HERBICIDAL BENZENE- AND PYRIDINE-SULFONAMIDE DERIVATIVES

Abstract: Compounds of the general formula wherein R₁ is R₃S[O] n ; R₃ is C₁-C₄ alkyl, C₃-C₄ alkenyl, cyclopentyl or cyclo­ propylmethyl; R₂ is H, F, Cl, Br, CH₃, OCH₃CF₃, NO₂, CN or NH₂; n is 0, 1 or 2; W is O or S; T is CH or N; Z is CH or N; X is CH₃, C₂H₅, OCH₃, OC₂H₅, or CH₂OCH₃; and Y is CH₃ or OCH₃; and their agriculturally suitable salts; exhibit general and selective herbicidal activities, and may also be used as plant growth regulants. The compounds can be formulated into agricultural com­ positions in conventional manner. They may be made e.g. by reacting a corresponding benzene- or pyridine- sulfonyl isocyanate or isothiocyanate with the appropriate 2-aminopyrimidine or 2-amino-1,3,4-triazine.

Description: "Herbicidal benzene- and pyridine sulfonamide derivatives" Background of the Invention This invention relates to novel alkyl sulfones. The compounds of this invention and their agriculturally suitable salts1 are useful as agricultural chemicals, e.g. plant growth regulants and herbicides. Netherlands Patent 121, 788, published September 15, 1966, discloses the preparation of compounds of the following Formula and theiruse as general or selective herbicides: EMI1.1 wherein R1 ane R2 may independently be alkyl of 1-4 carbon atoms; and R3 and R4 may idependently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. U.S. Patent 3,637,366 discloses compounds having the formula: EMI1.2 wherein R1 is hydrogen or lower saturated aliphatic acyi and R2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua. French Patent 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: EMI2.1 wherein R = H, halogen, CF3 or alkyl. Logemann et al. Chem Ab., 53 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: EMI2.2 wherein R is butyl, phenyl, or EMI2.3 and R1 is hydrogen or methyl. When testec for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive. Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: EMI2.4 In U.S. Patent 4,127,405, agricultural sulfonamides of the following formula are taught: EMI3.1 wherein R is EMI3.2 R1 is EMI3.3 EMI3.4 and R6 are idependently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 car bon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH3S(O)n - or CH3CH2S(O)n-; R4 is hydrogen, fluorine, chlorine, bromine or methyl; R 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; ; R9 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, trifluoro methyl, CH3 S- or Cv3OCH2-; and Z 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, R, R6 and R7 must be hydrogen; b) when R5 is hydrogen and all of R3, 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 R6 must be hydrogen. The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing 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 connonly referred to as herbicides. The need still exists however, for more effective herbicides. Summary of the Invention This invention relates to compounds of Formula (I) and their agriculturally suitable salts, suitable agricultural compositions containing them and methods of using them as general and/or selective preemergence and post-emergence herbicides and as plant growth regulants. EMI5.1 wherein R1 is R3S[O]n; R3 is C1-C4 alkyl, C3-C4 alkenyl, cyclopentyl or cyclopropylmethyl; R2 is H, F, C1, Br, CH3, OCH3, CF3, NO2, CN or NH2; n is O, 1 or 2; .W is O or S; T is CH or N; Z is CH or N; X is CH3, C2H5, OCH3, OC2H5, or CH2OCH3; and Y is .CH3 or OCH3; and their agricultural salts; provided that (1) when R2 is CN, then T is CH and is not ortho to the sulfonylurea group; (2) when W is S, then n is 0 or 2; (3) when T is N, then n is 2; and (4) when T is CH, then R3 is not C1-C2 alkyl and R1 is at the 2- or 4- position. Preferred Compounds Preferred in order of increasing activity and/or increasingly favorable ease of synthesis are: (1) Compounds of Formula(I)wherein W is O and R2 is H, F, C1, Br, CH3 or' OCR3; (2) Compounds of Preferred (1) wherein R1 is at the 2- or 4- position when T is N; (3) Compounds of Preferred (2) wherein n is 2; (4) Compounds of Preferred (3) wherein R2 is H; (5) Compounds of Preferred (4) wherein X is CH3 or OCH3; and (6) Compounds of Preferred (5) wherein R3 is C1-C4 alkyl. Specifically preferred compounds for reasons of highest activity and/or most favorable ease of synthesis are: N-t(4,6-dimethylpyrimidin-2-yl)aminocarbonyl3-2-E methylethyl)sulfonyl]benzenesulfonamide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2 [(1-methylethyl)sulfonyl]benzenesulfonamide; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(1 methylethyl)sulfonyl3benzenesulfonamide; N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2 [(1-methylethyl)sulfonyl]benzenesulfonamide; N-C(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar bonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide; N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2 [(1-methylethyl)sulfonyl]benzenesulfonamide; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzenesulfonamide; ; N-E(4-methoxy-6-methylpyrimidin-2-yl)amflnocarbon 2-(propylsulfonyl)benzenesulfonamide; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzenesulfonamide; N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzenesulfonamide; N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon yl]-2-(propylsulfonyl)benzenesulfonamide; N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] 2-(propylsulfonyl)benzenesulfonamide; N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide; N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] 2-(methylsulfonyl)-3-pyridinesulfonamide; N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] 2-(methylsulfonyl)-3-pyridinesulfonamide; N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide; ; N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl] 2- (methylsulfonyl) -3-pyridinesulfonamide; and N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]-2-(methylsulfonyl)-3-pyridinesulfon amide Any of these compounds may be used as their agriculturally suitable salts. The compounds of the present invention include those compounds of the general formula (I) within the scope of claims 1 of our U.S. Applications Serial Nos. 128,176 and 134,287, as defined in claims 9 and 10 herein. Svnthes is As shown in reaction la, compounds of Formula (I) can be prepared by reacting an appropiate 2-aminopyrimidine or 2-amino-l,3,5-triazine of Formula III with an aporooriately substituted sulfonyl isocyanate or isothiocyanate of Formula II ; R1 is R3SO2 or R3S and R2#amino: EMI8.1 This reaction is best carried cut in an inert or garlic solvent (such as acetonitrile, tetrahydrofuran, methylene chloride, etc.). The reactants may be added in any order; the reaction is generally exothermic.. Conveniently, the starting reaction temper- ature is ambient, but it can be varied from about 0 to 100 if desired. The product can be isolated by filtration if it piecipitates from the reaction mixture; otherwise the solvent can be evaporated and the residual product obtained thereby, with optional purification through trituration with an organic solvent (e.g. diethyl ether, l-chlorobutane, etc.) in which it is only sparingly soluble, or by recrystallization. The compounds of Formula (I) in which R2 is amino can be made by catalytic reduction of the corresponding nitro compound [R. N. Icke, et al., Org. Svn. Coll. Vol. 3, p. 59 [1955], or by chemical reduction by methods known in the art. An alternative method for preparation of compounds (I), with W=S, is to react the appropriate sulfonamide IV with a heterocyclic isothiocyanate: EMI9.1 (I), with W=S. The heterocyclic isothiocyanates used in this procedure can be made, for example, by the method of Japan Patent Application Pub: okapi 51-143686, June 5, 1976, or that of W. Abzaham and G. Barnikow Tetrahedron 29, 691 (1973). ReactionIb is best carried out in an inert, polar solvent (e.g., acetone or butanone) at 20 to 50 , in the presence of a basic catalyst (e.g., K2CO3 or Na2CO3), during about 1 to 10 hours. The alkali metal salt of (I), with W = S, is filtered off, suspended in water, and the pH adjusted down to 1-3 with acid (e.g., HCl or H2SO4) to form compound (I), with W ^ S, recovered by filtration. Compounds of Forrrtula (I), with W=O, can also be prepared by the reaction of the substituted sulfonamides of Formula IV with an aoorooriate heterocyclic isocyanate by the general method described in our European application No. 80304285.2. The intermediate sulfonyl isocyanate IIa within Formula II can be prepared by reacting appropriate sulfonamides IV with phosgene in the Presence of n-butyl isocyanate at reflux in a solvent such as xylene, according to the procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods of Precarative Oroanic Chemistry, Vol. VI, p. 223-2a1, Academic Press, New York and London, W. Foerst Ed., as shown in reaction 2a: EMI10.1 The sulfonamide IV, an alkyl isocyanate te.g. butyl isocyanate) and a catalytic amount of 1,4 dia za [2.2.2] bicyclooctane (DABCO) in xylene or other inert solvent of sufficiently high boiling point (e.g. > 1350) are mixed and heated to about 135e, phosgene is added until an excess is present (indicated by a drop in boiling point). The mixture is further heated and excess phosgene driven off. After the mixture is cooled and filtered from insoluble material, the solvent, alkyl isocyanate and excess phosgene are evaporated, leaving the sulfonyl isocyanate IIa. If desired, the alkyl isocyanate/sulfonamide adduct can be made and isolated before reaction with the phosgene; in that case the sulfonamide IV, alkyl isocyanate and anhydrous base (e.g. K2C03) in an unreactive solvent (e.g., acetone, butanone or acetonitrile) are mixed and boiled under reflux for 1/2 to 4 hours, followed by dilution of the reaction mixture with water and adjustment of pR to about 3 with acid (e.g., IJCl, H2S04, etc.), followed by filtration to provide the adduct, which can be reacted with phosgene as described above. Am alternative method for Drecaration of sulfonyl isocyanates IIa is the method of Ulrich et al. [J. Org. Chem. 34, 3200 (1969)1, from a suitably substituted sulfonamide of Formula IV as shown in reaction sequence 2b: EMI11.1 The sulfonamide is boiled under reflux with an excess of thionyl chloride, which functions as a reactant and solvent. The reaction is continued until the sulfonamide protons are undetectable in the proton resonance spectrum. An overnight reaction period (about 16 hours) is frequently sufficient, though several days (e.g. 5) may be required in some cases to convert completely the sulfonamide m7 to the thionylamide Vl . The thionyl chloride is evaporates and the residue treated with an inert solvent (e.g., xylene, toluene, benzene, etc.) at least one equivalent of phosgene, and a catalytic amount of pyridine. The mixture is heated to about 60-140 , with 80-1000 preferred. Conversion to the isocyanate is substantially complete within about 1/4 to 3 hours. The mixture containing the isocyanate can be used directly for the next reaction step [formation of compound (I), with W = OJ or isolated in purified form by filtration and/or evaporation of solvent. The intermediate sulfonyl isothiocyanates (IIb) within Formula II can be prepared by the method of Hartke [Chem. Abstr. 64, 15783e (1966)1 br U.S. Patent 3,346,590, as shown in reaction sequence 2c: EMI12.1 The appropriate sulfonamide in OF is treated with an equivalent of carbon disulfide and two equivalents of powdered potassium hydroxide at about 350; other bases, including non-nucleophilic bases such as sodium hydride, can be used instead of KOH. The mixture is stirred (about 1-6 hours) until solution is substantially complete, then diluted with an aprotic solvent (e.g., ethyl acetate) to precipitate the intermediate potassium salt VII. The latter is separated by filtration of the reaction mixture, suspended in an inert solvent (e.g., toluene or xylene) and treated with two moles of phosgene (or thionyl chloride6 etc.) at about 00. The mixture is allowed to warm to ambient temperature, filtered and the sulfonyl isothiocyanate used as-is for formation of compound (I), with W - S, or isolated by evaporation of the solvent. The sulfonyl isothiocyanates may dimerize or trimerize in some cases, but the dimers and trimers still produce the compounds (I) on reaction with the amine III. The intermediate sulfonamides IV can be prepared by well-known methods. For example, the preparation of sulfonamides from ammonium hydroxide and sulfonyl chloride is widely reported in the literature, e.g., Crossley et al., J. Am. Chem. Soc. 6, 2223 (1938). Preparation utilizing the reaction of sulfonyl chlorides with an excess of anhydrous ammonia at O in ethyl ether or chlorobutane is also known. Certain sulfonyl chlorides are best orepared by chlorosulfonation of a substituted benzene accordinq to the teaching of H. T. Clarke et al., Oro. Synth. Coll. Vol. 1, 2nd Ed., 1941, p. 85. Pvridinesulfonvl chlorides and other benzenesuifonyl chlorides are best prepared ky diazotization of the appropriate amino compound with sodium nitrite in HC1, followed by reaction of the diazoniurn salt with sulfur dioxide and cuorous chloride in acetic acid according to the teaching of H. L. Yale and F. Sowinski, 3. Org. Chem. 25, 1824 (1960). 2-(Alkylsulfonyl)benzenesulfonyl isocyanates are important intermediates for the preParation of certain of the compounds of this invention. The synthesis of the sulfonamide intermediates required for these sulfonyl isocyanates is described in reaction sequences 3, 4, 5 and 6. 3. EMI14.1 EMI14.2 The thioether of Formula VIII can be prepared from the appropriate 2-aminomercaptoaromatic and an alkyl halide p3X as described in the literature, e.g. R. N. Prasad, et al. Can. J. Chem. 44, 1247 (1966). The formation of the sulfonyl chloride and the corresponding sulfonamide IVa has been previously described (co-pending application U.S.S.N. 082,522, filed October 19, 1979). The oxidation of iVa to the corresponding 2-(alkylsulfonyl)benzenesulfonamides of Formula IVb can be carried out by a variety of standard literature procedures with m-chloroperbenzoic acid [C. R. Johnson, et al., Tetrahedron 25, 5649 (1969)], or with aqueous hydrogen peroxide in acetic acid [F. G. Bordwell, et al., J. Amer. Chem. Soc. 77, 1141 (1955)]. EMI15.1 Halide displacement by thiols (n=O) or sulfinates (n=2) is widely reported in the literature (for general reviews see, "Organic Chemistry of Sulfur", S. Oae, ed., Plenum Press, New York, 1977, pp. 232-233; Reid, "Organic Chemistry of Bivalent Sulfur," Chemical Publishing Co., New York, Vol. 2, pp. 16-21, 24-29; Vol. 3, pp. 11-14; Peach, in Patai, "The Chemistry of the Thiol Group," pt. 2, pp. 735-744, John Wiley and Sons, Inc., New York, 197h). Reduction of XII to the amine XIII can be carried out by a variety of standard literature procedures, including catalytic hydrogenation (Rylander,"Catalytic Hydrogenation over Platinum Metals ",pp. 168-202, Academic Press, Inc., New York, 1967) and reduction with iron [D. Cowsley et al., Svnthesis 118 (1977)l or stannous chloride [Org. Synth., Coil. Vol. 2, 130 (1943); ibid, 3, 240, 453 (1955)1 in 'acidic medium. Compounds of Formula XII can also be prepared as shown in reaction sequence 5, where n=O or 2 [in addition to references cited above, see, Zh Obshch. Khim, 35 (8) 1361 (1965), and J. Chem. Soc. 763, (1946)]. The mercaptan or sulfinic acid is alkylated with an alkyl halide R3X in the presence of a base (e.g., tertiary amine; metal oxide, hydroxide, hydride or carbonate) to produce the nitroaryl sulfide or sulfone XII, which is converted to the sulfonamide IVC: EMI16.1 Starting pyridinesulfonamides IVd can be made by the method shown in reaction sequence 6 Ref.: Chem. Abstr. 