HERBICIDAL SULFONAMIDES, AND PREPARATION AND USE THEREOF

Abstract: Sulfonamides of the general formula RSO₂NNHR₁ (I) or wherein R is optionally substituted phenyl or optionally substituted pyridyl; R₁₂ is selected from various organic groups; X is H, CH₃, CH₃O, Cl or OCH₂CH₃; Y is CH₂ or O; and W is O or S; and their agriculturally suitable salts, exhibit herbicidal activity. The compounds can be formu­ lated into herbicidal compositions in conventional manner. The compounds of formula I may made by reacting a cor­ responding sulfonyl thiocyanate or isothiocyanate of the formula RSO₂NCW with an appropriate aminopyrimidine derivative. The compound of formula II may be made by appropriate alkylation of an alkali metal or alkaline earth metal salt of a corresponding sulfonylthiourea.

Description: "Herbicidal sulfonamides, and preparation and use thereof" Background of the Invention This invention relates to N-(heterocyclicamino- carbonyl)aryl and pyridylsulfonamide agricultural chemicals. French Patent tio. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: EMI1.1 wherein R = , 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: EMI1.2 wherein R is butyl, phenyl or EMI1.3 and R1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl or phenyl were most potent. The others were- of low potency or inactive. Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) (Chem. Ab., 39 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocar bonyl]-4-methylbenzenesulfonamide: EMI1.4 Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound. Netherlands Patent 121,788, published September 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, EMI2.1 wherein and and R2 may independently be alkyl of 1-4 carbon atoms; and R3 and R may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. U.S. Patent 3,637,366 discloses compounds having the formula: EMI2.2 wherein R1 is hydrogen or lower saturated acyl, 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. Substituted pyrimidinyl sulfonyureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 59, 18052 g (1959)1: EMI2.3 where R = H o or C3. The presence of undesired vegetation causes substantial damage te useful crops, especially agri cultural products that satisfy manes 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 the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available such materials are commonly referred to as herbicides. Some weeds, (such as nutsedge) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause- damage to the crops themselves. Thus, a need exists for active herbicides which cause minimal damage to the crops Summary of the. Invention According to this invention,.there are provided compounds of Formulas I and II and their agriculturally suitable salts, suitable agricultural compositions containing them, and methods of using them as selective, as well as general herbicides having both preemergence and postemergence activity. EMI3.1 wherein EMI4.1 R2 is H, CH3, OCH3, F, Cl, Br, NO2, CF3, COR5, S(O)mR10, SO2NR10R11, RO2OCH2CF3, SO2OCH2CCl3 or SO2N(OCH3)CH3; R3 is H, F, Cl, Br, alkyl C1-C4 or CE30; R4 is , Cl, Br, F, alkyl C1-C4, alkoxy C1-C4, NO2, CO2R6 or R13-S-, provided that R4 is restricted to the 2- or 4 position of the pyridine ring; is alkoxy C1-C6; alkenyloxy C3-c6; haloalkoxy C2-C6 having 1 to 3 halogens selected from Cl, F and Br; cycloakoxy C5-C6; O#CH2CH2#nR7; OCH2CH2CH2OR7; NR8R9; N(OCH3)CH3 or C1-C4 alkylthio; R6 is alkyl C1-C6; R7 is alkyl C1-C2; R8 and. R9 are independently H or alkyl C1-C4 or R8 and R9 may be taken together to be (CH2)4, (CE2)5 or O(CE2CH2-)2; R10 and C11 are independently C1-Cs alkyl or C3-C4 alkenyl or R10 and R11 can be taken together to be (CE2)4, (CE2)5 or O(CH2CJ2)2; R12 is C1-C12 alkyl; CH2CE2OCH3; CH2CH2OCH2CH3; CH2CH2CH2OCH3; CH2A or CH-A; CH3 R13 is C1-C3 alkyl; X is H, CH3, CH3O, Cl or OCH2CH3; Y is CH2 or 0; A is CO2H, C02B, phenyl, CN, C2-C4 alkenyl, C2-C4 alkynyl, phenyl substituted with one or two methyl groups or with one or two chlorines; B is C1-C4 alkyl; m is 0, 1 or 2; n is 1 or 2; W is oxygen or sulfur; provided that i) when R1 is EMI5.1 then R2 is COR5, SO2NR10R11 or SO2N(CH3)(OCH3); and R4 is other than H; and ii) when R1 is EMI5.2 then X = CH3 or OCH3; and their agricultural suitable salts. Preferred in order of increasing preference for reasons of biological activity or ease of synthesis or both are the following groups of compounds: (1) Compounds of Formula : wherein N is oxygen; (2) Compounds of Preferred (b) wherein EMI6.1 (3) Compounds of Preferred (2) wherein EMI6.2 (4) Compounds of Preferred (3) where X is H, CH3 or OCH3; (5) Compounds of Preferred (4) wherein is NO2, COR5, SO2NR10R11, SO2R10 or SO2N(OCE3) (CE3); (6) Compounds of Preferred (5) wherein R3 is H, and (7) Compounds of Preferred (6) wherein R2 is NQ2; COR5 where R5 is C1-C3 alkoxy or allyloxy; SO2N(CH3)2; SO2N(CH2CH3)2 or SO2N(OCH3)(CH3). Specifically preferred for their outstanding herbicidal activity or highly favorable cost or both are: N-E(67-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl]-2-nitrobenzenesulfonamide; 2-{[(6, 7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester; N-[(6,7-Dihydro-4-methoxy-SH-cyclopentapyrimidin-2-yl) aminocarbonyl]-2-nitrobenzenesulfonamide; 2-Chloro-N-[(5,6-dihydro-4-methylfuro[2,3-dApyrimidin- 2-yl)aminocarbonyl]benzenesulfonamide; 2-{[(6r7-Dihydro-4-methyl-5E-cyclopentapyrimidin 2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, ethyl ester; 2-{[(5,6-Dihydro-4-methylfuro[2,3-dZpyrimidin-2-yl)- aminocarbonyl] aminosulfonyl )benzoic acid, ethyl ester; and 2-{[(5,6-Dihydro-4-methylfuro[2,3-dApyrimidin-2-yl)- aminocarbonyl]aminosulfonyl}benzoic acid, cyclohexyl ester; N-[(5, 6-Dihydro-4-methylfuro[2, 3-d]pyrimidin-2-yl) aminocarbonyl]-2-nitrobenzenesulfonamide; 2-{[(5,6-Dihydro-4-methylfurof2,3-dApyrimidin-2-yl)- aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester; and N'-[(5,6-Dihydro-4-methylfuro[2,3-dApyrimidin-2-yl)- aminocarbonyl]-N, N-dimethyl-1, 2-benzenedisulfonamide. Synthesis As shown in Equation 1, the compounds of Formula I can be prepared by combining an appropriate 2-aminopyrimidine of Formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula 'TV; R, X, Y and W being as previously defined and q being 1 or 2. Equation 1 EMI7.1 The reaction is best carried out in inert aprotic organic solvents such as methylene chloride, tetra- hydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate to- a stirred suspension of the aminopyrimidine. Since such isocyanates usually are liquids, their addition can be easily controlled. The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as l-chloro- butane or ethyl ether, and filtration. As shown in Equation 2, the compounds of Formula IT can be prepared by reacting an appropriately substituted carbamimidothioic acid salt of Formula V with an alkylating agent of Formula VI: Equation 2 EMI8.1 wherein R, R12, X and Y are as previously defined; - D is -a sulfateorrralogen, such as C1, Br or ; M is an alkali or alkaline earth metal, q is I or 2, and s is an integer corresponding to the valence of D. The reaction is best carried out in inert aprotic organic solvents such as tetrahydrofuran or diethyl ether at temperatures between about 250 and 1000C and at ambient pressure. The mode of addition is not critical; however, it is often convenient to add the alkylating agent in solution to a stirred suspension of said salt. The end product is isolated by evaporation of -the solvent and recrystallization of the residue from a solvent such as acetonitrile or ethanol. The metal salts of Formula V can be prepared by treating the corresponding sulfonylthiourea (Formula VII, Equation 3) with a solution of an alkali metal or alkaline earth metal salt having an anion sufficiently basic to abstract the proton (e.g..hydroxide, alkoxide, carbonate, or hydride). As shown in Equation 3, the sulfonylthiourea VII can be prepared by combining an appropriately substituted sulfonyl isothiocyanate of Formula VIII with an -appropriate 2-aminoheterocycle of Formula III; R, X, Y and g being as previously defined: Equation 3 EMI9.1 The reaction is best carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the isothic- cyanate to a stirred suspension of the aminoheterocycle. Since such isothiocyanates usually are liquids, their addition is more easily controlled. Catalysts, such as 1, 4-diazabicyclo[2.2.2]octane or dibutyltindilaurate, may be used. In some cases, sulfonylthioureas of Formula VII are more conveniently prepared, as shown in Equation 4, by reacting an appropriately substituted sulfonamide of Formula IX with the appropriate 2-isothiocyanatoheterocycle of Formula X; R, X, Y and q being as pre piously defined: Equation 4 EMI10.1 The preparation of 2-isothiocyanatoheterocycles of Formula X is taught in Japanese patent Kokai 51-143686. A process suitable for preparation of the sulfonyl thioureas of Formula V1I an reactants therefor is desc ribed your British Specification No. 1,561,120 to which the reader is referred for further information. The compounds of Formula II may also be prepared as shown in Equation 5. Equation 5 EMI11.1 A compound of Formula XI is reacted with the salt of the heterocyclic -amine at temperatures of 0 to 1000 in a suitable solvent e.g., dimethylformamide, dimethylsulfoxide or an ethereal solvent e.g., tetrahydrofuran; R, R12, X, Y and q are as previously defined. M' is an alkali metal cation, e.g., sodium or potassium. Compounds of Formula XI may be prepared as described in Chem. Ber. 99, 2885 (1966). a. Sulfonyl isocyanate or Isothiocyanate Intermediates The intermediate aryl sulfonyl isocyanate of Formula IV (W=O) can be prepared by reacting corresponding aryl sulfonamides with phosgene in the presence of n-butyl isocyanate at reflux in a solvent such as chlorobenzene, according to the procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241-, Academic Press, New York and London, .Foerst Ed. The intermediate pyridyl sulfonyl isocyanates of Formula IV (W=O) can be prepared by reacting an N-(alkylaminocarbonyl)pyridinesulfonamide with phosgene as described in European Patent Application 79302769.9, to which the reader is referred for further information. The N-(alkylaminocarbonyl)pyridinesulfonamide can be prepared, as described in European Patent Application 79302769.9, by the reaction of a pyridinesulfonamide, an alkyl isocyanate and an anhydrous base in an anhydrous solvent. 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. 60, 2223 (1938). The preparation of pyridylsulfonamide is described in G. Machek, Monatsch 2, 84 (1939) and L. Thunus and C. L. Lapiere, Ann. Farn 33, 663 (1975). Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene in carbon tetrachloride according to the teaching of H. T. Clarke et al., Org. Synth. Coll. Vol 1, 2nd Ed., 1941, p. 85. Other benzenesulfonyl chlorides are best made by diazotization of the appropriate aniline with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of H. L. Yale and F. Sowinski, J. Org. Chem. 25, 1824 (1960). The preparation of pyridyl sulfonyl chlorides is described in Chem. Abs. 88, 190603 m (1978). Sulfonylisothiocyanates of Formula IV (W=S) can be prepared by treatment of sulfonamides with carbon disulfide and potassium hydroxide followed by reaction of the dipotassium salt with phosgene according to the teaching of K. Bartke, Arch. Pharm., 229, 174 (1966). Pyridine sulfonylisothiocvanates canbe prepared according to the procedure taught by K. Dickere and E. Kuhle in U.S Patent 3,346,590. A suitable pyridinesulfonyliminodithiocarbonate is reacted with phosgene in the presence of a solvent such as toluene or xylene. A different method is used for preparing the intermediate sulfonyl isocyanate of Formula IV (W=O) when the intermediate is an o-sulfamoylbenzenesulfonyl isocyanate. This method is illustrated by Equations 2a-e. Equation 2a-d EMI13.1 R31 R10 and R11 are as defined previously. In step (2a), this o-nitrobenzenesulfonyl chlorides in Formula a, which are well-known in the art, are treated with an amine, R10R11NH, in an inert organic solvent such as methylene chloride, ethyl ether, or tetrahydrofuran at 0-50Q. The amine may be taken in excess to act as an acid acceptor; alternatively, a tertiary amine such as triethylamine or pyridine may be used as an acid acceptor. The by-product amine hydrochloride is filtered off or washed out of the solvent with water and the product isolated by evaporation of the solvent. The reduction described in step (2b) is accomplished by treating a solution of the compounds of Formula b in a solvent such as ethanol, ethyl acetate, or DMF, in a pressure vessel with 100-1000 pounds per square inch of hydrogen at 80-150 in the presence of a hydrogenation catalyst such as 5-10% palladium absorbed on carbon When the theoretical amount of hydrogen has been absorbed, the solution is cooled and the catalyst is removed by filtration. The product is then isolated by evaporation of the solvent. The diazotization and coupling with sulfur dioxide, described in step (2c), is accomplished in the following manner A solution of the o-sulfamoyl aniline of Formula c in a mixture of concentrated hydrochloric acid and glacial acetic acid is treated with a solution of sodium nitrite in water at -5 to 00. After stirring for 10-15 minutes at 0 to insure complete diazotization, this solution is added to a mixture of an excess of sulfur dioxide and a catalytic amount of cuprous chloride in glacial acetic acid at 0-5 . The temperature is kept. at 0-5Q for 1/4 to 1 hour and is then raised to 20-250 and hell at that temperature for 2-4 hours. This solution is then poured into a large excess of ice water The sulfonyl chloride products, d, can be isolated by filtration or by extraction into solvent such as ethyl ether or methylene chloride followed by evaporation of the solvent. The amination described in step (2d) is conveniently carried out by treating a solution of the sulfonyl chloride of Formula d with an excess of anhydrous ammonia in a solvent such as ethyl ether or methylene chloride at 0-25 . If the product sulfonamide is insoluble it may be isolated by filtration followed by washing out the salts with water. If the product sulfonamide is soluble in the reaction solution, it may be isolated by filtering off the precipitated ammonium chloride and evaporating the solvent. Sulfonylisocyanates of Formula IV in which R2 is SO2OCE2CCl3, SO2OCH2CF3 or SO2N(CR3)OCH3 can be prepared by a sequence analogous to 'that shown in Equations 2a-e. b. Aminopyrimidine Intermediates The synthesis of heterocyclic amine derivatives such as those depicted by Formula III has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., New York and London. Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series. Preparation of compounds of Formula III varies according to the definition of X, Y and q. Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc. 69, 3072 (1947) describe the preparation of 6,7-dihydro-4-methoxy-5E-cyclopentapyrimidin-)- amine by the following sequence of reactions. EMI16.1 6, 7-dihydro-4-methoxy-5H cyclopentapyrimidin-2-amine. An analogous sequence of reactions can be used to prepare 5, 6, 7, 8-tetrahydro-4-methoxy-2-quinazolinami EMI16.2 5, 6, 7, 8-tetrahydro-4 methoxy-2-quinazolinamine. Mitter and Bhattacharya, Quart. 5. Indian Chem. Soc. 4, 152 1927) describe the preparation ot 5, 6, 7, 8- tetrahydro-4-methyl-2-quinazolinamine as follows: EMI17.1 5, 6, 7, 8-tetrahydro-4 methyl-2-quinazolinamine. Similarly, 6, 7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine can be prepared by the condensation of 2-acetylcyclopentanone with guanidine carbonate, but preferably by heating in dimethylsulfoxide at 135 for several hours. EMI17.2 6,7-dihydro-4-methyl-5H- cyc lopentapyrimidin- 2 amine. Shrage and Hitchings, J. Org. Chem. 16, 1153 (1951) describe the preparation of 5,6-dihydro-4-methylfuro [2, 3-d]pyrimidin-2-amine by the following sequence of reactions EMI18.1 An analogous sequence of reactions- can be used to prepare 6,7-dihydto-4-methyl-5H pyranoC2,3-d]pyrimidin- 2-amine starting with 2-acetyl-8 valerolactone [Korte and Wusten, Tetrahedron 19, 1423 (1963)). EMI18.2 5, 6-Dihydro-4-hydroxyfuro [2, 3-d]pyrimidine-2amine [Svab, Budesinski and Vavrina, Collection Czech. Chem. Commun. 32, 1582 (1967)) can be converted to 2-amino-5-(2-chloroethyl)-4, 6-dichloropyrimidine by heating with phosphorus oxychloride. The product can be subsequently cyclized by treatment with two equivalents of aqueous sodium hydroxide to afford 4-chloro-5,6-dihydrofuro[2,3-dApyrimidin-2-amine, which is then converted to 5,6-dihydro-4-methoxyfuro [2, 3-d]pyrimidin-2-amine by heating with excess sodium methoxide in methanol. EMI19.1 6,7-Dihydro-4 hydroxy-5H-pyranoU2,3-d]pyrimidin- 2-amine can be prepared from diethyl 3^chloropropyl- malonate, guanidine carbonate and sodium ethoxide in ethanol. Treatment of the product with phosphorus oxychloride gives 4-chloro-6,7-dihydro5H-pyrano [2, 3-d]pyrimidin-2-amine and subsequent reaction with sodium methoxide in ref fluxing methanol affords 6,7-dihydro-4-methoxy-5E-pyranoC2,3-dApyrimidin-2-amine. Compounds of Formulas I and II where X is ethoxy can be prepared by a procedure analogous to the methoxy derivatives. EMI20.1 Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc. 63, 2188 (1941), describe the preparation of 6,7dihydro-5H-cyclopentapyrimidin-2-amine by the following sequence of reactions. EMI21.1 Fissekis, Myles and Brown, J. Org. Chem. 29, 267b (1964), describe the preparation of 2-amino-4 hydroxy-5- (2-hydroxyethyl) pyrimidine which can be converted to 5, 6-dihydrofuro [2, 3-d]pyrimidin-2-amine by dehydration. EMI21.2 c. Special Situations When R5 is NR8R9 in Formula I, the compounds of this invention can be prepared by reacting the appropriate compound of Formula XIII with the appropriate alkylaminodialkylaluminum derivative of Formula XIV. This is illustrated in Equation 6, wherein y to 6. Equation 6 EMI22.1 The compounds of Formula XIII are prepared in the manner described above. The intermediate alkylaminodialkylaluminum derivatives of Formula XIV, which are prepared according to A. Basha, M. Lipton and S. Weinreb, Tetrahedron Letters, 4171 (1977), are treated with suspensions of the appropriate esters in toluene or a similar inert solvent, and the mixture is refluxed for one to six hours. The product can be isolated by evaporation of the toluene, adding methy lene chloride, water and hydrochloric acid to decompose the residual reaction mass and extracting the product into methylene chloride. Evaporation of the methylene chloride yields the desired product, sufficiently pure for the purposes of this invention. When R5 is C1-C4 alkylthio, these compounds can be prepared from the esters of this invention wherein R5 is .C1-C4 alkoxy by the reaction of the esters with the appropriate diakylaluminum alky lthiolate according to Equation 7. Equation EMI23.1 The intermediate aluminum thiolates can be prepared according to R. P. Hatch and S. W. Weinreb, Journal of Organic Chemistry, Vol 42, 3960 (1977). The reaction of the thiolate with the ester of this invention is best carried out in a neutral solvent such as toluene or xylene at reflux -for one to three hours. Best results are obtained when the aluminum thiolate compound is present in excess of the stoichiometric amount required. An alternate rcute to prepare compounds where R5 is a secondary alcohol residue involves the reaction of the appropriate dialkylaluminum alcoholate and an ester of this invention wherein R' is a lower primary alkyl group, preferably methyl, according to Equation 8. Equation 8 EMI24.1 The reaction is carried out in a neutral solvent such as toluene with a boiling point sufficiently high to bring about the desired reaction during reflux. The dialkylaluminum alcoholate being present in greater than an equivalent amount to the ester for best yields. After ref fluxing for 1-15 hours, the reaction mixture is decomposed with dilute hydrochloric acid and the product extracted into methylene chloride. Evaporation of the methylene chloride yields the desired compound sufficiently pure for the purposes of this invention. The product can be triturated with a solvent, e.g. chlorobutane to remove impurities. The disclosures of all references cited above are herein incorporated by reference. Agriculturally suitable salts of compounds of Formula I or II are also useful herbicides and can be prepared by a number of ways knows to the art. For example, metal salts can be made by treating compounds of Formula I or II with a solution of alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I or II can also be prepared by exchange of one cation for another Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I or II (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper -salt, and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I or II (e.g., an alkali metal or quaternary amine salt) through a column paced with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is 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, e.g, a potassium, sodium or calcium salt. Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I or II with a suitable acid, e.g., p-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. Example 1 2-Amino-5-(2-chloroethyl)-4, 6-dichloropyrimidine A mixture of 10 g of 6,7-dihydro-4-hydroxyfuro [2, 3-d]pyrimidin-2-amine, 100 ml of phosphorus oxychloride and 6.5 ml N,N-dimethylaniline were heated at 100-1100 for 2 hours. Excess phosphorus oxychloride was removed under reduced pressure and the residue was mixed with 500 g ice then neutralized to pH 7 with ammonium hydroxide solution. The solid product was collected by filtration, rinsed with water and dried to yield 12 g of 2-amino-5-(2-chloroethyl)-4,6-di- chloropyrimidine, m.p. 210-213 . The mass spectrum exhibited a parent ion at m/e 225, 2-27, 229 and showed two triplets at 3.40 and 3.88 ppm by nuclear magnetic resonance spectrum (60 MRz), indicating the title compound. Example 2 4-Chloro-5, 6-dihydrofuro [2, 3-d]pyrimidin-2-amine A suspension of 6.0 g of 2-amino-5-(2-chloro ethyl)-4,6-dichloropyrimidine, 29 ml of 2N aqueous sodium hydroxide solution, 35 mi water and 75 ml of t-butanol was heated to reflux (600) for 24 hours then cooled. The solid was collected by filtration, rinsed with water and dried to yield 2.4 g of 4-chloro-5,6dihydrofuro [2, 3-d]pyrimidin-2-amine, m.p. 258-263 . The product showed characteristic triplet absorption bands at 3.40 and 5.10 ppm in the nuclear magnetic resonance spectrum (60 MHz), indicating the title compound. Example 3 5,6-Dihydro-4-methoxyfuroi2,3-d]pyrimidin-2-amine To a suspension of 27 g of 4-chloro-5,6-dihydro furo[2,3-dlpyrimidin-2-amine in 500 ml of anhydrous methanol was added '22 g of sodium methoxide and the mixture was heated to reflux (660) for 5.5 hours. The solvent was then removed under reduced pressure and the residue triturated with water (500 ml) then filtered and rinsed well with water. The solid was air dried to give 20 g of 5,6-dihydro-4-methoxyfuro [2,3-d]pyrimidin-2-amine, m.p. 172-177 . Two triplet absorptions at 3.42 and 5.02 ppm and a singlet absorption at 4.21 ppm in the nuclear magnetic resonance spectrum (60 MHz), indicated the title compound. Example 4 2-r{6,7-nihydro-4-methyl-5H-cyclopentapyrimidin-2- yl) aminocarbonyl]aminosulfonyl]benzoic acid, cyclo pentyl ester To 20 ml of dry toluene was added 2.4 ml of 2M trimethylaluminum in toluene under a nitrogen atmosphere. Subsequently, 0.82 g cyclopentanol in 1 ml toluene was added via syringe and the mixture stirred at ambient temperature for 15 minutes. After addition of 1.56 g of methyl 2-[[(6,7-dihydro-4-methyl-5H-cyclo pentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate to the mixture, the reaction was heated to 800 for 3.5 hours. The mixture was then cooled in ice while 40 ml of 58 aqueous hydrochloric acid was added. Ethyl acetate was then added and shaking of the two phase mixture resulted in the crystallization of the product which was collected and dried to yield 1.5 g of 2-[[(6,7 dihydro-4-methyl-5H-cyclopentapyrimidin-2-ylXamino- carbonyl) aminosulfonyl) benzoic acid, cyclopentyl ester, m.p. 183-1840, The product showed characteristic absorptions at 3120, 1725, 1720 cm 1 in the infrared spectrum and at 1.7-2.35, 2.50, 2.95, 5.4, 7.6, 8.4, 8.5 and 13.0 ppm in the nuclear magnetic.resonance spectrum (60 MHz), indicating the title compound. Example 5 Nst(6t7-Dihydro-4-methyl-5H-cyclopentapyrimidin 2-yl)- aminocarbonyl]-2-nitrobenzenesulfonamide To a dry, stirred solution of 10 g of 6,7-dihydro 4-methyl-5E-cyclopentapyrimidin-2-amine in 800 ml of methylene chloride at ambient temperature and pressure was added 14.9 g of 2-nitrobenzenesulfonylisocyanate. The resulting mixture was stirred at reflux temperature (420) for 2 hours after which the methylene chloride was removed under reduced pressure. The resulting solid was triturated with methanol or l-chlorobutane and filtered to yield 15 g of N-E(6,7-dihydro-4-methyl- 5H-cyclopentapyrimidin-2-yl)aminocarbonylJ-2-nitrobenzene- sulfonamide, m.p. 202-2050. The product showed charac teristic absorption bands in the infrared spectrum at 1675 cm 1 and at 1.7, 3.2 and 7.7 to 8.5 ppms by nuclear magnetic resonance spectrum (60 MHz),indicating the title compound. Example 6 20chloro-N[(5f6-dihydro-4-methylfurot2t3-d3pyrimidin- 2-yl)aminothioxomethyl]benzenesulfonamide To a dry stirred mixture of 4.9 g of 5,6-dihydro 4-methylfuro[2,3-d]pyrimidin-2-amine in 125 ml of acetonitrile at ambient temperature was added 7.6 g of 2-chlorophenyl sulfonylisothiocyanate The resulting mixture was- stirred at reflux temperature (840) for 24 hours. After cooling the reaction mixture, a white solid was filtered and washed with acetonitrile to yield 10.8 g of product, m.p. 190-191 dec. Elemental analyses, infrared spectrum and nuclear magnetic resonance spectrum indicated the title compound. Example 7 Methyl 2-[[(6, 7-dihydro-4-methoxy-5H-cyclopentapyrimidin 2-yl)aminothioxomethylZaminosulfor.ylAbenzoate A mixture of 4.3 g of methyl 2-(aminosulfonyl)benzoate, 4.2 g of 6,7-dihydro-2-isothiocyanato-4- methoxy-5H-cyclopentapyrimidine and 2.2 g of anhydrous potassium carbonate in 70 ml of acetone was warmed to 400 with stirring. After 2 hours, a thick precipitate formed and stirring was continued for three more hours at ambient temperature. The precipitate was filtered, suspended in 150 ml of water, stirred and the pH adjusted to 2 by the addition of hydrochloric acid. The white solid was filtered, washed with cold water and dried to yield 4.2 g of product. By application of one or more of -the procedures of Examples 1 to 7 and/or the methods described above, and using the appropriate reactants, the compounds of Table I can be prepared. Table I-A EMI30.1 R2 R3 W Y m.p. -H H O CE2 -C1 H O CH2 190-192 -F H O CE2 -Br H O CE2 -SCH3 H O CH2 -SO2CH3 H O CH2 -CF3 H O CH2 -NO2 H O CH2 202-205 -CO2CH3 H O CH2 193-194 -CO2CH2CH3 H O CH2 153-154 -CO2CH2CH2Cl H O CE2 -CO2CH2CH2CH3 H o CE2 -CO2CH2CH2OCH3 H O CH2 -CO2CH2CH2Br H O CH2 CO2CH(CH3)2 H O CH2 207-210 CO2CH2CH=CH2 H O CH2 167-172 CO2CH2CF3 H O CH2 CO2(CH2)3CH3 H O CH2 160-161 CO2CH(CH3)CH2CH3 H O CH2 CO2CH(CH2CH3)2 H O CH2 CO2CH2C(CH3)3 H O CH2 CO2CH2CH=CH-CH3 H O CH2 CO2CH(CH3)CH=CH2 H O CH2 190-191 Table I-A (continued) EMI31.1 <tb> <SEP> Ro <SEP> R3 <SEP> W <SEP> Y <SEP> m-p <tb> <SEP> 3 <SEP> w <SEP> y <SEP> m.. <tb> CO2CH2CH=CE(CH2)2CH3 <SEP> H <SEP> 0 <SEP> CH2 <tb> CO2(CX2)4C1 <SEP> E <SEP> O <SEP> CH2 <tb> CO2(CH2)6C1 <SEP> H <SEP> o <SEP> CH2 <tb> C02'1 <SEP> < <SEP> H <SEP> O <SEP> CH2 <SEP> 183* <SEP> <tb> CO2 <SEP> H <SEP> 0 <SEP> CE2 <SEP> l93l95o <tb> CO2(CE2CH2O)2CE3 <SEP> H <SEP> 0 <SEP> CE2 <tb> CO2(CH2CH2O)2C2H5 <SEP> H <SEP> o <SEP> CH2 <tb> C 2CE2CH2CH2 CH3 <SEP> a- <SEP> O <SEP> CH2 <tb> CO2CH2CH2CH2OC2H5 <SEP> H <SEP> o <SEP> CH2 <tb> CON(CH3) <SEP> 2 <SEP> H <SEP> o <SEP> CH2 <tb> CON(C2H5)2 <SEP> H <SEP> 0 <SEP> CH2 <tb> CON-CH3 <SEP> H <SEP> o <SEP> CH2 <tb> <SEP> CH(CH3)2 <tb> CONH2 <SEP> H <SEP> <SEP> CH2 <tb> CONCH3 <SEP> H <SEP> o <SEP> CH2 <tb> co2CE2CH2oC2R5 <SEP> H <SEP> O <SEP> CH2 <tb> CON(CH <SEP> (CH3)2) <SEP> 2 <SEP> H <SEP> O <SEP> 2 <tb> CONCE2CH(CH3)2 <SEP> H <SEP> o <SEP> CE2 <tb> <SEP> CH3 <tb> CoN(CH2CH2CH2CH3)2 <SEP> H <tb> <SEP> OCH3 <tb> CON <tb> <SEP> CE3 <SEP> -' <tb> <SEP> M <SEP> CE2CE2 <SEP> <tb> <SEP> CON <SEP> a <SEP> H <SEP> CE2 <tb> <SEP> CH2CH2 <tb> Table I-A (continued) R2 R3 W Y m.p. Cl 5-Cl O CH2 Cl 6-Cl O CH2 Cl 4-Cl O CH2 Cl 3-Cl O CH2 F 5-Cl O CH2 F 3-Cl O CH2 F 4-Cl O CH2 F 5-F O CH2 Cl 5-OCH3 O CH2 Cl 5-CH(CH3)2 O CH2 Cl 4-CH3 O CH2 Cl 4-F O CH2 Cl 5-Br O CH2 Cl 6-CH3 O CH2 NO2 5-Cl O CH2 NO2 6-Cl O CH2 NO2 5-F O CH2 Cl 5-CH(CH3)C2H5 O CH2 Br 5-F O CH2 SCH3 5-Cl O CH2 Cl 5-C2H5 O CH2 Table I-A (continued) EMI33.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> SCH3 <SEP> 4-C1 <SEP> <SEP> CH2 <tb> S 2CH3 <SEP> 5-Cl <SEP> o <SEP> CHz <tb> S 2CH3 <SEP> 6-Cl <SEP> <SEP> CH2 <tb> SCH3 <SEP> 6-C1 <SEP> <SEP> CE2 <tb> 4-OCH3 <SEP> <SEP> CH2 <tb> CF3 <SEP> 5-C1 <SEP> <SEP> CE2 <tb> CF3 <SEP> 5-CH3 <SEP> <SEP> CH2 <tb> CF3 <SEP> 5-F <SEP> <SEP> CH2 <tb> CF3 <SEP> 4-Cl <SEP> 0 <SEP> CH2 <tb> CF3 <SEP> 4-CH3 <SEP> <SEP> CH2 <tb> C 2CH3 <SEP> 5-CH3 <SEP> <SEP> CH2 <tb> C 2CH3 <SEP> 6-CH3 <SEP> <SEP> CH2 <tb> CO2CH3 <SEP> 5-C1 <SEP> <SEP> CH2 <tb> C 2CH3 <SEP> 3-C1 <SEP> <SEP> CH2 <tb> C 2CH3 <SEP> 6-Cl <SEP> <SEP> CH2 <tb> COUCH3 <SEP> 4-CH3 <SEP> O <SEP> CH2 <tb> SO2CH2CH3 <SEP> H <SEP> <SEP> CH2 <tb> S02CH2CH=CHZ <SEP> H <SEP> <SEP> CH2 <tb> SOCH3 <SEP> E <SEP> <SEP> CK2 <tb> SOCH2CH3 <SEP> 5-C1 <SEP> <SEP> CH2 <tb> <SEP> CH3 <tb> S 2N <SEP> \ <SEP> H <SEP> C <SEP> CH2 <tb> <SEP> CH3 <tb> <SEP> CH, <tb> SO2N <SEP> H <SEP> E <SEP> C <SEP> CX2 <tb> <SEP> CH2CH=CH2 <tb> <SEP> /CH2CE3 <tb> <SEP> 6-Cl <SEP> 0 <SEP> CE2 <tb> SO, <SEP> 6-C1 <SEP> O <SEP> C2 <tb> <SEP> CH2CH=CHCH3 <tb> <SEP> CE2-CE2 <tb> S 2N <SEP> I <SEP> | <SEP> 5-F <SEP> <SEP> CH2 <tb> <SEP> CH2-CH2 <tb> Table I-A (continued) EMI34.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> 0 <tb> <SEP> I' <tb> FCSCH3 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> O <SEP> CE3 <tb> -CSCH <SEP> / <SEP> 5-OCH3 <SEP> <SEP> CH2 <tb> <SEP> 3 <tb> <SEP> O <SEP> / <SEP> CH3 <tb> -CSCH <SEP> H <SEP> <SEP> CE2 <SEP> 175-177 <tb> <SEP> N <tb> <SEP> CE2GE3 <tb> eS020CH26F3 <SEP> H <SEP> <SEP> CH2 <tb> -SO2OCH2CCl3 <SEP> H <SEP> O <SEP> C2 <tb> <SEP> SOCH3 <tb> -SO2N <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> 2 <SEP> X <tb> <SEP> CH3 <tb> H <SEP> H <SEP> O <SEP> 0 <tb> <SEP> -Cl <SEP> H <SEP> 0 <SEP> 0 <SEP> 202-2050 <tb> -F <SEP> H- <SEP> O <SEP> 0 <tb> -Br <SEP> H <SEP> O <SEP> O <tb> -SCX3 <SEP> H <SEP> O <SEP> 0 <tb> -S02CH3 <SEP> H <SEP> O <SEP> 0 <tb> 3 <SEP> H <SEP> O <SEP> 0 <tb> -NOz <SEP> H <SEP> O <SEP> 0 <SEP> 180-187 <tb> -C02CH3 <SEP> H <SEP> O <SEP> 0 <SEP> 194.5-197 <tb> -CO2CH2CE3 <SEP> H <SEP> 0 <SEP> 0 <SEP> 187-1880 <tb> -C02CH2CH2C1 <SEP> H <SEP> 0 <SEP> O <tb> -CO2CE2CH2CE3 <SEP> H <SEP> O <SEP> 0 <tb> -CO2CE2CE2OCH3 <SEP> H <SEP> Q <SEP> 0 <tb> -CO2CE2CH2Br <SEP> H <SEP> 0 <SEP> 0 <tb> -S02OCE2CF3 <SEP> H <SEP> O <SEP> 0 <tb> -SO2OCE2CCl3 <SEP> H <SEP> O <SEP> 0 <tb> <SEP> 6CH3 <tb> -SO,N <SEP> H <SEP> O <SEP> 0 <tb> <SEP> CH3 <tb> Table I-A (continued) EMI35.1 <tb> <SEP> R2 <SEP> R3 <SEP> Y <SEP> .p. <tb> CO2CH <SEP> (CE3) <SEP> 2 <SEP> H <SEP> O <SEP> 0 <SEP> 196-1990 <tb> CO2CH2CH=CH2 <SEP> H <SEP> O <SEP> 0 <SEP> 205-206 <tb> C02CH2Cr3 <SEP> BOO <tb> C 2(CE2)3CH3 <SEP> H <SEP> O <SEP> 0 <SEP> 163-1650 <tb> CO2CH <SEP> (CE3) <SEP> CH2CH3 <SEP> H <SEP> CO <tb> CO2CH(CH2CH3)2 <SEP> HOO <tb> CO2CH2C(CH3)3 <SEP> BOO <tb> CO2CH2CH=CH-CH3 <SEP> H <SEP> 0 <SEP> O <tb> CC2CH(CE3)CH=CH2 <SEP> H <SEP> O <SEP> 0 <SEP> 192-194 <tb> <SEP> 2 <SEP> 3 <SEP> 2 <tb> C02CH2CH=CB(CH2)2CH3 <SEP> H <SEP> CO <tb> CO2 <SEP> (CE2) <SEP> 4C1 <SEP> H <SEP> CO <tb> C 2 <SEP> (CH2) <SEP> 6C1 <SEP> H <SEP> CO <tb> C 2 <SEP> < <SEP> H <SEP> O <SEP> 0 <SEP> 169-171 <tb> CO2 <SEP> < <SEP> K <SEP> o <SEP> 0 <SEP> 178-179 <tb> C02(CH2CE2O)2CH3 <SEP> H <SEP> 0 <SEP> 0 <tb> C02(CH2CE2O)2C2H5 <SEP> H <SEP> o <SEP> O <tb> Co2CH2CH2CH2OCX3 <SEP> H <SEP> O <SEP> <tb> C02CH2CX2CH20C2HS <tb> CON <SEP> (CE3)2 <SEP> H <SEP> CO <tb> CCN(C2H5) <SEP> 2 <SEP> H <SEP> CO <tb> CON-CH3 <SEP> R <SEP> O <SEP> O <tb> <SEP> CE(CE3)2 <tb> CONH2 <SEP> HOO <tb> CONECE3 <SEP> H <SEP> CO <tb> Table I-A (continued) EMI36.1 <tb> <SEP> R <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> CO2CE2CH2OC2H5 <SEP> E <SEP> 0 <SEP> 0 <tb> CON(CE(CE3)2)2 <SEP> E <SEP> 0 <SEP> 0 <tb> CON,CE2CE(CH3)2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> CE3 <tb> CON(CH2CE2CE2CH3)2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> OCH <tb> CON <SEP> E <SEP> O <SEP> O <tb> <SEP> CH3 <tb> Cl <SEP> 5-Cl <SEP> 0 <tb> Cl <SEP> 6-Cl <SEP> 0 <tb> CL <SEP> 4-Cl <SEP> 0 <tb> Cl <SEP> 3-Cl <SEP> 0 <tb> F <SEP> 5-Cl <SEP> o <tb> F <SEP> 3-Cl <SEP> 0 <tb> F <SEP> 4-el <SEP> 0 <tb> F <SEP> 5-F <SEP> O <SEP> O0 <tb> Cl <SEP> 5-OCE3 <SEP> 0 <tb> Cl <SEP> 5-CE(CE3)2 <SEP> 0 <tb> Cl <SEP> 4-CE3 <SEP> 0 <tb> Cl <SEP> 4-F <SEP> .0 <tb> Cl <SEP> 5-Br <SEP> 0 <SEP> 0 <tb> C1 <SEP> 6-CE3 <SEP> O <SEP> 0 <tb> NO2 <SEP> 5-Cl <SEP> 0 <tb> NO2 <SEP> 6-C1 <SEP> 0 <SEP> 0 <tb> N02 <SEP> 5-F <SEP> o <tb> Cl <SEP> 5-CX(CE3)C2Xs <SEP> <SEP> O0 <tb> Br <SEP> O <SEP> 0 <tb> SCE3 <SEP> 5-Cl <SEP> 0 <SEP> 0 <tb> C1 <SEP> 5-C <SEP> 2R5 <SEP> 0 <SEP> 0 <tb> SCE3 <SEP> 4-C1 <SEP> 0 <SEP> 0 <tb> S 2CE3 <SEP> 5-C1 <SEP> 0 <SEP> 0 <tb> S 2CH3 <SEP> 6-Cl <SEP> 0 <SEP> 0 <tb> Table I-A (continued) EMI37.1 <tb> <SEP> R2 <SEP> R3 <SEP> y <SEP> m.p. <tb> SCH3 <SEP> 6-Cl <SEP> 0 <SEP> 0 <tb> SCH3 <SEP> 4-OCH3 <SEP> 0 <SEP> 0 <tb> CF3 <SEP> 5-Cl <SEP> 0 <SEP> 0 <tb> Cr3 <SEP> 5-CH3 <SEP> 0 <SEP> 0 <tb> Cr3 <SEP> 5-F <SEP> 0 <SEP> 0 <tb> CF3 <SEP> 4-C1 <SEP> 0 <SEP> 0 <tb> CF3 <SEP> 4-CH3 <SEP> 0 <SEP> 0 <tb> CO2CH3 <SEP> 5-CH3 <SEP> 0 <SEP> 0 <tb> COUCH3 <SEP> 6-CH3 <SEP> 0 <SEP> 0 <tb> C 2CH3 <SEP> 5-Cl <SEP> 0 <SEP> O <tb> COUCH3 <SEP> 3-Cl <SEP> -O <SEP> 0 <tb> CO2CE3 <SEP> 6-Cl <SEP> 0 <SEP> 0 <tb> C 2CX3 <SEP> 4-CE3 <SEP> 0 <SEP> 0 <tb> <SEP> SOCH3 <SEP> H <SEP> O <SEP> 0 <tb> <SEP> SOCH2C=CH2 <SEP> 5-C1 <SEP> 0 <SEP> 0 <tb> <SEP> /JCH3 <tb> SO2NCE3 <tb> <SEP> CH3 <tb> <SEP> CH2CE <tb> SO <SEP> N <SEP> 5-F <SEP> 0 <SEP> 0 <tb> <SEP> CH2CH=CH2 <tb> <SEP> CH2CE2CX2CH3 <tb> S 2N <SEP> \ <SEP> 6-CH3 <SEP> O <SEP> 0 <tb> <SEP> CH2CE2CH2CF.3 <tb> <SEP> LLL <tb> 502N <SEP> &num; ;CH2CE2\0 <SEP> \ <SEP> O <SEP> 4-OCH3 <SEP> 0 <SEP> 0 <tb> <SEP> CH2CH2 <SEP> / <tb> O <SEP> CH3 <SEP> E <SEP> 0 <SEP> 0 <tb> <SEP> (1 <SEP> H <SEP> O <SEP> 0 <tb> <SEP> CE3 <tb> <SEP> Q <tb> -CS-CE2 <SEP> CE3 <SEP> 5-Cl <SEP> <SEP> O <tb> <SEP> S02N(C2Hg) <SEP> H <SEP> O <SEP> 0 <tb> Table I-A (continued) EMI38.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> O <SEP> / <SEP> CH3 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> -S-6H <SEP> H <SEP> O <SEP> 0 <tb> <SEP> N <SEP> CH2CE3 <tb> H <SEP> H <SEP> S <SEP> CH2 <tb> Cl <SEP> H <SEP> S <SEP> CH2 <tb> SCE3 <SEP> H <SEP> S <SEP> CE2 <tb> S 2CH3 <SEP> H <SEP> S <SEP> CE2 <tb> NO2 <SEP> E <SEP> S <SEP> CE2 <tb> CO <SEP> CE <SEP> H <SEP> S <SEP> CE2 <tb> CO2CE <SEP> 2CE-2C1 <SEP> E <SEP> S <SEP> CE2 <tb> CO2CE <SEP> 2CH <SEP> 20CE3 <SEP> E <SEP> S <SEP> CH2 <tb> CO2CE2CH=CE3 <SEP> H <SEP> S <SEP> CE2 <tb> COzCH2CF3 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CE(CE3)2 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CE2CE=CH2(CE2)2CE3 <SEP> H <SEP> S <SEP> CH2 <tb> CO <SEP> 2 <SEP> H <SEP> S <SEP> CE2 <tb> CO2CE2CE <SEP> 2CH2OCE3 <SEP> H <SEP> S <SEP> CE2 <tb> CONH2 <SEP> H <SEP> S <SEP> CE2 <tb> CON(CEa) <SEP> 2 <SEP> H. <SEP> S <SEP> CE2 <tb> CON[CE(CE3)2]2 <SEP> H <SEP> S <SEP> CH2 <tb> CON(OCE3)CH3 <SEP> H <SEP> S <SEP> CH2 <tb> CE3 <SEP> H <SEP> S <SEP> CH2 <tb> SO2N(CE3)2 <SEP> H <SEP> S <SEP> CE2 <tb> SO2N(OCE3)CH3 <SEP> H <SEP> S <SEP> CE2 <tb> SOCH3 <SEP> H <SEP> S <SEP> CH2 <tb> 0 <tb> CSCE3 <SEP> H <SEP> S <SEP> CH2 <tb> SO2OCH2CF3 <SEP> H <SEP> S <SEP> CH2 <tb> Cl <SEP> 5-C1. <SEP> S <SEP> CH2 <tb> F <SEP> 4-C1 <SEP> S <SEP> CH2 <tb> Table I-A (continued) EMI39.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> NO2 <SEP> 5-CH3 <SEP> S <SEP> CH2 <tb> CF3 <SEP> 5-F <SEP> S <SEP> CH2 <tb> OCH3 <SEP> 5-OCH3 <SEP> S <SEP> CH2 <tb> S02CH3 <SEP> 6-Br <SEP> S <SEP> CH2 <tb> CO2Cl3 <SEP> 5-C1 <SEP> S <SEP> CII2 <tb> CO2CH2CH3 <SEP> 4-CH(CH3)2 <SEP> S <SEP> CH2 <tb> <SEP> CP <tb> 6-Cl <SEP> / <SEP> 6-C1 <SEP> S <SEP> CH2 <tb> CH <SEP> CH: :CIi, <tb> 0 <tb> CSCH(CH3)2 <SEP> 5-OCH3 <SEP> S <SEP> CE2 <tb> H <SEP> H <SEP> S <SEP> 'O <tb> CH3 <SEP> H <SEP> S <SEP> O <tb> OCH3 <SEP> H <SEP> S <SEP> O <tb> C1 <SEP> H <SEP> S <SEP> 0 <tb> F <SEP> H <SEP> S <SEP> O <tb> 3 <SEP> H <SEP> S <SEP> o <tb> NO2 <SEP> n" <SEP> S <SEP> O <tb> Cm <SEP> cm <SEP> S <SEP> S <tb> CO2 <SEP> (CE2) <SEP> 3CH3 <SEP> H <SEP> S <SEP> O <tb> CO2 <SEP> (CE2) <SEP> 2C1 <SEP> H <SEP> S <SEP> 0 <tb> CO2CE2CE2OCE3 <SEP> H <SEP> -S <SEP> O <tb> 0 <tb> CSCE2CE3 <SEP> H <SEP> S <SEP> O <tb> CON(C2H5)2 <SEP> H <SEP> S <SEP> O <tb> COSHCE3 <SEP> H <SEP> S <SEP> O <tb> COM(OCH3)CH3 <SEP> H <SEP> S <SEP> O <tb> 502N(C2H)2 <SEP> H <SEP> S <SEP> O <tb> SO2OCH2C13 <SEP> H <SEP> S <SEP> O <tb> C1 <SEP> 5-Cl <SEP> S <SEP> O <tb> OCE3 <SEP> 5-OCH3 <SEP> S <SEP> O <tb> CO2CE3 <SEP> 4-CH3 <SEP> S <SEP> 0 <tb> F <SEP> 5-F <SEP> S <SEP> O <tb> Cl <SEP> 6-CH3 <SEP> S <SEP> O <tb> Table I-B EMI40.1 R2 R3 W Y m.p. Cl H O CH2 224 Cl 5-Cl O CH2 231.5-232 NO2 H O CH2 211-212 CO2CH3 H O CH2 169-184 CO2CH(CH3)2 H O CH2 207-209 -F H O CH2 -Br H O CH2 -SCH3 H O CH2 -SO2CH3 H O CH2 -CF3 H O CH2 -CO2CH2CH3 H O CH2 170-179 -CO2CH2CH2Cl H O CH2 -CO2CH2CH2CH3 H O CH2 -CO2CH2CH2OCH3 H O CH2 CO2CH2CH=CH2 H O CH2 137-140 CO2CH2CF3 H O CH2 CO2(CH2)3CH3 H O CH2 149-151 CO2(CH2)5CH3 H O CH2 CO2CH(CH3)CH2CH3 H O CH2 CO2CH(CH2CH3)2 H O CH2 CO2CH2C(CH3)3 H O CH2 CO2CH2CH=CH-CH3 H O CH2 H H O CH2 Table I-B (continued) EMI41.1 <tb> <SEP> g <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> R3 <SEP> ¯ <SEP> Y <SEP> m.p. <tb> <SEP> CO2CH(CH3)CH=CH2 <SEP> H <SEP> O <SEP> CH2 <SEP> 176-1770 <tb> <SEP> CO2CE2CE=CE(CH2)2CE3 <SEP> H <SEP> 0 <SEP> CE2 <tb> <SEP> CO2(CH2)4C1 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> CO2(CH2)6C1 <SEP> H <SEP> O <SEP> CH2 <tb> CO2 <SEP> < <SEP> H <SEP> O <SEP> CH2 <SEP> 174-175 <tb> CO2 <SEP> < <SEP> H <SEP> O <SEP> CH2 <SEP> 171-172 <tb> C 2 <SEP> (cH2CH2 <SEP> ) <SEP> 2CE3 <SEP> H <SEP> 0 <SEP> CE2 <tb> CO2(CH2CH2O)2C2E5 <SEP> H <SEP> O <SEP> CE2 <tb> CO2CH2CH2CE2OCE3 <SEP> H <SEP> O <SEP> CE2 <tb> CO2CH2CH2CH2OC2E5 <SEP> H <SEP> O <SEP> CH2 <tb> CON(CH3)2 <SEP> H <SEP> O <SEP> CE2 <tb> CON <SEP> (C2R5)2 <SEP> CE2 <tb> CON-CH3 <SEP> H <SEP> Q <SEP> CE2 <tb> <SEP> CE(CE3)2 <tb> CON(CH(CH3)2)2 <SEP> H <SEP> O <SEP> CE2 <tb> CONCE2CX(CH3)2 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> CH3 <tb> CON(CH2CE2CE2CE3)2 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> ocE3 <tb> <SEP> CON <SEP> H <SEP> O <SEP> <SEP> CE2 <tb> <SEP> CE3 <tb> Table I-B (continued R2 R3 W Y m.p. Cl 6-Cl O CH2 Cl 4-Cl O CH2 Cl 3-Cl O CH2 F 5-Cl O CH2 F 3-Cl O CH2 F 4-Cl O CH2 F 5-F O CH2 Cl 5-OCH3 O CH2 Cl 5-CH(CH3)2 O CH2 Cl 4-CH3 O CH2 Cl 4-F O CH2 Cl 5-Br O CH2 Cl 6-CH3 O CH2 NO2 5-Cl O CH2 NO2 6-Cl O CH2 NO2 5-F O CH2 Cl 5-CH(CH3)C2H5 O CH2 Br 5-F O CH2 SCH3 5-Cl O CH2 SCH3 4-Cl O CH2 SO2CH3 5-Cl O CH2 SO2CH3 6-Cl O CH2 SCH3 6-Cl O CH2 SCH3 4-OCH3 O CH2 CF3 5-Cl O CH2 CF3 5-CH3 O CH2 CF3 5-F O CH2 CF3 4-Cl O CH2 CF3 4-CH3 O CH2 CO2CH3 5-CH3 O CH2 Table I-B (continued) EMI43.1 <tb> <SEP> Y <SEP> R, <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> R3 <tb> C 2CH3 <SEP> 6-CH3 <SEP> O <SEP> CH2 <tb> C 2CH3 <SEP> 5-C1 <SEP> O <SEP> CE2 <tb> C 2CH3 <SEP> 3-C1 <SEP> <SEP> CH2 <tb> C02CK3 <SEP> 6-Cl <SEP> 0 <SEP> CH2 <tb> C 2CH3 <SEP> 4-CH3 <SEP> o <SEP> CE2 <tb> SOCH3 <SEP> H <SEP> <SEP> CH2 <tb> SOCH3 <SEP> 5-Br <SEP> <SEP> CH2 <tb> <SEP> CH <tb> SOCH <SEP> 6-CH3 <SEP> 3 <tb> <SEP> CH3 <tb> <SEP> CE <tb> SO <SEP> 2N <SEP> \ <tb> <SEP> CH3 <tb> <SEP> CE <tb> <SEP> /3 <tb> 502N <SEP> \ <SEP> H <SEP> <SEP> CH2 <tb> <SEP> CH2CH2CH=CH2 <tb> <SEP> CHZCH3 <tb> S02N <SEP> \ <SEP> 5-C1 <SEP> <SEP> CE2 <tb> <SEP> CB <SEP> CH3 <tb> <SEP> CE <SEP> CE <tb> 502N <SEP> 2 <SEP> 2\ <tb> S 2N <SEP> / <SEP> 2 <SEP> 4-OCH3 <SEP> <SEP> CH2 <tb> <SEP> CH2CE2 <tb> <SEP> 0 <tb> -C-SCE3 <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> O <SEP> CH3 <tb> -C-SCE2CE <SEP> / <SEP> 3-F <SEP> <SEP> CH2 <tb> <SEP> CE3 <tb> <SEP> 0 <tb> -C-S-CH2CH2CH3 <SEP> 5 <SEP> CH2CH3 <SEP> G <SEP> CH2 <tb> <SEP> /?CE3 <tb> -C-SCH <SEP> \ <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> CH2CH3 <tb> Table I-B (continued) EMI44.1 <tb> <SEP> R2 <SEP> R3 <SEP> N <SEP> Y <SEP> m.p. <tb> <SEP> / <SEP> OCE3 <tb> H <SEP> B <SEP> O <SEP> CE2 <tb> <SEP> 3 <tb> -S020CH2CE3 <SEP> 5-Cl <SEP> 0 <SEP> CX2 <tb> -SO2OCH2CCl3 <SEP> 3-F <SEP> <SEP> CE2 <tb> Cl <SEP> E <SEP> 0 <SEP> 0 <tb> Cl <SEP> S-Cl <SEP> 0 <SEP> 0 <tb> NO2 <SEP> H <SEP> O <SEP> 0 <tb> CO2CH3 <SEP> H <SEP> Q <SEP> o <SEP> 203-206 <tb> CO2CE(CE3)2 <SEP> H <SEP> 0 <SEP> 0 <SEP> 222-224 <tb> -F <SEP> H <SEP> o <SEP> 0 <SEP> 0 <tb> -Sr <SEP> H <SEP> O <SEP> 0 <tb> -SCE3 <SEP> H <SEP> o <SEP> o <tb> 502cm3 <SEP> H <SEP> o <SEP> 0 <tb> <SEP> Cr3 <SEP> H <SEP> O <SEP> o <tb> -C02CH2CE3 <SEP> H' <SEP> E <SEP> O <SEP> 0 <SEP> 211-214 <tb> -CO2CE2CH2Cl <SEP> H <SEP> O <SEP> 0 <tb> -CO2CE2CH2 <SEP> CE <SEP> H <SEP> O <SEP> 0 <tb> -CO2CH2CH2OCE3 <SEP> H <SEP> O <SEP> 0 <tb> CO2CH2CH=CH <SEP> H <SEP> O <SEP> 0 <SEP> 193-1950 <tb> C02CH2CF3 <SEP> H <SEP> O <SEP> 0 <tb> C02(CE2)3CH3 <SEP> H <SEP> O <SEP> 0 <SEP> 168-1714 <tb> CO2 <SEP> (CE2)5CE3 <SEP> H <SEP> O <SEP> O <tb> CO2CE(CH3)CE2CE3 <SEP> H <SEP> O <SEP> 0 <tb> CO2CH(CH2CH3)2 <SEP> H <SEP> 0 <SEP> 0 <tb> C02CE2(CE3)3 <SEP> H <SEP> O <SEP> 0 <tb> CO2CE2CE--CH-CH3 <SEP> H <SEP> 0 <SEP> 0 <tb> H <SEP> a <SEP> O <SEP> 0 <tb> Table I-B (continued) EMI45.1 <tb> <SEP> R2 <SEP> 3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> CO2CHtCH3)CH=CE2 <SEP> H <SEP> o <SEP> 0 <tb> <SEP> CO2CH2CH=CE <SEP> (CE2) <SEP> 2CE3 <SEP> H <SEP> OC <tb> <SEP> CO2 <SEP> (CE2') <SEP> 4C1 <SEP> H <SEP> OO <tb> <SEP> CO2 <SEP> (CE2) <SEP> 6C1 <SEP> H <SEP> OO <tb> CO2 <SEP> &num;j <SEP> E <SEP> O <SEP> 0 <SEP> 195-197 <tb> CO2 <SEP> < <SEP> H <SEP> 0 <SEP> 0 <SEP> 171-173 <tb> C02(CH2CE2O)2CH3 <SEP> H <SEP> 0 <SEP> 0 <tb> C02(CE2CE2O)2C2E5 <SEP> H <SEP> O <SEP> 0 <tb> CO2CH2CE2CE2OCE3 <SEP> H <SEP> o <SEP> 0 <tb> CO2CE2CH2CE2OC2E5 <SEP> H <SEP> 0 <SEP> 0 <tb> CON(CE3) <SEP> 2 <SEP> H <SEP> OO <tb> CON <SEP> (C2H5)2 <SEP> H <SEP> OO <tb> CON-CE <SEP> E <SEP> o <SEP> <tb> <SEP> 1 <SEP> 3 <tb> <SEP> CE(CE3)2 <tb> CON(CE(CE3)2)2 <SEP> H <SEP> 0 <SEP> 0 <tb> CONCII2Ch'(CH3a <SEP> o <SEP> o <tb> <SEP> CE3 <tb> CON <SEP> (CE2CE2CE2CE3) <SEP> 2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> yOCE3 <SEP> H <SEP> OO <tb> <SEP> H <SEP> O <SEP> 0 <tb> <SEP> CON <tb> <SEP> CH3 <tb> Table I-B (continued) R2 R3 W Y m.p. Cl 6-Cl O O Cl 4-Cl O O Cl 3-Cl O O F 5-Cl 0 F 3-Cl O O F 4-Cl O O F 5-F 0 0 Cl 5-OCH3 O O Cl 5-CH(CH3)2 O O Cl 4-CH3 O O Cl 4-F O O Cl 5-Br O O Cl 6-CH3 O O NO2 5-Cl O O NO2 6-Cl O O NO2 5-F O 0 Cl 5-CH(CH3)C2H5 O Br 5-F O 0 SCH3 5-Cl O O SCH3 4-Cl O O SO2CH3 5-Cl O O SO2CH3 6-Cl O O SCH3 6-Cl 0 0 SCE3 4-OCE3 0 0 CF3 5-C1 O 0 CF3 5-CE3 0 0 CF3 5-F O O CF3 4-Cl O O CF3 4-CH3 0 0 CO2CH3 5-CH3 O O Table I-B (continued) EMI47.