HERBICIDAL PYRROLE SULFONAMIDES

Abstract: Compounds of the formula:- wherein R₁ is H, alkyl, NO₂, CN, CO₂H, or various acyl or ester groups: R₂ is H or alkyl; R₃ is H, alkyl, Cl or Br; R₄ is H, alkyl, cyanoethyl, cycloalkyl, benzyl, substituted phenyl, or various acyl; ester or amide groups; R₉ is H, CH₃ or OCH₃; R₁₀ is wherein X is CH₃ or OCH₃; Y and Y¹ are H, Cl or various organic groups; Z is CH, N, CCH₃, CCH₂CH₃, CCH₂CH₂Cl, CCl, CBr or CF; and their agriculturally suitable salts; exhibit herbicidal activity. Some can be used as plant growth regulants. The compounds can be formulated for use in conventional man­ ner. The compounds (Ic) and (Ib) can be made by reacting The compounds of formula (III) are also novel; these may be made by reacting chlorosulfonyl isocyanate with the appropriate heterocyclic amine R₉R₁₀NH.

Description: "Herbicidal pyrrole sulfonamides and sulfamyl chloride intermediates" Background of the Invention This invention relates to pyrrole sulfonamides and in particular their use as agricultural chemicals and particularly as herbicides, to a process for the preparation of the pyrrole sulfonamides, and to sulfamyl chlorides which are useful intermediates for the preparation of the pyrrole sulfonamides. U.S. Patent 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula EMI1.1 where in EMI1.2 R3 and R6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, tri fluoromethyl, cyano, CHJS(O) or CH3CH2S(O)n R4 is hydrogen, fluorine, chlorine, bromine or methyl; R5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; R7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms R3 is hydrogen, methyl, chlorine or bromine; R3 and R10 are independently hydrogen, methyl, chlorine or bromine; W and Q are independently oxygen or sulfur; n is 0, 1 or 2; ; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH3S- or CE3OCX2-; and y is methyl or methoxy; or their agriculturally suitable salts; provided that: (a) when R5 is other than hydrogen, at least one of R3, R4, R6 and R7 is other than hydrogen and at least two of R3, R4, R6 and R7 must be hydrogen; (b) when R is hydrogen and all of R4, R6 and R7 are other than hydrogen, then all of R3, R4, R6 and R7 must be either chlorine or methyl; and (c) when R3 and R7 are both hydrogen, at least one of R4, R5 or R must be hydrogen. wrench Patent No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: EMI2.1 wherein R = H, halogen, cr3 or alkyl. Logemann et'al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: EMI3.1 wherein R is butyl, phenyl or EMI3.2 and R1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 b the compounds in which R is butyl and phenyl were most otent. The others were of low potency or inactive. Wojciechowski, J. Acta. Polon. Pharo. 19, p. 121-5 (1962) [Chem Ab., 59 1633 el describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: EMI3.3 Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound. Netherlands Patent 121,788, published Se?tzmber 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, EMI3.4 wherein R1 and R2 may independently be alkyl of 1-4 carbon atoms; and R3 and R4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974), EMI4.1 wherein R is pyridyl. German Patent 2,439,087 discloses the following compound: EMI4.2 The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, hcwever, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops. Summary of the Invention This invention relates to novel compounds of Formula I, to a process for preparing them, to compositions containing them and to the methods of using them as broad spectrum herbicides as well as pre-emergence and post-emergence selective herbicides and plant growth regulants. EMI6.1 wherein R1 is H, C1-C4 alkyl, NO2, CN, C(O)CC131 SO2Rll, C(O)R5 or C 2H; R2 is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, Cl or Br; R4 is H, C1-C4 alkyl, cyanoethyl, C5-C6 cycloalkyl, benzyl, phenyl substituted with Cl or NO2, or C(O)R6; R5 is C1-C4 alkyl or C1-C4 alkoxy; R6 is C1-C4 alkyl, C1-C4 alkoxy, or NR7R8; R7 and R8 are independently C1-C2 alkyl; Rg is H, CH3 or OCH3; R11 is C1-C4 alkyl; R10 is EMI7.1 X is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, OCH2CF3, C1, CH20CH3, CH2OCH2CH3 or CF3; is H, CH3, OCH3, C1 or OCH2CH3; and Z is CH, N, CCH3 CCH 2CH3, CCH2CH2C1, CC1, CBr or CF; and their agriculturally suitable salts; provided that (1) when R4 is C(O)R6, t-butyl or phenyl substituted with Cl or NO2, then R1 is H or C1-C4 alkyl and R1, R2 and R3 cannot be s-butyl Of isopropyl; (2) R11 R2, R3 and R11 cannot be t-butyl; (3) in Formula Ia, when R1 is NO2, then R1 cannot be in the 5-position; (4) in Formula Ia, when R1 is not in the 5-position, R2 and R3 are other than H, and R1 must be other than H unless both R2 and R3 are H; (5) in Formula Ia, R3 cannot be C1 or Br; (6) in Formula Ib, R1 cannot be C(O)CC13; and (7) in Formula Ib, when R3 is C1 or Br, then R3 is in the 3-position and R1 is in the 5-position.and R1 cannot be H or C1- C4 alkyl. Prefer red for their higher herbicidal activity and/or their more favorable ease of synthesis are: (1) Compounds of the generic scope wherein Rg is H or CH3; (2) Compounds of the Preferred (1) wherein R10 is EMI8.1 (3) Compounds of the Preferred (2) wherein Z is CH or N; R5 is C1-C4 alkoxy; R2 is H; R4 is H, C1-C4 alkyl or benzyl; (4) Compounds of the Preferred (3), of Structure Ia, wherein R1 is H, C1-C4 alkyl.or COR5; (5) Compounds of the Preferred (3), of Structure Ib, wherein R1 is H, C-C4 alkyl, NO2 or COR5; (6) Compounds of the Preferred (4) wherein R1 is in the 5 position; (7) Compounds of the Preferred (5) wherein R1 is H, NO2 or COR5; and (8) Compounds of the Preferred (6) or (7) wherein Y is CH3, OCH3 or OCH2CH3. Specifically preferred for highest herbicidal activity and/or greatest ease of synthesis are the following compounds: N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,5- dimethyl-lH-pyrrole-3-sulfonamide; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-lH- pyrrole-2-sulfonamide; N-[ (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl]- lH-pyrrole-2-sulfonamide; N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino- carbonyl] -2,5-dimethyl-lH-pyrrole-3-sulfonamide; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-methyl lH-pyrrole-X-sulfonamide; (X indicates mixtures of pyrrole-2- and pyrrole-3-sulfonamides) N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1- (phenylmethyl) -lH-pyrrole-X-sulfonamide; (X indi cates mixtures of pyrrole-2- and pyrrole-3-sulfon amides); X-[((4,6-dimethylpyrimidin-2-yl)aminocarbonyl)amino- sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid, methyl ester; (X indicates mixtures of 4- and 5-substituents); N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-X-nitro lH-pyrrole-2-sulfonamide; (X indicates mixtures of 3 and 4-substituents) 4-[((4,6-dìmethylpyrimidin-2-yl)aminocarbonyl)amino- sulfonyl]-lH-pyrrole-2-carboxylic acid, methyl ester; 5-[( (4,6-dimethylpyrimidin-2-yl)aminocarbonyl)amino- sulfonyl] -4-bromo-lH-pyrrole-2-carboxylic acid, methyl ester; X-[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl) aminosulfonyl] -lH-pyrrole-2-carboxylic acid, methyl ester; (X indicates mixtures of 4- and 5 substituents); and 4-bromo-5-[((4,6-dimethylpyrimidin-2-yl)aminocarbonyl) aminosulfonyl)-l-methyl-lH-pyrrole-2-carboxylic acid, ethyl ester. These compounds may be used as their agricuiturally suitable salts, where appropriate: This invention also relates to sulfamoyl chlorides of Formula III which are useful as intermediates for preparing pyrrole sulfonamides of Formula I: EMI10.1 III wherein Rg is H, CH3 or OCH3; Rio EMI10.2 X is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, OCH2CF3, C1, CH2OCH3, CH2OCH2CH3 or CF3; is H, CH3, OCH3, C1 or OCH2CH3; and Z is CH, N, CCH3,CCH2CH3, CCH2CH2C1, CC1, CBr or CF. Preferred Compounds Preferred intermediates for reasons of higher activity of the derived herbicides are: (1) Compounds of the generic scope wherein Rg is H or CH3; (2) Compounds of the Preferred (1) wherein Y is CH3, OCH3 or OCH2CH3; and Z is CH or N; (3) Compounds of Preferred (2) wherein yl is H, CH3 or OCH3; (4) Compounds of Preferred (1)-(3) wherein Rg is H; and (5) Compounds of Preferred (4) wherein R10 is EMI11.1 Specifically preferred for reasons of greatest activity of the resulting herbicides are: [(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamoyl chloride; [(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] sulfamoyl chloride; [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamoyl chloride; (4,6-dimethyl-1,3,5-triazin-2-yl)aminocabonyl]sul famoyl chloride; [(4-methOxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- sulfamoyl chloride; [(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]sul famoyl chloride; [(4-ethOxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- sulfamoyl chloride; [(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)amino carbonyl]sulfamoyl chloride; ; [(5,6-dihydrofuor[2,3-d]pyrimidin-2-yl)(methyl)aminocar sulfamoyl chloride; [(5,6-dihydro-4-methoxy[2,3-d]pyrimidin-2-yl)amino- carbonyl]sulfamoyl chloride; [(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]- sulfamoyl chloride; [(4,6-dimethylpyrimidin-2-yl) (methyl)aminocarbonyl]- sulfamoyl chloride; [(4,6-dimethoxypyrimidin-2-yl) (methyl)aminocarbonyl]- sulfamoyl chloride; [(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino bonyl]sulfamoyl chloride; [(4,6-dimethyl-1,3,5-triazin-2-yl)(methyl)aminocar- bonyl]sulfamoyl chloride; [(4,6-dimethoxy-l,3,5-triazin-2-yl) (methyl)aminocar- bonyl]sulfamoyl chloride; and [(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)amino carbonyl] sulfamoyl chloride. This invention also relates to a novel process for preparing compounds of Formula Ia and Ib. ThP process comprises contacting under reaction conditions, e.g. in a solvent and in the presence of a Friedel Crafts catalyst, a compound of Formula II with a compound of Formula III: : EMI13.1 wherein R1 is H, C1-C4 alkyl, NO2, CN, C(O)CC13, SO2R11, C(O)R5 or CO2H; R2 is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, C1 or Br; R4 is H, C1-C4 alkyl, cyanoethyl, C5-C6 cycloalkyl, benzyl, phenyl substituted with Cl or NO2, or C(O)R6; R5 is C1-C4 alkyl or C1-C4 alkoxy; R6 is C1-C4 alkyl, C1-C4 alkoxy, or NR7R8; R7 and R8 are independently C1-C2 alkyl; Rg is H, CH3 or OCH3; R11 is C1-C4 alkyl; R10 is EMI14.1 X is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, OCH2CF3, C1, CH20CH3, CH2OCH"CH3 or CF3; YÚ is H, CH3, OCH3, Cl or OCH2CH3; and Z is CH, N, CCH3 CCH2CH3, CCH2CH2C1, CC1, CBr or CF; and their agriculturally suitable salts; provided that (1) when R4 is C(O)R6, t-butyl or phenyl substituted with C1 or NO2, then R1 is H or C1-C4 alkyl and R1, R2 and R3 cannot be s-butyl or isopropyl; (2) R1, R2, R3 and R11 cannot be t-butyl; (3) in Formula Ia, when R1 is NO2, then R1 cannot be in the 5-position; (4) in Formula Ia, when R1 is not in the 5-position and R2 and R3 are other than H then R1 must be other than H; (5) in Formula Ia, R3 cannot be C1 or Br; (6) in Formula Ib, R1 cannot be C(O)CC13; and (7) in Formula Ib, when R3 is C1 or Br, then R3 is in the 