HERBICIDAL ORTHO-ALKYL- AND ORTHO-ALKENYL-SUBSTITUTED BENZENESULFONAMIDES

Abstract: Benzenesulfonamide derivatives of the formula wherein R₁ is selected from a variety of optionally substi­ tuted alkyl and alkenyl groups; R₂ is H, F, Cl, CH₃,OCH₃ or CF₃; R₃ is H or CH₃; A is selected from a variety of substituted heterocyclic groups, e.g pyrimidin-2-yl or 1,3,5-triazin-2-yl; and their agriculturally suitable salts, exhibit herbicidal and plant growth regulant activities. The novel compounds may be formulated for use in conventional manner. They may be made e.g. by reacting an appropriate arylsulfonyl isocyanate with an appropriate aminoheterocycle of formula R₃NHA.

Description: Title " Herbicidal ortho-Alkyl and ortho Alkenyl-substituted Benzenesulfonamides" Background of the Invention The present invention relstes to a class of ortho-alkyl- and ortho-alkenyl-substituted benzene- sulfonamides which are useful as general or selective pre-emergent or post-emergent herbicides and plant growth regulants. United States Patent 4,368,069 discloses and claims a class of herbicidal sulfonamides including compounds of the following structure: EMI1.1 R2 can be C2-C5 alkenyl; n is 0 or 1; R1 can be H; X and Y can be various substituents including CH3 or OCH3; and Z can be CH or N. In our EP-A-44,209 we have disclosed and claimed a large number of o-benzyl-substituted sulfonamides including the following: EMI1.2 These compounds are useful as plant growth regulants and as herbicides. Summary of the Invention This invention relates to novel compounds of Formula I, suitable agricultural compositions containing them and their method-of-use as general or selective pre-emergent or post-emergent herbicides and plant growth regulants. EMI2.1 CHClCH2Cl, CHClCHC12, CH=CBr2, CH=CHR9, CH=CHC02CH3 or CH=CF2; R2 is H, F, C1, CH3, OCH3 or CF3; R3 is H or CH3; is H, F, Cl, Br or CH3 ; Rf is F, C1, Br, OC(O)R6, OC(O)CF3, OH, OCH2@, OSD2R6, OSO2CF3, 0502C6H5R7, (S(O)mR6, OS02N(CH3)2 or C02R8; R6 is C1-C3 alkyl; R7 is H, F, C1, Br, CH3, OCH3 or CF3; R8 is C1-C3 alkyl, CH2CH=CH2, CH2CH2oCH3 or CH2CH2C1; R9 is OCH3 or OCH2CH3; R10 is H, OCH3 or OCH2CH3; R11 is H, Cl or OCH3; R12 is H or CH3; n is O or 1; m is 0, 1 or 2; EMI3.1 X is CH3, OCH3, C1, F, Br, CH2CH3, OCH2CH3 or OCF2H ; Y is H, NH2, NHCH3, N(CH3)2, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of a) F, b) Cl or c) Br, CH20CH3, CH2OCH2CH3, C1-C4 alkoxy, C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH20CH3, CH(OCH3)2, CH(OCH2CH3)2, EMI3.2 OCH2CF3, OCH2CH2F, OCH2CH2C1, OCH2CH2Br or GCF2T ; wherein G is 0 or S and T is H, CHC1F, CHBrF, CF2H or CHFCF3; Z is CH, N, CCH3, CBr, CC1, CF or CCH2CH3; X1 is o or CH2; Y1 is H, CH3, OCH3 or C1; X2 is CH3, OCH3 or SCH3 ; V2 is CH3, CH2CH3 or CH2CF3; and X3 is CH3 or OCH3; and their agriculturally suitable salts; provided that a) when R4 is halogen, R5 is the same halogen; b) when R5 is halogen, R4 is either hydrogen or the same halogen; c) when n is 1, R11 is hydrogen; d) when R12 is CH3 and R10 is alkoxy, R9 is the same alkoxy; and e) when X is C1, then Z is CH and Y is NH2, NHCH3, N(CH3)2, cH3, OCH3, or OCF2H. Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity and/or more favorable ease of synthesis are: 1) Compounds of generic Formula I wherein R2 is H and R1 is (CH2)nCH2CHR4R5, EMI4.1 2) Compounds of Preferred 1 wherein A is A-1; Z is CH or N; X is CH3, OCH3, Cl or OCF2H and Y is CH3, CH2CH3, OCH3, OCH2CH3, OCF2H, SCF2H, CH20CH3 or CF3. 3) Compounds of Preferred 2 wherein R1 is CH2CH2Cl, CH2CH20H CH(OCH3)CH2OCH3 or EMI4.2 4) Compounds of Preferred 3 wherein R3 is H. Specifically preferred for reasons of their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are: N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-methoxyethyl)benzenesulfonsmide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocàrbonyl]- aminosulfony1-2-(2-methoxyethyl)benzenesulfonamide; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino sulfonyl-2-(2-p-toluenesulfonyloxyethyl)benzene sulfonamide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)ben zenesulfonamide; Nw methoxy-.6-methyl-1,3,5-triazin-2-yl)aminocarbon- ylZaminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)ben- zenesulfonamide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-chloroethyl)benzenesulfonamide; ; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino sulfonyl-2-(2-chloroethyl)benzenesulfonamide; and N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-chloroethyl)benzenesulfonamide. Synthesis The compounds of Formula I may be prepared as shown below in Equation 1 by the reaction of an appropriate aryl sulfonyl isocyanate, II, with an appropriate amino heterocycle, III. Equation 1 EMI6.1 wherein R1, R2, R3 and A are as previously defined except that R5 is not OH. The reaction of Equation 1 is best carried out in an inert aprotic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at a temperature between 200C and BOOC. A catalytic amount of 1,4-di azabicyclol2,2,2)octane (DABCO) may be used to accelerate the reaction. In cases in which the products are insoluble in the reaction solvent, they may be isolated by simple filtration. When the products are soluble, they may be isolated by evaporation of the solvent and trituration of the residue with solvents such as l-chlorobutane, diethyl ether, or methanol, and filtration. The aryl sulfonyl isocyanates of Formula II may be prepared as shown in Equation 2, by phosgenation of the sulfonamides of Formula IV in the presence of butyl isocyanate. Equation 2 EMI7.1 wherein R1 and R2 are as previously defined except that R5 is not OH. The above reaction is carried out by heating a mixture of the appropriate sulfonamide IV, an alkyl isocyanate such as butyl isocyanate, and a catalytic amount of a tertiary amine such as 1,4-diazabicyclo 12,2,2)octane (DABCO) in xylene, or other inert solvent of boiling point ,1350C, to approximately 1350C. Phosgene is then added to the mixture over a 1-6 hour period at 125-1350C until an excess is present as indicated by a permanent drop in the boiling point to less than 130cC. The mixture is cooled and filtered to remove a small amount of insoluble by-products. The solvent and the alkyl isocyanate are distilled off in vacuo leaving a residue of the crude sulfonyl isocyanate II, which can be used without further purifi- cation. Sulfonyl isocyanates of Formula II may also be prepared as shown in Equation 3, by phosgenation of the appropriate butylureas of Formula V. Equation 3 EMI8.1 wherein R1 and R2 are as previously defined except that R5 is not OH. The compounds of Formula V are conveniently prepared by stirring a mixture of the sulfonamides, Iv, anhydrous potassium carbonate, and n-butyl isocyanate in acetone or methyl ethyl ketone at 25-800C until all of the isocyanate has reacted. The products are isolated by quenching in dilute mineral acid and recrystallizing the solid product. The compounds V are treated with phosgene and a catalytic amount of DABCO in refluxing xylene or chlorobenzene in a manner analogous to that described in Equation 2. Sultonyl isocyanates of Formula II may also be prepared by the two-step procedure shown below in Equation 4 starting from the appropriate sulfonamides. Equation 4 EMI8.2 EMI9.1 wherein R1 and R2 are as previously defined except that R5 is not OH. The reactions of Equation 4 (a) and (b) are best carried out according to the procedure of Ulrich et al. in 3. Org. Chem., 34, 3200 (1969). The sulfonamide is boiled under reflux with an excess of thionyl chloride which functions as both a reactant and solvent. When the sulfonamide protons are no longer detectable by proton NMR (15-20 hrs. on the average), the thionyl chloride is removed under reduced pressure and the residue is dissolved in an inert solvent such as toluene, benzene, xylenes, etc. A catalytic amount of pyridine is added. The mixture is treated with at least one equivalent of phosgene and heated to 600-1400C with 80 -100 preferred. Conversion to the isocyanate is substantially complete within about 1/4 to 3 hours. The mixture containing the sulfonyl isocyanate can be used directly or the sulfonyl isocyanate can be isolated in pure form by filtration and evaporation of the filtrate followed by vacuum distillation if necessary. Compounds of Formula Ia are conveniently prepared by mild hydrolysis of the corresponding trifluoroacetates using mild base followed by an appropriate acid-such as dilute hydrochloric acid, as shown in Equation 5. Equation 5 EMI10.1 wherein R2, R n, and A are as defined in the Summary of the Invention; and R4 is H or CH3. Alternatively, compounds of Formula I may be prepared as shown in Equation 6 by the reaction of an appropriate carbamate, VII, with an appropriate amino heterocycle, III. Equation 6 a) EMI10.2 III wherein R1, R2 R31 and A are as previously defined except that R5 is not OH. The reactions of Equation 6 are best carried out according to the methods taught in EPO Publication 44,807. Compounds of Formula Ib can be prepared by the reaction of an appropriately substituted sulfonamide, IV, with the methyl carbamate of the appropriate amino heterocycle, VIII, in the presence of one equivalent of trimethylaluminum as shown in Equation 7. Equation 7 EMI11.1 wherein R1, R2, R3, X, Y and Z are as previously defined. The reaction of Equation 7 is best carried out according to the procedure described in EPO Publication 44,210, 3anuary 10, 1982. Benzenesulfonamides of Formula IVa and IVb may be prepared as shown in Equation 8. Equation 8 EMI12.1 wherein R2 is H, 3-, 4- or 6-F, C1, OCH3 or CF3; and R4 is H or CH3. EMI12.2 wherein R2 is H, F, C1, CH3, OCH3 or CF3; R9 is OCH3 or OC2H5; and R12 is H or CH3. EMI13.1 ClS02CF3, C1C(O)R6, (R6CO)2O, ClSO2N(CH3)2 or ClSO2C6H4R7 ; EMI13.2 or t-BuOK/BrCH2Ph wherein R2 is H, F, C1, CH3, OCH3 or CF3; R4 is H or CH3; R5 is OC(O)R6, OC(O)CF3, OS02R6, OS02CF3, 0S02C6H4R7, OCH2Ph or DSO2N(CH3)2 ; and R6 and R7 are as previously defined. EMI13.3 wherein R2 is H, F, C1, CH3, OCH3 or CF3; R4 is H or CH3; and R5 is F, Cl or Br. EMI13.4 wherein R2 is as previously defined; R4 is H or CH3; R5 is OH, F, C1, Br, OC(O)R6, OC(O)CF3, 0S02R6, 0S02CF3, 3So2C6H4R7, OCH2Ph or OS02N (CH3)2 and R6 and R7 are as previously defined. EMI14.1 wherein R2, R9, R12, and n are as defined in the Summary of the Invention. Reaction Step 8(a) Reaction Step 8(a) is best carried out under nitrogen in an anhydrous aprotic solvent such as tetrahydrofuran, diethyl ether or hexane at temperatures between -450C and 400C according to the method of 3. G. Lombardino (a. Org. Chem., 36, 1843 (1971)]. The preferred mode of addition is to add the n-butyllithium to a cold solution of the sulfonamide in tetrahydrofuran. An exothermic reaction occurs accompanied by a color change and, in some cases, a precipitate. The appropriate electrophile (ethylene oxide or propylene oxide) is then added and the mixture is stirred at ambient to reflux temperatures for 6 to 20 hours. The addition of dilute acetic acid or ammonium chloride removes inorganic salts from the product contained in the organic phase. Evaporation of the solvent yields the crude product, which can be used without further purification or can be chromatographed. When R2 is in the 3- or 6-position, lithiation occurs at the 2-position. The lithiation of aromatic sulfones and sulfonamides is described in the following references: W. E. Truce and M. F. Amos, J. Am. Chem. Soc., 73, 3013 (1951) S. J. Shafer and W. D. Clossen, J. Org. Chem., 40, 889 (1975) D. Hellwinkel and M. Supp, Tetrahedron Lett., 1499 (1975) H. W. Gschwend and H. R. Rodriquez, Organic Reactions, 26, 1 (1979). Reaction Step 8(b) Compounds of Formula XIIa are conveniently prepared from the appropriate alcohols, XI. The reaction is best carried out by adding the alcohol to a suspension of at least two equivalents of potassium t-butoxide in tetrahydrofuran at temperatures between -780C and OOC. An alkyl halide is then added and the mixture stirred at -780C to ambient temperature for 15 minutes to 6 hours. The addition of a dilute acid such as hydrochloric acid removes the salts from the product in the organic phase. Evaporation of the solvent in vacuo yields the crude product which can be used without further purification. Reaction Step 8(c) Reaction Step 8(c) is best carried out by stirring a solution of the appropriate alcohol, XI, with triethylamine and the appropriate electrophile (alkanesulfonyl chloride, aryl sulfonyl chloride, trifluoromethanesulfonyl chloride, trifluoroacetyl chloride, acyl chloride or the corresponding anhydride or sulfamoyl chloride) in methylene chloride at ambient to reflux temperatures for 2 to 18 hours. The salts are washed out of the solvent with dilute hydrochloric acid and the product isolated by evaporation. The products can be triturated with solvents such as diethyl ether ox l-chlorobutane or purified by column chromatography. Benzyl ethers of Formula XIIb, in which R5 is OCH2Ph, can be most conveniently prepared by treatment of the appropriate alcohols, XI, first with potassium tert-butoxide in a suitable solvent such as tetrahydrofuran. The resulting alkoxide is then quenched with benzyl bromide and the product isolated as described above. Reaction Step 8(d) The conversion of methanesulfonate esters such as XIII to the corresponding alkyl halides XIIc (wherein Rg = F, C1, or Br) via nucleophilic displacement is well-precedented in the chemical literature. For example, alkyl bromides of Formula XIIc (R5 = Br) are best prepared according to the procedure described by Cason and Correia (3. Orq. Chem., 26, 3645 (1961)). A mixture of the methanesulfonate ester XIII and excess sodium bromide in a suitable solvent such as dimethylformamide, dimethyl sulfoxide, acetone, or methyl ethyl ketone is stirred rapidly under an inert atmosphere at temperatures between 250C and lOO0C. Reaction progress is conveniently followed by thin-layer chromatography and is complete when little or no starting material can be detected. The solution is then filtered to separate insoluble salts, and the filtrate concentrated to give the desired product which can be purified by crystallization or column chromatography. Alternatively, the reaction solution is diluted with water and the product extracted with a suitable solvent such as diethyl ether, dichloromethane or ethyl acetate. Evaporation of the solvent from the organic layer then affords the product which can be further purified if necessary. Alkyl chlorides of Formula XIIc (R5 r C1) can be synthesized in an analogous fashion as described by Buck and Foster (J. Am. Chem. Soc., 85, 2217 (1963)) via reaction of the methanesulfonate esters, XIII, with lithium chloride in dimethylformamide or ethanol. Alkyl fluorides of Formula XIIc (R5 = F) may be prepared according to the method of Kissman and Weiss (3. Am. Chem. Soc., 80, 5559 (1958)), in which the methanesulfonate esters XIII are treated with potassium fluoride monohydrate in methanol heated under pressure, or by the procedure of Taylor and Kent (3. Chem. Soc., 872 (1958)) using anhydrous potassium fluoride in glycol solvent. Alkyl fluorides can also be prepared from the corresponding chlorides or bromides. The methods for effecting this transformation have been reviewed by A. L. Henne (Org. Reactions, 2, 49 (1944)). Reaction Steps 8(e) and 8(f) Reaction Steps 8(e) and 8(f) are best carried out in trifluoroacetic acid or ethanolic hydrogen chloride between ambient and reflux temperatures for 18 to 48 hours according to the method of 3. G. Lombardino (3. Org. Chem., 36, 1843 (1971)J. The deprotection appears to be concentrationdependent. The yield of the sulfonamides, IVa and IVb, can usually be increased by using a large excess of the acid as a solvent, or by stripping off the volatile by-products after 18 hours, redissolving or resuspending the residue in the acid of choice, and stirring an additional 20 to 30 hours. The solvent is distilled off in vacuo and the residue treated with aqueous sodium bicarbonate and ether or methylene chloride. The products can be extracted from the organic phase with dilute aqueous sodium hydroxide and precipitated with aqueous hydrochloric acid. The products can be purified by recrystallization from solvents such as hexane/n-butyl chloride or hexane/ chloroform. The sulfonamides of Formula XIa can be prepared from compounds of Formula IXa as shown in Equation 9. Equation 9 EMI18.1 wherein R2 is as defined in the Summary of the Invention; R4 is H or CH; and n is O or 1. The above reaction is best carried out under the conditions described for Equation 8(a). The lithiation of o-toluenesulfonamide and its subsequent reaction with ketones is described by H. Watanabe and C. R. Hauser (J. Org. Chem., 33, 4278 (1968)). Compounds of Formula XIa can be elaborated and deprotected as described in Equation 8(a-f). The sulfonamides of Formulas IX and IXa preferably are prepared from the appropriate sulfonyl chlorides XIV or XIVa and t-butylamine according to the method of 3. G. Lombardino (3. Org. Chem., 36, 1843 (1971)), as shown in Equation 10. Equation 10 a) EMI19.1 wherein R2 is as previously defined. The sulfonyl chlorides of Formula XIVa can be prepared as shown in Equation 11. Equation 11 EMI19.2 wherein R2 is as previously defined. The reaction in Equation 11 is best carried out under nitrogen in an anhydrous, aprotic solvent such as tetrahydrofuran or diethyl ether with at least one equivalent of the alkyllithium at temperatures between -11OOC and -450C for 15 minutes to two hours. Sulfuryl chloride is then added and the mixture allowed to warm to ambient temperature over 1 to 4 hours. The reaction is often accompanied by several color chan ges. An aqueous wash removes inorganic salts, and the product is obtained after evaporation of the solvent in vacuo. The crude sulfonyl chlorides can be used without further purification. The reaction of sulfuryl chloride and phenyllithium is described by S. N. Bhattacharya et al. (3. Chem. Soc., C, 1265 (1968)). Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene 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 prepared by diazotization of the appropriate aniline with sodium nitrite in HC1, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of H. L. Vale and F. Sowinski, 3. Org. Chem., 25, 1824 (1960). In addition, the oxidative chlorination of mercaptans to prepare sulfonyl chlorides is widely reported in the literature, e.g., Gilbert, Sulfonation and Related Reactions, pp. 202-214, Interscience Publishers, New York, 1965. Benzenesulfonamides of Formula IVc can best be prepared via the two-step sequence shown in Equation 12 from the appropriate aryl bromides of Formula XVI. Equation 12 EMI20.1 EMI21.1 wherein R2, Rg, and n are as previously defined; and R10 is OCH3 or OC2H5 The reaction of Equation 12(a) is best effected according to the procedure of Bhattacharya et al. (J. Chem. Soc., C, 1265 (1968)), as described above for Equation 11. The reaction of Equation 12(b) is preferably carried out by treatment of a solution of the sulfonyl chlorides XVII in a suitable solvent such as tetrahydrofuran or methylene chloride at -OOC to 10 C with excess anhydrous ammonia gas or concentrated ammonium hydroxide. The reaction mixture is then stirred at ambient temperature for 0.5-3 hours. If ammonium chloride has precipitated, the solution is filtered and the filtrate concentrated in vacuo; otherwise the solvent is simply evaporated. The pure sulfonamides can be obtained by trituration or column chromatography. Aryl bromides of Formula XVI can be prepared as shown in Equation 13 starting from the appropriate aalkoxy ketone of Formula XVIII. Equation 13 EMI22.1 wherein R2, Rg, and n are as previously defined; and R10 is OCH3 or OC2H. The reduction of carbonyl compounds, particularly ketones, to the corresponding alcohols with sodium borohydride is well precedented in the chemical literature. For many pertinent examples see H. O. House, "Modern Synthetic Reactions," 2nd Ed., W. A. Benjamin, Inc., California, 1972, pp. 45-70. The alkylation of alcohols of Formula XIX as shown in -±quation 13(b) is best carried out as described for Equation 8(b) above. v-Alkoxy ketones of Formula XVII I can be synthesized according to the procedures described by Wissner (Tetrahedron Lett., 2749 (1967) and 3. Org. Chem., 44, 4617 (1979)). This process, which involves the reaction of an appropriate acid chloride of Formula XX with a suitable bis-trimethylsilyl ketone acetal of Formula XXI and subsequent mild acid hydrolysis, is summarized in Equation 14. Equation 14 EMI23.1 wherein R2, R9, and n are as previously defined. The preparation and use of ketone acetals of Formula XXI is discussed in the above references by Wissner. Benzenesulfonamides of Formula IVd also may be prepared as shown in Equation 15 by the procedure of Bhattacharya as described above in Equations 11 and 12. Equation 15 EMI23.2 wherein R2, R9, and R11 are as previously defined. The aryl bromides, XXIIa, (wherein Rll=H) can be prepared via acetalization of the appropriate aldehydes of Formula XXI II as shown in Equation 16. Equation 16 EMI24.1 wherein R2, Rg, and n are as previously defined. The reaction of Equation 16 is best carried out by heating a mixture of the appropriate aldehyde XXIII and at least one equivalent of an appropriate alcohol (methanol or ethanol) with a catalytic amount of acid catalyst such as p-toluenesulfonic or camphorsulfonic acid at reflux temperatures in a suitable solvent such as benzene, toluene, or xylene. Water given off during the reaction is most conveniently removed by use of a Dean-Stark water separator. When reaction is complete as evidenced by thin-layer chromatography or IR spectral analysis (typically 1-6 hours), inorganic and acidic materials are washed out of the organic layer with water and saturated sodium bicarbonate solution. Removal of the solvent in vacuo affords the aryl bromide acetals XXI Ia, which can be purified by distillation or column chromatography if necessary. The aryl bromides of Formula XXIIb, wherein Rll=Cl and n=O, may be prepared from the corresponding acetals XXI Ia (n=0, R11=H) by benzylic chlorination as shown in Equation 17. Equation 17 EMI25.1 wherein R2 and Rg are as previously defined; and R11 is C1. The chlorination reaction of Equation 17 preferably is carried out by heating a mixture of the appropriate acetal XXIIa and one equivalent of N-chlorosuccinimide (NCS) at reflux temperature in carbon tetrachloride solvent; a free-radical initiator