HERBICIDAL SULFONAMIDES

Abstract: Novel sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method-of-use of said compounds and compositions as general preemergence and/or postemergence herbicides or their use as plant growth regulants.

Description: Title HERBICIDAL SULFONAMIDES Background of the Invention This invention relates to novel sulfonylurea herbicidal compounds, agriculturally suitable compo¬ sitions thereof and a method of using them to control the growth of undesired vegetation. New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe. The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge. -SO NHCONH-. linking two aromatic or heteroaromatic rings. U.S. 4.514.211 discloses herbicidal βulfonamides of formula and wherein W L is SO„NHCNA: R 12 R_ is H. Cl. Br or C -C alkyl; R 6 is H. CH3. Cl or Br; and Q is O. S or SO . EP-A-107.979 discloses herbicidal sulfonamides of formula w JSO j NHCNRA wherein J is. in part. 13 14 18 19 n is 0. 1 or 2: R is H or CH ; is H or C -C alkyl; and is H or CH . U.S. 4,391, 627 discloses herbicidal sulfonamides of formula where W is O or S: and R- is H. Cl. Br. NO , C--C_ alkyl. C.-C, alkoxy. C0 2 R 2 . C(0)NR 3 R 4 . S0 2 R or S0 2 R 6 R 7 . EP-A-70,698 discloses herbicidal sulfonamides of formula where R is H. C__-C 4 alkyl. (CH 2 ) m C0 2 R 9 . CH 2 OC 2 H-.. SO 2 R 10 . CHO. B0 2 SH ll R l2 . CH 2 (CH 3 ) 2 or CH 2 OCH 3 ; R χ is H. C χ -C 4 alkyl. C0 2 R 6 . C(0)NR ? R 8 . C(0)R 1() , so 2 R 10 . or SO 2 HR 11 H 12 : and R -_. is H. C X.-C_J alkyl or SOJ_.Cfa.H_b. EP-A-168.246 discloses herbicidal sulfonamides of formula QSO,NHCNA wherein 2_l R is H or C -C alkyl optionally substituted with 0-3 halogen atoms selected from 1-3 F. 1-2 Cl or 1 Br. C -C 4 alkylthio. C -C alkoxy. CH-,OCH 3 . CH 2 CH 2 OCH 3 or CH^CH.,; is H or CH ; and W is O, S or NR . U.S. 4,502.882 discloses, in part, herbicidal sulfonamides of formula wherein is o, S, SO or S0 2 ; W is O. S, SO or SO ; R is H or CH : and R is H or C -C alkyl. U.S. 4,578.108 discloses, in part, herbicidal sulfonamides of formula LSO-.NHCN-A wherein Q is o, S(0) n or R 3 : n is 0, 1 or 2; iiss HH.. CCHH .. CCl or F; is H. Cl or F: R is H. Cl or F: and South African Patent Application 83/5165 (Swiss priority 7/16/82. published 1/16/84) discloses herbicidal sulfonamides of formula wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and., together with the linking carbon atom, forms a non- aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the -SO- or SO - group, and R is hydrogen, halogen, nitro. C -C alkyl. C. 1-C4. haloalkyl. C,1-C4_ alkoxy. C1-C2_ haloalkoxy, C,-C alkoxycarbonyl. C,-C alkylthio. C -C alkylsulfinyl. C^C^ alkyl- sulfonyl or C -C_ alkoxyalkoxy; and 2 b R is H. halogen. NO . C -C alkyl. C -C 4 halo- alkyl. C -C alkoxy. C -C haloalkoxy. C- ^ -C alkoxycarbonyl. C -C alkylthio. C -C 4 alkyl¬ sulfinyl. C,-C alkylsulfonyl or C -C.. alkoxyalkoxy. South African Patent Application 84/3522 (Swiss priority 5/11/83. published 11/11/84) discloses herbicidal sulfonamides of formula wherein R. is H. halogen. NO . C- ^ -C alkyl. C.-C 4 haloalkyl. CN. XR , COXR . CONR 7 R 8 . SOR 9 A is an unsubstituted or substituted unsatur- ated bridge of 4 atoms, of the formula -CH=CH-Y-, wherein Y is a bridge member of 2 atoms which is selected from the series consisting of -NH-CO-. -NH-SO - , -S-CO-, -S-SO2-. -O-CO- or -O-SO2-. East German Patent 134,184 (VEB Chemiekomb bitterfeld), published 2/14/79, discloses herbicidal sulphamoyl-2.1.3-benzothiadiazole derivatives of the formula wherein H 20 and R 30 are H or h .10 is carbamoyl N-substituted by a C.-C. aliphatic or C,-C- cycloaliphatic group. Summary of the Invention This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as general preemergence and/or postemergence herbicides or plant growth regulants. w JSO,NHCNA R wherein J-l J-2 J-5 J-6 J-7 W is O or S; R is H or CH 3 ; E is a single bond. CH 2 or 0; R. is H, C.-C. alkyl, C.-C 3 haloalkyl. halogen, nitro, C χ -C 3 alkoxy. S0 2 N a R b , C χ -C 3 alkyl¬ thio, C--C 3 alkylsulfinyl, C -C alkylsul- fonyl. CH 2 CN, CN. C0 2 R c . C χ -C 3 haloalkoxy. C -C 3 haloalkylthio, C -C alkoxyalkyl. C 2 -C 4 alkylthioalkyl. CH 2 3 or NR d R e : is H. C -C. alkyl. C 2 -C 3 cyanoalkyl. methoxy or ethoxy; R. is H. C.-C 4 alkyl or C 3 -C. alkenyl: or R and R. may be taken together as -(CH 2 ) 3 -. -(CH 2 ) 4 -. -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -; „ C is C.1-C4. alkyl. C,3-C4. alkenyl. C_3-C4- alkynyl. C_-C 4 haloalkyl. C -C 3 cyanoalkyl. C -C cycloalkyl. C 4 -C_ cycloalkylalkyl or C 2 «-C 4 alkoxyalkyl; R, and R are independently H or C.-C., alkyl; Q 1 is s. so 2 or NR 2 : Q 2 is o. s or NR 2 : Q 3 is O. S or R 3 ; R 2 is H. C.-C 3 alkyl. phenyl. benzyl. CH 2 CH»CH 2 . CH 2 C=CH. CN. C χ -C 3 haloalkyl. OH. OCH 3 or oc 2 H 5 ; 3 is H or C χ -C 3 alkyl: R4 Λ is H or CH_3: R is H. halogen. CH 3> CH 2 CH 3 . OCH 3 . OCH 2 CH 3 . OCF 2 H or halomethyl; R is C χ -C 4 alkyl ; A-l A- 2 A- 3 A- A- 5 ^6. A-7 X is H, C.-C 4 alkyl, C.-C. alkoxy, C.-C 4 halo¬ alkoxy, C,-C- haloalkyl. C.-C haloalkylthio. C -C alkylthio. halogen. C.-C alkoxyalkyl. C 2,-C_b alkoxyalkoxy. amino. C,JL-C_3 alkylamino. di(C.-C 3 alkyl)amino or C -C.. cycloalkyl; Y is H. C χ -C 4 alkyl. C χ -C 4 alkoxy. C χ -C 4 halo¬ alkoxy, C.-C haloalkylthio. C.-C alkylthio, C, 2-C_b alkoxyalkyl. C2,-C_5 alkoxyalkoxy, amino, C.-C- alkylamino. di(C.-C alkyl)amino. C.-C alkenyloxy. C._-C 4 alkynyloxy. C.-C.. alkylthio- alkyl. C.-C 4 haloalkyl. C 2 ~C 4 alkynyl. azido, cyano, C 2_-Cb_ alkylsulfinylalkyl, C2_-C_ alkylεul- f onylalkyl . CR f , NRα, (C2..-C3-. cyanoalkyl ) or N (OCH3, ) CH3, ; is 2 or 3; . and L_ are independently O or S; R f is H or C 1 -C 3 alkyl; Ry and II are independently C, JL-C 3 alkyl: Z is CH or N; Z is CH or N; Y is o or CH : χ is CH 3 , OCH 3 , OC 2 H 5 or OCF 2 H; 2, is CH,3, C2H C 5 or CH2.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 3 is CH 3 or OCH 3 ; Y 3 is H or CH 3 ; X4 Λ is CH,3. OCH,3. OC2„H_5. CH20CH,3 or Cl; and Y4_ is CH,3. OCH,3. OC,H_ or cl; and their agriculturally suitable salts; provided that a) when X is Cl. F. Br or I. then Z is CH and Y is OCH 3 . OC 2 H 5 . N(OCH 3 )CH 3 . NHCH 3 . N(CH 3 > 2 or OCF 2 H; b) when X or Y is C haloalkoxy. then Z is CH; c) X and Y are not simultaneously Cl; d) when W is S, then E is a single bond. R is H. A is A-l and Y is CH 3 . OCH 3 » OC 2 H... CH 2 OCH 3 . C 2 H 5 . CF 3 . SCH 3 . OCH 2 CH * CH 2 . OCH 2 C=CH. OCH 2 CH 2 OCH 3 . CH(OCH ) or 1.3-dioxolan- 2-yl: e) when the total number of carbons of X and Y is greater than four, then the number of carbons of must be less than or equal to two; f) Q and Q 4 are not simultaneously S; g) when J is J-5. then Q is NR and Q is NR ; and h) when n is 0, then Q is NR_ and Q is NR . i) when- R_ is other than H, then R is H. R., is H. W is O, A is A-l and E is a single bond, j) when J is J-6 or J-7. then A is A-l. In the above definitions, the term "alkyl" 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. isopropyloxy and the different butyl isomers. Alkynyl denotes straight chain or branch alkynes, e.g. ethynyl. 1-propynyl, 2-propynyl and the different butynyl isomers. Alkylsulfonyl denotes methylsulfonyl, ethylsul- fonyl and the different propylsulfonyl isomers. Alkylthio. alkylsulfinyl. alkylamino. alkylsul- famoyl, etc. are defined in an analogous manner. Cycloalkyl denotes, e.g.. cyclopropyl. cyclobutyl and cyclopentyl. The term "halogen", either alone or in compound words such as "haloalkyl". denotes fluorine, chlorine, bromine and iodine. The total number of carbon atoms in a substituent group as indicated by the C.-C. prefix where i and j are numbers from 1 to 5. For example. C.-C 3 alkylsulfonyl would designate methylsulfonyl through propylsulfonyl. C_ alkoxyalkoxy would designate OCH 2 OCH 3 . Compounds preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are: 1. Compounds of Formula I where E is a single bond. 5 2. Compounds of Formula I where E is CH_ and R_ 2 b is H. 3. Compounds of Formula I where E is O and R_b is H. 4. Compounds of Preferred 1 where is O; 10 χ is H. F. Cl. Br. C 1 -C 2 alkyl. C χ -C 3 alkoxy, C.-C 3 alkylthio, or C,-C- alkyl. C -C alkoxy or C.-C, alkylthio substituted with 1-3 atoms of F, Cl or Br; R 2 is H or C χ -C 3 alkyl; 15 5 is H; X is C--C_ alkyl, C.-C 2 alkoxy, Cl, F. Br. I. OCF H. CH F, CF . OCH CH F, OCH 2 CHF 2 , OCH 2 CF 3 . CH 2 C1 or CH 2 Br; and 20 Y is H. C χ -C 2 alkyl. C 1 -C 2 alkoxy. CH 2 OCH 3 . CH 2 OCH 2 CH 3 . HCH 3 . N(OCH 3 )CH 3 . N(CH 3 ) 2 . CF 3< SCΪ_ 3 . OCH2,CH=CH2,, OCH2„C≡CH. OCH2„CH2,OCH3_. ) m . OCF 2 H, SCF 2 H, cyclopropyl. C=CH, C≡CCH or OCF Br. 5. Compounds of Preferred 4 where A is A-l. 6. Compounds of Preferred 5 where J is J-l. 7. Compounds of Preferred 5 where J is J-2. 35 8. Compounds of Preferred 5 where J is J-3. 9. Compounds of Preferred 5 where J is J-4. 10. Compounds of Preferred 5 where J is J-5. 11. Compounds of Preferred 5 where J is J-6. 12. Compounds of Preferred 5 where J is J-7. 13. Compounds of Preferred 6 where R is H ■ R is H. Cl. CH or OCH 3 ; X is CH 3 . OCH 3 . Cl. OC 2 H 5 or OCF 2 H; and Y is CH 3 . OCH 3 . C 2 H_.. CH 2 OCH 3 . HCH 3 . CH(OCH 3 ) or cyclopropyl. 14. Compounds of Preferred 2 where R is H; J is J-l; R. is H; 2 is H or CH 3 : A is A-l; X is CH 3 . OCH 3 , OCH 2 CH 3 . Cl or OCF 2 H; and Y is CH 3 . OCH 3 . C 2 H-.. CH 2 OCH 3 . NHCH j . CH(OCH 3 )_ or cyclopropyl. 15. Compounds of Preferred 3 where R is H; J is J-l; R χ is H: is H or CH ; A is A-l; X is CH 3 . OCH 3 . OCH 2 CH 3 . Cl or OCF 2 H and Y is CH 3 . OCH 3 . C 2 H 5 . CH 2 OCH 3 . NHCH j . CH(OCH 3 ) 2 or cyclopropyl. Compounds specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are: N-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2,3-benzothiadiazole-4-sulfonamide. m.p. 120-129°C(d); and N-[ (4-methoxy-6-methyl-1.3.5-triazin-2-yl)aminocar- bon l]-5-methoxy-l,2.3-benzothiadiazole-4-sulfon¬ amide. m.p. 176-178°C. N-[[4-ethoxy-6-(methylamino)-l,3.5.-triazin-2-yl] aminocarbonyl]-l-methyl-lH-benzotriazole-4- sulfonamide, m.p. 203-209 β C. The compounds of this invention are highly active as preemergent and/or postemergent herbicides or plant growth regulants. Some of the compounds have utility for selective weed control in crops such as oilseed rape, rice, barley, cotton and sugar beets. . DETAILED DESCRIPTION OF THE INVENTION Synthesis The following discussion represents a general outline for the preparation of the compounds of this invention. All of the syntheses described below are multistep with one or more methods being taught for each step. This allows for a wide variety of possible synthetic pathways to prepare a particular compound of Formula I. The proper choice of the synthetic pathway and the best ordering of the reaction sequences for each individual compound will be known to one skilled in the art. The compounds of Formula I can be prepared by one or more of the methods described below in Equa¬ tions 1 through 5. As shown in Equation 1, many of the compounds of Formula I can be prepared by reacting a sulfonyl iso- cyanate ( * 0) or. a sulfonyl isothiocyanate (W » S) of Formula II with an appropriate heterocyclic amine of Formula III. R. A and W are as previously defined. Equation 1 J-S0 2 N=C=W + HN-A \ J-SO,NHCN-A 1 2 i R R I I I I I I The reaction is carried out at 25° to 100 β C in an inert, aprotic solvent such as methylene chloride or xylene for 0.5 to 24 hours as taught in U.S. Patent 4.127.405. Many of the compounds of Formula I. where W is S and R is H (la), can be prepared by reacting the appro¬ priate sulfonamide of Formula IV with a heterocyclic isothiocyanate of Formula V. as shown in Equation 2. Equation 2 J-SO.NH, + S= * C=N-A —^^—> J-SO,NHCNH-A * * 2 IV V la. The reaction is carried out at 25° to 80°C in an inert, aprotic solvent such as acetone or acetonitrile in the presence of a base such as potassium carbonate for 0.5 to 24 hours. The required heterocyclic iso- thiocyanates V are prepared from the corresponding amines III which would be known to one skilled in the art as taught in EPO Publication 35.893. Many of the compounds of Formula I. where W is O (lb), can be prepared by reacting a sulfonylcarbamate of Formula VI with an appropriate amine of Formula III. as shown in Equation 3. Equation 3 II « 11 J-SO,NHCOC,H. + H-N-A > J-SO.NHCN-A 2 6 5 Dioxane z VI ill lb. The reaction is carried out at 50° to 100 β C in a solvent such as dioxane for 0.5 to 24 hours. The required carba ates VI are prepared by reacting the corresponding sulfonamides IV with diphenylcarbonate in the presence of a strong base. Compounds of Formula lb can also be prepared, as shown in Equation 4, by reacting a heterocyclic car- bamate of Formula VII with an appropriate sulfonamide of Formula IV. Equation 4 J-SO-NH + PhO -A IV VII lb The reaction is carried out at 0° to 50°C in a solvent such as acetonitrile or dioxane in the pre¬ sence of a non-nucleophilic base such as DBU for 0.2 to 24 hours. The required phenylcarbamate VII are prepared by reacting the corresponding heterocyclic amines III with diphenylcarbonate or phenylchloro- formate in the presence of a strong base. Many of the compounds of Formula lb can be prepared by reacting the sulfonamides of Formula IV with an appropriate methylcarbamate of Formula VIII in the presence of an equimolar amount of trimethyl- aluminum, as shown in Equation 5. Equation 5 J-SO 2.-N"H"2 τ C v -H « 33 O w -A IV VIII lb The reaction is carried out at 25° to 40°C in a solvent such as methylene chloride for 10 to 96 hours under an inert atmosphere. The required carbamates VIII are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a strong base. The intermediate sulfonyl isocyanates (W ■ 0) and sulfonyl isothiocyanates ( » S) of Formula II from Equation 1 can be prepared as shown in Equations 6 through 10. As shown in Equation 6, many of the sulfonyl isocyanates of Formula Ila can be prepared by the reaction of sulfonamides of Formula IV with phosgene, in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in a solvent such as xylene by the method of U.S. Patent 4.238,621. Equation 6 J-S0 2 NH 2 COCyn-BuNCO ^ J-SO..N-C-0 DABCO/XYLENE/Δ IV Ila The sulfonyl isocyanates can also be prepared from the sulfonamides by a two step procedure in¬ volving (a) reacting the sulfonamides with n-butyl¬ isocyanate in the presence of a base such as K CO at reflux in an inert solvent such as 2-butanone forming a n-butylsulfonylurea; and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent. The method is similar to a procedure taught by Ulrich and Sayigh, Newer Methods of Preparative Organic Chemistry. Vol. VI, p. 223-241, Academic Press, New York and London. . Foerst Ed. An alternative two step procedure for preparing sulfonyl isocyanates of Formula Ila is shown in Equa¬ tion 7. Equation 7 a) J - S0 2 NH 2 Δ ^ J-S0 2 N=S-0 IV IX b) IX Ila The sulfonamides of Formula IV are heated with excess thionyl chloride forming N-sulfinyl sulfonamides of Formula IX. The intermediate N-sulfinyl sulfon- amides are heated in an inert solvent such as toluene with phosgene (e.g. 2-3 equivalents) and pyridine (e.g. 0.1 equivalents) to give sulfonyl isocyanates of Formula Ila. The method is similar to that taught by Ulrich et al. J. Org. Chem 34. 3200 (1969). Alternatively, as shown in Equation 8. many of the sulfonyl isocyanates of Formula Ila can be pre¬ pared by reacting the corresponding sulfonyl chlorides X with cyanic acid salts. Equation 8 J-S0 2 C1 M ° CN > J-S0 2 N=C=0 X Ila The reaction is carried out at 25° to 100 β C in an inert aprotic solvent such as acetonitrile for 0.5-24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium iodide. Many of the sulfonyl isocyanates of Formula lib can be prepared, as shown in Equation 9. by contacting phenols of Formula XI with chlorosulfonyl isocyanate according to the teachings of Lohaus, Chem. Ber.. 105. 2791 (1972) or U.S. Patent 4.191.553. Equation 9 C1S0 NCO J-OH = > J-OS0 2 NCO XI lib Many of the sulfonyl isothiocyanates of Formula lie can be prepared, as shown in Equation 10, by con¬ tacting the sulfonamides of Formula IV with carbon ' disulfide in the presence of two equivalents of a strong base. The resulting salt is then reacted with phosgene according to the teachings of K. Hartke, Arch. Pharm.. 299. 174 (1966). Equation 10 IV He The sulfonamides of Formula IV of Equations 2, 4, 5, 6, 7 and 10 as well as the other sulfonamides required to prepare the compounds of this invention can be prepared from the corresponding sulfonyl chlorides of Formula X by contacting with either anhydrous or aqueous ammonia as shown in Equation 11, Equation 11 J-S0 X IV The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature, for reviews see: F. Hawking and J. S. Lawrence. "The Sul¬ fonamides." H. K. Lewis and Co.. London. 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds." Rein- hold Publishing Corp.. New York, 1948. Similarly, many sulfonamides of Formula IV can be prepared from the corresponding lithium reagent of Formula XII as shown in Equation 12. M represents the lithium moiety of the metalated reagents. Equation 12 " "* H-N 3H "^ J-M S0 2 " J-S0 2 M <- OSO. J-S0 2 NH 2 XII XIII IV The etalated intermediates XII are contacted with sulfur dioxide to afford the lithium sulfinates of Formula XIII. Intermediates XIII are subsequently contacted with hydroxylamine-O-sulfonic acid to afford the sulfonamides of Formula IV. The procedure for preparing similar sulfonamides by this method is taught in South African Patent Appln. 85-1568. Alternatively, many sulfonamides IV can be pre¬ pared by dealkylation of their corresponding N-t.-butyl sulfonamides XIV as shown in Equation 13. Equation 13 J-S0 2 NHC(CH 3 ) 3 CF 3 C °2 > IV or HC1/CH 3 0H XIV The reaction is carried out by contacting the N-t_butγl sulfonamide XIV with a strong acid such as trifluoroacetic acid or methanolic HC1 at 25° to 50°C for 0.5 to 24 hours. The N-t.-butyl sulfonamides XIV are readily prepared by reacting sulfonyl chlorides X with Jt-butylamine and are useful either as an aid in purification, or to enhance solubility for subsequent reactions, or to protect the sulfonamide function from competing with reactions at other parts of the mole¬ cule. The sulfonyl chlorides of Formula X of Equations 8 and 11 are important intermediates for the prepara¬ tion of the compounds of this invention. The synthesis of the required sulfonyl chloride intermediates are described in Equations 14 through 20. As shown in Equation 14. many of the sulfonyl chlorides of Formula X can be prepared by chlorosul- fonating the parent ring compounds of Formula XV. Equation 14 XV The success of this reaction depends on the nature of compounds XV and their ring substituentβ which will be known to one skilled in the art. Methods for conducting this reaction are described by E. Gilbert in "Sulfonation and Related Reactions" p. 84-88. Interscience Publishers 1965 and the references cited therein. As shown in Equation 15, many of the sulfonyl chlorides of Formula X can be prepared from the corresponding amines XVI by a Meerwein reaction. Equation 15 J-NH 2 1 ) HONO/HC1 j.βo.Cl 2) S0 2 /CuCl 2 /HOAc XVI The reaction involves diazotization of the amine XVI with sodium nitrite in aqueous HCl. followed by reaction of the diazonium salt with sulfur dioxide and cupric chloride in acetic acid analogous to the teachings of Yale and Sowinski. J.. Orq. Chem.. 25. 1824 (1960). Alternatively, sulfonyl chlorides of Formula X can be prepared by a modification of the above pro¬ cedure as shown in Equation 16. Equation 16 j NH +c i " -^ R Q NO/Organic Solvent > J-NH 3 C1 - ^ S o 2 CuCl 2 ^ J-S0 2 C1 XVIa X The amine hydrochloride salts XVIa are diazotized with an alkylnitrite in an organic solvent, such as acetonitrile or acetone, and the resulting diazonium salts are reacted with sulfur dioxide and cupric chloride to give sulfonyl chlorides X. M. Doyle, in J. Orq. Chem. 42. 2426, 2431 (1977), describes conditions for doing similar Meerwein reactions. Many of the sulfonyl chlorides of Formula X can also be prepared by oxidative chlorination of the corresponding thio compounds of Formula XVII as shown in Equation 17. R* is H. alkyl. benzyl or carbamoyl. Equation 17 XVII The reaction is carried out by addition of molecular chlorine or a chlorine equivalent to the thio compound in the presence of water at 0° to 80 β C in an aliphatic carboxylic acid solvent such as acetic acid or an inert organic solvent such as dichioro- ethane for 1 to 24 hours. Specific reaction condi¬ tions are taught by A. Wagenaar in Reel. Trav. Chim. Pays-Bas. 101. 91 (1982). Alternatively, many of the sulfonyl chlorides of Formula X can be prepared by the two-step sequence shown in Equation 18 starting from the thio compounds > XVII where R' is H (XVIIa). Equation 18 XVIla The thiol XVIIa is contacted with excess hydrogen peroxide in the presence of base to give a sulfonic acid salt which in turn is converted to the desired sulfonyl chloride by contacting with a suit¬ able reagent such as thionyl chloride or phosphorous pentachloride as known to one skilled in the art. Thiols XVIIa can also be oxidized to sulfonyl chlor¬ ides X with sodium hypochlorite using the methods taught in South African Patent Appln. 84/8844. Many of the sulfonyl chlorides of Formula X can be prepared from the corresponding lithium or Grignard reagent of Formula XII and sulfuryl chloride as shown in Equation 19. M represents either the lithium or MgX 1 moiety of the metalated reagent. Equation 19 XII The metalated intermediates XII are contacted with sulfuryl chloride to afford sulfonyl chlorides X. The procedure for preparing similar sulfonyl chlorides by this method is taught by Bhattacharya et al., J. Chem. Soc. (C). 