3-position and R1 is in the 5-position and R1 cannot be H or C1-C4 alkyl. Preferred for reasons of the higher herbicidal activity of the derived products and/or greater ease of synthesis are: (1) The process of the generic scope wherein Rg is H or CH3; (2) The process of Preferred (1) wherein R10 is EMI15.1 (3) The process of Preferred (2) wherein Z is CH or N; R5 is C1 C4 alkoxy; R2 is H; and R4 is H, C1-C4 alkyl or benzyl; (4) The process of Preferred (3) for com pounds of structure Ia wherein R1 is H, C1-C4 alkyl or COR5; (5) The process of Preferred (3) for com pounds of structure Ib wherein R1 is H, C1-C4 alkyl, NO2 or COR5; (6) The process of Preferred (4) wherein R1 is in the 5-position; (7) The process of Preferred X5) wherein R1 is H, NO2, or COR5; (8) The process of Preferred (6) or (7) wherein Y is CH3, OCH3 or OCH2CH3; ; (9) The process of generic scope in which the Friedel-Crafts catalyst is selected from aluminum (III) chloride, aluminum (III) bromide, gallium (III) chloride, tin (IV) chloride, iron (III) chloride, antimony (V) chloride, antimony (V) fluoride, zinc (II) chloride, antimony (III) chloride, titanium (IV) chloride, boron (III) fluoride, sulfuric acid or hydrofluoric acid; (10) The process of generic scope wherein the catalyst is aluminum (III) chloride; (11) The process of generic scope wherein the solvent is methylene chloride, tetrahydrofuran, nitromethane, nitro ethane or nitropropanes; (12) The process of generic scope wherein the reaction takes place at a tempera ture of about -80 to 100C for a period of about 0.1 to 4 hours followed by a period of about 0.5 to 48 hours at a temperature of about 250C up to the boiling point of the solvent; ; (13) The process of generic scope wherein the reaction takes place at a temper an ture of about -80 to -400C for a period of about 0.1 to 1 hour in a solvent of tetrahydrofuran or nitroethane, fol lowed by a period of about 0.5 to 24 hours at about ambient temperature in the presence of a catalytic amount of aluminum (III) chloride; (14) The process of the generic scope wherein the reaction takes place at a temperature of about -10 to 100C for a period of about 0.1 to 1 hour in a sol vent of nitromethane, followed by a period of about 0.5 to 24 hours at a temperature of about ambient up to the boiling point of the solvent, in the presence of an equimolar amount of aluminum (III) chloride. Detailed Description of the Invention Methods A and B Two general methods (A and B) for the preparation of the compounds of this invention are illustrated by the following equation: EMI18.1 In Method A, Step I may be carried out at temperatures ranging from -80 to -40 C. Step II may be carried out at temperatures ranging from -80 to ambient and optionally in the presence of a Friedel Crafts catalyst. Method A is preferred for the preparation of compounds of the invention in which R1 is H or alkyl and R4 is other than substituted phenyl or C(O)R6. In general, the conditions of Method A are usually insufficient to effect conversion of pyrroles II in which R1 is other than alkyl or H or in which R4 is substituted phenyl or C(O)R6 to the compounds of the invention, Ia or Ib, in synthetically useful yields. In Method B, Step I is carried out at temperatures ranging from -100 to 100C. Step II is performed at temperatures ranging from -100 to the boiling point of the solvent employed and in the presence of equimolar Friedel-Crafts catalyst. Method B is preferred for the preparation of compounds of the invention in which R1 is other than H or alkyl or in which R4 is substituted phenyl or C(O)R6. Synthesis - Method A As indicated above, compounds of this invention may be prepared by contacting a heterocyclic amine R9R10NH and chlorosulfonyl isocyanate to form an intermediate compound of Formula III which is then contacted with a pyrrole of Formula II, optionally in the presence of a Friedel-Crafts catalyst, to produce herbicidal N-(substituted heterocyclic aminocarbonyl)pyrrole sulfonamides of Formulae Ia and Ib. In some instances, isomeric products are obtained and these materials may be separated by column chromatography, preparative high pressure or medium pressure liquid chromatography or similar methods. In cases in which isomer separation cannot be carried out successfully or can be accomplished only with great difficulty, the isomeric identity of the products is sometimes uncertain and it should be understood that the compounds of this invention may include these isomeric products. The heterocyclic amine RgRloNH is suspended or dissolved in an inert organic solvent, such as dichloromethane, nitroethane, nitropropanes or tetrahydrofuran. Tetrahydrofuran or nitroethane are preferred. The reaction mixture is preferably maintained in an inert atmosphere at a temperature of -80 to -400C. One equivalent of chlorosulfonyl isocyanate, either neat or, if tetrahydrofuran is not the solvent, dissolved in the corresponding solvent, is contacted with the starting material at such a rate as to maintain the reaction temperature within the preferred range. Reaction Step I proceeds rapidly and is allowed to continue for a period of 0.1 to 1 hour to insure complete formation of intermediate III. This compound is preferably not isolated, but is contacted at -80 to -40 with one to ten equivalents of pyrrole II, dissolved in the corresponding solvent. Use of one equivalent of pyrrole II is preferred. Step II is optionally carried out in the presence of a Friedel-Crafts catalyst such as aluminum (III) chloride, aluminum (III) bromide, gallium (III) chloride, tin (IV) chloride, iron (III) chloride, antimony (V) chloride, antimony'(V) fluoride, zinc (II) chloride, antimony (III) chloride, titanium (IV) chloride, boron (III) fluoride, sulfuric acid or hydrofluoric acid. The use of such a catalyst in Step II of the reaction is the method of choice. Preferred is aluminum (III) chloride in catalytic quantities, the exact amounts of which would be apparent to one skilled in the art. The reaction mixture is allowed to warm to ambient temperature and maintained there for a period of from O.5 to 24 hours. The reaction is conveniently monitored by observing the disappearance of starting pyrrole II by thin layer chromatography in a suitable solvent system. In some cases, the products of Formulae Ia and/or Ib may be isolated by partitioning the reaction mixture between dilute aqueous alkali and an organic solvent such as dichloromethane or chloroform. The products are soluble in the aqueous phase and may be precipitated from it, after separation of the layers, by the addition of an excess of an acid such as acetic acid or hydrochloric acid. If the products do not precipitate on acidification they may then be isolated by extraction into an organic solvent such as dichloromethane or ethyl acetate followed by evaporation of the solvent. This procedure is most useful in cases in which tetrahydrofuran is the reaction solvent. When the reaction is carried out in water-immiscible solvents such as dichloromethane or nitroethane, isolation of the products may best be carried out by contacting the reaction mixture with water, followed by separation of the organic phase and further extraction of the products into an organic solvent such as dichloromethane, nitromethane, nitroethane or ethyl acetate. After evaporation of the solvent, purification of the reaction products may be-accomplished by trituration with an appropriate solvent, recrystallization or chromatography. Synthesis - Method B Method B is procedurally similar to Method A. For this method, suitable solvents include but are not limited to nitromethane, nitroethane, nitropropanes and dichloromethane; nitromethane is the solvent of choice. The reaction mixture is initially maintained at a temperature of -200 to 0 and Step I is preferably carried out between -100 and 100C. Again, a reaction time of 0.1 to 1 hour is allowed for the formation of intermediate III. The compound is contacted at -100 to 100C with one equivalent of pyrrole II followed by an equimolar amount of Friedel-Crafts catalyst, preferably aluminum (III) chloride. The reaction mixture is allowed to warm to ambient temperatures and then, Step II of the reaction is allowed to proceed at temperatures ranging from ambient to the boiling point of the solvent for a period of from 0.5 to 24 hours. In general, the higher reaction temperatures and shorter reaction times (0.5 to 4 hours) afford the best yields in Step II. Products Ia and/or Ib may be isolated by the procedure described in Method A for the reaction in water-immiscible solvents and purification of the resulting compounds may be accomplished in like fashion. The synthesis of heterocyclic amine derivatives has been reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI'of the above series. The 2-amino-1,3,5-triazines are reviewed by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII of the same series. The synthesis of triazines is also described by F. C. Schaefer, U.S. 3,154,547 and by K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812-1821 (1963). The synthesis of the bicyclic heterocyclic amines IV and V wherein yl is as previously defined is described in the unexamined European Patent SpeÇi-fication 15,683, published September 17, 1980. EMI23.1 The pyrimidine intermediates of structure VI in which yl is methyl, have been reported in the literature by E. Bisagni, et. al., Bull. Soc. Chim. Fr., 803 (1969). A more efficient procedure is depicted in the equation below. EMI24.1 The known keto-ester precursor VII (e.g., J. F. Tinker and T. E. Whatmough, J. Amer. Chem. Soc., 74, 5235 (1952)) is treated with excess guanidine carbonate in an organic solvent, preferably a polar aprotic solvent such as dimethylsulfoxide (DMSO), dimethylformamide (DMF) or N,N-dimethylacetamide, at a temperature of 800 to 2000, preferably 1000 to 1600, ambient pressure and preferably under an inert atmosphere to yield both VIII and VI (where yl is CH3) . The products are isolated upon dilution of the reaction mixture with, for example, acetone and water successively. Higher reaction temperatures and longer reaction times (e.g., in DMSO at 1300 to 1500 for 2 to 8 hours) favor the production of VI over VIII. The pyrimidine intermediates VI in which yl is C1 may be prepared by condensing the known ethyl 2-carboethoxy-4-pentynoate IX with guanidine carbonate in an alcohol solvent such as ethanol to give the intermediate pyrimidine X as shown below. EMI25.1 Conversion to the dichloropyrimidine XI may be accomplished by heating X in phosphorous oxychloride. The product may be isolated by removal of the phosphorous oxychloride under reduced pressure, trituration of the residue with ice-water and filtration of th solid product. Contacting the dichloropyrimidine with two equivalents of an aqueous alkali metal hydroxide, such as sodium hydroxide, yields the furopyrimidine VI in which yl is C1. The reaction is best carried out in the presence of a solubilizing agent which is water miscible, such as t-butanol, dioxane or tetrahydrofuran, and at temperatures of 20 to 1000 or at the boiling point of the solvent