HERBICIDAL SULFONAMIDES

Abstract: Arylmethanesulfonylureas and arylsulamonlureas of the formula wherein J is an arylmethyl or aryloxy group; R is H or CH₃; and A is a mono- or bicylic heterocyclic group, e.g. pyrimidyl or triazinyl; and their agriculturally suitable salts, exhibit herbicidal activity. Some of these compounds may also be used as plant growth regulants. The compounds may be formulated for use in conven­ tional manner. They may be synthesised by a variety of routes, e.g. by reacting a sulfonyl isocyanate JSO₂NCO with an appropriate heterocyclic amine HA.

Description: Title HERBICIfAL SULFONAMIDES Background of the Invention This invention relates to novel arylmethane- and arylsulfamoyl- sulfonylureas which are useful as preand post-emergence herbicides. The compounds of this invention and their agriculturally suitable salts. are useful as agricultural chemicals such as herbicides. U.S. Patent Nos. 4.169,719 and 4.127.405 disclose herbicidal benzene and thiophene sulfonamides. U.S. Patent No. 4.435.206 discloses herbicidal pyridine sulfonamides U.S. Patent 4.420.325 discloses benzyl sulfonylureas such as: EMI1.1 EP-A-87,780 (published September 7, 1983), filed by Nissan Chemical Industries, discloses pyrazole sulfonamides of the general formula shown below. EMI1.2 wherein A is H. C1-C8 alkyl or optionally substituted phenyl; B and C are independently H. halogen, NO2, C1-C8 alkyl. CO2R, etc.: D is H or C1-C8 alkyl: Z is CH or N; and X and Y are methyl, methoxy, etc. European Patent Application 71.441, published February 9. 1983, discloses compounds of the formula EMI2.1 where Z is CH or N; X is CH3 or OCH3: Y is C1, CH3, OCH3. OC2H5, CH20CH3, NH2. NHCH3. N(CH3)2, CH(OCH3)2, EMI2.2 where R1 is H or C C1-C3 alkyl; R2 is H or CH3. R5 is H, CH3. OCH3, Cl, Br, NO2. CO2R7, S 2R8' 0502R9. S02NR10R11; R6 is H or C1-C3 alkyl; R6' is H or CH3; Q is 0. S, or SO2; and Q1 is CR3R4 or 0. Utility as a pre- or post-emergent herbicide and as a plant growth regulant is disclosed. European Patent Application 79.683. published May 25, 1983. discloses compounds, useful as herbicides or plant growth regulants, of the formula EMI2.3 where J is EMI3.1 Q is 0, S or S02; R is H or CH3; R1 is H, CH3. OCH3, Cl, Br, CO2R5. SO2R6. OSO2R7 or SO2NR8R9; R2 and R3 are independently H or C1-C3 alkyl; R4 is H or CH3; is C1-C3 alkyl, CH2CH=CH2 CH2CH2OCH3 or CH2CH2Cl; R6 is C1-C3 alkyl: R7 is 1 3 alkyl or CF ; and C -C 3 R8 and Rg are independently C1-C2 alkyl. The presence of undesired vegetation causes substantial damage to useful crops. especially agricultural products that satisfy mans' basic food and fiber needs. such as cotton, rice, corn, wheat and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available: such materials are commonly referred to as herbicides. Summarv of the Invention This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or as plant growth regulants. EMI5.1 wherein EMI5.2 EMI6.1 EMI7.1 n is 0 or 1: L is CH2 or O: Q is CH2 or O; Q1 is O, S or SO2; Q2 is 0 or S; R is H or CH3; R1 is H, C1-C3 alkyl, CO2R15, SO2NR16R17 or SO2R18; R2 is H or CH3; R3 is H or CH3; R4 is H or CH3: R5 is H, CH3, C1, Br, CO2R15, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; R6 is H, C1-C3 alkyl, CO2R15, SO2NR16R17 or SO2R18: R7 is H or CH3; R8 is CO2R15, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; R9 is H. C1-C3 alkyl or phenyl; R10 is CO2R15, SO2NR16R17, SO2N(OCH3)CH3 SO2R18 or NO2; R11 is H or CH3; 12 is H, CO2R15, SO2NR16R17, SO2N(OCH3)CH , SO2R18 or NO2; R13 is H. CO2R15. SO2NR16R17. SO2N(OCH3)CH3. SO2R18 or NO2; R14 is H or CH3; R15 is C1-C2 alkyl; R is C1-C2 alkyl; R17 is C C1-C2 alkyl; R18 is C1-C2 alkyl; R19 is CH3. Cl. Br, NO2, C1-C2 alkylthio or C1-C2 alkylsulfonyl: R20 is H, F. Cl, Br, CH3 or OCH3; R21 is H or C1-C3 alkyl; R22 is H, OH, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxylalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy, phenyl, C3-C6 cyclo alkyl, C4-C7 cycloalkylalkyl, C1-C6 alkyl carbonyl. C1-C6 alkoxycarbonyl, benzyl, C3-C4 haloalkenyl, C3-C6 haloalkynyl. C3-C6 alkyl carbonylalkyl. C3-C6 alkoxycarbonylalkyl or C1-C4 cyanoalkyl; R23 is H or CH3; R24 is H or CH3; R25 is H. CH3 or C2H5; R26 is H or CH3: R27 is H or CH3; R28 is F. C1. Br, OCH3, SCH3, S02CH3, CO2CH3, SO2N(CH3)2 or OSO2CH3; EMI9.1 X is CH3. OCH3, C1, Br, OCH2CF3 or OCHF2; Y is C1-C3 alkyl, CH2F, cyclopropyl. C=CH, OCH3, OC2H5. CH20CH3, NH2. NHCH3, N(CH3)2, OCH2CH2F, CF3, SCH3, OCH2CH=CH2, OCH2C=CH. OCH2CH2OCH3. CR(OCH3)2. EMI9.2 CR(OCH2CH3)2 or OCF2H; Z is CH or N: X1 is CH3, OCH3, OC2H5 or OCF2H; Y1 is 0 or CH2; X2 is CH3, C2H5 or CH2CF3; Y2 is OCH3, OC2H5, SCH3, SC2H5, OCF2H. SCF2H, CH3 or CH2CH3; X3 is CH3 or OCH3: Y3 is H or CH3: and agriculturally suitable salts thereof; provided that 1) when X is Cl or Br. then Z is CH and Y is OCH3. OC2H5, NHCH3, N(CH3)2 or OCF2H; 2) when X or Y is OCF H then Z is CH; 3) R5 and R6 are not simultaneously H: 4) when R6 is other than H or C1-C3 alkyl, then R5 must be H; 5) R12 and R13 are not simultaneously H: 6) when R12 is other than H, then R13 must be H: 7) R5 and R19 are not simultaneously H: and 8) when J is J-8 or J-ll then R5 is other than H. Preferred Compounds Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are: 1) Compounds of Formula I where R is H and A is A-i. 2) Compounds of Preferred 1 where Y is CH3, C2H5, OCH3, OC2H5, CH2OCH3, CH2F or CF and L i s CH2 . 3) Compounds of Preferred 2 where J is J12' J14' 18. J19, J26 or J27 4) Compounds of Preferred 3 where R20 is H and X is CH3 or OCH3. 5) Compounds of Preferred 1 where J is J-1, J-4, J-5 or J-6; X is CH3 or OCH3: and Y is C1-C2 alkoxy or C1-C2 alkyl. Other preferred groups of compounds within the scope of our invention include those disclosed and claimed in our U.S. Patent Applications Serial Nos. 581,817; 585,17Q; 699,145; and 686,796. Copies of these Applications are available on the file of the present Application. Specifically Preferred for reasons of their highest herbicidal activity. greatest plant growth regulant activity and/or most favorable ease of synthesis are: 1.3-dihydro-N-[(4.6-dimethoxypyrimidin-2-yl) aminocarbonyl]-1-oxo-benzo[C]furan-7-methane sulfonamide. m.p. 181-184 C(d); 1,3-dihydro-N-t(4-methoxy-6-methyl-1,3,5-triazin- 2-yl)aminocarbonyl]-1-oxo-benzo[C]furan-7-methane sulfonamide, m.p. 175-183 C(d): N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2.3 dihydro-2-methylbenzo[B]thiophene-7-methanesulfon amide-1.1-dioxide, m.p. 222-222.5 C; N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]-2-methylbenzo[B]thiophene-7-methane sulfonamide-l,l- dioxide, m.p. 186-187 C: : 3-[[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl] aminosulfonylmethyl]-1,5-dimethyl-1H-pyrazole-4 carboxylic acid, ethyl ester, m.p. 180-183 C; and o 5-[t(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- aminosulfonylmethyl]-1.3-dimethyl-1H-pyrazole-4 carboxylic acid, ethyl ester, m.p. 190 C. DETAILED DESCRIPTION OF THE INVENTION Synthesis The compounds of Formula I can be prepared by one or more of the methods described below in Equations 1, 2, 3 and 4. Preferred conditions and reagents are given below for each reaction, but these may be varied within the scope conventional in the art. As shown in Equation 1, compounds of Formula I can be prepared by reacting a sulfonyl isocyanate of Formula II with an appropriate heterocyclic amine of Formula III. J. R and A are as previously defined, R21 is C1-C3 alkyl and R22 is other than H or OH. Equation 1 EMI12.1 The reaction is carried out at 25 to 100 C in an inert, aprotic solvent such as methylene chloride or xylene for 0.5 to 24 hours as taught in U.S. Patent 4.127.405. Compounds of Formula I. where J is other than J14, J15, J16, J17, J19, J20, J21, J22 and J23, and where L is -CH2 -, and where R1, R5, R6. R8. R10, R12 and R13 of '3 are other than C02R15, can be prepared by reacting the sulfonamides of Formula IV with an appropriate methyl carbamate of Formula V in the presence of an equimolar or greater amount of trimethylaluminum, as shown in Equation 2. Equation 2 EMI13.1 The reaction Equation 2 is carried out at 25 to 40 C in a solvent such as methylene chloride under an inert atmosphere, as taught in our EP-A*84,244 (published July 27, 1983). The required carbamates V are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a base. Alternatively, compounds of Formula I, where J is other than J16' J J21, and J22' and where L is -CH2 -, can be prepared by reacting a sulfonyl carbamate of Formula VI with an appropriate amine of Formula III. as shown in Equation 3. Equation 3 EMI13.2 The reaction is carried out at 50 to 100 C in a solvent such as dioxane for 0.5 to 24 hours as taught for example in our EP-A-44,807. The required carbamates VI are prepared by reacting the corresponding sulfona mides IV with diphenylcarbonate in the presence of a strong base. Additionally. compounds of Formula I, where J is other than J16' J17, J21 and J and L is -CH2 -, can be prepared by reacting a sulfonamide of Formula IV with an appropriate heterocyclic phenyl carbamate of Formula VII. in the presence of a nonnucleophilic base, such as 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) as shown below in Equation 4. Equation 4 EMI14.1 The reaction is carried out at 200 to 100 C in an inert solvent, such as dioxane, for 0.5 to 24 hours by the methods taught in EPO publication No. 44.807. The required carbamates, VII, are prepared by reacting the corresponding heterocyclic amines, III, with phenylchloroformate in the presence of a base. Compounds of Formula I. where J is other than J1, J2, J3, J4, J5, J6, J7, J8, J9, 10' Jll' J26, J28 and J30, and where L is 0, can be prepared as shown below in Equation 5. The intermediate chlorosulfonylurea of Formula VIII is formed by treatment of the corresponding heterocyclic amine, III. with commercially available chlorosulfonyl isocyanate and is then allowed to react with an appropriate phenol of Formula IX. Equation 5 EMI14.2 wherein Ix J and A are as previously defined. The reaction shown in Equation 5 is best carried out according to the methods taught in United States Patent 4.391.976. The intermediate sulfonyl isocyanates of Formula II in Equation 1 can be prepared as shown in Equations 6 and 7. As shown in Equation 6, sulfonyl isocyanates of Formula II where J is other than J1' J2' J3 and J30, and R21 is C C1-C3 alkyl. R22 is other than hydrogen and hydroxy, and where L is -CH2 -. can be prepared by the reaction of sulfonamides of Formula IV with phosgene, in the presence of n-butyl isocyanate and a tertiary amine catalyst, such as diazabicyclo-(2.2.2ioctane (DABCOs), at reflux in a solvent such as xylene by the method of U.S. Patent 4.238.621. Equation 6 EMI15.1 The sulfonyl isocyanates can also be prepared from the sulfonamides by a two step procedure involving (a) reacting the sulfonamides with n-butyl isocyanate in the presence of a base such as K2C03 at reflux in an inert solvent such as 2-butanone forming a n-butyl sulfonylurea; and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent. The method is similar to a procedure taught by Ulrich and Sayigh. Newer Methods of Preparative Organic Chemistry, Vol. VI. p. 223-241. Academic Press. New York and London. W. Foerst Ed. Alternatively. as shown in Equation 7. the sulfonyl isocyanates of Formula II can be prepared by reacting the corresponding sulfonyl chlorides X with cyanic acid salts. Equation 7 EMI16.1 The reaction is carried out at 25 to 100"C in an inert aprotic solvent such as acetonitrile for 0.5-24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium iodide according to the teachings of Japanese Patent No. 76/26,816 (Chem. Abst., 85:77892e (1976)). Another method for the preparation of sulfonyl isocyanates II is shown in Equation 8. Treatment of sulfonamides of Formula IV with thionyl chloride gives intermediate N-sulfinylsulfonamides, XI, which afford sulfonyl isocyanates of Formula II upon exposure to phosgene in the presence of a catalytic amount of pyridine. Equation 8 EMI16.2 wherein J is as previously defined. The reaction of. Equation 8 can best be performed according to the procedure of H. Ulrich, B. Tucker, and A. Sayigh, J. Or. Chem.. 34. 3200 (1969). Sulfonyl isocyanates of Formula II. where J is other than Jl-Jll' J J28 or '330 R21 is C1-C3 alkyl, R22 is other than hydrogen and hydroxy. and L is 0. can be most easily prepared as shown below in Equation 9 by the reaction of appropriately substituted phenols of Formula IX with chlorosulfonyl isocyanate. This procedure is taught in United States Patents 4.191.553 and 4.394.153. and by Lohaus in Chem. Ber., 105. 2791 (1972). Equation 9 EMI17.1 wherein J is as previously defined. As shown in Equation 10. sulfonamides of Formula IV can be prepared from the cortesponding sulfonyl chlorides of Formula X by contacting with either anhydrous or aqueous ammonia. Equation 10 EMI17.2 The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature. for reviews see: F. Hawking and J. S. Lawrence. "The Sulfonamides." H. K. Lewis and Co.. London, 1950 and E. H. Northey. "The Sulfonamides and Allied Compounds, Reinhold Publishing Corp.. New York, 1948. The requisite methylsulfonyl chlorides of Formula X may be synthesized from appropriately substituted benzylic type chlorides or benzylic type bromides XII. by the two-step sequence of reactions outlined below in Equation 11 and Equation 12. Equation 11 (a) EMI18.1 wherein B is Cl or Br; and J is J1-J11, J12, J13, J14, J24, J25, J26, J27, J31 or J32; L is -CH2 -, and when J is 326 or J27' Q1 is SO2, Equation 12 (a) EMI18.2 SOCl2/DMF B is Cl or Br; J is other than J13' J16, J17' J21 or and L is -CH2-. Equation 11(a) The conversion of alkyl halides to isothiouronium salts is well precedented in the chemical literature. For relevant examples, see T. B. Johnson and J. M. Sprague. J. Am. Chem. Soc.. 58. 1348 (1936); ibid, 59, 1837 and 2439 (1937); ibid, 61, 176 (1939). In a typical procedure, a benzylic type halide of Formula XII is treated with thiourea in protic solvents such as methanol or ethanol. or aprotic solvents such as methylene chloride or benzene. Temperatures of 40-800 over one-half to 24 hours are typically required to complete the reaction. The product salts. XIII. are isolated by cooling and filtration or by concentration to remove the solvent. The salts. XI II. are generally sufficiently pure to be carried on directly to step (llb) without further purification. Equation ll(b) The oxidative chlorination of isothiouronium salts to afford sulfonyl chlorides is most efficiently carried out according to the procedure of Johnson as described in J. Am. Chem. Soc., 61. 2548 (1939). Thus, the salts of Formula XIII (B = chlorine or bromine) are dissolved or suspended in water or aqueous acetic acid and treated with at least three equivalents of chlorine at temperatures between 5-200C. When the hydrobromide salts XIII (B = bromine) are used, it is sometimes advantageous to exchange the bromide ion for nitrate ion before chlorination by treatment with an aqueous solution of one equivalent of silver nitrate; the precipitated silver bromide is removed by filtration and the filtrate treated as described above. The product sulfonyl chlorides are isolated either by simple filtration or extraction into a suitable solvent such as methylene chloride or n-butyl chloride followed by drying and evaporation of the combined organic extracts. No further purification of the sulfonyl chlorides. X. is necessary. The conversion of a benzylic type chloride or bromide of Formula XII to a sulfonic acid salt of Formula XIV as shown in Equation 12(a) is well known in the art. For a review, see Gilbert "Sulfonation and Related Reactions" Interscience Publishers, New York, 1965, pp. 136-148 and 161-163. The methods of conversion of a sulfonic acid salt of Formula XIV to a sulfonyl chloride of Formula X is well known to those skilled in the art. Benzylic type bromides of Formula XII (B = bromine) may be prepared as shown below in Equation 13 by treating the appropriate methyl aryl compound IX, with N-bromosuccinimide (NBS). Equation 13 EMI20.1 wherein J is other than J12' J13' J J J16, J17, J21, J22, J24, J25, J26 or J27; L is -CH2-: R20 is H. F. Cl, Br, OCH3; and when J is J19 or J23' R23 is H. and when J is J28' R23 and R24 are H. The reaction represented in Equation 13 can be most conveniently effected by heating a solution of the aryl methane derivatives. IX, and N-bromosuccinimide in a suitable solvent such as carbon tetrachloride at reflux temperature. A free radical catalyst such as azoisobutyronitrile (AIBN) or benzoyl peroxide is usually employed to initiate this reaction. When bromination is complete, the cooled reaction mixture is filtered to remove the by-product succinimide and the filtrate is concentrated in vacuo. The benzylic type bromides of Formula XII are often obtained in a sufficiently pure condition for further transformations. If not they can be purified by vacuum distillation or column chromatography. Benzylic type chlorides of Formula XII (L = chlorine) may be most efficiently synthesized by one of Lwo methods, both of which are well known in the chemical literature. First. benzylic type chlorides. XII. can be prepared from the appropriate aryl methane derivatives of Formula IX by reaction with N-chlorosuccinimide (NCS). This reaction is depicted below in Equation 14. Equation 14 EMI21.1 The reaction of Equation 14 can be carried out in a manner analogous to that described for the NBS bromination in Equation 13. In compounds of Formula IX where J is J-1, J-2 or 5-3, ring halogenation may occur together with benzylic-type halogenation in Equations L3 and 14. Subsequent removal of the ring halogen after conversion to the desired sulfonamide IV may be carried out by methods known in the art. Alternatively. benzylic type chlorides of Formula XII may be prepared from the appropriate benzylic type alcohols of Formula XV as shown below in Equation 15. Equation 15 EMI22.1 There exists a variety of well known methods for converting alkyl alcohols to the corresponding chlorides. One of the most common procedures involves react ion of the alcohol with thionyl chloride either alone or in the presence of a trace of a suitable base such as pyridine. For relevant examples. see the following references: H. Gilman and J. E. Kirby. J. Am. Chem. Soc., 51, 3475 (1929); H. Gilman and A. P. Hewlett, Rec. Trav. Chim., 51, 93 (1932); and M. S. Newman, J. Am. Chem. Soc., 62. 