such as 2,2'-azobisisobutyronitrile (AIBN) or benzoyl peroxide generally is employed in catalytic amount. When reaction is complete, as judged by proton NMR, the products may be isolated by simple filtration to remove insoluble by-products and evaporation of the filtrate in vacuo. Aryl bromides of Formula XXIIc, wherein Rll=OCH3 and n=O, may be most conveniently synthesized by the procedure summarized in Equation 18. Equation 18 EMI25.2 wherein R2 and R9 are as previously defined ; and R11 is OCH3. The reaction of Equation 18 is well known in the chemical literature as the Williamson ether synthesis. For relevant examples, see A. I. Vogel, J. Chem. Soc., 616 (1948). Benzenesulfonamides of Formulas IVe, IVf, and IVg also may be prepared by the method of Bhattacharya as described above for Equations 11 and 12. The synthesis of sulfonamides IVe, IVf, and IVg is summarized in Equations 19a, 19b and 19c, respectively. Equation 19 EMI26.1 wherein R2, Rill, and n are as previously defined. The aryl bromides XXIVa, XXIVb and XXIVc, wherein R11 is H, can most conveniently be prepared via acetalization of the appropriate aldehydes of Formula XXIII as shown in Equation 20(a-c). Equation 20 EMI27.1 EMI27.2 benzene or toluene, reflux XXIVa b) XXIII EMI27.3 benzene or toluene reflux XXIVb EMI27.4 benzene or toluene reflux wherein R2 and n are as previously defined. The reactions of Equation 20(a-c) are best carried out in a manner analogous to that described above for Equation 16 except that the appropriate glycol is used in lieu of methanol or ethanol to effect acetal formation. Aryl bromides of Formula XXIVd, XXIVe, and XXIVf, wherein R11=Cl and n=O, may be obtained via benzylic chlorination of the corresponding acetals XXIVa, XXIVb, and XXIVc, as shown in Equation 21(a-c). Equation 21 EMI28.1 wherein is as previously defined ; and R11 is C1. The reactions shown in Equation 21(a-c) are best carried out as described for Equation 17 above. Aryl bromides of Formula XXIVg, XXIVh, and XXIVi, wherein R11=OCH3 and n=0, can be most conveniently prepared by a Williamson ether synthesis, as shown in Equation 22(a-c), starting from the appropriate acetals of Formula XXIVd, XXIVe, or XXIVf. Equation 22 EMI29.1 wherein R2 is as previously defined; and R11 is OCH3. The aldehydes of Formula XXIIIa, wherein n=O, and R11=H, may be prepared from the corresponding alcohols XXV by oxidation with pyridinium chlorochromate (PCC), as shown in Equation 23. Equation 23 EMI30.1 wherein R2 is as previously defined. The oxidation of Equation 23 is best carried out according to the procedure of E. J. Corey, Tetrahedron Lett., 2644 (1975). Thus, a solution of pyridinium chlorochromate in methylene chloride is added to a stirred solution of the alcohol XXV in methylene chloride at room temperature; sodium acetate may be added to serve as a buffer. When the reaction is complete, as determined most conveniently by thin-layer chromatography, the reaction mixture is diluted with dimethyl ether and filtered through a pad of Celite. The filtrate is then further purified by passage through a short column of silica gel or Florisil. Removal of the solvents in vacuo affords the aldehyde XXIITa which generally can be used without additional purification. Alcohols of Formula XXV may be prepared by re duction f thecorresponding carboxylic acid esters, XXVI, as shown in Equation 24. Equation 24 EMI30.2 wherein R2 is as previously defined. The reaction of Equation 24 is conveniently carried out by adding a solution of the ester XXVI in a suitable solvent such as diethyl ether or tetrahydrofur an to a suspension of lithium aluminum hydride (LiAlH4) in the same solvent at ambient to reflux temperatures. After being heated at reflux temperature for 1 to 8 hours, the reaction mixture is cooled to 0 C, and excess hydride reagent destroyed by either the dropwise addition of saturated sodium sulfate (ether solvent) or by the procedure of Fieser (Reagents for Organic Synthesis, Vol. 1, 3ohn Wiley and Sons, Inc., New York, 1967, pp. 383-584). The suspension is filtered to remove insoluble aluminum salts and the filtrate is dried and concentrated to give the alcohol XXV, which can be used directly or purified by chromatography. The carboxylic acid esters, XXVI, are preferably prepared by hydrolysis of the corresponding nitriles of Formula XXVI I as shown in Equation 25. Equation 25 EMI31.1 wherein R2 is as previously defined. The reaction of Equation 25 is carried out by heating a solution of the appropriate nitrile of Formula XXVI I in ethanolic sulfuric acid at reflux temperature for 1 to 6 hours. The entire solution is then poured into ice water and the desired ester XXVI extracted with a suitable solvent such as diethyl ether or methylene chloride. Drying and evaporation of the organic layers yield the pure product. Many nitriles of Formula XXVI I are known in the literature. These compounds may be prepared by reaction of the appropriate benzyl bromides, XXVII I, with sodium or potassium cyanide, as shown in Equation 26. Equation 26 EMI32.1 wherein R2 is as previously defined. The displacement reaction of Equation 26 can best be effected according to the procedure of F. Bickelhaupt et al., Chem. Ber., 685 (1965). Thus, a solution of the bromide XXVII I in a suitable solvent such as ethanol is added dropwise to a room temperature solution of sodium or potassium cyanide in aqueous ethanol. The resultant mixture is then heated to reflux temperature for about 30 minutes. Removal of the solvent in vacuo affords a residue which is washed thoroughly with diethyl ether and filtered to remove Nabs. -The filtrate is then washed with several small portions of water, dried, and evaporated in vacuo to give the crude nitrile of Formula XXVII which can most conveniently be purified by either vacuum distillation or column chromatography. The aldehydes of Formula XXIIIb, wherein n=l and R11=H, can be prepared in a straightforward tanner from the appropriate alcohols of Formula XXV via a classical five-step homologation sequence as shown in Equation 27(a-e). Equation 27 EMI33.1 wherein R2 is as previously defined; and n is 1. The conversion of alcohols such as XXV to the corresponding bromides, XXIX, as shown in Equation 27(a), is well precedented in the literature and can be effected according to the procedure described by I. M. Downie, et al., Chem. Ind. (London), 900 (1966). The displacement reaction of Equation 27(b), whereby bromides, XXIX, are converted to the corresponding nitriles of Formula XXX, has been discussed above for Equation 26. For relevant procedures, see L. Friedman and H. Schechter, J. Org. Chem., 25, 877 (1960); also, R. A. Smiley and C. Arnold, ibid. 25, 257 (1960). The hydrolysis reaction of Equation 27(c) is preferably carried out as described above for Equation 25. Reduction of carboxylic acid esters of Formula XXXI to the corresponding alcohols, XXXI I, as shown in Equation 27(d), can be accomplished by use of lithium aluminum hydride as described for Equation 24. The desired aldehydes, XXIIIb, can be obtained as shown in Equation 27(e) via oxidation of the appropriate alcohols of Formula XXXI I with pyridinium chlorochromate (PCC) according to the method of Corey, Tetrahedron Lett., 2644 (1975). Benzenesulfonamides of Formula IVh may be prepared as illustrated in Equation 28. Equation 28 EMI34.1 EMI35.1 wherein X is F, Br, or C1; and R2 and n are as previously defined. Reaction Step 28(a) Reaction step 28(a) is conveniently carried out following the method of R. H. Smithers, 3. Org. Chem., 43, 2833 (1978). The synthesis of the appropriate Wittig reagents, XXXIII, is taught in the following references : Ph3P-CCl2/B. A. Clement and R. L. Soulen, J. Org. Chem., 41, 556 (1976). Ph3P-CBr2/E. J. Corey and P. L. Fuchs, Tetrahedron Lett., 3769 (1972). G. Naae and D. J. Burton, Fluorine Chem., 1, 123 (1971); Synth. Comm., 3, 197 (1973). Reaction Step 28(b) The reaction shown in Equation 28(b) is best effected according to the procedure of S. N. Bhattacharya et al., J. Chem. Soc., (C) 1265 (1968). This procedure is discussed under Equation 11 above. Step 3 of Equation 28(b) is carried out in a manner analogous to that described for Equation 12 above. Benzenesulfonamides of Formula IVi and IVj can also be synthesized by use of the appropriate Wittig or phosphonate reagents, XXXIIIa or XXXIIIb, respectively. The intermediate aryl bromides XXXVII and XXXVIII can then be treated according to the procedure of Bhattacharya as described above. These reactions are summarized in Equation 29. Equation 29 EMI36.1 wherein R2 and R9 are as previously defined. The reactions shown in Equation 29 are best carried out by employing the same procedures referenced above for Equation 28. Benzenesulfonamides of Formula IVk can be most conveniently obtained by reduction of the olefins of Formula XXXV followed by metallation, sulfuryl chloride addition, and treatment with ammonia as described above for Equation 11. This procedure is illustrated in Equation 30. Equation 30 EMI37.1 wherein R2 and n are as previously defined; and R45R5=F, C1, or Br. The-eduotion step of Equation 30(a) can be accomplished by following the procedure of J. W. Hamersma and E. I. Snyder, J. Org. Chem., 30, 3985 (1965). There are numerous ways of preparing alkyl thioethers such as XLII. One of the best-known methods starts with the corresponding alkyl bromides, XIb, as shown in Equation 31. Equation 31 EMI38.1 wherein R2, R6, and n are as previously defined; and R4 is H or CH3. The displacement of alkyl bromides with thiourea to generate thiouronium bromide salts, XL, is well known in the literature. This reaction can best be carried out according to the methods of T. B. Johnson and J. M. Sprague, 3. Am. Chem. Soc., 58, 1348 (1936); 59, 1837, 2439 (1937); 61, 176 (1939). The reaction of Equation 31(b), in which the thiouronium salts of Formula XL are hydrolyzed to the corresponding thiols, XL1, is most conveniently carried out by the procedure described by B. C. Cossar Qt al., 3. Org. Chem., 27, 93 (1962). The third step shown in Equation 31 involves alkylation of the sodium or potassium salts of thiols XLI with the appropriate C1-C3 alkyl iodide to give the desired alkyl thioethers of Formula XLI I. Mercaptide alkylations of this kind can be effected by a wide variety of methods. For reviews, see Reid, "Organic Chemistry of Bivalent Sulfur", Vol. 2, pp. 16-21, 24-49; Vol. 3, pp. 11-14 (1960); also, Patai, "The Chemistry of the Thiol Group", pt. 2, pp. 721-735, and references cited therein. The t-butyl sulfonamides of Formula XLII can be deprotected as described above in Equation 8(e) and elaborated further as in Equations 2, 3, 4, 6, or 7. Alternatively, the alkyl thio ethers of Formula XLII may be oxidized as represented in Equation 32 to give the cor.responding sulfoxides (XLIII, m or sulfones (XLIII, m=2). Equation 32 EMI39.1 wherein R2, R6, n, and m are as previously defined; and R4 is H or CH3. The oxidation of Equation 32 may be accomplished using a variety of literature procedures with m-chloroperoxybenzoic acid (m-CPBA); for example, see C. R. aohnson, et al., Tetrahedron, 25, 5649 (1969). The t-butyl sulfonamides of Formula XLII can be deprotected as described above in Equation 8(e) and elaborated further as in Equations 2, 3, 4, 6, or 7. Bromides of Formula XIb can be easily prepared from the corresponding alcohols, XIa, by treatment with triphenyl or trioctyl phosphine and carbon tetrabromide as shown above for XXV in Equation 27(a). For a detailed procedure, see I. M. Downie, et al., Chem. Ind. (Lodon), 900 (1966). Benzenesulfonamides of Formula IVm may be obtained as shown in Equation 33 via chlorination of the appropriate vinyl chlorides XXXVII. Equation 33 EMI40.1 wherein R2 is as previously defined. The addition of chlorine to olefins is a well known reaction and can be accomplished by a variety of methods. For pertinent examples, see Houben-Weyl, Methoden der Organischen Chemie, Ge org Thieme Verlag, Stuttgart, 4th Ed., Vol. 5, Pt. 3, p. 529. The intermediates obtained in reaction step 1 of Equation 33 can be converted to the appropriate sulfonamides of Formula IVm according to the procedure of Bhattacharya as described previously. Benzenesulfonamides of Formula IVn may also be prepared via chlorination of suitable olefins of Formula XLIV as shown below in Equation 34. Equation 34 EMI41.1 wherein R2 is as previously defined. The transformation shown above is best effected using the procedure referenced for Equation 33. The sulfonamides, IVn, may then be converted to the sulfonylureas by methods taught earlier. Olefins of general structure XLIV can most conveniently be prepared according to methods taught in United States Patent 4,368,069, issued January 11, 1982. Sultonylureas of Formula Id, wherein RS is C02R8 and R8 is C2-C3 alkyl, CHzCH=CH2, CH2CH20CH3, or CH7CH2C1, can most conveniently be prepared by a transesterification reaction of the corresponding compounds of Formula Ic, wherein R5 = C02R8 and R8 is CH3. This is summarized in Equation 35. Equation 35 EMI42.1 wherein R2, R3, n, and A are as previously defined; R4 is H or CH3; and R8 is C2-C3 alkyl, CH2CH=CH2, CH2CH20CH3 or CH2CH2C1. The reaction of Equation 35 is most conveniently carried out by adding a slight excess of trimethylaluminum (as a standardized toluene solution) to a solution of the appropriate alcohol of Formula R8OH in a dry suitable solvent such as benzene or toluene at temperatures of -50C to 50C. After being stirred at ambient temperature for about 30 minutes, the reaction mixture is treated with the appropriate sulfonylurea (Ic) and the solution is heated to reflux temperature (80-1100C) until most or all of the methyl ester has been converted to the desired product Id. The solution is then cooled to room temperature and acidified by the addition of 10X HC1. The desired product often separates from solution and may be isolated by filtration. If no precipitate forms, then extraction into a suitable solvent such as methylene chloride or ethyl acetate followed by drying and evaporation of the solvent in vacuo affords the product which may be purified by recrystallization or column chromatography if necessary. For examples of titanate-mediated transesterifications, refer to D. Seebach, Synthesis, 138 (1982). Sulfonylureas of Formula Ic are best prepared by methods described earlier starting from the appropriate benzenesulfonamides of Formula IVo. These sulfonamides, IVo, are most conveniently synthesized by the reduction of the corresponding a,8-unsaturated carboxylic acid esters of Formula XLV as shown in Equation 36. Equation 36 EMI43.1 wherein R2 and n are as previously defined; and R4 is H or CH3. The reaction of Equation 36 may be carried out in an inert solvent such as methanol or acetic acid using a suitable catalyst such as palladium-on-carbon and one to five atmospheres of hydrogen. When hydrogen uptake has ceased, the reaction mixture is filtered through a pad of Celite to remove the catalyst. Evaporation of the solvent in vacuo typically affords the pure sulfonamides IVo. Benzenesulfonamides of Formula XLV are best prepared by the two-step procedure shown in Equation 37. Equation 37 EMI44.1 wherein R2 and n are as previously defined; and R4 is H or CH3. Reaction step (a) of Equation 37 is best carried out as follows: the appropriate acrylate ester and bromide XLVI are mixed together and heated to 1000C in the presence of catalytic amounts of palladium acetate and tris-(o-tolyl)phosphine and excess triethylamine for a period of from 1 to 10 hours. The reaction preferably is performed in a sealed vessel. The mixture is allowed to cool and is poured into ammonium chloride solution. Extraction with a suitable solvent such as diethyl ether or methylene chloride followed by drying and evaporation of the organic layers gives the ass-unsaturated esters XLVII. Purification may be achieved by column chromatography if necessary. Removal of the t-butyl protecting group from compounds XLVI I can be accomplished using tritiuoro- acetic acid as described above in Equation 8(e and f). The t-butyl sulfonamides of Formula XLVIa, where n=0, can be conveniently prepared as described above in Equation 10. Sulfonamides of Formula XLVIb, where n=l, can be obtained by benzylic bromination of the appropriate compounds IXa as shown in Equation 38. Equation 38 EMI45.1 wherein R2 is as previously defined. The bromination of Equation 38 is best carried out according to methods taught by L. Homer and E. H. Winkelmann, Angew. Chem., 71, 349 (1959) and references cited therein. The heterocyclic amines of Formula III in Equation 1 are also important intermediates for the preparation of the compounds of this invention and can be prepared by the following methods. The pyximidines.and triazines of Formula IIIa to IIIc below, wherein R3=H, are either known or can be prepared by obvious methods by one skilled in the art. For instance, the synthesis of pyrimidines and triazines of the general formula VIIa has been reviewed in The Chemistry of Heterocyclic Compounds, a series published by Interscience Publishers, Inc., New York and London. 2-Aminopyrimidines are described by D. 3. Brown in The Pyrimidines, Vol. 16 of this series. 2-Amino-1,3,5-triazines are reviewed by E. M. Smolin and L. Rapaport in s-Triazines and Derivatives, Vol. 13 of the same series. The synthesis of triazines is also described by F. C. Schaefer, U.S. 3,154,547 and by K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963). The syntheses of the bicyclic amines IIIb and IIIc are described in EPO Publication No. 15,683. EMI46.1 wherein X, Y, Z, X1, and V1 are as previously defined, except that Y is not CH(OCH3)2, CH(OCH2CH3)2, EMI46.2 Pyrimidines below of Formula slid, where Y is CH(OC2H5)2, are described by W. Braker et al., 3. Am. Chem. Soc., 69, 3072 (1947), the disclosure of which is herein incorporated by reference. Using techniques taught by Braker, or suitable modifications that would be obvious to one skilled in the art, the pyrimidines Ilid can be prepared. EMI46.3 wherein X is CH3, OCH3, or C1; and V is CH(OCH3)2 or EMI47.1 Triazines of Formula IIIe may be prepared according to the methods outlined in Equations 39 and 40. Equation 39 EMI47.2 wherein X is CH3 or OCH3; and Y is CH(OCH3)2 or EMI47.3 Equation 40 EMI48.1 wherein X and Y are as defined in Equation 39. The reaction of Equation 39a is carried out according to the teachings of J. M. McElvain and R. L. Clarke, J. Am. Chem. Soc., 69, 2657 (1947), in which the preparation of ethyl diethoxyiminoacetate is described. The intermediate N-cyanoimidate or Formula L may be prepared according to the teaching of O. Lwowski in Synthesis, 1971, 263, by reacting XLVIX with cyanamide at pH 5.5, and this may be condensed according to reaction 39(c) with either acetamidine or Methyl isourea in an alcoholic solvent at 250C to 800C to provide the appropriate triazines. Alternatively, the reaction of Equation 40(a), described for substituted acetonitriles by F. C. Schaefer and G. A. Peters in 3. Org. Chem., 26, 412 (1961), may be used to convert nitriles of Formula XLVI II to the corresponding iminoesters. The free bases may be carried on through reactions 40(b) and 40(c), or, alternatively, converted to the amidinium hydrochloride salts LI as described in the aforementioned reference, and condensed with either methyl N-cyanoacetimidate or with dimethyl N-cyano imidocarbonate in the presence of one equivalent of sodium methoxide to provide the triazines of Formula Ille. Cyclic acetals of Formula IIIg also may be prepared from compounds of Formula IIIt according to Equation 41 by acetal exchange. Equation 41 EMI49.1 wherein X is CH3 or OCH; and Z is CH or N. The reaction of Equation 41 is carried out by heating the acyclic acetal in an inert solvent in the presence of one equivalent of ethylene glycol and slightly more than one equivalent of a strong acid, such as E-txlueneaul-fonic acid, with removal of the methanol or ethanol formed in the reaction by distillation. The product is isolated by treatment with aqueous base and extraction with an organic solvent, and purified by crystallization or column chromatography. Preparations of 3-amino-l,2,4-triazoles of Formula III in Equation 1 are known in the art and 1,2,4triazoles are reviewed in The Chemistry of Heterocyclic Compounds, "Triazoles 1,2,4" (aohn Wiley and Sons, New York, 1981). Commonly used starting materials containing nitrogen are N-aminoguanidine, hydrazine, alkylhydr azines, cyanamide, ethyl cyanoacetimidate, dimethyl cyanodithioimidocarbonate, dimethyl cyanoimidocarbonate, ethoxymethylenecyanamide, and acylhydrazines. Some literature syntheses are illustrated below. Using these techniques or suitable modifications that would be apparent to one skilled in the art, the 3-amino-l,2,4-triazole intermediates can be readily prepared. Heating equimolar amounts of ethyl propionimidate hydrochloride and N-aminoguanidine nitrate in pyridine gives 3-amino-5-ethyltriazole; German Patent 1,073,499 (1960); Chem. Ber., 96, 1064 (1963). EMI50.1 Condensation of hydrazine with ethyl N-cyanoacetimidate yields 3-amino-5-methyltriazole; J. Org. Chem., 28, 1816 (1963). EMI50.2 U.S. Patent 2,835,581 (1958) teaches the preparation of 3-amino-S- (hydroxymethyl ) triazole from N-aminoguanidine and glycolic acid and British Patent 736,568 (1955) describes the synthesis of 3-amino-5-mercapto triazole. EMI51.1 Condensing hydrazine with dimethyl cyanodithioimidocarbonate in acetonitrile gives 3-amino-5-methylthio- 1,2,4-triazole, while reaction of hydrazine with dimethyl N-cyanoimidocarbonate produces 3-amino-5-me- thoxy-1,2,4-triazole; J. Org. Chem., 39, 1522 (1974). EMI51.2 Reaction of substituted hydrazines with N-cyano thiolmidocarbonates (prepared according to the procedure given in D. M. Wieland, Ph.D. Thesis, 1971, pp. 123-124) yields disubstituted aminotriazoles as shown below. EMI51.3 Many of the aminoheterocyclic intermediates of Formula III where R3 is methyl may be prepared by a two-step procedure as described for IIIh in Equation 42. Equation 42 EMI52.1 wherein X, Y, and Z are as originally defined; and R3 is CH3. A solution of the amine LII in concentrated hydrochloric acid is treated with sodium nitrite solution and the chloro compound LIII is isolated in the usual manner by filtration of the acidic solution. A representative procedure is described by Bee and Rose in J. Chem. Soc., C, 2031 (1966), for the case in which Z = CH, and X = Y = OCH3. Displacement of the chlorine of LIII may be accomplished by heating with an excess of methylamine in water to obtain the methylamino heterocycle IIIh. Equation 43 below illustrates the preparation of the required methyl pyrimidinyl carbamates and methyl triazinyl carbamates of Formula VIII in Equation 7. By suitable modifications, other methyl carbamates of Formula VIII may be prepared by this method by one skilled in the art. Equation 43 EMI53.1 wherein X, Y, Z, and R3 are as originally defined. According to Equation 43, a heterocyclic amine is reacted with two equivalents of sodium hydride and excess dimethyl carbonate to form VIII. The reaction is run in an inert solvent such as tetrahydrofuran at 250C to reflux for 1 to 24 hours. The product is isolated by (a) adding about two equivalents of concentrated hydrochloric acid under nitrogen at OOC to 30 C ; (b) filteruing; and (c) separating out the organic phase, then drying (sodium sulfate and/or magnesium sulfate) and concentrating to dryness in vacuo. The product VIII may be purified further by recrystallization or chromatography procedures. The aminomethyl triazines of Formula lIli can most conveniently be prepared via a three-step sequence as shown in Equation 44. Equation 44 EMI54.1 wherein X3 is CH3 or OCH3. Reaction Step 44(a) The displacement reaction shown in Equation 44ta) above is preferably carried out by adding at least one equivalent of liquid trimethylamine to a cooled (0 C) solution of the appropriate 2-chlorotriazine LIV in a suitable solvent such as acetone or tetrahydrofuran. The reaction solution is stirred at ambient temperature for 1-24 hours, during which time the product LV typically precipitates. Filtration and drying in vacuo affords the pure salts of Formula LV. Reaction Step 44(b) The reaction of Equation 44(b) can best be ac complished by adding excess potassium cyanide to a warm (80-1000C) mixture of the salts of Formula LV and molten acetamide; the evolution of trimethylamine is immediately apparent. Following the addition, the solution is heated at temperatures of 80-lOOtC for 1 to 4 hours. Addition of water, extraction of the aqueous layer with a suitable solvent such as diethyl ether, and evaporation of the organic layer yields the nitriles, LVI, which are usually of sufficient purity to carry on to the next step. Alternatively, the salts LV may be treated with tetrabutyl ammonium cyanide according to the procedure of K. Hermann and G. Simchen, Ann., 1981 333. Reaction Step 44(c) The heterocyclic nitriles of Formula LVI may be hydrogenated in a suitable solvent such as methanol using a palladium-on-carbon catalyst and in the pre sence of one equivalent of concentrated hydrochloric acid; a hydrogen atmosphere of 40-30 p.s.i. is opti mal. When hydrogen uptake has ceased, the solution is filtered through Celite to remove the catalyst, and the volatiles are distilled off in vacuo. The residue - is taken u > -in water and sodium hydroxide is added until the aqueous layer is pH 10-12. In some cases1 the amines lIli precipitate from solution and may be obtained by filtration. If this does not occur, ex traction with a suitable solvent (e.g., methylene chloride) followed by drying and evaporation of the organic layer affords the desired amines of Formula IIIi. The requisite 2-chloro-l,3,3-triazines of For mula LIV are known compounds. See J. Kobe et al., Monatsh. 