1265 (1968). Sulfonyl chlorides of Formula Xa can be prepared from compounds of Formula XVIII by the sequence of reactions shown in Equation 20. [X] represents a suitable halogenating reagent and X represents a reactive halogen. This method is taught in U.S. Patent 4,420,325. Equation 20 J - H 3 ^ ^ J-CH 2 X XVIII XVIlb Xa Many of the S-arylthiocarbamates of Formula XVIIc (XVII. R'=C0N(CH ) ) can be prepared by the Newman-Kwart rearrangement starting with the corre¬ sponding phenols XI as shown in Equation 21. Equation 21 S S J-OH C1CN(CH 3 >2 J-0-C-N(CH 3 ) 2 Base Δ 0 tl XIX - J- -S-C- -N(CH 3 ) 2 XVIIc The phenol XI is first reacted with N.N-di- methylthiocarbamoyl chloride in the presence of a base. The resulting O-aryl-N.N-dimethylthiocarbamate XIX is then heated at 150°C to 300°C for 2 to 24 hours as taught by Newman and Karnes J. Orq. Chem.. 31. 3980 (1966) to give the desired S-aryl-N.N-dimethylthio- carbamate XVIIc. The corresponding thiols XVIIa can be obtained by hydrolysis of the thiocarbamates XVIIc. Many of the sulfides of Formula XVII where R' is alkyl or benzyl can be prepared by reacting a halo- compound of Formula XX with an appropriate mercaptan in the presence of a base as shown in Equation 22. R' is alkyl or benzyl and X' is F. Cl or Br. Equation 22 R'-SH J-X' J-S-R' Base XX XVII The reaction is carried out in a solvent such as DMF at 25° to 150 β C for 0.5 to 24 hours. The halo- compounds XX must not contain functionality which can be attacked by a mercaptide anion as will be known to one skilled in the art. The amines of Formula XVI in Equation 15 can be prepared by reduction of the corresponding nitro com¬ pounds of Formula XXI as shown in Equation 23. Equation 23 J-N0 2 Reduction > ^^ XXI XVI The reduction of nitro compounds to amines can be carried out by any of several known methods as described in Preparative Organic Chemistry. 4 Ed., p. 557-563. John Wiley and Sons. New York and London, G. Hilgetag and A. Martini Ed. The amines of Formula XVI are versatile interme¬ diates for preparing phenols of Formula XI and halo- compounds of Formula XX by the diazotization reactions of Equation 24. Compounds XXII represent diazonium salts derived from amines XVI. Equation 24 Hodgson and Dodgson. in J. Soc. Dyers Colour. 64. 65 (1948). teach methods for conducting the trans¬ formation of Equation 24 where J » J-l. J-2 (Q=S). For a general review of methods for diazotizing amines and reactions of diazonium salts see K. Schank. Ch. 14. p. 645 and D. J. Wulfman. Ch. 8. p. 247 in "The Chemistry of Diazonium and Diazo Groups." S. Patai Ed.. Wiley. 1978. Phenols of Formula XI can also be prepared from ethers of Formula XXIII. where A represents a suitable alkyl or arylalkyl protecting group, as shown in Equa¬ tion 25. T. Green teaches methods for deprotecting ethers to phenols in "Protective Groups in Organic Synthesis." Ch. 2, p. 10. Wiley, 1981. Equation 25 j -OA deprotection^ J _ 0H XXIII XI Metalated intermediates of Formula XII in Equa¬ tions 12 and 19 can be prepared from halocompounds of Formula XX by methods well known in the art. I 29 Many of the nitro compounds of Formula XXI in Equation 23 can be prepared from ring compounds XV by the reaction shown in Equation 26. Equation 26 Ό HNO J-H Δ > -J-N0 2 XV XXI 0 The success of this electrophilic substitution reaction depends on the nature of compounds XV and their ring substituents which will be known to one skilled in the art. Methods for nitrating many of the compounds of Formula XV are taught in "Comprehensive 15 Heterocyclic Chemistry" Vol. 5, Sec. 4.11 and Vol. 6. Sec. 4.22. 4.24. 4.26, K. T. Potts. Ed., Pergamon Press, Oxford 1984 and the reference cited therein. A general review of nitrating procedure is taught by J. G. Hoggett et al. in "Nitration and Aromatic 20 Reactivity", Cambridge University Press, 1971. Many intermediates of Formula XXIV (J-G) can be prepared by the ring-forming reactions exemplified by Equations 27 to 31. In these equations. G represents the S0 2 H 2 . S0 2 NHC(Me) 3 . H. SR'. CH 3 . X'. N0 . or OA 25 moiety, as defined above, of Compounds IV, XIV, XV, XVII, XVIII, XX, XXI or XXIII respectively. The suitability of a given reaction to form a particular compound of Formula XXIV will depend on the nature of G and will be known to one skilled in the art. 30 35 Equation 27 XXIVa XXIVa XXIVC Many of the compounds of Formula XXIV where J * J-l (XXIVa, XXIVb. XXIVc) can be prepared by the diazotization reactions of Equation 27. Methods for these reactions are described by a) L. L. Bambas. "The Chemistry of Heterocyclic Compounds", Vol. 4, p. 10, A. Weisberger Ed., Interscience. New York 1952: b) P. Kirby et al.. J. Chem. Soc. (C). 2250 (1970); c) R. W. Hoffmann et al.. Chem. Ber.. 98. 3470 (1965); d) H. Wamhoff, "Comprehensive Heterocyclic Chemistry", Vol. 5, p. 669, K. T. Potts Ed., Pergamon Press, Oxford 1984; and the references cited therein. Many of the compounds of Formula XXIV where J = J-2 can be prepared by the methods described in Equation 27, but starting with compounds in which the G and R_b substituents are interchanged. Equation 28 XXIVd XXIVd c) 111 XXIVd XXIVe f) XXIVf XXIVC Many of the compounds of Formula XXIV where J a j-3 (XXIVd-f) can be prepared by the reactions of Equation 28. Methods for these reactions are described by a), b). c) M. M. Campbell, "Comprehensive Organic Chemistry", Vol. 4, p. 961, Barton and Ollis Ed.. Pergamon Press, Oxford, 1979; d) W. R. Shipman, "Heterocyclic Compounds". Vol. 7. Ch. 7. R. C. Elderfield Ed.. Wiley, New York. 1961; e). f) H. Wamhoff. "Comprehensive Heterocyclic Chemistry", Vol. 5. p. 669; K. T. Potts Ed.. Pergamon Press, Oxford. 1984; and the references cited therein. Equation 29 XXV XXIVq XIVh c) xxivh XXIVi H,NSO,NH- RX d) XXV —- -—^-^ XXIVi XXIVi (R 4 -R 3 »H) (R 4 »R 3 -H) e) xxivi 34 XXIV Many compounds of Formula XXIV where J * J-4 (XXIVg-m) can be prepared by the reactions of Equation 29. Methods for these reactions are described by a) M. Bryce, J. Chem. Soc. Perk. Trans. I. 2591 (1984): b), c) R. M. Acheson et al.. J. Med. Chem.. 24. 1300 (1981): d) J. D. Carson. U.S. Patent 3,177.221: e), f), g) G. W. Fischer and T. Zimmermann, "Comprehensive Heterocyclic Chemistry". Vol. 6. p. 851. K. T. Potts Ed.. Pergamon Press, Oxford, 1984; and the references cited therein. 35 Equation 30 a) solvent b) Zn XXIVn (R 4 -H) Many of the compounds of Formula XXIV where J « J-5 (XXIVn) can be prepared by the reactions of Equation 30. Methods for these reactions are described by a) R. A. Abramovitch. J. Orq. Chem.. 42. 2920 (1977); b) R. W. Hoffmann et al.. Chem. Ber.. 98. 3470 (1965): and the references cited therein. Equation 31 Many of the compounds of Formula XXIV where J > J-6 (XXIVo) can be prepared as shown in Equation 31. A. W. Wagner and R. Banholzer teach methods for such reactions in Chem Ber.. 96,, 1177(1963). Similarly, many compounds of Formula XXIV where J » J-7 can be prepared as described in Equation 31. but starting with compounds in which the G and R c b substituents are interchanged, The heterocyclic amines of Formula III in Equa¬ tions 1 and 3 can be prepared by methods known in the literature, or simple modifications thereof, by one skilled in the art. For a review of the synthesis and reactions of 2-amino- and 2-methylaminopyrimidines III (A=A-1, Z=CH) see The Chemistry of Heterocyclic Compounds. Vol. 16. Wiley-Interscience. New York (1962). For a review of the synthesis and reactions of 2-amino- and 2-methylaraino-s-triazines III (A=A-1. Z=N) see The Chemistry of Heterocyclic Compounds. Vol. 13. Wiley- Interscience. New York (1959). F. C. Schaefer. U.S. Patent No. 3,154.547 and F. C. Schaefer and K. R. Huffman, J. Orq. Chem.. 28.. 1812 (1963). EP-A No. 84.224 and W. Braker et al., J. Chem. Soc. 69. 3072 (1947) describes methods for preparing aminopyri idines and triazines substituted by acetal groups such as dialkoxymethyl or 1.3-dioxolan-2-yl. South African Patent Application No. 83/7434 describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl. The 5.6-dihydrofuro[2.3-d]pyrimidine-2-amines, the cyclopenta[d]pyrimidines-2-amines (III, A is A-2) and the 6.7-dihydro-5H-pyrano[2.3-d]pyrimidin-2-amines (III, A is A-3) can be prepared as taught in EP-A No. 15.683. The furo[2.3-d]pyrimidin-2-amines (III, A is A-4) are described in EP-A No. 46.677. Compounds of Formula III. where A is A-5, are described in EP-A-73,562. Compounds of Formula III. where A is A-6. are described in EP-A-94,260. The amines of Formula III where A is A-7 can be prepared by methods taught in European Publication No. 125.864 (published 11/21/84) or by suitable modifica¬ tions that would be obvious to one skilled in the art. The preparation of the compounds of this inven¬ tion is further illustrated by the following examples. Example 1 5-Methoxy-l,2.3-benzothiadiazole-4-sulfonyl chloride To a stirred solution of 50 mL of chlorosulfonic acid at 0 β C was added 4.15 g of 5-methoxy-l,2,3-benzo- thiadiazole under an inert atmosphere. The resulting mixture was heated at reflux for 30 minutes. After cooling to room temperature, the reaction mixture was added to 600 mL ice-water mixture. The precipitate was collected, washed with water and ether, and air dried to give 5.6 g of the title compound as a white solid, m.p. 131-134°C. 90 MHz NMR (CDCl 3 )δ: 4.27 (s. 3H, CH j ) 7.71 (d, 1H, arom.); and 8.51 (d. 1H. arom.). IR (nujol) 1375, 1180. 832 cm "1 . Example 2 2.1.3-Benzothiadiazole-4-sulfonyl chloride To a stirred solution of 100 mL of chlorosulfonic acid at 0°C was added 10.0 g of 2,1,3-benzothiadiazole under an inert atmosphere. The resulting mixture was heated at reflux for 30 minutes and cooled to room temperature. The reaction mixture was added dropwise to 1000 mL ice. The precipitate was collected, washed with water, and air dried to give the title compound as a beige solid, m.p. 146-148°C. 90 MHz NMR (CDC1 )δ: 7.83 (m. 1H, arom.); and 8.42 (m. 2H, arom.). IR (nujol) 1370. 1165. 835. 815. 750, 730 cm "1 . Example 3 2.1.3-Benzoxadiazole-4-sulfonamide To a stirred solution of 3.0 g of 2,1,3-benzoxa- diazole-4-sulfonyl chloride and 200 mL of tetrahydro- furan at -30°C was added 10 mL of ammonia under an inert atmosphere. The resulting suspension was stir¬ red at ambient temperature for 3 hours. Concentrated ammonium hydroxide (20 mL) and water (20 mL) were added. The reaction was extracted with ethyl acetate and the organic extracts were combined, dried over magnesium sulfate, filtered, and stripped to give a crude solid. Recrystallization from chlorobutane- ethanol afforded 1.82 g of the title compound as an orange-tan solid, m.p. 157-159 β C. 90 MHz NMR (CDCl 3 -DMSO-d 6 )δ: 7.6 (m. 3H. arom. and NH 2 ); and 8.09 (m, 2H. arom.). IR (nujol) 3300. 3200. 1330, 1160 cm "1 . Example 4 l-Methyl-lH-benzotriazole-7-sulfonamide To a stirred solution of 1.5 g of 1-methyl-lH- benzotriazole-7-sulfonyl chloride and 75 mL of tetra- hydrofuran at 0°C was added 5 mL of ammonia under an inert atmosphere. The resulting suspension was stir¬ red at ambient temperature for 15 hours. Concentrated ammonium hydroxide (10 mL) and brine (10 mL) were added. The aqueous layer was adjusted to pH 7 with concentrated hydrochloric acid and was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate. filtered, and stripped to afford 1.38 g of the title compound as a white solid, m.p. 198-200°C. 90 MHZ NMR (CDCl 3 -DMSO-d 6 )δ: 4.63 (s, 3H, CH 3 ); 7.43 (m, 1H, arom.); 7.80 (s. 2H, NH 2 ) and 8.13 (m, 2H, arom.) IR (nujol) 3250. 1315, 1150 cm-1 Example 5 N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-l.2,3-benzothiadiazole-4-sulfonamide A solution of 5-methoxy-1.2.3-benzothiadiazole-4- sulfonamide (0.20 g) and of 0-phenyl-N-(4,6-dimethoxy- pyrimidin-2-yl)carbamate (0.24 g) in 7 mL of aceto¬ nitrile was treated with 0.12 mL of 1,8-diazabicyclo- [5.4.0]undec-7-ene. The solution was stirred for 2 hours. After diluting the reaction with water (10 mL) and acidifying it with IN hydrochloric acid, the resulting precipitate was filtered, washed with water and ether, and air dried to give 0.24 g of the title compound as a beige solid, m.p. 120-129°C with decomposition. 200 MHz NMR (DMSO-do-)δ: 3.94 (s. 6H, OCH,3); 3.99 (S. 3H, NCH 3 ); 6.04 (s. 1H. CH); 7.92 (d, 1H, arom.); 8.74 (d. 1H. arom.); 10.57 (s. 1H, NH); and 13.09 (s. 1H. NH). IR (nujol) 1700 cm " . Example 6 N-[(4-Methoxy-6-methyl-1.3,5-triazin-2-yl)aminocar- bonyπ-l-methyl-lH-benzotriazole-4-sulfonamide A solution of l-methyl-lH-benzotriazole-4-βul- fonamide (0.32 g) and of 0-phenyl-N-(4-methoxy-6- methyltriazin-2-yl)carbamate (0.42 g) in lOmL of acetonitrile was treated with 0.24 mL of 1,8-diaza- bicyclo[5.4.0]undec-7-ene. The mixture was stirred for 2 hours. After diluting the reaction with water (15 mL) and acidifying it with IN hydrochloric acid, the resulting precipitate was filtered, washed with ς water and ether, and air dried to give 0.40 g of the title compound as a white solid, m.p. 134-136°C with decomposition. 200 MHz NMR (DMSO-d g )6: 2.46 (s, 3H. CH 3 ); 4.02 (s. 3H. OCH 3 ); 4.35 (S. 3H. NCH,); 0 3 7.76 (m. 1H, arom.); 8.05 (d, 1H. arom.); 8.27 (d, 1H, arom.); 10.87 (s, 1H. NH); and 12.85 (s. 1H. NH). IR (nujol) 1730 cm "1 . Example 7 N-[(4-Ethoxy-6-(methylamino)-1,3.5-triazin-2-yl)amino- carbonyπ-l-methyl-lH-benzotriazole-4-sulfonamide 20 A solution of l-methyl-lH-benzotriazole-4- sulfonamide (0.32g) and of 0-phenyl-N-(4-ethoxy-6- (methylamino)triazin-2-yl)carbamate (0.46g) in lOmL of acetonitrile was treated with 0.24 mL of 1.8-diaza- bicyclo[5.4.0]undec-7-ene. The mixture was stirred 25 for 2 hours. After diluting the reaction with water (15 mL) and acidifying it with IN hydrochloric acid, the resulting precipitate was filtered, washed with water and ether, and air dried to give 0.31g of the title compound as a white solid, m.p. 203-209°C. 30 200 MHz NMR (DMSO-d fi )δ: 1.30 (m. 3H. CH 3 : 2. 81 and 2. 96 (m. 3H. NHCH 3 ) ; 4. 35 (bs . 5H. OCH 2 and NCH 3 ) ; 7. 6-8 .4 (m. 4H. NH and arom) ; 10. 28 and 10. 46 ( s , 1H. NH) ; 35 13 . 11 and 13 .76 ( s . 1H. NH) . IR (nujol ) 1730. 1720 cm "1 . Example 8 N-[(Butylamino)carbonyl]-l-methyl-lH-benzotriazole- 4-sulfonamide To a stirred mixture of l-methyl-lH-benzotriazole-4-sulfonamide (7.5g). potassium carbonate (5.1g), and 2-butanone (250 L) was added butylisocyanate (3.9mL) under an inert atmosphere. The reaction was heated at reflux for 15 hours. The cooled reaction mixture was poured into ice (500 mL), acidified with concentrated hydrochloric acid, and extracted with ethyl acetate-tetrahydrofuran. The extracts were dried over magnesium sulfate, filtered, and evaporated. The crude solid was washed with chlorobutane-hexanes and air dried to give 8.65g of the title compound as a white solid, m.p. 170-173°C. 90 MHZ NMR (CDC1 3 - DMSO-d )δ: 0.80 (m. 3H. CH 3 ); 1.27 (m. 4H. CH 2 ); 2.97 (q, 2H. CH 2 ); 4.41 (S, 3H. NCH,); 3 6.40 (t. 1H. NH); 7.67 (m, 1H, arom); 8.07 (m, 2H. arom); 10.73 (s, 1H, NH). IR (nujol) 1650 cm -1 Example 9 l-Methyl-lH-benzotriazole-4-sulfonylisocyanate To a stirred mixture of N-[(butylaraino)ca bonyl]-l-methyl-lH-benzotriazole-4- sulfonamide (8.25g), 1.4-diazabicyclo[2.2,2]octane (catalytic amount), and xylenes (175mL). heated at reflux under a nitrogen atmosphere, was added phosgene (2mL) in small portions over 1 hour. The resulting suspension was heated an additional 0.5 hours and was cooled prior to filtering off the insoluble material. The filtrate was evaporated to give 3.05g of the title compound as a pale yellow solid. IR (nujol) 2260 cm " . The compound was immediately diluted to lOOmL with dry acetonitrile and stored under nitrogen to give a 0.125M solution of the title compound for further use. Example 10 N-[(5.6-Dihydro-4-methγlfuro(2.3-d)pγriraidin-2-yl)- aminocarbonyll-l-methyl-lH-benzotriazole-4-sulfonamide To a stirred solution of 5.6-dihydro-4-methyl- furo(2.3-d)pyrimidin-2-amine (0.08g) and 1.4-diaza- bicyclo[2.2,2]octane (catalytic amount) in acetonitrile (5mL) was added 0.125M l-methyl-lH-benzotriazole-4- sulfonylisocyanate in acetonitrile (4.0mL) under a nitrogen atmosphere. After stirring for 4 hours, the reaction was diluted with water (20mL) and the precipitate was filtered, washed with water and ether. and dried to give 0.09g of the title compound as a white solid, m.p. 234-240°C with decomposition. 200 MHz NMR (DMSO-d 6 )δ: 2.40 (s. 3H. CH 3 ); 3.18 (t. 2H. CH ); 4.34 (S. 3H. NCH ): 4.70 (t. 2H, OCH ); 7.74 (t. 1H, arom): 7.98 (d. 1H, arom); 8.23 (d, 1H. arom): 10.38 (s. 1H. NH); 13.92 (S, 1H, NH). IR (nujol) 1720. 1700 cm "1 Example 11 1-Methyl-lH-l,3.2-benzodithiazole-4-sulfonamide. 3,3-dioxide To a stirred suspension of 3-methylthio-1.2- benzenedisulfonamide (1.55g) and methanol (50mL) was added bromine (2mL). The reaction was stirred under a nitrogen atmosphere for 6 days. It was stirred for an hour after adding 6N sodium hydroxide (2mL) and water (6mL). The resulting precipitate was filtered, washed with chlorobutane and ethanol, and dried to give 1.36g of the title compound as an off-white solid: m.p. 249-254 β C. 90 MHz NMR (DMSO-d ) 8: 3.12 (S.3H. CH 3 ) 7.42 (S.2H, NH 2 ) 8.0-8.4(m. 2H. arom.) 8.53 (d. 1H. arom.) IR (nujol) 3400.3250 cm -1 General Structures for Tables I through VI Table I JSO HI 4CHA (λ « A-l) « X J u E R Λ < 1 1 1 rn.p . CC) J-l 0 - H K H s CH 3 CH 3 CH 207-209 J-l 0 - H H H s CH 2 CH 2 CH 3 CH, CH J-l 0 - H H H s OCH 3 CH 3 CH 206-208 J-l 0 - H K H s ocr 3 CH 3 CH J-l 0 - K H K s OCH.CH.OCH. CH 3 CH 2 2 3 J-l 0 - H H H s SCH 3 CH 3 CH J-l 0 - H H H s Br CH 3 CH J-l 0 - H H H s M(CH 3 ) 2 ∞s CH J-l 0 - H H H s OCH OCH 3 CH 222-224 J-l 0 - H H H s »(CH 3 ) 2 OCH-CH 3 CH J-l 0 - H H H s Cl OCH. CH 211-213 J-l 0 - H H H s Br OCH. CH J-l 0 - H H H s OCH KHCH. V 263-271(d) 3 J-l 0 - H H H s CH 3 CH CT 3 J-l 0 - H H H s CH 3 CH 3 J-l 0 - H H H s CH 3 OCH 179-181 J-l 0 - H H H s ™3 OCH.CH.CH.CH. 2 2 2 3 J-l 0 - H H H s OCH 3 OCH 183-184 J-l 0 - H H H s MHCH OCH-CH. 233-234 2 3 J-l 0 - K H H s OCH CM J-l 0 - H H OCF.H s OCH 2 OCH. CH J-l 0 - H 5-CH- H s OCH OCH. J-l 0 - H 5-CH H s OCH ∞S J-l 0 - H 5-CH 3 H s OCH 3 CH j CH J-l 0 - H 5-CH. H s 0CH 3 OCH 3 CH J-l 0 - H 5-CH(CH 3 ) 2 H s OCH OCH 3 CH J-l 0 - H 5-CF 3 H s OCH 3 OCH CH J-l 0 - H 5-r H s OCH, OCH- CH Table I (continued) J w τ 8 h °1 X £ 2 Ji.P . CC) J-l 0 - H 5-r H S OCH OCHj 1 J-l 0 - H 5-Cl H S 0CH 3 OCH 3 ■ J-l 0 - H 5-C1 H s OCH OCH 3 CH J-l 0 - H 5-Cl H s OCH 3 CH ∞S J-l 0 - H 5-Cl H s Cl OCH 3 CH J-l 0 - H 5-Cl H s H 3 CH 3 « J-l 0 - H 5-Br H s CH 3 OCH M J-l 0 - K 5-BΓ H s CH 3 OCHj CH J-l 0 - H 5-SO H s CH 3 OCH CH J-l 0 - H 5-HO. K s OCH CT 3 a J-l 0 - H 5-OCH H s H H CH J-l 0 - H 5-OCH H s H CH m 3 J-l 0 - H 5-OCH 3 H s CH 3 ∞a CH 195-198 J-l 0 - H 5-OCH 3 H s 0CH 3 ∞a CH 192-194 J-l 0 - H S-OCH K s OCH 2 CF 3 CH OT 3 • J-l 0 - H 5-OCH 3 H s SCH CH ∞S J-l 0 - H 5-OCH 3 H s 0CH 3 C L CH 120-129(1.) J-l 0 - H 5-OCH 3 H s Cl OCH CH 130-137(<1) J-l 0 - H 5-OCH H s OCH 3 OCH 3 V 180-181 J-l 0 - H 5-OCH 3 H s CH 3 OCHj II 176-178 J-l 0 - H 5-OCH 3 H s CH 3 CH 1 190-191 3 J-l 0 - H 5-OCH H s OCH CH HHCH M J-l 0 - H 5-0CH 3 H s OCH C=CH H J-l 0 - H S-0CH 3 H s OCH OCHjCHCH -T J-l 0 - H 5-OCH 3 H s OCH 3 CH-SO-CH- -I . 2 2 3 J-l 0 - H 5-OCH 3 H s OCH 3 CH-COCH.CH. H 2 2 3 J-l 0 - H 5-S0 2 _l(CH 3 ) 2 H s OCH 3 CH 3 ■ J-l 0 - H 5-S0 2 H(CH 3 > 2 H s OCH CH 3 CH J-l 0 - H 5-S0,HHCH,ClI H 2 2 s OCH CH 3 CH J-l 0 - H 5-S0 2 H H s OCHj CH 3 CH J-l 0 - H 5-SCH 3 H s OCH 3 CH 3 CH J-l 0 - H 5-S0CH CH H s OCH 3 CH 3 CH Table I (continued) m.p.CC) 220-222 219-220 206-209 202 . 205 ^ , 5 Table I (continued) j u E E !ι !_. !