2295 (1940). The requisite aryl methanols of Formula XV (shown below in Equation 16 for the specific example of J = 527). may be prepared by reduction of an appropriately substituted aryl carboxylic acid of Formula XVI with diborane in a solvent such as tetrahydrofuran. Equation 16 EMI22.2 wherein R20, R23, R24 and Q1 are as previously defined. Although the reaction of Equation 16 is shown specifically for J-J27, this reduction is applicable to ring systems where J is other than J 16 J23 or J2a and where L is -CH2 -. For a description of the use of diborane for reduction of benzoic acid derivatives see H. C. Brown. J. Orq. Chem., 38. 2786 (1973). Alternatively. benzyl alcohols of Formula XV (shown below in Equation 17 for the specific example of J=J27) can be synthesized by reduction of the appropriately substituted benzaldehyde derivatives of Formula XVII with sodium borohydride in a solvent such as ethanol. Equation 17 EMI23.1 wherein R20, R23. R24 and Q1 are as previously defined. Although the reaction of Equation 17 is shown specifically for J=J27' this reduction is applicable to ring systems J1-J15, J18, J19, J20, J23' J24' J25' J26' J28' '29 ''330''331 and J32 where L is -CH2 -. For a description of the use of sodium borohydride for the selective reduction of aldehydes, see S. Chaikin and W. Brown, J Am. Chem. Soc., 71, 122 (1949). The aldehydes of Formula XVII can be prepared by the procedure shown in Equation 18 starting with the appropriate nitriles of Formula XVI II (shown for the specific example of J-J27) Ecuation 18 EMI24.1 wherein R20, 33' R34 and Q1 are as Previously defined. Although the reaction of Equation 18 is shown specifically for J=J27, this transformation is equally applicable to all of the ring systems (L=-CH2-) except J16, J17, J21, and J22 The reaction shown in Equation 18 can be carried out according to the procedures of H. C. Brown, C. J. Shoaf, and C. P. Garg, Tetrahedron Lett., 9 (1959), and J. A. Marshall, N. H. Andersen, and J. W. Schlicher, J. Org. Chem., 35. 858 (1970). Benzoic acid derivatives of Formula XVI (shown below in Equation 19 for the specific example of J=J27) can be prepared by hydrolysis of the appropriate nitriles of Formula XVI II which are, in turn, prepared by a Sandmeyer reaction on the corresponding aniline derivatives XIX. Equation 19 EMI24.2 wherein R20. R23, R R24 and Q1 are as previously defined. As before. while the reactions of Equation 19 are shown specifically for J=J27, these steps are applicable to all ring systems where J is other than 16' J17' J21 or J22' and L is -CH2-, Equation 19(a) The diazotization and cuprous cyanide coupling reaction of Equation 19(a) is best carried out according to the procedure described in Organic Syntheses, Coll. Vol. I, p. 514. Equation 19(b) Nitriles of Formula XVIII are most easily hydrolyzed to the desired carboxylic acids XVI by heating at reflux temperature in concentrated solutions of sulfuric acid or by treatment with 1008 phosphoric acid and subsequent exposure to nitrous acid. The products are typically isolated by extraction into aqueous base solution followed by washing with a suitable organic solvent such as ether and acidification of the water layer. For a compilation of references dealing with this process, see R. Wagner and H. Zook, "Synthetic Organic Chemistry," John Wiley & Sons, Inc.. New York. 1953. p. 412. A method similar to that described in Equation 19 above can be applied to the synthesis of phenols of Formula IX as shown below in Equation 20 (shown for the specific example of J=J27)- Equation 20 EMI25.1 wherein R200 R23. R24 and Q1 are as previously defined. The reaction of Equation 20 is applicable to ring systems J1-J25' J27' J29' J31 and J32, where L is 0. The diazotization and hydrolysis reactions shown in Equation 20 can be carried out according to the following procedures: Stevens and Beutel. J. Am. Chem. Soc., 63. 311 (1941): Grillot and Gormley, J. Am. Chem. Soc.. 67. 1968 (1945); and Mosettig and Stuart, J. Am. Chem. Soc., 61, 1 (1939). The requisite aryl amine derivatives of Formula XIX can be prepared in a straightforward manner by reduction of the corresponding nitro compounds of Formula XX as shown in Equation 21 (for the example where J=J27) Equation 21 EMI26.1 wherein R20, R23, R24, and Q are as previously defined. Although the reaction of Equation 21 is shown specifically for J=J27' this reduction is applicable to all ring systems J1-J32 There exists a wide variety of methods for effecting the reduction of aromatic nitro groups to the corresponding aryl amine derivatives. One of the more common procedures involves treating the nitro compounds of Formula XX with a slight excess of stannous chloride dihydrate in concentrated hydrochloric acid solution at temperatures between 25 and 80"C. Alternatively, reduction may be accomplished with iron powder in glacial acetic acid solution as described by Hazlet and Dornfeld, J. Am. Chem. Soc., 66, 1781 (1944), and by West in J. Chem. Soc.. 127, 494 (1925). For a general review, see Groggins. "Unit Processes In Organic Synthesis," McGraw-Hill Book Co., New York. 1947, pp. 73-128. Many of the substituted aromatic nitro compounds of Formula XX (where it is understood that all ring systems defined in the Summary of Invention are represented) can be synthesized by any of several possible synthetic routes known to one skilled in the art. The intermediate functionalized aryl methane derivatives of Formula IX (L = -CH2 -) and aryl methanols of Formula XV. (L = -CH2 -) may also be prepared by straightforward synthetic routes known to one skilled in the. art. The heterocyclic amines of Formula III can be prepared by methods known in the literature or simple modifications thereof, by those skilled in the art. For instance, EP-A 84,224 (published July 27, 1983) and W. Brakes et al, J. Am. Chem. Soc. 1947, 69, 3072 describe methods for preparing aminopyrimidines and triazines substituted by acetal groups. Also, South African Patent Application Nos. 825,045 and 825.671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as OCH2CH2F. OCH2CF3, SCK2H, and OCF2H among other groups. South African Patent Application 837,434 (published October 5. 1983) describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl. haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, and alkoxyalkyl. The 5.6-dihydrofuro[2.3-d)pyrimidin-2-amines, and the Cyclopenta[d]pyrimidin-2-amines, of formula III, where A is A-2, and the 6,7-dihydro-5H-pyrano [2.3-d]pyrimidin-2-amines, of formula III. where A is A 3, can be prepared as described in EP-A No. 15,863. The furo[2.3-dl-pyrimidin-2-amines, of formula III, where A is A-4, are described in EP-A No. 46,677. Heterocycles of formula III, where A is A-5, may be prepared as described in EP-A No. 73,562. Heterocycles of Formula III, where A is A-6, may be prepared by methods taught in EP-A 94,260. In addition, general methods for preparing aminopyrimidines and triazines have been reviewed in the following publications. "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publishers, Inc., New York and London: "Pyrimidines", Vol. 16 of the same series by D. J. Brown; "-Triazines and Derivatives". Vol. 13 of the same series by E. M. Smolin and L. Rappaport: and F. C. Schaefer, U.S. Patent 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describe the synethsis of triazines. 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 hydride). 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. Cat ironic exchange can be effected by direct contacting 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 an 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 cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt. Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., P-toluenesulfonic acid, trichloroacetic acid or the like. The preparation of the compounds of this invention is illustrated by the following examples. Example 1 Ethyl 5-(chloromethyl)-1,3-dimethvl-lH-pyrazole-4- carboxylate To 5.3 g (26.8 mmol) of 4-ethoxycarbonyl-5-(1- hydroxymethyl)-1,3-dimethylpyrazole prepared by the method of S. Gelin, et al., J. Heterocyclic Chem., 16, (1979) 1117-20, was added 1.95 ml (26.8 mmol) of thionyl chloride, dropwise. Gas evolution and an exotherm occurred. The solution was cooled with an ice bath. After ten minutes the solution gave a solid, m.p. 81-830C. H NMR (90 MHz, CDC13): 6 1.4 (t, OCCH3, 3H): 2.65 (s, CH3, 3H); 4.2 (s, NCH3, 3H); 4.4 (q, OCH C 2H); 5.2 (s, CH2C1, 2H). This material was combined with the product of a second reaction (5.0 g of 4-ethoxycarbonyl-5-(1- hydroxymethyl)-1,3-dimethylpyrazole and 1.93 ml thionyl chloride), dissolved in dichloromethane, washed with brine, dried (MgSO4) and concentrated to give 10.7 g of a solid, mp. 81-83"C. Example 2 Ethyl 5-[[(amino)(imino)methylthiomethyl-1,3 dimethyl-lH-pyrazole-4-carboxylate A solution under nitrogen was prepared from 10.7 g of the compound produced in Example 1 and 3.95 g of thiourea in 200 ml of ethanol. After refluxing the solution four hours, it was allowed to stir at room temperature overnight. The solvent was removed under reduced pressure. Then, the residue was triturated with hexane to give 16 g of solid (wet weight), m.p. 175-1800C. Example 3 Ethyl 5-methanesulfonamide-l,3-dimethyl-lH-pyrazole- 4-carboxylate To 14 g of the compound produced in Example 2, dissolved in 90 ml of water at 5 C was added 10 ml of chlorine dropwise. The rate of addition was monitored so that the temperature did not exceed 200C. A precipitate formed. The aqueous portion was decanted off and the residue was dissolved in dichloromethane, washed with a saturated sodium bicarbonate solution, dried (MgSO4) and concentrated. The residue was dissolved in 100 ml of THF. To a 75 ml portion of the THF solution, cooled to 50C, was added 1.5 ml of concentrated ammonium hydroxide solution in 10 ml of THF. A suspension formed, which was stirred for six hours. The reaction mixture was filtered and the mother liquor was concentrated under reduced pressure. The residue. triturated with ethyl acetatediethyl ether (40:60) gave 3.0 g of a light yellow solid, m.p. 135-1380C: H NMR (90 MHz, d6-DMSO): 6 1.2 (t, CH3, 3H); 2.3 (5, CH3, 3H); 3.8 (s, NCH3, 3H); 4.2 (q, OCH2. 2H): 4.8 (s, CH2S02, 2H); 7.1 (bs, NH2, 2H). Example 4 Ethyl 5-[[[[4.6-dimethoxypyrimidin-2-yl]aminocarbonyl]aminosulfonyl]methyl]-1.3-dimethyl-1H pyrazole-4-carboxylate In a dry flask under nitrogen was stirred 0.33 g of the sulfonamide from Example 3 and 0.35 g of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate and 30 ml of dry acetonitrile. Then 0.19 ml of 1,8-diazabicyclo [5.4.0]undec-7-ene was added via syringe and the solution stirred overnight. Then 50 ml of water was added. followed by a dropwise addition of 1 NHC1 until a precipitate formed. The suspension was filtered. The filtrant, after being triturated with diethyl ether, gave 0.4 g of solid, m.p. 1900C; IR (Nujol) 1711 and 1680 (C=0) cm : H NMR (200 MHz, CDCl3): 6 1.25 (t, CH3, 3H); 2.38 (s. CH3, 3H); 3.80 (s, OCH3, 6H); 3.94 (5, NCH3. 3H); 4.15 (q, OCH2, 2H); 5.23 (s, CH2S02, 2H); 5.71 (5, bs, CH. 1H); 7.35 (bs, NH, lH) and 12.4 (bs, NH, 1H). Example 5 2,6-Dimethvlbenzoic acid, methyl ester A solution of 10 g of 2,6-dimethylbenzoic acid in 22 g thionyl chloride was stirred at reflux temperature for 2 hours. Removal of the excess thionyl chloride afforded the crude acid chloride as a yellow oil. This intermediate was added to a stirred solution of 4 mL of methanol in 10.8 mL pyridine at 65-700C. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours and then poured into 75 mL ice-water. The aqueous layer was extracted with four 50-mL portions of ether and the combined organic extracts were backwashed with saturated sodium bicarbonate solution, 5% aqueous hydrochloric acid, and water. Drying and evaporation of the solvent gave a pale yellow oil which was purified by bulb-to-bulb distillation (40-500C, 0.5 mm Hg) to afford 9.5 g of pure 2,6dimethylbenzoic acid, methyl ester as a colorless liquid; IR (film) 1725 cm 1; NMR(CDC13) 6 2.3 (s, 6H), 3.9 (s, 3H), 7.0-7.4 (m. 3H). Example 6 2.6-Bis(a,a'-bromomethyl)benzoic acid, methyl ester A mixture of 5.0 g of the product from Example S, 11.1 g of N-bromosuccinimide and 0.1 g of azoisobutyronitrile in 76 mL carbon tetrachloride was heated at reflux temperature for one hour. The solution was cooled to room temperature, filtered, and the filtrate concentrated in vacuo to give a light orange oil. Treatment with ether-hexane (1:1, v/v) afforded 3.0 g of pure 2.6-bis(a,°'-bromomethyl)benzoic acid, methyl ester as a white solid, m.p. 67-70"C; IR(nuiol) 1720 cm ; NMR(CDC13) 6 4.0 (s. 3H), 4.65 (s. 4H), 7.5 (s, 3H). Example 7 7-Bromomethylphthalide The product from Example 6 (2.0g) was added to 8 mL of concentrated sulfuric acid and the suspension was warmed to about 600C for 3 hours. The solution was allowed to cool and was poured into ice-water. The resulting white precipitate was collected by filtration, washed well with water and dried. Recrystallization from acetone gave 1.0 g of pure 7-bromomethylphthalide as a white powder, m.p. 127.5-1310C: IR(KBr) 1755 cm 1 NMR(CDC13) 6 5.0 (s, 2H), 5.29 (s. 2H). 7.4 (br d, 1H), 7.5 (br d. 1H). 7.6 (dd, 1H). Example 8 7-[[(Amino)(imino)methyl]thiomethyl]phthalide A solution of 1.0 g of the product from Example 7 in 10 mL tetrahydrofuran was treated with 0.33 g of thiourea and the suspension was warmed to reflux temperature for 15 minutes as a thick, white precipitate formed. The reaction mixture was allowed to cool and was filtered. The collected solid was washed with l-chlorobutane and dried. The yield of the pure title compound was 1.2 g as a white powder, m.p. 206-2110C (dec.); NMR(DMSO-d6) 6 4.8(s, 2H), 5.4 (s, 2H), 7.61 (br to 2H). 7.73 (br t. 1H), 9.1 (brs, 1H), 9.23 (br s, 2H). Example 9 1.3-Dihydro-1-oxo-benzo[c]furan-7-methanesulfony] chloride A solution of 9.4 g of the product from Example 8 in 77 mL of 50% aqueous acetic acid was cooled to 0 C and treated with 8 mL of liquid chlorine. Following the addition, the mixture was stirred at O-100C for 2 hours. filtered, and the solid was washed well with water. The yield of 1,3-dihydro-1-oxo-benzotc]- furan-7-methanesulfonyl chloride was 5.6 g as an off-white solid, m.p. 103-105.50C (dec): lR(KBr) -1 1740, 1355. 1200 cm Example 10 1, 3-Dihydro-1-oxo-benzo r ci furan-7-methanesulfonamide A solution of 5.6 g of the product from Example 9 in 50 mL tetrahydrofuran was cooled to 0 C under an atmosphere of nitrogen and was treated with 1.5 mL of anhydrous ammonia. The resulting suspension was stirred at room temperature for 3 hours. The insoluble solids were collected by filtration and were washed with water and dried. The yield of the title compound was 3.8 g as a white powder, m.p. 192-1950C: IR(KBr) 3340, 3240, 1740, 1130 cm 1; NMR(DMSO-d6 / CDCl3) 6 # 4.9 (s, 2H), 5.4 (s, 2H), 6.7 (br s. 2H) 7.5-7.8 (m, 3H). Example 11 1,3-Dihydro-l-oxo-benzorclfuran-7-methanesulfonYl isocyanate A solution of 2.0 g of the product from Example 19 in 25 mL thionyl chloride was heated at reflux temperature for 18 hours. The reaction solution was allowed to cool to room temperature and excess thionyl chloride was removed in vacuo. The resulting residue was treated with 16 g of 10t phosgene in toluene and 5 drops of pyridine. This mixture was stirred at reflux temperature for 3 hours. The solution was allowed to cool, filtered under a stream of nitrogen, and the filtrate was concentrated to give l,3-dihydro-l-oxo benzo[c)furan-7-methanesulfonyl isocyanate as an orange oil. The infrared spectrum of this compound displayed a characteristic isocyanate stretching absorption at 2240 cm 1 as well as a carbonyl stretching signal at 1750 cm Example 12 1.3-Dihydro-N-[(4.6-dimethoxyprimidine-2-yl)amino carbonyl 1 -l-oxo-benzo r ci furan-7-methanesulfonamide A solution of 8 mmole of the product from Example 11 in 16 mL dry acetonitrile was treated with 1.2 g of 2-amino-4,6-dimethoxypyrimidine and the mixture was heated to 45-500C under an atmosphere of nitrogen for 2 hours. After being stirred at room temperature for an additional 12 hours, the suspension was filtered and the collected solid was washed well with warm acetonitrile. The yield of the title compound was 1.0 g as a yellow powder, m.p. 181-1840C (dec.); IR(KBr) 1765, 1710, 1620, 1355 cm-1; NMR(CDC13) 6 3.83 (s. 6H), 5.27 (s, 2H), 5.41 (s, 2H), 5.76 (s, 1H). 7.35 (br s, 1H), 7.5 (m, 1H). 7.7 (m, 2H), 12.4 (br s, 1H). The invention is further exemplified, but not limited to, the compounds in Tables I-XXII. The compounds depicted in these tables may be prepared by methods described in Examples 1-4, or by modifications thereof apparent to those skilled in the art. General Formulas for Tables General Formula 1 EMI37.1 General Formula 2 EMI37.2 General Formula 2a EMI37.3 General Formula 3 EMI37.4 General Formula 3a O # JSO2NHCNH-# N General Formula 4 EMI37.5 General Formulas for Tables (continued) General Formula 5 EMI38.1 General Formula 6 EMI38.2 General Formula 7 EMI38.3 General Formula 8 EMI38.4 Table I General Formula 1 (J = J1) R1 R2 R3 X Y Z m. p. ( C) H H H CH3 CH3 CH H H H CH3 OCH3 CH CH3 H H OCH3 OCH3 CH CH3 H H CH3 CH3 N CH3 H H CH3 OCH3 N CH2CH3 H H OCH3 OCH3 N CH2CH2CH3 H H CH3 OCH2CH3 CH CH(CH3)2 H H CH3 OCH3 N CO2CH3 H H OCH3 OCH3 N CO2CH3 H H Br OCH3 CH CO2CH3 H H CH3 OCH3 CH CO2CH3 H H OCH3 OCH3 CH CO2CH3 H H CH3 CH3 N CO2CH3 H H CH3 OCH3 N CO2CH2CH3 H H OCH3 OCH3 N CO2CH2CH3 H H CH3 OCH3 CH SO2N(CH3)2 H H OCH3 OCH3 CH SO2N(CH3)CH2CH3 H H CH3 CH3 N SO2N(CH2CH3)2 H H CH3 OCH3 N SO2CH3 H H OCH3 OCH3 N SO 2CH3 H H CH3 CH2F CH Table I (continued) R1 R2 R3 X Y Z m.p. ( C) SO2CH3 H H OCH3 OCH3 CH SO2CH3 H H Cl OCH3 CH SO2CH2CH3 H H OCH3 OCH3 CH H CH3 H CH3 CH3 CH H CH3 H CH3 OCH3 CH CH3 CH3 H OCH3 OCH3 CH CH3 CH3 H CH3 CH3 N CH3 CH3 H CH3 OCH3 N CH2CH3 CH3 H OCH3 OCH3 N CH2CH2CH3 CH3 H CH3 OCH2CH3 CH CH2CH2CH3 CH3 H CH3 CH3 N CH(CH3)2 CH3 H CH3 OCH3 N CO2CH3 CH3 H OCH3 OCH3 N CO2CH3 CH3 H OCH2CF3 CH3 CH CO2CH3 CH3 H CH3 OCH3 CH CO2CH3 CH3 H OCH3 OCH3 CH CO2CH3 CH3 H CH3 OCH3 N CO2CH2CH3 CH3 H OCH3 OCH3 N CO2CH2CH3 CH3 H OCH3 CH2OCH3 CH CO2CH2CH3 CH3 H CH3 OCH3 CH SO2N(CH3)2 CH3 H OCH3 OCH3 CH SO2N(CH3)CH2CH3 CH3 H CH3 CH3 N SO2N(CH2CH3)2 CH3 H CH3 OCH3 N SO2CH3 CH3 H OCH3 OCH3 N SO2CH3 CH3 H Cl OCH3 CH SO2CH2CH3 CH3 H OCH3 OCH3 CH Table I (continued) R1 R2 R3 X Y Z m. p. ( C) H H CH3 CH3 CH3 CH H H CH3 CH3 OCH3 CH CH3 H CH3 OCH3 OCH3 CH CH3 H CH3 CH3 CH3 N CH3 H CH3 CH3 OCH3 N CH2CH3 H CH3 OCH3 # N CH2CH2CH3 H CH3 OCH3 OCH3 CH CH2CH2CH3 H CH3 CH3 CH3 N CH(CH3)2 H CH3 CH3 OCH3 N CO2CH3 H CH3 CH3 CH3 CH CO2CH3 H CH3 CH3 OCH3 CH CO2CH3 H CH3 OCH3 OCH3 CH CO2CH3 H CH3 CH3 CH3 N CO2CH3 H CH3 CH3 OCH3 N C02CH2CH3 H CH3 OCH3 OCH3 U C02CH2CH3 H CH3 OCH3 CH2OCH3 CH CO2CH2CH3 H CH3 CH3 OCH3 CH SO2N(CH3)2 H CH3 OCH3 OCH3 CH SO2N(CH3)CH2CH3 H CH3 CH3 CH3 N SO2N(CH2CH3)2 H CH3 CH3 OCH2CH2F N SO2CH3 H CH3 OCH3 OCH3 N SO2CH3 H CH3 OCH3 OCH3 CH S02CH3 H CH3 Cl OCH3 CH SO2CH2CH3 H CH3 OCH3 OCH3 CH H CH3 CH3 CH3 CF3 CH H CH3 CH3 CH3 OCH3 CH CH3 CH3 CH3 OCH3 OCH3 CH Table I (continued) R1 R2 R3 X Y Z m. p. ( C) CH3 CH3 CH3 CH3 SCH3 U CH3 CH3 CH3 CH3 OCH3 N CH2CH3 CH3 CH3 OCH3 OCH3 N CH2CH2CH3 CH3 CH3 CH3 OCH2CH3 CH CH2CH2CH3 CH3 CH3 CH3 OCH3 CH CH2CH2CH3 CH3 CH3 OCH3 OCH2C=CH CH CH2CH2CH3 CH3 CH3 CH3 CH3 N CH(CH3)2 CH3 CH3 CH3 OCH3 N CO2CH3 CH3 CH3 OCH3 OCH3 N CO2CH3 CH3 CH3 CH3 OCH2CH30CH3 CH CO2CH3 CH3 CH3 CH3 OCH3 CH CO2CH3 CH3 CH3 OCH3 OCH3 CH CO2CH3 CH3 CH3 CH3 CH3 N CO2CH3 CH3 CH3 CH3 OCH3 N CO2CH2CH3 CH3 CH3 OCH3 CH2OCH3 CH CO2CH2CH3 CH3 CH3 CH3 OCH3 CH SO2N(CH3)2 CH3 CH3 OCH3 CH(OCH3) CH SO2N(CH3)CH2CH3 CH3 CH3 CH3 CH3 N SO2N(CH2CH3)2 CH3 CH3 CH3 OCH3 N SO2CH3 CH3 CH3 OCH3 OCH3 U SO2CH3 CH3 CH3 CH3 CH3 CH SO2CH3 CH3 CH3 CH3 OCH3 CH SO2CH3 CH3 CH3 OCH3 OCH3 CH SO2CH3 CH3 CH3 Cl OCH3 CH SO2CH2CH3 CH3 CH3 OCH3 1,3-dioxolan- CH 2-yl Table II General Formula 1 (J=J2) R4 R5 R6 X Y Z m.p.