101, 724 (1970), for the synthesis of triazines, 1111, wherein X3=CH3; and for the preparation of triazines, IIIi, wherein X3=OCH3. Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can-be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (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 sn aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the 7cation 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 with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid, or the like. The compounds of this invention and their pre paration are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless other wise indicated. Example 1 2-(2-Hydroxyethyl)-N-(l,l-dimethylethyl)benzene sulfonamide A solution of N-(l,l-dimethylbenzenesulfonamide (40.0 g) in 550 ml dry tetrahydrofuran was cooled to 0 and 250 ml of 1.6 M n-butyllithium added dropwise at 00. After the addition of one equivalent of base, the solution turned yellow. After stirring for 2 hours at room temperature, the resulting suspension was cooled to 0 and 13 ml of ethylene oxide added dropwise. After stirring of 3.5 hours at room temper ature, the homogeneous yellow solution was poured into water. The product was extracted with ether and dried (Na2504). Concentration gave a yellow oil which was purified by column chromatography t4ûO g silica gel, ether/hexane (1:1) followed by ethyl acetate). Pure 2-(2-hydroxyethyl)-N-(1,l-dimethylethyl)benzene sulfonamide was obtained as a colorless oil which solidified after several days; m.p. 43-45 . NMR (CDC13) 6: 8.09 (1H, d); 7.19-7.68 (3H, m); 5.53 (1H, s); 3.98 (2H, m); 3.31 (2H, t, 3=7Hz); 3.01 (1H, t, OH); and 1.25 (9H, s, C(CH3)3). IR (neat) 3400, 3200, 1300, 1140 cm-l. Example 2 2-(2-Methoxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide A suspension of 37.0 g of potassium t-butoxide in 400 ml dry tetrahydrofuran was cooled to OO and a solution of 39.2 g of the product from Example 1 in 300 ml tetrahydrofuran was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After cooling to 00, 9.3 ml of methyl iodide was added dropwise and the mixture stirred for 15 minutes at 00. The solution was diluted with ether, washed with water and dried (Na2SO4). Concentration gave a viscous brown oil which was used in the following example, without further purification. NMR (CDC13): 6 3.32 (3H, s, OCH3); and 1.23 (9H, s, C(CH3)3). Example 3 2-(2-Methoxyethyl)benzenesulfonamide A solution of the crude ether from Example 2 (35.0 g) and 80 ml trifluoroacetic acid was stirred at room temperature for 16 hours. The trifluoroacetic acid was removed in vacuo and ethylene chloride added to the residue. The organic phase was washed twice with cold saturated sodium bicarbonate, once with water and dried (Na2-S04). Concentration gave a viscous brown oil which was triturated with hexane. The resulting sticky solid was recrystallized from chloroform/hexane (1:1) to provide 11.0 g of pure 2-(2-methoxyethyl)benzenesulfonamide as a white solid; m.p. 79-81. NMR (CDCl3 + DMSO-d6): 6 7.93-8.12 (1H, m); 7.18-7.63 (3H, p 6.19 (2H, broad s, NH2); 3.60-3.82 (2H, m); and 3.18-3.49 (SH, m). IR (Nujol) 3420 and 3320 (NH2) cm 1. Example 4 N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2 (2-methoxyethyl )benzenesulfonamide To a solution of the product from Example 3 (2.0 g) in 100 ml methylene chloride was added 4.7 ml of 2 M trimethylaluminum in toluene via syringe. Gas evolution was observed. After 30 minutes, 1.98 g N-(4,6-dimethyoxypyrimidin-2-yl)methylcarbamate was added and the reaction mixture heated at reflux for 16 hours. The mixture was poured into cold 10% hydrochloric acid and diluted with methylene chloride. The organic phase was washed with water and dried (Na2SO4). Concentration gave a white solid which was stirred with 100 ml acetone and collected by filtration to provide 1.1 g of N-C(4-6)diethoxypyrimidin-2-yl)amino- carbonyl]-2-(2-methoxyethyl)benzenesulfonamide ; m.p. 178-181 . NMR (DMSO-d6): 12.80 (1H, broad s, NH); 10.55 (1H, s, NH); 8.01-8.20 (1H, m); 7.39-7.83 (3H, m); 6.00 (1H, s); 3.92 (6H, s, OCH3); 3.12-3.65 (4H, m); and 3.10 (3H, s, OCH3). IR (Nujol) 1700 (C=O) cm 1. Example 5 2-t2-(Acetyloxy)ethyl)-N-(l,l-dimethylethyl)benzene¯ sulfonamide A solution of 29.0 g of the product from Example 1 and 24 ml triethylamine in 290 ml of dichloromethane was cooled to 00C and treated with 13 ml acetic anhydride. The reaction mixture was stirred at room temperature for 22 hours. Dichloromethane (200 1) was added and the organic layer washed with three 50 ml portions of water and one portion of brine. Drying the organic layer over magnesium sulfate followed by concentrating in vacuo gave the crude product. Purification by silica gel chromatography (elution with hexanes-ethyl acetate, 70:30) afforded 19.5 g of pure 2-[2-(acetyloxy)ethyl]-N-(1,1-dimethylethyl)benzenesulfonamide as a colorless oil. NMR (CDCl3) : # 8.1-8.3 (1H, m) ; 7.3-7.5 (3H, mg 5.3 (1H, brs, NH); 4.4 (2H, t, J=7Hz, -CH20Ac); 3.4 (2H, t, 3=7Hz, -CH2-); 2.1 (3H, s, COCH3); and 1.3 (9H, s, t-Bu). IR (neat): 3290 (NH stretch), 1730 (C=0 stretch) cm Example 6 2-[2-(Acetyloxy)ethyl]benzenesulfonamide The product from Example 5 (13.8 g) was added in portions to 75 ml of trifluoroacetic acid at room temperature and the resulting solution was stirred for 21 hours. Removal of the trifluoroacetic acid in vacuo gave a light orange oil which crystallized upon addition of diethyl ether. Filtration and air drying yielded 9.18 g of pure 2-(2-(acetyloxy)ethyl)benzene- sulfonamide as a white powder, m.p. 116-117.50C. NMR (CDC13 + DMSO-d6): 6 8.0 (1H, m); 7.3-7.5 (3H, m); 7.1 (2H, brs, NH2); 4.3 (2H, t, a=7Hz, -CH2-), 3.4 (2H, t, J=7Hz, -CH20Ac); and 2.0 (3H, s, -COCH3). Example 7 2-[2-(Acetyloxy)ethyl]benzenesulfonyl isocyanate A solution of 9.18 g of the sulfonamide from Example 6 in 125 ml thionyl chloride was heated at reflux temperature for 46 hours; an aliquot withdrawn showed the complete absence of starting material by 1H NMR. Excess thionyl chloride was removed in vacuo and the resulting yellow oil was treated with 74.0 g of a 10% (wt/wt) phosgene/toluene solution and a catalytic amount (ca. 20 drops) of pyridine. The resulting reaction mixture was heated at reflux temperature for 4 hours. After being allowed to cool, the solution was filtered under a stream of nitrogen and all volatiles were removed in vacuo to afford 11.0 g of 2-[2-(acetyloxy)ethyl]benzenesulfonyl isocyanate as a viscous orange oil. NMR (CDC13): 8.1-8.2 (1H, m); 7.4-7.7 (3H, m); 4.4 (2H, t, 3=7Hz, -CH2OAc); 3.4 (2H, t, a=7Hz, -CH2-; and 2.0 (3H, s, COCH3). Example 8 2-[2-(Acetyloxy)ethyl]-N-[(4,6-dimethoxypyrimidin-2yl)aminocarbonyl]benzenesulfonamide To a stirred solution of 2.3 g of the sulfonyl isocyanate from Example 7 in 25 ml dry acetonitrile was added 1.2 g of 2-amino-4,6-dimethoxypyrimidine. The reaction mixture was warmed to 50 C for 1 1/4 hour and then stirred at room temperature for 2 days. Filtration of the insoluble solids and washing with l-chlorobutane followed by drying afforded 1.8 g of 2-[2-(acetyloxy)ethyl]-N-[(4,6-dimethoxypyrimidin-2yl)aminocarbonyl]benzenesulfonamide as a light yellow solid, m.p. 160-1620C. NMR (CDCl3 + DMSO-d6): # 12.9 (1H, brs, NH); 10.5 (1H, s, NH); 8.2 (1H, m) ; 7.4-7.7 (3H, m); 5.9 (1H, s, hetero cyclic H); 4.3 (2H, t, a=6Hz, -CH2-) ; 4.0 (6H, s, OCH3 . 3.4 (2H, t, J=6Hz, -CH20Ac); and 2.0 (3H, s, -COCH3). Example 9 2-[2-(Methylsulfonyloxy)ethyl]-N-(2,2-dimethylethyl) benzenesulfonamide The alcohol from Example 1 (33.1 g) and 20 ml of triethylamine were dissolved in 350 ml of dichloro methane, cooled to OOC, and treated with 11 ml methanol sulfonyl chloride. After being stirred at room tem perature for about 20 hours, the reaction mixture was diluted with dichloromethane (100 ml) and the organic layer was washed with three S0-ml portions of water and one of brine. Drying and concentration in vacuo gave the crude product which gradually crystallized upon standing. The solid was washed with diethyl ether, filtered, and dried to yield 12.0 g of 2-(2- (methylsulfonyloxy)ethyl]-N-(2,2-dimethylethyl)benzenesulfonamide as a white powder, m.p. 106-1080C. NMR (CDC13 DMSO-d6): 6 8.0 (1H, m); 7.5 (3H, m 7.2 (1H, brs, NH); 4.5 (2H, t, 3=7Hz, -CH2OMs); 3.5 (2H, t, 3=7Hz, -CH2-); 2.9 (3H, s, 3=6Hz, -CH2-); 4.0 (6H, s, OCH3's); 3.4 (2H, t, 3=6Hz, -CH20Ac); and 2.0 (3H, s, -COCH3). Example 10 2-(2-Bromoethyl)-N-(l,l-dimethylethyl)benzenesulfonamide A mixture of 8.0 g of the product from Example 9, 4.9 g sodium bromide and 1.0 g potassium bromide in methyl=ethy-l ketone was heated at reflux temperature for approximately 24 hours. The reaction solution was allowed to cool to room temperature and was filtered to remove the insoluble salts. Evaporation of the filtrate under reduced pressure gave the crude bromide as a yellow oil. Purification by silica gel chromato graphy (elution with hexanes-ethyl acetate, 60:40) afforded 6.4 g of pure 2-(2-bromoethyl)-N-(l,l-dimethylethyl)benzenesulfonamide as a viscous, colorless oil. NMR (CDCl3): 6 8.0-8.2 (1H, m); 7.3-7.6 (3H, m); 5.0 (1H, brs, NH); 3.6 (4H, brt, -CH2CH2-); and 1.2 (9H, s, t-Bu). Example 11 2- (2-Bromoethyl )benzenesulfonamide A solution of 6.3 g of the product from Example 10 in 30 ml trifluoroacetic acid was stirred at room temperature for one hour. The desired product was insoluble in the reaction mixture and was isolated by filtration. Washing with diethyl ether and drying gave 4.5 g of 2-(2-bromoethyl)benzenesulfonamide as a white solid, m.p. 1690-1710C (dec.). NMR (CDCl3): 6 8.0-8.1 (lH, m); 7.3-7.5 (3H, m); 6.9 (2H, brs, NH2); and 3.6-3.7 (4H, m, -CH2CH2-). Example 12 2-(2-Bromoethyl)benzenesulfonyl isocyanate A solution of 4.0 g of the product from Example 11 in 45 ml thionyl chloride was heated at reflux temperature for 19 hours at which time no starting material could be detected by 1H NMR. The solution was concentrated in vacuo and the resulting solid was taken up in 30 g of a 10% (wt/wt) phosgene/toluene mixture. A catalytic amount of pyridine was added (ca. 6 drops) and the reaction solution was heted to reflux for 4 hours. Insoluble material was removed by filtration under nitrogen and the filtrate was concentrated in vacuo to yield 4.5 g of the sulfonyl isocyanate as an orange oil. IR (neat): 2240 cm 1 (isocyanate stretch) Example 13 2-(2-Bromoethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl )benzenesulfonamide To a stirred solution of 2.2 g of the sulfonyl isocyanate from Example 12 in 15 ml dry acetonitrile was added 1.0 g of 2-amino-4,6-dimethoxypyrimidine and the mixture was warmed to 450C for 45 minutes. Upon cooling, the solution yielded the desired product which was collected by filtration, washed with 1chlorobutane, and dried. The yield of 2-(2-bromoethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbon ylJbenzenesulfonamide was 1.6 g light yellow powder1 m.p. 1630-1660C. NMR (CDC13 + DMSO-d6): 6 13.0 (1H, s, NH); 10.3 (1H, s, NH); 8.2 (lH, m); 7.4-7.7 (3H, m); 5.8 (1H, s, hetero cyclic H); 4.0 (6H, s, OCH3's); and 3.6 (4H, m, -CH2CH2-). IR (KBr) : 1710 cm-1 (C=0 stretch). Example 14 2-(2-Chloroethyl)-N-(1,1-dimethylethyl)benzene sulfonamide A solution of 32.5 g of the alcohol from Example 1 and 32.5 g triphenylphosphine in 244 ml of carbon tetrachloride was stirred at room temperature and under an atmosphere of nitrogen for 72 hours. Excess carbon tetrachloride was removed in vacuo to give 83 g of a crude yellow oil. Purification by silica gel chromatography (hexanes-20% ethyl acetate) afforded a colorless viscous oil which crystallized on standing. The product was isolated by trituration with hexanes, filtration, and drying. The yield of pure 2-(2-chloro ethyl)-N-(l,l-dimethylethyl)benzenesulfonamide, m.p. 64-650C, was 15.9 g. NMR (CDCl3) : 6 8.0-8.2 (1H, mult); 7.4-7.6 (3H, mult); 5.7 (1H, br s, NH); 3.9 (2H, br t, -CH2C1); 3.5 (2H, br t, ArCH2-); and 1.2 (9H, s). Example 15 2-(2-Chloroethyl)benzenesulfonamide The product from Example 14 (15.8 g) was added to 96 ml of trifluoroacetic acid at room temperature. After being stirred for 30 minutes, the reaction mixture yielded white crystals which were collected by filtration, washed well with diethyl ether, and dried to afford 10.9 g of the title compound, m.p. 168-171 C. NMR (CDCl3 + DMSO-d6): 6 8.0-8.1 (1H, mult); 7.4-7.6 (3H, mult); 7.0 (2H, s, NH2's); 3.9 (2H, t, 3=7Hz, -CH2C1); and 3.5 (2H, t, J=7Hz, ArCH2-). IR (KBr) : 3360 and 3260 cm-1. Example 16 2-(2-Chloroethyl)benzenesulfonyl isocyanate A solution of 10.1 g of the product from Example 15 in 140 ml thionyl chloride was heated at reflux temperature for 19 hours. The reaction mixture was then allowed to cool, 2 ml of dry toluene was added, and all volatile materials were removed in vacuo. To the resulting residue was added 91 g of a lOX (by weight) solution of phosgene in toluene and 25 drops of pyridine. The mixture was heated to gentle reflux for 4 hours and was then allowed to cool to room temperature. Filtration under a stream of dry nitrogen followed by concentration in vacuo gave the desired sulfonyl isocyanate as a yellow oil. The infrared spectrum of the product displayed a characteristic isocyanate stretching absorption at 2240 cm'l Example 17 2-(2-Chloroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]benzenesulfonamide The sulfonyl isocyanate (1.9 g) from Example 16 in 17 ml dry acetonitrile was treated with 1.2 g of 2-amino-4,6-dimethoxypyrimidine at room temperature. Within 10 minutes, a precipitate formed. The reaction mixture was warmed to 40-450C for one hour and then stirred at room temperature for several days. The solids were filtered, washed with l-chlorobutane, and dried in vacuo to give 1.7 g of 2-(2-chloroethyl)-N [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide as a white powder, m.p. 169-1710C. NMR (CDCl3 + DMSO-d6): 6 13.0 (1H, br s, NH); 9.2 (1H, br s, NH); 8.2 (1H, mult); 7.5 (3H, mult); 5.8 (1H, s, pyrimidine H); 4.0 (6H, s, OCH3's); 3.8 (2H, t, J=7Hz, -CH2C1); and 3.5 (2H, t, 3=7Hz, ArCH2-). IR(KBr): 1710, 1360, 1200 and 1170 cm 1. MS m/e (rel. intensity): 403 (M+ + 2, 3), 401 (M+, 8), 156 (100). Using the procedures and examples described above and choosing the appropriate aminoheterocycle and sulfonamide or sulfonyl isocyanate, the compounds described in Tables I-XXXVII may be prepared. Table I EMI69.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 H H F Cl OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-Cl H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 179-181 d H H Cl OCH3 CH3 162-1630d H H Cl OCH3 OCH3 167-169 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH@ H H Br OCH3 OCH3 163-166 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table I (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 143-145 H H OC(O)CH3 OCH3 OCH3 160-1620 H CH3 OC(O)CH3 OCH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 154-157 H H OC(O)CF3 OCH3 CH3 152-157 H H OC(O)CF3 OCH3 OCH3 154-164 (d) H H OC(O)CF3 Cl OCH3 H H OC(O)CF3 OCH2CH3 CH3 136-142 H H OC(O)CF3 CH3 CH(OCH3)2 152-155 6-CH3 H OC(O)CF3 OCH3 CH3 6-Cl H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 129-134 (d) H H OH OCH3 CH3 126-132 H H OH OCH3 OCH3 136-139 H H OH Cl OCH3 139-143 (d) H H OH OCH2CH3 CH3 134-136 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H CH3 OH Cl OCH3 H H OCH2C6H5 CH3 CH3 148-152 H H OCH2C6H5 OCH3 CH3 163-165 H H OCH2C6H5 OCH3 OCH3 137-143 H CH3 OCH2C6H5 OCH3 CH3 Table I (continued) R2 R4 R5 X Y m.p. ( C) H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 148-149 H H OSO2CH3 OCH3 OCH3 152-154 6-C1 H 0502CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-Cl H 0502CH3 OCH3 CH3 H H OSO2CH2CH3 OCH3 CH3 H H OS02CH2CH2CH3 OCH3 OCH3 H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-OSO2C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 141-143 H H 4'-OSO2C6H4CH3 OCH3 OCH3 122-124 H H 5'-0502C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(0)2CH3 OCH3 CH3 H H S(O)2CH3 OCH3 OCH3 Table I (continued) R2 R4 R5 X Y m.p. ( C) H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH H H S(O)CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H 0502N(CH3)2 CH3 CH3 H H OSO2N(CH3)2 OCH3 CH3 H H OSO2N(CH3)2 OCH3 OCH3 6-Cl H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H 0502N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH H H CO2CH3 OCH3 CH3 176-181 (d) H H C 2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H CO2CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H C02CH2CH20CH3 OCH3 OCH3 H H C02CH2CH2C1 OCH3 CH3 Table II EMI73.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-Cl H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 170-1720d H H Cl OCH3 OCH3 186-188 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 168-170 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table II (continued) R2 R4 R5 X Y m.p. (5C) H H OC(O)CH@ CH3 CH3 H H OC(O)CH3 OCH3 CH3 123-127 H H OC(O)CH3 OCH3 OCH3 124-1260 H CH3 OC(O)CH3 OCH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2OH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 145-150 H H OC(O)CF3 OCH3 CH3 142-1450(d) H H OC(O)CF3 OCH3 OCH3 156-162 H H OC(O)CF3 OCH2CH3 CH3 H H OC(O)CF3 OH3 CHtOCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-C1 H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 118-123 (d) H H OH OCH3 CH3 141-145 (d) H H OH OCH3 OCH3 134-138 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H H OCH2C6H5 CH3 CH3 141-144 H H OCH2C6H5 OCH3 CH3 158-162 H H OCH2C6H5 OCH3 OCH3 152-157 H CH3 OCH2C6H5 OCH3 CH3 H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 159-164 H H OSO2CH3 OCH3 OCH3 Table II (continued) R2 R4 R5 X V m.p.(0C) 6-C1 H 0502CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-C1 H 0502CH3 OCH3 CH3 H H OSO2CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH3 H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 0502CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-OSO2C@H@F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 132-136 C H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-0502C6H4CH3 CH3 CH3 H H 6'-OS02C6H40CH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(0)2CH3 CH3 CH3 H H S(0)2CH3 OCH3 CH3 H H S(O)2CH3 OCH3 OCH3 H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 Table II (continued) R2 R4 R5 X Y m.p. ( C) H H S(0)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(0)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H OSO@N(CH3)2 CH3 CH3 H H OSO2N(CH3)2 OCH3 CH3 H H 0502N(CH3)2 OCH3 OCH3 6-Cl H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H C02CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H C02CH2CH20CH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table III EMI77.