83, 163951 p (1975)]. Thus, a mercaptan reacts with the chloropyridine compound XIV in the presence of a base to form the sulfide XV, which is then oxidized to the sulfone IVd. EMI17.1 Compounds of Formula Ib, where R1=SOR3 and W=O can be prepared from the appropriate compounds of Formula Ia where R1=SR3 and W=O, by oxidation with m-chloroperbenzoic acid according to reaction 7. EMI17.2 The reaction can be carried out by mixing equivalent amounts of Ia with m-chloroperbenzoic acid in an inert solvent such as chloroform and stirring at 0 to reflux for 12-24 hours,2fter which the insoluble m-chlorobenzoic acid produced is removed by filtration and the chloroform solution containing the desired sulfoxide is concentrated to yield the crude product. The product can be purified further by dissolving it in aqueous base of pH 19 and adjusting the pH to 4 to precipitate the desired compound while leaving the m-chlorobenzoic acid in solution as its sodium salt. Oxidation of Ia with 1 equivalent of hydrogen peroxide in acetic acid at Oe to room temperature will also produce Ib. 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. 2-Amino-l,3,5-triazines can be synthesized according to the methods described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII of the same series. The synthesis of sulfur compounds of pyridine has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., .Y. and London. Pyridinesulfonamides are described by H. L. Tale in "Pyridine and Its Deri vatives" Supplement, Part 4 (1975), which is incor porated herein by reference. Agriculturally suitable salts of compounds of Formula (I) are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula (I) with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula (I) can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula (I)(e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanoed. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a comoound of Formula (I) (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be' exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble. Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula( I ) with a suitable acid, e.g., g-toluenesulfonic acid, trichloroacetic acid or the like. The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and parts are by weight unless otherwise designated. Example 1 2-(1-Methylethylthio)benzenamine To a solution of 2-aminothiophenol (90%, 100 q, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (509 ml) was added dropwise 2-bromopropane (89 9, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3 x 500 ml). The ether extracts were washed with water and brine, dried with MSOL and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(l-methylethylthio) benzenamine: bp 940 (2.2-2.4 mm). NMR (CDC13)C: 1.25 (d, 6H, -CH3), 3.15 (hept., 1H, -CH-); 4.25 (broad s, 2H, -NH2); 6.40-7.40 (m, 4H, Ar-H). Example 2 2-(1-Methylethylthio)benzenesulfonamide To a solution of 2-(l-methylethylthio)benzenamine (200 g, 1.20 mol) in a mixture o-f concentrated hydrochloric acid (429 ml) and glacial acetic acid (120 ml) was added a solution of sodium nitrite (91.2 g, 1.32 mol) in water (18D ml) at -5 to 0 . The solution was stirred at 0 for 1/2 hour and then poure.d, in several portions, into a mixture of cupric chloride dihydrate (24 g) and liquid sulfur dioxide (37 ml, 8.28 mol), in glacial acetic acid (1200 ml) at 00. The resulting solution was stirred at Do for one hour and then allowed to warm to room temperature. After several hours, ether (100D ml) was added, and the reaction mixture was stirred overniqht and then poured into iceuwater. The resulting oil was extracted into dichloromethane. The organic extracts were washed with water and 5% aqueous sodium bicarbonate (until neutral), dried (MgSO4) and concentrated in vacuo to give an oil. The crude sulfonyl chloride was dissolved in dry TH (2000 ml) and treated with anhydrous liquid ammonia (50 ml, 2.3 mol) at 40. The solution was stirred at 0 for one hour, allowed to warm to room temperature, and stirred an additional 2.5 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with water (100 ml) and extracted with dichloromethane. The extracts were washed with water, dried (MgSO4) and concentrated to yield the crude product. The oil was dissolved in hot (600) hexane/n-butyl chloride (5/2). Upon cooling, 2-(methylethylthio)benzenesulfonamide settled out as a dark oil. NMR (CDCl3)#: 1.30 (d, -CH3); 3.60 (hept. -CH-); 5.75 (broad s, -NH2); 7.0-8.2 (m, Ar-H); IR (Nujol): 3200-3300 doublet); 1300 and 1150 cm-1. Example 3 2-[(1-Methylethyl)sulfonyl]benzenesulfonamide To a solution of 2-[(1-methylethyl)thio]benzene- sulfonamide (79 g, 0.34 mol) in glacial acetic acid (29D ml) was added dropwise 30% aqueous hydrogen peroxide (100 ml, 1.16 mol) at room temperature. When the addition was complete, the reaction mixture was heated to 800 for 2 hours and then allowed to cool to room temperature. Addition of ice-water resulted in the precipitation of 2-[(1-methylethyl)sulfonyl)ben- zenesulfonamide as a liqht-yellow solid, m.D. 150.1530. NMR (CDC13)g: 1.25 (d, -CH3); 4.20 (hept, -CH-); 6.9tO (broad s, -NH2); 7.60-8.40 (m, Ar-H) IR (KBr) 3400-330S (d), 1330, 1290, 1160 and 1130 cm-1. Examole 4 N-[Butylaminocarbonyl]-2-[(1-methylethyl)sulfonyl)ben zenesulfonamide A mixture of 2-[(1-methylethyl)sulfonyl]benzene- sulfonamide (29 g, 0.11 mol), butyl isocyanate (14.7 g, 0.15 mol) and anhydrous potassium carbonate (15.6 g, 0.120 mol) in methyl ethyl ketone (325 ml) was refluxed with stirring for 3 hours. The reaction mixture was cooled to 0 and then poured into ice-water. The aqueous solution was acidified to pH 1 with concentrated hydrochloric acid. The resulting precipitate was filtered off, washed with water and recrystallized from ethanol to give N-tbutylamino- carbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfon amide, m.p. 164.5-165.5 . NMR (DMSO)#: 0.6-1.6 (m, 13H, -(CH2)2-, CH3); 2.7-3.20 (m, 2H, -CH2-); 4.15 (hept, 1H -CH-); 6.85 (t, 1E, -NH-); 7.8-8.5 (m, 4.6H, Ar-H, -NH-); IR (KBr) 3300, 1660, 1430, 1310, 117: and 1130 cm-1. Example 5 2-[(1-Methylethyl)sulfonyl]benzenesulfonyl isocyanate A solution of N-[butylaminocarbonyl]-2-[(1 methylethyl)sulfonyl]benzenesulfonamide (17.4 g, 0.048 mol) and 1,4-diaza[2.2e2Jbicyclooctane (0.1 a) in mixed xylenes (90 ml) was heated to 135-140 . Liquid phosgene (3.6 ml, 0-050 mol) was added at a rate to maintain an internal temperature between 125-135 . When the addition was complete, the solution was refluxed for 2 hours, cooled to room temperature and then filtered under a nitrogen atmosphere. Removal out solvent in vacuo gave 2-[(l-methylethyl)suIfonyl3- benzenesulfonyl isocyanate, which was used immediately without further purification. Example 6 N-[(a,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 ¯r ( 1- methylethyl)sulfonyl]benzenesulfonamide A solution of 2-[(1-methylethyl)sulfonyl]benzene- sulfonyl isocyanate, (2.3 9, 0.008 mol) in dichloromethane (12 ml) was added to 2-amino-4,6-dimethylpyrimi- dine (0.74 a, 0.û06 mol) and the suspension was stirred overnight at room temperature. The solvent was removed in vacuo and acetonitrile was added to the residue. The precipitated solid was filtered off and dried to give N-[(4,6-dimethylpyrimidin-2-yl)amino- carbonyl3-2-ttl-methylethyl)sulTonyljbenzenesulfonamide as a white powder, m.p. 188-193 (dec.). NMR (CDCl3)#: 1.3D (d, -C(CH3)2); 2.45 (s, het-CH3); 6.75 (s, het-H). IR (KBr) 1700, 16D3, 1553, 142S, 1333, 1300 1163 and 1130 cmbl. Example 7 Preparation of EMI24.1 EMI24.2 A mixture of 22.1 g (0.139 mole-) of 2-chloro3-nitropyridine, 14.5 g (0.142 mole) of sodium methanesulfinate and 150 ml cf D was boiled under reflux fcr 1 hour. The DIW was evaporated in vacuum and the residue extracted with ethyl acetate. The ethyl acetate extract was washed with water, dilute brine and saturated brine, dried (MgSO4) and evaporated in vacuum to an oil. The oil was crystallized from butyl chloride and the solid twice recrystallized from acetone/hexane to provide 9.1 g of the sulfone B as a tan solid, m.p. 104-107 . EMI24.3 A solution of 9.68 g (0.0479 mole) of the sulfone B in 50 ml acetic acid was treated with 12.5 ml of water, then, pqrtionwise with 11.5 g of powdered iron. The temperature was kept at during the exothermic reaction by periodic cooling. After an additional 10 minutes at about 830 the mixture was filtered, the filtrate diluted with water and the pH raised to about 6 by gradual addition c 50% NaOH, with cooling to < 250; the solution was then evaporated to dryness in vacuum. The residue was treated with ethyl acetate and sodium bicarbonate, the ethyl acetate solution drie- (MgSO4), filtered, and evaporated to 7.41 g of a syrup, which was the amine C. Mass spectral analysis of the syrup showed the expected mole- cular ion, m/e 172, for amine C. EMI25.1 A solution of 6.73 g (0.0391 mole) of the amino- pyridyl sulfone D in 9 ml of acetic acid was added to 29 ml of cold conc. HCl at 0 to 10 . The solution was treated, portionwise, at 0 to 5 , with a solution of 3.83 g of sodium nitrite in 10.2 ml of water, wit development of an orange color. After an additional 15 minutes at this temperature, the diazonium mixture was added, in Fortions, to a stirred mixture of 1.1 g of curious chloride, 8 ml (liquid) of sulfur dioxide and 42 ml of acetic acid at 5 to 150; gas evolution occurred rapidly throughout the addition. After an additional 15 minutes, the mixture was warmed to 250, and the resulting mixture poured into excess ice water. Pre- cipitated white solid was filtered off, washed with water, and dried, providing 5.26 g of the sulfonyl chloride D as a white solid, m.p. 162-163 (dec.). EMI26.1 The sulfonyl chloride D obtained in Part c was dissolved in THF, cooled in an ice bath ane gassed with ammonia, with a resulting exothermic reaction along with the precipitation of a white solid. The mixture was evaporated in vacuum to a white solid, which was washed with water to remove ammonium chloride, leaving the sulfonamide E as a white solid, m.F. 195-196.5 . M2ss spe-tral analysis of the solid showed molecular ic m/e 237 (m +1). EMI26.2 One gram (0.00423 mole) of the sulfonamide E was suspended in 100 ml of thionyl chloride. The mixture was boiled under reflux for about 3 days, dissolution of the sulfonamide occurring in 10-15 minutes. The solution was evaporated to a clear, brown oil F. An excess of solution of phosgene in toluene (13.8% phosgene solution) was added along with 3-4 drops of pyridine. The mixture was heated at 85 under phosgene reflux for 2 hours, cooled, and filtered. The filtrate was evaporated to a solid G, which showed a strong isocyanate absorption peak in the infrared spectrum (ca. 2250 cm-1. nujol mull). The solid isocyanate was dissolved in a little acetonitrile and treated with 0.5 o of 1-amino-4,6- dimethylprimi ine, a reaction quickly occurring with precipitation of white solid. After a fe minutes the mixture was filtered and the white solid washed with acetonitrile and butyl chloride, leaving 0.71 a of the pyridyl sulfone H as a white solid, m.p. 2340 (dec.). as spectral analysis showed m/e 236, EMI27.1 and m/e 149, EMI27.2 Anal. Calcd. for H , C13H15N5O5S2 (M. W. 385.42): C, 40.5; H, 3.9; N, 18.2. Anal. Found: C, 40.8; H, 4.0; N, 18.5. By procedures given in the discussion, included by reference, or illustrated in examples 1-7, the illustrative compounds in the following tables can readily be made by one skilled in the art. Table I EMI28.1 R2 R3 X Y W m.p. ( C) 2 H -n-C H CH3 CH3 0 200-202(D) 2 H -n-C3H7 OCH3 CH3 0 183-185tD) 2 H -n-C3H7 OCH3 OCH3 O 215-217 2 H -CH(CH3)2 CH3 CH3 0 188-193(D) 2 H -CH(CH3)2 OCH3 CH3 0 189-192 2 H -CH(CH3)2 OCH3 OCH3 O 237-239 2 H -n-C4H9 CH3 CH3 0 179-181.5(D) 2 H -n-C4H9 OCH3 CH3 0 152-155 2 H -n-C4Hg OCH3 OCH3 0 177-183 2 H CH2CH(CH3)2 CH3 CH3 0 185-191 2 H CH2CH(CH3)2 OCH3 CH3 0 180-185 2 H CH2CH(CH3)2 OCH3 OCH3 O 215-218 2 H CH(CH3)C2H5 CH3 CH3 O 174-178(D) 2 H CH(CH3)C2H5 OCH3 CH3 O 198-203 2 H CH(CH3)C2H5 OCH3 OCH3 O 203-213 2 H C(CH3)3 CH3 CH3 0 190-195(D) 2 H C(CH3)3 OCH3 CH3 0 192-195 2 H C(CH3)3 OCH3 OCH3 0 217-218 O H CH2CH=CH2 CH3 CH3 S O S-F CH=CHC2H5 C2H5 OCH3 S 0 1-Cl CH2CH2C=CH2H OC2H5 OCH3 S 0 4-Br CH=CHCH3 CH2OCH3 CH3 S 1 1-CH3 cyclopentyl C2H5 OCH3 O 1 5-OCH3 cyclopentyl CH3 OCH3 O 1 5-CF3 cyclopentyl OC2H5 CH3 O Table I (continued) EMI29.1 <tb> <SEP> R <SEP> R <tb> n <SEP> 2 <SEP> 3 <SEP> X <SEP> Y <SEP> W <SEP> m.p.(OC) <tb> <SEP> CH <tb> <SEP> /2 <tb> 1 <SEP> 4 <SEP> 8102 <SEP> CH2-CH <SEP> C <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> 23 <tb> <SEP> CH <tb> <SEP> C&num;2 <tb> 1 <SEP> 5-CN <SEP> CH2CH;C1H22 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> 2 <SEP> CH2 <tb> 1 <SEP> 4-NH2 <SEP> CH2 CHX <SEP> CH2OCH3 <SEP> 2 <SEP> C <SEP> 3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CH2 <tb> o <SEP> H <SEP> n-C3H7 <SEP> C2H5 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> n-C3H7 <SEP> tC2E5 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> n-C3H7 <SEP> CH2OCH3 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> n-C3H7 <SEP> C2H5 <SEP> OCH3 <SEP> O <tb> O <SEP> H <SEP> n-C3H7 <SEP> 0C2H5 <SEP> OCH3 <SEP> O <tb> O <SEP> H <SEP> n-C3H7 <SEP> CH2OCH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> C2H5 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> C2B5 <SEP> CH3 <SEP> O <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> CH20CH3 <SEP> CH3 <SEP> O <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> C2H5 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> n <SEP> C3 <SEP> 7 <SEP> C2H5 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> CH2OCH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> CH3 <SEP> 63 <SEP> OCH3 <SEP> S <tb> 2 <SEP> H <SEP> n-C3H7 <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> CH3 <SEP> O <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> CH3 <SEP> <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> CH2OCH3 <SEP> CH3 <SEP> O <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> OCH3 <SEP> 0 <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> 0C2H5 <SEP> OCH3 <SEP> <tb> O <SEP> H <SEP> -CH(CH3)2 <SEP> 2 <SEP> 3 <SEP> OCH3 <SEP> 0 <tb> Table I (continued) EMI30.1 <tb> n <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> W <SEP> m.p.