mixture used. The product may be isolated by cooling the mixture or further dilution with water to effect precipitation. Compounds of Formula VI in which yl is OCH3 or OCH2CH3 may be prepared by treatment of the corresponding compound in which yl is C1 with sodium methoxide in boiling methanol or with sodium ethoxide in refluxing ethanol, respectively. The product is obtained on evaporation of the alcohol solution, trituration of the residue with cold water and subsequent filtration. Compounds of Formula VI in which Y is H may be prepared by reaction of the corresponding compound in which yl is C1 with a reducing agent such as zinc dust in acetic acid or -toluenesulfonylhydrazide, the latter by a procedure similar to that described by Albert and Royer, J. Chem. Soc., 1148 (1949). The aminoheterocyclic intermediates of R9R1ONH in which Rg is CH3 may be prepared by the following procedure, or by obvious modifications: EMI27.1 A solution of the amine XII in concentrated hydrochloric acid is treated with an aqueous sodium nitrite solution and the chloro compound XIII is isolated in the usual manner by filtration of the acidic solution (see for example, Bee and Rose, J. Chem. Soc. C., 2051 (1966) for the case in which Z is CH and X and Y are OCH3) . Displacement of the chlorine may be accomplished by heating with an excess of methylamine in water to obtain the methylamino heterocycle XIV. N-Methoxyamino heterocycles can be prepared by procedures reported in the literature [see, for example, Belgian Patent 618,563 and J. T. Shaw, et al., J. Org. Chem., 27, 4054 (1962)] and illustrated below: EMI28.1 Chloro compound XIII is reacted with hydroxylamine to form derivative XV which may be alkylated with methyl bromide to afford the N-methoxy heterocyclic amine XVI. This compound may alternatively be prepared in one step by treatment of XIII and O-methyl hydroxylamine hydrochloride with an alkali metal hydroxide such as sodium hydroxide. The pyrroles required as starting materials for this invention are represented by the generalized structure II where R1, R2, R3 and R4 are as previously defined. EMI29.1 The synthesis of pyrroles has been extensively reviewed; e.g., by R. Alan Jones and G. P. Bean, "The Chemistry of Pyrroles", Academic Press, London (1977); by J. M. Patterson, Synthesis, 281-304 (1976); and by A. Gossauer, "Die Chemie der Pyrrole", Springer Verlag, West Berlin (1974). These articles are herein incorporated by reference. The preparation of a wide variety of alkyl substituted pyrroles by numerous routes has been reported in the literature and appropriate methods for this synthesis of pyrroles of Formula II wherein R1 is H or C1-C4 alkyl, R2 is H or C1-C4 alkyl, R3 is H or C1-C4 alkyl and R4 is H, C1-C4 alkyl, C5-C6 cycloalkyl or phenyl substituted by NO2 or C1 would be, from the above, apparent to one skilled in the art. For starting pyrroles in which R1 is C(O)R5, CN, NO2 or SO2Rll and R3 is other than C1 or Br, the accessability of the fourteen different generalized pyrrole substitution patterns shown below is required for this invention. In these structures, the values of R2 and R3 have been restricted to H or CH The methods described for the synthesis of these methyl substituted compounds are, however, applicable to the preparation of the higher alkyl homologs as well. EMI30.1 Pyrroles IIa-IIn in which R1 is CO2CH2CH3 and R4 is H are all known in the literature [see for example, "Beilsteins Handbuch der Organischen Chemie", Volume 22, Supplementary Series III/IV, Springer-Verlag (Berlin), 1979, pp. 225-275]. The other pyrrole esters (R1 is C(O)R5 and R5 is C1-C4 alkoxy) may be prepared from these compounds by methods which would be known to one skilled in the art. Pyrroles IIa-IIn in which R1 is CN or C(O)CH3 and R4 is H may also be found in the literature [see for example, "Beilstein's Handbuch der Organischen Chemie", Volume 22, Supplementary Series I-IV, System Number 3181, Springer-Verlag (Berlin); P. E. Sonnet and J. C. Moser, J. Agr. Food Chem., 20, (6) 1191-4 (1972); P. Pfaffli and C. Tamm, Helv. Chim. Acta., 52 (7) 1911-20 (1969); L. F. Elsom and R. A. Jones, J. Chem. Soc. B., (1) 79-81 (1970) and references therein; A. M. van Leusen, et. al., Tetrahedron Lett., 5337 (1972); J. W. Ducker and M. J. Gunter, Aust. J. Chem., 26 (7) 1551-69 (1973)]. The methods used for the preparation of these compounds in which R1 was C(O)CH3 can be readily applied to the synthesis of similar systems in which R1 is d(O)R5 and R5 is C1- C4 alkyl. Pyrroles of structures IIa, IIb, IIc, IIf and IIn in which R1 is NO2 and R4 is H are known in the literature fK. J. Morgan and D. P. Morrey, Tetrahedron 22, 57-62 (1966); P. E. Sonnet, J. Het. Chem., 7 (2) 399-400 (1970); T. A. Melent'eva, et. al., Zh. Obshch. Khim., 41, 179 (1971); T. A. Melent'eva, et. al., ibid, 42, 2274 (1972)]. Nitration of 3-methyl pyrrole with nitric acid in acetic anhydride at low temperatures affords a mixture of pyrroles IIg and IIh. Similarly, reaction with 2,3-dimethylpyrrole affords a mixture of IIk and IIm. These isomeric products may be separated by chromatography to afford the desired systems. Nitration of 2,5-dimethylpyrrole, 3,4-dimethylpyrrole and 2,4-dimethylpyrrole under the conditions described above affords II1, IIj and Ili respectively. Nitration of the known diethyl ester of 5-methyl-2,4-pyrroledicarboxylic acid, followed by alkaline hydrolysis to the diacid and decarboxylation in refluxing 2-aminoethanol or in quinoline with copper chromite at 1800 produces pyrrole IIe. A similar sequence beginning with the known diethyl ester of 3-methyl-2,5-pyrroledicarboxylic acid gives access to IId. The preparation of pyrrole IIa in which R1 is SO2CH3 and R4 is H is described by R. K. Olsen and H. R. Snyder, J. Org. Chem., 28, 3050 (1963). Procedures described in this reference, by R. L. N. Harris, Aust. J. Chem., 23, 1199-207 (1970); R. L. N. Harris and S. Beveridge, ibid, 24, 1229-36 (1971) and by R. L. N. Harris, ibid, 25, 985-91 (1972) are useful for the synthesis of alkylsulfonyl pyrroles. Contacting of the known pyrrole dicarboxylic acid esters XVIIa-c EMI33.1 ["Beilstein's Handbuch der Organischen Chemie", Volume 22, Supplementary Series III/IV, Springer-Verlag (Berlin) 1979, pp. 1543-1561] either with thiourea in the presence of iodine and potassium iodide or with a thiocyanogen-halide followed by alkaline hydrolysis to the thiol salt, alkylation with an appropriate alkyl halide, oxidation to the sulfone with 30% hydrogen peroxide in acetic acid, ester hydrolysis and decarboxylation as before affords IIb, IId and IIe, (where R1 is S02R11 and R4 is H), respectively. A similar reaction sequence starting with the mono-carboxylic acid esters IIh, IIg, IIf and IIk (R1 is CO2CH2CH3 and R4 is H) gives access to pyrroles IIg, IIh, IIc and IIm (where R1 is SO2R11 and R4 is H) , respectively. The remaining pyrrole sulfones II may be prepared from the corresponding alkyl pyrroles (R1 is H and R4 is H) by reaction with thiourea or a thiocyanogen halide, hydrolysis, alkylation and oxidation as above. Pyrroles IIa, IIf, Ili, IIk and III are starting materials when R1 is COCC13. When R1 is COCC13 and R4 is H, pyrroles IIa, Ili and II1 are known in the literature [J. W. Harbuck and H. Rapaport, J. Org. Chem., 37, 3618-22 (1972); A. Treibs and F.-H. Kreuzer, Ann. Chim., 721, 105-15 (-1969)]. Pyrroles IIf and IIk (R1 is COCC13 and R4 is H) may be prepared in like fashion by treatment of the corresponding alkyl pyrroles (R1 is H) with trichloroacetyl chloride in chloroform, optionally in the presence of a base such as 2,6-lutidine or potassium carbonate. The halopyrroles required as starting materials may be represented by structures xVIIIa-b in which R3 is C1 or Br and R1 is NO2, CN, S02R11 or C(O)R5. EMI34.1 Again, R2 has been illustrated by H and CH3 and R4 by H for simplicity and the methods described for the preparation of these compounds may be applied to the synthesis of higher alkyl homologs of R2. Pyrroles of structure XVII Ia in which R1 is NO2 and R3 is Br, R1 is C(O)CH3 and R3 is C1 or Br, and in which R1 is CO2CH3 and R3 is C1 or Br are known in the literature [P. E. Sonnet, J. Het. Chem., 7, 1101 (1970); P. E. Sonnet and J. C. Moser, Env. Ent., 2 (5) 851-4 (1973); and P. Hodge and R. W. Richards, J. Chem. Soc., 459-470 (1965)]. The remaining halopyrroles may be prepared by treatment of pyrroles XVIII (R3 = H) with bromine, chlorine or sulfuryl chloride. In some instances, mixtures of the 4- and 5-halopyrroles may be obtained and can be separated by chromatography. The preferred method for the preparation of structures XVIIIa in which R1 is C(O)R5 (R5 is alkoxy) involves the use of compound XIX as an intermediate [P. Belanger, Tetrahedron Lett., 2505-2508 (1979)]. EMI35.1 Compounds XIX may be converted first to the carboxylic acids and then to the corresponding acid chlorides and reacted with alkoxides to afford the desired products. For primary alkoxides this reaction may be carried out directly with pyrroles XIX in the corresponding alcohol or an inert aprotic solvent. The preceeding pyrroles in which R4 is H may be converted to the corresponding compounds in which R4 is alkyl, cycloalkyl, benzyl, cyanoethyl or C(O)R6 by formation of the alkali metal salt of the pyrrole nitrogen, preferably the potassium salt, and treatment with an appropriate reagent in an inert solvent such as benzene, toluene, tetrahydrofuran or dimethylformamide. The alkyl, cycloalkyl and benzyl derivatives may also be efficiently prepared by the phase transfer method of W. C. Guida and D. J. Mathre, J. Org. Chem., 45, 3172 (1980). Reaction of the appropriate N-pyrrole alkali metal salts with acrylonitrile, acyl halides, alkylhaloformates or dialkylcarbamoyl halides should afford the corresponding pyrroles in which R4 is cyanoethyl and C(O)R6 where R6 is alkyl, alkoxy and amino, respectively. Such conversions are well known in the literature and suitable conditions would be obvious to one skilled in the art. Compounds Ia and Ib of the invention with some values of R1 may be used in certain instances to conveniently prepare the corresponding systems with different values of R1. Compounds of structure Ia, in which R1 is C(O)CC13 (XX) are especially useful as intermediates and may be readily converted to the corresponding carboxylic acids or esters. Treatment of XX with two equivalents of an aqueous alkali metal alkoxide, followed by precipitation of the product with dilute aqueous acid and filtration affords the corresponding carboxylic acid XXI. Reaction of XX with two equivalents of primary alkoxides in the corresponding alcoholic solvent or in an aprotic solvent such as acetonitrile or tetrahydrofuran followed by dilution with water and acidification gives rise to esters of Formula XXII in which R5 is OCH3, OCH2CH3, O(CH2)2CH3, OCH2CH(CH3)2 or O(CH2)3CH3. EMI38.1 Methyl esters of Formulae Ia or Ib (R1 is C(O)R5 and R5 is OCH3) may be converted to the corresponding acids or to secondary carboxylic esters by methods disclosed in unexamined European Patent Specification 7687p filed February 6, 1980. Agriculturally suitable