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 H H F Cl OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-Cl H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F - H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table III (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H oC(O)CF3 Cl OCH3 H H OC(O(CF3 OCH2CH3 CH3 H H OC(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-Cl H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH Cl OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-Cl H OH OCH3 CH3 6-OCH3 H OH COH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H CH3 OH Cl OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6H5 OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 Table III (continued) R2 R4 R5 X Y m.p. ( C) H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 6-C1 H OSO2CH3 OCH3 CH3 3-och3 H OSO2CH3 OCH3 OCH3 5-Cl H 0502CH3 OCH3 CH3 H H OSO2CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH3 H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-OSO2C6H4F CH3 CH3 H H 3'-OS02C6H4C1 OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-0502C6H4CF3 OCH3 OCH H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(O)2CH3 OCH3 CH3 H H S(0)2CH3 OCH3 OCH3 Table III (continued) R2 R4 R5 X V m.p. ( C) H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H (S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H 0502N(CH3)2 CH3 CH3 H H OS02N(CH3)2 OCH3 CH3 H H 0502N(CH3)2 OCH3 OCH3 6-C1 H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H CO2CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H C02CH2CH=CH2 OCH3 CH3 H H CO2CH2CH2OCH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table IV EMI81.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-C1 H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table IV (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H OC(O)CF3 OCH2CH3 CH3 H H OC(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-C1 H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-Cl H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6H5 OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 Table IV (continued) R2 R4 R5 X Y m.p. ( C) 6-Cl H OSO2CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-Cl H OSO2CH3 OCH3 OCH3 H H OS02CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH3 H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OS02C6H5 OCH3 CH3 H H 2'-OS02C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OS02C6H40CH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH H H S(0)2CH3 CH3 CH3 H H S(O)2CH3 OCH3 CH3 H H S(O)2CH3 OCH3 OCH3 H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH2 H H S(O)CH2CH3 OCH3 CH3 Table IV (continued) R2 R4 R5 X Y m.p. ( C) H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(0)2CH2CH2CH3 OCH3 CH3 H H S(0)2CH2CH2CH3 OCH3 OCH3 H H OSO2N(CH3)2 CH3 CH3 H H OSO2N(CH3)2 OCH3 CH3 H H OSO2N(CH3)2 OCH3 OCH3 6-Cl H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H 0502N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H C02CH2CHn OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H C02CH2CH20CH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table V EMI85.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 H H F Cl OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-C1 H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table V (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OCtO)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H OC(O)CF3 Cl OCH3 H H OC(O)CF3 OCH2CH3 CH3 H H OC(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-Cl H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH Cl OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H CH3 OH Cl OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6H5 OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 Table V (continued) R2 R4 R5 X Y m.p. ( C) H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 6-C1 H OSO2CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-C1 H OSO2CH3 OCH3 CH3 H H OSO2CH2CH3 OCH3 CH3 H H OS02CH2CH2CH3 OCH3 OCH H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-OSO2C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(0)2CH3 OCH3 CH3 H H S(0)2CH3 OCH3 OCH Table V (continued) R2 R4 R5 X Y m.p. ( C) H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H OS02N(CH3)2 CH3 CH3 H H OSQ2N(CH3)2 OCH3 CH3 H H OS02N(CH3)2 OCH3 OCH3 6-Cl H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 C02CH3 OCH3 CH3 H H C02CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH H H C02CH2CH=CH2 OCH3 CH3 H H C02CH2CH20CH3 OCH3 OCH3 H H C 2CH2CH2C1 OCH3 CH3 Table VI EMI89.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-Cl H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table VI (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OCtO)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H OC(O)CF3 OCH2CH3 CH3 H H OC(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-C1 H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6H5 OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 H H OSO2CH3 CH3 CH3 H H OS02CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 Table VI (continued) R2 R4 R5 X Y m.p. ( C) 6-C1 H 0502CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-C1 H OSO2CH3 OCH3 CH3 H H OS02CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH3 H CH3 OS02CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-0502C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(O)2CH3 OCH3 CH3 H H S(0)2CH3 OCH3 OCH3 H CH3 S(0)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 Table VI (continued) R2 R4 R5 X Y m.p. ( C) H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H 0502N(CH3)2 CH3 CH3 H H OSO2N(CH3)2 OCH3 CH3 H H OSO2N(CH3)2 OCH3 OCH3 6-C1 H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H C02CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H CO2CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H CO2CH2CH2OCH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table VII EMI93.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 H H F Cl OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-C1 H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table VII (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H OC(O)CF3 Cl OCH3 H H OC(O)CF3 OCH2CH3 CH3 H H OC(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-C1 H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH Cl OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H @ OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H CH3 OH Cl OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6Hf OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 Table VII (continued) R2 R4 R5 X Y m.p. ( C) H H @ 0502CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 6-C1 H OSO2CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-Cl H OSO2CH3 OCH3 CH3 H H OSO2CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2'-OSO2C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(O)2CH3 OCH3 CH3 H H S(O)2CH3 OCH3 OCH Table VII (continued) R2 R4 R5 X Y m.p. ( C) H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H OSO2N(CH3)2 CH3 CH3 H H OSO2N(CH3)2 OCH3 CH3 H H OSO2N(CH3)2 OCH3 OCH3 6-Cl H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H CO2CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H C02CH2CH20CH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table VIII EMI97.1 R2 R4 R5 X Y m.p. ( C) H H F CH3 CH3 H H F OCH3 CH3 H H F OCH3 OCH3 3-CH3 H F OCH3 CH3 3-OCH3 H F OCH3 OCH3 6-C1 H F OCH3 CH3 H F F OCH3 CH3 H F F OCH3 OCH3 H H Cl CH3 CH3 H H Cl OCH3 CH3 H H Cl OCH3 OCH3 6-Cl H Cl OCH3 CH3 6-CH3 H Cl OCH3 OCH3 6-OCH3 H Cl CH3 CH3 3-CF3 H Cl OCH3 CH3 4-F H Cl OCH3 OCH3 5-CH3 H Cl OCH3 CH3 H Cl Cl OCH3 CH3 H Cl Cl OCH3 OCH3 H H Br CH3 CH3 H H Br OCH3 CH3 H H Br OCH3 OCH3 H Br Br OCH3 CH3 H Br Br OCH3 OCH3 Table VIII (continued) R2 R4 R5 X Y m.p. ( C) H H OC(O)CH3 CH3 CH3 H H OC(O)CH3 OCH3 CH3 H H OC(O)CH3 OCH3 OCH3 H CH3 OC(O)CH3 OCH3 CH3 H H OC(O)CH2CH3 OCH3 CH3 H H OC(O)CH2CH2CH3 OCH3 OCH3 H H OC(O)CF3 CH3 CH3 H H OC(O)CF3 OCH3 CH3 H H OC(O)CF3 OCH3 OCH3 H H OC(O)CF3 OCH2CH3 CH3 H H Oc(O)CF3 CH3 CH(OCH3)2 6-CH3 H OC(O)CF3 OCH3 CH3 6-C1 H OC(O)CF3 OCH3 OCH3 3-OCH3 H OC(O)CF3 OCH3 CH3 H CH3 OC(O)CF3 OCH3 CH3 H H OH CH3 CH3 H H OH OCH3 CH3 H H OH OCH3 OCH3 H H OH OCH2CH3 CH3 H H OH CH3 CH(OCH3)2 6-C1 H OH OCH3 CH3 6-OCH3 H OH OCH3 OCH3 3-CF3 H OH OCH3 CH3 H CH3 OH OCH3 CH3 H CH3 OH OCH3 OCH3 H H OCH2C6H5 CH3 CH3 H H OCH2C6H5 OCH3 CH3 H H OCH2C6H5 OCH3 OCH3 H CH3 OCH2C6H5 OCH3 CH3 H H OSO2CH3 CH3 CH3 H H OSO2CH3 OCH3 CH3 H H OSO2CH3 OCH3 OCH3 Table VIII (continued) R2 R4 R5 X Y m.p. ( C) 6-C1 H OSO2CH3 OCH3 CH3 3-OCH3 H OSO2CH3 OCH3 OCH3 5-Cl H OSO2CH3 OCH3 CH3 H H OS02CH2CH3 OCH3 CH3 H H OSO2CH2CH2CH3 OCH3 OCH3 H CH3 OSO2CH3 OCH3 CH3 H H OSO2CF3 CH3 CH3 H H OSO2CF3 OCH3 CH3 H H OSO2CF3 OCH3 OCH3 H CH3 OSO2CF3 OCH3 CH3 H H OSO2C6H5 OCH3 CH3 H H 2 OS02C6H4F CH3 CH3 H H 3'-OSO2C6H4Cl OCH3 CH3 H H 4'-OSO2C6H4Br OCH3 OCH3 H H 4'-OSO2C6H4CH3 CH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 CH3 H H 4'-OSO2C6H4CH3 OCH3 OCH3 H H 5'-OSO2C6H4CH3 CH3 CH3 H H 6'-OSO2C6H4OCH3 OCH3 CH3 H H 2'-OSO2C6H4CF3 OCH3 OCH3 H H SCH3 CH3 CH3 H H SCH3 OCH3 CH3 H H SCH3 OCH3 OCH3 H CH3 SCH3 OCH3 CH3 H H S(O)CH3 OCH3 CH3 H H S(O)CH3 OCH3 OCH3 H H S(O)2CH3 CH3 CH3 H H S(O)2CH3 OCH3 CH3 H H S(O)2CH3 OCH3 OCH3 H CH3 S(O)2CH3 OCH3 CH3 H H SCH2CH3 OCH3 CH3 H H S(O)CH2CH3 OCH3 CH3 Table VIII (continued) R2 R4 R5 X Y m.p. ( C) H H S(O)2CH2CH3 OCH3 OCH3 H H SCH2CH2CH3 OCH3 OCH3 H H S(O)CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 CH3 H H S(O)2CH2CH2CH3 OCH3 OCH3 H H 0502N(CH3)2 CH3 CH3 H H 0502N(CH3)2 OCH3 CH3 H H OSO2N(CH3)2 OCH3 OCH3 6-C1 H OSO2N(CH3)2 OCH3 CH3 3-OCH3 H OSO2N(CH3)2 OCH3 OCH3 H CH3 OSO2N(CH3)2 OCH3 CH3 H CH3 OSO2N(CH3)2 OCH3 OCH3 H H CO2CH3 OCH3 CH3 H H CO2CH3 OCH3 OCH3 H CH3 CO2CH3 OCH3 CH3 H H CO2CH2CH3 OCH3 CH3 H H CO2CH2CH2CH3 OCH3 OCH3 H H CO2CH2CH=CH2 OCH3 CH3 H H CO2CH2CH2OCH3 OCH3 OCH3 H H CO2CH2CH2Cl OCH3 CH3 Table IX EMI101.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 173-178 H OCH3 H H OCH3 CH3 147-1530 H OCH3 H H OCH3 OCH3 178-181 H OCH3 H H OCH2CH3 CH3 H OCH3 H H Cl OCH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH@ OCH3 OCH3 H OCH3 H CH3 Cl OCH3 H OCH3 H CH3 OCF2H CH3 6-C1 OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H Cl OCH3 Table IX (continued) R2 R9 R10 R12 X Y m.p. ( C) H OCH2CH3 H H OCF2H CH3 6-C1 OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 3-OCH3 OCH@CH@ H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-C1 OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH# Table X EMI103.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 154-156 H OCH3 H H OCH3 CH3 138-141 H OCH3 H H OCH3 OCH3 140-147 H OCH3 H H OCH2CH3 CH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 OCF2H CH3 6-C1 OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H OCF2H CH3 6-C1 OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 Table X (continued) R2 R9 R10 R12 X Y m.p. ( C) 3-OCH3 OCH2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-C1 OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XI EMI105.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH 2CH3 CH3 H OCH3 H H Cl OCH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 Cl OCH3 H OCH3 H CH3 OCF2H CH3 6-Cl OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H Cl OCH3 Table XI (continued) R2 R9 R10 R12 X Y m.p. ( C) H OCH2CH3 H H OCF2 CH3 6-C1 OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 3-OCH3 OCH2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-Cl OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 0CH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XII EMI107.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH2CH3 CH3 H OCH3 H H OCF2H CH3 3-Cl OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 OCF2H CH3 6-Cl OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H OCF2H CH3 6-Cl OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 Table XII (continued) R2 R9 R10 R12 X Y m.p. ( C) 3-OCH3 OCH2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-Cl OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XIII EMI109.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH2CH3 CH3 H OCH3 H H Cl OCH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 Cl OCH3 H OCH3 H CH3 OCF2H CH3 6-Cl OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H Cl OCH3 Table XIII (continued) R2 R9 R10 R12 X Y m.p. ( C) H OCH2CH3 H H OCF2H CH3 6-C1 OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 3-OCH3 OCH2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-C1 OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 175-176 H OCH3 OCH3 H OCH3 OCH3 204-206 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XIV EMI111.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH2CH3 CH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 OCF2H CH3 6-Cl OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H OCF2H CH3 6-Cl OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 Table XIV (continued) R2 R9 R10 R12 X Y m.p. ( C) 3-OCH3 OCH2CH3 H H SOCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-Cl OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XV EMI113.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH2CH3 CH3 H OCH3 H H Cl OCH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 Cl OCH3 H OCH3 H CH3 OCF2H CH3 6-C1 OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H Cl OCH3 Table XV (continued) R2 R9 R10 R12 X Y m.p. ( C) H OCH2CH3 H H OCF2H CH3 6-C1 OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 3-OCH3 OC H2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-Cl OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 OCH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XVI EMI115.1 R2 R9 R10 R12 X Y m.p. ( C) H OCH3 H H CH3 CH3 H OCH3 H H OCH3 CH3 H OCH3 H H OCH3 OCH3 H OCH3 H H OCH2CH3 CH3 H OCH3 H H OCF2H CH3 3-C1 OCH3 H H OCH3 CH3 4-CH3 OCH3 H H OCH3 OCH3 5-CF3 OCH3 H H OCH3 CH3 6-OCH3 OCH3 H H OCH3 OCH3 6-C1 OCH3 H H OCH3 CH3 3-F OCH3 H H OCH3 OCH3 H OCH3 H CH3 CH3 CH3 H OCH3 H CH3 OCH3 CH3 H OCH3 H CH3 OCH3 OCH3 H OCH3 H CH3 OCF2H CH3 6-Cl OCH3 H CH3 OCH3 CH3 6-OCH3 OCH3 H CH3 OCH3 OCH3 3-CF3 OCH3 H CH3 OCH3 CH3 H OCH2CH3 H H CH3 CH3 H OCH2CH3 H H OCH3 CH3 H OCH2CH3 H H OCH3 OCH3 H OCH2CH3 H H OCF2H CH3 6-Cl OCH2CH3 H H OCH3 CH3 6-OCH3 OCH2CH3 H H OCH3 OCH3 Table XVI (continued) R2 R9 R10 R12 X Y m.p. ( C) 3-OCH3 OCH2CH3 H H OCH3 CH3 H OCH2CH3 H CH3 OCH3 CH3 H OCH2CH3 H CH3 OCH3 OCH3 6-Cl OCH2CH3 H CH3 OCH3 CH3 H OCH3 OCH3 H CH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 H OCH3 CH3 H OCH3 OCH3 CH3 OCH3 CH3 H OCH3 OCH3 CH3 OCH3 OCH3 H OCH3 OCH2CH3 H OCH3 CH3 H OCH2CH3 OCH3 H OCH3 OCH3 H OCH2CH3 0CH2CH3 H OCH3 CH3 H OCH2CH3 OCH2CH3 H OCH3 OCH3 H OCH2CH3 OCH2CH3 CH3 OCH3 CH3 Table XVII EMI117.1 R2 R3 R9 R11 X Y m.p. ( C) H H OCH3 H CH3 CH3 H H OCH3 H OCH3 CH3 H H OCH3 H OCH3 OCH3 H H OCH3 H Cl OCH3 H H OCH3 H OCF2H CH3 H CH3 OCH3 H OCH3 CH3 H CH3 OCH3 H OCH3 OCH3 6-OCH3 H OCH3 H OCH3 CH3 3-Cl H OCH3 H OCH3 OCH3 3-OCH3 CH3 OCH3 H OCH3 CH3 H H OCH2CH3 H CH3 CH3 H H OCH2CH3 H OCH3 CH3 H H OCH2CH3 H OCH3 OCH3 H H OCH2CH3 H Cl OCH3 H CH3 OCH2CH3 H OCH3 CH3 6-OCH3 H OCH2CH3 H OCH3 OCH3 H H OCH3 Cl OCH3 CH3 H H OCH3 Cl OCH3 OCH3 6-Cl H OCH3 Cl OCH3 CH3 H CH3 OCH3 Cl OCH3 OCH3 H H OCH2CH3 Cl OCH3 CH3 H CH3 OCH2CH3 Cl OCH3 OCH3 H H OCH3 OCH3 CH3 CH3 H H OCH3 OCH3 OCH3 CH3 Table XVII (continued) R2 R3 R9 R11 X Y m.p. ( C) H H OCH3 OCH3 OCH3 OCH3 H CH3 OCH3 OCH3 OCH3 CH3 6-OCH3 H OCH3 OCH3 OCH3 OCH3 H H OCH2CH3 OCH3 OCH3 CH3 H CH3 OCH2CH3 OCH3 OCH3 OCH3 Table XVIII EMI119.1 R2 R3 R9 R11 X Y m.p. ( C) H H OCH3 H CH3 CH3 H H OCH3 H OCH3 CH3 H H OCH3 H OCH3 OCH3 H H OCH3 H OCF2H CH3 H CH3 OCH3 H OCH3 CH3 H CH3 OCH3 H OCH3 OCH 6-OCH3 H OCH3 H OCH3 CH3 3-Cl H OCH3 H OCH3 OCH3 3-OCH3 CH3 OCH3 H OCH3 CH3 H H OCH2CH3 H CH3 CH3 H H OCH2CH3 H OCH3 CH3 H H OCH2CH3 H OCH3 OCH H CH3 OCH2CH3 H OCH3 CH3 6-OCH3 H OCH2CH3 H OCH3 OCH3 H H OCH3 Cl OCH3 CH3 H H OCH3 Cl OCH3 OCH3 6-Cl H OCH3 Cl OCH3 CH3 H H OCH3 Cl OCH3 OCH3 H H OCH2CH3 Cl OCH3 CH3 H CH3 OCH2CH3 Cl OCH3 OCH3 H H OCH3 OCH3 CH3 CH3 H H OCH3 OCH3 OCH3 CH3 H H OCH3 OCH3 OCH3 OCH3 H CH3 OCH3 OCH3 OCH3 CH3 Table XVI II (continued) R2 R3 R9 R11 X Y m.p. ( C) 6-OCH3 H OCH3 OCH3 OCH3 OCH3 H H OCH2CH3 OCH3 OCH3 CH3 H CH3 OCH2CH3 OCH3 OCH3 OCH3 Table XIX EMI121.1 R2 R3 R9 X Y m.p. ( C) H H OCH3 CH3 CH3 H H OCH3 OCH3 CH3 H H OCH3 OCH3 OCH3 H H OCH3 Cl OCH3 H H OCH3 OCF2H CH3 H CH3 OCH3 OCH3 CH3 H CH3 OCH3 OCH3 OCH@ 6-OCH3 H OCH3 OCH3 CH3 3-Cl H OCH3 OCH3 OCH3 3-OCH3 CH3 OCH3 OCH3 CH3 H H OCH2CH3 CH3 CH3 H H OCH2CH3 OCH3 CH3 H H OCH2CH3 OCH3 OCH3 H H OCH2CH3 Cl OCH3 H CH3 OCH2CH3 OCH3 CH3 6-OCH3 H OCH2CH3 OCH3 OCH3 Table XX EMI122.1 R2 R3 R9 X Y m.p. ( C) H H OCH3 CH3 CH3 H H OCH3 OCH3 CH3 H H OCH3 OCH3 OCH3 H H OCH3 OCF2H CH3 H CH3 OCH3 OCH3 CH3 H CH3 OCH3 OCH3 OCH3 6-OCH3 H OCH3 OCH3 CH3 3-C1 H OCH3 OCH3 OCH3 3-OCH3 CH3 OCH3 OCH3 CH3 H H OCH2CH3 CH3 CH3 H H OCH2CH3 OCH3 CH3 H H OCH2CH3 OCH3 OCH3 H CH3 OCH2CH3 OCH3 CH3 6-OCH3 H OCH2CH3 OCH3 OCH3 Table XXI EMI123.1 R2 R3 N R11 X Y Z m.p. ( C) H H O H CH3 CH3 CH H H O H OCH3 CH3 CH 176-1800(d) H H O H OCH3 OCH3 CH 176-177 H H O H CH3 CH3 N H H O H OCH3 CH3 N H H O H OCH3 OCH3 N H H O H Cl OCH3 CH 6-C1 H O H OCH3 CH3 CH 6-OCH3 H O H OCH3 OCH3 N 3-CF3 H O H OCH3 CH3 N 4-CH3 H O H OCH3 CH3 CH H H O Cl OCH3 CH3 CH H H O OCH3 OCH3 OCH3 CH H H 1 H CH3 CH3 N H H 1 H OCH3 CH3 CH H H 1 H OCH3 OCH3 CH H H 1 H Cl OCH3 CH H H 1 H OCF2H CH3 N H H 1 H OCH3 OCH3 CH H H 1 H OCH3 CH3 N 6-OCH3 H 1 H OCH3 CH3 N 6-F H 1 H OCH3 OCH3 N 3-C1 H 1 H OCH3 CH3 CH 3-OCH3 H 1 H OCH3 CH3 CH Table XXI (continued) R2 R3 n R11 X Y Z m.p. ( C) H CH3 O H OCH3 OCH3 CH 3-OCH3 CH3 O H Cl OCH3 CH H CH3 1 H OCH3 CH3 N H CH3 1 H OCH3 OCH3 CH 3-Cl CH3 1 H OCF2H CH3 CH Table XXII EMI125.1 R2 R3 n R11 X Y Z m.p. ( C) H H O H CH3 CH3 CH H H O H OCH3 CH3 N H H O H OCH3 OCH3 N H H O H OCF2H CH3 CH 6-C1 H O H OCH'3 CH3 CH 6-OCH3 H O H OCH3 OCH3 N 3-CF3 H O H OCH3 CH3 N 4-CH3 H O H OCH3 OCH3 CH H H O Cl OCH3 CH3 CH H H O CH3 OCH3 OCH- N H H 1 H CH3 CH3 CH H H 1 H OCH3 CH3 CH H H 1 H OCH3 OCH3 N H H 1 H OCF2H CH3 N 6-OCH3 H 1 H OCH3 CH3 N 6-F H 1 H OCH3 OCH3 N 3-C1 H 1 H OCH3 CH3 CH 3-OCH3 H 1 H OCH3 CH3 CH H CH3 O H OCH3 OCH3 N 3-OCH3 CH3 O H OCH3 OCH3 CH H CH3 1 H OCH3 CH3 N H CH3 1 H OCH3 OCH3 N 3-Cl CH3 1 H OCF2H CH3 CH Table XXIII EMI126.1 R R2 R3 n R11 X Y m.p. ( C) H H O H CH3 CH3 H H O H OCH3 CH3 H H O H OCH3 OCH3 H H O H Cl OCH3 H H O H OCF2H CH3 6-C1 H O H OCH3 CH3 6-OCH3 H O H OCH OCH3 3-CF3 H O H OCH3 CH3 4-CH3 H O H OCH3 OCH3 H H O H OCH3 CH3 H H O H Cl OCH3 H H O CH3 CH3 CH3 H H O Cl OCH3 CH3 H H O CH3 OCH3 OCH3 H H O CH3 Cl OCH3 H H O CH3 OCF2H CH3 H H O OCH3 OCH3 CH3 H H O CH3 OCH3 OCH3 6-OCH3 H 0 CH3 OCH3 CH3 6-Cl H O CH3 OCH3 OCH3 3-Cl H O CH3 OCH3 CH3 H H 1 H CH3 CH3 H H 1 H OCH3 OCH3 H H 1 H OCH3 OCH3 Table XXIII (continued) R2 R3 n R11 X Y m.p. ( C) H H 1 H Cl OCH3 H H 1 H OCF2H CH3 H H 1 H OCH3 OCH3 H H 1 H OCH3 CH3 6-OCH3 H 1 H OCH3 CH3 6-F H 1 H OCH3 OCH3 3-C1 H 1 H OCH3 CH3 3-OCH3 H 1 H OCH3 CH3 H CH3 O H OCH3 OCH3 H CH3 O CH3 OCH3 CH3 3-OCH3 CH3 O H Cl OCH3 H CH3 1 H OCH3 CH3 H CH3 1 H OCH3 OCH3 3-Cl CH3 1 H OCF2H CH3 Table XXIV EMI128.1 R2 R3 n R11 X Y m.p. (0 C) H H O H CH3 CH H H O H OCH3 CH- H H O H OCH3 OCH3 H H O H OCF2H CH3 6-C1 H O H OCH3 CH3 6-OCH3 H O H OCH3 OCH3 3-CF3 H O H OCH3 CH3 4-CH3 H O H OCH3 OCH3 H H O H OCH3 CH3 H H O CH3 CH3 CH3 H H O Cl OCH3 CH3 H H O CH3 OCH3 OCH3 H H O CH3 OCF2H CH3 H H O OCH3 OCH3 CH3 H H O CH3 OCH3 OCH3 6-OCH3 H O CH3 OCH3 CH3 6-C1 H O CH3 OCH3 OCH3 3-Cl H O CH3 OCH3 CH3 H H 1 H CH3 CH3 H H 1 H OCH3 CH3 H H 1 H OCH3 OCH3 H H 1 H OCF2H CH3 H H 1 H OCH3 OCH3 H H 1 H OCH3 CH3 Table XXIV (continued) R2 R3 n R11 X Y m.p. ( C) 6-OCH3 H 1 H OCH3 CH3 6-F H 1 H OCH3 OCH3 3-C1 H 1 H OCH3 CH3 3-OCH3 H 1 H OCH3 CH3 H CH3 O H OCH3 OCH3 H CH3 O CH3 OCH3 CH3 H CH3 1 H OCH3 CH3 H CH3 1 H OCH3 OCH3 3-Cl CH3 1 H OCF2H CH3 Table XXV EMI130.1 R1 R2 R3 X Y m.p. ( C) CHClCH2Cl H H OCH3 CH3 CHClCH2Cl H CH3 OCH3 OCH3 CHClCH2C1 6-C1 H OCH3 CH3 CHClCHC12 H H OCH3 CH3 CHClCHCl2 H H OCH3 OCH3 CHClCHC12 H CH3 OCH3 CH3 CH=CBr2 H H OCH3 CH3 CH=CBr2 H H OCH3 OCH3 CH=CBr2 H CH3 OCH3 CH3 CH=CF2 H H OCH3 CH3 CH=CF2 6-OCH3 H OCH3 OCH3 CH=CF2 H H OCH3 OCH3 CH=CHOCH3 H H OCH3 CH3 CH=CHOCH3 H H OCH3 OCH3 CH=CHOCH3 H CH3 OCH3 CH3 CH=CHOCH2CH3 H H OCH3 CH3 CH=CHOCH2CH3 H H OCH3 OCH3 CH=CHCO2CH3 H H OCH3 CH3 CH=CHCO2CH3 H- H OCH3 OCH CH=CHCO2CH3 H CH3 OCH3 CH3 Table XXVI EMI131.1 R1 R2 R3 X Y m.p. ( C) CHClCH2Cl H H OCH3 CH3 CHClCH2Cl H CH3 OCH3 OCH3 CHClCH2C1 6-C1 H OCH3 CH3 CHClCHC12 H H OCH3 CH3 CHClCHCl2 H H OCH3 OCH3 CHClCHCl2 H CH3 OCH3 CH3 CH=C3r2 H H OCH3 CH3 CH=CBr2 H H OCH3 OCH3 CH=CBr2 H CH3 OCH3 CH3 CH=CF2 H H OCH3 CH3 CH=CF2 6-OCH3 H OCH3 OCH3 CH=CF2 H H OCH3 OCH3 CH=CHOCH3 H H OCH3 CH3 CH=CHOCH3 H H OCH3 OCH3 CH=CHOCH3 H CH3 OCH3 CH3 CH=CHOCH2CH3 H H OCH3 CH3 CH=CHOCH2CH3 H H OCH3 OCH3 CH=CHCO2CH3 H H OCH3 CH3 CH=CHC02CH3 H H OCH3 OCH3 CH=CHC02CH3 H CH3 OCH3 CH3 Table XXVII EMI132.1 R1 R2 R3 X1 Y1 m.p. ( C) CH2CH2F H H CH2 H CH2CH2F H H CH2 CH3 CH2CH2F H H CH2 OCH3 CH2CH2F H H CH2 Cl CH2CH2Br H H O H CH2CH2Br H H O CH3 CH2CH2Cl H H O OCH3 CH2CH2Cl H H O Cl CH2CH2C1 H CH3 O OCH3 CH2CH2C1 6-C1 H O CH3 CH2CH2C1 3-OCH3 CH3 O CH3 CH2CH2OC(O)CH3 H H CH2 Cl CH2CH2OC(O)CF3 H H O OCH3 CH2CH20H H H O Cl CH2CH20H H H O OCH3 CH2CH2OH H CH3 CH2 OCH3 CH2CH20H 6-OCH3 H O OCH3 CH2CH2OCH2C6H5 H H O Cl CH2CH2OSO2CH3 H CH3 CH2 OCH3 CH2CH2OSO2-4-C6H4CH3 H H O OCH3 CH2CH2SCH3 H H O H CH2CH2S(O)2CH3 H H O OCH3 CH2CH2OSO2N(CH3)2 H H CH2 Cl CH2CH2CO2CH3 H H O OCH3 CH2CH2OCH3 H H O OCH3 Table XXVII (continued) EMI133.1 <tb> R, <SEP> R2 <SEP> 3 <SEP> X1 <SEP> Y1 <SEP> m.p <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> O <SEP> Cl <tb> CH2CH20CH3 <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH2CH20CH3 <SEP> 6-C1 <SEP> H <SEP> 0 <SEP> CH3 <tb> CH2CH20CH3 <SEP> 3-OCH3 <SEP> CH3 <SEP> 0 <SEP> C1 <tb> CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH(OCH3)CH2(0CH3) <SEP> 6-OCH3 <SEP> H <SEP> O <SEP> CH3 <tb> CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> CH2 <SEP> C1 <tb> CH(OCH2CH3)CH2(OCH2CH3) <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH2CH(0CH3)2 <SEP> H <SEP> H <SEP> <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> O <SEP> Cl <tb> CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH2CH(OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> CH2 <SEP> H <tb> CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> CH2 <SEP> C1 <tb> CH(OCH3)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH(C1)CH(OCH3)2 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH(C1)CH( <SEP> OCH; ;2 <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH(Cl)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> <SEP> '2 <SEP> c <tb> CH2 <SEP> < <SEP> O <SEP> j <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH2 <SEP> H <SEP> H <SEP> H <SEP> CH2 <SEP> C1 <tb> <SEP> ,7 <SEP> 1 <tb> CH <SEP> < <SEP> ) <SEP> H <SEP> O <SEP> O <SEP> C1 <tb> C1 <tb> CH <SEP> X <SEP> O <SEP> 9 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> OCH3 <tb> Table XXVII (continued) EMI134.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X1 <SEP> V1 <SEP> m.p.