( C) H CH3 H CH3 OCH3 CH H CH3 H OCH3 OCH3 CH H CO2CH3 H CH3 CH3 N H CO2CH3 H CH3 OCH3 N H CO2CH3 H OCH3 OCH3 N H CO2CH3 H CH3 OCF2H CH H CO2CH3 H CH3 OCH3 CH H CO2CH3 H OCH3 OCH3 CH H CO2CH2CH3 H CH3 CH3 N H CO2CH2CH3 H CH3 OCH2CH3 N H SO2N(CH3)2 2 H OCH3 NHCH3 N H SO2N(CH3)2 H CH3 CH3 CH H SO2N(CH3)2 H CH3 C¯CH CH H SO2N(CH3)2 H OCH3 OCH3 CH H SO2N(CH3)2 H CH3 CH3 N H SO2N(CH3)2 H CH3 OCH3 N H SO2N(CH3)CH2CH3 H OCH3 OCH3 N H SO2N(OCH3)CH3 H CH3 CH3 CH H SO2N(CH2CH3)2 H CH3 OCH3 CH H SO2N(CH2CH3)2 H Br OCH3 CH HH Cl H OCH3 OCH3 N H SO2CH3 H CH3 CH2CH3 CH H SO2CH3 H CH3 OCH3 CH H 2 3 H OCH3 CH( OCH3)2 CH Table II (continued) R4 R5 R6 X Y Z m.p. ( C) H SO2CH2CH3 H Cl OCH3 CH H SO2CH2CH3 H OCH3 OCH3 N H H CH3 CH3 CH3 CH H CH3 CH3 CH3 OCH3 CH H CH3 CH3 OCH3 OCH3 CH H CO2CH3 CH3 CH3 CH3 N H CO2CH3 CH3 CH3 OCH3 N H CO2CH3 CH3 OCH3 OCH3 N H CO2CH3 CH3 CH3 CH3 CH H CO2CH3 CH3 CH3 OCH3 CH H CO2CH3 CH3 OCH3 OCH3 CH H CO2CH2CH3 CH3 CH3 CH3 N H CO2CH2CH3 CH3 CH3 OCH2CH3 N H SO2N(CH3)2 CH3 OCH3 OCH3 N H SO2N(CH3)2 CH3 CH3 CH3 CH H SO2N(CH3)2 CH3 CH3 OCH3 N H SO2N(CH3)CH2CH3 CH3 OCH3 OCH3 N H SO2N(OCH3)CH3 CH3 CH3 CH3 CH H SO2N(CH2CH3)2 CH3 CH3 OCH2CH=CH2 CH H SO2N(CH2CH3)2 CH3 OCH3 OCH3 CH H SO2CH3 CH3 CH3 CH3 N H SO2CH3 CH3 CH3 OCH3 N H SO2CH3 CH3 OCH3 OCH3 N H SO2CH3 CH3 CH3 CH2CH3 CH H Br CH3 CH3 OCH3 CH H SO2CH3 CH3 OCH3 OCH3 CH H SO2CH2CH3 CH3 Cl OCH3 CH H SO2CH2CH3 CH3 OCH3 OCH3 N Table II (continued) R4 R5 R6 X Y Z m.p. ( C) H H CH2CH2CH3 CH3 CH3 CH H CH3 CH2CH2CH3 CH3 OCH3 CH H CH3 CH2CH2CH3 OCH3 OCH3 CH H CO2CH3 CH2CH2CH3 CH3 CH3 N H CO2CH3 CH2CH2CH3 CH3 OCH3 N H CO2CH3 CH2CH2CH3 OCH3 OCH3 N H CO2CH3 CH2CH2CH3 CH3 CH3 CH H CO2CH3 CH2CH2CH3 CH3 OCH3 CH H CO2CH3 CH2CH2CH3 OCH3 SCH3 CH H CO2CH2CH3 CH2CH2CH3 CH3 CH3 N H CO2CH2CH3 CH2CH2CH3 CH3 OCH2CH3 N H SO2N(CH3)2 CH2CH2CH3 OCH2CF3 OCH3 N H SO2N(CH3)2 CH2CH2CH3 CH3 OCH3 CH H SO2N(CH3)2 CH2CH2CH3 OCH3 OCH3 CH H SO2N(CH3)2 CH2CH2CH3 CH3 OCH3 N H SO2N(CH3)CH2CH3 CH2CH2CH3 OCH OCH3 N H SO2N(OCH3)CH3 CH2CH2CH3 CH3 CH3 CH H SO2N(CH2CH3)2 CH2CH2CH3 CH3 OCH3 CH H SO2N(CH2CH3)2 CH2CH2CH3 OCH3 OCH3 CH H SO2CH3 CH2CH2CH3 CH3 OCH3 N H SO2CH3 CH2CH2CH3 OCH3 OCH3 N H SO2CH3 CH2CH2CH3 CH3 CH2CH3 CH H SO2CH3 CH2CH2CH3 CH3 OCH3 CH H SO2CH3 CH2CH2CH3 OCH3 OCH3 CH H SO2CH2CH3 CH2CH2CH3 C1 CH2F CH H SO2CH2CH3 CH2CH2CH3 OCH3 OCH3 N CH3 H CH3 CH3 CH3 CH CH3 CH3 CH3 CH3 OCH3 CH3 Table II (continued) R4 R5 R6 X Y Z m.p. ( C) CH3 CH3 CH3 OCH3 OCH3 CH CH3 CO2CH3 CH3 CH3 CH3 N CH3 CO2CH3 CH3 CH3 OCH3 N CH3 CO2CH3 CH3 OCH3 OCH3 N CH3 CO2CH3 CH3 CH3 CH3 CH CH3 CO2CH3 CH3 CH3 OCH3 CH CH3 CO2CH3 CH3 OCH3 NH2 CH CH3 CO2CH2CH3 CH3 CH3 CH3 N CH3 CO2CH2CH3 CH3 CH3 OCH2CH3 N CH3 SO2N(CH3)2 CH3 OCH3 OCH3 N CH3 SO2N(CH3)2 CH3 CH3 OCH3 CH CH3 SO2N(CH3)2 CH3 OCH3 OCH3 CH CH3 Br CH3 CH3 OCH3 N CH3 SO2N(CH3)CH2CH3 CH3 OCH3 OCH3 N CH3 SO2N(OCH3)CH3 CH3 CH3 CH3 CH CH3 SO2N(CH2CH3)2 CH3 CH3 OCH3 CH CH3 SO2N(CH2CH3)2 CH3 OCH3 OCH3 CH CH3 SO2CH3 CH3 OCH3 OCH3 N CH3 SO2CH3 CH3 CH3 CH2CH3 CH CH3 SO2CH3 CH3 CH3 OCH3 CH CH3 SO2CH3 CH3 OCF2H CH3 CH CH3 SO2CH2CH3 CH3 Cl OCH3 CH CH3 SO2CH2CH3 CH3 OCH3 OCH3 N CH3 H CH2CH2CH3 CH3 CH3 CH CH3 CH3 CH2CH2CH3 OCH3 OCH3 CH CH3 CO2CH3 CH2CH2CH3 CH3 CH3 N Table II (continued) m.p. R4 R5 R6 X Y Z ( C) CH3 CO2CH3 CH2CH2CH3 CH3 OCH3 N CH3 CO2CH3 CH2CH2CH3 OCH3 OCH3 N CH3 CO2CH3 CH2CH2CH3 CH3 CH3 CH CH3 CO2CH3 CH2CH2CH3 CH3 OCH3 CH CH3 CO2CH3 CH2CH2CH3 OCH3 OCH3 CH CH3 CO2CH2CH3 CH2CH2CH3 CH3 CH3 N CH3 CO2CH2CH3 CH2CH2CH3 CH3 OCH2CH3 N CH3 SO2N(CH3)2 CH(CH3)2 2 OCH3 OCH3 N CH3 SO2N(CH3)2 CHzCH2CH3 CH3 CH3 CH CH3 SO2N(CH3)2 CH2CH2CH3 CH3 OCH3 CH CH3 SO2N(CH3)2 CH2CH2CH3 OCH3 OCH3 CH CH3 SO2N(CH3)2 CH2CH2CH3 CH3 CH3 N CH3 SO2N(CH3)2 CH2CH2CH3 CH3 OCH3 N CH3 SO2N(CH3)CH2CH3 CH2CH2CH3 OCH3 OCH3 N CH3 SO2N(OCH3)CH3 CH2CH2CH3 CH3 CH3 CH CH3 SO2N(CH2CH3)2 CH2CH2CH3 CH3 OCH3 CH CH3 SO2N(CH2CH3)2 CH2CH2CH3 OCH3 OCH3 CH CH3 SO2CH3 CH2CH2CH3 OCH3 OCH3 N CH3 SO2CH3 CH2CH2CH3 CH3 CH2CH3 CH CH3 SO2CH3 CH2CH2CH3 CH3 OCH3 CH CH3 SO2CH3 CH2CH2CH3 OCH3 OCH2CH2F CH CH3 SO2CH2CH3 CH2CH2CH3 Cl OCH3 CH CH3 SO2CH2CH3 CH2CH3 OCH3 OCH3 N H H CO2CH3 CH3 CH2CH3 CH H H CO2CH3 CH3 OCH3 CH H H CO2CH3 OCH3 OCH3 CH H H C 2CH3 CH3 CH3 N H H CO2CH3 CH3 OCH3 N H H CO2CH3 OCH3 OCH3 N Table II (continued) R4 R5 R6 X Y Z m.p. ( C) H H CO2CH2CH3 CH3 CH3 CH H H CO2CH2CH3 CH3 SCH3 CH H H CO2CH2CH3 OCH3 OCH3 CH H H CO2CH2CH3 CH3 CH2CH2CH3 N H H CO2CH2CH3 CH3 OCH3 N H H CO2CH2CH3 OCH3 CH2OCH3 CH H H SO2N(CH3)2 CH3 OCH3 CH H H SO2N(CH3)2 OCH3 OCH3 CH H H SO2N(CH3)2 CH3 CH2CH3 N H H SO2N(CH3)2 CH3 OCH3 N H H SO2N(CH3)2 OCH3 OCH3 N H H SO2N(CH3)CH2CH3 CH3 CH3 CH H H SO2N(CH2CH3)2 CH3 OCH3 CH H H SO2CH3 OCH3 OCH3 CH H H SO2CH3 CH3 OCH2CH3 N H H SO2CH3 CH3 OCH3 N H H SO2CH3 OCH3 OCH3 N H H SO2CH3 CH3 CH3 CH H H SO2CH3 CH3 OCH3 CH H H SO2CH2CH3 OCH3 OCH3 CH H H SO2CH2CH3 Cl OCH2CH2OCH3 CH CH3 H CO2CH3 CH3 CH3 CH CH3 H CO2CH3 CH3 OCH3 CH CH3 H CO2CH3 OCH3 OCH3 CH CH3 H CO2CH3 CH3 CH3 N CH3 H CO2CH3 CH3 OCH3 N CH3 H CO2CH3 OCH3 OCH3 N CH3 H CO2CH2CH3 CH3 CH3 CH CH3 H CO2CH2CH3 CH3 OCH3 CH Table II (Continued) m. p. R4 R5 R6 X Y Z ( C) CH3 H CO2CH2CH3 OCH3 OCH3 CH CH3 H CO2CH2CH3 CH3 CH3 N CH3 H CO2CH2CH3 CH3 OCH3 N CH3 H CO2CH2CH3 OCH3 CH2OCH3 CH CH3 H SO2N(CH3)2 CH3 CH3 CH CH3 H SO2N(CH3)2 CH3 OCH3 CH CH3 H SO2N(CH3)2 OCH3 OCH3 CH CH3 H SO2N(CH3)2 CH3 CH2CH3 N CH3 H SO2N(CH3)2 CH3 OCH3 N CH3 H SO2N(CH3)2 OCH3 OCH3 N CH3 H SO2N(CH3)CH2CH3 CH3 CH3 CH CH3 H SO2N(CH2CH3)2 CH3 OCH3 CH CH3 H SO2CH3 OCH3 OCH3 CH CH3 H SO2CH3 CH3 OCH2CH3 N CH3 H SO2CH3 CH3 OCH3 N CH3 H SO2CH3 OCH3 OCH3 N CH3 H SO2CH3 CH3 CH3 CH CH3 H SO2CH3 CH3 OCH3 CH CH3 H SO2CH2CH3 OCH3 OCH3 CH CH3 H SO2CH2CH3 OCH3 CH2CH3 CH CH3 H SO2CH2CH3 Cl OCH3 CH CH3 NO2 H CH3 OCH3 CH CH3 NO2 CH3 CH3 OCH3 N CH3 NO2 CH3 OCH3 1,3-dioxo- N lan-2-yl Table III General Formula 1 (J = J3) R7 R8 X Y Z m.p. ( C) H CO2CH3 CH3 CH3 CH H CO2CH3 CH3 OCH3 CH H CO2CH3 OCH3 OCH3 CH H CO2CH3 CH3 CH3 N H CO2CH3 CH3 OCH3 N H CO2CH3 OCH3 OCH3 N H CO2CH2CH3 CH3 CH3 CH H SO2N(CH3)2 OCH3 CH2CH3 N H SO2N(CH3)2 CH3 OCH3 N H SO2N(CH3)2 OCH3 OCH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 Br OCH3 CH H SO2N(CH3)2 OCH3 OCH3 CH H SO2N(CH3)OCH3 CH3 CH3 N H SO2N(CH3)CH2CH3 CH3 OCH2CH3 N H SO2CH3 OCH3 OCH3 N H SO2CH3 CH3 CH3 CH H SO2CH3 CH3 OCH3 CH H SO2CH3 OCH3 OCH3 CH H SO2CH3 CH3 CH3 N H SO2CH3 CH3 OCH3 N H SO2CH2CH3 OCH3 SCH3 N Table III (continued) R7 R8 X Y Z m.p. ( C) H NO2 CH3 CH3 CH H NO2 CH3 OCH3 CH H NO2 OCH3 OCH3 CH H NO2 Cl OCH3 CH H NO2 OCH3 CH2OCH3 CH CH3 CO2CH3 CH3 CH3 CH CH3 CO2CH3 CH3 OCH3 CH CH3 CO2CH3 OCH3 OCH3 CH CH3 CO2CH3 CH3 CH3 N CH3 CO2CH3 CH3 OCH3 N CH3 CO2CH3 OCH3 OCH2CH2F N CH3 CO2CH2CH3 CH3 CH3 CH CH3 CO2CH2CH3 CH3 OCH3 CH CH3 CO2CH2CH3 OCF2H OCH3 CH CH3 SO2N(CH3)2 OCH3 CH2CH3 N CH3 SO2N(CH3)2 CH3 OCH3 N CH3 SO2N(CH3)2 OCH3 OCH3 N CH3 SO2N(CH3)2 OCH3 OCH3 CH CH3 SO2N(CH3)OCH3 CH3 CH3 N CH3 SO2N(CH3)CH2CH3 CH3 OCH2CH3 N CH3 SO2CH3 OCH3 OCH3 N CH3 SO2CH3 CH3 CH3 CH CH3 SO2CH3 CH3 OCH3 CH CH3 SO2CH3 OCH2CF3 OCH3 CH CH3 SO2CH3 CH3 CH3 N CH3 SO2CH3 CH3 OCH3 N CH3 SO2CH2CH3 OCH3 OCH3 N CH3 NO2 CH3 # CH Table III (continued) R7 R8 X Y Z m.p. ( C) CH3 NO2 OCH3 OCH3 CH CH3 NO2 Cl OCH3 CH CH3 NO2 OCH3 CH2OCH3 CH CH3 NO2 OCH3 1.3-dioxolan- CH 2-yl H CO2CH3 OCH3 CH2F CH H CO2CH3 OCH3 C=CH CH H CO2CH3 OCH3 CF3 CH H CO2CH3 OCH3 NHCH3 CH H CO2CH3 OCH3 N(CH3)2 CH H CO2CH3 OCH3 OCH2CH=CH2 CH H CO2CH3 OCH3 CH(OCH2CH3)2 CH Table IV General Formula 1 (J is J4) R9 R10 R11 X Y Z m. p. ( C) H CO2CH3 H CH3 CH3 CH H CO2CH3 H CH3 OCH3 CH H CO2CH3 H OCH3 OCH3 CH H CO2CH3 H CH3 CH3 N H CO2CH3 H CH3 OCH3 N H CO2CH2CH3 H OCH3 OCH3 N H CO2CH3 CH3 CH3 CF3 CH CH3 CO2CH3 H CH3 OCH3 CH CH3 CO2CH3 H CH3 OCH2CH3 CH CH3 CO2CH3 H Cl OCH3 CH CH3 CO2CH3 CH3 CH3 CH3 CH CH3 CO2CH3 CH3 CH3 OCH3 CH CH3 CO2CH3 CH3 OCH3 OCH2CH2OCH3 CH CH3 CO2CH3 CH3 CH3 CH3 N CH3 CO2CH3 CH3 CH3 OCH3 N CH3 CO2CH3 CH3 OCH3 OCH3 N CH3 CO2CH3CH H CH3 OCH3 CH CH3 CO2CH3CH H OCH3 OCH3 CH 198-200 CH3 CO2CH3CH H CH3 OCH3 N CH3 CO2CH3CH H OCH3 OCH3 N 199-201 CH3 CO2CH3CH H Cl OCH3 CH CH3 CO2CH2CH3 CH3 OCF2H CH3 CH CH3 CO2CH2CH3 CH3 CH3 OCH3 CH Table IV (continued) m. p. R9 R10 R11 X Y Z ( C) CH3 CO2CH2CH3 CH3 OCH3 OCH3 CH 190 CH3 CO2CH2CH3 CH3 CH3 CH3 N CH3 CO2CH2CH3 CH3 CH3 OCH3 N 183-184 CH3 CO2CH2CH3 CH3 OCH3 OCH3 N 165-167 CH3 CO2CH2CH3 CH3 Cl OCH3 CH 140.5-144.5 CH3 CO2CH2CH3 CH3 OCH3 OCH2CH3 CH CH2CH2CH3 CO2CH2CH3 CH3 OCH3 OCH3 N CH2CH2CH3 CO2CH2CH3 CH3 OCH3 OCH3 CH CH2CH2CH2 CO2CH2CH3 CH3 CH3 OCH3 CH CH2CH2CH2 CO2CH2CH3 H OCH3 CH2F CH CH2CH2CH3 CO2CH2CH3 H OCH3 OCH3 N CH2CH2CH2 CO2CH3 H OCH3 OCH3 CH CH2CH2CH3 CO2CH3 CH3 OCH3 OCH3 N C6H5 CO2CH3 H OCH3 OCH3 CH C6H5 CO2Et CH3 CH3 OCH3 N C6H5 CO2Et CH3 OCH3 OCH3 N C6H5 CO2CH3 CH3 CH3 CH3 CH C6H5 CO2Et CH3 CH3 SCH3 CH C6H5 CO2Et CH3 OCH3 OCH3 CH H SO2N(CH3)2 H Br OCH3 CH H SO2N(CH2CH3)2 H OCH3 OCH2CH3 N H SO2N(CH3)OCH3 H CH3 OCH3 CH H SO2N(CH3)2 CH3 OCH3 OCH3 CH H SO2N(CH2CH3)2 CH3 CH3 CH2F N H SO2N(OCH3)CH3 CH3 CH3 OCH3 N H NO2 CH3 OCH3 OCH3 N CH3 SO2N(CH3)2 H CH3 CH3 CH CH3 SO2N(CH3)2 CH3 CH3 OCH3 CH CH3 SO2N(CH3)OCH3 H OCH3 CH(OCH3)2 CH CH3 SO2N(CH3)CH2CH3 CH3 CH3 CH3 N Table IV (continued) R9 R10 R11 X Y Z m.p. ( C) CH3 NO2 H CH3 OCH2CH3 N CH3 NO2 CH3 OCH3 OCH3 N CH2CH2CH3 SO2N(CH3)2 H CH3 CH3 CH CH2CH2CH3 SO2N(CH3)2 CH3 CH3 OCH3 CH CH2CH2CH3 SO2N(CH3)OCH3 H OCH3 OCH3 CH CH2CH2CH3 SO2N(CH3)OCH3 CH3 CH3 CH3 N CH2CH2CH3 NO2 H CH3 OCH3 N CH2CH2CH3 NO2 CH3 OCH3 OCH3 N C6H5 SO2N(CH3)2 H CH3 CH3 CH C6H5 SO2N(CH3)CH2CH3 CH3 CH3 OCH3 CH C6H5 SO2N(CH3)OCH3 H OCH3 OCH3 CH C6H5 SO2N(CH3)OCH3 CH3 CH3 CH2CH3 N C6H5 NO2 H CH3 OCH3 N C6H5 NO2 CH3 OCH3 OCH3 N C6H5 NO2 CH3 CH3 CH3 CH H SO2CH2CH3 H CH3 N(CH3)2 N H SO2CH2CH3 CH3 OCH3 OCH2 N CH3 SO2CH2CH3 H OCH2CF3 CH3 CH CH2CH3 SO2CH2CH3 CH3 CH3 OCH3 CH CH(CH3)2 SO2CH2CH3 H OCH3 OCH3 CH C6H5 SO2CH2CH3 CH3 CH3 CH2CH2CH3 N Table V General Formula 1 (J is J5) R10 R11 X Y Z m.p.( C) CO2CH3 H CH3 CH3 CH CO2CH3 H CH3 OCH3 CH CO2CH3 H OCH3 OCH3 CH CO2CH3 H Cl OCH3 CH CO2CH3 H CH3 OCH3 N CO2CH3 H OCH3 OCH3 N CO2CH3 CH3 CH3 CH3 CH CO2CH3 CH3 CH3 OCH3 CH CO2CH3 CH3 OCH3 OCH3 CH CO2CH3 CH3 CH3 OCH2CH3 CH CO2CH3 CH3 CH3 OCH3 N CO2CH3 CH3 OCH3 OCH3 N CO2Et H CH3 CH3 CH CO2Et CH3 CH3 OCH3 CH CO2Et CH3 OCH3 OCH3 CH 180-183 CO2Et CH3 Br OCH3 CH CO2Et CH3 CH3 OCH2CH3 CH CO2Et CH3 CH3 CH3 N CO2Et CH3 CH3 OCH3 N 154-157 CO2Et CH3 OCH3 OCH3 N 188-188.5 CO2Et CH3 OCH3 OCH2CH3 N CO2Et CH3 CH3 CH2OCH3 CH CO2Et CH3 CH3 CH2OCH3 CH Table V (continued) 10 R11 X Y Z m.p.( C) SO2N(CH3)2 H OCF2H CH3 CH SO2N(CH3)2 H CH3 OCH3 CH SO2N(CH3)2 H OCH3 OCH3 CH SO2N(CH3)2 H CH3 CH3 N SO2N(CH3)2 H CH3 OCH3 N SO2NCH3(OCH3)2 H OCH3 OCH3 N SO2N(CH2CH3)2 CH3 CH3 CH3 CH SO2N(CH2CH3)2 H CH3 OCH3 CH SO2N(CH2CH3)2 H OCH3 OCH3 CH SO2N(CH2CH3)2 H CH3 CH3 N SO2N(CH2CH3)2 H CH3 OCH3 N SO2N(CH3)CH2CH3 H OCH3 OCH3 N SO2CH3 H CH3 CH3 CH SO2CH3 H CH3 OCH3 CH SO2CH3 H OCH3 OCH3 CH SO2CH3 H OCH3 CH3 N SO2CH3 H CH3 NHCH3 N SO2CH3 CH3 OCH2CF3 OCH3 N SO2CH3 CH3 OCH3 OCH3 N SO2CH2CH3 H OCH3 OCH3 CH SO2CH2CH3 H CH3 OCH3 CH SO2CH2CH3 CH3 OCH3 OCH3 CN SOCH2C3 CH3 CH3 CH3 N SO3CH2CH3 CH3 CH3 OCH3 N SO2CH2CH3 CH3 OCH3 OCH3 N SO2CH2CH3 CH3 OCH3 CH2CH3 CH SO2CH2CH CH3 CH3 OCH2CH3 CH SO2CH2CH3 CH3 Cl OCH3 CH NO2 H OCH3 CH3 CH NO2 H OCH3 CH3 N NO2 H OCH3 OCH2=CH CH Table VI General Formula 1 (J is R12 R13 R14 X Y m.p. R12 R13 R14 X Y Z ( C) CO2CH3 H H CH3 OCH3 CH CO2CH3 H H OCH3 OCH3 CH CO2CH3 H H CH3 CH3 N CO2CH3 H H CH3 OCH3 N CO2CH3 H H OCH3 OCH3 N CO2CH3 H H CH3 CH3 CH CO2CH2CH3 H H CH3 OCH3 CH CO2CH2CH3 H H OCH2CF3 OCH3 CH CO2CH2CH3 H H CH3 CH3 N CO2CH2CH3 H H CH3 OCH3 N CO2CH2CH3 H H OCH3 OCH3 N SO2N(CH3)2 H H CH3 OCH3 CH SO2N(CH3)2 H H OCH3 OCH3 CH SO2N(CH3)2 H H CH3 CH3 N SO2N(CH3)2 H H CH3 OCH3 N SO2N(CH3)2 H H OCH3 OCH3 N SO2N(CH3)2 H B OCH3 CH2CH3 N SO2N(CH3)OCH3 H H OCH3 OCH2CH3 CH SO2N(CH3)OCH3 H H Cl OCH3 CH SO2N(CH3)OCH3 H H OCH3 CH2OCH3 CH CO2CH3 H CH3 CH3 OCH3 CH CO2CH3 H CH3 OCH3 OCH3 CH CO2CH3 H CH3 CH3 CH3 N Table VI (continued) R12 R13 R14 X Y Z CO2CH3 H CH3 CH3 OCH3 N CO2CH3 H CH3 OCH3 OCH3 N CO2CH3 H CH3 CH3 CH3 CH CO2CH2CH3 H CH3 CH3 CH3 CH CO2CH2CH3 H CH3 CH3 OCH3 CH CO2CH2CH3 H CH3 OCH3 OCH3 CH CO2CH2CH3 H CH3 CH3 CH3 N CO2CH2CH3 H CH3 CH3 OCH3 N CO2CH2CH3 H CH3 OCH3 OCH3 N SO2N(CH3)2 H CH3 CH3 OCH3 CH SO2N(CH3)2 H CH3 OCH3 OCH3 CH SO2N(CH3)2 H CH3 CH3 CH3 N SO2N(CH3)2 H CH3 CH3 OCH3 N SO2N(CH3)2 H CH3 OCH3 OCH3 N SO2N(CH3)2 H CH3 OCH3 CH2CH3 N SO2N(CH3)OCH3 H CH3 OCH3 OCH2CH2F CH SO2N(CH3)OCH3 H CH3 Cl OCH3 CH SO2N(CH3)OCH3 H CH3 OCH3 CH2OCH3 CH SO2N(CH3)OCH3 H CH3 OCH3 OCH3 CH SO2CH3 H CH3 OCH3 CH3 CH SO2CH2CH3 H CH3 OCH3 OCH3 N NO2 H CH3 OCH3 OCH2CH3 CH SO2CH3 H H OCH3 OCH3 N SO2CH2CH3 H H OCH3 CH2OCH3 CH NO2 H H OCH3 OCH3 N NO2 H H OCH3 # N H CO2CH3 H CH3 OCH3 CH H CO2CH3 H OCH3 OCH3 CH H CO2CH3 H CH3 CH3 N H CO2CH3 H CH3 OCH3 N H CO2CH3 H OCH3 OCH3 N H CO2CH3 H CH3 CH2F CH Table VI (continued) R12 R13 R14 X Y Z m.p. ( C) H CO2CH2CH3 H CH3 OCH3 CH H CO2CH2CH3 H OCH3 OCH3 CH H CO2CH2CH3 H CH3 CH3 N H CO2CH2CH3 H CH3 OCH3 N H CO2CH2CH3 H OCH3 OCH3 N H CO2CH2CH3 H CH3 CH3 CH H SO2N(CH3)2 H CH3 OCH3CH2OCH3 CH H SO2N(CH3)2 H OCH3 OCH3 CH H SO2N(CH3)2 H CH3 CH3 N H SO2N(CH3)2 H CH3 N(CH3)2 N H SO2N(CH3)2 H OCH3 OCH3 N H SO2N(CH3)2 H OCH3 CH2CH3 N H SO2N(CH3)OCH3 H OCH3 OCH2CH3 CH H SO2N(CH3)OCH3 H Cl OCH3 CH H SO2N(CH3)OCH3 H OCH3 CH2OCH3 CH H CO2CH3 CH3 CH3 OCH2=CH CH H CO2CH3 CH3 OCH3 OCH3 CH H CO2CH3 CH3 CH3 CH3 N H CO2CH3 CH3 CH3 OCH3 N H CO2CH3 CH3 OCH3 OCH3 N H CO2CH3 CH3 CH3 # CH H CO2CH2CH3 CH3 CH3 CF3 CH H CO2CH2CH3 CH3 CH3 OCH3 CH H CO2CH2CH3 CH3 OCH3 OCH3 CH H CO2CH2CH3 CH3 CH3 CH3 N H SO2N(CH3)2 CH3 CH3 OCH3 CH H SO2N(CH3)2 CH OCH3 OCH3 CU H SO2N(CH3)2 CH3 CH3 CH3 N H SO2N(CH3)2 CH3 CH3 OCH3 N H SO2N(CH3)2 CH3 OCH3 OCH3 N Table VI (continued) R12 R13 R14 X Y Z m.p. ( C) H SO2N(CH3)2 CH3 OCH3 CH2CH3 N H SO2N(CH3)OCH3 CH3 OCH3 OCH2CH3 CH H SO2N(CH3)OCH3 CH3 Cl OCH3 CH H SO2N(CH3)OCH3 CH3 OCH3 CH2OCH3 CH H SO2N(CH2CH3)2 CH3 OCH3 OCH3 CH H SO2CH3 CH3 OCH3 CH3 CH H SO2CH2CH3 CH3 OCH3 OCH3 N H NO2 CH3 OCH3 OCH2CH3 CH H SO2CH3 H OCH3 OCH3 N H SO2CH2CH3 H OCH3 CH2OCH3 CH H NO2 H OCH3 SCH3 N H NO2 H OCH3 1.3-dioxo- CH lan-2-yl Table VII General Formula 1 J R5 R19 R X Y Z m. p. ( C) J-7 H CH3 H OCH3 CH3 CH J-7 H Cl H OCH3 CH3 CH J-7 H NO2 H OCH3 CH3 CH J-7 H SCH2CH3 H OCH3 N(CH3)2 CH J-7 H SO2CH3 H OCH2CF3 CH3 H J-7 CH3 SO2CH2CH3 H CH3 C#CH H J-7 CO2CH3 H H OCH3 OCH3 CH 192-194 J-7 CO2CH3 H H CH3 OCH3 CH 155-162 J-7 CO2CH3 H H CH3 CH3 CH 153-156 J-7 CO2CH3 H H OCH3 OCH3 N 167-169 J-7 CO2CM3 H H CH3 OCH3 N 166-167 J-7 CO2CH3 H H Cl OCH3 CH 185-186 -7 CO2CH3 H CH3 OCH3 OCH3 N 165-166 J-7 Cl H H OCH3 CH2CH2CH3 CH J-7 Cl CH3 H OCH3 OCH2CH3 CH J-7 SO2N(CH3)2 H H OCH3 CF3 CH J-7 SO2N(CH3)2 H H OCH3 SCH3 CH J-7 SO2CH3 Cl H OCH3 CH(OCH3)2 CH J-7 SO2CH3 H H OCH3 OCH3CH=CH2 CH J-7 SO2CH2CH3 H H OCHF3 CH3 CH J-8 H - H OCH3 CH3 CH J-8 CH3 - H OCH3 CH3 H J-8 CO2CH3 - H OCH3 CH3 CH J-8 CO2CH3 - H OCH3 CH3 H J-8 Cl - H OCH3 OCH2CH2F CH J-8 SO2N(CH3)2 - H OCH3 OCH2CH3 H Table VII (Continued) J R5 R19 R X Y Z J-8 SO2CH3 - H OCH3 CH3 CH J-8 NO2 - H OCH3 NHCH3 CH J-9 H Br H OCF2H CH3 CH J-9 H CH3 H CH3 OCH3 N J-9 CH3 NO2 H OCH3 OCF2H CH J-9 Cl SCH3 H CH3 OCH3 N J-9 CO2CH3 Cl H Cl OCH3 CH J-9 CO2CH3 CH3 H OCH3 OCH3 N J-9 CO2CH3 SO2CH3 H Br OCH3 CH J-9 SO2N(CH3)2 H H CH3 CH3 N J-9 SO2CH3 H H OCH3 CH2CH3 CH J-9 SO2CH2CH3 H H OCH3 # N J-10 H SO2CH2CH3 H OCH3 CH3 CH J-10 H NO2 H OCH3 CH3 N J-10 CH3 Cl H OCH3 CH2OCH3 CH J-10 Cl Cl H OCH3 OCH3 N J-10 CO2CH3 SCH3 H OCH3 OCH3 CH J-10 CO2CH3 H H OCH3 OCH3 N J-10 CO2CH2CH3 H H OCH3 CH(OEt)2 CH J-10 SO2N(CH3)Et H H OCH3 OCH3 N J-10 SO2CH3 H CH3 OCH3 OCH3 CH J-10 SO2CH3 CH3 H OCH3 OCH3 N J-11 Cl - H OCH3 OCH3 CH J-11 Br - H OCH3 OCH3 N J-11 CH3 - H OCH3 OCH2C#CH CH J-ll CO2CH3 - H OCH3 CH3 N J-11 CO2CH3 - H OCH3 CF3 CH J-ll CO2CH2CH3 - H OCH3 OCH3 N J-11 SO2N(CH3)2 - H CH3 C#CH CH J-ll 502CH3 - H CH3 N(CH3)2 N J-11 SO2CH2CH3 - H CH3 CH2F CH Table VIII General Formula 4 J R4 R5 R6 R19 X1 Y1 J2 H CH3 CH3 - CH3 O J2 CH3 Cl CH3 - OCH3 CH2 J2 H Br CH2CH2CH3 - OCH3 O J2 CH3 CO2CH3 CH2CH2CH3 - OCH3 O J2 CH3 SO2N(CH3)2 CH3 - CH3 O J2 CH3 H SO2CH3 - OCH3 CH2 J2 CH3 SO2CH2CH3 CH3 - CH3 O J7 - CH3 - SCH3 OCH3 O J7 - Cl - CH3 OCH3 CH2 J7 - CO2CH3 - CH3 CH3 O J7 - H - SO2CH3 OCH3 O J7 - SO2CH3 - Cl OCH3 O J7 - SO2N(CH3)2 - H CH3 O J8 - CH3 - - OCH3 CH2 J8 - Cl - - CH3 O J8 - CO2CH3 - - OCH3 O J8 - CO2CH2CH3 - - OCH2CH3 O J8 - NO2 - - CH3 O J8 - SO2CH3 - - OCF2H CH2 J8 - SO2CH3 - - OCH3 CH2 J9 - Cl - CH3 OCH3 O J9 - CO2CH3 - CH3 OCH3 O J9 - SO2CH2CH3 - CH3 CH3 O J10 - SO2CH3 - CH3 CH3 O J10 - Cl - CH3 OCH3 CH2 J10 - CO2CH3 - SCH3 OCH3 O J10 - SO2CH3 - Cl CH3 CH2 J11 - Cl - - CH3 O J11 - CO2CH3 - - OCH3 O J11 - SO2N(CH3)2 - - OCH2CH3 CH2 J11 - SO2CH3 - - CH3 O Table IX General Formula 4 J R1 R2 R3 R7 R8 X1 Y1 J1 CH3 H H - - CH3 O J1 CH3 CH3 CH3 - - OCH3 CH2 J1 CO2CH3 CH3 CH3 - - CH3 CH2 J1 CO2CH3 H H - - OCH3 O J1 CO2CH3 H H - - OCF2H CH2 J1 CO2CH3 CH3 H - - OCH3 O J1 CO2CH2CH3 H H - - CH3 O J1 CO2CH2CH3 CH3 H - - CH3 O J1 SO2N(CH3)2 H H - - CH3 O J1 SO2N(CH3)2 CH3 CH3 - - OCH2CH3 CH2 J1 SO2N(CH2CH3)2 H H - - OCH3 O J1 SO2CH3 H H - - OCH3 CH2 J1 SO2CH3 H CH3 - - OCH3 O J1 SO2CH3 CH3 CH3 - - CH3 O J1 SO2CH2CH3 CH3 CH3 - - CH3 CH2 J3 - - - H CO2CH3 CH3 O J3 - - - H CO2CH2CH3 CH3 O J3 - - - CH3 SO2N(CH3)2 OCH3 CH2 J3 - - - CH3 SO2N(OCH3)CH3 OCH3 CH2 J3 - - - H SO2CH3 OCH3 O J3 - - - H SO2CH3 OCH3 CH2 J3 - - - CH3 SO2CH2CH3 CH3 O J3 - - - CH3 NO2 CH3 O Table X General Formula 4 J R9 R10 R11 R12 R13 R14 X1 Y1 J4 H CO2CH3 H - - - OCH3 CH2 J4 CH3 CO2CH3 CH3 - - - CH3 O J4 CH3 CO2CH3 CH3 - - - CH3 O J4 CH3 CO2CH2CH3 H - - - OCH3 O J4 CH3 SO2N(CH3)2 CH3 - - - OCH3 O J4 CH3 SO2N(OCH3)CH3 CH3 - - - OCH2CH3 CH2 J4 CH3 SO2CH3 CH3 - - - CH3 O J4 CH3 SO2CH3 CH3 - - - OCF2H O J4 CH2CH2CH3 CO2CH3 CH3 - - - OCH3 CH2 J4 CH3 NO2 CH3 - - - OCH3 O J4 CH3 SO2CH2CH3 H - - - CH3 O J4 Ph CO2CH3 H - - - OCH3 CH2 J5 - CO2CH3 H - - - OCH3 O J5 - CO2CH3 CH3 - - - OCH3 O J5 - CO2H3 H - - - CH3 O J5 - SO2N(CH3)2 H - - - OCH3 CH2 J5 - SO2N(CH3)Et H - - - OCH3 O J5 - SO2CH3 CH3 - - - CH3 O J5 - SO2CH3 CH3 - - - OCH3 O J5 - SO2CH2CH3 CH3 - - - OCH3 CH2 J5 - NO2 H - - - OCH3 O J6 - - - H CO2CH3 H CH3 O J6 - - - H CO2CH3 CH3 OCH3 CH2 J6 - - - CH3 H CH3 CH3 O J6 - - - H SO2N(CH3)2 CH3 OCH3 O J6 - - - NO2 H CH3 OCH3 O J6 - - - H SO2CH3 CH3 OCH3 CH2 J6 - - - CO2CH3 H H CH3 O J6 - - - CO2CH3 H CH3 CH3 O J6 - - - SO2CH3 H CH3 OCH3 CH2 Table XI General Formula 5 J R1 R2 R3 R7 R8 X1 J1 CH3 H H - - CH3 J1 CH3 CH3 CH3 - - OCH3 J1 CO2CH3 CH3 CH3 - - CH3 J1 CO2CH3 H H - - OCH3 J1 CO2CH3 H H - - OCF2H J1 CO2CH3 CH3 H - - OCH3 J1 CO2CH3 CH3 H - - OCH3 J1 CO2CH2CH3 H H - - CH3 J1 CO2CH2CH3 CH3 H - - CH3 J1 SO2N(CH3)2 H H - - CH3 J1 SO2N(CH3)2 H CH3 - - OCH3 J1 SO2N(CH3)2 CH3 CH3 - - OCH2CH3 J1 SO2N(CH2CH3)2 H H - - OCH3 J1 SO2CH3 H H - - OCH3 J1 SO2CH3 H CH3 - - OCH3 J1 SO2CH3 CH3 CH3 - - CH3 J1 SO2CH2CH3 CH3 CH3 - - CH3 J3 - - - H CO2CH3 CH3 J3 - - - H CO2CH2CH3 CH3 J3 - - - H SO2N(CH3)2 OCH3 33 - - - CH3 SO2N(OCH3)CH3 OCH3 J3 - - - H SO2CH3 OCH3 J3 - - - H SO2CH3 OCH2CH3 J3 - - - CH3 SO2CH3 CH3 33 - - - CH3 NO2 CH3 Table XII General Formula 5 J R4 R5 R6 R19 X1 J2 H CH3 CH3 - CH3 J2 CH3 Cl CH3 - OCH3 J2 H Br CH2CH2CH3 - OCF2H J2 CH3 CO2CH3 CH3 - OCH3 J2 CH3 SO2N(CH3)2 CH3 - CH3 J2 CH3 SO2CH3 SO2CH3 - OCH3 J2 CH3 SO2CH2CH3 CH3 - CH3 J7 - CH3 - SCH3 OCH3 J7 - Cl - CH3 OCH3 J7 - CO2CH3 - CH3 CH3 J7 - H - SO2CH3 OCH3 J7 - SO2CH3 - Cl OCH3 J7 - SO2N(CH3)2 - SCH3 CH3 J8 - CH3 - - OCH3 J8 - Cl - - CH3 J8 - CO2CH3 - - OCH3 J8 - CO2CH2CH3 - - OCH2CH3 J8 - NO2 - - CH3 J8 - SO2CH3 - - OCH3 J9 - Cl - CH3 OCH3 J9 - CO2CH3 - H OCH3 J9 - SO2CH3 - CH3 CH3 J10 - Cl - CH3 OCH3 J10 - CO2CH3 - SCH3 OCH3 J10 - SO2CH3 - Cl CH3 J11 - Cl - - OCH3 Table XII (Continued) J R4 R5 R6 R19 X1 J11 - CO2CH3 - - OCH3 J11 - SO2N(CH3)2 - - OCH3 J11 - SO2CH3 - - CH3 Table XIII General Formula 5 J R9 R10 R11 R12 R13 R14 X1 J4 H CO2CH3 H - - - OCH3 J4 CH3 CO2CH3 CH3 - - - CH3 J4 CH3 CO2CH2CH3 H - - - OCH3 J4 CH3 SO2N(CH3)2 CH3 - - - OCH2CH3 J4 CH3 SO2CH3 CH3 - - - CH3 J4 CH3 SO2CH3 CH3 - - - OCF2H J4 CH2CH2CH3 CO2CH3 CH3 - - - OCH3 J4 CH3 NO2 CH3 - - - OCH3 J4 CH3 SO2CH2CH3 H - - - CH3 J4 Ph CO2CH3 H - - - OCH3 J5 - CO2CH3 CH3 - - - OCH3 J5 - CO2CH3 H - - - OCH3 J5 - CO2H3 H - - - CH3 J5 - SO2N(CH3)2 H - - - OCH3 J5 - SO2N(CH3)Et H - - - OCH3 J5 - SO2CH3 CH3 - - - CH3 J5 - SO2CH3 CH3 - - - OCH3 J5 - SO2CH2CH3 CH3 - - - OCH3 J5 - NO2 H - - - OCH3 J6 - - - H CO2CH3 H CH3 J6 - - - H CO2CH3 CH3 OCH3 J6 - - - CH3 H CH3 CH3 J6 - - - H SO2N(CH3)2 CH3 OCH3 J6 - - - NO2 H CH3 OCH3 J6 - - - H SO2CH3 CH3 OCH3 J6 - - - CO2CH3 H CH3 CH3 J6 - - - CO2CH3 H CH3 CH3 J6 - - - SO2CH3 H CH3 OCH3 Table XIV General Formula 6 J R1 R2 R3 R7 R8 X1 Y1 1 CH3 H H - - CH3 H J1 CH3 CH3 CH3 - OCH3 H J1 CO2CH3 CH3 CH3 - - CH3 H J1 CO2CH3 H H - - OCH3 H J1 CO2CH3 H H - - OCF2H CH3 J1 CO2CH3 CH3 H - - OCH3 CH3 J1 CO2CH2CH3 H H - - CH3 CH3 J1 CO2CH2CH3 CH3 H - - CH3 H J1 SO2N(CH3)2 H H - - CH3 H J1 SO2N(CH3)2 H CH3 - - OCH3 H J1 SO2N(CH3)2 CH3 CH3 - - OCH2CH3 CH3 J1 SO2N(CH2CH3)2 H H - - OCH3 CH3 J1 SO2CH3 H H - - OCH3 CH3 J1 SO2CH3 H CH3 - - OCH3 H J1 SO2CH3 CH3 CH3 - - CH3 H J1 SO2CH2CH3 CH3 CH3 - - CH3 H J3 - - - H CO2CH3 CH3 CH3 J3 - - - H CO2CH2CH3 CH3 CH3 J3 - - - CH3 SOzN(CH3)2 OCH3 CH3 J3 - - - CH3 SO2N(OCH3)CH3 OCH3 H J3 - - - H SO2CH3 OCH3 H J3 - - - CH3 SO2CH3 OCH3 H J3 - - - CH3 SO2CH3 CH3 CH3 J3 - - - CH3 NO2 CH3 CH3 Table XV General Formula 6 J R4 R5 R6 R19 X1 Y3 J2 H CH3 CH3 - CH3 H J2 CH3 Cl CH3 - OCH3 H J2 H Br CH2CH2CH3 - OCH3 H J2 CH3 CO2CH3 CH3 - OCH3 CH3 J2 CH3 SO2N(CH3)2 CH3 - CH3 CH3 J2 CH3 H SO2CH3 - OCH3 CH3 J2 CH3 SO2CH2CH3 CH3 - CH3 H J7 - CH3 - SCH3 OCH3 CH3 J7 - Cl - CH3 OCH3 CH3 J7 - CO2CH3 - CH3 CH3 CH3 J7 - H - SO2CH3 OCH3 CH3 J7 - SO2CH3 - Cl OCH3 CH3 J7 - SO2N(CH3)2 - SCH3 CH3 H J8 - CH3 - - OCH3 H J8 - Cl - - CH3 H J8 - CO2CH3 - - OCH3 H J8 - CO2CH2CH3 - - OCH2CH3 CH3 J8 - NO2 - - CH3 CH3 J8 - SO2CH3 - - OCH3 CH3 J9 - Cl - CH3 OCH3 H J9 - CO2CH3 - CH3 OCH3 H J9 - SO2CH3 - CH3 CH3 CH3 J10 - Cl - CH3 OCH3 H J10 - CO2CH3 - SCH3 OCH3 CH3 J10 - SO2CH3 - Cl CH3 CH3 J11 - Cl - - OCF2H CH3 J11 - CO2CH3 - - OCH3 H J11 - SO2N(CH3)2 - - OCH3 H J11 - SO2CH3 - - CH3 H Table XVI General Formula 6 J R9 R10 R11 R12 R13 R14 X1 Y3 J4 H CO2CH3 H - - - OCH3 H J4 CH3 CO2CH3 CH3 - - - CH3 H J4 CH3 CO2CH2CH3 H - - - OCH3 H J4 CH3 SO2N(CH3)2 CH3 - - - OCH3 H J4 CH3 SO2N(OCH3)CH3 CH3 - - - OCH2CH3 CH3 J4 CH3 SO2CH3 CH3 - - - OCF2H CH3 J4 CH2CH2CH3 CO2CH3 CH3 - - - OCH3 CH3 J4 CH3 NO2 CH3 - - - OCH3 CH3 J4 CH3 SO2CH2CH3 H - - - CH3 CH3 J4 Ph CO2CH3 H - - - OCH3 CH3 J5 - CO2CH3 H - - - OCH2CH3 H J5 - CO2CH3 H - - - OCH3 H J5 - CO2CH3 H - - - CH3 H J5 - SO2N(CH3)2 H - - - OCH3 H J5 - SO2N(CH3)Et H - - - OCH3 H J5 - SO2CH3 CH3 - - - CH3 H J5 - SO2CH3 CH3 - - - OCH3 H J5 - SO2CH2CH3 CH3 - - - OCH3 CH3 J5 - NO2 H - - - OCH3 CH3 J6 - - - H CO2CH3 H CH3 CH3 J6 - - - H CO2CH3 CH3 OCH3 CH3 J6 - - - CH3 H CH3 CH3 CH3 J6 - - - H SO2N(CH3)2 CH3 OCH3 CH3 J6 - - - NO2 H CH3 OCH3 H J6 - - - H SO2CH3 CH3 OCH3 H J6 - - - CO2CH3 H H CH3 H J6 - - - CO2CH3 H CH3 CH3 H J6 - - - SO2CH3 CH3 CH3 OCH3 H Table XVII General Formula 7 J R4 R5 R6 R19 X2 Y2 J2 H CH3 CH3 - CH3 OCH3 J2 CH3 Cl CH3 - CH3 OCH3 J2 H Br CH2CH2CH3 - CH3 OCH3 J2 CH3 CO2CH3 CH3 - CH3 OCH3 J2 CH3 SO2N(CH3)2 CH3 - CH3 OCH3 J2 CH3 H SO2CH3 - CH3 CH3 J2 CH3 SO2CH2CH3 CH3 - C2H5 OCH2CH3 J7 - CH3 - SCH3 CH2CF3 CH3 J7 - Cl - CH3 CH3 CH3 J7 - CO2CH3 - CH3 CH3 CH3 J7 - H - SO2CH3 CH3 CH3 J7 - SO2CH3 - Cl CH3 CH3 J7 - SO2N(CH3)2 - SCH3 C2H5 H J8 - CH3 - - CH2CF3 OCH3 J8 - Cl - - CH3 OCH3 J8 - CO2CH3 - - CH3 SCF2H J8 - CO2CH2CH3 - - CH3 OCH3 J8 - NO2 - - CH3 OCH3 J8 - SO2CH3 - - CH2CH3 OCH3 J9 - Cl - CH3 CH3 OCH3 J9 - CO2CH3 - SO2CH3 CH3 CH3 J9 - SO2CH3 - CH3 CH3 OCH3 J1 - Cl - CH3 CH3 SCH2CH3 J10 - CO2CH3 - SCH3 C2H5 OCH3 J10 - SO2CH3 - Cl CH2CF3 OCH3 J11 - Cl - - CH3 OCH3 J11 - CO2CH3 - - CH3 SC2H5 J11 - SO2N(CH3)2 - - CH3 OCH3 J11 - SO2CH3 - - CH3 OCH3 Table XVIII General Formula 7 J R1 R2 R3 R7 R8 X2 Y2 J1 CH3 H H - - CH3 OCH3 J1 CH3 CH3 CH3 - - CH3 OCH3 J1 CO2CH3 CH3 CH3 - - CH3 OCH3 J1 CO2CH3 H H - - CH3 OCH3 J1 CO2CH3 H H - - CH3 OCH3 J1 CO2CH3 CH3 H - - C 2H5 OCH3 J1 CO2CH2CH3 H H - - CH2CF3 OCH3 J1 CO2CH2CH3 CH3 H - - CH3 OCH3 J1 SO2N(CH3)2 H H - - CH3 CH3 J1 SO2N(CH3)2 H CH3 - - CH3 OEt J1 SO2N(CH3)2 CH3 CH3 - - CH3 OCH3 J1 SO2N(CH2CH3)2 H H - - CH3 OCH3 J1 SO2CH3 H H - - CH3 OCH3 J1 SO2CH3 H CH3 - - CH3 SCH3 J1 SO2CH3 CH3 CH3 - - CH3 CH2CH3 J1 SO2CH2CH3 CH3 CH3 - - C2H5 OCH3 J3 - - - H CO2CH3 CH2CF3 OCH3 J3 - - - H CO2CH2CH3 CH3 OCH3 J3 - - - CH3 SO2N(CH3)2 CH3 SCF2H J3 - - - CH3 SO2N(OCH3)CH3 CH3 OCH3 J3 - - - H SO2CH3 CH3 OCH3 J3 - - - H SO2CH3 CH3 OCH3 J3 - - - CH3 SO2CH2CH3 CH3 SCH2CH3 J3 - - - CH3 NO2 CH3 OCH3 Table XIX General Formula 7 J R9 R10 R11 R12 R13 R14 X2 Y2 J4 H CO2CH3 H - - - CH3 OCH3 J4 CH3 CO2CH3 CH3 - - - CH3 OCH3 J4 CH3 CO2CH2CH3 H - - - CH3 OCH3 J4 CH3 SO2N(CH3)2 CH3 - - - CH3 OCH3 J4 CH3 SO2N(OCH3)CH3 CH3 - - - CH3 OCH3 J4 CH3 SO2CH3 CH3 - - - C2H5 OCH3 J4 CH3 SO2CH3 CH3 - - - CH3 OCH3 J4 CH2CH2CH3 CO2CH3 CH3 - - - CH3 CH3 J4 CH3 NO2 CH3 - - - OCH3 OCH2CH3 J4 CH3 SO2CH2CH3 H - - - CH3 OCH3 J4 Ph CO2CH3 H - - - CH2CF3 CH3 J5 - CO2CH3 H - - - CH3 OCH3 J5 - CO2CH3 H - - - CH3 CH2CH3 J5 - CO2CH3 H - - - CH3 OCH3 5- S02N(CH3)2 H - - - CH3 OCH3 SO2N(CH3)Et H - - - CH3 SCHF2 3 CU3 - - - CM3 0CM3 J5 - SO2CH3 CH3 - - - CH2CH3 OCH3 J5 - SO2CH2CH3 CH3 - - - CH3 OCH3 J5 - NO2 H - - - CH3 OCH3 J6 - - - H CO2CH3 H CH3 SCH2CH3 J6 - - - H CO2CH3 CH3 CH3 OCH3 J6 - - - CH3 CO2CH3 CH3 CH3 OCH3 J6 - - - H SO2N(CH3)2 CH3 CH3 OCH3 J6 - - - CH3 SO2N(CH3)2 CH3 CH3 OCH3 J6 - - - H SO2CH3 CH3 CH2CF3 OCH3 J6 - - - CO2CH3 H H CH3 OCH3 J6 - - - CO2CH3 H CH3 CH3 OCH3 J6 - - - SO2CH3 CH3 CH3 CH3 OCH3 Table XX General Formula 8 J R9 R10 R11 R12 R13 R14 X3 J4 H CO2CH3 H - - - CH3 J4 CH3 CO2CH3 CH3 - - - OCH3 J4 CH3 CO2CH2CH3 H - - - CH3 J4 CH3 SO2N(CH3)2 CH3 - - - OCH3 J4 CH3 SO2N(OCH3)CH3 CH3 - - - CH3 J4 CH3 SO2CH3 CH3 - - - OCH3 J4 CH3 SO2CH3 CH3 - - - CH3 J4 CH2CH2CH3 CO2CH3 CH3 - - - OCH3 J4 CH3 NO2 CH3 - - - CH3 J4 CH3 SO2CH2CH3 H - - - OCH3 J4 Ph CO2CH3 H - - - CH3 J5 - CO2CH3 H - - - OCH3 J5 - CO2CH3 H - - - CH3 J5 - CO2CH3 CH3 - - - OCH3 J5 - SO2N(CH3)2 H - - - CH3 J5 - SO2N(CH3)Et H - - - OCH3 J5 - SO2CH3 CH3 - - - CH3 J5 - SO2CH3 CH3 - - - OCH3 J5 - SO2CH2CH3 CH3 - - - CH3 J5 - NO2 H - - - OCH3 J6 - - - H CO2CH3 H CH3 J6 - - - H CO2CH3 CH3 OCH3 J6 - - - CH3 H CH3 CH3 J6 - - - H SO2N(CH3)2 CH3 OCH3 J6 - - - NO2 H CH3 CH3 J6 - - - H SO2CH3 CH3 OCH3 J6 - - - CO2CH3 H H CH3 J6 - - - CO2CH3 H CH3 OCH3 J6 - - - SO2CH3 CH3 CH3 CH3 Table XXI General Formula 8 J R1 R 2 R3 R7 R8 X3 J1 CH3 H H - - CH3 J1 CH3 CH3 CH3 - - OCH3 J1 CO2CH3 CH3 CH3 - - CH3 J1 CO2CH3 H H - - OCH3 J1 CO2CH3 H H - - CH3 J1 CO2CH3 CH3 H - - OCH3 J1 CO2CH2CH3 H H - - CH3 J1 CO2CH2CH3 CH3 H - - CH3 J1 SO2N(CH3)2 H H - - OCH3 J1 SO2N(CH3)2 H CH3 - - CH3 J1 SO2N(CH3)2 CH3 CH3 - - OCH3 J1 SO2N(CH2CH3)2 H H - - CH3 J1 SO2CH3 H H - - OCH3 J1 SO2CH3 H CH3 - - CH3 J1 SO2CH3 CH3 CH3 - - CH3 J1 SO2CH2CH3 CH3 CH3 - - OCH3 J3 - - - H CO2CH3 CH3 33 - - - H CO2CH2CH3 OCH3 J3 - - - CH3 SO2N(CH3)2 CH3 33 - - - CH3 SO2N(OCH3)CH3 OCH3 J3 - - - H SO2CH3 CH3 J3 - - - H SO2CH3 OCH3 J3 - - - CH3 SO2CH3 CH3 J3 - - - CH3 NO2 OCH3 Table XXII General Formula 8 J R4 R5 R6 R19 X3 J2 H CH3 CH3 - CH3 J2 CH3 Cl CH3 - OCH3 J2 H Br CH2CH2CH3 - CH3 J2 CH3 CO2CH3 CH3 - OCH3 J2 CH3 SO2N(CH3)2 CH3 - CH3 J2 CH3 H SO2CH3 - OCH3 J2 CH3 SO2CH2CH3 CH3 - CH3 J7 - CH3 - SCH3 OCH3 J7 - Cl - CH3 CH3 J7 - CO2CH3 - CH3 OCH3 J7 - H - SO2CH3 CH3 J7 - SO2CH3 - Cl OCH3 J7 - SO2N(CH3)2 - SCH3 CH3 - CH3 - - OCH3 - Cl - - CH3 - CO2CH3 - - OCH3 - CO2CH2CH3 - - CH3 B - CO2CH2CH3 - CH3 J8 - NO2 - - OCH3 J8 - SO2CH3 - - CH3 J9 - Cl - CH3 OCH3 J9 - CO2CH3 - CH3 CH3 J9 - SO2CH3 - CH3 OCH3 J10 - Cl - CH3 CH3 J10 - CO2CH3 - SCH3 OCH3 J10 - SO2CH3 - Cl CH3 J11 - Cl - - OCH3 J11 - CO2CH3 - - CH3 J11 - SO2N(CH3)2 - - OCH3 J11 - SO2CH3 - - CH3 Table XXIII Generale Formula 2 m. p. J n L R20 R22 X Y ( C) J12 0 CH2 H CH3 CH3 OCH3 J12 0 CH2 H CH3 OCH3 OCH3 J12 0 CH2 H CH3 CH3 CH3 J12 0 CH2 H CH3 OCH3 C2H5 J12 0 CH2 H CH3 CH3 OC2H5 J12 0 CH2 H CH3 OCH3 CH2OCH3 J12 0 CH2 H CH3 Cl OCH3 J12 0 CH2 H CH3 Br OCH3 J12 0 CH2 H CH3 OCH3 CH2F J12 0 CH2 H CH3 OCH3 CF3 J12 1 CH2 H CH3 OCH3 OCH3 J12 0 CH2 H C2H5 OCH3 OCH3 J12 0 CH2 H n-C3H7 OCH3 OCH3 J12 0 CH2 H CH(CH3)2 OCH3 OCH3 J12 0 CH2 H H CH3 CH3 J12 0 CH2 H H OCH3 OCH3 J12 0 CH2 H H CH3 OCH3 J12 0 CH2 H H OCH3 Cl J12 0 O H H CH3 CH3 J12 0 O H H CH3 OCH3 J12 0 O H H OCH3 OCH3 J12 0 O H H OCH3 Cl J12 0 O H CH3 OCH3 OCH3 J12 0 O H CH3 CH3 OCH3 J12 0 O H CH3 CH3 CH3 J12 0 O H CH3 Cl OCH3 J12 0 O H CH3 Br OCH3 J12 0 O H C2H5 OCH3 OCH3 J12 0 O H n-C3H7 OCH3 OCH3 Table XXIII (continued) m.p. J n L R20 R22 X Y ( C) J12 0 O H CH(CH3)2 OCH3 OCH3 J12 1 O H CH3 OCH3 OCH3 J12 0 CH2 5-F CH3 OCH3 OCH3 J12 0 CH2 6-Cl CH3 OCH3 OCH3 J12 0 CH2 6-Br CH3 OCH3 OCH3 J12 0 CH2 6-CH3 CH3 OCH3 OCH3 J12 0 CH2 6-OCH3 CH3 OCH3 OCH3 J12 0 O H CH3 OCH2CF3 CH3 J12 0 O H CH3 OCHF2 OCH3 J12 0 O H CH3 OCH3 CH(CH3)2 J12 0 O H CH3 OCH3 cyclopropyl J12 0 O H CH3 OCH3 C#CH J12 0 O H CH3 OCH3 NH2 J12 0 O H CH3 OCH3 N(CH3)2 J12 0 O H CH3 OCH3 OCH2CH2F J12 0 O H CH3 OCH3 SCH3 J12 0 O H CH3 OCH3 OCH2CH=CH2 J12 0 O H CH3 OCH3 OCH2CH2OCH3 J12 0 O H CH3 OCH3 OCH2C#CH J12 0 O H CH3 OCH3 CH(OCH3)2 J12 0 O H CH3 OCH3 C(CH3)(OCH3)2 J12 0 O H CH3 OCH3 1,3-dioxolan 2-yl J12 0 O H CH3 OCH3 2-methyl-1,3 dioxolan-2-yl J12 0 O H CH3 OCH3 CH(OC2H5)2 J12 0 O H CH3 OCH3 C(CH3)(OC2H5)2 J12 0 O H CH3 OCH3 NHCH3 J12 0 O H CH3 Cl NHCH3 J12 0 O H -CH2CN OCH3 OCH3 J12 0 O H -(CH2)3CN CH3 OCH3 J12 0 CH2 H OH CH3 OCH3 J12 0 CH2 H -(CH2)3CH(CH3)2 Cl OCH3 Table XXIII (continued) m. p. J n L R20 R22 X Y ( C) J12 0 CH2 H -CF2H OCH3 OCH3 J12 0 CH2 H -CH2CH2Cl Cl OCH3 J12 0 CH2 H -(CH2)5Cl CH3 OCH3 J12 0 CH2 H -CH2OCH3 Cl OCH3 J12 0 CH2 H -(CH2)4OCH3 CH3 OCH3 J12 0 CH2 H -CH2CH=CH2 OCH3 OCH3 J12 0 CH2 H -CH2-CH=CHCH3 CH3 OCH3 J12 0 CH2 H -CH2C#CH OCH3 OCH3 J12 0 CH2 H -CH2C#C-CH3 Cl OCH3 J12 0 CH2 H -(CH2)4C#CH CH3 OCH3 J12 0 CH2 H -OCH3 CH3 OCH3 J12 0 CH2 H -O(CH2)4CH3 Cl OCH3 J12 0 CH2 H -C6H5 CH3 OCH3 J12 0 CH2 H cyclopropyl OCH3 OCH3 J12 0 CH2 H cyclohexyl OCH3 OCH3 J12 0 CH2 H cyclopropylmethyl OCH3 OCH3 J12 0 CH2 H cyclohexylmethyl Cl OCH3 J12 0 CH2 H -C(O)CH3 OCH3 OCH3 J12 0 CH2 H -C(O)(CH2)5H Cl OCH3 J12 0 CH2 H -CO2C2H5 Br OCH3 J12 0 CH2 H -CO2(CH2)4H Cl OCH3 J12 0 CH2 H -CH2C6H5 OCH3 OCH3 J12 0 CH2 H -CH2-CH=CH-CH2Cl CH3 OCH3 J12 0 CH2 H -CH2C#C-CH2Cl Cl OCH3 J12 0 CH2 H -CH2C(O)CH3 OCH3 OCH3 J12 0 CH2 H -CH(CH3)CO2C2H5 OCH3 OCH3 J12 0 CH2 H H CH3 OCH3 J12 0 CH2 H H CH3 OCH3 J12 0 CH2 H H Cl OCH3 J12 0 O H H OCH3 OCH3 J12 0 O H H CH3 OCH3 J12 0 O H H CH3 OCH3 J12 0 O H H Cl OCH3 Table XXIII (continued) m.p. J n L R20 R22 X Y ( C) J12 0 CH2 H n-C4H9 CH3 CH3 J12 0 CH2 H n-C4H9 CH3 OCH3 J12 0 CH2 H n-C4H9 OCH3 OCH3 J12 0 CH2 H n-C4H9 Cl OCH3 J12 0 O H n-C4H9 CH3 CH3 J12 0 O H n-C4H9 CH3 OCH3 J12 0 O H n-C4H9 OCH3 OCH3 J12 0 O H n-C4H9 Cl OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 CH3 OCH3 J18 - CH2 H CH3 Cl OCH3 J18 - CH2 H CH3 Br OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 CH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H H OCH3 OCH3 J18 - CH2 H C2H5 OCH3 OCH3 J18 - CH2 H n-C3H7 OCH3 OCH3 J18 - CH2 H CH(CH3)2 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 7-Cl CH3 OCH3 OCH3 J18 - CH2 7-Br CH3 OCH3 OCH3 J18 - CH2 6-F CH3 OCH3 OCH3 J18 - CH2 7-CH3 CH3 OCH3 OCH3 J18 - CH2 7-OCH3 CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH2F3 OCH3 J18 - CH2 H CH3 OCHF3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 Table XXIII (continued) m.p. J n L R20 R22 X Y ( C) J18 - CH2 H CH3 OCH3 OCH2CH=CH2 J18 - CH2 H CH3 OCH3 CH(OCH3)2 J18 - CH2 H CH3 OCH3 1,3-dioxolan 2-yl J18 - CH2 H CH3 OCH3 CH(OC2H5)2 J18 - CH2 H CH3 Cl NHCH3 J18 - CH2 H CH3 OCH3 -C#CH J18 - CH2 H CH3 OCH3 C(CH3)(OCH3)2 J18 - CH2 H OH OCH3 OCH3 J18 - CH2 H (CH2)2CH(CH3)2 Cl OCH3 J18 - CH2 H CH2CH2Cl OCH3 OCH3 J18 - CH2 H (CH2)5Cl CH3 OCH3 J18 - CH2 H CH2OCH3 Cl OCH3 J18 - CH2 H (CH2)2OCH3 Cl OCH3 J18 - CH2 H CH2CH=CH2 OCH3 OCH3 J18 - CH2 H CH2CH=CHCH2Cl CH3 OCH3 J18 - CH2 H CH2CH=CHCH3 CH3 OCH3 J18 - CH2 H CH2C#CCH3 OCH3 OCH3 J18 - CH2 H OCH3 Cl OCH3 J18 - CH2 H O(CH2)4CH3 Cl OCH3 J18 - CH2 H C6H5 OCH3 OCH3 J18 - CH2 H cyclopropyl Cl OCH3 J18 - CH2 H cyclopentyl OCH3 OCH3 J18 - CH2 H C(O)CH3 OCH3 OCH3 J18 - CH2 H CO2CH3 OCH3 OCH3 J18 - CH2 H CH2C6H5 Cl OCH3 J18 - CH2 H CH2CH=CHCl Cl OCH3 J18 - CH2 H CH(CH3)CO2CH3 Cl OCH3 Table XXIIIa General Formula 2a J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y J13 0 CH2 - - H CH3 - - - - - - OCH3 OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH3 J13 0 CH2 - - - H CH3 - - - - - - Cl OCH3 J13 0 CH2 - - - H CH3 - - - - - - Br OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 C2H5 J13 0 CH2 - - - H CH3 - - - - - - CH3 OC2H5 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH20CH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH2F J13 0 CH2 - - - H CH3 - - - - - - OCH3 CF3 J13 0 CH2 - - - H H - - - - - - OCH3 OCH3 J13 0 CH2 - - - H C2H5 - - - - - - OCH3 OCH3 J13 0 CH2 - - - H n-C3H7 - - - - - - OCH3 OCH3 J13 0 CH2 - - - H CH(CH3)2 - - - - - - OCH3 OCH3 J13 1 CH2 - - - H CH3 - - - - - - OCH3 OCH3 J13 0 O - - - H CH3 - - - - - - OCH3 OCH3 J13 0 O - - - H CH3 - - - - - - OCH3 CH3 J13 0 O - - - H CH3 - - - - - - Cl OCH3 J13 0 O - - - H CH3 - - - - - - Br OCH3 J13 1 O - - - H CH3 - - - - - - OCH3 OCH3 J13 0 0 - - - H C2H5 - - - - - - OCH3 OCH3 J13 0 CH2 - - - 6-Br CH3 - - - - - - OCH3 OCH3 J13 0 CH2 - - - 6-Cl CH3 - - - - - - OCH3 OCH3 J13 0 CH2 - - - 5-F CH3 - - - - - - OCH3 OCH3 J13 0 O - - - 6-CH3 CH3 - - - - - - OCH3 OCH3 J13 O 0 - - - 6-CH3 CH3 - - - - - - OCH3 OCH3 J13 0 0 - - - 6-OCH3 CH3 - - - - - - OCH3 OCH3 J14 O CH3 - - - H - H H - - - - OCH3 OCH3 181-184,d J14 0 CH2 - - - H - H H - - - - CH3 OCH3 180-185, d J14 0 CH2 - - - H - H H - - - - CH3 CH3 J14 0 CH2 - - H - H H - - - - Cl OCH3 Table XXIIIa (continued) m. p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J13 0 CH2 - - H CH3 - - - OCH3 CH(CH3)2 J13 0 CH2 - - - H CH3 - - - - - Cl NHCH3 J13 0 CH2 - - H CH3 - - - - - - Cl OCF2H J13 0 CH2 - - - H CH3 - - - - - - OCH2CF3 OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCF2H OCF2H J13 0 CH2 - - - H CH3 - - - - - - OCH3 cyclopropyl J13 0 CH2 - - - H CH3 - - - - - - OCH3 NHCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 N(CH3)2 J13 0 CH2 - - - H CH3 - - - OCH3 OCH2CH=CH2 J13 0 CH2 - - - H CH3 - - - - OCH3 CH(CH3)2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 1,3-dioxolan 2-yl J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH(OC2H5)2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 C#CH J13 0 CH2 - - - H CH3 - - - - - - OCH3 OCH2CH20CH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 SCH3 J13 0 CH2 - - - H CH3 - - - - - - OCF2H OCH3 J13 0 CH2 - - - H CH3 - - - - - - CH3 1,3-dioxolan 2-yl J14 0 CH2 - - - H - H H - - - - CH3 OCH2C#CH J14 0 CH2 - - - H - H H - - - - Br OCH3 J14 0 CH2 - - - H - H H - - - - OCH3 C2H5 J14 0 CH2 - - - H - H H - - - CH3 OC2H5 J14 0 CH2 - - H - H H - - - - CH3 CH2OCH3 J14 0 CH2 - - - H - H H - - - - OCH3 CH2F J14 0 CH2 - - - H - H H - - - - OCH3 CF J14 0 CH2 - - - H - H H - - - - OCH3 CF3 J14 1 CH2 - - - H - H H - - - - OCH3 OCH3 J14 1 CH2 - - - H - CH3 H - - OCH3 OCH3 J14 0 O - - - H - H H - - - - OCH3 CH3 Table XXIIIa (continued) m. p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J14 1 CH2 - - - H - CH3 H - - - CH3 CH3 J14 1 CH2 - - - H - CH3 H - - CH3 OCH3 J14 1 CH2 - - - H - CH3 H - - OCH3 OCH3 J14 1 CH2 - - - H - CH3 H - - - - Cl OCH3 J14 1 O - - - H - CH3 H - - - - CH3 CH3 J14 1 O - - - H - CH3 H - - - - OCH3 CH3 J14 1 O - - - H - CH3 H - - - - Cl OCH3 J14 1 CH2 - - - H - CH3 H - - - OCH3 OCH3 J14 0 O - - - H - H H - - - - OCH3 OCH3 J14 0 O - - - H - H H - - - OCH3 CH3 J14 0 O - - - H - H H - - - - Cl OCH3 J14 0 O - - - H - H H - - - - Br OCH3 J14 0 O - - - H - H H - - - - CH3 CH3 J14 0 CH2 - - - H - H H - - - - CH3 CH3 J14 0 CH2 - - - H - H H - - - - OCH3 CH3 J14 0 CH2 - - - H - H H - - - - OCH3 OCH3 J14 0 CH2 - - - H - H H - - - - Cl OCH3 J14 0 CH2 - - - 5-F - H H - - - - OCH3 OCH3 J14 0 CH2 - - - 6-Cl - H H - - - - OCH3 OCH3 J14 0 CH2 - - - 6-Br - H H - - - - OCH3 OCH3 J14 0 O - - - 5-CH3 - H H - - - OCH3 OCH3 J14 0 O - - - 6-OCH3 - H H - OCH3 OCH3 J14 1 O - - - H - H H - - - - OCH3 OCH3 J15 0 CH2 - - - H - - - - - - - OCH3 OCH3 J15 1 CH2 - - - H - - - - - - - OCH3 CH3 J15 0 O - - - H - - - - - - - OCH3 OCH3 J15 0 0 - - - H - - - - - - - OCH3 OCH3 J15 0 0 - - H - - - - - - OCH3 OCH3 J15 0 CH - - - H - - - - - - - Cl OCH3 J15 O - - - H - - - - - - - Cl OCH3 J16 0 - - - - H CH3 - - - - - - OCH3 OCH3 J16 0 - - - - H CH3 - - - - - - CH3 OCH3 Table XXIIIa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J16 0 - - - - H CH3 - - - - - - CH3 CH3 J16 0 - - - - H CH3 - - - - - - Cl OCH3 J16 1 - - - - H CH3 - - - - - - OCH3 OCH3 J16 0 - - - - H H - - - - - - OCH3 OCH3 J16 0 - - - - H H - - - - - - OCH3 OCH3 J17 0 - - - - H CH3 - - - - - - OCH3 OCH3 J17 0 - - - - H CH3 - - - - - - Cl OCH3 J17 0 - - - - H CH3 - - - - - - CH3 OCH3 J17 0 - - - - H H - - - - - - OCH3 OCH3 J17 1 - - - - H CH3 - - - - - - OCH3 OCH3 J19 - CH2 - - - H - H - - - - - OCH3 OCH3 J19 - CH2 - - - H - H - - - - - OCH3 