Abstract:
Specific iodopyrimidine compounds such as 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzoic acid, methyl ester and N&#39;-[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide are active preemergent and postemergent herbicides and plant growth regulants.

Description:
RELATED APPLICATION 
     This application is a continuation-in-part of my copending application U.S. Ser. No. 619,276 filed June 11, 1984 now abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates to specific iodopyrimidine compounds which are useful as general or selective preemergent or postemergent herbicides or as plant growth regulants. 
     U.S. Pat. No. 4,394,506, issued July 19, 1983 to Levitt discloses herbicidal N-(heterocyclicaminocarbonyl)arylsulfonamides of the formula ##STR1## wherein, among other substituents, X may be OCH 3  or OC 2  H 5  and Y may be F, Cl, or Br. 
     SUMMARY OF THE INVENTION 
     This invention relates to novel compounds of Formula I, argiculturally suitable compositions containing them, and their method-of-use as general or selective preemergent or postemergent herbicides or as plant growth regulants. ##STR2## wherein R is CH 3  or CH 2  CH 3  ; ##STR3## R 1  is C 1  -C 4  alkyl, C 1  -C 4  alkoxy, OCH 2  CH 2  OCH 3 , F, Cl, Br, NO 2 , CF 3 , CO 2  R 15 , SO 2  NR 16  R 17 , C(O)R 21 , CR 21  (OR 22 ) 2 , SO 2  N(OCH 3 )CH 3 , OSO 2  R 18 , S(O) n  R 19 , WCF 3 , WCHF 2 , C 3  -C 4  alkenyloxy, C 3  -C 4  alkynyloxy, C 1  -C 2  alkyl substituted with OCH 3  or OCH 2  CH 3 , C 6  H 5 , ##STR4## R 2  is H, F, Cl, Br, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 3  -C 4  alkenyloxy, C 3  -C 4  alkynyloxy, C 1  -C 4  haloalkoxy, C 1  -C 4  haloalkyl, S(O) p  C 1  -C 4  alkyl, S(O) p  C 3  -C 4  alkenyl, S(O) p  C 3  -C 4  alkynyl or C 1  -C 2  alkyl substituted with OCH 3  or SCH 3  ; 
     R 3  is H, CH 3 , OCH 3 , F, Cl, Br, SO 2  N(CH 3 ) 2 , OSO 2  CH 3  or S(O) n  CH 3  ; 
     R 4  is CH 3 , CH 2  CH 3 , OCH 3 , OCH 2  CH 3 , F, Cl, Br, SO 2  NR 16  R 17 , SO 2  N(OCH 3 )CH 3 , S(O) n  R 19 , C 3  -C 4  alkenyloxy or C 3  -C 4  alkynyloxy; 
     R 5  is C 1  -C 3  alkyl, F, Cl, Br, NO 2 , CO 2  R 15 , SO 2  NR 16  R 17 , SO 2  N(OCH 3 )CH 3  or S(O) n  R 19  ; 
     R 6  is Cl, NO 2 , CO 2  CH 3 , CO 2  CH 2  CH 3 , SO 2  N(CH 3 ) 2 , OSO 2  CH 3 , SO 2  CH 3 , SO 2  CH 2  CH 3 , OCH 3  or OCH 2  CH 3  ; 
     R 7  is H, CH 3  or CH 2  CH 3  ; 
     R 8  is H, CH 3  or CH 2  CH 3  ; 
     R 9  is H or CH 3  ; 
     R 10  is H or CH 3  ; 
     R 11  is H or CH 3  ; 
     R 12  is H, C 1  -C 4  alkyl, C 3  -C 4  alkenyl, C 3  -C 4  alkynyl, benzyl, C 1  -C 4  alkylcarbonyl, C 1  -C 4   alkoxycarbonyl, CH 2  CN, CH 2  C(O)CH 3 , CH 2  CO 2  (C 1  -C 2  alkyl), C 1  -C 4  alkyl substituted with 0-3F, 0-1Cl, OH, OCH 3  or OC 2  H 5  or C 3  -C 4  alkenyl substituted with 1-3F or 1-3Cl; 
     R 13  is H or CH 3  ; 
     R 14  is CH 3  or C 2  H 5  ; 
     R 15  is C 1  -C 4  alkyl, CH 2  CH 2  OCH 3 , CH 2  CH 2  Cl or CH 2  CH═CH 2  ; 
     R 16  is H, C 1  -C 3  alkyl; 
     R 17  is C 1  -C 3  alkyl; 
     R 18  is C 1  -C 3  alkyl or N(CH 3 ) 2  ; 
     R 19  is C 1  -C 3  alkyl or CH 2  CH═CH 2  ; 
     R 20  is H, Cl or CH 3  ; 
     R 21  is H, C 1  -C 4  alkyl, C 3  -C 4  alkenyl, C 3  -C 4  alkynyl or C 3  -C 6  cycloalkyl; 
     R 22  is C 1  -C 2  alkyl; 
     m is 0 or 1; 
     n is 0 or 2; 
     p is 0, 1 or 2; 
     Q 1  is O, S or SO 2  ; 
     Q 2  is O or S; and 
     W is O, S or SO 2  ; 
     provided that 
     (1) the total number of carbon atoms of R 16  and R 17  is less than or equal to four; and 
     (2) when m is 1, then R 9  is H; and their agriculturally suitable salts. 
     Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are: 
     (1) Compunds of Formula I where R is CH 3 . 
     (2) Compounds of Preferred 1 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17. 
     (3) Compounds of Preferred 2 where 
     L is L-1; 
     R 1  is OCH 3 , OC 2  H 5 , Cl, NO 2 , CF 3 , CO 2  CH 3 , CO 2  C 2  H 5 , SO 2  N(CH 3 ) 2 , SO 2  N(OCH 3 )CH 3 , OSO 2  R 18 , S(O) n  R 19 , OCF 2  H, SCF 2  H, C(O)CH 3 , C(O)C 2  H 5 , OCH 2  CH═CH 2 , OCH 2  C.tbd.CH, ##STR5## R 2  is H, F, Cl, Br, CH 3 , C 2  H 5 , S(O) p  C 1  -C 2  alkyl, S(O) p  CH 2  CH═CH 2 , S(O) p  CH 2  C.tbd.CH, C 1  -C 3  alkoxy, OCH 2  CH═CH 2 , OCH 2  C.tbd.CH, C 1  -C 2  haloalkoxy, C 1  -C 2  haloalkyl, CH 2  OCH 3  or CH 2  SCH 3  ; 
     R 18  is C 1  -C 3  alkyl; 
     R 19  is CH 3  or C 2  H 5  ; and 
     n is 2. 
     (4) Compounds of Preferred 3 where 
     L is ##STR6##  and R 2  is H, F, Cl, Br, CH 3 , CH 2  CH 3 , SCH 3 , SC 2  H 5 , OCH 3 , OC 2  H 5 , CF 3 , CH 2  OCH 3  or CH 2  SCH 3 . 
     (5) Compounds of Preferred 2 where 
     L is L-2; and 
     R 3  is Cl, CH 3 , OCH 3 , SCH 3  or Br. 
     (6) Compounds of Preferred 2 where 
     L is L-3; and 
     R 4  is Cl, SO 2  CH 3  or SO 2  N(CH 3 ) 2 . 
     (7) Compounds of Preferred 2 where 
     R 20  is H; 
     L is L-5; and 
     R 5  is CO 2  CH 3  or CO 2  C 2  H 5 . 
     (8) Compounds of Preferred 2 where L is L-8. 
     (9) Compounds of Preferred 2 where 
     R 9  is H; 
     R 2  is H, F, Cl, Br, CH 3 , CH 2  CH 3 , SCH 3 , SC 2  H 5 , OCH 3 , OC 2  H 5 , CF 3 , CH 2  OCH 3  or CH 2  SCH 3 . 
     L is L-10; and 
     R 12  is H, C 1  -C 4  alkyl, C 1  -C 4  alkylcarbonyl, CH 2  F or C 2  -C 3  alkyl substituted with 1F or 1Cl. 
     (10) Compounds of Preferred 2 where 
     L is L-11; 
     R 9  is H; and 
     R 2  is H, F, Cl, Br, CH 3 , CH 2  CH 3 , SCH 3 , SC 2  H 5 , OCH 3 , OC 2  H 5 , CF 3 , CH 2  OCH 3  or CH 2  SCH 3 . 
     (11) Compounds of Preferred 2 where 
     L is L-16; 
     R 2  is H, F, Cl, Br, CH 3 , CH 2  CH 3 , SCH 3 , SC 2  H 5 , OCH 3 , OC 2  H 5 , CF 3 , CH 2  OCH 3  or CH 2  SCH 3 . 
     (12) Compounds of Preferred 2 where 
     L is L-17; 
     R 2  is H, F, Cl, Br, CH 3 , CH 2  CH 3 , SCH 3 , SC 2  H 5 , OCH 3 , OC 2  H 5 , CF 3 , CH 2  OCH 3  or CH 2  SCH 3 . 
     Specifically preferred for reasons of their highest herbicidal activity, greatest growth regulant activity and/or most favorable ease of synthesis are: 
     2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 194°-196° C.(d); 
     N&#39;-[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide, m.p. 231°-232.5° C.; and 
     2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-4-methylbenzoic acid, methyl ester, m.p. 185°-186° C. 
     DETAILED DESCRIPTION OF THE INVENTION 
     Synthesis 
     The compounds of Formula I can be prepared by one or more of the following methods described below in Equations 1, 4, 5 and 6. 
     As shown in Equation 1 below, compounds of Formula I can be prepared by reacting an appropriately substituted sulfonyl isocyanate of Formula II with an aminoheterocycle of Formula III where L and R are as previously defined. ##STR7## 