_, * . Y z m.p.CO J-l 0 - H H H CH 3 OCH 3 CH S0 2 J-l 0 - H H K so 2 Cl OCH CH J-l 0 - H H H so 2 Cl H(CH 3 ) 2 CH J-l 0 - H 5-CH.CF, H OCH H 2 3 so 2 CH 3 J-l 0 - H 5-Br H so 2 OCH 11 ra 3 ■ ° J-l 0 - H 5-OCH CH H so 2 CH 3 OCH ■ J-l 0 - H 5-OCF 3 H so 2 CH 3 OCH 3 CH J-l 0 - K 5-OCF.H H 2 H so 2 OCH C ^S J-l 0 - H 5-H(CH 3 2 H so 2 CH 3 OCH CH J-l 0 - H 5-H(CH 3 ) 2 H OCH OCH CH S0 2 J-l 0 - H 5-*(CH 3 ) 2 H so 2 OCH OCH * L5 J - χ 0 - H 5-H(CH 3 ) 2 H so 2 OCH 3 CH ■ 3 J-l 0 - K 6-C1 H so 2 OCH 3 CH II 3 J-l 0 - H 6-C1 H so 2 OCH CH CH 3 J-l 0 - H 6-OCH H so 2 OCH 3 CH CH 3 J-l 0 - H 6-OCH H so 2 OCH CH « 3 J-l 0 - H 6-CH H so 2 0CH 3 ■ ∞S J-l 0 - H 6-CH H so 2 OCH CH 3 u 20 j-i 0 - H 6-SCH CH H so 2 OCH > m 3 J-l 0 - H 6-SCH H so 2 OCH CH 3 II J-l 0 - H 6-SCH H so 2 OCH CH 3 CH J-l 0 - K H H m CH 3 H CH J-l 0 - H H K m CH 3 CH 3 CH J-l 0 - H H Cl HH OCH 3 CH 3 CH 0 - H H H HH OCH CH 3 H _>ς J'x 25 J-l 0 - H H H HH OCH 3 H(CH 3 ) 2 V J-l 0 - H 5-Cl H HH OCH CH 3 II J-l 0 - H 5-Cl H m OCH CH 3 CH J-l 0 - H 5-Cl H HH OCH 3 OCH 3 CH Λ J-l 0 - H 6-OCH H HH OCH OCH 3 CH J-l 0 - H 6- CH H HH CH 3 OCH CH 1 30 J - 1 0 - H H H HCH CH 3 OCH CH 210-216 35 Table I (continued) J « E i ϋ X z m. p . CO J-l 0 - H H K HCK CH CH, CH 3 216-218 J-l 0 - H H H HCH 3 SCH H 3 CH «-. J-l 0 - H H H HCH 3 OCH 3 OCH 3 CH 195-200 J-l 0 - H H H HCH OCH 3 0CH 3 194-197 J-l 0 - H H H HCH. OCH 3 134-136 (d) 10 J-l 0 - H H H HCH 3 CH, CH, 221-226 J-l 0 - H H H HCH 3 »( H 3 2 CH 3 J-l 0 - H H K HCH 3 VHCH 3 OCH j CH. 203-209 J-l 0 - H H H HCH. HHCH OCH. 265-270(d) J-l 0 - H H H HCH 3 Cl OCHj CH 123-126 (d) J-l 0 - H " H H HCH. OCH OCH,, 0CH 3 CH 15 J-l 0 - H H K HCH, OC ft, °°A V 154-159 o J-l 0 - H H H HCH 3 CCH 3 CH CT 3 J-l 0 - H H H MCH. CH 3 CH(OCH 3 ) 2 CH J-l 0 - H H H HCH 3 *(CH 3 2 OCH- 197-200 J-l 0 - H H H HCH. H(CH 3 2 C 2 H- 193-196 J-l 0 - H H H HCH 3 ocH 2 cr 3 H(CH 3 ) 2 185-188 20 J-l 0 - H H H HCH 3 SC 2 H 5 MHCH, 232-234 J-l 0 - H H H HCH. HHCH j OCH(CH 3 ) 2 217-221(d) J-l 0 - H H H HCH 3 OCH 3 IKCH.X-H-CH 192-193(d) J-l 0 H H H HCH 3 OCH 3 HHCH-OI 190-195(d) J-l 0 - H H H HCH 3 CH OCH 2 C=CH 120-124 (d) 3 J-l 0 - H H H HCH 3 OCH CF HHCH 3 229-235 (d) J-l 0 - H H H HCH. ■HCH. CH OC 2 H 5 218-221 25 J-l 0 - H K H HCHj CH, CΆJXH. CH 193-195 J-l 0 - H 5-CH 3 H HCH 3 CH 3 0CH 3 CH 212-214 J-l 0 - H 5-CH 3 H HCH. OCH 3 H 177-183 J-l 0 - H H Br HCH 3 CH 3 OCH 3 CH J-l 0 - H 5-CH 3 H HCH- CH 3 CH 226-228 CT 3 J-l 0 - H 5-CH 3 H HCH 3 OCH 3 OCH 3 CH 194-197 J-l 0 - H 5-CH 3 H MCH 3 OCH 3 Cl CH 203-205 30 J-l 0 - H 5-OCH. H HCH. CH. OCH. H 35 Table I (continued) J w E R i X Y z m.p. CO J-l 0 - H 5-OCH 3 H HCH OCH CH 3 V J-l 0 - H 5-OCH H HCH CH, CH 3 H J-l 0 - H 5-OCH, H HCH OC 2 H 5 HHCH H J-l 0 -. H 5-OCH H HCH CH 3 CH ra 3 J-l 0 — H 5-OCH K HCH « OCH CH J-l 0 _, H 5-OCH, H HCH 3 OCH OCH 3 CH OCH CH J-l 0 — H 5-OCH K HCH Cl J-l 0 - H 5-OCF . H ICH Cl OCH CH 2 J-l 0 — H 5-Cl H HCH 3 Cl OCH CH CH J-l 0 — H 5-Cl H HCH 0CH 3 CH 3 _, CH If J-l 0 H 5-H0 2 H HCH OCH 3 3 . J-l 0 - K 5-H0 2 H HCH OCH, HHCHjCHj H J-l 0 -. H 5-CH H MCH 3 OCH 3 1 ra J-l 0 — H 5-CH H HCH OCH CH, CH J-l 0 -. H 6-Br H HCH 3 CH H 3 m 3 J-l 0 _ B H 6-Br K ■CH CH, OCM ■ J-l 0 _ K 6-CH 3 H ■CH, CH 3 m z CH 215-217 04-208 J-l 0 H 6-CH 3 H HCH 3 OCH CH 2 ∞s 9-212 J-l 0 _ H 6-CH 3 H HCH 3 OCH. OCH CH 20 3 J-l 0 H 6-CH 3 H HCH 3 CL OCH CH 208-212 J-l 0 H 6-CH 3 H HCH 3 CH 3 CH 3 H 141-143(d) J-l 0 H 6-CH H HCH 3 CH 3 OCH H 198-205 (d) J-l 0 _ H 6-CH H HCH OCH 3 OCH ■ 186-195 J-l 0 — H 6-CH H HCH "A HHCH H 234-237 J-l 0 — H 6-SCH 3 H HCH 3 CH 3 OCH 3 ■ J-l 0 — H 6-SCH 3 H HCH 3 CH 3 OCH 3 CH J-l 0 - H 6-H(CH 3 ) 2 H HCH 3 CH 3 OCH CH J-l 0 - H 6-H(CH 3 ) 2 H HCH 3 CH 3 0CH 3 H J-l 0 - H H H HC 6 H 5 CH 3 OCH 3 H J-l 0 . H 5-Cl H HCH C H. CH, OCH 3 H OCH ■ J-l 0 - H S-OCH 3 H HCH.CHCH, 2 2 "> CH ■ J-l 0 . H 6-OCH H HCH CH 3 O J-l 0 - H 6-HHCH H HCH.CH,C1 OCH H 2 2 CH 3 51 Table I (continued) J-l 0 - H 6-C0.CH, H HOCH CH, OCH 3 ■ J-l 0 - CH. H H HCH CH 3 OCH 3 1 J-l 0 - CH 3 5- -OCH. H S CH CH 3 CH J-l 0 - CH 3 5- -Cl H HH CH, OCH. CH J-l 0 - CH 3 6-0CH 3 H S OCH CH ∞S J-l 0 - 6- -S(CH 3 ) 2 H S m 3 OCHj OCH 3 CH J-l 0 CH 2 H H H s OCH CH 3 ■ J-l 0 CH, H H H s OCH. OCH CH J-l 0 CH 2 H H H HCH 3 OCH C1L CH 3 J-l 0 CH. H 5- •Cl H HCH OCH 3 OCH 3 CH J-l 0 CH 2 H 5-0CH, H S OCH 3 OCH CH J-l 0 0 H H H s OCH 3 OCH, CH J-l 0 0 H 5-OCH. H s OCH OCH, CH J-l 0 0 H 5- ■OCH. H s OCH 3 OCH. ■ J-l 0 0 H H H HCH 3 OCH OCH, ■ J-l 0 0 H H H HCH 3 OCH OCH, CH J-l s - H H H 8 OCH j OCH i CH J-l S - H 5- •H(CH_) 2 H S OCH 0CH 3 CH J-l s - H 5- •OCF H S OCH OCH, CH J-l s - H 6-OCH. H s OCH CH 3 CH J-l S - H H H HCH. OCH 3 0CH 3 CH J-l s - H H H HCH_C.H 5 OCH 3 OCH, CH J-l s - H 5- Cl H HCH 3 OCH 3 OCH, CH J-l s - H 6- SCH 3 H HCH. OCH 3 OCH. CH J-l s CH 2 H H H HCH 3 OCH OCH, CH J-2 0 H H H S CH 3 CH 3 CH 207-208(d) J-2 0 - H H H s CH j CH j CH. CH 3 CH J-2 0 - H H H s OCH 3 CH 3 CH 195-197 J-2 0 - H H H s OCF 3 CH 3 CH J-2 0 - H H H s OCH,CH-OCH_ CH 2 2 3 ∞S J-2 0 - H H H s OCH. OCH 3 CH 220-223(d) . J-2 0 - H H H s Br CH 3. CH J-2 0 - H H H s H(CH 3 )_ CH 3 CH J-2 0 - H H H s H(CH 3 ) 2 OCH j CH J-2 0 - K H H s H(CH 3 2 OCH CH CH Table I (continued) J W E R !ι h. 5ι X Y Z a.p . CC) J-2 0 - H H OCH, s Cl OCH, CH J-2 0 - H H H s Br OCH CH J-2 0 - H H H 8 CH, HHCH CH J-2 0 - H H H S CH ra 3 CT 3 J-2 0 - H H H s CH, CH, J-2 0 - H H H s OCH, 187-196 (d) CT 3 J-2 0 - H H H s OCHjCH CHjCH, ∞S J-2 0 - H H H s 0CH 3 OCH, 198-200(d) J-2 0 - H H H s HHCH 3 OCH CH, J-2 0 - H H K s 0CH 3 Cl J-2 0 - H 6-CH, H s OCH OCH J-2 0 - H 6-CH, H s OCH, CH, J-2 0 - H 6-CH H s OCH CH, CH J-2 0 - H 6-CH, H s OCH, OCH, CH J-2 0 - H 6-CH(CH 3 ) 2 H s OCH, OCH CH J-2 0 - H 6-CF, H s OCH, OCH, CH J-2 0 - H 6-F H s OCH OCH, CH J-2 0 - H 6-F H s OCH, OCH ■ J-2 0 - H 6-C1 H s OCH OCH, I J-2 0 - H 6-C1 H s OCH, OCH, CH J-2 0 - H 6-C1 H s OCH CH, CH J-2 0 - H 6-C1 H s Cl OCH, CH J-2 0 - H 6-C1 * H s OCH, H ∞a J-2 0 - H 6-Br H s CH, OCH 1 J-2 0 - H 6-Br H s CH, OCH, CH J-2 0 - H 6-H0 2 H s CH, OCH, CH J-2 0 - H 6-H0. H s OCH, H m 3 J-2 0 - H 6-OCH H s H H CH J-2 0 - H 6-OCH, H s H CH, CH J-2 0 - H 6-OCH, H s CH, CH, CH J-2 0 - H 6-OCH H s OCH, CH, CH J-2 0 - H 6-OCH, H s OCH-CF- CH, CH 2 3 Table I (continued) K ϋ h. 2ι s Y 1 m. p . CO J U E J-2 0 - H 6- CH, H s SCH, CH, CH J-2 0 - H 6-OCH, H s OCH 3 OCH CH J-2 0 - H 6-OCH, H s Cl OCH, CH J-2 0 - H 6-OCH, H s OCHj OCH, J-2 0 - H 6-OCH H s OCH CT 3 J-2 0 - H 6- CH H 8 CH, «» J-2 0 - H 6-OCH H s OCH CH, HHCH, J-2 0 - H 6-OCH H s OCH 3 C=CH J-2 0 - H 6-OCH, H s OCH 3 OCH.CHCH- 2 2 J-2 0 - H 6-OCH, H s OCH 3 CH-SO-CH- 2 2 3 J-2 0 - H 6-OCH, H s OCH 3 CH j COCH j CH, J-2 0 - H 6-S0 2 H(CH 3 ) 2 H s OCH, CH, J-2 0 - H 6-S0_H(CH 3 ) 2 H s OCH, CH, CH O.HHCH-CH H H J-2 0 - H 6-S 2 2 s OCH, CH, C J-2 0 - H 6-S0 2 H H s OCH, CH, CH J-2 0 — H 6-SCH, H s OCH, CH ^ J-2 0 - H 6-SOCH-CH, H 2 3 s OCH, CH, CH J-2 0 - H 6-S0.CH-CH- K 2 2 3 s OCH, CH ∞S J-2 0 - H 6-CH CH H s OCH, CH, CH J-2 0 - H 6-C0.CH-CF- H 2 2 3 s OCH, CH, CH J-2 0 - H 6-OCF.H H s OCH, CH, CH J-2 0 - H 6-CH OCH H s OCH CH CT 3 J-2 0 - H -H(CH 3 ) 2 H s OCH CH, CH J-2 0 - H 5-Cl H s OCH, " CH J-2 0 - H 5-Cl H s OCH H ∞S J-2 0 - H 5-Cl H s OCH, OCH, H J-2 0 - H 5-0CH 3 H s OCH, OCH, CH J-2 0 - H 5-OCH 3 H s CH, OCH, CH J-2 0 - H 5-OCH 3 H s OCH, OCH, H J-2 0 - H 5-OCH(CH 3 ) 2 H s OCH OCH, CH J-2 0 - H 5-OCH (CH ) H s HHCH, OCH, CH Table I (continued) j w R X Y Z m. p . CO J-2 0 H 5-0CH(CH,) 2 H S HHCH HHCH 3 CH J-2 0 H 5-SCH CH H s CH 3 OCH 3 H J-2 0 H 5-SCH CH, H s CH, H(CH 3 ) 2 H J-2 O H 5-SCH CH, H s CH, H M 3 J-2 0 H 5-SCH CH 3 H s CH, CH CH J-2 0 H 5-SO-CH, H 2 3 s CH, OCH, CH J-2 0 H 5-SO.CH, H s CH, OCH, II J-2 0 K 5-H(CH,) 2 K s CH, OCH H J-2 0 H 5-H(CH 3 ) 2 H s CH, CH 3 CH J-2 0 H 5-H(CH 3 ) 2 H s OCH, OCH, CH J-2 0 H 5-H(CH 3 2 H s OCH, OCH I J-2 0 H 5-H(CH 3 ) 2 H s OCH CH, V J-2 0 H H H so. OCH. CH, II J-2 0 H H H so 2 OCH OCH > J-2 0 H H H so 2 OCH OCH, CH J-2 0 H H H CH, OCH 3 CH S0 2 J-2 0 H H H so 2 Cl OCH CH J-2 0 H K H Cl H(CH 3 ) 2 CH S0 2 J-2 0 H 6-CH 2 CF 3 K CH, OCH 3 V S °2 J-2 0 H 6-Br H so 2 CH, OCH I J-2 0 K 6-0CH 2 CH H so 2 CH, OCH H J-2 0 H 6-OCF 3 H CH, OCH CH S0 2 J-2 0 H 6-OCF H H so 2 CH, OCH CH J-2 0 H 6-H(CH 3 2 H CH, OCH CH S °2 J-2 0 H 6-H(CH 3 2 K s 2 OCH, OCH CH 3 j_ 2 0 H 6-H(CH 3 ) 2 H so 2 OCH, OCH H 3 J-2 0 H 6-H(CH 3 ) 2 H so 2 OCH CH 3 H J-2 0 H 5-Cl H OCH. CH 3 H S °2 3 J-2 0 H 5-Cl H OCH CH S °2 ra 3 J-2 0 H 5-OCH, H so 2 OCH CH 3 CH J-2 o H 5-OCH H so 2 OCH. CH 3 H 0 H 5-CH H SO. OCH. CH. H C J - 2 5 Table I (continued) 1 ϊ E K ϋ h. X X Z m.p . CO J-2 0 - H 5-CH 3 H OCH, CH 3 ■ S0 2 J-2 0 - H 5-SCH CH H OCH, CH 3 H S0 2 J-2 0 — H 5-SCH, H so 2 OCH, V ∞ 3 J-2 0 - H 5-SCH 3 H so 2 OCH CH 3 CH J-2 0 - H H 0C 2 H 5 HH CH, H CH J-2 0 _ H H H H HH CH 3 C «*» J-2 0 - H H H HH OCH, CH 3 m 3 J-2 0 — H H H HH OCH, H ∞S J-2 0 - H H H HH OCH, H(CH 3 2 H J-2 0 — H 6-C1 H HH OCH. ∞S ■ J-2 0 — H 6-C1 H HH 0CH 3 CH, CH J-2 0 β H 5-Cl H HH OCH. OCH 3 CH J-2 0 _ H 5-Cl H HH CH 3 OCH 3 CH 184-187 (d) J-2 0 H 5-Cl H HH Cl OCH 3 CH 165-175(d) J-2 0 . H 5-Cl H HH CH 3 CH 3 CH 189-192(d) J-2 0 H 5-Cl H HH OCH 3 °S H 107-110 (d) J-2 0 _ H 5-Cl H HH OCH, OCH ■ 174-176 (d) J-2 0 _, H 5-Cl H HH HHCH, OCH CH H 156-162(d) CH 3 CH J-2 0 — H 5-OCH, H HH OCH, O J-2 0 — H 5-OCH, H HH CH, OCH 3 CH J-2 0 β H H H HCH, CH, OCH CH 192-194 J-2 0 — H H H HCH, CH, CH 3 CH 198-200 J-2 0 — H H H HCH, SCH CH, CH J-2 0 — H H H HCH OCH, OCH CH 199-200 J-2 0 ., H H H HCH, OCH, OCH H 203-207 J-2 0 _. H H H HCH, OCH, CH, H 190-I98(d) 91-194 J-2 0 - H H H CH, CH, H 1 HCH 3 J-2 0 - H H H HCH, H(CH. ) 2 CH, H J-2 0 - H H H HCH, HHCH OCH CH H J-2 0 — H H H HCH, HHCH C=CH H 3-T 0 — H H H HCH Cl OCH, CH 170-175 J-2 0 — H H H HCH OCH OCH OCH, CH Table I (continued) U E R Y m.P . CO O J-2 - H H . H HCK 3 CH, CCH, CH J-2 - H H H HCH, CH, CH(0CH,) 2 CH J-2 - H 6-CH H HCH, OCH, OCH CH 206-210 J-2 - H 6-CH 3 H HCH 3 CH, OCH 3 H J-2 - H 6- CH H HCH OCH, OCH H 185-188 J-2 - H 6-OCH 3 H HCH 3 CH, OCH 3 H 113-118(d) J-2 - H 6-OCH H HCH OC 2 H 5 HHCH H 221-225(d) J-2 - H 6-OCH H HCH OCH CH 168-170 OT 3 J-2 - H 6-OCH H HCH 3 OCH, OCH CH 157-161 J-2 - H 6-OCH 3 H HCH 3 CH, CH, CH 180-182 J-2 - H 6-OCH H HCH 3 Cl OCH, CH 122-129 (d) J-2 - H 6-OCF H H HCH 3 Cl OCH CH J-2 - H 6-C1 H HCH Cl OCH CH J-2 - H 6-C1 H HCH 3 OCH, CH CH 3 J-2 - H 6-H0 2 H ■CH, OCH, CH 3 ■ J-2 - H «-H0 2 H HCH OCH, HHCH CH H J-2 - H 6-CH H HCH OCH, CH, H J-2 - H 6-CH H HCH OCH CH, CH J-2 - H 5-Br H HCH CH, CH, H J-2 - H 5-Br H HCH, CH, OCH, I J-2 - H 5-SCH, H HCH, CH, OCH, H J-2 - H 5-SCH H HCH CH, OCH, CH J-2 - H 5-H(CH 3 ) 2 H HCH, CH, OCH, CH J-2 - H 5-H(CH 3 ) 2 H HCH. CH. OCH, H J-2 - H H H K Λ CH, OCH, H J-2 - H 6-Cl H HCH 2 C 6 H 5 CH, OCH, H J-2 - H 6-OCH H HCH CH CH CH, OCH, H J-2 - H 5-OCH 3 H HCH OCH, H CT 3 J-2 - H 5-HHCH H HCH CH Cl CH, OCH, H J-2 - H 5-CO.CH. H HOCH OCH H 2 3 CH 3 J-2 - CH 3 H H HCH CH, OCH, H J-2 - CH, 6-OCH. H S CH, OCH CH J-2 - CH, 6-C1 H HH CH, OCH 3 CH J-2 - CH. 5-OCH H S CH. OCH. CH Table I (continued) J W E R !ι h. I X Z m.p.CO J-2 0 - CH, 5-N(CH,) 2 H S OCH OCH j CH J-2 0 CH 2 H H H s OCH, OCH j I J-2 0 CH 2 H H H s OCH, OCH 3 CH J-2 0 CH 2 H H H HCH, OCH OCH, CH J-2 0 CH 2 H 6-C1 H HCH, OCH, OCH, CH J-2 0 CH 2 K 6-OCH H S OCH 3 OCH CH J-2 0 0 H H H s OCH 3 OCH, CH J-2 0 0 H 6-OCH H s OCH 3 OCH, CH J-2 0 0 H 6-OCH H 8 OCH. OCH ■ J-2 0 0 H H H HCH OCH. OCH, H J-2 0 0 H K H HCH, CH 3 OCH 3 CH JJ--22 sS -- HH HH HH SS OOCCHH 3 , OOCCHH 3 , CH J-2 s - H 6-H(CH,) 2 H S OCH OCH, CH J-2 s - H 6-ocr, H S OCH 3 OCH, CH J-2 s - H 5-OCH H S OCH 3 OCH, CH J-2 s - H H H HCH, OCH 3 OCH, CH J-2 s - H H H HCH.C.H S CH 3 OCH, CH J-2 s - H 6-C1 H HCH OCH 3 OCH, CH J-2 s - H 5-SCH H HCH, OCHj OCH, CH J-2 s CH, H H H HCH OCH OCH CH Table II J - J-3 JSO.NHCHA * I A - A-l I w E R ι !_. v X Y Z a. P . CO 0 - H H OCF. ,H O CH, H H 0 - H H H 0 CH, CH H 189-191 3 0 - H H H 0 CH, OCH, 1 181-183 0 - H H H 0 CH, HHCH ■ 0 - H H H 0 OCH CH, HHCH, ■ 237-239 0 - H H H 0 OCH, OCH, H 191-194 0 - H H H 0 OCH, OCH, CH 232-233 0 - H H H 0 OCH, CH 188-189 CT 3 0 - H H H 0 Cl OCH, CH 214-215 0 - H H H 0 OCF, CH OT 3 0 - H K H 0 ∞s CH 179-181 CT 3 0 - H K K 0 CH m 3 »3 0 - H K H 0 CH, SCH-CH- CH 2 3 0 - H H H 0 CH OCH CH m 3 0 - K H H 0 C=CH H m 0 - H 5-Cl H 0 OCH, 1 CH 3 0 - H 5-Cl H 0 OCH, CH ∞S 0 - H 5-Cl H 0 Cl OCH, CH 0 - H 5-Br H 0 OCH, OCH, CH 0 - H 5-F H 0 OCH, CH, 1 0 - H 5-CH, H 0 OCH, CH, H 0 - H 5-CH, H 0 OCH, CH, CH 0 - H 5-CF 2 H H 0 OCH, CH, CH 0 - H 5-OCH, H 0 OCH, CH ∞S 0 - H 5-OCH, H 0 OCH, CH, 1 0 - H 5-OCH, H 0 HHCH, CH, 1 0 - H 5-OCH 2 CH 2 CH, H 0 HHCH, OCH, H 0 - H 5-SCH 2 CH, H 0 CH, OCH-CF- CH 2 3 0 - H 5-SOCH H 0 CH, OCH CH Table II (continued) u E R ι h. £ X 2. a.p. CO 0 - H 5-CH H 0 CH, OCH CH 0 - H 5-H0 2 H 0 •CH, OCH, CH 0 - H 5-CO.CH.CHCH, OCH, CH 2 2 2 ι H 0 ∞S 0 - H 5-C0 2 CH, K 0 CH, . ^ CH 0 - H 5-NHCH H 0 OCH CH ^3 0 - H 5-HHCH H 0 CH, OCH 1 0 - H 5-HHCH H 0 SCH 3 OCH 1 0 - H 5-H(CH_CH,) 2 H 0 CH 3 OCH H 0 - H 6-OCH K 0 CH 3 CH m 0 - K 6-OCH, H 0 CH, OCH CH 0 - H 6-Br H 0 CH, OCH, 1 0 - H 6-Br H 0 CH, SCH 1 0 - H 6-SCH CH H 0 OCH, CH, CH 0 - H 6-SCH CH H 0 Cl CH, CH 0 - H 6-SOCH K 0 Cl OCFjH CH 0 - H 6-CH H 0 OCH OCH, CH 0 - H 6-OCH 2 CF, H 0 OCH, OCH 3 CH 0 - H 6-HH 2 H 0 OCH, CH 3 CH 0 - H 6-H(CH,) 2 H 0 CH, OCH 3 I 0 - H 6-H(CH,) 2 H 0 OCH C≡CH H 0 - H 6-H(CH,) 2 H 0 OCH COCH CH 0 - H 6-H(CH,CH_), H 0 OCH CH 3 CH 2 3 2 0 - CH, H H 0 OCH, CH, CH 0 - CH, H H 0 OCH, CH, 1 0 - CH, 5-Br H 0 OCH CH, H 0 - CH, 6-OCH H 0 OCH, X m 0 CH, H H H 0 OCH, CH, H 0 CH 2 H K H 0 OCH CH m 3 0 CH 2 H 5-F H 0 OCH OCH, CH 0 CH 2 H 6-NHCH CH H 0 OCH, OCH, CH 0 0 H H H 0 OCH OCH CH 0 0 H 5-HO, H 0 OCH. OCH. CH Table : II (continued) u E R _ X Y Z m.p. O. 0 0 H 5- -OCH, H 0 OCH CH, OCH, CH 0 0 H 6- -Br H 0 OCH CH HHCH 3 1 s - H H H 0 OCH.CH. CH 3 H 2 3 s - H H H 0 OCH, CH 3 I s - H 6- -OCH, H 0 OCH CH, 1 S 0 H H H 0 OCH CH , » 3 0 - H H H 5 CH, H 1 0 - H H H s CH, CH 1 199-201 3 0 - H H H s CH, OCH, H 195-199 0 - H H H s CH, HHCH ■ 0 - H H H s OCH CH HHCH H 183-185 0 - H H H s OCH OCH H 216-217 0 - H H K s OCH OCH CH 216-219 0 - H H H s CH, OCH CH 220-221 0 - K H K s Cl OCH, CH 227-228 0 - K H H s OCF, CH CH 3 0 - H H K s CH, CH, CH 204-206 0 - H H H s CH, CH *3 0 - H H H S CH, SCH.CH, CH 2 3 0 - H H H S CH, CH.OCH, CH 2 3 0 - H H H s CH, C≡CH H 0 - H H CH 2 Br S CH, H(CH,) 2 H 0 - H 5- •Cl H s CH, OCH, H 0 - H 5- Cl H S CH, OCH, CH 0 - H 5- ■Cl H s Cl OCH, CH 0 - H 5- ■ Br H s OCH OCH, CH 0 - H 5- •F H s OCH, "s H 0 - H 5- CH, H s OCH H m 3 0 - H 5- CH, H s OCH CH m 3 0 - H 5- CF.H H s OCH CH, CH 0 - H 5- OCH, H s OCH CH, CH 0 - H 5- OCH, H s OCH CH, H 0 - H 5- OCH, H s HHCH CH, H Table II (continued) w E R !ι I X 2 m.p. CO 0 - H 5-OCH CH.CH, H S HHCH, OCH, ■ 0 - H 5-SCH CH H s CH, OCH 2 CF 3 CH 0 - H 5-S0CH H s CH, OCH CH 0 - H 5-CH H s CH, OCH CH 0 - H 5-H0 2 H s CH, OCH, CH 0 - H 5-CO.CH.CH, 2 2 3 H s CH, OCH, CH 0 - H 5-C0 2 CH 3 H s CH, OCH CH 0 - H 5-HHCH, 3 H s CH, OCH CH 0 - H 5-HHCH H s CH, OCH 1 0 - H 5-NHCH H s SCH OCH H 0 - H 5-M(CH 2 CH_) 2 H s CH, OCH 1 0 - H 6-OCH H s CH, CH, CH 0 - H 6-OCH 3 H s CH, OCH, CH 0 - H 6-Br K s CH, OCH X 0 - H 6-Br H s CH, ?CH, H 0 - H 6-SCH CH K s OCH, CH, CH 0 - H 6-SCH 2 CH. H s Cl CH, CH 0 - H 6-SOCH H S Cl OCF 2 H CH 0 - H 6-CH H s OCH 3 OCH, CH 0 - H 6-OCH.CF, H s OCH OCH CH 0 - H 6-HH 2 H s OCH OCH CH 0 - H 6-H(CH,) 2 H S CH, OCH. 1 0 - H 6-H(CH,) 2 H s OCH C≡CH H 0 - H 6-H(CH,) 2 H s OCH, COCH CH 0 - H 6-H(CH.CH,), H S OCH CH 3 CH 2 3 2 0 - CH, H H s OCH, CH 3 CH 0 - H H S OCH CH, H CH 3 0 - 5-Br ^3 H s OCH, CH, H 0 - CH, 6-OCH, H S OCH, CH, H 0 CH. H H H s OCH CH, H 0 CH 2 H H H S OCH CH, CH 0 CH 2 H 5-F H S OCH_ OCH, CH 0 CH 2 H 6-NHCH CH H s OCH, OCH CH 0 0 H H H s OCH OCH, CH u E R ι h. Q X X Z m.p. rc) 0 0 H 5-H0 2 K s OCH OCH, CH 0 0 H 5-OCH H S - OCH CH OCH, CH 0 0 H 6-Br H s OCH CH HHCH H s - H H H 5 OCH CH H m s - H H H s OCH CH, H s - H 6-OCH, H 3 s OCH CH, 11 s 0 K H H s OCH CH, H 0 - H K H HH H II OT 3 0 - H H H HH CH, CH, ■ 0 - H H H HH CH, OCH ■ 0 - H H H HCH, CH, OCH, H 188-192 0 - H H H HCH OCH CH HHCH H 225-230 0 - H H H HCH. OCH, *(CH,) 2 If 203-205 3 0 - H H H HCH, OCH OCH, H 214-216 0 - H H H HCH, OCH Cl CH 217-218 0 - H H K HCH, OCH, OCH, CH 218-219 0 - H H H HCH, CH, OCH CH 209-211 0 - H H H HCH CH, CH, CH 210-211 0 - H H H HCH CH Cl OCH CH 0 - H H H CH, CH " C 6 H 5 Cr 3 0 - H H H HCH 2 C.H 5 CH, CH, CH 0 - H H H HCH, CH, CH "3 0 - H H H HH CH, SCH CH CH 0 - H H H HH CH, CH OCH CH 0 - H H H HH CH, C=CH H 0 - K 5-Cl H HH CH, OCH H 0 - H 5-Cl H HCH CH, OCH, CH 0 - H 5-Cl H HCH, Cl OCH, CH 208-210 0 - H 5-Cl H HCH, OCH, OCH CH 181-185 0 - H 5-Cl H HCH OCH, CH 169-172 3 CH 3 - 0 - H 5-Cl H HCH, CH, CH, CH 206-207 0 - H 5-Cl H HCH, CH, CH, H 191-194 0 - H 5-Cl H HCH, OCH, CH, H 189-190 Table II (continued) w E R ι !_. X X z a.p. C 0 - H 5-Cl H HCH, OCH, OCH, H 198-199 0 - H 5-Cl H HCH, OC 2 H 5 HHCH H 168-173 0 - H 5-Br H HCH 2 C 6 H- OCH CH, H 0 - H 5-CH, H HCH, CH, CH m 212-213 0 - H 5-CH, H HCH, CH, OCH CH 207-208 0 - H 5-CH, H HCH, OCH, OCH, CH 193-194 0 - H 5-CH, H HCH 3 Cl OCH 3 CH 192-194 0 - H 5-CH, K HCH, CH, CH, H 213-216 0 - H 5-CH H HCH, OCH 3 CH, H 203-206 0 - H 5-CH, H HCH, OCH. OCH, H 199-201 0 - H 5-CH, H HCH, HHCH 3 OC 2 H 5 H 232-233 0 - H 5-CH, H HCH C H OCH, CH, H 2 6 5 0 - H 5-CH H HCH 2 C.H 5 OCH, CH, CH 0 - H S-CF 2 H H HCH, OCH, CH, CH 0 - H 5-OCH, H HCH, OCH, Cl CH 192-194 0 - H 5-OCH H HCH, OCH, CH, CH 197-200 0 - H 5-OCH, H HCH, OCH, OCH, CH 223-225 0 - H 5-OCH, H HCH 3 OCH, CH, X 189-193 0 - H 5-OCH H HCH, HHCH, OC 2 H s H 232-237 0 - H 5-OCH(CH,) 2 H HH HHCH, OCH, H 0 - H 5-SCH H HH m » OCH 2 CF, CH 0 - H 5-S0 2 CH, H HH CH, OCH, CH 0 - H 5-CH H HH CH, OCH CH 0 - H 5-H0 2 H HCH, OCH, CH OT 3 o - H 5-CO CH j CH H HCH, CH, OCH CH 0 - H 5-CO CH j CH H HCH, CH, OCH, CH 0 - H 5-H(CH 3 ) 2 H HCH, CH, OCH, CH 0 - H S-H(CH,) 2 H HCH, CH, OCH, H 0 - H 5-H(CH_ ). H HH SCH, OCH, H 0 - H 5-HHCH CH, H HH CH, OCH, H 0 - H 6-OCH H HH ^3 CH, CH 0 - H 6-OCH, H HCH, CH, OCH, CH 0 - H 6-Br H HCH CH, OCH H 0 - H 6-Br H NCH.CH. CH, SCH H 2 3 0 - H 6-OCH CH H HCH CH OCH CH, CH Table II (continued) u E R ι 2t X Y Z m.p . CO 0 - H 6-OCH CH H rfCH-C^ H s C CH, CH 0 - H 6-SCH H HCH Cl OC jH CH 0 - H 6-CH H HCH, OCH, OCH CH 0 - K 6-S0CH.CH, H HCH OCH OCH CH 2 3 0 - H 6-HH, H HH OCH OCH CH 2 0 - K 6-NHCH H HCH, OCH, H m 3 0 - H 6-NHCH H HCH, OCH C≡CH X ς - H 6-NHCH H OCH, COCH CH HC 6 H 5 0 - H 6-H(CH,) 2 H HH OCH, CH, CH 0 - CH, H H HCH OCH CH, CH 0 - CH, H H NOCH OCH 3 X m 3 0 - CH, 5-Cl H HH OCH CH, X 0 - CH, 6-Br H HH OCH X m 0 CH 2 H H H HCH OCH CH, X 0 CH 2 H H H S OCH CH, CH 0 CH 2 H H K 0 OCH, OCH CH 0 CH 2 H 5-OCH H s OCH OCH CH • 0 0 H H H s OCH OCH, CH 0 0 H 6-H(CH,) 2 K s OCH OCH, CH 0 0 H 6-C1 H HCH, OCH.CH. OCH, ' CH 2 3 0 0 H 5-OCH, H 0 OCH CH HHCH X S - H H H 0 OCH.CH. CH, H 2 3 S - H H H s OCH CH, H S - H 5-H(CH,) 2 H HCH, OCH, CH, X S CH. H H H s OCH. CH. X Table III " J m J-4 JSO-NHCHA . . - 2 . A ■ A-l a.p. u E R h. n °4 X X Ά CO 0 - H H H 0 HH HH CH, OCH, X 0 - H H H 0 HCH HH CH, OCH CH 212- •215 0 - H H H 0 HCH, HH CH, OCH X 202- ■205 0 - H H H 0 HCH, HH OCH, OCH, CH 222- ■225 0 - H H H 0 HCH HCH, CH, OCH, X 0 - H H H 0 HCH, HCH CH, Ot-R CH 0 - H H C.H. 0 HCH HCH Cl OCH, CH 0 - H 5- •Cl H 0 HCH HCH, OCH OCH, CH 0 - H 5- •OCH, H 0 HCH XCH, OCH OCH, CH 0 - H 6- *(CH,) 2 H 0 HCH, HCH OCH HHCH. CH 3 0 - H H H 0 HCH CH XCH OCH CH CH 3 0 - H H H 0 HCH(CH.) , XCH, OCH CH, X 3 2 0 - H H H 1 0 0 CH, CH m 3 0 - H H H 1 0 0 CH, OCH, CH 0 - H H H 1 0 0 Cl OCH, CH 0 - H H H 1 0 0 XCCH,) 2 OCH, CH 0 - H H H 1 0 0 X(CH,) 2 CΞrCH X 0 - H 5- ■Br H 1 0 0 OCH, CH, X 0 - H 5- H0 2 H 1 0 0 OCH, CH, X 0 - H 5- OCH H 1 0 0 OCH, CH, X 0 - H 5- OCH, H 1 0 0 OCH CH, CH 0 - H 5- S0 2 N(CH 2 CH 3 ) 2 H 1 0 0 OCH CH, OCH CH, CH 0 - H 6- SCH 3 H 1 0 0 CH, CH OCH CH 0 - H 6- CH H 1 0 0 CH, CH 3 CH 0 - H 6- OCF H 1 0 0 CH, OCH, X 0 - H 6- H(CH 3 ) 2 H 1 0 0 CH, SCH X 0 - H H H 1 0 s CH, OCH. X 3 0 - H H H 1 0 s CH, OCH. CH 3 0 - H H H 1 0 s OCH, OCH. X 3 Table III (continued) 0 - H H H 10 s Cl OCH, CH 0 - H H H 10 s OCH OCH, CH 0 - H 5-Cl H 1 0 s OCH, OCH, CH 0 - H 5-Cl K 1 s 0 OCH, OCH H 0 - H 5-CH H 1 s 0 OCH, CH, X 0 - H 5-C H 1 s 0 OCH, CH, X 0 - H 5-C H 10 s OCH CH, X 0 - H 5-CH H 10 s OCF 2 H CH, CH 0 - H 5-HHCH, H 10 s CF 2 H CH, CH 0 - H 6-Br H 1 s 0 CH, OCH, CH 0 - H 6-HCH,(CH CH * i K 1 s 0 CH, OCH CH 0 - H H H 10 HH C 2 H OCH, CH 0 - H H H 10 HH HHCH, OCH X 0 - H H H 10 HH HHCH, OCH j CH X 0 - H H H 1 HH 0 HHCH, OCH CH X 0 - H H H 1 HCH 3 0 H(CH,) 2 CH ∞S 0 - H 5-CH CH H 1 HCH 0 CH, CH, CH 0 - H 5-CF H H 1 HCH 0 CH, OCH, CH 0 - H 5-OCH, H 1 HCH CH 0 CH, OCH, CH 0 - H 5-SCH K 1 0 HCH OCH OCH CH 0 - H 5-S0CH 2 CH, H 1 HCH 2 CH, 0 OCH, OCH X 0 - H 6-F H 10 HCH OCH, OCH X 0 - H 6-OCH H 1 0 HCH, OCH, CH, H 0 - H 6-S0 2 CH(CH,) 2 H 1 HCH, 0 OCH, CH, X 0 - H 6-HCH,(CH 2 CH,) H 10 HCH, OCH, CH, CH 0 - H H H 1 S HH OCH CH CT 3 0 - H H H 1 S HCH, CH.-eyclo- CH, CH propyl 0 - H H H 1 HH S CH, CH, CH 0 - H H H 1 HCH s CH, OCH, CH 0 - H H H 1 HCH s CH, OCH, X 0 - H H H 1 HCH j CH S CH, OCH, X Tablie III (continued) 0 - H 5-Br H 1 s HCH CH, OCH, X 0 - K 5-CX H 1 s HCH, OCH, CH m 3 0 - H 5-CH, H 1 HH S OCH, OCH, CH 0 - H 5-OCH H 1 S HH OCH, OCH CH 0 - H 5-CH.OCH. H 1 S HCH, OCH, OCH, CH 2 3 0 - H 6-CH H 1 HCH S OCH OCH CH 0 - H 6-Cl H 1 S HCH, OCH, OCH, X 0 - H 6-X0 2 H 1 s HCH, OCH, CH, X 0 - H H H 1 X HH OCH X ∞ 3 0 - H H H 1 X HH CH, X CH 3 0 - H H H 1 XCH, HH CH, CH m 3 0 - H H H 1 HCH, HCH, OCH CH CH, CH 0 - H H H 1 HCH, HCH, OCH CH CH, X 0 - H H H 1 HCH HCH, CF 2 H CF 2 H CH 0 - H 5-Cl H 1 HH HCH, OC CH, CH 0 - H 5-CF 2 H H 1 HCH CH HCH OCH CH, CH 0 - H 5-OCF H 1 HC,H_ HCH OCH, CH , CH 0 - H 5-H(CH,) 2 H 1 HCH HCH OCH, CH, CH 0 - H 6-Br H 1 HH HH OCH CH, X 0 - H 6-SCH, H 1 HCH, HCH OCH, CH, X 0 - H 6-CH, H 1 HCH, HCH OCH, CH, X 0 - H 6-OCH H 1 HCH. 3 HCH OCH X ∞S 0 - H H H 2 0 0 CH, CH m 0 - H H H 2 0 0 CH, OCH CH 0 - H H H 2 0 0 Cl OCH CH 0 - H H H 2 0 0 X(CH,) 2 OCH CH 0 - H H H 2 0 0 X(CH,) 2 CΞCH X 0 - H H F 2 0 0 CH, CH OT 3 0 - H 5-Br H 2 0 0 OCH CH, X 0 - H 5-H0 2 H 2 0 0 OCH X m 3 0 - H 5-OCH H 2 0 0 OCH CH, X 0 - H 5-OCH, H 2 0 0 OCH, CH, CH 0 - H 5-S0 2 H(CH 2 CH, ) 2 H 2 0 0 OCH CH OCH CH, CH Ta le III (continued) a. . w 5 S _t ". > « q -i ?4 X Y Z CO 0 - H 6-SCH H 20 0 CH, CH OCH CH 0 - H 6-CH H 20 0 CH, CH, CH 0 - H 6-OCF H 20 0 CH, OCH, H 0 - H 6-H(CH,) 2 H 20 0 CH, SCH, X 0 - H H H 20 s CH, OCH, X 0 - H H H 20 s OCH, CH OT 3 0 - H H H 20 s OCH, OCH, X 0 - H H H 20 s Cl OCH, CH 0 - H H H 20 s OCH OCH, CH 0 - H 5-Cl H 20 s OCH OCH, CH 0 - H 5-Cl H 2 S 0 OCH, OCH, X 0 - H 5-CH, H 2 S 0 OCH CH, X 0 - H 5-CF H 2 S 0 OCH, CH, X 0 - H 5-CF H 20 s OCH, CH, X ' 0 - H 5-CH H 20 s OCF H CH, CH 0 - H 5-HHCH H 20 s OCF 2 H CH, CH 0 - H 6-Br H 2 S 0 CH, OCH, CH 0 - H 6-HCH,(CH CH ) H 2 S 0 CH, OCH, CH 0 - H H H 20 HH C 2 H OCH, CH 0 - H H H 20 HH HHCH, OCH, X 0 - H H H 20 HH HHCH, OCH j CH, X 0 - H H H 2 HH 0 HHCH, OCH.CH- X 2 3 0 - H K H 2 HCH, 0 H(CH,) 2 CH, CH 0 - H 5-CH CH H 2 HCH, 0 CH, CH m 3 0 - H 5-CF.H H 2 HCH 2 0 CH, OCH, CH 0 - H 5-OCH H 2 HCH CH 0 CH, OCH CH 0 - H 5-SCH H 20 HCH OCH OCH CH 0 - H 5-SOCH 2 CH, H 2 HCH j CH, 0 OCH OCH, X 0 - H 6-F H 20 HCH, OCH, OCH X 0 - H 6-OCH H 20 HCH OCH, CH, X 0 - H 6-SO CH(CH ) H 2 HCH, 0 OCH, CH, X 0 - H 6-HCH (CH CH ) H 20 HCH OCH CH, CH Table III (continued) m.p. w E R !i h. n *_3 2i i X . 