HERBICIDAL N-HYDROXY-N'-SULFONYLGUANIDINES AND SULFONAMIDE INNER SALTS

Abstract: Sulfonamide derivatives of formulae wherein: L is selected from specific optionally substituted aryl and benzyl groups; R a and R b are independently CH₃ or C₂H₅; R c is H, C(O)R₁, C(O)NR₂R₃ or CO₂R₄; R₁-R₄ are aliphatic groups, or R₂ may be H; R d is H or CH₃; R d is lower alkyl; and A is a substituted mono- or bicyclic heterocyclic group; and their agriculturally suitable salts, exhibit herbicidal and plant growth regulant activities. They may be formulated for agricultural use in conventional manner. The compounds of Formula I may be made e.g. by reacting The compounds for Formula III may be made e.g. by reacting The compounds of Formula II may be made by reacting a compound of Formula III with hydroxylamine and optional transformation of the hydroxyimino group.

Description: Title HERBICIDAL N-HYDROXY-N' -SULFONYL- GUANIDINES AND SULFONAMIDE INNER SALTS Background of the Invention This invention relates to novel sulfonamide inner salts, to novel N-hydroxy-N'-sulfonylguanidine -compounds, to herbicidal compositions containing them and to methods of using them to control the growth of undesired vegetation. U.S. Patent 4,169,719 discloses herbicidal sulfonamides of the general formula EMI1.1 where R1 can be substituted phenyl, optionally substituted thiophene or naphthalene. U.S. 4.127,405 discloses the corresponding triazine compounds. A number of additional patents or patent applications have issued or been published which disclose herbicidal sulfonamide derivatives, but no references are known which disclose the dialkylsulfonium inner salts of this invention. U.S. Patent 4,127,405 issued November 28, 1978 discloses substituted triazinyl arylsulfonylurea compounds of the following formula: EMI1.2 while U.S. Patent 4.169,719 issued October 2. 1979 discloses substituted pyrimidinyl arylsulfonylurea compounds of the following formula: EMI2.1 The triazine and pyrimidine compounds within the scope of the '405 and '719 patents include those wherein W can be oxygen or sulfur. U.S. Patent 4.310,346 issued January 12, 1982 discloses sulfonylisothiourea compounds of the formula EMI2.2 wherein B is C1-C6 alkyl. CH2CH2OCH31 CH2CH2OCH2CH3, CH2CH2CH2OCH3, EMI2.3 where Q is C 2-C1-3 alkyl. EMI2.4 EMI2.5 phenyl. phenyl substituted with chlorine, CN, C2-4 alkenyl, C2-4 alkynyl, OR11, where R11 is C1-C4 alkyl. -CH2OCH2CH2OCH3 or -CH2OCH2CH2OCH2CH3. South African Patent No. 79/2657, published June 30, 1980 discloses sulfonylisothiourea compounds of the formula EMI3.1 wherein R2 is C1-C20 alkyl: CH2CH2OCH3; CH2CH2OCH2CH3; CH2CH2CH2OCH3; CH2OA' where A' is Cl-Cl2 alkyl, -CH2CH2OCH3, -CH2CH2OCH2CH3, phenyl or phenyl substituted with 1-2 NO2. 1-2 C1, or 1-2 CH3; CH2A, EMI3.2 where A is CO2 (H, C1-C4 alkyl), EMI3.3 EMI3.4 phenyl. CN, C2-C4 alkenyl. C1-C4 alkynyl, phenyl substi tuted with 1-2 CH3, 1-2 NO2. 1-2 OCH3, 1-2 chlorine or phenoxy. U.S. 4,301,286 issued November 17, 1981 discloses O-alkylsulfonylisoureas of the formula EMI3.5 wherein W is Cl, Br or OR12; and R12 is C1-C12 alkyl. C3-C4 alkenyl, CH2CH20CH3, CH2CH2OCH2CH3 (CH2)3OCH3, benzyl, CHRÚ CO2R14, where R13 is H or CH3 and R14 is C1-4 alkyl. The compounds taught in the above five references are useful as general or selective herbicides having both preemergent and postemergent herbicidal activity or plant growth regulant activity. Summary of the Invention This invention relates to novel compounds of Formulas I-III, agriculturally suitable compositions containing them and their method-of-use as pre-emergent and/or post-emergent herbicides or plant growth regulants. EMI4.1 wherein Ra is CH3 or CH2CH3; Rb is CH3 or CH2CH3; Rc is H, C(O)R1, C(O)NR2R3 or CO2R4; Rd is C1-C3 alkyl; R is H or CH3; R1 is C1-C3 alkyl or CF3; R2 is H, CH3 or C2H5; R3 is C1-C3 alkyl: R4 is C1-C3 alkyl; L is EMI4.2 EMI5.1 R5 is C1-C4 alkyl. C1-C4 alkoxy, OCH2CH2OCH3, F, C1, Br. NO2, CF3, C02R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy. C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI6.1 EMI6.2 R6 is H. F. Cl, Br, CF3, CH3, OCH3, SCH3 or OCF2H; R7 is H. CH3. OCH3, F. Cl, Br, OSO2CH3, SO2N(CH3)2 or S(O)nCH3: R8 is CH3, CH2CH3, OCH3, OCH2CH3, F, Cl, Br. S02NR20R21, SO2N(OCH3)CH3 or S(O)nR23: R9 is C1-C3 alkyl, F, Cl, Br, NO2. @ @ CO2R19. SO2NR20R21. SO2N(OCH3)CH3 or S(O)nR23 R10 is C1, NO2. CO2CH3. C02CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3: R11 is H, CH3 or CH2CH3: R12 is H, CH3 or CH2CH3: R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl: R18 is H or CH3; Rl9 is C1-C4 alkyl. CH2CH2OCH3, CH2CH2C1 or CH2CH=CH2: R20 is C1-C3 alkyl: R21 is C1-C3 alkyl: R22 is C1-C3 alkyl or N(CH3)2: R23 is C1-C3 alkyl or CH2CH=CH2: m is O or 1: n is 0 or 2; Q1 is O, S, SO2 or NR Q2 is 0, S or NR17: and W is O, S or SO2: EMI7.1 X is CH3. OCH3. OCH2CH3. Cl. F. Br. OCF2H, CH2F or CF3: Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C#CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24(QCH3)2, EMI7.2 EMI7.3 or CR24(QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; is CH2 or O: X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 is H or CH3; X2 is CH3, CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3; X3 is CH3 or OCH3; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1, then R13 is H; 3) when L is L-17, then R17 and R18 are not simultaneously H; and 4) when X is Cl, F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2H; and also provided that for compounds of Formula I when L is L-l, R5 is not EMI8.1 and further provided that for compounds of Formula III 5) when L is L-1 and A is A-1, R5 is C2-C4 alkyl, C2-C4 alkoxy, OCH2CH20CH3. OS02R22, S(O)nCH2CH=CH2, WCF2, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI8.2 EMI8.3 6) when L is L-l and A is A-2 or A-3. then R5 is C2-C4 alkyl. C2-C4 alkoxy, OCH2CH2OCH3, OSO2R22. WCF3. WCHF2, C3-C4 alkenyloxy, C3 -C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI9.1 EMI9.2 7) when L is L-3 and A is A-1, A-2 or A-3, then R8 is SO2NR20R21. SO2N(OCH3)CH3 or SO2R23: 8) when L is L-4. L-5 or L-6 and A is A-1, A-2 and A-3. then R9 is C1-C3 alkyl, F, Cl, Br, NO2, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23: and 9) when L is L-2, then A is A-5 or A-6. Preferred for reasons of higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are: 1) Compounds of Formula I where A is A-1. 