(0C) <tb> C <SEP> H < 0 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <tb> C1 <tb> <SEP> CH3 <tb> CH2(o <SEP> T <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> <SEP> O+H <tb> CH < <SEP> J <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> C1 <tb> g WCH3 <SEP> H <SEP> H <SEP> O <SEP> CH3 <tb> SOCH, <tb> <SEP> o <tb> C <SEP> 24 <SEP> ) <SEP> H <SEP> H <SEP> <SEP> OCH3 <tb> <SEP> 0 <tb> CHO <SEP> ) <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH-( <SEP> L <tb> <SEP> o <tb> C <SEP> ) <SEP> H <SEP> H <SEP> O <SEP> CH3 <tb> OCH3 <SEP> 0 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CHClCHCl2 <SEP> H <SEP> H <SEP> H2 <SEP> C1 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH=CBr2 <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> CH:CF2 <SEP> H <SEP> H <SEP> O <SEP> CH3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> <SEP> OCH3 <tb> CH:CH(0CH3) <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> Table XXVII (continued) R1 R2 R3 X1 Y1 m.p. ( C) CH=CH(OCH2CH3) H H CH2 OCH3 CH=CHCO2CH3 H H O OCH3 Table XXVII I EMI136.1 R1 R2 R3 X1 Y1 m.p. ( C) CH2CH2CH2F H H CH2 H CH2CH2CH2F H H CH2 CH3 CH2CH2CH2F H H CH2 OCH3 CH2CH2CH2F H H CH2 Cl CH2CH2CH2Br H H O H CH2CH2CH2Br H H O CH3 CH2CH2CH2Cl H H O -OCH3 CH2CH2CH2C1 H H O Cl CH2CH2CH2Cl H CH3 O OCH3 CH2CH2CH2Cl 6-Cl H O CH3 CH2CH2CH2Cl 3-OCH3 CH3 O CH3 CH2CH2CH2OC(O)CH3 H H CH2 Cl CH2CH2CH2OC(O)CF3 H H O OCH3 CH2CH2CH2OH H H O Cl CH2CH2CH2 H H H O OCH3 CH2CH2CH2OH H CH2 CH2 OCH3 CH2CH2CH2OH 6-OCH3 H O OCH3 CH2CH2CH2OCH2C6H5 H H O Cl CH2CH2CH2OSO2CH3 H CH3 CH2 OCH3 CH2CH2CH2OSO2-4-C6H4CH3 H H O OCH3 CH2CH2CH2SCH3 H H O H CH2CH2CH2S(O)2CH3 H H O OCH3 CH2CH2CH2OSO2N(CH3)2 H H CH2 Cl CH2CH2CH2CO2CH3 H H O OCH3 CH2CH2CH2OCH3 H H O OCH3 Table XXVIII (continued) EMI137.1 R1 <SEP> R2 <SEP> R3 <SEP> X1 <SEP> Y1 <SEP> m.p. <tb> R1 <SEP> R, <SEP> R3 <SEP> X1 <SEP> Y1 <SEP> ( <SEP> (oc) <tb> CH2CH2CH20CH3 <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH2CH2CH2OCH3 <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH2CH2CH2OCH3 <SEP> 6-Cl <SEP> H <SEP> 0 <SEP> CH3 <tb> CH2CH2CH2OCH3 <SEP> 3-OCH3 <SEP> CH3 <SEP> 0 <SEP> C1 <tb> CH2CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> <SEP> OCH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH2CH(0CH3)CH2(OCH3) <SEP> 6-OCH3 <SEP> H <SEP> O <SEP> CH3 <tb> 2CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> CH2 <SEP> C1 <tb> CH2CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> CH2CH2CH(oCH3)2 <SEP> H <SEP> H <SEP> O <SEP> CH3 <tb> CH2CH2CH( <SEP> OCH3 <SEP> )2 <SEP> H <SEP> H <SEP> O <SEP> C1 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> O <SEP> OCH3 <tb> CH2CH2CH( <SEP> OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> CH2 <SEP> H <tb> CH2CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> o <SEP> C1 <tb> <SEP> L <SEP> L <tb> CH2CH2 < <SEP> 3 <SEP> H <SEP> H <SEP> O <SEP> OCH3 <tb> <SEP> o <tb> CH2CH2 <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> CH2 <SEP> C1 <tb> CH2CH2 <SEP> (o <SEP> WCH3 <SEP> H <SEP> H <SEP> CH2 <SEP> OCH3 <tb> <SEP> 0 <tb> CH2CH2- < <SEP> H <SEP> H <SEP> H <SEP> <SEP> OCH3 <tb> <SEP> o <tb> Table XXIX EMI138.1 R1 R2 R3 Y1 m.p. ( C) CH2CH2F H H H CH2CH2F H H CH3 CH2CH2F H H OCH3 CH2CH2F H H Cl CH2CH2Br H H H CH2CH2Br H H CH3 CH2CH2C1 H H OCH3 CH2CH2Cl H H Cl CH2CH2C1 H CH3 OCH3 CH2CH2Cl 6-C1 H CH3 CH2CH2C1 3-OCH3 CH3 CH3 CH2CH2OC(O)CH3 H H Cl CH2CH2OC(O)CF3 H H OCH3 CH2CH2OH H H Cl CH2CH20H H H OCH3 CH2CH2OH H CH3 OCH3 CH2CH2OH 6-OCH3 H OCH3 CH2CH2OCH2C6H5 H H Cl CH2CH20S02CH3 H CH3 OCH3 CH2CH2OSO2-4-C6H4CH3 H H OCH3 CH2CH2SCH3 H H H CH2CH2S(0)2CH3 H H OCH3 CH2CH2OSO2N(CH3)2 H H Cl CH2CH2CO2CH3 H H OCH3 CH2CH2OCH3 H H OCH3 Table XXIX (continued) EMI139.1 <tb> <SEP> R1 <SEP> R2 <SEP> R3 <SEP> Y1 <SEP> m.p. <tb> <SEP> (0C) <tb> <SEP> CH2CH20CH3 <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH2CH20CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> CH2CH20CH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <tb> <SEP> CH2CH2OCH3 <SEP> 3-OCH3 <SEP> CH3 <SEP> C1 <tb> <SEP> CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH(OCH3)CH2(OCH3) <SEP> H <SEP> CH3 <SEP> OCH3 <tb> .CH(OCH3)CH2(OCH3) <SEP> 6-OCH3 <SEP> H <SEP> CH3 <tb> <SEP> CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> CH2CH(OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> H <tb> <SEP> CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> C1 <tb> <SEP> CH(OCH3)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH(Cl)CH(OCH3 <SEP> 2 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH(C1)CH(OCH3)2 <SEP> H <SEP> H <SEP> C1 <tb> <SEP> CH(C1)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CHLCH <tb> <SEP> H <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH2 < ) <SEP> H <SEP> H <SEP> Cl <tb> <SEP> L <tb> <SEP> o <tb> <SEP> CH-(D <SEP> H <SEP> H <SEP> C1 <tb> <SEP> C1 <tb> <SEP> 0 <tb> <SEP> cH-(o <SEP> H <SEP> H <SEP> OCH, <tb> <SEP> OCH30 <tb> Table XXIX (continued) EMI140.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> Y1 <SEP> m.p.( C) <tb> <SEP> L <SEP> '1 <tb> CH3 <SEP> < 0 <SEP> j <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> ^rCH3 <tb> CH(0T <SEP> H <SEP> H <SEP> CHy <tb> C1 <SEP> o <tb> <SEP> OCH <tb> OCH30 <tb> <SEP> 3 <tb> CH2 <SEP> < <SEP> ) <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> 0 <tb> <SEP> 0 <tb> SH( <SEP> H <SEP> H <SEP> ci <tb> C1 <SEP> H <SEP> H <SEP> Cl <tb> <SEP> o <tb> CH <SEP> H <SEP> H <SEP> CH, <tb> OCH3 <SEP> 0 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> OCH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> C1 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> C1 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CBr2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CF2 <SEP> H <SEP> H <SEP> CK3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> Cl <tb> CH=CH(OCH2CH) <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CHCO2CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> Table XXX EMI141.1 R1 R2 R3 V1 m.p. ( C) CH2CH2CH2F H H H CH2CH2CH2F H H CH3 CH2CH2CH2F H H OCH3 CH2CH2CH2F H H Cl CH2CH2CH2Br H H H CH2CH2CH2Br H H CH3 CH2CH2CH2C1 H H OCH3 CH2CH2CH2C1 H H Cl CH2CH2CH2C1 H CH3 OCH3 CH2CH2CH2C1 6-C1 H CH3 CH2CH2CH2C1 3-OCH3 CH3 CH3 CH2CH2CH2OC(O)CH3 H H Cl CH2CH2CH2OC(O)CF3 H H OCH3 CH2CH2CH2OH H H Cl CH2CH2CH2OH H H OCH3 CH2CH2CH2OH H CH3 OCH3 CH2CH2CH2OH 6-OCH3 H OCH3 CH2CH2CH2OCH2C6H5 H H Cl CH2CH2CH2OSO2CH3 H CH3 OCH3 CH2CH2CH2OSO2-4-C6H4CH3 H H OCH3 CH2CH2CH2SCH3 H H H CH2CH2CH2S(O)2CH3 H H OCH3 CH2CH2CH2OSO2N(CH3)2 H H Cl CH2CH2CH2C02CH3 H H OCH3 CH2CH2CH2OCH3 H H OCH3 Table XXX (continued) EMI142.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> Y1 <SEP> m.p. <tb> <SEP> (0C) <tb> CH2CH2CH2OCH3 <SEP> H <SEP> H <SEP> Cl <tb> CH2CH2CH20CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH2CH20CH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <tb> CH2CH2CH2OCH3 <SEP> 3 <SEP> OCH3 <SEP> CH3 <SEP> C1 <tb> CH2CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> C1 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> 6-OCH3 <SEP> H <SEP> CH3 <tb> CH2CH(OCH2CH3)CH2(OCH2CH3) <SEP> H <SEP> H <SEP> C1 <tb> CH2CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> C1 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH2CH(OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> H <tb> CH2CH2CH(0CH2CH3)2 <SEP> H <SEP> H <SEP> C1 <tb> <SEP> o <tb> CH2CH2" < <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> o <tb> CH2CH2 <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> Cl <tb> <SEP> L <tb> CH2CH2 < 00 <SEP> CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> o <tb> CH2CH2- <SEP> H <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> o <tb> Table XXXI EMI143.1 R1 R2 R3 X2 Y2 m.p. ( C) CH2CH2F H H H3 CH3 CH2CH2F H H CH3 CH2CH3 CH2CH2F H H CH3 CH2CF3 CH2CH2F H H OCH3 CH3 CH2CH2Br H H OCH3 CH2CH3 CH2CH2Br H H OCH3 CH2CF3 CH2CH2C1 H H OCH3 CH3 CH2CH2Cl H H OCH3 CH2CH3 CH2CH2Cl H CH2 SCH3 CH3 CH2CH2Cl 6-Cl H SCH3 CH2CH3 CH2CH2Cl 3-OCH3 CH3 SCH3 CH2CF3 CH2CH20C(0)CH3 H H OCH3 CH3 CH2CH2OC(O)CF3 H H SCH3 CH3 CH2CH2OH H H OCH3 CH2CH3 CH2CH2OH H H OCH3 CH2CF3 CH2CH2OH H CH3 OCH3 CH3 CH2CH2OH 6-OCH3 H CH3 CH3 CH2CH2OCH2C6H5 H H CH3 CH2CH3 CH2CH2OSO2CH3 H CH3 CH3 CH2CF3 CH2CH2OSO2-4-C6H4CH3 H H OCH3 CH3 CH2CH2SCH3 H H SCH3 CH@ CH2CH2S(O)2CH3 H H CH3 CH3 CH2CH2OSO2N(CH3)2 H H OCH3 CH3 CH2CH2CO2CH3 H H CH3 CH3 CH2CH2OCH3 H H CH3 CH3 Table XXXI (continued) EMI144.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X2 <SEP> V2 <SEP> m.p. <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH20CH3 <SEP> H <SEP> CH3 <SEP> SCH3 <SEP> CH3 <tb> CH2CH20CH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH20CH3 <SEP> 3-OCH3 <SEP> CH3 <SEP> OCH3 <SEP> CH3 <tb> CH2CH2OCH2CH3 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH2CF3 <tb> CH(OCH3)CH2(OCH3) <SEP> 6-OCH3 <SEP> H. <SEP> OCH3 <SEP> CH3 <tb> CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> SCH3 <SEP> CH2CH3 <tb> CH(OCH2CH3)CH2(OCH2CH3) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> SCH3 <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH3 <tb> CH(OCH3)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> CH(C1)CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH(C1)CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH(Cl)CHcOCH2CH3)2 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> <SEP> o <tb> CH2 <SEP> < <SEP> O <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> o <tb> CH2 <tb> <SEP> tt <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> Cl <tb> CH0 <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> OCH <tb> Table XXXI (continued) EMI145.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X2 <SEP> V2 <SEP> m.p.(0C) <tb> <SEP> 1 <SEP> 2 <tb> CH2 < 0OCh3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> o <SEP> CH3 <tb> CH < : :CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> <SEP> O <SEP> CHg <SEP> H <SEP> H <SEP> CH, <SEP> CH, <tb> C, <SEP> HYO0CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> OCH3, <tb> <SEP> 0 <tb> CH, <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> o <tb> <SEP> 0 <tb> c,T > <SEP> H <SEP> H <SEP> CH3 <SEP> C <SEP> H2CH3 <tb> <SEP> 0 <tb> Chit <SEP> ) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> OCH, <SEP> O <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH2CH3 <tb> CH=CBr2 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH2CH3 <tb> CH=CF2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH=CH(0CH3) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH=CH(OCH2CH3) <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH=CHCO2CH3 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> Table XXXI I EMI146.1 R1 R2 R3 X2 Y2 m.p. ( C). CH2CH2CH2F H H CH3 CH3 CH2CH2CH2F H H CH3 CH2CH3 CH2CH2CH2F H H CH3 CH2CF3 CH2CH2CH2F H H OCH3 CH3 CH2CH2CH2Br H H OCH3 CH2CH3 CH2CH2CH2Br H H OCH3 CH2CF3 CH2CH2CH2Cl H H OCH3 CH3 CH2CH2CH2C1 H H OCH3 CH2CH3 CH2CH2CH2Cl H CH3 SCH3 CH3 CH2CH2CH2C1 6-C1 H SCH3 CH2CH3 CH2CH2CH2Cl OCH3 CH3 SCH3 CH2CF3 CH2CH2CH2OC(O)CH3 H H OCH3 CH3 CH2CH2CH2OC(O)CH3 H H SCH3 CH3 CH2CH2CH2OH H H OCH3 CH2CH3 CH2CH2CH2OH H H OCH3 CH2CF3 CH2CH2CH2OH H CH3 OCH3 CH3 CH2CH2CH2OH 6-OCH3 H CH3 CH3 CH2CH2CH2OCH2C6H5 H H CH3 CH2CH3 CH2CH2CH2OSO2CH3 H CH3 CH3 CH2CF3 CH2CH2CH2OSO2-4-C6H4CH3 H H OCH3 CH3 CH2CH2CH2SCH3 H H SCH3 CH3 CH2CH2CH2s(0)2CH3 H H CH3 CH3 CH2CH2CH20S02N(CH3)2 H H OCH3 CH3 CH2CH2CH2CO2CH3 H H CH3 CH3 CH2CH2CH20CH3 H H CH3 CH3 Table XXXII (continued) EMI147.1 Ri <SEP> R2 <SEP> R3 <SEP> X2 <SEP> V2 <SEP> m.p. <tb> L,2 <SEP> L <SEP> (OC) <tb> CH2CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH2CH20CH3 <SEP> H <SEP> CH3 <SEP> SCH3 <SEP> CH3 <tb> CCH2CH2OCH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH2CH20CH3 <SEP> 3-OCH) <SEP> CH3 <SEP> OCH3 <SEP> CH3 <tb> CH2CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> CH2CH(CCH3)CH2(CCH3) <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH(OCH3)cH2(OCH3) <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH(0CH3)CH2(oCH3) <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH2CF3 <tb> CH2CH(OCH3)CH2(OCH3) <SEP> 6-OCH3 <SEP> H <SEP> OCH3 <SEP> CH3 <tb> ChCHC0CH2CH3)CH2( <SEP> DCH2CH3) <SEP> H <SEP> H <SEP> SCH3 <SEP> CH2CH3 <tb> CH2CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> OCH7 <SEP> .CH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> CH2CH2CH(OCH)2 <SEP> H <SEP> CH3 <SEP> SCH3 <SEP> CH3 <tb> CH2CH2CH(OSH3)2 <SEP> 6-CF3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> CH2CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> <SEP> 3 <tb> CH2CH2 <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> H <SEP> < <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <tb> <SEP> o <SEP> ct <tb> CC <SEP> KO <SEP> J <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> o <tb> H <SEP> H <SEP> C <SEP> C <tb> <SEP> 0 <tb> CHClCC1 <SEP> H <SEP> H <SEP> SCH3 <SEP> CH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH3 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH <tb> CHClCHC12 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH2CH3 <tb> Table XXXIII EMI148.1 R1 R2 R3 X3 m.p. ( C) CH2CH2F H H CH3 CH2CH2F H H OCH3 CH2CH2Br H H CH3 CH2CH2C1 H H OCH3 CH2CH2Cl H CH3 OCH3 CH2CH2C1 6-C1 H CH3 CH2CH2Cl 3-OCH3 CH3 CH3 CH2CH2OC(O)CH3 H H CH3 CH2CH2QC(O)CF3 H H OCH3 CH2CH2OH H H CH3 CH2CH2OH H H OCH3 CH2CH20H H CH3 OCH3 CH2CH2OH 6-OCH3 H OCH3 CH2CH2OCH2C6H5 H H CH3 CH2CH2OSO2CH3 H CH3 OCH3 CH2CH2OSO2-4-C6H4 CH3 H H OCH3 CH2CH2SCH3 H H CH3 CH2CH2S(O)2CH3 H H OCH3 CH2CH2OSO2N(CH3)2 H H CH3 CH2CH2CO2CH3 H H OCH3 CH2CH20CH3 H H OCH3 CH2CH2OCH3 H H CH3 CH2CH2OCH3 H CH3 OCH3 CH2CH2OCH3 6-Cl H CH3 CH2CH2OCH3 3-OCH3 CH3 CH3 Table XXXIII (continued) EMI149.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X3 <SEP> m.p.( C) <tb> CH2CH2OC <SEP> H2CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH(0CH3)CH2(OCH3) <SEP> H <SEP> H <SEP> CH3 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH(OCH3)CH2(0CH3) <SEP> 6-OCH3 <SEP> H <SEP> CH3 <tb> CH(0CH2CH3)CH2(OCH2CH3) <SEP> H <SEP> H <SEP> CH3 <tb> CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH(OCH3)2 <SEP> 6- <SEP> CF3 <SEP> H <SEP> OCH3 <tb> CH2CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH(OCH3)CH( <SEP> OCH3 <SEP> )2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH(OCH3)CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH(OCH3)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH(Cl)CH(oCH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH(C1)CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH(C1)CH(OCH2CH3)2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH2 < 00 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> 0¯, <tb> CH2 < 00) <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> Oy <tb> CHX <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> C1 <tb> C <SEP> < <SEP> 9 <SEP> H <SEP> H <SEP> OCH3 <tb> OCH <tb> <SEP> 3 <tb> CH2(o <SEP> CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> CH2 < 0 <SEP> W <SEP> H <SEP> H <SEP> OCH3 <tb> Table XXXIII (continued) EMI150.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X3 <SEP> m.p.( O) <tb> <SEP> O <SEP> > - <SEP> CH3 <tb> C1 <SEP> H0 <SEP> H <SEP> H <SEP> CH3 <tb> OCH3 <tb> CC1Hl < OOCH3 <SEP> H <SEP> H <SEP> OCH3 <tb> t <tb> <SEP> 0 <tb> CH2 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> 0 <tb> CHK <SEP> ) <SEP> H <SEP> H <SEP> CH3 <tb> C1 <SEP> <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> OCH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <tb> CHClCHCl2 <SEP> H <SEP> H <SEP> OCH3 <tb> CHClCHC12 <SEP> H <SEP> H <SEP> CH3 <tb> CH=CBr2 <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CF2 <SEP> H <SEP> H <SEP> CH3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CH(OCH3) <SEP> H <SEP> H <SEP> CH3 <tb> CH=CH( <SEP> OCH2CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH=CHC02CHa <SEP> H <SEP> H <SEP> OCH3 <tb> Table XXXI V EMI151.1 R1 R2 R3 X3 m.p. ( C) CH2CH2CH2F H H CH3 CH2CH2CH2F H H OCH3 CH2CH2CH2Br H H CH3 CH2CH2CH2Cl H H OCH3 CH2CH2CH2Cl H CH3 OCH3 CH2CH2CH2Cl 6-Cl H CH3 CH2CH2CH2C1 3-OCH3 CH3 CH3 CH2CH2CH2OC(O)CH3 H H CH3 CH2CH2CH20C(0)CF3 H H OCH3 CH2CH2CH2OH H H CH3 CH2CH2CH2OH H H OCH3 CH2CH2CH2OH H CH3 OCH3 CH2CH2CH2OH 6-OCH3 H OCH3 CH2CH2CH2OCH2C6H5 H H CH3 CH2CH2CH2OSO2CH3 H CH3 OCH3 CH2CH2CH2OSO2-4-C6H4CH3 H H OCH3 CH2CH2CH2SCH3 H H CH3 CH2CH2CH2S(O)CH3 H H OCH3 CH2CH2CH2OSO2N(CH3)2 H H CH3 CH2CH2CH2CO2CH3 H H OCH3 CH2CH2CH2OCH3 H H OCH3 CH2CH2CH2OCH3 H H CH3 CH2CH2CH2OCH3 H CH3 OCH3 CH2CH2CH20CH3 6-C1 H CH3 CH2CH2CH2OCH3 3-OCH3 CH3 CH3 Table XXXIV (continued) EMI152.1 R1 <SEP> R2 <SEP> R3 <SEP> X3 <SEP> m.p. <tb> R1 <SEP> R2 <SEP> R3 <SEP> X3 <SEP> (oC <tb> CH2CH2CH20CH2CH3 <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH(OCH33CH2(0CH3) <SEP> H <SEP> H <SEP> OCH3 <tb> CH2CH(OCH3)CH2(OCH7) <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH(OCH3)CH2(0CH3) <SEP> 6-OCH3 <SEP> H <SEP> CH3 <tb> CH2CH(OCH2CH3)CH2(0CH2CH3) <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH(OCH2CH3)CH2(OCH2CH3) <SEP> H <SEP> M <SEP> 0CM3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH2CH2CH(OCH3)2 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> CH2CH2CH(OCH3)2 <SEP> 6-CF3 <SEP> H <SEP> OCH3 <tb> CH2CH2CH(oCH2CH3)2 <SEP> H <SEP> H <SEP> CH3 <tb> CH <SEP> D <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> 0I <SEP> H <SEP> H <SEP> DCH3 <tb> C <SEP> H2 <SEP> CH2 <SEP> H <SEP> J <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 0 <tb> CH2CH2 <SEP> 40 <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> 70 <SEP> I <SEP> 5 <tb> CH2CH2 <SEP> < <SEP> ) <SEP> H <SEP> H <SEP> OCH3 <tb> Table XXXV EMI153.1 EMI153.2 R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> V <SEP> m. <SEP> p. <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> m <SEP> pi <tb> <SEP> 1 <SEP> L <SEP> X <SEP> Y <SEP> (oC) <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> H <tb> CM2CH2OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> NM2 <tb> CM2CH2OH <SEP> H <SEP> H <SEP> CH3 <SEP> NHCH3 <tb> CH2CH20C(O)CH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <SEP> N(CM3)2 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH2CH3 <tb> CH2CH(OCH3) <SEP> 2 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> CH2CF3 <tb> CH2 < 03 <SEP> H <SEP> H <SEP> CH3 <SEP> CH20CH3 <tb> <SEP> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> CH20CH2CH3 <tb> CH2CM2OCH3 <SEP> 6-OCH3 <SEP> H <SEP> CH3 <SEP> OCH2CH3 <tb> CH2CM2OH <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH2CH2CH3 <tb> CH2CH(0CM3)2 <SEP> H <SEP> H <SEP> CH2CHD <SEP> OCM2CH2CM2CM3 <tb> CH(0CH3)CH2(0CH3) <SEP> H <SEP> H <SEP> CH3 <SEP> SCH3 <tb> CH2"(D <SEP> | <SEP> H <SEP> H <SEP> CH3 <SEP> SCH2CH3 <tb> <SEP> CHClCM2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CHrCH2 <tb> CH2CH2C1 <SEP> 3-C1 <SEP> H <SEP> CH3 <SEP> OCH2CH=CHCM3 <tb> C <SEP> H2CH20CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2C-CH <tb> <SEP> CM2CH2OH <SEP> H <SEP> H <SEP> CH2CH3 <SEP> OCH2CH2C2CH <tb> <SEP> CH2CH20C(O)CF3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH2CH20CH3 <tb> <SEP> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> CH(OCH3)2 <tb> <SEP> /0s <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> CHo <tb> <SEP> '0 <tb> Table XXXV (continued) EMI154.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> ( <SEP> C; ; <tb> <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CF3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CM2F <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH2Cl <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH2Br <tb> CM2CH2OC(0)CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2H <tb> CH2CH20H <SEP> 6-C1 <SEP> H <SEP> CH3 <SEP> OCF2CHC1F <tb> <SEP> L <tb> CH,-H <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CHErF <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CF2H <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CHFCF3 <tb> CH(0CM3)CH2(0CH3) <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2H <tb> CH2CH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CHClF <tb> CH2CM2OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CHBrF <tb> CH2CH20H <SEP> H <SEP> H <SEP> CM3 <SEP> SCF2CF2H <tb> CH2CHt <SEP> OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CF2H <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> NHCH3 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <tb> CH <SEP> / <SEP> > <SEP> H <SEP> H <tb> <SEP> J <SEP> H <SEP> H <SEP> OCH3 <SEP> CCKZCF <tb> CH2CH2C1 <SEP> H <SEP> CH3 <SEP> OCH2CH3 <SEP> CH20CH3 <tb> CH2CH20CH3 <SEP> 3 <SEP> OCH3 <SEP> H <SEP> OCH3 <SEP> CH2OCH2CH3 <tb> CH2CH20C(O)CF3 <SEP> H <SEP> H <SEP> OCH3 <SEP> H2CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> SCH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2C <SEP> 3 <SEP> SCH2CH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH=CH2 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH2OCH3 <tb> CH2CH2OSO2N(CH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH(OOH3)2 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> Cj <SEP> 3 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CF3 <tb> Table XXXV (continued) EMI155.1 R1 <SEP> R2 <SEP> R3 <SEP> V <SEP> m.p <tb> R1 <SEP> R2 <SEP> R <SEP> X <SEP> Y <SEP> (0C) <tb> <SEP> 3 <SEP> (Oc) <tb> CM2 < 00) <SEP> H <SEP> H <SEP> OCH3 <SEP> ÛCH2CH2F <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH2C1 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCF2H <tb> CH2CH2OH <SEP> H <SEP> H <SEP> OCH3 <SEP> SCF2H <tb> CH(OCH3 <SEP> )CH2 <SEP> (OCH3 <SEP> ) <SEP> H <SEP> H <SEP> C1 <SEP> NH2 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> C1 <SEP> NHCH3 <tb> CH2CH20CH3 <SEP> 6-OCH3 <SEP> H <SEP> C1 <SEP> N(CH3)2 <tb> CH2CH2OSO2N(CH3)2 <SEP> H <SEP> H <SEP> C1 <SEP> CH3 <tb> CHClCH2Cl <SEP> M <SEP> H <SEP> C1 <SEP> OC <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> C1 <SEP> CCF2H <tb> CM2 <SEP> CH20C <SEP> H3 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> NHCH3 <tb> 2- < oD <SEP> H <SEP> H <SEP> CH2CM3 <SEP> N(CH3)2 <tb> CH2CH20H <SEP> H <SEP> CH3 <SEP> CH2CH3 <SEP> CH20CH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> SCH3 <tb> CM2CH2OCH3 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> CH(OCH3)2 <tb> CH2CH20H <SEP> H <SEP> H <SEP> CH2CH3 <SEP> C(0o <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> CH2CH3 <SEP> OCH2CF3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> OCF2H <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> NHCH3 <tb> CH2CH2OH <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> N(CH3)2 <tb> CH2CH20C(O)CF3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> CH2OCH3 <tb> CH2CH2SCH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> SCH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> CH(OCH3)2 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> OCH2CF3 <tb> CH(OCH3)CH2(OCH3) <SEP> H <SEP> H <SEP> OCH2CH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> OCF2H <tb> Table XXXV (continued) EMI156.