(OC) <tb> <SEP> J <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> CH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> CH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH2OCH3 <SEP> CH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> C2H5 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH2OCH3 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> o <SEP> H <SEP> n-C <SEP> 3H7 <SEP> CH3 <SEP> CH3 <SEP> O <SEP> 191-200(D) <tb> o <SEP> H <SEP> 3 <SEP> 7 <SEP> CH3 <SEP> OCH3 <SEP> 0 <SEP> 160-165 <tb> o <SEP> H <SEP> n-C3 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 165-170 <tb> 1 <SEP> H <SEP> n <SEP> C3 <SEP> 7 <SEP> CH3 <SEP> CH3 <SEP> O <SEP> 110-116 <tb> 1 <SEP> H <SEP> n <SEP> C3 <SEP> 7 <SEP> CH3 <SEP> OCH3 <SEP> 0 <SEP> 80-96 <tb> 1 <SEP> H <SEP> 3 <SEP> 7 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 175-178 <tb> o <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> o <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 0 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 1 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> 1 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> OCH3 <SEP> O <tb> 1 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> <SEP> CH2 <tb> o <SEP> 'H <SEP> -CH-CH <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> C2 <tb> <SEP> H2 <tb> O <SEP> H <SEP> -CH-CH <SEP> CH, <SEP> OCM3 <SEP> O <tb> 0 <SEP> H <SEP> CR3 <SEP> 0CR3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> ,'H2 <tb> 0 <SEP> H <SEP> -CH-CH <SEP> | <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> <SEP> CE2 <tb> Table I (continued) EMI31.1 <tb> n <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> W <SEP> m.p.(OC) <tb> <SEP> CH <tb> 2 <SEP> H <SEP> -CH-GH <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> OH2 <tb> <SEP> CH2 <tb> 2 <SEP> H <SEP> -CH-CH <SEP> | <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> oCH2 <tb> 2 <SEP> H <SEP> -CH- <SEP> -CH-CHH, <SEP> OCH3 <SEP> OCH3 <SEP> <tb> <SEP> CH2 <tb> O <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> O <SEP> H <SEP> cyclopentyl <SEP> SOCH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 206-208(D) <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> OCH <SEP> 3 <SEP> 0 <SEP> 211-214 <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 219-224 <tb> O <SEP> H <SEP> -CH2CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> -CH2CH=CH2 <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> O <SEP> H <SEP> -CH2CH=CH2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH2CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH2CH=CH2 <SEP> cH3 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH2CH=CH2 <SEP> OCH3 <SEP> OCH3 <SEP> <tb> 2 <SEP> H <SEP> cH(CH3)CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH(CH3)CH=CH2 <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH(0H3)CH=0H2 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH2cH2cH=cH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -OH2OH2OH=0H2 <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH2C 2C=cH2 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> o <SEP> H <SEP> n <SEP> 3H7 <SEP> CH3 <SEP> CH3 <SEP> S <tb> O <SEP> H <SEP> n=C3H7 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> O <SEP> H <SEP> n <SEP> C3H7 <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> Table II EMI32.1 EMI32.2 <tb> n <SEP> R2 <SEP> R3 <SEP> X <SEP> V <SEP> W <SEP> m.p.( C) <tb> n <SEP> L <tb> 2 <SEP> H <SEP> -n-C3H7 <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 189-l91(D) <tb> 2 <SEP> H <SEP> -n-C3H7 <SEP> OCH3 <SEP> CH3 <SEP> 0 <SEP> 200-201(D) <tb> 2 <SEP> H <SEP> -n-C3H7 <SEP> OCH3 <SEP> OCH3 <SEP> <SEP> 184-187 <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3. <SEP> CH3 <SEP> 0 <SEP> 115-119(D) <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> CH3 <SEP> 0 <SEP> 108-125 <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 108-130 <tb> 2 <SEP> H <SEP> -n-CaHg <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 173-173 <tb> 2 <SEP> H <SEP> -n-C4Hg <SEP> OCH3 <SEP> CH3 <SEP> 0 <SEP> 173-177 <tb> 2 <SEP> H <SEP> -n-C4Hg <SEP> OCH3 <SEP> OCH3 <SEP> <SEP> 175-179 <tb> 2 <SEP> H <SEP> CH2CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 180-183 <tb> 2 <SEP> H <SEP> CH2CH(CH3)2 <SEP> OCH3 <SEP> CH3 <SEP> 0 <SEP> 175-178 <tb> 2 <SEP> H <SEP> CH2CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 180-188 <tb> 2 <SEP> H <SEP> CH(CH3)C2H5 <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 160-163 <tb> 2 <SEP> H <SEP> CH(OH3)C2 <SEP> H5 <SEP> OCH3 <SEP> CH3 <SEP> 0 <SEP> 170-173.5 <tb> 2 <SEP> H <SEP> OH(0H3)02H5 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 173-181 <tb> 2 <SEP> H <SEP> C(CH3)3 <SEP> CH3 <SEP> CH3 <SEP> 0 <SEP> 193-195 <tb> 2 <SEP> H <SEP> C(CH3)3 <SEP> 0CH3 <SEP> CH3 <SEP> 0 <SEP> 175-179 <tb> 2 <SEP> H <SEP> C(CH3)3 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 178-181 <tb> 2 <SEP> 1-NH2 <SEP> CH2CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 0 <SEP> 4-F <SEP> OH=0H02H5 <SEP> CH20CH3 <SEP> OCH3 <SEP> S <tb> 0 <SEP> 1-Br <SEP> CH,CH2CH=CH2 <SEP> 02H5 <SEP> CH3 <SEP> S <tb> <SEP> CH2 <tb> s <SEP> 5-Cl <SEP> CH2-CKX <SEP> CH20CH3 <SEP> CH3 <SEP> S <tb> <SEP> CH2 <tb> <SEP> ,rCH2 <tb> 0 <SEP> 4-CH3 <SEP> CH2-CH <SEP> | <SEP> C2H5 <SEP> OCH3 <SEP> S <tb> <SEP> CH2 <tb> Table II (continued) n R2 R3 X Y W m.o. ( C) 1 1-OCH3 cyclopentyl CH3 CH3 O 1 5-CF3 cyclopentyl OC2H5 CH3O O 1 4-NO2 cyclopentyl CH3 CH3 O 1 5-CN cyclopentyl CH2OCH3 CH3 O 0 H n-C3H7 C2H5 CH3 O 0 H n-C3H7 OC2H5 CH3 O 0 H n-C3H7 C2OCH3 CH3 O 0 H n-C3H7 C2H5 OCH3 O 0 H n-C3H7 OC2H5 OCH3 O 0 H n-C3H7 CH2OH3 OCH3 O 2 H n-C3H7 C2H5 CH3 O 2 H n-C3H7 OC2H5 CH3 O 2 H n-C3H7 CH2OCH3 CH3 O 2 H n-C3H7 C2H5 OCH3 O 2 H n-C3H7 OC2H5 OCH3 O 2 H n-C3H7 C2OCH3 OCH3 O 2 H n-C3H7 CH3 CH3 S 2 H n-C3H7 CH3 OCH3 S 2 H n-C3H7 OCH3 OCH3 S 0 H -CH(CH3)2 C2H5 CH3 O 0 H -CH(CH3)2 OC2H5 CH3 O 0 H -CH(CH3)2 CH2OCH3 CH3 O 0 H -CH(CH3)2 C2H5 OCH3 O 0 H -CH(CH3)2 OC2H5 OCH3 O 0 H -CH(CH3)2 CH2OH3 OCH3 O 2 H -CH(CH3)2 C2H5 CH3 O 2 H -CH(CH3)2 OC2H5 CH3 O 2 H -CH(CH3)2 CH2OCH3 CH3 O 2 H -CH(CH3)2 C2H5 CH3 O 2 H -CH(CH3)2 OC2H5 OCH3 O 2 H -CH(CH3)2 CH2OCH3 OCH3 O Table II (continued) EMI34.1 <tb> n <SEP> 2 <SEP> R3 <SEP> X <SEP> Y <SEP> W <SEP> m.p.( C) <tb> <SEP> 3 <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> 2 <SEP> H <SEP> -CH(CH3)2 <SEP> OOH3 <SEP> OOH3 <SEP> S <tb> 0 <SEP> H <SEP> n-C <SEP> H <SEP> OH3 <SEP> CH3 <SEP> c <SEP> 0 <SEP> 150-157 <tb> o <SEP> H <SEP> n-C3H7 <SEP> CH3 <SEP> OCH3 <SEP> O <SEP> 128-135 <tb> 0 <SEP> H <SEP> n-C3H7 <SEP> OCH3 <SEP> OCH3 <SEP> O <SEP> 152-155 <tb> 1 <SEP> H <SEP> n <SEP> C3 <SEP> 7 <SEP> CH3 <SEP> CH3 <SEP> O <SEP> 163-166 <tb> 1 <SEP> H <SEP> n <SEP> C3 <SEP> 7 <SEP> CH3 <SEP> OCH3 <SEP> 0 <SEP> 75-95 <tb> 1 <SEP> H <SEP> n-C <SEP> 3H7 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <SEP> 122-125 <tb> o <SEP> H <SEP> -CH(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> o <SEP> H <SEP> -CH(CH)2 <SEP> CH3 <SEP> C <SEP> 3 <tb> 0 <SEP> H <SEP> -CH(CH)2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 1 <SEP> H <SEP> -OH <SEP> (CR3)2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> 1 <SEP> H <SEP> -CH(CH)2 <SEP> CH3 <SEP> OCH3 <SEP> O <tb> 1 <SEP> H <SEP> -CH(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> <SEP> CH <tb> 0 <SEP> H <SEP> -CH-CH <SEP> OH3 <SEP> CH3 <SEP> O <tb> <SEP> H2 <tb> <SEP> OH <tb> 0 <SEP> H <SEP> -CH-CH <SEP> CM <SEP> CH3 <SEP> OCH3 <SEP> O <tb> <SEP> CH2 <tb> <SEP> OH2 <tb> 0 <SEP> H <SEP> -CH-CH <SEP> | <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> <SEP> OH2 <tb> Table II (continued) EMI35.1 <tb> n <SEP> R2 <SEP> Elm <SEP> R3 <SEP> X <SEP> Y <SEP> W <SEP> m.p.("C) <tb> <SEP> CH <tb> 2 <SEP> H <SEP> ZCH-CH <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> 6/CH2 <tb> 2 <SEP> H <SEP> such <SEP> CH <SEP> CRCR¸i <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CHz <tb> <SEP> CR <tb> 2 <SEP> H <SEP> -CH- <SEP> -CH-CHH, <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CH2 <tb> O <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> O <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> O <SEP> H <SEP> cyclopentyl <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> CE3 <SEP> 0 <SEP> 183-186 <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> CH3 <SEP> OCH3 <SEP> 0 <SEP> 191-200 <tb> 2 <SEP> H <SEP> cyclopentyl <SEP> OCH3 <SEP> OCH3 <SEP> O <SEP> 174-179 <tb> O <SEP> H <SEP> -OR2CH=0H2 <SEP> CX3 <SEP> CH3 <SEP> 0 <tb> o <SEP> H <SEP> -CH2CR=CR2 <SEP> CR3 <SEP> OCH3 <SEP> 0 <tb> o <SEP> H <SEP> -CHzCH=CH2 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> CHzCX=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH2CH=C <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> -CH2CH=CH2 <SEP> OCH3 <SEP> OCR3 <SEP> 0 <tb> 2 <SEP> H <SEP> -OH <SEP> (CR3) <SEP> CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> CH(CH3)CH=CH2 <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> sCHtCH3)CH=CE2 <SEP> OCR3 <SEP> OCH3 <SEP> 0 <tb> 2 <SEP> H <SEP> CH2CH2CH=CH2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2 <SEP> H <SEP> CE2cH2cH=cH2 <SEP> CH3 <SEP> OCH3 <SEP> O <tb> 2 <SEP> H <SEP> -CH2CH2H'CH2 <SEP> SOCH3 <SEP> OCR3 <SEP> 3 <tb> o <SEP> H <SEP> 3 <SEP> 7 <SEP> CH3 <SEP> CH3 <SEP> S <tb> O <SEP> H <SEP> n <SEP> C3H7 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> O <SEP> H <SEP> n-03R7 <SEP> OCH3 <SEP> 06H3 <SEP> S <tb> Table III EMI36.1 R1 R2 X Y W 2-CH3SO2 H CH3 CH3 O 2-CH3SO2 H CH3 OCH3 O 2-CH3SO2 H OCH3 OCH3 0 2-CH3SO2 H C2H5 CH3 O 2-CH3SO2 H OC2H5 OCH3 O 2-CH3SO2 H CH2OCH3 CH3 O 2-C2H5S02 H CH3 CH3 C 2-C2H5SO2 H CH3 OCH3 O 2-C2H5S02 H OCH3 OCH3 O 2-C2H5SO2 H C2H5 OCH3 O 2-C2H5SO2 H CH2OCH3 CH3 O 2-C2H5SO2 H OC2H5 CH3 O 2-n-C3H7SO2 H CH3 CH3 O 2-n-C3H7SO2 H OCH3 CH3 O 2-n-C3H7SO2 H OCH3 OCH3 O 2-(CH3)2CHSO2 H CH3 CH3 O 2-(CH3)2CHSO2 H CH3 OCH3 O 2-(CH3)2CHS02 H OCH3 OCH3 O 2-(CH3)2CHSO2 H OC2H5 CH3 O 2-n-C4H9SO2 H CH3 CH3 O 2-n-C4H9SO2 H OCH3 CH3 O 2-n-C4H9SO2 H OCH3 OCH3 O 2-CH3CH=CHSO2 H CH2OCH3 CH3 O 2-CH2=CHCH2SO2 H CH3 OCH3 O 2-CH3CH=CHCH2S02 H OCH3 OCH3 O Table III (continued) EMI37.1 <tb> <SEP> R1 <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 2-CH2=CHCH2CH2S02 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 2-CH=CHCH(CH3)So2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> CH2 <tb> 2- <SEP> | <SEP> / <SEP> CHCH2S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> 2 <tb> 2 <SEP> | <SEP> sCHCH2SOz <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> <SEP> CH2 <tb> <SEP> CH2 <tb> 2- <SEP> | <SEP> / <SEP> CHCH2S02 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> <SEP> CR2 <tb> 502 <SEP> 502 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 502 <SEP> SO, <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> 0 <tb> %-0 <SEP> S02 <SEP> H <SEP> SOCH3 <SEP> SOCH3 <SEP> O <tb> 4-CR3SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 4-CH3SO2 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 4-CR3SO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 4-CH3S02 <SEP> H <SEP> CH20CH3 <SEP> CH3 <SEP> 0 <tb> 4-C2HsS02 <SEP> H <SEP> C <SEP> H <SEP> OCH3 <SEP> O <tb> 4-C2H5S02 <SEP> H <SEP> 5 <SEP> CR3 <SEP> 3 <tb> 4-n-C3R <SEP> 7502 <SEP> H <SEP> CH3 <SEP> OH3 <SEP> S <tb> 4-n-C3H7so2 <SEP> H <SEP> SOCH3 <SEP> CH3 <SEP> S <tb> 4-n-C3H7so2 <SEP> H <SEP> OCH3 <SEP> ocH3 <SEP> S <tb> 4- <SEP> (CR3) <SEP> 2CHCH2S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-(CH3)"CHCH,SO <SEP> H <SEP> OCH3 <SEP> CR3 <SEP> S <tb> 4- <SEP> (CR3) <SEP> 2CRCH2SO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> Table III (continued) EMI38.1 <tb> <SEP> R1 <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 4-CH3CH2CH(CH3)502 <SEP> 2-F <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-CH3CH2CH(CH3)S02 <SEP> 2-C1 <SEP> OCH3 <SEP> CH3 <SEP> S <tb> 4-CH3OH2CH <SEP> (OH3) <SEP> 502 <SEP> 5-Br <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 4 <SEP> (CH3)3CS02 <SEP> 2 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4- <SEP> (CR3) <SEP> 30S02 <SEP> 2-OCH3 <SEP> 02H5 <SEP> OCH3 <SEP> S <tb> 4- <SEP> (OH3) <SEP> 3CSO2 <SEP> 5-CF3 <SEP> CH2OCH3 <SEP> CH3 <SEP> S <tb> 4-CH2=CHCH2S02 <SEP> 2 <SEP> N02 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-CH2=CHCH2S02 <SEP> 2-C1 <SEP> OCH3 <SEP> CH3 <SEP> S <tb> 4-CH2=CHCH2S02 <SEP> 5-NH2 <SEP> OCH, <SEP> SOCH3 <SEP> S <tb> 4-CH3CH2CH=CHS02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-OR3CH2CH=CHSO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> S <tb> 4-CH3CH2CH=CHS02 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 4-(CH3)2C=CHSo2 <SEP> E <SEP> CH20CH3 <SEP> CH3 <SEP> S <tb> 4- <SEP> > <SEP> CH2S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4- <SEP> LL.CH2502 <SEP> t <SEP> CH3 <SEP> OH3 <SEP> OCH3 <SEP> S <tb> <SEP> 502 <SEP> 2-Br <SEP> OC2H5 <SEP> CH3 <SEP> S <tb> <SEP> 9 <SEP> 2 <SEP> 2-C1 <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 4- <SEP> ID' <SEP> 2 <SEP> 5-OCH3 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5-CH3S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 5-CH3S02 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> 0 <tb> 5 <SEP> 3 <SEP> 2 <SEP> H <SEP> OCH3 <SEP> SOCH3 <SEP> 0 <tb> 5 <SEP> CH3S 2 <SEP> 2-F <SEP> ' <SEP> C2H5 <SEP> CH3 <SEP> 0 <tb> 5CR3SO2 <SEP> 2 <SEP> 3 <SEP> SOCH3 <SEP> OCH3 <SEP> 0 <tb> 5-C <SEP> 2H <SEP> 55.02 <SEP> 2-C1 <SEP> CH20CH3 <SEP> CH3 <SEP> 0 <tb> Table III (continued) EMI39.1 <tb> <SEP> R1 <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 5-n-CBH7S02 <SEP> 4 <SEP> CF <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 5-n-C4H9 <SEP> SO2 <SEP> 4-N 2 <SEP> OCR3 <SEP> CH3 <SEP> 0 <tb> 5-(cH3)2cHSo2 <SEP> 4-OCH3 <SEP> C2H5 <SEP> OCH3 <SEP> 0 <tb> 5-(0H3)20H0h.2502 <SEP> 2 <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 5-C2H5CH(0H3)S02 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> 0 <tb> 5-0H2=CHCH2 <SEP> SO2 <SEP> H <SEP> CR3 <SEP> cH3 <SEP> S <tb> 5-CH3CH=CHS02 <SEP> H <SEP> CH2OCH3 <SEP> CH3 <SEP> S <tb> 5-0R2=OHOR2CR2SO2 <SEP> H <SEP> 2 <SEP> 5 <SEP> 3 <SEP> S <tb> 5-OH3CH=OHCH2SO2 <SEP> 2-C1 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5-OH3CH2CH=OHSO2 <SEP> 2-Br <SEP> . <SEP> CH20CH3 <SEP> OCH3 <SEP> S <tb> 5 <SEP> C <SEP> 2 <SEP> C(C <SEP> 3) <SEP> 2 <SEP> 2 <SEP> 2-F <SEP> CH3 <SEP> OCH3 <SEP> S <tb> 5- <SEP> (OH3) <SEP> 2C=OHSO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 5- <SEP> > <SEP> CHESS02 <SEP> 4-C1 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5 <SEP> 9 <SEP> S02 <SEP> 4-NO2 <SEP> 00.2 <SEP> H5 <SEP> OCH3 <SEP> S <tb> 2-OH3 <SEP> SO2 <SEP> 4-C1 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2-CH3S02 <SEP> 4-Br <SEP> CH3 <SEP> qH3 <SEP> 0 <tb> 2-eH3S02 <SEP> 4-F <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2"6H3S02 <SEP> 4-OH3 <SEP> CR3 <SEP> CH3 <SEP> 0 <tb> 2-0H3S02 <SEP> 3 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2-CR3SO2 <SEP> 5-0F3 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> H3S02 <SEP> 5-NO2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2-CR3 <SEP> SO2 <SEP> S <SEP> 2 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> Table IV EMI40.1 R1 R2 X Y W 2-CH3SO2 H CH3 CH3 O 2-CH3SO2 H CH3 OCH3 <RTI ID=40.1> O 2-CH3SO2 H OCH3 OCH3 O 2-CH3SO2 H C2H5 CH3 O 2-CH3SO2 H C2H5 OCH3 O 2-CH3SO2 H OC2H5 CH3 O 2-CH3SO2 H OC2H5 OCH3 O 2-CH3SO2 H CH2OCH3 CH3 O 2-CH3So2 H CH2OCH3 OCH3 O 2-C2H5SO2 H CH3 CH3 O 2-C2H5SO2 H CH3 OCH3 O 2-C2H5SO2 H OCH3 OCH3 O 2-C2H5SO2 H 02H5 CX3 O 2-C2H5SO2 H OC2H5 OCH3 O 2-C2H5SO2 H CH2OCH3 CH3 O 2-n-C3H7SO2 H CH3 CH3 O 2-n-C3H7SO2 H OCH3 CH3 O 2-n-C3H7SO2 H OCH3 OCH3 O 2-(CH3)2CHSO2 H CH3 CH3 0 2-(CH3)2CHSO2 H OCH3 CH3 O 2-(CH3)2CHSO2 H OCH3 OCH3 O 2-n-C4H9SO2 H CH3 CH3 O 2-n-C4H9S 2 H OCH3 CH3 O 2-n-C4H9SO2 H OCH3 OCH3 O 2-(CH3)2CHCH2SO2 H CH3 O 2-(CH3)2CHCH2SO2 H OCH3 CH3 O 2-(CH3)2CHCH2SO2 H OCH3 OCH3 <RTI ID=40.11> O Table IV (continued) EMI41.1 <tb> <SEP> R1 <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 2=CH3CH2CH <SEP> (CH3) <SEP> SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 2-CH3CH2CH <SEP> (CH3 <SEP> ) <SEP> SO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> 0 <tb> 2-CH3CR2CH <SEP> (CR3) <SEP> SO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 2-(CH3)3C502 <SEP> EI <SEP> CH3 <SEP> OR3 <SEP> 3 <tb> 2 <SEP> (cm33) <SEP> 30502 <SEP> H <SEP> OCH3 <SEP> CR3 <SEP> 0 <tb> 2-(0H3)3C502 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 2-CH2=CHCH2SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 2-CH3CH=CHSO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> O <tb> 2-6H2=C(CH3)S02 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 2-CH2=CHCH2CH2SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 20CH2=C <SEP> (CH3) <SEP> CH2SO2 <SEP> H <SEP> SOCH3 <SEP> OCH3 <SEP> O <tb> 20CH2=CHCH <SEP> (CH3) <SEP> S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2-CH3CH=CHCH2S02 <SEP> H <SEP> SOCH3 <SEP> CH3 <SEP> O <tb> 2-CH3CH2CH=CHSOZ <SEP> H <SEP> CB <SEP> CH3 <SEP> 0 <tb> 2 <SEP> (CH3) <SEP> zC=CHSO2 <SEP> H <SEP> OC <SEP> H <SEP> OCH <SEP> O <tb> <SEP> CH,SO, <SEP> CH2S 2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 2- <SEP> SO2 <SEP> H <SEP> OCH <SEP> OR3 <SEP> 0 <tb> 2- <SEP> > <SEP> CH2S 2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> so2 <SEP> H <SEP> SO, <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> 2- <SEP> 0¯ <SEP> S02 <SEP> H <SEP> SOCH3 <SEP> CR3 <SEP> 0 <tb> SO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 2-CH3SO2 <SEP> 4-F <SEP> CH3 <SEP> CH3 <SEP> C <tb> 2-0H3502 <SEP> 4-e1 <SEP> OCHS <SEP> CR3 <SEP> 0 <tb> Table IV (continued) R1 R2 X Y W 2-CH3S02 4-Br CH3 CH3 O 2-CH3SO2 4-CH3 OCH3 OCH3 S 2-CH3S02 4-CF3 CH3 CH3 S 2-CH3SO2 4-NO2 OC2H5 CH3 S 2-CH3SO2 4-NH2 C2H5 OCH3 S 2-CH3S02 5-C1 CH2OCH3 CH3 S 2-CH3S02 5-Br CH3 CH3 S 2-CH3S02 5-F OCH3 OCH3 S 2-CH3SO2 5-CH3 CH3 CH3 S 2-CH3SO2 5-OCH3 OCH3 OCH3 S 2-CH3S02 5-NO2 C2H5 OCH3 S 2-CH3SO2 5-NH2 CH3 CH3 S 4-CH3SO2 H CH3 CH3 0 4-CH3SO2 H OCH3 CH3 O 4-CH3SO2 H OCH3 OCH3 O 4-C2H5SO2 H CH3 CH3 O 4-C2H5SO2 H OCH3 CH3 O 4-C2H5SO2 H OCH3 OCH3 O 4-n-C3H7so2 H CH3 CH3 O 4-n-C3H7SO2 H OCH3 CH3 O 4-n-C3H7SO2 H OCH3 OCH3 O 4-(CH3)2CHSO2 H CH3 CH3 O 4-(CH3)2CHSO2 H OCH3 CH3 O 4-(CH3)2CHSO2 H OCH3 OCH3 O 4-C4H9SO2 H CH3 CH3 O 4-n-C4H9SO2 H OCH3 CH3 O 4-n-C4H9SO2 H OCH3 OCH3 O 4-(CH3)2CHCH2SO2 H C2H5 CH3 O 4-CH3CH2CH(CH3)SO2 H OC2H5 OCH3 O Table IV (continued) EMI43.1 <tb> <SEP> R1 <SEP> R2 <SEP> .X <SEP> Y <SEP> W <tb> 4-(CH3)3CSo2 <SEP> H <SEP> CH2OCH3 <SEP> CH3 <SEP> O <tb> 4- <SEP> > <SEP> CH2SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> <SEP> s <SEP> L <tb> 4- <SEP> < <SEP> 2SO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> O <tb> 4- <SEP> 2SO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> 0 <tb> 4- <SEP> > <SEP> SOz <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 4- <SEP> 9 <SEP> SO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> 0 <tb> 4- <SEP> 9 <SEP> SO2 <SEP> H <SEP> OCH3 <SEP> OCR3 <SEP> O <tb> 4-0R3502 <SEP> 2-Cl <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-CR3502 <SEP> 2-CR3 <SEP> CH3 <SEP> SOCH3 <SEP> S <tb> 4-CH3SO2 <SEP> 5-CF3 <SEP> E3 <SEP> CH3 <SEP> S <tb> 4-C2H5SO2 <SEP> 2OCH3 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> 4 <SEP> CzH5SO2 <SEP> 2-NO2 <SEP> C <SEP> 2R5 <SEP> CH3 <SEP> S <tb> 4-n-C3H7502 <SEP> 5-Br <SEP> CH3 <SEP> CH3 <SEP> S <tb> 4-n-C3H7502 <SEP> 5-F <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 4 <SEP> n <SEP> C4HgSO2 <SEP> 2-NH2 <SEP> CH2OCH3 <SEP> CH3 <SEP> S <tb> 4-n-C4R9 <SEP> SO2 <SEP> 5-C1 <SEP> C <SEP> 2R5 <SEP> OCR3 <SEP> S <tb> 5-CE3S 2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5-CH3502 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> S <tb> 5-6H3S02 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> S <tb> 5-C2HSSO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5-C2H5SO2 <SEP> H <SEP> SOCH3 <SEP> CH3 <SEP> S <tb> 5-C2H5S02 <SEP> H <SEP> SOCH3 <SEP> SOCH3 <SEP> S <tb> Table IV (continued) EMI44.1 <tb> <SEP> R1. <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 5-C3H7S02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-C3H7SO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> O <tb> 5-C3H7SO2 <SEP> H <SEP> ' <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 5- <SEP> (CR3) <SEP> 2CHS02 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-(CH3)2CHSO2 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> O <tb> 5-(CH3)2CHSO2 <SEP> H <SEP> OCR. <SEP> OCH3 <SEP> O <tb> 5 <SEP> ¯ <SEP> C4HgSO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-n-C,HgS02 <SEP> H <SEP> OCR3 <SEP> CH3 <SEP> O <tb> 5-n-CaRgSo2 <SEP> H <SEP> OCH <SEP> OCH3 <SEP> O <tb> 5-(CH3)2CH2CH2SO2 <SEP> H <SEP> . <SEP> C2H5 <SEP> OCH3 <SEP> 0 <tb> 5-CH3CH2CH(CH3)SO2 <SEP> H <SEP> CH2OCH3 <SEP> CH3 <SEP> 0 <tb> 5- <SEP> (OH3) <SEP> 30502 <SEP> H <SEP> CH2OCH3 <SEP> OCH3 <SEP> O <tb> 5-CHz=CHCH2SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-CH3CH=CHSO2 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 5-CH2=CHCH2C <SEP> H2S02 <SEP> H <SEP> C <SEP> 2H5 <SEP> CH3 <SEP> O <tb> 5¯ <SEP> > <SEP> CH2SO2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-CH2S02 <SEP> - <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> O <tb> 5-CH2S02 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 5- <SEP> 2 <SEP> H <SEP> CH3 <SEP> C <SEP> O <tb> 5- <SEP> 0 <SEP> SO, <SEP> H <SEP> OCH3. <SEP> CH3 <SEP> O <tb> 5- <SEP> 0 <SEP> SO, <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 5-C2H5SO2 <SEP> 2-Br <SEP> CH3 <SEP> CH3 <SEP> O <tb> 5-C2H5SO2 <SEP> 4-C1 <SEP> OCH3 <SEP> OCH3 <SEP> O <tb> 5-n-C3H7so2 <SEP> 2-NO2 <SEP> CH2OCH3 <SEP> CH3 <SEP> O <tb> 5-n-C4H9st2 <SEP> 4-CH3 <SEP> CH3 <SEP> CH3 <SEP> O <tb> Table IV (continued) EMI45.1 <tb> <SEP> R1 <SEP> R2 <SEP> X <SEP> Y <SEP> W <tb> 5(CH3)2CHSO2 <SEP> 2-CF3 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5- <SEP> (CR3) <SEP> 2CHSO2 <SEP> 2-NH2 <SEP> CH3 <SEP> CH3 <SEP> S <tb> 5-(CR3)3C5o2 <SEP> 4-OCR3 <SEP> CH3 <SEP> OCH3 <SEP> S <tb> 5- <SEP> > <SEP> 84,56 <SEP> 4-F <SEP> SOCH3 <SEP> SOCH3 <SEP> S <tb> 5- <SEP> 0 <SEP> SO, <SEP> 2-CR3 <SEP> OCH3 <SEP> SOCH3 <SEP> S <tb> 2-CR3502 <SEP> 5-CF3 <SEP> CH3 <SEP> CH3 <SEP> O <tb> 2-6H3S62 <SEP> 5-NO2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> 2-CR3 <SEP> SO2 <SEP> 5-NH2 <SEP> CH3 <SEP> CH3 <SEP> O <tb> Formulations Useful formulations of the comoounds of Formula (I) can be prepared in conventional ways. They include dusts, granules, oellets, solutions, suspensions, emulsions, wettable powders, and the like. Many of these may be aoplied 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 soecifically, they will contain these ingredients in the following approximate oroportions: TABLE V Weight Percent* Active Inaredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil SusDenslons, 3-50 49-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 4-84 1-20 Dusts 1-25 7-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High-Strength 90-99 0-10 0-2 Comoosltions + 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 manufac- tured, may be used. The more absorotive 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 3.1X is preferred for suspension concentrates; solution concen- trates are preferably stable against Dhase separation at se. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Coro., 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 Enaineerina, December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,351, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 1O 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, 5, 132, 138-140, 162-164, 165, 167 and 159-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; C. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. 4. Evans, "Weed Control Hand- book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the followinq examples, all oarts are by weight unless otherwise indicated. Example 8 Wettable Powder N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] [(1-methylethyl)sulfonyl]benzene 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 53 microns and then reblended. Example 9 Wettable Powder N E(4-methoxy-5-methyl-1,3,5-triazin-2-yl)aminocar- bonyl]-2-[(1-methylethyl)sulfonyl]benzene sulfonamide 50% sodium alkylnaohthalenesulfonate 2 low-viscosity methyl cellulose 2% diatomaceous earth The inqredients are blended, coarsely hamme. milled and then air-milled to oroduce particles essentially all below 1 microns in diameter. The product is reblended before packaging. Example 10 Granule Wettable Powder of Example 9 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 oranules are dried and packaged. Example 11 Extruded Pellet N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-[(1 meghy9ethyl)suafonyl]benzen- sulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignisulfonate 5% sodium alkylnaphthalenesulfonate 1S calcium/maonesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cyclinders 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 packed for use and the fines recycled. Example 12 Oil Suspension N-C(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- (proDylsulfonyl)benzene- sulfonamide 25% polyoxyethylene sorbitol hexaoleate 5S highly aliphatic hydrocarbon oil 70% The ingredients are qround together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be aoplied directly, but preferably after beino extended with oils or emulsified in water. Example 13 Wettable Powder N-t(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl3-2- (propylsulfonyl )benzene- sulfonamide 20S sodium alkylnaphthalenesulfonate 4S sodium lignisulfonate 4% low-viscosity methyl cellulose 3E attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 10.0 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example 14 Low-Strenhth Granule N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon yl)-2-(propylsulfonyl)benzene sulfonamide 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-50 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After sprayinq of the solution has been comoleted, the blender is allowed to run for a short period and then the granules are packaged. Examole 15 Aoueous Susoension N-[(4,.6-dimethyl-)-1,3,5-triazin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzene sulfonamide 40% qolyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether m.5S disodium phosphate 1% monosodium phosphate O.5t 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 16 Solution N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl)-2-[(1-methylethyl)sulfonyl benzenesulfonamide, 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. Examole 17 Low Strength Granule N-E(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl3- 2-(propylsulfonyl)betzene- sulfonamide 0.1% attapulgite granules 99.9% (U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After soraying of the solution has been completed, the material is warmed to evaoorate the solvent. The material is allowed to cool and then packaged. Examole 18 Granule N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 (Propylsulfonyl)benzene- sulfonamide 80% wetting agent 1% crude ligninsulfonate salt (containIng 10% 5-2s% of the natural sugars) attapulgite clay 9S 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 19 High Strength Concentrate N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] 2-[(1-methylethyl)sulfonyl)benzene sulfonamide 99 silica aerogel a.5 synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all massing a U.S.S. No. 59 screen (O.3 mm opening). The concentrate may be formulated further if necessary. Example 29 wettable Powder N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl-2 [(1-methylethyl)sulfonyl]benzene- sulfonamide 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 129 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. Examole 21 Wettable Powder N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 [(1-methylethyl)sulfonyl]benzene sulfonamide 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 22 Oil Suspension N-[(4,6-dimethoxy-1,3,6-triazin-2-yl)aminocarbonyl-2 [(1-methylethyl)sulfonyl]benzene 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 oroduct can be used directly, ¯¯¯ extended with oils, or emulsified in water. Examole 23 Dust N- (a-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon- yl9-2-[(1-methylethyl)sulfonyl]benzene sulfonamide attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 230 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example 24 Wettable Powder N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide 95% dioctyl sodium sulfosuccinate 0.1% sodium ligninsulftnate 1% synthetic fine silica .3.9% The ingredients are blended and ground in a hammer-mill to produce particles almost all of which are below 100 microns in size. That material is sifted through a U.S.S. No. 50 screen and packaged. Example 25 Wettable Powder N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl) -3-pyridinesulfonamide 40% dioctyl sodium sulfosuccinate loSE sodium ligninsulfonate low-viscosity methyl cellulose 1.5% attapulgite 54 The ingredients are thoroughly blended and passed through an air mill to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging. Example 26 Granule wettable powder of Example 25 258 gypsum 64E potassium sulfate 11% The ingredients are blended in a rotating mixer, and water is sprayed onto that blend so as to effect granulation. When most of the granules have reached 1.0 to 0.42 mm (U.S.S. #18 to 40 sieves) in size, they are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. The resulting granules contain 10% of the active ingredient. Example 27 Wettable Powder N- (4, 6-Dimethylpyrimidin-2-yl) aminocarbonyl]--2- (methylsulfonyl)-3-pyridinesulfonamide 65% dodecylphenol polyethylene glycol ether 2% sodium ligninsulfonate 4% sodium silicoaluminate 6% montmorillonite (calcined) 23% The ingredients are thoroughly blended. The liquid surfactant is added by spraying on the solid ingredients in a blender. After grinding in a hammer-mill to produce particles almost all of which are below 100 microns in size, the material is reblended, sifted through a U.S.S. i50 sieve (0.3 mm opening) and packaged. Example 28 Oil Suspension N-[(4,6-Dimethylpyrimidin-2-ylaminocarbonyl3-2- (methylsulfonyl) -3-pyridinesulfonamide 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 suspension may be applied directly, but preferably after being extended further with oils or emulsified in water. Example 29 Aqueous Suspension N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2- (methylsulfonyl) -3-pyridinesulfonamide 25% hydrated attapulgite 38 crude calcium ligninsulfonate 10% sodium dihydrogen phosphate 0.5% water 61.5% The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to sizes under 10 microns, and then packaged. Example 30 Extruded Pellet N-{(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2- (methylsulfonyl)-3-pyridinesulfonamide 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer milled and then moistened with about 128 water. The mixture is extruded in the form of cylinders about 3 mm in dia- meter which are cut to produce pellets about 3 mm long. The pellets may be used directly, after dry- ing, o dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a 13.5.5. No. 40 sieve (0.42 mm openings) may be packaged for use and the f-ines recycled. Example 31 Solution N-[4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide 5% dimethylformamide 95% The ingredients are combined and stirred to produce a solution, which can be used for low-volume. applications. Example 32 Wettable Powder N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite . 13% The ingredients are thoroughly blended after grinding in a hammer mill to produce particles essentially all of which are under 100 microns in size; the material is reblended, sifted through a U.S.S. No. 50 sieve and packaged. Example 33 Granule N-[(4,6-Dimethylpyrimidin-2-ylEaminocarbonyl3-2- (methylsulfonyl) -3-pyrid.inesulfonamide 80% wetting agent 15 crude ligninsulfonate salt (con taining 5-205 of the natural sugars) 10% attapulgite clay 9E 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 ad- justed 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 mad. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 18. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Tne compounds of Formula I can be formulated using the procedures of Examples 8-33. UTILITY The compounds of the present invention are ac -tive 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, MX missile sites, parkins lots, drive-n theaters, around billboards, highway and railra2d structures. In addition, the subject com- pounds distinguish themselves in being highly useful for the selective pre or post-emergence weed control in a wide range cf coos, such as soybeans, dry beans, green beans, alfalfe, tobacco, corn, cotton, wheat, barley, cucumbers, tomatoes, flax and potatoes. - properly selecting rate and time of application, co-- pounds of this invention nay be used also to modif \, plantgrowth beneficially. The rates of application for the compounds of the invention are determined hy a number cf factors including their use as selective or general herbi- cites, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required. The compounds of this invention may be used in combination with other commercial herbicides. They are particularly useful in combination with the following herbicides. Common Nam Chemical Name acifluorfen 5-[2-chloro-4-(trifluoromethyl)phenoxy] 2-nitrobenzoic acid alachlor 2-chloro-2', 6'-diethyl-N-(methoxymethyl) acetanilide amintrole 3-amino-s-triazole atrazine 2-chloro-4-(ethylamino)-6-(isopropyl amino)-s-triazine barban 4-chloro-2-butynyl m-chlorocarbanilate bentazon 3-isopropyl-1H-2,1,3-benzothiadiazin 4(3H)-one-2,2-dioxide benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL alpine bromacil 5-bromo-3-sec-butyl-6methyluracil bromoxynil 3,5-dibromo-4-hydroxybenzonitrile butylate S-ethyl-diisobutylthiocarbamate cyanazine 2-[[4-chloro-6-(ethylamino)-s-triazin 2-yl]amino]-2-methylpropionitrile diallate S-(2,3-dichloroallyl)diisopropylthio carbamate dicamba 3,6-dichloro-o-anisic acid dichloroprop 2-[2,4-dichlorophenoxy)propionic acid diclofop 2-[4-(2,4-dichlorophenoxy)phenoxy] propanoic acid difenzoquat 1,2-dimethyl-3,5-diphenyl-1H-pyrazolion dinoseb 2-sec-butyl-4,6-dinitrophenol diuron 3-(3,4-dichlorophenyl)-1,1-dimethylurea EPTC S-ethyl-dipropylthiocarbamate flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL alanine fluometuron 1,1-dimethyl-3-(&alpha;,&alpha;,&alpha; ;-trifluoro-m-tolyl)- urea Common Nare Chemical Name fosamine ethyl hydrogen (aminocarbonyl)phosohonate glyphosate N.(phosphonomethyl)glycine hexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl 1,3,5-triazine-2,4(1H, 3H)-dione ioxynil 4-hydroxy-3,5-diiodobenzonitrile lenacil 3-cyclohexyl-6,7-dihydro-1H-cyclopenta pyrimidine-2, 4(3H,5H)-dione linuron 3-(3,4-dichlorophenyl)-1-methoxy-1 methylurea MCPA [(4-chloro-o-tolyl)oxy]acetic acid MCPB 4-[(4-chloro-o-tolyl)oxy]propionic acid metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N (2-methoxy-1-methylethyl)acetamide metribuzin 4-amino-6-tert-butyl-3-(methylthio)-as triazin-5(4H)-one MSMA monosodium methanearsonate neburon 1-butyl-3-(3,4-dichlorophenyl)-1-methyl urea paraouat 1,1'-dimethyl-4,4'-biopyridinium ion propanil 3', 4'-dichloropropionalide siduron 1-(2-methylcyclohexyl)-3-phenylurea terbacil 3-tert-butyl-5-chloro-6-methyluracil triallate S-(2,3,3-trichloroallyl)diisopropylthio carbamate trifluralin &alpha;,&alpha;,&alpha; ;-trifluoro-2,6-dinitro-N,N-dipropyl p-toluidine 2,4-0 (2,4-dichlorophenoxy)acetic acid 2,4-DB 4-(2,4-dichlorprophenoxy)butyric acid 3,4-diaryl-4-cyanobutyrates methabenz thiazuron 1,3-dimethyl-3-(2-benzothiazolyl)urea chlortoluron N'-(3-chloro-4-methylphenyl-N', N' dimethylurea isoproturon N-(4-isopropylphenyl)-N',N'-dimethylurea methoxuron N'-(3-chloro-4-methoxyphenyl)N,N dimethylurea The activity of these compounds was discovered in a number of greenhouse and field tests. The tests are described and the data resulting from them are shown below. o = no effect 10 t maximum effect C = chlorosis or necrosis D = defoliation E = emergence inhibition G = growth retardation H = formative effects U = unusual pigmentation X = axillary stimulation 5F = earlier flowering 6Y = abscised buds or flowers. Test A Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusoalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedae tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with a non-phytotoxic solvent solution. of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones), busY beans with the third trifoliate leaf expanding, crab- grass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), mornigglory and cocklebur with four leaves (including the cotyledonary ones), sorohumand corn with four leaves, soybean with two cotyledonary leaves, rice with thee leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed with a non-phytotoxic solvent solution of the compounds of Table . Other containers of the above mentioned weeds and croos were treated pre- or post-emeroenoe with the same non-phytotoxic solvent so as to provide a solvent control. A set of untreated control plants was also included for comparison. Pre-emergence and post-emergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment. The data in Table A shows that compounds of this invention are very effective as herbicides and ray have utility for selective post-emergence weed control in wheat. Compound No. 1 EMI64.1 Compound No. 2 EMI64.2 Compound No. 3 EMI64.3 Compound No. 4 EMI64.4 Compound No. 5 EMI65.1 Compound No. 6 EMI65.2 Compound No. 7 EMI65.3 Compound No. 8 EMI65.4 Compound No. 9 EMI66.1 Compound No. 10 EMI66.2 Compound No. 11 EMI66.3 Compound No. 12 EMI66.4 Table A Compound No. 1 2 3 kg/ha 0,1 0,1 0,1 POST-EMERGENCE Bushbean 2C,5G,6Y 5C,8G,6Y 9C Cotton 3C,3H,6G 4C,7G 5C,9G Morningglory 2C,5G,5F 1OC 1C,2H Cocklebur 2C,5G 9C 9C Cassia 3C 5C,8G 4C,8G Nutsedge 2G 5G 7G Crabgrass 2G 2G 2G Barnyardgrass 2C,5H 9C 8H Wild Oats 2C,6G 2C,5G 1C Wheat 1C,2G 2C,3G 1C Corn 2C 1C,3G 1C,5H Soybean 2C,6G 5C,9G 2C,8G Rice - - Sorghum 3C,9H 3C,9G 2C,9G PRE-EMERGENCE Morningglory 8G 9G 9G Cocklebur 5H 9H 9H Cassia 1C 8G 8G Nutsedge 0 10E 10E Crabgrass 2G 5G 1C,8G Barnyardgrass 1C,3G 9H 9H Wild Oats 1C,2G 2C,8H 7G Wheat 1C 1C,5G 4G Corn 3G 1C,7G 1C.9H Soybean 0 8H 7H Rice 2C,6H 9H 1OE Sorghum 1C,8G 5C,9H 2C,9H Table A (continued) Compound No. 5 6 kg/ha 0.1 0.1 0.1 POST-EMERGENCE Bushbean 3C,6Y 9C 9C Cotton 3C,3H 6C,8G 6C,9G Morningglory 2C,4G,5F 60,90 100 Cocklebur 2C,2H 5C,9G 9C Cassia 1C 2C,5G 5C,8G Nutsedge 0 10 50 Crabgrass 1C,2G 1C,5G 2C,8G Barnyardgrass 9C 5C,9H 2C,9H Wild Oats 2C,3G 2C 1C,2G Wheat 10 1C,2G 1G Corn 1C,5H 4C,9H 9C Soybean 20 50,90 6C,9G Rice Sorghum 1C,9G 2C,9G 4C,9G PRE-EMERGENCE Morningglory 7G 9C,9G 9C,9G Cocklebur 4G 9H 9H Cassia 1C 2C,9G 2C,9G Nutsedge 1C,5G 9G 10E Crabgrass 2C 2C,8G 2C,8G Barnyardgrass 2C,4G 2C,9H 3C,9H Wild Oats 2C 20,70 10,20 Wheat 0 10,5 50 Corn 10,60 lU,9G lU,9G Soybean 0 8H 8H Rice 9H 9H 9H Sorghum 1C,9G 5C,9H 3C,9H Table A (continued) Compound No. 7 8 9 kg/ha 0,4 0,4 0,4 POST-EMERGENCE Bushbean 9C 9C 9C Cotton 2C,6C,9G 9C 9C Morningglory 2C,5G,5F 1OC 1C,2H Cocklebur 9C 1OC 9C Cassia 4C,8G 9C 9C Nutsedge 1C,8G 5C,9G 5C,9G Crabgrass 3C,9G 5C,9G 7C,9G Barnyardgrass 9C 9C 9C Wild Oats 9C 9C 5C,9H Wheat 3C,9G 3C,9G 3C,9G Corn 2U,9H 7U,9G 3U,9H Soybean 9C 9C 9C Rice 9C 9C 8C Sorghum 9C 1OC 9C PRE-EMERGENCE Morningglory 9C 9H 9H Cocklebur 9H 1OE 9H Cassia 2C,9G 2C,9G 2C,9G Nutsedge 1OE 10E 10E Crabgrass 1C,5G 5C,9G 5C,9H Barnyardgrass 3C,9H 5C,9H 5C,9H Wild Oats 4C,9H 5C,9H 5C,9H Wheat 1C,9G 2C,9G 3C,9H Corn 2C,9G 9H 9G Soybean 9H 9H 9H Rice 1OE 1OE 1OH Sorghum 3C,9H 6C,9H 1OH Table A (continued) Compound No. 10 11 12 kg/ha 0,4 0,4 0,4 POST-EMERGENCE Bushbean 90 9r 5C,9G Cotton 2U,S0,9G 90 9C Morningglory 90 10C 10C Cocklebur 90 90 1OC Cassia 5C,8G 9C 9C Nutsedge 4G 6G 1C,6G Crabgrass 2C,8G 8C,9G 4C,9G Barnyardgrass 2C,9H 90 90 Wild Oats 5C,8G 6C,9G 3C,7H Wheat 1C,7G,5X 2C,9G,5X 1C,6G,5X Corn 2U,9G 8U,9G 6U,9C Soybean 2C,8G,5X 9C 9C Rice 5C,9G 7C,9G 9C Sorghum 9C 9C 4U,9C PRE-EMERGENCE Morningglory 9G 9H 9H Cocklebur 9H 9H 9H Cassia 4C,9G 2C,9G 1C,9G Nutsedge 4G 2C,8G 8G Crabgrass 2G 40,90 20,80 Barnyardgrass 4C,9H 5C,9H 4C,9H Wild Oats 2C,8G 5C,9H 5C,9H Wheat 10,80 3C,9G 10,90 Corn 9H 1OE 1OE Soybean 1O,2G 9H 2C,9H Rice 1OE 1OE 1OE Sorghum 3C,9H 10H 6C,9H Table A (cont'd) EMI71.1 EMI71.2 <tb> <SEP> kg/ha <SEP> 0.4 <tb> <SEP> POST-EMERGENCE <tb> <SEP> BUSHBEAN <SEP> 5C,9G,6Y <tb> <SEP> COTTON <SEP> 9C <tb> <SEP> MORNINGGLORY <SEP> 1OC <tb> COCKLEBUR <SEP> 9C <tb> CASSIA <SEP> 5C,8G <tb> NUTSEDGE <SEP> 8G <tb> CRABGRASS <SEP> 9C <tb> <SEP> BARNYARDGRASS <SEP> 7C,9H <tb> <SEP> WILD <SEP> OATS <SEP> 7C <tb> <SEP> WHEAT <SEP> 5C,8G <tb> CORN <SEP> 5U,9G <tb> SOYBEAN <SEP> 9C <tb> <SEP> RICE <SEP> 5C,7G <tb> <SEP> SORGHUM <SEP> 9C <tb> <SEP> PRE-EMERGENCE <tb> <SEP> MORNINGGLORY <SEP> 9G <tb> COCKLEBUR <SEP> 9H <tb> <SEP> CASSIA <SEP> 9G <tb> <SEP> NUTSEDGE <SEP> 10E <tb> <SEP> CRABGRASS <SEP> 2C,9G <tb> <SEP> BARNYARDGRASS <SEP> 9H <tb> <SEP> WILD <SEP> OATS <SEP> 3C,8H <tb> WHEAT <SEP> 9H <tb> <SEP> CORN <SEP> 9H <tb> <SEP> SOYBEAN <SEP> 9H <tb> <SEP> RICE <SEP> 1OE <tb> <SEP> SORGHUM <SEP> 5C,9H <tb> 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 (Cvperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Dicitari snouinalis), bernyardgrass (Echinochloa crusgalli), wild oats (Avena fatua) johnsong=ass (Sorghum halepense), dallisgrass (PasDalum di.latatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Erassica arvensis), cocklebur (Xanthium pensylyanicum), pigweed (Amaranthus retroflexus), mornungglory (Ipomoea hederaces), cassia (Cassis tora), teaweed (Sida spinosa), velvetleaf (Abutilon theoohrasti), 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 slanted with suoarbeets. 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 previous-ly for Test A. The data are summarized in. Table Be It will be readily seen that certain compounds are useful as pre-emergence treatments for weed control in crops such as soybeans, wheat, corn and cotton. Table B PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 7 8 kg/ha 0.03 0.12 0.03 0.12 Crabgrass 0 2G 5G 6G Barnyardgrass 5G 7G,3H 9G,8C 9G,9C Sorghum 9G,5H 9G,9C 10C 10C Wild Oats 7G,3H 7G,4C 7G,6C 7G,6C Johnsongrass 6G,3H 8G,3H 8G,4C 7G,4C Dallisgrass 0 6G 8G 9G,8C Giant Foxtail 0 6G,3H 7G,4C 7G,4C Ky. Bluegrass 5G 7G 9G,9C 10C Cheatgrass 7G,5E 9G,9C 10C 10C Sugarbeets 6G,7C 8G,8C 8G,8C 8G,9C Corn 2G 4G,2C 6G,3H 8G,5H Mustard 9G,9C 9G,9C 9G,9C 10C Cocklebur 3G 5G 7G 8G Pigweed 7G 7G 10C 10C Nutsedge 0 3G 8G 7G Cotton 0 4G,2H 7G,5H 7G,5H Morningglory 7G,5H 8G,5H 7G,5H 8G,5H Cassia 5G 5G 7G,4C 10E Teaweed 0 8G,3C 5G,3C 6G,3C Velvetleaf 5G,3H 7G,3H 8G,5C 9G,9C Jimsonweed 4G 5G 6G,3C 7G,5C Soybean 0 3G 4G,3H 6G,5H Rice 7G 10E 9G,9C 10C Wheat 3G 3G 5G 6G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 2 kg/ha 0.03 0.06 0.12 0.25 Crabgrass 0 6G 3G 5G Barnyardgrass 6G,3C 8G,3H 8G,4C 9G,9C Sorghum 8G,5H 9G,9C 10C 10C Wild Oats 4G 4G,3C 7G,4C 6G,5C Johnsongrass 6G,3H 8G,5H 7G,3H 9G,7C Dallisgrass 6G - 7G Giant Foxtail 5G 6G,3C 7G,3C 7G,3C Ky.Bluegrass 8G,5C 6G,3C 8G,8C 8G,5C Cheatgrass 7G,3C 8G,8C 8G,3C 10E Sugarbeets 5G 7G,3H 6G,3C 8G,8C Corn 0 5G 2H 5G,3H Mustard 9G,9C 9G,8C 10C 10C Cocklebur 6G 5G,3H 6G 6G,3H Pigweed 3G 6G 10C 8G,8C Nutsedge 5G 6G 6G 7G Cotton 0 4G 5G,5H 6G,5H Morninggiory 4G 4G,2H 8G 8G,5H Cassia 0 2G,2C 5G,3C 8G,3H Teaweed 2G 0 3G 5G,3H Velvetleaf 3H 3H 6G,5H 6G,5H Jimsonweed 4G,3C 7G 7G,5C 7G,3C Soybean 0 4G 4G,2C 6G,3H Rice 5G 6G,3H 7G,3C 7G,5H Wheat 2G 2G 5G 3G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 9 Kg/ha 0.03 0.06 0.12 0.25 Crabgrass 5G 7G 6G 8G Barnyardgrass 8G,34 9G,5H 9G,9C 10C Sorghum 9G,9C 10C 10C 10C Wild Oats 5G,3C 3G 7G,3C 6G,3C Johnsongrass 7G,3H 8G,3H 8G,3C 9G,9C Dallisgrass 7G - 8G Giant Foxtail 6G,3C 7G,5H 8G,6C 9G,8C Ky. Bluegrass 8G,7C 8G,5C 8G,8C 8G,8C Cheatgrass 8G,4C 10 E 8G,6C 10 E Sugarbeets 7G,7C 6G,3H 7G,7C 8G,8C Corn 0 5G,2C 4G,3H 6G,3C Mustard 9G,9C 10C 10C 10C Cocklebur 6G 5G,3H 7G 7G,3H Pigweed 5G 4G 9G,9C 10C Nutsedge 10 E 7G 8G 10 E Cotton 4G,3H 6G 7G,5H 8G,5H Morningglory 6G 7G,5H 7G 10C Cassia 8G,5C 6G,3C 8G,5C 9G,6C Teaweed 5G,2C 3G 5G,2C 7G Velvetleaf 8G,5H 7G,5H 9G,9C 8G,7C Jimsonweed 3G 0 4G 4G Soybean 0 0 4G 5G,3H Rice 10E 8G,8C 10E 10E Wheat 0 2E 3G 5G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAK Compound No. 3 Kg/ha 0.03 0.06 0.12 0.25 Crabgrass 3G 0 6G 5G Barnyardgrass 5G,2C 7G,3H 8G,3C 8G,3H Sorghum 9G,9C 10C 9G,9C 10C Wild Oats 4G 0 7G,3C 5G Johnsongrass 7G,3H 7G,5H 8G,5C 8G,5H Dallisgrass 6G 0 8G 6G,3H Giant Foxtail 8G,4C 8G,5H 9G,9C 9G,5H Ky. Bluegrass 7G,5C 7G,8C 8G,9C 9G,9C Cheatgrass 8G,5C 8G,5H 8G,8C 8G,9C Sugarbeets 6G,3C 7G,5H 8G,8C 9G,9C Corn 2G 0 6G,3H 5G,3H Mustard 9G,8C 9G,9C 10C 10C Cocklebur 7G 7G,3H 7G 7G,5H Pigweed 6G,5C 10C 10C 10C Nutsedoe 9G 7G 10E 8G Cotton 0 3G 4H 6G,5H Morningglory 7G 3G 7G 6G Cassia 0 5G 8G,3C 8G Teaweed 3G 7G 6G,3C 8G Velvetleaf 7G,5H 4G,5H 8G,5H 8G,5E Jimsonweed 4G 0 5G 0 Soybean 0 1C 3G,2H 5G,2C Rice 8G,9C 10E 8G,9C 10C Wheat 2G 2G 2G 3G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 11 Kg/ha 0.03 0.06 0.12 0.25 Crabgrass 2G 4G 6G 7G Barnyardgrass 4G 6G 8G,7C 8G,6C Sorghum 9G,9C 10C 10E 10C Wild Oats 6G,2H 4G,3C 7G,3H 6G,4C Johnsongrass 8G,5C 9C,7C 8G 9G,9C Dallisgrass 5G - 5G Giant Foxtail 3G,2C 5G 6G,3C 6G,2C Ky. Bluegrass 6G.2C 7G,4C 7G,3C 8G,8C Cheatgrass 7G 10C 8G,3C 7G,3C Sugarbeets 8G,8C 10C 9G,9C 10C Corn 9G,3C 6G,5H 9G,5C 10C Mustard 10C 10C 10C 10C Cocklebur 8G,5H 7G,5H 8G,5H 8G,5H Pigweed 10C 8G,8C 8G,9C 10C Nutsedoe 6G 0 6G 5G Cotton 8G,5H 8G,5H 8G,5H 9G,5H Morningglory 8G 8G,5H 8G 9G,8C Cassia 9G,5C 7G,3H 9G,8C 9G,7C Teaweed 7G,2C 5G,5H 8G,2C 7G,5H Velvetleaf 8G,7C 7G,5H 8G,7C 8G,6C Jimsonweed 5G,3C 8G 7G,5C 8G Soybean 0 0 3G,2H 5G,5H Rice 8G,8C 7G,3H 10E 10E Wheat 4G 0 5G 5G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 10 5 Kg/ha 0.03 0.12 0.03 0.12 Crabgrass 0 20 0 50 Barnyardgrass 3G 30 4G 70,30 Sorghum 3G 8G,5H 9G,8C 10C Wild Oats 0 6G,3H 3G 6G Johnsongrass 0 6G,3H 7G,3H 8G Dallisgrass 0 5G 0 4G Giant Foxtail 0 0 4G 6G,3C Ky. Bluegrass 0 3G 6G 7G,3C Cheatgrass 6G 6G, 5E 3; ; 70 Sugarbeets 0 7G,5H 10C 8G,7C Corn O 5G,3C 7G,3H 80 Mustard 4G 8G,8C 8G,8C 10C Cocklebur - 3G 7G,3H 8G,5H Pigweed 0 5G 9G,9C 10E Nutsedge 0 0 5G 6G Cotton 0 5H 6G,5H 8G,5H Morningglory 0 5H 7G,5H 8G,3C Cassia 0 0 7G,5C 9G Teaweed 0 0 0 4G,3H Velvetleaf 0 4G 6G,5H 8G,5C Jimsonweed 0 0 4G,3C 7G,4C Soybean 0 0 4G,3H 8G,5H Rice 2G 6G,3C 5G 7G,8C Wheat 0 4G 0 5G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No 12 kg/ha 0.03 0.06 0.12 0.25 Crabgrass O 3G 5G 7G Barnyardgrass 6G 5G 8G,4C 8G,3C Sorghum 9C,9C 9G,9C 10C 10C Wild Oats 9G,9C 9G,4C 6G,3H 6G,3H Johnsongrass 7G,3H 7G,3H 8G,3H 8G,5H Dalisgrass O - O Giant Foxtail O O 4G 5G,3C Ky. Bluegrass 5G 5G 7G,3C 7G,5C Cheatgrass O 5G,5C 6G,3C 4G,3C Sugarbeets 8G,7C 10C 8G,8C 10C Corn 7G,3H 7G,5H 7G,3H 7G,5H Mustard 1OC 9G,9C 100 100 Cocklebur 7G,3H 6G,3H 8G,5H 8G,5H Pigweed 9G,9C 9G,9C 10E 9G,9C Nutsedge 