2) Compounds of Preferred 1 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3, OCH3. Cl or CF3. 3) Compounds of Preferred 2 where L is L-1, L-2, L-3, L-5, L-8. L-10, L-ll. L-16 or L-17. 4) Compounds of Preferred 3 where L is L-1, R5 is OCH3, OCH2CH3. C1, NO2, CF3, CO2CH3, CO2CH2CH3, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R22, S(O)R23, OCF2H, SCF2H, OCH2CH=CH2, OCH2C#CH, EMI10.1 EMI10.2 R22 is C1-C3 alkyl; R23 is CH3 and n is 2. 5) Compounds of Preferred 3 where L is L-2 and R7 is Cl, CH3, OCH3, SCH3 or Br. 6) Compounds of Preferred 3 where L is L-3 and R8 is Cl, SO2CH3 or SO2N(CH3)2. 7) Compounds of Preferred 3 where L is L-5 and R9 is CO2CH3 or CO2CH2CH3. 8) Compounds of Preferred 3 where L is L-8. 9) Compounds of Preferred 3 where L is L-lO. 10) Compounds of Preferred 3 where L is L-il. 11) Compounds of Preferred 3 where L is L-16. 12) Compounds of Preferred 3 where L is L-17. 13) Compounds of Formula II where R is H, Rc is H and A is A-1. 14) compounds of Preferred 13 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3, OCH3, Cl or CF3. 15) Compounds of Preferred 14 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-ll, L-16 or L-17. 16) Compounds of Preferred 15 where L is L-1, R5 is OCH3, OCH2CH3. Cl, NO2. CF3. C02CH3, CO2CH2CH3, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF2H. SCF2H, OCH2CH=CH2, OCH2C#CH, EMI11.1 EMI11.2 R22 is C1-C3 alkyl; R23 is CH3 and n is 2. 17) Compounds of Preferred 15 where L is L-2 and R7 is Cl. CH3, OCH3, SCH3 or Br. 18) Compounds of Preferred 15 where L is L-3 and is is Cl, SO2CH3 or SO2N(CH3)2. 19) Compounds of Preferred 15 where L is L-5 and R9 is CO2CH3 or CO2CH2CH3. 20) Compounds of Preferred 15 where L is L-8. 21) Compounds of Preferred 15 where L is L-10. 22) Compounds of Preferred 15 where L is L-1l. 23) Compounds of Preferred 15 where L is L-16. 24) Compounds of Preferred 15 where L is L-17. 25) Compounds of Formula III where R is H and A is A-1. 26) Compounds of Preferred 25 where Y is CH3, OCH2, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3. OCH3, Cl or CF3; 27) Compounds of Preferred 26 where L is L-l and R5 is OSO2R22, SO2CH2CH=CH2, OCF2H, SCF2H, OCH2CH=CH2, OCH2C#H, EMI11.3 Specifically Preferred for reasons of their highest herbicidal activity or greatest plant growth regulant activity or most favorable ease of synthesis are: : * 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar carbonyl)aminosulfonyl)benzoic acid methyl ester, dimethylsulfonium inner salt; * 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid methyl ester, dimethyl sulfonium inner salt; * N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 methylsulfonylbenzenesulfonamide, dimethylsulfonium inner salt; * 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid methyl ester, dimethyl sulfonium inner salt; * N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2 dimethylaminosulfonylbenzenesulfonamide, dimethyl sulfonium inner salt; * 2-[[(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxy imino)methyl]aminosulfonyl]benzoic acid. methyl ester; 2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1 (hydroxyimino)methyl]aminosulfonyl]benzoic acid. methyl ester; * N'.N'-dimethyl-N-[[1-(4,6-dimethyl-1,3,5,-triazin 2-yl)amino]-1-(hydroxyimino)methyl]-1,2-benzene disulfonamide; and * N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin 2-yl)amino]-1-(hydroxyimino)methyl]-1,2-benzene disulfonamide. Compounds of particular interest include those disclosed and claimed in our U.S. Applications Serial Nos. 455,504; 467,650; 551,004 and 551,381, all of which may be inspected on the file of the present Application. Detailed Description of the Invention Synthesis The compounds of Formula I can be prepared by contacting an appropriate sulfonyl isocyanate IV with an S,S-dialkyl-N-(heterocyclic)sulfilimine V as illustrated in Equation 1. (L, Ra, Rb and A are as previously defined.) Equation 1 EMI13.1 The reaction of Equation 1 is best carried out in an inert aprotic solvent, such as methylene chloride, tetrahydrofuran, acetonitrile, ether or chloroform, at temperatures ranging from about -20 t6 500C. In some cases, the desired product may crystallize from the reaction medium and may be filtered. Reaction products which are soluble in the reaction medium may be isolated by evaporation of the solvent, trituration of the residue with solvents such as diethyl ether, ethyl acetate, l-chlorobutane or hexane. Chromatography (e.g., silica gel) may also be necessary for purification. The sulfonyl isocyanates IV used as starting materials are generally known in the art and can be prepared by known methods. One method involves reacting an appropriate benzene or heterocyclic sulfonamide with phosgene in the presence of an alkyl isocyanate, such as n-butyl isocyanate. and a tertiary amine catalyst, such as 1,4-diazabicyclot2,2.23Octane, at reflux in a solvent such as xylene or chloroben zene. See H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry,Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed. The sulfonyl isocyanates It can also be prepared from sulfonamides by a two step procedure involving (a) reacting the sulfonamides with an alkyl isocyanate in the presence of a base such as K2CO3 at reflux in an inert solvent such as 2-butanone. forming an alkylsulfonylurea, and (b) reacting this compound with phosgene and tertiary amine catalyst at reflux in xylene solvent. The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature. e.g. Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene. or thiophene in carbon tetrachloride according to the teaching of H. T. Clarke et al., Org. Synth. Coll., Vol. 1, 2nd Ed. 1941, p. 85. Other sulfonyl chlorides can be made by diazotization of the appropriate amine with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teachings of H. L. Yale and F. Sowinski, a. Ors. Chem., 25, 1824 (1960). Reference to the following patents and patent applications is suggested for further details regarding the preparation of the sulfonyl isocyanates IV: U.S. Patent 4,169.719. U.S. Patent 4,127,405; U.S. Patent 4.383,113; U.S. Patent 4,394,506; U.S. Patent 4,120,691; U.S. Patent 4.238.621; EP-A-30,141;, EP-A--13,48Q; Canadian Patent 1,128,042; EP-A-64,804 and EP-A-51,466. The sulfilimine (V) starting materials may be made in a number of ways. S,S-Dimethyl-N-(4,6-di methylpyrimidin-2-yl)sulfilimine and S,S-dimethyl-N (4-methylpyrimidin-2-yl)sulfilimine are taught by T. L. Gilchrist, C. J. Harris and C. W. Rees in J.C.S. Chem. Comm., 486 (l974). The procedure taught in this article can be adapted to prepare other sulfilimines of Formula V as shown in Equation 2. Equation 2 EMI15.1 A heterocyclic amine VI is contacted successively with tert-butyloxy chloride, a dialkylmercaptide and sodium methoxide. The reaction may be best carried out in an inert aprotic solvent, such as methylene chloride, chloroform or ethyl acetate at temperatures between -60 to 600C for 1-48 hours with ambient pressure. The resulting solution may be washed with water. In some cases. the desired product may crystallize from the organic solvent and may be filtered. Reaction products which are soluble in the organic solvent may be isolated by evaporation of the solvent after the organic solution is dried over a drying agent such as sodium sulfate or magnesium sulfate and trituration of the residue with solvents such as diethyl ether, 1chlorobutane or hexane. Chromatography (e.g., silica gel) may also be necessary for purification. Sulfilimines of Formula V can also be prepared by the general procedure illustrated in Equation 3. Equation 3 EMI16.1 The appropriate amine VI is contacted with the appropriate dialkylmercaptide in the presence of N-chlorosuccinimide. The reaction is best carried out in an inert aprotic solvent, such as methylene chloride. chloroform or ethyl acetate at temperatures between -300 to 600C for 1-48 hours with ambient pressure. The resulting solution is then washed with aqueous sodium hydroxide solution and then water. The desired product can be isolated as described in the previous paragraph. Yet another method for preparing the sulfilimines V is shown in Equation 4. Equation 4 EMI16.2 The reaction of Equation 4 may be best carried out in an inert aprotic solvent, such as methylene chloride or chloroform at temperatures between -700 to 700C for 1-48 hours with ambient pressure. The resulting solution may be washed with sodium hydroxide aqueous solution and then water. The desired product can be isolated as described in the previous paragraph. Heterocyclic amines of Formula VI and methods for preparing them are known in the art. The synthe sis of heterocyclic amines such as those of Formula VI has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of this series. 2-Amino-1,3,5-triazines can be prepared according to methods described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives", Vol. XIII of the same series. The synthesis of triazines is also described by F. C. Schaefer, U.S. 3,154,547 and by S. R. Huffman and F. C. Schaefer; J. Or. Chem., 28, 1816 (1963). See also European Patent Application Number 80300505.7, published September 17, 1980 (Pub. No. 15,683), European Patent Application Number 81303837.9, published March 3, 1982 (Pub. No. 46,677), European Patent Application Number 82306492.8, published July 27, 1983 (Pub. No. 84,224), and European Patent Application Number 82303611.6, published March 9, 1983 (Pub. No. 73,562), for description of methods for preparing heterocyclic amine derivatives. The compounds of Formula IIa may be prepared by the reaction of hydroxylamine with an appropriately substituted S-alkyl benzenesulfonyl isothiourea of Formula III, as shown in Equation 5. Equation 5 EMI17.1 wherein L, R. Rd and A are as previously defined. The reaction of Equation 5 is conducted by contacting 1-3 equivalents of hydroxylamine hydrochloride and an equivalent amount of sodium acetate with a compound of Formula III in a suitable solvent, such as tetrahydrofuran, at 0-30 for 1-24 hours. The product may be isolated by removal of solvent and trituration of the residue with water. The compounds of Formula III may be prepared by the methods described in U.S. 4,301.286 to which the reader is referred for further information. Briefly, these products may be made by reacting a