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> m.p. <tb> 1 <SEP> 2 <SEP> (or) <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCF2M <SEP> N(CH3)2 <tb> CH2CH2OH <SEP> H <SEP> H <SEP> OCF2H <SEP> CH20CH3 <tb> CH2 <SEP> < <SEP> 9 <SEP> H <SEP> H <SEP> OCF2H <SEP> SCH3 <tb> CH2 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> OCF2H <SEP> CH(OCH3)2 <tb> <SEP> L <SEP> '2 <tb> CHC1CH2C1 <SEP> H <SEP> H <SEP> OCF <SEP> H <SEP> CH <tb> <SEP> 2 <SEP> 2 <SEP> 0¯ <tb> CH2CH2SCH3 <SEP> H <SEP> H <SEP> OCF2H <SEP> OCH2CF3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCF2H <SEP> OCF2H <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> Br <SEP> NM2 <tb> CM2CH2OCH3 <SEP> H <SEP> H <SEP> Br <SEP> OCH3 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> Br <SEP> CM3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> Br <SEP> OCF2H <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> F <SEP> NH2 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> F <SEP> OCH3 <tb> C2CH2ÛCH3 <SEP> H <SEP> H <SEP> F <SEP> CH3 <tb> Table XXXVI EMI157.1 EMI157.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> V <SEP> ( Cj <tb> <SEP> 3 <SEP> X <SEP> (oC) <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> H <tb> CH2CH20CH7 <SEP> H <SEP> H <SEP> CH3 <SEP> NH2 <tb> CH2CH2OH <SEP> H <SEP> H <SEP> CH3 <SEP> NHCH3 <tb> CH2CH20C(O)CH3 <SEP> 6-C1 <SEP> H <SEP> CH3 <SEP> N(CH3)2 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH2CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CM <SEP> 2CM3 <SEP> CH2CF3 <tb> n2(a, <SEP> H <SEP> H <SEP> CHg <SEP> CH,OCH, <tb> <SEP> H <SEP> H <SEP> CM3 <SEP> C <SEP> H20CH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> C <SEP> H2OCH2CH3 <tb> CH2CH20CH3 <SEP> 6-OCH3 <SEP> H <SEP> CH3 <SEP> 0CH2CH3 <tb> CH2CM2OH <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH2CH2CH3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> 0CM2CH2CH2CM3 <tb> CH(OCH7)CH2(0CH7) <SEP> H <SEP> H <SEP> CM3 <SEP> SCH3 <tb> H <SEP> H <SEP> CM3 <SEP> SCH2CH3 <tb> CHClCH2Cl <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH=CH2 <tb> CH2CH2C1 <SEP> 3-C1 <SEP> H <SEP> CH3 <SEP> OCH2CH=CHCH3 <tb> CH2CH2OCM3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CtCH <tb> CH2CM2OH <SEP> H <SEP> H <SEP> CH2CH3 <SEP> OCX2CH2CCH <tb> CH2CH20C(O)CF3 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> OCH2CH20CH3 <tb> CM2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH <SEP> CM(OCM3)2 <tb> CH=CHC1 <SEP> H <SEP> CM3 <SEP> CM3 <SEP> CH( CH2CH3)2 <tb> <SEP> /08 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH2CHD <SEP> CXO <tb> Table XXXVI (continued) EMI158.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> V <SEP> m.p. <tb> <SEP> (oC) <tb> CM2CH2OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCM2CF3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH2F <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH2C1 <tb> CH2CM2OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH2CH2Br <tb> CH2CH20C(O)CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2H <tb> CM2CM2OM <SEP> 6-Cl <SEP> H <SEP> CH3 <SEP> OCF2CHC1F <tb> CH2 <SEP> < 03 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CHBrF <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CF2H <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCF2CHFCF3 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2H <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CHC1F <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CHBrF <tb> CH2CH20H <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CF2H <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> SCF2CF2H <tb> CM2CH2Cl <SEP> H <SEP> H <SEP> OCH3 <SEP> NHCH3 <tb> CH2CH2OCH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <tb> CH2 <SEP> < D3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CCH2CF3 <tb> CH2CH2C1 <SEP> H <SEP> CH3 <SEP> OCH2CH3 <SEP> CH20CH3 <tb> CH2CH20CH3 <SEP> 3-OCH3 <SEP> H <SEP> OCH3 <SEP> CH20CH2CH3 <tb> CH2CH20C(O)CF3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CM3 <tb> CH2CH(OCH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> SCH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2CM3 <SEP> SCH2CH3 <tb> CH2CH2Cl <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH=CH2 <tb> CH2CM2OCH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH20CH3 <tb> CH2CH2oso2N(CH3)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH(OCH3)2 <tb> <SEP> L <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> CHo, <tb> CH2CM2OCH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCM2CF3 <tb> Table XXXVI (continued) EMI159.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> V <SEP> m <SEP> p <tb> <SEP> 3 <SEP> Y <SEP> (oC) <tb> H <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2 <SEP> H2 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH2C1 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCF2H <tb> CH2CM2OH <SEP> H <SEP> H <SEP> OCH3 <SEP> SCF2H <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> NHCH3 <tb> CH2 < 00 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> N(CH3)2 <tb> CH2CH20H <SEP> H <SEP> CH3 <SEP> CH2CH3 <SEP> CH20CH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> SCH3 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> CH2CH3 <SEP> CH(OCHs)2 <tb> CH2CM2OH <SEP> H <SEP> H <SEP> CH2CH3 <SEP> C: :J <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> CH2CH3 <SEP> OCH2CF3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> CM <SEP> 2CM3 <SEP> OCF2M <tb> CH2C <SEP> M2OCH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> NHCH3 <tb> CH2CH20H <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> N(CH3 > 2 <tb> CH2CH20C(O <SEP> )CF3 <SEP> H <SEP> H <SEP> 2C <SEP> 3 <SEP> CH20CH3 <tb> CH2C <SEP> 2sCH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> SCH3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> CH(OCH3)2 <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> OCH2CF3 <tb> CH(OCH3)CH2(0CH3) <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> C(Oo <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> OCF2H <tb> CH2CH20CH3 <SEP> H <SEP> H <SEP> OCF2H <SEP> N(CM3)2 <tb> CH2CH20H <SEP> H <SEP> H <SEP> OCF2H <SEP> CH20CH3 <tb> <SEP> 0 <tb> CH2K0) <SEP> ) <SEP> H <SEP> H <SEP> OCF2H <SEP> SCH3 <tb> CH(OCH3)CH,(oCH3) <SEP> H <SEP> H <SEP> OCF2H <SEP> CM(OCH3)2 <tb> Table XXXVI (continued) EMI160.1 R1 <SEP> R2 <SEP> R3 <SEP> V <SEP> m.p. <tb> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> Y <SEP> ( C) <tb> CHClCH2C1 <SEP> H <SEP> H <SEP> OCF2H <SEP> CH0 <tb> CH2CH25CH3 <SEP> H <SEP> H <SEP> DCF2H <SEP> OCH2CF3 <tb> CH2CH2C1 <SEP> H <SEP> H <SEP> OCF2H <SEP> OCF2H <tb> Table XXXVII EMI161.1 EMI161.2 R1 <SEP> R2 <SEP> X <SEP> V <SEP> m.p. <tb> <SEP> Z <SEP> (0C) <tb> CH2CH2C1 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CCHD <tb> CH2CH20CH3 <SEP> 6-OCH3 <SEP> OCH3 <SEP> OCH3 <SEP> CCM3 <tb> CH2CH2C1 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CBr <tb> CH2 < 00) <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CBr <tb> CH2CH20CH3 <SEP> H <SEP> C1 <SEP> OCH3 <SEP> CC1 <tb> CH2CH2C1 <SEP> 3-C1 <SEP> CH3 <SEP> CH3 <SEP> CCl <tb> CH2CM20CH3 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CF <tb> 2 <SEP> 1 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CF <tb> CH2CH2C1 <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CCM2CH3 <tb> CH2CH20CH3 <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CCH2CH3 <tb> Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, con tain about 0.1S to 99% by weight of active ingre dient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or li quid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Table XXXVI II Weight Percent* Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts -l-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0 C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions -are-repared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147ff. and "Perrys Chemical Engineers Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and O. D. Fryer and S. A. Evans, "Weed Control Hand book, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 18 Wettable Powder N-±(4,6-dimethoxy-l,3,S-triazin-2-yl)aminocarbonyl) aminosulfonyl-2-(2-methoxyethyl )benzene- sulfonamide 80% sodium alkylnaphthalenesulfonate 2X sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example 19 Wettable Powder N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino sulfonyl-2-(2-chloroethyl)benzenesulfonamide 50X sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. Example 20 Granule Wettable Powder of Example 19 5% attapulgite granules 95% (U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing wS25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. Example 21 Extruded Pellet N-± (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)- aminosulfonyl-2-(2-chloroethyl)benzenesulfon amide 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5X sodium alkylnaphthalenesulfonate 1X calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. Example 22 Oil Suspension N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino sulfonyl-2-(2-chloroethyl)benzenesulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 23 Wettable Powder N-L (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)- aminosulfonyl-2-(2-chloroethyl )benzenesulfon- amide 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example 24 Low Strength Granule N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-methoxyethyl)benzene sulfonamide 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted gran ules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 25 Aqueous Suspension N-( (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)- aminosulfonyl-2-(2-g-toluenesulfonyloxyethyl)benzene- sulfonamide 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5X polyvinyl alcohol 1.0% water 56.7X The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. Example 26 Solution N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon- yl]aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)ben zenesulfonamide, sodium salt 5% weter 95% The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. Example 27 Low Strength Granule N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-methoxyethyl)benzenesulfon- amide 0.1% attapulgite granules 99.9% (U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged. Example 28 Granule N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-chloroethyl)benzenesu amide 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20S of the natural sugars) attapulgite clay 9% The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example 29 High Strength Concentrate N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-chloroethyl)benzenesulfon- amide 99% silica aerogel 0.5X synthetic amorphous silica 0.5% The ingredients.are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. SO screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 30 Wettable Powder N-± (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl) aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl) benzenesulfonamide 40x sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 31 Oil Suspension N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] eminosulfonyl-2-(2-methoxyethyl)benzenesulfon amide 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water. Example 32 Dust N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]aminosulfonyl-2-(2-p-toluenesulfonyl oxyethyl)benzenesulfonamide 10% attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapul gite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example 33 Emulsifiable Concentrate N-±(4 ,6-dimethoxypyrimidin-2-yl)aminocarbonyl)amino- sulfonyl-2-(2-p-toluenesulfonyloxyethyl)benzene- sulfonamide 20% chlorobenzene 74% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. Utility The compounds of the present invention are active herbicides. They have utility for broad-spectrum preand/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, barley, rice, sorghum, and corn, or as plant growth modifiers. 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 weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.0005 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types. The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. Test A Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis; D = defoliation; E = emergence inhibition; G = growth retardation; H = formative effect; I = darker green color; U = unusual pigmentation; X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers. The compounds also have plant growth modifying properties, e.g., they may retard the growth of various plant species, effect defoliation, etc. Compounds Compound 1 EMI173.1 Compound 2 EMI173.2 Compound 3 EMI173.3 Compound 4 EMI173.4 Compounds (continued) Compound 5 EMI174.1 Compound 6 EMI174.2 Compound 7 EMI174.3 Compound 8 EMI174.4 Compounds (continued) Compound 9 EMI175.1 Compound 10 EMI175.2 Compound 11 EMI175.3 Compound 12 EMI175.4 Compounds (continued) Compound 15 EMI176.1 Compound 14 EMI176.2 Compound 15 EMI176.3 Compound 16 EMI176.4 Compounds (continued) Compound 17 EMI177.1 Compound 18 EMI177.2 Compound 19 EMI177.3 Compound 20 EMI177.4 Compounds (continued) Compound 21 EMI178.1 Compound 22 EMI178.2 Compound 23 EMI178.3 Compounds (continued) Compound 24 EMI179.1 Compound 25 EMI179.2 Compound 26 EMI179.3 Compound 27 EMI179.4 Compound 28 EMI179.5 Compounds (continued) Compound 29 EMI180.1 Compound 30 EMI180.2 Compound 31 EMI180.3 Compound 32 EMI180.4 Compound 33 EMI180.5 Compounds (continued) Compound 34 EMI181.1 Compound 35 EMI181.2 Compound 36 EMI181.3 Compound 37 EMI181.4 Compound 38 EMI181.5 Compounds (continued) Compound 39 EMI182.1 Compound 40 EMI182.2 Compound 41 EMI182.3 Compound 42 EMI182.4 Compound 43 EMI182.5 Compounds (continued) Compound 44 EMI183.1 Table A Cmpd. 1 Cmpd. 1 Cmpd. 2 Cmpd. 3 Rate g/ha 50 400 400 400 POST-EMERGENCE Bush bean 5C,9G,6Y 9C 9C 6C,9G,6Y Cotton 3C,7G 5C,9G 5C,9G 6C,9G Morningglory 5C,9G 5C,9G 5C,9G 9C Cocklebur 2C,9G 9C 9H 9C Sicklepod 3C,5H 5C,9G 5C,9G 4C,8G Nutsedge 0 3G 5C,9G 4G Crabgrass 0 3G 1C,5G 0 Barnyardgrass 0 2C,3H 3C,9H 0 Wild Oats O 2G 3G O Wheat O 2G 0 0 Corn 2G 2C,7H 3C,8H 2C,7H Soybean 4C,9G 9C 5C,9G 5C,9G Rice 2G 5G 3C,9G 5G Sorghum 1C 2C,7H 2C,9H 2C,5G Sugar beet 5C,9G 5C,9G 9C 5C,9G PRE-EMERGENCE Morningglory 9C 9C 9G 9C Cocklebur 9H 9H 9H Sicklepod 90 5C,9G 90 90 Nutsedge O 2C 10E 3G Crabgrass 1C 2C 50 0 Barnyardgrass 1H 2C,3H 3C,8H 0 Wild Oats 2H 1C O 6G Wheat 2H 1C O 30 Corn 5G 2C,8G 2C,8H 2C,8H Soybean 8H 9H 3C,9H 3C,8H Rice O 6G 3C,7G 4G Sorghum 2C 2C,8G 5G 2C,7H Sugar beet 9C lOE 90 5C,9G Table A (continued) Cmpd. 4 Cmpd. S Cmpd. 6 Cmpd. 7 Rate g/ha 400 50 50 50 POST-EMERGENCE Bush bean 9C 5C,9G,6Y 4C,8G,6Y 4C,9G,6Y Cotton 5C,9G 5C,9G 4C,5G 2C,5G Morningglory 9C 2C 0 3C,4H Cocklebur 9C - 0 4C,9G Sicklepod 9C 2C 2C 4C,9G Nutsedge 5C,9G 0 0 3C,8G Crabgrass 2C,5G 0 0 2C,7G Barnyardgrass 5C,9H O 1C,4H 5C,9H Wild Oats 3C,9G 0 0 0 Wheat 3C,9G 0 0 0 Corn 2C,9G 1H 2C,6H 5C,9G Soybean 5C,9G 5C,9G 2C,8G 5C,8G Rice 5C,9G 0 2G 5C,9G Sorghum 9C O 1C 4C,8H Sugar beet 9C - - PRE-EMERGENCE Morningglory 9G 7G 3G 9G Cocklebur 9H - 8H 8H Sicklepod 9G 4G 7G 9G Nutsedge 9G 0 0 10E Crabgrass 2C,5G 0 2G 6G Barnyardgrass 4C,9H 0 2C,6G 4C,9H Wild Oats 3C,9H O O 1C,5G Wheat 9H 0 0 5G Corn 9H 1C 3C,7G 9H Soybean 9H O 0 4C,6H Rice 5C,9H 0 2C lOE Sorghum 5C,9H O 2G 3C,9H Sugar beet lOE - - lOE Table A (continued) Cmpd. 7 Cmpd. 8 Cmpd. 8 Cmpd. 9 Rate g/ha 400 50 400 50 POST-EMERGENCE Bush bean 9C 6C,9G,6Y 5C,9G,6Y 9D,9G,6Y Cotton 4C,9G 5C,9G 5C,9G 5C,9G Morningglory 4C,9G 6C,9G lOC 9C Cocklebur 5C,9G 4C,9G 9C 9C Sicklepod 5C,9G 4C,8G 5C,9G 6C,9G Nutsedge 2C,9G 1C,5G 4C,8G 8G Crabgrass 2C,9G 2C,6G 3C,7G 8G Barnyardgrass 5C,9H 5C,9H 5C,9G 2C,9H Wild Oats 2C,4G 2C,4G 2C,9G 2C,9G,5X Wheat 1C 38 8G 5C,9G Corn 2C,9G 4C,9G 4C,9G 5C,9G Soybean 9C 4C,9G 9C 9C Rice 6C,9G 4C,9G SC,9G 5C,9G Sorghum 3C,9G 2C,9G 2C,9G 9G Sugar beet - - - - PRE-EMERGENCE Morningglory 9G 9G 5C,9G 9G Cocklebur 9G 9H 9H 9H Sicklepod 9G 9G 9H 9G Nutsedge 10E 9G lOE 10E Crabgrass 2C,9G 4C,8G 5C,8G 4C,8G Barnyardgrass 5C,9H 9H 5C,9H 5C,9G Wild Oats 2C,6G 4C,8G 4C,8H 4C,8H Wheat 1C,8G 2C,9G 4C,9G 9G Corn 9H 9H lOH 9G Soybean 9H 9H 9H 8H Rice lOE lOE lOE 5C,9H Sorghum 6C,9H 5C,9H 7C,9H 5C,9H Sugar beet lOE lOE lOE Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 11 Rate g/ha 400 50 50 400 POST-EMERGENCE Bush bean 9C, 6C,9G,6Y 9C 9C Cotton 9C - - Morningglory 9C 3C,9H 2C,8G lOC Cocklebur 9C 3C,9G 10C 10C Sicklepod 9C 3C,5G 9C 9C Nutsedge 3C,9G O 2C,8G 2C,9G Crabgrass 3C,9G 2C,5G 3C,5G 2C,7G Barnyardgress 5C,9H 2C,9H 3C,9H 9C Wild Oats 4C,9G 2C,9H 2G 3C,5G Wheat 4C,9G 3G O 2C,5G Corn 4U,9G 1C,6H 2U,9G Soybean 9C 2C,5H 5C,9G 9C Rice 6C,9G 3C,9G 5C,9G 9C Sorghum 9G 2C,9G 3C,9G 2C,9H Sugar beet - PRE-EMERGENCE Morningglory 9G 9G 8H 9H Cocklebur 9H 9H 9H 9H Sicklepod 9G - 9H 9G Nutsedge 10E O 10E 10E Crabgrass 4C,9G 5G 2C 2C,8G Barnyardgrass 4C,9H 2C,8G 2C,8H 3C,9H Wild Oats 5C,9H 2C,7H 4G 2C,8H Wheat 9H 5G 2G 7G Corn lOE 2C,7G 2C,7G 9H Soybean 9H 0 7H 9H Rice 10E 3C,7G 9H lOE Sorghum 5C,9H 3C,9H 3C,8H 5C,9H Sugar beet - - - Table A (continued) Cmpd. 12 Cmpd. 13 Cmpd. 14 Rate g/ha 50 50 50 POST-EMERGENCE Bush bean 9D,9G,6Y 4C,8G,6Y 9C Cotton Morningglory 2C,8H 6C,9G lOC Cocklebur 2C,8H 6C,9G lOC Sicklepod 3C 2C,8G 4C,9G Nutsedge O 1C,4G 0 Crabgrass 2C O 1H Barnyardgrass 2C O 1H Wild Oats O 0 0 Wheat O 0 0 Corn 1H 2U,6G 3C,9H Soybean 2C,5G 9C 5C,9G Rice - - 7G 2C,4G 3C,7G Sorghum 2G 3H 2C,7H Sugar beet - 5C,9G 5C,9G PRE-EMERGENCE Morningglory 8H 9G lOC Cocklebur 3H 8H 9H Sicklepod 0 2C,9G 5C,9G Nutsedge O 0 0 Crabgrass 2C O 1C Barnyardgrass 2C 2C,2H 2G Wild Oats O 1C 3G Wheat O 1C O Corn 2G 2C,8H 2C,9H Soybean 2G 3C,5H 3C,7H Rice 2G 2C 2C Sorghum 3G 2C 1C,5G Sugar beet - 5C,9G lOE Table A (continued) Cmpd. 15 Cmpd. 15 Cmpd. 16 Cmpd. 16 Rate g/ha 50 400 50 400 POST-EMERGENCE Bush bean 4S,9G,6Y 5C,9G,6Y 4C,8G,6Y 9C Cotton 2C,2H 4C,9G 4C,4G 4C,9G Morningglory 2C,4H 4C,8H 4C,8H 5C,9G Cocklebur 2C 4C,9H 3C,7H 4C,9G Sicklepod 4C,6G 4C,7H 4C,5H 4C,9G Nutsedge 3G 3G O 1C,2G Crabgrass 3G 3G 2C 1C,3G Barnyardgrass 2C,4H 2C,2H 2C 2C,6H Wild Oats O 0 0 0 Wheat O O O 2G Corn 3C,7H 2C,9H 2C,9G 2C,9G Soybean 3C,6G 4C,8G 4C,9G 3C,9G Rice 1C 2C,6G 1C,5G 3C,9G Sorghum 1C 1C,3G 1C,4G 2C,7G Sugar beet - - - PRE-EMERGENCE Morningglory 1C,2H 9G 8H 2C,8G Cocklebur - 8H 8H 9H Sicklepod 2C,4H 8H 1C 9G Nutsedge O 10E 2C,5G 1C,5G Crabgrass O 1C O 0 Barnyardgrass 2C,4G 2C,7H 2C 4C,8H Wild Oats O 0 0 0 Wheat O 0 0 0 Corn 3C 3C,9G 3C,8G 2C,9G Soybean 1C 4C,6H 1C,1H 4C,7H Rice 0 3C,7H 2C,3G 5C,9H Sorghum O 1C,4G 2C,70 3C,8G Sugar beet 1H lOE 1C,5G lOE Table A (continued) Cmpd. 17 Cmpd. 17 Rate g/ha 50 400 POST-EMERGENCE Bush bean 5C,9G,6Y 9C Cotton 2C,7G 4C,9G Morningglory 2C,4G 5C,9G Cocklebur 1H,4G 9C Sicklepod 2C,8G 6C,9G Nutsedge 2C,9G 2C,9G Crabgrass O 1C,4G Barnyardgrass 2C,8H 5C,9H Wild Oats O 0 Wheat O 0 Corn 1C,5H 2C,8H Soybean 5C,9G 5C,9G Rice 3G 8G Sorghum 1C 3C,8H Sugar beet 2C,9G 4C,9G PRE-EMERGENCE Morningglory 8H 9G Cocklebur 9H 9H Sicklepod 9G 9G Nutsedge 4G lOE Crabgrass O 1C Barnyardgrass 2C,7H 4C,9H Wild Oats 0 4G Wheat 0 2G Corn 2C,3G 2U,9H Soybean 1C,2H 9H Rice 60 9H Sorghum 6G 2C,8H Sugar beet 10E 10E Table A (continued) Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Rate g/ha 50 50 50 50 POST-EMERGENCE Bush bean 6C,9G,6Y 9C 9C 9C Cotton 4C,9G 5C,9G 9C 5C,9G Morningglory 2C,7G 2C,7G 5C,9G 3C,7G Cocklebur 9C 4C,9G 9C 9C Sicklepod 3C,8G 5C,9G 9C 6C,9G Nutsedge 9H 7G 1C,5G 5C,9G Crabgrass 1C,5G 3G 3G 4G Barnyardgrass 2C,8H 3C,9H O 3C,9H Wild Oats 2C,8G 2C,5G 0 0 Wheat O 1C,3G 0 0 Corn 1C,6H 2C,9H O 1C,6G Soybean 2C,9G 5C,9G 5C,9G 5C,9G Rice 1C,8H 6G O 3G Sorghum 9G 2C,9G 0 1C,5H Sugar beet 2C,9G 5C,9G 9C 5C,9G PRE-EMERGENCE Morningglory 8G 9C 9G 9G Cocklebur 9H 9H 9H 9H Sicklepod 9G 9G 5C,9G Nutsedge 8G 8G 4G 10E Crabgrass 0 4G 0 2G Barnyardgrass 3C,6G 5C,9H 1C 2C,8H Wild Oats 2C,8G 3C,8G O 2C,5G Wheat 6G 7G O 1C,3G Corn 2C,9G 9H 7G 8G Soybean 6H 4C,8H 9H 9H Rice 3C,9H 2C,8G 3G 2C,6G Sorghum 3C,8H 2C,8G 2G 2C,8G Sugar beet 9G 4C,9G 9G 5C,9G Table A (continued) Compound 22 Cmpd. 23 Rate g/ha 50 400 50 POST-EMERGENCE Bush bean 2C,3G 4C,8G,6Y 9D,9G,6Y Cotton 3C,7G 4C,8G 9C Morningglory 3C,8G 5C,9G 5C,9G Cocklebur 3C,9G 9C 9C Sicklepod 2C,5G 5C,9G 9C Nutsedge 5C,9G 9G 2C Crabgrass 5G 1C,5G 2G Barnyardgrass 2C,6H 3C,9H 1H Wild Oats O 1C,3G O Wheat O 1C 2G Corn 4G 2C,7H 2C,6H Soybean 1C,7G 5C,9G 9C Rice 3H 2C,7G 1C,3G Sorghum 2C,6H 2C,9H 2C,6H Sugar beet 4C,9G 5C,9G 9C PRE-EMERGENCE @@ @@ @@,@@ 9H 9H 9H Sicklepod 3C,6G 9G 9G Nutsedge 8G lOE 4G Crabgrass 1C 1C,3G O Barnyardgrass 2C,7H 3C,9H 2C Wild Oats O 2C,5G O Wheat 0 2C,6G 0 Corn 2C,6G 2C,8G 2C,8G Soybean 2C 2C,6H 9H Rice 2C,.3G 2C,8H 2C,3G Sorghum 3C,8H 2C,9H 2C,8H Sugar beet 9G lOE lOE Table A (continued) Cmpd. 24 Cmpd. 25 Rate g/ha 50 50 POST-EMERGENCE Bush bean 9C 9C Cotton 4C,9G 5C,8G Morningglory 4C,9G 4C,9G Cocklebur 9C 5C,9G Sicklepod 5C,9G 5C,9G Nutsedge 3C,9G lOC Crabgrass 3C,9H 2C,8G Barnyardgrass 5C,9H 9C Wild Oats 2C 0 Wheat 4G 1C,2G Corn 2C,9G 4U,9G Soybean 5C,9G 5C,9G Rice 5C,9G 5C,9G Sorghum 2C,9G 3U,9G Sugar beet 4C,9G 9C PRE-EMERGENCE Morningglory 9G 8G Cocklebur 9H 9H Sicklepod 5C,9G 4C,9G Nutsedge 9G lOE Crabgrass 2C,4G 1C,2G Barnyardgrass 3C,9H 3C,9H Wild Oats 2C,7G 2C,5G Wheat 2C,6G 1C,7G Corn 5C,9H 2C,9G Soybean 9H 9H Rice 4C,9H 9H Sorghum 3C,9H 2C,9H Sugar beet 9C 9C Test B Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, cotton, soybean, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. Treated plants and controls were maintained in a greenhouse for sixteen days, after which 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: C = chlorosis/necrosis; E = emergence inhibition; G = growth retardation; H = formative effects; and U = unusual pigmentation. The ratings for the compounds tested by this procedure are presented in Table B. Table B Cmpd. 26 Compound 27 Rate g/ha 50 50 400 POST-EMERGENCE Morningglory 2C 1C,2H 2C Cocklebur 4G O 2H Sicklepod 2C O 2C Nutsedge o 0 0 Crabgrass 2G O 3G Barnyardgrass 3H 0 0 Wild Oats o 0 0 Wheat o 0 0 Corn 2C,6G 2H 2C,5H Soybean 2C,8G 2H 4G Rice 2C,5G O 2C,4G Sorghum 2C,4G O 2C,3H Sugar beet 3C,8G 2C,5G 2C,8G Cotton 2G 3C,5G 4C,8G PRE-EMERGENCE Morningglory 7G 7G Cocklebur 8H 9H 9H Sicklepod 8G 1H 7G Nutsedge O 0 0 Crabgrass O 0 2C Barnyardgrass 