Abstract:
This invention comprises novel fluoroalkoxy amino triazines, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants.

Description:
RELATED APPLICATION 
     This application is a continuation-in-part of my copending application U.S. Pat. application Ser. No. 07/172,593, filed Mar. 24, 1988 now abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     U.S. Pat. No. 4,744,816, issued May 17, 1988, and EP-A-164,269, published on Dec. 11, 1985, disclose herbicidal sulfonylureas of the formula ##STR1## wherein R 1  is, inter alia, CO 2  R 10 , etc.; 
     R 2  is H, F, Cl, Br, CF 3 , CH 3 , C 2  H 5 , OCH 3 , OC 2  H 5 , SCH 3  or SC 2  H 5  ; 
     R 10  is C 1  -C 4  alkyl, CH 2  CH 2  OCH3, CH 2  CH 2  Cl, CH 2  CH═CH 2  or CH 2  C.tbd.CH; 
     R 14  is H or C 1  -C 2  alkyl; 
     R 15  is C 1  -C 2  alkyl, OCH 3 , OC 2  H 5  or CH 2  CN; 
     X is NR 14  R 15  ; 
     Y is OCH 2  CH 2  F, OCH 2  CHF 2  or OCH 2  CF 3  ; and 
     Z is CH or N. 
     South African Application No. 84/2245, published 9/28/84, discloses herbicidal sulfonylureas of the formula ##STR2## wherein A is C 1  -C 6  haloalkyl 
     Z is O or S; 
     E is CH or N; 
     R 1  is, inter alia. H, COR 6 , etc.; 
     R 2  is, inter alia, H, etc.; 
     R 3  and R 4  are independently H, halogen, C 1  -C 4  alkyl, C 2  -C 4  haloalkoxy, NR 12  R 13 , etc.; 
     R 6  is, inter alia, C 1  -C 4  alkoxy, C 1  -C 4  haloalkoxy, C 2  -C 6  alkoxyalkoxy, etc.; and 
     R 12  and R 13  are independently H or C 1  -C 4  alkyl. 
     While these two references generically disclose some of the compounds of the instant invention, there is no specific mention of the instant compounds or their utility in sugar beets. 
     U.S Pat. No. 4,618,363 discloses herbicidal sulfonylureas of the formula ##STR3## wherein R 1  is H, halogen, NO 2 , C 1  -C 4  haloalkyl, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 5  alkenyl or C 1  --C 4  alkoxycarbonyl; 
     X is O, S, --SO-- or SO 2  ; 
     m is 0 or 1; 
     Q is, inter alia, R 13 , etc.; 
     R 13  is phenyl or phenyl substituted by halogen, NO 2 , CN, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  alkylthio, C 2  -C 5  alkenyl, C 1  -C 4  haloalkyl, C 1  -C 4  alkoxycarbonyl, --NR 45  R 46 , --SO 3  H or --SO2NR 47  R 48  ; 
     R 2  is C 1  -C 3  alkyl or C 1  -C 3  alkoxy, each unsubstituted by 1 to 3 halogen atoms; 
     R 3  is, inter alia, --NR 4  R 5 , etc.; and 
     E is N or CH. 
     While this reference generically discloses some of the compounds of the instant invention, there is no specific mention of the instant compounds or their utility in sugar beets. 
     SUMMARY OF THE INVENTION 
     This invention comprises novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants. ##STR4## wherein R is C 1  -C 4  alkyl, CH 2  CH═CH 2 , CH 2  C.tbd.CH, cyclopropylmethyl or CH 2  CH 2  R 2  ; 
     R 1  is C 1  -C 2  alkyl, C 1  -C 2  haloalkyl, CH 2  CN, CH 2  CH 3 , C 1  -C 3  alkoxy, C 1  -C 3  alkylthio, phenylthio or NR 3  R 4  ; 
     R 2  is C 1  -C 2  alkoxy, C 1  -C 2  alkylthio, CN or halogen; 
     R 3  and R 4  are independently H or CH 3  ; and 
     X is NHCH 3 , N(CH 3 )2 or N(CH 3 )OCH 3  ; provided that when R 1  is OCH 2  CH 3  or CH 2  OCH 3 , then R is other than CH 3  ; 
     and their agriculturally suitable salts. 
     In the above definitions, the term &#34;alkyl&#34; includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. 
     Alkoxy includes methoxy and ethoxy. 
     Alkylthio includes methylthio and ethylthio. 
     The term &#34;halogen,&#34; either alone or in compound words such as &#34;haloalkyl,&#34; means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as &#34;haloalkyl&#34; said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CF 3 , CH 2  CH 2  F, CF 2  CF 3  and CH 2  CHFCl. 
     The total number of carbon atoms in a substituent group is indicated by the C i  -C j  prefix where i and j are numbers from 1 to 4. For example, C 1  -C 4  alkyl would designate methyl, ethyl and the different propyl and butyl isomers; C 1  -C 2  alkylthio would designate methylthio and ethylthio; C 1  -C 2  alkoxy would designate methoxy and ethoxy. 
     Preferred for reasons of their higher herbicidal activity, greater safety to sugar beets and/or more favorable ease of synthesis are: 
     1. Compounds of Formula I wherein 
     R is C 1  -C 4  alkyl; 
     R 1  is C 1  -C 2  alkyl; and 
     X is NHCH 3  or N(CH 3 ) 2 . 
     2. Compounds of Formula I wherein 
     R is C 1  -C 4  alkyl; 
     R 1  is C 1  -C 2  haloalkyl; and 
     X is NHCH 3  or N(CH 3 ) 2 . 
     3. Compounds of Preferred 1 wherein 
     R is C 1  -C 3  alkyl; and 
     X is NHCH 3 . 
     4. Compounds of Preferred 1 wherein 
     R is C 1  -C 3  alkyl; and 
     X is N(CH 3 ) 2 . 
     Specifically preferred for reasons of highest herbicidal activity, greatest safety to sugar beets and/or most favorable ease of synthesis are: 
     Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, melting point 134-142° C.; and 
     Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethyoxy) -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, melting point 150-160° C. 
    