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> c <tb> C 2CH3 <SEP> 6-CH3 <SEP> O <SEP> 0 <tb> C 2CH3 <SEP> 5-Cl <SEP> 0 <SEP> 0 <tb> C 2CH3 <SEP> 3-C1 <SEP> 0 <SEP> O <tb> C 2CH3 <SEP> 6-Cl <SEP> 0 <SEP> 0 <tb> C 2CH3 <SEP> 4-CE3 <SEP> 0 <SEP> 0 <tb> SOCH3 <SEP> H <SEP> O <SEP> 0 <tb> SOCH3 <SEP> 5-C1 <SEP> 0 <SEP> 0 <tb> SOCH2CH=CH3 <SEP> 6-F <SEP> 0 <SEP> 0 <tb> <SEP> ,'CE3 <tb> SO <SEP> 2N <SEP> E <SEP> 0 <SEP> 0 <tb> <SEP> CH3 <tb> <SEP> CE3 <tb> SO2N <SEP> \ <SEP> E <SEP> o <SEP> 0 <tb> <SEP> CH2CH3 <tb> <SEP> / <SEP> CH2CH=CH2 <tb> SO2N <SEP> \ <SEP> -OCH3 <SEP> O <SEP> 0 <tb> <SEP> CH2CH=CH2 <tb> <SEP> ,CH2 <SEP> CH2 <tb> 502N\ <SEP> I <tb> <SEP> CM <SEP> 'CHO <tb> <SEP> 0 <tb> -C-SCE3 <SEP> H <SEP> o <SEP> 0, <tb> <SEP> /-CE3 <tb> -C-SCH <SEP> / <SEP> 3 <SEP> 5 <SEP> 0 <tb> <SEP> CH3 <tb> 0 <tb> CS-CHCH2CH3 <SEP> H <SEP> o <SEP> 0 <tb> <SEP> CH3 <tb> <SEP> O <SEP> CH3 <tb> -C-S-CCE3 <SEP> 6-CE3 <SEP> 0 <SEP> 0 <tb> <SEP> CE3 <tb> Table I-B (continued) EMI48.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m-Pe <tb> -SO2OCH2CF3 <SEP> H <SEP> Q <SEP> <tb> -SO2OCE2CC13 <SEP> 5-Cl <SEP> O <SEP> 0 <tb> <SEP> /OCE3 <tb> -SO2N <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> cE3 <tb> H <SEP> H <SEP> S <SEP> CE2 <tb> Cl <SEP> H <SEP> S <SEP> CH2 <tb> 2 <SEP> H <SEP> S <SEP> CE2 <tb> C02CX3 <SEP> H <SEP> S <SEP> CE2 <tb> SCE3 <SEP> H <SEP> S <SEP> CE2 <tb> SOCE3 <SEP> H <SEP> S <SEP> CUE <SEP> 2 <tb> CF3 <SEP> H <SEP> S <SEP> CE2 <tb> CO2CH2CE2OCE3 <SEP> H <SEP> S <SEP> CE2 <tb> CO2CE2CE2Br <SEP> H <SEP> S <SEP> CX2 <tb> CO <SEP> CE <SEP> CF <SEP> H <SEP> S <SEP> CE2 <tb> CO2CE2CH=CH2 <SEP> H <SEP> S <SEP> CE2 <tb> CO <SEP> CECE <SEP> CE <SEP> E <SEP> S <SEP> CH2 <tb> <SEP> 2, <SEP> 2 <SEP> 3 <SEP> H <SEP> 2 <tb> <SEP> CE3 <tb> C02(CE2CH2O)2CE3 <SEP> H <SEP> S <SEP> CE2 <tb> CON(CE3)2 <SEP> H <SEP> S <SEP> CX2 <tb> CON(OCE3)-CH3 <SEP> H <SEP> S <SEP> CE2 <tb> SO2N(OCE3)CE3 <SEP> H <SEP> S <SEP> CE2 <tb> <SEP> / <SEP> CE2CH2 <SEP> \ <tb> SO2N) <SEP> O <SEP> H <SEP> S <SEP> CH2 <tb> <SEP> CE2CE2 <tb> 0 <tb> n <tb> CSCE(CH3)2 <SEP> H <SEP> S <SEP> CE2 <tb> S020ClI2CF3 <SEP> H <SEP> S <SEP> CE2 <tb> Cl <SEP> 5-Cl <SEP> S <SEP> CE2 <tb> CE3 <SEP> 3 <SEP> 5-F <SEP> S <SEP> CH2 <tb> OCE3 <SEP> 5--OCE3 <SEP> S <SEP> CE2 <tb> CO2CH2CE3 <SEP> 4-F <SEP> S <SEP> CE2 <tb> Table I-B (continued) EMI49.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> ms <tb> S02CH3 <SEP> 5-CH3 <SEP> S <SEP> CH2 <tb> SO2N(CE3)2 <SEP> 4-OCH3 <SEP> S <SEP> CH2 <tb> d <tb> It <tb> SUCH3 <SEP> 5-C1 <SEP> S <SEP> CH2 <tb> SO2OCH2CC13 <SEP> 3-F <SEP> S <SEP> CH2 <tb> CH3 <SEP> H <SEP> -S <SEP> 0 <tb> CI <SEP> E <SEP> S <SEP> O <tb> 2 <SEP> H <SEP> S <SEP> O <tb> CO2CE2 <SEP> CR3 <SEP> H <SEP> S <SEP> 0 <tb> 502CM3 <SEP> H <SEP> S <SEP> O <tb> CF3 <SEP> E <SEP> -S <SEP> o <tb> CO2 <SEP> (CE2) <SEP> 3 <SEP> H <SEP> S <SEP> O <tb> C02CH2CH2C1 <SEP> E <SEP> S <SEP> 0 <tb> COvCH2CE=CHCH3 <SEP> H <SEP> S <SEP> O <tb> CON(OCH3)CH3 <SEP> E <SEP> S <SEP> O <tb> CON(CR) <SEP> [CE(CE3)2) <SEP> S <SEP> S <SEP> 0 <tb> <SEP> CE2CE2 <tb> 502N <SEP> CH2 <SEP> E <SEP> S <SEP> O <tb> <SEP> CE2CE2 <tb> <SEP> CR <tb> 502N <SEP> \ <SEP> H <SEP> S <SEP> O <tb> <SEP> C2E5 <tb> 0 <tb> C11 <SEP> S-CE2 <SEP> CE3 <SEP> H <SEP> S <SEP> O <tb> SO2OCH2CC13 <SEP> H <SEP> S <SEP> O <tb> C1 <SEP> 5-C1 <SEP> S <SEP> O <tb> NO2 <SEP> 5-C1 <SEP> S <SEP> o <tb> C 2CH3 <SEP> 4-Br <SEP> S <SEP> O <tb> SOC2H5 <SEP> 4-F <SEP> S <SEP> O <tb> <SEP> OCH3 <tb> SO <SEP> 2N <SEP> 5-C1 <SEP> S <SEP> O <tb> <SEP> CH3 <tb> Table I-B (continued) EMI50.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m-P <tb> ocE3 <SEP> 5 OCE3 <SEP> S <SEP> O <tb> o <tb> .. <tb> CSCH(CE3)2 <SEP> 4-CE3 <SEP> S <SEP> 0 <tb> SO2OCH2CF3 <SEP> S-Cl <SEP> S <SEP> 0 <tb> Table I-C EMI51.1 R2 R3 W Y m. p. Cl H O CH2 193-195 Cl 5-Cl O CH2 NO2 H O CH2 CO2CH3 H O CH2 208-209 CO2CH(CH3)2 H O CH2 -F H O CH2 -Br H O CH2 -SCH3 H O CH2 -SO2CH3 H O CH2 -CF3 H O CH2 -CO2CH2CH3 H O CH2 -CO2CH2CH2Cl H O CH2 -CO2CH2CH2CH3 H O CH2 -CO2CH2CH2OCH3 H O CH2 CO2CH(CH3)2 H O CH2 CO2CH2CH=CH2 H O CH2 CO2CH2CF3 H O CH2 CO2(CH2)3CH3 H O CH2 CO2(CH2)5CH3 H O CH2 CO2CH(CH3)CH2CH3 H O CH2 CO2CH(CH2CH3)2 H O CH2 CO2CH2C(CH3)3 H O CH2 CO2CH2CH=CH-CH3 H O CH2 H H O CH2 Table I-C (continued) EMI52.1 <tb> <SEP> R3 <SEP> Fif <SEP> Y <SEP> m.p. <tb> <SEP> s <tb> <SEP> CO2CH(CH3)CH=CH2 <SEP> n <SEP> O <SEP> C <SEP> 2 <SEP> CE2 <tb> <SEP> CO2CE2CE=CE(CE2)2CE3' <SEP> CH2 <tb> <SEP> CO2 <SEP> (CE2) <SEP> 4C1 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> coz <SEP> (CE2) <SEP> óCl <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> COZ <SEP> < <SEP> H <SEP> <SEP> CE2 <tb> <SEP> CO2 <SEP> H <SEP> 0 <SEP> CX2 <tb> CO2 <SEP> (cE2CE2Q > 2 <SEP> H <SEP> O <SEP> cE2 <tb> C <SEP> 2( <SEP> 2O)2C2? <SEP> <SEP> H <SEP> 0 <SEP> CE2 <tb> CO2CE2CE2CE2OCE3 <SEP> H <SEP> 0 <SEP> CE2 <tb> C02CECH2CE20C2E5 <SEP> O <SEP> cue2 <tb> CON <SEP> 2 <SEP> H <SEP> 0 <SEP> CE2 <tb> GOES(CB) <SEP> % <tb> CQ(Cn <SEP> H <SEP> 0 <SEP> CE2 <tb> <SEP> w: <SEP> 2 <SEP> X <SEP> <SEP> CE2 <tb> CON CE3 <tb> .3 <tb> <SEP> C'A(CE3) <SEP> 2 <tb> CON(CE(CH3) <SEP> 2 <SEP> 2 <SEP> H <SEP> 0 <SEP> CE2 <tb> C0CE2CE(CE3) <SEP> 2 <SEP> H <SEP> 0 <SEP> CE2 <tb> <SEP> cE3 <tb> CON(CE2CE2CE2CE3)2 <SEP> i <SEP> h' <SEP> O <SEP> CE2 <tb> <SEP> 0 <tb> <SEP> ocE3 <tb> CON <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> -3 <tb> Table I-C (continued) R2 R3 W Y m.p. Cl 6-Cl O CH2 Cl 4-Cl O CH2 Cl 3-Cl O CH2 F 5-Cl O CH2 F 3-Cl O CH2 F 4-Cl O CH2 F 5-F O CH2 Cl 5-OCH3 O CH2 Cl 5-CH(CH3)2 O CH2 Cl 4-CH3 O CH2 Cl 4-F O CH2 Cl 5-Br O CH2 Cl 6-CH3 O CH2 NO2 5-Cl O CH2 NO2 6-Cl O CH2 NO2 5-F O CH2 Cl 5-CH(CH3)C2H5 O CH2 Br 5-F O CH2 SCH3 5-Cl O CH2 SCH3 4-Cl O CH2 SO2CH3 5-Cl O CH2 SO2CH3 6-Cl O CH2 SCH3 6-Cl O CH2 SCH3 4-OCH3 O CH2 CF3 5-Cl O CH2 CF3 5-CH3 O CH2 CF3 5-F O CH2 CF3 4-Cl O CH2 CF3 4-CH3 O CH2 CO2CH3 5-CH3 O XH2 Table I-C (continued) EMI54.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> C <SEP> c;R <SEP> 6-CE3 <SEP> Q <SEP> C52 <tb> CO2CR3 <SEP> -c1 <SEP> <SEP> Ct2 <tb> CO2CE3 <SEP> 3-Cl <SEP> 0 <SEP> C22 <tb> CO2CE3 <SEP> 6-Cl <SEP> 0 <SEP> CEX <tb> CO2CE3 <SEP> 4-C!;3 <SEP> 0 <SEP> CH2 <tb> 50CR3 <SEP> H <SEP> <SEP> CH2 <tb> E3 <SEP> 5-Br <SEP> O <SEP> CE2 <tb> <SEP> cE3 <tb> SOCE <SEP> 6-CE <SEP> O <SEP> CE2 <tb> <SEP> 3 <tb> <SEP> > <SEP> cE3 <tb> <SEP> 3 <tb> <SEP> 3 <tb> SO <SEP> N <SEP> / <SEP> g <tb> SO,N <tb> <SEP> scE3 <tb> <SEP> CR <tb> 2 <SEP> Q <SEP> X <SEP> <SEP> CE2 <tb> <SEP> N <tb> <SEP> CE2CE <SEP> E=CE2 <tb> <SEP> CE <SEP> CE3 <tb> <SEP> CE2CE3 <SEP> S-Cl <SEP> <SEP> CE2 <tb> <SEP> CH2 <tb> <SEP> C <tb> <SEP> SO <SEP> 0. <SEP> C6, <tb> <SEP> 2 <SEP> \ <SEP> CH2 <SEP> 4-OCE3 <SEP> 0 <SEP> CE2 <tb> <SEP> CE <tb> <SEP> 0 <tb> <SEP> -C-SCE3 <SEP> H <SEP> 0 <SEP> CE2 <tb> <SEP> O <SEP> CE <tb> <SEP> =2cE <SEP> / <SEP> 3 <SEP> > <SEP> <SEP> C=2 <tb> <SEP> cuff, <tb> <SEP> o <tb> <SEP> -C-S-CR <SEP> 2CR <SEP> 2CE3 <SEP> 5-CE2Cv3 <SEP> 0 <SEP> Cw;2 <tb> <SEP> OCE <tb> <SEP> 3 <tb> <SEP> 5-C1 <SEP> 5-Cl <SEP> O <SEP> CE2 <tb> <SEP> NICE3 <tb> Table I-C (continued) R2 R3 W Y m.p. Cl H O O Cl 5-C1 0 0 N02 E O 0 C 2CH3 H 0 O CO2CH(CH3) 2 H O 0 -F H O O -Er H O 0 -SCH3 H O O -S02CE3 H 0 O -Cf3 H C O -CO2CH2CH3 H O O -CO2CH2CH2Cl H O O -CO2CH2CH2CH3 H O O -CO2CH2CH2OCH3 H O O -SO2OCH2CF3 H O CH2 CO2CH2CH=CH2 H O O CO2CH2CF3 H O O CO2(CH2)3CH3 E O 0 CO2(CH2)5CH3 H O O CO2CH(CH3)CH2CH3 H O O CO2CH(CH2CH3)2 H O O CO2CH2C(CH3)3 H O O CO2CH2CH=CH-CH3 H O 0 H H O 0 Table I-C (continued) EMI56.1 <tb> <SEP> R2 <SEP> R3N <SEP> W <SEP> Y <SEP> m <SEP> Fj <tb> <SEP> eBcl <tb> <SEP> C02CE2-c <SEP> R <SEP> <SEP> <tb> <SEP> CEo3 <tb> <SEP> CO2CH2CE=CE(CE2)2CE3 <SEP> H <SEP> 0 <SEP> 0 <tb> CO2 <SEP> (CE2) <SEP> 4C1 <SEP> H <SEP> O <SEP> 0 <tb> <SEP> C02,(CE2) <SEP> 6C1 <SEP> H <SEP> OO <tb> <SEP> CO2 <SEP> &num; ;j <SEP> H <SEP> OO <tb> <SEP> CO2 <SEP> H <SEP> OO <tb> CO{CH2CE20) <SEP> 2cm.3 <SEP> H <SEP> O <SEP> 0 <tb> C02(CH2CH2O)2C2E5 <SEP> H <SEP> O <tb> CO2CH2CH2CH2OCH3 <SEP> H <SEP> OC <tb> C02CH2CE2CH2OC2E5 <SEP> H <SEP> 0 <SEP> 0 <tb> CON(CH3) <SEP> 2 <SEP> H <SEP> o <tb> CON(C2E5) <SEP> 2 <SEP> O <SEP> 0 <tb> CON-CE3 <SEP> H <SEP> OO <tb> <SEP> CE(CE3)2 <tb> <SEP> CONL(CH(CH3)2)2 <SEP> H <SEP> -O <SEP> 0 <tb> <SEP> CON,CH2CH(CE3)2 <SEP> H <SEP> OO <tb> <SEP> cE3 <tb> <SEP> CON <SEP> (CE2CH2CH2CH3) <SEP> 2 <SEP> H <SEP> 0 <SEP> 0' <tb> <SEP> 2 <tb> <SEP> /IXti3 <tb> <SEP> CON <tb> <SEP> CH3 <tb> Table I-C (continued) R2 R3 W Y m. p. Cl 6-Cl O O Cl 4-Cl O O Cl 3-Cl O O F 5-Cl O O F 3-Cl O 0 F 4-Cl 0 0 F 5-F O O Cl 5-OCH3 O O Cl 5-CH(CH3)2 O O Cl 4-CH3 O O Cl 4-F O O Cl 5-Br O O Cl 6-CE3 0 NO2 5-C1 0 0 NO2 6-Cl O O NO 5-F O 0 Cl 5-CH(CH3)C2H5 O O Br 5-F O SCH3 5-C1 0 0 SCH3 4-C1 0 0 SO2CH3 5-Cl O O SO2CH3 6-Cl O O SCH3 6-Cl O O SCH3 4-OCH3 O O CF 5-C1 0 0 CF3 5-CH3 O O CF3 5-F O O CF3 4-C1 0 0 CF3 4-CH3 O O CO2CH3 5-CH3 O O Table I-C (continued) EMI58.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> C02CE3 <SEP> 6-CE3 <SEP> 0 <SEP> 0 <tb> C:2CE3 <SEP> :-C1 <SEP> 0 <SEP> O <tb> CO2CX3 <SEP> 3-c1 <SEP> 0 <SEP> 0 <tb> CO2CH3 <SEP> 6-Cl <SEP> o <SEP> 0 <tb> C02CE3 <SEP> 4 <SEP> 3 <SEP> O <SEP> <tb> SOCE <SEP> H <SEP> O <SEP> 0 <tb> 3 <SEP> 5-Cl <SEP> 0 <SEP> O <tb> SOCR2CE=CE3 <SEP> 6-P <SEP> 0 <SEP> 0 <tb> <SEP> CR <tb> <SEP> ,/ <SEP> 3 <tb> SO <SEP> 2N <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> NCR <tb> <SEP> 3 <tb> <SEP> CE3 <tb> <SEP> H <SEP> 0 <SEP> 0 <tb> .cO <SEP> O <SEP> N <tb> <SEP> 2 <SEP> \ <tb> <SEP> a2CE3 <tb> <SEP> -/- <SEP> CE2CE=CE2 <tb> 502N <SEP> \ <SEP> 5-OCE3 <SEP> 0 <SEP> 0 <tb> <SEP> NCR2'CE=CE2 <tb> <SEP> CE <tb> <SEP> zC2 <SEP> CE2 <tb> SO <SEP> 2N <SEP> 3 <SEP> 3-Br <SEP> O <SEP> 0 <tb> <SEP> CE2-CE2 <tb> <SEP> o <tb> CeSCE3 <SEP> B <SEP> 0 <SEP> 0 <tb> <SEP> CH3 <tb> -e-sc8 <SEP> 5 <SEP> 0 <SEP> 0 <tb> SUCH3 <tb> <SEP> CR3 <tb> a <tb> C-S-CEC- <SEP> Cr.3 <SEP> H <SEP> O <SEP> 0 <tb> <SEP> CE3 <tb> <SEP> O <SEP> 1 <SEP> C,R3 <tb> -C-S-CCH <SEP> 6-CE3 <SEP> 0 <SEP> 0 <tb> <SEP> C.ij <tb> Table I-C (continued) EMI59.1 <tb> <SEP> R <tb> <SEP> R2 <SEP> F7 <SEP> 3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> / <SEP> OCH3 <tb> -SO2N <SEP> H <tb> <SEP> CH3 <tb> -SO2OCE2CC13 <SEP> 3-C1 <SEP> 0 <SEP> 0 <tb> H <SEP> H <SEP> S <SEP> CE, <tb> C1 <SEP> H <SEP> S <SEP> CH2 <tb> Br <SEP> H <SEP> S <SEP> CH2 <tb> NO2 <SEP> H <SEP> S <SEP> CE2 <tb> 2 <SEP> 3 <SEP> H <SEP> S <SEP> e2 <tb> CO2(CH2)2CH3 <SEP> H <SEP> S <SEP> CH2 <tb> S-CE2CX3 <SEP> H <SEP> S <SEP> CH2 <tb> SOCH, <SEP> t <SEP> S <SEP> CH2 <tb> <SEP> 2 <tb> SO2 <SEP> 3 <SEP> H <SEP> S <SEP> CR2 <tb> CF3 <SEP> H <SEP> S <SEP> CE2 <tb> CO2CH2CH2OC2E5 <SEP> H <SEP> S <SEP> CE2 <tb> C 2CE2CH2C1 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CHCH=CH2 <SEP> H <SEP> S <SEP> CHz <tb> <SEP> CE3 <tb> CON(C2E5)2 <SEP> H <SEP> S <SEP> CE2 <tb> COt{i2 <SEP> H <SEP> S <SEP> CH2 <tb> <SEP> ,'CE2CH2 <SEP> CE2 <tb> S02N <SEP> H <SEP> S <SEP> H <SEP> S <tb> <SEP> CH2CH2 <tb> SO2N(CH3)2 <SEP> H <SEP> S <SEP> CE2 <tb> 0 <tb> CSCE2CE3 <SEP> H <SEP> S <SEP> CE2 <tb> SO2OCE2CF3 <SEP> H <SEP> S <SEP> CH2 <tb> C1 <SEP> 5-Cl <SEP> S <SEP> CE2 <tb> Br <SEP> 5-Br <SEP> S <SEP> CH2 <tb> OCR3 <SEP> 5-OCE3 <SEP> S <SEP> CR2 <tb> CH3 <SEP> 6 <SEP> CH3 <SEP> S <SEP> CH2 <tb> 2 <SEP> 3 <SEP> 4-F <SEP> S <SEP> CH2 <tb> Table I-C (continued) EMI60.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> SCE3 <SEP> 3-Cl <SEP> S <SEP> CE2 <tb> 5O2N(OCH3)CH3 <SEP> 6-C1 <SEP> S <SEP> CX2 <tb> 0 <tb> I' <tb> CSCH3 <SEP> 6-OCE3 <SEP> S <SEP> CE2 <tb> R <SEP> H <SEP> S <SEP> O <tb> C1 <SEP> H <SEP> S <SEP> O <tb> F <SEP> H <SEP> S <SEP> O <tb> N02, <SEP> H <SEP> S <SEP> O <tb> SCE3 <SEP> H <SEP> S <SEP> Q <tb> QCE3 <SEP> H <SEP> S <SEP> 0 <tb> SOCE(CH3) <SEP> 2 <SEP> S <SEP> 0. <tb> CF3 <SEP> H <SEP> S <SEP> o <tb> CO <SEP> 2CE3 <SEP> H <SEP> S <SEP> O <tb> C 2CE2C223r <SEP> H <SEP> S <SEP> O <tb> CO2C2CE2CH2OCH3 <SEP> H <SEP> S <SEP> O <tb> CO <SEP> 2CE2CCl3 <SEP> H <SEP> S <SEP> O <tb> CO2CH2CR=CH2 <SEP> E <SEP> S <SEP> O <tb> CO2CR(CE3) <SEP> 2 <SEP> H <SEP> S <SEP> G <tb> CON(OCH3)CH3 <SEP> H <SEP> S <SEP> O <tb> CON <SEP> [CE <SEP> (CR3) <SEP> 2 <SEP> 2 <SEP> H <SEP> S <SEP> 0 <tb> <SEP> /CE2CEx <tb> CON <SEP> CE <SEP> H <SEP> S <SEP> O <tb> <SEP> N <tb> <SEP> CH2CE2 <tb> Q <tb> CS-CE2CE2CE3. <SEP> R <SEP> S <SEP> O <tb> SO <SEP> OC' <SEP> CC1 <SEP> E <SEP> S <SEP> O <tb> H <SEP> 5-F <SEP> S <SEP> O <tb> Cl <SEP> 5-Cl <SEP> S <SEP> O <tb> C 2CE3 <SEP> 5-OCE3 <SEP> S <SEP> O <tb> NO2 <SEP> < <SEP> 6-Cl <SEP> S <SEP> 0 <tb> 0CE3 <SEP> 5-OCE3 <SEP> S <SEP> O <tb> S02N(CR3)2 <SEP> 4-Cl <SEP> S <SEP> 0 <tb> CON(CH3)2 <SEP> 5-Br <SEP> S <SEP> O <tb> SO2OCE2Cv3 <SEP> 5-CX3 <SEP> S <SEP> O <tb> Table I-D EMI61.1 EMI61.2 <tb> <SEP> R2 <SEP> a3 <SEP> W <SEP> ¯ <SEP> ffi <tb> C 2CH3 <SEP> H <SEP> <SEP> CH2 <SEP> 190.5-192 <tb> C 2CH3 <SEP> 3-Cl <SEP> <SEP> CH2 <tb> COUCH3 <SEP> 4-C2H5 <SEP> <SEP> CE2 <tb> CO2C2H5 <SEP> H <SEP> <SEP> CE2 <tb> C02C2H5 <SEP> 4 <SEP> 9 <SEP> CEACh <SEP> <SEP> CH2 <tb> CQ2CH2CH2CH3 <SEP> H <SEP> <SEP> CH2 <tb> C 2CH2CH2CH3 <SEP> 4-F <SEP> CH2 <tb> CO2CHCH2CX3 <SEP> H <SEP> <SEP> CH2 <tb> <SEP> CH3 <tb> CO2iHCH2CH3 <SEP> 3-C1 <SEP> G <SEP> CH2 <tb> <SEP> CH3 <tb> CO2 <SEP> (CE2) <SEP> 4CE=CE2 <SEP> H <SEP> <SEP> CH2 <tb> C 2 <SEP> 4 <SEP> H <SEP> <SEP> CH2 <tb> CO2CE2CH2OC2HS <SEP> H <SEP> <SEP> CH2 <tb> CO2 <SEP> (CE2) <SEP> 30-CE3 <SEP> 4-CH3 <SEP> <SEP> cH2 <tb> <SEP> C2E5 <tb> CON <SEP> \ <SEP> C1 <SEP> O <SEP> CE2 <tb> <SEP> CE(CH3)2 <tb> <SEP> SOCH3 <tb> CON <SEP> s <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> CE2 <tb> <SEP> CH3 <tb> <SEP> SOzN(CH3)2 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> SO2NtC2H5)2 <SEP> E <SEP> O <SEP> CE2 <tb> <SEP> / <SEP> OCH3 <tb> <SEP> SO2N <SEP> H <SEP> · <SEP> O <SEP> CH2 <tb> <SEP> ¯ <SEP> CH3 <tb> Table I-D (continued) EMI62.1 <tb> <SEP> R2 <SEP> R3 <SEP> <tb> <SEP> 3 <SEP> N <SEP> Y <SEP> m.p. <tb> COSCX3 <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> Cm3 <SEP> 2 <tb> COS-CH <SEP> 5-C1 <SEP> O <SEP> CX2 <tb> S-Cl <SEP> 0 <SEP> CE2 <tb> <SEP> CH <tb> CoSCxzcE3 <SEP> 6-OCHr <SEP> O <SEP> CE2 <tb> CO2CH3 <SEP> H <SEP> 0 <tb> : 2:E3 <SEP> 3-Cl <SEP> 0 <tb> C02CH3 <SEP> 4-C2E5 <SEP> 0 <tb> cO2C2zs <SEP> H <SEP> 0 <tb> CO2C2H5 <SEP> 4*CEA*CE^ <SEP> ffi <SEP> O <SEP> 0 <tb> CO2CE2CH2CE3 <SEP> H <SEP> o <SEP> O0 <tb> COzCH2CH2CH3 <SEP> 4¯F <SEP> 0 <tb> CO2CE,CH2CE3 <SEP> H <SEP> o <tb> <SEP> CE3 <tb> <SEP> CO2CECE2CE3 <SEP> 3-C1 <SEP> 0 <SEP> 0 <tb> <SEP> CX3 <tb> <SEP> CO(CH2)4CH=CH2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> CQ <SEP> a <SEP> o <SEP> 0 <tb> <SEP> CO2CH2CH2OC2H <SEP> H <SEP> O <SEP> 0 <tb> <SEP> C02(CE2)30-CH3 <SEP> 4-CE3 <SEP> 0 <SEP> 0 <tb> <SEP> C <tb> <SEP> 2H5 <tb> <SEP> CON <SEP> Cl <SEP> G <SEP> o <tb> <SEP> CE <SEP> (CE3) <SEP> 2 <tb> <SEP> / <SEP> OCE3 <tb> <SEP> CON <SEP> H <SEP> O <SEP> <tb> <SEP> CH3 <tb> <SEP> COSH, <SEP> H <SEP> o <SEP> 0 <tb> <SEP> COSCE-CE2CE3 <SEP> 3-Br <SEP> 0 <SEP> 0 <tb> <SEP> cE3 <tb> <SEP> COS-CE2CE2CE3 <SEP> 6-C1 <SEP> 0 <SEP> 0 <tb> <SEP> SO2N(CR3)2 <SEP> R <SEP> O <SEP> 0 <tb> <SEP> SO2N(C2X5)2 <SEP> H <SEP> o <SEP> 0 <tb> Table I-D (continued) EMI63.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> OCE3 <tb> SO2 <SEP> N <SEP> E <SEP> o <SEP> 0 <tb> <SEP> CH3 <tb> COnCH3 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CHCH2CH3 <SEP> H <SEP> S <SEP> C82 <tb> <SEP> CE3 <tb> CO2CE2CE=CE2 <SEP> H <SEP> S <SEP> CH2 <tb> CO2 <SEP> < <SEP> E <SEP> S <SEP> CE2 <tb> CO2CH2CF3 <SEP> H <SEP> S <SEP> CH2 <tb> Co2CH2CE2OCE3 <SEP> H <SEP> S <SEP> CE2 <tb> SO2EJ(OCH3)CH3 <SEP> E <SEP> S <SEP> CH2 <tb> SO2M(CIK3)2 <SEP> H <SEP> S <SEP> CH2 <tb> CON(CB3) <SEP> 2 <SEP> H <SEP> S <SEP> CE2 <tb> 0 <tb> CSCE3 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CR3 <SEP> 5-C1 <SEP> S <SEP> CH2 <tb> CO2CH(CH3)2 <SEP> 4-CH3 <SEP> S <SEP> CH2 <tb> SO2N(OCH3)CH3 <SEP> 6-F <SEP> S <SEP> CE2 <tb> CO2CF <SEP> H <SEP> S <SEP> O <tb> CO2CH(CH3)2 <SEP> H <SEP> S <SEP> O <tb> CO2CE2CR2OCR2CE3 <SEP> H <SEP> S <SEP> O <tb> CO2CH2CH=CHCH3 <SEP> H <SEP> S <SEP> O <tb> CON <SEP> (OCE3) <SEP> CE3 <SEP> H <SEP> S <SEP> O <tb> <SEP> / <SEP> cli2cEI2 <tb> CON <SEP> O <SEP> H <SEP> S <SEP> O <tb> <SEP> CH22 <SEP> / <tb> SO2tJ(C2H,)2 <SEP> H <SEP> S <SEP> O <tb> <SEP> CE2CE2 <tb> SO2N <SEP> H <SEP> H <SEP> H <SEP> S <SEP> O <tb> <SEP> CH2CH2 <tb> Table I-D (continued) EMI64.