     The reaction is best carried out in inert aprotic organic solvents such as dichloromethane, 1,2-dichloroethane, tetrahydrofuran, or acetonitrile, at a temperature between 20° and 85° C. The order of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate or a solution of it in the reaction solvent to a stirred solution of the amine. 
     In some cases, the desired product is insoluble in the reaction solvent at ambient temperature and crystallizes from it in pure form. Products soluble in the reaction solvent are isolated by evaporation of the solvent. Compounds of Formula I then may be purified by trituration of the evaporation residue with solvents such as 1-chlorobutane or ethyl ether and filtration, by recrystallization from mixtures of solvents such as 1,2-dichloroethane, 1-chlorobutane and heptane or by chromatography on silica gel. 
     Sulfonylisocyanates of Formula II are known in the art and are prepared from the corresponding sulfonamides (IV) by one of the following two general methods. ##STR8## 
     The sulfonamide IV and an alkyl isocyanate (e.g., n-butyl isocyanate) in xylene or other solvent boiling above 135° C. are mixed in the presence or absence of a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) and heated to 135°-140° C. After 5-60 minutes phosgene is slowly added to the heated mixture at such a rate that the temperature remains between 133° and 135° C. When the consumption of phosgene has ceased, the mixture is cooled and filtered to remove insoluble material. Finally, the solvent, alkyl isocyanate, and excess phosgene are evaporated, leaving the sulfonyl isocyanate (II). 
     If desired, the alkyl isocyanate-sulfonamide adduct can be made and isolated before reaction with the phosgene. In this case the sulfonamide (IV), alkyl isocyanate, and anhydrous base (e.g., K 2  CO 3 ) in a polar, aprotic solvent (e.g., acetone, butanone, or acetonitrile) are mixed and heated under reflux for 1 to 6 hours. The reaction mixture is then diluted with water, and the pH is adjusted to about 3 with acid (e.g., HCl, H 2  SO 4 ). The adduct is filtered out and dried, and then reacted with phosgene as described above. This procedure modification is especially useful when sulfonamide (IV) is high melting and has low solubility in the phosgenation solvent. 
     Sulfonyl isocyanates (II) can also be prepared by the following method. ##STR9## 
     The sulfonamide (IV) is heated at reflux in an excess of thionyl chloride. The reaction is continued until the sulfonamide protons are no longer detectable in the proton magnetic resonance spectrum. From 16 hours to 5 days is typically sufficient for complete conversion to the thionylamide (V) (Equation 3a). 
     The thionyl chloride is evaporated and the residue is treated with an inert solvent (e.g., toluene) containing at least one equivalent (typically 2-3 equivalents) of phosgene. A catalytic amount of pyridine (typically 0.1 equivalent) is added, and the mixture is heated to about 60°-140° C., with 80°-100° preferred. Conversion to the isocyanate (II) is usually substantially complete within 15 minutes to 3 hours (Equation 3b). The mixture is then cooled and filtered, and the solvent is evaporated, leaving the sulfonyl isocyanate (II). 
     Many of the compounds of Formula I can be prepared by the procedure shown in Equation 4. ##STR10## 
     The reaction shown in Equation 4 is carried out by contacting phenylcarbamates of Formula VI with aminoheterocycles of Formula III in an inert organic solvent such as dioxane or tetrahydrofuran at temperatures of about 20°-100° C. for a period of about one-half to twenty-four hours. The product can be isolated by evaporation of the reaction solvent and purified by methods previously described. 
     Phenyl carbamates of Formula VI can be prepared by the methods described, or modifications thereof known to those skilled in the art, in European Patent Application No. 81810282.4 (Publ. No. 44,808), published Jan. 27, 1982; or South African Patent Application No. 825042. 
     Alternatively, many of the compounds of Formula I can be prepared by the method described in Equation 5. ##STR11## 
     The reaction of Equation 5 can be carried out by contacting equimolar amounts of a sulfonamide of Formula IV with a heterocyclic phenylcarbamate of Formula VII in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analagous to those described in South African Patent Application No. 830441. The phenyl carbamates of Formula VII can be prepared by methods, or modifications thereof known to those skilled in the art, described in South African Patent Application No. 825671 and South African Patent Application No. 825045. 
     Rarely, a sulfonamide of Formula IV may not be of sufficient stability to be useful as a starting material in any of the above procedures. In these cases, as well as others, the sulfonyl isocyanate of Formula II can be prepared as an unisolated intermediate by treating the corresponding sulfonyl chloride (VIII) with isocyanate anion in the presence of the heterocyclic amine of Formula III as shown in Equation 6. ##STR12## 
     The reaction is best carried out by adding over one to six hours a solution of at least one equivalent of a tetraalkylammonium isocyanate, such as tetra-n-butylammonium isocyanate, in a suitable aprotic organic solvent, such as dichloromethane or tetrahydrofuran, to a well-stirred mixture of one equivalent of sulfonyl chloride of Formula VIII and at least one equivalent of heterocyclic amine of Formula III in a similar suitable organic solvent at 20°-40° C. The reaction mixture is then diluted with dichloromethane, washed with 1N sulfuric acid, and dried over sodium sulfate. Rotary evaporation of the solvent leaves the product of Formula I in crude form. This may be purified as has already been described for Equation 1. 
     Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene, or thiophene in tetrachloromethane according to the teachings of H. T. Clarke et al., Org. Synth. Coll., Vol. 1, 2nd Ed. 1941, p. 85. Other sulfonyl chlorides can be made by diazotization of the appropriate amine with sodium nitrite in hydrochloric acid, followed by reaction of the diazonium salt with sulfur dioxide and cuprous or cupric chloride in acetic acid according to the teachings of H. L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960) and of H. Meerwein et al., Chem. Ber., 90, 841 (1957). 
     Reference to the following patents is suggested for further details regarding the preparation of the sulfonamides (IV) and sulfonyl isocyanates (II): U.S. Pat. No. 4,169,719; U.S. Pat. No. 4,127,405; U.S. Pat. No. 4,394,506; and E.P.-A-No. 79,683. 
     Iodopyrimidines of Formula III can be prepared by the procedure shown in Equation 7. ##STR13## 
     Treatment of a 2-amino-4-chloro-6-alkoxypyrimidines of Formula IX with 57% aqueous hydroiodic acid according to procedures found in J. Chem. Soc. C, 1204 (1967) gives the iodopyrimidines of Formula III. The chloropyrimidines of Formula IX are known in the art. 
     The following examples further illustrate the synthesis of this invention. 
    