2C 2C 2C,6G Wild Oats 2C,3G 0 2C,7G Wheat 5G 0 4G Corn 2C,6G 2C,7G 3C,9M Soybean 2C,4H 2C,2H 3C,7G Rice 3C,5G 3G 3C,8G Sorghum 3C,7G 2C,3H 2C,8G Sugar beet 2C,8G 8G 9G Cotton SG 8G 9G Table B (continued) Compound 28 Compound 29 Rate g/ha 50 400 50 400 POST-EMERGENCE Morningglory 88 8B 4C,8G 5C,9H Cocklebur 4H 5H 2C,5H 2C,8H Sicklepod 3C,4H 4C,5H 5C,9G 5C,9G Nutsedge 2C,3G 2C,5G 5G 2C,5G Crabgrass O 1C 2G 2C,5G Barnyardgrass 0 3C,3H 2C,8H 4C,9H Wild Oats O 0 0 2G Wheat O 0 0 2G Corn 0 2G 3C,8H 2C,8H Soybean 1C,3H 2C,8H 3C,9G 4C,9H Rice 2C,9G 4C,9G 2C,9G 5C,9G Sorghum 2C 4C,5G 2C,6G 3C,8H Sugar beet 3C,6G 4C,8G 4C,8G 4C,9G Cotton 5C,9H 4C,9H 4C,9G lOC PRE-EMERGENCE Morningglory 2C,2H 7G 9G 9H Cocklebur 1H 6H 9H 9H Sicklepod 0 3G 6G 2C,7G Nutsedge 0 2C,6G O 9G Crabgrass O 0 0 2C,5G Barnyardgrass 2C,5G 2C,8H 2C,9H 5C,9H Wild Oats 0 2C,5G 2C,7G 3C,8H Wheat O 4G 1C,7G 2C,8G Corn 2C,6G 9G 3C,9G 5C,9H Soybean 2C 3C,3H 3C,8G 4C,8H Rice 3C,8H lOE 5C,9H 10E Sorghum 3C,6G 4C,9G 3C,9G 4C,9H Sugar beet 9G 3C,9G 5C,9G 10E Cotton - 5G 2C,7H 9G Table B (continued) Compound 30 Cmpd. 31 Rate g/ha 50 400 50 POST-EMERGENCE Morningglory 2C,7G lOC 0 Cocklebur 3C,8H lOC 0 Sicklepod 5C,9G lOC 0 Nutsedge 4C,8G 9C 0 Crabgrass 2C,3G 5C,9G 0 Barnyardgrass 9H lOC 0 Wild Oats 0 2C,6G 0 Wheat 0 2C,4G 0 Corn 2U,9G 3U,9G 0 Soybean 5C,9G 5C,9G 0 Rice 5C,9G 6C,9G 0 Sorghum 3C,5G 2C,9H 0 Sugar beet 9C lOC 0 Cotton lOC lOC 0 PRE-EMERGENCE Morningglory 8G 10E 0 Cocklebur 9H 9H O Sicklepoo 9G 9G O Nutsedge 5G lOE 0 Crabgrass 3G 3C,8G 0 Barnyardgrass 4C,9H 5C,9H 0 Wild Oats 3C,6G 4C,8G 0 Wheat 2G 4C,8G 0 Corn 2C,9G 4C,9H 0 Soybean 3C,8H 9H O Rice 5C,9H lOE 0 Sorghum 4C,9H 9C 0 Sugar beet 9C 10E 0 Cotton 9G 3C,9G 0 Table B (continued) Compound 32 Compound 33 Rate g/ha 50 400 50 400 POST-EMERGENCE Morningglory 5C,9G 5C,9G 2C,5G 5C,9H Cocklebur 3C,8G 4C,8G 3G 2C,8G Sicklepod 2C,4G 3C,7G 3C,6H 5C,9G Nutsedge 3G 0 0 0 Crabgrass 2E 3G 0 3G Barnyardgrass 0 3H O 1H Wild Oats O 0 0 0 Wheat O 0 0 0 Corn 2C,8H 2C,8H 2G 2C,5G Soybean 4C,9G 5C,9G 4C,9G 5C,9G Rice 5G 4G 0 4G Sorghum 2C,3H 2C,3H O 1C Sugar beet 4C,8G 9C 4C,9G 5C,9G Cotton PRE-EMERGENCE Morningglory 9G 2C,9H 8H Cocklebur 2G 9H 6H 8H Sicklepod 9G 9G 6G 7G Nutsedge O 0 0 0 Crabgrass O 2G O 1C Barnyardgrass 3G 3C,7H 0 2C,2H Wild Oats 1C 2C O O Wheat O 0 0- 0 Corn 2C 9G 3C,8G 2C,9H Soybean 8H 3C,8H 2C,2H 8H Rice 2C 3C,7G 2G 3G Sorghum 2C,4G 3C,8H 0 2G Sugar beet 2C,5G 9G 8G 5C,9G Cotton 6G 9G 7G Table B (continued) Compound 34 Compound 35 Rate g/ha 50 400 50 400 POST-EMERGENCE Morningglory 2C,3G 9C 6C,9G 9C Cocklebur 2C 4C,9G 3C,7H SG Sicklepod 2C,3H 4C,8H 4C,9H 5C,9G Nutsedge 2C 2C,8G 3C,7G 3C,9G Crabgrass 2G 1C 2G 5C,8G Barnyardgrass 2C,3H 4C,9H 3C,9H 5C,9G Wild Oats O 1C,4G 0 2C,7G Wheat O 1C,2G 0 SG Corn 2C,7H 2C,9H 9G 9C Soybean 2C,5H 2C,8H 5C,9G 5C,9G Rice 3C,8H 5C,9G 4C,9G 5C,9G Sorghum 2C,6G 4C,8H 2C,7G 2C,9G Sugar beet 2C,6G 4C,8G 9C 9C Cotton 4C,8G 4C,9G 9C 9C PRE-EMERGENCE Morningglory 2C 9G 9G 2C,9G Cocklebur O 8H 9G 9H Sicklepod 2C,4G 7H 9G 9G Nutsedge O 0 5G 4C,9G Crabgrass 0 4G 2C 2C,8G Barnyardgrass 2C,5G 3C,8H 5C,9H 3C,9H Wild Oats 2C,4G 3C,7G 4C,8G 5C,9H Wheat 2C 2C,5G 2C,5G 2C,9G Corn 2C,4G 4C,9H 5C,9H lOM Soybean 1C,1H 4C,7H 9H 9H Rice 3C,7H 4C,9H 5C,9H 10E Sorghum 3C, 5C,9H 5C,9H 5C,9G Sugar beet 2C,7G 3C,9G lOE lOE Cotton 6G 9G 5C,9G 5C,9G Table B (continued) Cmpd. 36 Cmpd. 37 Cmpd. 38 Cmpd. 39 Rate g/ha 50 50 50 50 POST-EMERGENCE Morningglory 3C,5H 1C,2H 5C,9G 1C,2H Cocklebur 3C,8H SG 2C,9G 9C Sicklepod 4C,9G 2C,3H 5C,9G 5C,9G Nutsedge 6C,9G 4G 2C,9G 3C,9G Crabgrass 2G 0 2C,8G 5G Barnyardgrass 2C,9H 3C,5H 3C,9H 5C,9H Wild Oats O 0 4G 0 Wheat O 0 0 0 Corn 4C,9G 2C,7H 2C,9G 3C,9G Soybean 5C,9G 2C,8G 5C,9G 5C,9G Rice 4C,9G 9G 6C,9G 4C,9G Sorghum 2C,7H 2C,6G 4C,9H 2C,9H Sugar beet 2C,8G 6G 5C,9G 3C,9G Cotton 9C 3C,6G 5C,9G 9H PRE-EMERGENCE Morningglory 8G 2G 9G 8G Cocklebur 9H 9H 9H 9H Sicklepod 2C,9G 5G 9G 9G Nutsedge 8G O 7G 9G Crabgrass 2G 0 4G 2G Barnyardgrass 2C,9H 2G 9H 3C,9H Wild Oats 5G 6G 2C,8H 2C,6G Wheat 2G 2G 8G 3G Corn 3C,9H 3C,7H 5C,9H 2C,9G Soybean 3C,9H lC,lH 9H 8H Rice 2C,8H 2C,7H 10E 3C,9H Sorghum 2C,7G 2C,8H 5C,9H 3C,9H Sugar beet 9G 8G lOE 9G Cotton 9G 7G 9H 90 Table B (continued) Cmpd. 40 Compound 41 Rate g/ha 400 50 400 POST-EMERGENCE Morningglory 2C 2C,5H 9C Cocklebur 1C 1H 9C Sicklepod 1C 2C 5C,9G Nutsedge O 0 7G Crabgrass O 2G 2C,5G Barnyardgrass O O 2C,7H Wild Oats O O 1C Wheat O 0 0 Corn 1U,9G 2C,8H 2U,9G Soybean 2C,2H 4C,9G 5C,9G Rice 2C,9G 2G 4C,9G Sorghum 2C,3G O 2C,9H Sugar beet 3C,8G 4C,9H 9C Cotton 1C 2C,8G 10C PRE-EMERGENCE Morningglory 8G 7G 9H Cocklebur 0 7H 9H Sicklepod 0 2G 9G Nutsedge O 0 2C,5G Crabgrass O O 1C Barnyardgrass O 2H 7H Wild Oats O 2C 2C,3G Wheat O O 2G Corn 1C,3G 2C,8G 3C,9H Soybean lC,lH 2C,4H Rice O 2C,3G 5C,9H Sorghum O 2C,5G 5C,9H Sugar beet 2C,3H 4C,9G 5C,9G Cotton O 6G 9G Table B (continued) Cmpd. 42 Cmpd. 43 Cmpd. 44 Rate g/ha 400 400 400 POST-EMERGENCE Morningglory 10C lOC 9C Cocklebur 9C 9C 9C Sicklepod 5C,9G 4C,9G 4C,9G Nutsedge 9G 5G SG Crabgrass 2C,9G 2C,7G 2C,8G Barnyardgrass 5C,9G 2C,6H 5C,9G Wild Oats 2C,8G 3G 3C,8G Wheat 7G 0 3C,8G Corn 2U,9G 2U,9G 2C,9.G Soybean 5C,9G 4C,9G 5C,9G Rice 4C,9G 4C,8G 4C,9G Sorghum 2C,9G 3C,8H 2C,9G Sugar beet 5C,9G 9C 5C,9G Cotton 9C lOC lOC PRE-EMERGENCE Morningglory 9E 9G 9C Cocklebur 9H 9H 9H Sicklepod 9G 9G 8G Nutsedge 10E 5G lOE Crabgrass 4G 1C 4C,8G Barnyardgrass 3C,8H 2C,3G 4C,9H Wild Oats 2C,7G 2C,5G 4C,8H Wheat 1C,8G 0 9H Corn 2C,9H 2C,9G 9H Soybean 8H 3C,7H 9H Rice lOE 3C,8H lOE Sorghum 5C,9H 3C,7H 2C,9G Sugar beet 5C,9G 10E 5C,9G Cotton 5C,9G 9G 9G Test C Twenty-five cm diameter plastic pots filled with Woodstown sandy loam soil were planted to soybeans, cotton, corn, rice, wheat, velvetleaf (Abutilon theophrasti), sicklepod (Cassia obtusifolia), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii), johnsongrass (Sorghum halepense), and wild oats (Avena fatua). Additional plant species such as sunflower, rape, sugar beets, sorghum, bush bean, alfalfa, mustard (Brassica kaber), field bindweed (Convolvulus arvensis), teaweed (Sida spinoza), and sesbania (Sesbania exaltata) were sometimes added to this standard test in order to further evaluate selectivity. 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 nonphytotoxic solvent. Approximately 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 C. Under greenhouse conditions, several of the test compounds controlled a number of weed species at rates of application which were non-injurious to corn and sorghum. Table C Over-the-Top Soil/Foliage Treatment Compound 2 Compound 3 Rate g/ha 125 500 125 500 Soybeans 9G 9G 8G 9G Velvet leaf 8G lOC 9C lOC Sesbania lOC lOC 9G lOC Sicklepod 8G 10G 2C 6G Cotton 9G lOC 9C lOC Morningglory 7G 10G 8g 10g Bush bean 6G 8G 8C 9C Jimsonweed O 0 0 2G Cocklebur O 4G 0 4G Sunflower 80 lOC lOC lOC Rape lOC lOC lOC lOC Sugar beets 8G 10G 10G 10G Corn O 8H 0 0 Crabgrass O 0 0 0 Rice O 40 0 0 Nutsedge 60 80 0 0 Barnyardgrass O 7G 0 0 Wheat O 1G O 0 Giant Foxtail O 0 0 0 Wild Oats O 0 0 0 Sorghum O 8G O O Johnsongrass O 0 0 0 Field Bindweed O 0 0 0 Alfalfa - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 4 Compound 7 Rate g/ha 125 500 16 62 Soybeans lOC lOC 8G,6C lOC Velvetleaf 9G lOC 7G 7G Sesbania lOC lOC 7G lOC Sicklepod 10G 10G 8G 9G Cotton 10G 10G 7G 9G Morningglory 10G 10G 9G 10C Bush bean 9G 10G - Jimsonweed O 5C 8G 9G Cocklebur 9G 9G 7G 8G Sunflower lOC lOC 7G 9G Rape lOC lOC 9G lOC Sugar beets 10G 10G - Corn 6G 8G 4G 7G,4C Crabgrass O 0 0 3G Rice 2G 5G 2G 6G,5C Nutsedge 5G 7G 1G 5G Barnyardgrass 9G 9G 5G,5C 7G,6C Wheat O 0 8G,4C SG,3C Giant Foxtail 5G 5G - Wild Oats 3G 4G 2G,1C 2G,3C Sorghum 7G 8G 2G 8G Johnsongrass O 4G 2G 4G Field Bindweed 6G 8G 1G 5G Alfalfa - - 6G 7G Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 8 Compound 9 Rate g/ha 16 62 4 16 62 Soybeans 7G,7C lOC 9G 9G lOC Velvetleaf 7G 8G 8G 10C 10C Sesbania 7G 8G 9G 10C 10C Sicklepod 5G 8G 2G 6G 10G Cotton 8G - 6G 8G 9G Morningglory 3G 4G 7G 7G 10G Alfalfa 7G lOC 7G 6G 9G Jimsonweed 7G 8G 6G 8G 9G Cocklebur 2G 7G 5G 8G 9G Sunflower 7G 8G 6G 9G 10C Rape 3G 7G 7G 9G 9G Corn 4G,3H 6G,2C 4G 9G 9G Crabgrass 0 2G 0 6G 8G Rice 3G 5G 6S 7G 8G Nutsedge O - 7G 8G 8G Barnyardgrass 4G 6G 8G 8G 9G Wheat 4G 4G 2G 8G 8G Giant Foxtail 0 O 3G 7G 8G Wild Oats - 2G,2C 4G 8G 8G Sorghum 2G 5G 6G 8G 9G Johnsongrass O O 6G 8G 9G Field Bindweed O 0 0 3G 9G Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 10 Rate g/ha 1 4 16 62 Soybeans 2G 0 5G 7G Velvetleaf 2G 2G 7G 9G Sesbania 6G 0 7G 8C Sicklepod 3G 0 0 2G Cotton - 7G 8G 9G Morningglory 3G 2C 8G 3C,8G Alfalfa - 0 0 ' 0 Jimsonweed 9G 0 2G 4G Cocklebur 7G 5G 7G 7G Sunflower 6G 5G,2H 9G lOC Rape 6G 9G lOC lOC Corn 1G 0 0 6G,2H Crabgrass O 0 0 0 Rice 1G 3G 7G 8G Nutsedge O - 0 0 Barnyardgrass 0 2G 3G 8G Wheat O 0 0 2G Giant Foxtail O 0 0 0 Wild Oats O 0 0 2G Sorghum 0 3G 7G 9G Johnsongrass O 7G 9G 9G Field Bindweed O 0 0 9C Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 11 Rate g/ha 1 4 16 62 Soybeans 2G 4C,5G lOC lOC Velvetleaf 4G 4C 9G lOC Sesbania 6G 7C,8G 9C lOC Sicklepod 4G - 8G 9G Cotton 5G 10C 9C 10C Morningglory 2G 6G lOC lOC Alfalfa 3G 4G lOC lOC Jimsonweed 4G 6G 7G 8G Cocklebur 3G 4G 9C lOC Sunflower 3G 10C 10C 10C Rape 4G 10C 10C 10C Corn O 2H,2G 4G 5G Crabgrass O O O 1G Rice O O 3G 3C,5G Nutsedge O O 5C,3G 4C,5G Barnyardgrass O 2G 3G 4G Wheat O O 1G 4G Giant Foxtail O 2G 3G 8G Wild Oats O 1G 2G 5G Sorghum O O 2 8G Johnsongrass O O O 2G Field Bindweed O 4G 3G 10C Bush bean O - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 14 Compound 18 Rate g/ha 4 16 16 62 Soybeans O 4G 6G 9G,9C Velvetleaf 7G 9G 5G 4G Sesbanis 7G 10C 10C 10C Sicklepod 0 4G 4G,3C 9G Cotton 3G 9G - 6G Morningglory 8G 9G 5G 3G Alfalfa - - 3G 4G Jimsonweed O 3G 0 2G Cocklebur - lOC 2G 3G Sunflower 7G 9C 6G Rape 8G 9C 8G 9G Sugar beets 9G 9G - Corn O 0 1G 4G Crabgrass O 0 0 2G Rice O 0 0 0 Nutsedge O 0 0 2G Barnyardgrass O O 1G 4G Wheat O 0 0 2G Giant Foxtail O 0 0 1G Wild Oats O 0 O 1G Sorghum O O 8G 9G Johnsongrass O O 1G 1G Field Bindweed O 0 0 0 Bush bean 7G 8G - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 19 Rate g/ha 1 4 4 16 16 62 62 Soybeans 6G 8G 9G,7C 9G,8C 10G 10G lOC Velvetleaf 6G 10G 9G,6C 10C 10G 10G 10C Sesbania 8G 10G 10C 10C 10G 10G 10C Sicklepod 6G 10G 10C 10C 10G 10G 9G,3C Cotton 5G 10G 8G,4C 10C 10G 10G 10C Morningglory 3G 5G 4G 7G 6G 8G lOC Alfalfa - - 7G 8G,2C - - 8G,2C Jimsonweed O 10G 7G - 10G 10G 8G,2C Cocklebur 2G 10G - - 9G 10G lOC Sunflower - - 7G lOC - - lOG Rape - - lOC lOC - - lOG Sugar beets 4G 10G - - 10G 10G Corn O O 1G 5G,3H 7G 7G 8G,3H Crabgrass O 0 3G 3G 0 0 0 Rice O 0 2G 3G 3G 2G 5G Nutsedge O 0 2G 2G 0 0 8G Barnyardgrass 0 0 - 9G 0 0 9G Wheat O 0 0 0 0 0 0 Giant Foxtail 0 0 0 0 0 0 0 Wild Oats O 0 0 0 0 0 0 Sorghum - - 2G 2G - - 8G Johnsongrass O 0 7G,2U 3G 0 0 2G Field Bindweed - - 0 O - - - Bush bean - - - - - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 20 Rate g/ha 4 4 4 16 62 Soybeans lOC lOC 9G,7C 9G,7C 9G,7C Velvetleaf 6G 4G lOC lOC lOC Sesbania lOC lOC 9G lOC lOC Sicklepod 2C,7G 6G 8G lOC lOC Cotton lOC lOC 9G 9G,3C lOC Morningglory 8G 7G 7G,2C 9G lOC Alfalfa 7G 5G 4G 8G 9G 3imsonweed 7G 8G 4G 8G 9G,4C Cocklebur 8G 5G - 6G 7G Sunflower 9G lOC 9G lOC 10C Rape 8C,9G 10C 9G 10C 10C Sugar beets - - - - Corn O 0 0 0 0 Crabgrass O 0 0 0 0 Rice 8G O 0 0 0 Nutsedge O 0 0 0 0 Barnyardgrass O O O O O Wheat O O O O O Giant Foxtail O 0 0 0 0 Wild Oats O 0 0 0 0 Sorghum O 0 0 0 0 Johnsongrass O O O O O Field Bindweed O O O O O Bush bean - - - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 21 Rate g/ha 1 4 16 16 62 62 Soybeans lOC lOC 10C 9G lOC lOC Velvetleaf 6G 9G 10G 9C 10C 9C Sesbania 7G 10C 10C 10C 10C 10C Sicklepod 2C 7C 10G 8G 10G 8G Cotton 3G 7C 9G lOC 9G 9G Morningglory 0 2G 8G 8G 8C lOC Alfalfa - - - SG - 7G Jimsonweed 4G 3G 6G 2G - 9G Cocklebur - 3G 7G 5G lOC 8G Sunflower - - - lOC - lOC Rape - - - 7G - 8G Sugar beets 6G 7C lOC - lOC Corn 2C 3C 3C 6G,3H 6G 7G Crabgrass O 0 0 3G 0 5G Rice 2G 0 0 2G 0 4G Nutsedge O 0 8G 4C,7G 8G 7G Barnyardgrass O O 2G 7G,4C 8G 8G Wheat O O O 3G O 3G Giant Foxtail 2G O O 4G O 10C Wild Oats O O O 5G O 7G Sorghum - - - 4G - 7G Johnsongrass O O O O O 2G Field Bindweed - - - O - 3G Bush bean - - - - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 22 Compound 23 Rate g/ha 16 62 16 62 Soybeans 3G 4G lOC lOC Velvetleaf 3G 6G 6G 6G Sesbania lOC lOC lOC lOC Sicklepod 2G 3G 7G 8G Cotton 9G lOC lOC Morningglory 3G 6G,4C 3G 8G Alfalfa 1C,2G 2C,7G 5G 8C,7G Jimsonweed 3G 6G 6G 10C Cocklebur 8G lOC 7C,7G 9G Sunflower 9G lOC 9G lOC Rape 8G 8G 9G 10C Sugar beets - - - Corn O 0 0 0 Crabgrass O 0 0 0 Rice O O 1G 4G Nutsedge O 0 0 0 Barnyard grass O 0 0 0 Wheat O 1G O 0 Giant Foxtail O O O O Wild Oats O O O O Sorghum O 0 0 0 Johnsongrass O O O O Field Bindweed 2G 4G,3C 6G 5G Bush bean - - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 24 Rate g/ha 4 16 Soybeans 7G 9G Velvetleaf 3G 5G Sesbanis 5G 6G Sicklepod 5G 8G Cotton 4G 7G Morningglory 5G 5G Bush bean Jimsonweed 4G 8G Cocklebur 6G 9G Sunflower Rape Sugar beets 7G 9G Corn 3G 7G Crabgrass 0 2G Rice 0 4G Nutsedge 0 7G Barnyardgrass Wheat o 0 Giant Foxtail O 0 Wild Oats O 0 Sorghum Johnsongrass O 4G Field Bindweed Alfalfa Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 42 Rate g/ha 4 16 62 250 Soybeans 3G 8G 9G 9C Velvetleaf 5G 8C 10C 10C Sesbania - - - Sicklepod 0 7G 9G 9G Cotton O 5G 10C 9G Morningglory O 5G 6G 10C Teaweed 5G 6G lOC lOC Jimsonweed O 0 7G 9G Cocklebur 3G 6G 8G 10C Sunflower - - - Rape - - - Sugar beets 4G 8G 10G 10G Corn 0 6G 9G 9G Crabgrass O 0 0 4G Rice O 0 6G 9G Nutsedge 0 5G 7G 9G Barnyardgrass O 0 9C 9C Wheat O 0 0 0 Giant Foxtail O 0 4G 6G Wild Oats O 0 0 3G Sorghum - - - Johnsongrass O 7G 8G 8G Field Bindweed - - - Bush bean - - - Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 43 Rate g/ha 4 16 62 250 Soybeans 2G 4G 8G 9G Velvet leaf 0 3G 9G lOC Sesbania Sicklepod 0 3G 4G 8G Cotton 0 6G 9G 9G Morningglory 4G 7G 8G lOC Teaweed O 5G 10C 10C Jimsonweed O O 8G 9G Cocklebur 0 3G 9G lOC Sunflower Rape Sugar beets 10C 10C 10C 10C Corn O 0 5G 8G Crabgrass O O O 2G Rice O O O O Nutsedge O O 3G 3G Barnyardgrass O 0 0 0 Wheat O 0 0 0 Giant Foxtail O O 3G 3G Mild Oats O O O O Sorghum Johnsongrass O 0 0 3G Field Bindweed - - - Bush bean Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 44 Rate g/ha 1 4 16 62 Soybeans 2G 3G 7G 9G Velvetleaf O O 3G 3G Sesbania - - - Sicklepod O 0 0 3G Cotton 0 2G 4G 5G Morningglory O 3G 4G 7G Teaweed O O 4G 5G Jimsonweed O 3G 5G 6G Cocklebur 0 2G 4G 6G Sunflower - - - Rape Sugar beets 0 4G 8G 9G Corn 0 2G 6G 7G Crabgrass O 0 0 0 Rice O 0 4G 8G Nutsedge O 0 0 0 Barnyardgrass O 0 3G 7G Wheat O 0 0 3G Giant Foxtail O 0 0 Wild Oats O 0 0 0 Sorghum - - - Johnsongrass O 0 3G 7G Field Bindweed - - - Bush bean - - - Test D Two plastic bulb pans were filled with ferti lized and limed Woodstown sandy loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum hale pense), dallisgrass (Paspalum dilatatum), giant fox tail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pen sylvanicum), morningglory Cipomoea hederacea), sickle -pod (Cassia obtusifolia), teaweed (Sida spinosa), vel vetleaf (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 sugar beets. The above four containers were treated pre emergence with several test compounds within the scope of the invention. Approximately twenty-eight days after treatment, the plants were evaluated and visually rated for re sponse to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table D. Table D PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 1 Compound 2 Rate g/ha 62 250 31 125 Crabgrass O 0 2G 3G Barnyardgrass 0 2G 2G 3G Sorghum 2G 5G O 2G Wild Oats O 2G O 2G Johnsongrass O O O O Dallisgrass O 0 0 2G Giant foxtail 0 0 0 2G Ky. bluegrass 0 2G O 3G Cheatgrass O 0 0 2G Sugar beets lOC lOC 6G 8G Corn 3G 4G 2C 4G,3C Mustard lOC lOC 9G lOC Cocklebur 3G 7G 5G 8G Nutsedge 3G 4G 4G 7G Cotton 5G 7G 2G 2G Morningglory 4G 6G 0 0 Sicklepod 3G 8G O 3G Teaweed 2G 8G O 0 Velvetleaf 8G 9G 4G 7G 3imsonweed 8G 9G 6G 6G Soybean 6G,5H 8G,7H 0 3G,4H Rice 0 3G 0 2G Wheat O 0 0 0 Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 3 Compound 4 Rate g/ha 31 125 -31 125 Crabgrass 0 0 2G 5G Barnyardgrass 0 0 8G 9G Sorghum O 0 6G 9G Wild Oats O 0 4G 6G Johnsongrass 0 0 2G 6G Dallisgrass O 0 3G 4G Giant foxtail 0 0 5G 7G Ky. bluegrass O 0 7G 9G Cheatgrass O O 8G 9G Sugar beets 4G 8G 9G 10C Corn O 3G 6G,5H 9G Mustard 8G 9G 9G lOC Cocklebur - 6G 8G 9G Nutsedge 0 2G 9G 9G Cotton 3G 6G 7G 8G Morningglory 0 2G 8G 9G Sickle pod O 0 7G 8G Teaweed O 0 7G 8G Velvetleaf 2G 5G 8G 9G Jimsonweed 6G 7G 9G 9G Soybean O 3G,5H 8G,5H 8G,7H Rice O 0 7G 9G Wheat O 0 <RTI ID=220.25> 2G 4G Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 7 Compound 8 Rate g/ha 31 125 31 125 Crabgrass 0 3G 0 5G Barnyardgrass 6G 8G 7G Sorghum 5G 9G 8G 10C Wild Oats 2G 3G 2G 4G Johnsongrass 0 0 0 2G Dallisgrass O 0 0 2G Giant foxtail 2G 6G 0 2G Ky. bluegrass O 0 3G 0 Cheatgrass O 0 0 3G Sugar beets 9G lOC 7G lOC Corn 5G 8G,7H 6G,5H 9G Mustard 9G lOC 9G lOC Cocklebur 0 3G 2G 6G,3H Nutsedge lOC lOC 2E lOC Cotton 0 3G O 8G Morningglory 4G 4G 4G 5G Sicklepod 6G 7G 2E Teaweed O 3G O 0 Velvetleaf 2G 7G 0 36 Jimsonweed O 5G O 4G Soybean 7G,5H 9G 5G,2H 9G Rice 7G lOC 7G lOC Wheat 26 3G O 2G Table 0 (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 9 Rate g/ha 16 31 125 Crabgrass O 4G 8G Barnyardgrass 7G 8G 9G Sorghum 8G 9G 10C Wild Oats 5G 6G 8G Johnspongrass 0 2G 7G Dallisgrass O 0 8G Giant foxtail 0 2G 7G Ky. bluegrass 8G 9G lOC Cheatgrass 9G 9G lOC Sugar beets lOC lOC lOC Corn 3G 8G,7H 9G,9C Mustard 9G lOC lOC Cocklebur 5G 5G 8G,5H Nutsedge 8G 9G 10C Cotton 5G 6G 9G Morningglory 6G 7G 8G Sicklepod 2G 8G 9G Teaweed O 4G 7G Velvetleaf 8G 8G 9G Jimsonweed 8G 8G 9G Soybean 6G,3C 8G 9G Rice 7G 8G lOC Wheat 2G 3G 7G Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 10 Compound 11 Rate g/ha 31 125 31 125 Cr abgrass 0 3G 2G 6G Barnyardgrass 3G, 6G,5H 6G 7G,5H Sorghum 8G,8H 10C 7G,5H 9G,9C Wild Oats 3G 6G,3H 0 2G Johnsongrass 2G 7G,5H 5G 5G Dallisgrass 2G 2G 0 3G Giant foxtail 0 0 3G 6G,5C Ky. bluegrass 3G 8G 7G 8G Cheatgrass 7G,5H 8G,8C 8G,8C 9G,9C Sugar beets 6G 9G 10C 10C Corn 2G 7G,7H 5G,7H 9G,9C Mustard 9G lOC 9G,9C 9G,9C Cocklebur 2G 6G,5H 3G 6G,5H Nutsedge 4G 7G lOC lOC Cotton O 6G 2G,5H 7G Morningglory 2G 7G,3H O 3G Sicklepod O 3G 5G 8G,5C Teaweed O 2G 2G 6G Velvetleaf 5G,3H 7G,5C 5G 8G Jimsonweed O 2G 4G 8G Soybean 4G 2G 4G,5H 6G,7H Rice 8G 10@ 8G 9G Wheat 3G 4G 0 2G Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 13 Cmpd. 17 Cmpd. 18 Rate g/ha 8 31 62 250 31 125 Crabgrass O 0 0 0 0 3G Barnyardgrass 0 2G 4G 6G 5G 7G Sorghum O 2G 3G 5G 6G 8G Wild Oats 0 2G 0 3G 2G 5G Johnsongrass O 3G 0 0 7G 8G Dallisgrass 0 0 0 0 2G 3G Giant foxtail 0 4G 0 0 0 2G Ky.. bluegrass. 2G 3G 0 0 6G 9G Cheatgrass 0 2G 2G 4G 5G 9G Sugar beets 8G 1OC 2G 9G 7G 8G Corn 2G 4E 2G 3G 6G,5C 8G,5H Mustard 8G 9G 9G 10G - Cocklebur O 5G 2G 2G - Nutsedge 4G 5G 8G 8G - Cotton 2G 5G 0 2G - Morningglory 3G,3C 6C,5C 2G 4G - Sicklepod 0 8G 0 3G - Teaweed 3G <RTI ID=224.33> 7G 0 2G - Velvetleaf 3G,3C 8G,7H 5G 6G - aimsonweed 2G 7G 4G 8G - Soybean 0 2G 0 2G - Rice 0 3G 0 3G - Wheat 0 3G 0 3G - Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 19 Rate g/ha 31 31 125 125 Crabgrass O 5G O 6G Barnyardgrass 4G 8G 6G,3C 9G Sorghum 3G 8G 5G,5H 9G Wild Oats 2G 5G 4G 7G Johnsongrass 9G 5G 4G 7G Dallisgrass 0 6G 2G 8G Giant foxtail 0 5G O 70 Ky. bluegrass -5G 8G 8G 9G Cheat grass 6G 9G 7G 9G Sugar beets 7G 7G 8G 8G Corn 5G,5H 7G 5G,5H 9G Mustard 9G 9G 9G,9C 9G Cocklebur 2G,2H 5G 3G,3H 7G Nutsedge 8G 7G 9G 8G Cotton 0 6G 3G 8G Morningglory 0 5G O 7G Sicklepod 6G 8G 7G <RTI ID=225.29> 9G Teaweed 3G 7G lOC 7G Velvetleaf 4G 7G 8G 9G Jimsonweed 5G 7G 5G 8G Soybean 4G,3H 7G 5G,5H 8G,7H Rice 5G 5G 7G 7G Wheat 0 2G 2G 4G Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 20 Rate g/ha 31 125 Crabgrass O 0 Barnyardgrass O 0 Sorghum O 5G Wild Oats O 0 Johnsongrass O O Dallisgrass O 0 Giant foxtail 0 0 Ky. bluegrass 0 0 Cheatgrass O 0 Sugar beets 9G lOC Corn O 0 Mustard 9G lOC Cocklebur O 5G,2H Nutsedge 2G 8G Cotton 7G 9G Morningglory 3G 7G Sicklepod 2G 5G Tesweed O 3G Velvetleaf 0 4G Jimsonweed O 4G Soybean 6G 9G Rice 2G 3G Wheat O 0 Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 21 Rate g/ha 31 31 125 125 Crabgrass 0 5G 3G 6G Barnyardgrass 6G 5G 8G 9G Sorghum 4G 3G 7G 4G Wild Oats 4G 0 4G 2G Johnsongrass 40 4G 4G 5G Dallisgrass 0 5G 2G 6G Giant foxtail 2G 4G 6G 6G Ky. bluegrass 0 5G 4G 8G Cheatgrass 6G 5G 8G 7G Sugar beets lOC 8G lOC lOC Corn 3G 3C 9G 5G,5H Mustard 9G,9C 9G 9G,9C lOC Cocklebur 7G - 8G 7G Nutsedge 8G 8G 10C 10C Cotton 7G 2G 9G 4G Morningglory 6G 3G 9G 4G Sicklepod 7G 4G 9G 8G Teaweed 2G 4G 5G 6G Velvetleaf 7G 4G 9G 6G Jimsonweed 8G 4G 9G 5G Soybean 6G 3G,3H 8G 6G,5H Rice 6G 3G 8G 5G Wheat O 0 2G 0 Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 22 Compound 24 Rate g/ha 31 125 2 16 Crabgrass O 6G O 3G Barnyardgrass 2G 4G 0 6G Sorghum 2G 3G O 9G Wild Oats O 2G O O Johnsongrass O 2G O 5G Dallisgrass O 0 0 5G Giant foxtail O O O 6G Ky. bluegrass O O - Cheatgrass O 3G 3G 8G Sugar beets 6G 7G 2G 6G Corn 2G,3C 3G,3C O O Mustard - - 7G 9G Cocklebur - - O 8G Nutsedge - - O 2G Cotton - - O 4G Morningglory - - O 6G Sicklepod - - 7G 9G Teaweed - - O 5G Velvetleaf - - O 5G Jimsonweed - - O O Soybean - - 4G 6G,5H Rice - - 5G 8G Wheat - - 0 O Table O (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Cmpd. 25 Compound 42 Rate g/ha 2 16 16 62 250 Crabgrass 0 3G 0 4G 5G Barnyard grass 2G 4G 3G 6G 6G Sorghum 5G 7G - - Wild Oats O O O 6G 6G Johnsongrass O 5G 3G 6G 8G Dallisgrass 0 5G - - Giant foxtail 0 4G 0 0 3G Ky. bluegrass - - - - Cheatgrass 0 7G - - Sugar beets 3G 7G 5G 8G 9G Corn 0 4G 2G 8G 9G Mustard 6G 9G - - Cocklebur 6G 8G 0 7G 8G Nutsedge 2G 7G 3G 5G 9G Cotton 3G 7G O 3G <RTI ID=229.42> 8G Morningllory O 6G 3G 8G 8G Sicklepod O 6G 3G 8G 8G Teaweed 3G 5G 0 7G 5G Velvetleaf 3G 4G 0 5G 8G Jimsonweed O 2G O 7G 7G Soybean 3G 7G,5H 4G 7G 8G Rice 30 7G 0 8G 8G Wheat O 0 0 O 30 Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 43 Rate g/ha 4 16 62 250 Crabgrass O 0 4G 4G Barnyardgrass O 0 0 0 Sorghum - - - Wild Oats O O O 3G Johnsongrass 0 0 0 4G Dallisgrass - - - Giant foxtail 0 0 0 0 Ky. bluegrass -- - - Cheatgrass - - - Sugar beets 3G 8G 9G 9G Corn O O 3G 7G Mustard - - - Cocklebur O O 6G 8G Nutsedge O 3G 5G 7G Cotton O O 8G 9G Morningglory O 6G 7G 8G Sicklepod 0 3G 5G 8G Teaweed 0 4G 4G 5G Velvetleaf O 0 3G 7G Jimsonweed O 3G 5G 7G Soybean O O 5G 8G Rice O O 5G 8G Wheat O 0 0 0 Table D (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 