    
     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 will be known to one skilled in the art. 
     The compounds of Formula I can be prepared by the methods shown in Equations 1 and 2. 
     As shown in Equation 1, many of the compounds of Formula I can be prepared by reacting a silyl sulfonamide of Formula II with a heterocyclic carbamate of Formula III. ##STR5## 
     The reaction is carried out at 0° to 50° C. in a solvent such as acetonitrile, dioxane, or tetrahydrofuran in the presence of a fluoride ion source such as cesium fluoride or tetrabutylammonium fluoride for 0.1 to 2 hours. 
     Alternatively, some of the sulfonamides of Formula IV can be prepared and reacted with heterocyclic carbamates of Formula III to give compounds of Formula I as shown in Equation 2. ##STR6## 
     The reaction is carried out at 0° to 50° C. in a solvent such as acetonitrile, dioxane, or tetrahydrofuran in the presence of a non-nucleophilic base such as DBU for 0.2 to 2 hours. 
     Many of the silyl sulfonamides of Formula II can be prepared by reacting sulfonyl chlorides of Formula V with t-butyldimethylsilylamine (J. R. Bowser, et al., Inorganic Chemistry. 17. 1882 (1978)) as shown in Equation 3. ##STR7## 
     The reaction is carried out at 0° to 30° C. in a solvent such as dichloromethane in the presence of 1 to 2 equivalents of the amine and 1 equivalent of sodium bicarbonate. 
     Alternatively, many silyl sulfonamides of Formula II can be prepared by reacting silylsulfonamides of Formula VI with alkyl chloroformates as shown in Equation 4. ##STR8## 
     The reaction is carried out by contacting suitable silyl sulfonamides of Formula VI with an organolithium reagent such as n-butyllithium in an inert aprotic solvent such as tetrahydrofuran at -78° to 0° C. for 0.5 to 3 hours. The dilithio-intermediate VIa is then reacted with an alkyl orthoformate at -78° to 0° C. for 0.5 to 5 hours. Silylsulfonamides II are isolated by standard methods which are well known to one skilled in the art. 
     Many silyl sulfonamides of Formula II can be prepared by the indirect route shown in Equation 5. ##STR9## 
     The first two steps are done as described above for Equation 4. J. G. Lombardino (J. Org. Chem., 36, 1843 (1971)) also describes methods for preparing acid intermediate which are similar to acids of Formula VII. Methods to esterify acids under mild conditions are well known in the art. 
     Many sulfonamides of Formula IV can be prepared by deprotecting t-butylsulfonamides of Formula IIa as in Equation 6. ##STR10## 
     The reaction is carried out at -78° to 30° C. in an inert solvent such as hexane in the presence of an acid such as trifluoroacetic acid. The success of this reaction depends on the nature of R 1  and R and will be known to one skilled in the art. 
     Sulfonamides of Formula IIa can be prepared by methods similar to those described in Equations 3, 4 and 5 in which the t-butyldimethylsilyl moiety has been replaced by the t-butyl moiety. 
     The sulfonyl chlorides of Formula V can be prepared by oxidatively chlorinating the corresponding sulfur-containing compounds of Formula VIII as shown in Equation 7. R &#39; is H, alkyl, benzyl or carbamoyl. ##STR11## 
     The reaction of Equation 7 is carried out by contacting compounds of Formula VIII in a solvent such as acetic acid or proprionic acid with at least 3.0 equivalents of chlorine in the presence of at least 2.5 equivalents of water at about -20° to 30° C. for 0.2 to 5 hours. A. Wagenaar teaches specific reaction conditions for related compounds in Recl. Trav. Chim. Pays-Bas 101, 91 (1982). 
     Alternatively, reaction of compounds of Formula VIII, wherein R&#39; is H or benzyl, with a hypochlorite solution such as 5% NaOCl can provide sulfonyl chlorides of Formula V. Reaction conditions for similar reactions are described in South African Patent Application No. 84/8845 and EP-A-142,152. 
     As shown in Equation 8, many of the sulfonyl chlorides of Formula V can be prepared from the corresponding amines of Formula IX by a Meerwein reaction. ##STR12## 
     The reaction involves diazotization of the amine IX 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. Org.. Chem., 25, 1824 (1960). 
     Alternatively, sulfonyl chlorides of Formula V can be prepared by a modification of the above procedure as shown in Equation 9. ##STR13## 
     The amine hydrochloride salts IXa are diazotized with an alkyl nitrite 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. V. M. Doyle, in J. Org. Chem., 42. 2426, 2431 (1977), describes conditions for doing similar Meerwein reactions. 
     The heterocyclic carbamates of Formula III in Equations 1 and 2 can be prepared by methods described in U.S. Pat. No. 4,744,816. 
     The preparation of compounds of this invention is further illustrated by the following examples. 
     EXAMPLE 1 
     3-Methyl-2-(phenylmethylthio)-benzoic acid, 1-methylethyl ester 
     To a stirred suspension of dry tetrahydrofuran (125mL) and 35% potassium hydride in oil (6.3 g) was slowly added benzyl mercaptan (6.1 mL) at 0° C. under an inert atmosphere. After 15 minutes, 3-methyl-2-nitrobenzoic acid, 1-methylethyl ester (11.23 g) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between 6N sodium hydroxide (25 mL) and ethyl acetate (150 mL). The organic phase was dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel eluted with 5% ethyl acetate in hexanes to give 13.7 g of the title compound as a yellow oil, n D  1.5642. 
     90 MHz NMR (CDCl 3 ): δ 1 39 (d, 6H, CH 3 ); 2.39 (s, 3H, CH 3 ); 3.99 (s, 2H, CH 2 ); 5.32 (m, 1H, CH); and 7.26 (m, 8H, arom.). 
     IR (neat) 1720 cm -1  . 
     EXAMPLE 2 
     Methyl 2-(chlorosulfonyl)-3-methylbenzoate 
     To a stirred suspension of methyl 3-methyl-2-(Phenylmethylthio)-benzoate (24 g), dichloromethane (700 mL), water (150 mL), and concentrated hydrochloric acid (34 mL), kept at 0° C., was slowly added 5% sodium hypochlorite (450 mL). The resulting yellow suspension was stirred at 0° C. for 1 hour. The dichloromethane phase was dried over magnesium sulfate, filtered, concentrated, and triturated with chlorobutane-hexanes to give 14 g of the title compound as a white solid, m.p. 114-116° C. 
     90 MHz NMR (CDCl 3 ): δ 2.82 (s, 3H, CH 3 ); 3.97 (s, 3H, OCH 3 ); and 7.5 (m, 3H, arom.). 
     IR (nujol) 1730, 1360, and 1175 cm -1 . 
     EXAMPLE 3 
     Ethyl 2-[((dimethyl)-(1.1-dimethylethyl)silylamino)sulfonyl]-3-nitrobenzoate 
     A suspension of ethyl 2-(chlorosulfonyl)-3-nitrobenzoate (14.7 g), amino-t-butyldimethylsilane (15.4 g), and sodium bicarbonate (3.5 g) in dichloromethane (300 mL) was stirred at room temperature in a stoppered flask for 4 days. Water (90 mL) and saturated aqueous bicarbonate (45 mL) were added, and the mixture was stirred. The dichloromethane phase was dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel eluted with 20% ethyl acetate in hexanes to give 12.9 g of the title compound as a white solid, m.p. 101-102° C. 
     90 MHz NMR (CDCl 3 ): δ 0.30 (s, 6H, SiCH 3 ); 0.97 (s, 9H, CH 3 ); 1.41 (t, 3H, CH 3 ); 4.48 (q, 2H, OCH 2 ); 5.86 (s, 1H, NH); and 7.7 (m, 3H, arom.). 
     IR (nujol) 3200, 1730 and 1700 cm -1 . 
     EXAMPLE 4 
     Methyl 2-[((dimethyl)-1,1-dimethylethyl)silylamino)sulfonyl]-3-trifluoromethylbenzoate 
     A solution of N-[(dimethyl)-(1,1-dimethylethyl)silyl]-2-trifluoromethylbenzenesulfonamide (17.5 g) in dry tetrahydrofuran (250 mL) was contacted with 2.5 M butyllithium (46 mL) at 50° C. and allowed to warm to 0° C. over 1.5 hours under an inert atmosphere. The mixture was cooled to -78° C. and added to a solution of methyl chloroformate in dry tetrahydrofuran (300 mL) at -78° C. The mixture was stirred at -78° C. under an inert atmosphere for 1.5 hours and then quenched with saturated aqueous ammonium chloride (100 mL). After warming to 0° C., the tetrahydrofuran layer was dried over magnesium sulfate, filtered, evaporated, and chromatographed on silica gel eluted with 20% chlorobutane, 10% tetrahydrofuran and 70% hexanes to give 2.13 g of the title compound as a white solid, m.p. 80-84° C. 
     MHz NMR (CDCl 3 ): δ0.29 (s, 6H, SiCH 3 ); 0.96 (s, 9H, CH 3 ); 4.02 (s, 3H, OCH 3 ); 5.63 (s, 1H, NH); 7.8 (m, 2H, arom.); and 8 (m, 1H, arom.). 
     IR (nujol) 3250, 1725 cm -1   
     EXAMPLE 5 
     Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate 
     A solution of 2-(dimethyl-(1,1-dimethylethyl)-silylamino)-3-methylbenzoic acid, ethyl ester (0.36 g) and 0-phenyl-N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamate (0.39 g) in acetonitrile (10 mL) was treated with 1M tetrabutylammonium fluoride in tetrahydrofuran (1.1 mL). The mixture was stirred for 2 hours. After diluting the reaction with water (20 mL) and acidifying with 1N hydrochloric acid, the resulting precipitate was filtered, washed with water and hexane/ether, and air dried to give 0.28 g of the title compound as a white solid, m.p. 134-142° C. 
     200 MHz NMR (CDCl 3 ): δ 6 1.38 (t, 3H, CH 3 ); 2.89 (s, 3H, CH 3 ); 3.24 (s, 6H, NCH 3 ); 4.36 (q, 2H, OCH 2 ); 4.74 (q, 2H, CH 2 ); 7.4 (m, 4H, arom. and NH); and 12.38 (s, 1H, NH). 
     IR (nujol) 1710, 1695 cm -1   
     EXAMPLE 6 
     Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate 
     A solution of methyl 2-(dimethyl-(1,1-dimethylethyl)silylamino)-3-methylbenzoate (0.68 g) and -phenyl-N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamate (0.79 g) in tetrahydrofuran (10 mL) was treated with 1M tetrabutylammonium fluoride in tetrahydrofuran (2.2 mL). The mixture was stirred for 1 hour. After diluting the reaction with water (30 mL) and acidifying with 1N hydrochloric acid, the resulting precipitate was filtered, washed with water and chlorobutane/hexane, and air dried to give 0.58 g of the title compound as a white solid, m.p. 151-159° C. with decomposition. Another sample previously prepared by this method melted at 150-160° C. with decomposition. 
     300 MHz NMR (DMSO): δ6 3.04 (s, 3H, CH 3 ); 3.46 (s, 6H, NCH 3 ); 4.10 (s, 3H, OCH 3 ); 5.32 (m, 2H, CH 2 ); 7.78 (d, 1H, arom.); 7.84 (d, 1H, arom.); 7.98 (m, 1H, arom.); 11.1 (s, 1H, NH); and 13.1 (s, 1H, NH). 
     IR (nujol) 1730 cm -1 . 
     The following compounds may be prepared by one skilled in the art using the general methods described earlier and exemplified in Examples 1 to 6. 
     