1 1S1 0 - H K H 2 S HH OCH CH, CH 0 - H H H 2 S NCH CH -cyclo¬ CH, CH propyl 0 - H H H 2 HH S CH CH ^ 0 - H H H 2 HCH S CH, OCH, CH 0 - H K H 2 HCH S CH, OCH, X 0 - H H H 2 HCH 2 CH 3 S CH OCH, X 0 - H 5-Br H 2 S HCH • CH OCH X 0 - H 5-CH H 2 s HCH CH OCH, CH 0 - H 5-CH, H 2 HH S OCH OCH, CH 0 - H 5-OCH H 2 S HH OCH OCH, CH 0 - H 5-CH 2 OCH, H 2 s HCH OCH OCH, CH 0 - H 6-CH, H 2 HCH, S OCH OCH, CH 0 - H 6-C1 H 2 S HCH OCH OCH, X 0 - H 6-H0 2 H 2 s HCH OCH X m 0 - H H H 2 X HH OCH X CT 3 0 - H H H 2 X HH CH, CH, X 0 - H H H 2 HCH . HH CH CH, CH 0 - H H H 2 HCH. NCH, OCH.CH. CH, CH 3 2 3 0 - H H H 2 HCH HCH OCH CH CH, X 0 - H H CH 3 2 HCH HCH CF H CF.H 2 CH 0 - H 5-Cl H 2 HH HCH OCF CH, CH 0 - H 5-CF H H 2 NCH.CH, HCH. OCH. CH, CH 2 3 3 3 0 - H 5-OCF, H 2 HCH OCH CH C 3 H 7 m 3 0 - H 5-H(CH,) 2 H 2 HCH 3 HCH OCH CH, CH 0 - H 6-Br H 2 HH HH OCH CH, 0 - H 6-SCH H 2 HCH, HCH, OCH, CH, 3 3 0 - H 6-CH. H 2 HCH HCH OCH CH, 0 - H 6-OCH H 2 HCH NCH OCH CH, 0 - CH H 0 HCH NCH, CH, 3 H 3 3 OT 3 0 - CH H 1 0 0 OCH CH, 3 H 0 - CH H 2 0 0 OCH 3 H ∞S Table III (continued) m.p. u E X i h. n °3 ?4 X 1 Z CO 0 - CH ,5-Cl H 1 0 0 OCH CH, CH 0 CH 2 H K H 2 0 0 OCH OCH CH 0 CH 2 H H H 1 0 0 OCH, OCH, CH 0 CH 2 H H H 1 0 HCH, OCH OCH, CH 0 CH 2 K 6-OCH K 1 s 0 OCH OCH, CH 0 0 H H H 2 0 S CH, OCH X 0 0 K H H 2 0 S CH, OCH, X 0 0 H H H 1 0 s CH, HHCH X 0 0 K H H 1 HCH HCH CH, CH, CH s - H 5-CH H 1 s HCH OCH, CH, CH s - H H H 2 s 0 OCF.H CH, CH S - H H H 2 0 0 OCH, OCH CH s - H H H 0 HCH HCH OCH, OCH X s CH 2 H 6-Br H 1 0 0 OCH, OCH CH 71 Table IV J JSO-NHCHA J-5 A A-l X.p. u E R h 2a s ± I X 2 ilSl 0 - H H H HH HH H H 0 - H H H HH HH H CT 3 0 - H H H HH HH ∞S ∞3 0 - H H H HH NH CH, OCH, 0 - H H H HH HH OCH, OCH, 0 - H H H HH HH OCH, HHCH, 0 - H H H HH HH HHCH, HHCH, CH 0 - H H H HH HH HHCH OCH CH 0 - H H H HH HH OCH, OCH CH 0 - H H H HH HH CH, OCH, CH 0 - H K H HH HH CH, CH m 0 - H H H HH HH Cl CH, CH 0 - H H H HH HH Br OCH, CH 0 - H H H HH HH OCH 2 CH, OCH, X 0 - H H Cl HH HH SCH, OCH X 0 - H 5- CH 2 CH 2 CH, H HH HH OCH, X ∞S 0 - H 5- CH 2 CH 2 CH, H NH HH CH, OCH, CH 0 - H 5- CH.CH.C1 H NH HH OCH 3 OCH, CH 0 - H 5- Cl K HH NH OCH 3 OCH, CH 0 - H 5- Cl H HH HH OCH j ∞S CH 0 - H 5- OCH(CH-). H HH HH OCH, CH m 0 - H 5- OCH 3 H HH HH OCH, m 3 CH 0 - H 5- SCH, K HH HH OCH, ∞S 0 - H 5- SO,CH,CH, H HH HH OCH, CH, 2 2 3 0 - H 5- CH H HH HH OCH 3 CH, 0 - H 5- N(CH,) 2 H NH HH OCH, m 0 - H 6- Br H NH NH OCH, m 3 0 — H 6- BΓ H HH NH OCH- CH, CH Table IV (continued) 73 Table V J w E R κ ι H 5 ± Y Z m.p. CO J-6 0 - H H H CH, CH, H CH J-6 0 - H H H CH, CH, CH 226-230(d) CH 3 J-6 0 - H H H CH, OCH, OCH, CH 232-235(d) J-6 0 - H H H CH, OCH, OC 2 H 5 CH 237-240(d) J-6 0 - H H H CH, Cl OCH, CH 195-198 J-6 0 - H H H CH. HHCH, OCH, CH J-6 0 - H H H CH, HHCH, OC 2 H 5 X 216-220Cd) J-6 0 - H H H CH, OCH, 0C 2 H_ X OCH H 222-226(d) J - 6 0 - H H H CH, CT 3 J-6 0 - H H H CH, CH, CH, X J-6 0 - H H H CH, CH, Cl X J-6 0 - H H Cl CH. OCH. OCH, CH J-6 0 - H H H C 2 H 5 OCH, OCH, CH J-6 0 - H H H OCH, CH, CH C 2 H S J-6 0 - H H H C.H, OCH. CH, X 2 5 3 j- 6 0 - H H H CH 2 CH(CH,) 2 OCH, CH, X J-6 0 - H 5-Cl H OCH, CH, X CH 3 J-6 0 - H 5-Cl H CH, OCH- CH, CH J-6 0 - H 5-Cl H CH, OCH OCH, CH J-6 0 - H 5-OCH, H CH. OCH. OCH 3 CH J-6 0 - H 5-OCH, H CH-CH.CH. OCH 3 OCH, CH 0 - H 5-OCH, H CH.CH.CH. CH. OCH, CH J - 6 2 2 "3 3 J-6 0 H 5-CN H CH.CH.CH, CH, OCH H 2 2 3 J-6 0 - H 5-H(CH,) 2 H CH.CH. CH, OCH, H 2 3 J-6 0 - H 5-CF, H CH 3 CH, OCH, CH J-6 0 - H 6-Br H CH, OCH, CH CH 3 J-6 0 - H 6-Br H CH. OCH. OCH, CH J-6 0 - H 6-OCH, H CH, OCH, OCH. CH Table V (continued) J W E R __1 R, Y 2 m. .CO J-6 0 - H 6-OC_H 5 H CH, OCH, OCH CH J-6 0 - H 6-SCH H CH, OCH, OCH j CH J-6 0 - H 6-HO H CH, OCH, OCH, CH J-6 o - CH H H CH, OCH, OCH, CH J-6 0 CH 2 H H H CH, OCH OCH, CH J-6 0 0 H H H CH, OCH, OCH, CH J-6 s - H H H CH, OCH, OCH, CH J-7 0 - H H H CH, H CH, X J-7 0 - H H H CH, CH, X CT 3 J-7 0 - H H H CH, OCH CH, X J-7 0 - H H H CH, OCH, CH, CH J-7 0 - H H H CH, OCH OCH CH J-7 0 - H H H CH, Cl OCH CH J-7 0 - H H H CH, OCH 2 F OCH CH J-7 0 - H H H CH, H(CH,) 2 OC 2 H 5 X J-7 0 - H H OC OCH, CH 3 OCH, CH J-7 0 - H H H OCH, OCH, CH C 2 H S J-7 0 - H H H C 2 H 5 OCH. CH, X J-7 0 - H H H CH(CH.) CH 3 CH 3 X 3'2 J-7 0 - H H H CH(CH ) CH, CH CH 3 J-7 0 - H H H CH.CH.CH, Cl CH 2 2 3 «*_ J-7 0 - H H H CH.CH.CH. Cl HHCH X 2 2 3 J-7 0 - K H H CH.CH.CH.CH OCH. HHCH H 2 2 2 3 3 J-7 0 - H H K CH.CH.CH.CH. OOCCHH,. OCH, CH 2 2 2 3 3 J-7 0 - H H H CH 2 CH(CH,) 2 OCH. CH, CH J-7 0 - H H H CH 2 CH(CH,) 2 OCH, H CH 3 J-7 0 - H 6-Br H CH, OCH. CH, CH 3 J-7 0 - H 6-Br H Cl OCH 3 CH CH 3 J-7 0 - H 6-SCH H CH, OCH 3 CH CH 3 J-7 0 - H 6-SCH H ∞3 OCH 3 H CH 3 J-7 0 - H 6-OCH H CH.CH.CH. CH, 2 2 3 OCH 3 H J-7 0 - H 6-OCH, H CH 3 CH 3 CH CH 3 J-7 0 - H 6-NHCH H CH, OCH, CH CH 3 J-7 0 - H 5-F H C 2 H 5 OCH. CH. CH Table V (continued) J W E X !ι !* !* I X 2 a-p- c? J-7 0 - H 5-H0 2 H CH, OCH, CH, CH J-7 0 - K 5-OCH 2 H CH, OCH CH ∞S J-7 0 - CH 3 H H CH, OCH, CH, CH J-7 0 CH 2 H H H CH, OCH, CH, CH OCH, CH, CH J-7 0 0 H H H CH 3 J-7 5 - H H H OCH, CH, CH CH 3 Table VI JSO.HH∞A J - "l ^P β ndin β on J 2 , J « 1-4 depending on A J W E R n 2 2_ L λ τ Λ !ι J-l 0 - H H - s - A-2 CH, 0 - J-l 0 - H 5-Cl - s - A-2 OCH, 0 - J-l 0 - H 5-OCH, - s - A-2 OCH CH 0 - J-l 0 - H 6-Br - s - A-2 OCH CH H 2 - J-l 0 - H 6-OCH - so 2 - A-2 CH, CH 2 - J-l 0 - H H - so. - A-2 OCH, CH 2 - J-l 0 - H H - so 2 - A-2 OCH CH 2 - J-l 0 - H 5-CH - HH - A-2 OCH, 0 3 - J-l 0 - H H - HCH - A-2 OCF . 0 - J-l 0 - H H - HCH, - A-2 CH, 0 - 234-240 (d) J-l 0 - H 5-CF - HCH - A-2 OCH, CH 2 - J-l 0 - H 6-C1 - HCH - A-2 OCH, CH 2 - J-l 0 - H H - A-2 OCF CH 2 BC 6 H 5 - H - J-l 0 - H H - HCH 2 C 6 H 5 - A-2 OCH, CH 2 - J-l 0 0 H H - S - A-2 OCH, CH 2 T J-l 0 - CH, H - HCH, - A-2 CH, 0 - J-2 0 - H H - S - A-2 OCF H 0 - J-2 0 - H 5-SCH - S - A-2 OCH, 0 - J-2 0 - H 5-CH - S - A-2 OCH CH 2 - J-2 0 - H 6-H(CH,) 2 - s - A-2 OCH CH 2 - J-2 0 - H H - so. - A-2 OCH CH CH 2 - J-2 0 - H H - so 2 - A-2 OCH 0 - J-2 0 - H 6-CH - so 2 - A-2 OCH CH 2 - J-2 0 - H H - HH - A-2 CH 2 CH 3 - J-2 0 - H H - HCH - A-2 CH, 0 - J-2 0 - H 5-OCH - HCH - A-2 CH, 0 - J-2 0 - H 6-SCH - HCH CH - A-2 CH, 0 - J-2 0 - H H - HC 6 H 5 - A-2 OCH, 0 Table VI (continued) x.p. J w E 1 1 n i & i ϊl fli-Sl J-20 - H H - NCH CHCH-, - A-20CH 3 CH 2 - J-2 0 CH 2 H H - S - A-2 OCH CH 2 - J-2 S H H - HCH - A-2 OCH, CH 2 - J-3 0 - H H - 0 - A-2 OCH 0 - J-3 0 - H H - 0 - A-2 OCH, CH 2 - J-3 0 - H H - 0 - A-2 CH 2 - m J-3 0 - H 5-CH 2 CH, - 0 - A-2 OCH, CH 2 - J-3 0 - H 5-F - 0 - A-2 OCH 0 - J-30 - H 6-HHCH - 0 - A-2 OCH 0 - J-3 0 - H 6-CH - 0 - A-2 CH, 0 - J-3 0 - H H - S - A-2 CH 2 - m J-3 0 - H H - S - A-2 OCH, CH 2 - J-3 0 - H 5-F - s - A-2 OCH CH 2 - J-3 0 - H 6-OCH - s - A-2 OCF j H CH 2 - J-3 0 - H H - HCH - A-2 OCF 2 H 0 - J-3 0 - H 5-Cl - HCH, - A-2 OCH, 0 - J-3 0 - H 6-H(CH,) 2 - HCH, - A-2 OCH 0 - J-3 0 - H H - ."CH.CH, - A-2 OCH.CH. 0 - 2 3 J-3 S - H H - 0 - A-2 CH, CH 2 - J-3 0 - CH, H - s - A-2 CH, CH 2 - J-4 0 - H H 0 HCH HCH, A-2 CH, 0 - J-4 0 - H H 1 0 0 A-2 OCF H 0 - J-4 0 - H H 1 0 NCH A-2 OCH CH 0 - J-4 0 - H H 1 s 0 A-2 OCH CH 2 - J-4 0 - H H 1 s HCH. A-2 CH, CH 2 - J-4 0 - H H 1 HCH, HCH A-2 CH, CH 2 - J-4 0 - H H 2 0 0 A-2 OCH, CH 2 - J-4 0 - H 5-Cl 2 0 0 A-2 OCH CH 2 - J-4 0 - H H 2 S 0 A-2 CH, CH 2 - J-4 0 - H H 2 HCH. 0 A-2 CH, 0 - J-4 0 CH 2 H H I 0 0 * A-2 OCH 0 - J-4 0 H H 2 0 0 A-2 OCF H 0 - 78 Table VI (continued) J-5 O - H H - HH NH A-2 OCH, 0 - J-5 0 - H H - HH HH A-2 OCH, CH 2 - J-5 0 - H H - HCH, NH A-2 CH, CH 2 - J-5 0 - H H - NCH, . NCH A-2 CH, CH 2 - J-5 0 - H 5- ■OCH - NCH.CH. NCH. 3 A-2 CH, CH 2 - 2 3 J-5 0 - H 6-C1 - NCH. HH A-2 CH, CH 2 - J-5 0 - CH, H - HH HH A-2 OCH, CH 2 - J-l 0 - H H - S - A-3 CH, - J-l 0 - H 5- ■Cl - S - A-3 OCH - - J-l 0 - H 5- •OCH, - s - A-3 C 2 H s - - J-l 0 - H 6- ■Br - s - A-3 OCH, - - J-l 0 - H 6- •OCH, - so 2 - A-3 OCH - - J-l 0 - K H - S0 2 - A-3 OCH, - - J-l 0 - H H - - A-3 - - S0 2 " J-l 0 - H 5- •CH, - HH - A-3 OCH, - - J-l 0 - K H - HCH 3 - A-3 CH - - 3 J-l 0 - H 5- CF, - HCH 3 - A-3 m 3 - - J-l 0 - H 6- •ci - XCH - A-3 CH, - - J-l 0 - H H - NC 6 H S - A-3 CH, - - J-l 0 - H H - HCH 2 C.H S - A-3 OCH, - - J-l 0 0 H H - S - A-3 OCH - - J-l 0 - CH, H - NCH - A-3 CH, - - J-2 0 - H H - S - A-3 CH, - - J-2 0 - H 5- SCH, - s - A-3 OCH, - - J-2 0 - H 5- CH - s - A-3 OCH, - - J-2 0 - H 6- H(CH,) 2 - s - A-3 OCH, - - J-2 0 - H H - so 2 - A-3 OCH, - - J-2 0 - H H - so. - A-3 CH, - - J-2 0 - H 6- CH, - so 2 - A-3 CH, - - J-2 0 - H H - HH - A-3 CH, - - J-2 0 - H H - HCH - A-3 OCF 2 H - - J-2 0 - H 5- OCH - HCH, - A-3 OCH, - - Ci C C| C| C Ci Cl Cι C| Cι -a C| C l C4 C| C l Ci Ci C| C| C| C| C| I I I I I I I I I I I I I I I I I I I I I I I σ o o o o o o o o o o oi o o o o 0 O O O O 0 o 0 o I I I I I I I I I I I I I I I I 1 I I I I 1 I 1 I I X X X X X X X X X X O X X X X X X X X X X X X X X u X X X M M M M • I I I I I I X 01 o o O O O O O O o K X o o O o X I I I I I I X X X U U I I I u» u ri w r» r u» r ui r ui u u I u I u I u I u I u I u I ur u u ur u r ur u u r u r o id 3 8 >q u 8 x 8 8 x 8 X u 8 X 8 «4 U 3 ! M U U U d U U U U U M d U ! u 3 u 8 U X u X a u u in • I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I I Table VI (cont.inue:d) J-4 0 CH 2 H H 1 0 0 A-3 CH, - - J-4 s - H H 2 0 0 A-3 CH, - - J-5 0 - H H - HH HH A-3 CH - - J-5 0 - H H - HH HH A-3 OCH, - - J-5 0 - H H - NCH, HH A-3 OCHJCHJ 1 " - J-5 0 - H 5-OCH, - NCH 2 CH HCH 3 A"3 ra 3 - - J-5 0 - H 6-Cl - HCH, HH A-3 OCHJ - - J-5 0 - CH, H - HH HH A-3 OCH 3 - - J-l 0 - H K - S - A-4 CH 3 H - J-l 0 - H 5-Cl - s - A-4 OCH 3 H - J-l 0 - H 5-OCH, - s - A-4 OCH 3 H - J-l 0 - H 6-Br - s - A-4 OCH, K - J-l 0 - K 6-OCH, - so 2 - A-4 OCH, H - J-l 0 - H H - A-4 CH CH, S0 2 - - J-l 0 - H H - so 2 - A-4 OCH, CH, - J-l 0 - H 5-CH, - HH - A-4 OCH CH, - J-l 0 - H H - HCH, - A-4 OCH CH CH, - J-l 0 - H 5-CF, - HCH, - A-4 CH CH, - J-l 0 - H 6-Cl - HCH, - A-4 CH, CH, - J-l 0 - H H - CH, " C 6 H 5 - A-4 CH, - J-l 0 - H H - HCH 2 C.H S - A-4 CH H - J-l 0 0 H H - S - A-4 OCH, K - J-l 0 - CH, H - HCH, - A-4 OCH H - J-2 0 - H H - S - A-4 OCH, H - J-2 0 - H 5-SCH, - s - A-4 CH, H - J-2 0 - H 5-CH - s - A-4 CH, CH, - J-2 0 - H 6-H(CH, CH, >2 " s - A-4 CH, - J-2 0 - H H S0 2 - A-4 OCH, CH, - J-2 0 - H H - so 2 - A-4 OCH, H - J-2 0 - H 6-CH, - so 2 - A-4 OCH H - J-2 0 - H H - HH - A-4 OCH H - Table VI (continued ) J-30 - H H - 0 - A-4 CH, αt, - J-30 - H H - 0 - A-4 CH 3 H - J-30 - H 5-CH 2 CH, - 0 - A-4 CH, H - J-30 - H 5-F - 0 - A-4 OCH, H - J-30 - H 6-HHCH, - 0 - A-4 OCH, H - J-30 - H 6-CH - 0 - A-4 OCH, H - J-30 - H H - s - A-4 OCF j H H - J-30 - H H - s - A-4 OCH, H - J-30 - H 5-F - s - A-4 CH 3 H - J-30 - K 6-0CH 3 - s - A- CH, H - J-30 - H H - HCH, - A-4 CH, H - J-30 - K 5-Cl - XCH, - A-4 CH, H - 6-H(CH_) - A-4 OCH, H - J-30 - H 2 " "∞S J-30 - H H - HCH j CH, - A-4 OCH CH, - J-3 S - H H - 0 - A-4 OCH, CH, - J-30 - CH - S - A-4 CH, CH, - 3 H J-40 - H H 0 HCH, HCH, A-4 CH, CH, - H, - J-40 - H H 1 0 0 A-4 CH, C J-40 - H H 1 0 HCH, A-4 OCH, CH, - J-40 - H H 1 S 0 A-4 CH, CH, - J-40 - H H 1 s HCH, A-4 OCF. H CH, - 3 2 J-40 - H H I HCH, HCH, A-4 CH CH, - J-40 - H H 2 0 0 A-4 CH, H J-40 - H 5-Cl 2 0 0 A-4 OCH . H " Table VI (continued) J E R _1 n Q i 2* A --i li iΪ!≤i j -4 0 - H H 2 S 0 A-4 CH 2 CH, H j -4 0 - H H 2 HCH, 0 A-4 OC^CH, H J-4 0 CH 2 H H 10 0 A-4 0CH 2 CH, CH, - J-4 S - H H 20 0 A-4 CH, CH, j _S 0 - H H - SH HH A-4 CH, CH, j _5 0 - H H - HH HH A-4 OCH, CH, j -5 O - H H - HCH, HH A-4 OCH, H j -5 0 - H H - HCH, HCH, A-4 CH, H j -5 O - H 5-OCH, - HCH 2 CH, HCH, A-4 CH, H j -5 0 - H 6-Cl - HCH, HH A-4 OCH, H J-5 0 - CH H - HH HH A-4 CH, H j -10 - H H - S - A-5 CH, OCH, - W O - H 5-Cl - S - A-5 CH, CH, - j -l 0 - H 5-OCH, - S - A-5 CH, OCH, - J-l 0 - H 6-Br - S - A-5 CH, CH, j -l 0 - H 6-OCH, - S0 2 - A-5 CH, CH, J-l 0 - H H - S0 2 - A-5 CH, CH, J-l 0 - H H - S0 2 - A-5 CH, OCH, - J-l 0 - H 5-CH, - HH - A-5 CH j CH, OCH, J-10 - H H - HCH, - A-5 CH 2 CH, CH, J-l 0 - H 5-CF, - HCH, - A-S CH, CH, j .l 0 - H 6-Cl - HCH, - A-5 CH, OCH, j -10 - H H - HC 6 H 5 - A-5 CH, OCH^H, • J-1 0 - H H - HCH 2 C 6 H S - A-5 CH, SCH, J-l 00 H H - S - A-5 CH, CH, J-l O - CH H - HCH, - A-5 CH, CH, j -2 0 - H H - S - A-5 CH 2 CF, CH, J-2 0 - H 5-SCH, - S - A-5 CH^F, OCH j j -2 0 - H 5-CH - S - A-5 CH, OCH, -2 0 - H 6-H(CH,) 2 - S - A-5 CH, SCH, j -2 0 - H H - S0 2 - A-5 CH, OC^CH, J-2 0 - H H - S0 2 - A-S CH, C^CH, 83 Table VI (continued) tt n ft T v v * # P* 1 ϊ £ S !l a -Li i i !i !i fl i__21 J-2 0 - H 6-CH, - S0 2 - A-S CH j CF, CH, J-2 0 - H H - XH - A-5 CH, OCH, J-2 0 - H H - HCH, - A-5 CH, OCH.CH, - J-2 0 - H 5-OCH - HCH - A-5 CH, OCH, J-2 0 - H 6-SCH - NCH CH, - A-5 CH OCH 0 J-2 0 - H H - HC H - A-5 CH, OCH, J-2 0 - H H - HCH.CHCH, - A-5 CH, CH, 2 2 3 3 J-2 0 CH 2 H H - S - A-5 CH, CH, J-2 S - H H - HCH - A-5 CH CH, J-3 0 - H H - 0 - A-5 CH CH, CH, J-3 0 - H H - 0 A-5 CH OCH J-3 0 - H H - 0 A-5 CH, SCH J-3 0 - H 5-CH CH - 0 - A-5 CH, CH, J-3 0 - H 5-F - 0 - A-5 CH, CH J-3 0 - H 6-HHCH - 0 A-5 CH OCH, J-3 0 - H 6-CX - 0 - A-5 CH OCH J-3 0 - H H - S A-5 CH OCH J-3 0 - H H - S - A-5 CH. OCH.CH, - 3 2 3 20 J-3 0 - H 5-F - S - A-5 CH SCH J-3 0 - H 6-OCH - S A-5 CH, CH, J-3 0 - H H - HCH, - A-5 CH,CF, CH. 3 2 3 3 J-3 0 - H 5-Cl - HCH. - A-5 CH, CH, 3 3 3 J-3 0 - H 6-H(CH 2 - HCH, - A-5 CH CH CH, J-3 0 - H H - HCH CH - A-5 CH CH SCH J-3 S - H H - 0 A-S CH SCH, 2 5 J-3 0 - CH H - S - A-5 CH, CH, J-4 0 - H H 0 HCH, HCH, A-5 CH, OCH, 3 3 3 3 J-4 0 - H H 1 0 0 A-5 CH m m 3 " J-4 0 - H H 0 HCH. A-5 CH,CH, CH, 3 2 3 3 J-4 0 - H H I S 0 A-5 CH,CH, OCH, 2 3 3 J-4 0 - H H I S HCH A-5 CH CF OCH -, « J-4 0 - H H 1 HCH. HCH, A-5 CH,CF, CH, 30 3 3 2 3 3 35 Table VI (continued) J E R !ι « 2i i A ϊi li _1 J-4 0 - H H 2 0 0 A-5 SCH, - C 3 J-4 0 - H 5-Cl 2 0 0 A-5 OCH, - m J-4 0 - H H 2 S 0 A-5 CH, - 3 J-4 0 - H H 2 HCH 0 A-5 OCH, - m 3 J-4 0 CH , H H 1 0 0 A-5 CH 2 CH, OCH, - J-4 S - H H 2 0 0 A-5 CH OCH - J-5 0 - H H - XH HH A-5 CH, - ∞S J-5 0 - H H - XH HH A-S SCH CH, - CT 3 J-5 0 - H H - XCH HH A-5 OCH, - OT 3 J-5 0 - H H - HCH HCH, A-5 CH, CH, - J-5 0 - H 5-OCH, - HCH,CH. HCH, A-5 OCH, - 2 3 ∞3 J-5 0 - K 6-Cl - HCH, HH A-5 CH, ∞S - J-5 0 - CH, H - HH HH A-5 CH, CH, - J-l 0 - H H - S - A-6 CH, - J-l 0 - H 5-Cl - s - A-6 CH, - - J-l 0 - H 5-OCH - s - A-6 CH, - - J-l 0 - H 6-Br - s - A-6 CH, - - J-l 0 - H 6-OCH, - so 2 - A-6 CH, - - J-l 0 - H K - so 2 - A-6 CH, - - J-l 0 - H H - so 2 - A-6 OCH, - - j-l o - H 5-CH. - HH 3 - A-6 OCH - - J-l 0 - H H - HCH - A-6 OCH - - J-l 0 - H 5-CF, - HCH, - A-6 OCH - - J-l 0 - H 6-Cl - HCH, - A-6 CH, - - J-l 0 - H H * " C Λ - A-6 m 3 - - J-l 0 - H H - HCH 2 C.H 5 - A-6 CH, - - J-l 0 0 H H - S - A-6 OCH, - - J-l 0 - CH, H - HCH, - A-6 CH, - - J-2 0 - K H - S - A-6 OCH - - J-2 0 - H 5-SCH - s - A-6 CH, - - J-2 0 - H 5-CH - s - A-6 OCH, - - J-2 0 - H 6-H(CH,) 2 - s - A-6 OCH - - Table i VI (continued) - B.p. J U E R n 2ι 2ι !ι li Il -ISl J-2 0 - H H - so 2 - A-6 OCH, - - J-2 0 - H H - so 2 - A-6 CH, - - J-2 0 - H 6-CH 3 - so 2 - A-6 OCH, - - J-2 0 - H H - HH - A-6 OCH, - - J-2 0 - H H - HCH, - A-6 OCH, - - J-2 0 - H 5-OCH, - HCH, - A-6 OCH, - - J-2 0 - H 6-SCH, - HCHjCH, - A-6 OCH, - - J-2 0 - H H - HC 6 H S - A-6 m 3 - - J-2 0 - H H - HCH.CHCH. A-6 2 2 m - - J-2 0 CH. , H H - S - A-6 CH, - - J-2 s H H - XCH, - A-6 OCH, - - J-3 0 - H H - 0 - A-6 CH, - - J-3 Q - H H - 0 - A-6 OCH, - - J-3 0 - H 5-CH 2 CH, - 0 - A-6 CH, - - J-3 0 - H 5-F - 0 - A-6 OCH, - - J-3 0 - H 6-NHCH, - 0 - A-6 OCH - - J-3 0 - H 6-CH - 0 - A-6 OCH, - - J-3 0 - H K - s - A-6 CH, - - J-3 0 - H H - s - A-6 OCH, - - J-3 0 - H 5-F - s - A-6 OCH - - J-3 0 - H 6-OCH, - s - A-6 OCH, - - J-3 0 - H H - HCH, - A-6 CH, - - J-3 0 - H 5-Cl - HCH, - A-6 OCH, - - J-3 0 - H 6-H(CH,) 2 - HCH, - A-6 CH, - - J-3 0 - H H - NCHjCH, - A-6 CH, - - J-3 s - H H - 0 - A-6 CH, - - J-3 0 - CH, H - S - A-6 CH, - - J-4 0 - H H 0 HCH, HCH, A-6 OCH, - - J-4 0 - H H 1 0 0 A-6 OCH, - - J-4 0 - H H 1 0 HCH A-6 CH, - - J-4 0 - H H 1 S 0 A-6 CH, - - J-4 0 - H H 1 s HCH, A-6 OCH - - Table VI (continued) J-4 0 - H H 1 HCH, HCH ( A-6 OCH, - - J-4 0 - H H 20 0 A-6 OCH - - J-4 0 - • H 5-Cl 2 0 0 A-6 OCH - - J-4 0 - H H 2 S 0 A-6 OCH, - - J-4 0 - H H 2 HCH 0 A-6 OCH, - - J-4 0 CH H H 10 0 A-6 CH, - - J-4 S - H H 20 0 A-6 CH, - - J-5 0 - H H - HH HH A-6 CH, - - J-50 - H H - HH HH A-6 OCH - - J-5 0 - H H - HCH, HH A-6 OCH - - J-5 0 - H H - HCH HCH A-6 CH, - - J-5 0 - H 5-OCH - HCH CH, HCH, A-6 OCH, - - J-5 0 - H 6-Cl - HCH, XH A-6 OCH, - - J-5 0 - CH, H - HH XH A-6 CH, - - J-l 0 - H H - S - A-7 CH, CH, CH J-l 0 - H 5-Cl - S - A-7 Cl CH, CH J-l 0 - H 5-OCH .- s - A-7 OCH CH ∞S J-l 0 - H 6-Br - S - A-7 OCH OCH CH J-l 0 - H 6-OCH - so 2 - A-7 CH, Cl CH J-l 0 - H H - so 2 - A-7 CH OCH CH, CH J-l 0 - H H - so 2 - A-7 CH CH, X J-l 0 - H 5-CH, - HH - A-7 OCH CH, H J-l 0 - H H - HCH, - A-7 OCH CH CH, H J-l o - H 5-CF, - HCH, - A-7 OCH, CH, CH J-l 0 - H 6-Cl - HCH, - A-7 OCH, OCH, CH J-l 0 - H H " " C 6 H 5 - A-7 Cl OCH, CH J-l 0 - H H " HCH 2 C 6 H 5 - A-7 CH, OCH, CH J-l 00 H H - s - A-7 CH OCH, CH J-l 0 - CH, H - HCH, - A-7 OCH, OCH, CH J-2 0 - H H - s - A-7 CH, OCH, CH J-2 0 - H 5-SCH, - S - A-7 CH, OCH CH, CH J-2 0 - H 5-CH - S - A-7 CH CH, H Table VI (continued) J-2 0 - H 6-H(CH,) 2 s - A-7 OCH, CH, X J-2 0 - H H - so 2 - A-7 OCH X ra 3 J-2 0 - K H - so 2 - A-7 CH, CH, X J-2 0 - H 6-CH, - so 2 - A-7 CH, CH ∞S J-20 - H H - HH - A-7 OCH, CH m 3 J-20 - H H - HCH, - A-7 ™ 3 OCH CH J-2 0 - H 5-OCH, - HCH, - A-7 CH, OCH, CH J-20 - H 6-SCH, - HCH.CH, - A-7 CH 3 OCH, CH J-20 - H H - - A-7 CH 3 OCH CH MC 6 H 5 J-2 0 - H H - NCH CHCH A-7 OCH OCH, CH J-2 0 CH 2 H H - S - A-7 OCH 3 OCH, X J-2 S H H - HCH, - A-7 OCH CH, X J-3 0 - H H - 0 - A-7 OCH. X OT 3 J-3 0 - H H - 0 - A-7 OCH CH, CH J-3 0 - H H - 0 - A-7 OCH OCH, CH J-3 0 - H 5-CH,CH. - 0 - A-7 Cl OCH CH 2 3 J-3 0 - H 5-F - 0 - A-7 CH 3 OCH CH J-3 0 - H 6-NHCH. - 0 - A-7 CH 3 OCH, CH J-3 0 - H 6-CH - 0 - A-7 CH 3 OCH CH J-3 0 - H H - s - A-7 CH¬ CH, X J-3 0 - H H - s - A-7 OCK, X m 3 J-3 0 - H 5-F - s - A-7 OCH, CH, X J-3 0 - K 6-OCH - s - A-7 OCH, CH, X J-3 0 - H H - HCH, - A-7 OCH CH, X J-3 0 - H 5-Cl - HCH, - A-7 OCH CH, CH J-3 0 - H 6-H CH 3 ) 2 - HCH - A-7 OCH CH, CH J-3 0 - H H - HCH 2 CH, - A-7 OCH, CH, CH J-3 S - H H - 0 - A-7 OCH CH, CH J-3 0 - CH, H - s - A-7 OCH, CH CT 3 J-4 0 - H H 0 HCH HCH A-7 OCH OCH CH J-4 0 - H H 1 0 0 A-7 OCH, X ra 3 J-4 0 - H H 1 0 HCH A-7 CH, OCH, CH 88 Table VI (continued). J-4 0 - H H 1 s 0 A-7 CH-OCH- ( OCH, CH J-4 0 - H H 1 s HCH, A-7 OCH OCH, CH J-4 0 .- H H 1 HCH, HCH, A-7 OCH, Cl CH J-4 0 - H K 2 0 0 A-7 OCH, CH, X J-4 0 - H 5-Cl 2 0 0 A-7 OCH, CH, H J-4 0 - H H 2 s 0 A-7 OCH, CH, X J-4 0 - H H 2 HCH 0 A-7 OCH, CH, X J-4 0 CH 2 H H 1 0 0 A-7 OCH, CH, CH J-4 s H H 2 0 0 A-7 OCH, OCH, CH J-5 0 - K H - HH HH A-7 OCH, CH ∞S J-5 0 - H H - HH HH A-7 CH, CH CT 3 J-5 0 - H H - HCH, HH A-7 CH, OCH j CH, CH J-5 0 - K H - HCH, HCH, A-7 OCH 2 CH, CH, CH J-5 0 - H S-OCH, - HCH CH HCH, A-7 OCH, CH, X J-5 0 - H 6-Cl - HCH HH A-7 OCH, CH, X J-5 0 - CH, H - HH HH A-7 OCH, CH, CH 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: Table VII 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, micro¬ biological 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. 1973. 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. Kling an, "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 Hand¬ book", 5th Ed., Blackwell Scientific Publications, Oxford. 1968. pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 12 Wettable Powder N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-l,2.3-benzothiadiazole-4-sulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, re- blended, and packaged. Example 13 Wettable Powder N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2.3-benzothiadiazole-4-sulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely ammer- milled and then air-milled to produce particles essen¬ tially all below 10 microns in diameter. The product is reblended before packaging. Example 14 Granule Wettable Powder of Example 13 5% attapulgite granules 95% (U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. Example 15 Extruded Pellet N-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2.3-benzothiadiazole-4-sulfonamide 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 16 Oil Suspension N-[ (4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2,3-benzothiadiazole-4-6Ulfonamide 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 17 Wettable Powder N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2.3-benzothiadiazole-4-sulfonamide 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essen- tially 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 18 Low Strength Granule N-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1, ,3-benzothiadiazole-4-sulfonamide 1% N.N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 19 Agueous Suspension N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-l,2.3-benzothiadiazole-4-sulfonamide 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium 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 20 Solution N-[ (4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2,3-benzothiadiazole-4-sulfonamide, ammonium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. Example 21 Low Strength Granule N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1,2,3-benzothiadiazole-4-sulfonamide 0.1% attapulgite granules 99.9% (U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged. . Example 22 Granule N-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonγl]-5- methoxy-1.2,3-benzothiadiazole-4-sulfonamide 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20% of the natural sugars) attapulgite clay 9% The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidiza- tion and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat. until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example 23 Hig ' h Strength Concentrate N-[ (4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2.3-benzothiadiazole-4-βulfonamide 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 24 Wettable Powder N-[(4.6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1.2,3-benzothiadiazole-4-sulfonamide 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. Example 25 Wettable Powder N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1,2,3-benzothiadiazole-4-sulfonamide 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 26 Oil Suspension N-[(4,6-Dimethoxγpγrimidin-2-yl)aminocarbonyl]-5- methoxy-1,2,3-benzothiadiazole-4-sulfonamide 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water. Example 27 Dust N-[ (4.6-Dimethoxypy imidin-2-yl)aminocarbonyl]-5- methoxy-1.2.3-benzothiadiazole-4-sulfonamide 10% attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapul¬ gite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example 28 Emulsifiable Concentrate N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-l,2,3-benzothiadiazole-4-sulfonamide 10% chlorobenzene 84% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to pro¬ duce a solution which can be emulsified in water for application. Uti lity Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. 