CH3 J19 - CH2 - - - H - H - - - - - Cl OCH3 J19 - CH2 - - - H - H - - - - - Br OCH3 J19 - CH2 - - - H - H - - - - - OCH3 C2H5 J19 - CH2 - - - H - H - - - - - CH3 OC2H5 J19 - CH2 - - - H - H - - - - - OCH3 CH2OCH3 J19 - CH2 - - - H - H - - - - - OCH3 CH2F J19 - CH2 - - - H - H - - - - - OCH3 CF3 J19 - 0 - - - H - H - - - - - OCH3 OCH3 J19 - 0 - - - H - H - - - - - Cl OCH3 J19 - CH2 - - - 7-Cl - H - - - - - OCH3 OCH3 J19 - CH2 - - - H - - - - - - - OCH3 OCH3 J20 - CH2 - - - H - - - - - - - Cl OCH3 J20 - 0 - - - H - - - - - - - OCH3 OCH3 J21 - - - - - H CH3 - - - - - - OCH3 OCH3 J21 - - - - - H CH3 - - - - - - Cl OCH3 J21 - - - - - H C2H5 - - - - - - OCH3 OCH3 J22 - - - - - H CH3 - - - - - - OCH3 OCH3 J22 - - - - - H C2H5 - - - - - - OCH3 OCH3 J23 - CH2 - - - H - H - - - - - OCH3 OCH3 J23 - CH2 - - - H - H - - - - - OCH3 CH3 J23 - CH2 - - - H - H - - - - - Cl OCH3 Table XXIIIa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J23 - CH2 - - - H - H - - - - - Br OCH3 J23 - CH2 - - - H - CH3 - - - - - OCH3 OCH3 J23 - 0 - - - H - H - - - - - OCH3 OCH3 J23 - 0 - - - H - H - - - - - Cl OCH3 J23 - 0 - - - H - CH3 - - - - - OCH3 OCH3 J24 - CH2 0 - - H - - - - - - - OCH3 OCH3 J24 - CH2 0 - - H - - - - - - - Cl OCH3 J24 - 0 0 - - H - - - - - - - OCH3 OCH3 J24 - 0 0 - - H - - - - - - - Cl OCH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 OCH3 J24 - CH2 CH2 - - H - - - - - - - Cl OCH3 J24 - 0 CH2 - - H - - - - - - - OCH3 OCH3 J24 - 0 CH2 - - H - - - - - - - Cl OCH3 J25 - CH2 - - - H - - - - - - - OCH3 OCH3 J25 - CH2 - - - H - - - - - - - Cl OCH3 J25 - 0 - - - H - - - - - - - OCH3 OCH3 J25 - 0 - - - H - - - - - - - Cl OCH3 J26 - - - 0 - H - CH3 H H - - - OCH3 OCH3 J26 - - - 0 - H - CH3 H H - - - OCH3 CH3 J26 - - - 0 - H - H H CH3 - - - CH3 CH3 J26 - - - 0 - H - H H CH3 - - - Cl OCH3 J26 - - - 0 - H - CH3 H H - - - Br OCH3 J26 - - - 0 - H - H H CH3 - - - OCH3 C2H5 J26 - - - 0 - H - CH3 H H - - - CH3 OC2H5 J26 - - - 0 - H - CH3 H H - - - OCH3 CF3 J26 - - - 0 - H - H H C2H5 - - - OCH3 OCH3 J26 - - - 0 - H - CH3 H H - - - OCH3 OCH3 J26 - - - 0 - H - CH3 H CH3 - - - OCH3 OCH3 J26 - - - 0 - H - CH3 H CH3 - - - OCH3 CH3 J26 - - - 0 - H - CH3 H CH3 - - - CH3 CH3 J26 - - - 0 - H - CH3 H CH3 - - - Cl OCH3 J26 - - - 0 - H - CH3 H CH3 - - - Br OCH3 Table XXIIIa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J26 - - - 0 - H - CH3 H CH3 - - - OCH3 C2H5 J26 - - - 0 - H - CH3 H CH3 - - - CH3 OC2H5 J26 - - - 0 - H - CH3 H CH3 - - - OCH3 CH2OCH3 J26 - - - 0 - H - CH3 H CH3 - - - OCH3 CH2F J26 - - - 0 - H - CH3 H CH3 - - - OCH3 CF3 J26 - - - S - H - CH3 H H - - - OCH3 OCH3 J26 - - - S - H - CH3 H H - - - OCH3 CH3 J26 - - - S - H - CH3 H H - - - CH3 CH3 J26 - - - S - H - CH3 H H - - - Cl OCH3 J26 - - - S - H - CH3 H H - - - Br OCH3 J26 - - - S - H - H CH3 CH3 - - - OCH3 OCH3 222-222.5 J26 - - - SO2 - H - CH3 H H - - - OCH3 CH3 208-209 J26 - - - SO2 - H - CH3 H H - - - CH3 CH3 192-193 J26 - - - SO2 - H - CH3 H H - - - Cl OCH3 J26 - - - SO2 - H - CH3 H H - - - Br OCH3 J26 - - - SO2 - H - CH3 H H - - - OCH3 C2H5 J26 - - - SO2 - H - CH3 H H - - - CH3 OC2H5 J26 - - - SO2 - H - CH3 H H - - - OCH3 CH2OCH3 J26 - - - SO2 - H - CH3 H H - - - OCH3 CH2F J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CF3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 OCH3 J26 - - - SO2 - H - CH3 CH3 CH3 - - - OCH3 OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH3 J26 - - - SO2 - H - CH3 H CH3 - - - CH3 CH3 J26 - - - SO2 - H - CH3 H CH3 - - - Cl OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - Br OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 C2H5 J26 - - - SO2 - H - CH3 H CH3 - - - CH3 OC2H5 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH2OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH2F J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH2F J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CF3 Table XXIIIa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J26 - - - SO2 - H - H H H - - - CH3 CH3 J26 - - - SO2 - H - H H H - - - CH3 OCH3 J26 - - - SO2 - H - H H H - - - OCH3 OCH3 J26 - - - SO2 - H - H H H - - - Cl OCH3 J26 - - - SO2 - 6-Cl CH3 H H H - - - CH3 CH3 J26 - - - SO2 - 6-Cl CH3 H H H - - - OCH3 OCH3 J26 - - - SO2 - 6-Cl CH3 H H H - - - Cl OCH3 J26 - - - SO2 - 6-Cl CH3 H H H - - - CH3 OCH3 J26 - - - S - H - CH3 H CH3 - - - CH3 OCH3 J26 - - - S - H - CH3 H CH3 - - - OCH3 CH3 J26 - - - S - H - CH3 H CH3 - - - CH3 CH3 J26 - - - S - H - CH3 H CH3 - - - Cl OCH3 J26 - - - S - H - CH3 H CH3 - - - Br OCH3 J26 - - - 0 - 6-Cl - CH3 H H - - - OCH3 OCH3 J26 - - - 0 - 5-Br - H H CH3 - - - OCH3 OCH3 J26 - - - 0 - 6-F - CH3 H H - - - OCH3 C2H5 J26 - - - 0 - 5-CH3 - CH3 H H - - - OCH3 OCH3 J26 - - - O - 6-OCH3 - CH3 H H - - - OCH3 OCH3 J26 - - - S - 6-OCH3 - CH3 H H - - - OCH3 OCH3 J27 - CH2 - O - H - CH3 H - - - - OCH3 OCH3 J27 - CH2 - S - H - H CH3 - - - - OCH3 OCH3 J27 - 0 - SO2 - H - CH3 H - - - - OCH3 OCH3 J27 - 0 - SO2 - H - CH3 H - - - - Cl OCH3 J28 - - - - O H - CH3 H - - - - OCH3 OCH3 J28 - - - - S H - CH3 H - - - - OCH3 OCH3 J28 - - - - O H - CH3 CH3 - - - - OCH3 OCH3 J28 - - - - O H - H H - - - - OCH3 OCH3 J29 - CH2 - - - H - H H - H H - OCH3 OCH3 J29 - CH2 - - - H - H H - CH3 H - Cl OCH3 J29 - 0 - - - H - H H - H CH3 - OCH3 OCH3 J30 - - - - - H - CH3 CH3 - - - - OCH3 OCH3 J30 - - - - - H - H H - - - - OCH3 OCH3 Table XXIIIn (continued) m.p. J n L 0 Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J30 - - - - - H - H H - - - - Cl OCH3 J30 - - - - - H - CH3 CH3 - - Cl OCH3 J31 - CH2 - - - H - - - - - OCH3 OCH3 J31 - CH2 - - - H - - - - - OCH3 CH3 J31 - CH2 - - - H - - - - - - Cl OCH3 J31 - CH2 - - - H - - - - - - CH3 CH3 J31 - CH2 - - - 7-Cl - - - - - - - OCH3 OCH3 J31 - O - - - H - - - - - - - OCH3 CH3 J31 - O - - - H - - - - - - - OCH3 OCH3 J31 - O - - - H - - - - - - - Cl OCH3 J31 - O - - - H - - - - - - - CH3 CH3 J31 - CH2 - - - - - - - - - - F OCH3 OCH3 J31 - CH2 - - - - - - - - - - Cl Cl OCH3 J31 - CH2 - - - - - - - - - - Br OCH3 CH3 J32 - CH - - - - - - - - - - Br OCH3 CH3 J32 - CH2 - - - - - - - - - OCH3 OCH3 OCH3 J32 - CH2 - - - - - - - - - - SCH3 OCH3 OCH3 J32 - CH2 - - - - - - - - - - SO2CH3 OCH3 OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 OCH3 J32 - CH2 - - - - - - - - - - SO2N(CH3) OCH3 OCH3 332 - CH2 - - - - - -- - - - S02S(CH3)2 OCH3 OCH3 J32 - CH2 - - - - - - - - - - OSO2CH3 OCH3 OCH3 J32 - CH2 - - - - - - - - Cl OCH3 OCH3 J32 - CH2 - - - - - - - - - Cl Br OCH3 J32 - CH2 - - - - - - - - - Cl OCH3 CH2F J32 - CH2 - - - - - - - - - Cl CH3 OC2H5 J32 - CH2 - - - - - - - - - Cl OCH3 C2H5 J32 - O - - - - - - - - - - F OCH3 OCH3 J32 - O - - - - - - - - - - Cl OCH3 OCH3 J32 - O - - - - - - - - - - Br Cl OCH3 J32 - O - - - - - - - - - - OCH3 OCH3 OCH3 J32 - O - - - - - - - - - - SCH3 OCH3 OCH3 J32 - O - - - - - - - - - - SO2CH3 OCH3 OCH3 Table XXIIIn (continued) m.p. J n L 0 Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J32 - O - - - - - - - - - - CO2CH3 OCH3 OCH3 J32 - O - - - - - - - - - - SO2N(CH3)2 OCH3 OCH3 J32 - O - - - - - - - - - - OSO2CH3 OCH3 CH3 J32 - CH2 - - - - - - - - - - CO2CH3 CH3 OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 CH3 CH3 J32 - CH2 - - - - - - - - - - CO2CH3 C1 OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 Br OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 C2H5 J32 - CH2 - - - - - - - - - - CO2CH3 CH3 OC2H5 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 CH2OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 CH2F J32 - CH - - - - - - - - - - CO2CH3 OCH3 CF3 J15 0 CH2 - - - H - H H - - - - OCH3 CH2CH2CH2 J15 0 CH2 - - - H - H H - - - - C1 NHCH3 J15 O CH2 - - - H. - H H - - - - C1 OCF2H J15 0 CH2 - - - H - H H - - - - C1 N(CH3)2 J15 O CH2 - - - H - H H - - - OCH3 cyclopropyl J15 0 CH2 - - - H - H H - - - - OCH3 C#CH J15 0 CH2 - - - H - H H - - - - OCH3 OCH2CH=CH2 J15 0 CH2 - - - H - H H - - - - OCH3 OCH2CH2F J16 0 - - - - H CH3 - - - - - - OCH3 CH(CH3)2 J16 0 - - - - H CH3 - - - - - - C1 NCH3 J16 0 - - - - H CH3 - - - - C1 OCF2H J16 0 - - - - H CH3 - - - - - C1 N(CH3)2 J16 0 - - - - H CH3 - - - - - - OCH3 cyclopropyl J16 0 - - - - H CH3 - - - - - OCH3 C#CH J16 0 - - - - H CH3 - - - - - OCH3 OCH2C#CH J16 0 - - - - H CH3 - OCH3 OCH2CH2F J16 0 - - - - H CH3 - - - - - - C1 OCF2H J16 0 - - - - H CH3 - - - OCH3 SCH3 J16 0 - - - - H CH3 - - OCH3 CH(OCH3)2 Table XXIIIa (continued) m.p. J n L 0 Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J16 O - - - - H CH3 - - - - - - OCH3 1,3-dioxolan 2-yl J17 O CH2 - - - H CH3 - - - - - - OCH3 CH(CH3)2 J17 0 CH2 - - - H CH3 - - - - - - OCH3 cyclopropyl J17 O CH2 - - - H CH3 - - - - - - OCH3 C#CH J17 O CH2 - - - H CH3 - - - - - - C1 N(CH3)2 J17 O CH2 - - - H CH3 - - - - - - C1 N(NCH3)2 J17 O CH2 - - - H CH3 - - - - - - OCH3 OCH2CH2F J17 O CH2 - - - H CH3 - - - - - - OCH3 SCH3 J17 O CH2 - - - H CH3 - - - - - - OCH3 CH(OCH3)2 J19 - CH2 - - - H - - - - - - - OCH3 NCH3 J19 - CH2 - - - H - - - - - - - OCH3 C#CH J19 - CH2 - - - H - - - - - - - C1 NHCH3 J19 - CH2 - - - H - - - - - - - OCH3 CH(OCH3)2 J19 - CH2 - - - H - - - - - - - OCH3 OCH2C#CH J19 - CH2 - - - H - - - - - - - OCH3 OCH2CH2F J19 - CH2 - - - H - - - - - - - OCH3 SCH3 <RTI ID=94.5> J19 - CH2 - - - H - - - - - - - OCH3 1,3-dioxolan 2-yl J19 - CH2 - - - H - - - - - - - OCH3 cyclopropyl J20 - O - - - H - - - - - - - OCH3 CH(OCH3)2 J20 - O - - - H - - - - - - - C1 N(CH3)2 J20 - O - - - H - - - - - - - OCH3 NHCH3 J21 - - - - - H CH3 - - - - - - C1 NHCH3 J21 - - - - - H CH3 - - - - - - C1 OCH3 J22 - - - - - H CH3 - - - - - - C1 OCH3 J22 - - - - - H H - - - - - - OCH3 NHCH3 J23 - O - - - H - H - - - - - C1 NHCH3 J23 - O - - - H - CH3 - - - - - OCH3 N(CH3)2 J23 - O - - - H - CH3 - - - - - OCH3 1,3-dioxolan 2-yl J24 - CH2 CH2 - H - - - - - - - OCH3 N(CH3)2 Table XXIIIa (continued) m.p. J n L 0 Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J24 - CH2 CH2 - - H - - - - - - - OCH SCH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 CH(OCH3)2 J24 - CH2 CH2 - - H - - - - - - - OCH3 OCH2CH#CH J25 - CH2 - - - H - - - - - - - OCH3 OCH2CH#CH2 J25 - CH2 - - - H - - - - - - - CH3 OCH2CH2F J25 - CH2 - - - H - - - - - - - OCH2CF3 OCH3 J25 - CH2 - - - H - - - - - - - OCHF2 OCHF2 J25 - CH2 - - - H - - - - - - - OCH3 OCH2CH2OCH3 J26 - - - O - H - CH3 H H - - - OCH3 NHCH3 J26 - - - O - H - CH3 H H - OCH3 NHCH3 J26 - - - O - H - H H H - - - OCH3 C#CH J26 - - - O - H - H H H - - - OCH3 OCH2CH2F J26 - - - O - H - CH3 H H - - - OCH3 OCH2CH#CHC1 J26 - - - O - H - H H H - - - C1 NHCH3 J26 - - - O - H - H H CH3 - - - C1 N(CH3)2 J26 - - - O - H - H H CH3 - - - OCH3 cyclopropyl J26 - - - O - H - H H CH3 - - - OCH3 CH(OCH3)2 J26 - - - O - H - CH3 CH3 H - - - NHCH3 J26 - - - O - H - CH3 CH3 H - - - OCH3 CH(OCH3)2 J26 - - - O - H - CH3 H H - - - OCH3 OCH2C#CH J26 - - - O - H - CH3 CH3 H - - - OCH3 SCH3 J26 - - - S - H - CH3 H H - OCH3 NHCH3 J26 - - - S - H - CH3 H H - - - OCH3 N(CH3) 26 - - - S - H - ""3 H U - - - ""3 """3'2 J26 - - - S - H - CH3 H H - - - OCH3 OCH2#CH2 J26 - - - S - H - CH3 H H - - - OCH3 cyclopropyl J - - - S - H - CH3 H H - - - C1 N(CH) J26 - - - S - H - CH3 3 H - - - C1 N(CH3)2 J26 - - - S - H - CH3 CH3 CH3 - - - OCH3 CH(OCH3)2 J26 - - - SO2 - H - CH3 H H - - - OCH3 NHCH3 J26 - - - SO - H - CH3 H H - - - C1 N(CH) 32 J26 - - - SO2 - H - CH3 H H - - - OCH3 OCH2CH#CH2 J26 - - - SO2 - H - CH3 H H - - OCHF2 SCH3 J26 - - - SO2 - H - CH3 H H - - - CH3 OCH2CH2OCH3 Table XXXIIIn (continued) m.p. J n L 0 Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J26 - - - SO2 - H - CH3 H H - - - CH3 CH(OCH3)2 J27 - CH2 - O - H - CH3 H - - - OCH3 N(CH3)2 J27 - CH2 - S - H - H CH3 CH3 - - - OCH3 OCH2CH#CH2 J27 - O - SO2 - H - CH3 H ¯ - - - OCH3 OCH2CH2F J27 - O - SO2 - H - CH3 H - - - - OCH3 OCH2CH2OCH3 J28 - - - - O H - CH3 H - - - - C1 N(CH3)2 J28 - - - - O H - CH3 H - - - - CH3 CH(OCH3)2 J28 - - - - S H - CH3 H - - - - OCH3 NHCH3 J29 - CH2 - - - H - H H - H H - OCH3 NHCH3 J29 - CH2 - - - H - H H - CH3 H - C1 N(CH3)2 J29 - O - - - H - H H - H CH3 - CH3 OCH2CH2OCH3 J30 - - - - - H - H H - - - - CH3 OCH2CH2F J30 - - - - - H - CH3 CH3 - - - - OCH3 NHCH3 J30 - - - - - H - H CH3 - - - - OCH3 C#CH J31 - CH2 - - - H - - - - - - - OCH3 NHCH3 J31 - CH2 - - - H - - - - - - - CH3 OCH2CH2F J31 - O - - - H - - - - - OCH3 <RTI ID=96.4> C#CH J31 - O - - - H - - - - - - - OCH3 CH(OCH3)2 J32 - CH2 - - - - - - - - - - Cl OCH3 NHCH3 J32 - CH2 - - - - - - - - - Br OCH3 N(CH)2 J32 - CH2 - - - - - - - - - - F OCH3 NHCH3 J32 - CH2 - - - - - - - - - - OCH3 OCH3 NHCH3 J32 - CH2 - - - - - - - - - - SO2N(CH3)2 OCH3 C#CH J32 - CH2 - - - - - - - - - - Cl OCH3 OCH2CH2F J32 - O - - - - - - - - - - CL CL NHCH3 J32 - O - - - - - - - - - - Br CL NHCH3 J32 - O - - - - - - - - - - OCH3 OCH3 NHCH3 J32 - O - - - - - - - - - - SO2N(CH3)2 OCH3 NHCH3 J32 - O - - - - - - - - - - SO2CH3 OCH3 NHCH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 OCH3 148-151.5 J32 - CH2 - - - - - - - - - - CO2CH3 CH3 CH3 191-193.5 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 CH3 Table XXIV General Formula 3 m.p. J n L R20 R22 X Y ( C) J12 0 CH2 H CH3 CH3 OCH3 J12 0 CH2 H CH3 OCH3 OCH3 J12 0 CH2 H CH3 CH3 CH3 J12 0 CH2 H CH3 OCH3 C2H5 J12 0 CH2 H CH3 CH3 OC2H5 J12 0 CH2 H CH3 OCH3 CH2OCH3 J12 0 CH2 H CH3 OCH3 CH2F J12 0 CH2 H CH3 OCH3 CF3 J12 1 CH2 H CH3 OCH3 CH3 J12 0 CH2 H C2H5 OCH3 CH3 J12 0 CH2 H n-C3H7 OCH3 CH3 J12 0 CH2 H CH(CH3)2 OCH3 CH3 J12 0 CH2 H H OCH3 OCH3 J12 0 CH2 H H OCH3 CH3 J12 0 CH2 H H CH3 CH3 J12 0 O H H CH3 CH3 J12 0 O H H CH3 OCH3 J12 0 O H H OCH3 OCH3 J12 0 O H CH3 OCH3 OCH3 J12 0 O H CH3 CH3 OCH3 J12 0 O H CH3 CH3 CH3 J12 0 O H C2H5 OCH3 OCH3 J12 0 O H n-C3H7 OCH3 CH3 J12 0 O H CH(CH3)2 OCH3 CH3 J12 1 O H CH3 OCH3 CH3 J12 0 CH2 H CH3 OCH3 CH3 J12 0 CH2 H CH3 OCH3 CH3 J12 0 CH2 H CH3 OCH3 OCH3 J12 0 CH2 H CH3 OCH3 OCH3 J12 0 CH2 H CH3 OCH3 OCH3 J12 0 O H CH3 OCH2CF3 CH3 J12 0 O H CH3 OCH3 CH(CH3)2 Table XXIV (continued) m.p. J n L R20 R22 X Y ( C) J12 0 O H CH3 OCH3 cyclopropyl J12 0 O H CH3 OCH3 C#CH J12 0 O H CH3 OCH3 NH2 J12 0 O H CH3 OCH3 N(CH3)2 J12 0 O H CH3 OCH3 OCH2CH2F J12 0 O H CH3 OCH3 SCH3 J12 0 O H CH3 OCH3 OCH2CH=CH2 J12 0 O H CH3 OCH3 OCH2CH2OCH3 J12 0 O H CH3 OCH3 OCH2C#CH J12 0 O H CH3 OCH3 CH(OCH3)2 J12 0 O H CH3 OCH3 C(CH3)(OCH3)2 J12 0 O H CH3 OCH3 1,3-dioxolan 2-yl J12 0 O H CH3 OCH3 1-methyl-1,3 dioxolan-2-yl J12 0 O H CH3 OCH3 CH(OC2H5)2 J12 0 O H CH3 OCH3 C(CH3)(OC2H5)2 J12 0 O H CH3 OCH3 NHCH3 J12 0 O H -CH2CN OCH3 OCH3 J12 0 O H -(CH2)3CN CH3 OCH3 J12 0 CH2 H OH CH3 OCH3 J12 0 CH2 H OH CH3 OCH3 J12 0 CH2 H -CF2H OCH3 OCH3 J12 0 CH2 H -CH2CH2Cl Cl OCH3 J12 0 CH2 H -(CH2)5Cl CH3 OCH3 J12 0 CH2 H -CH2OCH3 Cl OCH3 J12 0 CH2 H -(CH2)4OCH3 CH3 OCH3 J12 0 CH2 H -CH2CH=CH2 OCH3 OCH3 J12 0 CH2 H -CH2CH=CHCH3 CH3 OCH3 J12 0 CH2 H -CH2C#CH OCH3 OCH3 J12 0 CH2 H -(CH2)4C#CH CH3 OCH3 J12 0 CH2 H -OCH3 CH3 OCH3 J12 0 CH2 H -C6H5 CH3 OCH3 J12 0 CH2 H cyclopropyl OCH3 OCH3 Table XXIV (continued) m.p. J n L R20 R22 X Y ( C) J12 0 CH2 H cyclohexyl OCH3 OCH3 J12 0 CH2 H cyclopropylmethyl OCH3 OCH3 J12 0 CH2 H cyclohexylmethyl CH3 OCH3 J12 0 CH2 H -C(O)CH3 OCH3 OCH3 J12 0 CH2 H -C(O)(CH2)5H OCH3 OCH3 J12 0 CH2 H -CO2C2H5 CH3 OCH3 J12 0 CH2 H -CO2(CH2)4H CH3 OCH3 J12 0 CH2 H -CH2C6H5 OCH3 OCH3 J12 0 CH2 H -CH2-CH=CH-CH2Cl CH3 OCH3 J12 0 CH2 H -CH2C#C-CH2Cl CH3 OCH3 J12 0 CH2 H -CH2C(O)CH3 OCH3 OCH3 J12 0 CH2 H -CH(CH3)CO2C2H5 OCH3 OCH3 J12 0 CH2 H H OCH3 OCH3 J12 0 CH2 H H CH3 CH3 J12 0 O H H CH3 CH3 J12 0 O H H OCH3 CH3 J12 0 O H H OCH3 OCH3 J12 0 CH2 H n-C4H9 CH3 CH3 J12 0 CH2 H n-C4H9 CH3 OCH3 J12 0 CH2 H n-C4H9 OCH3 OCH3 J12 0 O H n-C4H9 CH3 CH3 J12 0 O H n-C4H9 OCH3 CH3 J12 0 O H n-C4H9 OCH3 OCH3 J18 - CH2 H n-C3H7 CH3 OCH3 J18 - CH2 H CH(CH3)2 CH3 OCH3 J18 - O H CH3 CH3 OCH3 J18 - CH2 7-Cl CH3 CH3 OCH3 J18 - O 7-Br CH3 CH3 OCH3 J18 - CH2 6-F CH3 CH3 OCH3 J18 - O 7-CH3 CH3 CH3 OCH3 J18 - O 7-OCH3 CH3 CH3 OCH3 J18 - CH2 H CH3 OCH3 OCH3 J18 - CH2 H CH3 OCH3 CH3 Table XXIV (continued) m.p. J n L R20 R22 X Y ( C) J18 - CH2 H CH3 CH3 CH3 J18 - CH2 H CH3 OCH3 C2H5 J18 - CH2 H CH3 CH3 OC2H5 J18 - CH2 H CH3 OCH3 CH2OCH3 J18 - CH2 H CH3 OCH3 CH2F J18 - CH2 H CH3 OCH3 CF3 J18 - CH2 H H CH3 OCH3 J18 - CH2 H C2H5 CH3 OCH3 J18 - CH2 H CH3 OCH2CF3 OCH3 J18 - CH2 H CH3 OCH3 cyclopropyl J18 - CH2 H CH3 OCH3 NHCH3 J18 - CH2 H CH3 OCH3 N(CH3)2 J18 - CH2 H CH3 OCH3 OCH2CH=CH2 J18 - CH2 H CH3 OCH3 CH(OCH3)2 J18 - CH2 H CH3 OCH3 1,3-dioxolan 2-yl J18 - CH2 H CH3 OCH3 CH(OC2H5)2 J18 - CH2 H CH3 OCH3 -C#CH J18 - CH2 H CH3 OCH3 C(CH3)(OCH3)2 J18 - CH2 H OH OCH3 OCH3 J18 - CH2 H (CH2)2CH(CH3)2 CH3 OCH3 J18 - CH2 H CH2CH2Cl OCH3 OCH3 J18 - CH2 H (CH2)5Cl CH3 OCH3 J18 - CH2 H CH2OCH3 CH3 OCH3 J18 - CH2 H (CH2)2OCH3 CH3 OCH3 J18 - CH2 H CH2CH=CH2 OCH3 OCH3 J18 - CH2 H CH2CH=CHCH2Cl CH3 OCH3 J18 - CH2 H CH2CH=CHCH3 CH3 OCH3 J18 - CH2 H <RTI ID=100.2> CH2C#CCH3 OCH3 OCH3 J18 - CH2 H OCH3 OCH3 OCH3 J18 - CH2 H O(CH2)4CH3 CH3 OCH3 J18 - CH2 H C6H5 OCH3 OCH3 Table XXIV (continued) m.p. J n L R20 R22 X Y ( C) J18 - CH2 H cyclopropyl CH3 OCH3 J18 - CH2 H cyclopentyl OCH3 OCH3 J18 - CH2 H COCH3 OCH3 OCH3 J18 - CH2 H CO2CH3 OCH3 OCH3 J18 - CH2 H CH2C6H5 CH3 OCH3 J18 - CH2 H CH2CH=CHCl CH3 OCH3 J18 - CH2 H CH(CH3)CO2CH3 CH3 OCH3 Table XXIVa General Formula 3a m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J13 0 CH2 - - - H H - - - - - - OCH3 OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 C2H5 J13 0 CH2 - - - H CH3 - - - - - - OCH3 OC2H5 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH2OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH2F J13 0 CH2 - - - H CH3 - - - - - - OCH3 CF3 J13 0 CH2 - - - H H - - - - - - CH3 OCH3 J13 0 CH2 - - - H C2H5 - - - - - - CH3 OCH3 J13 0 CH2 - - - H n-C3H7 - - - - - - CH3 OCH3 J13 0 CH2 - - - H CH(CH3)2 - - - - - - CH3 OCH3 J13 1 CH2 - - - H CH3 - - - - - - CH3 OCH3 J13 0 O - - - H CH3 - - - - - - OCH3 OCH3 J13 0 O - - - H CH3 - - - - - - OCH3 CH3 J13 1 O - - - H CH3 - - - - - - CH3 OCH3 J13 0 O - - - H CH3 - - - - - - CH3 OCH3 J13 0 0 - - - H C2H5 - - - - - - CH3 OCH3 J13 0 CH2 - - - 6-Br CH3 - - - - - - CH3 OCH3 J13 0 CH2 - - - 6-Cl CH3 - - - - - - CH3 OCH3 J13 0 CH2 - - - 5-F CH3 - - - - - - CH3 OCH3 J13 0 0 - - 6-CH3 CH3 - - - - - - CH3 OCH3 J13 0 0 - - - 6-OCH3 CH3 - - - - - - CH3 OCH3 J14 0 CH2 - - - H - H H - - - - OCH3 OCH3 J14 0 CH2 - - - H - H H - - - - CH3 OCH3 175-183.d J14 0 CH2 - - - H - H H - - - - CH3 CH3 J14 0 CH2 - - - H - H H - - - - OCH3 C2H5 J14 0 CH2 - - - H - H H - - - - CH3 OC2H5 J14 0 CH2 - - - H - H H - - - - CH3 CH2OCH3 J14 0 CH2 - - - H - H H - - - - OCH3 CH2F J14 0 CH2 - - - H - H H - - - - OCH3 CF3 J14 1 CH2 - - - H - H H - - - - CH3 OCH3 J14 0 CH2 - - - H - CH3 H - - - - CH3 OCH3 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J14 0 CH2 - - - H - H CH3 - - - - CH3 CH3 J14 0 O - - - H - H H - - - - OCH3 OCH3 J14 0 0 - - - H - H H - - - - CU3 CU3 J14 0 O - - - H - H H - - - - OCH3 CH3 J14 0 O - - - H - H H - - - - CH3 CH3 J14 0 CH2 - - - 5-F - H H - - - - CH3 OCH3 J14 0 CH2 - - - 6-Cl - H H - - - - OCH3 