6G 3G 6G 6G Cotton 7G,3H 8G,5H 8G,5H 9G,5H Morningglory 8G 8G,7C 9G,8C 9G,3C Cassia 7G,3C 7G,3H 8G,5H 8G,7C Teaweed 5G,5H 3H 6G,5H 8G,5H Velvetleaf 6G,5H 6G,5H 8G,5C 9G,9C Jimsonweed 2G 5G 5G 7G Soybean O 2G 2G 2G Rice 5G,3C 9G,9C 9G,9C 9G,9E Wheat O 4G 4G 4G Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 6 kg/ha 0.03 0.12 Crabgrass 20 7G Barnyardgrass 5G 7G,2C Sorghum 9G,8C 10C Wild Oats 2G 6G,2H Johnsongrass 7G,3H 8G,3H Dalisgrass O 4G Giant Foxtail 0 40 Ky. Bluegrass 5G 60 Cheatgrass 3G 7G,3C Sugarbeets 100 80,80 Corn 7G,5H 8G,4C Mustard 60 7G,2C Cocklebur 6G,3H 7G,5H Pigweed 8G,7C 10C Nutsedge 6G 60 Cotton 7G,5G 8G,5H Morningglory 6G,5H 80 Cassia 70,30 80,50 Teaweed O 4G,3H Velvetleaf 4G,3H 7G,5H Jimsonweed 0 70,50 Soybean 0 6G,3H Rice 6G,3C 7G,8C Wheat s 30,20 Test C The high herbicidal activity and selective properties of several of the compounds from within the scope of the invention is evident from the results obtained in this test. The experiment concerned pre-emergence applications on soil. The containers used were 25 em diameter plastic pots filled with Fallsington silt loam. One set of pots was planted to weeds, the seeds of which were uniformly mixed with the top 1.2 cm layer of soil. The species selected were: johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusoalli), crabgrass (Disitaria sancuinalis), giant foxtail (Setaria faberii), velvetleaf (Abutilon theoohrasti), jimsonweed (Datura stramonium), mustard (Brassica arvensis), and pigweed (Amaranthus retroflexus). Another set of pots was planted to the following crops with from one to four species per pot: corn (planting dept 3.7 cm), cotton, soybeans, sunflower, Clinton oats, wheat, Black Velentine beans, rice, sorghum, peas, flax, and peanuts (all at 2.5 cm depth), cucumbers, cabbage, alfalfa, safflower, sugarbeets, tomato, spinach, barley, and Kentucky bluegrass (all at 1.2 cm depth). Immediately after planting, the test chemicals were applied to the soil surfaces dissolved in a non-phyto- toxic solvent. In the case of tobacco, a solution containing the test chemical was drenched on the surface of the soil surrounding newly transplanted tobacco seedlings. One pot from the weed phase and one of each of the crop species were left untreated for the purpose of comparison. The treated and untreated pots were promptly watered with approximately 4 mm of simulated rainfall and then held in a greenhouse for several weeks. Visual weed and crop response ratings were made 28 days after treatment utilizing the rating system as described above. The data are given in Table C. The data clearly indicate that compounds from within the scope of the present invention have utility for selective pre-emergence weed control in crops such as soybeans, alfalfa, wheat, oats, barley, cucumber, and tomato. In the case of at least one compound, weed control is obtained by applying the chemical in the form of a drench on the soil around newly-transplanted tobacco seedlings. Table C PRE-EMERGENCE ON FALLSINGTCs SILT LOAM Compound No. 3 kg/ha 1/64 1/32 1/16 1/8 Corn 7G,5H Cotton 7G,5H Soybean 7G,5H Peanut 7G,5H Sunflower 8G,5H Oats Whheat 2G Sorghum 10E Sugarbeet 8G,7C Pea 9G,9C Flax 9G,9C Alfalfa 8G,8C Bean 7G,5H Spinach 9G,8C Cabbage 9G,9C Tomato 4G Rice 1DE Safflower 8G,6C Cucumber 9G,5H Ky. Bluegrass 8G,9C Barley 8G,6C Tobacco 0 Broadleaves 2G,3C 4G,4C 5G,4C Grasses 5G,2C 6G,3C 7G,5C Table C (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compqund No. 11 kg/ha 1/128 1/64- 1/32 1/16 Corn 8G,8C Cotton 7G,5H Soybean. O Peanut Sunflower 9G,8C Oats 6G,2C Wheat 50 Sorghum 90,90 Sugarbeet 9G,9C Pea 10E Flax 7G,5E Alfalfa 70,30 Bean 8G,5H Spinach 80,80 Cabbage 8G,7C Tomato 7G,5H Rice 70,70 Safflower 80,30 Cucumber 9G Ky. Bluegrass 7G Barley 3G Tobacco Broadleaves 50,30 70,70 80,70 Grasses 20 30 4G Table C (continued) PRE- EMERGENCE ON FALLSINGTON SILT LOAM Compound No. 12 ko/ha 1/128 1/64 1/32 1/16 Corn 8G98C Cotton 8G,5H Soybean O Peanut Sunflower 9G,8C Oats 5G,2C Whheat 4G Sorghum 8G,8C Sugarbeet 9G,9C Pea 10E Flax 8G,8C Alfalfa 4G Bean 5G,3H Spinach 8G,9C Cabbage 8G,5C Tomato 2G Rice 9G,8C Sofflower 8G,3C Cucumber 5G Ky. Bluegrass 6G Barley 3G Tobacco Broadleaves 3G 2G 5G,3C Grasses 3G O 3G Test D Twenty-five cm diameter plastic Pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sestania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (D2tura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (D8igitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Rchinochloa crusoalli), giant foxtail (Setarim faterii) and wild oats (Avena fatua). In the case of compound No. 13, the following additional species were included: sunflower, mustard, sugarbeets and bushbean. Approximately 2 weeks after Slanting, the youna 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 D. Several of the compounds tested by this procedure are useful for the post-emergence control 0: weeps in wheat, corn and soybeans. Table D Over-the Top Soil/Foliage Tretment Compound No. 7 kg/ha 0.016 0.031 0.063 0.125 Sovbeans O 9G,4C 4G,2C 10G,7C Velvetleaf 8G,3C 9G,4C 8G,3C 10G,7C Sesbania 5G,3C 7G,3C 7G,3C 10G,5C Cassia 4G,2C 9G,3C 6G,2C 10G,6C Cotton 3G,2C 7G,3C 5G,3C 9G,6C Morningglory 9G,4C 10G,7C 10G,7C 10G,8C Alfalfa 2C,3G 5G,2C 2C,3G 8G,5C Jimsonweed 1C 3G,2C 4G,2C 7G,3C Cocklebur 1C 10G,5C 5G,3C 10G,7C Corn 1H O 2G,1C 1G,2H Crabgrass 1G O 1G 4G Rice 7G,2C 8G,3C 8G,5C 9G,6C Nutsedge 2G 3G,3C 2G,1C 6G,2C Barnyardgrass 1C,6G 7G,3C 1C,6G 10C Wheat O 1G 2G 3G Giant Foxtail - 7G,2C 2G 9C Wild Oats 6G 7G,2C 7G 7G,10C Sorghum 8G,1C 9G,3C 8G,4C 10C Table O (continued) Over-the-Top Soil/Foliage Treatment Compound No. 8 kg/ha 0.016 0.031 0.125 Soybeans 8G,3C 10G,7C 10G,7C Velvetleaf 8G,3C 10G,6C lOG,8C Sesbania 9G,5C 9G,5C 1OG,8C Cassia 5G,3C 10G,4C 100,60 Cotton 8G,4C 9G,4C 10G,6C Morningglory 90,50 10G,8C 10G,8C Alfalfa 5G,3C 7G,4C 8G,5C Jimsonweed 1G,1C 7G,3C 9G,4C Cocklebur 60,20 90,30 10G,7C Corn 7G,4H 1H 6G,3C Crabgrass 20 4G 6G Rice 8G,3C . 80,30 8G,5C Nutsedge 4Gs1C 50,10 7G Barnyardgrass 60,20 80,50 9G,7C Wheat 1G 20 Giant Foxtail 5G 7G,3C 8G,3C Wild Oats 70 80 8G Sorghum 8G,1U 90 90 Table D (continued) Over-the Top Soil/Foliage Tretment Compound No. 9 kg/ha 0.016 0.031 0.063 0.125 Sovbeans 10G,7C 10G,6C 10G,7C 10G,8C Velvetleaf 8G 10G,7C 10G,3C 10G,9C Sesbania 10G,8C 10G,8C 10G,8C 10G,9C Cassia 9G,5C 10G,7C 10G,7C 10G,7C Cotton 7G,3C 9G,3C 10G,6C 10G,7C Morningglory 10G,6C 10G,7C 10G,7C 10G,8C Alfalfa 8G,4C 6G,2C 8G,3C 7G,4C Jimsonweed O 1G 4G,1C 1G Cocklebur 9G,6C 10G,9C 10G,7C 10G,9C Corn 3G,2H O 4G,4H 1G,1H Crabgrass 1C 7G 2G 9G,5C Rice 8G,5C 9G,6C 8G,7C 10G,7C Nutsedge 5G,2C 6G,2C 7G,3C 8G Barnyardgrass 6G,3C 10C 8G,5C 10C Wheat 1G 2G 4G 2G Giant Foxtail 5G,1C 8G,3C 6G,1C 8G,4C Wild Oats 5G 7G,1C 7G,2C 8G,2C Sorghum 9G,3C 10G,8C 9G,4C 9C Table D (continued) Over-the Top Soil/Foliage Tretment Compound No. 10 kg/ha 0.016 0.031 0.063 0.125 Sovbeans O O 1G,1C 5G,3C Velvetleaf 8G,3C 6C,3C 8G,3C 7G,3C Sesbania 2C 7G,3C 4G,3C 7G,3C Cassia 2C 10G,8C 4G,3C 7G,3C Cotton 3G,2C 7G,3C 5G,3C 8G,3C Morningglory 8G,3C 10G,4C 9G,3C 10G,6C Alfalfa 2C 7G,4C 3G,2C 8G,4C Jimsonweed 5G,2C 7G,3C 5G,2C 7G,3C Cocklebur 1C 9G,3C 3G,2C 10G,5C Corn 2H,1C 6G,5H 3G,2H 7G,3U Crabgrass 1G 3G,1C 1G 6G,2C Rice 7G,1C 9G,3C 7G,1C 10G,7C Nutsedge 2G O 2G,1C O Barnyardgrass 1G,1C 6G 1G,1C 8G,2C Wheat O 1G O 1G Giant Foxtail 1G 6G,2C 3G,1C 7G,3C Wild Oats 2G 7G 2G 7G Sorghum 8G,1C 9G,3C 8G,2U 9C Table D (continued Over-the-Top Soil/Foliage Treatment Compound No. 11 kg/ha 0.016 0.031 0.125 Soybeans 1C 10G,7C 10G,7C Velvetleaf 8G,3C 10G,8C 10G,9C Sesbania 10G,6C 10G,7C 10G,9C Cassia 8G,3C .7G,4C 9G,5C Cotton 6G,3C 10G,7C 10G,7C Morningglory 10G,4C 10G,8C 10G,9C Alfalfa 7G,4C 7G,7C 9G,8C Jimsonweed 3G,1C 9G,7C 10G,7C Cocklebur 10G,7C 10G,8C 10G,8C Corn 9G,4C 10G,6C 10G,6C Crabgrass 0 8G,5C 8G,5C Rice 6G,2C 8G,6C 8G,6C Nutsedge 1G 1G 2G Barnyardgrass 6G,1C 8G,3C 10C Wheat 0 0 1G Giant Foxtail 3G - 8G,3C Wild Oats 1G 8G,2C 8G,1C Sorghum 9G,2C 9C 9C Table D (continued) Over-the-Top Soil/Foliage Treatment Compound No. 12 Kg/ha 0.016 0.031 0.125 Soybeans 0 7G,3C 10G,7C Velvetleaf 7G,3C 10G,8C 10G,8C Sesbania 6G,3C 10G,8C 10G,8C Cassia 4G,3C 10G,7C 10G,4C Cotton 4G,3C 10G,4C 10G,7C Morningglory 9G,3C 10G,7C 10G,9C Alfalfa 0 2G 5G,1C Jimsonweed 2G,1C 0 6G,1C Cocklebur IC 10G,8C 10G,8C Corn 9G,2C 9G,3U . 10G,8U Crabgrass 0 . 3G 7G,4C Rice 4G 7G,2C 8G,3C Nutsedge 4G 2G 3G Barnyardgrass 3G 7G,3C 8G,4C Wheat 0 0 0 Giant Foxtail 0 3G,1C 6G,2C Wild Oats- 0 3G 7G Sorghum 8G 9G,7C 9C Table D (continued) Over-the Top Soil/Foliage Tretment Compound No. 2 kg/ha 0.016 0.031 0.125 Sovbeans 5G,3C 9G,7C 10G,7C Velvetleaf 6G,3C 9G,5C 10G,9C Sesbania 5G,3C 9G,4C 10G,8C Cassia 3G,2C 10G,6C 10G,8C Cotton 3G,2C 7G,4C 10G,7C Morningglory 6G,2C 10G,5C 10G,9C Alfalfa 4G,2C 7G,3C 7G,4C Jimsonweed 2G,1C 5G,2C 7G,3C Cocklebur 5G,2C 9G,4C 10G,7C Corn O 2G 3G Crabgrass 1G,1C 1G 3G Rice 4G 5G,2C 7G,3C Nutsedge 3G 6G,1C 7G,1C Barnyardgrass 5G,1C 8G,3C 9G,4C Wheat O 3G 4G Giant Foxtail O 6G,2C 7G,1C Wild Oats O 4G 7G,2C Sorghum 8G,1C 10G 10G,2U Table D (continued) Over-the-Top Soil/Foliage Treatment Compound No. 3 Kg/ha 0.016 0.031 0.063 0.125 Soybeans 6G,3C 10G,7C 9G,3C 8G,5C Velvetleaf 5G,3C 10G,7C 8G,3C 10G,9C Sesbania 5G,3C 10G,8C 7G,3C 10G,8C Cassia 4G,3C 10G,8C 5G,3C 10G,8C Cotton 3C 8G,5C 7G,2C 8G,7C Morningglory 6G,3C 10G,9C 7G,3C 10G,8C Alfalfa 7G,3C 8G,5C 7G,3C 8G,5C Jimsonweed 4G,1C 0 3G,1C 5G,1C Cocklebur 5G,2C 10G,7C 7G,4C 10G,7C Corn 0 0 2G,1C 0 Crabgrass 1G 0 3G 6G,1C Rice 5G,1C 3G,3C 8G,1C 5G,4C Nutsedge 2G 7G,3C 3G 6G Barnyardgrass 4G,1C 8G 6G,1C 8G,3C Wheat 0 0 0 0 Giant Foxtail 3G 7G,3C 3G 8G,1C Wild Oats 0 4G,1C 5G 3G Sorghum 9G 7G,3C 9G,2U 8G,3C Table D (continued) Over-the-Top Soil/Foliage Treatment Compound No 5 Kg/ha 0.016 0.031 0.125 Soybeans 6H,3C 9G,5C lOG,70 Velvetleaf 8G,4C 10G,7C Sesbania SG,.3C 9G,5C 10G,7C Cassia 4G,3C 10G,8C 10G,8C Cotton 5G,2C 9G,2C 10G,6C Morningglory 7G,3C 10G,7C 10G,7C Alfalfa 4G,3C 7G,3C 7G,4C Jimsonweed 5G,2C 6G,3C 8G,3C Cocklebur 7G,3C 9G,4C 10G,7C Corn 9G,3C 8G,6H 8G,8H Crabgrass O 2G 3G Rice 4G 5G,2C 7G,3C Nutsedge 1G 3G 4G Barnyardgrass 6G,1C 8G,4C 9G,4C Wheat Q 3G 3G Giant Foxtail 3G 4G 6G Wild Oats 1G 2G 3G,1C Sorghum 9G,2C 9G,3U 9G,3U Table D (continued) Over-the-Top Soil/Foliage Treatment Compound No. 6 kg/ha 0.016 0.031 0.125 Soybeans 7G,3C 10G,7C 10G,8C Velvetleaf 7G,3C 9G,4C 10G,7C Sesbania 4G,3C 8G,4C 10G,8C Cassia 4G,3C 10G,7C 10G,8C Cotton 6G,3C 9G,3C 10G,6C Morningglory 8G,3C 10G,7C 10G,8C Alfalfa 4G,2C 6G,2C 8G,4C Jimsonweed 2G,2C 7G,1C 8G,2C Cocklebur 1C 10G,6C 10G,8C Corn 9G,3C 8G,4C 9G,4C Crabgrass 0 1G 6G Rice 4G,1C 4G,2C 7G,3C Nutsedge 0 2G 3G Barnyardgrass 0 8G,2C 8G,4C Wheat 0 0 2G Giant Foxtail O 7G,1C 7G Wild Oats O 2G 3G,1C Sorghum 8G,1C 9G,3U 9G,3U Table D (continued) Over-the-Top Soil/Foliage Treatment Compound No. 13 kg/ha 0.016 0.031 0.062 0.125 Soybeans 3G 3G 7G,1C 7G,2C Velvetleaf 7G,2C 7G,2C 9G,3C 9G,4C Sesbania 7G,3C 8G,4C 9G,4C 9G,4C Cassia 8G,4C 9G,5C 9G,6C 10G,5C Cotton 1C 4G,3C 7G,C 9G,3C Morningglory 8G,4C 8G,4C 9G,5C 9G,5C Alfalfa 2C 4G,2C 5G,2C 6G,2C Jimsonweed 3G - 6G 8G Cocklebur 4G,3C 6G,3C 7G,4C 10G,3C Corn 4H 8G,4H 9G,4C 9G,3U Crabgrass 0 0 2G 2G Rice 2G 2G 5G 6G Nutsedge 0 1G 2G 5G Barnyardgrass 0 3G 5G,3C 5G,3C Wheat 0 1G 2G 3G Giant Foxtail 2G 2G 4G 4G Wild Oats O 0 2G 2G Sorghum 4G 6G 7G 7G,3C Sunflower 0 9G,7C 10G,8C 10G,8C Mustard 9G,3C 9G,3C 9G,3C 9G,3C Sugarbeets 1C 2C 4G,3C 5G,3C Bushbean O 0 0 0 Test E Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats Arena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus). The other pan was planted with seeds of Russian thistle (Salsola kali), tansy mustard (Descuraina pinnata), smartweed (Polygo um pennsylvanicum),, jimhill or tumble mustard (Sisymbrium altissium),kochia (Kochia scoparia), shepherdtspurse (Capsella bursa-pastoris), Matricaria inordora, black nightshade (Solanum nigrum), yellow rocket (Barbarea vulgaris), wild mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). The above two pans were treated pre-emergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species. The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans An untreated control and a solvent-alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated in accordance with the previously described rating system. The recorded data are presented in Table E. Severa1 of the compounds included in this table provide excellent weed control at very low rates c application, yet are tolerated with little or no in jiury by wheat and barley at rates which are multiples of those required for weed control. This observation apolies to both pre- and post-emergence tretments. Table E Compound No. 2 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 0 0 1G Barley 2C,4G 5C,4G 1G 4C,6G Wild Oats 3C,2G 5C,5G 1G 6C,6G Downy Brome 7C,4G 8C,7G 2C,2G 10C Cheatgrass 6C,5G 10C 3C,5G 8C,7G Blackgrass 7C,7G 10C 5C,5G 7C,7G Annual Bluegrass 3G 6C,7G 4C 6C,7G Green Foxtail 4C,2G 6C,6G 2G 6C,6G Quackgrass 3G 4C,6G 2C,4G 3C,7G Italian Ryegrass 2G 2C,5G 3G 6G Ripgut Brome 2C,4G 6C,7G 1G 2C,4G Russian Thistle 9C,8G 9C,9G 2C,2G 5C,7G Tansy Mustard 10C 10C 10C 10C Smartweed Jimhill Mustard 10C 10C 10C 10C Kochia 4G 2C,5G 7C,6G 7C,7G Shepherd's Purse <RTI ID=100.12> 10C 10C 7C,7G 8C,7G False Chamomile 4C,6G 7C,8G 5C,5G 7C,7G Black Nightshad 1C,7G 2C,8G 3G 1C,5G Yellow Rocket 9C,9G 9C,9G 5C,6G 10C Wild Mustard 8C,8G 9C,9G 10C 10C Wild Buckeheat 3G 4C,4G 2C,2G 5C,5G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 1G 0 1C,1C Barley 3G 3C,7G 6C,5G 7C,7G Wild Oats 3G 5C,7G 1C,2G 5C,6G Downy Brome 7C,7G 10C 7C,7G 10C Cheatgrass 10C 10C 8C,8G 10C Blackgrass 100 10C 10C 10C Annual Bluegrass 7C,7G 7C,8G 7C,6G 9C,7G Green Foxtail 7C,6G 7C,8G 3C,6G 7C,7G Quackgrass 7G 5C,8G 1C,6G 5C,7G Italian Ryegrass 6G 2C,7G 2G 2C,4G Ripgut Brome 3C,7G 4C,8G 1C,2G 3C,5G Russian Thistle 4C,5G 7C,7G 2C,3G 10C Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard lOC 100 100 100 Kochia 6G 3C,7G 2G 2C,4G Shepherd's Purse 7C,7G 9C,9G 9C,8G 10C False Chamomile 9C,9G 9C,9G 9C,9G 10C Black Nightshade 7C,8G 7C,8G 7C,8G <RTI ID=101.8> 10C Yellow Rocket 9C,9G 9C,9G 10C 10C Wild Mustard 7C,8G 9C,9G 10C 10C Wild Buckwheat 3C,4G 4C,5G 10C,2G 4C,4G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 2C,1G 0 1C,2G Barley 5G 3C,8G 5C,7G 8C,7G Wild Oats 1C,5G 5C,7G 4C,5G 6C,6G Downy Brome 6C,7G 10C 7C,8G 10C Cheatgrass 9C,8G 10C 10C 10C Blackgrass 10C 10C 10C 10C Annual Bluegrass 5C,6G 9C,9G 9C 10C Green Foxtail 3C,4G 9C,9G 6C,6G 7C,6G Quackgrass 5C,6G 9C,8G 3C,6G 8C,7G Italian Ryegrass 3G 4C,6G 1C,3G 4C,5G Ripgut Brome 3G 5C,7G 3C,4G 6C,7G Russian Thistle - - - tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 10C 10C 10C 10C Kochia 2C,5G 5C,6G 0 2G Shepherd's Purse 10C 10C 10C 10C False Chamomile 8C,8G 9C,9G 10C 10C Black Nightshade 3C,6G 5C,6G 9C,8G 10C Yellow Rocket 9C,9G 10C 10C 10C Wild Mustard 9C,8G 9C,9G 10C 10C Wild Buckwheat 2C,4G 5C,6G 3C,4G 4C,4G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.02 0006 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 lC,lG 0 0 Barley 5G 6C,7G 4C,6G 8C,8G Wild Oats 5G 4C,6G 1G 1C,2G Downy Brome 7C,7G 10C 6C,SG 7C,8G Cheatgrass 100 100 8C,7G 8C,8G Blackgrass 10C 10C 9C,8G 10C Annual Bluegrass 7C,8G 7C,8G 4C,6G 7C,8G Green Foxtail 5C,6G 8C,8G 2C,2G 3C,3G Quackgrass 7C,6G 9C,8G 5C,6G 5C, 7G Italian Ryegrass 3G 1C,7G 1G 3G Ripqut Brome 2C,6G 7C,7G 2C,5G 3C,6G Russian Thistle 0 2C,2G 10C 10C Tansy Mustard 9C,9G 