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 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 crops, such as rice, barley, cotton, oilseed rape and sugarbeets. Some of the compounds were found to be especially selective to sugarbeets and oilseed rape. 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 regulants or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formula¬ tions selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.001 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 situa¬ tions where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole. uracil. urea, amide, diphenylether, carbamate and bipyridylium types. Some of them are particularly useful when combined with the herbicides below: DESMEDIPHAM (BETANEX®) Ethyl m-hydroxycarbanilate carbonilate (ester) PHENMED1PHAM (BETANAL®) Methyl m-hydroxycarbanilate m-methylcarbanilate ETHOFUMESATE (NORTRON®) (+ > )-2-ethoxy-2.3-dihydro-3.3-dimethyl-5-benzo = furanyl methanesulfonate DIETHATYL ETHYL (ANTOR®) N-chloroacetyl-N-(2.6-diethylphenyl)-glycine ethyl ester ENDOTHALL 7-oxabicyclo [2,2,1] heptane-2.3-dicarboxylic acid TCA Trichloroacetic acid DALAPON (DOWPON®) 2,2-dichloroproprionic acid FENURON 1,l-dimethyl-3-phenylurea CHLORPROPHAM Isopropyl m-chlorocarbanilate PROPHAM Isopropyl carbanilate PYRAZON (PYRAMIN®) 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone METAMITRON (GOLTIX®) 4-amino-3-methyl-6-phenyl-1.2,4-triazia-5(4H)- one LENACIL (VENZAR®) 3-cyclohexyl-6,7-dihydro-lH-cyclopenta- pyrimidine-2.4(3H,5H)-dione SETHOXYDIM (POAST®) (±)2-[l-(ethoxyimino)butyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexene-l-one FLUAZIFOP-BUTYL (FUSILADE®) ( ± )-butyl-2-[4-[(5-(trifluoromethyl)-2- pyridinyl)oxy]phenoxy]propanoate DIALLATE (AVADEX®) S-(2,3-dichloroallyl)diisopropylthio carbamate BARBAN (CARBYNE®) 4-chloro-2-butynyl m-chlorocarbanilate DICLOFOP-METHYL (HOELON®) Methyl 2-[4-(2.4-dichlorophenoxy)phenoxy] propanoate QUIZALOFOP (RS)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy] proprionic acid The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. It is believed that the compounds which show weak activity at low rates will show herbicidal activity at higher rates. Compound X Y Z. 1 OCH 3 CH 3 CH 3 CH 2 OCH 3 CH 3 0 CH 3 CH 3 OCH 3 CH 3 0 CH 3 0 CH 4 OCH 3 Cl CH 3 0 CH Ϊ01 Compounds (Continued) Compound . *1 X Y Z 5 OCH 3 CH, CH, N 6 OCH 3 CH 3 0 CH 3 N 7 OCH 3 CH 3 0 CH 3 0 N 8 H CH 3 CH 3 CH 9 H OCH 3 CH 3 CH 10 H OCH 3 OCH 3 CH 11 H Cl OCH 3 CH 12 H CH 3 OCH 3 N 13 H OCH 3 OCH 3 N 14 H OCH 2 CH. - NHCH 3 N Compound X Y Z 15 CH 3 CH, CH 16 CH 3 OCH 3 CH 17 OCH OCH 3 N [ 3 18 OCH CH 3 N [ 3 19 OCF NHCH 3 N [ 2 C 3 20 Cl OCH, CH Compoundsi (Continued) Compound X Y Z 21 CH 3 CH 3 CH 22 OCH 3 CH 3 CH 23 OCH 3 OCH 3 CH 24 Cl OCH 3 CH 25 CH 3 CH 3 H 26 CH 3 OCH 3 N 27 OCH 3 OCH 3 N Compound X Y Z 29 CH 3 CH 3 CH 30 CH 3 OCH 3 CH 31 OCH 3 OCH 3 CH 32 Cl OCH 3 CH 33 CH 3 CH 3 N 34 OCH 3 CH 3 N 35 OCH 3 OCH 3 N 36 OCH 2 CH 3 NHCH N Compounds; (Continued) Compound X Y Z 37 CH 3 CH 3 CH 38 0CH 3 CH 3 CH 39 OCH 3 OCH 3 CH 40 Cl OCH 3 CH 41 CH 3 CH 3 N 42 CH 3 OCH 3 N 43 OCH 3 OCH 3 N 44 OCH 2 CH 3 NHCH 3 N Compound X Y Z. 45 CH 3 CH 3 CH 46 OCH 3 CH 3 CH 47 OCH 3 OCH CH 48 OCH 3 CH 3 N 49 OCH, OCH N Compound "l X Y Z 50 H CH. CH. CH 104 Compounds (Continued) Compound II X Y Z 51 H CH 3 OCH 3 CH 52 H OCH. OCH, CH 53 H Cl OCH, CH 54 H CH 3 CH N 55 H OCH. CH N 56 H OCH. OCH 3 N 57 CH, OCH. OCH, CH Compound X Y Z 58 H CH. CH. CH 3 CH 59 H CH, CH 3 OCH 3 CH 60 H CH. OCH. OCH. CH 61 H CH: Cl J OCH 3 CH 62 H CH * . CH, CH, N 63 H CH, CH OCH 3 N 64 H CH, OCH 3 OCH 3 N 65 Η CH, OCH 2 CH 3 NHCH, N 66 CH, H CH, CH, * CH 67 CH, H CH, OCH 3 CH 68 CH, H OCH 3 OCH 3 CH 69 CH, H Cl OCH 3 CH 70 CΗ. H CH 3 OCH 3 N 71 CH " H CH, CH, N Compounds (Continued) Compound [ X Y z 72 OCH 3 CH 3 CH 73 OCH 3 OCH 3 CH 74 Cl OCH 3 CH 75 OCH 3 CH 3 N 76 OCH 3 N(CH 3 ) 2 N Compound X Y Z 77 CH 3 CH 3 CH 78 OCH 3 CH 3 CH 79 OCH 3 OCH 3 CH 80 Cl OCH 3 CH 81 OCH 3 CH 3 N 82 OCH 3 (CH 3 ) 2 N Compounds (Continued) Compound i X Y Z 83 CH 3 CH 3 CH 3 CH 84 CH 3 CH 3 OCH 3 CH 85 CH 3 OCH 3 OCH 3 CH 86 CH 3 OCH 3 Cl CH 87 CH 3 CH 3 CH 3 N 88 CH 3 OCH 3 CH 3 N 89 CH 3 OCH 3 OCH 3 N 90 CH 3 OCH 2 CH, NHCH N 91 H CH 3 • CH 3 CH 92 H CH 3 OCH 3 CH 93 H OCH 3 OCH 3 CH 94 H Cl OCH 3 CH 95 H OCH 3 CH 3 N 96 H OCH 3 OCH 3 N 97 H OCH 2 CH 3 NHCH N 98 H OCH 3 (CH 3 ) 2 N 99 Cl CH 3 CH 3 CH 100 Cl OCH 3 CH 3 CH 101 Cl OCH 3 OCH 3 CH 102 Cl Cl 0CH 3 CH 103 Cl CH 3 CH N 104 Cl OCH 3 CH 3 N 105 Cl OCH 3 OCH 3 N 106 Cl OCH 2 CH 3 NHCH N Compounds (Continued) H Compound X Y Z 107 OCH 3 CH 3 CH 108 OCH 3 OCH 3 CH 109 OCH 3 CH 3 N Compound X Y Z. 110 N(CH 3 ) 2 OCH 3 N 111 (CH 3 ) 2 C 2 H 5 N 112 OCH 2 CF 3 (CH 3 ) 2 N 113 SC 2 H 5 NHCH 3 N 114 NHCH OCH(CH 3 ) 2 N 115 OCH 3 N(CH 3 )CH 2 CN N 116 OCH 3 NHCH CN N 117 NHCH OC 2 H 5 CH 118 CH 3 CH 2 OCH 3 CH 119 OCH C=CH CH 3 N 120 OCH CF NHCH N Compounds (Continued) Compound X Y Z. 121 CH 3 CH 3 CH 122 OCH 3 CH 3 CH 123 OCH 3 OCH 3 CH 124 Cl OCH 3 CH 125 OCH 3 CH 3 N 126 OCH 2 CH 3 NHCH N Test A Seeds of crabgrass (Diqitaria spp.), barnyard- grass (Echinochloa crusgalli). wild oats (Avena fatua). cheatgrass (Bromus secalinus). velvetleaf (Abutilon theophrasti). morningglory (Ipomoea spp.). cocklebur (Xanthium pensylvanicum). sorghum, corn, soybean, sugarbeet, cotton, rice, wheat and purple nutsedge (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 con¬ trols 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. Table A Compound 1 Compound 2 Rate k/ha 0.05 0.01 0.05 0.01 POSTEMERGENCE • Morningglory 2C.7G 2G 3C.9G 7G Cocklebur 7G 5H IOC 8G Velvetleaf 5C.9G 6G 9C 5G Nutsedge 9G 0 3C.9G 0 Crabgrass 9G 5G 5C.9G 5G Barnyardgrass 9C 3C.9H IOC 8H Cheatgrass 9G 9G 9C 6G Wild Oats 9C 3C.9G 9C 9C Wheat 9C 9G 9C 9G Corn 9C 9G 9C 5U.9H Soybean 9C 9C IOC 9C Rice 6C.8G — 9C 2C.8G Sorghum 4C.9G 9G 9C 3C.9H Sugar beet 5C.9G 3C.5G 9C 2G Cotton IOC 2C.9G IOC 9C PREEMERGENCE Morningglory 3G 0 6G 0 Cocklebur - - 5G 1H Velvetleaf 5H 0 7G 5H Nutsedge 10E 0 10E 5G Crabgrass 6G 0 4C.9G 4G Barnyardgrass 7G 0 9H 5G Cheatgrass 9G 5G 9H 8G Wild Oats 2C.8G 0 3C.8G 0 Wheat 9H 0 3C.9H 8G Corn 9H 2C 2C.9H 9G Soybean 5G 0 2C.7H 0 Rice 9H 7G 9H 9G Sorghum 4C.9H 5G 9H 5G Sugar beet 4G 4H 7G 2H Cotton 7G 0 9G 2G Table A (continued) Compound 3 Compound 4 Rate k/ha 0.05 0.01 0.05 0.01 POSTEMERGENCE Morningglory IOC 4C.9G 3C.7G 3H Cocklebur IOC 9C IOC IOC Velvetleaf 9C 4C.9G 9C 7G Nutsedge 9C 3C.7G 3C.9G 5G Crabgrass 2C.9G 2C.9G 3C.9G 3C.9G Barnyardgrass 9C 9C 9C 9C Cheatgrass 5C.9G 4C.9G 4C.9G 7G Wild Oats 9C 9C 4C.8G 6G Wheat 9C 2C.9G 9G 7G Corn IOC 7U.9C 9C 9C Soybean 9C 9C 9C 9C Rice 5C.9G 5C.9G 5C.9G 8G Sorghum 9C 5C.9G 9C 5C.9G Sugar beet 6C.9G 4C.9G 9C 2H Cotton IOC - 5C.9G 6G PREEMERGENCE Morningglory 9G 5G 9G 6H Cocklebur 5H 0 4H 0 Velvetleaf 8G 0 3C.8G 0 Nutsedge 9G 8G 4G 0 Crabgrass 8G 2G 5G 0 Barnyardgrass 9H 0 8H 2G Cheatgrass 9H 5G 9G 7G Wild Oats 8G 0 0 0 Wheat 9G 7G 4G 0 Corn 9H 2C.5G 3C.9H 3G Soybean 3C.7H 0 2C.5G 2G Rice 9H 9H 9H 9H Sorghum 9H 8G 10H 9H Sugar beet 6G 0 5G 2H Cotton 9G 5G 8G 5G Table A (continued) Compound 5 Compound 6 Rate k/ha 0.05 0.01 0.05 0.01 POSTEMERGENCE Morningglory 0 0 3C.7G 0 Cocklebur 0 0 - 8H Velvetleaf 0 0 6G 2H Nutsedge 0 0 0 0 Crabgrass 0 0 3C.9G 0 Barnyardgrass 5C.9H 3H 9C 9C Cheatgrass 8G 3G 5C.9G 9G Wild Oats 9G 4G 9C 9C Wheat 9G 6G 5C.9G 9C Corn 5C.9G 2C.8H 9C 9C Soybean 5H 1H 9C 2C.9G Rice 8G 5G 9C 5C.9G Sorghum 9G 6G 9C 9C Sugar beet 0 0 3C.8G 3G Cotton 2G 0 6G 0 PREEMERGENCE Morningglory 0 0 9G 4G Cocklebur 0 0 8G 0 Velvetleaf 0 0 7G 0 Nutsedge 0 0 8G 0 Crabgrass 0 0 2C.8G 7G Barnyardgrass 0 0 9H 5G Cheatgrass 0 0 9H 6G Wild Oats 0 0 2C.8G 0 Wheat 7G 0 3C.9H 9H Corn 2C.3G 0 3C.9G 2C.7H Soybean 0 0 3C.7H 0 Rice 9G 0 10H 10H Sorghum 9G 0 9H 9H Sugar beet 0 0 8G 0 Cotton 2G 0 9G 0 Table A (continued) Compound 7 Rate k/ha 0.05 0.01 POSTEMERGENCE Morningglory 2C.5G 0 Cocklebur 9C 4C.9G Velvetleaf 5G 1H Nutsedge 2C.8G 0 Crabgrass 3C.9G 3C.8G Barnyardgrass 9C 3C.9H Cheatgrass 9G 2C.9G Wild Oats 9C 9C Wheat 3C.9G 9G Corn 9C 3C.9G Soybean 9C 3C.8H Rice 9C 4C.9G Sorghum 9C 3C.9G Sugar beet IOC 6G Cotton 5C.9G 1H PREEMERGENCE Morningglory 8G 0 Cocklebur 1H 0 Velvetleaf 0 0 Nutsedge 10E 0 Crabgrass 3C.8G 5G Barnyardgrass 4G 0 Cheatgrass 8G 0 Wild Oats 3C.9G 0 Wheat 3C.9H 3G Corn 3C.9H 3C.8H Soybean 2G 0 Rice 10H 8G Sorghum 10H 3C.9H Sugar beet 3C.9G 3H Cotton 7G 9H Table A (continued) CMPD 8 CMPD 9 RATE=KG/Hλ 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 10C 6G IOC IOC COCKLEBUR 10C 10C IOC 9C VELVETLEAF IOC 10C IOC IOC NUTSEDGE 10C SC,9G IOC 9C CRABGRASS 9C 4C.9G IOC 5C,9G GIANT FOXTAIL IOC 4C.9G IOC 9C BARNYARD GRASS 9C 9C IOC 9C CHEATGRASS 9C 7G IOC 9C WILD OATS 2G 0 5C,9G 7G WHEAT IOC 9C 9C 9C CORN 10C 10C IOC IOC BARLEY 5C.9G 2G 9G 7G SOYBEAN 9C 9C 9C 5C,9G RICE 9C 9C 9C 9C SORGHUM 9C IOC 9C 5C.9G SUGAR BEETS 10C IOC IOC IOC COTTON 10C 10C IOC 10C PREEMERGENCE MORNING GLORY 9G 7G 9G 9G COCKLEBUR 7H 0 9H 0 VELVETLEAF 9G 9G 9G 7H NUTSEDGE loε 2G 5G 3G CRABGRASS 8G 0 8G 7G GIANT FOXTAIL 9H 0 9H 8G BARNYARD GRASS 9H 0 9H 5H CHEATGRASS 9G 3G 9H 9G WILD OATS 2C.4G 2G 3C.7G 3G WHEAT 9H 7G 4C.9H 9H CORN 9H 8H 3C.9H 8H BARLEY 2G 0 9G 7G SOYBEAN 9H 2C.7H 9H 2C.8H RICE 10H 9H 10H 9H SORGHUM 10H 10H 9H 9H SUGAR BEETS 9C 4G 9C 4G COTTON 9G SG 9G 8G Table.A (continued) CMPD 10 CMPD 11 RATE»KG/HA 0.05 O.Oi 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 9C IOC IOC COCKLEBUR IOC 9C 9C 9C VELVETLEAF IOC IOC IOC IOC NUTSEDGE OC 3C.7G 9C 3C.5G C RAB G RASS 9C 3C.8G 9C 4C.8G G IANT FOXTAIL IOC IOC IOC 9C BARNYARD GRASS 9C 9C IOC 9C CHEATGRASS IOC 9C 9C 6G WILD O ATS 6C.9G 3C.9G 5G 0 4C.9G 6G WHEAT 9C 5C.9G CORN IOC IOC IOC 9C BARLEY 5C.9G 4C.9G 4G 0 2C.6H SOYBEAN 9C 9C 9C RICE 9C 9C 9C 9C SORGHUM IOC 9C 9C IOC SUGAR BEETS IOC 9C IOC IOC C O TTON IOC IOC IOC IOC PREEMERGENCE MORNING GLORY 9H 3G 9G 7G COCKLEBUR 8H 5G VELVETLEAF 4C,9G 8 G 8G 7H NUTSEDGE 4C.9G 2C.6G 3C.6G 0 CRABGRASS 3C.9G 2C.5G 7G 4G G IANT FOXTAIL 9H 9H 8G 3C.6G BARNYARD GRASS 9H 3H 9H 3H CHEATGRASS 4C.9G 7G 7G 0 WILD OATS 6G 8G 3G 2C WHEAT 4C.9H 9H 8G 2G CORN 4C.9H 3C.9H 9H 9H BARLEY 8G 4G 7G 0 SOYBEAN 9H 7G 3C.8H 2G RICE 9H 9G 9K 9H S O R G HUM 4C.9H 8H 9H 9H SUGAR BEETS 9C 9C 9C 7G C O TTON 9G 7G 8G 2G Table A ( continued ) CMPD : 12 CMPD 13 RATE=KG/Hλ 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 10C IOC IOC COCKLEBUR 9C 10C IOC IOC VELVETLEAF IOC IOC IOC IOC NUTSEDGE 2C.5G 2G 5C, 9G 2C.8G CRABGRASS IOC 9C 9C 9C GIANT FOXTAIL IOC IOC IOC IOC BARNYARD GRASS 9C IOC 9C 9C CHEATGRASS 9C 4C.8G 60 60 WILD OATS 0 0 2C 0 WHEAT 9C 5C-9G 9C 9G CORN IOC IOC IOC 6C.9G BARLEY 9G 8G 9G 4G SOYBEAN 9C 9C 9C 9C RICE 9C 9C 9C 9C SORGHUM 9C IOC 9C 9C SUGAR BEETS IOC IOC OC 7G COTTON IOC 9C IOC IOC PREEMERGENCE MORNING GLORY 9G 9G 9G 9G COCKLEBUR 9H 9G 7H 0 VELVETLEAF 4C,9G 3C.7G 4C, 9G 0 NUTSEDGE 9G 0 loε 0 CRABGRASS 5C.9G 4C.8G 4C, 9G 6G GIANT FOXTAIL 9H 4C.9H 4C, 9H 5G BARNYARD GRASS 9H 3C.9H 9H 5H CHEATGRASS 9H 7G 8H 0 WILD OATS 2C.4G 0 2G 0 WHEAT 9H 9H 9H 8G CORN 9C 3C.9H 9G 2C.7H BARLEY 9G 7G 9G 3G SOYBEAN 9H 8G 4C, 8H 6G RICE 10E 5C.9H 5C, 9H 9H SORGHUM 10H 4C.9H 10H 9G SUGAR BEETS 9C 4C.9G 7H 3G COTTON 4C.9G 7G 2C, 9G 4G Table A ( continued ) CMPD 14 CMPD 15 RATE=-KG/HA 0.05 0.01 0 . 05 0 . 01 POSTEMERGENCE MORNING GLORY 4C, 9G 2C,2H COCKLEBUR IOC 3G 0 VELVETLEAF IOC 8G 0 NUTSEDGE 4G 0 0 CRABGRASS 9C 8G 0 GIANT FOXTAIL 9C 4C,9H 0 BARNYARD GRASS 4C, 9G 6H 0 CHEATGRASS 5C, 9G 7G 0 WILD OATS 3C, 8G 5G 0 WHEAT 5C, 9G 2C,7G 0 CORN 5U. 9G 5C.9G 0 BARLEY 7G 4G 0 SOYBEAN 4C, 9G 5C.9G 0 RICE 9C 5C.9G 0 SORGHUM 4C, 9G 9G 0 SUGAR BEETS 6G 2G 0 COTTON IOC 7G 0 PREEMERGENCE MORNING GLORY 9G 2G 0 COCKLEBUR - 0 0 VELVETLEAF 8H 0 0 NUTSEDGE 7G 0 0 CRABGRASS 7G 2G 0 GIANT FOXTAIL 8G 2G 0 BARNYARD GRASS 8H 0 0 CHEATGRASS 9G 0 0 WILD OATS 3G 0 0 WHEAT 3G 0 0 CORN 2C, 9H 5G 0 BARLEY 0 0 0 SOYBEAN 7H 2G 0 RICE loε 7G 0 SORGHUM 9H 9G 0 SUGAR BEETS 0 0 0 COTTON 7G 0 0 Table A (continued) CMPD 16 CMPD 17 RATEsKG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 - 0 COCKLEBUR 3C, 7H - 0 VELVETLEAF 0 - 0 NUTSEDGE 0 - 0 CRABGRASS 0 - 0 GIANT FOXTAIL 0 - 0 BARNYARD GRASS 0 - 0 CHEATGRASS 0 - 0 WILD OATS 0 • - 0 WHEAT 0 - 0 CORN 0 - 0 BARLEY 0 - 0 SOYBEAN 7β - 0 RICE 0 - 0 SORGHUM 0 - 0 SUGAR BEETS 3C, SG - 0 COTTON 0 - 0 PREEMERGENCE " MORNING GLORY 0 - 0 COCKLEBUR 0 - 0 VELVETLEAF 0 - 0 NUTSEDGE 0 - 0 CRABGRASS 0 - 0 GIANT FOXTAIL 0 - 0 BARNYARD GRASS 0 - 0 CHEATGRASS 0 - 0 WILD OATS 0 - 0 WHEAT 0 - 0 CORN 0 - 0 BARLEY 0 - 0 SOYBEAN 0 - 0 RICE 0 - 0 SORGHUM 0 - 0 SUGAR BEETS 5G - 0 COTTON 2G - 0 Table A (continued) CMPD 18 CMPD 19 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 COCKLEBUR 2G 0 VELVETLEAF 0 0 NUTSEDGE 0 0 CRABGRASS 0 0 GIANT FOXTAIL 0 0 BARNYARD GRASS 0 0 CHEATGRASS 0 0 WILD OATS 0 0 WHEAT 0 0 CORN 2C.5H 0 BARLEY 0 0 SOYBEAN 0 0 RICE 2G 0 SORGHUM 2C,5G 2C.5G SUGAR BEETS 0 2H COTTON 2H 0 PREEMERGENCE MORNING GLORY 0 0 COCKLEBUR 0 0 VELVETLEAF 0 0 NUTSEDGE 0 0 CRABGRASS 0 0 GIANT FOXTAIL 0 0 BARNYARD GRASS 0 0 CHEATGRASS 0 0 WILD OATS 0 0 WHEAT 0 0 CORN 0 0 BARLEY 0 0 SOYBEAN 0 0 RICE 0 0 SORGHUM 0 0 SUGAR BEETS 0 0 COTTON 0 0 T a b l e A (continued ) CMPD 20 CMPD 21 RATE=KG/HA 0.05 0 . 0 1 0 . 0 5 0 . 01 POSTEMERGENCE MORNING GLORY 0 1C 0 COCKLEBUR 0 1C 0 VELVETLEAF 0 0 0 NUTSEDGE 0 0 0 CRABGRASS 0 0 0 GIANT FOXTAIL 0 0 0 BARNYARD GRASS 0 0 0 CHEATGRASS 0 0 0 WILD OATS 0 0 0 WHEAT 0 0 0 CORN 0 0 0 BARLEY 0 0 0 SOYBEAN 0 1C 0 RICE 0 0 0 SORGHUM 0 2C 0 SUGAR BEETS 0 2C 0 COTTON 0 2C 0 PREEMERGENCE MORNING GLORY 0 0 0 COCKLEBUR 0 0 — VELVETLEAF 0 0 0 NUTSEDGE 0 0 0 CRABGRASS 0 0 0 GIANT FOXTAIL 0 0 0 BARNYARD GRASS 0 0 0 CHEATGRASS 0 0 0 WILD OATS 0 0 0 WHEAT 0 0 0 CORN 0 0 0 BARLEY 0 0 0 SOYBEAN 0 0 0 RICE 0 0 0 SORGHUM 0 0 0 SUGAR BEETS 4G 0 0 COTTON 0 0 0 121 Table A (continued) CMPD 22 CMPD 23 RATE-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2C.3G 0 0 0 COCKLEBUR 2C, 3H 0 3H 0 VELVETLEAF 4C.9H 2C.6G 5C,9G 4C.9G NUTSEDGE 2G 0 5C.9G 5G CRABGRASS 2G 0 0 0 GIANT FOXTAIL 2C,5G 0 0 0 BARNYARD GRASS 2C.7G 2G 0 0 CHEATGRASS 2C.6G 0 0 0 WILD OATS 2C 0 0 0 .7G PREEMERGENCE MORNING GLORY 2C 0 0 0 COCKLEBUR 2C 0 0 0 VELVETLEAF 2C f 6H 0 1H 0 NUTSEDGE 0 0 3G 0 CRABGRASS 4G 0 2G 0 GIANT FOXTAIL 3C,3H 0 0 0 BARNYARD GRASS 3C-3H 0 0 0 CHEATGRASS 5G 0 8G 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 3C,4G 2C 2C 0 BARLEY 3C.3G 0 0 0 SOYBEAN 3C,4G 2C 2C.2H 0 RICE 6G 0 3G 0 SORGHUM 3C.4G 0 2C 0 SUGAR BEETS 4C.9H 7G 7H 0 COTTON 2C 0 0 0 Table A ( continued ) CMPD 24 CMP D 25 RATE=KG/HA 0. 05 0 .01 0 . 05 0 . 0 1 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 2C 3H 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 2H 0 2G 0 COTTON 0 0 0 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 . 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 26 CMPD 27 RATE*KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2H 0 2G 0 COCKLEBUR 3H 1H 0 0 VELVETLEAF 3C.7G IC 2C,6G IC NUTSEDGE 5G 0 0 0 CRABGRASS 6G 0 0 0 GIANT FOXTAIL 3C.6G 0 0 0 BARNYARD GRASS 4C.8H 2G 2H 0 CHEATGRASS 3G 0 0 0 WILD OATS 1C 0 0 0 WHEAT 0 0 0 0 CORN 3C.8H 5H 0 0 BARLEY 0 0 0 0 SOYBEAN 3C.7H 3G 3C,5H 0 RICE 8G 3G 3G 0 SORGHUM 4C,9G 3G 2C.5G 0 SUGAR BEETS 4C.9G 2C.4G 5C.9G 0 COTTON 4C.8H 2C,2G 5C,9H 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 2H 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 2G 0 CRABGRASS 2G 0 0 0 GIANT FOXTAIL 5G 0 0 0 BARNYARD GRASS 2C 0 0 0 CHEATGRASS 3G 0 0 0 WILD OATS 0 0 0 0 WHEAT 2G 0 0 0 CORN 3C,5G 0 0 0 BARLEY 7G 0 0 0 SOYBEAN 0 0 0 0 RICE 7G 0 0 0 SORGHUM 8H 2C 0 0 SUGAR BEETS 4H 1H 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 28 CMPD 29 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 4C,SH 2C.4G COCKLEBUR 0 0 9C 3C.6G VELVETLEAF 0 0 5C,9H 3C.7H NUTSEDGE 0 0 3C.7G 0 CRABGRASS 0 0 3C,3G 0 GIANT FOXTAIL 0 0 4G 0 BARNYARD GRASS 0 0 3C.7G 3G CHEATGRASS 0 0 5C.9G 2C.5G WILD OATS 0 0 2C,7G 3G WHEAT 0 0 8G 3G CORN 0 0 4C.9H 2C.8G BARLEY 0 0 2G 0 SOYBEAN 0 0 4C,8G 2G RICE 0 0 9C 3C.8G SORGHUM 0 0 5C-9G 5G SUGAR BEETS 2G 0 9C 3C.8H COTTON 2G 0 4C.9H 7G PREEMERGENCE MORNING GLORY IC 0 0 0 COCKLEBUR 0 0 — 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 2G 0 WILD OATS 0 0 3G 0 WHEAT 0 0 3G 0 CORN 0 0 IC 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 3C.4G 0 SORGHUM 0 0 0 0 ' SUGAR BEETS 0 0 5G 3G COTTON 0 0 0 0 Table A (continued) CMPD 30 CMPD 31 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 9C 9C 10C 9C COCKLEBUR IOC IOC 10C IOC VELVETLEAF IOC 9C IOC IOC NUTSEDGE 4C,8G 2C, 8G IOC 9C CRABGRASS 4C.9G 7G 4C.9G 2C.8G GIANT FOXTAIL 9C 8G IOC 9C BARNYARD GRASS 9C 8H 9C 5C.9H CHEATGRASS 9C 9C IOC 9C WILD OATS 9C 9G 4C.9G 3C,9G WHEAT 2C.9G 9G 3C.9G 2C.9G CORN 9C 3C. 9G 9C 4U.9C BARLEY 3C,9G SG 4C.9G 8G SOYBEAN 9C 9C 9C 9C RICE 9C 9C 9C 9C SORGHUM 9C 5C, 9G 9C 9C SUGAR BEETS 9C 9C IOC 9C COTTON IOC 5C, 9G IOC 9C PREEMERGENCE MORNING GLORY 9G 0 9H 8B COCKLEBUR 3C.7H 0 8H 2C.3H VELVETLEAF 3C.8G 0 4C.9G 7G NUTSEDGE 9G 0 loε 9G CRABGRASS 3C.7G 0 6G 2G GIANT FOXTAIL 2G 0 6H 2G BARNYARD GRASS 7G 0 3C.9H 1H CHEATGRASS 4C.9G 0 4C.9G 8G WILD OATS 2C,5G 0 3C-7G 2C-5G WHEAT 9H 0 9H 8G CORN 3C.9H 2C 9H 9H BARLEY 8G 0 7G 8G SOYBEAN 9H 1H 3C.9H 3C.8H RICE 4C.9H 4G 4C.9H 9H SORGHUM 2C.9H 3C, 3G 5C.9H 9H SUGAR BEETS 3C.8G 0 4C.9G IG COTTON 8G 0 9G IG Table A (continued) CMPD 32 C CMMPD 33 RATE=KG/HA 0.05 0.01 0. 05 0.01 POSTEMERGENCE MORNING GLORY 5C.9G 3C, 8G 0 0 COCKLEBUR IOC 10C IC 0 VELVETLEAF IOC 9C IC 0 NUTSEDGE 4C.9G 6G 0 0 CRABGRASS 2C.5G 0 0 0 GIANT FOXTAIL 6G 1H 0 0 BARNYARD GRASS 3C.9H 3C,7H 1H 0 CHEATGRASS 7G 6G 0 0 WILD OATS 2G 0 0 0 WHEAT 2G 0 0 0 CORN 4C.9G 9G 0 0 BARLEY 2G 0 0 0 SOYBEAN 2C.6H 3H 0 0 RICE 9C 9C 2G 0 SORGHUM 4C-9G 4C,9G 2G 0 SUGAR BEETS 9C 9C 0 0 COTTON IOC 9C 0 0 PREEMERGENCE MORNING GLORY 9G 5G 0 COCKLEBUR 9H 0 0 VELVETLEAF 4C,9H 2C 0 0 NUTSEDGE 2C.5G 0 0 0 CRABGRASS 3C,5G 0 0 0 GIANT FOXTAIL 2G 0 0 0 BARNYARD GRASS 3C,8H 0 0 0 CHEATGRASS 6G 2G 0 0 WILD OATS 2G 0 0 0 WHEAT 0 0 0 0 CORN 3C.9H 2C 0 0 BARLEY 5G 0 0 0 SOYBEAN 2C.5G 4G 0 0 SORGHUM 3C.9H 2C,5G 0 0 SUGAR BEETS 4C.9G 4G 0 0 COTTON 9G 4G 0 0 127 Table A (continued) CMPD 34 CMPD 35 RATE-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY . 3C.8G 1H 4C.8H 3G COCKLEBUR 4C,9G 3C, 3H 4C.9H 2G VELVETLEAF 8H 2C, 5G 3C.BH 2C.5G NUTSEDGE 3C.8G 0 8G 0 CRABGRASS 3C.8G 2C ( 4G 2C.8G 3G GIANT FOXTAIL 2C.8G 2H 9C 3C.8G BARNYARD GRASS 9C 3C, 9H 9C 3C.7G CHEATGRASS 9C 4C, 9G 9C 5C.9G WILD OATS 9G 3G 3C.9G 8G WHEAT 4C.9G 9G 3C.9G 9G CORN 3C.9G 2C, 9G 2C.9G 2C.9G BARLEY 9G 2G 2C.9G 6G SOYBEAN 4C.9G 3C, 7G 3C.9G 2C.6G RICE 9C 9C 9C 9C SORGHUM 4C.9G 3C, 9G 3C.9G 2C.9G SUGAR BEETS 5C.9G 3C, 6G 3C.8G 5G COTTON 3C-8H 5G 2C.7G 2G PREEMERGENCE MORNING GLORY 2G 1H 3G 0 COCKLEBUR 4G 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 8G 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 2G 0 BARNYARD GRASS 2C.5G 0 2C.SG 0 CHEATGRASS 4G 0 8G 0 WILD OATS 2C.2G 2G 3C,3G 0 WHEAT 9G 4G 2C.9H 5G CORN 3C,9G 3C, 5G 3C.8H 2C BARLEY 9G 0 8G IC SOYBEAN 2C.4H 0 3G 0 RICE 8G 3G 9H 3G SORGHUM 3C.9H 3C 9H 2C SUGAR BEETS 3H 2C 3H 0 COTTON 4G 2G IG 0 Table A (continued) CMPD 36 CMPD 37 RATE=-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 3C.7H 2C.3G 0 0 COCKLEBUR 7H 2C.2H 2C.6H 0 VELVETLEAF 4C.8G 3C.8G 3C.9H 2G NUTSEDGE 3G 0 0 0 CRABGRASS 6G 4G 2G 0 GIANT FOXTAIL 4C,9G 4C.9H 0 0 BARNYARD GRASS 3G 2C 0 0 CHEATGRASS 4C.9G 4C.9G 0 0 WILD OATS 3C.9G 2C.9G 0 0 WHEAT 9G 7G 0 0 CORN 9G 3C,9G 2C,6H IC BARLEY 8G 3C.7G 3G 0 SOYBEAN 4C,9G 3C.7H 5H 0 RICE 9C 9C 1C.8H 5G SORGHUM 3C-9G 3C,9G 1C.5G 5G SUGAR BEETS 0 0 10C 4C.9G COTTON 7G 2C.4G 2C.6H 3G PREEMERGENCE MORNING GLORY 2G 0 2G 0 COCKLEBUR - 0 - 0 VELVETLEAF 0 0 1C.3H 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 3G 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 8G 0 0 0 WILD OATS 3G 0 0 0 WHEAT 0 0 0 0 CORN 3C,4G 0 2C.4G 0 BARLEY 0 0 0 0 SOYBEAN 2H 0 IC 0 RICE 2C.5G 0 7H 0 SORGHUM 2C.5G 0 3C.6H 0 SUGAR BEETS 0 0 2C.4H 2H COTTON 0 0 1H 0 Table A (continued) CMPD 38 CMPD 39 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 7G 4G 6G 3G COCKLEBUR 4C, ,8H 4H 5G 0 VELVETLEAF IOC 10C 10C 10C NUTSEDGE 2C, ,9G 1C.8G 9G 2C.8G CRABGRASS 4G 0 4G 0 GIANT FOXTAIL 6G 0 4G 0 BARNYARD GRASS 2C, ,7G 0 5G 0 CHEATGRASS 8G 0 2C.8G 0 WILD OATS 3G 0 4G 0 WHEAT 5G 0 4G 0 CORN 9G 2C,7G 2C-8H 2C.5H BARLEY 7G 0 6G 0 SOYBEAN 3C, 8H 2C,7H 4C.9G 2C,8G SORGHUM 2C, ,9G 1C.6H 7H 0 SUGAR BEETS IOC 5C.9G 10C IOC COTTON IOC 2C.8H 9C 1C.8G PREEMERGENCE MORNING GLORY 6G 4G £G 1H COCKLEBUR 2H 1H 2G 0 VELVETLEAF 2C, 7G 1H 2C,9G 8H NUTSEDGE 2C, 8G 0 10E 2C.8G CRABGRASS 3G 0 5G 0 GIANT FOXTAIL 4G 0 4G 0 BARNYARD GRASS 5H 0 6H 0 CHEATGRASS 8G 3G 9G 0 WILD OATS 0 0 6G 0 WHEAT 2G 0 5G 0 CORN 9G 3C,5G 2C,7H 0 BARLEY 0 0 0 0 SOYBEAN 3C, 9H 2C.4G 2C.8H 1C,4G Ricε 2C, 7H 2G 6G 0 SORGHUM 3C, 9H 2C,6G 2C.IH 2C, 4G SUGAR BEETS 3C, 9G 2C.9G 9C 2C.IG COTTON 2C, 8G 0 2C.7G 0 Table A (continued) CMPD 40 CMPD 41 RATEaKG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2G 0 0 0 COCKLEBUR 4G 0 0 0 VELVETLEAF 3G 0 0 0 NUTSEDGE 4G 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 C HEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 C O RN 0 0 0 0 BARLEY 0 - 0- 0 0 2H IC 0— _-. SOYBEAN 0 RICE 0 0 0 0 ή S O RGHUM 0 0 0 0 SUGAR BEETS 3C,8G 2C,6G 0 0 CO TT O N 2C,9G 3G 0 0 PREEMERGENCε M O RNING GLORY 1H 0 0 0 C O CKLEBUR 0 0 2G 3H VELVETLEAF 0 0 0 0 NUTSEDGε 4G 0 0 0 C RABGRASS 0 5G 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 C HEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 S O YBελN 0 1H 0 0 RICE 2G 0 0 0 S O RGHUM 2G 0 0 0 SUGAR BE8TS 3C.8G 2H 0 0 C O TTON 2G 0 0 0 Table A ( continued ) CMPD 42 CMPD 43 RATEsKG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IC 0 7H 0 COCKLEBUR 1C.7H 4H 0 0 VELVETLEAF 1C,6H 3G 7H 0 NUTSEDGE 0 0 0 0 CRABGRASS 2G 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2C,8H 2C, 7H 1C.2H 0 BARLEY 0 0 0 0 SOYBEAN 2C.7H 1H 2C.4H 0 RICE 2G 0 4G 0 SORGHUM 1H,6G 0 0 0 SUGAR BEETS 5C,9G 3C, 8G 2C.8G 2C.8G COTTON 1C,5H 2C 5G 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 4G 0 GIANT FOXTAIL 2G 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 8G 2C, 7H 0 0 BARLEY 0 0 0 0 SOYBEAN 2H 0 0 0 RICE 2C.7G 2G 0 0 SORGHUM 2C.8H 2C, 4G 0 0 SUGAR BEETS 3C.7H 4H 1H 0 COTTON 0 0 0 0 Table A (continued) CMPD 44 CMPD 45 RATE»KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2G C 1—OυCv.KtMLjECiBθUwRn 2C.5H VELVETLEAF 2C.6H 0 5G 0 NUTSEDGE 1C.7G 0 2G 0 CRABGRASS 3G 0 0 0 GIANT FOXTAIL 2G 0 0 0 NYARD GRASS 0 0 2H 0 BAR CHEEAATTGGRRAASSSS 0 0 0 0 CH WIILLDD OOAATTSS 0 0 0 0 W 0 0 0 0 WWHHEEAATT 2C.7H 2C,7H 3G 0 CCOORRNN 0 0 0 BBAARRLLEEYY 0 SSOOYYBBEEAANN 3C,8G 0 0 0 RRIICCEE 2G 0 2G 0 SSOORRGGHHUUMM 3G 0 0 0 SSUUGGAARR BBEEEETTSS 3C,9G 0 4C.8G 2C-5G COTTON 5G 8H PREEMERGENCε MORNING GLORY 0 0 0 0 COCKLεSUR 0 0 3G 0 VELVETLEAF IC IC 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 3G 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 1C,2G 0 0 0 BARLEY 0 0 0 0 SOYBEAN 2C 0 0 0 RICE 0 0 0 0 S O RGHUM 1C.6G 0 0 0 SUGAR BEETS 5G 2H 3G 0 COTTON o o o o Table A (continued) CMPD 46 CMPD 47 RATE=KG/Hλ 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 4C, 9G 5H 0 0 VELVETLEAF IOC 4C, 8G 2C, 8H 7G NUTSEDGE 2C, 8G 3G 2C. 7G 2C,7G CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 2G 0 CHEATGRASS 2G 0 0 0 WILD OATS 0 θ 0 0 WHEAT 0 0 0 0 CORN 0 0 3G 2H BARLEY 0 0 0 0 SOYBEAN 2H 0 2C, 7H 2C,7H RICE 0 0 4G 0 SORGHUM 3C, 8G 2C, 5G 0 0 SUGAR BEETS IOC IOC 10C 4C,8G COTTON IOC 4C, 8G 2C, 8H 7H PREEMERGENCE " MORNING GLORY 0 0 0 0 COCKLEBUR 2H 0 — 0 VELVETLEAF 3H 0 1H 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 2C, 5G 0 0 0 SUGAR BEETS 8G 4H 0 0 COTTON 5G 0 0 0 Table A (continued ) CMPD 48 CMPD 49 RATEaKG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2C 2C 0 1H COCKLEBUR - 0 0 0 VELVETLEAF 2C| ,4β 7G 4G 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 . 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 2G 0 3G 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 2G 0 BARLEY 0 0 0 0 SOYBEAN 2C, 7H 4H 2C, 7H 3G SORGHUM 0 0 5G 0 SUGAR BEETS 4C, 8G 3C,3G 3C, 6G 0 COTTON 2C. 8H 4G 7H 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 1H 1H NUTSEDGE 9G 0 0 0 CRABGRASS 0 - 2G - GIANT FOXTAIL 0 0 0 - BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 4H 0 0 COTTON 0 0 0 0 Table A ( continued ) CMPD 50 CMPD 51 RATE-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 5H 0 COCKLEBUR 0 0 5G 0 VELVETLEAF 0 0 3C, 6G 2G NUTSEDGE 0 0 0 0 CRABGRASS 0 0 5G 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 2H 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 1H 0 RICE 0 0 2G 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 5C, 9H 3G COTTON 0 0 4C, 9H 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 - 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 4H 0 - 0 COTTON 0 0 0 0 Table A (continued ) CMPD 52 CMPD 53 RATE*KG/HA 0.05 0.01 0.05 0. 01 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 3G 0 0 0 VELVETLEAF 3C.8G 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS - 7H 0 0 COTTON 0 0 0 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR - 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 - 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 54 CMPD 55 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 0 0 COTTON 0 0 0 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 4G 0 0 0 COTTON 0 d 0 0 138 Table A (continued) CMPD 56 CMPD 57 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 4C,9G 2G COCKLEBUR 0 0 10C 0 VELVETLEAF 0 0 10C 9C NUTSEDGE 0 0 3C.9G 5G CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 2G 0 BARNYARD GRASS 0 0 3H 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 2C,9G 4H RICE 0 0 4G 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 10C 4C.9G COTTON 0 0 4C.9G — PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 9G 0 VELVETLEAF 0 0 SH 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 4H 0 CHEATGRASS 0 0 2G 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 2G 0 BARLEY 0 0 0 0 SOYBEAN 0 0 2H 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 0 0 7G 2G COTTON 0 0 2G 0 Table A (continued) CMPD 58 CMPD 59 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2G 1H 10C 3C,8G COCKLEBUR IOC 3C, ,9G 10C 10C VELVETLEAF 9C 3C, ,7H 9C 9C NUTSEDGE 2C.8G 7G 4C.9G 4C.9G CRABGRASS 5G 3G 5β 0 GIANT FOXTAIL 0 0 7G 3G BARNYARD GRASS 3C.9H 3C, 6H 9C 9C CHEATGRASS 3C.9G 3C, 8G 4C.9G 2C,8G WILD OATS 3C,8G 3C, , 7G 4C,8G 2G WHEAT 3C.9G 3C, ,7G 4C.9G 9G CORN 3C.9G 4C, 9H 10C 9C BARLEY 3C,6G 0 2C.6G 3G SOYBEAN 4C,9G 5G 5C.9G 9C RICE 6C,9G 6C, 9G 5C.9G 9C SORGHUM 3C,9G 2C, 7G 10C 9C SUGAR BEETS 9C 4C, 8G 10C 10C COTTON 4C.9H 2G 9C 4C,9G PREEMERGENCE MORNING GLORY 0 0 2G 0 COCKLEBUR 2H - 2C 0 VELVETLEAF 0 0 5H 0 NUTSEDGE 0 0 5G 0 CRABGRASS 0 0 2G 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 4H 0 CHEATGRASS 0 0 8G 0 WILD OATS 0 0 2G 0 WHEAT 0 0 2G 0 CORN 0 0 2C.7H 2G BARLEY 0 0 2G 0 SOYBEAN 0 0 7H 2C,5G RICE 0 0 9G 3G SORGHUM 0 0 3C,9H 2C.6G SUGAR BEETS 2H 0 7H 3G COTTON 8G 0 4G 0 140 Table A ( continued ) CMPD 60 CMPD 61 RATE=KG/HA 0.05 0.01 0.05 0. POSTEMERGENCE MORNING GLORY 4C.8G 1H 2G 0 COCKLEBUR 10C 10C 7G 0 VELVETLEAF 9C 10C 1H 0 NUTSEDGE 10C 9C 4G 0 CRABGRASS 6G 3G 0 0 GIANT FOXTAIL 3C.8G 2C, 5G 0 0 BARNYARD GRASS 9C 9C 2H 0 CHEATGRASS 9C 2C, 8G 4G 0 WILD OATS 4C.9G 0 0 0 WHEAT 9C 8G 2G 0 CORN 10C 10C 3C, 9G 0 BARLEY 9G 3G 0 0 SOYBEAN 9C IOC 2C, 3H 0 RICE 9C 9C 5C, 9G 0 SORGHUM 9C 9C 4C, 8H 0 SUGAR BEETS 10C IOC 3C, 3G 0 COTTON 10C 9C 0 0 PREEMERGENCE MORNING GLORY 3G 1H 0 0 COCKLEBUR 9H 2C, 5H 0 0 VELVETLEAF 2C,9G 5G 0 0 NUTSEDGE 9G 4G 0 0 CRABGRASS 2G 0 0 0 GIANT FOXTAIL 2G 0 0 0 BARNYARD GRASS 9H 3G 0 0 CHEATGRASS 9H 3G 0 0 WILD OATS 5G 0 0 0 WHEAT 8G 6G 0 0 CORN 3C,9G 5H 0 0 BARLEY 2C.7G 0 0 0 SOYBEAN 9H 3C, 8H 0 0 RICE 9H loε 0 0 SORGHUM 9H 10H 0 0 SUGAR BEETS 9C 6H 0 0 COTTON 9G 8G 0 0 Table A ( continued ) CMPD 62 CMPD 63 RATE»KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 4C.9G 2H COCKLEBUR 0 0 10C 4C,9H VELVETLEAF 2G 0 4C,8H 2C.6H NUTSEDGE 0 0 4C.9G 8G CRABGRASS 0 0 6G 2G GIANT FOXTAIL 0 0 3C.6G 2G BARNYARD GRASS 0 0 9C 9C CHEATGRASS 5G 0 9C 9G WILD OATS 0 0 9C 3C,8G WHEAT 0 0 6C.9G 9G CORN 6H 0 10C 5U,9C BARLEY 0 0 4C.9G 6G SOYBEAN 0 0 5C.9G 3C,8H RICE 8G 0 10C 9C SORGHUM 2C.5G 0 10C 4C.9G SUGAR BEETS 1H 0 9C 5C,9G COTTON 0 0 5C.9G 2C.5G PREEMERGENCE MORNING GLORY 0 0 6G 2G COCKLEBUR 2H 0 2C.2H 0 VELVETLEAF 0 0 1C.2H 0 NUTSEDGE 0 0 0 0 * "_ CRABGRASS 0 0 2G 0 GIANT FOXTAIL 0 0 1H 0 BARNYARD GRASS 0 0 7H 0 CHEATGRASS 0 0 7G 0 WILD OATS 0 0 2C,8H 0 WHEAT 0 0 9H 6G CORN 0 0 3C.8H 1H BARLEY 0 0 2G 0 SOYBEAN 0 0 2C.4G 6G RICE 0 0 10E IG SORGHUM 0 0 5C.9H 3C.4H SUGAR BEETS 0 0 0 ' 0 COTTON 0 0 8G 0 Table A (continued) CMPD 64 CMPD 65 RATE * KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 3C.8G 2C,4G 0 0 COCKLEBUR 5C.9H 3C.9G 3C, 9H 2G VELVETLEAF 3C.9H 3C.8H 3C, 7H 0 NUTSEDGE 3C.9G 3C.6G 0 0 CRABGRASS 7G 2G 0 0 GIANT FOXTAIL 9C 5G 2C, 5G 3G BARNYARD GRASS 9C 5C.9H 0 0 CHEATGRASS 9C 4C.9G 2G 3G WILD OATS 4C.9G 8G 2G 0 WHEAT 3C,9G 3C.9G 2G 2G CORN 9C 4C.9G 3C, 7H 3C,9H BARLEY 4C,9G 9G 3G 0 SOYBEAN 5C.9G 2C,5G 3C, 7H 0 RICE 9C 9C 4C, 9G 8G SORGHUM 9C 4C.9G 4G 2C.7G SUGAR BEETS 5C.9G 3C,8G 0 0 COTTON 4C-9G 3C.7H 2G 0 PREEMERGENCE MORNING GLORY 2G 0 0 0 COCKLEBUR 0 0 - 1H VELVETLEAF 2H 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 3G 0 0 0 BARNYARD GRASS 7G 0 0 0 CHEATGRASS 7G 0 0 0 WILD OATS 2C.2G 0 0 0 WHEAT 7G 0 0 0 CORN 3C.8H 1H 0 0 BARLEY 0 0 0 0 SOYBEAN 2C.5G 1H 0 0 RICE 5C.9G 4C.9G 0 0 SORGHUM 4C.9H 3C.8H 0 0 SUGAR BEETS 0 1H 2H 0 COTTON 3G 3G 0 0 Table A (continued) CMPD 66 CMPD 67 RATEsKG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 3C.8H 3C.6G 10C IOC COCKLEBUR 9C 2C,7G 9C 10C VELVETLEAF 9C 3C,8G 10C 10C NUTSEDGE 2C,9G 0 9C 4C.9G CRABGRASS 3G 0 5C.9G 3C.8G GIANT FOXTAIL 5G 0 . 9C 3C.8H BARNYARD GRASS 3C,9H 3C,7H 10C 9C CHEATGRASS 5C.9G 3C,7G 9C 9C WILD OATS 4C.8G 2C.5G 9C 5C.9G WHEAT 4C.9G 2C,8G 9C 3C.9G CORN 5C.9G 2C.9G 10C 9C BARLEY 3C.6G 2G 5C.9G 3C.9G SOYBEAN 4C.9G 3C.6G 5C-9G 4C,9G RICE 9C 5C.9G 9C 6C.9G SORGHUM 3C.9G 9G IOC 10C SUGAR BEETS IOC 5C,9G 10C 10C COTTON - - - PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 5H 0 VELVETLEAF 0 0 5H 0 NUTSEDGE 0 0 3C.7G 0 CRABGRASS 0 0 7G 0 GIANT FOXTAIL 0 0 3G 0 BARNYARD GRASS 0 0 8H 0 CHEATGRASS 0 0 8G 0 WILD OATS 0 0 8H 0 WHEAT 0 0 9H 0 CORN 0 0 3C.9H 0 BARLEY 0 0 5G 0 SOYBEAN 0 0 2C.4G 0 RICE 0 0 8G 0 SORGHUM 0 0 5C,9G 0 SUGAR BEETS 0 0 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 64t CMP! D 6 9 RATE-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC IOC IOC IOC COCKLEBUR IOC IOC IOC IOC VELVETLEAF IOC IOC IOC 4C,9G NUTSEDGE 9C IOC 9C 3C,8G CRABGRASS 5C, 9G 7G 5G 2G GIANT FOXTAIL IOC IOC 3C, 5G 3G BARNYARD GRASS IOC IOC 4C, 9H 3C,9H CHEATGRASS IOC 9C 5C, 9G 3C,5G WILD OATS 9C 5C, 9G 3G 0 WHEAT IOC 6C, 9G 8G 3G CORN OC IOC 9C 3C,9G BARLEY 9C 3C. 9G 2C. 5G 0 SOYBEAN 9C 9C 3C. 8G 1H RICE 9C 9C 9C 4C.9G SORGHUM IOC 9C 9C 3C.9G SUGAR BEETS IOC IOC IOC IOC COTTON — ^ PREEMERGENCE MORNING GLORY 9H 4G 5G 0 COCKLEBUR 8H 0 2C 0 VELVETLEAF 4C, 9G 4G 7G 0 NUTSEDGE 9G 0 0 0 CRABGRASS 9G 7G 0 0 GIANT FOXTAIL 9G 3G 0 0 BARNYARD GRASS 9H 5H 0 0 CHEATGRASS 9G 6G 7G 0 WILD OATS 3C, 8G 2C, ,5β 2G 0 WHEAT 8H 8G SG 0 CORN 9H 3C, , 6G 7G 0 BARLEY 9G 2C, ,7G 0 0 SOYBEAN 3C, 8G 2C, -2G 2G 0 Ricε 3C, ,9G 9H 8G 5G SORGHUM 9H 3C, ,8H 9G 3C.6G SUGAR BEETS 7G 0 0 0 COTTON 9G 2G 0 0 Table A (continued) CMPD 70 CMPD 71 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 10C 2H 3G COCKLEBUR 10C 9C 10C 9C VELVETLEAF 10C 9C 9C 4C.9G NUTSEDGE 9C 9C 5C.9G 5C.8G CRABGRASS 3C,8G 6G 5G 0 GIANT FOXTAIL 9C 3G 2G 3G BARNYARD GRASS 9C 9C 5C.9H 3C.8G CHEATGRASS 10C 9C 9G 3C,7G WILD OATS 5C.9G 9C 3C,7G 2C WHEAT 10C 9C 9G 3G CORN IOC IOC 9C 9G BARLEY 6C.9G 4C.9G 2C,3G 0 SOYBEAN 6C.9G 5C.9G 4C.9G 4C.9G RICE 9C 9C 5C.9G 3C.7G SORGHUM 9C 9C 5C.9G 3C.8H SUGAR BEETS IOC IOC 10C 10C COTTON 4C.9G 6G PREEMERGENCE MORNING GLORY 9G 6G 0 0 COCKLEBUR 3C.7H 0 2G 0 VELVETLEAF 3C.8H 3H 1H 0 NUTSEDGE 10E 0 0 0 CRABGRASS 5G 3G 3G 0 GIANT FOXTAIL 2G 0 2G 0 BARNYARD GRASS 9H 8H 2H 0 CHEATGRASS 9G 6G 3G 0 WILD OATS 7G 2C,4G 0 0 WHEAT 9H 7G 0 0 CORN 3C.9H 3C.8H 3C,3G 0 BARLEY 9G 3C.4G 0 0 SOYBEAN 3C.9H 3C.4G 2C 0 RICE 10E 3C,8H 3G 0 SORGHUM 6C.9H 9H 3C,7G 0 SUGAR BEETS 3C,7H 3H IG 0 COTTON 8G 3G O 0 Table A ( cont inued ) CMPD 72 CMPD 73 RATE=-KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 4C.9G 4C.9G 2C,7G COCKLEBUR IOC 10C 10C 10C VELVETLEAF IOC 10C 10C 9C NUTSEDGE 3C.8G 3C.9G 9C 3C,8G CRABGRASS 3C.8G 7G 3C.7G 4G GIANT FOXTAIL 3C.6G 3C.5G 5C,9G 9C BARNYARD GRASS 9C 9C 9C 9C CHEATGRASS 5C,9G 7G 5C.9G 4C, 9G WILD OATS 4C,8G 3C.6G 3C.7G 3C.7G WHEAT 9G 4G 4C.9G 5G CORN 9C 9C 9C 5C.9G BARLEY 3C.5G IC 3G 3C.5G SOYBEAN 9C 4C.8G 9C 9C RICE 5C.9G 8G 5C.9G 9C SORGHUM 5C,9G 4C-9G 4C.9G 4C,9G SUGAR BEETS 9C 10C 9C 9C COTTON 9C 9C 10C 10C PREEMERGENCE MORNING GLORY 2H 0 2G 0 COCKLEBUR 0 0 5H 0 VELVETLEAF 6G 1H 5H 0 NUTSEDGE 9G 0 7G 0 CRABGRASS 6G 0 3G 0 GIANT FOXTAIL 3G 0 4G 0 BARNYARD GRASS 7H 0 3C,9H 0 CHEATGRASS 6G 4G 7G 0 WILD OATS 2G 0 2G 0 WHEAT 4G 0 3G 0 CORN 3C.9G 2C.2G 3C.7G 2C.2G BARLEY 2G 0 0 0 SOYBEAN 3C.6H 0 3C,4H 1H RICE 8G SG 9H 3G SORGHUM 3C.9H 3C,4G 9H 3C.6G SUGAR BEETS- 4G 2H 8G 2H COTTON 5G 0 2G 2G Table A (continued) CMPD 74 CMPD 75 RATE--KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 3C,7G 3C, 6G 4C.9G 3C.7H COCKLEBUR IOC 10C 10C 9H VELVETLEAF 8G 7H 4C-9G 3H NUTSEDGE 3C.5G 3C, 5G 3C.6G 2C.5G CRABGRASS 0 0 4G 0 GIANT FOXTAIL 2C 2C 3G 3C.3G BARNYARD GRASS 4C.9H 3C, 8H 4C.9H 4C.9H CHEATGRASS SG 2G 2C.6G 3C.5G WILD OATS 0 2C 3C.8G 2C.4G WHEAT 0 2C 9G 8G CORN 9C 5C, 9G 9C 5C.9G BARLEY 0 2G 2G 0 SOYBEAN 4H 4H 4C.9G 5C.9G RICE 9G 8G 9C 9C SORGHUM 3C.9H 4C, 8H 9C 3C.9H SUGAR BEETS IOC 9C 9C 9C COTTON 5C,9G 4G 3C,7G 2G PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 - 2C.2H 0 VELVETLEAF 0 0 2C,2H 0 NUTSEDGE 0 0 2C 0 CRABGRASS 0 0 3C.4G 0 GIANT FOXTAIL 0 0 3G 3G BARNYARD GRASS 0 0 3C.5G 2G CHEATGRASS 0 0 7β 2G WILD OATS 0 0 3C.5G 0 WHEAT 0 0 7G 3G CORN 3C.4G 3G 3C.8G 3C,4G BARLEY IC 0 2G IC SOYBEAN 2H 0 3C.3H 0 RICE 5G 2G 5C,9H 8H SORGHUM 4C.8G 3C, 3G 4C,9H 3C,SH SUGAR BEETS 2H 0 5C.9G 3H COTTON 0 0 2G 0 Table A ( continued ) CMPD 76 CMPD RATE»KG/HA 0.05 0.01 0.05 0 .01 POSTEMERGENCE MORNING GLORY 0 0 0 COCKLEBUR 2C, , 5G 2G 1H VELVETLEAF 5G 0 3C.8H NUTSEDGE 0 0 3C,8G CRABGRASS 0 0 0 GIANT FOXTAIL 2G 2G 0 BARNYARD GRASS 0 0 0 CHEATGRASS 3G 0 0 WILD OATS 2C, 5G 4G 0 WHEAT 5G 3C, 8H 0 CORN 4C, 9H 3C, 8H 0 BARLEY 4G 0 0 SOYBEAN 4C. 8G 3C, 8G 3C.7H RICE 3C, 9G 9G 3G SORGHUM 2C, 5G 3C, 8G 0 SUGAR BEETS 0 0 9C COTTON 3G 0 3C.9G PREEMERGENCE MORNING GLORY 0 0 0 COCKLEBUR 2H 0 0 VELVETLEAF 0 0 0 NUTSEDGE 0 0 0 CRABGRASS 0 0 0 GIANT FOXTAIL 0 0 0 BARNYARD GRASS 0 0 0 CHEATGRASS 0 0 0 WILD OATS 0 0 0 WHEAT 0 0 0 CORN 0 0 0 BARLEY 0 0 0 SOYBEAN 2H 0 0 RICE 0 0 0 SORGHUM 5G 0 0 SUGAR BEETS 0 0 0 COTTON 0 0 0 149 Table A (continued) CMPD 78 CMPD 79 RATE»KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2C.5G 9C COCKLEBUR 9C 9C VELVETLEAF IOC 9C NUTSEDGE 3C.8G CRABGRASS 0 2G GIANT FOXTAIL 2G 5G BARNYARD GRASS 7H 3C.8H CHEATGRASS 2G 0 - WILD OATS 2G 0 - WHEAT 2G 0 - CORN 2C.4H 2C.7H BARLEY 2C 0 - SOYBEAN 5C,9G 5C,9G RICE 4G 3G SORGHUM 2C,4G 9H SUGAR BEETS 9C 9C COTTON 5C,9G 9C PREEMERGENCE MORNING GLORY 0 COCKLEBUR 0 VELVETLEAF 3C,6H 8G NUTSEDGE 3C,7G 9G CRABGRASS 0 0 GIANT FOXTAIL 0 3G BARNYARD GRASS 3C.7H 8H CHEATGRASS 0 2G WILD OATS 0 0 WHEAT 0 0 CORN 2C 2C.3G BARLEY 0 0 SOYBEAN 3C.4H 2C,2H RICE 7G 5G SORGHUM 0 8H SUGAR BEETS 3C.8G 6G COTTON 3G 3G Table A ( conti nued ) CMPD 80 CMPD 81 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 3C.8H 2C.1H COCKLEBUR 9C 6H - VELVETLEAF 3C.8H 2C.4G NUTSEDGE 0 0 - CRABGRASS 0 0 - GIANT FOXTAIL 0 5G BARNYARD GRASS 0 4H CHEATGRASS 0 2G WILD OATS 0 0 - WHEAT 0 0 - CORN 0 3C.9H BARLEY 0 0 - SOYBEAN 5H 3C.3H RICE 0 2C.5G SORGHUM 0 7G SUGAR BEETS 3C.8G 3C.8H COTTON 7G 6G PREEMERGENCE MORNING GLORY 0 COCKLEBUR 0 VELVETLEAF 0 IK NUTSEDGE 0 0 CRABGRASS 0 0 GIANT FOXTAIL 0 0 BARNYARD GRASS 0 0 CHEATGRASS 0 0 WILD OATS 0 0 WHEAT 0 0 CORN 0 IC BARLEY 0 ' 0 SOYBEAN 0 0 RICE 2G 3C.7G SORGHUM 2C 3C.6G SUGAR BEETS 3H 1H COTTON 0 0 Table A ( continued ) CMPD 82 CMPD 13 RATEaKG/HA 0.05 0 . 01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 0 COCKLEBUR 7G 5G 4G VELVETLEAF 7H 3C.7H 2C,7H NUTSEDGE 0 2C.8G 0 CRABGRASS 0 0 0 GIANT FOXTAIL 3G 3G 0 BARNYARD GRASS 0 2C.7H 4G CHEATGRASS 4G 7G 4G WILD OATS 0 3C.9G 2C.3G WHEAT 0 2C-8G 2C.3G CORN 2H 9G 2C.6H BARLEY 0 2C.7G 4G SOYBEAN 2C.5H 2C.8G 2C,6H RICE 3C.8G 9G 2C.8G SORGHUM 2C.7G 2C.9H 2C.7G SUGAR BEETS 2C.5G 2C.6G 0 COTTON 6G 2C,7H 2C.5H PREEMERGENCE MORNING GLORY 0 0 0 COCKLEBUR 0 0 7H VELVETLEAF 0 0 0 NUTSEDGE 0 0 0 CRABGRASS 0 - 0 GIANT FOXTAIL 0 0 0 BARNYARD GRASS 0 0 0 CHEATGRASS 0 0 0 WILD OATS 0 0 0 WHEAT 0 0 0 CORN 0 0 0 BARLEY 0 0 0 SOYBEAN 0 0 0 RICE 5G 0 0 SORGHUM 2C 0 0 SUGAR BEETS 0 3H 2H COTTON 0 0 0 Table A (continued) CMPD 84 CMPD 8 5 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 4C.9G 2C.6G 10C IOC COCKLEBUR IOC 2C.9H 10C 10C VELVETLEAF IOC 10C 10C IOC NUTSEDGE 5C,9G 3C.9G 10C 10C CRABGRASS 2C.9G 5G 2C.8G 2C.7G GIANT FOXTAIL 3C,βG 7G 3C.7G 2C,7G BARNYARD GRASS 9C 9C 9C 9C CHEATGRASS 2C.7G 2C.8G 9C 2C.8G WILD OATS 9C 2C.9G 2C.9G 2C.9G WHEAT 9C 10C 2C.9G 2C.8G CORN 2C.9G 2C.9G 2C.9G 3C.9G BARLEY 4C,9G 2C.7G 9G 6G SOYBEAN 3C.8G 3C.7H 3C.9G 3C.9G RICE 3C,8G 2C.9G 5C.9G 3C.9G SORGHUM 9C 2C.9G 9C 4C,9G SUGAR BEETS 9C 3C,7G 10C IOC COTTON 5C.9G 2C,8K 9C 3C.9G PREEMERGENCE MORNING GLORY 5G 3G 1H.7G 4G COCKLEBUR 2C,4H 0 5G 0 VELVETLEAF 2C,7H 2C,4H 2C.7H 5H NUTSEDGE 2C,9G 0 9G 7G CRABGRASS 2C.7G 0 2C.8G 2G GIANT FOXTAIL 2C.7H 0 2C.6H 0 BARNYARD GRASS 2C.9H 2C.7H 3C.9H 2C.9H CHEATGRASS 3C,9H 2C.8H 2C.9H 5G WILD OATS 3C.8G 3G 2C.7G 5G WHEAT 2C.9G 0 6G 2G CORN 3C.8H 0 3C.9H 0 BARLEY 6G 5G 7G 4G SOYBEAN 3C.7H 2C,5G 2C.7H 4G RICE 3C.9H 2C-6G 3C.9H 2C.6H SORGHUM 10H 3C.8H 10H 3C.9H SUGAR BEETS 3C.8G 2C.3G 9C 2C.3G COTTON 2C.7G 2C.3G 7G 6G Table A (continued) CMPD 86 CMPD 87 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 2C, 5G 0 0 COCKLEBUR 7H 0 0 0 VELVETLEAF 3C.8H 7G 2C, 5G 0 NUTSEDGE 5C,9G 2C, 6G 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 3G 0 3H 0 CHEATGRASS 6G 0 5G 0 WILD OATS 3C.8G 6G 0 0 WHEAT 3G 3G 0 0 CORN 3C,7H 3C, 4H 2C, 5H 0 BARLEY 0 0 0 0 SOYBEAN 2C,7H 4H 3C, 7H 0 RICE 2C.9G 7G 3C, 9G 7G SORGHUM 2C.9G 3C, 9G 3C, 8G 3C.6H SUGAR BEETS 3C.7G 3C, 7G IC, 3G 0 COTTON 3C,8H 2C, 7H 2C, 7H 0 PREEMERGENCE MORNING GLORY 5G 0 0 0 COCKLEBUR 2G 0 0 — VELVETLEAF 4H 0 0 2H NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 2C,7H 0 2C 0 SORGHUM 3C,9H 0 3C 0 SUGAR BEETS 2C,7G 0 2H 0 COTTON 2G 0 0 0 Table A (continued) RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY IOC 7G 10C 10C COCKLEBUR IOC 3C,9G 10C 2C,8G VELVETLEAF 9C 4C.9H 6C.9H 2C.8H NUTSEDGE IOC 10C 10C 5C.9G CRABGRASS 4G 0 4G 0 GIANT FOXTAIL 3C,8G 6G 5G 0 BARNYARD GRASS 5C.9G 3C.7H 3C.8H 2C.6H CHEATGRASS 2C.9G 2C.6G 3C.7G 5G WILD OATS 5C.9G 3C.9G 5C.9G 3C.9G WHEAT 4C.9G 2C.8G 2C.7G 2C.7G CORN 4C.9G 3C.9G 3C.8G 2C,9H BARLEY 2C.8G 5G 7G 0 SOYBEAN 3C.9G * 4C.8G 5C.8H 3C,8H RICE 6C.9G 6C.9G 5C.9G 5C.9G SORGHUM 4C.9G 4C.9G 3C.9G 3C.9G SUGAR BEETS IOC 9C 10C 10C COTTON 4C.9G 2C,7H 9C 3C.7H PREEMERGENCE MORNING GLORY 9H 6G 9H 7H COCKLEBUR 8H 0 3C.6G 6G VELVETLEAF 2C,7H 3C.4H 2C.7H 3C.6H NUTSEDGE 10E 2C.9G 2C.9G 7G CRABGRASS 2C 2G 5G 2G GIANT FOXTAIL 2C.6G 0 2G 0 BARNYARD GRASS 2C.7H 4H 0 0 CHEATGRASS 2C,8H 2C.3G 2C.3G 3G WILD OATS 3C.8G 2C.6G 2C.6G 0 WHEAT 3C.8G 2G 4G 0 CORN 2C.9H 2C.7G 2C,8H 0 BARLEY 8G 5G 4G 0 SOYBEAN 4C.7G 2C.5G 4C.7H 2C.6G RICE 4C.9H 4C.8H 4C.9H 2C.7H SORGHUM 10H 3C.9H 3C.9H 3C.6G SUGAR BEETS 9C 4C.6G 5C.7G 2C.5G COTTON 3C.7G 2C.4H 2C.7H 2C.4H 155 Table A (continued. CMPD 90 CMPD 91 RATE * KG/HA 0.05 0.01 0.05 0. POSTEMERGENCE MORNING GLORY 2C.7G 2C, 5G 0 0 COCKLEBUR 3G 3G 3H 0 VELVETLEAF 3G 0 3G 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 2G 2G 2G 0 CHEATGRASS 4G 4G 2G 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2C,4H 2C, 3H 0 0 BARLEY 0 0 0 0 SOYBEAN 2C.7H 3H 0 0 Ricε 8G 2C, 7G 2G 0 SORGHUM 3C,8H 3C, 7H 3G 0 SUGAR BEETS 2C,6G 0 5G 0 COTTON 3C,6H 2C 3C,3G 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 2H 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SUGAR BEETS 4H 0 0 0 COTTON 0 - 0 0 Table A (continued) CMPD 92 CMPD 93 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR IOC 2C,9G 9C 8H VELVETLEAF 9C 3C,8K 5C.9G 3C.7H NUTSEDGE 8G 3C.5G 3C.8G 8G CRABGRASS 3G 0 0 0 GIANT FOXTAIL 4G 0 3G 0 BARNYARD GRASS 3C, ,8H 5H 3C,7H 3C.5H CHEATGRASS 3C, ,9G 4G 3C.9G 3G WILD OATS 2C, ,2G 0 4G 0 WHEAT 4G 0 2G 0 CORN 4C ( ,9G 3C-9H 9H 3C.8G BARLEY 0 0 5G 0 SOYBEAN 5C, 9G 3C,7H 4C.9G 4C t 8G RICE 5C, ,9G 5G 4C.9G 3G SORGHUM 3C, 9G 3C,5G 4C.9H 4C.8H SUGAR BEETS 9C 3C.8H 10C 5C.9G COTTON 9H 4C.7G 3C.9G 4C.9H PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 3C, 3H 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2C, 2G 0 2C 0 BARLEY 0 0 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 94 CMPD 95 RATEsKG/HA 0.05 0.01 0.05 0.01 OSTEMERGENCE MORNING GLORY 1H 0 0 0 C O CKLEBUR 9H 3G 8H 2H VELVETLEAF 5G 2H 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 0 GIANT FOXTAIL 0 0 7G BARNYARD GRASS 0 0 7H 2H CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2G 0 3C.9G 2C.5H BARLEY 0 0 0 0 SOYBEAN 0 0 3H 0 RICE 2G 2G SC,! 