OCH3 J14 0 CH2 - - - 6-Br - H H - - - - OCH3 CH3 J14 0 O - - - 5-CH3 - H H - - - - OCH3 CH3 J14 0 O - - - 6-OCH3 - H H - - - - OCH3 CH3 J14 1 O - - - H - H H - - - - OCH3 CH3 J14 1 CH2 - - - H - CH3 H - - - - CH3 CH3 J14 1 CH2 - - - H - CH3 H - - - - CH3 OCH3 J14 1 CH2 - - - H - CH3 H - - - - OCH3 OCH3 J14 1 0 - - - H - CH3 H - - - - CH3 CH3 J14 1 0 - - - H - CH3 H - - - - CH3 OCH3 J14 1 0 - - - H - CH3 H - - - - OCH3 OCH3 J15 O CH2 - - - H - - - - - - - CH3 OCH3 J15 1 CH2 - - - H - H H - - - - CH3 CH3 J15 0 0 - - - H - - - - - - - CH3 OCH J15 1 0 - - - H - - - - - - - CH3 OCH3 J15 0 - - - - H - - - - - - - OCH3 OCH3 J16 0 - - - - H CH3 - - - - - - CH3 OCH J16 0 - - - - H CH3 - - - - - - CH3 CH3 J16 1 - - - - H CH3 - - - - - - CH3 OCH3 J16 0 - - - - H H - - - - - - CH3 OCH3 J17 0 - - - - H CH3 - - - - - - OCH3 OCH3 J17 0 - - - - H CH3 - - - - - - CH3 OCH3 J17 0 - - - - H H - - - - - - - CH3 OCH3 J17 1 - - - - H CH3 - - - - - - - CH3 OCH3 J19 - CH2 - - - H - H - - - - - - OCH3 OCH3 J19 - CH2 - - - H - H H - - - - - OCH3 CH3 J19 - CH2 - - - H - CH3 H - - - - - OCH3 CH3 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J19 - CH2 - - - H - H CH3 - - - - OCH3 C2H5 J19 - CH2 - - - H - H - - - - - CH3 OC2H5 J19 - CH2 - - - H - H - - - - - OCH3 CH2OCH3 J19 - CH2 - - - H - H - - - - - OCH3 CH2F J19 - CH2 - - - H - H - - - - - OCH3 CF3 J19 - O - - - H - H - - - - - OCH3 OCH3 J19 - 0 - - - H - H - - - - - OCH3 CH3 J19 - CH2 - - - 7-Cl - H - - - - - CH3 OCH3 J20 - CH2 - - - H - - - - - - - OCH3 OCH3 J20 - CH2 - - - H - - - - - - - OCH3 CH3 J20 - O - - - H - - - - - - - CH3 OCH3 J21 - - - - - H CH3 - - - - - - OCH3 OCH3 J21 - - - - - H CH3 - - - - - - OCH3 CH3 J21 - - - - - H C2H5 - - - - - - CH3 OCH3 J22 - - - - - H CH3 - - - - - - CH3 OCH3 J22 - - - - - H C2H5 - - - - - - CH3 OCH3 J23 - CH2 - - - H - H - - - - - OCH3 OCH3 J23 - CH2 - - - H - H - - - - - OCH3 CH3 J23 - CH2 - - - H - CH3 - - - - - OCH3 OCH3 J23 - O - - - H - H - - - - - OCH3 OCH3 J23 - O - - - H - H - - - - - OCH3 CH3 J23 - O - - - H - CH3 - - - - - OCH3 CH3 J24 - CH2 O - - H - - - - - - - OCH3 OCH3 J24 - CH2 O - - H - - - - - - - OCH3 CH3 J24 - O O - - H - - - - - - - OCH3 OCH3 J24 - O O - - H - - - - - - - OCH3 CH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 OCH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 CH3 J24 - O CH2 - - H - - - - - - - OCH3 OCH3 J24 - O CH2 - - H - - - - - - - OCH3 CH3 J25 - CH2 - - - H - - - - - - - OCH3 OCH3 J25 - CH2 - - - H - - - - - - - OCH3 CH3 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J25 - O - - - H - - - - - - - OCH3 OCH3 J25 - O - - - H - - - - - - - OCH3 CH3 J26 - - - O - H - CH3 H H - - - OCH3 OCH3 J26 - - - O - H - CH3 H H - - - OCH3 CH3 J26 - - - O - H - H H CH3 - - - CH3 CH3 J26 - - - O - H - H H CH3 - - - OCH3 C2H5 J26 - - - O - H - CH3 H H - - - CH3 OC2H5 J26 - - - O - H - CH3 H H - - - OCH3 CH2OCH3 J26 - - - O - H - H H C2H5 - - - OCH3 CF3 J26 - - - 0 - H - CH3 CH3 H - - CH3 OCH3 J26 - - - SO2 - H - H H H - - - CH3 CH3 J26 - - - SO2 - H - H H H - - - CH3 OCH3 J26 - - - SO2 - H - H H H - - - OCH3 OCH3 J26 - - - O - H - CH3 H CH3 - - - OCH3 OCH3 J26 - - - O - H - CH3 H CH3 - - - OCH3 CH3 J26 - - - O - H - CH3 H CH3 - - - CH3 CH3 J26 - - - O - H - CH3 H CH3 - - - OCH3 C2H5 J26 - - - O - H - CH3 H CH3 - - - CH3 OC2H5 J26 - - - O - H - CH3 H CH3 - - - OCH3 CH2OCH3 J26 - - - O - H - CH3 H CH3 - - - OCH3 CH2F J26 - - - O - H - CH3 H CH3 - - - OCH3 CF3 J26 - - - S - H - CH3 H H - - - OCH3 OCH3 J26 - - - S - H - CH3 H H - - - OCH3 CH3 J26 - - - S - H - CH3 3 H - - - CH3 CH3 J26 - - - S - H - H CH3 CH3 - - - OCH3 CH3 J26 - - - SO2 - H - H H H - - - CH3 CH3 J26 - - - SO2 - H - H H H - - - CH3 OCH3 J26 - - - SO2 - H - H H H - - - OCH3 OCH3 J26 - - - SO2 - H - CH3 H H - - - OCH3 OCH3 192-194 J26 - - - SO2 - H - CH3 H H - - - OCH3 CH3 186-187 J26 - - - SO2 - H - CH3 H H - - - CH3 CH3 J26 - - - SO2 - H - CH3 H H - - - OCH3 C2H5 J26 - - - SO2 - H - CH3 H H - - - CH3 OC2H5 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J26 - - - SO2 - H - CH3 H H - OCH3 CH2OCH3 J26 - - - SO2 - H - CH3 H H - - OCH3 CH2F J26 - - - SO2 - H - CH3 H H - - OCH3 CF3 J26 - - - SO2 - H - CH3 CH3 H - - - OCH3 OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 OCH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH3 J26 - - - SO2 - H - CH3 H CH3 - - - CH3 CH3 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 C2H5 J26 - - - SO2 - H - CH3 H CH3 - - - CH3 OC2H5 J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CH2OCH3 J26 - - - SO2 - H - CH3 H CH3 - OCH3 CH2F J26 - - - SO2 - H - CH3 H CH3 - - - OCH3 CF3 J26 - - - S - H - CH3 H CH3 - - OCH3 OCH3 J26 - - - S - H - CH3 H CH3 - - OCH3 CH3 J26 - - - S - H - CH3 H CH3 - - CH3 CH3 J26 - - - SO2 - 6-Cl - CH3 H H - - - CH3 CH3 J26 - - - SO2 - 6-Cl - CH3 H H - - - OCH3 OCH3 J26 - - - O - 6-Cl - CH3 H H - - - CH3 OCH3 J26 - - - O - 5-Br - H H CH3 - - - CH3 OCH3 J26 - - - O - 6-F - CH3 H H - - - CH3 OCH3 J26 - - - O - 5-CH3 - CH3 H H - - - CH3 OCH3 J26 - - - O - 6-OCH3 - CH3 H H - - - CH3 OCH3 J26 - - - SO2 - 6-Cl - CH3 H H - - - CH3 OCH3 J26 - - - S - 6-Cl - CH3 H H - - - CH3 OCH3 J27 - CH2 - O - H - CH3 H - - - - CH3 OCH3 J27 - CH2 - S - H - H CH3 - - - - CH3 OCH3 J27 - O - SO2 - H - CH3 H - - - - CH3 OCH3 J27 - O - SO2 - H - CH3 H - - - - CH3 CH3 J28 - - - - O H - CH3 H - CH3 OCH3 J28 - - - - S H - CH3 H - - - - CH3 OCH3 J28 - - - - O H - CH3 CH3 - - - CH3 OCH3 J28 - - - - O H - H H - - - - CH3 OCH3 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J29 - CH2 - - - H - H H - H H - CH3 OCH3 J29 - CH2 - - - H - H H - CH3 H - OCH3 CH3 J29 - O - - - H - H H - H CH3 - CH3 OCH3 J30 - - - - - H - CH3 CH3 - CH3 OCH3 J30 - - - - - H - H H - - OCH3 OCH3 J30 - - - - - H - H H - - - - OCH3 CH3 J30 - - - - - H - CH3 CH3 - - - - OCH3 CH3 J31 - CH2 - - - H - - - - - - - OCH3 OCH3 J31 - CH2 - - - H - - - - - - - OCH3 CH3 J31- CH2 - - - H - - - - - - - CH3 CH3 J31 -CH2 - - - 7-Cl - - - - - - - OCH3 OCH3 J31 - O - - - H - - - - - - - OCH3 OCH3 J31 - O - - - H - - - - - - - OCH3 CH3 J31 - O - - - H - - - - - - - CH3 CH3 J32 - CH - - - - - - - - - - F OCH3 CH3 J32 - CH2 - - - - - - - - - - F OCH3 CH3 J32 - CH2 - - - - - - - - - - Cl OCH3 CH3 J32 - CH2 - - - - - - - - - - Br OCH3 CH3 J32 - CH2 - - - - - - - - - - OCH3 OCH3 OCH3 J32 - CH2 - - - - - - - - - - SCH3 OCH3 CH3 J32 - CH2 - - - - - - - - - - SO2CH3 OCH3 CH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 OCH3 122-122.5 J32 - CH2 - - - - - - - - - - SO2N(CH3)2 OCH3 CH3 J32 - CH2 - - - - - - - - - - S02N(CH3)2 OCH3 CH3 J32 - CH2 - - - - - - - - - - OSO2CH3 OCH3 CH3 J32 - CH2 - - - - - - - - - - Cl OCH3 CH3 J32 - CH2 - - - - - - - - - - Cl CH3 OCH3 J32 - CH2 - - - - - - - - - - Cl CH3 OC2H5 J32 - CH2 - - - - - - - - - - Cl OCH3 C2H5 J32 - O - - - - - - - - - - F OCH3 CH3 J32 - O - - - - - - - - - - Cl OCH3 CH3 J32 - O - - - - - - - - - - Br OCH3 CH3 J32 - O - - - - - - - - - - OCH3 OCH3 CH3 J32 - O - - - - - - - - - - SCH3 OCH3 CH3 J32 - O - - - - - - - - - - SO2CH3 OCH3 CH3 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J32 - O - - - - - - - - - - CO2CH3 OCH3 CH3 J32 - O - - - - - - - - - - SO2N(CH3)2 OCH3 CH3 J32 - O - - - - - - - - - - OSO2CH3 OCH3 CH3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 CH3 187-190 J32 - CH2 - - - - - - - - - - CO2CH3 CH3 OC2H5 J - CH - - - - - - - - - - CO2CH3 OCH3 CF3 J32 - CH2 - - - - - - - - - - CO2CH3 OCH3 C2H5 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH(CH3)2 J13 0 CH2 - - - H CH3 - - - - - - OCH2CF3 OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 cyclo propyl J13 0 CH2 - - - H CH3 - - - - - - OCH3 NHCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 N(CH3)2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 OCH2CH=CH2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH(OCH3)2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 1,3-dioxolan 2-yl J13 0 CH2 - - - H CH3 - - - - - - OCH3 CH(OC2H5)2 J13 0 CH2 - - - H CH3 - - - - - - OCH3 C#CH J13 0 CH2 - - - H CH3 - - - - - - OCH3 OCH2CH2OCH3 J13 0 CH2 - - - H CH3 - - - - - - OCH3 SCH3 J14 0 CH2 - - - H CH3 - - - - - - OCH3 NHCH3 J14 0 CH2 - - - H CH3 - - - - - - OCF2H OCH3 J14 0 CH2 - - - H CH3 - - - - - - OCH3 cyclo L J14 O CH2 - - - H CH3 - - - - - - OCH3 CH(OCH3)2 J14 0 CH2 - - - H CH - - - - - - OCH3 C#CH J14 0 CH2 - - - H CH3 - - - - - - OCH3 OCH2CH20CH3 J14 0 CH2 - - - H CH3 - - - - - - CH3 1,3-dioxolan 2-yl J14 0 CH2 - - - H CH3 - - - - - - CH3 OCH2C#CH J15 0 CH2 - - - H - H H - - - - OCH3 CH2CH2CH3 J15 0 CH2 - - - H - H H - - - - OCH3 cyclopropyl J15 0 CH2 - - - H - H H - - - - OCH3 C#CH J15 0 CH2 - - - H - H H - - - - OCH3 OCH2CH=CH2 J15 <RTI ID=108.10> O CH2 - - - H - H H - - - OCH3 OCH2CH2F Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J16 0 - - - - H CH3 - - - - - OCH3 CH(CH3)2 J16 0 - - - - H CH3 - - - - - OCH3 cyclopropyl J16 0 - - - - H CH3 - - - - - OCH3 C#CH J16 0 - - - - H CH3 - - - - - OCH3 OCH2C#CH J16 0 - - - - H CH3 - - - - - OCH3 OCH2CH2F J16 0 - - - - H CH3 - - - - - - OCH3 SCH3 J16 0 - - - - H CH3 - - - - - OCH3 CH(OCH3)2 J16 0 - - - - H CH3 - - - - - OCH3 1,3-dioxalan 2-yl J17 O CH2 - - - H CH3 - - - - - - OCH3 CH(CH3)2 J17 0 CH2 - - - H CH3 - - - - - OCH3 cyclopropyl J17 0 CH2 - - - H CH3 - - - - - OCH3 C#CH J17 0 CH2 - - - H CH3 - - - - - OCH3 OCH2CH2F J17 0 CH2 - - - H CH3 - - - - - OCH3 SCH3 J17 CH2 - - - H CH - - - - - - OCH3 CH(OCH3)2 J19 - CH2 - - - H - - - - - - OCH3 NHCH3 J19 - CH2 - - - H - - - - - - OCH3 C#CH J19 - CH2 - - - H - - - - - - OCH3 NHCH3 J19 - CH2 - - - H - - - - - - OCH3 CH(OCH3)2 J19 - CH2 - - - H - - - - - - OCH3 OCH2C#CH J19 - CH2 - - - H - - - - - - OCH3 OCH2CH2F J19 - CH2 - - - H - - - - - - OCH3 SCH3 J19 - CH2 - - - H - - - - - - OCH3 1,3-dioxalan 2-yl J19 - CH2 - - - H - - - - - - OCH3 cyclopropyl J20 0 CH2 - - - H - - - - - - OCH3 CH(OCH3)2 J20 0 CH2 - - - H - - - - - - OCH3 N(CH3)2 J20 0 CH2 - - - H - - - - - - OCH3 NHCH3 J21 - - - - - H CH3 - - - - - OCH3 NHCH3 J21 - - - - - H CH3 - - - - - CH3 CH(OCH3)2 J23 - CH2 - - - H CH3 - - - - - OCH3 CH(OCH3)2 J23 - CH2 - - - H CH3 - - - - - OCH3 NHCH3 J23 - O - - - H CH3 - - - - - CH3 NHCH3 Table XXIV. (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J23 - O - - - H - - - - - - - OCH3 N(CH3)2 J23 - O - - - H - - - - - - - OCH3 1,3-dioxolan 2-yl J24 - CH2 CH2 - - H - - - - - - - OCH3 NHCH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 SCH3 J24 - CH2 CH2 - - H - - - - - - - OCH3 CH(OCH3)2 J24 - CH2 CH2 - - H - - - - - - - OCH3 OCH2CH#CH J24 - CH2 - - - H - - - - - - - OCH3 OCH3CH=CH J25 CH2 - - - H -- - - - - - OCH3 OCH2CH=CH2 J25 - CH2 - - - H - - - - - - - CH3 OCH2CH2F J25 - CH2 - - - H - - - - - - - OCH2CF3 OCH3 J25 - CH2 - - - H - - - - - - - OCH3 OCH2CH2OCH3 J26 - - - O - H - CH3 H H - - - OCH3 NHCH3 J26 - - - O - H - CH3 H H - - OCH3 OCH2CH=CH2 J26 - - - O - H - H H H - - - OCH3 C#CH J26 - - - O - H - H H H - - - OCH3 OCH2CH2F J26 - - - O - H - H H H - - - OCH3 OCH2CH=CHCl J26 - - - O - H - H H H - - - CH3 NHCH3 J26 - - - O - H - H H CH3 - - - OCH3 N(CH3)2 J26 - - - O - H - H H CH3 - - - OCH3 cyclopropyl J26 - - - O - H - H H CH3 - - - OCH3 CH(OCH3)2 J26 - - - O - H - CH3 CH3 H - - - OCH3 NHCH3 J26 - - - O - H - CH3 CH3 H - - - OCH3 CH(OCH3)2 J26 - - - O - H - CH3 H H - - - OCH3 OCH3C#CH J26 - - - O - H - CH3 CH3 H - - - OCH3 SCH3 J26 - - - S - H - CH3 H H - - - OCH3 NHCH3 J26 - - - S - H - CH3 H H - - - OCH3 N(CH3)2 J26 - - - S - H - CH3 H H - - - OCH3 OCH2CH=CH2 J26 - - - S - H - CH3 H H - - - OCH3 cyclopropyl J26 - - - S - H - CH3 H H - - - OCH3 N(CH3)2 J26 - - - S - H - CH3 CH3 CH3 - - - OCH3 CH(OCH3)2 J26 - - - SO2 - H - CH3 H H - - - OCH3 NHCH3 J26 - - - SO2 - H - CH3 H H - - - OCH3 N(CH3)2 Table XXIVa (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 X Y ( C) J26 - - - SO2 - H - CH3 H H - OCH3 OCH2CH=CH2 J26 - - - SO2 - H - CH3 H H - CH3 OCH2CH2OCH3 J26 - - - SO2 - H - CH3 H H - - CH3 CH(OCH3)2 J27 - CH2 - O - H - CH3 H - OCH3 N(CH3)2 J27 - CH2 - S - H - H CH3 - - OCH3 OCH2CH=CH2 J27 - O - SO2 - H - CH3 H - - - - OCH3 OCH2CH2F J27 - O - SO2 - H - CH3 H - - - - OCH3 OCH2CH2OCH3 J28 - - - - O H - CH3 H - - - - OCH3 N(CH3)2 J28 - - - - O H - CH3 H - - CH3 CH(OCH3)2 J28 - - - - S H - CH3 H - - - - OCH3 NHCH3 J29 - CH2 - - - H - H H - H H - OCH3 NHCH3 J29 - CH2 - - - H - H H - CH3 H - OCH3 N(CH3)2 J29 - O - - - H - H H - H CH3 - CH3 OCH2CH2OCH3 J30 - - - - - H - H H - - - - CH3 OCH2CH2F J30 - - - - - H - CH3 CH3 - - - - OCH3 NHCH3 J30 - - - - - H - H CH3 - - - - OCH3 C#CH J31 - CH2 - - - H - - - - - - - OCH3 NHCH3 J31 - CH2 - - - H - - - - - - - CH3 OCH2CH2F J31 - O - - - H - - - - - - - OCH3 C#CH J31 - O - - - H - - - - - - - OCH3 CH(OCH3)2 J32 - CH2 - - - - - - - - - - Cl OCH3 NHCH3 J32 - CH2 - - - H - - - - - - Br OCH3 N(CH3)2 J32 - CH2 - - - H - - - - - - F OCH3 NHCH3 J32 - CH2 - - - H - - - - - - OCH3 OCH3 NHCH3 J32 - CH2 - - - H - - - - - - SO2N(CH3)2 OCH3 C#CH J32 - O - - - H - - - - - - Cl OCH3 OCH2CH2F J32 - O - - - H - - - - - - Cl OCH3 NHCH3 J32 - O - - - H - - - - - - Br OCH3 NHCH3 J32 - O - - - H - - - - - - OCH3 OCH3 NHCH3 J32 - O - - - H - - - - - - SO2W(CH3)2 OCH3 NHCH3 J32 - O - - - H - - - - - - SO2CH3 OCH3 NHCH3 Table XXV General Formula 4 m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X Y ( C) J12 0 CH2 - - - H - - - - - - - CH3 OCH3 O J12 0 CH2 - - - H - - - - - - - CH3 OCH3 O J12 0 CH2 - - - H - - - - - - - CH3 OCH3 CH2 J12 0 CH2 - - - H - - - - - - - CH3 OC2H5 O J12 0 CH2 - - - H - - - - - - - CH3 OCF2H O J12 0 O - - - H - - - - - - - CH3 OCH3 CH2 J12 0 0 - - - H - - - - - - - CH3 CH3 O J12 0 0 - - - H - - - - - - - CH3 OCF2H O J13 0 CH2 - - - H CH3 - - - - - - - OCH3 O J13 0 CH2 - - - H CH3 - - - - - - - CH3 O J13 0 CH2 - - - H CH3 - - - - - - - OCH3 CH2 J13 0 O - - - H CH3 - - - - - - - OCF2H O J13 1 CH2 - - - H CH3 - - - - - - - OCH3 CH2 J13 1 CH2 - - - H CH3 - - - - - - - CH3 O J13 1 0 - - - H CH3 - - - - - - - OCH3 O J14 0 CH2 - - - H - H U - - - - - OCH3 O J14 0 CH2 - - - H H H H - - - - - CH3 O J14 0 CH2 - - - H - H H - - - - - OCH3 CH2 J14 0 CH2 - - - H - H H - - - - - OCF2H O J14 1 CH2 - - - H - H H - - - - - OCH3 O J14 1 CH2 - - - H - H H - - - - - OCH3 CH2 J14 1 CH2 - - - H - H H - - - - - OC2H5 O J14 1 O - - - H - H H - - - - - OCH3 O J15 O CH2 - - - H - - - - - - - S- OCH3 CH2 J15 0 O - - - H - - - - - - - - OCH3 O J15 1 CH2 - - - H - - - - - - - - CH3 O J16 0 - - - - H CH3 - - - - - - - OCH3 CH2 J16 0 - - - - H CH3 - - - - - - - OCH3 O J16 0 - - - - H CH3 - - - - - - - CH3 O J17 0 - - - - H CH3 - - - - - - - OCH3 CH2 Table XXV (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X Y ( C) J18 - CH2 - - - H CH3 - - - - - - CH3 OCH3 CH2 J18 - CH2 - - - H CH3 - - - - - - CH3 CH3 O J19 - CH2 - - - H - H - - - - - - OCH3 O J19 - O - - - H - H - - - - - - CH3 O J20 - CH2 - - - H - - - - - - - - OCH3 CH2 J21 - - - - - H CH3 - - - - - - - OCH3 CH2 J21 - - - - - H CH3 - - - - - - - OCH3 O J22 - - - - - H CH3 - - - - - - - OCH3 O J23 - CH2 - - - H - H - - - - - - OCH3 CH2 J23 - CH2 - - - H - H - - - - - - OCH3 O J23 - O - - - H - H - - - - - - CH3 O J23 - O - - - H - H - - - - - - OCH3 CH2 J24 - CH2 O - - H - - - - - - - - OCH3 CH2 J24 - O O - - H - - - - - - - - CH3 O J24 - CH2 CH2 - - H - - - - - - - - OCH3 O J25 - CH2 - - - H - - - - - - - - OCH3 O J25 - CH2 - - - H - - - - - - - - CH3 O J25 - O - - - H - - - - - - - - OCH3 CH2 J26 - - - O - H - CH3 H H - - - - OCH3 O J26 - - - O - H - CH3 H H - - - - OCH3 CH2 J26 - - - O - H - CH3 H H - - - - CH3 O J26 - - - S - H - CH3 H H - - - - OCH3 O J26 - - - S - H - CH3 H H - - - - CH3 O J26 - - - SO2 - H - CH3 H H - - - - OCH3 O J26 - - - SO2 - H - CH3 H H - - - - OCH3 CH2 J27 - CH2 - O - H - CH3 H - - - - - OCH3 CH2 J27 - CH2 - S - H - CH3 H - OCH3 O J27 - CH2 - SO2 - H - CH3 H - - - - - CH3 O J27 - O - SO2 - H - CH3 H - - - - - CH3 O J28 - - - - O H - H H - - - - - OCH3 O J28 - - - - S H - H H - - - - - OCH3 O Table XXV (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 Y1 ( C) J29 - CH2 - - - H - H H - H H - - OCH3 O J29 - CH2 - - - H - H H - CH3 H - - CH3 O J30 - - - - - H - H H - - - - OCH3 O J30 - - - - - H - H H - - - - - CH3 O J31 - CH2 - - - H - - - - - - - - CH3 O J31 - CH2 - - - H - - - - - - - - OCH3 O J31 - O - - - H - - - - - - - - OCH3 CH2 J31 - O - - - H - - - - - - - - OCH3 O J32 - CH2 - - - - - - - - - - Cl - OCH3 O J32 - CH2 - - - - - - - - - - F - OCH3 O J32 - CH2 - - - - - - - - - - Br - OCH3 O J32 - CH2 - - - - - - - - - - SO2CH3 - OCH3 O J32 - CH2 - - - - - - - - - - OSO2CH3 - OCH3 CH2 J32 - CH2 - - - - - - - - - - SO2W(CH3)2 - OCH3 CH2 J32 - CH2 - - - - - - - - - - CO2CH3 - OCH3 CH2 J32 - O - - - - - - - - - - Cl - OCH3 O J32 - O - - - - - - - - - - F - OCH3 O J32 - O - - - - - - - - - - Br - OCH3 O J32 - O - - - - - - - - - - SO2CH3 - OCH3 O J32 - O - - - - - - - - - - OSO2CH3 - OCH3 O J32 - O - - - - - - - - - - SO2N(CH3)2 - OCH3 O J32 - O - - - - - - - - - - CO2CH3 - OCH3 O Table XXVI General Formula 5 m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 ( C) J12 0 CH2 - - - H - - - - - - - CH3 CH3 J12 0 CH2 - - - H - - - - - - - CH3 OCH3 J12 0 CH2 - - - H - - - - - - CH3 OC2H5 J12 O CH2 - - - H - - - - - - - CH3 OCF2H J12 0 O - - - H - - - - - - - CH3 CH3 J12 0 O - - - H - - - - - - - CH3 OCH3 J12 0 O - - - H - - - - - - - CH3 OCF2H J13 0 CH2 - - - H CH3 - - - - - - - CH3 J13 0 CH2 - - - H CH3 - - - - - - - OCH3 J13 0 O - - - H CH3 - - - - - - - CH3 J13 1 CH2 - - - H CH3 - - - - - - - OCH3 J13 1 CH2 - - - H CH3 - - - - - - - OC2H5 J13 1 O - - - H CH3 - - - - - - - OCH3 J14 0 CH2 - - - H - H H - - - - - OCH3 J14 0 CH2 - - - H - H H - - - - - CH3 J14 0 CH2 - - - H - H H - - - - - OC2H5 J14 1 CH2 - - - H - H H - - - - - OCH3 J14 1 CH2 - - - H - H H - - - - - CH3 J14 1 0 - - - H - H H - - - - - OCH3 J15 O CH2 - - - H - - - - - - - - OCH3 J15 0 O - - - H - H H - - - - - OCH3 J15 1 CH2 - - - H - - - - - - - - OCH3 J16 0 - - - - H CH3 - - - - - - - CH3 J16 0 - - - - H CH3 - - - - - - - OCH3 J16 0 - - - - H CH3 - - - - - - - OC2H5 J17 0 - - - - H CH3 - - - - - - - OCF2H J18 - CH2 - - - H CH3 - - - - - - CH3 OCH3 J18 - CH3 - - - H CH3 - - - - - - CU3 CU3 J19 - CH2 - - - H - H - - - - - - OCH3 J19 - O - - - H - H - - - - - - OCH3 Table XXVI (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 ( C) J20 - CH2 - - - H - - - - - - - - OCH3 J21 - CH2 - - - H CH3 - - - - - - - OCH3 J21 - CH2 - - - H CH3 - - - - - - - CH3 J22 - - - - - H CH3 - - - - - - - OC2H5 J23 - CH2 - - - H - H - - - - - - CH3 J23 - CH2 - - - H - H - - - - - - OCH3 J23 - O - - - H - H - - - - - - OCH3 J23 - O - - - H - H - - - - - - OCF2H J23 - O - - - H - H - - - - - - CH3 J24 - CH2 O - - H - - - - - - - - OCH3 J24 - O O - - H - - - - - - - - OC2H5 J24 - CH2 CH2 - - H - - - - - - - - CH3 J25 - CH2 - - - H - - - - - - - - OCH3 J25 - CH2 - - - H - - - - - - - - CH3 J25 - O - - - H - - - - - - - - OCH3 J26 - - - O - H - CH3 H H - - - - OCH3 J26 - - - O - H - CH3 H H - - - - CH3 J26 - - - O - H - CH3 H