compound of formula EMI18.1 wherein Xt is C1 or Br, with MSRd, where M is alkali metal i.e. Na, K or Li; or by reacting a compound of formula EMI18.2 with the lithium salt of a 2-aminoheterocycle of formula EMI18.3 Reaction conditions and the preparation of intermediates for these reactions are described in our aforesaid U.S. patent. Alternatively, the compound of formula III may be prepared by the procedure outlined in Equation 6. Equation 6 EMI18.4 wherein L, R, Rd and A are as previously defined. The reaction of Equation 6 may be carried out by contacting a sulfonyl chloride of Formula VII with an appropriately substituted S-alkyl isothiourea of Formula VIII in an inert solvent, such as methylene chloride or tetrahydrofuran, in the presence of an acid scavenger, such as aqueous sodium bicarbonate or a tertiary amine, such as triethylamine, for 1-3 days at 20-400. The product is isolated by removal of solvent and trituration of the residue with water, or by extraction from water with an organic solvent, concentration, and chromatography. Those references provided above for the preparation of the sulfonyl isocyanates IV also provide details for the preparation of the sulfonyl chlorides VII. The preparation of the compounds of Formula VIII is shown in Equations 7. 8 and 9. Equation 7 EMI20.1 wherein R, Rd and A are as previously defined. The reaction of Equation 7a may be carried out by saturation of a solution of a compound of Formula IX in pyridine with hydrogen sulfide, allowing to react for 1 to 5 days at 25 to 40 , removal of pyridine in vacuo, and crystallization of the product with water or an organic solvent such as ether or methylene chloride. The resulting compound of Formula X may be reacted according to Equation 7b with one equivalent of a dialkyl sulfate or alkyl iodide at 20 to 800 for 1 to 3 days to provide the corresponding alkyl sulfate or iodide salt of VIII. The free base may be obtained by extraction from aqueous sodium bicarbonate with an organic solvent, such as ethyl acetate. An alternative synthesis of compounds of Formula X is shown in Equation 8. Equation 8 EMI21.1 wherein R and A are as previously defined; and J is C H or C HO The reaction of Equation 8a is carried out by contacting a compound of Formula XI with 1-1.5 equivalents of benzoyl- or phenoxycarbonylisothio- cyanate at 30-80 for 1-24 hours in a suitable solvent. such as acetonitrile or tetrahydrofuran. The product may be isolated by cooling or concentration and filtration. The reaction of Equation 8b may be performed by heating the compound of Formula XII in an aqueous medium, with or without a cosolvent, in the presence of 1 to 2 equivalents of an alkali metal hydroxide or an alkali earth oxide at 30 to 800 for 1-24 hours. The product is isolated by cooling. neutralization to pH 8, and filtration in the case where an alkali metal hydroxide is used. and in the case where an alkali earth oxide is used, the reaction mixture is filtered and the filtrate is concentrated, cooled. and filtered. Heterocyclic amines of Formula XI may be prepared by the same methods cited for the synthesis of the amines of Formula VI. A third method by which certain compounds of Formula VIlla may be obtained is shown in Equation 9. Equation 9 EMI22.1 wherein R. Rd, X and Y are as previously defined. The reaction of Equation 9 may be carried out by contacting a chiorotriazine of Formula XIII with an S-alkyl isothiourea of Formula XIV in the same manner as was described in the reaction of Equation 6. Compounds of Formulae IIb and IIc may be obtained from those of Formula IIa by the reactions of Equation 10. Equation 10 EMI22.2 EMI23.1 wherein Ec is C(O)R1, C(O)NR2R3, or CO2R, and L, R, R1. R2, R3, R4, and A are as previously defined. The reaction of Equation 10a is carried out by contacting IIa with 1-10 equivalents of the appropriate carboxylic acid chloride or anhydride, or alkyl chloroformate. or dialkyl carbamoyl chloride in the presence of an acid scavenger, such as pyridine or a tertiary amine, at 0 to 400 for 2 to 24 hours. adding ice-water, and filtering or extracting the product into an organic solvent. The reaction of Equation 10b may be conducted by treating a solution of IIa in an inert solvent such as methylene chloride or acetonitrile with 1-1.5 equivalents of an alkyl isocyanate at 20-80 for 1 to 24 hours. The product is isolated by concentrating the reaction mixture and trituration with a solvent such as ether or chlorobutane. Agriculturally suitable salts of compounds of Formulae II and III are also useful herbicides. Salts of compounds of Formulae II and III can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formulae II and III 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 Formulae II and III can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formulae II and III (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 Formulae II and III (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 Formulae II and III with a suitable acid, e.g., -toluenesulfonic acid, trichioroacetic acid or the like. The disclosures of all references cited above are herein incorporated by reference. In the following examples. all parts are by weight and temperatures in "C unless otherwise indicated. Example 1 Preparation of S,S-dimethyl-N-t4,6-dimethylpyrimi-din-2- yl)sulfilimine, To a solution of 12.3 g (0.10 mole) of 2-amino4,6-dimethylpyrimidine and 8 ml (0.109 mole) of methylsulfide in 100 ml of methylene chloride at -200C was added dropwise a solution of 13.3 g (0.10 mole) of Nchlorosuccinimide in 300 ml