9G 3C.6G S O RGHUM 3C,5G 2G 3C. 9G 2C.5G SUGAR BEETS 5G 2G 3C, 6G 0 C O TT O N 3C.7G 3C.5G 3C, 7G 2G PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 2G 0 0 0 RICE 0 0 2C ,5G 0 SORGHUM 2C.5G 0 3C ,5G 0 SUGAR BEETS 2G 0 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 96 CMPD 9 7 RATE=KG/HA 0.05 0.01 0.05 0.0 POSTEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 3C, ,8H 0 0 0 VELVETLEAF IC 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 2G 0 0 0 BARNYARD GRASS 4G 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 3C, 7H 0 0 0 BARLEY 0 0 0 0 SOYBEAN 2C, 2H 0 0 0 RICE 4C, 9G 0 0 0 SORGHUM 3C, 5G 0 0 0 SUGAR BEETS 2C 0 0 0 COTTON 3C, 6H 0 0 0 PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 2H 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 ιoε loε CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 0 0 SOYBEAN 7G 0 0 0 RICE 2G 0 0 0 SORGHUM 3C, 4G 0 0 0 SUGAR BEETS SG 3G 0 0 COTTON 0 0 0 0 Table A (continued) CMPD 98 CMPD 99 RATE*KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 0 0 2C 0 COCKLEBUR 5H 0 5C.9G 7H VELVETLEAF 2C 0 5C.9G 3G NUTSEDGE - 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 IC 0 BARNYARD GRASS 0 0 3C,6H 0 CHEATGRASS 0 0 4C.8G 6G WILD OATS 0 0 4G 0 WHEAT 0 0 4G 0 CORN 2C, 3G 0 9H 3C.8H BARLEY 0 0 2G 0 SOYBEAN 0 0 4C,9G 4C.9G COTTON 0 0 3C.9H 3G PREEMERGENCE MORNING GLORY 0 0 0 0 COCKLEBUR 0 0 0 0 VELVETLEAF 0 0 0 0 NUTSEDGE 0 0 0 0 . CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 2C 0 BARLEY 0 0 0 0 SOYBEAN 0 0 2C 0 RICE 0 0 7G 0 SORGHUM 0 0 3C.7H 0 SUGAR BEETS 0 0 0 0 COTTON 0 0 0 0 Table A ( continued ) CMPD100 CMPD101 RATE*KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 10C IOC IOC IOC COCKLEBUR IOC 9C IOC IOC VELVETLEAF IOC 9C IOC 5C.9G N U TSEDGE 5C.9G 4C,9G IOC 9C CRABGRASS 3C.9H 7G 4C, 9G 2C.8G GIANT FOXTAIL 4C.9H 3C.7G 4C. 9G 3C.7G BARNYARD GRASS 6C,9G 9C 9C 9C CHEATGRASS 9C 9C 9C 9C WILD OATS 9C 3C,8G 3C, 9G 4C,9G WHEAT 9C 3C-9G 3C, 9G 9C CO RN 9C 5C.9G 9C 3C.9G BARLEY 3C,9G 7G 3C, 9G 6G SOYBEAN 9C 9C 9C 9C RICE 9C 6C-9G 9C 9C S ORGHUM SC,9G 4C,9H 9C 9C SUGAR BEETS IOC 9C IOC IOC C OTTON IOC 4C.9G IOC IOC PREEMERGENCE MORNING GLORY 5G 3G 9H 3G COCKLEBUR 8H 2H 9H 8H VELVETLEAF 9H 2H 9G 7G NUTSEDGE 8G 0 ιoε 9G CRABGRASS 5G 3G 9H 2G GIANT FOXTAIL 3C.9H 2G 9H 4G BARNYARD GRASS 9H 4G 9H 8H CHEATGRASS 9G 8G 9G 8G W ILD OATS 3C,7G 2C.5G 9G 3G WHEAT 9H 2C.8G 9H 3C.7G CORN 3C.9H 9H 9H 9H BARLEY 9G 3C,7G 9G 2G SOYBEAN 9H 3C,7H 9H 3C.7H RICE 9H 4C.9H 9H 3C.9H SORGHUM 9H 4C,9H 10H 9G SUGAR BEETS 3C.9G 7H 9G 8G COTTON 3C.8H 0 9G 7H Table A (continued) CMPD102 CMPD103 RATE=KG/HA 0.05 0.01 0.05 0. POSTEMERGENCE MORNING GLORY 9C 2C. ,6G ' 0 0 COCKLEBUR IOC 4C, 9G 0 0 VELVETLEAF 9C 4C, ,8H 0 0 NUTSEDGE 5C, 9G 2G 0 0 CRABGRASS 3G 0 0 0 GIANT FOXTAIL 2G 0 0 0 BARNYARD GRASS 8H 7H 0 0 CHEATGRASS 8G 4G 5G 0 WILD OATS 3G 0 0 0 WHEAT 5G 0 0 0 CORN 9H 3C, 9H 2H 0 BARLEY 0 0 0 0 SOYBEAN 3C, 9G 5H 2H 0 RICE 5C, 9G 8G 3C,βG 0 SORGHUM 4C, 9H 3C, 9H 5G 0 SUGAR BEETS 9C 9C 0 0 COTTON 9C 7G 0 0 PREEMERGENCE MORNING GLORY 4H 0 0 0 COCKLEBUR 1H 1H 0 0 VELVETLEAF 4H 1H 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 8H 0 0 0 CHEATGRASS 6G 5G 0 0 WILD OATS 3G 0 0 0 WHEAT 5G 0 0 0 CORN 3C, 9G 0 0 0 BARLEY 3G 0 0 0 SOYBEAN 3C, 6G 2G 0 0 RICE 9H 9H 0 0 SORGHUM 9H 3C, 8H 0 0 SUGAR BEETS 8H 3H 0 0 COTTON 4G 0 0 0 Table A (continued) CMPD104 CMPD10. RATE»KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 5C.9G 3C.8H 9C 3C.8H COCKLEBUR 9C 3C.9H 5C.9G 3C.7H VELVETLEAF 5C-9H 3C.7H 5C.9H 2C.4G NUTSEDGE 3C.7G 4G 4C.8G 0 CRABGRASS 5C.9G 3C,7G 5C.9G 3G GIANT FOXTAIL 9C 3C.7H 5C.9G 3G BARNYARD GRASS IOC 9C 9C 4C.9H CHEATGRASS 9C 9C 9C 6C.9G WILD OATS 6C.9G 5C.9G 9C 6C.9G WHEAT 9C 5C.9G 10C 6C.9G CORN 9C 5C.9G 5C.9G 4C,9G BARLEY 4C,9G 5C.9G 5C.9G 2C.8G SOYBEAN 5C, 9G 4C.9G 5C.9G 4C.8G RICE 9C 9C 9C 5C.9G SORGHUM IOC 9C 9C 5C.9G SUGAR BEETS IOC 9C 9C 9C COTTON 7G 4C.9H 4C,9H 4C.8H PREEMERGENCE MORNING GLORY 7G 1H 0 0 COCKLEBUR - 2C IC 0 VELVETLEAF 6G 0 0 0 NUTSEDGE 4G 0 5G 0 CRABGRASS 3C.5G 0 0 0 GIANT FOXTAIL 3C.5G 0 0 0 BARNYARD GRASS 9H 3G 7H 0 CHEATGRASS 3C.9H 9G 9G 7G WILD OATS 3C.8H 3C.6G 3C.7G 2G WHEAT 9H 9H 8H 4G CORN 3C.9H 2C-9G 2C.9G 3C.7H BARLEY 9H 3C.8G 2C.9G 3C.8G SOYBEAN 3C.8H 3C.4G 3C.6G 2C,4G Ricε 10E 5C,9H 9H 9H SORGHUM 4C.9H 5C.9H 9H 3C.9H SUGAR BEETS 9G 7G 9G 2H COTTON 5G C 0 0 Table A (continued) CMPD106 CMPD10" 1 RATE»KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 2C, ,4H 0 9C 3C.6H COCKLEBUR 0 0 10C 5C.9K VELVETLEAF SH 0 6C,9G 3C.8H NUTSEDGE 0 0 2C.8G 3C.6G CRABGRASS 0 0 6G 0 GIANT FOXTAIL 2G 0 3C.8G 4G BARNYARD GRASS 5H 0 4C.9H 3C.8H CHEATGRASS 4C, 9G 5G 2C.8G 3C.6G WILD OATS 5G 0 3G 0 WHEAT 2G 0 7G 0 CORN 9G 4H 3C.9G 3C.9G BARLEY 0 0 IC 0 SOYBEAN 4C, 8G 3C,4G 4C.9G 3C.8H RICE 4C, 8G 2G 3C,9G 3C.7G SORGHUM 3C, 9H 3C.8H 4C.9G 3C.9H SUGAR BEETS 2H 0 4C,9G 3C.5G COTTON IC 0 9G 5C.9G PREEMERGENCE MORNING GLORY 0 0 3C.5G 0 COCKLEBUR 0 0 - - VELVETLEAF 0 0 2H 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 BARLEY 0 0 IC 0 SOYBEAN 0 0 2C 0 RICE 0 0 0 0 SORGHUM 3C, SG 0 0 0 SUGAR BEETS 0 0 3G 0 COTTON 0 0 0 0 Table A (continued) CMPD108 CMPD109 RATE=KG/HA 0.05 0.01 0.05 0.01 POSTEMERGENCE MORNING GLORY 4C.9G 3C ( ,8H 9C 4C.9H COCKLEBUR IOC 9C 10C IOC VELVETLEAF 5C,9G 3C, 8H 10C 3C.7H NUTSEDGE 3C.9G 8G 9G 3C.8G CRABGRASS 3G 2G 3C.8G 3C,3G GIANT FOXTAIL 3C,7H 2C, 4G 4C.9G 4C,8G BARNYARD GRASS 4C.9H 3C, 8H 9C 5C.9H CHEATGRASS 7G 6G 6C,9G 2C.8G WILD OATS 2G 0 3C.5G 3G WHEAT 2G 0 2C.9G 4G CORN 5C.9G 9G 9C 3C.9G BARLEY IC 0 0 0 SOYBEAN 4C.9G 3C, 9G 4C.9G 4C.9G RICE 4C.9G 7G 9C 2C.9G SORGHUM 4C,9G 2C, 9G 9C SC.9G SUGAR BEETS 5C.9G 2G 9C 4C,8H COTTON 2C.9G 9G 9G 4C.9H PREEMERGENCE MORNING GLORY 0 0 3C.5G 0 COCKLEBUR 2C.3H 0 2C.3H 0 VELVETLEAF 1H 0 2C,2H 0 NUTSEDGE 0 0 10E 0 CRABGRASS 0 0 3G 0 GIANT FOXTAIL 0 0 3C,7G 0 BARNYARD GRASS 0 0 3C.8G 2H CHEATGRASS 0 0 9G 0 WILD OATS 0 0 2G 0 WHEAT 0 0 8G 0 CORN 0 0 3C.4G 0 BARLEY 0 0 4G 0 SOYBEAN 4G 0 3C.6H 2C.2H RICE 0 0 3C.7G 0 SORGHUM 0 0 3C.8H 2G SUGAR BEETS 7G 0 5C.9G 2H COTTON 0 0 2C.3G 4G 165 Table A ( cont inued ) CMPD 110 CMPD 111 CMPD 112 CMPD 113 RATE=»KG/HJ- 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0. POSTEMERGENCE BARLEY 5C,8G 10C 3C,7G 6C.9G 2C.4G 4C.8G 0 0 BARNYARD GRASS 0 3C, 6U O 3C,6H 2C 3C.8H 0 0 CHEATGRASS 5C.8G 9C .C,IG 5C.9G 3C.70 8G 0 0 COCKLEBUR 9C IOC 6H 10C 4G 9C 0 0 CORN 6C.9G IOC SC.9G 9C 3C,4G 4C.8G 0 0 COTTON 2C,4G 9C 2C.4G 9C 2G 2C.3G 0 0 CRABGRASS 0 8G 2G 7G 0 2G 0 0 GIANT FOXTAIL 2C,5G 9C 3C.5G 5C.9G 0 3G 0 0 HORNING GLORY 3H 2C, ,7H 3C.4H 6C.9H 2C,3H 2C.5H 0 0 NUTSEDGE 2G 9C 4C 4C.8G 0 6C 0 0 RICE 5C.9G 5C, 9G 5C,9G 10C 3C.7G 5C,9G 0 0 SORGHUM 3C.7H 3d 9G 3C.7H 4C,9H 4C.7H 4C.9H 0 0 SOYBEAN 6C,9G 5C, 9G 4C.8G 6C,9G 5C,8G 5C,4G 0 0 SUGAR BEETS 3G 7G 2G 3G 5G 8H 0 0 VELVETLEAF 2C.6H 3C, 8H 2C,6H 4C.9H 0 3C.7H 0 0 WHEAT 9G 5C, 9G 4C.6G 5C,9G 5G 3C.9G 0 0 WILD OATS 9G 5C, 9G 4C,5G 9C 3C,6G 3C.9G 0 0 PREEMERGENCE BARLEY 0 4G 0 2G 0 4G 0 0 BARNYARD GRASS 3G 5G 4G 2C,4G 0 4G 0 0 CHEATGRASS 2G 8G 4β 3G 0 7H 0 0 COCKLEBUR 2G 3H 3G 7β - 3G 0 _ cost? 0 3C 0 0 0 4G 0 0 COTTON 0 3G €G 3G 3C 6β 0 0 CRABGRASS 2G 5G 2G 3C.4G 0 7H 0 0 GIANT FOXTAIL 2G 7H 2G 3C.6H 2G 6G 0 • MORNING GLORY 2G 5H 3C.4G 3G 2G 6H 0 0 NUTSEDGE 0 2G 2G 2C 0 6G 0 0 RICE 2C 10H 2G 3G 3C 3C,5G 0 0 SORGHUM 0 3C, 6H 0 3G 2G 3C.5H 0 0 SOYBEAN 2C.3G 3C, 5G 3G 2C,3G 2G 2C,4G 0 0 SUGAR BEETS 0 5G 4B 4G 0 6G 0 0 VELVETLEAF 2C.3G 2G 4C 3C 2C 2C 0 0 WHEAT 2G 2C, 6G 3G 4G 0 5H 0 0 WILD OATS 0 -G 6H 2C.4G 0 6H 0 0 Table A ( continued ) CMPD 114 CMPD 115 CMPD 116 CMPD 117 RATE-iKG/HA 0.01 0.05 0.-01 0.05 0.01 0.05 0.01 0.05 POSTEMERGENCE BARLEY 3C, ,9G 9C 0 0 0 0 - 0 BARNYARD GRASS 3C, 5H 9H 0 0 0 0 0 0 CHEATGRASS 9G 9G 0 0 0 0 7G 3C,7G COCKLEBUR 2G 3C, ,9G 0 0 0 0 4G 2G CORN 3C, 9H 5U, ,9G 0 0 0 0 3C, 9G 3C.9G COTTON 2G 3C, ,6G 0 0 0 0 IC 3C.6G CRABGRASS 6G 7G 0 0 0 0 5G 4G GIANT FOXTAIL 4G 3C, ,ββ 0 0 0 0 4G 5G MORNING GLORY 3C, 6G 4C, ,8G 0 0 0 0 5G 4G NUTSEDGE 0 8G 0 0 0 0 2G 0 RICE 7G 6C, 9G 0 0 0 0 4C, 9G 3C.8G SORGHUM 3G 4C, 8H 0 0 0 0 4C, SH 4C.9G SOYBEAN 4C, 8G 5C, 9G 0 0 0 0 4C, 8G 5C.9G SUGAR BEETS 3H 3C. 7H 0 0 0 0 3C, 7G 5C.9G VELVETLEAF 3C. 6G 3C, 7G 0 0 0 0 0 3C.6G WHEAT 5G 3C, 8G 0 0 0 0 8G 9G WILD OATS 4G 5C, 9G 0 0 0 0 4C, 8G 2C,6G PREEMERGENCE BARLEY 2G 0 0 0 0 0 0 0 BARNYARD GRASS 5G 2G 0 0 0 0 0 0 CHEATGRASS 6G 2G 0 0 0 0 0 0 COCKLEBUR 0 0 0 0 - 0 0 — CORN 0 0 0 0 0 0 0 0 COTTON 0 0 0 0 0 0 0 2G CRABGRASS 0 3G 0 0 - 0 - 5G GIANT FOXTAIL 0 5G 0 0 0 0 — 6G MORNING GLORY 0 0 0 0 0 0 0 2G NUTSEDGE 10E 0 0 0 0 0 0 0 RICE 3G 0 0 0 0 0 0 0 SORGHUM 2G 0 0 0 0 0 0 0 SOYBEAN 0 0 0 0 0 0 0 0 SUGAR BEETS 0 0 0 0 0 0 3G 7G VELVETLEAF 0 0 0 0 0 0 0 2G WHEAT 0 0 0 0 0 0 0 0 WILD OATS 0 0 0 0 0 0 0 0 Table A (continued) CMPD 118 CMPD 119 CMPD 120 RATE-KG/HΛ 0.01 0.05 0.01 0.05 0.01 0.05 POSTEMERGENCE BARLEY 0 4G 0 0 3C, 6G 4C.9G BARNYARD GRASS 0 3C, 8H 0 0 3C, 7H 4C.9G CHEATGRASS 2C, 9G 4C, 9G 0 3G 0 9G COCXLEBUR 0 4C, 9H 0 0 0 4C,9G CORN 3C, 5H 4U, 9G 0 3C,9H 2C, 9G 4U.9G COTTON 3C, 3G 4C, 9G 0 0 2G 4C.8G CRABGRASS 3G 7β 0 0 3G 3C.8G GIANT ΓOXTAIL 4G 3C,sσ 0 0 3G 4C-9G MORNING GLORY 0 4C, 9G 0 0 0 4C.8G NUTSEDGE 0 3C, 9G 0 0 0 6G RICE 5C, 9G 5C, 9G 0 5G 3C, 7G 6C,9G SORGHUM 2G 3C, 6G 0 0 3C, 6G 4C,9G SOYBEAN 3C, 7G 3d 9G 0 0 3d 5β 4C.9G SUGAR BEETS 3C, 6H 6C, 9G 0 0 0 2G VELVETLEAF 3C, 3H 4C, 9H 0 0 0 3C.5G WHEAT 0 7G 0 0 7β 9G PREEMERGENCE BARLEY 0 0 0 0 0 0 BARNYARD GRASS 0 0 0 0 0 2G CHEATGRASS 0 0 0 0 0 3G COCKLEBUR 0 - 0 0 0 0 CORN 0 0 0 2G 0 2C COTTON 0 0 0 0 0 0 CRABGRASS 0 - 0 0 - 7G GIANT FOXTAIL 0 3G 0 - 0 4G MORNING GLORY 0 0 0 0 0 0 NUTSEDGE 0 0 0 0 0 0 RICE 0 2G 0 0 0 0 SORGHUM 0 0 0 0 0 0 SOYBEAN 0 2G 0 0 0 0 SUGAR BEETS 0 2G 0 0 0 3G VELVETLEAF 0 0 0 4G 0 0 WHEAT 0 0 0 0 0 0 WILD OATS 0 0 0 0 0 3G Table A ( continued ) CMPD 121 CMPD 122 CMPD 123 CMPD 124 RATE=KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSTEMERGENCE BARLEY 0 0 0 0 8G 2C.9G 0 SG BARNYARD GRASS 0 3G 0 4G 3C, ,9H 4C.9G 0 6G CHEATGRASS 0 2C, ,9G 0 8G 3C, 9G 3C,9G 0 5G COCKLEBUR 0 2G 0 2C.5G 3C, 8G 5C,9G 0 5G CORN 0 4G 0 1C.2G 9G 9C 0 2C,6G COTTON 0 0 0 1C,7G 2C, 6β 3C,8G 0 2G CRABGRASS 0 0 0 0 2C, 60 3C,9G 0 0 GIANT FOXTAIL 0 2C, 9G 0 6G 9G 10C 0 6G MORNING GLORY 0 0 0 1C,2G sc, 9H 6C,9G 0 0 NUTSEDGE 0 0 0 0 5G 8G 0 0 RICE 0 0 0 1C,2G 2C, 8G 4C.9G 0 2C.5G SORGHUM 0 0 0 0 2C, 7G 2C,9G 0 4G SOYBEAN 0 IC, 3G 1C.2G 2C,4G 3C, .8G 3C.8G 0 2C,2G SUGAR BEETS 0 2C, 8H 0 3C-7G 3C, 8G 3C.8G 0 2C,6G VELVETLEAF 0 0 0 2C.8G 4C, SG 6C.9G 0 4G WHEAT 0 0 0 8G 9G 3C,9G 0 2G WILD OATS 0 0 0 2C-5G 9G 3C-9G 0 2G PREEMERGENCE BARLEY 0 0 0 0 0 2G 0 0 BARNYARD GRASS 0 0 0 0 2G 4G 0 0 CHEATGRASS 0 0 0 0 0 6G 0 0 COCKLEBUR 0 0 0 0 4G 5G 0 7G CORN 0 0 0 0 0 2C.7G 0 0 COTTON 0 0 0 0 0 0 0 0 CRABGRASS 0 0 0 0 0 2C,8G 0 4G GIANT FOXTAIL 0 0 0 0 4G 2C.7G 0 5G MORNING GLORY 0 0 0 0 3G SG 0 6G NUTSEDGE 0 4G 0 0 0 10E 0 3G RICE 0 0 0 0 5G 2C,8H 0 0 SORGHUM 0 0 0 0 0 0 0 3G SOYBEAN 0 0 0 0 2G IC 0 0 SUGAR BEETS 0 5G 0 0 7G 4C,9G 0 0 VELVETLEAF 0 4G 0 0 3G 3G 0 IC, 2G WHEAT 0 0 0 0 0 2G 0 0 WILD OATS 0 0 0 0 0 0 0 0 Table A (continued) CMPD 12S CMPD 126 RATE-KG/HA 0.01 0. 0.01 0.1 POSTEMERGENCE BARLEY 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 COCKLEBUR 0 0 0 0 CORN 0 0 0 0 COTTON 0 0 0 0 CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 MORNING GLORY 0 0 0 0 NUTSEDGE 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SOYBEAN 0 0 0 0 SUGAR BEETS 0 0 0 0 VELVETLEAF 0 0 0 0 WHEAT 0 0 0 0 WILD OATS 0 0 0 0 PREEMERGENCE BARLEY 0 0 0 0 BARNYARD GRASS 0 0 0 0 CHEATGRASS 0 0 0 0 COCKLEBUR 0 0 0 0 CORN 0 0 0 0 COTTON 0 0 0 3G CRABGRASS 0 0 0 0 GIANT FOXTAIL 0 0 0 0 MORNING GLORY 0 0 0 2G NUTSEDGE 0 4G 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 SOYBEAN 0 2G 0 0 SUGAR BEETS 0 0 0 0 VELVETLEAF 0 0 0 2G WHEAT 0 0 0 0 WILD OATS 0 0 0 0 Test B Postemergence Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafra.s sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Diqitaria sanquinalis). sicklepod (Cassia obtusifolia). jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti). lambsquarters (Chenopodium album). rice (Orvza sativa) and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis). cocklebur (Xantium pensyl- vanicu ) . morningglory (Ipomoea hederacea). cotton (Gossypium hirsutum). johnsongrass (Sorghum halepense). barnyardgrass (Echinochloa crusqalli). corn (Zea mays), soybean (Glycine max) and giant foxtail (Setaria faberi) . The third pot was planted with wheat (Triticum aestivum). barley (Hordeum vulqare). wild buckwheat (Polqonum convolvulus .), cheatgrass (Bromus secalinus .). sugarbeet (Beta vulqaris). wild oats (Avena fatua) . viola (Viola arvensis). blackgrass (Alopecurus mvosuroides) , and rape (Brassica napus) . The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic 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. barnyardgrass. 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. Table B Compound 1 POSTEMERGENCE PREEMERGENCE Rate g/ha 62 16 4 1 250 62 16 4 Corn 100 70 50 20 60 30 20 0 Wheat 70 40 30 0 50 20 0 0 Barley 40 0 0 0 50 20 0 0 Rice 90 60 30 0 100 100 50 0 Soybean 90 40 0 0 60 0 0 0 Cotton 40 0 0 0 60 30 0 0 Sugar beet 90 70 50 30 90 70 50 30 Rape 60 30 0 0 100 90 60 30 Crabgrass 70 50 30 0 90 70 50 30 Johnsongrass 70 50 30 0 90 70 50 30 Blackgrass 70 50 30 0 90 60 30 0 Barnyardgrass 70 30 0 0 50 30 0 0 Nutsedge 50 30 0 0 90 70 50 30 Giant Foxtail 0 0 0 0 60 40 0 0 Green Foxtail 0 0 0 0 70 50 30 0 Cheatgrass 90 60 30 0 90 70 30 0 Wild Oats 70 40 0 0 40 0 0 0 Wild Buckwheat 60 30 0 0 100 60 30 0 Viola 50 30 0 0 90 80 60 30 Lambsquarter 60 30 0 0 100 60 30 0 Cocklebur 60 30 0 0 90 90 60 30 Morningglory 40 0 0 0 70 40 0 0 Teaweed 70 50 30 0 70 50 30 0 Sicklepod - 50 30 0 90 70 50 30 Jimsonweed 30 0 0 0 70 50 30 0 Velvetleaf 90 30 20 0 70 50 30 0 Table B (continued) Compound 2 POSTEMERGENCE PREEMERGENCE Rate g/ha 62 16 4 1 250 62 16 4 Corn 100 100 90 60 90 70 40 0 Wheat 90 70 50 30 90 60 30 0 Barley 60 50 30 0 90 50 30 0 Rice 100 60 40 0 100 100 90 70 Soybean 100 90 60 30 90 70 30 0 Cotton 90 90 90 30 90 60 30 0 Sugar beet 100 60 30 0 90 90 70 50 Rape 100 40 0 0 100 90 70 50 Crabgrass 90 70 50 30 100 100 100 70 Johnsongrass 90 70 50 30 100 90 60 30 Blackgrass 100 70 50 0 100 100 90 60 Barnyardgrass 100 60 30 0 100 100 60 30 Nutsedge 70 50 30 0 100 70 50 30 Giant Foxtail 100 50 30 0 90 70 50 30 Green Foxtail 30 30 30 0 90 80 70 50 Cheatgrass 80 50 30 0 100 70 30 0 Wild Oats 80 60 40 0 70 50 0 0 Wild Buckwheat 50 30 0 0 90 70 50 30 Viola 70 50 30 0 100 100 70 50 ambsquarter 100 70 50 30 100 100 90 70 Cocklebur 100 70 50 30 90 80 70 50 Morningglory 90 90 60 40 90 80 60 30 Teaweed 90 70 50 30 90 70 50 30 Sicklepod 100 90 70 50 90 70 50 30 Jimsonweed 90 70 50 30 100 90 60 30 Velvetleaf 100 100 40 0 90 70 50 30 Table B (continued) Compound 3 POST EMERGI SNCE PREEMERGENCE Rate g/ha 62 16 1 250 62 16 4 Corn 100 100 70 100 100 40 20 Wheat 90 60 30 70 50 30 0 Barley 90 60 30 70 30 0 0 Rice 100 100 0 100 100 90 70 Soybean 100 100 50 90 70 30 0 Cotton 90 90 40 90 70 50 30 Sugar beet 100 70 30 90 80 70 50 Rape 100 90 0 100. 90 70 50 Crabgrass 100 70 30 100 * 90 60 30 Johnsongrass 90 50 o- 100 90 60 30 Blackgrass 100 70 30 90 80 70 50 Barnyardgrass 100 70 30 90 70 50 30 Nutsedge 100 40 0 100 90 70 50 Giant Foxtail 80 60 0 90 60 30 0 Green Foxtail 90 70 30 90 70 50 30 Cheatgrass 90 60 0 90 80 60 30 Wild Oats 100 70 30 70 50 30 0 Wild Buckwheat 70 30 0 90 70 50 30 Viola 100 100 30 100 100 100 70 Lambsquarter 100 100 50 100 100 70 50 Cocklebur 100 100 50 90 80 60 30 Morningglory 100 70 30 90 80 50 30 Teaweed 90 70 30 90 80 60 30 Sicklepod 100 100 70 90 70 50 30 Jimsonweed 100 90 30 90 70 50 30 Velvetleaf 100 100 30 90 70 50 30 Table B (continued) Compound 4 POSTEMERGENCE PREEMERGENCE Rate g/ha 62 16 4 1 250 62 16 4 Corn 100 90 80 60 70 40 0 0 Wheat 70 50 30 0 50 30 0 0 Barley 0 0 0 0 30 0 0 0 Rice 100 100 0 0 100 90 70 30 Soybean 60 30 0 0 80 40 0 0 Cotton 100 60 30 0 80 30 0 0 Sugar beet 70 50 30 0 90 70 50 30 Rape 70 50 0 0 100 90 60 30 Crabgrass 80 50 30 0 90 70 50 30 Johnsongrass 70 30 0 0 100 90 70 30 Blackgrass 50 30 0 0 90 70 50 30 Barnyardgrass 70 30 0 0 90 70 30 0 Nutsedge 40 0 0 0 100 90 70 50 Giant Foxtail 40 0 0 0 50 30 0 0 Green Foxtail 50 30 0 0 50 30 0 0 Cheatgrass 50 0 0 0 90 60 30 0 Wild Oats 0 0- 0 0 30 0 0 0 Wild Buckwheat 70 50 30 0 90 70 50 30 Viola 70 50 30 0 100 90 60 30 La bsquarter 100 70 50 30 90 70 50 30 Cocklebur 90 60 30 0 90 80 70 50 Morningglory 100 60 30 0 90 70 50 30 Teaweed 90 60 30 0 90 70 50 30 Sicklepod 100 60 30 0 100 70 50 30 Jimsonweed 100 60 30 0 90 80 50 30 Velvetleaf 100 60 30 0 90 70 50 30 Table B (continued) Compound 6 POSTEMERGENCE PREEMERGENCE Rate g/ha 62 16 4 1 250 62 16 4 Corn 100 100 70 40 90 70 30 0 Wheat 100 90 70 40 90 60 30 0 Barley 90 60 30 0 70 30 0 0 Rice 100 70 30 0 100 90 70 50 Soybean 90 70 30 0 90 70 30 0 Cotton 30 0 0 0 80 50 30 0 Sugar beet 90 60 30 0 100 70 30 0 Rape 60 30 0 0 90 80 60 30 Crabgrass 90 70 50 30 90 70 50 30 Johnsongrass 90 70 50 30 90 80 70 50 Blackgrass 100 90 70 40 100 90 70 50 Barnyardgrass 90 70 30 0 100 90 60 30 Nutsedge 50 30 0 0 90 60 30 0 Giant Foxtail 40 0 0 0 90 50 30 0 Green Foxtail 30 0 0 0 100 60 30 0 Cheatgrass 90 60 30 0 100 70 50 30 Wild Oats 100 70 50 30 80 30 0 0 Wild Buckwheat 30 0 0 0 90 60 30 0 Viola 90 70 50 30 90 80 70 40 La bsquarter 80 70 50 30 100 100 100 100 Cocklebur 90 70 50 30 90 70 50 30 Morningglory 90 60 30 0 90 80 70 50 Teaweed 70 50 30 0 80 60 30 0 Sicklepod 100 70 50 30 90 70 50 30 Jimsonweed 90 70 30 0 90 80 60 30 Velvetleaf 70 30 0 0 90 70 50 30 Table B (continued) Compound 7 POSTEMERGENCE PREEMERGENCE :ate g/ha 62 16 4 1 250 62 16 4 Corn 100 100 70 50 80 50 0 0 Wheat 100 70 50 40 90 50 0 0 Barley 90 60 30 0 70 50 30 0 Rice 100 60 0 0 100 100 90 70 Soybean 90 60 0 0 80 30 0 0 Cotton 30 0 0 0 70 30 0 0 Sugar beet 70 50 30 0 90 80 70 50 Rape 100 60 20 0 90 60 30 0 Crabgrass 90 40 0 0 90 70 50 30 Johnsongrass 90 70 50 30 90 80 70 50 Blackgrass 100 90 70 50 100 90 70 50 Barnyardgrass 80 40 30 0 90 70 20 0 Nutsedge 40 0 0 0 100 80 30 30 Giant Foxtail 0 0 0 0 50 30 0 0 Green Foxtail 0 0 0 0 70 50 30 0 Cheatgrass 90 60 30 0 90 60 30 0 Wild Oats 90 60 30 0 70 50 30 0 Wild Buckwheat 0 0 0 0 50 30 0 0 Viola 70 30 0 0 90 70 50 30 ambsquarter 70 50 30 0 100 100 100 90 Cocklebur 100 90 60 30 90 60 30 0 Morningglory 70 50 30 0 90 60 30 0 Teaweed 70 50 30 0 80 60 30 0 Sicklepod 90 70 50 30 90 70 50 30 Jimsonweed 100 70 50 30 90 70 50 30 Velvetleaf 50 40 20 0 70 40 0 0 178 Table B (continued). CMPD 59 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL - 30 20 0 0 VELVETLEAF 100 100 70 30 SUGAR BEETS 100 60 30 0 CRABGRASS 60 30 0 0 TEAWEED 80 50 30 0 JIMSONWEED 100 60 30 0 RICE 100 100 90 60 COCKLEBUR 100 100 60 30 COTTON 70 20 0 0 SOYBEAN 100 100 70 50 BARNYARD GRASS 100 100 70 50 WILD OATS 70 30 0 0 MORNINGGLORY 60 30 0 0 WHEAT 100 90 60 30 CASSIA 100 90 80 70 JOHNSONGRASS 100 80 50 30 NUTSEDGE 90 60 30 0 CORN 100 100 90 70 WILD BUCKWHEAT 70 50 30 0 BLACK GRASS 70 30 0 0 RAPESEED 100 90 70 50 BARLEY 70 50 30 0 GREEN FOXTAIL 30 20 0 0 CHEAT GRASS 60 30 0 0 BUCKWHEAT VIOLA 90 50 30 0 LAMBSQUARTER 100 90 70 50 CHICK WEED CT/US87/0U 179 Table B (continued) CMPD 59 RATEβG/HA 0250 00 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 50 30 VELVETLEAF 90 60 SUGAR BEETS 70 50 CRABGRASS 70 30 TEAWEED 70 50 JIMSONWEED 90 60 COCKLEBUR 80 60 COTTON 0 0 SOYBEAN 80 40 BARNYARD GRASS 90 50 WILD OATS 40 0 MORNINGGLORY 50 30 WHEAT 70 30 CASSIA 70 50 JOHNSONGRASS 90 70 NUTSEDGε 0 0 CORN 80 0 WILD BUCKWHεAT 50 30 BLACK GRASS 70 50 RAPESEED 90 60 BARLEY 0 0 GREEN FOXTAIL 50 30 CHEAT GRASS 30 0 BUCKWHEAT - - VIOLA - - LAMBSQUARTER 90 70 CHICK WEED — — 180 Table B (continued ) CMPD 60 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 70 50 30 0 VELVETLEAF 100 90 70 60 SUGAR BEETS 100 100 90 60 CRABGRASS 60 30 0 0 TEAWEED 100 70 50 30 JIMSONWEED 100 100 90 70 RICE 100 100 90 70 COCKLEBUR 90 80 70 60 COTTON 100 70 30 0 SOYBEAN 100 100 100 100 BARNYARD GRASS 100 100 100 60 WILD OATS 60 30 0 0 MORNINGGLORY 60 50 40 30 WHEAT 100 70 50 30 CASSIA 100 100 100 70 JOHNSONGRASS 100 100 100 60 NUTSEDGE 100 100 100 50 CORN 100 100 100 100 WILD BUCKWHEAT 100 90 60 30 BLACK GRASS 90 70 50 30 RAPESεεD 100 100 100 90 BARLEY 0 0 0 0 GREEN FOXTAIL 70 50 30 0 CHEAT GRASS 60 30 0 0 BUCKWHEAT VIOLA 100 100 60 30 LAMBSQUARTER 100 100 90 70 CHICK WEED Table B (continued) CMPD 60 RATE-G/HA 0250 0062 0016 0004 0001 PREEMERGENCE , Q G I AN T F O XT A IL 70 50 30 20 VEL V ETLεAF 90 80 60 30 S U G AR BEETS 90 70 50 30 CRABGRASS 90 70 50 30 TEAWEED 100 80 60 40 JIMS O NWEED 100 70 50 30 RI C E 100 100 90 8 0 C OCKLEBUR 90 80 50 30 - CO TTON 50 30 0 0 S O YBEAN 90 70 50 30 BARNYARD GRASS 100 90 70 30 WILD OATS 50 M O RNINGGLORY 0 0 « W HEAT 80 50 30 0 CAS SIA 90 70 50 30 J O HNS O N G RASS 100 100 90 60 NUTSEDGE 100 60 30 0 W C0 I R L N D BUCKWHEAT 10 8°0 ξ7!0 I S S O 30 BLACK GRASS 90 60 30 0 RAPεsεεσ 100 90 80 70 0 0 0 BARLEY ° GREεN FOXTAIL 70 50 30 20 C HεAT GRASS 70 50 30 0 BUCKWHεAT VIOLA LAMBSQUARTER 100 100 90 70 CHICK WEED Table B (continued) CMPD 63 RATE= G /HA 0250 0062 0016 0004 0001 POSTEMERGENCE G IANT FOXTAIL 40 0 0 0 VEL V ETLEAF - 90 70 50 30 S U G AR BEETS - 70 30 0 0 C RAB G RASS - 50 30 0 0 T E A WEED - 60 30 0 0 JIMS O NWEED - 90 70 50 30 RI C E - 100 90 60 30 C O C KLEBUR - 100 . 70 50 30 C OTT O N - 50 30 0 . 