    
     EXAMPLE 1 
     2-Amino-4-iodo-6-methoxypyrimidine 
     18.0 g of 2-amino-4-chloro-6-methoxypyrimidine was added to 65 mL of 57% aqueous hydroiodic acid with ice bath cooling. The resulting thick mixture was kept at ambient temperature for 65 hours, diluted with water and neutralized with potassium carbonate. The solid was collected and recrystallized from aqueous ethanol to give 5.0 g of white crystals, m.p. 141.5°-144° C. 
     NMR(CDCl 3 ): 3.82 (s, 3H, OCH 3 ); 5.3 (br s, 2H, NH 2 ); and 6.54 (s, 1H, pyr C5-H). 
     EXAMPLE 2 
     2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 
     To a solution of 0.25 g of 2-amino-4-iodo-6-methoxypyrimidine in 5 mL of dry methylene chloride was added 0.30 g 2-carbomethoxybenzenesulfonyl isocyanate. The resulting solution was allowed to stand for 20 hours at ambient temperature. The solution was cooled in an ice bath and crystallization induced with scratching. The crystals were collected, washed with n-butylchloride and dried to afford 0.10 g of the title compound, m.p. b 194°-196° C. (dec). 
     IR (nujol) 1728 cm -1  (ester) and 1705 cm 31  1 (sulfonylurea). 
     NMR (CDCl 3 ): 3.94 (s, 3H, CO 2  CH 3 ); 4.06 (s, 3H, OCH 3 ); 6.95 (s, 1H, pyr. C5-H); 7.4 (br s, 1H, NH); 7.75 (m, 3H, aromatics); 8.4 (m, 1H, aromatic); and 12.15 (br s, 1H, NH). 
     Using the procedures and examples shown above, the compounds in Tables 1-17 can be prepared. ##STR14## 
     