44 Rate g/ha 4 16 62 250 Crabgrass O 0 3G 6G Barnyard grass 3G 6G 9G 9G Sorghum - - Wild Oats O 0 3G 6G ohnsongrass 5G 6G 8G 9G Dallisgrass - - - Giant foxtail O - - 4G Ky. bluegrass - - - Cheatgrass Sugar beets 3G 8G 9G 9G Corn 0 4G 9G 9G Mustard g Cocklebur 0 6G 7G 9G Nutsedge O 0 4G 8G Cotton 0 3G 5G 9G Morningglory O O 2G 8G Sicklepod O O 4G 8G Teaweed O 3G 4G 8G Velvetleaf 0 3G 7G 9G Jimsonweed 2G 7G 8G 9G Soybean 2G 4G 7G 9G Rice O 6G 9G 10G Wheat O 0 3G 7G Test E Plastic pans lined with polyethylene liners were filled with prepared Woodstown sandy loam soil. Seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), rapeseed (Brassica napus), downy brome (Bromus tectorum), ripgut brome (Bromus rigidus), Russian thistle (Salsola kali), Galium aparine, speedwell (Veronica persica), kochia (Kochia scoparia), shepherd's purse (Capsella bursapastoris), Matricaria inodora, black nightshade (Solanum nigrum), wild buckwheat (Polygonum convolvulus), tansy mustard (Descurainia pinnata), tumble mustard (Sisymbrium altissium), yellow rocket (Barbarea vulgaris) and sugar beets (Beta vulgaris) were planted. These pans were treated pre-emergence. At the same time pans in which these plant species were already growing were treated post-emergence. Plant height at the time of treatment ranged from 1-20 cm, depending upon plant species. The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 19-22 days, at which time the treatments were compared to the controls and the effects visually rated. The recorded data are presented in Table E. Several of the compounds tested provided selective weed control in wheat and/or barley. Table E Compound 7 Rate g/ha 30 125 500 Pre-Emergence wheat 1G 7G 8G barley 3G 6G 7G wild oats 3G 6G 7G downy brome 3G 9G 9G cheatgrass 3G 7G 7G blackgrass 6G 7G 2C,8G annual bluegrass 6G 9G 2C,9G green foxtail 5G 7G 9C,9G quackgrass 6G 8G 3C,9G Italien ryegrass 6G 8G 5C,9G ripgut brome 5G 8G 5C,9G Russian thistle O 3G 2C,9G tansy mustard - - Galium aparine 10C 10C 8G tumble mustard 9G 10C 10C kochia 4G 3G lOC shepherd's purse lOC lOC lOC Matricaria inodora 8G 9G lOC black nightshade 0 6G 6G yellow rocket 9G 9G 9G rapeseed 9G 9G 5C,9G wild buckwheat 4G 6G 3C,9G Post-Emergence wheat 2G 2G 38 barley <RTI ID=233.10> 2G 4G 4G wild oats 0 3G 4G downy trome 0 6G 5G cheatgrass 0 5G 3G blackgrass 3G 0 5G annual bluegrass 5G 0 5G green foxtail quackgrass 0 0 4G Italian ryegrass 3G 5G 68 ripgut brome 2G 3G 6G Russian thistle - - 8G tansy mustard 10C 10C 10C Gallum aparine 3C,7G 10C 3C,9G tumble mustard 8C,8G 10C 10C kochia 2G 9C 7G shepherd's purse 9C,9G 10C 9C,9G Matricaria inodora 3C,5G 3C,8G 3C,8G black nightshade 4G 7G 4G yellow rocket 8G 10C 10C rapeseed 8G 7C,9G 7G wild buckwheat 10C 10C 7G Table E (continued) Compound 8 Compound 10 Rate g/ha 16 62 62 16 Pre-Emergence wheat 2G 3G 0 0 barley 3G 5G 0 0 wild oats 3G 4G 5G 0 downy brome 5G 8G 8G 6G cheatgrass 4G 7G 5G 6G blackgrass 5G 8G 1C,8G 4G annual bluegrass 5G 7G 8G 5G green foxtail 36 7G 1C O quackgrass <RTI ID=234.21> 4G 8G 8G 7G Italian ryegrass 4G 8G 2C,8G 1C,4G ripgut brome 4G 8G 7G 5G Russian thistle 0 3G 1C,2G 2G tansy mustard - - 2C,9G 8G Galium aparine 8G 7G 2C,6G 3G tumble mustard 9G 10C 2C,9G 8G kochia 0 0 5G 0 shepherd's purse 9G 10C 2C,9G 8G Matricaria inodora 8G - 8G 0 0 black night shade O O 2G O yellow rocket 9G 9G 9G 9G rapeseed 9G 9G 2C,9G 6G wild buckwheat 2G 4G 5G 1C Post-Emergence wheat 3G <RTI ID=234.38> 2G 4G 1G barley 2G 4G 2G 1G wild oats 5G 5G 5G 4G downy brome 7G 4G - 6G 4G cheatgrass 5G 5G 5G 2G blackgrass 4G 4G 2C,9G 2C,8G annual bluegrass 6G 6G 8G 5G green foxtail - - 5G 4G quackgrass 8G 5G 7G 6G Italian rye grass 5G 6G 7G <RTI ID=234.61> 7G ripgut brome 4G 5G 7G 6G Russian thistle - 2G 0 0 tansy mustard 10C 10C 8C,9G 8C,9G Galium aparine 3C,7G 10C 2C,4G 2C,4G tumble mustard 7G lOC lOC 9C,90 kochia 0 0 2G 0 shepherd's purse 6G 7C,8G lOC lOC Matricaria inodora 5G 3C,7G 2C,6G 2C,5G black nightshade 0 5G 5G 5G yellow rocket 8C 3C,8G 10C 2C,8G rapeseed 5G 8G 8C,9G 8G wild buckwheat 5G 7G 6G 5G Veronica persica 2G 5G - Table E (continued) Compound 11 Rate g/ha 1 4 16 62 Pre-Emergence wheat 0 0 0 0 barley 0 0 20 20 wild oats 0 0 2G 2G cheatgrass 0 0 60 60 blackgrass 20 40 3C,90 3C,90 annual bluegrass 30 20 80 2C,8G green foxtail 0 20 60 1C,6G Italian ryegrass 0 30 1C,2G 40 rapeseed 8G 10C 6C,9G 5C,9G Matricaria inodora 70 2C,9G 80 90 Galium aparine - 6G 2C,8G 4C,8G Russian thistle O O 1C,2G 2C,6G shepherd's purse 10E 10E 8C,9G 7C,9G kochia 20 80 5C,7G 50 black nightshade 0 40 70 70 speedwell 30 30 - wild buckwheat 2G 7G 3C,7G 3C,6G sugar beets 60 80 downy brome - - 60 60 quackgrass - - 70 9G ripgut brome - - 7G 8G tansy mustard - - 7C,9G 7C,9G tumble mustard - - 9C,9G 9C,9G yellow rocket - - 3C,9G 3C,9G Post-Emergence wheat 0 0 40 50 barley O <RTI ID=235.7> 0 30 30 wild oats 0 0 4G 30 cheatgrass 0 o 30 30 blackgrass O 4G 2C,8G 3C,9G annual bluegrass O O 2C,9G 2C,8G green foxtail 0 0 80 70 Italian rye grass 0 0 50 60 rapeseed 70 lOC 10C lOC Matricaria inodora 3G 2C,7G 8C,9G 9C,9G Galium aparine 0 30 2C,8G 30,70 Russian thistle lOC 7c shepherd's purse 10C 10C 10C 10C kochia 3G 5G 7C,8G 3C,8G black nightshade 0 0 80 50 speedwell 0 30 - - wild buckwheat O 8G 5C,8G 3C,8G sugar beets 8G 90 - downy brome - - 40 50 quackgrass - - 7G 6G ripgut brome - - 5G 5G tansy mustard - - lOC 10C tumble mustard - - lOC lOC yellow rocket - - lOC lOC Table E (continued) Compound 13 Compound 18 Rate g/ha 4 16 16 62 Pre-Emergence wheat 0 0 0 5G barley 0 0 0 4G wild oats O 0 3G 6G cheatgrass 0 0 8G 8G blackgrass 0 0 8G 9G,9C annual bluegrass 0 0 8G 9G green foxtail 0 0 0 2G Italian ryegrass 0 0 7G 8G,8C rapeseed 0 7G 9G 9G Matricaria inodora 2G 7G 7G 9G Galium aparine 4G 7G 2G,3U 2G,3U Russian thistle 0 6G 0 0 shepherd's purse 7G lOC 8G 9G,9C kochia 0 0 6G 6G black nightshade 0 3G 2G 6G speedwell 0 2G 8G 7G wild buckwheat 1C,2G 1C,9G 2G 2G sugar beets 4G 2C,90 7G 9G Post-Emergence wheat 0 0 0 0 barley 0 0 O 1G wild oats 0 0 O 1G cheatgrass O 0 5G 7G blackgrass 0 0 4G 7G annual bluegrass 0 0 4G 6G green foxtail 0 0 3G 4G Italian ryegrass 0 0 5G 7G,6C rapeseed <RTI ID=236.43> 9G lOC lOG lOG Matricaria inodora 0 5G 4G 9G Galium aParlne 0 5G 0 0 Russian thistle 3G 8G shepherd's purse 5G 8G lOG lOG kochia 0 0 0 8G black nightshade 0 0 0 3G speedwell 0 0 0 5G wild buckwheat 6G 8G lOG lOG sugar beets 7G 9G 5G <RTI ID=236.66> 6G Table E (continued) Compound 19 Rate g/ha 16 62 Pre-Emergence wheat O 2G barley O 3G wild oats O 4G cheatgrass 2G 7G blackgrass 3G 6G annual bluegrass 3G 7G green foxtail O O Italian ryegrass O 8G repeseed 10C 10C Matricaria inodora 10C 10C Galium aparine O O Russian thistle 6G 7G shepherd's purse 10C 10C kochia 5G 6G black nightshade 0 4G speedwell 9G 9G wild buckwheat O 5G,1C sugar beets 9G,3C 10C Post-Emergence wheat 1G 2G barley 1G 2G wild oats 1G 1G cheatgrass 1G 4G blackgrass 1G 6G annual bluegrass 1G 5G green foxtail O O Italian ryegrass 2G 8G rapeseed 4G,1C 10C Matricaria inodora 3G,1C 5G,7C Galium aparine O O Russian thistle 2G 5G shepherd's purse 1G 5G kochia O 5G black nightshade O O speedwell 0 5G wild buchwheat 5G,4C 5G,4C sugar beets 8G 7G,7C Table E (continued) Compound 20 Rate g/ha 4 16 62 Pre-Emergence wheat 0 0 2G barley 0 0 2G wild oats 0 O 1G cheatgrass 0 0 3G blackgrass 0 2G 6G annual bluegrass 0 2G 5G green foxtail 0 0 2G Italian ryegrass 0 3G 5G rapeseed 2G 8G lOC Matricaria inodora 3G 9G lOC Galium aparine 6G 8G 8C,9G, <RTI ID=238.18> Russian thistle 0 0 3C,50 shepherd's purse 7G 9G lOC kochia 0 4G 8G black nightshade 6G 5G 6G speedwell 4G SO wild buckwheat 0 8G 9G sugar beets 5G 8G 2C,90 Post-Emergence wheat- 0 0 0 barley 0 0 0 wild oats 0 0 3G cheatgrass 0 0 0 blackgrass 0 0 0 annual bluegrass 0 0 3G green foxtail 0 0 0 Italian ryegrass 0 0 0 rapeseed 8G 9C,9G lOC Matricaria inodora 4G 7G 8G Galium aparine - - Russian thistle 0 0 SC shepherd's purse 0 9C lOC kochia 0 O 2G black nightshade 0 2G 4G speedwell 0 2G 2G wild buckwheat 0 5C 8G sugar beets 0 3G 7G Table E (continued) Compound 21 Rate g/ha 16 62 Pre-Emergence wheat 0 Q barley 0 0 wild oats 0 0 cheatgrass 0 0 blackgrass 0 2G annual bluegrass 0 0 green foxtail 0 0 Italian ryegrass 0 0 rapeseed 10C 10C Matricaria inodora 8G 9G Galium aparine O 4G Russian thistle 5G 9G shepherd's purse lOC lOC kochia 3G 8G black nightshade 0 5G speedwell 0 0 wild buckwheat 1G 5G sugar beets 6G 10C Post-Emergence wheat 0 1G barley 0 0 wild oats 0 0 cheatgrass O O blackgrass 0 0 annual bluegrass 0 0 green foxtail 0 0 Italian rye grass 0 0 rapeseed lOC lOC Matricaria inodora 4G 9G Galium aparine 0 6G Russian thistle 4G 10C shepherd's purse 8G lOC kochia 4G 9G black nightshade 0 0 speedwell 0 0 wild buckwheat 9G,7C lOC sugar beets lOC lOC Table E (continued) Compound 23 Rate g/ha 16 62 1 4 Pre-Emergence wheat - 0 0 0 barley - 0 0 0 wild oats - 0 0 0 cheatgrass - 0 0 0 blackgrass - 9G,3C 0 0 annual bluegrass - 6G 0 0 green foxtail - <RTI ID=240.3> 2G 0 0 Italian ryegrass - 8G 0 0 rapeseed - lOC 3G 9G Matricaria inodora lOC - 4G 7G Galium aparine 8G - 0 3G Russian thistle 8G - 4G 9G shepherd's purse lOC - 4G 8G kochia 9G - 0 7G black nightshade 7G - 0 7G speedwell lOC - 0 6G,1C wild buckwheat 10C - 3G lOC sugar beets lOC - 4G 7G Post-Emergence wheat 0 0 0 0 barley 0 0 0 0 wild oats 0 0 0 0 cheatgrass <RTI ID=240.22> 1G 4G 0 0 blackgrass 6G S0,7C 0 0 annual bluegrass 6G 7G 0 0 green foxtail 0 6G 0 0 Italian rye grass 0 8G 0 0 rapeseed 9G 9G,9C 0 0 Matricaria inodora 8G,7C lOC lG,lC 8G,3C Galium aparine 0 6G 0 0 Russian thistle 10C 10C 10C 10C shepherd's purse 10C 10C 8G,7C 10C kochia 10C 10C 7G 8G,7C black nightshade 0 5G 0 0 speedwell 8G lOC 0 4G wild buckwheat lOC lOC 3G,1C 5G sugar beets 9G lOC <RTI ID=240.39> 4G,2C lOC Test F This test was designed to evaluate the potential utility of compounds from within the scope of the invention for selective weed control in rice. The crop was transplanted into simulated paddies containing soil and propagules of barnyardgrass (Echinochloa sp.), water chestnut (Eleocharis sp.), and arrowhead (Sagittaria sp.). Direct seeded rice, Scirpus mucronatus, Cyperus difformis, water plantain (Alisma trivale), and Monochoria vaginalis were also treated with several of the test chemicals to further determine selectivity. Three days after transplanting, the test chemicals were applied to the paddy water in a non-phytotoxic solvent at the rates shown in Table F. The paddies were maintained in a greenhouse, and plant response ratings were taken several weeks after application utilizing either the rating system as described for Test A or a O to 100 rating system where 0 is no injury and 100 is plant death. It will be seen that several of the compounds tested provide control of troublesome weeds at rates which are non-injurious to rice. Table F Compound 2 Rate g/ha 8 8 16 16 30 63 63 Rice transplants 0 0 0 0 0 0 Rice direct seeded - - 0 - - 0 Barnyardgrass 0 80 75 90 90 100 Water chestnut 60 100 80 90 100 95 Arrowhead 70 - 90 90 - 95 Scirpus 50 0 50 50 80 70 Cypress 20 90 50 95 90 100 Water plantain 80 70 100 90 90 100 Monocharia 50 - 70 70 - 100 Table F (continued) Compound 7 Rate g/ha .12 .25 2.5 10 Rice transplants 0 0 0 0 Rice direct seeded 0 0 - Barnyardgrass O 0 9C 9C Water chestnut 0 100 40 90 Arrowhead O 0 3H 5G,2H Scirpus O 0 - Cypress O 0 - 0 Water plantain 0 70 - Compound 9 Rate g/ha 2.5 10 Rice transplants 0 40 Barnyardgrass 8G 10C Water chestnut 30 80 Arrowhead 9G,6C 9G,5C Compound 11 Rate g/ha .5 2 2.5 10 Rice transplants 0 40 4G 2C,8G Rice direct seeded 90 90 - - Barnyardgrass 80 100 90 lOC Water chestnut 100 100 90 2C,9G Arrowhead 100 100 90 Scirpus 50 80 - Cypress 100 100 - - Water plantain 100 100 - Table F (continued) Compound 17 Rate g/ha 10 25 40 100 Rice transplants 5G O 3G 51 Barnyardgrass 4G 9C 8G 9C Water chestnut 5G - 3C,9G 9G Arrowhead 2G lOE 9G 10E Compound 19 Rate g/ha 1 2.5 5 5 5 Rice transplants 0 0 0 0 <RTI ID=243.9> 4G Barnyardgrass 3G 5G 6G 9C lOC Water chestnut 10C 10C 10C 9G 2C,7G Arrowhead 1H 5G,2H 8G,3H lOE Compound 19 (continued) Rate g/ha 10 10 20 20 20 20 Rice transplants 2G 0 2G,1C 3G 7G 1G Barnyardgrass 9C lOC 9C lOC 8G lOC Water chestnut lOC 8G lOC 9G,2C 9G 9G,3C Arrowhead 9G,3C 10E 9G,4C 9G,5C - 9G,3C Compound 19 (continued) Rate g/ha 40 40 80 80 160 Rice transplants 3G 8G 2C,8G 7G 8G,4C Barnyardgrass lOC lOC lOC lOC lOC Water chestnut 9G,2C 9G,3C 2C,9G 9G,4C 10G,7C Arrowhead 9G,5C 9G,2C - 9G,6C 9G,3C Table F (continued) Compound 20 Rate g/ha 20 40 80 160 Rice transplants O - O 8G Barnyardgrass O - - 6G Water chestnut 50 90 80 80 Arrowhead O 0 0 0 Compound 21 Rate g/ha 1 2.5 5 5 Rice transplants 0 0 0 1G Barnyardgrass 1G 1G 6G 3C,8G Water chestnut lOC lOC lOC lOC Arrowhead O 2H 2G,3H Compound 21 (continued) Rate g/ha 10 10 10 10 15 Rice transplants 0 0 0 0 0 Barnyardgrass 9C 9C 9C 9C 9C Water chestnut lOC lOC lOC lOC 1OC Arrowhead 5G,2H 4G,2H 6G,3H 5G,3H 90 Compound 21 (continued) Rate g/ha 20 20 20 20 20 Rice transplants 0 4G 0 0 0 Barnyardgrass lOC 2C,9G 9C lOC lOC Water chestnut lOC 90 lOC 6G 10G Arrowhead 90 - 50 4G,2H 9G,3H Table F (continued) Compound 21 (continued) Rate g/ha 30 30 30 40 40 40 Rice transplants 0 0 0 0 0 0 Barnyardgrass lOC 9C lOC lOC 9C lOC Water chestnut lOC 90 90 10C 90 lOC Arrowhead 90 10G 90 lOE lOE lOC Compound 21 (continued) Rate g/ha 50 50 60 80 80 Rice transplants 0 0 70 70 30 Barnyardgrass 9C lOC lOC lOC lOC Water chestnut 90 9G,6C lOC lOC lOC Arrowhead 8G 90 lOE - lOE Compound 22 Rate g/ha 4 16 Rice transplants 0 0 Rice direct seeded 20 20 Barnyardgrass 70 Water chestnut 0 20 Arrowhead 100 100 Scirpus 0 30 Cypress Water Plantain 70 70

Claims: Claims 1. A compound of the formula: EMI246.1 wherein EMI246.2 CHClCH2Cl, CHClCHCl2, CH=CBr2, CH=CHR9, CH=CHCO2CH3 or CH=CF2; R2 is H, F, C1, CH3, OCH3 or CF3; R3 is H or CH3; R4 is H, F, C1, Br or CH3; R5 is F, C1, Br, OC(O)R6, OC(O)CF3, OH, OCH2#, OSO2R6, OSO2CF3, OSO2C6H5R7, S(O)mR6, OSO2N(CH3)2 or CO2R8; R6 is C1-C3 alkyl; R7 is H, F, C1, Br, CH3, OCH3 or CF3; R8 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl; R9 is OCH3 or OCH2CH3; R10 is H, OCH} or 0CH2CH3; R11 is H, Cl or OCH3; R12 is H or CM3; n is O or 1; m is O, 1 or 2; EMI247.1 X is CM3, OCH3, C1, F, Br, CH2CH3, OCH2CH3 or OCF2H; Y is H, NH2, NHCH3, N(CH3)2, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of a) F, b) Cl or c) Br, CH2OCH3, CH2OCH2CH3, C1-C4 alkoxy, C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH2OCH3, CH(OCH3)2, CH(OCH2CH3)2, EMI247.2 OCH2CF3, OCH2CH2F, OcH2CH2Cl, OCH2CH2Br or GCF2T; wherein G is O or S and T is H, CHC1F, CHBrF, CF2H or CHFCF3; Z is CH, N, CCH3, CBr, CCl, CF or CCH2CM3; X1 is O or CH2 Y1 is H, CH3, OCH3 or Cl; X2 is CH3, OCH3 or SCH3; Y2 is CH3, CH2CH3 or CH2CF3; and X3 is CH3 or OCH3; and their agriculturally suitable salts; provided that a) when R4 is halogen, R5 is the same halogen; b) when R5 is halogen, R4 is either hydrogen or the same halogen; c) when n is 1, R11 is hydrogen; d) when R12 is CH3 and R10 is alkoxy, R@ is the same alkoxy;. and e) then X is C1, then Z is CH and Y is NH2, NHCH3, N(CH3)2, CH3 OCH3 or OCF2H. 2. A compound of Claim 1 wherein R2 is H, and R1 is (CH2)nCH2CHR4R5, EMI248.1 3. A compound of Claim 2 wherein A is A-l; Z is CH or N; X is CH3, OCH3, Cl or OCF2H and Y is CH3, CH2CH3, OCH3, OCH2CH3, OCF2H, SCF2H, CH2OCM3 or CF3. 4. A compound of Claim 3 wherein R1 is CH2CH2Cl, CH2CH20H, CH(OCH3)CH2OCH3 or EMI248.2 5. A compound of Claim 4 wherein R3 is H. 6. The compound of Claim 1 which is N-[(4,6- dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-methoxyethyl)benzensulfonamide. 7. The compound of Claim 1 which is N-t(4- methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]amino sulfonyl-2-(2-methoxyethyl)benzenesulfonamide. 8. The compound of Claim 1 which is N-[(4,6dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl 2-(2-p-toluenesulfonyloxyethyl)benzenesulfonamide. 9. The compound of Claim 1 which is N-((4- methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)benzenesulfonamide. 1Q. The compound of Claim 1 which is N-t(4- methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)bEm ene- sulfonamide. 11. The compound of Claim 1 which is N-±(4- methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-chloroethyl)benzenesulfonamide. 12. The compound of Claim 1 which is N-[(4,6- dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl2-(2-chloroethyl)benzenesulfonamide. 13. The compound of Claim 1 which is N-f(4,6- dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-chloroethyl)benzenesulfonamide. 14. A compound of Claim 1 of the formula EMI249.1 wherein R1 is CH2CHR4R5, CH=CBr2, CH=CH(OCH3), CH=CHCO2CH3 or CH=CF2; R2, R3, R6, R7, R8 and m are as defined in claim 1; R4 is H, C1, Br or CH3; R5 is F. C1, Br, OC(O)R6, OC(O)CF3, OH, OSO2R6, OSO2CF3; OSO2C6H5R7, S(O)mR6 or CO2R8; X is CH3, OCH3 or C1; Y is CH3, OCH3, C2H5, OC2H5, CH2OCH3, CH(OCH3)2, N(CH3)2, NH2 or NHCH3; EMI249.2 Z is N or CH; and agriculturally suitable salts thereof. 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a herbicide compound and at least one of the following: surfactant, solid or liquid inert diluent, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 14. 16. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 14. 17. A method for regulating the growth of plants by applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of any of claims 1 to 14. 18. A process for the preparation of compounds.of Claim 1 which comprises (a) reacting an appropriate aryl sulfonylisocyanate of formula (II) or an appropriate carbamate of formula (VII) with an appropriate amino heterocycle of formula (III): EMI250.1 wherein R1, R2, R3 and A are as defined in Claim 1 except that R5 is not OH; or (b) for the.preparation of compounds of Claim 1 wherein R5 is OH, hydrolysing under mild conditions a trifluoroacetyl compound of formula EMI250.2 wherein R2, R3, n and A are as defined in Claim 1 and R4 is H or CH3; or (c) reacting an appropriate sulfonamide of formula (IV) with an appropriate methyl carbamate of formula (VIII); EMI251.1 wherein R1, R2, R3, and A, X, Y and Z are as defined in Claim 1 except that R5 is not OH. Claims: 1. A process for the preparation of a compound of the formula: EMI252.1 wherein EMI252.2 CHClCH2Cl, CHClCHCl2, CH=CBr2, CH=CHR9, CH=CHCO2CH3 or CH=CF2; R2 is H, F, Cl, CH3, OCH3 or CF3; R3 is H or CH3 R4 is H, F, C1, Br or CH3; R5 is F, C1, Br, OC(O)R6, OC(O)CF3, OH, OCH2@, OSO2R6, OSO2CF3, OSO2C6H5R7, @@@@ m@6' OSO2N(CH3)2 or CO2R8; R6 is C1-C3 alkyl; R7 is H, F, C1, Br, CH3, OCH3 or CF3; R8 is C1-CD alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl; R9 is OCH3 or OCH2CH3; R10 is H, OCH3 or OCH2CH3; R11 is H, Cl or OCH3; R12 is H or CH3; n is O or 1; m is 0, 1 or 2; EMI253.1 X is CH3, OCH3, C1, F, Br, CH2CH3, OCH2CH3 or OCF2H; Y is H, NH2, NHCH3, N(CH3)2, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of a) F, b) Cl or c) Br, CH2OCH3, CH20CH2cH3, C1-C4 alkoxy, C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH2OCH3, CH(OCH3)2, CH(OCH2CH3)2, EMI253.2 OCH2CF3, OCH2CH2F, OCH2CH2C1, OCH2CH2Br or GCF2T; wherein G is O or S and T is H, CHC1F, CHBrF, CF2H or CHFCF3; Z is CH, N, CCH3, CBr, CC1, CF or CCH2CH3; X1 is O or CM2; Y1 is H, CH3, OCH3 or Cl; X2 is CM3, OCH3 or SCH3; Y2 is CH3, CH2CH3 or CH2CF3; and X3 is CH3 or OCH3; or an agriculturally suitable salt thereof: provided that a) when R4 is halogen, R5 is the same halogen; b) when R5 is halogen, R4 is either hydrogen or the same halogen; c) when n is 1, R11 is hydrogen; d) when R12 is CH3 and R10 is alkoxy, R9 is the same alkoxy; and e) when X is C1, then Z is CH and Y is NH2, NHCH3, N(CH3)2, CM3, OCH3 or OCF2H,which comprises (a) reacting an appropriate arylsulfonyl isocyanate of formula (II) or an appropriate carbamate of formula (VII) EMI254.1 with an appropriate aminoheterocycle of formula R3NHA (III) wherein R1, R2, R3 and A are as defined above except that R5 is not OH; or (b) hydrolysing under mild conditions a compound of formula (I) wherein R5 is O.CO.Cr3 and R4 is H or CH3 to obtain a corresponding compound of formula (I) wherein R5 is OH; or (c) reacting an appropriate sulfonamide of formula (IV) EMI254.2 with an appropriate methylcarbamate of formula (VIII) EMI254.3 wherein R1, R2, R3 A, X, Y and Z are as defined ab.ove except that R5 is not OH. 2. The process of claim 1 wherein said product has the formula EMI255.1 wherein R1 is CH2CHR4R5, CH=CBr2, CH=CH(OCH3), CH=CHCO2CH3 or CH=CF2; R2, R3, R6, R7, R8 and m are as defined in claim 1; R4 is H, C1, Br or CH3 R5 is F, C1, Br, OC(O)R6, OC(O)CF3, OH, OSO2R6, OSO2CF3, OS02C6H5R7, S(O) mR6 or CO2R8; X is CH3, OCH3 or Cl, Y is CH3, OCH3, C2H5, OC2H5, CH2OCH3, CH(OCH3)2, N(CH3)2, NH2 or NHCH3; EMI255.2 Z is N or CH; 3. The process of claim 1 or 2 wherein R2 is H, and R1 is (CH2)nCH2CHR4R5, (CH2)nCHCH2R9 or (CH2)nCHCH(R9)2 R10 R10 4. The process of Claim 3 wherein A is A-1;-.Z is CH or N; X is CH3, OCH3, Cl or OCF2H and Y is CH3, CH2CH3, OCH3, OCH2CH3, OCF2M, SCF2H, CH2OCH3 - - or CF3. 5. The process of Claim 4 wherein P1 is CH2CH2C1, CH2CH20H, CH(OCH3)CH2OCH3 or EMI255.3 6. The process of Claim 5 wherein R3 is H. 7. The process of Claim 1 or 2 wherein the product is selected from N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-methoxyethyl0benzenesulfonamide; N-[(4t6-dimethOxypyrimidin-2-ylaminocarbonyl]2minosulsonyl- 2-(2-p-toluenesulfonyloxyethyl)benzenesuflonamide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-p-toluenesulfonyloxyethyl)benzenesulfonamide; N-[(4-methOxy-6-methylpyrimidin-2-yl)aminocarbonyl]amino- sulfonyl-2-(2-chloroethyl)benzenesulfonamide; or N-I(4,6-dimethOxyp.rimidin-2-ylXaminocarbonyl]aminosulfonyl- 2-(2-chloroethyl)benzenesulfonamide. 8. The process of Claim 1 or 2 wherein the product is selected from N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl-2-(2-methoxyethyl)benzenesulfonamide; N-[(4-methOxy-6-methyl-1,3,5-triazxn-2-ylaminocarbonyl3- amino sulfonyl - 2- (2-2-toluenesul fonyloxyethyl) benzenesulfonamide; N-t(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl3amino- sulfonyl-2-(2-chloroethyl)benzenesulfonamide. 9. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound1 characterised in that said herbicidal compound comprises a compound of formula (I) as defined in any of Claims 1 to 8. 10. A method for regulating the growth of plants by applying to the locus -of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of formula (I) as defined in any of Claims 1 to 8.

Inventors: HANAGAN, MARY ANN, THOMPSON, MARK EWELL
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1983
Main classification: A01N47
IPC codes: A01N47, C07D521