salts of the compounds of formulae Ia or Ib may be made by the methods disclosed in our U.S. Patent No. 4,127,405. The compounds of the invention and their preparation are further illustrated by the following examples. In the following examples, unless otherwise indicated, all parts are by weight and all temperatures in OC. Example 1 Preparation of N-[(4,6-dimethylpyrimidin-2-yl)amino carbonyl]-2,5-dimethyl-lH-pyrrole-3-sulfonamide. To a mechanically stirred suspension of 12.3 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine in 200 ml of dry dichloromethane maintained at 0 to 50C under a nitrogen atmosphere was added dropwise over 30 minutes a solution of 9.2 ml (0.1 mole) of chlorosulfonyl isocyanate in 50 ml of ice-cold dichloromethane. After 30 minutes at 0 to 50C the resulting yellow solution was treated dropwise over 15 minutes with 20 ml (0.197 mole) of 2,5-dimethylpyrrole. This mixture was stirred 30 minutes at 0 to 50C and allowed to stand overnight at room temperature. The dichloromethane solution was decanted and the resulting reddish solid dissolved in a mixture of 50 ml methanol and 600 ml of 1N sodium hydroxide solution, acidified with 10% HC1 and extracted with 4 portions of ethyl acetate. The ethyl acetate was evaporated in vacuo to afford a brown solid which was dissolved in 50 ml methanol and 300 ml of dilute NaOH solution. The aqueous solution was washed with 2 portions of CH2C12, acidified with glacial acetic acid and extracted with 2 portions of CH2C12. The latter CH2Cl2 solutions were evaporated to afford the crude product which was purified by fractional crystallization from 20% acetone in CH2C12 to afford a white solid, m.p. 220-222#. Mass spectral analysis showed m/e 123, EMI40.1 and m/e 200, EMI40.2 Anal. Calcd. for C13H17N5O35: C, 48.3; H, 5.3; N, 21.7; S, 9.9 Found: C, 48.4; H, 5.4; N, 22.0; S, 9.8. Example 2 Preparation of N-[(4,6-dimethylpyrimidin-2-yl)amino- carbonyl]-1H-pyrrole-2-sulfonamide. Method A: To a mechanically stirred mixture of 12.3 g Co.l mole) of 2-amino-4,6-dimethylpyrimidine in 200 ml dry tetrahydrofuran a 0 to 50C under a nitrogen atmosphere was added dropwise via syringe 9.2 ml (0.1 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 5 C. After 10 minutes at 0 the solution was treated with 14.0 ml (0.2 mole) of pyrrole, stirred 15 minutes at 0 then allowed to stand at room temperature overnight. The resulting gummy slurry was diluted with 50 ml methanol and 100 ml dilute NaOH solution. After 30 minutes, this solution was washed with 2 portions of CH2C12 and acidified with glacial acetic acid. The precipitate was collected and washed with water to afford 9.5 g (32%) of crude product. A pure sample was obtained by separation from the minor pyrrole-3sulfonamide using high pressure liquid chromatography to give a white solid, m.p. 226-227 (d). Mass spectral analysis showed m/e 123, EMI41.1 and m/e 172, EMI41.2 Anal. Calcd. for C11H13N5O3S: C, 44.7; H, 4.4; N, 23.7. Found: C, 45.2; H, 4.6; N, 24.0. Preferred Method B: To a stirred mixture of 7.1 g (.057 mole) of 2amino-4,6-dimethylpyrimidine in 35 ml of dry tetrahydrofuran at -780C under a nitrogen atmosphere was added dropwise via syringe 5.0 ml (0.057 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below -500C. After 30 minutes at -700C, this solution was added dropwise over 10 minutes to a mixture of 8.0 ml (0.115 mole) of pyrrole, 0.3-0.5 g of aluminum (III) chloride and 35 ml dry THF at -780C under a nitrogen atmosphere. The reaction mixture was allowed to warm gradually to room temperature and allowed to stand at room temperature overnight. The reaction mixture was diluted with 150 ml H2O and made alkaline by addition of 50% NaOH solution. This slurry was filtered and the filtrate washed with 2 portions CH2C12 and acidified with glacial acetic acid. The precipitate was collected, washed well with water and dried to afford 11.5 g (68%) of crude product as above. Example 3 Preparation of 1- (2-cyanoethyl)-N-[ (4,6-dimethylpyrimi- din-2-yl)aminocarbonyl]-lH-pyrrole-2-sulfonamide. To a stirred suspension of 2.59 g (0.021 mole) of 2-amino-4,6-dimethylpyrimidine in 80 ml dry tetrahydrofuran at -700C under nitrogen was added dropwise via syringe 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature of the reaction mixture below -550C. The resulting solution was stirred 0.5 hour at -700, then treated dropwise with a solution of 2.4 ml (0.021 mol) of N-(2-cyanoethyl)pyrole in 10 ml dry THF. A catalytic amount (approximately 0.2 to 0.3 gm) of aluminum (III) chloride was added and the reaction mixture allowed to warm to ambient temperatures and stirred for an additional 18 hours. The reaction mixture was poured into 300 ml of H2O and extracted with three portions of dichloromethane. The organic solutions were washed with water, dried over MgSO4 and evaporated. Trituration with a small volume of CH2C12 afforded 1.2 g of the desired product as a white microcrystalline solid, m.p. 158-1590C. The infrared spectrum of the product included absorptions at 3250 and 3110 (NH), 2240 (C=N) , 1685 (C=O), 1350 and 1160 cm (SO2) Example 4 Preparation of 4-[((4,6-dimethylpyrimidin-2-yl)aminocarbonyl)aminosulfonyl]-1H-pyrrole-2-carboxylic acid, methyl ester. To a stirred suspension of 2.58 g (0.021 mol) of 2-amino-4,6-dimethylpyrimidine in 75 ml dry nitromethane at -10 was added dropwise, via syringe, under nitrogen, 2.0 ml. (0.023 mol) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 00. The resulting clear solution was stirred 0.5 hour at -5 to -10 , then treated dropwise with a solution of 2.29 g (0.021 mole) of methyl pyrrole-2carboxylate in 25 ml dry mitromethane. Upon completion of the addition, 2.95 gm (0.022 mole) of aluminum (III) chloride was added in one portion. The reaction mixture was heated at reflux for 2 hours, then allowed to stand overnight at ambient temperatures. The mixture was poured into 300 ml H2O and the two phase system extracted with three portions of CH2C12. The organic solutions were washed with water, dried over MgSO4 and evaporated to a tan foam which was triturated with minimal CH2C12 to afford the product as a white solid, m.p. 202-2040. Anal. Calcd. for C13H15N5O5S: C, 44.19; H, 4.28; N, 19.82; S, 9.07. Found: C, 42.4; H, 4.1; N, 19.4; S, 8.95. Example 5 Preparation of the methyl ester of 4-bromo-5-[((4,6 dimethylpyrimidin-2-yl)aminocarbonyl)aminosulfonyl]-lH pyrrole-2-carboxylic acid. To a stirred suspension of 2.58 g (0.021 mole) of 2-amino-4,6-dimethylpyrimidine in 75 ml dry nitromethane at -10 was added dropwise, via syringe, under nitrogen, 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 00. The resulting clear solution was stirred 0.5 hour at -5 to -10 , then treated dropwise with a solution of 4.28 g (0.021 mol) of methyl 4-bromopyrrole-2-carboxylate in 25 ml dry CH3NO2. Upon completion of the addition, 2.95 g (0.022 mol) of aluminum (III) chloride was added in one portion and the reaction mixture heated at reflux for 3 hours. Workup as in Example 4 and chloroform trituration afforded 4.51 g (50%) of product as a white, microcrystalline solid, m.p. 126-128 . The infrared spectrum of the product included resonances at 3160 (NH), 1710 (C=O), 1340 and 1160 (S02)cm Example 6 Preparation of N-[ (4,6-dimethylpyrimidin-2-yl)amino carbonyl] -5-trichloroacetyl-lH-pyrrole-2-sulfonamide. To a stirred suspension of 2.59 g (0.021 mol) of 2-amino-4,6-dimethylpyrimidine in 60 ml dry CH3NO2 at -100 was added dropwise, via syringe, under nitrogen, 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 5 . The resulting clear solution was stirred 0.5 hour at -5 , then treated dropwise with a solution of 4.46 g (0.021 mole) of 2-trichloroacetyl-lH-pyrrole in 30 ml dry CH3NO2. Upon completion of the addition, 2.95 g (0.022 mole) of aluminum (III) chloride was added in one portion and the reaction mixture stirred 1.5 hour at ambient temperatures followed by 0.5 hour under reflux. The cool solution was poured into H2O, diluted with CH2C12 and the layers separated. A precipitate was present in the aqueous layer and was collected by filtration and washed well with water. The organic solution was washed with H2O, dried over MsSO4, evaporated and triturated with CH2C12 to afford a second crop of product. Total yield of product was 2.45 g of a tan solid, m.p. 215-2180(d) . The infrared spectrum of the product included absorptions at 3230 (NH), 1692 (C=O), 1340 and 1160 cm (SO2). By using methods described generally above and illustrated in Examples 1-6, compounds as shown in the following tables can similarly be prepared. These tables are not meant to be all inclusive but only illustrative of the breadth of the invention. Table I EMI47.1 EMI47.2 <tb> RI <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R9 <SEP> X <SEP> Y <SEP> Z <SEP> m.p.( C) <tb> H <SEP> H <SEP> H <SEP> . <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <tb> H <SEP> H <SEP> H <SEP> H <SEP> 3 <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> > 300* <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <SEP> CC1 <tb> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CF3 <SEP> CCH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> OC2H5 <SEP> CC2H5 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 190-192* <tb> H <SEP> H <SEP> H <SEP> CH2C6H5 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 132-140* <tb> H <SEP> H <SEP> H <SEP> t-C4Hg <SEP> CH3 <SEP> OCH3 <SEP> CH3 <SEP> CC2H5 <tb> H <SEP> H <SEP> H <SEP> C(O)C3H7 <SEP> CH3 <SEP> OCH3 <SEP> CC2H5 <SEP> N <tb> H <SEP> H <SEP> H <SEP> C(O)N(Me)2 <SEP> H <SEP> OCH3 <SEP> H <SEP> N <tb> H <SEP> H <SEP> H <SEP> NO <SEP> C <SEP> H <SEP> H <SEP> OCH3 <SEP> H <SEP> CF <tb> 5-CH3 <SEP> H <SEP> 2-CH3 <SEP> CO2C2H5 <SEP> H <SEP> OCH3 <SEP> H <SEP> CBr <tb> 5 <SEP> C4Hg <SEP> H <SEP> H <SEP> COCH3 <SEP> OCH3 <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> 5-CH3 <SEP> H <SEP> 2-CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 220-222 <tb> 5 <SEP> Ct3 <SEP> 2 <SEP> C <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <SEP> 127-131 <tb> 5-CH3 <SEP> 2-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 209-211 <tb> 5-CH3 <SEP> 2-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 205-207 <tb> S-CH3 <SEP> 2-CH3 <SEP> H <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 200-204 <tb> 5-C2H5 <SEP> 2-C2H5 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> C <SEP> (CH2) <SEP> 1 <tb> 5-CH3 <SEP> 2-CH <SEP> H <SEP> O-ClC6d4 <SEP> H <SEP> CH <SEP> Cl <tb> <SEP> 3 <tb> 5-CH <SEP> 2-CH <SEP> H <SEP> ( <SEP> 2)2 <SEP> OCH3 <SEP> CH3 <SEP> CH2OC <SEP> 2H5 <SEP> CH3 <tb> <SEP> 3 <tb> 4-NO2 <SEP> 2-CH3 <SEP> 5-CH3 <SEP> H <SEP> CH3 <SEP> CCH3 <SEP> CH20C2H5 <SEP> N <tb> 2-5 2 <SEP> 5-C4H9 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> OCH <SEP> C1 <SEP> CCH3 <tb> Table I (continued) R1 R2 R3 R4 R9 X Y Z m.p.