                       TABLE 1______________________________________ ##STR14##                     IR.sub.1       R               X______________________________________CH.sub.3      CH.sub.3        NHCH.sub.3CH.sub.3      CH.sub.3        N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH(CH.sub.3).sub.2                         NHCH.sub.3CH.sub.3      CH(CH.sub.3).sub.2                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH(CH.sub.3).sub.2                         NHCH.sub.3CH.sub.3      CH.sub.2 CH(CH.sub.3).sub.2                         N(CH.sub.3).sub.2CH.sub.3      CH(CH.sub.3)CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.3      CH(CH.sub.3)CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CHCH.sub.2                         NHCH.sub.3CH.sub.3      CH.sub.2 CHCH.sub.2                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CCH    NHCH.sub.3CH.sub.3      CH.sub.2 CCH    N(CH.sub.3).sub.2CH.sub.3          ##STR15##      NHCH.sub.3CH.sub.3          ##STR16##      N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.3                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 CN                         NHCH.sub.3CH.sub.3      CH.sub.2 CH.sub.2 CN                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub. 2 Cl                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 F                         N(CH.sub.3).sub.2CH.sub.3      CH.sub.2 CH.sub.2 Br                         N(CH.sub.3).sub.2CH.sub.2 CH.sub.3         CH.sub.3        N(CH.sub.3).sub.2CH.sub.2 CH.sub.3         CH.sub.3        NHCH.sub.3CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.2 CH.sub.3         CH(CH.sub.3).sub.2                         N(CH.sub.3).sub.2CH.sub.2 CH.sub.3         CH.sub.2 CHCH.sub.2                         N(CH.sub.3).sub.2CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 Cl                         N(CH.sub.3).sub.2CF.sub.3      CH.sub.3        N(CH.sub.3).sub.2CF.sub.3      CH.sub.3        NHCH.sub.3CF.sub.3      CH.sub.2 CH.sub.3                         NHCH.sub.3CF.sub.3      CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CF.sub.3          ##STR17##      N(CH.sub.3).sub.2CF.sub.3          ##STR18##      NHCH.sub.3CF.sub.3      CH.sub.2 CN     NHCH.sub.3CH.sub.2 CH.sub.2 Cl         CH.sub.3        NHCH.sub.3CH.sub.2 CH.sub.2 Cl         CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CH.sub.2 Cl         CH.sub.2 CH.sub. 2 CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CN   CH.sub.3        NHCH.sub.3CH.sub.2 CN   CH.sub.3        N(CH.sub.3).sub.2CH.sub.2 CN   CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.2 CN   CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CN   CH.sub.2 CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CN   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 CN   CH.sub.2 CHCH.sub.2                         NHCH.sub.3CH.sub.2 CN   CH.sub.2 CHCH.sub.2                         N(CH.sub.3).sub.2CH.sub.2 CN   CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.2 CN   CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 OCH.sub.3         CH.sub.2 CH.sub.3                         NHCH.sub.3CH.sub.2 OCH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2CH.sub.2 OCH.sub.3         CH(CH.sub.3).sub.2                         N(CH.sub.3).sub.2CH.sub.2 OCH.sub.3         CH(CH.sub.3).sub.2                         NHCH.sub.3CH.sub.2 OCH.sub.3          ##STR19##      NHCH.sub.3CH.sub.2 OCH.sub.3          ##STR20##      N(CH.sub.3).sub.2OCH.sub.3     CH.sub.3        N(CH.sub.3).sub.2OCH.sub.3     CH.sub.3        NHCH.sub.3OCH.sub.3     CH.sub.2 CH.sub.3                         NHCH.sub.3OCH.sub.3     CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH.sub.3     CH(CH.sub.3).sub.2                         N(CH.sub.3).sub.2OCH.sub.3     CH(CH.sub.3).sub.2                         NHCH.sub.3OCH.sub.3     CH.sub.2 CHCH.sub.2                         NHCH.sub.3OCH.sub.3     CH.sub.2 CHCH.sub.2                         N(CH.sub.3).sub.2OCH.sub.3          ##STR21##      N(CH.sub.3).sub.2OCH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH.sub.3     CH.sub.2 CH.sub.2 SCH.sub.3                         N(CH.sub.3).sub.2OCH.sub.3     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH.sub.3     CH.sub.2 CH.sub.2 CN                         N(CH.sub.3).sub.2OCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         NHCH.sub.3OCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 OCH.sub.3                         NHCH.sub.3OCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 Br                         NHCH.sub.3OCH.sub.2 CH.sub.2 CH.sub.3         CH.sub.3        N(CH.sub.3).sub.2OCH.sub.2 CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH(CH.sub. 3).sub.2         CH.sub.3        N(CH.sub.3).sub.2OCH(CH.sub.3).sub.2         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2OCH(CH.sub.3).sub.2         CH.sub.2 CH.sub.2 OCH.sub.3                         N(CH.sub.3).sub.2SCH.sub.3     CH.sub.3        NHCH.sub.3SCH.sub.3     CH.sub.3        N(CH.sub.3).sub.2SCH.sub.3     CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2SCH.sub.3     CH.sub.2 CH.sub.3                         NHCH.sub.3SCH.sub.3     CH.sub.2 CH.sub.2 CH.sub.3                         NHCH.sub.3SCH.sub.3     CH.sub.2 CCH    NHCH.sub.3SCH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.3                         NHCH.sub.3SCH.sub.2 CH.sub.3         CH.sub.3        NHCH.sub.3SCH.sub.2 CH.sub.3         CH.sub.3        N(CH.sub.3).sub.2SCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2SCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         NHCH.sub.3SCH.sub.2 CH.sub.3          ##STR22##      NHCH.sub.3SCH.sub.2 CH.sub.3          ##STR23##      NH(CH.sub.3).sub.2SCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 SCH.sub.3                         N(CH.sub.3).sub.2SCH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 OCH.sub.3                         N(CH.sub. 3).sub.2SCH.sub.2 CH.sub.2 CH.sub.3         CH.sub.3        N(CH.sub.3).sub.2SCH.sub.2 CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2SCH.sub.2 CH.sub.2 CH.sub.3         CH.sub.2 CH.sub.2 Br                         N(CH.sub.3).sub.2SCH(CH.sub.3).sub.2         CH.sub.3        N(CH.sub.3).sub.2SCH(CH.sub.3).sub.2         CH.sub.2 CH.sub.2 OCH.sub.3                         N(CH.sub.3).sub.2SCH(CH.sub.3).sub.2          ##STR24##      N(CH.sub.3).sub.2SC.sub.6 H.sub.5         CH.sub.3        NHCH.sub.3SC.sub.6 H.sub.5         CH.sub.3        N(CH.sub.3).sub.2SC.sub.6 H.sub.5         CH.sub.2 CH.sub.3                         NHCH.sub.3SC.sub.6 H.sub.5         CH.sub.2 CH.sub.3                         N(CH.sub.3).sub.2______________________________________ 
    