100 10C 10C Smartweed - - - Jimhill Mustard 9C,9G 10C 10C 10C Kochia 5G 3C,8G 3C,2G 2C,4G Shepherd's Purse 9C,9G 9C,9G 8C,7G 8C,8G False Chamomile 8C,9G 9C,9G 9C,8G 10C Black Nightshade 2C,7G 4C,7G 5C,6G 7C,7G Yellow Rocket 8C,8G 9C,8G 100 10C Wild Mustard 8C,8G 9C,8G 10C 10C Wild Buckwheat 4G 3C,6G 1C,5G 5C,6G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.002 0.02 0.12 Pre-Emergence Wheat 0 0 0 Bardley 0 0 3G Wild Oats 0 0 1C,3G Downy Brome 1G 2C,3G 3C,5G Cheatgrass 2G 6C,7G 7C,8G Blackgrass 1C,4G 7C,7G 10C Annual Bluegrass 2G 1C,4G 4C,6G Green Foxtail 0 1C,1G 3C,6G Ouackgrass 0 2G 2C,6G Italian Ryegrass 0 1G 1C,4G Ripgut Brome 0 0 5G Russian Thistle 0 0 1C,2G Tansy 8C,8G 8C,8G 9C,9G Smartweed - - Jimhill Mustard 2C,3G 7C,8G 9C,9G Kochia 0 2G 3G Shepherd's Purse 3C,5G 9C,9G 9C,9G Matricaria inodora 3C,4G 7C,7G 7C,8G Black Nightshade 0 1C,3G 3C,6G Yellow Rocket 2C,4G 3C,8G 7C,9G Wild Mustard 3C,4G 7C,7G 8C,8G Wild Buckwheat lC,lG 2G 3C,4G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.002 0.02 0.12 Post-Emergence Wheat 0 1G 3G Barley 0 3G 6G Wild Oats 0 1G 1C,5G Downy Brome 2G 4C,5G 6C,5G Cheatgrass 5C,6G 7C,6G 7C,6G Blackgrass 6C,6G 10C 10C Annual Bluegrass 1C,4G 7C,7G 8C,8G Green Foxtail 0 2C,3G 8C,8G Quackgrass 0 2G 1C,3G Italian Ryegrass 0 0 2G Ripgut Brome 0 2G 1C,5G Russian Thisthle 2C,2G 3C,4G 7C,7G Tansy Mustard 8C,7G 10C 10C Smartweed Jimhill Mustard lOC lOC lOC Kochia 0 0 1G Shepherd's Purse 10C 9C,8G 10C Matricaria inodora 9C,7G 9C,8G 10C Black Nightshade 2C,3G 2C,4G 4C,7G Yellow Rocket 10C 10C 10C Wild Mustard 10C 10C 10C Wild Buckwheat 2C,2G 3C,4G 3C,4G Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.002 0.02 0.12* Pre-Emeroence Wheat 0 0 0 Barley 0 0 3G Wild Oats 0 0 35 Downy Brome 3G 3G 4C,6G Cheatgrass 2C,4G 4C,6G 7C,7G Blackqrass 1C,6G 5C,6G 100 Annual Bluegrass 2G 1C,3G 4C,6G Green Foxtail 0 3C,4G 4C,7G Quackgrass 1G 3G 2C,6G Italian Ryegrass 0 2G 1C,3G Rioqut Brome 0 2G 35 Russian Thisthle 0 0 1C,2G Tansy Mustard 5C,6G 9C,9G 9C,9G Smartweed - - Jimhill Mustard 7C,7G 9C,8G 9C,9G Kochia n 1G 2C,3G Shepherd's Purse 8C,8G 9C,9G 10C Matricaria inodora 6C,5G 7C,7G 8C,8G Black Nightshade 1C,4G 3C,5G 5C,6G Yellow Rocket 4C,7G 7C,8G 7C,8G Wild Mustard 7C,7G 7C,7G 8C,8G Wild Buckwheat 1G 1C,1G 2C,3G *80% wettable powder formulation Table E (continued) Compound No. 3 TEST PLANT kg/ha 0.002 0.02 0.12* Post-Emergence Wheat n 10 2e Barley 0 2G 2C,4G Wild Oats 0 1G 1G Downy Brome 2e 3E 4C,5G Cheatgrass 4G 1C,5G 8C,5G Blackgrass 3C,4G 5C,5G 10C Annual Bluegrass 1C,4G 5C,6G 10C Green Foxtail 9 3e 6C,6G Quackgrass 0 3G 4G Italian Ryegrass 0 1G 1C,3G Ripgut Brome 0 2G 2C,4G Russian Thisthle 0 2C,3G 2C,3G Tansy Mustard 7C,7G 10C 10C Smartweed - - Jimhill Mustard 10C 10C 10C Kochia 0 1G 2C,2G Shepherd's Purse 10C 8C,8G 9C,8G Matricaria inodora 6C,5G 8C,8G 9C,8G Black Nightshade 2C,2G 3C,3G 4C,5G Yellow Rocket 7C,7G 8C,7G 8C,8G Wild Mustard 10C 10C 10C Wild Buckwheat 1C,2G 2C,3G 3C,4G *80% wettable powder formulation Table E (continued) Comoound No. 5 TEST PLANT kg/ha 0.002 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 0 0 0 Barley 1G 3G 0 1C,2G Wild Oats C,G C,G C,G Downy Brome C,G C,G C,G Cheatgrass C,G C,G C,G Blackgrass C,G C,G C,G Annual Bluegrass C,G C,G C,G Green Foxtail C,G C,G C,G Quackgrass C,G C,G C,G Italian Ryegrass C,G C,G C,G Ripgut Brome C,G C,G C,G Russian Thisthle C,G C,G C,G Tansy Mustard lBC 1C 1C 100 Smartweed - ° Jimhill Mustard 8C,9G 10C 10C 10C Kochia 1C,6G 5C,7G 7C,8G 10C Shepherd's Purse 8C,8G 10C 8C,8G 10C False Chamomile 2G 6C,7G 7C,7G 10C Black Nightshade 6G 6C,7G 6C,7G 10C Yellow Rocket 8C,8G 9C,9G 8C,8G 10C Wild Mustard 4C,7G 9C,9G 10C 10C Wild Buckwheat 3C,6G 5C,7G 4C,5G 10C Table E (continued) Compound No. 5 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 1C,1G 0 0 Barley 0 2C,7G 0 2C,5G Wild Oats 1C,2G 2C,5G 0 1C,2G Downy Brome 4G 4C,7G 2G 7C,7G Cheatgrass 4C,7G 5C,7G 2C,3G 10C Blackgrass 10C 7C,8G 7C,6G 10C Annual Bluegrass 6G 7G 1C,2G 9C Green Foxtail 1G 3C,4G 0 6C,5G Quackgrass 0 2C,7G 0 2C,4G Italian Ryegrass 0 2C,7G 0 1C,3G Ripgut Brome 0 3C,3G 0 2C,2G Russian Thisthle - - - Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 2C,6G 10C 10C 10C Kochia 2C,4G 5C,6G 7C,7G 10C Shepherd's Purse 1C,5G 10C 10C 10C False Chamomile 3G 5C,8G 7C,6G 10C Black Nightshade 1C,2G 4C,7G 4C,6G 10C Yellow Rocket 7G 10C 10C 10C Wild Mustard 9C,9G 9C,9G 10C 10C Wild Buckwheat 3C,5G 5C,6G 6C,6G 10C Tab-le E (continued) Compound No. 6 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 0 0 0 Barley 0 2G 0 1G Wild Oats 0 3G 0 1G Downy Brome 2G 2C,6G 1C,2G 3C,5G Cheatgrass 3G 4C,7G 1C,3G 5C,7G Blackgrass 3C,4G 7C,7G 5C,6G 7C,8G Annual Bluegrass 3G 2C,7G 3G 4G Green Foxtail 1G 1C,3G 0 1C,2G Quackgrass 0 5G 0 2C,3G Italian Ryegrass 0 2G 0 0 Ripgut Brome 0 1G 0 0 Russian Thisthle 2C,3G 7C,8G 10C 10C Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 10C 10C 10C 10C Kochia 2G 2C,5G 3C,4G 4C,7G Shepherd's Purse 8C,9G 9C,9G 7C,7G 10C False Chamomile 2G 5C,6G 3C,6G 10C Black Nightshade 1C,6G 5C,7G 2C,6G 9C,8G Yellow Rocket 7G 4C,7G 0 2G Wild Mustard 5G 8C,8G 2C,3G 7C,6G Wild Buckwheat 2G 2C,3G 1C,2G 4C,5G Table E (continued) Compound No. 6 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 1C,1G 0 0 Barley 0 2C,3G 2G 1C,3G Wild Oats 0 3C,4G 0 2G Downy Brome 2G 7C,7G 2G 3C,4G Cheatgrass 1C,7G 7C,8G 1C,3G 10C Blackgrass 3C,7G 10C 3C,4G 8C,7G Annual Bluegrass 6G 7G 1G 2C,2G Green Foxtail 2G 4C,6G 1C,2G 2C,3G Quackgrass 2C,3G 3C,6G 1G 1C,2G Italian Ryegrass 1C,2G 2C,3G 1G 1C,2G Ripgut Brome 1G 1C,2G 2G 1C,3G Russian Thisthle - - - Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 3C,6G 10C 8C 10C Kochia 2G 2C,4G 0 5C,6G Shepherd's Purse 5C,6G 10C 10C 10C False Chamomile 1G 7C,8G 8C,8G 9C,8G Black Nightshade 1C,2G 2C,4G 2C,4G 7C,8G Yellow Rocket 6G 7G 0 2C,4G Wild Mustard 2C,5G 3C,6G 8C,8G 7C,6G Wild Buckwheat 2C,4G 2C,5G 2C,2G 5C,5G Table E (continued) Compound No. 8 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 1C,1G 3C,1G 2G 2C,3G Barley 2C,6G 3C,7G 6C,6G 7C,8G Wild Oats 6C,6G 6C,6G 4C,5G 8C,8G Downy Brome 8C,8G 9C,9G 7C,8G 10C Cheatgrass 10C 10C 8C,8G 10C Blackgrass 10C 10C 8C,8G 10C Annual Bluegrass 8C,7G 8C,8G 7C,7G 9C,8G Green Foxtail 7C,6G 7C,8G 4C,3G 7C,6G Quackgrass 4C,5G 8C,8G 7C,7G 7C,7G Italian Ryegrass 3C,6G 8C,8G 4C,6G 5C,7G Ripgut Brome 5C,7G 6C,8G 3C,5G 5C,7G Russian Thisthle 2C,4G 10C 8C,7G 9C,8G Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 9C,9G 10C 10C 10C Kochia 5C,6G 5C,7G 4G 4C,5G Shepherd's Purse 9C,9G 10C 9C,7G 10C False Chamomile 7C,8G 8C,9G 9C,8G 10C Black Nightshade 2C,7G 3C,8G 5G 6G Yellow Rocket 9C,9G 9C,9G 9C,7G 9C,8G Wild Mustard 9C,9G 9C,9G 10C 10C Wild Buckwheat 2C,4G 5C,6G 7C,5G 7C,7G Table E (continued) Compound No. 9 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 1C,2G 2C,2G 1C,2G 2C,2G Barley 3C,7G 6C,8G 8C,7G 8C,8G Wild Oats 3C,7G 6C,7G 3C,4G 5C,6G Downy Brome 8C,7G 10C 8C,8G 10C Cheatgrass 10C 10C 10C 10C Blackgrass 10C 10C 10C 10C Annual Bluegrass 7C,7G 9C,8G 10C 10C Green Foxtail 7C,7G 7C,8G 6C,7G 7C,8G Quackgrass 8G 8C,8G 7C,6G 9C,7G Italian Ryegrass 2C,8G 7C,8G 10C 10C Ripgut Brome 8G 7C,8G 4C,6G 6C,7G Russian Thisthle 2G 5C,5G 6C,5G 10C Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 10C 10C 10C 10C Kochia 7G 3C,8G 5C,6G 10C Shepherd's Purse 10C 10C 10C 10C False Chamomile 7C,8G 9C,9G 10C 10C Black Nightshade 5C,8G 6C,8G 8C,8G 10C Yellow Rocket 9C,9G 10C 10C 10C Wild Mustard 9C,9G 9C,9G 10C 10C Wild Buckwheat 4C,6G 5C,7G 3C,3G 9C,8G Table E (continued) Compound No. 11 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 0 0 1C,4G Barley 2C,2G 2C,4G 0 3C,3G Wild Oats 2C,3G 3C,6G 0 3C,3G Downy Brome 4C,6G 7C,7G 2C,2G 10C Cheatgrass 3C,7G 10C 2C,6G 9C,8G Blackgrass 7C,8G 10C 3C,7G 10C Annual Bluegrass 7G 7C,8G 7C,7G 10C Green Foxtail 2C,4G 5C,8G 3G 7C,7G Quackgrass 6G 4C,7G 1C,4G 5C,7G Italian Ryegrass 7G 5C,8G 2C,4G 10C Ripgut Brome 3C,3G 3C,6G 0 3C,6G Russian Thisthle 3C,3G 8C,7G 10C 10C Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 10C 10C 10C 10C Kochia 3C,7G 5C,8G 5C,5G 10C Shepherd's Purse 10C 10C 10C 10C False Chamomile 7C,7G 8C,8G 10C 10C Black Nightshade 7C,8G 8C,8G 10C 10C Yellow Rocket 10C 9C,9G 10C 10C Wild Mustard 9C,9G 9C,9G 10C 10C Wild Buckwheat 7C,7G 8C,8G 8C,7G 10C Table E (continued) Compound No. 12 TEST PLANT kg/ha 0.02 0.06 0.02 0.06 Pre-Emergence Post-Emergence Wheat 0 0 0 0 Barley 2G 3G 0 2G Wild Oats 3G 6G 0 1C,3G Downy Brome 2C,5G 3C,6G 2G 5C,4G Cheatgrass 1C,7G 7C,7G 3G 2C,6G Blackgrass 5C,7G 8C,8G 2C,2G 5C,7G Annual Bluegrass 5G 4C,7G 2G 3G Green Foxtail 1C,2G 2C,5G 0 1G Quackgrass 2G 5G 0 1C,2G Italian Ryegrass 3G 5G 0 3G Ripgut Brome 2G 3G 0 0 Russian Thisthle 2C,2G 2C,3G 2C,3G 10C Tansy Mustard 10C 10C 10C 10C Smartweed - - - Jimhill Mustard 10C 10C 10C 10C Kochia 2C,5G 3C,6G 0 7C,7G Shepherd's Purse 9C,9G 9C,9G 10C 10C False Chamomile 5C,6G 7C,8G 10C 10C Black Nightshade 7C,7G 7C,8G 10C 10C Yellow Rocket 7C,8G 7C,8G 0 1C,2G Wild Mustard 9C,9G 9C,9G 0 1C,2G Wild Buckwheat 7C,8G 7C,8G 4C,3G 8C,7G Test F The results obtained from this test demonstrate the high herbicidal activity of a compound selected from the scope of the invention when it is mixed with the water of simulated rice paddies. The test samples were applied directly into the water of paddies three days after transplantino of M7 rice plants. The test was maintained in a greenhouse, and plant response ratings were ta4en 3 days after application, utilizing the rating system as previously described. Table F Compound No. 3 Barnyard- Water Treatment Rice crass Chestnut Arrowhead 10 g/ha 6G 5E 8G 0 40 g/ha 10G,4C 10E 10G,3C 5F A field study was conducted to determine the crop selectivity and herbicidal activities of various chemicals. The test was conducted on a Wea silt loam having an organic matter content of 2.8 percent and a p i of 7.2. The plots were planted to sugarbeets, oats, giant foxtail, wild oats, barley, rape, wheat, soybeans, velvetleaf, dry beans, corn and sunflower. The area had a natural infestation of pigweed. The test included.both pre- and post-emergence treatments. The pre-emergence treatments were applied directly after planting. The post emergence treatments were applied 21 days after planting. Ratings were made on the percent control of both crops and weeds at various times after application. Pre-Emergence Test o Table G-I The n-propyl-dimethoxypyrimidine material showed crop selectivity on wheat, corn and soybeans while controlling giant foxtail, velvetleaf and pigweed at selected rates. The isopropyl-dimethoxypyrimidine material exhibited crop selectivity on wheat and corn. The compound controls giant foxtail and pigweed. Post-Emergence Test - Table G-II The isopropyl-dimethoxypyrimidine compound exhibited selectivity in all of the cereal crops tested (oats, barley and wheat) while some corn tolerance was noted. The compound provided control of broadleaf weeds including velvetleaf and pigweed. The n-propyldimethoxypyrimidine exhibited selectivity in wheat, oats, corn and soybeans- it controlled pigweed and velvetleaf. Test G A field study was conducted to determine the crop selectivity and herbicidal activities of various chemicals. The test was conducted on a Wea silt loam having an organic matter content of 2.8 percent and a pH of 7.2. The plots were planted to sugarbeets, oats, giant foxtail, wild oats, barley, rape, wheat, soybeans, velvetleaf, dry beans, corn and sunflower. The area had a natural infestation of pigweed. The test included both pre- and post-emergence treatments. The pre-emergence treatments were applied directly after planting. The post-emergence treatments were applied 21 days after planting. Ratings were made on the percent control of both crops and weeds and various times after application. Pre-Emgaence Test - Table G-I The n-propyl-dimethoxypyridmine material showed crop selectivity on wheat, corn and soybeans while controlling giant foxtail, velvetleaf and pigweed at selected rates. The isopropyl-dimethoxypyrimidine material exhibited crop selectivity on wheat and corn. The compound controls giant foxtail and pigweed. Post-Emergence Test - Table G-II The isopropyl-dimethoxypyrimidine compound exhibited selectivity in all of the cereal crops tested (oats, barley and wheat) while some corn tolerance was noted. The compound provided control of broadleaf weeds including velvetleaf and pigweed. The n-propyldimethoxypyrimidine exhibited selectivity in wheat, oats, corn and soybeans- it controlled pigweed and velvetleaf. Table G-I PRE-EMERGENCE FIELD TEST Compound No. 9 kg ai/ha 1/2 1/4 1/16 * + o * + o * + o Sucarbeets 8.0 8.5 7.0 9.0 9.0 9.0 8.0 8.0 6.0 Oats 5.5 5.0 5.5 4.0 5.0 3.0 2.0 1.5 1.0 Giant Foxtail 10.0 9.5 10.0 9.5 9.0 5.0 8.5 5.0 6.0 Wild Oats 6.5 8.0 6.5 5.0 6.0 5.0 4.0 2.5 2.5 Barley 7.5 8.5 8.0 5.0 6.0 2.5 5.0 4.0 2.5 Rape 9.0 10.0 10.0 9.0 10.0 10.0 8.5 10.0 10.0 Wheat 1.0 2.0 0.3 1.0 1.0 1.0 1.0 0.0 0.0 Soybeans 6.0 3.0 5.5 3.5 0.5 1.0 2.0 1.0 0.0 Velvetleaf 6.0 9.5 9.5 3.5 9.0 8.0 0.5 2.5 1.5 Dry Beans 5.5 8.5 9.0 4.0 7.5 5.0 1.5 2.5 1.5 Corn 3.0 2.5 4.0 1.0 0.5 1.0 1.5 0.0 1.0 Sunflower 10.0 10.0 9.5 8.0 9.0 8.5 9.5 9.5 9.5 Pigweed 10.0 10.0 10.0 9.5 10.0 9.5 9.5 10.0 9.5 * Averaged plant response of two replication taken 21 days after treatment. + Averaged plant response of two replication taken 38 days after treatment. o Averaged plant response of two replication taken 55 days after treatment. Rating Scale -0-10, 0 = no control, 10 = 100% control. Table C-I (continued) PRE-EMERGENCE FIELD TEST Compound No. 3 kg ai/ha 1/2 1/4 1/16 * + o * + o * + o Sucarbeets 9.0 10.0 10.0 9.0 9.5 8.5 9.5 9.0 8.0 Oats 6.0 6.5 6.0 4.0 4.0 2.5 2.5 2.0 1.5 Giant Foxtail 10.0 9.5 8.5 9.5 8.5 7.5 19.0 8.5 6.5 Wild Oats 7.0 7.0 5.5 5.0 5.0 3.0 2.0 2.0 2.0 Barley 6.0 7.0 4.0 7.0 6.5 4.0 4.5 4.5 3.0 Rape 9.5 10.0 10.0 9.5 9.5 10.0 9.5 10.0 9.5 Wheat 2.0 2.5 0.0 1.0 1.0 0.0 0.5 0.5 0.0 Soybeans 8.0 8.0 9.0 3.5 2.5 2.5 5.0 2.0 3.5 Velvetleaf 4.0 8.5 7.5 4.5 6.0 1.5 5.0 4.0 3.5 Dry Beans 5.0 7.0 4.0 4.0 4.5 2.0 4.5 4.0 2.5 Corn 4.5 4.0 3.5 1.0 1.0 1.5 3.0 0.5 0.5 Sunflower 10.0 10.0 10.0 8.5 9.0 8.5 4.0 9.5 8.0 Pigweed 10.0 10.0 10.0 1.00 10.0 9.5 10.0 10.0 9.0 * Averaged plant response of two replications taken 21 days after treatment. + Averanged plant response of two replication taken 38 days after treatment. o Averaged plant response of two replications ta4en 55 days after treatment. Rating Scale - 0-10, 0 = no control, 11 = 100% control. Table G-II POST-EMERGENCE FIELD TEST Compound No. 3 kg ai/ha 1/4 1/16 1/64 1/4 1/16 1/64 + o + o + o Sucarbeets 8.5 6.5 8.5 6.0 5.5 2.5 Oats 2.5 1.5 2.0 1.0 0.5 0.0 Giant Foxtail 2.5 3.0 2.5 2.0 3.5 2.0 Wild Oats 3.5 1.0 2.5 0.5 2.5 0.0 Barley 6.5 1.5 3.0 1.0 2.5 2.0 Rape 9.0 10.0 8.5 8.0 7.5 4.5 Wheat 0.0 0.0 0.0 0.0 1.0 0.0 Soybeans 7.0 6.5 5.5 3.0 1.5 1.0 Velvetleaf 8.5 8.0 8.5 4.5 7.0 2.5 Dry Beans 8.0 7.0 8.0 5.0 7.5 3.5 Corn 4.0 4.5 4.0 2.5 1.0 1.0 Sunflower 9.0 10.0 8.5 8.5 8.0 5.5 Pigweed 9.5 8.5 9.0 7.5 7.0 5.0 +Averaged plant response of two replication taken 17 days after treatment. Q Averaged plant response of two replications taken 34 days after treatment. Rating scale 0-10, 0 = no control; 10 = 100% control. Table G-II (continued) POST-EMERGENCE FIELD TEST Compound No. 9 kg ai/ha 1/4 1/16 1/64 1/4 1/16 1/64 + o + o + o Sugarbeets 7.5 4.0 9.0 6.5 6.0 4.5 Oats 4.0 1.0 3.0 0.5 2.0 0.5 Giant Foxtail 6.5 3.5 7.0 6.5 4.5 4.5 Wild Oats 4.0 1.0 4.0 1.5 2.5 1.0 Barley 7.0 4.0 4.5 2.0 3.5 2.0 Rape 9.0 10.0 