of methylene chloride. After addition, the resulting solution was warmed to room temperature and was kept at room temperature for one hour with stirring. The solution was then washed with 400 ml of 2.5% sodium hydroxide aqueous solution and then 400 ml of water. This solution was dried over sodium sulfate and filtered. The filtrate was washed with ethyl ether, and dried under vacuum at ambient temperature to afford 4 g of the title compound as a white solid, m.p. 117-1200C. NMR: 6 2.23 (s, CH3); 6 2.7 (s, SCH3); and 6 6.23 (s, ArH). Example 2 Preparation of S,S-dimethyl-N-(4,6-dimethoxypyrimidin 2-sl)sulfilimine To a solution of 15.5 g (0.10 mole) of 2-amino4,6-dimethoxypyrimidine and 8 ml (0.109 mole) of methylsulfide in 100 ml of methylene chloride at -200C was added dropwise a solution of 13.3 g (0.10 mole) of N-chlorosuccinimide in 300 ml of methylene chloride. After addition, the resulting solution stirred at -200C for 2 hours and then warmed up to room temperature. The solution was stirred at room temperature for another hour. The solution was washed with 400 ml of 2.5% sodium hydroxide aqueous solution and then 400 ml of water. The organic layer was separated. dried over sodium sulfate and concentrated under reduced pressure. The residue was washed with ethyl ether, and dried under vacuum at ambient temperature to afford 6 g of the title compound as a solid, m.p. 102-1030C (dec.). NMR: 6 2.73 (s. SCH3); 6 3.9 (s, OCH3); and 6 5.37 (s. ArH). Example 3 [[N-(2-Chlorophenylsulfonylaminocarbonyl)-N-(4,6 dimethylpyrimidin-2-yl) ]aminojdimethylsulfonium inner salt To a solution of 0.6 g (0.0033 mole) of S,S dimethyl-N-(4, 6-dimethylpyrimidin-2-yl)sulfilimine in 15 ml of methylene chloride was added 1.5 g (0.0069 mole) of 2-chlorophenylsulfonyl isocyanate. The resulting solution was stirred at ambient temperature for 12 hours. The solution was then concentrated under reduced pressure. The residue was washed with l-chlorobutane, ethyl ether and ethyl acetate. The solid was collected by filtration and dried under vacuum to afford 1.1 g of the title compound, m.p. 104-105"C (dec.). NMR: 6 2.43 (s, CH3); 6 2.87 (s, SCH3); and 6 6.5-8.5 (m, ArH). Example 4 2-Chloro-N-[[(4.6-dimethylpyrimidin-2-yl)aminoJhydroxy- iminomethYllbenzenesulfonamide To a solution of 0.5 g of methyl N'-(2-chloro phenylsu1fonyl)-N-(4,6-dimethylpyrimdin-2-yl)carbam imidothioate in 10 ml of tetrahydrofuran was added 0.3 g of hydroxylamine hydrochloride and 0.3 g of sodium acetate. The mixture was stirred at room temperature for 2 hours a whereupon the product was precipitated with ice-water, filtered a washed with water, and dried by suction to afford 0.3 g of the title compound a m.p. l65l670. NMR(CDCl3/DMSO-d6) 6 2.6 (s, 6), 6.8 (s, 1), 7.4 (m, 3), 8.2 (m, 1), 10.2 (br, 1), 12.0 (br, 1). m/e: 355 (M+). Example 5 N-(4,6-Dimethylyrimidin-2-yl)thiourea A suspension of 10 g of 2-cyanoamino-4,6-di- methylpyrimidine in 50 ml of pyridine was saturated with hydrogen sulfide and stored for 1 hour at 250. The H2S treatment was repeated twice more, and the mixture was allowed to stir at 250 for 16 hours. Methylene chloride was added1 and the product was filtered and washed with methylene chloride to afford 8 g of 4,6-dimethylpyrimidin-2-yl thiourea, m.p. > 2600. IR (Nujol) 3280, 3180, 3120, 1610 cm Example 6 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminothioxomethyl]benzamide To a hot solution of 14 g of ammonium thiocyanate in 300 ml of acetonitrile was added 24 ml of benzoyl chloride. The mixture was heated on the steam bath for 30 minutes and filtered. The filtrate was heated with 21 g of 4-methoxy-6-methylpyrimidine-2amine for 30 minutes and cooled. The product was collected by filtration and washed with a little acetonitrile to provide 28 g of N-[((4-methoxy-6- methylpyrimidin-2-yl)aminothiocarbonyl]amino]benzamide, m.p. 193-195 . IR (Nujol) 3290, 1720 cm1. Example 7 N-(4-Methoxy-6-methylpyrimidin-2-yl)thiourea A mixture of 25 g of the compound from Example 3 and 55 ml of 10% aqueous sodium hydroxide was heated on the steam bath for 30 minutes, cooled, neutralized with aqueous HC1 to pH 8, filtered. washed with water, dried by suction. and washed with ether to afford 16 g of the title compound, m.p. 220 d. Anal. Calc'd.: C: 42.4, H: 5.06. N: 28.2, S: 16.2 Found: C: 42.6. H: 4.8, N: 28.8. S: 15.3 m/e 198 (M ). Example 8 Methyl 2-[[1-(4-methoxy-6-methylpyrimidin-2-ylimino)-1 (methylthio)methyl]aminosulfonyl]benzcate To 9 g of the compound from Example 4 and 100 ml of tetrahydrofuran was added 7.6 g of dimethyl sulfate and the mixture was stirred for 2 days at room temperature. The product was filtered and washed with a little tetrahydrofuran to give 22 g of crude product. Five grams of this material was suspended in 150 ml of methylene chloride and 1 ml of water, and 5 g of sodium bicarbonate and 6 g of methyl 2-chlorosulfonyl benzoate were added. The mixture was stirred for 24 hours, washed with dilute aqueous HCl, dried with sodium sulfate, filtered, and chromatographed on silica gel to afford 2.8 g of the title compound as a crystalline solid, m.p. 143-144". Anal. Calc'd.: C: 45.22, H: 4.55. N: 14.06. S: 16.1 Found: C: 46.8, H: 4.35. N: 13.2, S: 16 m/e 395 (M -CH3) NMR(CDC13) 6 2.35 (s, 3), 2.45 (s, 3). 3.90 (s, 3), 4.0 (s. 3) 6.35 (s. 1). 7.7 (m, 3), 8.2 (m. 1). 