, is H or C.-C2. alkyl; Re is C.-C2. alkoxy; Z is CH. N, CCH 3 . CC 2 H 5 . CC1 or CBr; Y χ is O or CH 2 ; X is CH . OCH 3 , OC 2 H g or OCF 2 H; 2 is CH 3 . C 2 H 5 or CH 2 CF 3 ; Y 2 is OCH 3 . OC 2 H 5 . SCH 3 . SC 2 H 5 , CH 3 or CH 2 CH 3 ; X is CH or OCH ; Y is H or CH 3 ; X Λ is CH,, OCH,, OC.H_. CH o 0CH, or Cl; 4 3 3 2 5 2 3 Y is CH,. OCH , OC H or Cl; and their agriculturally suitable salts; provided that 1) when X is halogen, then Z is CH and Y is OCH , OC 2 H 5 . NH 2 . NHCH 3 . N(CH 3 2 or N(OCH 3 CH 3 2) when W is S, then R is H. A is A-l, Z is CH or N. and Y is CH 3 » OCH 3 . OC 2 H g . CH OCH , C H , CF 3 , SCH 3 . OCH 2 CH=CH 2 , OCH 2 C=CH. OCH 2 CH 2 OCH 3 , 3) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R 1, , R_. R3,. R4.. R5_ or R6, iβ less than or equal to six; 4) when J is J-1 and R 2 is C.-C 4 alkylsulfonyl. S0 2 NRaR e . S0 2 NR'R 8 or C0 2 R'. or when J is J-2 and R3 is CF 3 , S0 2 NR^R e , SO2 R7R8 or C0 2 R' , then Y is other than C -Cs alkylthioalkyl. C -C. alkylsulfinylalkyl. C_-C- alkylsulfonylalkyl. 5) when J is J-2 or J-3 and R, 3 .-ocr R4.ris C,-C. alkyl- sulfinyl. then X and Y are other than NH. or NHCH 3 6) when J is J-2 and R 3 is C.-C 4 alkylsul inyl or SO2.NRα.Re. or R„/ is H. then X and Y are other than C 2 -C 4 haloalkoxy: 7) when J is J-5. then R_ is other than H and R- is other than S0 2 NR.R ; 8 when J is J-2 and R 3 is S0 2 NH 2 or S0 2 NR d R e . • or R-/ is H, then X is other than iodine; 9) when J is J-2 and R 7_ iβ H or R3. iβ SO2_NRα,Re. then Y is other than C._-C 4 alkynyl; 10) X. and Y. are not simultaneouβly Cl: 4 4 11) when J iβ J-1. J-2. J-3. J-4 and A is A-5. then R- iβ other than H; 12) when J iβ J-1 or J-2. then A iβ other than A-6; 13) wwhheenn JJ iiββ JJ--11 aanndd AA iiββ AA--'7. then R 2 is other than C..-C- alkylβulfonyl: SUBSTITUTE SHEET 14) when R 2 or 3 is C0 2 R or S0 2 NR^R 8 , then R, iβ R and when R. or R, iβ other than 1 g 2 3 C0 2 R' or S0 2 NR^R 8 . then R-L iβ ; and 15) when J iβ J-2 and R. iβ adjacent to the sulfonylurea bridge, then R i haloalkyl. C 2 -C 3 alkyl, cyclopropyl, CN, amino, C.-C 3 alkylamino or C.-C dialkylamino. 2. A compound of Claim 1 where X is C -C alkyl, C -C alkoxy, Cl, F. Br, I, CH 2 F. CF 3 . OCH 2 CH 2 F. OCH 2 CHF 2 . OCH 2 CF 3 . CH Cl or CH 2 Br; and Y is H. C 1 -C 2 alkyl. C χ -C 2 alkoxy, CH 2 OCH 3 . CH 2 OCH 2 CH 3 , NHCH 3 . N(OCH 3 )CH 3 . (CH 3 ) 2 » CF 3 . SCH , OCH CH=CH . OCH C≡CH. OCH CH OCH , _3 »& & -_£ - £ * Δ 3 CH SCH , cyclop cpyl. CΞCH or C≡CCH ; R is H or CH ; and Z is CH or N. 3. A compound of Claim 2 where W is O; R_ is H, CH . C. haloalkyl, halogen or OCH ; is C -C 2 haloalkyl, ethyl. W R , CH 2 OCH , CH 2 SCH 3 . CH 2 CN. C χ -C 2 alkylamino or N(CH 3 ) 2 »* R 2 iβ C -C alkylβulfinyl, C -C alkylβulfonyl, S0 2 NH 2 . S0 2 NR d R e . S0 2 NR 7 R 8 . S0 2 NR^R 8 , OS0 2 R 8 . S0 2 OR 8 . 3 , P(W 1 )(OC 1 -C 2 alkyl) 2 . CN. C0 2 R 9 . C0 2 R g . CHF 2 . CF 2 H. CH 2 C1. CC1 2 H or C 2 -C 4 haloalkyl; R, iβ C -C A alkylβulfinyl. SO„NH„. SO„NR.R , 3 1 4 . 