     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: 
     
         ______________________________________       Active  Weight Percent*       Ingredient               Diluent(s)                         Surfactant(s)______________________________________Wettable Powders         20-90      0-74     1-10Oil Suspensions,          3-50     40-95     0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension         10-50     40-84     1-20Dusts          1-25     70-99     0-5Granules and Pellets         0.1-95      5-99.9  0-15High Strength 90-99      0-10     0-2Compositions______________________________________ *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 sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. 
     Typical solid diluents are described in Watkins, et al., &#34;Handbook of Insecticide Dust Diluents and Carriers&#34; , 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, 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, &#34;Solvents Guide,&#34; 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. &#34;McCutcheon&#39;s Detergents and Emulsifiers Annual&#34;, MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, &#34;Encyclopedia of Surface Active Agents&#34;, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. 
     The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 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, &#34;Agglomeration&#34;, Chemical Engineering, Dec. 4, 1967, pp. 147ff. and &#34;Perry&#39;s Chemical Engineer&#39;s Handbook&#34;, 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. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; 
     R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 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. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; 
     G. C. Klingman, &#34;Weed Control as a Science&#34;, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and 
     J. D. Fryer and S. A. Evans, &#34;Weed Control Handbook&#34;, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. 
     In the following Examples, all parts are by weight unless otherwise indicated. 
     EXAMPLE 7 
     Wettable Powder 
     
         ______________________________________Wettable Powder______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       80%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatesodium 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, reblended, and packaged. 
     EXAMPLE 8 
     
         ______________________________________Wettable Powder______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       50%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatesodium alkylnaphthalenesulfonate                       2%low viscosity methyl cellulose                       2%diatomaceous earth          46%______________________________________ 
    
     The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. 
     EXAMPLE 9 
     
         ______________________________________Granule______________________________________Wettable Powder of Example 8                      5%attapulgite granules       95%(U.S.S. 20 to 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 10 
     
         ______________________________________Extruded Pellet______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       25%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoateanhydrous 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 11 
     
         ______________________________________Low Strength Granule______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                      0.1%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoateattapulgite granules       99.9%(U.S.S. 20 to 40 mesh, 0.42 to 0.84 mm)______________________________________ 
    
     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 12 
     
         ______________________________________Granule______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       80%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatewetting agent               1%crude ligninsulfonate salt (containing                       10%5 to 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 fluidization 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 to 100 mesh (1410 to 149 microns), and packaged for use. 
     EXAMPLE 13 
     
         ______________________________________Low Strength Granule______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       1%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoateN,N-dimethylformamide       9%attapulgite granules        90%(U.S.S. 20 to 40 sieve, 0.42 to 0.84 mm)______________________________________ 
    
     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 14 
     
         ______________________________________Aqueous Suspension______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       40%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatepolyacrylic 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 15 
     
         ______________________________________Solution______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       5%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, sodium saltwater                       95%______________________________________ 
    
     The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. 
     EXAMPLE 16 
     
         ______________________________________High Strength Concentrate______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       99%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatesilica 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 17 
     
         ______________________________________Wettable Powder______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       90%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatedioctyl 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 18 
     
         ______________________________________Wettable Powder______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       40%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatesodium 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 19 
     
         ______________________________________Oil Suspension______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       35%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoateblend of polyalcohol carboxylic                       6%esters and oil soluble petroleum sulfonatesxylene                      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 20 
     
         ______________________________________Dust______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       10%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoateattapulgite                 10%Pyrophyllite                80%______________________________________ 
    
     The active ingredient is blended with attapulgite 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 21 
     
         ______________________________________Oil Suspension______________________________________Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       25%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatePolyoxyethylene 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 22 
     
         ______________________________________Wettable Powder______________________________________Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                       20%ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoatesodium 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 essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. 
     Utility 
     The compounds of this invention are particularly useful for the control of undesired vegetation in sugar beets, fodder beets, and red beets. These are crops that take long time periods to become established. In this interval, the crop seedlings must be nurtured carefully, with particular attention to weed control to prevent damage and yield loss due to competition. The subject compounds can be used either pre- or post-emergence and will control numerous problem weeds including catchweed bedstraw (Galium aparine) wild buckwheat (Polygonum convolvulus), wild mustard (Sinapsis arvensis) and bIackgrass (Alopercurus mysoroides). 
     The rate of application for these compounds is determined by a number of factors including the weeds to be controlled, weather and climate, soil type, time of application, age and size of crop and weeds, method of application, etc. In general terms, the rate will vary between about 0.5 and 1000 g/ha, with preferred rates of about 10 to 125 g/ha. The rate to be used in any given situation can be selected by one with ordinary skill in the art. 
     These compounds can and will often be used in mixtures with one or more other herbicides. They may be mixed with other herbicides selective on beet crops, including metamitron, phenmedipham, desmedipham, chloridazon, lenacil, ethofumesate, cycloate, clopyralid, diallate, triallate, diclofop-methyl, quizalofop-ethyl, fuzalifop-butyl, haloxafop, sethoxidym and alloxidym. 
     The selective properties of these compounds were discovered in greenhouse tests. The results of these tests clearly show the activity and selectivity of these compounds and are shown in the tables below. 
     