10.8 brs, 1). Example 9 Methyl N-(4,6-dimethoxy-1,3,5,-triazin-2-yl)carbamini dothioate A mixture of 20 g of 2-chloro-4,6-dimethoxy-striazine, 20 g of S-methyl isothiouronium sulfate, 16 g of sodium carbonate, and 50 ml of water was stirred for 72 hours. concentrated at reduced pressure, and extracted with 300 ml of methylene chloride. The organic layer was dried with Na2S04, filtered, concentrated to dryness, and recrystallized from chlorobutane to afford 10 g of title compound a m.p. 94-100 . NMR(CDCl3) 6 2.6 (s, 3), 4.0 (s, 6), 8.2 (brs, 1). Using the procedures and examples shown above a the compounds in Tables 1-35 can be prepared. Table 1 EMI30.1 R5 Ra Rb R6 X Y m.p.( C) CO2CH3 CH3 CH3 H CH3 CH3 88-90 (d CO2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH3 C2H5 CH3 H CH3 CH3 CO2CH3 C2H5 CH3 H CH3 CH3 CO2CH2CH2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH2CH=CH2 CH3 CH3 H CH3 CH3 CO2CH2CH2OCH3 CH3 CH3 H CH3 CH3 CO2CH2CH2Cl CH3 CH3 H CH3 CH3 SCH3 CH3 CH3 H CH3 CH3 SCH2CH3 CH3 CH3 H CH3 CH3 SCH(CH3)2 CH3 CH3 H CH3 CH3 SCH2CH=CH2 CH3 CH3 H CH3 CH3 SCF3 CH3 CH3 H CH3 CH3 SCF2H CH3 CH3 H CH3 CH3 SO2CH3 CH3 CH3 H CH3 CH3 90-91 (d) SO2CH2CH3 CH3 CH3 H CH3 CH3 SO2CH3 C2H5 C2H5 H CH3 CH3 SO2CH3 C2H5 CH3 H CH3 CH3 SO2CF3 CH3 CH3 H CH3 CH3 SO2CF2H CH3 CH3 H CH3 CH3 OSO2CH3 CH3 CH3 H CH3 CH3 OSO2CH2CH3 CH3 CH3 H CH3 CH3 OSO2CH(CH3)2 CH3 CH3 H CH3 CH3 OCH3 CH3 CH3 H CH3 CH3 OCH2CH3 CH3 CH3 H CH3 CH3 29 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) OCH2CH2CH3 CH3 CH3 H CH3 CH3 OCH(CH3)CH2CH3 CH3 CH3 H CH3 CH3 OCH2CH=CH2 CH3 CH3 H CH3 CH3 OCH2CH2CH=CH2 CH3 CH3 H CH3 CH3 OCH(CH3)CH=CH2 CH3 CH3 H CH3 CH3 SO2N(CH3)2 CH3 CH3 H CH3 CH3 SON(CH3)CH(CH3)2 CH3 CH3 H CH3 CH3 SO2N(OCH3)CH3 CH3 CH3 H CH3 CH3 CH2OCH3 CH3 CH3 H CH3 CH3 CH2CH2OCH3 CH3 CH3 H CH3 CH3 F CH3 CH3 H CH3 CH3 Cl CH3 CH3 H CH3 CH3 104-105 (d) Br CH3 CH3 H CH3 CH3 NO2 CH3 CH3 H CH3 CH3 118-120 (d) CF3 CH3 CH3 H CH3 CH3 CH3 CH3 CH3 H CH3 CH3 CH2CH3 CH3 CH3 H CH3 CH3 CH(CH3)2 CH3 CH3 H CH3 CH3 CH2CH2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH2CH2CH3 CH3 CH3 H CH3 CH3 SCH3 C2H5 C2H5 H CH3 CH3 SCF3 C2H5 CH3 H CH3 CH3 SO2CH2CH3 C2H5 C2H5 H CH3 CH3 NO2 CH3 CH3 H CH3 CH3 CF3 CH3 CH3 H CH3 CH3 CH3 CH3 CH3 H CH3 CH3 NO2 CH3 CH3 5-CF3 CH3 CH3 NO2 CH3 CH3 3-Cl CH3 CH3 Cl CH3 CH3 6-SCH3 CH3 CH3 CF3 CH3 CH3 5-SCH3 CH3 CH3 Cl CH3 CH3 5-Cl CH3 CH3 NO2 CH3 CH3 5-Cl CH3 CH3 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) SO2N(CH3)2 C2H5 C2H5 3-Cl CH3 CH3 CO2CH3 CH3 CH3 5-CH3 CH3 CH3 Cl CH3 CH3 3-Br CH3 CH3 Cl CH3 CH3 5-Br CH3 CH3 NO2 CH3 CH3 6-F CH3 CH3 Cl CH3 CH3 6-F CH3 CH3 Br CH3 CH3 3-F CH3 CH3 NO2 C2H5 C2H5 5-OCF2H CH3 CH3 CO2CH3 CH3 CH3 3-OCH3 CH3 CH3 CH3 CH3 CH3 3-OCH3 CH3 CH3 CO2CH3 CH3 CH3 H Cl OCH3 NO2 CH3 CH3 H Cl OCH3 Cl CH3 CH3 H Cl OCH3 CO2CH3 C2H5 CH3 H CH3 OCH3 CO2CH3 C2H5 C2H5 H CH3 OCH3 NO2 C2H5 CH3 H CH3 OCH3 SO2N(CH3)2 C2H5 CH3 H CH3 OCH3 CO2CH3 CH3 CH3 H CH3 CH2OCH3 CO2CH3 CH3 CH3 H CH3 CH(OCH3)2 CO2CH3 CH3 CH3 H CH3 CH(OCH2CH2O) NO2 C2H5 C2H5 H CH3 OCH3 SO2N(CH3)2 C2H5 C2H5 H CH3 OCH3 CO2CH3 CH3 CH3 H CH3 OCH3 90-91 (d) CO2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH(CH3)2 CH3 CH3 H CH3 OCH3 CO2CH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH2CH=CH2 CH3 CH3 H CH3 OCH3 CO2CH2CH2OCH3 CH3 CH3 H CH3 OCH3 CO2CH2CH2Cl CH3 CH3 H CH3 OCH3 SCH3 CH3 CH3 H CH3 OCH3 SCH2CH3 CH3 CH3 H CH3 OCH3 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) SCH(CH3)2 CH3 CH3 H CH3 OCH3 SCH2CH=CH2 CH3 CH3 H CH3 OCH3 SCF3 CH3 CH3 H CH3 OCH3 SCF2H CH3 CH3 H CH3 OCH3 SO2CH3 CH3 CH3 H CH3 OCH3 SO2CH2CH3 CH3 CH3 H CH3 OCH3 SO2CH(CH3)2 CH3 CH3 H CH3 OCH3 SO2CH2CH=CH2 CH3 CH3 H CH3 OCH3 SO2CF3 CH3 CH3 H CH3 OCH3 SO2CF2H CH3 CH3 H CH3 OCH3 OSO2CH3 CH3 CH3 H CH3 OCH3 OSO2CH2CH3 CH3 CH3 H CH3 OCH3 OSO2CH(CH3)2 CH3 CH3 H CH3 OCH3 OCH3 CH3 CH3 H CH3 OCH3 OCH2CH3 CH3 CH3 H CH3 OCH3 OCH(CH3)2 CH3 CH3 H CH3 OCH3 OCH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 OCH2CH=CH2 CH3 CH3 H CH3 OCH3 OCH2CH2CH=CH2 CH3 CH3 H CH3 OCH3 OCH(CH3)CH=CH2 CH3 CH3 H CH3 OCH3 SO2N(CH3)2 CH3 CH3 H CH3 OCH3 95-96 (d) SO2N(CH3)CH(CH3)2 CH3 CH3 H CH3 OCH3 SO2N(OCH3)CH3 CH3 CH3 H CH3 OCH3 CH2OCH3 CH3 CH3 H CH3 OCH3 CH2CH2OCH3 CH3 CH3 H CH3 OCH3 F CH3 CH3 H CH3 OCH3 Cl CH3 CH3 H CH3 OCH3 89-90 C(d) Br CH3 CH3 H CH3 OCH3 NO2 CH3 CH3 H CH3 OCH3 172-173 (d) CF3 CH3 CH3 H CH3 OCH3 CH3 CH3 CH3 H CH3 OCH3 CH2CH3 CH3 CH3 H CH3 OCH3 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) CH(CH3)2 CH3 CH3 H CH3 OCH3 CH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH3 CH3 CH3 H Br OCH3 @ @ @ @ @ SCH3 C2H5 CH3 H CH3 OCH3 SCF3 C2H5 CH3 H CH3 OCH3 NO2 CH3 CH3 5-CF3 CH3 OCH3 NO2 CH3 CH3 3-Cl CH3 OCH3 CI CH3 CH3 6-SCH3 CH3 OCH3 @ @ @ @ @ CF3 CH3 CH3 5-OCF2H CH3 OCH3 Cl CH3 CH3 5-Cl CH3 OCH3 NO2 CH3 CH3 5-Cl CH3 OCH3 SO2N(CH3)2 CH3 CH3 3-Cl CH3 OCH3 CO2CH3 CH3 CH3 5-CH3 CH3 OCH3 Cl CH3 CH3 3-Br CH3 OCH3 Cl CH3 CH3 5-Br CH3 OCH3 NO2 CH3 CH3 6-F CH3 OCH3 Cl CH3 CH3 6-F CH3 OCH3 Br CH3 CH3 3-F CH3 OCH3 NO2 CH3 CH3 5-SCH3 CH3 OCH3 CO2CH3 CH3 CH3 3-OCH3 CH3 OCH3 CH3 CH3 CH3 3-OCH3 CH3 OCH3 CO2CH3 C2H5 CH3 H OCH3 OCH3 CO2CH3 C2H5 C2H5 H OCH3 OCH3 NO2 C2H5 CH3 H OCH3 OCH3 SO2N(CH3)2 C2H5 CH3 H OCH3 OCH3 CO2CH3 CH3 CH3 H OCH3 CH2OCH3 CO2CH3 CH3 CH3 H OCH3 CH(OCH3)2 CO2CH3 CH3 CH3 H OCH3 CH(OCH2CH2O) NO2 C2H5 C2H5 H OCH3 OCH3 SO2N(CH3)2 C2H5 C2H5 H OCH3 OCH3 CO2CH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH3 CH3 CH3 H OCH3 OCH3 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) CO2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 CO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 152-1540(d) CO2CH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 151-1530(d) CO2CH2CH2OCH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH2Cl CH3 CH3 H OCH3 OCH3 SCH3 CH3 CH3 H OCH3 OCH3 SCH2CH3 CH3 CH3 H OCH3 OCH3 SCH(CH3)2 CH3 CH3 H OCH3 OCH3 SCH2CH=CH2 CH3 CH3 H