2 2 Z α e S0 2 R 7 R 8 . S0 2 NR^R 8 . OS0 2 R 8 . S0 2 OR 8 . N 3 . P( I )(OC 1 -C 2 alkyl) 2 « CN. C0 2 R 9 , C0 2 g or C -C haloalkyl; SUB R 4 is C χ -C 4 alkylsulfinyl, S0 2 NH 2 . S0 2 N(OCH 3 -_.« 3 , S0 2 R ? R 8 , OS0 2 R 8 . S0 2 OR 8 . N 3 » FW^(OC^C j alkyl) 2 , CN, C0 2 R g or ^-^ haloalkyl; R is C -C alkylsulfinyl, C -C alkylsulfonyl, S0 2 NH 2 , S0 2 N(OCH 3 )CH 3 , S0 2 OR 8 . N 3 . P(W 1 )(OC 1 -C 2 alkyl) 2 , CN. CO^ or C.1-C4. haloalkyl; R 6, is C1,-C4. alkylthio, C1.-C4. alkylsulfinyl, C -C haloalkylthio. C.-C haloalkylsul- finyl. C.-C haloalkylsulfonyl, C 3 -C 4 alkenylthio, C -C alkenylsulfinyl, C_-C alkenylsulfonyl, C 3 -C 4 alkynylthio, C.-C alkynylsulfinyl, C -C alkynylsulfonyl. S0 2 N(OCH 3 )CH 3 . S0 2 NR ? R 8 . . N 3 . P(W 1 )(OC 1 -C 2 alkyl) 2 , CN. CO^ or C^^ haloalkyl; R is H. C -C cyanoalkyl. C -C alkenyl or C 3 ~ a l Jζ y n Y 1 ϊ R β is C.-C. alkyl. C -C Λ haloalkyl. C.-C. 8 1 4 1 4 3 4 alkenyl. C 3 -C alkynyl, C -C alkoxyalkyl or cyclopropyl; and R is C -C alkyl, C -C haloalkyl, allyl or propargyl. 4. A compound of Claim 3 where J is J-1. 5. A compound of Claim 3 where J iβ J-2. 6. A compound of Claim 3 where J is J-3. 7. A compound of Claim 3 where J iβ J-4. 8. A compound of Claim 3 where J iβ J-5. 9. A compound of Claim 4 where is H, C -C cyanoalkyl, allyl or propargyl; R' iβ C 1 -C 3 alkyl; R 8. iβ C.1-C 'alkyl, allyl, propargyl or cyclo- propyl; g is CH 2 CH 2 R 1£J . CH 2 CH 2 SCH 3 . propargyl or cyclopropylmethyl; CH 2 CH 2 0CH 3 or 10. A compound of Claim 9 where A is A-l; X is CH 3 , OCH 3 « OCH 2 CH 3 . Cl or OCH 2 CF 3 ; and Y is CH 3 . OCH 3 . CH 2 CH 3 . CH 2 OCH 3 . NHCH j or CH(OCH 3 ) 2 . 11. A compound of Claim 10 where Z iβ CH. 12. A compound of Claim 10 where Z iβ N. 13. A compound of Claim 5 where R_ is H. C 2 -C 3 cyanoalkyl, allyl or propargyl; and R_ iβ C.-C 3 alkyl. allyl, propargyl or cyclo¬ propyl. 14. A compound of Claim 13 where X iβ CH 3 . OCH 3 , OCH 2 CH 3 « Cl or OCH 2 CF 3 ; and Y iβ CH 3 . OCH 3 . CH 2 CH 3 . CH 2 OCH 3 , NHCH 3 or CH(OCH 3 ) 2 . 15. A compound of Claim 14 where Z is CH. 16. A compound of Claim 14 where Z iβ N. 17. A compound of Claim 2 where W is O; R 2 iβ C.-C 4 alkylβulfinyl or C 1 ~C 4 alkylβulfonyl; and R f iβ H, C^^ alkyl. C haloalkyl. C χ -C 2 alkoxy or C j -C 2 thioalkyl. „ Q c 285 18. A compound of Claim 17 where kylsulfonyl; 19. The compound of Claim 1 which iβ N-[(4.6-di- methoxypyrimidin-2-yl)aminocarbonyl]-3-(l-propylβul- fonyl)-2-pyridinesulfonamide. 20. The compound of Claim 1 which iβ N-[(4,6-di- methoxyρyrimidin-2-yl)aminocarbonyl]-3-(l-propyl- sulfinyl)-2-pyridineβulfonamide. 21. The compound of Claim 1 which is N-[(4,6-di- methoxypyrimidin-2-yl)aminocarbonyl3-3-(ethylsul- fonyl)-2-ρyridineβulfonamide. 22. The compound of Claim 1 which iβ N2-[(4,6-di- methoxypyrimidin-2-yl)aminocarbonyl]-N3-ethyl-2,3- pyridinedisulfonamide. 23. The compound of Claim 1 which iβ N-[(4.6-di- methoxypyrimidin-2-yl)aminocarbonyl]-3-(methylsul- fonyloxy)-2-pyridinesulfonamide. 