                                           TABLE 1__________________________________________________________________________General Structure 1R    R.sub.1      R.sub.2     m.p. (°C.)__________________________________________________________________________CH.sub.3CH.sub.3     HCH.sub.3CH.sub.2 CH.sub.3             HCH.sub.3CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3CH(CH.sub.3).sub.2             HCH.sub.3CH(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.3OCH.sub.3    HCH.sub.3OCH.sub.2 CH.sub.3             HCH.sub.3OCH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3OCH(CH.sub.3).sub.2             HCH.sub.3OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3OCH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.3F            HCH.sub.3Cl           H           197-200 (dec)CH.sub.3Br           HCH.sub.3NO.sub.2     H           223.5-225 (dec)CH.sub.3CF.sub.3     H           217-220 (dec)CH.sub.3CO.sub.2 CH.sub.3             H           194-196 (dec)CH.sub.3CO.sub.2 CH.sub.3             5-FCH.sub.3CO.sub.2 CH.sub.3             3-ClCH.sub.3CO.sub.2 CH.sub.3             5-ClCH.sub.3CO.sub.2 CH.sub.3             6-ClCH.sub.3CO.sub.2 CH.sub.3             5-BrCH.sub.3CO.sub.2 CH.sub.3             5-CF.sub.3  148-150CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.3  185-187CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.3 195-197CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.3CH.sub. 3CO.sub.2 CH.sub.3             5-SCH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-OCF.sub.2 HCH.sub.3CO.sub.2 CH.sub.3             3-CH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             H           186-187.5 (dec)CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             3-ClCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-ClCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             6-ClCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-CF.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             3-CH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-CH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-SCH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCF.sub.2 HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             3-ClCH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-ClCH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             6-ClCH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-CF.sub.3CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             3-CH.sub.3CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-CH.sub.3CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-OCH.sub.3CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-OCF.sub.2 HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             5-CH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2             HCH.sub.3CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-CF.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-ClCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-OCH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             5-CH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             HCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             5-OCH.sub.3CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             HCH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             5-CF.sub.3CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             5-OCH.sub.3CH.sub.3SO.sub.2 N(CH.sub.3).sub.2             H           231-232.5 (dec)CH.sub.3SO.sub.2 N(CH.sub.3).sub.2             3-ClCH.sub.3SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.3SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2             HCH.sub.3SO.sub.2 N(CH.sub. 3)CH(CH.sub.3).sub.2             HCH.sub.3SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3OSO.sub.2 CH.sub.3             H           217-219 (dec)CH.sub.3OSO.sub.2 CH.sub.3             5-ClCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3OSO.sub.2 CH(CH.sub.3).sub.2             HCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3OSO.sub.2 N(CH.sub.3).sub.2             HCH.sub.3SCH.sub.3    H           116-120CH.sub.3SCH.sub.2 CH.sub.3             HCH.sub.3SCH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3SCH(CH.sub.3).sub.2             HCH.sub.3SCH.sub.2 CHCH.sub.2             HCH.sub.3SOCH.sub.3   HCH.sub.3SOCH.sub.2 CH.sub.3             HCH.sub.3SO.sub.2 CH.sub.3             H           239-241 (dec)CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.3SO.sub.2 CH(CH.sub.3).sub.2             HCH.sub.3SO.sub.2 CH.sub.2 CHCH.sub.2             HCH.sub.3SCF.sub.3    HCH.sub.3SO.sub.2 CF.sub.3             HCH.sub.3OCF.sub.3    HCH.sub.3SCF.sub.2 H  HCH.sub.3SO.sub.2 CF.sub.2 H             HCH.sub.3OCF.sub.2 H  HCH.sub.3OCH.sub.2 CHCH.sub.2             HCH.sub.3OCH.sub.2 CHCHCH.sub.3             HCH.sub.3OCH(CH.sub.3)CHCH.sub.2             HCH.sub.3OCH.sub.2 CCH             HCH.sub.3OCH.sub.2 CCCH.sub.3             HCH.sub.3OCH(CH.sub.3)CCH             HCH.sub.3CH.sub.2 OCH.sub.3             HCH.sub.3CH.sub.2 OCH.sub.2 CH.sub.3             HCH.sub.3CH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.3CH(CH.sub.3)OCH.sub.3             HCH.sub.3C.sub.6 H.sub.5             HCH.sub.3             HCH.sub.3 ##STR15##   HCH.sub.3 ##STR16##   HCH.sub.3 ##STR17##   HCH.sub.3 ##STR18##   HCH.sub.3 ##STR19##   5-ClCH.sub.3 ##STR20##   HCH.sub.3 ##STR21##   HCH.sub.3 ##STR22##   HCH.sub.3 ##STR23##   HCH.sub.3 ##STR24##   HCH.sub.3 ##STR25##   HCH.sub.3 ##STR26##   HCH.sub.3 ##STR27##   HCH.sub.3 ##STR28##   HCH.sub.3 ##STR29##   HCH.sub.2 CH.sub.3CH.sub.3     HCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3CH(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OCH.sub.3    HCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OCH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.2 CH.sub.3F            HCH.sub.2 CH.sub.3Cl           HCH.sub.2 CH.sub.3Br           HCH.sub.2 CH.sub.3NO.sub.2     HCH.sub.2 CH.sub.3CF.sub.3     HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-FCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             3-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             6-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-BrCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-CF.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3CO.sub. 2 CH.sub.3             5-SCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             5-OCF.sub.2 HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.3             3-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             3-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             6-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-CF.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             3-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-SCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCF.sub.2 HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             3-ClCH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-ClCH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             6-ClCH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-CF.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             3-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3).sub.2             5-OCF.sub.2 HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             5-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-CF.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-ClCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             5-CH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 Cl             5-OCH.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             HCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             5-CF.sub.3CH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2             5-OCH.sub.3CH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2             3-ClCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3)CH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.3             5-ClCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OSO.sub.2 CH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3OSO.sub.2 N(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SCH.sub.3    HCH.sub.2 CH.sub.3SCH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SCH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SCH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SCH.sub.2 CHCH.sub.2             HCH.sub.2 CH.sub.3SOCH.sub.3   HCH.sub. 2 CH.sub.3SOCH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SO.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3             HCH.sub.2 CH.sub.3SO.sub.2 CH(CH.sub.3).sub.2             HCH.sub.2 CH.sub.3SO.sub.2 CH.sub.2 CHCH.sub.2             HCH.sub.2 CH.sub.3SCF.sub.3    HCH.sub.2 CH.sub.3SO.sub.2 CF.sub.3             HCH.sub.2 CH.sub.3OCF.sub.3    HCH.sub.2 CH.sub.3SCF.sub.2 H  HCH.sub.2 CH.sub.3SO.sub.2 CF.sub.2 H             HCH.sub.2 CH.sub.3OCF.sub.2 H  HCH.sub.2 CH.sub.3OCH.sub.2 CHCH.sub.2             HCH.sub.2 CH.sub.3OCH.sub.2 CHCHCH.sub.3             HCH.sub.2 CH.sub.3OCH(CH.sub.3)CHCH.sub.2             HCH.sub.2 CH.sub.3OCH.sub.2 CCH             HCH.sub.2 CH.sub.3OCH.sub.2 CCCH.sub.3             HCH.sub.2 CH.sub.3OCH(CH.sub.3)CCH             HCH.sub.2 CH.sub.3CH.sub.2 OCH.sub.3             HCH.sub.2 CH.sub.3CH.sub.2 OCH.sub.2 CH.sub.3             HCH.sub. 2 CH.sub.3CH.sub.2 CH.sub.2 OCH.sub.3             HCH.sub.2 CH.sub.3CH(CH.sub.3)OCH.sub.3             HCH.sub.2 CH.sub.3C.sub.6 H.sub.5             HCH.sub.2 CH.sub.3 ##STR30##   HCH.sub.2 CH.sub.3 ##STR31##   HCH.sub.2 CH.sub.3 ##STR32##   HCH.sub.2 CH.sub.3 ##STR33##   HCH.sub.2 CH.sub.3 ##STR34##   HCH.sub.2 CH.sub.3 ##STR35##   HCH.sub.2 CH.sub.3 ##STR36##   5-ClCH.sub.2 CH.sub.3 ##STR37##   HCH.sub.2 CH.sub.3 ##STR38##   HCH.sub.2 CH.sub.3 ##STR39##   HCH.sub.2 CH.sub.3 ##STR40##   HCH.sub.2 CH.sub.3 ##STR41##   HCH.sub.2 CH.sub.3 ##STR42##   HCH.sub.2 CH.sub.3 ##STR43##   HCH.sub.2 CH.sub.3 ##STR44##   HCH.sub.2 CH.sub.3 ##STR45##   HCH.sub.2 CH.sub.3 ##STR46##   HCH.sub.2 CH.sub.3 ##STR47##   HCH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CHCH.sub.2CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CCHCH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CHClCH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SOCH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SCH.sub.2 CHCH.sub.2CH.sub.3CO.sub.2 CH.sub.3             5-SCH.sub.2 CCHCH.sub.3CO.sub.2 CH.sub.3             5-SCH.sub.2 CH.sub.2 CCHCH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 OCH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 SCH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.2 CHCH.sub.2CH.sub.3CO.sub.2 CH.sub.3             5-OCH.sub.2 CH.sub.2 C CHCH.sub.3CO.sub.2 CH.sub.3             5-OCF.sub.2 CF.sub.2 HCH.sub.3CO.sub.2 CH.sub.3             5-SO.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SCH.sub.2 CH.sub.2 CHCH.sub.2CH.sub.3CO.sub.2 CH.sub.3             5-CH.sub.2 CH.sub.2 OCH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SO.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3CO.sub.2 CH.sub.3             5-SO.sub.2 CH.sub.2 CHCH.sub.2CH.sub.3CO.sub.2 CH.sub.3             5-SO.sub.2 CH.sub.2 CCHCH.sub.3C(O)CH.sub.3 HCH.sub.3C(CH.sub.3)(OCH.sub.3).sub.2             HCH.sub.3SO.sub.2 NHCH.sub.3             H__________________________________________________________________________ 
    
     
                       TABLE 2______________________________________General Structure 2R            R.sub.3       m.p. (°C.)______________________________________CH.sub.3     CH.sub.3CH.sub.2 CH.sub.3        CH.sub.3CH.sub.3     OCH.sub.3CH.sub.2 CH.sub.3        OCH.sub.3CH.sub.3     FCH.sub.3     HCH.sub.3     ClCH.sub.2 CH.sub.3        ClCH.sub.3     BrCH.sub.2 CH.sub.3        BrCH.sub.3     SO.sub.2 N(CH.sub.3).sub.2CH.sub.3     OSO.sub.2 CH.sub.3CH.sub.3     SCH.sub.3CH.sub.3     SOCH.sub.3CH.sub.3     SO.sub.2 CH.sub.3______________________________________ 
    