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> CO2CH3 <SEP> S-F <SEP> S <SEP> O <tb> CO2CH3 <SEP> 5-OCH3 <SEP> S <SEP> O <tb> CON(CH3)2 <SEP> 6-Cl <SEP> S <SEP> O <tb> SO2N(OCE3)CEa <SEP> 3-Cl <SEP> S <SEP> O <tb> 0 <tb> 1, <tb> C-SCH3 <SEP> 4-CH3 <SEP> S <SEP> O <tb> Table I-E EMI65.1 EMI65.2 <tb> <SEP> R <SEP> R <tb> <SEP> 2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> <SEP> L <tb> <SEP> COUCH <SEP> H <SEP> O <SEP> CH2 <tb> COUCH <SEP> 4-CE3 <SEP> 0 <SEP> O <SEP> CE2 <tb> C02C2H5 <SEP> H <SEP> <SEP> CH2 <tb> CO2C2H5 <SEP> C1 <SEP> <SEP> CH2 <tb> CO2CE(CE3)2 <SEP> E <SEP> CE2 <tb> CO2CR2-CE=CE2 <SEP> H <SEP> O <SEP> CE2 <tb> CO2CH2CH=CHCH2CH3 <SEP> 5-Br <SEP> O <SEP> CH2 <tb> CO2CE2C, <SEP> H-C, <SEP> H <SEP> H <SEP> CH2 <tb> <SEP> Br <SEP> Br <tb> cho20 <SEP> R <SEP> <SEP> CH2 <tb> CO2(CX2CH2)2OC2BS <SEP> H <SEP> O <SEP> CH2 <tb> CO2CH2CH2CH2OC2E5 <SEP> H <SEP> O <SEP> CH2 <tb> CON(CH2CR2CE2CE3)2 <SEP> H <SEP> O <SEP> CE2 <tb> <SEP> CONCH, <tb> CON <SEP> / <SEP> H <SEP> <SEP> CH2 <tb> <SEP> CR3 <tb> <SEP> COSH3 <SEP> <SEP> 0 <SEP> CR2 <tb> <SEP> CE <tb> <SEP> COSCH2CH <SEP> H <SEP> <SEP> CH2 <tb> <SEP> CX3 <tb> <SEP> COSCH2CH2CX2CH3 <SEP> 3-C1 <SEP> O <SEP> CH2 <tb> SO2N(CH3)2 <SEP> E <SEP> <SEP> CH2 <tb> SO2N(C2H5)2 <SEP> H <SEP> O <SEP> CH2 <tb> <SEP> LH, <SEP> H <SEP> O <SEP> CH2 <tb> SO2N <SEP> CE3 <tb> <SEP> s <SEP> CH3 <tb> Table I-E (continued) EMI66.1 <tb> <SEP> R2 <SEP> R3 <SEP> N <SEP> Y <SEP> m.p. <tb> COUCH3 <SEP> H <SEP> o <SEP> 0 <tb> CO2CH3 <SEP> 4-CE3O <SEP> 0 <SEP> 0 <tb> CO <SEP> C <SEP> H <SEP> H <SEP> 0 <SEP> 0 <tb> C02C2X5 <SEP> Cl <SEP> o <SEP> O <tb> CO2CR(CH3)2 <SEP> H <SEP> O <SEP> O <tb> CO2CH2-CH=CH2 <SEP> H <SEP> 0 <SEP> 0 <tb> CO2CE2CR=CHCH <SEP> 2CR3 <SEP> Br <SEP> O <SEP> 0 <tb> CO2CE <SEP> 2-?E'2 <SEP> H <SEP> o <SEP> 0 <tb> <SEP> L <SEP> r <SEP> L <tb> <SEP> Br <SEP> Br <tb> CO-e) <SEP> H <SEP> E <SEP> O <tb> <SEP> C02(CH2CH2) <SEP> 2 C2Hs <tb> <SEP> CO2CH2CH2CE2OC2H5 <SEP> H' <SEP> o <SEP> 0 <tb> <SEP> CON(CH2CE2CE2CH3)z <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> OCI93 <tb> <SEP> CON <tb> <SEP> CH3 <tb> <SEP> COSCE3 <SEP> O <SEP> 6 <SEP> 0 <tb> <SEP> CE <tb> <SEP> COSCE2CE <SEP> H <SEP> CR3 <SEP> O <SEP> 0 <tb> <SEP> CH, <tb> <SEP> CO-SCB,aCH, <SEP> 2Cz3 <SEP> 6-CE3 <SEP> O <SEP> 0 <tb> <SEP> C0S-C,RCR2CE3 <SEP> 3-F <SEP> 0 <SEP> 0 <tb> <SEP> cE3 <tb> <SEP> SO2N(CH3)2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> S02N(C2H5)2 <SEP> H <SEP> 0 <SEP> 0 <tb> <SEP> CB, <tb> <SEP> S02N <SEP> H <SEP> O <SEP> 0 <tb> <SEP> SO2N <SEP> H <SEP> O <SEP> O <tb> <SEP> ocE3 <tb> Table I-E (continued) EMI67.1 <tb> <SEP> R2 <SEP> R3 <SEP> W <SEP> Y <SEP> m.p. <tb> C02CE3 <SEP> H <SEP> S <SEP> C;i2 <tb> CO2CE2 <SEP> CF3 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CH2CE=CHCH3 <SEP> H <SEP> S <SEP> CE2 <tb> C 2CH2Ca2C1 <SEP> H <SEP> S <SEP> CH2 <tb> C02CE2CE20CH3 <SEP> H <SEP> S <SEP> CH2 <tb> CON(C2Hg)2 <SEP> H <SEP> S <SEP> CE2 <tb> CON(OCH3)CH3 <SEP> H <SEP> S <SEP> CH2 <tb> SO2N(OCH3)CH3 <SEP> H <SEP> S <SEP> CH2 <tb> S02N(CH3)2 <SEP> E <SEP> S <SEP> CH2 <tb> 0 <tb> CS-CH(CH3)2 <SEP> H <SEP> S <SEP> CH2 <tb> CO2CH3 <SEP> 5-CH3 <SEP> S <SEP> CR2 <tb> CON(CE3)2 <SEP> 5-OCH3 <SEP> S <SEP> CH2 <tb> SO2N(CH3)2 <SEP> 6-Cl <SEP> S <SEP> CH2 <tb> o <tb> CS-CH3 <SEP> 4-F <SEP> S <SEP> CH2 <tb> C02CH2CH3 <SEP> H <SEP> S <SEP> O <tb> CO2CH(CH3)2 <SEP> E <SEP> S <SEP> O <tb> C 2CH2CH2Br <SEP> H <SEP> S <SEP> O <tb> CO2CH2CH=CE2 <SEP> H <SEP> S <SEP> O <tb> CO2 <SEP> (CE2CE2O) <SEP> 2CE3 <SEP> H <SEP> S <SEP> O <tb> CON[CE(CE3)2)2 <SEP> .H <SEP> S <SEP> O <tb> SO2N(OCH3)CH3 <SEP> H <SEP> SO <tb> C 2CH3 <SEP> 6-CE3 <SEP> S <SEP> 0 <tb> CO2CE <SEP> (CE3) <SEP> 2 <SEP> 5-C1 <SEP> S <SEP> O <tb> CON(OCH3)CH3 <SEP> 5-OCH3 <SEP> S <SEP> O <tb> SO2N(CE3)2 <SEP> 4-F <SEP> S <SEP> O <tb> <SEP> sCH2CH2s <tb> SO2N <SEP> O <SEP> 3-Br <SEP> S <SEP> O <tb> <SEP> H2CH2 <tb> The compounds in Table II are prepared by reacting pyridinesulfonylisocyanates or pyridinesulfonylisothiocyanates with the appropriate 2-aminopyrimidine as illustrated by Examples 8 and 9. Example 8 2-Chloro-3-pyridinesulfonylisocyanate To 125 ml of dry xylene was added with stirring 20.7 g of 2-chloro-N-(butylcarbamoyl)-3-pyridinesulf- fonamide. This solution was heated to reflux, and phosgene added until no further uptake of this gas was observed. It was then cooled, filtered. and the solvent was removed in vacuo to yield 2-chloro-3pyridinesulfonylisocyanate as an oil 3p 108-1100 (0.7 mm Hg). This product showed a sharp absorption peak in the infrared region at 2220 cm Example 9 2-Chloro-N-[(6,7-dihydro-4-methyl-5H-cyclopenta pyrimidin-2-yl) aminocarbonyl) pyridine-3-sulfonamide To a dry, stirred solution of 7.5 g of 6,7dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine in 200 ml of methylene chloride at ait'ient temperature and pressure is added 13 g of 2-chloropyrimidine-3- sulfonylisocyanate. The resulting mixture is stirred at reflux for 2 hours and then concentrated at reduced pressure. The residue is triturated with l-chlorobutane and filtered to yield the desired solid product. EMI69.1 EMI69.2 <tb> <SEP> R4 <SEP> W <tb> <SEP> I <tb> <SEP> 2-F <SEP> o <SEP> CH2 <tb> <SEP> 2-Br <SEP> o <SEP> CH2 <tb> <SEP> 2-CH3 <SEP> O <SEP> CH2 <tb> <SEP> 2-OCK3 <SEP> O <SEP> CH2 <tb> <SEP> 2-N02 <SEP> 0 <SEP> CH2 <tb> <SEP> 2-CO2CE3 <SEP> 0 <SEP> CH2 <tb> <SEP> 2-CO2CE(CE3)2 <SEP> 0 <SEP> CE2 <tb> <SEP> 2-CO2CECE2CH3 <SEP> O <SEP> 2 <tb> <SEP> cE3 <tb> <SEP> 2-SCE3 <SEP> 0 <SEP> CE2 <tb> <SEP> 2-SCX3 <tb> <SEP> 4-Cl <SEP> O <SEP> CH2 <tb> <SEP> 4-F <SEP> O <SEP> CE2 <tb> 4-Br <SEP> o <SEP> CH2 <tb> 4-C2E5 <SEP> O <SEP> CE2 <tb> 4-CE2 <SEP> CE2 <SEP> CE2CE3 <SEP> O <SEP> CE2 <tb> 4-OCR2CE2CR2CE3 <SEP> CE2 <tb> 4-NO2 <SEP> 0 <SEP> CE2 <tb> 4-C02C2H5 <SEP> O <SEP> CE2 <tb> 4-CO2CH2CH2CH3 <SEP> 0 <SEP> CR2 <tb> 3 <SEP> 0 <SEP> CE2 <tb> 4-C02(CE2)4CE3 <SEP> O <SEP> CE2 <tb> 4-CO2(CH2)4CH3 <SEP> 2 <tb> 4-CO2 <SEP> (CE2) <SEP> 5CE3 <SEP> 0 <SEP> CH2 <tb> 4-SCE3 <SEP> 0 <SEP> CH2 <tb> H <SEP> 0 <SEP> CE2 <tb> H <SEP> 2 <tb> 2-S <SEP> (CR2) <SEP> 3CE3 <SEP> 0 <SEP> CR2 <tb> Table II-A (continued) EMI70.1 <tb> <SEP> R4 <SEP> N <SEP> Y <tb> 2-F <SEP> O <SEP> 0 <tb> 2-Br <SEP> Q <SEP> 0 <tb> 2-CE3 <SEP> O <SEP> O <tb> 2-OCE3 <SEP> 0 <SEP> O <tb> 2NO2 <SEP> 0 <SEP> 0 <tb> 2-C02CX3 <SEP> 0 <SEP> 0 <tb> 2-CO2CH(CH3)2 <SEP> 0 <SEP> 0 <tb> 2-CO2C,ECE2CE3 <SEP> 0 <SEP> 0 <tb> <SEP> cx3 <tb> 2-SCE3 <SEP> O <SEP> 0 <tb> 4-Cl <SEP> 0 <SEP> 0 <tb> 4-F <SEP> O <SEP> O <tb> 4-Br <SEP> 0 <SEP> 0 <tb> 4 <SEP> Cs5 <SEP> O <SEP> 0 <tb> 4-CH2CE2CH2CE3 <SEP> 0 <SEP> 0 <tb> 4-OC;f; ;CB2 <SEP> 0 <SEP> 0 <tb> Q-NO2 <SEP> 0 <SEP> 0 <tb> 4'CO2C2E5 <SEP> 0 <SEP> 0 <tb> 4-CO2CH2CE2CR3 <SEP> 0 <SEP> 0 <tb> 4-CO2CH2CR(CH3)2 <SEP> 0 <SEP> 0 <tb> 4-CO2 <SEP> (CE2) <SEP> 4CH3 <SEP> 0 <SEP> 0 <tb> 4-C02(CH2)5CE3 <SEP> 0 <SEP> 0 <tb> 4-SCE3 <SEP> 0 <SEP> 0 <tb> 2-Cl <SEP> 0 <SEP> 0 <tb> 2-S <SEP> (CE2) <SEP> 3CE3 <SEP> 0 <SEP> 0 <tb> Table II-A (continued) R4 W Y H S CE2 2-C1 S CH2 2-F S CE2 2-CH3 S CH2 2-OCH3 S CH2 2-NO2 S CH2 2-CO2CH3 S CH2 2-SCH3 S CH2 4-C1 S CE2 4-Br S CE2 4-CH(CH3)2 S CH2 4-OC2H5 S CH2 4-NO2 S CH2 4-CO2C2H5 S CH2 H S O 2-C1 S. O 2-Br S O 2-CE3 S O 2-OCH3 S O 2-CO2CH(CH3)2 S O 2-SCH3 S O 4-Cl S O 4-F S O 4-C2H5 S O 4-OCH(CH3)2 S O 4-NO2 S O 4-CO2CH3 S O Table II-B EMI72.1 EMI72.2 <tb> <SEP> a4 <SEP> N <tb> <SEP> 4 <tb> 2-Br <SEP> o <SEP> CE2 <tb> 2-CE3 <SEP> O <SEP> CE2 <tb> 2eCECH2CE3 <SEP> 0 <SEP> CX2 <tb> <SEP> CE3 <tb> <SEP> 3 <tb> 2-CE2CH2CE3 <SEP> <SEP> CE2 <tb> 2-OCH3 <SEP> O <SEP> Cue <SEP> 2 <tb> <SEP> 3 <tb> 2-NO.2 <SEP> <SEP> CE2 <tb> 2 C02CH3 <SEP> <SEP> CX2 <tb> 2-CO2 <SEP> (CE2) <SEP> 5CE3 <SEP> 0 <SEP> CE2 <tb> 2-CO2CH2CE3 <SEP> O- <SEP> CE2 <tb> 4-Cl <SEP> O <SEP> CE2 <tb> 4-F <SEP> O <SEP> CE2 <tb> 4 <SEP> Br <SEP> O <SEP> CE2 <tb> 4-CE3 <SEP> O <SEP> CE2 <tb> 4-C2H5 <SEP> 0 <SEP> CX2 <tb> 4-CE(CE3)2 <SEP> O <SEP> CE2 <tb> 4-OCE3 <SEP> O <SEP> CE2 <tb> 4-NO2 <SEP> 0 <SEP> CE2 <tb> 4-CO2CE2CE2CE2CE3 <SEP> 0 <SEP> Cue <SEP> 2 <tb> 4-CO2CE(CE3)2 <SEP> 0 <SEP> cos2 <tb> 4-SCE3 <SEP> O <SEP> Cue <SEP> 2 <tb> 2-Cl <SEP> O <SEP> CE2 <tb> 2-F- <SEP> 0 <SEP> CE2 <tb> 2-OCE2CH2CR3 <SEP> O <SEP> CE2 <tb> 2-OCR2CH2CE2CH3 <SEP> CH2 <tb> H <SEP> O <SEP> CX2 <tb> Table II-B (continued) EMI73.1 <tb> <SEP> R4 <SEP> W <SEP> Y <tb> <SEP> 4 <SEP> F7 <SEP> Y <tb> 2-Br <SEP> 0 <SEP> 0 <tb> 2-CR3 <SEP> 0 <SEP> 0 <tb> 2-C,ECR2CH3 <SEP> o <SEP> 0 <tb> <SEP> CH3 <tb> 2-CX2CH2CH3 <SEP> o <SEP> 0 <tb> 2-OCH3 <SEP> 0 <SEP> O <tb> 2-NO2 <SEP> 0 <SEP> 0 <tb> 2-C02CH3 <SEP> 0 <SEP> 0 <tb> 2-cO2(CH2)5CE3 <SEP> 0 <SEP> 0 <tb> 2-CO2CH2CE3 <SEP> 0 <SEP> 0 <tb> 4-Cl <SEP> 0 <SEP> 0 <tb> 4-F <SEP> 0 <SEP> 0 <tb> 4-Br <SEP> 0 <SEP> 0 <tb> 4-CE3 <SEP> 0 <SEP> 0 <tb> 4-C2E5 <SEP> 0 <SEP> 0 <tb> 4-CH(CH3)2 <SEP> 0 <SEP> 0 <tb> 4-OCH3 <SEP> 0 <SEP> o <tb> 4-N02 <SEP> 0 <SEP> 0 <tb> 4-C02CR2CHZB2CR3 <SEP> O <SEP> 0 <tb> 4-CO2CE(CH3)2 <SEP> 0 <SEP> 0 <tb> 4-SCH3 <SEP> O <SEP> Q <tb> 2-C1 <SEP> 0 <SEP> 0 <tb> 2-F <SEP> 0 <SEP> 0 <tb> 2-OCH2CH2CX3 <SEP> 0 <SEP> 0 <tb> 2 <SEP> CH2cH2cH2cR3 <SEP> <SEP> 0 <tb> H <SEP> O <SEP> 0 <tb> Table II-B (continued) EMI74.1 <tb> <SEP> R4 <SEP> W <tb> <SEP> 6 <tb> H <SEP> S <SEP> CE2 <tb> 2-Cl <SEP> S <SEP> cue2 <tb> 2-Br <SEP> S <SEP> CE2 <tb> <SEP> 3 <tb> 2-CECzE5 <SEP> S <SEP> CE2 <tb> 2-OCE5 <SEP> S <SEP> CX2 <tb> 2-N 2 <SEP> S <SEP> CE2 <tb> 2-CO2CE3 <SEP> S <SEP> CE2 <tb> 4 <SEP> S <SEP> CE2 <tb> 4-F <SEP> S <SEP> CE2 <tb> 4-Br <SEP> S <SEP> cue2 <tb> 4-CE3 <SEP> S <SEP> CE2 <tb> 4OCE3 <SEP> S <SEP> CE2 <tb> 4 <SEP> : <SEP> S <SEP> CH2 <tb> 4-SCE3 <SEP> S <SEP> CE2 <tb> H <SEP> S <SEP> O <tb> 2-Cl <SEP> S <SEP> O <tb> 2-Br <SEP> S <SEP> Q <tb> 2-F <SEP> S <SEP> O <tb> 2CH3 <SEP> S <SEP> O <tb> 2-OCH3 <SEP> S <SEP> O <tb> 2-N 2 <SEP> S <SEP> O <tb> 2-CO2CH3 <SEP> S <SEP> O <tb> 4-Cl <SEP> S <SEP> O <tb> <SEP> S <SEP> O <tb> 4-C2s5 <SEP> S <SEP> O <tb> 4-N 2- <SEP> S <SEP> O <tb> 4 <SEP> C <SEP> 2 <SEP> 2E5 <SEP> S <SEP> O <tb> Table II-C EMI75.1 EMI75.2 <tb> <SEP> R4 <SEP> N <SEP> Y <tb> <SEP> d <SEP> Y <tb> 2-Br <SEP> O <SEP> CR2 <tb> 2-CH3 <SEP> 0 <SEP> CE2 <tb> 2-CHCE2CH3 <SEP> 0 <SEP> CH2 <tb> <SEP> C: :;.3 <tb> 2-CH2CH2CH3 <SEP> O <SEP> CE2 <tb> 2-OCR3 <SEP> O <SEP> CH2 <tb> 2-NO2 <SEP> 0 <SEP> CE2 <tb> 2-CO2CH3 <SEP> O <SEP> CH2 <tb> 2-CO2(CH2);CX3 <SEP> 0 <SEP> CE2 <tb> 2-CO2CH2Cn3 <SEP> O <SEP> CH2 <tb> 4-Ci <SEP> O <SEP> CE2 <tb> 4-F <SEP> O <SEP> CR2 <tb> 4-Br <SEP> O <SEP> CH2 <tb> 4-CE3 <SEP> O <SEP> CE2 <tb> 4-C2H5 <SEP> 0 <SEP> CR2 <tb> 4-CH(CH3)2 <SEP> O <SEP> CE2 <tb> 4-OCR3 <SEP> O <SEP> CH2 <tb> 4-NO2 <SEP> 0 <SEP> CR2 <tb> 4-CO2CE2CE2CR2 <SEP> CR3 <SEP> 0 <SEP> CR2 <tb> ¯CO2C-(Cw3) <SEP> 0 <SEP> CR2 <tb> 4-SCE3 <SEP> O <SEP> Cup,2 <tb> <SEP> 2-C1 <SEP> O <SEP> CH2 <tb> <SEP> 2-F <SEP> 0 <SEP> CE2 <tb> <SEP> 2-OCR2CE2CE3 <SEP> CE2 <tb> <SEP> 0 <SEP> CR <tb> <SEP> 2-OCEnC'2CH2CE3 <SEP> 2 <tb> <SEP> H <SEP> O <SEP> CH2 <tb> Table II-C (continued) EMI76.1 <tb> <SEP> R4 <SEP> N <tb> 2-S(CH2)2CH3 <SEP> 0 <SEP> CE2 <tb> 2-Br <SEP> O <SEP> Q <tb> 2-CE3 <SEP> Q <SEP> O <tb> 2-CECE2CEs <SEP> O <SEP> O <tb> <SEP> cE3 <tb> 2-CE2CE2CE3 <SEP> O. <SEP> 0 <tb> 2-OCE3 <SEP> o <SEP> 0 <tb> 2 <SEP> O2 <SEP> O <SEP> 0 <tb> 2 < Q2CE3 <SEP> 0 <SEP> 0 <tb> 2-CO2(CE2)5CE3 <SEP> 0 <SEP> 0 <tb> 2-C02CE2CE3 <SEP> <SEP> O <tb> 4-C1 <SEP> 0 <SEP> 0 <tb> 4-r <SEP> 0 <SEP> o <tb> 4-Br <SEP> O <SEP> O <tb> 4--CR3 <SEP> 0 <SEP> 0 <tb> 4-C2E5 <SEP> 0 <SEP> 0 <tb> 4-CE(CE3)2 <SEP> Q <SEP> O <tb> 4-OCH3 <SEP> <SEP> 0 <tb> 4-N02 <SEP> 0 <SEP> 0 <tb> <SEP> 4-Co2CE2CE2CE2CE3 <tb> <SEP> 4-CO2CE(CH3)2 <SEP> O <SEP> O <tb> <SEP> 4-SCE3 <SEP> 0 <SEP> 0 <tb> <SEP> 2-Cl <SEP> 0 <SEP> 0 <tb> <SEP> 2-F <SEP> O <SEP> O <tb> <SEP> 0 <SEP> 0 <tb> <SEP> 2-OCE2CX2CE3 <tb> <SEP> 0 <tb> <SEP> 2¯OcE2CC2CE2C}3 <SEP> 3 <SEP> O <tb> <SEP> R <tb> <SEP> 2 <SEP> (CR2) <SEP> 2CE3 <SEP> 0 <SEP> 0 <tb> Table II-C (continued) R4 W Y H S CH2 2-Cl S CH2 2-Br S CH2 2-F S CH2 2-CH2CH2CH3 S CE2 2-O(CH2)3CH3 S CH2 2-NO2 S CH2 2-CO2CH3 S CH2 2-SCH3 S CE2 4-Cl S CH2 4-F S CH2 4-CE3 S CH2 4-OCH3 S CH2 4-NO2 S CH2 4-C02C2H5 S CE2 2-C1 S O 2-Br S O 2-CH3 S O 2-OCH3 S O 2-NO2 S O 2-CO2CH(CH3)2 S O 2-SCE3 S O 4-Cl S O 4-F S O 4-CH3 S O 4-OCH3 S O 4-CO2CH3 S O Table II-O EMI78.1 R4 W Y 2-Cl O CH2 2-F O CH2 2-Br O CH2 2-CH3 O CH2 2-CH2CH2CH3 O CH2 2-NO2 O CH2 2-CO2CH3 O CH2 2-CO2CH2CH(CH3)2 O CH2 2-SCH3 O CH2 4-Cl O CH2 4-F O CH2 4-CH2CH2CH3 O CH2 4-CH3 O CH2 4-CH3O O CH2 4-NO2 O CH2 4-CO2CH(CH3)2 O CH2 4-SCH3 O CH2 2-S(CH2)3CH3 O CH2 2-Cl O O 2-F O O 2-Br O O 2-CH3 O O 2-CH2CH2CH3 O O 2-NO2 O O Table II-D (continued) R4 W Y 2-CO2CH3 O O 2-CO2CH2CH(CH3)2 O O 2-SCE3 O 0 4-C1 0 0 4-F 0 0 4-CH2CH2CH3 O O 4-CE3 O 0 4-CH3O O O 4-NO2 O O 4-CO2CH(CH3)2 O O 4-SCE3 O 0 2-S(CH2)3CH3 O O 2-Cl S CH2 2-F S CE2 2-CE3 S CE2 2-OCH3 S CH2 2-NO2 S CH2 2-CO2CH3 S CH2 2-SCE3 S CH2 4-C1 S CE2 4-Br S CE2 4-C2H5 S CH2 4-OCH3 S CH2 4-NO2 S CE2 4-CO2C2H5 S CH2 4-SC2H5 S CH2 2-C1 S O 2-F S O Table II-D (continued) R4 W Y 2-Br S O 2-C2H5 S O 2-OC2H5 S O 2-NO2 S O 2-CH2CH3 S O 2-SCH(CH3)2 S O 4-Cl S O 4-F S 0 4-CH3 S O 4-OCH3 S O 4-NO2 S O 4-CO2CH3 S O Table II-E EMI81.1 R4 W Y 4-Cl O CH2 4-Br 0 CH2 4-CH3 O CH2 4-OCH3 O CH2 4-NO2 O CH2 4-C02CE3 0 . CE2 4-CO2(CH2)4CH3 O CH2 4-SCH3 O CH2 2-Cl O CH2 2-F O CH2 2-Br CE2 2-CH(CH3)2 O CH2 2-CH2O O CH2 2-NO2 O CH2 2-COOC2H5 O CH2 2-SCH3 O CH2 4-SCH3CH3 O CH2 Table II-E (continued) R4 W Y 4-Cl O O 4-Br 0 0 4-CH3 O O 4-OCH3 O O 4-NO2 O O 4-CO2CH3 O O 4-CO2(CH2)4CH3 O O 4-SCH3 O O 2-Cl O O 2-F O O 2-Br O O 2-CH(CH3)2 O O 2-CH3O O O 2-NO2 O O 2-COOC2H5 O O 2-SCH3 O O 4-SCH2CH3 O O 2-Cl S CH2 2-F S CH2 2-Br S CH2 2-CH3 S CH2 2-OCH3 S CH2 2-NO2 S CH2 2-CO2CH3 S CH2 2-SCH3 S CH2 4-Cl S CH2 4-F S CH2 4-CH3 S CH2 4-OC2H5 S CH2 Table II-E (continued) R4 W Y 4-NO2 S CH2 4-CO2CH(CE3)2 S CE2 4-SC2H5 S CH2 2-Cl S O 2-F S O 2-Br S O 2-C2H5 S O 2-OCH(CE3)2 S O 2-NO2 S O 2-CO2CH3 S O 2-SCH3 S O 4-C1 S 0 4-Br S O 4-CH3 S O 4-OCH3 S O 4-NO2 S O 4-C02CE3 S O Example 10 2-Isopropylaminocarbonyl-N-[(6,7-dihydro-4-methyl- 5H-cyclopentapyrimidln-2-yl)aminocarbonyl]benzene- sulfonamide. To 21.2 ml of 25% trimethylaluminum in hexane (2.36 molar) under nitrogen is added 2.9 g of isopropyl amine in 100 ml of dried methylene chloride. The mixture is stirred at ambient temperature until evolution of methane gas ceases and then 19.5 g of methyl 2Ec(6,7-dihydro-4-methyl-5E-cyclopentapyrimidin- 2-yl)aminocarbonyl]aminosulfonylAbenzoatP and 200 ml of dry toluene is added. The resulting mixture is heated to distill off the methylene chloride and hexane, after which heating is continued at the reflux temperature of toluene. After 2. hours, the toluene is removed in vacuo, -and 200 ml of methylene chloride and 100 ml of 10% hydrochloric acid are added. The phases are separated, and the methylene chloride phase is washed once with water, dried over magnesium sulfate, and filtered, and the methylene chloride distilled to yield the desired compound. By using the procedure of Example 10 with an equivalent amount of an appropriately substituted benzoic acid ester and alkylaminodialkylaluminum, the compounds of Table III can be prepared. Table II-A EMI85.1 R3 R9 R8 W X Y H CH3 H O CH3 CH2 H C2H5 H O CH3 CH2 H CH(CH3)2 H O CH3 CH2 5-Cl CH3 H O CH3 CH2 6-Cl CH(CH3)2 H O CH3 CH2 H CH2CH2CH2CH3 H O CH3 CH2 H CH(CH3)2 H O OCH3 CH2 5-Cl C2H5 H O OCH3 CH2 6-Cl CH2CH2CH3 H O OCH3 CH2 H CH(CH3)2 CH3 O CH3 CH2 H C2H5 C2H5 O CH3 CH2 H CH(CH3)2 CH(CH3)2 O CH3 CH2 H (CH2)4H (CH2)4H O CH3 CH2 H H H O CH3 CH2 H CH3 H O H CH2 5-C1 C2E5 H O H CE2 6-Cl CH(CH3)2 H O H CH2 H CH2CH2CH3 CH3 O H CH2 H C2H5 C2H5 O H CH2 H H H O H CH2 H CH3 CH3 O Cl CH2 H C2H5 H O Cl CH2 H CH(CH3)2 H O Cl CH2 H CH3 H O Cl CH2 Table III-A (continued) R3 R9 R8 W X Y 5-Cl CH3 CH3 O OC2H5 CH2 6-Cl C2H5 C2H5 O OC2H5 CH2 H -CH2CH2CH2CH2CH2- O OC2H5 CH2 H CH3 H O CH3 O H C2H5 H O CH3 O H CH(CH3)2 H O CE3 O 5-Cl CE3 H O CE3 o 6-Cl CH(CH3)2 H O CH3 O H CH2CH2CH2CH3 H O CH3 O H CH(CH3)2 H O OCE3 O 5-Cl C2H5 H O OCE3 O 6-Cl CH2CH2CH3 H O OCH3 O H CH(CH3)2 CH3 O CH3 O H C2H5 C2H5 O CH3 O H CH(CH3)2 CH(CH3)2 O CH3 O H (CH2)4H (CH2)4H O CH3 O H H H O CE3 O H CH3 H O H O 5-Cl CH3 H O H O 6-Cl C2E5 H O H O H CH2CH2CH3 CH3 O H O H CH(CH3)2 C2H5 O H O H (CH2)4H CH3 O H O H H H O H- O H CH3 CH3 O Cl O H C2H5 H O Cl O H CH(CH3)2 H O Cl O H CH3 H O Cl O 5-Cl CH3 CH3 O C2H5 O 6-Cl C2H5 C2H5 O OC2H5 O H -CH2CH2CH2CH2CH2- O OC2H5 O Table II-A (continued) R3 R9 R8 W X Y H H H S CH3 O H CH3 H S CH3 O H CH(CH3)2 H S CH3 O H CHC2H5 H S CH3 O CH3 H CE3 CE3 S CE3 O H CH(CH3)2 CH(CH3)2 S CH3 O 5-C1 C2E5 H S CH3 O 6-Cl CH3 CH3 S CH3 O H H H S OCE3 O H CH3 H S OCH3 O H CE3 CH3 S OCE3 O 5-Cl CH3 CH3 S OCH3 O H CH3 H S H O H CH3 C2H5 S H O H CH(CH3)2 CH(CH3)2 S H O H CE3 H S Cl O H CE3 CE3 S Cl O 6-Cl CH2CH2CH3 H S Cl O H -CH2CH2CH2CH2- S Cl O H H H S OC2H5 0 H CE3 CE3 S OC2E5 0 5-C1 CH3 H S OC2H5 H -CH2CH2O-CH2CH2- S OC2H5 O H H H S CE3 O .H CE3 H S CH3 O H C2H5 H S CH3 O H CE3 CE3 S CE3 O H CH3 C2H5 S CH3 O 6-C1 -CH(Cv3)2 H S CH3 O 5-Cl CH3 CH3 S CH3 O Table III-A (continued) EMI88.1 <tb> <SEP> R3 <SEP> R8 <SEP> Rg <SEP> W <SEP> X <tb> <SEP> o <tb> H <SEP> H <SEP> H <SEP> S <SEP> OCE3 <SEP> O <tb> H <SEP> CE3 <SEP> H <SEP> S <SEP> OCR3 <SEP> 0 <tb> H <SEP> C2H5 <SEP> Cz <SEP> S <SEP> OCE3 <SEP> O <tb> 5-C1 <SEP> CH3 <SEP> -CE(CX3)2 <SEP> S <SEP> OCE3 <SEP> 0 <tb> H <SEP> CE3 <SEP> H <SEP> S <SEP> H <SEP> O <tb> H <SEP> -(CH2)3CH3 <SEP> H <SEP> S <SEP> H <SEP> O <tb> H <SEP> CE3 <SEP> CE3 <SEP> S <SEP> H <SEP> o <tb> H <SEP> C2R5 <SEP> H <SEP> S <SEP> C1 <SEP> O <tb> H <SEP> C2E5 <SEP> 3 <SEP> S <SEP> C1. <SEP> O <tb> g <SEP> -CH2CE2CE2CH2CE2- <SEP> S <SEP> C1 <SEP> O <tb> 5-C1 <SEP> CE <SEP> 3 <SEP> E <SEP> S <SEP> Cl <SEP> O <tb> <SEP> t <tb> <SEP> CE3 <tb> H <SEP> H <SEP> H <SEP> S <SEP> 0C2H5 <SEP> O <tb> H <SEP> CH3 <SEP> CH3 <SEP> S <SEP> OC2zq <SEP> O <tb> H <SEP> -CH2CH2OCH2CH2- <SEP> S <SEP> OC2Hg <SEP> O <tb> E <SEP> -CH(CE3)2 <SEP> CX3 <SEP> S <SEP> 0C2H5 <SEP> O <tb> 6-Cl <SEP> C2H5 <SEP> C2a5 <SEP> S <SEP> C,C2H5 <SEP> O <tb> Table III-B EMI89.1 EMI89.2 <tb> <SEP> R3 <SEP> Rg <SEP> R8 <SEP> W <SEP> X <SEP> Y <tb> E <SEP> C2H5 <SEP> H <SEP> O <SEP> CE3 <SEP> CH2 <tb> H <SEP> CE(CH3)2 <SEP> H <SEP> O <SEP> CH3 <SEP> CH2 <tb> H2CB2CH3 <SEP> H <SEP> <SEP> CE3 <SEP> CH2 <tb> <SEP> 6/cm3 <tb> <SEP> 5-C1 <SEP> CH <SEP> \ <SEP> H <SEP> <SEP> CE3 <SEP> CH2 <tb> <SEP> C2E5 <tb> H <SEP> CE3 <SEP> CH3 <SEP> <SEP> CE3 <SEP> C <SEP> 2 <tb> C2H5 <SEP> CR3 <SEP> <SEP> CH3 <SEP> CH2 <tb> H <SEP> C2H5 <SEP> C2H5 <SEP> <SEP> CH3 <SEP> CH2 <tb> H <SEP> H <SEP> H <SEP> <SEP> CH3 <SEP> CH2 <tb> H <SEP> C2H5 <SEP> H <SEP> O <SEP> CE3 <SEP> O <tb> H <SEP> CE(CH3)2 <SEP> H <SEP> 0 <SEP> CH3 <SEP> O <tb> H <SEP> CH2CH2CH3 <SEP> H <SEP> O <SEP> CE3 <SEP> O <tb> <SEP> CH3 <tb> 5-C1 <SEP> CE <SEP> H <SEP> 0 <SEP> CE3 <SEP> 0 <tb> 5-C1 <SEP> CE <SEP> E <SEP> o <SEP> CE3 <SEP> O <tb> <SEP> "'\'C2H5 <tb> H <SEP> CE3 <SEP> CE3 <SEP> o <SEP> CE3 <SEP> O <tb> H <SEP> C2E5 <SEP> CE3 <SEP> o <SEP> CR3 <SEP> o <tb> H <SEP> C2E5 <SEP> C2H5 <SEP> o <SEP> CE3 <SEP> 0 <tb> H <SEP> H <SEP> H. <SEP> o <SEP> CH3 <SEP> o <tb> H <SEP> C <SEP> H <SEP> CK3 <SEP> o <SEP> OCH3 <SEP> CR2 <tb> H <SEP> CH(CH3)2 <SEP> H <SEP> O <SEP> OCE3 <SEP> 2 <tb> H <SEP> CH3 <SEP> CH3 <SEP> O <SEP> OCH3 <SEP> O <tb> H <SEP> C <SEP> 2E5 <SEP> C <SEP> 2R5 <SEP> 0 <SEP> OCE3 <SEP> O <tb> Table III-B (continued) R3 R9 R8 W X Y H CH3 H S CH3 CH2 H CH(CH3)2 E S CE3 CE2 H -CH2CH(CH3)2H S CH3 CH2 5-Cl -C2H5 H S CH3 CH2 H CE3 CE3 S CE3 CH2 H C2H5 CH3 S CH3 CH2 6-Cl CE3 CE3 S CE3 CE2 H H H S OCH3 CH2 H CH3 H S OCH3 CH2 H CE3 CE3 S OCX3 CH2 H C2H5 -CH(CH3)2 S OCH3 CH2 H CE3 H S CE3 O H -CH2CH2CH3 E S CH3 O H -CH2CH2CH2CH2- S CH3 O 5-Cl CH3 CH3 S CH3 O H C2H5 CH3 S CH3 O H C2H5 H S OCH3 O H CH2(CH3)3 H S OCH3 O H CH3 CH3 S OCH3 O H CH3 CH2CH2CH3 S OCH3 O 6-Cl -CH2CH2CH2CH2CH2- S OCE3 O By using the procedures described above and the appropriate reactants and 4-chloro or 4-ethoxy-5,6dihydrofuro[2,3-d]pyrimidin-2-amine or 4-chloro or 4-ethoxy-6,7-dihydro-5H-cyclopentapyrimidin-2amine, the compounds of Table IV-A can be prepared. Similarly, compounds of Table IV-B can be prepared using the appropriate reactants and starting from 6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amine substituted in the 4-position with hydrogen, chlorine or ethoxy. Table IV-A EMI91.1 EMI91.2 <tb> <SEP> R2 <SEP> R3 <SEP> R, <SEP> -W <SEP> X <SEP> Y <SEP> m.p. <tb> H <SEP> H <SEP> - <SEP> O <SEP> C1 <SEP> O <tb> <SEP> CR <tb> C 2CH3 <SEP> H <SEP> - <SEP> O <SEP> 0 <SEP> C1 <SEP> 0 <SEP> 215-2190 <tb> <SEP> CR <tb> Cm2 <SEP> 3 <SEP> 5-C1 <SEP> - <SEP> O <SEP> C1 <SEP> CH2 <tb> SO <SEP> N(CH3)2 <SEP> H <SEP> O <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> Cl <SEP> H <SEP> - <SEP> 2 <SEP> 0C2H5 <SEP> 5 <tb> NO2 <SEP> H <SEP> - <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> S02CH3 <SEP> H <SEP> - <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> CO <SEP> 22 <SEP> CH=CR2 <SEP> H <SEP> O <SEP> OC <SEP> 2R5 <SEP> O <tb> CON(CH3)2 <SEP> H <SEP> o <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> <SEP> O <SEP> OCH3 <tb> H <SEP> H <SEP> O <SEP> 2 <SEP> O <tb> <SEP> CH3 <tb> F <SEP> H <SEP> - <SEP> O <SEP> OC <SEP> 2H5 <SEP> CH2 <tb> <SEP> 2 <tb> <SEP> - <SEP> - <SEP> 2-CO2CH3 <SEP> O <SEP> C1 <SEP> O <tb> <SEP> 4-C02CH2C3 <SEP> O <SEP> C1 <SEP> CH2 <tb> <SEP> - <SEP> - <SEP> 4-NO2 <SEP> O <SEP> Cl <SEP> O <tb> <SEP> - <SEP> - <SEP> 2CH3 <SEP> 0 <SEP> O <SEP> C1 <SEP> O <tb> - <SEP> - <SEP> 2-Br <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> - <SEP> - <SEP> 2CH3 <SEP> O <SEP> OC2H5 <SEP> CH2 <tb> - <SEP> - <SEP> 2-CO2CH(CH3)2 <SEP> 0 <SEP> OC2H5 <SEP> O <tb> <SEP> - <SEP> - <SEP> 4-F <SEP> 0 <SEP> OC2H5 <SEP> CH2 <tb> - <SEP> - <SEP> 2-No2 <SEP> 0 <SEP> OC2H5 <SEP> CH2 <tb> Table IV-A (continued) EMI92.1 <tb> <SEP> R2 <SEP> R3 <SEP> w <SEP> x <SEP> rn.p. <tb> Cl <SEP> a <SEP> - <SEP> S <SEP> Cl <SEP> 0 <tb> NO <SEP> H <SEP> - <SEP> S <SEP> CI <SEP> O <tb> <SEP> 2 <tb> CO2CH3 <SEP> H <SEP> z <SEP> S <SEP> Cl <SEP> 0 <tb> SO2N(CE3)2 <SEP> E <SEP> . <SEP> S <SEP> C1 <SEP> O <tb> Cl <SEP> 5-Cl <SEP> <SEP> S <SEP> Cl <SEP> O <tb> C1 <SEP> H <SEP> - <SEP> S <SEP> C2HS <SEP> O <tb> 2 <SEP> H <SEP> - <SEP> S <SEP> C2H5 <SEP> 0 <tb> CO2C2R5 <SEP> E <SEP> <SEP> S <SEP> OC2s5 <SEP> O <tb> <SEP> OCR <tb> <SEP> /3 <tb> CON <SEP> H <SEP> - <SEP> S <SEP> OC2 <SEP> S <SEP> <tb> <SEP> ca3 <tb> <SEP> 3 <tb> OCH3 <SEP> 5-eCE3 <SEP> - <SEP> S <SEP> OC <SEP> 2H5 <SEP> 0 <tb> 5CR3 <SEP> H <SEP> - <SEP> S <SEP> OC2E5 <SEP> 0 <tb> SO <SEP> C <SEP> H <SEP> H <SEP> O <SEP> S <SEP> C2R5 <SEP> 0 <tb> Cl <SEP> E <SEP> <SEP> S <SEP> Cl <SEP> CR2 <tb> 2 <SEP> H <SEP> - <SEP> S <SEP> C1 <SEP> CR2 <tb> CO2CE3 <SEP> R <SEP> > <SEP> S <SEP> Cl <SEP> CE2 <tb> Cl <SEP> 5-C1 <SEP> - <SEP> S <SEP> Cl <SEP> CR2 <tb> SO2N(C2z5) <SEP> 2 <SEP> b <SEP> S <SEP> C1 <SEP> CR2 <tb> CI <SEP> H <SEP> - <SEP> S <SEP> OC2a5 <SEP> ClI2 <tb> N0 <SEP> a <SEP> E <SEP> S <SEP> OC2X5 <SEP> CR2 <tb> C02CE3 <SEP> H <SEP> - <SEP> S <SEP> OC2H5 <SEP> CH2 <tb> SCE3 <SEP> 5SCH3 <SEP> - <SEP> S <SEP> OC <SEP> 2E5 <SEP> CH2 <tb> CONCCR3)z <SEP> H <SEP> - <SEP> S <SEP> OC2R5 <SEP> CR2 <tb> SO2NCCR3)2 <SEP> K <SEP> - <SEP> S <SEP> OC2H5 <SEP> CR2 <tb> - <SEP> - <SEP> 2-Cl <SEP> S <SEP> C1 <SEP> O <tb> - <SEP> - <SEP> 4-F <SEP> S <SEP> C1 <SEP> O <tb> - <SEP> - <SEP> 2-NO2 <SEP> S <SEP> Cl <SEP> 0 <tb> - <SEP> -- <SEP> 4-C02Ca3 <SEP> S <SEP> C1 <SEP> O <tb> - <SEP> * <SEP> 2-OClI3 <SEP> S <SEP> C1 <SEP> O <tb> - <SEP> - <SEP> 2CH3 <SEP> S <SEP> C1 <SEP> O <tb> Table IV-A (continued) R2 R3 R4 W X Y m.p. - 4-Cl S Cl CH2 - 4-NO2 S Cl CH2 - 2-CO2CH3 S Cl CH2 - 4-CO2CG(CH3)2 S Cl CH2 - 2-Cl S OC2H5 O - 2-NO2 S OC2H5 O - 4-CO2C2H5 S OC2H5 O - 4-SCH3 S OC2H5 O - 2-OCH3 S OC2H5 O - 4-CH3 S OC2H5 O - 4-F S OC2H5 CH2 - - 2-Br S OC2H5 CH2 - 2-NO2 S C2H5 CH2 - 4-CO2CH3 S OC2H5 CH2 - 2-C2H5 S OC2H5 CH2 Table IV-B EMI94.1 EMI94.2 <tb> <SEP> R <SEP> R <SEP> R <tb> <SEP> 2 <SEP> 3 <SEP> 4 <SEP> w <SEP> x <tb> CO <SEP> CR <SEP> H <SEP> - <SEP> o <SEP> Cl <tb> CO <SEP> 2CR3 <SEP> 5-Cl <SEP> - <SEP> 0 <SEP> C1 <tb> SOg(CH3) <SEP> 2 <SEP> H <SEP> - <SEP> O <SEP> OC2R3 <tb> <SEP> L <SEP> L <tb> C02CH2CH=CH2 <SEP> H <SEP> - <SEP> O <SEP> C2H5 <tb> CONCCR3)2 <SEP> H <SEP> - <SEP> O <SEP> 5 <tb> <SEP> O <SEP> / <SEP> OCR3 <tb> -C-N? <SEP> H <SEP> < <SEP> O <SEP> OC <SEP> 2R5 <tb> <SEP> CH3 <tb> - <SEP> - <SEP> 2-CO <SEP> 2CR3 <SEP> 0 <SEP> C1 <tb> 4-C02CH2CH3 <SEP> o <SEP> C1 <tb> - <SEP> - <SEP> 4-NO2 <SEP> 0 <SEP> C1 <tb> 2-CH30 <SEP> 0 <SEP> Cl <tb> - <SEP> - <SEP> 2-Br <SEP> 0 <SEP> OC2H, <tb> - <SEP> - <SEP> 2-CR3 <SEP> O <SEP> OC <SEP> 2R5 <tb> 2-C02CH(CH3)2 <SEP> O <SEP> C2H5 <tb> - <SEP> - <SEP> 4-F <SEP> 0 <SEP> 5 <tb> <SEP> - <SEP> 2-N02 <SEP> 2 <SEP> OC <SEP> 2R5 <tb> Table IV-B (continued) EMI95.1 <tb> <SEP> R2 <SEP> R3 <SEP> R <SEP> W <SEP> X <tb> <SEP> 2 <SEP> 3 <SEP> 4 <SEP> w <SEP> X <tb> CO <SEP> CR <SEP> H <SEP> - <SEP> S <SEP> C1 <tb> 502N(CH3) <SEP> 2 <SEP> H <SEP> - <SEP> S <SEP> C1 <tb> C02C2H5 <SEP> H <SEP> - <SEP> S <SEP> OC2H5 <tb> <SEP> OCH3 <tb> CON <SEP> H <SEP> - <SEP> S <SEP> OC <SEP> H <tb> <SEP> CH3 <tb> C 2CH3 <SEP> H <SEP> - <SEP> S <SEP> C1 <tb> SO2N(C2F,3)2 <SEP> H <SEP> - <SEP> S <SEP> C1 <tb> CO <SEP> 2CR'3 <SEP> H <SEP> - <SEP> S <SEP> OC2HS <tb> CON(CH3) <SEP> ) <SEP> H <SEP> - <SEP> S <SEP> OC2H5 <tb> SO2N(CR3)2 <SEP> H <SEP> - <SEP> S <SEP> 0C2H5 <tb> <SEP> - <SEP> - <SEP> 2-C1 <SEP> S <SEP> C1 <tb> <SEP> - <SEP> - <SEP> 4-F <SEP> S <SEP> Cl <tb> <SEP> - <SEP> ¯ <SEP> 2-N 2 <SEP> S <SEP> C1 <tb> <SEP> - <SEP> - <SEP> 4-CO <SEP> CR <SEP> S <SEP> C1 <tb> <SEP> - <SEP> - <SEP> 2-OCH3 <SEP> S <SEP> Cl <tb> <SEP> - <SEP> - <SEP> 2-CR3 <SEP> S <SEP> C1 <tb> Table IV-B (continued) R2 R3 R4 W X - - 4-Cl S Cl - - 4-NO2 S Cl - - 2-CO2CH3 S S Cl - 4-CO2CH(CH3)2 S Cl - 2-Cl S OC2H5 - 2-NO2 S OC2H5 - 4-CO2C2H5 S OC2H5 - 4-SCH3 S OC2H5 - 2-OCH3 S OC2H5 - 4-CH3 S OC2H5 - 4-F S OC2H5 - - 2-Br S OC2H5 - 2-NO2 S OC2H5 - 4-CO2CH3 S OC2H5 - 2-C2H5 S OC2H5 Table IV-B(continued) EMI97.1 <tb> <SEP> R2 <SEP> R3 <SEP> R4 <SEP> W <SEP> x <tb> <SEP> CO <SEP> 2CH3 <SEP> H <SEP> - <SEP> O <SEP> H <tb> <SEP> 2 <SEP> 3 <SEP> 5-C1 <SEP> - <SEP> O <SEP> H <tb> <SEP> S02N(CH3)2 <SEP> H <SEP> - <SEP> O <SEP> H <tb> C02CH2CH=CH2 <SEP> H <SEP> - <SEP> O <SEP> H <tb> CoN:(CR3)2 <SEP> H <SEP> - <SEP> O <SEP> H <tb> <SEP> :H, <tb> H <SEP> / <SEP> 0 <SEP> H <tb> -C-X <SEP> H <SEP> - <SEP> O <SEP> H <tb> <SEP> \ <SEP> CH3 <tb> <SEP> - <SEP> - <SEP> 2-CO <SEP> CR <SEP> o <SEP> H <tb> <SEP> - <SEP> - <SEP> 4-CO <SEP> CR <SEP> 0 <SEP> H <tb> <SEP> - <SEP> - <SEP> 4-NO2 <SEP> 0 <SEP> H <tb> - <SEP> - <SEP> 2-CR <SEP> O <SEP> H <tb> <SEP> 3 <tb> <SEP> - <SEP> - <SEP> 2-Br <SEP> O <SEP> H <tb> <SEP> - <SEP> - <SEP> 2-CR3 <SEP> 0 <SEP> H <tb> <SEP> - <SEP> - <SEP> 2-C02CH(CH3)2 <SEP> 0 <SEP> H <tb> <SEP> - <SEP> - <SEP> 4-F <SEP> O <SEP> H <tb> <SEP> - <SEP> - <SEP> 2-NO2 <SEP> 0 <SEP> H <tb> Table IV-B (continued) EMI98.1 <tb> <SEP> R2 <SEP> R3 <SEP> R4 <SEP> W <SEP> X <tb> CO <SEP> CR <SEP> H <SEP> < <SEP> S <SEP> H <tb> C 2CH3 <SEP> 5-Cl <SEP> <SEP> S <SEP> H <tb> <SEP> SO2N(CR3)2 <SEP> H <SEP> S <SEP> H <tb> C02CH2CH=CH <SEP> 2 <SEP> H <SEP> - <SEP> S <SEP> H <tb> CON(CH3)2 <SEP> H <SEP> - <SEP> S <SEP> H <tb> <SEP> O <SEP> SOCH, <tb> <SEP> It <tb> -C-N <SEP> H <SEP> < <SEP> S <SEP> H <tb> <SEP> cH3 <tb> <SEP> 2-CO,CH, <SEP> S <SEP> H <tb> <SEP> - <SEP> 4-CO <SEP> CR <SEP> CR <SEP> S <SEP> H <tb> <SEP> - <SEP> ¯ <SEP> 4-N 2 <SEP> S <SEP> H <tb> <SEP> - <SEP> - <SEP> 2-CR3 <SEP> O <SEP> S <SEP> H <tb> <SEP> - <SEP> 2-Br <SEP> S <SEP> H <tb> <SEP> - <SEP> < <SEP> 2-CR3 <SEP> - <SEP> S <SEP> H <tb> <SEP> ¯ <SEP> -- <SEP> 2-Co2CH(CH3) <SEP> 2 <SEP> S <SEP> H <tb> <SEP> - <SEP> 4-F <SEP> S <SEP> H <tb> 2-N02 <SEP> S <SEP> H <tb> Compounds of Formula II are prepared according to the procedures of Equations 2 and 5 and Examples 11, 12 and 13 wherein temperatures are given in degrees centigrade. Example 11 Methyl N'-(2-chlorophenylsulfonyl)-N-(5,6-dihydro-4 methylfuro [2, 3-d] pyrimidin-2-yl) carbamimidothioate To a suspension of 3.85 g 2-chloro-N-[(5,6dihydro-2-methylfuro[2,3-d]pyrimidine-2-yl)amino thioxo,methyl]benzenesulfonamide in 150 ml of anhydrous tetrahydrofuran was added 4.3 ml of 3M NaOCE3/CH3OH solution. The reaction reaction mixture was refluxed for 1.25 hour, whereupon 1.85 g of methyl iodide in 10 ml of anhydrous tetrahydrofuran was added. After refluxing and stirring for an additional 12 hours, the reaction mixture was cooled, solvent was removed under vacuum and the residue was recrystallized from acetonitrile to yield 1 g.of the product. Example 12 Methyl 2-{[1-(6,7-dihydro-4-methoxy-5H-cyclopenrapyrimi din-2-yl-amino)-l-(ethylthio)methylenej2minosulfonyl] benzoate To a suspension at 4.2 g of methyl 2-[[(6,7 dihydro-4-methoxy-5E-cycropentapyrimin-2-yl)?menothioXo- methyl)aminosulfonyl]benzoate' in 200 ml of anhydrous tetrahydrofuran was added 4.3 ml of 3M NaOCH3/CR3OE solution. The reaction was refluxed for 5 min. whereupon 2 g of ethyl iodide in 10 ml of anhydrous tetrahydrofuran was added. After refluxing and stirring for an additional 6 hours, the reaction mixture was cooled, solvent was removed under vacuum and the residue was recrystallized from acetonitrile to yield 0.5 g of the product. Example 13 Methyl N-(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2yl)N'-(2,5-dimethoxyphenylsulfonyl)carbamimidothioate 1.5 grams. of 6,7-dihydro-4-methyl-5H-cyclopenta- pyrimidin-2-amine was dissolved in a mixture of 20 ml of anhydrous tetrahydrofuran and 60 ml of anhydrous dimethylformamide. 0.48 grams of sodium hydride (50% mineral oil dispersion) was added. The reaction was stirred until hydrogen evolution ceased. 2.75 grams of N(2,5- dimethoxyphenylsulfonyl) carbonimidodithoic acid, S,5- dimethyl ester was added all at once. The reaction mixture was stirred 24 hours at ambient temperature. The mixture was poured into 300 ml of water and acidi field to pE 5 with 20% hydrochloric acid. The mixture was filtered. The solid obtained was recrystallized from ethyl acetate to yield 1 g of product. Table V-a EMI101.1 R12 R2 R3 X Y m.p. CH3 Cl 5-Cl CH3O O C3CH2 Cl 5-Cl CH3 O Ch3 Cl 5-Cl CH3CH2O O CH3 CH3 5-CH3 H O CH3 CH3 5-CH3 CH3 O CH3 CH3 H CH3O O CH3 CH3 H CH3 O CH3(CH2)3 H H CH3O O CH3 H H CH3 O CH3CH2 Cl H H O CH3 F H CH3 O CH3 CH3O 5-Cl CH3 O CH3 Cl 6-Cl CH3 O CH3 Cl 5-CH3 H O CH3 F H CH3O O CH3 CH3O 5-Cl CH3O O CH3 NO2 H CH3 O CH3 NO2 H CH3O O CH3 SO2N(CH3)2 H CH3 O CH3 CH3SO- H CH3 O CH3 Cl 3-Cl H O (CH3)2CHCH2 CH3O 5-CH3O CH3 O CH3 CF3 H CH3 O CH3 CH3O H Cl O CH3 H 3-Cl CH3 O CH3 H 3-F CH3 O Table V-a (continued) R12 R2 R3 X Y m.p. CH3 H 3-CH3 CH3 O (CH3)2CH H 3-Br CH3O O CH3 SO2N(OCH3)CH3 H CH3 O CH3 F 6-F H O CGH3 F 5-F CH3 O CH3 SO2CH2CF3 H CH3 O CH3 SO2OCH2CCl3 H H O CH3 Cl 5-CH3 CH3 O CH3 Cl H CH3 CH2 CH3 Cl 5-Cl CH3CH2O CH2 CH3 Cl 3-F CH3 CH2 CH3CH2 Br 5-Br Cl CH2 CH3 Cl 6-Cl CH3 CH2 CH3 CH3S H Cl CH2 CH3 CH3 5-Br CH3 CH2 CH3CH2 CH3 5-Cl CH3CH2O CH2 CH3 CH3 5-F CH3 CH2 CH3 CH3O 5-Cl CH3CH2O CH2 (CH3)2CH H H CH3CH2O CH2 CH3CH2 Cl H CH3CH2O CH2 CH3CH2 Cl 5-Cl CH3CH2O CH2 CH3CH2 CH3O 5-CH3O Cl CH2 CH3 CH3 5-CH3 CH3CH2O CH2 CH3 Cl 6-Cl Cl CH2 CH3CH2 Br H CH3 CH2 CH3 CH3 H Cl CH2 CH3 CF3 H CH3CH2O CH2 CH3 NO2 H CH3CH2O CH2 CH3 F H H CH2 CH3 F 6-F Cl CH2 CH3CH2 Cl 6-Cl CH3CH2O CH2 CH3 Cl H Cl CH2 CH3 Br H CH3 CH2 Table V-a (continued) EMI103.1 <tb> <SEP> R <SEP> R <SEP> R <tb> <SEP> 12 <SEP> 2 <SEP> 3 <SEP> X <SEP> Y <SEP> rn.p. <tb> CE <SEP> CR <SEP> N02 <SEP> H <SEP> CR3 <SEP> CH2 <tb> CR3(CR2)2 <SEP> NO2 <SEP> H <SEP> CR <SEP> 0 <SEP> CR2 <tb> CX3CH2(CH3)CH <SEP> C1 <SEP> 5-C1 <SEP> Cur3 <SEP> 0 <SEP> CH2 <tb> (CH3)2cHcE2 <SEP> NO2 <SEP> H <SEP> H <SEP> CH2 <tb> CH3 <SEP> Cm3 <SEP> 502 <SEP> 5-C2X5 <SEP> CR3 <SEP> 0 <SEP> CH2 <tb> CH3 <SEP> CR3 <SEP> SO2 <SEP> 6-C1 <SEP> CH2CH30 <SEP> CH2 <tb> (CH3)2CH <SEP> Cl <SEP> 'H <SEP> CE30 <SEP> CH2 <tb> CH3(CH2)3 <SEP> C1 <SEP> H <SEP> C1 <SEP> 0 <tb> (CH3)2cHcH2 <SEP> Cl <SEP> H <SEP> CE3 <SEP> CH2 <tb> CE3(CH2)3 <SEP> C1 <SEP> H <SEP> CR30 <SEP> CH2 <tb> (CK3)2CH <SEP> Cm30 <SEP> 5-CR30 <SEP> CR30 <SEP> CR2 <tb> CH3CH2 <SEP> CR3 <SEP> 0 <SEP> 5-CR30 <SEP> CR30 <SEP> 0 <tb> CR3 <SEP> (CE2)5 <SEP> Cl <SEP> H <SEP> CR30 <SEP> CR2 <tb> CR3(CR2)3CH, <SEP> CR30 <SEP> 5-CH3Q <SEP> g <SEP> O <tb> <SEP> cE3 <tb> CH3(CH2)3 <SEP> CR3 <SEP> H <SEP> CR30 <SEP> O <tb> (CH3)2CH <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 0 <tb> CR3(CR2)4 <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> (CH3)2CH <SEP> C1 <SEP> H <SEP> CH3 <SEP> CH2 <tb> (CE3)2cHcH2 <SEP> Cl <SEP> E <SEP> CH3 <SEP> CH2 <tb> CR3CR2CR, <SEP> C1 <SEP> H <SEP> H <SEP> CH2 <tb> <SEP> CH3 <tb> CH3 <SEP> Cl <SEP> H <SEP> Cur3 <SEP> 0 <SEP> 0 <tb> n-C7H15 <SEP> Cl <SEP> H <SEP> CH3 <SEP> CH2 <tb> n-ClOH21 <SEP> Cl <SEP> H <SEP> Cl <SEP> 0 <tb> C,(CH2)7CH3 <SEP> C1 <SEP> H <SEP> CH3 <SEP> 0 <tb> CH3 <tb> CH2CB20CB3 <SEP> Cl <SEP> H <SEP> CH3 <SEP> CH2 <tb> <SEP> 0 <tb> <SEP> re <tb> CH3 <SEP> C"5CR3 <SEP> H <SEP> CR3 <SEP> 0 <tb> <SEP> 0 <tb> CHICS <SEP> CSC <SEP> 2H5 <SEP> H <SEP> Coif30 <SEP> 0 <tb> Table V-a (continued) EMI104.1 <tb> <SEP> R12 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> mep. <tb> <SEP> 1L <SEP> L <tb> CR2CR2 <SEP> OCR2 <SEP> CR3 <SEP> C02CE3 <SEP> H <SEP> ca3 <SEP> cur2 <tb> CR2CR2CR2OCR3 <SEP> C02CX3 <SEP> H <SEP> CR3 <SEP> Caz <tb> CE2C02CE3 <SEP> C1 <SEP> H <SEP> R <SEP> Ci2 <tb> CR2CO2CR(CR3)2 <SEP> Cl <SEP> H <SEP> CR3 <SEP> CR2 <tb> CRCO2n-C4'R9 <SEP> C1 <SEP> H <SEP> CR3 <SEP> CR2 <tb> CXC02CE3 <SEP> Cl <SEP> H <SEP> C1 <SEP> 0 <tb> CH3 <tb> CR,-CO2CR(CR3)2 <SEP> F <SEP> H <SEP> CH3 <SEP> 0 <tb> cE3 <tb> <SEP> CE2CN <SEP> Cl <SEP> H <SEP> CR3 <SEP> 0 <tb> -CR2COOR <SEP> Cl <SEP> H <SEP> CR3 <SEP> 0 <tb> -CECOOH <SEP> Cl <SEP> H <SEP> C1 <SEP> 0 <tb> <SEP> cE3 <tb> Ca2-CR5 <SEP> Cl <SEP> H <SEP> CH3 <SEP> O <tb> CR,-C6R5 <SEP> Cl <SEP> H <SEP> CE3 <SEP> O <tb> CR <tb> CH2 <SEP> t <SEP> C1 <SEP> C1 <SEP> E <SEP> E <SEP> <tb> CE2 <SEP> e <SEP> Ça3 <SEP> Cl <SEP> H <SEP> CR3 <SEP> 0 <tb> CE2CN <SEP> C02CE3 <SEP> H <SEP> CR3 <SEP> 0 <tb> 2CRCR2 <SEP> CH2 <SEP> C 2CX3 <SEP> H <SEP> CH3 <SEP> 0 <tb> -CR2CRCR2 <SEP> Cl <SEP> H <SEP> C1 <SEP> 0 <tb> <SEP> cE2cE-cx-ca3 <SEP> C1 <SEP> H <SEP> ca3o <SEP> 0 <tb> CE2C=CE <SEP> CE31CEZ-CE <SEP> CO2CR(CR3)2 <SEP> H <SEP> H <SEP> O <tb> CR2C-CR <SEP> Cl <SEP> H <SEP> CR3 <SEP> CH2 <tb> Table V-a (continued) EMI105.1 <tb> <SEP> R12 <SEP> R2 <SEP> F3 <SEP> X <SEP> Y <tb> CH2C'-C-CE3 <SEP> CO <SEP> CR <SEP> H <SEP> CR3 <SEP> CH2 <tb> -CH-CH-C(CH3)2 <SEP> CO2CR3 <SEP> H <SEP> CH3 <SEP> CR2 <tb> <SEP> CH3 <tb> -CH2C-C-C2H5 <SEP> CO2CH3 <SEP> H <SEP> H <SEP> CH2 <tb> -CE2CE2CE(CE3)2 <SEP> Cl <SEP> H <SEP> CR3 <SEP> CH2 <tb> -CR, <SEP> CR <SEP> CR <SEP> CR <SEP> C1 <SEP> H <SEP> CR3 <SEP> CR2 <tb> <SEP> CH3 <tb> -(CR2)5CR3 <SEP> Cl <SEP> H <SEP> CR3O <SEP> 0 <tb> -(CR2)7CR3 <SEP> C1 <SEP> H <SEP> CE30 <SEP> 0 <tb> n-C12H25 <SEP> C1 <SEP> o <SEP> C1 <SEP> 0 <tb> -CR2CN <SEP> C1 <SEP> H <SEP> CR3 <SEP> 0 <SEP> CH2 <tb> -CH2COOH <SEP> F <SEP> H <SEP> Cm30 <SEP> CH2 <tb> -CHCOOH <SEP> CR30 <SEP> 5-CE3 <SEP> 0 <SEP> CE <SEP> 0 <SEP> 0 <tb> <SEP> CH3 <tb> -CE2CN <SEP> Cr3 <SEP> H <SEP> CH3 <SEP> CE2 <tb> CE3 <SEP> Cm30 <SEP> 3-CR3 <SEP> 0 <SEP> CR3 <SEP> 0 <SEP> 0 <tb> -CH2CE <SEP> F <SEP> H <SEP> H <SEP> O <tb> <SEP> 9 <SEP> CH2 <SEP> NO2- <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> 1 <tb> ClCR2 <SEP> Br <SEP> 5-Br <SEP> CH3 <SEP> 0 <tb> -CE2COOH <SEP> CON(CH3)2 <SEP> H <SEP> CR3 <SEP> 0 <SEP> 0 <tb> <SEP> CE3 <tb> <SEP> C1 <tb> <SEP> X <SEP> CH2- <SEP> Cl <SEP> 5-Cl <SEP> cE3 <SEP> CR2 <tb> <SEP> C1 <tb> <SEP> cE3 <tb> <SEP> CR2- <SEP> CR3 <SEP> (CR2) <SEP> 5502 <SEP> H <SEP> CE3CH20 <SEP> 0 <tb> <SEP> CH3 <tb> Table V-a (continued) EMI106.1 <tb> <SEP> R12 <SEP> R2 <SEP> R3 <SEP> g <SEP> y <SEP> rn-p. <tb> <SEP> r?SO,- <SEP> 9 <SEP> S02 <SEP> 5-CE3 <SEP> C1 <SEP> 0 <tb> <SEP> ca3 <tb> <SEP> 2 <SEP> H <SEP> Cl <SEP> CR2 <tb> <SEP> ; <SEP> \ <SEP> cEz <SEP> NO, <SEP> H <SEP> 61 <tb> <SEP> , <SEP> m <SEP> ,cE3 <tb> <SEP> s <SEP> ¯C <SEP> E <SEP> CH3 <SEP> 5CE3 <SEP> 3 <SEP> 0 <tb> <SEP> -CECEN <SEP> (CH3)2CH2S02 <SEP> H <SEP> H <SEP> O <tb> <SEP> CR3 <tb> -CE3 <SEP> S02N(C2z5)2 <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> / <SEP> CE2CE <tb> <SEP> 2E5 <SEP> SO <SEP> H <SEP> | <SEP> E <SEP> CH3 <SEP> 0 <tb> <SEP> CE2az <tb> <SEP> -CR3 <SEP> SO2OCR2 <SEP> CF3 <SEP> H <SEP> CR3 <SEP> 0 <tb> <SEP> -CE(CE3)2 <SEP> SO2OCRzCCl3 <SEP> H <SEP> CE3O <SEP> 0 <tb> <SEP> / <SEP> CH2CH2 <SEP> \ <tb> <SEP> -CR2CN <SEP> SO2N <SEP> O <SEP> H <SEP> H <SEP> CH2 <tb> <SEP> CXzCH2 <tb> <SEP> CHzCE <tb> <SEP> -CE-COOCE3 <SEP> S02 <SEP> CH2 <SEP> H <SEP> CH <SEP> /CE2 <tb> <SEP> CH3 <SEP> ca2ci2 <tb> <SEP> -CE2COOH <SEP> S02N(0CH3)CE3 <SEP> H <SEP> CE3 <SEP> CH2 <tb> <SEP> -CR(CR3)2 <SEP> SO2OCR2 <SEP> CF3 <SEP> a <SEP> CR3 <SEP> 0 <SEP> CH2 <tb> <SEP> -CR <SEP> COOCR' <SEP> SO,OCH,CC13 <SEP> 5-C1 <SEP> C1 <SEP> CCI <tb> <SEP> 2- <SEP> 3 <SEP> 2 <SEP> 2 <SEP> 3 <SEP> 5-Cl <SEP> Cl <SEP> CR2 <tb> TABLE V-b EMI107.1 EMI107.2 <tb> <SEP> R3 <SEP> X <SEP> Y <tb> <SEP> CR3 <SEP> 3 <SEP> CR3 <SEP> CH3 <SEP> 0 <tb> <SEP> CH3 <SEP> H <SEP> CE3 <SEP> 3 <SEP> 0 <tb> <SEP> CR3(CR2)4 <SEP> H <SEP> CR3 <SEP> CX3CE20 <SEP> CE2 <tb> <SEP> CE3 <SEP> 5-F <SEP> cE3 <SEP> H <SEP> CH2 <tb> <SEP> 3CH2 <SEP> 5-C1 <SEP> CR3 <SEP> CR30 <SEP> O <tb> <SEP> (CR3)2CR <SEP> 5-Br <SEP> cE3 <SEP> CH3 <SEP> 0 <tb> <SEP> CE3CE2 <SEP> 5-Cl <SEP> CH3 <SEP> CR3 <SEP> 0 <tb> <SEP> CR3 <SEP> (CR2)3 <SEP> 5-CH30 <SEP> CE3 <SEP> CR <SEP> 0 <tb> <SEP> CR3 <SEP> (CE2)5 <SEP> 5-CR3 <SEP> CX3 <SEP> CR3 <SEP> CR2 <tb> <SEP> (CR3) <SEP> 2CRCR2 <SEP> 5-CR3O <SEP> cE3 <SEP> H3 <SEP> 0 <tb> <SEP> CE <tb> <SEP> CE3(CH2)3CH <SEP> 5-caw <SEP> CR3 <SEP> CH3CX20 <SEP> CR2 <tb> <SEP> CH3 <SEP> 5-CEZ,O <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> <SEP> CH3 <SEP> 5-Cl <SEP> CR <SEP> CR <SEP> H <SEP> CH2 <tb> <SEP> CfI, <SEP> H <SEP> O <tb> <SEP> '3 <tb> <SEP> CH3 <SEP> H <SEP> CH3CX2CX <SEP> E <SEP> O <tb> <SEP> CE3CH2(CH3)CE <SEP> H <SEP> CE3(CX2)3 <SEP> CX3 <SEP> O <tb> <SEP> CR <SEP> CR <SEP> CR <SEP> H <SEP> CE <SEP> CR <SEP> CR <SEP> CR <SEP> CR <SEP> 0 <SEP> CE2 <tb> 3 <SEP> 2 <SEP> 5-F <SEP> 3 <SEP> CE2 <tb> <SEP> CE3 <SEP> 5-CR-3-O <SEP> CR3 <SEP> CR3 <SEP> 0 <SEP> O <tb> <SEP> CR3 <SEP> 3-CR3 <SEP> CR3CR <SEP> CR3 <SEP> 0 <tb> <SEP> (CE3)2CR <SEP> 6-C1 <SEP> (CR3)2CR <SEP> CX3CE20 <SEP> CE2 <tb> <SEP> 1 <SEP> 3 <tb> <SEP> cE3 <SEP> 5-Br <SEP> CX3CE2CH <SEP> CR <SEP> 0 <SEP> cur2 <tb> <SEP> 3 <tb> <SEP> CH3 <SEP> 5-c2E5 <SEP> CH3 <SEP> CE3 <SEP> CE2 <tb> <SEP> C2E5 <SEP> H <SEP> CH3 <SEP> CR3 <SEP> 0 <SEP> 0 <tb> <SEP> -CHCOOCR3 <SEP> H <SEP> CR3 <SEP> CR30 <SEP> O <tb> <SEP> ca3 <tb> Table V-b cont'd EMI108.1 <tb> <SEP> E <SEP> R3 <SEP> R5 <SEP> X <SEP> Y <tb> <SEP> CR3 <SEP> H <SEP> CR2CR-CR2 <SEP> CH3 <SEP> 0 <tb> <SEP> 3 <SEP> ' <SEP> H <SEP> CR(CR3)CRnCR2 <SEP> CR3 <SEP> 0 <tb> <SEP> -Ca2= <SEP> E <SEP> CR3 <SEP> CR30 <SEP> cur2 <tb> <SEP> -CR2CR-CR2 <SEP> H <SEP> CR30CR <SEP> CR <SEP> CR3 <SEP> 0 <tb> <SEP> CE <tb> <SEP> CR32 <SEP> CH2 <SEP> H <SEP> CE2wCECXz <SEP> H <SEP> CH2 <tb> <SEP> CH3 <tb> <SEP> -CaCN <SEP> H <SEP> 9 <SEP> H <SEP> O <tb> <SEP> cE3 <tb> <SEP> CE2COOH <SEP> H <SEP> CR3 <SEP> (CR2) <SEP> 2CH-CHCR2 <SEP> CH30 <SEP> CH2 <tb> <SEP> CII <SEP> 2C; ;CR <SEP> 5-Cl <SEP> CE3CH20CH2CH2 <SEP> CH30 <SEP> 0 <tb> <SEP> flC11Hz3 <SEP> 5-F <SEP> CR3(CR2)2C1R- <SEP> H <SEP> O <tb> <SEP> cE3 <tb> <SEP> -CEzCOOC2H5 <SEP> 6-C1 <SEP> CE3Cff <SEP> CX <SEP> CEz <SEP> Cur30 <SEP> 0 <tb> <SEP> CR3OCR2CR2 <SEP> 5-Br <SEP> (GE3)2CH - <SEP> Cur30 <SEP> 0 <tb> <SEP> -CEC02CH(CH3)2 <SEP> H <SEP> CH3 <SEP> CR3 <SEP> 0 <tb> <SEP> CH3 <tb> <SEP> 2 <SEP> S <SEP> CH30CE2CH2 <SEP> H <SEP> O <tb> <SEP> de <tb> <SEP> CE2 <SEP> 4 <SEP> C1 <SEP> 3 <SEP> C2H5 <SEP> CR30 <SEP> CR2 <tb> <SEP> CECOOR <SEP> 5-CH3 <SEP> n-C4E9 <SEP> - <SEP> Cm30 <SEP> CH2 <tb> <SEP> CH3 <tb> <SEP> CE2COOCH3 <SEP> H <SEP> n-C6E13- <SEP> CH3 <SEP> 0 <tb> <SEP> -CR2CR2CR2OCR3 <SEP> H <SEP> CR2-CR-CR2- <SEP> H <SEP> O <tb> <SEP> 3 <SEP> H <SEP> CR3 <SEP> C1 <SEP> CH2 <tb> <SEP> 2 <SEP> E <SEP> -CE(CE3)2 <SEP> C1 <SEP> CH2 <tb> ,CRCO0CR3 <SEP> H <SEP> CXzCF3 <SEP> C1 <SEP> CH2 <tb> <SEP> 3 <tb> <SEP> -CH(CE3)2 <SEP> H <SEP> -CRC-CR <SEP> C1 <SEP> 0 <tb> <SEP> CICI <tb> Table V-b cont'd EMI109.1 <tb> R12 <SEP> R3 <SEP> R5 <SEP> x <tb> -CE2C-CE <SEP> .5-C1 <SEP> 9 <SEP> C1 <SEP> 0 <tb> <SEP> CR <SEP> COOCR3 <SEP> H <SEP> CR3 <SEP> CR30 <SEP> O <tb> CR3 <tb> -CR2CO2CR2 <SEP> CE3 <SEP> 3-F <SEP> CR3CR2 <SEP> CR3 <SEP> 0 <tb> <SEP> CR3 <tb> -CE2C=CE <SEP> 6-CR3 <SEP> CE3(cE2)2 <SEP> H <SEP> 0 <tb> -CE2CS,: :ECE3 <SEP> R <SEP> CE2-CH(CR2)2 <SEP> CR30 <SEP> CR2 <tb> -C <SEP> t <SEP> CR3 <SEP> H <SEP> CR3CR <SEP> OCR2CR2 <SEP> CR3CR20 <SEP> 2 <tb> <SEP> CR <tb> 4 <SEP> CE3 <SEP> H <SEP> CR3 <SEP> CR3 <SEP> cur2 <tb> -CR2CR2CR3 <SEP> 6-Cl <SEP> -CE2CC13 <SEP> Cl <SEP> O <tb> -CECN <SEP> R <SEP> (CR2)3C3 <SEP> Cl <SEP> 0 <tb> <SEP> CR <tb> CZE5 <SEP> 3-CR3 <SEP> -CRCR2CR3 <SEP> E <SEP> CR2 <tb> <SEP> CE3 <tb> 2C0OCE(CE3) <SEP> 5-OCH3 <SEP> -cE2CE2 CE3 <SEP> H <SEP> CH2 <tb> -(CE2)5CE3 <SEP> H <SEP> CR2CHaCE2 <SEP> % <SEP> H <SEP> O <tb> -CR2COOE <SEP> 5-Br <SEP> C <SEP> H <SEP> H <SEP> 0 <tb> Tavble V-c EMI110.1 EMI110.2 <tb> <SEP> 2 <SEP> 3 <SEP> R8 <SEP> N <SEP> X <SEP> Y <tb> <SEP> ,ca3 <tb> <SEP> '3 <tb> CR <SEP> CR <SEP> CR <SEP> H <SEP> CE3 <SEP> C83 <SEP> CE3 <SEP> CH2 <tb> Ca3(CE2)5 <SEP> H <SEP> CR3 <SEP> CR3 <SEP> CE30 <SEP> 0 <tb> <SEP> CH3 <tb> CR2(CR2)3CH <SEP> H <SEP> CR3 <SEP> CE3 <SEP> C;;3O <SEP> CR, <tb> CR3 <SEP> 5 <SEP> CH3GE2 <SEP> CE3Ca2 <SEP> CX30 <SEP> 0 <tb> CK3tcE2) <SEP> H. <SEP> CR30 <SEP> CR3 <SEP> CE30 <SEP> CH <tb> <SEP> C83 <SEP> R <SEP> CR3(CR2)2 <SEP> CR3(CH2)2 <SEP> CR30 <SEP> cur2 <tb> H <SEP> E <SEP> (CE3)2CE <SEP> (CH <SEP> CR30 <SEP> CR2 <tb> 3 <SEP> 6-C <SEP> CI3 <SEP> H <SEP> CR30 <SEP> 0 <tb> CR3(CR2) <SEP> 6-Cl <SEP> CR3 <tb> (CR3)2CHCR2 <SEP> H <SEP> CR3 <SEP> E3 <SEP> CE30 <SEP> CR2 <tb> CR <SEP> CR <SEP> H <SEP> CR3 <SEP> Cg3 <SEP> CE30 <SEP> 0 <tb> (CE3)2CE <SEP> H <SEP> CE3CE2 <SEP> CE3C82 <SEP> CR30 <SEP> CE2 <tb> CH3 <SEP> 3-CR3 <SEP> CR30 <SEP> CR3 <SEP> CR30 <SEP> O <tb> CR3 <SEP> H <SEP> CR3(CR2)2 <SEP> CR3CCR2)2 <SEP> H <SEP> 0 <tb> CR3 <SEP> H <SEP> (CE3)2CE <SEP> (CE3)2cE <SEP> CR3CH20 <SEP> CR2 <tb> (CE3)2C <SEP> H <SEP> H <SEP> H <SEP> CE30 <SEP> CR2 <tb> CR3 <SEP> R <SEP> H <SEP> (CR3)2CR <SEP> CR3O <SEP> 0 <tb> -CaCOOCE3 <SEP> H <SEP> ca3 <SEP> CR3 <SEP> CE30 <SEP> 0 <tb> <SEP> CR <tb> CR33CR- <SEP> 5-CH3 <SEP> CR30 <SEP> CR3 <SEP> H <SEP> O <tb> <SEP> CR3 <tb> CR3(CR2)9CR- <SEP> H <SEP> CR3 <SEP> CE3(CE2)4 <SEP> CR30 <SEP> CR2 <tb> CR <SEP> CR3 <tb> <SEP> CR(CR2) <SEP> 8 <SEP> H <SEP> CR2=CHCR2 <SEP> CR2=CRCR2 <SEP> CR30 <SEP> O <SEP> 0 <tb> CR'3 <tb> -CE3 <SEP> H <SEP> CR <SEP> CR <SEP> H <SEP> O <tb> <SEP> 3 <SEP> 3 <tb> -CRCN <SEP> E <SEP> H <SEP> CR3 <SEP> H <SEP> CR2 <tb> -C2H5 <SEP> H <SEP> CR3 <SEP> CR3 <SEP> C1 <SEP> 0 <tb> Table V-c Continued EMI111.1 <tb> <SEP> R12 <SEP> R3 <SEP> R8 <SEP> R9 <SEP> X <SEP> Y <tb> <SEP> -CH2COOH <SEP> 5-Cl <SEP> H <SEP> H <SEP> Cl <SEP> CR2 <tb> <SEP> CUR <SEP> CHO <SEP> CEI2),CH, <SEP> H <SEP> 3 <SEP> 3 <SEP> -CR2CE2CR2CR2- <SEP> CR3CR2O <SEP> 0 <tb> <SEP> cE3 <tb> <SEP> C1' <tb> <SEP> Ii. <SEP> CH2 <SEP> H <SEP> -CR2CE2OCR2 <SEP> CR2- <SEP> CR3CR2 <SEP> 0 <SEP> CR2 <tb> <SEP> CSX <SEP> \ <SEP> CH2 <SEP> 5-CH30 <SEP> -CE2 <SEP> CR2CR2 <SEP> CR2 <SEP> CR2- <SEP> H <SEP> O <tb> <SEP> -a-C12E25 <SEP> H <SEP> Cue <SEP> 30 <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> -n-C10E21- <SEP> 6-Cl <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> CE3OCR2CR2 <SEP> 5-F <SEP> H <SEP> CR3 <SEP> CR30 <SEP> O <tb> <SEP> -n10E21 <SEP> H <SEP> g <SEP> CR2-CRCE2 <SEP> CR <SEP> 3 <SEP> 2 <SEP> CH2 <tb> <SEP> Cl <tb> <SEP> C1 <SEP> v <SEP> CH2 <SEP> H <SEP> H <SEP> (CR3)2CH <SEP> CR3O <SEP> CH2 <tb> <SEP> CE2C <SEP> 6-CR3 <SEP> ^ <SEP> CR3 <SEP> CH3 <SEP> CR30 <SEP> CR2 <tb> <SEP> CE2C02CE3 <SEP> 5-CE3 <SEP> CE3CE2 <SEP> CR3 <SEP> H <SEP> O <tb> <SEP> CR-CO <SEP> 2CE(CR3)2 <SEP> H <SEP> n-C4Hg <SEP> n-C <SEP> 4R9 <SEP> O <tb> <SEP> CR3 <tb> <SEP> CM2 <SEP> COOT <SEP> H <SEP> CH30 <SEP> CH3 <SEP> CH3 <SEP> CH2 <tb> <SEP> CRCOOH <SEP> R <SEP> - <SEP> -CR2CCR2 <SEP> CR2 <SEP> - <SEP> CE30 <SEP> CH2 <tb> <SEP> CR <tb> <SEP> CHCEN <SEP> H <SEP> -CR2CR2CR2CR2CR2 <SEP> - <SEP> CR3 <SEP> 0 <tb> <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> - <SEP> CH2CE2CE20CH2CH2- <SEP> CR320 <SEP> 0 <tb> <SEP> CR2CR3 <SEP> 6-Cl <SEP> CE3 <SEP> 0 <SEP> CE3 <SEP> Cur3 <SEP> 0 <SEP> 0 <tb> <SEP> CH <SEP> CH-CH <SEP> 5-CR3O <SEP> H <SEP> H <SEP> CH3O <SEP> O <tb> <SEP> CR2CR'CR <SEP> E <SEP> E <SEP> CE3CE-CHCE2 <SEP> CR3O <SEP> CR2 <tb> <SEP> CHCOOCH3 <SEP> H <SEP> CR30 <SEP> CH3 <SEP> C1 <SEP> cur2 <tb> <SEP> CR3 <tb> Table V-c Continued R12 R3 R8 R9 X Y -CH2CH2OCH3 H H CH3 Cl CH2 -CH2CH2CH2OCH3 H C2H5- CH3 Cl O -CH2C#N H -CH(CH3)2 CH3 Cl O Table V-d EMI113.1 EMI113.2 <tb> <SEP> R12 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <tb> 3 <SEP> S02N(CR3)2 <SEP> H <SEP> CH3 <SEP> 0 <tb> -CH(CH3)2 <SEP> CO <SEP> CR <SEP> H <SEP> CR30 <SEP> O <tb> -CHCH2CH3 <SEP> S02N(C2H5)2 <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> CR <SEP> 3 <tb> <SEP> -(CR2)4CE(CR3)2 <SEP> CON(CH3)2 <SEP> H <SEP> H <SEP> o <tb> <SEP> CE12CH2 <tb> -(CE2)7CE3 <SEP> SO2N <SEP> <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> CE2CH2/ <tb> -(CR2)9CR3 <SEP> S02N(CE3)2 <SEP> H <SEP> CH3 <SEP> 0 <tb> -(CH2)llCH3 <SEP> CoN(oCH3)CH3 <SEP> 5-C1 <SEP> C2H50 <SEP> 0 <tb> <SEP> CH2COOu <SEP> S02N(CE3)2 <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> CHCOOH <SEP> S02N(OCH3)CH3 <SEP> H <SEP> CE3O <SEP> O <tb> <SEP> CH3 <tb> <SEP> CR <tb> <SEP> /CH3 <tb> <SEP> CH2COOCH3 <SEP> S02NX <SEP> H <SEP> Cl <SEP> O <tb> <SEP> o <SEP> CH(CE3)2 <SEP> H <tb> <SEP> CRCOOC2R5 <SEP> CSCR3 <SEP> 5-CH3 <SEP> CR30 <SEP> O <tb> <SEP> CH3 <tb> <SEP> CR2 <SEP> < <SEP> C02CH(CH3)2 <SEP> E <SEP> CR3 <SEP> 0 <tb> <SEP> CEI2 <SEP> -( <SEP> (3 <SEP> ) <SEP> 2 <tb> <SEP> CH2 <SEP> 4 <SEP> CON(C2H5)2 <SEP> H <SEP> CR30 <SEP> 0 <tb> <SEP> H2 <SEP> e <SEP> CH3 <SEP> S02N(CE3)2 <SEP> 6-OCE3 <SEP> C2H5Q <tb> <SEP> sCH2ClI2 <tb> <SEP> CE2CH-CE2 <SEP> SO <SEP> CR1 <SEP> H <SEP> CR30 <SEP> 30 <tb> <SEP> CE2CH2 <tb> -ca <SEP> C=CH <SEP> C 2CH3 <SEP> H <SEP> C1 <SEP> O <tb> Table V-d Continued EMI114.1 <tb> <SEP> R12 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <tb> <SEP> CR <tb> Ca2CX20CX3 <SEP> CON <SEP> H <SEP> CE30 <SEP> 0 <tb> <SEP> C2Hs <tb> CR2CR2CR20CR3 <SEP> C02CR2CR2CR3 <SEP> 5-F <SEP> CR3 <SEP> 0 <tb> C%2C N <SEP> S02N(OCE3)CE3 <SEP> s <SEP> H <SEP> O <tb> 3 <SEP> CO2CR3 <SEP> H <SEP> CR3 <SEP> CR2 <tb> CE2CE(CE352 <SEP> CON(CE3)2 <SEP> H <SEP> CE30 <SEP> CR2 <tb> (CH2)5CH3 <SEP> SO2N(CR3)2 <SEP> H <SEP> CE3 <SEP> cur2 <tb> <SEP> CE2CE2 <tb> CR <SEP> (CR2)5CR3 <SEP> so2 <SEP> | <SEP> H <SEP> CR30 <SEP> CE2 <tb> cs3 <SEP> CR2CR2 <tb> (CE2)4CX3 <SEP> C02 <SEP> CE-CE2 <SEP> H <SEP> CE3 <SEP> CR2 <tb> CHCOOH <SEP> CO <SEP> CR <SEP> CF <SEP> 6-ca3 <SEP> CR30 <SEP> CH2 <tb> CR3 <tb> CE2COOH <SEP> CO2CR'2CR-CR2 <SEP> H <SEP> CR3 <SEP> CR2 <tb> CR2COOC2H5 <SEP> cON(OCE3)C <SEP> h <SEP> H <SEP> CH3 <SEP> CR2 <tb> <SEP> / <SEP> CE2CEi2 <tb> <SEP> 2 <SEP> 2 <tb> CECOOCE3 <SEP> SO2 <SEP> 8 <SEP> H <SEP> CH3 <SEP> CH2 <tb> cE3 <SEP> CE2CE2 <tb> Cm2 <SEP> 4 <SEP> SO2N <SEP> (OCR3) <SEP> CR3 <SEP> 5-Cl <SEP> CR30 <SEP> CX2 <tb> <SEP> Cl <SEP> / <SEP> CR <tb> CR2-'0Cl <SEP> S 2N <SEP> H <SEP> CR3 <SEP> CR2 <tb> <SEP> CE(CE3)2 <tb> <SEP> CR3 <SEP> SCE2CH2 <tb> CR? <SEP> CON <SEP> CH2 <SEP> H <SEP> CE30 <SEP> CH2 <tb> <SEP> CR <SEP> CR <tb> CE2CR-CIICR3 <SEP> CQ2CR2CR2Cl <SEP> 3-CX3 <SEP> CR3 <SEP> CE2 <tb> <SEP> '0 <tb> <SEP> ii <tb> CRzC"'tE= <SEP> CSCE(CH3)2 <SEP> H <SEP> ca3o <SEP> CH2 <tb> -CR2CH20C2H5 <SEP> C02CRtCR2CH3 <SEP> 5-OCR3 <SEP> CR3 <SEP> CH2 <tb> <SEP> CR3 <tb> -CR2CR20CR2 <SEP> CONE2 <SEP> H <SEP> CR3 <SEP> 0 <SEP> CH2 <tb> -Ca2C3N <SEP> C0NECH3 <SEP> CH3 <SEP> 2 <tb> Table V-e EMI115.1 EMI115.2 <tb> R <SEP> R4 <SEP> X <SEP> Y <tb> CR3 <SEP> H <SEP> CH30 <SEP> O <tb> CH3 <SEP> 2-Cl <SEP> CH3 <SEP> 0 <tb> CH3(CH2)3 <SEP> 4-F <SEP> CH3 <SEP> 0 <tb> CH3 <SEP> 2-CH3 <SEP> CR3 <SEP> CH2 <tb> CH3 <SEP> 4-OCH3 <SEP> CR3CE2O <SEP> 3 <SEP> 2 <SEP> 2 <tb> CR3 <SEP> 2-NO2 <SEP> CR30 <SEP> 2 <tb> (CH3)2CE <SEP> 4-CO2CR3 <SEP> CH30 <SEP> . <SEP> CH2 <tb> CH3CH2(CH3)CH <SEP> 2-SCR3 <SEP> Cur30 <SEP> 0 <tb> CH3(CH2)5 <SEP> 4-C1 <SEP> CH30 <SEP> CH2 <tb> CH3(CH2)3CH <SEP> .2-Br <SEP> CH3 <SEP> 0 <tb> <SEP> CR3 <tb> n-C8H17 <SEP> 2-F <SEP> CH3 <SEP> CH2 <tb> n-C12R25 <SEP> C2 <SEP> 5 <SEP> CR3O <SEP> 'CR2 <tb> CH3(CH2)3CH <SEP> 82-OC2R5 <SEP> CH3O <SEP> 3 <tb> <SEP> CR <tb> CR3OCE <SEP> CR <SEP> CR <SEP> 4-NO2 <SEP> CE30 <SEP> 0 <tb> CR <SEP> 3OCR <SEP> CR <SEP> 2-CO <SEP> CR <SEP> CR3CH2 <SEP> 0 <SEP> CE2 <tb> CH30CH2CE2 <SEP> 4-SC2H5 <SEP> CR30 <SEP> CH2 <tb> CHURN <SEP> 4-Br <SEP> Cm30 <SEP> CH2 <tb> CH3 <tb> CH2COOH <SEP> .2-F <SEP> CH3 <SEP> 0 <tb> CR2COOCR3 <SEP> 2-CX(CE3)2 <SEP> CR3CR20 <SEP> 0 <tb> CH-COOCH3 <SEP> 4 <SEP> CR <tb> I <SEP> 4-OCR3 <SEP> CR30 <SEP> 0 <tb> CH3 <tb> Table V-a cont'd EMI116.1 <tb> <SEP> R4 <SEP> X <SEP> Y <tb> <SEP> caCEsca2 <SEP> 2(CR2)zCR3 <SEP> CE3 <SEP> CE2 <tb> <SEP> CR3 <tb> <SEP> p-s <tb> <SEP> cE2 <SEP> S <SEP> 20N02 <SEP> CR30 <SEP> CR2 <tb> <SEP> CR3 <SEP> C-CCR2 <SEP> 4-CO <SEP> CR <SEP> H <SEP> CE2 <tb> <SEP> CR3CE2 <SEP> 2-SO2CR3 <SEP> C1 <SEP> O <tb> <SEP> (CE3)2CE <SEP> 4-No2 <SEP> Cl <SEP> CR2 <tb> <SEP> Cl <SEP> 9 <SEP> CR2 <SEP> 4-Cl <SEP> H <SEP> CR2 <tb> <SEP> CH <SEP> 5 <SEP> CR2 <SEP> 2-F <SEP> H <SEP> O <tb> <SEP> Cl <SEP> 9 <SEP> CRz <SEP> 4-SCE3 <SEP> C1 <SEP> O <tb> <SEP> Cl <tb> <SEP> CE3(CE2)2 <SEP> 4-Cl <SEP> H <SEP> CR2 <tb> <SEP> CE3O(CS2)3 <SEP> 2-Br <SEP> H <SEP> 0 <tb> <SEP> C13o(CX2)2 <SEP> 2-CR3 <SEP> Cl <SEP> CE2 <tb> <SEP> 5 <SEP> 2 <SEP> 2-CO <SEP> 2 <SEP> 2 <SEP> H <SEP> O <tb> <SEP> CR2CRCR2CRz <SEP> 2-NO2 <SEP> C1 <SEP> O <tb> <SEP> CR(CR3)CN <SEP> 4-F <SEP> H <SEP> CR2 <tb> <SEP> CR(CR3)CO <SEP> 2-C02e2H, <SEP> K <SEP> CR2 <tb> <SEP> 3 <tb> <SEP> O <SEP> CE <SEP> 4-Cl <SEP> C1 <SEP> 0 <tb> <SEP> 2 <tb> <SEP> cR3 <tb> <SEP> CR <tb> <SEP> , <SEP> 3 <tb> CR2CCR3 <SEP> 4-OCX3 <SEP> H <SEP> CR2 <tb> Table V-f EMI117.1 EMI117.2 <tb> <SEP> R <SEP> R <tb> <SEP> R12 <SEP> 4 <SEP> X <SEP> Y <SEP> m.p. <tb> <SEP> L <SEP> 4 <SEP> li <SEP> Y <SEP> mrP. <tb> CH3 <SEP> 2-Cl <SEP> 3 <SEP> 0 <tb> CE3 <SEP> CE2 <SEP> 4-Cl <SEP> E <SEP> o <tb> CH3(CX2)2 <SEP> 2-F <SEP> CR3 <SEP> 0 <tb> Clef3 <SEP> 4-Br <SEP> 2 <SEP> O <tb> cE3 <SEP> 2-CR3 <SEP> CR30 <SEP> CR2 <tb> CH3 <SEP> 4-OCH3 <SEP> CH3 <SEP> CR2 <tb> (CH3)2CH <SEP> 2 <SEP> 3 <SEP> CR2 <tb> (CR3)2CRCR2 <SEP> 4-NO2 <SEP> CR30 <SEP> O <tb> CR3 <SEP> CR2(CR3)CR <SEP> 2-CO2CE3 <SEP> CR <SEP> 0 <SEP> CR2 <tb> CR3 <SEP> (CR2)5 <SEP> 4-SCR3 <SEP> CH30 <SEP> CH2 <tb> n-C10E21 <SEP> 2-F <SEP> CX3 <SEP> CH2 <tb> -CHCOOCX3 <SEP> 4-Cl <SEP> CR3 <SEP> 0 <SEP> CR2 <tb> <SEP> cE3 <tb> -CE2CX=CH2 <SEP> 2-C2H5 <SEP> C1 <SEP> 0 <tb> <SEP> Cl <tb> <SEP> 2 <SEP> 4 <SEP> 2-OCH3 <SEP> CH3 <SEP> 0 <tb> CR3 <SEP> 0CR2CR2CR2 <SEP> 4 <SEP> Nd2 <SEP> CR3 <SEP> 0 <SEP> CH2 <tb> CR,COOR <SEP> 4-C02C2E5 <SEP> CH3 <SEP> 0 <tb> CH3 <tb> -CX2COOH <SEP> 2-SC <SEP> 2 <SEP> 5 <SEP> H <SEP> O <tb> CH2C-N <SEP> .2-SCR3 <SEP> CR3 <SEP> 0 <SEP> CR2 <tb> CH <SEP> < <SEP> 2-C1 <SEP> CE3 <SEP> 0 <tb> CH3 <tb> CR3OCR2CR2 <SEP> 2-Br <SEP> 2 <SEP> 0 <tb> Formulations Useful formulations of the compounds of Formulas I and II can be prepared in conventional ways. They include dusts, granules, pellets, suspensions, emulsions, wettable powders, emulsifiatle concentrates and the like. Many of these can be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactant(s) and b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the approximate proportions set forth in Table VI. Table VI Weight Percent* Active Surfac Ingredient Diluent(s) tant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, Solutions, Emulsions (including Emulsifi- able Concentrates) 3-50 40-95 0-15 Aqueous Suspensions 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 *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 oatios of surfactant to active ingredient are some times 'desirable, and are achieved by incorporation into the fÏrmulation, or by tank mixing. Some typical solid diluents are described in Watkins, et al., "Hadbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, -Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable -powders and the denser ones for dusts. Typical liquid diluents and solvents are described -in Marsden., "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under oil is preferred for suspension concentrates, solution concentrates are preferably stable against phase separation at OOC. "McCutcheon'-s Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surgfactants 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 on preformed granular carriers or by agglomeration techniques. See J. E. Brownie, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41. R. W. Luckenbaugh, U.S. Patent 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, 169-182. E. Gysin and E. Knusli, U.S. Patent 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 164 e G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96. J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. The disclosures of the above-cited references are herein incorporated by reference. Unless indicated. otherwise, all parts are by weight in the following examples. Example 14 Wettable Powder N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide 40% dioctyl sodium sulfosuccinate- 1.5% sodium ligninsulfonate. 3% low viscosity methyl cellulose 1.5% attapulg ite 548 The ingredients are thoroughly blended, 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 15 Granule wettable powder of Example 14 10% attapulgite granules 90% (U.S.S. &num;20-40; 0.84-0.42 mm) A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. Example 16 Wettable Powder N-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended and ground in a hammer mill to produce an average particle -size under 100 microns. The material is reblended, sifted through a U.S.S. 50 sieve and packaged. example 17 Granule wettable powder of Example 16 15% gypsum 69% potassium sulfate 168 The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm. (U.S.S. 18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 128 active ingredient. Example 18 ettable Powder N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl.) -2- (methoxycarbonyl) benzenesul- fonamide 658 dodecylphenol polyethylene glycol ether 2% sodium ligninsulfonate 48 sodium. silicoaluminate 6% montmorillonite (calcined) 23% The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended, sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example 19 High Strength Concentrate N-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve-(0.3 mm openings). This material may then be formulated in a variety of ways Example 20 Aqueous Suspension N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl 2- -(methoxycarbonyl) benzenesul- f onamide 25% hydrated attapulgite 3% 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 diameters under 10 microns. Example 21 Oil Suspension N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl]-2-nitrobenzenesulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 708 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 with oils or emulsified in water. Example 22 Extruded Pellet N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl) aminocarbonyl) -2- (methoxycarbonyl) benzenesulfon- amide 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or' the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (or42 mm openings) may be packaged for use and the fines recyeled. Utility The compounds of the present invention are powerful herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds are useful for the selective pre- or post-emergence weed control in crops, such as wheat and soybeans. The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of needs 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 0.02 to 10 kg/ha, the -l-ower -rates -being suggested for use-on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide examples of which are -those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bi pyridylium types. The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. Test A Seeds of crabgrass (DigtariA spp.), barnyard grass (Echinochloa crusgalli), wild oats (Avena fatua), Cassia tora, morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat as well as nutsedge tubers were planted in a growth medium and treated preemergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyle donary ones), bush beans with the third trifoliate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyle donary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment. The ratings are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: G = growth retardation; C = chlorosis/necrosis; D = defoliation; S = albinism; 6Y = abscised buds or flowers; U = unusual pigmentation; E = emergence inhibition; and H = formative effects. The ratings for the compounds tested by this procedure are presented in Table A. It will be seen that certain of the compounds tested have utility for selective preemergence weed control in wheat and soybeans. Table A EMI127.1 <tb> <SEP> W <SEP> W. <tb> <SEP> Y <tb> <SEP> == <tb> <SEP> o:j <SEP> c: <tb> <SEP> 5 <SEP> n <SEP> ¯= <tb> <SEP> 0 <SEP> 0 <tb> <SEP> 0 <tb> <SEP> BUSHBLS <SEP> 9C <SEP> 1 <SEP> se <tb> <SEP> COTTON <SEP> 3G¯,6C <SEP> 10C <tb> <SEP> ORNINGGLORY <SEP> 10C <SEP> 10C <tb> <SEP> COCKLEBT;'R <SEP> 9C <SEP> -s¯c <tb> <SEP> CASSIA <SEP> 9C <SEP> 9C <tb> <SEP> NUTSEDGE <SEP> 10C <SEP> 2C,SG <tb> <SEP> CRABCPASS <SEP> 9C <SEP> SCIBG <tb> <SEP> BAILYARDCRASS <SEP> 10C <SEP> 9C <tb> <SEP> WILD <SEP> OiTS <SEP> ¯ <SEP> 9G,5C <SEP> 9C <tb> ¯ <SEP> k'HEA <SEP> ¯8G,2C <SEP> ¯gC <tb> <SEP> CORE' <SEP> 9H,SU <SEP> I <SEP> 9e <tb> <SEP> SOYBULP: <SEP> 90 <SEP> 90 <tb> I <SEP> RICE <SEP> gC <SEP> C <SEP> 9G- <SEP> <tb> <SEP> SORGHZM--- <SEP> sa,m <SEP> ¯ <SEP> se <SEP> - <tb> I <tb> <SEP> PRE-EMERGEh'CE <tb> <SEP> MOREINGGLDRY <SEP> ¯¯: <SEP> 9G <SEP> -- <SEP> re <tb> ¯ <SEP> COCffLEBtTR <SEP> 9G <SEP> -s <SEP> 99 <tb> <SEP> NUTSEDGE <tb> <SEP> CASSIA <SEP> 90 <SEP> 90 <tb> <SEP> BARNYARDGRAS <SEP> S <SEP> lOR <tb> <SEP> WILD <SEP> OATS <SEP> 9G,2C <SEP> 5C,9R <tb> <SEP> WHEAT <SEP> 9H <SEP> . <SEP> ¯ <SEP> 9H <tb> <SEP> CORN <SEP> 9G <SEP> 10H <tb> <SEP> SOYBEAN <SEP> 9R <SEP> 9H <tb> <SEP> RICE <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> lOE <SEP> j <SEP> lOE <tb> <SEP> SORGHEMI <SEP> 9G.lC <SEP> = <tb> Table A (continued) EMI128.1 <SEP> 0 <SEP> tti; <tb> <SEP> . <SEP> <SEP> N <SEP> < <SEP> 3 <tb> <SEP> oNH-C'-! <tb> <SEP> N <tb> <SEP> C1 <tb> <SEP> 1 <tb> <SEP> kg/ha <SEP> 2 <SEP> 0.4 <tb> <SEP> POST-mLRGZNCE <tb> <SEP> BUSEBEAdS <SEP> 9C <tb> <SEP> COTTON <SEP> 9C <SEP> 6C <SEP> 9G <tb> <SEP> MORNhNGGLORY <SEP> lOC <SEP> 8C <tb> <SEP> COCKLEBUR <SEP> 9C <SEP> 9C <tb> <SEP> CASSIA <SEP> se <SEP> 9C <tb> <SEP> NUTSEI)GE <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> 8C <SEP> 5C <SEP> ,9G <tb> <SEP> CRABG¯XASS <SEP> ¯ <SEP> 9C <SEP> 9% <tb> <SEP> BARLAEDGRASS <tb> <SEP> ¯ <SEP> 9C <SEP> 6C,G <tb> <SEP> alrslro7irs <SEP> e <SEP> .7e <tb> <SEP> krfT <SEP> 8e <SEP> 3C <SEP> ,86 <SEP> 1 <tb> ,co¯Riu <SEP> 9U <SEP> 9C <SEP> 9C <SEP> I <tb> <SEP> SOYB¯EAL <SEP> gC <SEP> 6C <SEP> Dr <tb> <SEP> ,rJ <tb> ¯ <SEP> RLCE <SEP> SC,8G <SEP> 5C <SEP> ,9G <tb> j¯ <SEP> SORGHM <SEP> se <tb> IPRE-EMEICCefCE <tb> <SEP> ¯MORN'IJGGLORY <SEP> se <SEP> 9G <tb> <SEP> ¯BG <SEP> 9G <tb> <SEP> BARNYARDGRASS <SEP> ¯ <SEP> 9H <SEP> - <SEP> SC <SEP> ,9R <tb> <SEP> WILD <SEP> OATS <SEP> ¯ <SEP> 1C,8G <SEP> IC <SEP> ,9G <tb> <SEP> JEAT <SEP> 9H <SEP> sH <tb> <SEP> CORN <SEP> 9G <SEP> . <SEP> - <SEP> lC <SEP> 9G <tb> <SEP> ¯ <SEP> 9E <tb> <SEP> RICE <SEP> - <SEP> lOE <tb> <SEP> 5C <SEP> * <SEP> , <SEP> 9H <SEP> G <tb> Table A (continued) EMI129.1 <tb> <SEP> 20= <tb> Y <SEP> = <SEP> 2 <tb> <SEP> 0 <tb> <SEP> 0 <tb> <SEP> 9 <SEP> : : <tb> <SEP> (WI <tb> <SEP> k <SEP> !ha <SEP> 2 <SEP> | <SEP> 0.4 <SEP> ¯ <SEP> 0.4 <tb> <SEP> POST <SEP> CC <tb> <SEP> 3 <SEP> SE <SEP> 3F <SEP> t <SEP> 9D,9G <SEP> ' <SEP> 5C,7G,6Y <SEP> 6C <SEP> 8G,6Y <tb> <SEP> COTTON <SEP> t <SEP> 3C,5G <SEP> ¯j <SEP> 3C,5G <tb> <SEP> MORNINGGLORY <SEP> 1 <SEP> 3C,9G <SEP> I <SEP> lC, <SEP> G <SEP> lOC <tb> COCK23UE <SEP> 5C,9G <SEP> i <SEP> I <SEP> 2C,7G <SEP> I <SEP> 9C <tb> <SEP> CASSIA <SEP> 3C <SEP> t <SEP> lC,8G <tb> <SEP> NDTSEDGE <SEP> qG <tb> <SEP> CBABCRaSS <SEP> 2C,G <SEP> i <SEP> pr <SEP> I <SEP> 3C.86 <tb> <SEP> BARNYARDGRASS <SEP> 2C <SEP> I <SEP> 12r <SEP> I <SEP> 3C,BH <tb> <SEP> I <tb> <SEP> WIf9 <SEP> OATS <SEP> 1C <SEP> O <SEP> I <SEP> 2C <tb> <SEP> wriEr <SEP> pe <SEP> I <SEP> -u <SEP> ¯I <SEP> 1C,se <tb> <SEP> CORN <SEP> 1C,5n <SEP> Td,sH <tb> <SEP> sa <tb> <SEP> SOYBE <SEP> 6H <tb> <SEP> RfCE <SEP> 86 <SEP> n <tb> <SEP> SOBGHUM <SEP> 8H <SEP> JR. <tb> <SEP> MORNINGCLORP. <SEP> ¯ <tb> <SEP> == <SEP> iG <SEP> = <SEP> X <SEP> 9Q <tb> CASSIA <SEP> 8G <SEP> | <SEP> 1C, <SEP> G <SEP> 7G <tb> NUTSEDGE <SEP> G <SEP> G <SEP> 9G <tb> CUBGRASS <SEP> 3G <SEP> 2G <SEP> zr; <SEP> 4G <tb> <SEP> BAARDGRASS <SEP> 9H <SEP> 9Ef <SEP> 7G <SEP> 9H <tb> WTLD <SEP> OATS <SEP> - <SEP> 25GG <SEP> 6G <tb> WHEAT <SEP> 8G <tb> CORN <SEP> 2C,8G <SEP> lC,6G <SEP> 2C.9G <tb> SOYBEAN <SEP> 3H <SEP> 2R <SEP> 7 <SEP> SH <tb> RICE <SEP> 9H <SEP> 9H <SEP> 9H <tb> SORGEQn <SEP> ¯ <SEP> 8H <SEP> 1C,8H <SEP> I <SEP> 2C,9G <tb> Table A (continued) EMI130.1 <SEP> -mC) <SEP> n <tb> <SEP> ¸ <tb> <SEP> = <SEP> = <tb> <SEP> = <tb> <SEP> t <tb> <SEP> 0 <SEP> The <tb> <SEP> 0 <tb> <SEP> c-8 <SEP> o <tb> <SEP> o <SEP> ta <tb> <SEP> I <tb> <SEP> k <SEP> Iba <SEP> 2 <SEP> | <SEP> 0.4 <SEP> 2 <SEP> 0.4 <tb> <SEP> g <SEP> .. <SEP> . <SEP> . <SEP> .- <SEP> .. <tb> <SEP> POST <SEP> EKERGEN <tb> BUSH <SEP> BEh <SEP> <SEP> BEAN <SEP> 9C <SEP> 9C <SEP> L <SEP> 1C <tb> <SEP> COTTON <SEP> 3C,,9G <SEP> i <SEP> 8C <SEP> 9G <SEP> C, <SEP> Ego <SEP> 0 <tb> MORNINGGLORY <SEP> loc <SEP> 0C <SEP> I <SEP> I <SEP> ¯ <SEP> IC <SEP> 1 <SEP> IC <SEP> 2C <tb> <SEP> CO: <SEP> L <SEP> 10C <SEP> I <SEP> lOC <SEP> ! <SEP> fez1 <SEP> O <SEP> - <SEP> O0 <tb> <SEP> CASSIA <SEP> 5C,8G <SEP> I <SEP> SC,8G <SEP> I <SEP> 0 <SEP> 0 <tb> NSTSEDGE <SEP> ¯¯ <SEP> 9C <SEP> lUC <SEP> ¯j <SEP> 0 <SEP> 0 <tb> <SEP> CABGuS5 <SEP> 9C <SEP> se <SEP> 0 <SEP> O <tb> <SEP> NGSYARDGlASS <SEP> loc <SEP> lOc <SEP> i <SEP> 0 <tb> WTLD <SEP> OATS <SEP> SC, <SEP> G <SEP> 5C,9G <SEP> j <SEP> 0 <tb> wHSAT <SEP> U, <SEP> G <SEP> 5U,8G <SEP> 0 <tb> <SEP> CORN <SEP> 9C <SEP> lOC <SEP> j <SEP> 0 <SEP> 0 <tb> <SEP> S0"'S <SEP> I <SEP> C <SEP> 9C <SEP> 0 <tb> <SEP> R'ICZ <SEP> C <SEP> C <SEP> 0 <tb> <SEP> SOR <SEP> C <SEP> 9C <SEP> 1 <tb> PRE <SEP> PiERCEE3CE <tb> MORNINGGLORY <SEP> 9C <SEP> I <SEP> 9G <SEP> 9G <SEP> ¯ <SEP> 5G <tb> <SEP> COOE3UR <SEP> G <SEP> 9G <SEP> 9 & 4G <tb> CASSIA <SEP> 9G <SEP> csc- <SEP> 9G <SEP> 2H <SEP> 0 <tb> NUTSEDGE <SEP> las <SEP> 1UX <SEP> O <SEP> -- <SEP> o <tb> NUT¯SEDGZ <SEP> 9H <SEP> I <SEP> o <SEP> I <tb> CXABGBASS <SEP> IsH <SEP> o <tb> <SEP> 10H <SEP> I <tb> WTLD <SEP> OATS <SEP> 2C,8G <SEP> , <SEP> 2C,9G <tb> <SEP> lOR <SEP> t <SEP> 10H <SEP> t <SEP> IOE <SEP> 0 <tb> CORN <SEP> 1 <SEP> lOE <SEP> t <SEP> 10E <SEP> 0 <tb> <SEP> SOYBEAN <SEP> lOE <SEP> 9H <SEP> I <tb> <SEP> l <tb> RICE <SEP> E <SEP> LOE <SEP> I <SEP> 3G <SEP> U <SEP> G <tb> <SEP> SORGEUt. <SEP> i0H <SEP> 1 <SEP> H <SEP> j <SEP> 2G <SEP> G <tb> Table A (continued) EMI131.1 <tb> <SEP> m <tb> <SEP> fuzz <tb> <SEP> = <SEP> = <tb> <SEP> 0='3 <tb> <SEP> 0 <SEP> -= <tb> <SEP> 0 <tb> <SEP> Zu <tb> <SEP> toN <SEP> f <tb> <SEP> I <tb> <SEP> kg/ha <SEP> 2 <SEP> 1 <SEP> 0.4 <SEP> 2 <tb> <SEP> POST <SEP> EMERGENCE <tb> <SEP> BUSE <SEP> BEAN <SEP> 5C*qG <SEP> C <SEP> 9G <SEP> SC <SEP> 9G <SEP> I <tb> <SEP> COTTON <SEP> 2C.2H,4G <SEP> I <SEP> 2C <SEP> 2H <SEP> 4G <SEP> 2C <SEP> 2H <tb> <SEP> MORNTNCGLORY <SEP> ¯ <SEP> lOC <SEP> I <SEP> 5C,9G <tb> <SEP> COCU <SEP> 2C. <SEP> 9G <SEP> [ <SEP> I <SEP> iC <tb> CAS5IA <SEP> 5C, <SEP> 7G <SEP> l <SEP> SC,9G <tb> <SEP> N[JISZDGE <SEP> Ot <SEP> bK <tb> <SEP> CEiGRASS <SEP> 3C1 <SEP> 7G3C,7H¯ <SEP> 2C. <SEP> f6 <SEP> ¯ <tb> <SEP> .I <SEP> 1C.56 <SEP> ¯I <tb> <SEP> BARNYARD6RASS <SEP> 96 <SEP> 26. <SEP> 9H <tb> <SEP> uILS <SEP> OATS <SEP> 2C,66 <SEP> +I: :3G¯ <SEP> I¯ <SEP> 26,76 <tb> CORN <tb> <SEP> SOYBEAN <SEP> lC,9H <SEP> H <SEP> 5H,9G <tb> <SEP> RICE <SEP> 56,96 <SEP> - <SEP> 5C,9G <SEP> ! <SEP> C, <SEP> G <SEP> 4C <SEP> 9G <tb> <SEP> SORGHtThf <SEP> 3E,9G <SEP> , <SEP> , <SEP> 9G <tb> '888 <SEP> 'PiEICGENCE <SEP> / <tb> <SEP> PRE <SEP> =ESCE <SEP> , <SEP> g <SEP> I <SEP> , <SEP> , <tb> MOREHZ <SEP> LRKI <SEP> G <SEP> 9G <SEP> 9G <tb> <SEP> 96 <tb> <SEP> co <SEP> i <SEP> ¯ <SEP> 96 <SEP> 86 <SEP> ¯ <SEP> ¯¯ <SEP> 96 <tb> <SEP> NUTSEDGE <SEP> 9G <SEP> G <SEP> 9G <tb> CRAB6RASS <SEP> G <SEP> /G <SEP> , <SEP> 4G <tb> <SEP> BARNYARNRASS <SEP> 9E <SEP> H <SEP> 9H <tb> WILD <SEP> OATS <SEP> 2C.8H <SEP> 8G <SEP> 7G <tb> A'T <SEP> 9G <SEP> ¯ <SEP> Z <SEP> 9G <tb> CORN <SEP> 2C.9G <SEP> f <SEP> G <tb> SOYBEAN <SEP> 9H <SEP> 8H <SEP> . <tb> RICE <SEP> 10± <SEP> 9R <tb> SORGEUM <SEP> i <SEP> 9H <SEP> 9G <SEP> ¯ <SEP> . <SEP> 9E <tb> Tabnle A (continued) EMI132.1 <tb> <SEP> Qo <tb> <SEP> z <tb> = <SEP> -I <tb> <SEP> 0 <SEP> 2,"" <tb> <SEP> z <tb> <SEP> k <SEP> Iha <SEP> 2 <SEP> 0.4 <SEP> 0.4 <tb> <SEP> kglha <SEP> 2 <SEP> 1 <SEP> 0.4 <SEP> 0.4 <tb> <SEP> POST <SEP> GZNCL <SEP> I <SEP> I <tb> <SEP> BUSH <SEP> BEAN <SEP> I <SEP> 2C <SEP> 1C,1H <SEP> 9C <tb> <SEP> COTTON <SEP> iC <SEP> I <SEP> O <SEP> o <SEP> zs6G <tb> <SEP> MORNINGGLORY <SEP> 1C <SEP> I <SEP> O <SEP> SC <SEP> 9G <tb> COCXLBUR <SEP> U <SEP> I <SEP> O <SEP> 2C <tb> <SEP> CASSIA <SEP> - <SEP> C <SEP> O <SEP> 3C <tb> <SEP> NUTSEDGE <SEP> --0 <SEP> - <SEP> O <SEP> ¯ <SEP> 2G <tb> <SEP> CRABGRASS <SEP> . <SEP> O <SEP> 1C <tb> <SEP> BARNYAIQI3CAS <SEP> 2H--- <SEP> 0' <SEP> 1 <tb> <SEP> tLD <SEP> OA'iS <SEP> 3 <SEP> o <SEP> I <tb> <SEP> WHEAT¯ <SEP> o <SEP> I <SEP> o <tb> <SEP> co <SEP> bHIIDI <SEP> 0- <SEP> I <tb> <SEP> SOYBEAP: <SEP> 0 <tb> <SEP> RICE <SEP> 5G <SEP> G <tb> <SEP> SORGHlfil <SEP> 5G <SEP> 0 <tb> <SEP> TZ <tb> PRE¯ <SEP> ePERGEJCZ¯¯ <tb> <SEP> ORNINGGLORP, <SEP> 4G <SEP> ¯1¯9G <SEP> ¯I <tb> <SEP> COCKI;EBUR <SEP> ¯¯¯2G <SEP> 1¯ <SEP> sG <tb> <SEP> MORNING & ORY. <SEP> . <SEP> 4G <SEP> 9G <SEP> &verbar; <SEP> 8G <tb> <SEP> COCKL <SEP> AL <SEP> <tb> CASSIA <SEP> 6G <SEP> 5G <SEP> ¯ <SEP> ¯/ <SEP> ¯ <SEP> 6G <tb> IJT¯S'IG'E¯ <SEP> SG <SEP> ¯ <SEP> I¯ <SEP> 0 <tb> CABGE1S <SEP> ¯ <SEP> ¯0 <SEP> 3G <tb> BARNPARDGRASS <SEP> zc¯, <SEP> fG <SEP> 1 <SEP> 56 <tb> wlLD <SEP> OATS¯ <SEP> i <SEP> ¯ <SEP> IC <SEP> ' <SEP> 0 <tb> REEAT <SEP> 1C <SEP> 0 <SEP> 1G <tb> CORN <SEP> 3G <SEP> ¯ <SEP> 3G <SEP> ¯ <SEP> 1C,SG <tb> SOYBEAN <SEP> Q <SEP> O <SEP> IR <tb> RICE <SEP> sH <SEP> 7G <SEP> 8H <tb> . <SEP> SORGEU! <SEP> SG <SEP> 4G <SEP> C <tb> Table A (continued) EMI133.1 <tb> <SEP> j, <SEP> a <tb> <SEP> 3 <SEP> %?