         ______________________________________COMPOUNDS ##STR25##CMPD   R.sub.1 R             X       m.p. (°C.)______________________________________1      CH.sub.3          CH.sub.2 CH.sub.3                        N(CH.sub.3).sub.2                                134-1422      CH.sub.3          CH.sub.3      NHCH.sub.3                                123-129(d)3      CH.sub.3          CH.sub.3      N(CH.sub.3).sub.2                                150-160(d)4      CH.sub.3          (CH.sub.2).sub.2 CH.sub.3                        N(CH.sub.3).sub.2                                143-150(d)5      CH.sub.3          (CH.sub.2).sub.2 CH.sub.3                        NHCH.sub.3                                159-1636      CH.sub.3          CH(CH.sub.3).sub.2                        NHCH.sub.3                                185-1867      CH.sub.3          CH(CH.sub.3).sub.2                        N(CH.sub.3).sub.2                                155-1568      CH.sub.3          CH.sub.2 -cyclo-C.sub.3 H.sub.5                        N(CH.sub.3).sub.2                                105-115(d)9      CH.sub.3          CH.sub.2 CH.sub.3                        NHCH.sub.3                                149- 15210     CH.sub.3          C(CH.sub.3).sub.3                        NHCH.sub.3                                181-18311     CH.sub.3          C(CH.sub.3).sub.3                        N(CH.sub.3).sub.2                                 82-89______________________________________ 
    
     TEST A 
     Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), cheatgrass (Bromus secalinus) or downy brome (Bromus tectorum), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoea spp.), rice (Oryz sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated Plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually evaluated. The ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (--) response means no test. The accompanying descriptive symbols have the following meanings: 
     C=chlorosis/necrosis; 
     G=growth retardation; and 
     H=formative effect. 
     
                                           TABLE A__________________________________________________________________________POSTEMERGENCE   Cmpd 1   2        3        4       5RATE (g/ha)   50   10  50   10  50   10  50  10  50  10__________________________________________________________________________Barley   3C, 9G        8G   3C, 9G                 3C, 9G                      2C, 9G                          3C, 9G                              8G  4G  9G  7GBarnyardgrass    9C  3C, 9H             9C  3C, 9G                      9C  4C, 9H                              3C, 7H                                  3C, 6G                                      3C, 7G                                          3C, 5GCheatgrass   --   --   2C, 9G                 3C, 8G                      5C, 9G                          4C, 9G                              4G  0   3C, 9G                                          0Cocklebur   10C  3C, 9H             9C  3C, 7H                     10C  4C, 9G                              4C, 9G                                  2C, 7G                                      3C, 8G                                          2C, 7GCorn     3C, 9G        3C, 9G             3C, 9G                 3C, 9H                      9G  3C, 9H                              3C, 7H                                  3G  3C, 5G                                          4GCotton   9G  3C, 6G             5C, 9G                 4C, 9H                      4C, 9G                          4C, 9H                              3C, 8H                                  8H  4C, 9H                                          3C, 8HCrabgrass    0   0    3C, 7G                 3G   3C, 8G                          2C, 4G                              0   0   2G  0Downy brome    5C, 9G        3C, 9G            --   --  --   --  --  --  --  --Giant foxtail    3C, 7G        2G   3C, 9G                 3C, 7G                      3C, 9G                          3C, 6G                              2G  0   5G  2GMorningglory   10C  4C, 9H             9C  5C, 9G                      9C  4C, 8H                              5C, 9G                                  4C, 8H                                      5C, 9G                                          3C, 8HNutsedge    5G  --   2C, 9G                 --   9C  9C  0   0   --  0Rice     9C  5C, 9G             9C  9C   5C, 9G                          5C, 9G                              3C, 7G                                  2G  3C, 7G                                          5GSorghum  4C, 9G        9H   5C, 9G                 5C, 9G                      5C, 9G                          4C, 9G                              2C, 3G                                  2G  2C, 5G                                          2GSoybean  4C, 9G        4C, 9G             9C  4C, 9G                      4C, 9G                          4C, 9G                              3C, 8H                                  3C, 4G                                      4C, 9G                                          4C, 8HSugar beet    0   0    2G  0    4G  0   0   0   3G  0Velvetleaf    9C  4C, 8H            10C  3C, 8G                     10C  4C, 9G                              2C, 8H                                  2G  8G  2C, 6GWheat    4C, 9G        7G   9G  9G   3C, 9G                          9G  3G  0   4G  2GWild oat    4C, 9G        3C, 6G             3C, 8G                 3C, 5G                      3C, 8G                          3C, 5G                              3G  0   3C, 4G                                          1C__________________________________________________________________________POSTEMERGENCE              6       7       8       9      RATE (g/ha)              50  10  50  10  50  10  50  10__________________________________________________________________________      Barley  4C, 9G                  3C, 8H                      9G  7G  4G  0   9G  8G      Barnyardgrass              3C, 9H                  3C, 7H                      3C, 8H                          2C, 6H                              2C, 4G                                  0   9G  3C, 7H      Cheatgrass              7G  6G  7G  4G  0   0   9G  3G      Cocklebur              3C, 8H                  3C, 8H                      5C, 9G                          3C, 8G                              3C, 4G                                  1C, 2G                                      4C, 9G                                          4C, 7G      Corn    3C, 8H                  3C, 8G                      3C, 9G                          2C, 7G                              2C, 4G                                  0   3C, 9H                                          3C, 6G      Cotton  4C, 9G                  9H  3C, 9G                          3G  1C, 3G                                  0   4C, 8G                                          3C, 7G      Crabgrass              3G  0   0   0   0   0   6G  3G      Downy brome              --  --  --  --  --  --  --  --      Giant foxtail              3G  0   2G  0   0   0   7G  3G      Morningglory              4C, 9G                  3C, 8H                      3C, 9G                          3C, 8G                              3C, 6G                                  2C  9C  4C, 8G      Nutsedge              --  --  --  --  0   0   9G  4G      Rice    4C, 8G                  3C, 7G                      3C, 8G                          2C, 3G                              2C, 2G                                  0   5C, 9G                                          5C, 9G      Sorghum 4C, 9G                  4C, 9G                      3C, 8H                          3C, 8G                              6G  0   9G  9G      Soybean 5C, 9H                  4C, 8G                      4C, 9G                          4C, 8G                              3C, 4G                                  0   5C, 9G                                          5C, 9G      Sugar beet              1H  0   0   0   0   0   0   0      velvetleaf              2C, 8H                  2C, 5G                      3C, 8H                          0   0   0   9C  4C, 9G      Wheat   8G  6G  8G  7G  3G  0   9G  9G      Wild oat              9G  3C, 7G                      2C, 6G                          2C, 5G                              0   0   3C, 9G                                          7G__________________________________________________________________________PREEMERGENCE   Cmpd 1 2       3       4    5      6RATE (g/ha)   50  10 50  10  50  10  50 10                               50  10 50  10__________________________________________________________________________Barley  9G  0  3C, 8G              3C, 8G                  9G  4G  2G 0 8G  3G 8G  2GBarnyardgrass   2G  0  3C, 8H              7H  3C, 8H                      1H  3G 0 6G  0  3C, 7H                                          3GCheatgrass   --  -- 8G  4G  3C, 8H                      0   0  0 6G  0  3C, 7G                                          5GCocklebur   3C, 4H       0  4G  0   2C, 2H                      0   3G 0 8G  2H 3C, 5H                                          3GCorn    3C, 7G       2G 4C, 9H              3C, 3G                  4C, 9H                      4G  3G 0 3C, 7G                                   3G 3C, 8G                                          3C, 7GCotton  0   0  0   2G  2G  0   5G 0 2G  0  3G  0Crabgrass   0   0  3C, 5G              2G  3C, 6G                      4G  0  0 2G  0  3C, 7G                                          2GDowny brome   5G  0  --  --  --  --  -- --                               --  -- --  --Giant foxtail   2G  0  3C, 7H              5G  2C, 3G                      0   0  0 2G  0  2C, 7G                                          2GMorningglory   3C, 3H       0  4C, 9G              5G  3C, 4H                      0   2G 0 7G  3G 9H  3GNutsedge   0   0  3C, 3G              0   4G  0   7G 0 0   0  9G  0Rice    3C, 5G       0  5C, 9H              4G  7G  4G  2G 0 7G  2G 4G  0Sorghum 3C, 7G       0  4C, 9H              3C, 7G                  4C, 9H                      2C, 5G                          3G 0 3C, 7G                                   2G 3C, 8H                                          3C, 5GSoybean 2C, 2H       1C 4C, 6H              3C, 3G                  3H  2G  3G 0 3C, 5G                                   3G 3C, 6H                                          2HSugar beet   0   0  4G  0   0   0   2G 0 0   0  0   0Velvetleaf   2H  0  4H  0   5H  0   3G 0 6G  0  6H  2GWheat   4G  0  2C, 8G              3G  8G  0   0  0 4G  0  2C, 3G                                          0Wild oat   2C, 5G       0  2G  0   2G  0   0  0 5G  0  6G  3G__________________________________________________________________________PREEMERGENCE                        7       8     9                RATE (g/ha)                        50  10  50 10 50  10__________________________________________________________________________                Barley  2C, 5G                            0   0  0  8G  8G                Barnyardgrass                        3C, 7G                            0   0  0  3C, 7H                                          2G                Cheatgrass                        6G  0   0  0  6G  0                Cocklebur                        7H  0   0  0  3C, 7H                                          0                Corn    3C, 8G                            2C, 4G                                0  0  3C, 9G                                          3C, 4G                Cotton  2G  0   0  0  0   0                Crabgrass                        5G  0   0  0  0   0                Downy brome                        --  --  -- -- --  --                Giant foxtail                        4G  0   2G 0  5G  2G                Morningglory                        8H  0   0  0  9G  3C, 4G                Nutsedge                        0   0   0  0  0   0                Rice    4G  0   0  0  2C, 5G                                          2G                Sorghum 3C, 8G                            2C, 2G                                0  0  4C, 9G                                          2C, 4H                Soybean 2C, 4H                            2C, 2G                                0  0  4C, 8H                                          2G                Sugar beet                        0   0   0  0  0   0                Velvetleaf                        7H  0   2H 0  6H  3H                Wheat   2G  0   0  0  8G  2G                Wild oat                        6G  0   0  0  7G  2G__________________________________________________________________________ 
    