H - - - - OCHF2 J26 - - - S - H - CH3 H H - - - - CH3 J26 - - - S - H - CH3 H H - - - - OCH3 J26 - - - SO2 - H - CH3 H H - - - - CH3 J26 - - - SO2 - H - CH3 H H - - - - OCH3 J27 - CH2 - O - H - CH3 H - - - - - OCH3 J27 - CH2 - S - H - CH3 H - - - - - OCH3 J27 - CH2 - SO2 - H - CH3 H - - - - - OCH3 J27 - O - SO2 - H - CH3 H - - - - - OCH3 J28 - - - - O H - H H - - - - - OCH3 J28 - - - - S H - H H - - - - - OCH3 J29 - CH2 - - - H - H H - CH3 H - - CH3 J29 - CH2 - - - H - H H - H H - - OCH3 J30 - - - - - H - H H - - - - - OCH3 Table XXVI (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 ( C) J30 - - - - - H - H H - - - - - OC2H5 J31 - CH2 - - - H - - - - - - - - OCH3 J31 - CH2 - - - H - - - - - - OC2H5 J31 - O - - - H - - - - - - - OCH3 J31 - O - - - H - - - - - - - OC2H5 J32 - CH2 - - - - - - - - - Cl - OCH3 J32 - CH2 - - - - - - - - - F - OCH3 J32 - CH2 - - - - - - - - - Br - OCH3 J32 - CH2 - - - - - - - - - SO2CH3 - OCH3 J32 - CH2 - - - - - - - - - OSO2CH3 - OCH3 J32 - CH2 - - - - - - - - - SO2N(CH3)2 - OCH3 J32 - CH2 - - - - - - - - - CO2CH3 - OCH3 J32 - O - - - - - - - - - Cl - OCH3 J32 - O - - - - - - - - - F - OCH3 J32 - O - - - - - - - - - Br - OCH3 J32 - O - - - - - - - - - SO2CH3 - OCH3 J32 - O - - - - - - - - - OSO2CH3 - OCH3 J32 - O - - - - - - - - - SO2N(CH3)2 - OCH3 J32 - O - - - - - - - - - CO2CH3 - OCH3 Table XXVII General Formula 6 m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 Y3 ( C) J O CH2 - - - H - - - - - - - CH3 OCH3 CH3 J12 0 CH2 - - - H - - - - - - - CH3 OCH3 H J12 0 CH2 - - - H - - - - - - - CH3 CH3 CH3 J12 0 O - - - H - - - - - - - CH3 OCH3 CH3 J12 0 O - - - H - - - - - - - CH3 OCH3 H J12 0 0 - - - H - - - - - - - CH3 CH3 CH3 J13 0 CH2 - - - H CH3 - - - - - - - OCH3 H J13 0 CH2 - - - H CH3 - - - - - - - OC2H5 H J13 0 CH2 - - - H CH3 - - - - - - - CH3 CH3 J13 0 CH2 - - - K CH3 - - - - - - CH3 H J13 0 CH2 - - - H CH3 - - - - - - - OCH3 H J13 1 CH2 - - - H CH3 - - - - - - - OCH3 H J13 1 CH2 - - - H CH3 - - - - - - - CH3 CH3 J13 1 O - - - H CH3 - - - - - - - OCH3 CH3 J14 0 CH2 - - - H - H H - - - - - OCH3 H J14 1 CH2 - - - H - H H - - - - - CH3 H J14 1 CH2 - - - H - H H - - - - - CH3 CH3 J14 1 CH2 - - - H - H H - - - - - CH3 H J14 1 CH2 - - - H - H H - - - - - OCH3 H J14 1 0 - - - H - H H - - - - - CH3 H J15 0 CH2 - - - H - - - - - - - - OCH3 H J15 0 0 - - - H - - - - - - - - OCH3 CH3 15 1 CH2 - - - H - - - - - - - - OCH3 H J16 0 - - - - H CH3 - - - - - - - OCH3 H J16 0 - - - - H CH3 - - - - - - - OC2H5 CH3 J17 0 - - - - H CH - - - - - OCH3 H J18 - CH2 - - - H CH3 - - - - - - CH3 OCH3 CH3 J18 - CH2 - - - H CH3 - - - - - - CH3 OCH3 H J19 - CH2 - - - H - H - - - - - - OCH3 H J19 - O - - - H - H - - - - - - OCH3 CH3 Table XXVII (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 Y3 ( C) J20 - CH2 - - - H - - - - - - - - OCH3 CH3 J21 - - - - - H CH3 - - - - - - - OCH3 H J21 - - - - - H CH3 - - - - - - - CH3 H J22 - - - - - H CH3 - - - - - - - OCH3 H J23 - CH2 - - - H - H - - - - - - OCH3 H J23 - CH2 - - - H - H - - - - - - CH3 H J23 - O - - - H - H - - - - - - OCH3 H J23 - O - - - H - H - - - - - - CH3 H J24 - CH2 O - - H - - - - - - - - OCH3 H J24 - O O - - H - - - - - - - - OCH3 H J24 - CH2 CH2 - - H - - - - - - - - OCH3 H J25 - CH2 - - - H - - - - - - - - OCH3 H J25 - CH2 - - - H - - - - - - - - CH3 H J25 - O - - - H - - - - - - - - CH3 CH3 J26 - - - O - H - CH3 H H - - - - OCH3 CH3 J26 - - - O - H - CH3 H H - - - - OCH3 H J26 - - - S - H - CH3 H H - - - - OCH3 H J26 - - - S - H - CH3 H H - - - - OCH3 CH3 J26 - - - SO2 - H - CH3 H H - - - - OCH3 H J26 - - - SO2 - H - CH3 H H - - - - OCH3 CH3 J27 - CH2 - O - H - CH3 H - - - - - OCH3 H J27 - CH2 - S - H - CH3 H - - - - - OCH3 H J27 - CH2 - SO2 - H - CH3 H - - - - - OCH3 H J27 - O - SO2 - H - CH3 H - - - - - OCH3 H J28 - - - - O H - H H - - - - - OCH3 CH3 J28 - - - - S H - H H - - - - - OCH3 H J29 - CH2 - - - H - H H - H H - - OCH3 H J29 - CH2 - - - H - H H - CH3 H - - OCH3 H J29 - - - - - H - H H - H H - - OCH3 H J29 - - - - - H - H H - CH3 H - - OCH3 H J30 - CH2 - - - H - - - - - - - - OCH3 H Table XXVII (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X1 Y2 ( C) J31 - CH2 - - - H - - - - - - - - OCH3 CH3 J31 - O - - - H - - - - - - - - OCH3 H J31 - O - - - H - - - - - - - - OCH3 CH3 J32 - CH2 - - - - - - - - - - Cl - CH3 H J32 - CH2 - - - - - - - - - - F - OCH3 H J32 - CH2 - - - - - - - - - - Br - OCH3 H J32 - CH2 - - - - - - - - - - SO2CH3 - OCH3 H J32 - CH2 - - - - - - - - - - OSO2CH3 - OCH3 H J32 - CH2 - - - - - - - - - - SO2N(CH3)2 - OCH3 H J32 - CH2 - - - - - - - - - - CO2CH3 - OCH3 H J32 - O - - - - - - - - - - Cl - CH3 H J32 - O - - - - - - - - - - F - OCH3 H J32 - O - - - - - - - - - - Br - OCH3 H J32 - O - - - - - - - - - - SO2CH3 - OCH3 H J32 - O - - - - - - - - - - OSO2CH3 - OCH3 H J32 - O - - - - - - - - - - SO2N(CH3)2 - OCH3 H J32 - O - - - - - - - - - - CO2CH3 - OCH3 H Table XXVIII General Formula 7 m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X2 Y2 ( C) J12 0 CH2 - - - H - - - - - - - CH3 CH3 OCH3 J12 0 CH2 - - - H - - - - - - - CH3 C2H5 OC2H5 J12 0 CH2 - - - H - - - - - - - CH3 CH2CF3 SCH3 J12 0 CH2 - - - H - - - - - - - CH3 CH3 SC2H5 J12 0 CH2 - - - H - - - - - - - CH3 C2H5 OCF2H J12 0 CH2 - - - H - - - - - - - CH3 C2H5 SCF2H J12 0 O - - - H - - - - - - - CH3 C2H5 OCH3 J12 0 0 - - H - - - - - - - CH3 C2H5 SCH3 J12 0 O - - - H - - - - - - - CH3 C2H5 SCF2H J13 O CH2 - - - H CH - - -- - - - - CH2CF3 SCH3 J13 0 CH2 - - - H CH3 - - - - - - - CH2CH3 SC2H J13 0 0 - - - H CH3 - - - - - - - CH2CH3 SC2H5 J13 1 CH2 - - - H CH3 - - - - - - - CH2CH3 SCH3 J13 1 CH2 - - - H CH3 - - - - - - - CH2CF3 SC2H J13 1 0 - - - H CH3 - - - - - - - C2H5 SCH3 J14 0 CH2 - - - H - H H - - - - - CH3 SC2H5 J14 0 CH2 - - - H - H H - - - - - CH3 SCH3 J14 1 CH2 - - - H - H H - - - - - CH3 SCH3 J14 1 CH2 - - - H - H H - - - - - CH3 SC2H5 J14 1 0 - - - H - H H - - - - CH3 SC2H J15 0 CH2 - - - H - - - - - - - - CH3 SCH3 J15 0 O - - - H - - - - - - - - C2H5 SCH3 J15 1 CH2 - - - H - - - - - - - - CH3 SCH3 J16 0 - - - - H CH3 - - - - - - - CH3 SCH3 J16 0 - - - - H CH3 - - - - - - C2H5 SCH3 J16 0 - - - - H CH3 - - - - - - CH2CF3 SCH3 J17 0 - - - - H CH3 - - - - - - CH3 SCH3 J18 - CH2 - - - H CH3 - - - - - CH3 CH2CH3 SC2H5 J18 - CH2 - - - H CH3 - - - - - CH3 CH3 SC2H5 J19 - CH2 - - - H - H - - - - - CH3 SCH3 Table XXVIII (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X2 Y2 ( C) J19 0 O - - - H - H - - - - - - CH3 SCH3 J20 - CH2 - - - H - - - - - - - - CH3 SCH3 J21 - - - - - H CH3 - - - - - CH3 SCH3 J21 - - - - - H CH3 - - - - - C2H5 SC2H5 J22 - - - - - H CH3 - - - - - - - CH3 SCH3 J23 - CH2 - - - H - H - - - - - - C2H5 SCH3 J23 - CH2 - - - H - H - - - - - - CH3 SCH3 J23 - O - - - H - H - - - - - - CH3 SC2H5 J23 - O - - - H - H - - - - - - C2H5 SCH3 J24 - CH2 O - - H - - - - - - - - CH3 SCH3 J24 - O O - - H - - - - - - - - CH3 SCH3 J24 - CH2 CH2 - - H - - - - - - - - CH3 SCH3 J25 - CH2 - - - H - - - - - - - - CH3 SCH3 J25 - CH2 - - - H - - - - - - - - CH3 SC2H5 J25 - O - - - H - - - - - - - - CH3 SCH3 J26 - - - O - H - CH3 H H - - - - CH3 SCH3 J26 - - - O - H - CH3 H H - - - - CH3 SC2H5 J26 - - - O - H - CH3 H H - - - C2H5 SCH3 J26 - - - S - H - CH3 H H - - - - CH3 SCH3 J26 - - - S - H - CH3 H H - - - - CH3 SC2H5 J26 - - - SO2 - H - CH3 H H - - - - CH3 SCH3 J26 - - - SO2 - H - CH3 H H - - - - CH3 SC2H5 J27 - CH2 - O - H - CH3 H - - - - - C2H5 SCH3 J27 - CH2 - S - H - CH3 H - - - - - CH3 SCH3 J27 - CH2 - SO2 - H - CH3 H - - - - - CH3 SCH3 J27 - O - SO2 - H - CH3 H - - - - - CH3 SCH3 J28 - - - - O H - H H - - - - - CH3 SCH3 J28 - - - - S H - H H - - - - - CH3 SCH3 J29 - CH2 - - - H - H H - H H - - CH3 SCH3 J29 - CH2 - - - H - H H - CH3 H - - CH3 SCH3 J30 - - - - - H - H H - - - - - CH3 SCH3 Table XXVIII (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X2 Y2 ( C) J30 - - - - - H - H H - - - CH3 SC2H5 J31 - CH2 - - - H - - - - - - - - CH3 SCH3 J31 - CH2 - - - H - - - - - - - - CH3 SC2H5 J31 - O - - - H - - - - - - - - CH3 SCH3 J31 - O - - - H - - - - - - - - C2H5 SCH3 J32 - CH2 - - - - - - - - - - Cl - CH3 SCH3 J32 - CH2 - - - - - - - - - - F - CH3 SCH3 J32 - CH2 - - - - - - - - - - Br - CH3 SCH3 J32 - CH2 - - - - - - - - - - SO2CH3 - CH3 SCH3 J32 - CH2 - - - - - - - - - - OSO2CH3 - CH3 SCH3 J32 - CU2 - . - - - - - - - - SO2N(CH3)2 - CH3 SCH3 J32 - CH2 - - - - - - - - - - C02CH3 - CH3 SCM3 J32 - O - - - - - - - - - - Cl - CH3 SCH3 J32 - O - - - - - - - - - - F - CH3 SCH3 J32 - O - - - - - - - - - - Br - CH3 SCH3 J32 - O - - - - - - - - - - SO2CH3 - CH3 SCH3 J32 - O - - - - - - - - - - OSO2CH3 - CH3 SCH3 J32 - O - - - - - - - - - - SO2N(CH3)2 - CH3 SCH3 J32 - O - - - - - - - - - - CO2CH3 - CH3 SCH3 Table XXIX General Formula 8 m.p J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X3 ( C J12 0 CH2 - - - H - - - - - - - CH3 OCH3 J12 0 CH2 - - - H - - - - - - - CH3 CH3 J12 0 0 - - - H - - - - - - - CH3 CH3 J12 0 0 - - - H - - - - - - - CH3 OCH3 J13 0 CH2 - - - H CH3 - - - - - - - OCH3 J13 0 CH2 - - - H CH3 - - - - - - - CH3 J13 0 O - - - H CH3 - - - - - - - CH3 J13 1 CH2 J13 1 CH2 - - - H CH3 - - - - - - - CH3 J13 1 0 - - - H CH3 - - - - - - - OCH3 J14 0 CH2 - - - H - H H - - - - - CH3 J14 0 CH2 - - - H - H H - - - - - OCH3 J14 1 CH2 - - - H - H H - - - - - OCH3 J14 1 0 - - - H - H H - - - - - OCH3 J15 0 CH2 - - - H - - - - - - - - CH3 J15 0 0 - - - H - - - - - - - - OCH3 J15 1 CH2 - - - H - - - - - - - - OCH3 J16 0 - - - - H CH3 - - - - - - - CH3 J16 0 - - - - H CH3 - - - - - - - OCH3 J17 0 - - - - H CH3 - - - - - - - OCH3 J18 - CH2 - - - H CH3 - - - - - - CH3 CH3 J18 - CH - - - H CH3 - - - - - - CH3 OCH3 J19 - CH2 - - - H - H - - - - - - CH3 J19 - 0 - - - H - H - - - - - - OCH3 J20 - CH2 - - - H - - - - - - - - CH3 J21 - - - - - H CH3 - - - - - - - CH3 J21 - - - - - H CH3 - - - - - - - OCH3 J22 - - - - - H CH3 - - - - - - - CH3 J23 - CH2 - - - H - H - - - - - - OCH3 J23 - CH2 - - - H - H - - - - - - CH3 Table XXIX (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X3 ( C) J23 - O - - - H - H - - - - - - OCH3 J23 - 0 - - - n - H - - - - - - CH3 J24 - CH2 O - - H - - - - - - - - CH3 J24 - O O - - H - - - - - - - - OCH3 J24 - CH2 CH2- - H - - - - - - - - OCH3 J25 - CH2 - - - H - - - - - - - - CH3 J25 - CH2 - - - H - - - - - - - - OCH3 J25 - O - - - H - - - - - - - - OCH3 J26 - - - O - H - CH3 H H - - - - OCH3 J26 - - - O - H - CH3 H H - - - - CH3 J26 - - - S - H - CH3 H H - - - - CH3 J26 - - - S - H - CH3 H H - - - - OCH3 J26 - - - SO2 - H - CH3 H H - - - - CH3 J26 - - - SO2 - H - CH3 H H - - - - OCH3 J27 - CH2 - O - H - CH3 H - - - - - CH3 J27 - CH2 - S - H - CH3 H - - - - - OCH3 J27 - CH2 - SO2 - H - CH3 H - - - - - CH3 J27 - O - SO2 - H - CH3 H - - - - - OCH3 J28 - - - - O H - H H - - - - - CH3 J28 - - - - S H - H H - - - - - CH3 J29 - CH2 - - - H - H H - H H - - OCH3 J29 - CH2 - - - H - H H - CH3 H - - CH3 J30 - - - - - H - H H - - - - - OCH3 J30 - - - - - H - H H - - - - - CH3 J31 - CH2 - - - H - - - - - - - - OCH3 J31 - CH2 - - - H - - - - - - - - CH3 J31 - O - - H - - - - - - - - OCH3 J31 - O - - - H - - - - - - - - CH3 J32 - CH2 - - - - - - - - - - Cl - OCH3 J32 - CH2 - - - - - - - - - - F - OCH3 J32 - CH2 - - - - - - - - - - Br - OCH3 Table XXIE (continued) m.p. J n L O Q1 Q2 R20 R21 R23 R24 R25 R26 R27 R28 R22 X3 ( C) J32 - CH2 - - - - - - - - - - SO2CH3 - OCH3 J32 - CH2 - - - - - - - - - - OSO2CH3 - OCH3 J32 - CH2 - - - - - - - - - - SO2N(CH3)2 - OCH3 J32 - CH2 - - - - - - - - - - CO2CH3 - OCH3 J32 - O - - - - - - - - - - Cl - OCH3 J32 - O - - - - - - - - - - F - OCH3 J32 - O - - - - - - - - - - Br - OCH3 J32 - O - - - - - - - - - - SO2CH3 - OCH3 J32 - O - - - - - - - - - - OSO2CH3 - OCH3 J32 - O - - - - - - - - - - SO2N(CH3)2 - OCH3 J32 - O - - - - - - - - - - CO2CH3 - OCH3 Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions. suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1As to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Table XXX Percent by Weight Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 5-50 40-95 0-15 Emulsions, Solutions. (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 1-95 5-99 0-15 High Strength 90-99 0-10 0-2 Compositions Lower or higher levels of active ingredients 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. Edn., Dorland Books, Caldwell, N.J. 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", Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th. Edn., McGraw-Hill, N.Y., 1963, pp. 8-59ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, Feb. 15, 1966, Col. 6, Line 16 through Col. 7. Line 19 and Examples 10 through 41. R. W. Luckenbaugh. U.S. Patent 3,309,192, March 14, 1967, Col. 5, Line 43 through Col. 7, Line 62 and Ex. 8. 12. 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, 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 & Sons, Inc., New York, 1961 pp. 81-96. J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Edn., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. J. B. Buchanan, U.S. Patent 3,576,834, April 27, 1971, Col. 5, Line 36 through Col. 7, Line 70 and Ex. 1-4, 17, 106, 123-140. R. R. Shaffer, U.S. Patent 3,560.616 Feb. 2, 1971, Col. 3, Line 48 through Col. 7, Line 26 and Examples 3-9. 11-18. E. Somers, "Formulation", Chapter 6 in Torgeson, "Fungicides", Vol. I, Academic Press. New York, 1967. In the following examples, all parts are by weight unless otherwise indicated. Example 13 Wettable Powder 5-t[(4,6-dimethoxyprimidin-2-yl)aminocarbonyl]amino- sulfonylmethyl]-1,3-dimethyl-lH-pyrazole-4-carboxylic acid. ethyl ester 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are thoroughly blended, passed through a mill, such as an air mill or hammer mill, to produce an average particle size under 25 microns, reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging. Example 14 Wettable Powder N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2.3- dihydro-2-methylbenzo[B]thiophene-7-methanesulfon amide-l,l-dioxide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. Example 15 Granule Wettable Powder of Example 10 5% attapulgite granules 95% (U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. Example 16 High Strenqth Concentrate 3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino- sulfonylmethyl 3-1, 5-dimethyl-lU-pyrazole-4-carboxylic acid, ethyl ester 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways. Example 17 Dust wettable powder of Example 16 5% pyrophyllite (powder) 95b The wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged. The product is suitable for use as a dust. Example 18 Low Strength Granule 1.3-dihydro-N-t(4,6-dimethoxypyrimidin-2-yl)amino- carbonyl)-l-oxo-benzo[c)furan-7-methanesulfon- amide 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve:; 0.84-0.42 mm) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 19 Aqueous Suspension N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl]-2-methylbenzot8]thiophene-7-methanesulfon- amide-1, 1-dioxide 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. Example 20 Aqueous Suspension 5-[t(4,6-dimethoxypryimidin-2-yl)aminocarbonyl]amino- sulfonylmethyl]-1,3-dimethyl-lES-pyrazole-4-carboxylic acid, ethyl ester 25% hydrated attapulgite 3% crude calcium ligninsulfonate 10% water 62% The ingredients are ground together in a ball, sand or roller mill until the solid particles have been reduced to diameters under 10 microns. Example 21 Solution N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3- dihydro-2-methylbenzotB]thiophene-7-methanesulfon- amide-111-dioxide, sodium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. Example 22 High Strength Concentrate 1,3-dihydro-N-((4,6-dimethoxypyrimidin-2-yl)amino- carbonyl)-l-oxo-benzo[c)furan-7-methanesulfon- amide 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 23 Wettable Powder 1,3-dihydro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amlnocarbonyl)-l-oxo-benzo[c)furan-7-methanesulfon amide 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 24 Oil Suspension N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl]-2-methylbenzo[B]thiophene-7-methanesulfon- amide-l.l-dioxide 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 25 Dust N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl]-2-methylbenzo[B]thiopene-7-methanesulfon amide-l,l-dioxide 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 pyro phyllite until homogeneous. ExamPle 26 Extruded Pellet 3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino sulfonylmethyl]-1,5-dimethyl-1H-pyrazole-4-carboxylic acid. ethyl ester 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1S calcium/magnesium bentonite 59% The ingredients are blended, hammer milled and then moistened with about 12% water. The mixture is extruded as cylinders about 1-3 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 27 Solution 5-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino- sulfonylmethyl]-1,3-dimethyl-lH-pyrazole-4-carboxylic acid, ethyl ester 5% dimethylformamide 95% Utility The compounds of the present invention are active herbicides, having utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, billboards, and highway and railroad structures. The rates of application for the compounds of the invention are determined by a number of factors, including 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 0.05 to 5 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content. 