==' <SEP> ='Y"' <SEP> = <tb> <SEP> L <SEP> I <tb> <SEP> = <SEP> I <tb> <SEP> 0 <SEP> o' <SEP> "", <SEP> U <tb> <SEP> 0 <tb> <SEP> 5 <tb> <SEP> &commat;9 <SEP> ¯ <SEP> es <tb> kzXha <SEP> ¯ <SEP> 0.4 <SEP> 0.4 <SEP> 1 <SEP> 0.4 <tb> POST <SEP> EME= <SEP> ERICE <tb> 'BUSH <SEP> BtE <SEP> ' <SEP> 9C <SEP> ' <SEP> 3C,5G,6? <SEP> I <SEP> SC <tb> COTTON <SEP> 2C <SEP> 6G <SEP> I <SEP> 1C <SEP> t <SEP> 2C <tb> MORgINGGLOBY <SEP> 9C <SEP> I <SEP> 3G <SEP> 5C,8G <tb> COCKLEBUR <SEP> 1C,3H <SEP> I <SEP> lC <SEP> I- <SEP> 2C <tb> CASSIA <SEP> - <SEP> 2C,7G <SEP> i <SEP> - <SEP> I <SEP> 1C <tb> NL'TSEDGE <SEP> I <SEP> 2G <SEP> O <SEP> G <tb> CWGWS <SEP> 2C,7G <SEP> 0 <tb> <SEP> I <SEP> G <tb> <SEP> 16 <tb> <SEP> 2C,76 <SEP> o <SEP> I <SEP> 0 <tb> <SEP> 26,96 <SEP> 0 <SEP> 1" <SEP> ?r <tb> SO'5EM <SEP> ¯, <SEP> 5C, <SEP> 9G <SEP> : <SEP> O <SEP> 7 <SEP> ¯I <SEP> 1C <SEP> ¯ <tb> ISOYBEL <SEP> ¯ <SEP> 5C,9G <SEP> o <SEP> t <tb> <SEP> 16 <tb> 12165. <SEP> 3C,8G <SEP> 16,36 <tb> I <SEP> SORCIUM <SEP> ¯ <SEP> 2C, <SEP> 9G <SEP> 0 <SEP> 2¯6, <SEP> 76 <tb> MOILINGCLOBY. <SEP> - <SEP> 9G <SEP> .fe <tb> COCKLEBUR <SEP> 9G <SEP> 0 <SEP> ¯ <SEP> ¯ <SEP> 8G <tb> CASSIA <SEP> 9G <SEP> . <SEP> 0 <tb> NUTSEDGE <SEP> 9G <SEP> j <SEP> O <SEP> O0 <tb> CRABGESS <SEP> 3C, <SEP> 8G <SEP> 3C, <SEP> G <SEP> 1C <tb> <SEP> hASTTARDo <SEP> A55 <SEP> sH <SEP> u <SEP> H <SEP> 2C <SEP> SR <tb> WILD <SEP> OATS <SEP> 2C,8G <SEP> -0 <SEP> 7 <SEP> 0 <SEP> 2G <tb> WHEAT <SEP> 2G <tb> CORN <SEP> 2C,9G <SEP> o <SEP> 1C,3G <tb> SOYSELU' <SEP> ¯ <SEP> 8B <SEP> u <SEP> i <SEP> U <SEP> ¯ <SEP> 7 <SEP> 0 <tb> RICE <SEP> ADE <SEP> u <SEP> 1C,7G <tb> SORGHUE <SEP> C <SEP> ric <SEP> i <SEP> lC,8G <tb> Table A (continued) EMI134.1 <tb> <SEP> 0 <tb> <SEP> " <tb> <SEP> SO <SEP> C <SEP> <tb> <SEP> 2 <SEP> > <SEP> 5 <SEP> ii <SEP> 2 <tb> <SEP> SO2N(cR3)2 <SEP> N; ;C <SEP> )C, <tb> <SEP> 2 <SEP> 1 <SEP> 'lizC <tb> <SEP> cE3 <tb> <SEP> I <tb> <SEP> kg/ha <SEP> 1/10 <tb> <SEP> POST-ESERGEN'CE <tb> <SEP> BUSHBEMv <SEP> 9D.9G,6Y <tb> <SEP> COTTON <SEP> Sc <SEP> 9G <tb> <SEP> MORNINGGLORY <SEP> 9C <tb> <SEP> COC¯KLEBUP¯ <SEP> 39G <tb> <SEP> CASSIA <SEP> , <SEP> 3C <SEP> . <SEP> 9G <tb> <SEP> MjTS3E <SEP> I. <SEP> 7¯G <tb> <SEP> CRA8GRASS. <SEP> 9C <tb> <SEP> BALTARDGRASS <SEP> ioc <tb> <SEP> WILD <SEP> OATS <SEP> 9C <tb> <SEP> 1' <SEP> , <SEP> 1C <SEP> . <SEP> ¯ <SEP> 1C, <SEP> 7G <tb> L <SEP> CON¯ <SEP> ¯¯¯ <SEP> ¯gC <tb> 1 <SEP> SOYBE <SEP> ¯ <SEP> 9C <SEP> ¯ <tb> <SEP> RLCE <SEP> 9C <tb> <SEP> SORQnaM <SEP> 10C <tb> <SEP> PREEMERGENCE <tb> <SEP> MORN1'ACGtORY <SEP> 9G <tb> <SEP> COCKLEBUR <SEP> 9G <tb> <SEP> CASSIA <SEP> 1C,9G <tb> <SEP> NUTSEDGE <SEP> 10E <tb> <SEP> CRABGRASS <SEP> lC,9G <tb> <SEP> BARNYARDGRASS <SEP> ¯ <SEP> 2C,9B <tb> <SEP> WILD <SEP> OATS <SEP> ¯ <SEP> 2C19G <tb> <SEP> WREAA' <SEP> 9G <tb> <SEP> COLN <SEP> 1C19G <tb> <SEP> SOYBEAN <SEP> 9X <tb> <SEP> RICE <SEP> ' <SEP> IOE <tb> <SEP> SORGEM <SEP> sd <tb> Table A (continued) EMI135.1 <tb> <SEP> =H <tb> <SEP> v <SEP> v <tb> <SEP> 2 <SEP> 2 <tb> <SEP> O=U <SEP> O=U <tb> <SEP> = <tb> = <SEP> I <tb> <SEP> c; ; <tb> <SEP> 10 <SEP> 0 <tb> <SEP> 101 <tb> <SEP> kg/ha <SEP> 2 <SEP> 0.4 <SEP> 2 <SEP> 0.4 <tb> <SEP> POSItEHERGEN'= <SEP> l <tb> <SEP> BUSHBEA <SEP> 50. <SEP> eG.6Y <tb> <SEP> BYSEBELN <SEP> Y <SEP> 6 <SEP> 6? <SEP> 2E <SEP> 6F <SEP> 0 <tb> <SEP> COTTON <SEP> 3C <SEP> . <SEP> 9G <SEP> ¯ <SEP> 2C <SEP> . <SEP> 2H <SEP> 8G <SEP> it <SEP> 0 <tb> <SEP> MORNINGGLORY <SEP> lOC <SEP> 2C <SEP> SC <SEP> 2H <SEP> | <SEP> 1H <tb> <SEP> COCKLEBUR <SEP> 1C, <SEP> 8G <SEP> 2C <SEP> 1C <SEP> O <tb> <SEP> CASSIA <SEP> 2C <SEP> . <SEP> SC <SEP> 3C <SEP> .. <SEP> .. <SEP> 0 <SEP> 1 <SEP> 0 <tb> <SEP> NUTSBDGE <SEP> 1C <SEP> 9G <tb> <SEP> CRABGRAS <SEP> S <SEP> i <SEP> 1C, <SEP> 76 <SEP> 0 <SEP> o <tb> <SEP> BARPARDGRASS <SEP> 1 <SEP> 90 <SEP> 3C,9H <SEP> 0 <SEP> I <SEP> o <tb> <SEP> WZLI) <SEP> OATS <SEP> 1C,7G <SEP> 3C,5G <SEP> 0 <SEP> 0 <tb> <SEP> WLIEAT <SEP> ] <SEP> 4C.8G <SEP> 1 <SEP> 2C.4G <SEP> 0 <SEP> 1 <SEP> 0 <tb> <SEP> L <tb> <SEP> I <tb> <SEP> RCE <SEP> 3C,9G <SEP> 50,96 <SEP> i <SEP> 0 <tb> <SEP> SORGIIUMI <SEP> 9% <SEP> o <SEP> o <tb> <SEP> I <tb> <SEP> PRE-EMEIGEh"CE <tb> <SEP> MORyIsCGLORY <SEP> 96 <SEP> - <SEP> sc¯ <SEP> SG <SEP> 36 <SEP> ¯ <tb> <SEP> COCIEBUR <SEP> 90 <SEP> 8LL'5G <SEP> ¯ <tb> <SEP> 8G <SEP> 5H <SEP> I <tb> <SEP> CASSIA <SEP> 1C, <SEP> 96 <SEP> 0 <tb> <SEP> NUTSED0E <SEP> 1 <SEP> 10'8 <SEP> 96 <SEP> ¯¯0 <SEP> ¯ <SEP> o <tb> <SEP> CEABGRASS <SEP> 46 <SEP> 0¯ <SEP> ¯0 <tb> <SEP> BARL'WARDGRASS <SEP> 20 <SEP> . <SEP> 9H <SEP> ¯ <SEP> 20 <SEP> ,9H <SEP> 20 <SEP> 0 <tb> <SEP> WILD <SEP> OATS <SEP> 20,96 <SEP> 86 <SEP> 0 <SEP> -0 <tb> <SEP> WHEAT <SEP> 90 <SEP> ¯ <SEP> 56 <SEP> li <SEP> -0 <tb> <SEP> I <tb> <SEP> RICE <SEP> 1 <SEP> no <SEP> 10E <tb> <SEP> SORGHUR.T <SEP> 1 <SEP> H <SEP> 2C <SEP> 1 <SEP> 9H <SEP> O <SEP> . <SEP> I <SEP> O <SEP> 0 <tb> Table A (continued) EMI136.1 <tb> <SEP> c <tb> <SEP> I <tb> <SEP> = <tb> <SEP> I <SEP> I <tb> <SEP> 3¯e; <SEP> C-" <tb> <SEP> I <SEP> -I. <tb> <SEP> o <SEP> : <SEP> Z <tb> <SEP> 0 <tb> <SEP> V1 <SEP> IX <SEP> n <tb> <SEP> kgiha <SEP> 0.4 <SEP> 2 <SEP> s <SEP> 0.4 <tb> <SEP> ... <SEP> .......... <SEP> , <SEP> .. <SEP> . <SEP> .. <SEP> . <SEP> . <SEP> , <tb> <SEP> P0ST-EMERGZS'CE <tb> <SEP> BUSHB <SEP> t <SEP> 7C <SEP> 9G <SEP> 6C <SEP> 9G <SEP> 6Y <SEP> 6C <SEP> SG <SEP> 6Y <tb> <SEP> COTTON <SEP> ,, <SEP> ¯ <SEP> 6C <SEP> 9G <SEP> 9c <SEP> sc <SEP> 9G <tb> <SEP> MORNlNGGLOR? <SEP> sc <SEP> 9G <SEP> loc <SEP> ioc <tb> <SEP> COCKLEBUR <SEP> SC <SEP> lOC <SEP> 10C <SEP> ' <SEP> Sc <tb> <SEP> 6AS5ZA¯¯ <SEP> 1¯ <SEP> 5C <SEP> 76¯ <SEP> 9C <SEP> 36 <SEP> 66 <SEP> i <tb> <SEP> NUTSEDG <SEP> ¯16¯ <SEP> 86¯ <SEP> ¯ <SEP> 16¯ <SEP> 96 <SEP> 3¯6 <tb> <SEP> ¯ <SEP> CRABGASS¯ <SEP> 96¯ <SEP> 9C <SEP> 26 <SEP> 8G <tb> I <tb> <SEP> ¯ <SEP> BALYYXao¯cXA'sj <SEP> 9C <SEP> 9C <SEP> 9C <tb> <SEP> WLLD <SEP> OATS <SEP> 9C <SEP> 16 <SEP> 36 <SEP> ¯ <SEP> 4 <tb> <SEP> ¯ <SEP> W85A'6¯¯ <SEP> ,9,e <SEP> 26 <SEP> 76 <SEP> 1C <SEP> 56 <tb> <SEP> CORN <SEP> 3Ü <SEP> 9G <SEP> 2C <SEP> SG <SEP> . <SEP> 2C <SEP> 7H <tb> <SEP> SOPBk <SEP> L <SEP> BC <SEP> 9G <SEP> 3C <SEP> BG <tb> <SEP> ,RCE <SEP> 9C <SEP> I <SEP> 76 <SEP> .¯ <SEP> 26 <SEP> 76 <SEP> i <tb> <SEP> ¯ <SEP> SORGECr <SEP> - <SEP> se <SEP> / <SEP> 26 <SEP> 96 <SEP> 16 <SEP> /H <SEP> ¯ <tb> <SEP> i"PREaEMRGEC <SEP> I <tb> <SEP> ¯ <SEP> MOILTJGGLORY3 <tb> <SEP> 9G <SEP> 96 <tb> <SEP> 9¯6 <tb> <SEP> COCKLEBUR <SEP> ¯ <SEP> 96 <SEP> 9H <SEP> 98 <tb> <SEP> CjSIA <SEP> 96 <SEP> 96 <SEP> ¯76 <tb> <SEP> NUTSEDGE¯ <SEP> ¯¯IOE- <SEP> 10E <SEP> 96 <tb> <SEP> ! <SEP> CIABGS <SEP> ¯ <SEP> 1C <SEP> 96 <SEP> ¯. <SEP> ¯1C <SEP> 86 <SEP> 2G <tb> <SEP> BARNYARDGRASS <SEP> ¯ <SEP> ¯5e <SEP> ¯PH <SEP> , <SEP> ¯ <SEP> 98 <SEP> '¯ <SEP> 1C <SEP> 98 <tb> .¯ <SEP> WILD¯OS <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯4C <SEP> 98 <SEP> ¯66 <SEP> ¯ <SEP> 5G <tb> <SEP> WBEAT <SEP> 2¯6 <SEP> ¯98 <SEP> [ <SEP> 66 <tb> <SEP> ¯ <SEP> CORN <SEP> 96 <SEP> 16 <SEP> 96 <SEP> 1C <SEP> 96 <tb> <SEP> ¯ <SEP> SOYBEAN <SEP> ¯ <SEP> 9a <SEP> ¯ <SEP> 9H <SEP> i <SEP> 26 <SEP> 7K <tb> <SEP> ¯ <SEP> 8165 <SEP> 10E <SEP> 10E <SEP> 98 <tb> <SEP> SR <SEP> ¯ <SEP> . <SEP> . <SEP> 1C <SEP> SG <SEP> ; <SEP> SG <tb> Table A (continued) EMI137.1 <tb> <SEP> :""' <tb> <SEP> -s <SEP> z <SEP> a <tb> <SEP> z <SEP> 2 <tb> <SEP> o <SEP> 0 <SEP> : <tb> <SEP> := <SEP> In <SEP> -= <SEP> In <tb> <SEP> = <tb> <SEP> 0 <tb> <SEP> so <SEP> N <SEP> z <SEP> ¯U <tb> <SEP> 8 <SEP> o <tb> <SEP> 1111 <SEP> 11111; <SEP> 11111 <SEP> 1111 <tb> <SEP> kg/ha <SEP> 0.4 <SEP> 0.4 <SEP> ¯ <tb> <SEP> POSI-IERCECE <tb> <SEP> 3USABLE <SEP> 9D <SEP> 9G <SEP> 6Y <SEP> 7C <SEP> 9G7 <tb> <SEP> COTTON <SEP> 9C <SEP> .... <SEP> 9C <tb> <SEP> MORINGCLORY <SEP> lOC <SEP> , <SEP> 10 <tb> <SEP> COCKLEBUR <SEP> 3C <SEP> 9G <SEP> 4r <tb> <SEP> CASSIA <SEP> SC <SEP> 9G <SEP> I <SEP> 9C <tb> <SEP> NtTSEDGE <SEP> 1C <SEP> 80 <SEP> kC <SEP> 9G <tb> <SEP> CRBGRASS <SEP> 3C <SEP> 6C <SEP> 4C <SEP> 90 <tb> <SEP> BARYYARDGRASS <SEP> 50 <SEP> 9H <SEP> IOC <tb> <SEP> WILD <SEP> OATS <SEP> -2C <SEP> BH <SEP> 5C <SEP> 96 <tb> ¯ <SEP> WHMT <SEP> 3C <SEP> /G <SEP> 4C¯ <SEP> 90 <tb> <SEP> CORN <SEP> 8U <SEP> 9G <SEP> 9e <tb> <SEP> SOYBE1 <SEP> 3C <SEP> 9G <SEP> 9C <tb> <SEP> JICE <SEP> 6C <SEP> 9G <SEP> 5C <SEP> 96 <tb> <SEP> SORCHUM <SEP> 3C <SEP> 90 <SEP> 10C <tb> <SEP> SORG}IUM <SEP> 3C <SEP> 9G <SEP> lOC <tb> <SEP> PRE-PIERCEECE <SEP> ¯ <tb> <SEP> MORNIJGGLORY <SEP> 96 <SEP> G: <SEP> ¯ <tb> <SEP> COCEtEBtTR <SEP> .91r <SEP> 9L <tb> <SEP> COCKLEBIJR <SEP> 9H <SEP> 9H, <SEP> .... <tb> <SEP> CASSIA <SEP> 9G <tb> <SEP> EZ"TSEDGE <SEP> 10E <SEP> 10E <tb> <SEP> CRABGRASS <SEP> 1 <SEP> 2C <SEP> 46 <SEP> - <SEP> -- <SEP> 5C <SEP> -46 <tb> <SEP> BAR"JYARDCI1ASS <SEP> ¯30 <SEP> 9H- <SEP> ¯sa <tb> <SEP> Wf19 <SEP> OATS <SEP> 2C <SEP> 9H <SEP> 9H¯ <SEP> ¯ <SEP> ¯ <tb> <SEP> WHEAT <SEP> 1C <SEP> 9G <SEP> lOE <tb> <SEP> CORN <SEP> 9G <SEP> lOE <tb> <SEP> SOYBEAN <SEP> SB <SEP> 9H <tb> <SEP> RICE <SEP> lOË <SEP> - <SEP> - <SEP> ''- <SEP> 10E <SEP> OE <tb> <SEP> SORZ! <SEP> 3C <SEP> . <SEP> lOE <tb> Table A (continued) EMI138.1 <tb> <SEP> m <tb> <SEP> 2 <SEP> J <tb> <SEP> z <SEP> 2 <tb> 0 <SEP> C <SEP> :' <tb> <SEP> = <SEP> cu <SEP> = <tb> <SEP> o <SEP> = <tb> <SEP> 0 <tb> <SEP> to <SEP> tu <tb> <SEP> kg/ha <SEP> 0.4 <SEP> 0.4 <tb> <SEP> POST <SEP> -ERGACE <tb> <SEP> BUSHBE*E <SEP> 3C <SEP> 9G <SEP> 6Y <SEP> 6C <SEP> 9G <SEP> 6Y <tb> <SEP> COTTON <SEP> 4C <SEP> 9G <SEP> 3C <SEP> 3E <SEP> 9G <tb> <SEP> MORNINGGLORY <SEP> L <SEP> lOC <SEP> lOC <tb> <SEP> COCKLEBUR <SEP> 3C <SEP> 9G <SEP> ¯ <SEP> ¯I <SEP> 1C <SEP> 4G <tb> <SEP> CASSIA <SEP> 3C <SEP> 6 <SEP> - <SEP> 5G <SEP> 2C <SEP> 6G <tb> <SEP> NlJTSEDGE <SEP> G <tb> <SEP> CRABGRASS <SEP> ¯ <SEP> 2G <SEP> I <SEP> SC <SEP> 9G <tb> <SEP> AR'YAIWGRASS <SEP> 3C <SEP> 9H <SEP> SC <SEP> 9R <tb> <SEP> WILD <SEP> OATS <SEP> i <SEP> ¯ <SEP> SG <SEP> L <SEP> lC <SEP> 5G <tb> <SEP> WHEAT <SEP> 6G <SEP> go¯ <SEP> 5X <SEP> 1C <SEP> SG <tb> <SEP> CORN <SEP> 2C <SEP> 2C <SEP> 9H <SEP> -' <SEP> - <SEP> 4C <SEP> 9G <tb> <SEP> SOYBEAN <SEP> 3C <SEP> 9G <SEP> 26 <SEP> 8G <SEP> 5X <tb> <SEP> RICE <SEP> SC <SEP> 9G <tb> <SEP> / <SEP> SORCHUM <SEP> 56 <SEP> 96 <tb> <SEP> PRE-ERGEN <SEP> CE <tb> <SEP> MORNI?.;GGLORY <SEP> 9G <tb> - <SEP> OCI(LEBUR <SEP> 9H <SEP> 9H <tb> <SEP> CASS¯f <SEP> tC <SEP> 86 <SEP> 2C <SEP> 96 <tb> <SEP> NLTSEBGE <SEP> I <SEP> X; <SEP> 1C <SEP> 96¯ <tb> <SEP> ¯ <SEP> CPGBCRASS¯¯le <SEP> 66 <SEP> Ic <SEP> 56¯ <tb> <SEP> BARNYARDGRASS <SEP> 9H <SEP> 9H <tb> <SEP> WILD <SEP> OATS <SEP> ¯ <SEP> 1C <SEP> 7G <tb> . <SEP> WHEAT <SEP> 1C <SEP> 8G <SEP> 9G <tb> <SEP> CORaY <SEP> 1C <SEP> 9G <SEP> 2s <SEP> 9G <tb> <SEP> SOYBEAN <SEP> 1C <SEP> 4H <SEP> 1C <SEP> 4H <tb> <SEP> RICE <SEP> 9E <SEP> ¯ <SEP> 9H <tb> <SEP> ¯ <SEP> SORG$UM <SEP> ¯ <SEP> ¯ <SEP> C <SEP> 1C <SEP> 9Ç <tb> Table A (continued) EMI139.1 <tb> <SEP> -"' <SEP> r?\ <SEP> = <tb> <SEP> 0 <SEP> m0 <tb> <SEP> V <tb> <SEP> = <SEP> = <tb> o <SEP> : <SEP> 0 <SEP> 0:0 <tb> <SEP> I <SEP> = <SEP> I <tb> <SEP> 0 <SEP> = <SEP> 0 <SEP> 0 <SEP> "'1 <tb> <SEP> 0 <SEP> = <SEP> 0 <tb> <SEP> 'a <SEP> 0 <SEP> 0 <tb> <SEP> 0 <SEP> Z <SEP> 0 <tb> <SEP> (4,00 <SEP> t¸"-,'0 <tb> <SEP> kg/ha <SEP> 0.4 <SEP> 0.4 <tb> <SEP> POsT-EEERGZNCE <tb> <SEP> BUSHBL <SEP> SC <SEP> 9G <SEP> 35 <SEP> 9G <SEP> 6? <tb> <SEP> COTTON <SEP> 5C,9G <SEP> 2C <SEP> 7G <tb> <SEP> MORh'INGGLORY <SEP> , <SEP> 9C <SEP> 2C <SEP> 90 <tb> <SEP> COCKLEBUR <SEP> SC <SEP> 90 <SEP> 1C*6G <tb> <SEP> CASSIA <SEP> 3C <SEP> 2C <SEP> 50 <tb> <SEP> NUTSEDGE <SEP> O <SEP> 0 <tb> <SEP> CWGRASS <SEP> iC <SEP> 50 <SEP> 20 <tb> <SEP> tARDGRASS <SEP> 3C,9H <SEP> 2C,5H <tb> <SEP> WILD <SEP> OATS <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> 4G <SEP> 0 <tb> <SEP> WHEAT <SEP> O <SEP> 0 <tb> <SEP> CORN <SEP> 8H <SEP> lC <SEP> 80 <tb> <SEP> SOYBEAN <SEP> 2C,9G <SEP> 1C, <SEP> 6G <tb> <SEP> RICE <SEP> ; <SEP> 9C <SEP> lC <SEP> 30 <tb> <SEP> SOROKL'M <SEP> 9R <SEP> ic <SEP> 1 <SEP> 7R <tb> <SEP> PRE-EMERGEN <SEP> CE <tb> <SEP> MORN3GGLORY <SEP> 9G <SEP> i <SEP> 9G <tb> <SEP> COCKLEBUR <SEP> 9G <SEP> 8 <tb> <SEP> CASSIA <SEP> . <SEP> ¯ <SEP> , <SEP> , <SEP> 9G <SEP> 9G <tb> <SEP> NUTSEDGE <SEP> ¯ <SEP> 9G <SEP> ¯¯ <SEP> 50 <tb> <SEP> CRABORASS <SEP> 2G <SEP> . <SEP> IC <SEP> 30 <tb> <SEP> BARNYARDGRA <SEP> SS <SEP> 2C <SEP> * <SEP> 9R <SEP> 2C <SEP> 9E <tb> WILD <SEP> OATS <SEP> 1C, <SEP> 6G <SEP> 5G <tb> <SEP> WHEAT <SEP> 3G <SEP> O <tb> <SEP> CORN <SEP> 9E <SEP> 911 <SEP> 1C, <SEP> 6G <tb> <SEP> SOYBEAN <SEP> ' <SEP> 1X,3G <SEP> 2C <tb> <SEP> RICE <SEP> 9H <SEP> 1C, <SEP> 8H <tb> <SEP> H <SEP> i <SEP> I <SEP> 9H <SEP> iC <SEP> 9G <tb> Table A (continued) EMI140.1 <tb> <SEP> n <tb> <SEP> j <tb> iu <SEP> 0 <SEP> :' <SEP> ¯¯¯ <tb> <SEP> =1 <tb> <SEP> zo <SEP> N <SEP> z <SEP> f <tb> 0 <SEP> cu9 <SEP> 0 <tb> <SEP> "I <SEP> 0 <tb> <SEP> 0 <SEP> ," <SEP> 0 <tb> <SEP> t; <SEP> tO <tb> <SEP> kg/ha <SEP> ¯¯ <SEP> ¯ <SEP> 0.4 <SEP> 0.4 <tb> <SEP> POSTu <SEP> GiCCE <tb> <SEP> BUSEI <SEP> 3S <SEP> 9G <SEP> 6? <SEP> 45, <SEP> G, <SEP> Y <tb> <SEP> COTTON <SEP> ¯ <SEP> ¯ <SEP> 21115G <SEP> 3C,5G <tb> <SEP> MOXSINGGLORX <SEP> 3C <SEP> 9H <SEP> C <tb> <SEP> COCK=BUR <SEP> 3C <SEP> 7 <SEP> 9G <SEP> 1C,3H <SEP> H <tb> <SEP> CASSIA <SEP> 3C <SEP> 4H <SEP> 1C <SEP> lC <tb> i <SEP> NUTSEDCE <SEP> ¯ <SEP> ¯ <SEP> 1C4G <SEP> 0 <tb> <SEP> ¯CRABGRASS¯ <SEP> ¯a <SEP> ¯ <SEP> -0 <tb> <SEP> IBAR,P¯IRDG¯XAS¯4EI <SEP> 1C,58 <tb> <SEP> ¯wnJAs <SEP> ¯ <SEP> o <tb> <SEP> .... <SEP> .. <SEP> .. <SEP> ... <SEP> . <SEP> .. <tb> <SEP> ,¯WfpiT <SEP> O¯ <tb> <SEP> CORN <SEP> 2H <SEP> 2C,9H <SEP> 7G <tb> <SEP> p <tb> <SEP> SOYB¯EAr <SEP> ¯i <SEP> ¯ <SEP> 2II,8 <SEP> 2C,86 <tb> <SEP> RICE <SEP> ¯ <SEP> ' <SEP> IC <SEP> 1C, <SEP> 7G <tb> <SEP> SQRGENM <SEP> 3 <SEP> ou <SEP> 2C, <SEP> 9-G <tb> <SEP> PRE-EMT;IIGZNCE <SEP> L <tb> <SEP> MORNoJcnoRY <SEP> 13---- <SEP> 10E <tb> <SEP> ,COCXLEBUR <SEP> i¯ <SEP> 8C <tb> <SEP> I <SEP> 9H <tb> <SEP> 1 <SEP> 86 <SEP> - <SEP> CXSSIA <SEP> 8G <tb> <SEP> BARNYARDGRASS <SEP> 1C, <SEP> iC <SEP> 2C, <SEP> SG5G <tb> <SEP> WILD <SEP> OATS <SEP> 3 & <SEP> G <tb> WHR'I"T <SEP> o <tb> <SEP> CORN <SEP> lC,6G <tb> <SEP> SO?'BEM." <SEP> - <SEP> '- <SEP> 3G <tb> <SEP> RICE <SEP> I <SEP> 1C <SEP> . <SEP> 6G <SEP> 9E <tb> <SEP> SOBGHUI <SEP> j <SEP> 1.8G <SEP> IC,9G <tb> Table A (continued) EMI141.1 <tb> j <SEP> C <SEP> O <tb> <SEP> = <SEP> = <tb> <SEP> = <SEP> = <tb> <SEP> o <SEP> : <SEP> o: <tb> <SEP> c"'I <tb> 6 <SEP> 0 <tb> <SEP> z <SEP> c <tb> <SEP> to <SEP> tc <tb> <SEP> - <tb> kg/ha <SEP> 0.4 <SEP> 0.4 <tb> <SEP> POSI-FMvRGEN'CE <tb> <SEP> BUSH3riN <SEP> 2C <SEP> 6G <SEP> 5C,8G,6Y <tb> <SEP> COTTON <SEP> 1C,3G <SEP> 3C,2E <tb> <SEP> MORNINGGLOR? <SEP> IT <SEP> 1C <SEP> IC <SEP> lOC <tb> <SEP> COCKLEBUR <SEP> 1C <SEP> - <SEP> 2C,9B <tb> <SEP> CASSIA <SEP> -- <SEP> O <tb> <SEP> NtTSEDGE <SEP> O <SEP> 26 <tb> <SEP> CRABGRASS <SEP> 2C,4G <tb> <SEP> BARVYARDGEZASS <SEP> i <SEP> 1C,4G <SEP> 2C,8H <tb> <SEP> WILD <SEP> OXTS <SEP> V <SEP> IC;,LG <tb> <SEP> 0 <SEP> Ic;,G <tb> <SEP> CORN <SEP> I <SEP> Ic,sa <SEP> LL; ;,n <tb> <SEP> soYsElesF'---- <SEP> 4H <SEP> '6G¯¯ <tb> <SEP> BICE <SEP> - <SEP> IC,9G <tb> <SEP> PR'-EMERGEXCE <tb> <SEP> PI(E-MIRGECE <tb> <SEP> I <tb> <SEP> MORIBGGLORY <SEP> se <tb> <SEP> IOE <SEP> 9ff¯ <tb> <SEP> I <SEP> COCESEBCR <SEP> 9G <SEP> se <tb> <SEP> i <SEP> CASSTP, <SEP> SG <tb> <SEP> ; <SEP> NL'TSEDG'r' <SEP> - <SEP> 1 <SEP> 46 <SEP> --g <tb> <SEP> tG <tb> <SEP> WHEAT <SEP> ¯ <SEP> 3G <tb> <SEP> CORN <SEP> 1C,7G <SEP> 1U,9G <SEP> G <tb> <SEP> SOYBEAN <SEP> C <tb> <SEP> RICE <SEP> - <SEP> 9H <SEP> 911 <tb> <SEP> SORGHt'M <SEP> ¯LC.9G <SEP> 911 <tb> Table A (continued) EMI142.1 <tb> <SEP> C', <tb> <SEP> = <tb> <SEP> i <SEP> W <SEP> ar <SEP> i <tb> <SEP> -I <SEP> o <tb> <SEP> = <SEP> 0 <tb> - <SEP> or <tb> <SEP> - <SEP> 0 <SEP> - <SEP> I <tb> <SEP> Z <SEP> m <SEP> I <SEP> = <tb> <SEP> y2 <SEP> = <tb> <SEP> o <SEP> 0-0 <SEP> i <SEP> Gla <tb> <SEP> "I <SEP> 0 <tb> <SEP> o <SEP> 4U <tb> <SEP> X <SEP> W <tb> <SEP> kg/ha <SEP> 0.4. <SEP> 0.4 <tb> I <tb> <SEP> POST-EMERGB'CE <tb> <SEP> BUSHBEMv <SEP> 9D <SEP> 9G <SEP> 6Y <SEP> 3C <SEP> 7G <SEP> 6? <tb> <SEP> COTTON <SEP> 3C <SEP> 3H <SEP> 9G <SEP> 3B <tb> <SEP> bfORINGGLORY <SEP> lOC <SEP> lC,9G <tb> <SEP> COCKLE3L"'R <SEP> 3C,SG <SEP> 2H <tb> <SEP> CASSIA <SEP> ¯ <SEP> lC,5G <SEP> 1C,4G <tb> NUTSEDGE <SEP> lC,SG <SEP> 0 <tb> <SEP> CRABGRASS <SEP> -- <SEP> -- <SEP> 2C <SEP> I <SEP> 3G <tb> <SEP> BARNUADGOSS <SEP> 2C,9 <tb> <SEP> WILD <SEP> OATS <tb> PLEAT <SEP> -- <SEP> 46 <SEP> 1 <tb> <SEP> CORN <SEP> C, <SEP> H <SEP> -2C, <SEP> we <SEP> G <tb> <SEP> SOYBEiiN---- <SEP> ac <SEP> 7G <SEP> x- <SEP> 2f, <SEP> 6G <tb> <SEP> r <SEP> 2C,iG <SEP> ' <SEP> - <SEP> ' <SEP> 5; <SEP> ''- <SEP> ¯ <SEP> RICE <SEP> rr;,vcj <SEP> 5% <tb> - <SEP> SORGHZM <SEP> LCp, <SEP> YCt <SEP> I <tb> <SEP> PRE-PIERGCJCI: <tb> <SEP> HoRcnoRn <tb> <SEP> - <SEP> 8G <SEP> 8G <tb> <SEP> I <SEP> COCESFBUR <SEP> I <SEP> 8H <SEP> sH <tb> <SEP> I7G <tb> <SEP> ¯ <SEP> CASSSB <SEP> 5G <tb> <SEP> BARNYARDGRASS <SEP> ¯ <SEP> 4G <tb> <SEP> WILD <SEP> OATS <SEP> 3G <SEP> 0 <tb> <SEP> WHEAT <SEP> 3G <SEP> O <tb> C,SG <SEP> 1C,8G <SEP> 1C,3G <tb> <SEP> SO?BEAN <SEP> lE <SEP> 2G <tb> <SEP> RICE <SEP> 1 <SEP> E <tb> <SEP> S] <SEP> I <SEP> 98 <SEP> lr <SEP> G <tb> Test B Two plastic bulb pans were filled with fer tilized-and limedFallsIngton silt loam soil. One pan was planted with corn, sorghum, Kentucky blue grass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (cyprus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Pas palum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Erassica arvensis), cocklebur (Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated preemergence 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 de scribed previously for Test A. The data are summarized in Table B. Note that certain compounds are useful as preemergence treatments for weed control in crops such as soybeans and wheat. PRE-EMERGENCE ON FALLSINGTON SILT LOAM EMI144.1 EMI144.2 <tb> Rat <SEP> ¯kgi/ha <SEP> k°/h <SEP> O.0 <tb> <SEP> Craerass <SEP> n <SEP> IC <tb> <SEP> Crab <SEP> rasps <SEP> Q <tb> <SEP> kC: <SEP> ?C: <SEP> 8G5H <tb> <SEP> Sorghum <SEP> .Cr, <SEP> hut <tb> WLI <SEP> Oaes <SEP> 26, <SEP> I <SEP> 36 <SEP> 36 <tb> <SEP> Johnsoanras¯s <SEP> 46 <SEP> 6G,5H <SEP> 76,5H <tb> <SEP> Daisarass¯ <SEP> , <SEP> I <SEP> ¯56 <SEP> I <SEP> ¯se <SEP> 66 <tb> <SEP> Giant <SEP> xtail <SEP> 3C;--C"- <SEP> 8G17C <tb> <SEP> I(v. <SEP> hluearass <SEP> ¯¯ <SEP> fG <SEP> ¯ <SEP> ¯ <SEP> ¯86,46 <SEP> 8G,8C <tb> <SEP> Ck¯earnrass <SEP> ¯76¯ <SEP> ¯ <SEP> 86,8C <SEP> 86,96 <tb> Su <SEP> arbeets <SEP> 4G <SEP> 7G <SEP> 4C <SEP> 8G,8C <tb> <SEP> Corn <SEP> ¯¯¯ <SEP> 5G.3E <SEP> 5G <SEP> . <SEP> 3H <SEP> 5G1 <SEP> H <tb> <SEP> Mustard <SEP> 7G <SEP> 7G,3C <SEP> 7G, <SEP> C <tb> <SEP> Cocklebur <SEP> 3G <SEP> 7G <SEP> 7G <tb> <SEP> Pigweed <SEP> 3G <SEP> lOE <SEP> lOE <tb> <SEP> Nutsed <SEP> e <SEP> 6G <SEP> 66¯ <SEP> 6 <SEP> 9G <tb> <SEP> ton <SEP> ¯ <SEP> 3G <SEP> 5G, <SEP> 3H <SEP> 6G,3E <tb> <SEP> Mornintç <SEP> iors <SEP> 0 <SEP> 7G <SEP> 8G <tb> <SEP> Cassla <SEP> O <SEP> 8G <SEP> . <SEP> SC <SEP> 8G <SEP> . <SEP> 8C <tb> <SEP> seaweed <SEP> O <SEP> lOC <SEP> lOC <tb> <SEP> Velvety <SEP> eaf <SEP> O, <SEP> , <SEP> 4G <SEP> , <SEP> 6G.2C <tb> <SEP> JimszTlwd <SEP> 8 <SEP> 3G <SEP> 3G <tb> <SEP> ¯Savbea <SEP> 36 <SEP> ¯ <SEP> 0¯sc,s <tb> <SEP> Rice <SEP> , <SEP> 7G <SEP> 7C <SEP> lOE <SEP> lOE <tb> <SEP> Wheat <SEP> , <SEP> , <SEP> 3G <SEP> 5G <SEP> 6G, <SEP> 3C <SEP> 5 <SEP> 6G,3C <tb> PRE-EMERGENCE ON FALLSINGTON SILT LOAM EMI145.1 <tb> <SEP> m <tb> <SEP> A <SEP> fri <tb> <SEP> 'a <tb> <SEP> '¸ <tb> <SEP> Aste <SEP> k <SEP> ha <SEP> 0.06 <SEP> 0.25 <SEP> 0.25 <tb> <SEP> Crabarass <SEP> 46 <SEP> 5G <tb> <SEP> Barnvarderass <SEP> 46 <SEP> 5G <tb> <SEP> Sornhum <SEP> o <SEP> I <SEP> 4G <SEP> 4(3 <tb> <SEP> wld <SEP> ats <SEP> o <SEP> I <SEP> o <SEP> .o <tb> <SEP> Johnsonnras <SEP> S <SEP> 0 <SEP> 36 <SEP> 5G <tb> <SEP> 'Dalliserass <SEP> O <SEP> I <SEP> 56 <SEP> i <SEP> 8G <tb> <SEP> 0.25 <tb> <SEP> Giant <SEP> foxtail <SEP> 0 <SEP> 3G <SEP> 6G <SEP> SR <tb> <SEP> K <SEP> . <SEP> blue <SEP> rass <SEP> 4G <SEP> 8G <SEP> 8G. <SEP> so <SEP> lOC <tb> <SEP> Cheattrass <SEP> S0 <SEP> 50 <SEP> SR <SEP> lOE <tb> Sugarbeets <SEP> 70 <SEP> R <SEP> SC <SEP> 70 <SEP> SC <SEP> <tb> <SEP> Corn <SEP> O <SEP> O <SEP> 5G <SEP> 7G <SEP> SH <tb> <SEP> Mustard <SEP> 60 <SEP> 7G <SEP> 8G <SEP> lOC <tb> <SEP> Cocklebur <SEP> 3G <SEP> 7G <tb> <SEP> Pi <SEP> eed <SEP> ¯ <SEP> 30 <SEP> <SEP> Piveed <SEP> O <SEP> 3G <SEP> ¯ <SEP> ¯ <tb> <SEP> Nutsed <SEP> e <SEP> 0 <SEP> 0 <SEP> 5 <SEP> iOE <tb> <SEP> Cotton <SEP> O <SEP> O <SEP> 4G <SEP> 1 <SEP> 7G <tb> <SEP> M;rninzz <SEP> lorv <SEP> O <SEP> 5G <SEP> . <SEP> ¯ <SEP> 6G <tb> <SEP> Cassla <SEP> O <SEP> . <SEP> <SEP> 6G <SEP> 7G <tb> <SEP> Teaweed <SEP> , <SEP> . <SEP> <SEP> O <SEP> 1 <SEP> nc <SEP> loc <tb> <SEP> 1 <SEP> 0 <SEP> O <SEP> 7C. <SEP> q <tb> <SEP> Jflmsonweed <SEP> . <SEP> <SEP> O <SEP> n <SEP> ¯ <tb> <SEP> Sovbean <SEP> 2G <SEP> 7G <SEP> * <SEP> 5H <SEP> EG <SEP> w <SEP> ¯ <SEP> 7G <SEP> . <SEP> 5H <SEP> ¯ <tb> <SEP> Rice <SEP> ¯ <SEP> ' <SEP> 3G <SEP> 6G. <SEP> 3H <SEP> 7G <SEP> 5C <SEP> ¯ <SEP> lOE <tb> <SEP> tieat <SEP> O <SEP> ¯ <SEP> 3G <SEP> 5G <SEP> X <SEP> 7G, <SEP> ECt <tb> <SEP> I <tb> PRE-EMERGENCE ON FALLSINGTON SILT LOAM EMI146.1 <tb> <SEP> A <SEP> Uy,t <tb> <SEP> 0 <SEP> -,In <tb> w <SEP> t8 <tb> <SEP> .o <SEP> 8 <tb> <SEP> Crab <SEP> rasps <SEP> ,, <SEP> . <tb> <SEP> 3 <SEP> n <SEP> s <SEP> s <SEP> 9G <SEP> 8G <SEP> . <SEP> oC <SEP> O <SEP> S <tb> <SEP> Sorghum <SEP> iG <SEP> 5E <SEP> 9G. <SEP> 9C <SEP> 6G. <SEP> 3H <SEP> ; <SEP> lOC <tb> <SEP> wil <SEP> d <SEP> Oats <SEP> O <SEP> 4G <SEP> O <SEP> 1 <tb> <SEP> r <tb> <SEP> Johnson <SEP> rass <SEP> G <SEP> 8G <SEP> SG.SH <SEP> :.SG.3H <SEP> <tb> <SEP> Dallistrass <SEP> 7 <SEP> 5G <tb> <SEP> Giant <SEP> foxtail <SEP> G <SEP> 8G <SEP> 3G <SEP> - <SEP> 9G <SEP> . <SEP> 9C <tb> <SEP> K. <SEP> blue <SEP> rasps <SEP> SG <SEP> 7 <SEP> 3C <SEP> 8G. <SEP> 7C <SEP> 7G <SEP> . <SEP> 7G <SEP> Sc <tb> <SEP> Cheat <SEP> rasps <SEP> G <SEP> . <SEP> SO <SEP> . <SEP> . <SEP> 9G <SEP> . <SEP> SC <SEP> 8 & . <SEP> 8C <SEP> lOE <tb> <SEP> Suzarbeers <SEP> 3G, <SEP> ?G <SEP> * <SEP> ,6C <SEP> 5 & <SEP> 3C <SEP> 7G.7C <tb> <SEP> Corn- <SEP> Q <SEP> o <SEP> 50 <SEP> 3H <SEP> 8GUSH <tb> <SEP> Mustard <SEP> 6G <SEP> ¯ <SEP> 8G <SEP> . <SEP> 70 <SEP> 50 <SEP> 8G,5C. <tb> <SEP> Cocklebur <SEP> . <SEP> 0 <SEP> . <SEP> . <SEP> 70 <SEP> SR <SEP> SG <SEP> SR <tb> <SEP> Pi <SEP> eed <SEP> - <SEP> - <SEP> <tb> <SEP> NutSedee <SEP> 56 <SEP> 96 <SEP> 7G <SEP> se <tb> <SEP> Cottan <SEP> ¯ <SEP> Q <SEP> 70 <SEP> ¯56 <SEP> 66 <tb> <SEP> Morroinnnlorv <SEP> O <SEP> 46 <SEP> O <SEP> 70 <tb> <SEP> Cassia <SEP> Q <SEP> 6G.lC <SEP> 66 <SEP> 70.36 <tb> <SEP> Tawe9d <SEP> , <SEP> 7G <SEP> 5G.SC <SEP> 5G <SEP> 5G <tb> <SEP> Vcy¯erleaf <SEP> O <SEP> 0 <SEP> 7G.8C <tb> <SEP> JimsoTzle <SEP> ,, <SEP> Q <SEP> 46 <SEP> 46 <SEP> 5G <tb> <SEP> L¯ <SEP> 2E <SEP> O <tb> <SEP> Rice <SEP> . <SEP> i <SEP> 6G <SEP> . <SEP> 6C <SEP> 1 <tb> <SEP> < <SEP> vG <SEP> 4 <tb> PRE-EMERGENCE ON FALLSINGTON SILT LOAM EMI147.1 <tb> <SEP> flo <SEP> A <tb> <SEP> Y <tb> 2 <SEP> 1 <tb> <SEP> 0 <SEP> : <tb> <SEP> = <SEP> In <SEP> -= <tb> <SEP> = <SEP> I <tb> <SEP> "'1 <SEP> 0 <tb> <SEP> "1 <tb> <SEP> y <tb> <SEP> Irate <SEP> kp/hr <SEP> O.03 <SEP> O.125 <SEP> = <SEP> 0.25 <tb> <SEP> Ii <SEP> 0.25 <tb> <SEP> Crabnrass <SEP> 56 <SEP> .2C <SEP> 0 <SEP> o <SEP> Barnvarderass <SEP> 8G.5C <SEP> 9C <SEP> I <tb> <SEP> 0 <SEP> I <SEP> 0 <tb> <SEP> 0 <SEP> 3C, <SEP> I <tb> <SEP> So¯rhum <SEP> 10C <SEP> 9 <SEP> 3G <tb> <SEP> Wild <SEP> Oats <SEP> BG.SC <SEP> fG,6C <SEP> O <SEP> ¯ <SEP> 0 <tb> <SEP> Johnsonarass <SEP> $G,3C <SEP> 9G.9C <SEP> 0 <SEP> 0 <tb> <SEP> Dallisnrass <SEP> 8G.4 <SEP> 9G.9C <SEP> 0 <SEP> 4G <tb> <SEP> Giant <SEP> fbxtail <SEP> 7G.3C <SEP> IOC <SEP> 0 <SEP> 56 <tb> <SEP> Kv. <SEP> bluearass <SEP> 76. <SEP> 7C <SEP> 8G.9C <SEP> 0 <SEP> 5G <tb> <SEP> Cheatnrass <SEP> 10E <SEP> i <SEP> 10E <SEP> O <SEP> 46 <tb> <SEP> Suaarbeets <SEP> 7G.7C <SEP> i <SEP> 7G.7C <SEP> 0 <SEP> 3G,4C <tb> <SEP> Cocklebut <SEP> 7G,5H <SEP> 86.8 <SEP> 0 <tb> <SEP> Pi <SEP> eed <SEP> - <SEP> - <SEP> <tb> <SEP> Nutsedne <SEP> 1SE <SEP> 10E- <SEP> e <tb> <SEP> Cotton <SEP> ron <tb> <SEP> ¯ <SEP> 13 <tb> <SEP> Mornnnnlorv <SEP> 3G <SEP> 8r: <SEP> ¯ <SEP> O, <SEP> a <tb> <SEP> Cassia <SEP> 6G <SEP> ¯n <tb> <SEP> Teatreed <SEP> 5G <SEP> 76 <SEP> 46 <tb> <SEP> Velvet <SEP> esf <SEP> iO <SEP> 6C;.5 & 36 <SEP> 36, <SEP> 3H <tb> <SEP> V <SEP> 36 <SEP> O <SEP> 3G <SEP> 0 <SEP> 3G <SEP> 0 <tb> <SEP> Rice <SEP> lOE <SEP> lOE <tb> <SEP> Wheat <SEP> 7G <SEP> * <SEP> 5C <SEP> 8G <SEP> * <SEP> 7C <SEP> O <SEP> ¯ <SEP> ¯ <SEP> 0¯ <tb> <SEP> l <tb> PRE-EMJERGENCE ON FALLSIMGTON SILT LOAM EMI148.1 <tb> <SEP> CF, <tb> <SEP> CF, <SEP> =0= <tb> <SEP> rt <SEP> 1 <SEP> z <tb> <SEP> o=Zz <SEP> t <tb> <SEP> = <SEP> -= <SEP> -Ln <tb> <SEP> iN <tb> <SEP> 0' <SEP> b <tb> ha <SEP> 0.03 <SEP> (¸2S <SEP> ;.06 <SEP> 0.a25 <tb> <SEP> r <tb> <SEP> Craberass <SEP> O <SEP> O <SEP> O <SEP> 0 <SEP> -J <tb> <SEP> Barsdzra <SEP> s <SEP> s <SEP> O <SEP> . <SEP> 3G <SEP> 6y <tb> <SEP> Sorehum <SEP> O <SEP> . <SEP> & 2H <SEP> 6G.3X <SEP> 1OC <tb> <SEP> Wild <SEP> Oats <SEP> 2G <SEP> 0 <SEP> 3G <tb> <SEP> JohnsonYrass <SEP> . <SEP> .. <SEP> . <SEP> 3G <SEP> ' <SEP> O <SEP> 4G,.3H <tb> <SEP> Dalliscass <SEP> 3G <SEP> 3G <SEP> <tb> <SEP> Giant <SEP> foxtail <SEP> SC <SEP> SG <SEP> 8G <tb> <SEP> blue <SEP> rasps <SEP> SC <SEP> 5G <SEP> 7 <SEP> 6G, <SEP> 3H <tb> <SEP> Cheat <SEP> rasps <SEP> 4G <SEP> SC3C <SEP> 6C <SEP> 7G <SEP> . <SEP> 4C <tb> <SEP> Su <SEP> arbeets <SEP> S <SEP> <SEP> .. <SEP> 2G <SEP> SC <SEP> 7G <SEP> 3C <tb> <SEP> Corn <SEP> 0 <SEP> , <SEP> O <SEP> ¯ <SEP> 6C.SE <tb> <SEP> Mustard <SEP> 6C <SEP> 7G <SEP> ¯ <SEP> 6G <SEP> I <SEP> I <SEP> 7C <tb> <SEP> Cocklebur <SEP> . <SEP> 6G <SEP> 7C <SEP> 3E <SEP> - <SEP> 1 <SEP> SC <tb> <SEP> Pi <SEP> aed <SEP> - <SEP> - <SEP> - <SEP> <tb> <SEP> Nuts <SEP> e <SEP> XG <SEP> 3G <SEP> " <SEP> SC <SEP> SC <tb> <SEP> ot <SEP> on <SEP> ; <SEP> 0 <SEP> 0 <SEP> 6G <SEP> . <SEP> 3H <tb> <SEP> Morninzzlorsr <SEP> O <SEP> O <SEP> O <SEP> 6G <tb> <SEP> Cassia <SEP> D <SEP> O <SEP> 4G <SEP> 4G <SEP> 6G <tb> <SEP> Oweed¯ <SEP> O <SEP> 5C <SEP> 0 <SEP> 0 <tb> <SEP> Velvety <SEP> eaf <SEP> .) <SEP> O <SEP> ¯ <tb> <SEP> z <SEP> S <SEP> . <SEP> o, <SEP> ... <SEP> o,, <SEP> 0 <tb> <SEP> Soybean <SEP> O <tb> <SEP> Rice <SEP> ?. <SEP> . <SEP> L <SEP> dug,, <SEP> 1G <SEP> * <SEP> 7C <tb> <SEP> Wheat, <SEP> O <SEP> 4 <SEP> 4G <tb> PRE-EMERGENCE ON FALLSINGTON SILT LOAM EMI149.1 <tb> <SEP> m <tb> <SEP> 2 <SEP> r? <tb> <SEP> u <tb> <SEP> I <tb> <SEP> l <SEP> o <SEP> o <tb> <SEP> == <SEP> = <tb> <SEP> 0 <tb> <SEP> o <SEP> \ <tb> <SEP> l <SEP> o <tb> <SEP> Io <tb> <SEP> u <tb> Rats <SEP> ha <SEP> | <SEP> 0.06 <SEP> 1 <SEP> 0.25 <tb> <SEP> 1 <tb> <SEP> Crabçrass <SEP> O <SEP> 1 <SEP> 3G <tb> <SEP> Rarnvardrass <SEP> G==t <SEP> 7Gq3H <tb> <SEP> S <SEP> huin <SEP> C <SEP> 6G <SEP> 3E <tb> <SEP> Wild <SEP> Oats <SEP> O <SEP> 6G <tb> <SEP> Johnsonerass <SEP> 5G,3H <tb> <SEP> DallissrrLss <SEP> 66 <tb> I <SEP> Giant <SEP> f-oxtail <SEP> ?P <SEP> I <SEP> 10E <tb> / <SEP> Kv, <SEP> bluearass <SEP> 46 <SEP> i <SEP> 66.36 <tb> <SEP> U <SEP> arbeets <SEP> 7G <SEP> 6G <SEP> 8G,SC <SEP> 3R <tb> <SEP> Corn <SEP> I <SEP> 0 <SEP> 66,3'6 <tb> 1 <SEP> Nustard <SEP> 66 <SEP> 66 <tb> / <SEP> C6ck1ebur <SEP> 46 <SEP> 5G,3EI <tb> i <SEP> Pigweed <tb> i <SEP> Nutsedne <SEP> 0 <tb> Cotton <SEP> 3G <SEP> ¯ <SEP> ¯ <SEP> 6G, <SEP> 3H <tb> <SEP> Morninte <SEP> lors <SEP> 3G <SEP> 7G <tb> : <SEP> Cassia <SEP> 2G <SEP> I <SEP> SC <tb> <SEP> 'I" <SEP> O <SEP> .O <SEP> 0 <tb> <SEP> Velvetleaf <SEP> O <SEP> 3G <tb> <SEP> J=nsorweed <SEP> O <SEP> 0 <tb> <SEP> Rice <SEP> XG <SEP> 2H <tb> <SEP> Wheat <SEP> G <SEP> 3G <tb> Test C Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pebnnsylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately 2-1/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved. in a non-phytotoxic solvent. Fourteen days 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 B. It is evident that the test compounds possess high post- emergence activity. Table C EMI151.1 <tb> <SEP> OVER-TIE-TOP-SOIL/FOLIAGE' <SEP> TREA'IIMENT <tb> <SEP> 0 <SEP> CH3 <tb> <SEP> W <SEP> <SEP> N43 <tb> <SEP> COUCH; <tb> <SEP> 1 <tb> rzrte <SEP> kg/ho <SEP> 0¯ <SEP> f? <SEP> 0,06 <SEP> 0.25 <tb> <SEP> o <tb> <SEP> opDeans <SEP> 10G,9C <SEP> 'I <SEP> 10C <tb> Velvetleaf <SEP> 5G <SEP> 10G,7C <tb> <SEP> Sesbania <SEP> IOG. <SEP> 7C <SEP> 10G,9C <SEP> i <SEP> 10C'---- <tb> Cassia <SEP> 1 <SEP> 8G <SEP> i <SEP> 7G <tb> Cotton <SEP> j <SEP> 100.60 <SEP> 10C <SEP> 100,90 <tb> trlorningglorv <SEP> 1 <SEP> 10G, <SEP> 6C <SEP> I <SEP> 10C <SEP> r <SEP> 10G, <SEP> 80 <SEP> -' <tb> Ufalfa <SEP> 10G, <SEP> 60 <SEP> j <SEP> 10G, <SEP> C <SEP> I <SEP> 10C <tb> Jimsonweed <SEP> I¯ <SEP> 80 <SEP> 90,20 <SEP> I <SEP> IOG, <SEP> 70 <tb> <SEP> Cocklebur <SEP> O <SEP> 7G,3H <SEP> I <SEP> 10G,9C <tb> <SEP> Carn <SEP> 9G. <SEP> 3U <SEP> 10G,6U <SEP> I <SEP> 10G,9C <tb> <SEP> Crat,grass <SEP> O <SEP> 40 <SEP> 90 <tb> Rice <SEP> 10G.4C <SEP> 10G,6C <SEP> I <SEP> 10G,6C <SEP> ¯ <tb> <SEP> Nutsedge <SEP> 7G <SEP> IOG <SEP> ,'20 <SEP> 10G,8C <tb> <SEP> Bmyard <SEP> grass <SEP> 10G <SEP> . <SEP> 5C <SEP> IOG, <SEP> 60 <SEP> ¯ <SEP> 10G, <SEP> 9C <tb> <SEP> Barnyard <SEP> grass <SEP> lOG, <SEP> 5C <SEP> lOG, <SEP> 6C <SEP> lOG, <SEP> SC <tb> <SEP> Wheat <SEP> lOG <SEP> ZC <SEP> 10G¯, <SEP> 3C <SEP> IOG,3C <tb> <SEP> Giant <SEP> Foxtail <SEP> ¯ <SEP> lOG <SEP> 2C <SEP> lOG <SEP> 3C <SEP> lOG, <SEP> C <tb> Wild <SEP> Oats <SEP> OG <SEP> 2C <SEP> lOG <SEP> z <SEP> 2C <SEP> lOG, <SEP> 4C <tb> <SEP> Sorghum <SEP> C <SEP> C <SEP> 3C <SEP> lOG <SEP> 5C <SEP> lOC <tb> <SEP> &verbar; <SEP> &verbar; <tb> <SEP> 5 <tb> S <tb> a <tb> d <tb> Table C cont'd EMI152.1 <tb> <SEP> 1 <tb> <SEP> Cl <SEP> CH <tb> <SEP> --SO,NHCNH <tb> <SEP> SO2 <SEP> Nto <SEP> j <tb> <SEP> 0 <tb> I <tb> :sL,,C--- <SEP> O <SEP> ,007 <SEP> 0.03 <tb> I <SEP> soytaeans¯ <SEP> ¯ <SEP> ¯ <SEP> 106, <SEP> 56 <SEP> I <tb> <SEP> velvtlear¯ <SEP> ¯7C, <SEP> 3C¯ <SEP> 10G,7C <tb> Ige¯sbaa <SEP> ¯ <SEP> ¯ <SEP> , <tb> <SEP> LT <SEP> -IV <tb> <SEP> cas <SEP> 56, <SEP> 20 <SEP> 76, <SEP> 3C <tb> I <SEP> Co9ton¯ <SEP> ¯ <SEP> 76. <SEP> 1C <SEP> 86.26 <SEP> <tb> <SEP> 130rnfnggjyjr- <SEP> 9G.1C <SEP> 96,36 <SEP> I <tb> <SEP> Jimsoweed <SEP> 0 <tb> <SEP> ¯0 <SEP> 0 <tb> <SEP> Cocklebur <SEP> , <SEP> ,,, <SEP> ,, <SEP> ,1G,, <SEP> , <SEP> 6G <SEP> 2C <tb> <SEP> ¯ <SEP> . <SEP> iG4.5E <SEP> 7Gs3C <tb> <SEP> Crgsass <SEP> 16 <SEP> 26 <tb> <SEP> Rice <SEP> 86,10 <SEP> 86,36 <tb> <SEP> Nuf%edge <SEP> 6 <SEP> 86 <tb> <SEP> aaayardgrass¯ <SEP> ¯7G,IC <SEP> 86, <SEP> 3C <tb> <SEP> FJat <SEP> ¯ <SEP> 26 <SEP> 46, <SEP> 26 <tb> <SEP> aP6 <SEP> roxtaa <SEP> 36 <SEP> 56 <tb> <SEP> Jil <SEP> aats <SEP> 0 <SEP> 16 <tb> <SEP> soipaum <SEP> 36 <SEP> 36 <tb> I <SEP> <tb> <SEP> lE <tb> <SEP> 1 <tb> i <SEP> <tb> <SEP> i <SEP> s <tb> <SEP> &verbar; <SEP> &verbar; <SEP> w <tb> <SEP> - <SEP> - <SEP> &verbar; <SEP> l <SEP> X <tb> <SEP> w <SEP> ---- <SEP> -- <SEP> Test D Purple nutsedge (Cyperus rotundus) tubers were planted about 2. deep in Fallsington silt loam soil contained in 10 cm diameter plastic pots. Five tubers were planted in each pot. Compounds of this. invention were dissolved in an non-phytotoxic diluent and sprayed at 560 l/ha in four methods of application: soil surface, tuber/soil, soil incorporated, and postemergence. The soil surface spray consisted of spraying the compound on the surface of the firmed covering soil. The tuber/soil spray consisted of spraying the compound on exposed tubers and subtending soil before adding -the untreated covering soil. Soil incorporated treatment consisted in mixing the compound with the covering soil before using it to cover the tubers. The postemergence treatment was sprayed on nutsedge foliage and the surrounding soil surface when nutsedge had emerged and grown to a height of about 12 cm. Pots receiving the postemergence treatments were placed directly in the greenhouse. Pots receiving the other treatments were misted with about 0.3 cm water before being transferred to the greenhouse. Response ratings assessed after four weeks are recorded in Table D based on the same rating system as described in Test A. The data indicate that the compounds tested are highly active for the control of nutsedge. Table D RESPONSE OF NUTSEDGE EMI154.1 <SEP> 0 <SEP> ii-c"e <tb> <SEP> eS02aK <SEP> 04 <tb> <SEP> L1 2 <tb> <SEP> L <tb> <SEP> REPONE <SEP> EIGING <SEP> AfiEE <SEP> 4 <SEP> WEEKS <tb> <SEP> . <SEP> .¯ <SEP> Pre-emerg. <SEP> Tuber <SEP> Soil <tb> V <SEP> nc <SEP> ro. <SEP> . <SEP> .Surface <SEP> I <SEP> SDr,av <SEP> IncorD. <SEP> Post-emer <tb> <SEP> - <SEP> - <SEP> 0.125 <SEP> T <SEP> 7G <SEP> &verbar; <SEP> 7G <SEP> 7G <SEP> 2G <tb> <SEP> - <SEP> ?r <SEP> 7G <SEP> 7G <SEP> G <tb> <SEP> <SEP> .5 <SEP> 9G <SEP> , <SEP> 9 & <SEP> 2G <tb> <SEP> l <SEP> &verbar; <SEP> u <SEP> li <tb> <SEP> hfl <tb> <SEP> - <SEP> - <SEP> &verbar; <SEP> h <SEP> w <SEP> < <SEP> < <tb> <SEP> E <SEP> h <SEP> w <tb> &verbar; <SEP> &verbar; <tb> <SEP> ; <SEP> &verbar; <SEP> w <SEP> w <tb> 41 <SEP> - <SEP> - <SEP> &verbar; <tb> <SEP> h <SEP> u <tb> <SEP> b <tb> <SEP> f <SEP> &verbar; <SEP> &verbar; <tb> s <SEP> -- <SEP> &verbar; <tb> &verbar; <SEP> &verbar; <SEP> &verbar; <SEP> &verbar; <SEP> i <tb> <SEP> - <SEP> -S <SEP> u <SEP> &verbar; <SEP> &verbar; <tb> <SEP> W <SEP> &num;l <tb> <SEP> &verbar; <tb> <SEP> &verbar; <SEP> w <SEP> <SEP> i <SEP> &verbar; <tb> <SEP> L <tb> <SEP> &verbar; <SEP> &verbar; <SEP> &verbar; <tb> <SEP> &verbar; <SEP> l- <SEP> TABLE D-cont'd RESPONSE OF NUTSEDGE EMI155.1 <tb> <SEP> 0 <SEP> cur3 <tb> <SEP> ,NH-C-NEI-( <tb> <SEP> COCKY <tb> <SEP> v <tb> <SEP> 1 <tb> <SEP> RES-POSE <SEP> RATING <SEP> afiER <SEP> 4 <SEP> WEEKS <tb> <SEP> I <SEP> 1 <tb> Rate <SEP> k°/Aa <SEP> Surface <SEP> sPraY <SEP> IncorP! <SEP> Pos,t-emerg. <tb> 1 <tb> <SEP> F <SEP> <tb> <SEP> G <SEP> 6E <SEP> 8G <SEP> , <SEP> 8E.9 & 6E.9G <SEP> L <SEP> SG <tb> <SEP> iOE <SEP> lOE <SEP> 1 <SEP> E <SEP> C, <SEP> G <tb> L <SEP> w <tb> <SEP> S <SEP> &verbar; <tb> <SEP> 4 <tb> <SEP> l <SEP> - <SEP> w <SEP> - <SEP> h <tb> <SEP> l <SEP> i <SEP> - <SEP> &verbar; <tb> <SEP> -&verbar; <SEP> - <SEP> . <SEP> R <tb> <SEP> w <SEP> s <tb> <SEP> &verbar; <SEP> = <tb>

Claims: Claims: 1. A compound selected from EMI156.1 R2 is H, CE3, OCH3, F, C1, Br, NO2, CF3, COR5, S(O)mR10, SO2NR10R11, SO2OCH2CF3, SO2OCH2CCl3 or SO2N(OCH3)CH3; R3 is H, F, C1, Br, alkyl C1-C4 or CH3O, R4 is H, Cl, Br, F, alkyl C1-C4, alkoxy C1-C4, NO2, C02R6 or R13 -S- provided that R4 is restricted to the 2- or 4-position of the pyridine ring; R5 is alkoxy C1-C6; alkenyloxy C3-C6; haloalkoxy C2-C6 having 1 to 3 halogens selected from C1, F and Br; cycloalkoxy C5-C6; O-(CH2CH2I)-nR7; OCH2CH2CH2OR7; NR8R9; N(OCH3)CH3 or C1-C4 alkylthio; R6 is alkyl C1-C6; R7 is alkyl C1-C2; R8 and R9 are independently H or alkyl C1-C4, or R8 and R9 may be taken together to be (CH2)4, (CH2)5 or O(CH2CH2-)2; R10 and R1L are independently C1-C6 alkyl or C3-C4 alkenyl, or R10 and R11 can be taken together to be (CH2)4, (CH2)5 or O(CH2CH2)2; R12 is C1-C12 alkyl; CH2CH2OCH3; CH2CH2OCH2CH3; CH2CH2CH2OCH3; CH2A or EMI157.1 R13 is C -C3 alkyl; X is H, CR3, CH30, Cl or OCH2CH3 Y is CH2 or 0; A is CO2H, C02B, phenyl, CN, C2-C4 alkenyl, C2-C4 alkyl, phenyl substituted with one or two. methyl groups or with one or two chlorines; B is C1-C4 alkyl; m is 0, 1 or 2; n is 1 or 2; W is oxygen or sulfur; provided that i) when R1 is EMI157.2 then is COR5, SO2NR10R11 or SO2N(CH3)(ICH3); and isd other than H; and ii) when R1 is EMI157.3 then X = CH3 or OCH3; and their agricuiturally suitable salts. 2. A compound of Claim 1 wherein W is oxygen 3. A compound of Claim 2 wherein R is EMI157.4 4. A compound of Cla im 3 wherein R1 is EMI158.1 5. A compound of Claim 4 wherein X is H, CH3 or OCH3. 6. A compound of Claim 5 wherein R2 is NO2,, COR5, SO2NR10R11, SO2R10, or SO2N(OCH3) (CH3). 7. A compound of Claim 6 wherein R3 is H. 8. A compound of Claim 7 wherein R2 is- NO2, CORN, SO2N(CH3)2, 502N(CE2CH3)2 or SO2N(OCH3) (CE3) and R5 is C1-C3 alkoxy or allyloxy. 9. N-[(6,7-Dyhydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide and its agriculturally suitable salts. 10. 2-[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzensulfonamide methyl ester and its agriculturally suitable salts. 11. N-[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzensulfonamide and its agriculturally suitable salts. 12. 2-Chloro-N[(5,6-dihydro-4-methylfuro [2,3-d]-pyrimidin-2-yl)aminocarbonyl]-2-benzenesulfonamide and its agriculturally suitable salts. 13. N-[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-2-nitrobenzensulfonamide and its agriculturally suitable salts. 14. 2-[(5,6-Dihydro-4-methyl pyrimidin-2-yl) -aminocarbonyl)benzoic acid, methyl ester and its agriculturally suitable salts. 15. N'-[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide and its agriculturally suitable salts 16. 2-[[(6,7-Dihydro-4-methyl-5H-cyclopentapyrimidin- 2-yl)aminocarbonyl]aminosulfonyl benzoic acid, ethyl ester and its agriculturally suitable salts. 17. 2-[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2 yl)arainocarbonyl)aminosulfony] benzoic acid, ethyl ester and its agriculturally suitable salts. 18. 2-[(5,6-Dihydro-4-methylfuro[2.3-d]pyrimidin2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, cyclohexyl ester and its agriculturally suitable salts. 19. A composition for the control of undesirable vegetation comprising a herbicidal compound and at least one of (a) a surface active agent, and (b) a solid or liquid diluent characterised in that said herbicidal compound is a compound of any of claims 1-18. 20. A method for the control of undesirable vegetation by applying to the locus of such undesirable vegetation an effective amount of herbicidal compound characterised in that said herbicidal compound is a compound of any of claims 1-18. 21. A method for the control of nutsedge by applying to the locus of such nutsedge an effective amount of a herbicidal compound characterised in that said herbicidal compound is a compound of any of claims 1-18. 22. A process for preparing a compound of claim 1 of the formula EMI159.1 which comprises reacting a 2-amino-pyrimidine of the formula EMI160.1 where X and Y are as defined in claim 1 and where q is 1 or 2, with a sulfonyl isocyanate or isothiocyanate of the formula RSO2NCW, where R and W are as defined in claim 1 23. A process for preparing a compound of claim 1 of the formula EMI160.2 which comprises reacting a carbamimidothioic acid salt of the formula EMI160.3 where R, -X and Y are as defined in claim 1, M.is an alkali or alkaline earth metal, and q is 1 or 2, with an alkylating agent of the formula (R12) sD where R12 is as defined in claim 1, D is sulfate or halogen, and S is an integer corresponding to the valence of D.

Inventors: LEVITT, GEORGE
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1980
Main classification: C07D239
IPC codes: C07D213, C07D239, C07D521, A01N47, C07D491, C07D401