OCH3 OCH3 SCF3 CH3 CH3 H OCH3 OCH3 SCF2H CH3 CH3 H OCH3 OCH3 SO2CH3 CH3 CH3 H OCH3 OCH3 SO2CH2CH3 CH3 CH3 H OCH3 OCH3 SO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 SO2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 SO2CF3 CH3 CH3 H OCH3 OCH3 SO2CF2H CH3 CH3 H OCH3 OCH3 OSO2CH3 CH3 CH3 H OCH3 OCH3 OSO2CH2CH3 CH3 CH3 H OCH3 OCH3 OSO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 OCH3 CH3 CH3 H OCH3 OCH3 OCH2CH3 CH3 CH3 H OCH3 OCH3 OCH(CH3)2 CH3 CH3 H OCH3 OCH3 OCH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 OCH2CH=CH2 CH3 CH3 H OCH3 OCH3 OCH2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 OCH(CH3)CH=CH2 CH3 CH3 H OCH3 OCH3 SO2N(CH3)2 CH3 CH3 H OCH3 OCH3 173-175 (d) SO2N(CH3)CH(CH3)2 CH3 CH3 H OCH3 OCH3 SO2N(OCH3)CH3 CH3 CH3 H OCH3 OCH3 CH2OCH3 CH3 CH3 H OCH3 OCH3 Table 1 (continued) R5 Ra Rb R6 X Y m.p.( C) CH2CH2OCH3 CH3 CH3 H OCH3 OCH3 F CH3 CH3 H OCH3 OCH3 Cl CH3 CH3 H OCH3 OCH3 Br CH3 CH3 H OCH3 OCH3 NO2 CH3 CH3 H OCH3 OCH3 CF3 CH3 CH3 H OCH3 OCH3 CH3 CH3 CH3 H OCH3 OCH3 CH2CH3 CH3 CH3 H OCH3 OCH3 CH(CH3)2 CH3 CH3 H OCH3 OCH3 CH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 SO2N(CH3)2 CH3 CH3 H Cl OCH3 SCH3 C2H5 CH3 H OCH3 OCH3 SCF3 C2H5 CH3 H OCH3 OCH3 NO2 CH3 CH3 5-CF3 OCH3 OCH3 NO2 CH3 CH3 3-Cl OCH3 OCH3 Cl CH3 CH3 6-SCH3 OCH3 OCH3 CF3 CH3 CH3 5-OCF2H OCH3 OCH3 Cl CH3 CH3 5-Cl OCH3 OCH3 NO2 CH3 CH3 5-Cl OCH3 OCH3 SO2N(CH3)2 CH3 CH3 3-Cl OCH3 OCH3 CO2CH3 CH3 CH3 5-CH3 OCH3 OCH3 Cl CH3 CH3 3-Br OCH3 OCH3 Cl CH3 CH3 5-Br OCH3 OCH3 NO2 CH3 CH3 6-F OCH3 OCH3 Cl CH3 CH3 6-F OCH3 OCH3 Br CH3 CH3 3-F OCH3 OCH3 NO2 CH3 CH3 5-SCH3 OCH3 OCH3 CO2CH3 CH3 CH3 3-OCH3 OCH3 OCH3 CH3 CH3 CH3 3-OCH3 OCH3 OCH3 CO2CH3 CH3 CH3 H OCH2H CH3 CO2CH3 CH3 CH3 H CH2F OCH3 CO2CH3 CH3 CH3 H CH3 C2H5 Table 1 (continued) EMI37.1 <tb> R5 <SEP> Ra <SEP> Rb <SEP> 6 <SEP> X <SEP> Y <SEP> m.P.(oc) <tb> 5 <SEP> a <SEP> b <SEP> 6 <SEP> m.P.("c) <tb> COUCH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> C <SEP> 2H5 <tb> COUCH3 <SEP> CH3 <SEP> CM3 <SEP> H <SEP> CF3 <SEP> OCH3 <tb> CO2CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CF3 <SEP> CH3 <tb> COUCH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> 2 <SEP> 5 <SEP> CH3 <tb> C 2CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> 0C2H5 <SEP> OCH3 <tb> COUCH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH2CF3 <tb> COUCH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> OCM2CF3 <tb> <SEP> - <SEP> N-N <tb> <SEP> /I <SEP> CH3 <SEP> CH <SEP> H <SEP> CH3 <SEP> CH3 <tb> /\0¯ <SEP> 3 <SEP> 3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> N-N <tb> <SEP> o <SEP> CHB <SEP> CH3 <SEP> H <SEP> CH, <SEP> OCH3 <tb> <SEP> H <tb> <SEP> N-N <tb> AN0·\ <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> <SEP> H <tb> <SEP> N-N <tb> <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH, <SEP> CH3 <tb> <SEP> / <SEP> > <SEP> w13 <SEP> WA3 <SEP> A <SEP> WA3 <SEP> çH3 <tb> <SEP> CH3 <tb> <SEP> N'N <tb> <SEP> CM3 <SEP> )\ <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> CH3 <tb> <SEP> N-N <tb> <SEP> /I <SEP> CH, <SEP> CH3 <SEP> H <SEP> OCH <SEP> OCH, <tb> <SEP> CH3 <tb> <SEP> CM3 <tb> /ICH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> N-O <tb> <SEP> 9 > <SEP> 3 <SEP> 3 <SEP> 3 <SEP> 3 <tb> <SEP> NO <tb> <SEP> Q <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> Table 1 (continued) EMI38.1 <tb> R5 <SEP> R <SEP> R <SEP> R <tb> a <SEP> a <SEP> b <SEP> 6 <SEP> X <SEP> Y <SEP> mAffA..aC <tb> <SEP> N-O <tb> <SEP> /I <SEP> CK, <SEP> CH, <SEP> H <SEP> OCH, <SEP> OCK3 <tb> <SEP> J <tb> <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CM3 <SEP> CH3 <tb> <SEP> o-N <tb> <SEP> CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> O-N <tb> <SEP> CH3 <SEP> CKB <SEP> H <SEP> OCH, <SEP> OCH3 <tb> <SEP> N=N <tb> <SEP> 4 <SEP> S <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> J <SEP> S <SEP> 3 <tb> <SEP> )%JN's <SEP> CM3 <SEP> 3 <SEP> H <SEP> CM3 <SEP> OCH3 <tb> <SEP> N=N <tb> <SEP> CM3 <SEP> CM3 <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> CM <SEP> CM <SEP> CM3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <tb> CM <SEP> CM <SEP> CM3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> SCH3 <tb> 2 <SEP> 3 <SEP> CH3 <SEP> CM3 <SEP> H <SEP> OCH3 <SEP> OCH2CH=CH2 <tb> COUCH3 <SEP> CH3 <SEP> CM3 <SEP> H <SEP> OCH3 <SEP> OCM2C=CH <tb> 2 <SEP> CM3 <SEP> CH3 <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <tb> CO2CH3 <SEP> CH3 <SEP> CM3 <SEP> H <SEP> OCH3 <SEP> SCF2H <tb> Table 2 EMI39.1 R5 Ra Rb R6 X Y m.p.( C) CO2CH3 CH3 CH3 H CH3 CH3 CO2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH3 C2H5 CH3 H CH3 CH3 CO2CH3 C2H5 CH3 H CH3 CH3 CO2CH2CH=CH2 CH3 CH3 H CH3 CH3 CO2CH2CH2OCH3 CH3 CH3 H CH3 CH3 CO2CH2CH2Cl CH3 CH3 H CH3 CH3 SCH3 CH3 CH3 H CH3 CH3 SCH2CH3 CH3 CH3 H CH3 CH3 SCH(CH3)2 CH3 CH3 H CH3 CH3 SCH2CH=CH2 CH3 CH3 H CH3 CH3 SCF3 CH3 CH3 H CH3 CH3 SCF2H CH3 CH3 H CH3 CH3 SO2CH3 CH3 CH3 H CH3 CH3 SO2CH3 C2H5 C2H5 H CH3 CH3 SO2CH3 C2H5 C2H5 H CH3 CH3 SO2CH2CH=CH2 CH3 CH3 H CH3 CH3 SO2CF3 CH3 CH3 H CH3 CH3 SO2CF2H CH3 CH3 H CH3 CH3 OSO2CH3 CH3 CH3 H CH3 CH3 OS02CH2CH3 CH3 CH3 H CH3 CH3 OSO2CH(CH3)2 CH3 CH3 H CH3 CH3 OCH3 CH3 CH3 H CH3 CH3 OCH2CH3 CH3 CH3 H CH3 CH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) OCH2CH2CH3 CH3 CH3 H CH3 CH3 OCH(CH3)CH2CH3 CH3 CH3 H CH3 CH3 OCH2CH=CH2 CH3 CH3 H CH3 CH3 OCH2CH2CH=CH2 CH3 CH3 H CH3 CH3 OCH(CH3)CH=CH2 CH3 CH3 H CH3 CH3 SO2N(CH3)2 CH3 CH3 H CH3 CH3 SO2N(CH3)CH(CH3)2 CH3 CH3 H CH3 CH3 SO2N(OCH3)CH3 CH3 CH3 H CH3 CH3 CH2OCH3 CH3 CH3 H CH3 CH3 CH2CH2OCH3 CH3 CH3 H CH3 CH3 F CH3 CH3 H CH3 CH3 Cl CH3 CH3 H CH3 CH3 Br