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 compounds may also be used in combination with mefluidide. The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedure 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, cotton 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 post-emergence 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 or necrosis: E = emergence inhibition; G = growth retardation; and H = formative effects. The test compounds are referenced in the table of results as follows. Compounds Compound 1 EMI137.1 Compound 2 EMI137.2 Compound 3 EMI137.3 Compound 4 EMI137.4 Compounds (Continued) Compound 5 EMI138.1 Compound 6 EMI138.2 Compound 7 EMI138.3 Compounds (Continued) Compound 8 EMI139.1 Compound 9. EMI139.2 Compound 10 EMI139.3 Compound 11 EMI139.4 Compounds (Continued) Compound 12 EMI140.1 Compound 13 EMI140.2 Compound 14 EMI140.3 Compounds (Continued) Compound 15 EMI141.1 Compound 16 EMI141.2 Compound 17 EMI141.3 Compound 18 EMI141.4 Compounds (continued) Compound 19 EMI142.1 Compound 20 EMI142.2 Compound 21 EMI142.3 Compound 22 EMI142.4 Compounds (continued) Compound 23 EMI143.1 Compound 24 EMI143.2 Compound 25 EMI143.3 Compound 26 EMI143.4 Table A Compound 1 Rate kg/ha 2.0 0.4 0.05 POST-EMERGENCE Morningglory 5C,9G 2C.8G 4G Cocklebur 2C.8G 1C 0 Sicklepod 2C.9H 3C.7H 3C.5G Nutsedge 8G 5G 7G Crabgrass 6G 2G 0 Barnyardgrass 3C.8H 3C.8H 2C.5H Wild Oats 2C,5G 0 0 Wheat 4G 0 0 Corn 2C,9G 3C,8G 3C.8H Soybean 3C,9H 4C.8H 3C,9G Rice 2G 2G 0 Sorghum 3C.8H 3C.8H 3C.8H Sugar beet 3C,:7G 3C.5G 3G Cotton 3C,9G 4C.7G 3C.5H PRE-EMERGENCE Morningglory 5C,9G 4C.7G 3H Cocklebur - O 5H Sicklepod 4C.8G 4C.6G 3G Nutsedge 10E 0 0 Crabgrass 6G 2C,5G 2C.3G Barnyardgrass 4C,9H 2C,5G 0 Wild Oats 4C,8G 2C,3G 0 . Wheat 8G 3G 0 Corn 5C.9G 4C.5G 2C,2G Soybean 3C,5H 2C.2H 1C Rice 3C,8H 2C.5G 0 Sorghum 3C.9H 3C.8G 2C,3G Sugar beet 4C.8G 3C.8G 2C.4G Cotton 2C 0 0 Table A (continued) Compound 2 Rate kg/ha 2.0 0.4 0.05 POST-EMERGENCE Morningglory 9C 9C 9C Cocklebur 3H 5G 1H Sicklepod 5C.6G 3C,4H 4C,4H Nutsedge 8G 8G 8G Crabgrass 4G 2G 0 Barnyardgrass 5C,9H 3C,9H 2C,3H Wild Oats 2G 0 0 Wheat 0 0 0 Corn 2C,8H 3C,8H 2C,5H Soybean 4C.9G 5C.9G 3C.7G Rice 2C,7G 2C,7G 4G Sorghum 3C.8H 3C.7G 5G Sugar beet 3C.8H 1C.4G 4G Cotton 4C.8G 3C,8G 2C,7G PRE-EMERGENCE Morningglory 9C 9G 8G Cocklebur 9H 8H 0 Sicklepod 9G - 8G Nutsedge 10E 10E 0 Crabgrass 4G 3G 0 Barnyardgrass 4C.9H 3C.8H 3G Wild Oats 2C.6G 1C.3G 2G Wheat 2C.8H 4G 0 Corn 2C.9H 4C.9H 2C Soybean 4C.7G 3C.3H 0 Rice 10E 4C,9H 2C Sorghum 6G,9H 4C.9G 2C,3H Sugar beet 5C.9G 9G 7G Cotton 9G 2C.8G 0 Table A (continued) Compound 3 Compound 4 Rate kg/ha 0.4 0.05 0.4 POST-EMERGENCE Morningglory 4C.9G 3C.6H 2C.2H Cocklebur 2C.5H 0 0 Nutsedge 3G 4G 0 Crabgrass 1C 0 0 Barnyardgrass 0 0 0 Wild Oats 0 0 0 Wheat 0 0 0 Corn 0 0 0 Soybean 2C.8G 2C.2H 0 Rice 0 0 0 Sorghum 3C,5G 2G 0 Sugar beets 3C.6G 2C.3G 1C.1H Cotton 3C.8H 0 0 Sicklepod 3C.8H 3C,3H 0 PRE-EMERGENCE Morningglory 2C.5H 0 1C Cocklebur O 0 0 Nutsedge 10E 0 0 Crabgrass 0 0 0 Barnyardgrass 0 0 0 Wild Oats 0 0 0 Wheat O 0 0 Corn 2C 0 3G Soybean 2C.3H 0 0 Bice 0 0 0 Sorghum 4C,5G 0 0 Sugar beet 3C.8G 2C 2C,3G Cotton 4G 0 0 Sicklepod 2C 0 0 Table A (continued) Cmpd. 5 Cmpd. 6 Cmpd. 7 Rate kg/ha 0.4 0.4 0.4 POST-EMERGENCE Morningglory 5C.8H 2C.3H 3C.5G Cocklebur 0 3G . 0 Nutsedge 0 0 0 Crabgrass o 0 0 Barnyardgrass 2C.4H 2C.5H 0 Wild Oats o 0 0 Wheat 3G 0 0 Corn 3C.8H 2C.5H 0 Soybean 2C.3H 2C.3H 3C.6G Rice 4C.8G 2C.6G 4G Sorghum 5C,9H 3C.5H 3G Sugar beets 4C,8H 3C.6H 3C,6G Cotton 4G 2H 0 Sicklepod o O 1C PRE-EMERGENCE Morningglory 2C 0 0 Cocklebur 0 0 0 Nutsedge 0 0 0 Crabgrass 0 O Barnyardgrass 0 0 0 Wild Oats 0 0 0 Wheat 2G 0 0 Corn 3G 0 0 Soybean 1C O 0 Rice 2C 0 0 Sorghum 2C.5G 2C,6G 0 Sugar beet 0 0 0 Cotton 0 0 0 Sicklepod 0 0 0 TABLE A (Continued) Compound 8 Compound 9 Rate (kg/ha) 0.4 0.4 0.05 POSTEMERGENCE Morningglory 2C,3H 4C.5G 8G,2C Cocklebur 0 1H 0 Nutsedge <RTI ID=148.3> 0 2C,8G 2C,5G Crabgrass 0 4H 0 Barnyardgrass 0 1H 0 Wild Oats 0 0 0 Wheat 0 0 0 Corn 0 0 0 Soybean 3C,7G 3C.8G 2C,9G Rice 3G 2C,3G 2G Sorghum 3C.5H 2C.2H 0 Sugar Beets 2C 5C.8H 1C.4G Cotton 0 3C.7G 2C.5G Cassia 0 2C,5G 0 PREEMERGENCE Morningglory 0 9G 7G Cocklebur 0 2G 0 Nut sedge 0 8G 5G Crabgrass 0 2G 0 Barnyardgrass 0 4G 1C Wild Oats 0 2G 0 Wheat 0 0 0 Corn 0 2C.8H 2C.5G Soybean 0 2C 0 Rice 0 4G 2G Sorghum 0 2C,7G 3G Sugar Beets 0 9G 4G Cotton 0 5G 0 Cassia 0 2C.7G 0 Table A (continued) Cmpd. 10 Cmpd. 11 Rate kg/ha 0.4 0.4 2.0 0.4 0.4 POST-EMERGENCE Morningglory 3C.7H 1C 2C.9G 5C.9G Cocklebur 4C,9H 2C.5G 6H 0 5C,9G Nutsedge 0 0 0 3G 5G Crabgrass 0 0 0 2G 4G Barnyardgrass 0 0 0 2H 2G Wild Oats 0 0 0 0 0 Wheat 0 0 0 0 2G Corn 0 0 0 2H 2C.8H Soybean 3C.8G 0 2C.5G 3C.9G 4C.9G Rice 0 0 0 3C,9G 2C,8H Sorghum 0 0 0 2C.9H 3C.9G Sugar beets 2C.2G 0 2H 9C 9C Cotton 3G 0 0 4C.9G 3C.8G Sicklepod 2C 0 - 2C,3G 4C,6G PRE-EMERGENCE Morningglory 8G 0 4H 2C,8H 9G Cocklebur 3C,6G 0 3H 0 9H Nutsedge 0 0 0 2G 2G Crabgrass 0 0 0 0 0 Barnyardgrass 0 0 O 6H 5H Wild Oats 0 0 0 2C.4G 2G Wheat 0 0 0 8G 4G Corn 2C.4G 0 0 2C.8G 9G Soybean 0 0 0 2C,3H 2C,4H Rice 0 0 0 3C.5G 2C,2G Sorghum 2C,3G 0 0 2C,9H 9H Sugar beet 8G 0 4H 5C.9G 5C.9G Cotton O 0 0 2C.4G 5G Bicklepod 0 0 - 1C 3C.5G TABLE A (Continued) Compound 14 Rate (kg/ha) 0.4 2.0 POSTEMERGENCE Morningglory 1C 0 Cocklebur 3C.8H 2C.7H Nutsedge 0 0 Crabgrass 0 0 Barnyardgrass 0 0 Wild Oats 0 0 Wheat 0 0 Corn 0 2H Soybean 0 0 Rice 0 0 Sorghum 0 0 Sugar Beets 0 0 Cotton 0 2H Cassia 0 0 PREEMERGENCE Morningglory 1C 7G Cocklebur 2C.5H 5H Nutsedge 0 0 Crabgrass 0 0 Barnyardgrass 0 0 Wild Oats 0 0 Wheat 0 0 Corn 0 0 Soybean O 0 Rice 0 0 Sorghum O 0 Sugar Beets 0 0 Cotton O 0 Cassia o - Table A (Continued) Cmpd. 15 Cmpd. 16 Cmpd. 17 Cmpd.18 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 6C.9G 3C.9G 3C.6H 10C Cocklebur 5C.8G 5C.9G 3C.5G 10C Sicklepod 4C.8G 3C.3H 2C,5G 9C Nutsedge 3C,8G 2G 2C.3G 5G Crabgrass 0 0 2C,5G 3C.8G Barnyardgrass 0 0 3C.6H 4C,9H Wild Oats 0 0 3C.6G 3C,8G Wheat 0 0 3C.8G 6G Corn 3C.9H 1H 3C.9G 2U.9G Soybean 3C.9G 2C.8G 3H 9C Rice 2C,6G 2G 5C.9G 6C,9G Sorghum 3C.9H 2C.9H 4C.9H 6C.9H Sugar beet 9C 4C,9G 3C,4H 10C Cotton 3C,8H 3c.5G 0 9C PRE-EMERGENCE Morningglory 8G 2C.3H 0 9G Cocklebur 2C.5H 2C.2H - 8H Sicklepod 1C.2G 0 0 2C,7G Nutsedge 2G 0 0 4G Crabgrass 1C 0 2G 2C.5G Barnyardgrass 0 0 1H 4C.9H Wild Oats O 0 2C,7G 2C,8H Wheat 4G 3G 2C.8G 3C,9H Corn 2C.8H 0 3c.7H 2U.9G Soybean 2C,8H 0 0 3C.8H Rice 2C.7G 2G 3C.8H 5C.9H Sorghum 3C.8H 3C.8H 3C.9G 5C.9H Sugar beet 9C 3C,8G 0 9C Cotton 8H 1C 0 9G Table A (continued) Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 8G 10C 2C,6G 10C Cocklebur 5G 3C.9G 3G 10C Nutsedge 2C,3G 3G 0 3G Crabgrass 3C.7G 3G 0 5G Barnyardgrass 9C 3C.6H 3C.8H 3C,8H Wild Oats 9C 2C,4G 4C.8G 2C Wheat 10C 3G 9C 9G Corn 9C 4C,9H 4C,9G 3C.9G Soybean 5C,9H 5C,9G 3C,8H 9C Rice 9C 9C 9C 9C Sorghum 9C 5C,9H 5C.9G 5C,9H Sugar beet 3C.7H 9C 3C.7G 5C,9G Cotton 3C.7H 5C,9G 3C.5G 5C.9G Sicklepod 3C.3H 4C.7H 2C.5G 9C PRE-EMERGENCE Morningglory 3C.5H 9G 8G 9G Cocklebur O 5R 2H 8H Nutsedge O 0 2C 3G Crabgrass O 0 0 2C.5G Barnyardgrass 3C,5G 0 1H 2C,6G Wild Oats 8G 2C,3G 5G 2C.5G Wheat 2C.8H 2G 2C.9H 2C.7G Corn 3C.8H 3C,3G 2C,8H 4C.9H Soybean 1C 3C.5H 2C,2H 4C.6H Rice 5C.9H 7H 5C.9H 5C.9H Sorghum 4C.9H 3C.7H 5C.9H 4C.9G Sugar beet 8G 9C 5G 9C Cotton 2G 5G 5G 3C,7G Sicklepod 2C 2C.2H 1H 2C.4G Table A (continued) Cmpd. 23 Cmpd. 24 Cmpd. 25 Cmpd. 26 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 3C,9G 3G 9C 10C Cocklebur 2G 3G 2C 5c.9G Nutsedge 5G 0 2C.7G 2C.6G Crabgrass 0 0 2G 2C Barnyardgrass 0 0 0 0 Wild Oats 0 0 0 0 Wheat 0 0 0 0 Corn 0 0 1H 3C,8H Soybean 3C.9G 3C.9G 5C.9G 5C.9G Rice 0 0 0 o Sorghum 0 0 3G 3C.8H Sugar beet 3C.6G 0 5C.9G 5C.9G Cotton 9C 2G 4C.9G 4C,9G Sicklepod 2C.3G 1C 3C.8G 4C,6G PRE-EMERGENCE Morningglory 8G 3G 9G 9G Cocklebur 2H 3G - 8H Nutsedge 3G 0 5G 0 Crabgrass 4G 3G 0 0 Barnyardgrass 0 0 3G 3G Wild Oats 0 0 3G 5G Wheat 0 0 4G 8G Corn 0 3G 2C.7G 9G Soybean 1H 0 2H 3C.9G Rice 0 0 2G 2G Sorghum 0 2G 5G 9G Sugar beet 5G 2G 5C,9G 5C,9G Cotton 2G 0 8G 8G Sicklepod 5G 4G 2C,7G 2C Test B Postemergence Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass (Alpecurus myosuroides). sugar beets, nutsedge (Cyperus rotundus) tubers. crabgrass (Digitaria sansuinalis). sicklepod (Cassia obtusifolia), teaweed (Sida spinosa). jimsonweed (Datura stramonium). velvetleaf (Abutilon theophrasti), oil seed rape (Brassica naPus), and giant foxtail (Setaria faberii). The other pan was planted with wheat, cotton, rice, corn, soybean. wild oats (Avena fatua), cocklebur (Xantium pensylvanicum), morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusqalli). The plants were grown for approximately fourteen days, then sprayed post-emergence with the chemicals dissolved in a non-phytotoxic solvent. Preemergence Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass, sugar beets, nutsedge, crabgrass. sicklepod, teaweed, jimsonweed, velvetleaf, oil seed rape. and giant foxtail. The other pan was planted with wheat,cotton, rice. corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response utilizing the rating system as described for Test A. Response ratings are contained in Table B. The data show the potential utility of several of the compounds tested for selective weed control in crops such as wheat, soybeans and cotton. Table B PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 15 POST-EMERGENCE Rate g/ha 62 16 4 Corn 3G 0 0 Wheat O 0 0 Rice SG 3G 0 Soybean 9G 6G 3G Cotton 7G 3G 0 Sugar beet 7G 3G 0 Rape - - . Crabgrass 0 0 0 Johnsongrass 9G 4G 0 Blackgrass 0 0 0 Barnyardgrass 3G 0 0 Nutsedge 5G 2G 0 Giant Foxtail 6G 0 0 Wild Oats 0 0 0 Cocklebur 8G 3G 0 Morningglory 9G 8G 3G Teaweed 0 0 0 Sicklepod 3G 0 0 Jimsonweed 8G 6G 2G Velvetleaf 9G 7G 3G PRE-EMERGENCE Rate 250 62 Corn 2G 0 Wheat O 0 Rice 7G 4G Soybean 3G 0 Cotton 7G 2G Sugar beet 9G 3G Rape - Crabgrass 9G 5G Johnsongrass 8G 4G Blackgrass 8G 3G Barnyardgrass 4G 2G Nutsedge 8G 5G Giant Foxtail 6G 2G Wild Oats 0 <RTI ID=155.8> 0 Cocklebur 8G 0 Morningglory 0 0 Teaweed 9G 5G Sicklepod 10B 6G Jimsonweed 8G 6G Velvetleaf 8G 4G Table B (Continued) Compound 16 POST-EMERGENCE Rate g/ha 62 16 4 Corn O 0 0 Wheat O 0 0 Rice 6G 4G 0 Soybean 9G 8G 5G Cotton 5G 3G 0 Sugar beet 9G 5G 0 Rape - Crabgrass 3G 0 0 Johnsongrass 5G 2G 0 Blackgrass 0 0 0 Barnyardgrass 3G 0 0 Nutsedge 7G 3G 0 Giant Foxtail 7G 4G 0 Wild Oats 0 0 0 Cocklebur 9G 5G 2G Morningglory 9G 6G 3G Teaweed 4G 0 0 Sicklepod 6G 3G 0 Jimsonweed 8G 4G 2G Velvetleaf 9G 5G 0 PRE-EMERGENCE Rate g/ha 250 62 16 Corn 0 0 0 Wheat 2G 0 0 Rice 7G 6G 6G Soybean 2C 0 0 Cotton 0 0 0 Sugar beet <RTI ID=156.7> 10G 8G 0 Rape Crabgrass 9G 8G 6G Johnsongrass 8G 5G 0 Blackgrass 8G 4G 0 Barnyardgrass 3G 0 0 Nutsedge 8G 5G 2G Giant Foxtail 4G 2G 0 Wild Oats 0 0 0 Cocklebur 3G 0 0 Morningglory 3G 0 0 Teaweed 9G 5G 0 Sicklepod 8G 8G 5G Jimsonweed 9G 6G 0 Velvet leaf 8G 3G 0 Table B (Continued) Compound 18 POST-EMERGENCE Rate g/ha 62 16 4 1 Corn 100.70 100,60 90.30 80 Wheat 0.0 0.0 0.0 0.0 Rice 80,0 70,0 30.0 0.0 Soybean 100.90 100,90 100.80 70.20 Cotton 100,50 100.20 40,0 0.0 Sugar beet 100,90 40,90 0,40 0,0 Rape 100,100 100,90 100,90 50,40 Crabgrass 20,0 0,0 0.0 0,0 Johnsongrass 100,90 100,0 60,0 20 Blackgrass 100.70 70.0 30.0 0,0 Barnyardgrass 70.50 40.0 0,0 0,0 Nutsedge 40,- 30.0 0,0 0.0 Giant Foxtail 50,0 0.0 0.0 0,0 Wild Oats 30,0 0,0 0.0 0,0 Cocklebur 100,90 60,70 30,0 0.0 Morningglory 100,90 40.90 0,90 0.50 Teaweed 80,80 50.80 30,0 0,0 Sicklepod 100.100 90,90 30,70 0.0 Jimsonweed 100.90 90,90 60.70 30,30 Velvetleaf 100.100 100.90 100.90 30,50 PRE-EMERGENCE Rate g/ha 250 62 16 Corn 90,100 40,30 0,0 Wheat 30,30 0,0 0.0 Rice 100 90.100 40.60 Soybean 80,100 60,50 20,0 Cotton 40,60 0,50 0.0 Sugar beet 90,100 30,100 0.50 Rape 100 80,50 30,0 Crabgrass 90,60 0,30 0,0 Johnsongrass 90.100 90,90 80.60 Blackgrass 90.100 70,80 0.40 Barnyardgrass 90.100 70.60 20,20 Nutsedge 0,0 0,0 0.0 Giant Foxtail 100 70,70 0.0 Wild Oats 60.40 30,0 0.0 Cocklebur 80,90 70.60 0.40 Morningglory 90,80 20,30 0.0 Teaweed 90.90 50.50 0,0 Sicklepod 70.50 30,20 0,0 Jimsonweed 90,100 70,90 20.30 Velvetleaf 90,100 70,60 20.30 1 Note: there are two sets of data for each rate tested. Table B (Continued) Compound 19 POST-EMERGENCE Rate g/ha 62 16 4 Corn 80 50 0 Wheat 0 0 0 Rice o 0 0 Soybean 90 80 60 Cotton 60 0 0 Sugar beet 70 60 30 Rape 100 90 60 Crabgrass o 0 0 Johnsongrass O 0 0 Blackgrass 80 0 0 Barnyardgrass O 0 0 Nutsedge O 0 0 Giant Foxtail O 0 0 Wild Oats O 0 0 Cocklebur 100 90 70 Morningglory 100 90 80 Teaweed 50 20 0 Sicklepod o 0 0 Jimsonweed 90 80 0 Velvetleaf 80 0 0 PRE -EMERGENCE Rate g/ha 250 62 Corn 80 0 Wheat O 0 Rice 80 30 Soybean 70 20 Cotton 20 0 Sugar beet 80 20 Rape 90 30 Crabgrass o 0 Johnsongrass 90 80 Blackgrass 90 80 Barnyardgrass 70 0 Nutsedge 70 20 Giant Foxtail 70 0 Wild Oats O 0 Cocklebur 90 0 Morningglory 90 0 Teaweed 60 20 Sicklepod O 0 Jimsonweed 90 50 Velvetleaf 50 0 Table B (Continued) Compound 20 POST-EMERGENCE Rate g/ha 62 16 Corn 70 40 Wheat 50 0 Rice 70 30 Soybean 90 90 Cotton O 0 Sugar beet 80 70 Rape 90 70 Crabgrass 20 o Johnsongrass 20 0 Blackgrass 70 0 Barnyardgrass O 0 Nutsedge O 0 Giant Foxtail O 0 Wild Oats 50 0 Cocklebur o 0 Morningglory 90 60 Teaweed 30 0 Sicklepod 50 0 Jimsonweed 30 0 Velvetleaf 70 0 PRE-EMERGENCE Rate g/ha 250 62 Corn 40 0 Wheat O 0 Rice 90 70 Soybean 40 0 Cotton 20 0 Sugar beet 80 30 Rape 60 20 Crabgrass 20 0 Johnsongrass 70 30 Blackgrass 90 60 Barnyardgrass O 0 Nutsedge 30 0 Giant Foxtail 20 0 Wild Oats O 0 Cocklebur o 0 Morningglory O 0 Teaweed 60 0 Sicklepod 50 0 Jimsonweed 50 30 Velvetleaf 50 30 Table B (Continued) Compound 21 POST-EMERGENCE Rate g/ha 62 16 4 Corn 100 90 60 Wheat 70 0 0 Rice 90 30 0 Soybean 100 90 90 Cotton 90 20 0 Sugar beet 70 20 0 Rape 100 90 70 Crabgrass 60 0 0 Johnsongrass 90 90 70 Blackgrass 90 80 20 Barnyardgrass 60 20 0 Nutsedge o 0 0 Giant Foxtail 40 0 0 Wild Oats 40 0 0 Cocklebur 80 90 30 Morningglory 100 100 90 Teaweed 90 80 20 Sicklepod 90 60 20 Jimsonweed 80 50 0 Velvetleaf 100 90 40 PRE-EMERGENCE Rate g/ha 250 62 16 Corn 50 0 0 Wheat 40 0 0 Rice 100 90 50 Soybean 70 0 0 Cotton 30 0 0 Sugar beet 60 0 0 Rape 90 20 0 Crabgrass 60 30 0 Johnsongrass 90 90 30 Blackgrass 90 80 30 Barnyardgrass 90 50 0 Nutsedge 20 0 0 Giant Foxtail 90 50 0 Wild Oats 80 20 0 Cocklebur 60 0 0 Morningglory O 0 0 Teaweed 90 50 20 Sicklepod 70 20 0 Jimsonweed 90 40 0 Velvet leaf 80 30 0

Claims: Claims: 1. A compound of the formula: EMI161.1 wherein EMI161.2 EMI161.3 EMI161.4 J-7 J-8 J-9 EMI162.1 EMI163.1 n is O or 1; L is CH2 or 0: Q is CH2 or 0; Q1 is 0, S or SO2: Q2 is O or S: R is H or CH3; R1 is H. C1-C3 alkyl. CO2R15. SO2NR16R17 or SO2R18: R2 is H or CH3: R3 is H or CH3: R4 is H or CH3; R5 is H. CH3. Cl. Br. CO2R15. SO2NR16R17 SO2N(OCH3)CH3. SO2R18 or NO2: R6 is H. C1-C3 alkyl. CO2R15. SO2NR16R17 or SO2R18: R7 is H or CH3: R8 is CO2R15. SO2NR16R17. SO2N(OCH3)CH3. S02R18 or NO2; R9 is H. C1-C3 alkyl or phenyl; R10 CO2R15. SO2NR16R17. SO2N(OCH3)CH3. S02R18 or NO2; R11 is H or CH3: R12 is H. CO2R15. SO2NR16R17. SO2N(OCH3)CH3. SO2R18 or NO2: R13 is H. CO2R15. SO2NR16R17. SO2N(OCH3)CH3. SO2R18 or NO2: R14 is H or CH3: R15 is C1-C2 alkyl; R is C1-C2 alkyl: R17 is C1-C2 alkyl; R18 is C1-C2 alkyl: R19 is CH3. Cl. Br. NO2. C1-C2 alkylthio or C1-C2 alkylsulfonyl; R20 is H. F. C1, Br, CH3 or OCH3: R21 is H or C1-C2 alkyl: R22 is H, OH. C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxylalkyl, C3 -C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy, phenyl. C3-C6 cyclo alkyl, C4-C7 cycloalkylalkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxycarbonyl. benzyl, C3-C4 haloalkenyl, C3-C6 haloalkynyl, C3-C6 alkyl carbonylalkyl, C3-C6 alkoxycarbonylalkyl or C1-C4 cyanoalkyl: R23 is H or CH3: R24 is H or CH3: R25 is H, CH3 or C2H5; R26 is H or CH3: R27 is H or CH2: R28 is F, C1, Br, OCH3, SCH3. SO2CH3. C02CH3, SO2N(CH3)2 or OSO2CH3: EMI165.1 X is CH3, OCH3, C1, Br, OCH2CF3 or OCHF2: Y is C1-C3 alkyl, CH2F, cyclopropyl, C#CH. OCH3, OC2H5. CH2OCH3. NH2. NHCH3. N(CH3)2. OCH2CH2F, CF3, SCH3, OCH2CH=CH2. OCH2C#CH. OCH2CH2OCH3. CR(OCH3)2. EMI165.2 CR(OCH2CH3)2 or OCF2H; Z is CH or N: X1 is CH3. OCH3. OC2H5 or OCF2H: Y1 is O or CH2. X2 is CH2. C2H5 or CH2CF3: Y2 is OCH3. OC2H5. SCH3. SC2H5. OCF2H. SCF2H. CH3 or CH2CH3: X3 is CH3 or OCH3: Y3 is H or CH3: and agriculturally suitable salts thereof; provided that 1) when X is Cl or Br, then Z is CH and Y is OCH3. OC2H5. NHCH3. N(CH3)2 or OCF2H; 2) when X or Y is OCF2H, then Z is CH: 3) R5 and R6 are not simultaneously H; 4) when R6 is other than H or C1-C3 alkyl. then R5 must be H: 5) R12 and R13 are not simultaneously H: 6) when R12 is other than H. then R13 must be H; 7) R5 and R19 are not simultaneously H: and 8) when J is J-8 or J-ll then R5 is other than H. 2. The compound of Claim 1 where R is H and A is A-1. 3. The compound of Claim 2 where Y is CH3. C2H5, OCH3. OC2H5. CH2OCH3. CH2F or CF3: and L is CH2 4. The compound of Claim 3 where J is J13. J14. J18. J19. J26 or J27 5. The compound of Claim 4 where R20 is H and X is CH3 or OCH3. 6. The compound of Claim 2 where J is J-1, J-4. J-5 or J-6; X is CH3 or OCH3; and Y is C1-C2 alkoxy or C1-C2 alkyl. 7. The compound of Claim 1 which is 1,3-dihydro N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-oxo benzo[C]furan-7-methanesulfonamide, or an agriculturally suitable salt thereof. 8. The compound of Claim 1 which is 1.3-dihydro N-[(4-methoxy-6-methyl-1,3,5-triazin-Z-yl)amino- carbonyl]-1-oxo-benzo[C]furan-7-methanesulfonamide, or an agriculturally suitable salt thereof, 9. The compound of Claim 1 which is N-t(4,6- dimethoxypyrimidin-2-yl)aminocarbonyl]-2.3-dihydro-2methylbenzo[B]thiopene-7-methanesulfonamide 1.1dioxide, or an agriculturally suitable salt thereof. 10. The compound of Claim 1 which is N-t(4- methoxy-6-methyl-1.3.5-triazin-2-yl)aminocarbonyl]-2methylbenzo[B]thiopene-7-methanesulfonamide-1.1dioxide, or an agriculturally suitable salt thereof. 11. The compound of Claim 1 which is 3-[[(4,6dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]-1.5-dimethyl-1H-pyrazole-4-carboxylic acid, ethyl ester, or an agriculturally suitable salt thereof 0 12. The compound of Claim 1 which is 5-[[(4,6- dimethoxypyrimidin-2-yl)aminocacbonyl]aminosulfonyl- methyl]-1.3-dimethyl-1H-pyrazole-4-carboxylic acid, ethyl ester, or an agriculturally suitable salt thereof. 13. A composition suitable for controlling the growth af undesired vegetation which comprises an effective amount of a compound of any of Claims 1 to 12 and at least one of the following: surfactant, solid or liquid diluent. 14. A method for controlling the growth of undesired vegetation which comprises applying to the locus to he protected an effective amount of a compound of any of Clams 1 to 12. 15. A method for regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially nonophytotoxic amount of a plant growth regulant selected from compounds of any of claims 1 to 12. 16, A process for the production of a compound of claim 1 which Comprises: (a) reacting a sulfonyl isocyanate of formula JSO2NCO (tri) with an appropriate heterocyclic amine of formula EMI168.1 wherein J, R and A are as defined in claim 1, with the proyisos that R21 is C1-C3 alkyl and R22 is not H or OH; or (b) reacting a sulfonamide of formula JSO2NH2 (IV) wherein J is selected from J1-J13, J18 or J24-J32' L is -CH2- and R1, R5, R6, R8, R101 R12 and R13 of J are other than C02R15; with an appropriate methyl carbamate of formula EMI168.2 wherein X, Y and Z are as defined in claim 1; or (c) reacting a sulfonyl carbamate of formula EMI168.3 where J is as defined in claim 1, other than J16, J17' J21 or J22 and where L is -CH2-, with an appropriate heterocyclic amine of formula (III) as defined above; or (d) reacting a sulfonamide of formula (III) wherein J is other than J16' J17' J21 and J22 and L is -CU2-, with an appropriate heterocyclic phenyl carbamate of formula EMI168.4 wherein A is as defined in claim 1; or (e) reacting a phenol of formula J-H (IX) wherein J is selected from J12-J25' J27' J29' J31 or J32 as defined in claim 1 and L is 0, with a chlorosulfonylurea of formula EMI169.1 wherein A and R are as defined in claim 1.

Inventors: PASTERIS, ROBERT JAMES, THOMPSON, MARK EWELL, WEXLER, BARRY ARTHUR
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1985
Main classification: C07D403
IPC codes: C07D521, C07D491, C07D231, C07D307, A01N47