( C) 5-CN H H C3H7 CH3 CH3 OCH3 CC1 2-CN C2H5 C2H5 H H CH3 OCH2CF3 N 4-CN CH3 CH3 H H CH3 OC2H5 5-COOCl3 H H H H CH3 CH3 CH 215-218 5-COOCl3 H H CH3 H CH3 CH3 CH 203-205 4-COOCl3 5-C3H7 2-C3H7 H CH3 CH3 OCH3 N 5-SO2CH3 H H CH3 H CH3 H N 5-SO2CH3 2-C3H7 H H H CH H CH 2-SO2C3H7 4-C2H5 5-CH3 H H CH3 Cl CH 4-SO2C4H9 5-CH3 2-CH3 H H CH3 Cl OCH3 5-COCH3 H H C3H7 H CH3 CH3 C(CH2)2Cl 5-COC4H9 H H H OCH3 CH3 CH3 CH 2-COCH3 4-C4H9 5-CH3 H OCH3 CH3 CH3 CCl 5-CO2CH3 H H H H CH3 OCH3 N 110(d)* 5-CO2CH3 H H H H OCH3 OCH3 N 184-188 5-COC4H9 H H H H CH3 CH3 CH 202-204 5-CO2CH3 H H CH3 H CH3 CH3 CH 91-96* 4-CO2C2H5 2-CH3 5-CH3 H H CH3 CH3 CH 223-225 4-C02t-C4Hg H H H H OCH3 OC2H5 CC1 5-CO2H H H H H CH3 CH3 CH 198-200 5-CO2H H H n-C4Hg CH3 OCH3 Cl CH 4-CO2H 5-CH3 2-CH3 H H OCH3 OC2H5 OCH3 2-CO2H 5-C2H5 4-C2H5 H H OCH3 Cl N *m.p. is for an isomeric product mixture consisting of this compound and the corresponding entry in Table V. Table II EMI49.1 R1 R2 R3 R4 R9 YÚ m.p.( C) H H H H H CH3 H H H H H Cl H H , H H . S OC2H5 H H H H CH3 Cl H H H H OCH3 OCH3 H H H C2H5 H OCH3 H H H (CH2)2ON H CH3 H H H t-C4H9 CH3 CH3 H H H n-Cl-C6H4 H CH3 H H H CO2C2H5 CH3 H 5-CH3 H 2-CH3 COC4H9 H CH3 5-CH3 2-CH3 H COCH3 H H 5-CH3 H 2-CH3 CONMe2 H CH3 5-C2H5 2-C2H5 H p-NO2C6H4 H CH3 5-CH3 2-CH3 H CH3 CH3 CH3 5-C4H9 2-C4H9 H H OCH3 OCH3 CH3 CH3 CH3 H OCH3 OCH3 5-COCl3 H H CH3 CH3 OCH3 5-COCC13 H 5-C H H H Cl 4-COCl3 i-C3H7 i-C3H7 H H CH3 2-NO2 5-CH3 5-i-C4H9 H H CH3 5-CN H H CH3 H CH3 2-CN CH3 CH3 CH2C6H5 H Cl 4-CN C2H5 C2H5 H CH3 OCH3 Table II (continued) EMI50.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> N <SEP> Y1 <SEP> m.p.(4C) <tb> 5 <SEP> C 2C <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <tb> 5-CO2C3H7 <SEP> H <SEP> H <SEP> C2H5 <SEP> OCH3 <SEP> CH3 <tb> 5COCH3 <SEP> 4-CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-COC4Hg <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 2-COCH3 <SEP> 5-CH3 <SEP> 4-C3H7 <SEP> CH3 <SEP> CH3 <SEP> C1 <tb> 5-SO2CH3 <SEP> H <SEP> H <SEP> 4 <SEP> H <SEP> H <tb> 5-S02C3H7 <SEP> H <SEP> 2-CH3 <SEP> H <SEP> CH3 <SEP> OC2H5 <tb> 4-SO2CH3 <SEP> 2-C2H5 <SEP> 5-C2H5 <SEP> i-C3H7 <SEP> CH3 <tb> 4-CO2H <SEP> C2H5 <SEP> C2H5 <SEP> H <SEP> OCH3 <SEP> H <tb> 5-CO2H <SEP> H <SEP> H <SEP> C3H7 <SEP> H <SEP> CH3 <tb> Table III EMI51.1 R1 R2 R3 R4 R9 YÚ m.p.( C) H H H H H CH3 H H H H H Cl H H H H H OC2H5 H H H H CH3 Cl H H H H OCH3 OCH3 H H H C2H5 H OCH3 H H H (CH2)2CN H CH3 H H H t-C4H9 CH3 CH3 H H H n-Cl-C6H4 H CH3 H H H CO2C2H5 CH3 H 5-CH3 H 2-CH3 COC4H9 H CH3 5-CH3 2-CH3 H COCH3 H H 5-CH3 H 2-CH3 CONMe2 H CH3 5-C2H5 2-C2H5 H p-NO2C6H4 H CH3 5-CH3 2-CH3 H CH3 CH3 CH3 5-C4H9 2-C4H9 H H OCH3 OCH3 CH3 CH3 CH3 H OCH3 OCH3 5-COCCl3 H H CH3 CH3 OCH3 5-COCCl3 H 5-C2H5 H H Cl 4-COCCl3 i-C3H7 i-C3H7 H H CH3 2-NO2 5-CH3 5-i-C4H9 H H CH3 5-CN H H CH3 H CH3 2-CN CH3 CH3 CH2C6H5 H Cl 4-CN C2H5 C2H5 H CH3 OCH3 Table III (continued) EMI52.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R, <SEP> R9 <SEP> yl <SEP> m.p.( C) <tb> 5-m2CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <tb> 5 <SEP> 2C3 <SEP> H <SEP> H <SEP> C2H5 <SEP> OCH3 <SEP> CH3 <tb> 5-COCH3 <SEP> 4-CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-COC4H9 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 2-COCH3 <SEP> 5-CH <SEP> 3 <SEP> 4-C3H, <SEP> CH3 <SEP> CH3 <SEP> C1 <tb> 5-SO2CH3 <SEP> H <SEP> H <SEP> H <SEP> H <tb> 5 <SEP> S 2C3 <SEP> 7 <SEP> H <SEP> 2-CH <SEP> 3 <SEP> H <SEP> CH3 <SEP> OC2H5 <tb> 4-SO2CH3 <SEP> 2-C2H5 <SEP> 5-C2H5 <SEP> i-C3H7 <SEP> H <SEP> CH3 <tb> 4-CO2H <SEP> C2H5 <SEP> C2 <SEP> H <SEP> H <SEP> OCH3 <SEP> H <tb> 5-CO2H <SEP> H <SEP> H <SEP> C3H? <SEP> H <SEP> CH3 <tb> Table IV EMI53.1 R1 R2 R3 R4 R9 YÚ m.p.( C) H H H H H CH3 H H H H H Cl H H H H H OC2H5 H H H H CH3 Cl H H H H OCH3 OCH3 H H H C2H5 H OCH3 H H H (CH2)2CN H CH3 H H H t-C4H9 CH3 CH3 H H H n-Cl-C6H4 H CH3 H H H CO2C2H5 CH3 H 5-CH3 H 2-CH3 COC4H9 H CH3 5-CH3 2-CH3 H COCH3 H H 5-CH3 H 2-CH3 CONMe2 H CH3 5-C2H5 2-C2H5 H p-NO2C6H4 H CH3 5-CH3 2-CH3 H CH3 CH3 CH3 5-C4H9 2-C4H9 H H OCH3 OCH3 CH3 CH3 CH3 H OCH3 OCH3 5-COCCl3 H H CH3 CH3 OCH3 5-COCCl3 H 5-C2H5 H H Cl 4-COCl3 i-C3H7 i-C3H7 H H CH3 2-NO2 5-CH3 5-i-C4H9 H H CH3 5-CN H H CH3 H CH3 2-CN CH3 CH3 CH2C6H5 H Cl 4-CN C2H5 C2H5 H CH3 OCH3 Table IV (continued) EMI54.1 <tb> R1 <SEP> 2 <SEP> 3 <SEP> R. <SEP> R9 <SEP> yl <SEP> m.p.(OC) <tb> 5-CO2CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <tb> 5-032C3K7 <SEP> H <SEP> H <SEP> C2H5 <SEP> OCH3 <SEP> CH3 <tb> 5CCCH3 <SEP> 4-CH <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 3 <tb> 5CCC4H9 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 2-COCH3 <SEP> 5-CH3 <SEP> 4-C3H7 <SEP> CH3 <SEP> CH3 <SEP> C1 <tb> 5-SO2CH3 <SEP> H <SEP> H <SEP> < <SEP> H <SEP> H <tb> 5-S02C3H7 <SEP> H <SEP> 2-CH3 <SEP> H <SEP> CH3 <SEP> CC2H5 <tb> 4 <SEP> SO2CH3 <SEP> . <SEP> 2-C2Hg <SEP> 5-C2H <SEP> i-C3H7 <SEP> CH3 <tb> 4-CO2H <SEP> C2H5 <SEP> C2H5 <SEP> H <SEP> . <SEP> OCH3 <SEP> H <tb> 5-CO <SEP> 2H <SEP> H <SEP> H <SEP> C <SEP> H <SEP> H <SEP> CH3 <tb> Table V EMI55.1 EMI55.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Rg <SEP> X <SEP> Y <SEP> z <SEP> m.p.( C) <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 226-227 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <SEP> 214-217 <tb> 9 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> > 300* <tb> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> C1 <SEP> CC1 <tb> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CF3 <SEP> 3 <SEP> CCH3 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> CH <SEP> 3 <SEP> CH3 <SEP> CH <SEP> 190-192* <tb> H <SEP> H <SEP> H <SEP> (CH2)2CN <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 158-159 <tb> H <SEP> H <SEP> H <SEP> CH <SEP> C <SEP> H <SEP> H <SEP> CH <SEP> 3 <SEP> CH3 <SEP> CH <SEP> 132-140* <tb> H <SEP> H <SEP> H <SEP> t-C4Hg <SEP> CH3 <SEP> OCH3 <SEP> OC <SEP> 2H5 <SEP> CC2H5 <tb> H <SEP> H <SEP> H <SEP> C(O)C3d7 <SEP> CH3 <SEP> CCH3 <SEP> H <SEP> N <tb> H <SEP> H <SEP> H <SEP> C(O)NMe2 <SEP> H <SEP> OCH3 <SEP> H <SEP> N <tb> H <SEP> H <SEP> H <SEP> E7N 2C6H4 <SEP> H <SEP> . <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 198-204 <tb> 5-CH3 <SEP> H <SEP> H <SEP> CO2C2H5 <SEP> H <SEP> CH <SEP> OCH <SEP> CBr <tb> 5-C4H9 <SEP> 4-CH3 <SEP> H <SEP> COCH3 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> 4-CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> Ci <SEP> N <tb> 5-CqHg <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> OCH <SEP> 2CF3 <SEP> N <tb> H <SEP> 3-C2H5 <SEP> 4-C2H5 <SEP> CiC6H4 <SEP> H <SEP> 0CH3 <SEP> CH3 <SEP> C <SEP> (CH2) <SEP> 2C1 <tb> H <SEP> 3-CH <SEP> 3 <SEP> 4-C3H7 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> OCH3 <SEP> CC2H5 <tb> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH <SEP> OCH3 <SEP> CF <SEP> CF <tb> H <SEP> 4-CH3 <SEP> 5-C2H5 <SEP> H <SEP> < <SEP> 1, <SEP> CH2OCH3 <SEP> CH <tb> 5-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 166-176* <tb> 5-N02 <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> OCH3 <SEP> CF <tb> 4-N02 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 115-122** <tb> <SEP> 3-NO, <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 115-122** <tb> Table V (continued) EMI56.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> N <SEP> x <SEP> Y <SEP> Z <SEP> m.p.(0C) <tb> 4-N02 <SEP> H <SEP> S-C3H7 <SEP> H <SEP> CH3 <SEP> OC2H5 <SEP> CCH3 <tb> 5-N 2 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> CH3 <SEP> CCH3 <SEP> CH <tb> 5-NO2 <SEP> H <SEP> 3-C1 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> 5-CN <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> 5-CS <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH <SEP> CH3 <SEP> C1 <SEP> CBr <tb> 3 <SEP> H: : <SEP> 3 <tb> 4-CN <SEP> H <SEP> H <SEP> 4 <SEP> CH3 <SEP> CH3 <SEP> N <tb> 3-ON <SEP> H <SEP> H <SEP> (CH2)2ON <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> S-S 2cH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> 5-502C3H7 <SEP> H <SEP> 3-Br <SEP> H <SEP> H. <SEP> CH3 <SEP> CCH3 <SEP> CH <tb> 5 <SEP> S 2CH3 <SEP> 3-C2H5 <SEP> 4-C2H5 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> 4-502C2H5 <SEP> H <SEP> H <SEP> C3H7 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> 4-sO2CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> C1 <SEP> CH <tb> H <SEP> $ 2CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> C1 <SEP> N <tb> 3-COCH3 <SEP> H <SEP> 5-CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> OC2H5 <SEP> CF <tb> 3-COC3H7 <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CF <SEP> OCH3 <tb> 4CCCH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH <SEP> CH <tb> 4-CO-i-C3H7 <SEP> 5-CH3 <SEP> 3-C2H5 <SEP> H <SEP> H <SEP> CH3 <SEP> CH22H5 <SEP> N <tb> S-CCC4Hg <SEP> H <SEP> 3-Br <SEP> 4 <SEP> CH3 <SEP> CH3 <SEP> CH2OCH3 <SEP> N <tb> 5CCCH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> 5-CCCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CF <tb> 5-C32C2H5 <SEP> H <SEP> 3-Br <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 214-216 <tb> 5-CO2CH3 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 126-128 <tb> 5 <SEP> C 2CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <SEP> 110(d)* <tb> 5 <SEP> o 2CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 91-96* <tb> 5 <SEP> CO2C4H9 <SEP> 3-C2H5 <SEP> H <SEP> H <SEP> H <SEP> OCH <SEP> 3 <SEP> C1 <SEP> CF <tb> 3-C02CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> OCH3 <SEP> OCH3 <tb> 4-002C3H7 <SEP> H <SEP> 5 <SEP> C4Hg <SEP> H <SEP> H <SEP> OCH3 <SEP> CH20CH3 <SEP> N <tb> 5-CO2H <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 139-145 <tb> 5-CO2H <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> Table V (continued) EMI57.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Rg <SEP> X <SEP> Y <SEP> Z <SEP> m.p. <SEP> ( C) <tb> 3-C02H <SEP> 4-C5 <SEP> 5-C2H5 <SEP> 0 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> 4-CO2H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> *m.p. is for an isomeric product mixture consisting of this compound and the corresponding entry in Table I. **these compounds obtained as an isomeric mixture. Table VI EMI58.1 EMI58.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Rg <SEP> yl <SEP> m.p.