     
                       TABLE 3______________________________________General Structure 3R          R.sub.4          m.p. (°C.)______________________________________CH.sub.3   CH.sub.3CH.sub.3   CH.sub.2 CH.sub.3CH.sub.3   OCH.sub.3CH.sub.2 CH.sub.3      OCH.sub.3CH.sub.3   OCH.sub.2 CH.sub.3CH.sub.3   FCH.sub.3   ClCH.sub.2 CH.sub.3      ClCH.sub.3   BrCH.sub.3   SO.sub.2 N(CH.sub.3).sub.2CH.sub.3   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2CH.sub.3   SO.sub.2 N(OCH.sub.3)CH.sub.3CH.sub.3   SO.sub.2 CH.sub.3CH.sub.3   SCH.sub.3CH.sub.3   SOCH.sub.3CH.sub.3   SCH.sub.2 CH.sub.3CH.sub.3   SO.sub.2 CH.sub.2 CH.sub.3CH.sub.3   SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2CH.sub.3   SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3   SCH.sub.2 CH═CH.sub.2CH.sub.3   SO.sub.2 CH.sub.2 CH═CH.sub.2CH.sub.3   OCH.sub.2 CH═CH.sub.2CH.sub.2 CH.sub.3      OCH.sub.2 CH═CH.sub.2CH.sub.3   OCH(CH.sub.3)CH═CH.sub.2CH.sub.3   OCH.sub. 2 C.tbd.CHCH.sub.3   OCH.sub.2 C.tbd.CCH.sub.3______________________________________ 
    
     
                       TABLE 4______________________________________General Structure 4R       R.sub.5         R.sub.20 m.p. (°C.)______________________________________CH.sub.3   CH.sub.3        HCH.sub.3   CH.sub.2 CH.sub.3                   HCH.sub.3   CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CH(CH.sub.3).sub.2                   5-ClCH.sub.3   F               HCH.sub.3   Cl              HCH.sub.3   Br              HCH.sub.3   NO.sub.2        HCH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3).sub.2                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 Cl                   HCH.sub.3   CO.sub.2 CH.sub.2 CH═CH.sub.2                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   5-CH.sub.3CH.sub.3   SO.sub.2 N(CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(OCH.sub.3)CH.sub.3                   HCH.sub.3   SCH.sub. 3      HCH.sub.3   SOCH.sub.3      HCH.sub.3   SO.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH═CH.sub.2                   H______________________________________ 
    
     
                       TABLE 5______________________________________General Structure 5R       R.sub.5         R.sub.20 m.p. (°C.)______________________________________CH.sub.3   CH.sub.3        HCH.sub.3   CH.sub.2 CH.sub.3                   HCH.sub.3   CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CH(CH.sub.3).sub.2                   5-ClCH.sub.3   F               HCH.sub.3   Cl              HCH.sub.3   Br              HCH.sub.3   NO.sub.2        HCH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3).sub.2                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 Cl                   HCH.sub.3   CO.sub.2 CH.sub.2 CH═CH.sub.2                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   5-CH.sub.3CH.sub.3   SO.sub.2 N(CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(OCH.sub.3)CH.sub.3                   HCH.sub.3   SCH.sub. 3      HCH.sub.3   SOCH.sub.3      HCH.sub.3   SO.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH═CH.sub.2                   H______________________________________ 
    
     
                       TABLE 6______________________________________General Structure 6R       R.sub.5         R.sub.20 m.p. (°C.)______________________________________CH.sub.3   CH.sub.3        HCH.sub.3   CH.sub.2 CH.sub.3                   HCH.sub.3   CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CH(CH.sub.3).sub.2                   2-ClCH.sub.3   F               HCH.sub.3   Cl              HCH.sub.3   Br              HCH.sub.3   NO.sub.2        HCH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3).sub.2                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                   HCH.sub.3   CO.sub.2 CH.sub.2 CH.sub.2 Cl                   HCH.sub.3   CO.sub.2 CH.sub.2 CH═CH.sub.2                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.3                   HCH.sub.2 CH.sub.3   CO.sub.2 CH.sub.2 CH.sub.3                   2-CH.sub.3CH.sub.3   SO.sub.2 N(CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                   HCH.sub.3   SO.sub.2 N(OCH.sub.3)CH.sub.3                   HCH.sub.3   SCH.sub.3       HCH.sub.3   SOCH.sub.3      HCH.sub.3   SO.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH.sub.2 CH.sub.3                   HCH.sub.3   SCH.sub.2 CH═CH.sub.2                   H______________________________________ 
    
     
                       TABLE 7______________________________________General Structure 7R            R.sub.6       m.p. (°C.)______________________________________CH.sub.3     ClCH.sub.3     NO.sub.2CH.sub.3     CO.sub.2 CH.sub.3CH.sub.2 CH.sub.3        CO.sub.2 CH.sub.3CH.sub.3     CO.sub.2 CH.sub.2 CH.sub.3CH.sub.2 CH.sub.3        CO.sub.2 CH.sub.2 CH.sub.3CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2CH.sub.3     OSO.sub.2 CH.sub.3CH.sub.3     SO.sub.2 CH.sub.3CH.sub.3     SO.sub.2 CH.sub.2 CH.sub.3CH.sub.3     OCH.sub.3CH.sub.3     OCH.sub.2 CH.sub.3______________________________________ 
    
     
                       TABLE 8______________________________________General Structure 8R      R.sub.2         R.sub.7  R.sub.8                       R.sub.9                            m    Q.sub.1                                      m.p. (°C.)______________________________________CH.sub.3  H      H        H    H    0    OCH.sub.3  H      CH.sub.3 H    H    0    OCH.sub.3  H      CH.sub.3 CH.sub.3                       H    0    OCH.sub.3  H      H        H    CH.sub.3                            0    OCH.sub.3  H      H        CH.sub.3                       H    1    OCH.sub.3  H      CH.sub.3 CH.sub.3                       H    1    OCH.sub.3  H      CH.sub.3 H    H    0    SCH.sub.3  H      CH.sub.3 CH.sub.3                       H    0    SCH.sub.3  H      H        H    CH.sub.3                            0    SCH.sub.3  H      CH.sub.3 H    H    1    SCH.sub.3  H      CH.sub.3 CH.sub.3                       H    1    SCH.sub.3  H      H        H    H    0    SO.sub.2CH.sub.3  H      CH.sub.3 H    H    0    SO.sub.2CH.sub.2 CH.sub.3  H      CH.sub.3 H    H    0    SO.sub.2CH.sub.3  H      CH.sub.3 CH.sub.3                       H    0    SO.sub.2CH.sub.2 CH.sub.3  H      CH.sub. 3                  CH.sub.3                       H    0    SO.sub.2CH.sub.3  H      CH.sub.3 H    CH.sub.3                            0    SO.sub.2CH.sub.3  H      CH.sub.3 H    H    1    SO.sub.2CH.sub.3  H      CH.sub.3 CH.sub.3                       H    1    SO.sub.2CH.sub.3  H      CH.sub.2 CH.sub.3                  H    H    0    SO.sub.2CH.sub.3  H      CH.sub.2 CH.sub.3                  H    H    1    SO.sub.2CH.sub.3  6-Cl   CH.sub.3 H    H    0    SO.sub.2CH.sub.3  7-Cl   CH.sub.3 H    H    1    SO.sub.2CH.sub.3  5-Br   CH.sub.3 H    H    0    OCH.sub.3  6-CH.sub.3         CH.sub.3 H    H    0    SO.sub.2CH.sub.3  7-Cl   CH.sub.3 H    H    1    SCH.sub.3  6-Cl   CH.sub.3 CH.sub.3                       H    0    SO.sub.2______________________________________ 
    