24. The compound of Claim 1 which is N2-[(4.6-di- methoxypyrimidin-2-yl)aminocarbonyl]-N3-methyl-2,3- pyridinedisulfonamide. 25. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 1 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 26. A composition suitable for controlling the growth of undesired vegetation which compriβeβ an effective amount of a compound of Claim 2 and at least one of the following: surfactant, βolid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 27. A composition βuitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 3 and at leaβt one of the following: βurfactant, βolid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 28. A composition εuitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 4 and at leaβt one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 29. A composition βuitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 5 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 30. A composition βuitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 6 and at least one of the following: surfactant, βolid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 31. A composition βuitable for controlling the growth of undesired vegetation which compriseβ an effective amount of a compound of Claim 7 and at least one of the following: εurfactant, βolid inert diluent or liquid inert'diluent and mixtureβ of the foregoing. 32. A compoβition βuitable for controlling the growth of undeβired vegetation which comprises an effective amount of a compound of Claim 8 and at leaβt one of the following: βurfactant, βolid inert diluent or liquid inert diluent and mixtureβ of the foregoing. 33. A method for controlling the growth of undesired vegetation which compriβeβ applying to the locus to be protected an effective amount of a compound of Claim 1. 34. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 2. 35. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3. 36. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4. 37. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5. 38. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6. 39. A method for controlling the growth of undesired vegetation which compriseβ applying to the locus to be protected an effective amount of a compound of Claim 7. 40. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 8. 41. A method for controlling the growth of undesired vegetation which compriβeβ applying to the locuβ to be protected an effective amount of a compound selected from Claims 19 to 24. 42. A method for controlling the growth of undesired vegetation which comprises applying to the corn crop to be protected an effective amount of a compound βelected from Claims 19, 21 or 24.

Inventors: LIANG PAUL HSIAO-TSENG, LIANG, PAUL, HSIAO-TSENG
Applicants: DU PONT, E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1987
Main classification: C07D401
IPC codes: A01N47, A01P13, C07D213, C07D239, C07D251, C07D401, C07D405, C07D409, C07D491, C07D521