9.0 9.0 8.0 7.0 Wheat 1.0 0.0 0.0 0.0 1.0 0.0 Soybeans 4.0 2.5 5.0 2.0 1.5 0.5 Velvetleaf 10.0 10.0 9.5 8.5 8.5 5.0 Dry Beans 9.0 9.0 9.0 8.0 8.0 4.0 Corn 2.5 3.0 2.0 4.0 0.5 1.0 Sunflower 9.5 10.0 9.0 10.0 9.0 8.5 Pigweed 9.0 9.0 9.5 8.5 9.0 8.5 + Averaged plant response of two replications taken 17 days after treatment. o Averaged plant response of two replications taken 34 days after treatment. Rating scale 0-10, 0 = no control; 10 = 100% control. Test H A field test site containing Matapeake silt loam. soil with 10% organic matter content was plowed and disoed in preparation for seeding. Just prior to final discing, 539 lbs/a of 10-10-10 fertilizer was applied to the soil. Twenty-eight crops and five weed species were drilled. Shortly after planting chemical treatments were apolied to the soil surface of the plots All treatments were replicated twice. within five days after the application, 2.5 cm of water was applied to plots using overhead sprinkler irrigation. Evaluation of the effect of the chemicals began 30 days after application. The effect of the chemicals on crons and weeds was rated on a scale of 0-100 where 0 represented no effect and 100 represented complete kill. 1. Untreated controls were included in the experi- anent for comparison. The results obtained are ore- sented in Table H. It will be seen that certain com- pounds from the soqe of the invention can be used for selective pre-emergence weed control in such crops-as soybeans, corn, wheat, cotton, flax and liana beans. Table H Pre-Emergence Multicrop Field Test % Effect1 Compound No. 3 9 kg ai/ha .031 .062 .125 .062 .125 .250 Safflower 0 0 0 5 65 90 Sunflower 0 0 0 0 45 90 Corn 0 0 5 0 5 0 Sorghum 5 0 5 0 30 90 Clover 0 0 0 0 0 20 Alfalfa 0 0 0 0 10 30 Soybeans 0 0 5 0 0 0 Sugarbeets 0 0 0 0 0 30 Rape 0 0 5 15 85 100 Squash 0 0 0 0 0 60 Potatoes 0 0 5 0 15 40 Cucumbers 10 0 0 20 0 20 Lespedela 0 0 10 0 0 30 Wheat 0 0 0 0 0 0 Rice 45 0 10 0 0 70 Okra 0 0 5 0 0 10 Oats 0 0 0 0 0 60 Cotton 0 0 0 0 0 0 Carrots 0 0 0 0 5 80 Red beets 0 0 0 5 5 20 Cabbage 0 0 0 0 35 90 Endive 0 0 10 0 0 Flax 0 0 0 0 0 0 Spinach 13 0 5 0 0 70 Snap beans 10 0 5 0 0 0 Tomatoe 0 0 5 10 0 10 Peanuts - - - - - Lima beans 0 0 0 15 0 0 Velvetleaf 0 0 0 0 0 70 Wild Oats 0 0 0 0 25 10 Ryegrass 0 0 5 5 35 20 Barnyardgrass 0 0 0 0 25 60 Foxtail 5 5 15 1O 35 70 Crabgrass 0 0 0 0 30 70 Ragweed 10 0 5 5 35 70 lambsquarter 15 0 25 1O 25 Smartweed 0 - 10 0 30 70 Purscane - 0 0 - - Jimsonweed 0 - - 0 0 60 Pigweed 0 0 - 0 - 60 Morningglory O 0 0 0 0 50 Nutsedge 0 0 0 0 0 Flower-of an Hour 15 3 10 10 10 70 10 0 = no effect; 100 = complete kill. Test I A post-emergence field test was conducted using. the same plantings as described in Test H. Twenty-one days after plantino, chemical treatments were applied to emerged crops and weeds in each plot. All treat- ments were applied in water containing 0.1% surfactant and were replicated twice. Evaluation bean 3 days after application. Again, the effeot of a treatment on crops and weeds was rated on a scale of 0-100, where 0 = no effect and 100 = complete kill. Untreated controls were included in the experiment for comparison. The data are summarized in Table I. The compounds tested provided excellent post- emergence weed control in a number of crops, including corn, wheat, oats, potatoes, flax and tomatoes. Table I Post-Emergence MulticroD Field Test % Effect1 Compound No. 3 9 kg ai/ha .015 .031 .052 .031 .062 .125 Safflower 85 90 95 90 100 100 Sunflower 90 90 90 95 100 100 Corn 0 20 45 0 0 0 Sorghum 90 90 90 95 90 95 Clover 25 50 65 65 75 85 Alfalfa 55 55 75 65 70 70 Soybeans 25 50 65 25 50 70 Sugarbeets 15 15 50 25 30 35 Rape 55 75 65 95 95 100 Squash 65 73 80 85 85 95 Potatoes 0 5 10 0 0 15 Cucumbers 30 45 45 5 10 35 Lespedela 70 65 70 70 70 95 Wheat 0 0 20 0 0 0 Rice 25 30 30 35 40 45 Okra 10 60 55 55 60 65 Oats 0 5 10 0 0 15 Cotton 45 50 70 89 70 73 Carrots 2n 40 85 90 85 95 Red beets 30 45 93 90 93 95 Cabbage 25 60 75 80 90 100 Endive 20 - - - - Flax 0 20 15 10 25 45 Spinach 45 90 90 90 95 100 Snap beans 55 65 75 55 80 85 Tomatoe 5 0 10 0 5 15 Peanuts - - - - - Lima beans 5 60 70 80 85 90 Velvetleaf 55 95 95 90 100 100 Wild Oats 10 10 15 5 40 30 Ryegrass 5 5 25 20 70 60 Barnyardgrass 0 0 10 8n 90 9: Foxtail 10 5 35 5 40 50 Crabgrass - 0 40 - 10 Ragweed 55 70 85 70 80 85 Lambsquarter 30 90 75 55 90 70 Smartweed - - 80 60 70 80 Purscane - - 90 - 90 85 Jimsonweed - - 30 0 - 0 Pigweed 40 90 85 80 90 85 Morningglory - - - - - Nutsedge - - - 0 - Flower-of an Hour 70 80 75 70 90 80 1 0 = no effect; 100 = complete kill. Test J In a pre-emergence field test study, Matapeake silt loam soil with 1% organic matter content was plowed and disked in preparation for seeding. Just prior to final discing 509 lbs/a of 10-10-10 fertllizer was applied to the soil. Corn was planted into single row plots. Shortly after planting, chemical treatments were applied to the soil surface of the slots. All treatments were aoplied in water. The experiment was designed as a partially randomized com- delete block with 3 replications. The first replica- tion was layed out in numerical sequence and not ran domized. Evaluation of treatments began 43 days aster application. The effect of---a treatment on crops and indigenous weeds was rated on a scale of 0-100, where 0 = no effect and 100 = complete kill. Untreated controlls were included in the experiment for comparison. The results obtained are given in Table J. It will be apparent from Table 0 that the compound tested can be used for selective pre-emeroence weed control in con. Table J Pre-Emergence Corn Field Test % Effectl Compound No. 9 Untreated Control kg ai/ha 0.031 0.062 0.125 0.250 Cult. Uncult. Corn 0 3 0 7 0 0 Fall Panicum 53 73 80 93 - 0 Crabgrass 43 57 70 90 - 0 Yellow Foxtail 53 63 80 90 - 0 Purslane 70 87 86 96 - 0 Flower-of-an-hour 53 70 80 90 - 0 Galinsoga - 0 - - - 0 Velvetleaf 33 57 90 90 - 0 1 % effect: O = no effect; 100 = complete kill. Average of 3 replications Test K For a post-emergence field test, a site as de scribed in Test J was selected. Twenty-one days after planting the corn chemical treatments were applied to the emerged crop and weeds in each plot. Each treatment included applications to both previously untreated plots and to plots whiCh earlier had received a pre-emerqence application of alachlor herbicide. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replications. The first replication was layed out in numerical sequence and not randomized. Ev:lua- tion of treatments began 39 days after application. The effect of a chemical on corn and indigenous weeds was rated on a scale of 0-100, where 0 is no effect and 12 is complete kill. Untreated controls were included in the experiment for comparison. The data, shown in Table K, indicate the potential utility of a compound from the scope of the present invention for selective post-emergence weed control in corn, both when applied by itself or in conjunction with a prior pre-emergence treatment of alachlor. Table K Post-Emergence Corn Field Test % Effect Compound No. 9 kg ai/ha 0.031 0.062 0.125 0.250 Cult Uncult w/o Alachlor Corn 0 7 0 30 0 3 Fall Panicum 0 7 20 27 - 0 Purslane 37 60 53 70 - 0 Galinsoga - - - - - 0 Flower-of an-Hour - - - 80 - 0 with Alachlor Corn Fall Panicum 0 3 0 23 0 0 Purslane 100 100 100 97 - 100 Galinsoga 100 100 100 100 - 97 Flower-of- 100 100 - 100 - 100 an Hour 95 100 1 100 - 87 1 % Effect, 0 = no effect, 1Q3 = complete kill. Test L This field test was conducted on a site as previously described for tests H through K. Wheat, wild oats and mustard were drilled into plots. Herbicide treatments were applied in the spring when wheat was fully tillered and 12X23 cm tall. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replica- tions. The first replication was layed out in nurneri- cal sequence and not randomized. Evaluation of treatments began 25 days after application. The effect of a treatment on crops and weeds was rated on a scale of O - 100, where 0 o no effect and 100 = complete kill. Untreated controls were included in the experiment for comparison. The data, presented in Table L, indicate that the test compound provides control of certain weed species without injuring the cro: when applied post-emergence to wheat. Table L Post-Emergence Sprint Wheat Field Test X Effectl Compound No. 3 Untreated kg ai/ha .0O8 .015 .031 .062 Control Wheat 0 0 0 0 0 Yellow Foxtail 0 3 7 7 0 Ragweed 0 7 17 27 0 Wild Oats 0 0 0 0 0 Velvetleaf 3 7 3 3 0 Flower-of-an-hour 3 10 3 3 0 Mustard 40 65 - - 0 Wheat Yieldê 169 223 190 259 203 I % Effect - 0 = no effect, 100 = complete kill; Average of 3 replicates. 2 Wheat Yield - Yield from all 4 rows/Dlot. Data Average of 3 replicates. Test M For a pre-plant incorporated field test on winter wheat, a Keyport silt loam with 1% organic matter content was plowed and disked in preparation for fall seeding. Just prior to final disking 500 lbs/a of 10-10-10 fertilizer was applied to the field. Chemical treatments were then applied to the soil surface of plots. All chemicals were applied in water. Immediately after applicaton the chemical was incorporated into the upper 5 cm of soil utilizing a rototiller. Wheat, wild oats and wild mustard were then drilled into plots. The experiment was designed as a partially randomized complete block with 3 repli- cations. The first replication was layed out in nu- merical sequence and not randomized. Evaluation of the treatments was made 31 days after aoolication. The effect of a chemical on wheat and weeds was rated on a scale of 0-100, where O o no effect and 100 comolete kill. Untreated controls were included in the experiment for comparison; The test results are tabulated in Table L. The test chemicals used as pre-plant incorporated treatments provided excellent control of mustard without causing injury to the wheat crop. Table M Pre-plant incorporated field test on wheat % Effectl (31 days after treatment) Compound Wild Wild Nc. ko ai/ha Wheat Oats Mustard 3 .062 0 0 60 .125 0 0 90 .250 0 3 92 9 .062 0 0 90 .125 0 0 90 .25" 3 3 90 Untreated Control - 0 0 0 1 % Effect - 0 = no effect, 1O0 = complete kill. Test N For a pre-emergence field test on winter wheat, a site as described in Test M was selected. Wheat, wild oats and wild mustard were drilled into the plots and herbicide treatments were applied to the soil sur- face of the plots immediately after planting. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replicatons. The first replication was layed out in numerical sequence and not randomized. Evaluation of treatments were made 31 days after application. The effect of a chemical on wheat and weeds was rated on a scale of of O , where 2 = no effect and 10 = complete kill. Untreated controls were included in the experi- ment for comparison. The ratings are presented in Table N. The chemicals used in this test provide ev- cellent pre-emergence weed control in wheat. Table N Pre-emergence Field Test on Wheat % Effectl (31 days after treatment) Compound Wild Wild No. kg ai/ha Wheat Oats Mustard 3 .062 0 0 83 .125 0 0 90 .250 0 0 90 9 .062 3 0 90 .125 0 0 90 .250 3 19 9n Untreated Control 3 l 0 0 1 % Effect - 0 = no effect, 100 = complete kill.

Claims: CLAIMS: 1. A compound selected from EMI137.1 wherein R1 is R3S[O]n; R3 is C1-C4 alkyl, C3-C4 alkenyl, cyclopentyl or cyclopropylmethyl; R2 is H, F, Cl, Br, CH3, OCH3, CF3, NO2, CN or NH2; n is 0, 1 or 2; W is O or S; T is CH or N; Z is CH or N; X is CH3, C2H5, OCH3, C2H5, or CH2OCH3; and Y is CH3 or OCH-; and their agriculturally suitable salts; provided that (1) when R2 is CN, then T is CH and is not ortho to the sulfonylurea group; (2) when W is S, then n is O or 2; (3) when T is N, then n is 2; and (4) when T is CH, then R3 is not C1-C2 alkyl and R1 is at the 2- or 4- position. 2. A compound of Claim 1 wherein W is O and R2 is H, F, Cl. Br, CH3 or OCH3. 3. A compound of Claim 2 wherein R1 is at the 2- or 4- position when T is N. 4. A compound of Claim 3 wherein n is 2. 5. A compound of Claim 4 wherein R2 is H. 6. A compound of Claim 5 wherein X is CH3 or OCH3. 7. A compound of Claim 6 wherein R3 is Cl-C4 alkyl. 8. The compounds of Claim 1, which are N-E (4,6-dimethylpyrimidin-2-yl)aminocarbonyl3-2-E methylethyl)sulfonyl]benzenesulfonamide, N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2 [ (l-methylethyl )sulfonylzbenzenesul fonamide, N-[(4,6-dimethoxypyridimin-2-yl)aminocarbonyl]-2-[(1 methylethyl)sulfonyl]benzenesulfonamide, N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2 [(1-methylethyl)sulfonyl]benzenesulfonamide, N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar bonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2 I ( 1 -methyl ethyl ) sul fonyl 3 benzenesul fonami de, N- 6-dimethylpyrimidin-2-vl)aminocarbonyll-2 (propylsulfonyl)benzenesulfonamide; ; N-[(4-methoxy-6-methylpyridimin-2-yl)aminocarbonyl] 2-(propylsulfonyl)benzenesulfonamide, N-[(4,6-dimethoxypyridimin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzenesulfonamide, N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2 (propylsulfonyl)benzenesulfonamide, N¯[ methOxy-6-methy 3 5-triazin-2-yl ) aminQcc-bon yl]-2-(propylsulfonyl)benzenesulfonamide, N-[(4,6-dimethoxy-1,3,5-riazin-2-yl)aminocarbonyl] 2-(propylsulfonyl)benzenesulfonamide, N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2 (methylsulfonyl)-3-pyridinesulfonamide, ( 4-Hethoxy-6-methylpyrimidin-2-yl ) aminocarbonyl ] - 2- (methylsulfonyl) -3-pyridinesulfonamide, N-[(4,6-Dimethoxy-1,3,5,-triazin-2-yl)aminocarbonyl] 2-(methylsulfonyl)-3-pyridinesulfonamide, N-[(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2 (methylsulfonyl)-3-pyrimidinesulfonamide, N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl] 2-(methylsulfonyl)-3-pyridinesulfonamide; and N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]-2-(methylsulfonyl)-3-pridiensulfon amide; and their agriculturally suitable salts. 9. A compound of claim 1 wherein R1 is R3S02; R3 is C1¯C4 alkyl, C3-4 alkenyl or cyclopentyl; R2 is H, F, C1, Br, CH3 or OCH3, and T is N: 10. A compound of claim 1 wherein: EMI139.1 R3 is C3 or C4 alkyl or alkenyl. 11.A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a herbicidal compound and at least one of the following: surfactant, solid or liquid diluent, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 10. 12. A method for controlling the growth of undesired vegetation by applying to th-e 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 10. 13. The method of claim 10 wherein said undesired vegetation is selectively controlled in the presence of crop plants. 14. 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 10. 15. A process for preparing a compound of claim 1 which comprises: (a) reacting together compounds of general formulae EMI140.1 wherein R1 is R3SO2 or R3S R2 is as defined in claim 1, other than NH2 R3, T, W, X, Y and Z are as defined in claim 1; or (b) to prepare a compound of claim 1 wherein R2 is NH2, reducing a corresponding compound wherein R2 is NO2; or (c) reacting together compounds of general formulae EMI140.2 wherein R2 is R@S or R@SO and R T W X Y and Z 3 2 2' T, W, are as defined in claim 1; or (d) to prepare a compound of claim 1 wherein n is 1 and W is.O, oxidizing a corresponding compound wherein n is- zero.

Inventors: ADAMS, JOHN BENJAMIN, JR., LEVITT, GEORGE
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1981
Main classification: A01N47
IPC codes: C07D521, A01N47