     
                       TABLE 9______________________________________General Structure 9R         R.sub.2            R.sub.10                    R.sub.11                          Q.sub.2                                m.p. (°C.)______________________________________CH.sub.3  H      H       H     OCH.sub.3  H      CH.sub.3                    H     OCH.sub.3  H      CH.sub.3                    CH.sub.3                          OCH.sub.2 CH.sub.3     H      H       H     OCH.sub.2 CH.sub.3     H      CH.sub.3                    H     OCH.sub.2 CH.sub.3     H      CH.sub.3                    CH.sub.3                          OCH.sub.3  H      H       H     SCH.sub.3  H      CH.sub.3                    H     SCH.sub.3  H      CH.sub.3                    CH.sub.3                          SCH.sub.2 CH.sub.3     H      H       H     SCH.sub.2 CH.sub.3     H      CH.sub.3                    H     SCH.sub.2 CH.sub.3     H      CH.sub.3                    CH.sub.3                          S______________________________________ 
    
     
                       TABLE 10______________________________________General Structure 10R       R.sub.2          R.sub.9                 R.sub.12   m    m.p. (°C.)______________________________________CH.sub.3   H      H      CH.sub.3   0CH.sub.3   H      CH.sub.3                 CH.sub.3   0CH.sub.3   H      H      CH.sub.3   1CH.sub.2 CH.sub.3   H      H      CH.sub.3   0CH.sub.2 CH.sub.3   H      CH.sub.3                 CH.sub.3   0CH.sub.2 CH.sub.3   H      H      CH.sub.3   1CH.sub.3   H      H      CH.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CH.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH(CH.sub.3).sub.2                            0CH.sub.3   H      H      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH(CH.sub.3)CH.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CH(CH.sub.3).sub.2                            0CH.sub.3   H      H      CH.sub.2 CH.sub.3                            1CH.sub.3   H      H      CH(CH.sub.3).sub.2                            1CH.sub.3   H      H      CH.sub.2 CH.sub.2 CH.sub.3                            1CH.sub.3   6-Cl   H      CH.sub.3   0CH.sub.3   H      H      CH.sub.2 CH.sub.2 F                            0CH.sub.3   H      H      CH.sub.2 CH.sub.2 OCH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CH═CH.sub.2                            0CH.sub.3   H      H      CH.sub.2 C.tbd.CH                            0CH.sub.3   H      H      CH.sub.2 C.sub.6 H.sub.5                            0CH.sub.3   H      H      C(O)CH.sub.3                            0CH.sub.3   H      H      C(O)CH.sub.2 CH.sub.2 CH.sub.3                            1CH.sub.3   H      H      CO.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CN                            0CH.sub.3   H      H      CH.sub.2 C(O)CH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CO.sub.2 CH.sub.3                            0CH.sub.3   H      H      CH.sub.2 CF═CF.sub.2                            1CH.sub.3   H      H      CH.sub.2 CH═CCL.sub.2                            0CH.sub.3   H      H      CH.sub.2 CH.sub.2 F                            0CH.sub.3   H      H      CH.sub.2 OCH.sub.3                            0______________________________________ 
    
     
                       TABLE 11______________________________________General Structure 11R         R.sub.2   R.sub.9  m     m.p. (°C.)______________________________________CH.sub.3  H         H        0CH.sub.3  H         CH.sub.3 0CH.sub.3  H         H        1     183-186CH.sub.2 CH.sub.3     H         H        0CH.sub.2 CH.sub.3     H         CH.sub.3 0CH.sub.2 CH.sub.3     H         H        1CH.sub.3  6-Cl      H        0CH.sub.3  7-Cl      H        1CH.sub.3  6-Cl      H        1CH.sub.3  6-CH.sub.3               H        1______________________________________ 
    
     
                       TABLE 12______________________________________General Structure 12R          R.sub.2 R.sub.9  m     m.p. (°C.)______________________________________CH.sub.3   H       H        0CH.sub.3   H       CH.sub.3 0CH.sub.3   H       H        1CH.sub.2 CH.sub.3      H       H        0CH.sub.2 CH.sub.3      H       CH.sub.3 0CH.sub.2 CH.sub.3      H       H        1______________________________________ 
    
     
                       TABLE 13______________________________________General Structure 13R          R.sub.2 R.sub.9  m     m.p. (°C.)______________________________________CH.sub.3   H       H        0CH.sub.3   H       CH.sub.3 0CH.sub.3   H       H        1CH.sub.2 CH.sub.3      H       H        0CH.sub.2 CH.sub.3      H       CH.sub.3 0CH.sub.2 CH.sub.3      H       H        1______________________________________ 
    
     
                       TABLE 14______________________________________General Structure 14R          R.sub.2             R.sub.12       m.p. (°C.)______________________________________CH.sub.3   H      CH.sub.3CH.sub.2 CH.sub.3      H      CH.sub.3CH.sub.3   H      CH.sub.2 CH.sub.3CH.sub.2 CH.sub.3      H      CH.sub.2 CH.sub.3CH.sub.3   H      CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3   H      CH(CH.sub.3).sub.2CH.sub.3   H      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3   H      CH(CH.sub.3)CH.sub.2 CH.sub.3CH.sub.3   H      CH.sub.2 CH(CH.sub.3).sub.2______________________________________ 
    
     
                       TABLE 15______________________________________General Structure 15R            R.sub.2  R.sub.13  m.p. (°C.)______________________________________CH.sub.3     H        HCH.sub.3     H        CH.sub.3CH.sub.2 CH.sub.3        H        HCH.sub.2 CH.sub.3        H        CH.sub.3______________________________________ 
    
     
                       TABLE 16______________________________________General Structure 16R            R.sub.2  R.sub.13  m.p. (°C.)______________________________________CH.sub.3     H        HCH.sub.3     H        CH.sub.3CH.sub.2 CH.sub.3        H        HCH.sub.2 CH.sub.3        H        CH.sub.3______________________________________ 
    
     
                       TABLE 17______________________________________General Structure 17R         R.sub.2  R.sub.13                      R.sub.14                              m.p. (°C.)______________________________________CH.sub.3  H        H       CH.sub.3CH.sub.3  H        H       CH.sub.2 CH.sub.3CH.sub.3  H        CH.sub.3                      CH.sub.3CH.sub.3  H        CH.sub.3                      CH.sub.2 CH.sub.3CH.sub.2 CH.sub.3     H        H       CH.sub.3CH.sub.2 CH.sub.3     H        H       CH.sub.2 CH.sub.3CH.sub.2 CH.sub.3     H        CH.sub.3                      CH.sub.3CH.sub.2 CH.sub.3     H        CH.sub.3                      CH.sub.2 CH.sub.3CH.sub.3  6-Cl     H       CH.sub.3CH.sub.3  6-CH.sub.3              H       CH.sub.3CH.sub.3  6-Cl     CH.sub.3                      CH.sub.3CH.sub.3  7-Cl     H       CH.sub.3______________________________________ 
    
     FORMULATIONS 
     Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further information. 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 18______________________________________       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, N.J., 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 3 
     Wettable Powder 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      80%aminosulfonyl]benzoic acid, methyl estersodium 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 4 
     Wettable Powder 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      50%aminosulfonyl]benzoic acid, methyl estersodium 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 5 
     Granule 
     
         ______________________________________Wettable Powder of Example 3                   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 while tumbling in a double-cone blender. The granules are dried and packaged. 
     EXAMPLE 6 
     Extruded Pellet 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      25%aminosulfonyl]benzoic acid, methyl esteranhydrous 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 7 
     Oil Suspension 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      25%aminosulfonyl]benzoic acid, methyl esterpolyoxyethylene 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 8 
     Wettable Powder 
     