     TEST B 
     Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setaria faberi), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea spp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassia obtusifolia), soybean (Glycine max), sugar beet (Beta vulgaris), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Titicum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. The ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (--) response means no test. 
     
                                           TABLE B__________________________________________________________________________POSTEMERGENCE    Cmpd 1     2          3           4       5RATE (g/ha)    250       62 16 4 250                  62 16 4 250                             62 16 4  62                                        16                                          4 1 250                                                 62 16 4__________________________________________________________________________Barley   100       80 60 30               90 90 80 30                          90 90 60 40 60                                        30                                          0 0 70 60     50                                                 30Barnyardgrass    100       90 80 30               100                  90 60 40                          100                             100                                70 30 50                                        30                                          0 0 80 50     30                                                 0Blackgrass    100       100          30 0 95 95 60 50                          100                             90 90 60 60                                        30                                          0 0 90 80     70                                                 30Chickweed    100       90 70 40               80 30 0  0 80 70 20 0  30                                        0 0 0 50 30     0                                                 0Cocklebur    100       90 70 0 80 30 0  0 70 40 20 0  60                                        30                                          0 0 50 40     30                                                 0Corn     100       100          90 70               100                  100                     80 60                          100                             100                                60 50 30                                        0 0 0 0  0      0                                                 0Cotton   80 70 20 10               90 90 80 50                          90 90 80 70 30                                        0 0 0 50 30     0                                                 0Crabgrass    90 20 0  0 70 30 20 0 60 40 20 0  0 0 0 0 40 30     20                                                 0Downy brome    100       100          100             60               95 95 90 40                          95 95 70 50 60                                        30                                          0 0 70 50     30                                                 0Giant foxtail    70 40 0  0 100                  40 20 0 90 70 0  0  0 0 0 0 50 30     0                                                 0Green foxtail    40 10 0  0 90 60 40 20                          50 40 0  0  0 0 0 0 40 20     0                                                 0Jimsonweed    100       100          90 70               100                  90 70 50                          100                             90 90 80 70                                        50                                          30                                            0 50 40     30                                                 20Johnsongrass    -- 100          80 40               100                  90 60 40                          100                             90 40 30 60                                        30                                          0 0 70 50     40                                                 30Lambsquarters    100       80 30 --               50 30 0  0 90 0  0  0  70                                        60                                          50                                            40                                              90 70     50                                                 0Morningglory    100       90 80 50               100                  100                     100                        0 100                             100                                90 80 90                                        50                                          30                                            0 80 50     30                                                 0Nutsedge 100       100          90 40               100                  100                     100                        0 100                             100                                100                                   100                                      50                                        30                                          0 0 90 30     0                                                 0Rape     100       100          100             80               90 90 30 0 100                             100                                80 50 90                                        70                                          50                                            30                                              100                                                 100    100                                                 100Rice     100       100          80 50               100                  100                     100                        90                          100                             100                                100                                   70 30                                        0 0 0 60 40     30                                                 0Sicklepod    100       100          90 80               100                  90 90 0 100                             100                                90 70 0 0 0 0 30 0      0                                                 0Soybean  90 90 80 80               90 90 90 70                          90 90 80 50 90                                        60                                          30                                            0 90 70     60                                                 50Sugar beet    20 0  0  0 70 0  0  0 40 0  0  0  0 0 0 0 30 0      0                                                 0Teaweed  90 80 70 50               80 30 0  0 70 50 20 0  40                                        30                                          20                                            0 50 30     0                                                 0Velvetleaf    100       100          80 80               90 90 70 50                          100                             100                                100                                   90 60                                        30                                          0 0 90 70     50                                                 40Wheat    90 70 70 40               90 90 80 40                          90 90 60 30 40                                        0 0 0 40 30     0                                                 0Wild buckwheat    100       80 70 20               80 80 20 0 100                             50 0  0  0 0 0 0 60 0      0                                                 0Wild oat 100       60 60 30               95 60 40 0 95 80 40 20 30                                        0 0 0 70 60     30                                                 0__________________________________________________________________________                         6          7          9                RATE (g/ha)                         250                            62 16 4 250                                       62 16 4 250                                                  62 16 4__________________________________________________________________________                Barley   70 60 50 40                                    90 70 60 50                                               80 60 60 60                Barnyardgrass                         50 40 30 20                                    80 70 60 30                                               80 75 70 50                Blackgrass                         100                            100                               90 70                                    90 80 70 30                                               90 80 70 40                Chickweed                         70 60 50 30                                    90 80 50 30                                               80 70 50 30                Cocklebur                         75 70 60 50                                    100                                       90 80 70                                               90 80 60 30                Corn     70 60 50 40                                    75 70 60 50                                               90 80 70 50                Cotton   70 60 40 30                                    80 70 60 50                                               70 60 50 40                Crabgrass                         60 50 40 30                                    50 30 0  0 40 30 0  0                Downy brome                         80 70 60 40                                    90 70 60 50                                               90 80 70 60                Giant foxtail                         30 30 20 20                                    60 30 0  0 60 50 30 0                Green foxtail                         50 40 30 20                                    60 30 0  0 80 70 50 40                Jimsonweed                         90 85 80 70                                    100                                       100                                          90 80                                               100                                                  100                                                     90 70                Johnsongrass                         90 80 70 60                                    90 80 70 50                                               90 80 70 60                Lambsquarters                         90 80 70 60                                    90 80 70 60                                               40 30 0  0                Morningglory                         85 80 75 70                                    100                                       100                                          100                                             90                                               100                                                  100                                                     90 80                Nutsedge 70 60 50 30                                    90 80 70 60                                               100                                                  90 60 30                Rape     100                            100                               100                                  70                                    100                                       100                                          90 70                                               100                                                  100                                                     100                                                        90                Rice     80 70 60 50                                    80 70 60 50                                               70 70 70 70                Sicklepod                         80 70 60 50                                    95 90 80 70                                               