(O) <tb> <SEP> 4 <tb> H <SEP> H <SEP> H <SEP> . <SEP> H <SEP> H <SEP> H <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> OCH <SEP> 3 <tb> H <SEP> H <SEP> H <SEP> t-C4Hg <SEP> CH3 <SEP> OCH <tb> H <SEP> H <SEP> H <SEP> 4 <SEP> H3 <SEP> OCH3 <SEP> OCH3 <tb> H <SEP> H <SEP> H <SEP> (CH2)2CN <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> CH2C6H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> o-ClC6H4 <SEP> CH3 <SEP> CH3 <tb> 5-CH3 <SEP> H <SEP> H <SEP> COCH3 <SEP> H <SEP> CH3 <tb> 5 <SEP> 3-CH <SEP> 3 <SEP> H <SEP> CONMe2 <SEP> H <SEP> CH3 <tb> H <SEP> 3 <SEP> C2H5 <SEP> H <SEP> CO2C2H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> COC <SEP> 4H9 <SEP> H <SEP> OCH3 <tb> ;-CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH <SEP> 3 <tb> 4 <SEP> 9 <SEP> H <SEP> H <SEP> H <SEP> CH <SEP> CH3 <tb> H <SEP> 3-C2H5 <SEP> 4-C2H5 <SEP> NO2C6· <SEP> H <SEP> CH3 <tb> H <SEP> 3-CH <SEP> 3 <SEP> 4-C3H7 <SEP> H <SEP> CH3 <SEP> CH <SEP> 3 <tb> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> H <SEP> 4-CH3 <SEP> 5-C2H5 <SEP> 4 <SEP> H <SEP> OCH <tb> 5-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <tb> 5-NO <SEP> 3-CH <SEP> 4-CH3 <SEP> H <SEP> OH, <SEP> 3 <tb> <SEP> L <SEP> 3 <SEP> OCH <SEP> Cl <tb> 5-NO2 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> C1 <tb> Table VI (continued) EMI59.1 <tb> ¯ <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R9 <SEP> yl <SEP> m.D. <SEP> (OC) <tb> H <SEP> H <SEP> 5-C3H7 <SEP> H <SEP> CH3 <SEP> C1 <tb> 3-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <tb> 5-CS <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> H <tb> 5-CN <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH <SEP> 3 <SEP> H <tb> 4-CN <SEP> H <SEP> H <SEP> 4 <SEP> H <SEP> OC2H5 <tb> 3-CN <SEP> H <SEP> H <SEP> (CH2)2CN <SEP> H <SEP> OC <SEP> 2H5 <tb> 5-S02CEI3 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> OC2H5 <tb> 5-502C3H7 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-SO2CH3 <SEP> 3-C2H5 <SEP> 4 <SEP> 4-C2H5 <SEP> H <SEP> H <SEP> OCH3 <tb> 4-S02C2H5 <SEP> H <SEP> H <SEP> C3H7 <SEP> H <SEP> ' <SEP> C1 <tb> 4-SO <SEP> 2H3 <SEP> 5-CH <SEP> 3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 3-So2CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH <tb> 3-COCH3 <SEP> H <SEP> 5-CH3 <SEP> CH3 <SEP> H <SEP> CH3 <tb> 3-COC <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH <SEP> 3 <tb> 4-COCH <SEP> 5-CH <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5 <SEP> COC4Hg <SEP> H <SEP> 3-Br <SEP> 4 <SEP> CH3 <SEP> C1 <tb> 5COCH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> C1 <tb> 5-COCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-C 2c2H5 <SEP> H <SEP> 3-Br <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-002CH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> C1 <tb> 5-CD2CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> 5-COC <SEP> H <SEP> 2 <SEP> H <SEP> i-C <SEP> H <SEP> H <SEP> OCH3 <tb> 3-CO2C <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH3 <tb> 4-CO2C3H7 <SEP> H <SEP> 5 <SEP> C4Hg <SEP> H <SEP> OCH3 <SEP> OCH <tb> S-CO2H <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> CH3 <tb> 5-C02H <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> OC2H5 <tb> 3-CO2H <SEP> 4-C2H5 <SEP> 5-C2H5 <SEP> 4 <SEP> H <SEP> OCH3 <tb> 4-CO2H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH <SEP> 3 <tb> Table VII EMI60.1 EMI60.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Rg <SEP> yl <SEP> m <SEP> m.P.(O) <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <tb> H <SEP> H <SEP> H <SEP> ' <SEP> H <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> OCH <SEP> 3 <tb> H <SEP> H <SEP> H <SEP> t-C4Hg <SEP> CH3 <SEP> OCH2CH3 <tb> H <SEP> H <SEP> H <SEP> < <SEP> OCH <SEP> OCH3 <tb> H <SEP> H <SEP> H <SEP> (CH2)2ON <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> CH2C6H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> o-ClC6H4 <SEP> CH3 <SEP> CH3 <tb> 5-CH3 <SEP> H <SEP> H <SEP> COCH3 <SEP> H <SEP> CH3 <tb> 5-C4H9 <SEP> 3 <SEP> CH3 <SEP> H <SEP> CONMe2 <SEP> H <SEP> - <SEP> CH3 <tb> H <SEP> 3 <SEP> C2H5 <SEP> H <SEP> CO2C2H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> COC4H9 <SEP> H <SEP> OCH3 <tb> 43 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <tb> 5-CHg <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> H <SEP> 3-C2Hg <SEP> 4-C2H5 <SEP> E <SEP> N 2C6H4 <SEP> H <SEP> CH3 <tb> H <SEP> 3-CH3 <SEP> 4-C3H7 <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH3 <SEP> CH3 <SEP> CH <SEP> 3 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> H <SEP> 4-CH3 <SEP> S-C2H5 <SEP> 4 <SEP> H <SEP> OCH <SEP> 3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> OCH <tb> 5-NO2 <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> C1 <tb> 5-NO2 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> C1 <tb> Table VII (continued) EMI61.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R9 <SEP> yl <SEP> m.p.(OC) <tb> H <SEP> H <SEP> 5-C3H7 <SEP> H <SEP> CH3 <SEP> C1 <tb> 3-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <tb> 5-CS <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> H <tb> 5-CN <SEP> 3-CH <SEP> 3 <SEP> 4-CH <SEP> H <SEP> OCH3 <SEP> H <tb> 4-CN <SEP> H <SEP> H <SEP> 4 <SEP> H <SEP> OC <SEP> 2H5 <tb> 3-CN <SEP> H <SEP> H <SEP> (CH2) <SEP> 2ON <SEP> H <SEP> OC2H5 <tb> 5-S02CH3 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> OC2H5 <tb> 5-SO <SEP> C <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-S02CH3 <SEP> 3-C2H5 <SEP> 4-C2H5 <SEP> H <SEP> H <SEP> OCH3 <tb> 4-502C2H5 <SEP> H <SEP> H <SEP> C3H7 <SEP> H <SEP> C1 <tb> 4-S02CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 3-502CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> CH <SEP> 3 <tb> 3COCH3 <SEP> H <SEP> 5-CH3 <SEP> CH3 <SEP> H <SEP> CH3 <tb> 3-COC <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> 4-CCCH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-CCC4Hg <SEP> H <SEP> 3-Br <SEP> < <SEP> CH3 <SEP> C1 <tb> 5COCH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> Cl <tb> 5-COCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-CO2C2H; <SEP> H <SEP> 3-Br <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-CO2CH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> C1 <tb> S <SEP> 2C <SEP> 3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> 5 <SEP> 4 <SEP> 9 <SEP> 3-C2H5 <SEP> H <SEP> i-C3H7 <SEP> H <SEP> OCH3 <tb> 3-CO2CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH3 <tb> 4-CO <SEP> C <SEP> H <SEP> H <SEP> 5-C4H9 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> 5-CO2H <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> CH3 <tb> S-CO2H <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> OC2H5 <tb> 3-CO <SEP> 2H <SEP> 4-C2H5 <SEP> 5-C2H5 <SEP> 4 <SEP> H <SEP> OCH3 <tb> 4-CO <SEP> 2H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> Table VIII EMI62.1 EMI62.2 <tb> RI <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Rg <SEP> yl <SEP> me. <SEP> (0) <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> OCH <SEP> 3 <tb> H <SEP> H <SEP> H <SEP> t-C4H9 <SEP> CH3 <SEP> CCH <tb> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> H <SEP> H <SEP> H <SEP> (CH2)2ON <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> CH2C6H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> orClC6H4 <SEP> CH3 <SEP> CH3 <tb> 5-CH3 <SEP> H <SEP> H <SEP> COUCH3 <SEP> H <SEP> CH3 <tb> 5-C4H9 <SEP> 3 <SEP> H <SEP> CONMe2 <SEP> H <SEP> CH3 <tb> H <SEP> 3-C2Hg <SEP> H <SEP> CO <SEP> *2H5 <SEP> H <SEP> CH3 <tb> H <SEP> H <SEP> H <SEP> COC4H9 <SEP> H <SEP> OCH <tb> 4-CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> H <SEP> OCH <tb> 5 <SEP> C4Hg <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> H <SEP> 3-C2Hg <SEP> 4-C2H5 <SEP> i7N 2C6 <SEP> H <SEP> CH3 <tb> H <SEP> 3-CH3 <SEP> 4-C3H7 <SEP> H <SEP> CH3 <SEP> CH <SEP> 3 <tb> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> H <SEP> 4-CH3 <SEP> 5-C2H5 <SEP> 4 <SEP> H <SEP> OCH <SEP> 3 <tb> 5-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> OCH3 <tb> 5-NO2 <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH <SEP> 3 <SEP> Ci <tb> H <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> C1 <tb> Table VIII (continued) EMI63.1 <tb> R1 <SEP> R, <SEP> R3 <SEP> R4 <SEP> R9 <SEP> 0 <SEP> m.p.( C) <tb> 4-NO2 <SEP> H <SEP> 5-C3H7 <SEP> H <SEP> 3 <SEP> C1 <tb> 3-NO2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <tb> S-ON <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> H <tb> 5-CN <SEP> 3-CH <SEP> 3 <SEP> 4-CH <SEP> H <SEP> OCH3 <SEP> H <tb> 4-CN <SEP> H <SEP> H <SEP> 4 <SEP> H <SEP> OC2H5 <tb> 3-ON <SEP> H <SEP> H <SEP> (CH2) <SEP> 2ON <SEP> H <SEP> OC2H5 <tb> 5 <SEP> S 2CH3 <SEP> H <SEP> 3-Br <SEP> H <SEP> H <SEP> OC2H5 <tb> 5-S02C387 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 23 <SEP> 3-C2H5 <SEP> 4-C2H5 <SEP> H <SEP> C2g5 <SEP> H <SEP> OCH3 <tb> 4-502C2H5 <SEP> H <SEP> H <SEP> C <SEP> H <SEP> H <SEP> C1 <tb> 2 <SEP> 3 <SEP> C <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 3-S020H, <SEP> 8 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> 3-COCH3 <SEP> H <SEP> 5-CH3 <SEP> CH3 <SEP> H <SEP> CH3 <tb> 3-COC3H7 <SEP> H <SEP> H <SEP> H <SEP> CH <SEP> 3 <SEP> CH <tb> 4-C <SEP> Xi3 <SEP> 5-CH <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 5-CCC4Hg <SEP> H <SEP> 3-Br <SEP> < <SEP> CH3 <SEP> Cl <tb> 5-CCCH3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> C1 <tb> 5-COCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-C 2C2Hs <SEP> H <SEP> 3-Br <SEP> CH3 <SEP> H <SEP> C1 <tb> 5-co22Y3 <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> C1 <tb> 5-o <SEP> 2CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> 5-CCC4H9 <SEP> 3-C <SEP> H <SEP> H <SEP> i-C3H7 <SEP> H <SEP> OCH3 <tb> 3-C 2CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH3 <tb> 4-CO2C3H7 <SEP> H <SEP> 5-C4H9 <SEP> OCH3 <SEP> OCH3 <tb> 5-CO2H <SEP> H <SEP> 3-C1 <SEP> H <SEP> H <SEP> CH3 <tb> 5-CO2H <SEP> 3-CH3 <SEP> 4-CH3 <SEP> H <SEP> OCH3 <SEP> OC2H5 <tb> 3-CO2H <SEP> 4-C2H5 <SEP> 5-C2H5 <SEP> 4 <SEP> H <SEP> OCH3 <tb> 4-CO2H <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> TABLE IX EMI64.1 R X y 2 9 H CH3 OCH3 CH H OCH3 OCH3 CH H CH3 OC2H5 CH H CH3 Cl CH H CH3 H CH H CH3 OCH2CF2 CH H CH3 CH2OCH3 CH H OCH3 CH2OCH3 CH OCH3 CH2OC2H5 CH H CH3 CF3 CH H OCH3 CF3 CH H CH3 CH2OC2H5 CH CH3 OCH3 CH3 CH CH3 OCH3 OCH3 CH CH3 OCH3 OC2H5 CH H OCH3 Cl CH H OCH3 CH2OCH3 CH H OCH3 OCH2CF3 CH H OCH3 CH3 CCl H CH3 OCH3 CCl H OCH3 OCH3 CCl H CH3 CH3 CCH3 H CH3 H CCH3 H OCH3 H CCH3 H CH3 H CC1 Table IX (continued) X Y H CH3 CH3 CF H CH3 CH3O CF H CH3 CH3 CBr H CH3 H CBr H CH3 H CCH2CH3 H CH3 H CCH2CH2Cl H CH3 CH3 CCH2CH2Cl H CH3 H CF H OCH3 H CH H OCH3 Cl CH CH3 CH3 CH3 CH OCH3 CH3 CH3 CH OCH3 CH3 OCH3 CH OCH3 OCH3 OCH3 CH TableIX-a EMI66.1 R9 X Y H CH3 CH3 H CH3 OCH3 H OCH3 OCH3 H CH3 OCH2CH3 H CH3 Cl H CH3 H H CH3 OCH2CF3 H CH3 CH2OCH3 H OCH3 CH2OCH3 H OCH3 CH2OCH2CH3 H CH3 CF3 H OCH3 CF3 H CH3 CH2OC2H5 CH3 OCH3 CH3 CH3 OCH3 OCH3 CH3 OCH3 OC2H5 H OCH3 Cl H OCH3 OCH2CF3 OCH3 CH3 CH3 OCH3 OCH3 CH3 OCH3 OCH3 OCH3 OCH3 CH3 OCH2CH3 OCH3 CH3 OCH2CF3 OCH3 CH3 CH2OCH3 OCH3 CH3 OCH2CF3 CH3 CH3 CH3 Table IX-b EMI67.1 R9 YÚ H H H OCH3 H CH3 H Cl H OCH2CH3 OCH3 OCH3 OCH3 CH3 OCH3 Cl OCH3 OC2H5 OCH3 H CH3 CH3 CH3 OCH3 CH3 OCH2CH3 CH3 Cl CH3 H Table IX-c EMI68.1 R9 Y1 H CH3 H OCH3 CH3 CH3 CH3 OCH3 OCH3 CH3 OCH3 OCH3 H H CH3 H OCH3 H H Cl CH3 Cl OCH3 Cl H OCH2CH3 CH3 H OCH3 OCH2CH3 Tabel IX-d EMI69.1 R9 Y1 H CH3 H OCH3 CH3 CH3 CH3 OCH3 OCH3 CH3 OCH3 OCH H H CH3 H OCH3 H H Cl CH3 Cl OCH3 Cl H OCH2CH3 CH3 OCH2CH3 OCH3 OCH2CH3 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 diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Table X Weight Percent* Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or 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, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at OOC. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147ff. and APerry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. S, line 17 and Examples 1-4; - G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York,.1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 7 Wettable Powder N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino- carbonyl]-2,5-dimethyl-1H-pyrrole-3 sulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example 8 Wettable Powder N-t(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,5- dimethyl-lH-pyrrole-3-sulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammermilled 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 12 5% attapulgite granules 95% (U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. Example 10 Extruded Pellet N-[ (4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-lR- pyrrole-2-sulfonamide 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. these may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. Example 11 Oil Suspension N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- lH-pyrrole-2-sulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 12 Wettable Powder N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]-2,5-dimethyl-lH-pyrrole-3- sulfonamide 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles 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 13 Low Strength Granule N-[ (4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-l- methyl-lH-pyrrole-X-sulfonamide; (X indicates mixtures of pyrrole-2- and pyrrole-3 sulfonamides) 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. -20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 14 Aqueous susPension N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1- (phenylmethyl) -lH-pyrrole-X-sulfonamide, (X indi cates mixtures of pyrrole-2- and pyrrole-3 sulfonamides) 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. Example 15 Solution x-[ ( (4,6-dimethylpyrimidin-2-yl) aminocarbonyl)- aminosulfonyl]-l-methyl-lS-pyrrole-2-carboxylic acid, methyl ester, (X indicates mixtures of 4 and 5-substituents), sodium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. ExamPle 16 Low Strength Granule N-[(4,6-dlmethylpyrimidin-2-yl)aminocarbonyl]-X- nitro-lR-pyrrole-2-sulfonamide, (X indicates mixtures of 3- and 4-substituents) 0.1% attapulgite granules 99.9% (U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged. Example 17 Granule 4-[( (4,6-dimethylpyrimidin-2-yl)aminocarbonyl)amino sulfonyl]-lH-pyrrole-2-carboxylic acid, methyl ester 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20% of the natural sugars) attapulgite clay 9% The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the. fluidized material. The 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 18 High Strength Concentrate 5-[((4,6-dimethySpyrimidin-2-yl)aminocarbonyl)amino- sulfonyl]-4-bromo-lH-pyrrole-2-carboxylic acid, methyl ester 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 19 Wettable Powder 4-bromo-S-[ ( (4,6-dimethylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl) -l-methyl-lH-pyrrole-2-carboxylic acid, ethyl ester 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. Example 20 Wettable Powder X-[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino- carbonyl)aminosulfonyl]-lH-pyrrole-2-carboxylic acid, methyl ester (X indicates mixtures of 4 and.5-substituents) 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 21 Oil Suspension N-[(4,6-dimethylpyrimidin-2-ylaminocarbonyl]-lH- pyrrole-2-sulfonamide 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water. Utility 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, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate, time and method of application, compounds of this invention may also be used to modify plant growth beneficially; some of the compounds may be used to selectively control weeds in crops such as wheat, barley., cotton and soybeans. The precise amount of the compounds of Formula I to be used in any given situation will vary according to the particular end result desired,. the amount of foliage present, the weeds to be controlled, the crop species involved, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situa tions. Broadly speaking, the compounds of this inven tion are used at levels of about 0.01 to 20 kg/ha with a preferred range of 0.03 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired. The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with the ureas: such as 3-(3,4-dichlorophenyl)l,l-dimethylurea (diuron); the triazines: such as 2 chloro-4- (ethylamino)-6-(isopropylamino)-s-triazine (atrazine); the uracils: such as 5-bromo-3-sec-butyl6-methyluracil (bromacil); N-(phosponomethyl)glycine (glyphosate); 3-cyclohexyl-1-methyl-6-dimethylaminos-triazine-2,4(1H,3H)-dione (hexazinone); N,N-dimethyl2,2-diphenylacetamide (diphenamid); 2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate (barban); S-(2,3-dichloroallyl)-diisopropylthiocarbamate (diallate); S-(2,3,3-trichloroallyl-diisopropyltiocarbamate (triallate); 1,2-dimethyl-3,5 diphenyl-lA-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxylpropanoate (dichlofop methyl); 4-amino-6tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (metribuzin); 3-(3,4-dichlorophenyl)-l-methoxy-l- methylurea (linuron); 3-isopropyl-lH-2,1,3-benzo- thiodiazin-4(3H)-one-2,2-dioxide (bentazon); &alpha;,&alpha;,&alpha;- trifluoro-2,6-dinitro-N,N-dipropyl-2-toluidine (trifluralin); l,l'-dimethyl-4,4'-bipyridinium ion (paraquat); monosodium methanearsonate (MSMA); 2-chloro-2'.,6'-diethyl (methoxymethyl)acetanilide (alachlor); 1,1-dimethyl-3-(&alpha;,&alpha;,&alpha;-trifluoro- m-tolyl)-urea (fluometuron); and 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoic acid, methyl ester (acifluorfen-methyl) The activity of these compounds was discovered in greenhouse tests. The tests are described and data resulting from them are shown below. Compound 1 EMI81.1 mixture of 2- and 3-isomers Compound 2 EMI81.2 mixture of 2- and 3-isomers Compound 3 EMI81.3 Compound 4 EMI81.4 mixture of 2- and 3-isomers Compound 5 EMI82.1 Compound 6 EMI82.2 Comoound 7 EMI82.3 Compound 8 EMI82.4 Compound 9 EMI83.1 Compound 10 EMI83.2 Compound 11 EMI83.3 Compound 12 EMI83.4 mixture of 4- and 5-isomers Compound 13 EMI84.1 mixture of 2- and 5-isomers ComPound 14 EMI84.2 Compound 15 EMI84.3 Compound 16 EMI84.4 mixture of 4- and 5-isomers Compound 17 EMI85.1 Compound 18 EMI85.2 Compound 19 EMI85.3 Test A Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a nonphytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the second trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with two leaves, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, then all species were compare to controls and visually rated for response to treatment as recorded in Table A. The ratings are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: G = growth retardation; C = chlorosis/necrosis; E = emergence inhibition; H = formative effects; 6Y = flowerbuds abscised; U = unusual pigmentation; A = accelerated growth; 6F = delayed flowering; and X = axillary stimulation. Table A Compound Compound Compound Compound 1 2 3 4 Rate kg/ha 0.4 2 0.4 0.4 POST-EMERGENCE Bush bean 7C,9G 7C,9G 7C,6G,6Y 8C,7G Cotton 4C,9G 3C,4G 7C,6G 7C,6G Morningglory 6C,9G 2C,7G 10C 10C Cocklebur 5C,9G 2C,7G 5C,5G 7C,7G Cassia . 2C,4H 2C,7G 7C,6G 8C,7G Nutsedge 7G 4G 7C,6G 8C,5G Crabgrass 3C,6G 3C,7G 10C 10C Barnyardgrass 9C 3C,8H 10C 10C Wild Oats 5C,8G 2C,7G . 10C 7C,7G Wheat SC,9G 2C,8G 7C,6G 6C,5G Corn 5U,9G 1C,8G 6C,5G 10C Soybean 9C 1C,8G 7C,6G 7C,6G Rice 9C 2C,8G 8C,7G 8C,7G Sorghum 9C 1C,8G 8C,6G 5C,3G PRE-EMERGENCE Morningglory 9G 9G 7C,7G 7C,6G Cocklebur - 8H 3C,6G 8C,8G Cassia 8G 2C,8G 4C,6G 8C,8G Nutsedge 10E 8G 10E 10E Crabgrass 1C,5G 3C,9H 8C,8G 7C,8G Barnyardgrass. 9H 2C,9H 10C 8C,9G Wild Oats 1C,8H 2C,7G 8C,7G 7C,6G Wheat 1C,8G 2C,9H 10E 7C,8G Corn 3C,9G 2C,9G 10E 10E Soybean 7H 4H 9H,9G 7C,8G Rice 10E 9H 10E 10E Sorghum 3C,9H 2C,9H 10E 7G,8G Table A (continued) Compound Compound Compound Compound 5 6 7 8 Rate kg/ha 0.4 0.4 0.4 0.4 POST-EMERGENCE Bush bean 5C,6G,6F 4C,6G,6Y 9C,8G 0 Cotton 2C,3G 3G 2G 0 Morningglory 2C,3G 2C,3G 5C,4G 0 Cocklebur 2G 2G 2C,4G 0 Cassia . 0 0 2C,2G 0 Nutsedge 0. 0 3G 0 Crabgrass 0 2C,3G 10C 0 Barnyardgrass 2C,3G 5C,3G 10C 0 Wild Oats 3C,3G 5C,6G 10C 5C Wheat 4C,3G 2C,3G 8C,6G 1C Corn 3C,3G 2C,3U,4G 7C,5G 1C,2G Soybean 0 0 4C,5G 0 Rice 3C,4G 2C,3G 7C,6G 0 Sorghum 2C,3G 4G 8C,6G 2C,8G PRE-EMERGENCE Morningglory 4G 5C,7G 7G,7C 0 Cocklebur 5C,4G 10C 10C 2C,2H Cassia 3C,5G 7C,5G 7C,6G 1C Nutsedge 0 8C,8G 10E 2C,6G Crabgrass 4G 2C,5G 5C,8G 2C,5G Barnyardgrass 7C,8G 7C,7G 10C 3C,8H Wild Oats 7C,6G 5C,6G 7C,7G 3C,9G Wheat 8C,8G 10E 10C 2C,9G Corn 7C,8G 7C,8G 10C 3C,9G Soybean 7C,6G 7C,6G 8C,8G 0 Rice 7C,8G 10E 10C 3C,9G Sorghum 10E 8C,8G 10C 3C,9G Table A (continued) Compound 9 Rate kg/ha 0.4 POST-EMERGENCE Bush bean 2G Cotton 0 Morningglory O Cocklebur 5G,6F Cassia 2A Nutsedge 0 Crabgrass 0 Barnyardgrass O Wild Oats 0 Wheat O Corn 0 Soybean 1H Rice 3G Sorghum 2C,9G Table A (continued) Compound Compound 10 11 Rate kg/ha 0.4 0.1 0.05 POST-EMERGENCE Bush bean 3C,9G,6Y 5C,9G,6Y 6C,9G,6Y Cotton 2C,2H 3C,6H 2C,6G Morningglory 3C,5G 5C,9G 2C,8H Cocklebur 2C 9C 3C,9G Cassia . 2C,9G 9C 2C,9G Nutsedge . 3G 6G 2C,9G Crabgrass 2C,8H 9C 2C,8G Barnyardgrass 2C,8H 2C,8H 3C,9H Wild Oats 1C,3G 6C,9G 3C,9G Wheat 8G,5X 1C,8G 3C,9G Corn 2C,7G 2C,9G 2C,9G Soybean 1C,2H 9C 2C,9G Rice 4G 5C,8G 5C,9G Sorghum lC,9G 2C,9G 3C,9G PRE-EMERGENCE Morningglory 7G 9H 4C,9H Cocklebur 8H 9H 4C, 9H Cassia 7G 3C,9G 4C,9G Nutsedge 7G 10E SC,9G Crabgrass 2C,7G 5C,9G 2C,8G Barnyardgrass 9H 4G,9H 2C,8H Wild Oats 2C,8G 5C,9H 3C,8G Wheat lC,9G 2C,9H 9H Corn lC,9G 10E SC,9H Soybean 3H 9H 3C,8H Rice 7G 9H 9H Sorghum lC,9H 5H,9H 10H Table A (continued) Compound Compound 12 13 Rate kg/ha 0.4 0.4 POST-EMERGENCE Bush bean 6C,9G,6Y 2C,6F Cotton 4C,9G Morningglory 6C,9G 4C,8G Cocklebur 6C,9G 3C,6G Cassia . 6C,9G 3C,6G Nutsedge . 5G 8G Crabgrass 3C,9G 4C,9G Barnyardgrass 9C 5C,9H Wild Oats 5C,8G . 7G Wheat 5U,9G 2C,8G Corn 7U,9G 6U,9G Soybean 9C 2C,8G Rice 5C,9G 6C,9G Sorghum 5C,9G 6C,9G PRE-EMERGENCE Morningglory 9G 8G Cocklebur 9H 8H Cassia 2C,9G 7G Nutsedge 10G 10G Crabgrass 8G,2C 5C,9G Barnyardgrass 2C,9H 5C,9H Wild Oats 3C,9G 2C,7G Wheat 3C,9H 3C,9H Corn 3C,9G 2C,9G Soybean 2C,5H 2G Rice 10E 10E Sorghum 3C,9H 10H Table A (continued) Compound 14 Rate kg/ha 0.4 POST-EMERGENCE Bush bean 5C,8G,6Y Cotton 5C,8G Morningglory 9C Cocklebur 3C Cassia . 10E Nutsedge 2C,9G Crabgrass 5C,9H Barnyardgrass 2C,9G Wild Oats 2C,9G Wheat 2C,9G Corn 4U,9G Soybean 3C,9G Rice 3C,9G Sorghum 3C,9G PRE-EMERGENCE Morningglory 9G Cocklebur 5H Cassia 3C Nutsedge <RTI ID=92.3> 10E Crabgrass 3C,6G Barnyardgrass 3C,8H Wild Oats 2C,5G Wheat 9H Corn 2C,9H Soybean 2C,2H Rice 9H Sorghum 2C,9H Table A (continued) Compound Compound Compound 15 16 17 Rate kg/ha 0.4 0.4 0.4 POST-EMERGENCE Bush bean 6C,9G,6Y 9C 3C,7G,6Y Cotton 2C,8G 5C,9G 2C Morningglory 2C,6G 9C 1C Cocklebur 4C,9G 10C 2C,5G Cassia 2C,3H 6C,9G 1C Nutsedge . 2C,5G 3C,9G 0 Crabgrass 3C,8G 9G 0 Barnyardgrass 5C,9H- 9C 1H Wild Oats 2C,9G 6C,9G 0 Wheat 3C,9G 6C,9G 0 Corn 9C 9C 3C,8H Soybean 9C 5C,9G 1H Rice 2C,9G 6C,9G 2C,8G Sorghum 2C,9G 6C,9G 2C,9H PRE-EMERGENCE Morningglory 9G 9C Cocklebur 9H 8H Cassia 5G 9H Nutsedge 5G 10E Crabgrass 1C 6C,9G Barnyardgrass 4C -6C,9H Wild Oats 4G 6C,9G Wheat 3G 9H Corn 8G 10E Soybean 3H 9H Rice 9H 10E Sorghum 2C,9H 6C,9H Table A (continued) Compound Compound 18 19 Rate kg/ha 0.4 0.05 POST-EMERGENCE Bush bean 3C,9G,6Y 3C,6Y Cotton - 1C Morningglory 3G 1C,3H Cocklebur 9C 2C Cassia 2C,5G 1C Nutsedge , 2C,8G 2G Crabgrass 4C,9G 2C,5G Barnyardgrass 5C,9H 3G Wild Oats 4C,8G 4G Wheat 3C,8G 4G Corn 5C,9H 1C,4H Soybean 6C,9G 2C,2H Rice 5C,9G 8G Sorghum 4C,9G 2C,9G PRE-EMERGENCE Morningglory 8G Cocklebur 9H Cassia 8H Nutsedge 10E Crabgrass 3G Barnyardgrass 2C,9H Wild Oats 2C,8G Wheat 9H Corn 3C,9H Soybean 4H Rice 10E Sorghum 2C,9H Test B Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanquinalis) barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (S ida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention. Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Table B Compound 10 Rate kg/ha 0.5 Crabgrass 2G Barnyardgrass 4G Sorghum 9G,5H Wild Oats 6G Johnsongrass 7G,3H Dallisgrass 3G Giant Foxtail 7G,5C Ky. bluegrass 6G,5C Cheatgrass 8G,8C Sugarbeets SG Corn O Mustard 8G Cocklebur 0 Pigweed 3G Nutsedge O Cotton 2G Morningglory 3G Cassia Teaweed 4G Velvetleaf 4G,3H Jimsonweed o Soybean 0 Rice 7G,3C Wheat 4G Table B (continued) Compound 11 Pre-emergence Rate kg/ha 0.13 Crabgrass 6G,2C Barnyardgrass 5G,4C Sorghum 10C Wild Oats . 7G,4C Johnsongrass 7G,3C Dallisgrass 6G Giant Foxtail 7G,5C Ky. bluegrass 6G,3C Cheatgrass 9G,8C Sugarbeets 7G,5C Corn 9G,9C Mustard 8G,SC Cocklebur 4G,2C Pigweed Nutsedge 10E Cotton 2H Morningglory 7G Cassia 8G Teaweed 5G Velvetleaf 7G,5H Jimsonweed Soybean O Rice 10C Wheat 6G,4C Table B (continued) Compound 1 Rate kg/ha 0.03 0.13 Crabgrass 0 0 Barnyardgrass 0 0 Sorghum 3G 8G,5H Wild Oats , 0 5G Johnsongrass . 0 3G Dallisgrass 0 0 Giant Foxtail 0 0 Ky. bluegrass 0 . 5G Cheatgrass 4G 7G,2C Sugarbeets 3G 8G,5C Corn 0 1C Mustard 7G,3C 8G,6C Cocklebur 0 0 Pigweed a 2G Nutsedge 3G 7G,3C Cotton 0 0 Morningglory 0 5G Cassia 3G 5G Teaweed 0 5G Velvetleaf 0 5G,3H Jimsonweed 0 . 3G Soybean 0 0 Rice 5G 8G,8C Wheat 0 3G Table B (continued) Compound 3 Rate kg/ha 0.02 0.5 Crabgrass 6G 9G,8C Barnyardgrass 6G,3H 10C Sorghum 9G,9C 10E Wild Oats 3G 8G,6C Johnsongrass . 6G,3H 9G,8C Dallisgrass 4G 9G,5H Giant Foxtail 6G,3H 10C Ky. bluegrass 6G 9G,8C Cheatgrass 7G,8C 10E Sugarbeets 4G 10C Corn 4G 9G,9C Mustard 8G,8C 10C Cocklebur 0 8G,5H Pigweed 9G,9C 10E Nutsedge 0 10E Cotton 0 7G,5H Morningglory 6G 9G,8C Cassia 6G 9G,5C Teaweed 3G 7G,6C Velvetleaf 4G,2H 9G,9C Jimsonweed 4G . 9G,9C Soybean 0 8G,3H Rice 7G,5C 10E Wheat 3G 8G,8C Table B (continued) Compound 12 Rate kg/ha 0.13 Crabgrass 4G Barnyardgrass 7G,3H Sorghum 9G,5H Wild Oats . 7G Johnsongrass . 6G,3H Dallisgrass 4G,3H Giant Foxtail 3G Ky. bluegrass 4G Cheatgrass 8G,SH Sugarbeets 7G,8C Corn 2H Mustard 8G,5C Cocklebur 0 Pigweed Nutsedge O Cotton 3G,3H Morningglory 3H Cassia Teaweed 3G Velvetleaf 7G,SH Jimsonweed 4G. Soybean SG,3H Rice 10C Wheat 4G Table B (continued) Compound 13 Compound 18 Rate kg/ha 0.13 0.25 Crabgrass 3G 0 Barnyardgrass 2G 3C Sorghum 8G,5H 5G,3H Wild Oats . 2G 6G,3H Johnsongrass 4G,3H 5G,2H Dallisgrass - 3G Giant Foxtail 4G,3H 4G,2H Ky. bluegrass 2G . 6G,2H Cheatgrass 7G,5E 8G,5E Sugarbeets - 8G,7C Corn 0 7G,SH Mustard 7G,3C 7G,5C Cocklebur 2G 7G,3C Pigweed - 6G Nutsedge SG 8G Cotton 3G 5G Morningglory 3G 5G Cassia 3G 6G Teaweed 0 4G Velvetleaf 3G 6G,3H Jimsonweed - 4G Soybean 0 6G,3H Rice 8G,5H 10E Wheat 0 5G,2H Test C Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Diqitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua) . Approximately 2-1/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. Table C Over-the-Top Soil/Foliage Treatment Compound 3 Compound 4 Rate kg/ha 0.25 0.06 0.25 0.06 Soybeans 10G,6C 10G,5C 9G,9C 8G,2C Velvetleaf 7G,3C 4G,2C 8G,5C 4G,2C Sesbania 10G,9C 10G,7C 9G,9C 6G Cassia . 10G,5C 8G,4C - 8G,4C Cotton 7G,3C 5G,3C 6G,4C 3G,4C Morningglory 8G,3C 7G,4C 8G,4C 7G Alfalfa 5C 5G,3C - Jimsonweed 10G,5C 5G,2C - 0 Cocklebur , 10G,4C 7G,2C 2G 0 Corn 9G,5U 8G,3U 8G,7U 6G,7U Crabgrass 8G,4C 5G,3C 9G,9C 8G,7C Rice 8G,3C 7G,3C 8G,8C 8G,8C Nutsedge 5C,5G 5G,3C 5G 0 Barnyardgrass 9G,7C 7G,7H 10C 10C Wheat 2C '2C 8G,7C 8G,7C Giant foxtail - - 8G,7U 10C Wild Oats 7G,3C 4G 7G,6C 8G,7C Sorghum 8G,4C 7G,3C 5G,9U 5G,7U Yellow mustard - - 8G,8C 8G Pigweed - - - Johnsongrass <RTI ID=103.7> - - - Sunflower - - 6G 3G Sugarbeets - - 9G,9C 8G Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 7 Compound 1 Rate kg/ha 0.25 0.12 Soybeans 9G,9C 9G,5C Velvetleaf 5G,2C 10G,5C Sesbania 6G,4C 9G,4C Cassia . 6G 7G,3C Cotton . 4G 4G,2C Morningglory . 6G 7G,3C Alfalfa , 3G ' 3G,2C Jimsonweed 5G 4G,2C Cocklebur 8G 8G,3C Corn 10C 9G,4C Crabgrass 7G 2G Rice 8G,6C 8G,5C Nutsedge 7G,3C 7G,2C Barnyardgrass 9G,9C 2C,8G Wheat 9G,9C 3G Giant foxtail 7G,5C 6G,2C Wild Oats 7G,5C 5G Sorghum 8G,6C 9G,5C Yellow mustard 10C Pigweed Johnsongrass Sunflower 8G,3R Sugarbeets Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 11 Rate kg/ha 0.12 0.03 Soybeans 10G,7C 10G,7C Velvetleaf 9G,6C 9G,5C Sesbania 10G,8C 10G,5C Cassia . 10G,8C 10G,7C Cotton . 8G,6C 6G,3C Morninggiory 10G,7C 8G,4C Alfalfa 9G,4C 6G,3C Jimsonweed 7G,2C 3G,3C Cocklebur 10G,8C 10G,6C Corn 9G,5C 9G,5C Crabgrass 10G,8C 9G,5C Rice 8G,5C 8G,4C Nutsedge 9G 8G Barnyardgrass 9G,4C 7G,3C Wheat 8G,5C 7G,4C Giant foxtail 9G,5C 7G,3C Wild Oats 9G,5C 9G,3C Sorghum Yellow mustard Pigweed Johnsongrass Sunflower Sugarbeets

Claims: Claims: 1. A compound of the formula: EMI106.1 wherein R1 is H, C1-C4 alkyl, NO2, CN, C(O)CC13, SO2Rll, C(O)R5 or CO2H; R2 is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, Cl or Br; R4 is H, C1- C4 alkyl, cyanoethyl, C5-C6 cycloalkyl, benzyl, phenyl substituted with Cl or NO2, or C(O)R6; R5 is C1-C4 alkyl or C1-C4 alkoxy; R6 is C1-C4 alkyl, C1-C4 alkoxy, or NR7R8; R7 and R8 are independently C1-C2 alkyl; R9 is H, CH3 or OCH3; R11 is C1-C4 alkyl; R10 is EMI107.1 X is CH3 or OCH3t Y is H, CH3, OCH3, OCH2CH3, OCH2CF3, Cl, CH20CH3, CH2OCH2CH3 or CF3; YÚ is H, CH3, OCH3, Cl or OCH2CH3; and Z is CH, N, CCR3 CCH2CH3, CCH2CH2C1, CC1, CBr or CF; and their agriculturally suitable salts; provided that (1) when R4 is C(O)R6, t-butyl or phenyl substituted with Cl or NO2, then R1 is H or C1-C4 alkyl and R1, R2 and R3 cannot be s-butyl or isopropyl; (2) R1, R2, R3 and Rll cannot be t-butyl; (3) in Formula Ia, when R1 is NO2, then R1 cannot be in the 5-position; (4) in Formula Ia, when R1 is not in the 5-position, R2 and R3 are other than H, and R1 must be other than H unless both R2 and R3 are H; (5) in Formula Ia, R3 cannot be C1 or Br; (6) in Formula Ib, R1 cannot be C(O)CC13; and (7) in Formula Ib, when R3 is Cl or Br, then R3 is in the 3-position and R1 is in the 5-position and R1 cannot be H or C1-C4 alkyl. 2. A compound of Claim 1 wherein R9 is H or CR3. 3. A compound of Claim 2 wherein R10 is EMI108.1 4. A compound of Claim 3 wherein Z is CH or N; R5 is C1 C4 alkoxy; R2 is H; R4 is H, C1-C4 alkyl or benzyl. 5. A compound of Claim 4, structure Ia, wherein R1 is H, C1-C4 alkyl or COR5. 6. A compound of Claim 4, structure Ib, wherein R1 is H, C1-C4 alkyl, NO2 or COR5. 7. A compound of Claim 5 wherein R1 is in the 5 position. 8. A compound of Claim 6 wherein R1 is H, NO2 or COR5. 9. A compound of Claim 7 wherein Y is CH3, OCH3 or OCH2CH3. 10. A compound of Claim 8 wherein Y is CH3, OCH3 or OCH2CH3. 11. The compound of Claim 1, N-[(4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl]-2,5-dimethyl-lR-pyrrole- 3-sulfonamide. 12. The compound of Claim 1, N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-lH-pyrrole-2-sulfonamide. 13. The compound of Claim 1, N-[(4-methoxy-6 methylpyrimidin-2-yl)aminocarbonyl]-lH-pyrrole-2- sulfonamide. 14. The compound of Claim 1, N-[(4-methoxy-6- methyl-1,3,5-triazin-2-yl) aminocarbonyl)-2,5-dimethyllH-pyrrole-3-sulfonamide. 15. The compound of Claim 1, N-1(4,6-dimethyl- pyrimidin-2-yl) aminocarbonyl] -l-methyl-lH-pyrrole-X- sulfonamide; (X indicates mixtures of pyrrole-2- and pyrrole-3-sulfonamides). 16. The compound of Claim 1, N-[(4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl]-1-(phenylmethyl)-lHpyrrole-X-sulfonamide; (X indicates mixtures of pyrrole-2- and pyrrole-3-sulfonamides). 17. The compound of Claim 1, X-[((4,6-dimethyl pyrimidin-2-yl)aminocarbonyl)aminosulfonyl]-1-methyl- lH-pyrrole-2-carboxylic acid, methyl ester; (X indicates mixtures of 4- and 5-substituents). 18. The compound of Claim 1, N-[(4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl]-X-nitro-lH-pyrrole-2- sulfonamide; (X indicates mixtures of 3- and 4-substituents). 19. The compound of Claim 1, 4-[((4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl)aminosulfonyl]-lH-pyrrole- 2-carboxylic acid, methyl ester. 20. The compound of Claim, 1,5-[((4,6-dimethyl pyrimidin-2-yl)aminocarbonyl)aminosulfonyl]-4-bromo-lH- pyrrole-2-carboxylic acid, methyl ester. 21. The compound of Claim 1, X-[((4-methoxy-6- methyl-1,3,5-triazin-2-yl)aminocarbonyl)aminosulfonyl]lH-pyrrole-2-carboxylic acid, methyl ester (X indicates mixtures of 4- and 5-substituents). 22. The compound of Claim 1, 4-bromo-5-[((4,6dimethylpyrimidin-2-yl)aminocarbonyl)aminosulfonyl)-1 methyl-lR-pyrrole-2-carboxylic acid, ethyl ester. 23. A compound of claim 1 of the formula EMI110.1 wherein R1 is H, C1-C4 alkyl or NO2; or when the compounds are of formula (Ic) may also be C(O)CC13, CO2H, or CO(C1-C4 alkoxy); R2 is H or C1 C4 alkyl; R3 is H or CH3; R4 is H, C1-C4 alkyl, C5-C6 cycloalkyl or C(O)R6; R6 is as defined in claim 1; R9 is H or CH3; R10 is EMI111.1 wherein X, Y, yl and Z are as defined in claim 1; with the further proviso that (8) when R1 is NO2 then R4 is not C(O)R6; and their agriculturally suitable salts. 24. A composition suitable for controlling the growth of undesired vegetation or for use as a plantgrowth regulant which comprises an effective amount of a herbicidal compound or plant growth regulant and at least one of the following: surfactant, solid or liquid diluent, characterised in that said herbicidal compound or plant-growth regulant comprises a compound of any of claims 1 to 23. 25. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 23. 26. A method for regulating the growth of plants by applying to the locus of said plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of any of claims 1 to 23. 27. A process for preparing a compound of claim 1 which comprises contacting under reaction conditions EMI112.1 wherein R1, R2, R3 R4, R5 and R10 are as defined in claim 1. 28. A process of claim 27 wherein the reaction is performed in a solvent, in the presence of a Friedel Crafts catalyst. 29. A process of claim 28 in which the Friedel Crafts catalyst is selected from aluminum (III) chloride, aluminum (III) bromide, gallium (III) chloride, tin (IV) chloride, iron (III) chloride, antimony (V) chloride, antimony (V) fluoride, zinc (II) chloride, antimony (III) chloride, titanium (IV) chloride, boron (III) fluoride, sulfuric acid or hydrofluoric acid. 30. A process of Claim 28 or 29 wherein the solvent is methylene chloride, tetrahydrofuran, nitromethane, nitroethane or nitropropanes. 31. A compound of the formula EMI112.2 wherein Rg and R10 are as defined in claim 1. 32. A process for the preparation of a compound of claim 31 which comprise reacting a corresponding heterocyclic amine of formula R9R10NH with chlorosulfonyl isocyanate.

Inventors: BUDZINSKI, JOHN CHARLES, LEVITT, GEORGE, ZIMMERMAN, DONNA FRIEZE
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1981
Main classification: A01N47
IPC codes: C07D491, A01N47, C07D521