         ______________________________________N&#39;--[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      20%N,N--dimethyl-1,2-benzenedisulfonamidesodium alkylnaphthalenesulfonate                       4%sodium ligninsulfonate      4%low viscosity methyl cellulose                       3%attapulgite                69%______________________________________ 
    
     The ingredients are thoroughly blended. After grinding a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. 
     EXAMPLE 9 
     Low Strength Granule 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       1%aminosulfonyl]benzoic acid, methyl esterN,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 10 
     Aqueous Suspension 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       40%aminosulfonyl]benzoic acid, methyl esterpolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether                      0.5%disodium phosphate         1.0%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 11 
     Solution 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       5%aminosulfonyl]benzoic acid, methyl ester, sodiumsaltwater                      95%______________________________________ 
    
     The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. 
     EXAMPLE 12 
     Low Strength Granule 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       0.1%aminosulfonyl]benzoic acid, methyl esterattapulgite 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 13 
     Granule 
     
         ______________________________________N&#39;--[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      80%N,N--dimethyl-1,2-benzenedisulfonamidewetting 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 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 14-100 mesh (1410-149 microns), and packaged for use. 
     EXAMPLE 14 
     High Strength Concentrate 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       99%aminosulfonyl]benzoic acid, methyl estersilica 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 15 
     Wettable Powder 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                       90%aminosulfonyl]benzoic acid, methyl esterdioctyl 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 16 
     Wettable Powder 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      40%aminosulfonyl]benzoic acid, methyl estersodium 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 17 
     Oil Suspension 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      35%aminosulfonyl]benzoic acid, methyl esterblend of polyalcohol carboxylic esters                       6%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 18 
     Dust 
     
         ______________________________________2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]-                      10%aminosulfonyl]benzoic acid, methyl esterattapulgite                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. 
     UTILITY 
     Test results indicate that the compounds of the present invention are active herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, 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, wheat, barley, cotton, corn and soybeans. 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 selective or general herbicides, the crop species involved, the type of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 5 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations 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. 
     The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. ##STR48## 
     TEST A 
     Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugar beet, 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 greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings: 
     C=chlorosis/necrosis 
     B=burn 
     D=defoliation 
     E=emergence inhibition 
     G=growth retardation 
     H=formative effect 
     U=unusual pigmentation 
     X=axilliary stimulation 
     S=albinism 
     6Y=abscised buds or flowers 
     
                                           TABLE A__________________________________________________________________________  Cmpd. 1       Cmpd.           Cmpd. 3                Cmpd.                    Cmpd. 5                         Cmpd. 6                              Cmpd. 7                                   Cmpd.                                       Cmpd. 9                                            Cmpd.                                                Cmpd.                                                     Cmpd. 12Rate (kg/ha)  0.05 2 0.05           0.05 4 0.05                    0.05 0.05 0.05 8 0.05                                       0.05 10 0.05                                                0.05 0.05__________________________________________________________________________POSTEMERGENCEMorningglory  2C   5C,9G           1C,4G                4C,9G                    5C,9G                         5C,9G                              3C,8H                                   2C,8G                                       9C   5C,9G                                                5C,9G                                                     2CCocklebur  9C   10C 10C  10C 9C   9C   9C   10C 10C  9C  10C  5C,9GCassia 2C   6C,9G           2C,6G                4C,8G                    5C,9G                         3C,5G                              3C,8H                                   4C,9G                                       9C   9C  4C,9G                                                     1CNutsedge  2C   3C,8G           7G   2C,5G                    2C,9G                         2C,9G                              2C,8G                                   9C  2C,9G                                            5C,9G                                                9C   2C,5GCrabgrass  0    2C,6G           2G   4G  4G   3G   2C,5G                                   2C,4G                                       5C,9G                                            5C,8G                                                3C,8G                                                     2GBarnyardgrass  0    3C,9H           2C,9H                3C,9H                    9H   3C,8G                              3C,9H                                   3C,8H                                       9C   5C,9H                                                3C,7H                                                     2C,2GWild Oats  0    2C,6G           2G   0   1C   2C   2G   2G  5C,9H                                            1C  3G   0Wheat  0    2C,4G           2G   1C,4G                    0    0    2G   2G  9C   0   2G   0Corn   3G   1U,7H           2C,6H                3H  2C,9H                         3C,6G                              2C,8H                                   2C,5G                                       9C   2C,8H                                                9H   0Soybean  0    3C,5G           3G   1C,1H                    3C,7G                         3C,5G                              2C,2H                                   3H  2C,4H                                            3C,8G                                                4C,9G                                                     1HRice   2G   3C,8G           2C,8G                2C,8G                    3C,8G                         2C,8G                              4C,9G                                   2C,7G                                       5C,9G                                            9G  2C,8G                                                     0Sorghum  0    2C,8G           9G   7H  9G   5G   1C,9G                                   5G  5C,9G                                            2C,9G                                                3C,8H                                                     0Sugar Beets  5C,9G       4C,9G           3C,8G                3C,5G                    4C,8G                         4C,8G                              3C,7G                                   9C  10C  9C  5C,9G                                                     3C,7GCotton 2C,4G       9C  5C,9G                5C,9G                    9C   6C,9G                              10C  10C 10C  9C  5C,9G                                                     3C,7GPREEMERGENCEMorningglory  2C,8G       9G  5G   7G  9G   9G   9G   9G  9G   9G  9G   6GCocklebur  9H   5G  7H   8G  9H   --   8H   --  8G   --  9G   9HCassia 6G   5G  0    5G  7G   8G   8G   7G  8G   7G  8G   6GNutsedge  0    2G  7G   10E 10E  0    10E  5G  9G   10E 5G   0Crabgrass  0    0   0    0   5G   2G   7G   0   3C,8G                                            3G  2G   0Barnyardgrass  1C   3G  4G   5G  4G   3C,3H                              2C,8G                                   0   2C,8G                                            2C,7G                                                3G   0Wild Oats  0    5G  3G   0   2C,4G                         2C,3G                              5G   0   5G   2C  2C,6G                                                     0Wheat  0    3G  0    0   0    0    0    2G  4G   0   4G   0Corn   2C,6G       6G  4G   5G  2C,7G                         3C,6G                              8G   1C,6G                                       2C,8G                                            3C,8G                                                2C,8G                                                     2C,5GSoybean  0    0   0    0   2C,4H                         2C,3H                              3H   2H  2H   0   3C,6G                                                     0Rice   4G   8G  9G   2C,7H                    7G   3C,7G                              10E  5G  10E  2C,7G                                                6G   0Sorghum  3G   7G  5G   6G  8G   2C,6G                              2C,9G                                   3G  2C,9G                                            2C,9H                                                8G   0Sugar Beets  9G   7G  8G   6G  9G   9G   8G   8G  4C,9G                                            2C,8G                                                9G   3GCotton 9G   8G  4G   10E 9G   8G   9G   9G  9G   9G  9G   7G__________________________________________________________________________ 
    
     TEST B 
     Postemergence 
     Two round pans (25 cm diameter by 12.5 cm deep) were filled with sassafras sandy loam soil. One pan was planted with blackgrass (Alopecurus myosuroides), sugar beets, nutsedge (Cyperus rotundus) tubers, crabgrass, (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), and giant foxtail (Setaria faverii). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusgalli). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic solvent. 
     Preemergence 
     Two round pans (25 cm diameter by 12.5 cm deep) were filled with sassafras sandy loam soil. One pan was planted with blackgrass, sugar beets, nutsedge, crabgrass, sicklepod, teaweed, jimsonweed, velvetleaf, and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent. 
     Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response. The response rating system was described for Test A. 
     Response ratings are contained in Table B. 
     