0 SOYBEAN 6 600 5 _t0u 30 20 BARNYARD GRASS 100 70 50 30 WILD OATS 50 30 0 0 MORNINGGLORY 80 50 30 0 90 70 50 30 WHEAT CASSIA 90 60 30 0 J O HNSONGRASS 100 70 50 30 NUTSEDGE 0 0 0 0 CORN 100 100 90 70 WILD BUCKWHEAT 80 50 30 0 BLACK GRASS 90 40 0 0 RAPESεεD 90 70 50 30 BARLεY 70 30 0 0 GREEN FOXTAIL 40 0 0 0 n 0 0 CHEAT GRASS 40 BUCKWHEAT ~ 0 VI A - 1 0 50 0 0 LAMBS Q UARTER - 00 100 70 50 CHICK WEED - 183 Table B (continued) CMPD 63 RATE=G/HA 0250 00 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 60 30 VELVETLεAF 80 70 SUGAR BEETS 90 70 CRABGRASS 60 30 TEAWEεD 100 90 JIMSONWEED 100 90 RICE 100 90 COCKLEBUR 70 60 COTTON 50 30 SOYBEAN 60 0 BARNYARD GRASS 90 60 WILD OATS 80 50 MORNINGGLORY 90 80 WHEAT 80 60 CASSIA 90 70 JOHNSONGRASS 100 90 NUTSEDGE 0 0 CORN 100 100 WILD BUCKWHEAT 50 30 BLACK GRASS 100 70 RAPESEED 80 0 BARLEY 60 0 GREEN FOXTAIL 60 30 CHEAT GRASS 50 30 BUCKWHEAT - - VIOLA - - LAMBSQUARTER 90 70 CHICK εεo — — 184 Table B (continued) CMPD 64 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 70 50 30 0 VELVETLEAF 100 50 0 0 SUGAR BEETS 30 0 0 0 CRABGRASS 60 30 0 0 TEAWEED 60 30 20 0 JIMSONWEED 100 80 50 30 RICE 100 90 80 70 COCKLEBUR 100 70 30 0 COTTON 50 0 0 0 SOYBEAN 90 60 30 0 BARNYARD GRASS 100 90 70 50 WILD OATS 40 0 0 0 MORNINGGLORY 70 50 30 0 WHEAT 100 90 70 50 CASSIA 90 60 30 0 JOHNSONGRASS 100 100 70 50 NUTSEDGE 50 0 0 0 CORN 100 90 70 50 WILD BUCKWHEAT 80 50 30 0 BLACK GRASS 60 30 0 0 RAPESEED 100 100 90 60 BARLEY 90 70 50 30 GREEN FOXTAIL 70 50 30 0 CHEAT GRASS 40 0 0 0 BUCKWHEAT VIOLA 70 50 30 * 0 LAMBS UARTER 70 50 30 0 CHICK WEED 185 Table B (continued) CMPD 64 RATE=G/HA 0250 00 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 70 30 VELVETLEAF 90 30 SUGAR BEETS 100 90 CRABGRASS 80 50 TEAWEED 100 70 JIMSONWEED 90 80 RICE 100 90 COCKLEBUR 60 40 COTTON 60 0 SOYBEAN 60 0 BARNYARD GRASS 90 40 WILD OATS 90 70 MORNINGGLORY 80 30 WHEAT 90 60 CASSIA 100 80 JOHNSONGRASS 90 70 NUTSEDGE 80 0 CORN 100 70 WILD BUCKWHEAT 60 30 BLACK GRASS 100 70 RAPESEED 90 40 BARLEY 70 0 GREEN FOXTAIL 90 40 CHEAT GRASS 80 50 BUCKWHEAT - - VIOLA - - LAMBS UARTER 80 60 CHICK WEED - — 186 Table B (continued) CMPD 67 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 70 30 0 VELVETLEAF 100 70 50 SUGAR BEETS 90 70 50 CRABGRASS 80 60 40 TEAWεED 60 30 0 JIMSONWEED 90 70 50 RICE 90 60 30 COCKLEBUR 100 100 30 COTTON 100 60 30 SOYBεAN 100 80 50 BARNYARD GRASS 100 100 70 WILD OATS 50 30 0 MORNINGGLORY 100 70 50 WHεAT 70 50 30 CASSIA 90 60 30 JOHNSONGRASS 100 100 80 NUTSEDGE 100 70 30 CORN 100 90 70 WILD BUCKWHEAT 40 0 0 BLACK GRASS 50 30 0 RAPESεED 100 100 70 BARLEY 40 0 0 GREEN FOXTAIL 80 60 30 CHEAT GRASS 70 50 30 BUCKWHEAT - VIOLA - - LAMBSQUARTER - - 100 100 70 CHICK EεD _ _ _ _ _ Table B (continued) CMPD 67 RATE=G/HA 0250 0062 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 70 50 30 0 VELVETLEAF 60 30 20 0 SUGAR BEETS 50 30 0 0 CRABGRASS 80 50 30 0 TEAWEED 70 30 0 0 JIMSONWEED 70 50 30 0 RICE 80 50 30 0 COCKLEBUR 50 30 0 0 COTTON 20 0 0 0 SOYBEAN 60 30 0 0 BARNYARD GRASS 50 30 0 0 WILD OATS 30 20 0 0 MORNINGGLORY 0 0 0 0 WHEAT 30 0 0 0 CASSIA 40 0 0 0 JOHNSONGRASS 90 60 30 0 NUTSEDGE 30 20 0 0 CORN 60 20 0 0 WILD BUCKWHEAT 60 30 0 0 BLACK GRASS 70 30 0 0 RAPESEED 60 30 0 0 BARLEY 30 0 0 0 GREEN FOXTAIL 70 30 0 0 CHEAT GRASS 70 30 0 0 BUCKWHEAT _ _ _ _ _ VIOLA - LAMBSQUARTεR - 100 90 70 50 CHICK WEED _ _ _ _ _ 188 Table B (continued) CMPD 68 RATE=-G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 100 100 60 VELVETLEAF 100 100 90 SUGAR BEETS 100 100 70 CRABGRASS 80 60 40 TEAWEED 90 70 50 JIMSONWEED 80 70 50 RICE 80 70 50 COCKLEBUR 100 100 60 COTTON 100 70 30 SOYBEAN 100 100 80 BARNYARD GRASS 100 100 70 WILD OATS 60 30 0 MORNINGGLORY 100 100 100 WHEAT 90 70 50 CASSIA 100 80 60 JOHNSONGRASS 100 100 90 NUTSEDGE 100 100 80 CORN 100 100 100 WILD BUCKWHEAT 70 50 30 BLACK GRASS 80 50 30 RAPESEED 100 100 90 BARLεY 70 50 30 GREEN FOXTAIL 100 90 70 CHEAT GRASS 80 50 30 BUCKWHEAT - VIOLA - LAMBSQUARTER - - 100 100 70 CHICK WEED _ _ _ _ _ 189 Table B ( continued . CMPD 68 RATE=G/HA 0250 0062 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 90 70 50 30 VELVETLεAF 90 60 30 0 SUGAR BEETS 90 60 30 0 CRABGRASS 90 70 50 30 TEAWεED 90 70 50 30 JIMSONWEED 70 50 30 0 RICE 90 70 50 30 COCKLEBUR 90 70 50 30 COTTON 60 30 20 0 SOYBEAN 50 30 0 0 BARNYARD GRASS 90 70 50 30 WILD OATS 50 30 0 0 MORNINGGLORY 50 30 0 0 WHEAT 70 50 30 0 CASSIA 70 60 50 30 JOHNSONGRASS 90 60 30 0 NUTSEDGE 90 70 50 30 CORN 80 30 0 0 WILD BUCKWHEAT 70 50 30 0 BLACK GRASS 80 50 30 0 RAPESEED 80 50 30 0 BARLEY 60 30 0 0 GREEN FOXTAIL 00 80 50 30 CHEAT GRASS 90 60 30 0 BUCKWHEAT _ _ _ _ _ VIOLA _ _ _ _ _ LAMBSQUARTER - 90 80 60 30 CHICK WEED - 190 Table B (continued) CMPD 69 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 50 30 0 VELVETLEAF 90 70 50 SUGAR BEETS 80 70 50 CRABGRASS 60 30 0 TEAWEED 60 30 0 JIMSONWEED 50 40 30 RICE 80 50 30 COCKLEBUR 60 30 0 COTTON 50 30 0 SOYBEAN 50 30 0 BARNYARD GRASS 70 50 30 WILD OATS 0 0 0 MORNINGGLORY 90 60 20 WHEAT 0 0 0 CASSIA 70 50 30 JOHNSONGRASS 100 70 50 NUTSEDGE 90 30 0 CORN 80 70 50 WILD BUCKWHEAT - 0 0 BLACK GRASS 0 0 0 RAPESEED 90 70 50 BARLEY 0 0 0 GREEN FOXTAIL 50 30 0 CHEAT GRASS 0 0 0 BUCKWHEAT - VIOLA _ _ _ _ _ LAMBSQUARTER - - 70 50 30 CHICK WEED _ _ _ _ _ Table B (continued) CMPD 69 RATE=G/HA 0250 0062 0016 0004 0001 PREEMERGENCE G IANT F O XTAIL 30 0 0 0 VELVETLεAF. - 0 0 0 0 S UG AR BεETS - 80 30 0 0 CR A B G RASS 30 0 0 0 TEAWEED - 60 30 0 0 JIMSONWEED - 70 50 30 0 RI C E - 90 60 30 0 COC KLEBUR - 50 30 0 0 C O TTON - 0 0 0 0 SOY BE A N 20 0 0 0 BARNYARD GRASS 70 30 0 0 WILD O ATS - 0 0 0 0 M OR NIN G GLORY - 0 0 0 0 WHEAT - 0 0 0 0 C ASSIA 30 0 0 0 JOHNSONGRASS - 80 50 30 0 NUT S ED G E - 50 30 0 0 C ORN - 30 20 0 0 W ILD BUCKWHEAT - 50 30 0 0 BLA C K G RASS 30 0 0 0 RAPESEED 70 40 0 0 BARLEY - 0 0 0 0 GREεN FOXTAIL 30 0 0 0 0 0 0 0 CHεAT GRASS BUCKWHεAT VIOLA LAMBSQUARTεR 90 60 30 CHICK εED 192 Table B (continued). CMPD 70 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 30 0 0 VELVETLEAF 100 90 60 SUGAR BEETS 100 100 ' 90 CRABGRASS 80 50 30 TEAWEED 60 30 0 JIMSONWEED 100 100 90 RICE 100 100 ' 100 COCKLεBUR 100 70 50 COTTON 70 40 20 SOYBεAN 100 100 90 BARNYARD GRASS 100 100 60 WILD OATS 50 30 0 MORNINGGLORY 90 80 50 WHEAT 100 100 90 CASSIA 90 80 70 JOHNSONGRASS 100 100 100 NUTSEDGE 100 60 30 CORN 100 100 90 WILD BUCKWHEAT 60 30 — BLACK GRASS 70 50 30 RAPESEED 100 100 80 SARLεY 70 50 30 GREEN FOXTAIL 30 0 0 CHEAT GRASS 90 60 30 BUCKWHEAT _ _ _ _ _ VIOLA _ _ _ _ _ LAMBSQUARTεR - - 100 90 70 CHICK wεεσ _ _ _ _ _ Table B (continued) CMPD 70 RATE=G/HA 0250 0062 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 30 20 0 0 VELVETLεAF 80 50 30 0 SUGAR BBεTS 70 50 30 0 CRABGRASS 80 40 0 0 T AWEED 80 60 40 20 JIMSONWEED 90 70 50 30 RICE 100 90 60 30 COCKLEBUR 50 30 0 0 COTTON 50 30 • 0 0 SOYBEAN 50 30 0 0 BARNYARD GRASS 90 60 30 0 WILD OATS 50 30 0 0 MORNINGGLORY 0 0 0 0 WHEAT 60 30 0 0 CASSIA 40 0 0 0 JOHNSONGRASS 100 70 50 30 NUTSEDGE 80 30 0 0 CORN 60 30 0 0 WILD BUCKWHEAT 60 30 0 0 BLACK GRASS 80 50 30 0 RAPESEεD 60 30 0 0 BARLεY 60 30 0 0 GREEN FOXTAIL 60 30 0 0 CHEAT GRASS - 70 50 30 0 BUCKWHEAT _ _ _ _ _ VIOLA - LAMBSQUARTER - 100 90 60 30 CHICK WEED _ _ _ _ _ 194 Table B (continued) CMPD 71 RATE=G/HA 0250 0062 0016 0004 0001 POSTEMERGENCE GIANT FOXTAIL 0 0 0 VELVETLEAF 100 0 0 SUGAR BEETS 90 80 20 CRABGRASS 30 0 0 TEAWEED 30 0 0 JIMSONWEED 40 — 0 RICE 50 50 40 COCKLEBUR 30 0 0 COTTON 0 0 0 SOYBEAN 80 30 0 BARNYARD GRASS 60 •30 0 WILD OATS 30 0 0 MORNINGGLORY 0 0 0 WHEAT 20 0 0 CASSIA 50 0 - JOHNSONGRASS 50 40 20 NUTSEDGE 30 20 0 CORN 60 60 20 WILD BUCKWHEAT 60 20 20 BLACK GRASS 0 0 0 RAPESEED 80 50 30 BARLEY 20 0 0 GREεN FOXTAIL 0 0 0 CHEAT GRASS 30 0 0 BUCKWHEAT VIOLA 0 0 0 LAMBSQUARTER 0 0 0 CHICK WEED Table B (continued) CMPD 71 RATE=G/HA 0250 0062 0016 0004 0001 PREEMERGENCE GIANT FOXTAIL 30 0 40 0 - VELVETLεAF 70 30 30 0 - SUGAR BEETS 90 90 40 50 CRABGRASS 60 60 0 0 - TEAWEED 80 80 20 0 - JIMSONWEED 30 20 20 0 - RICE 90 70 40 0 - COCKLEBUR 50 50 0 0 - COTTON 60 60 20 - SOYBEAN 30 30 0 0 - BARNYARD GRASS 50 20 0 0 - WILD OATS 50 30 20 - MORNINGGLORY 50 50 20 20 WHEAT 0 0 0 0 - CASSIA - 0 0 - JOHNSONGRASS 70 40 30 20 NUTSEDGE 30 20 0 0 - CORN 30 20 20 0 - WILD BUCKWHEAT 80 80 40 30 BLACK GRASS 70 30 30 0 - RAPESEED 70 50 50 50 BARLEY 40 30 30 .30 GREEN FOXTAIL 30 30 40 30 CHEAT GRASS 70 40 30 20 BUCKWHEAT - VIOLA 80 20 20 0 - LAMBSQUARTER 80 80 0 0 CHICK WEED - Table B (continued ) • CMPD 72 RATE=G/HA 0250 0062 0016 00 0001 PREEMERGENCE GIANT FOXTAIL 30 30 20 — VELVETLEAF 90 80 20 0 SUGAR BEETS 90 90 30 0 CRABGRASS 80 50 30 0 TEAWEED 90 50 50 0 JIMSONWEεD 90 50 0 0 RICE 90 80 30 0 COCKLEBUR 80 50 30 30 COTTON 80 70 70 30 SOYBEAN 50 40 30 30 BARNYARD GRASS 80 30 20 20 WILD OATS 50 30 20 0 MORNINGGLORY 80 70 50 50 WHEAT 40 0 0 0 CASSIA — — - — JOHNSONGRASS 90 50 40 20 NUTSEDGE 70 20 20 20 CORN 70 30 30 20 WILD BUCKWHEAT 90 - 80 70 BLACK GRASS 90 40 30 30 RAPESεED 90 60 50 40 BARLEY 30 30 30 20 GREEN FOXTAIL 50 40 20 - CHEAT GRASS 70 80 40 30 BUCKWHEAT - - - - VIOLA 90 80 0 0 LAMBSQUARTER 100 90 30 0 CHICK wεεD — _ _ — Test C Two plastic windowsill trays were filled with planting medium. One was planted with seeds of speedwell (Veronica persica) . chickweed (Stellaria media). redroot pigweed (Amaranthus retroflexus) . wild mustard (Brassica kaber). wild raddish (Raphanus raphanistrum) . wild buckwheat (Polygonum convolvulus), common lambsquarters (Chenopodiu album) . stinkweed (Thlaspi arvense) . and rape (Brassica napus and B. campestries) . The other tray was planted with seeds of Italian ryegrass ( olium ultiflorum) . green foxtail (Setaria viridis) . wild oats (Avena fatua) . blackgrass (Alopecurus myosuroides), wheat (Triticum aestivum - vars. 'Nacozari'. 'Centurk' and Park') and barley (Hordeum vulgare - vars. 'Klages' and 'Morex'). The trays were treated when crops and weeds had grown to 2 to 3-leaf stage (postemergence) with compounds formulated in a non-phytotoxic solvent. The degree of crop injury and weed control was visually rated 2 to 4 weeks after compound application. The plant response ratings were either based on the scale of 0 to 100 where 0 - no effect, 10 = minimal injury and 100 = complete control or on a scale of 0 to 10 where 0 » no effect and 10 = complete control. The type of response is represented by letters where G - growth retardation. The results are given in Table C. 198 Table C CMPD 14 RATE GM/HA 0016 0032 00 POSTEMERGENCE BLACK GRASS 0 40 80 CANADA RAPE 0 0 0 CENTURK WHEAT 0 0 50 CHICKWEεD 0 0 0 GRεEN FOXTAIL 0 40 40 KLAGES BARLEY 20 20 50 MOREX BARLEY 40 60 70 NACOZARI WHEAT 20 30 70 PARK WHEAT 60 70 80 PIGWEεD 0 40 80 RYE GRASS 50 70 70 sτiNκwεεD 30 60 80 VERONICA PERSCA 0 0 0 WILD BUCKWHEAT 0 0 0 WILD MUSTARD 0 70 80 WILD OATS 0 0 30 WILD RADISH 0 0 0 Test D Seeds of the following crops and weeds are sown into 15 cm diameter pots containing Sassafras sandy loam soil: wheat (Triticum aestivum) . barley (Hordeum vulgare). sugarbeet (Beta vulqaris) . black nightshade (Solanum niqrum). chickweed (Stellaria media), common lambsquarters (Chenopodium album) . Galium (Galium aparine) . knotweed (Polygonum aviculare), Kochia (Kochia scoparia) . Matricaria (Martricaria inodora) . redroot pigweed (Amaranthus retroflexus) . smartweek (Polygonum persicaria). speedwell (Veronica persica), wild buckwheat (Polygonum convolvulus). wild mustard (Brassica kaber). wild radish (Raphanus raphanistrura) , annual bluegrass (Poa annua). annual ryegrass (Lolium mul iflorum) , blackgrass (Alopecurus mvosuroides) , green foxtail (Setaria viridis) . and wild oats (Avena fatua) . Compounds are formulated in a non-phytotoxic solvent and applied to the plants as a foliar spray. Plants are treated at three stages: 1) preemergence, 2) postemergence when sugarbeets are at the 1st true leaf stage, and 3) postemergence when sugarbeets have three leaves. Plants are grown in a temperature controlled greenhouse for the duration of the experiment. Wee control and crop injury are evaluated visually (3 to 4 weeks following compound application), using a scale of 0 to 100%, where 0 = no injury or control and 100 = complete death of the plants. The results are in Table D. Table D CMPD 36 RATE GM/HA 0030 00*3 0125 02 POSTEMERGENCE BARLEY 75 100 70 50 SUGARBEET CHOPS _ — _ - BLCK NIGHTSHADE 70 100 100 100 BLUE GRASS 10 100 100 100 BUCKWHEAT 0 0 0 0 CHICX WEED 0 0 0 0 GALIUM 0 0 0 100 GREEN FOXTAIL •0 95 100 100 KOCHIA 0 0 30 30 LAMBSQUΛRTER 0 0 0 0 MATRA INDORA 20 40 100 100 MUSTARD 100 100 100 100 PIG WEED 100 100 100 100 RYE GRASS 90 95 90 100 SMART WEED 0 0 0 0 SPEEDWELL 0 0 0 0 SUGARBEET C/TOL 0 0 0 0 WHEAT so 100 100 100 WILD OATS 100 100 100 100 WILD RADISH 0 0 0 0 PREEMERGENCE BARLEY 0 0 20 75 SUGARBEET CHOPS _ - — - BLCK NIGHTSHADE 0 20 25 30 BLUE GRASS 0 75 100 100 BUCKWHEAT 0 0 0 0 CHICK WEED 0 0 0 0 GALIUM 0 0 0 0 GREEN FOXTAIL 40 100 100 100 KOCHIA 0 0 0 0 LAHBSQUARTES 0 0 0 0 MATRΛ INDORA CO 95 100 100 MUSTARD • 0 0 50 75 FIG WEED 100 100 100 100 RYE GRASS 20 100 100 100 SMART WEED 0 0 50 100 SPEEDWELL 0 20 20 20 SUGARBEET C/TOL 0 10 20 40 WHEAT 0 10 15 20 WILD OATS 0 65 10 95 WILD RADISH 0 0 0 25

Claims: WHAT IS CLAIMED IS: 1. A compound of the Formula I: W JSO„NHCNA wherein J-l J-2 J-5 J-6 w is O or S ; R is H or CH : E is a single bond, CH or O; R χ is H. C -C alkyl, C -C haloalkyl. halogen. nitro, C.-C, alkoxy, SO NR R , C -C alkyl- thio. C.-C. alkylsulfinyl, C -C alkylsul- fonyl, CH CN, CN. CO R , C,-C haloalkoxy. C.-C haloalkylthio, C -C alkoxyalkyl, C -C alkylthioalkyl. CH or NR R ; Rα is H, CX-CTt alkyl, C&-C•_> cyanoalkyl. methoxy or ethoxy; R.b is H. C.1-C4_ alkyl or C3-C4_ alkenyl: or R. and R. may be taken together as -(CH.)--, -(CH 2 ) 4 -. -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -; R is C«_-CTt alkyl. C -Ct alkenyl. C«3-CTt alkynyl, C 2_-C4. haloalkyl, C2-C_3 cyanoalkyl, C_-Co. cycloalkyl. C -C cycloalkylalkyl or C,-C- alkoxyalkyl; R, and R are independently H or C_-C_ alkyl: α e 1 2 Q is s, so or NR,: Q 2 is O, S or R 2 : is O. S or NR ; R is H, C,-C. alkyl, phenyl, benzyl, CH CH=CH 2 , CH C≡CH. CN. C -C haloalkyl. OH. OCH or OC.H.; . 3 alkyl: R_ -> is H. halogen. CH i ' . OCH,, OCH2-CH,. OCF H or halomethyl: R6 £ is C.1-C4- alkyl: A-l A-2 A-3 A-4 A-5 A-6 5 20 A-7 X is H, C.1-C4. alkyl . C.1-C4. alkoxy , C, 1-C4. halo- alkoxy. C. -C haloalkyl . C , -C . haloalkylthio . , e s C.1-C4. alkylthio . halogen. C 2_-C_b alkoxyalkyl . C -C_ alkoxyalkoxy, amino. C,-C, alkylamino, di(C_ L-C.i alkyl)amino or C.3-C_b cycloalkyl; Y is H, C.1-C4 Λ alkyl, C,1-C4_ alkoxy, C,1-C4_ halo- alkoxy. C.-C haloalkylthio. C.-C alkylthio, 30 C 2 ~ C 5 -IfcoxY-lfcyl* C 2 _ 5 -l^oxyalltoxY' amino, C -C alkylamino, di(C -C alkyl)amino, C -C. alkenyloxy, C.-C alkynyloxy, C -C alkylthio- alkyl, C.-C haloalkyl. C -C alkynyl, azido, cyano, C -C_ alkylsulfinylalkyl, C_-C_ alkylsul- 2 b Z b NR d (C 2 -C 3 cyanoalkyl) or N(OCH 3 )CH 3 : m is 2 or 3; L and are independently O or S; R is H or C -C alkyl: R and R. are independently C -C alkyl: Z is CH or N; Z is CH or N: Y λ is O or CH 2 : X is CH . OCH . OC H 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_.. CH.. or CH 2 CH 3 : X is CH or OCH : Y 3 is H or CH 3 : X is CH . OCH , OC H , CH OCH or Cl; and Y 4 is CH 3 . OCH 3 . OC 2 H 5 or Cl; and their agriculturally suitable salts; provided that a) when X is Cl. F, Br or I, then Z is CH and Y is OCH 3 . OC 2 H-.. N(OCH 3 )CH 3 . NHCH 3 . N(CH_.) 2 or OCF H; b) when X or Y is C haloalkoxy. then Z is CH; c) X. and Y_ are not simultaneously Cl; 4 4 d) when W is S. then E is a single bond. R is H, A is A-l and Y is CH 3 . OCH 3# C 2 H 5 . CH 2 OCH 3 . C 2 H 5 , CF 3 . SCH 3 . OCH 2 CH=CH 2 , OO^C≡CH. OCH 2 CH 2 OCH , CH(OCH ) or 1.3-dioxolan- 2-yl; e) when the total number of carbons of X and Y is greater than four, then the number of carbons of R. must be less than or equal to two; f) Q and Q are not simultaneously S; g) when J is J-5, then Q_ is , and Q is NR ; h) when n is 0. then Q. is NR. and Q. is NR.: and 3 3 4 4 i) when R_b is other than H. then R is H. R,1 is H, W is O. A is A-l and E is a single bond. j) when J is J-6 or J-7. then A is A-l. 2. The compounds of Claim 1 where E is a single bond. 3. The compounds of Claim 1 where E is CH he compounds of Claim 1 where E is 0 and 5. The compounds of Claim 2 where W is 0; R χ is H, F. Cl. Br. C-^C.. alkyl. C- ^ -C- j alkoxy, C.-C 3 alkylthio. C.-C 2 alkyl. C.-C, alkoxy substituted with 1-3 atoms of F, Cl, or Br or C.-C, alkylthio substituted with 1-3 atoms of F. Cl or Br; R 2 is H or C.-C 3 alkyl; R 5 is H: X is C.-C 2 alkyl. C.-C alkoxy. Cl. F, Br, I. OCF 2 H, CH 2 F. CF 3 . OCH 2 CH 2 F. OCH 2 CHF 2 » OCH 2 CF 3 CH 2 C1 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 . 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.. CR-. -CT ' L Λ 9 . -C (CH,)... R f L 2 R h C≡CH or C=CCH 3 6. The compounds of Claim 5 where A is A-l. 7. The compounds of Claim 6 where J is J-l. 8. The compounds of Claim 6 where J is J-2. 9. The compounds of Claim 6 where J is J-3. 10. The compounds of Claim 6 where J is J-4. 11. The compounds of Claim 6 where J is J-5. 12. The compounds of Claim 6 where J is J-6. 13. The compounds of Claim 6 where J is J-7. 14. The compounds of Claim 7 where R is H; is H, ci. CH 3 or OCH 3 ; X is CH 3 . OCH 3 . Cl or OCF 2 H: and Y is CH 3 . OCH 3 . C 2 H 5 . CH 2 OCH 3 . NHCH 3 . CH(OCH ) or cyclopropyl. 15. The compounds of Claim 3 where R is H: J is J-l; is H; R l R 2 is H or CH 3 ; A is A-l; X is CH 3 . OCH 3 . Cl or OCF 2 H; and Y is CH 3 . OCH 3 . C 2 H 5 . CH 2 OCH 3 . NHCH 3 . CH(OCH ), or cyclopropyl. 16. The compounds of Claim 4 where R is H; J is J-l: R χ is H; X is CH 3 . OCH 3 . OCH 2 CH 3 . Cl or OCF 2 H and Y is CH 3 , OCH 3 . C 2 H 5 . CH 2 OCH 3 . NHCH 3 . CH(OCH 3 ), or cyclopropyl. 17. The compound of Claim 1 which is N-[(4.6- dimethoxypyrimidin-2-yl)aminocarbonyl]-5-methoxy- 1,2.3-benzothiadiazole-4-sulfonamide. 18. The compound of Claim 1 which is N-[(4- methoxy-6-methyl-l,3.5-triazin-2-yl)aminocarbonyl]- 5-methoxy-l.2.3-benzothiadiazole-4-sulfonamide. 19. The compound of claim 1 which is N-[[4-ethoxy-6-(methylamino)-l.3,5-triazin-2-yl]amino- carbonyl]-l-methyl-lH-benzotrizole-4-sulfonamide. 20. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 1 and at least one of the following: surfactant, solid or liquid diluent. 21. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 2 and at least one of the following: surfactant, solid or liquid diluent. 22. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 3 and at least one of the following: surfactant, solid or liquid diluent. 23. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 4 and at least one of the following: surfactant, solid or liquid diluent. 24. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 5 and at least one of the following: surfactant, solid or liquid diluent. 25. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 6 and at least one of the following: surfactant, solid or liquid diluent. 26. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 7 and at least one of the following: surfactant, solid or liquid diluent. 27. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 8 and at least one of the following: surfactant, solid or liquid diluent. 28. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 9 and at least one of the following: surfactant, solid or liquid diluent. 29. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 10 and at least one of the following: surfactant, solid or liquid diluent. 30. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 11 and at least one of the following: surfactant, solid or liquid diluent. 31. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 12 and at least one of the following: surfactant, solid or liquid diluent. 32. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 13 and at least one of the following: surfactant, solid or liquid diluent. 33. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 14 and at least one of the following: surfactant, solid or liquid diluent. 34. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 15 and at least one of the following: surfactant, solid or liquid diluent. 35. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 16 and at least one of the following: surfactant, solid or liquid diluent. 36. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 17 and at least one of the following: surfactant, solid or liquid diluent. 37. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 18 and at least one of the following: surfactant, solid or liquid diluent. 38. An agriculturally suitable composition for controlling the growth of undesired vegetation com¬ prising an effective amount of a compound of Claim 19 and at least one of the following: surfactant, solid or liquid diluent. 39. 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 1. 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 2. 41. 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. 42. 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. 43. 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. 44. 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. 45. 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 7. 46. 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. 47. 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 9. 48. 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 10. 49. 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 11. 50. 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 12. 51. 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 13. 52. 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 14. 53. 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 15. 54. 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 16. 55. 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 17. 56. 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 18. 57. 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 19.

Inventors: DOUGLASS DAVID L, MOON MARCUS P, DOUGLASS, DAVID, L., MOON, MARCUS, P.
Applicants: DU PONT, E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1987
Main classification: A01N43
IPC codes: A01N47, C07D521