100                                                  80 70 60                Soybean  90 85 80 70                                    100                                       90 80 70                                               100                                                  100                                                     90 60                Sugar beet                         20 0  0  0 20 0  0  0 0  0  0  0                Teaweed  70 60 50 30                                    70 60 50 40                                               80 70 60 50                Velvetleaf                         95 90 80 70                                    95 90 80 70                                               100                                                  100                                                     90 70                Wheat    60 50 30 0 100                                       70 50 30                                               60 50 50 50                Wild buckwheat                         100                            100                               90 70                                    90 80 70 60                                               -- -- -- --                Wild oat 80 75 70 60                                    90 70 50 0 70 60 50 40__________________________________________________________________________PREEMERGENCE    Cmpd 1   2           3           4        5RATE (g/ha)    250       62 16 250                62 16 4  250                            62 16 4  250                                        62 16 250                                                 62 16 4__________________________________________________________________________Barley   90 80 40 70 60 20 0  80 70 40 0  30 0  0  70 50 0  0Barnyardgrass    100       100          60 100                70 20 0  70 20 0  0  90 60 30 90 70 50 0Blackgrass    80 -- 40 80 50 30 0  70 70 40 30 80 50 0  90 60 30 0Chickweed    90 80 50 30 20 0  0  70 70 30 30 60 30 0  70 50 30 0Cocklebur    90 80 30 90 30 0  0  60 40 30 0  80 30 0  70 50 30 0Corn     100       90 70 100                70 70 20 100                            100                               30 0  60 20 0  80 60 0  0Cotton   30 20 0  80 20 0  0  0  0  0  0  0  0  0  0  0  0  0Crabgrass    50 50 30 50 30 30 0  90 80 70 0  80 50 30 100                                                 80 30 0Downy brome    90 80 40 100                70 20 0  100                            40 20 0  70 30 0  70 50 0  0Giant foxtail    90 70 40 90 50 20 0  70 30 0  0  60 30 0  90 80 50 30Green foxtail    100       80 60 90 90 70 20 70 30 0  0  80 30 0  90 70 50 0Jimsonweed    100       50 30 90 50 20 0  70 40 30 0  70 30 0  70 50 30 0Johnsongrass    100       100          90 90 80 20 0  90 80 40 0  60 30 0  80 60 30 0Lambsquarters    100       60 20 80 70 70 0  80 70 50 0  90 60 30 90 80 70 60Morningglory    100       80 40 100                60 20 0  70 70 0  0  60 30 0  90 60 50 30Nutsedge 100       70 20 30 20 0  0  40 -- 20 0  50 30 0  90 70 0  0Rape     100       90 50 100                50 0  0  100                            70 20 0  70 50 30 90 70 30 0Rice     100       80 30 70 30 20 0  90 60 20 0  40 0  0  40 20 0  0Sicklepod    100       60 50 30 20 0  0  40 20 0  0  30 0  0  70 50 30 0Soybean  90 50 30 100                20 0  0  30 0  0  0  20 0  0  60 30 0  0Sugar beet    70 30 0  70 20 0  0  40 20 0  0  30 0  0  30 0  0  0Teaweed  80 60 30 50 40 20 0  100                            100                               30 0  70 50 30 70 60 50 30Velvetleaf    90 80 70 80 20 -- -- 80 80 0  0  90 50 0  70 30 0  0Wheat    90 70 40 80 50 20 0  70 40 20 0  40 0  0  60 30 0  0Wild buckwheat    90 60 20 90 80 80 20 90 80 80 80 0  0  0  0  0  0  0Wild oat 60 60 20 60 20 0  0  80 50 30 0  40 0  0  40 30 0  0__________________________________________________________________________                            6         7         9                   RATE (g/ha)                            250                               62 16                                    4 250                                         62 16                                              4 250                                                   62 16                                                        4__________________________________________________________________________                   Barley   90 80 70                                    30                                      70 60 30                                              0 90 70 50                                                        30                   Barnyardgrass                            100                               90 50                                    30                                      90 80 50                                              30                                                100                                                   90 80                                                        30                   Blackgrass                            100                               100                                  90                                    70                                      90 80 70                                              30                                                100                                                   100                                                      90                                                        50                   Chickweed                            100                               100                                  90                                    70                                      100                                         100                                            90                                              70                                                70 50 30                                                        0                   Cocklebur                            90 70 50                                    30                                      70 60 50                                              0 90 70 40                                                        0                   Corn     100                               80 70                                    20                                      90 60 30                                              0 90 80 70                                                        30                   Cotton   60 0  0 0 30 20 0 0 50 40 0 0                   Crabgrass                            80 50 30                                    0 80 50 30                                              0 80 30 0 0                   Downy brome                            100                               100                                  80                                    50                                      100                                         80 50                                              0 100                                                   90 70                                                        60                   Giant foxtail                            80 50 30                                    0 60 30 0 0 90 70 30                                                        0                   Green foxtail                            80 50 30                                    0 70 30 0 0 90 70 50                                                        30                   Jimsonweed                            90 80 70                                    60                                      90 70 50                                              30                                                90 70 50                                                        30                   Johnsongrass                            90 80 70                                    50                                      80 70 30                                              0 95 90 80                                                        50                   Lambsquarters                            100                               100                                  90                                    80                                      100                                         100                                            50                                              30                                                90 70 50                                                        0                   Morningglory                            90 80 70                                    60                                      90 70 50                                              30                                                90 80 70                                                        50                   Nutsedge 90 60 30                                    0 70 50 30                                              0 100                                                   50 0 0                   Rape     100                               100                                  90                                    70                                      100                                         100                                            70                                              30                                                100                                                   100                                                      90                                                        70                   Rice     100                               100                                  80                                    30                                      80 60 30                                              0 100                                                   80 50                                                        30                   Sicklepod                            90 70 60                                    50                                      70 60 0 0 80 70 40                                                        0                   Soybean  80 40 0 0 70 30 0 0 70 60 40                                                        0                   Sugar beet                            90 70 60                                    50                                      50 40 30                                              0 50 30 0 0                   Teaweed  90 80 --                                    50                                      90 70 40                                              30                                                80 70 50                                                        0                   Velvetleaf                            90 70 50                                    30                                      80 70 50                                              0 100                                                   100                                                      95                                                        90                   Wheat    90 60 30                                    0 80 30 0 0 100                                                   70 50                                                        30                   Wild buckwheat                            95 90 85                                    80                                      100                                         70 60                                              50                                                -- -- --                                                        --                   Wild oat 80 50 30                                    0 70 50 30                                              0 70 60 50                                                        30__________________________________________________________________________ 
    