                                           TABLE B__________________________________________________________________________  Compound 2         Compound 4                   Compound 5                          Compound 6                                 Compound 7                                         Compound 10                                                Compound 11Rate (g/ha)  62 16       04         250            62              16 04                   62 16                        04                          250                             62                               16                                 250                                    62                                      16 62  04 62 16 04                                                         01__________________________________________________________________________POSTEMERGENCECorn   5G 0 0 3G 2G              0  0 4G 0 0 0  0 0 8G 3G                                      0  2G  0  7G 3G 0 0Wheat  0  0 0 0  0 0  0 0  0 0 0  0 0 0  0 0  0   0          0                                                        0                                                        0                                                        0Rice   9G 5G       2G         9G 8G              5G 0 5G 0 0 7G 3G                               0 9G 5G                                      2G 5G  0          2G                                                        0                                                        0                                                        0Soybean  2G 0 0 2G 0 0  0 0  0 0 2G 0 0 4G 2G                                      0  0   0          8G                                                        3G                                                        0                                                        0Cotton 9G 7G       2G         9G 8G              6G 2G                   7G 4G                        0 6G 2G                               0 9G 7G                                      3G 7G  0          10C                                                        10C                                                        8G                                                        0Sugar beet  9G 8G       2G         9G 7G              3G 0 7G 2G                        0 9G 7G                               3G                                 7G 0 0  9G  6G         10C                                                        9G                                                        5G                                                        2GCrabgrass  7G 3G       0 9G 9G              8G 4G                   6G 2G                        0 6G 2G                               0 9G 3G                                      0  6G  2G         3G                                                        0                                                        0                                                        0Johnsongrass  8G 7G       3G         9G 7G              5G 0 8G 3G                        0 5G 2G                               0 10G                                    9G                                      9G 10G 5G         6G                                                        2G                                                        0                                                        0Blackgrass  8G 7G       2G         10G            9G              5G 0 2G 0 0 4G 0 0 8G 4G                                      0  4G  0          2G                                                        0                                                        0                                                        0Barnyardgrass  9G 8G       4G         9G 8G              4G 0 7G 3G                        0 7G 2G                               0 9G 8G                                      7G 8G  2G         5G                                                        0                                                        0                                                        0Nutsedge  9G 4G       0 9G 8G              5G 2G                   9G 4G                        0 6G 0 0 9G 8G                                      3G 9G  4G         5G                                                        2G                                                        0                                                        0Giant Foxtail  6G 2G       0 8G 6G              2G 0 9G 2G                        0 4G 0 0 9G 9G                                      6G 8G  0          3G                                                        0                                                        0                                                        0Wild Oats  4G 0 0 0  0 0  0 0  0 0 0  0 0 0  0 0  0   0          0                                                        0                                                        0                                                        0Cocklebur  9G 7G       0 10G            9G              4G 0 9G 5G                        0 9G 6G                               0 9G 9G                                      3G 10G 5G         10C                                                        8G                                                        6G                                                        2GMorningglory  9G 8G       2G         10G            7G              3G 0 9G 4G                        0 10G                             9G                               2G                                 8G 4G                                      0  10G 2G         10G                                                        10G                                                        4G                                                        0Teaweed  9G 5G       0 9G 9G              8G 2G                   9G 7G                        2G                          9G 7G                               2G                                 10G                                    6G                                      2G 9G  4G         8G                                                        7G                                                        4G                                                        2GCassia 9G 5G       0 9G 9G              6G 2G                   10G                      9G                        3G                          9G 8G                               3G                                 9G 5G                                      3G 10G 5G         10C                                                        9G                                                        7G                                                        5GJimsonweed  9G 7G       3G         10G            8G              6G 2G                   10G                      5G                        0 9G 9G                               2G                                 10G                                    8G                                      6G 9G  3G         10C                                                        9G                                                        8G                                                        3GVelvetleaf  9G 7G       4G         9G 9G              7G 3G                   9G 4G                        0 9G 8G                               3G                                 10G                                    9G                                      3G 9G  6G         10C                                                        7G                                                        5G                                                        0__________________________________________________________________________Rate (g/ha)  250     62       16         250            62     250                      62                        16                          250                             62  250                                    62                                      16 250 62 250                                                   62 16__________________________________________________________________________PREEMERGENCECorn   3G 0 0 0  0      5G 2G                        0 0  0   7G 5G                                      0  2G  0  3G 0  0Wheat  3G 0 0 0  0      0  0 0 0  0   0  0 0  0   0  0  0  0Rice   9G 9G       8G         9G 8G     9G 6G                        4G                          9G 7G  9G 9G                                      8G 9G  8G 8G 4G 0Soybean  3G 0 0 0  0      0  0 0 0  0   0  0 0  4G  0  3G 0  0Cotton 6G 3G       0 2G 0      5G 2G                        0 2G 0   3G 0 0  5G  0  6G 2G 0Sugar beet  8G 7G       3G         5G 3G     6G 3G                        0 7G 3G  3G 0 0  7G  3G 10G                                                   10G                                                      6GCrabgrass  8G 7G       2G         9G 3G     7G 3G                        0 0  0   9G 4G                                      2G 9G  5G 5G 2G 0Johnsongrass  9G 8G       3G         8G 6G     8G 6G                        2G                          3G 0   9G 9G                                      4G 10G 9G 5G 0  0Blackgrass  9G 9G       8G         9G 9G     8G 6G                        2G                          8G 6G  9G 9G                                      6G 8G  7G 8G 6G 2GBarnyardgrass  9G 7G       3G         9G 7G     8G 4G                        0 6G 2G  9G 8G                                      4G 9G  7G 4G 0  0Nutsedge  9G 8G       0 9G 8G     9G 9G                        3G                          2G 0   10E                                    9G                                      3G 9G  8G 8G 3G 0Giant Foxtail  10E     7G       2G         9G 8G     8G 3G                        0 8G 2G  8G 7G                                      3G 9G  7G 5G 0  0Wild Oats  6G 4G       0 0  0      0  0 0 0  0   0  0 0  2G  0  0  0  0Cocklebur  7G 3G       0 6G 0      6G 3G                        0 6G 0   0  0 0  9G  6G 4G 2G 0Morningglory  8G 4G       0 7G 0      7G 3G                        0 3G 0   3G 0 0  8G  5G 5G 2G 0Teaweed  9G 9G       4G         9G 7G     8G 5G                        0 8G 3G  9G 6G                                      0  9G  8G 10G                                                   8G 5GCassia 8G 6G       2G         7G 2G     7G 2G                        0 4G 0   4G 0 0  7G  0  10G                                                   9G 4GJimsonweed  9G 7G       4G         9G 9G     9G 8G                        3G                          9G 7G  9G 8G                                      7G 9G  7G 10G                                                   9G 3GVelvetleaf  9G 8G       4G         7G 5G     8G 4G                        0 8G 6G  7G 0 0  9G  7G 10G                                                   9G 3G__________________________________________________________________________