     TEST C 
     Seeds selected from crop and weed species consisting of annual bluegrass (Poa annua), barley (Hordeum vulgare), black nightshade (Solanum nigrum), blackgrass (Alopecurues myosuroides), catchweed bedstraw (Galium aparine), chickweed (Stellaria media), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), knotweed (polygonum aviculare), kochia (Kochia scoparia), lambsquarters (Chenopodium album), pigweed (Amaranthus retroflexus), rape (Brassica napus), scentless chamomile (Matricaria inodora), smartweed (Polygonum persicaria), speedwell (Veronica persica), sugar beet (Beta vulgaris), viola (Viola arvensis), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica spp.), wild oat (Avena fatua) and wild radish (Raphanus raphanistrum) were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. Selected species from this list of crops and weeds were also treated with postemergence applications of test chemicals. Plants ranged in height from two to twenty cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. The ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (--) response means no test. 
     
                                           TABLE C__________________________________________________________________________POSTEMERGENCE      Cmpd 1      2              3              4RATE (g/ha)      64 32 16 8  250                     125                        64 32 16 250                                    125                                       64 32 16 64 32 16                                                        8__________________________________________________________________________Annual bluegrass      70 70 30 0  100                     80 80 40 0  100                                    60 60 20 20Barley     85 70 75 50 100                     100                        80 80 70 80 80 80 70 50Black nightshade      100         100            100               75Blackgrass 100         100            80 50 100                     100                        100                           100                              0  100                                    100                                       80 30 20 50 50 30                                                        0Catchweed bedstraw      100         90 75 0                                20 20 0 0Chickweed  85 60 40 20 20 20 0  0  0  90 50 20 20 0  30 20 0 0Green foxtail      50 0  0  0  80 80 40 40 40 90 80 40 40 20Italian ryegrass      100         50 50 0Knotweed                                             -- 20 0 0Kochia     90 100            50 20Lambsquarters      0  0  0  0  100                     60 60 60 30 100                                    30 0  0  0  20 0  --                                                        --Pigweed    40 40 30 0  100                     100                        80 60 60 100                                    100                                       40 20Rape       90 90 75 60Scentless chamomile      100         100            90 30                               70 50 50                                                        50Smartweed              100                     100                        90 90 90 100                                    100                                       100                                          90 90Speedwell  100         90 50 30                               80 50 30                                                        30Sugar beet 0  0  0  0  50 30 0  0  0  20 0  0  0  0  20 0  0 0Viola                                                0  0  0 0Wheat      75 75 50 50                               40 40 30                                                        30Wild buckwheat      100         80 60 40 100                     100                        100                           100                              80 100                                    95 100                                          90 90 40 30 20                                                        0Wild mustard      100         100            100               100                  100                     100                        100                           100                              100                                 100                                    100                                       100                                          100                                             100Wild oat   70 70 50 30 90 80 70 60 50 50 50 0  0  0  50 40 40                                                        40Wild radish      100         100            100               100__________________________________________________________________________POSTEMERGENCE      5           6          7           8 9RATE (g/ha)      125         64 32 16 125                     64 32                          16 125                                64 32 16                                        125                                           125                                              64 32 16 8__________________________________________________________________________Blackgrass 50 50 50 20 100                     80 80                          50 90 90 50 50                                        50 100                                              100                                                 100                                                    100                                                       100Catchweed bedstraw      70 70 70 30 90 60 60                          30 80 80 80 50                                        60 100                                              90 90 90 70Chickweed  0  0  0  0  0  0  0 0  80 50 20 0 30 80 30 30 0  0Knotweed   -- 50 50 0  -- 50 --                          50               90 90 90 70 70Lambsquarters      -- -- -- 0                        0Scentless chamomile      50 30 20 20 100                     80 80                          80 100                                100                                   100                                      80                                        85 100                                              100                                                 100                                                    70 50Speedwell  80 60 50 50 100                     80 80                          30 100                                100                                   50 50                                        80 100                                              100                                                 100                                                    80 80Sugar beet 15 0  0  0  20 0  0 0  0  0  0  0 30 15 0  0  0  0Viola      30 30 0  0  70 70 70                          20 100                                100                                   50 30                                        60 100                                              100                                                 80 50 30Wheat      50 30 30 30 80 80 70                          50 80 80 70 50                                        70 100                                              60 50 50 50Wild buckwheat      50 50 20 20 100                     100                        80                          70 100                                90 80 80                                        70 100                                              90 80 70 60Wild oat   70 50 50 50 100                     70 70                          70 80 80 50 50   100                                              90 80 80 80__________________________________________________________________________PREEMERGENCE      Cmpd 1 2    3   4 5    6        7        8 9RATE (g/ha)      64 32 64 32                 64                   32                     64 125                           64                             125                                64 32 125                                         64                                           32 125                                                 125                                                    64 32__________________________________________________________________________Annual bluegrass      75 30 20 0 20                   0Barley     70 40 70 30                 50                   30Black nightshade      30 0Blackgrass 100         100            70 40                 30                   30                     50 90 70                             100                                80 80 80 80                                           40 50 100                                                    100 90Catchweed bedstraw      100         0           90 90 80                             90 90 80 90 90                                           90 0  100                                                    100 90Chickweed  60 0  0  0 0 0 30 80 50                             80 80 70 80 70                                           70 30 100                                                    100 100Green foxtail      0  0  60 20                 20                   0Italian ryegrass      60 50Knotweed                          -- -- 30 0  0 0     100                                                    100 100Kochia     0  0Lambsquarters      0  0  0  0 50                   0Pigweed    0  0  40 20                 0 0Rape       75 20Scentless chamomile      90 90          80 90 90                             90 80 80 90 90                                           50 0  100                                                    100 100Smartweed        90 80                 50                   50Speedwell  60 --          30 100                           80                             100                                100                                   100                                      100                                         80                                           50 50 100                                                    100 100Sugar beet 0  0  0  0 30                   0 0  80 30                             90 90 80 30 30                                           10 0  100                                                    80  80Wheat      40 20          20 70 30                             70 60 40 0  0 0  0  90 90  70Wild buckwheat      20 0  20 0 0 0 0  30 30                             90 90 80 85 70                                           70 30 100                                                    100 100Wild mustard      75 20 100               50                 80                   0Wild oat   70 50 70 0 30                   0 30 70 70                             80 80 60 80 50                                           30 40 90 80  70Wild radish      30 0__________________________________________________________________________