CH3 CH3 H CH3 CH3 NO2 CH3 CH3 H CH3 CH3 CF3 CH3 CH3 H CH3 CH3 CH3 CH3 CH3 H CH3 CH3 CH2CH3 CH3 CH3 H CH3 CH3 CH(CH3)2 CH3 CH3 H CH3 CH3 CH2CH2CH2CH3 CH3 CH3 H CH3 CH3 CO2CH2CH2CH3 CH3 CH3 H CH3 CH3 SO2CH2CH3 C2H5 C2H5 H CH3 CH3 CH2OCH3 CH3 CH3 H CH3 CH3 CH2CH2OCH3 CH3 CH3 H CH3 CH3 NO2 CH3 CH3 5-CF3 CH3 CH3 NO2 CH3 CH3 3-Cl CH3 CH3 Cl CH3 CH3 6-SCH3 CH3 CH3 CF3 CH3 CH3 5-OCF2H CH3 CH3 Cl CH3 CH3 5-Cl CH3 CH3 NO2 CH3 CH3 5-Cl CH3 CH3 SO2N(CH3)2 C2H5 C2H5 3-Cl CH3 CH3 CO2CH3 CH3 CH3 5-CH3 CH3 CH3 Cl CH3 CH3 3-Br CH3 CH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) Cl CH3 CH3 5-Br CH3 CH3 N02 CH3 CH3 6-F CH3 CH3 Cl CH3 CH3 6-F CH3 CH3 Br CH3 CH3 3-F CH3 CH3 NO2 C2H5 C2H5 5-SCH3 CH3 CH3 CO2CH3 CH3 CH3 3-OCH3 CH3 CH3 CH3 CH3 CH3 3-OCH3 CH3 CH3 CO2CH3 C2H5 CH3 H CH3 OCH3 CO2CH3 C2H5 C2H5 H CH3 OCH3 NO2 C2H5 CH3 H CH3 OCH3 SO2N(CH3)2 C2H5 CH3 H CH3 OCH3 CO2CH3 CH3 CH3 H CH3 CH2OCH3 CO2CH3 CH3 CH3 H CH3 CH(OCH3)2 CO2CH3 CH3 CH3 H CH3 CH(OCH2CH2O) NO2 C2H5 C2H5 H CH3 OCH3 SO2N(CH3)2 C2H5 C2H5 H CH3 OCH3 CO2CH3 CH3 CH3 H CH3 OCH3 CO2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH(CH3)2 CH3 CH3 H CH3 OCH3 89-91 (d) CO2CH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 CO2CH2CH=CH2 CH3 CH3 H CH3 OCH3 CO2CH2CH2OCH3 CH3 CH3 H CH3 OCH3 CO2CH2CH2Cl CH3 CH3 H CH3 OCH3 SCH3 CH3 CH3 H CH3 OCH3 SCH2 CH3 CH3 CH3 H CH3 OCH3 SCH(CH3)2 CH3 CH3 H CH3 OCH3 SCH2CH=CH2 CH3 CH3 H CH3 OCH3 SCF3 CH3 CH3 H CH3 OCH3 SCF2H CH3 CH3 H CH3 OCH3 SO2CH3 CH3 CH3 H CH3 OCH3 SO2CH2CH3 CH3 CH3 H CH3 OCH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) SO2CH(CH3)2 CH3 CH3 H CH3 OCH3 SO2CH2CH=CH2 CH3 CH3 H CH3 OCH3 SO2CF3 CH3 CH3 H CH3 OCH3 SO2CF2H CH3 CH3 H CH3 OCH3 OSO2CH3 CH3 Cf'3 H CH3 OCH3 OSO2CH2CH3 CH3 CH3 H CH3 OCH3 OSO2CH(CH3)2 CH3 CH3 H CH3 OCH3 OCH3 CH3 CH3 H CH3 OCH3 OCH2CH3 CH3 CH3 H CH3 OCH3 OCH(CH3)2 CH3 CH3 H CH3 OCH3 OCH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 OCH2CH=CH2 CH3 CH3 R CH3 OCH3 OCH2CH2CH=CH2 CH3 CH3 H CH3 OCH3 OCH(CH3)CH=CH2 CH3 CH3 H CH3 OCH3 SO2N(CH3)2 CH3 CH3 H CH3 OCH3 SO2N(CH3)CH(CH3)2 CH3 CH3 H CH3 OCH3 SO2N(OCH3)CH3 CH3 CH3 H CH3 OCH3 CH2OCH3 CH3 CH3 H CH3 OCH3 CH2CH2OCH3 CH3 CH3 H CH3 OCH3 F CH3 CH3 H CH3 OCH3 Cl CH3 CH3 H CH3 OCH3 Br CH3 Cf'3 H CH3 OCH3 NO2 CH3 CH3 H CH3 OCH3 CF3 CH3 CH3 H CH3 OCH3 CH3 CH3 CH3 H CH3 OCH3 CH2CH3 CH3 CH3 H CH3 OCH3 CH(CH3)2 CH3 CH3 H CH3 OCH3 CH2CH2CH2CH3 CH3 CH3 H CH3 OCH3 SCH3 C2H5 CH3 H CH3 OCH3 SCF3 C2H5 CH3 H CH3 OCH3 NO2 CH3 CH3 5-CF3 CH3 OCH3 NO2 CH3 CH3 3-Cl CH3 OCH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) Cl CH3 CH3 6-SCH3 CH3 OCH3 CF3 CH3 CH3 5-OCF2H CH3 OCH3 Cl CH3 CH3 5-Cl CH3 OCH3 NO2 CH3 CH3 5-Cl CH3 OCH3 SO2N(CH3)2 CH3 CH3 3-Cl CH3 OCH3 CO2CH3 CH3 CH3 5-CH3 CH3 OCH3 Cl CH3 CH3 3-Br CH3 OCH3 Cl CH3 CH3 5-Br CH3 OCH3 NO2 CH3 CH3 6-F CH3 OCH3 Cl CH3 CH3 6-F CH3 OCH3 Br CH3 CH3 3-F CH3 OCH3 N02 CH3 CH3 5-SCH3 CH3 OCH3 CO2CH3 CH3 CH3 3-OCH3 CH3 OCH3 CH3 CH3 CH3 3-OCH3 CH3 OCH3 CO2CH3 C2H5 CH3 H OCH3 OCH3 CO2CH3 C2H5 CH3 H OCH3 OCH3 NO2 C2H5 CH3 H OCH3 OCH3 SO2N(CH3)2 C2H5 CH3 H OCH3 OCH3 CO2CH3 CH3 CH3 H OCF2H OCH3 CO2CH3 CH3 CH3 H CF3 OCH3 CO2CH3 CH3 CH3 H CH2F OCH3 NO2 C2H5 C2H5 H OCH3 OCH3 SO2N(CH3)2 C2H5 C2H5 H OCH3 OCH3 CO2CH3 CH3 CH3 H OCH3 OCH3 88-90 (d) CO2CH2CH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 CO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 CO2CH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 CO2CH2CH2OCH3 CH3 CH3 H OCH3 OCH3 CO2CH2CH2Cl CH3 CH3 H OCH3 OCH3 SCH3 CH3 CH3 H OCH3 OCH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) SCH2CH3 CH3 CH3 H OCH3 OCH3 SCH(CH3)2 CH3 CH3 H OCH3 OCH3 SCH2CH=CH2 CH3 CH3 H OCH3 OCH3 SCF3 CH3 CH3 H OCH3 OCH3 SCF2H CH3 CH3 H OCH3 OCH3 SO2CH3 CH3 CH3 H OCH3 OCH3 SO2CH2CH3 CH3 CH3 H OCH3 OCH3 SO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 SO2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 SO2CF3 CH3 CH3 H OCH3 OCH3 SO2CF2H CH3 CH3 H OCH3 OCH3 OSO2CH3 CH3 CH3 H OCH3 OCH3 OSO2CH2CH3 CH3 CH3 H OCH3 OCR3 OSO2CH(CH3)2 CH3 CH3 H OCH3 OCH3 OCH3 CH3 CH3 H OCH3 OCH3 OCH2CH3 CH3 CH3 H OCH3 OCH3 OCH(CH3)2 CH3 CH3 H OCH3 OCH3 OCH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 OCH2CH=CH2 CH3 CH3 H OCH3 OCH3 OCH2CH2CH=CH2 CH3 CH3 H OCH3 OCH3 OCH(CH3)CH=CH2 CH3 CH3 H OCH3 OCH3 SO2N(CH3)2 CH3 CH3 H OCH3 OCH3 SO2N(CH3)CH(CH3)2 CH3 CH3 H OCH3 OCH3 SO2N(OCH3)OCH3 CH3 CH3 H OCH3 OCH3 CH2OCH3 CH3 CH3 H OCH3 OCH3 CH2CH2OCH3 CH3 CH3 H OCH3 OCH3 F CH3 CH3 H OCH3 OCH3 Cl CH3 CH3 H OCH3 OCH3 98-99 (d) Br CH3 CH3 H OCH3 OCH3 NO2 CH3 CH3 H OCH3 OCH3 125-127 (d) CF3 CH3 CH3 H OCH3 OCH3 CH3 CH3 CH3 H OCH3 OCH3 Table 2 (continued) R5 Ra Rb R6 X Y m.p.( C) CH2CH3 CH3 CH3 H OCH3 OCH3 CH(CH3)2 CH3 CH3 H OCH3 OCH3 CH2CH2CH2CH3 CH3 CH3 H OCH3 OCH3 SCH3 C2H5 CH3 H OCH3 OCH3 SCF3 C2H5 CH3 H OCH3 OCH3 N02 CH3 CH3 5-CF3 OCH3 OCH3 NO2 CH3 CH3 3-Cl OCH3 OCH3 Cl CH3 CH3 6-SCH3 OCH3 OCH3 CF3 CH3 CH3 5-OCF2H OCH3 OCH3 Cl CH3 CH3 5-Cl OCH3 OCH3 NO2 CH3 CH3 5-C1 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 3-Cl OCH3 OCH3 CO2CH3 CH3 CH3 5-CH3 OCH3 OCH3 Cl CH3 CH3 3-Br OCH3 OCH3 Cl CH3 CH3 5-Br OCH3 OCH3 NO2 CH3 CH3 6-F OCH3 OCH3 Cl CH3 CH3 6-F OCH3 OCH3 Br CH3 CH3 3-F OCH3 OCH3 NO2 CH3 CH3 5-SCH3 OCH3 OCH3 CO2CH3 CH3 CH3 3-OCH3 OCH3 OCH3 CH3 CH3 CH3 3-OCH3 OCH3 OCH3 CO2CH3 CH3 CH3 H CH3 H CO2CH3 CH3 CH3 H OCH3 H CO2CH3 CH3 CH3 H CH3 C2H5 CO2CH3 CH3 CH3 H OCH3 C2H5 CO2CH3 CH3 CH3 H CF3 OCH3 CO2CH3 CH3 CH3 H CF3 CH3 CO2CH3 CH3 CH3 H OC2H5 N(CH3)2 CO2CH3 CH3 CH3 H OC2H5 CH3 CO2CH3 CH3 CH3 H OCH3 OCH2CF3 CO2CH3 CH3 CH3 H OCH3 OCH2CF3 Table 2 (continued) EMI46.1 <tb> R5 <SEP> Ra <SEP> Rb <SEP> R6 <SEP> X <SEP> Y <SEP> m.P.( C) <tb> <SEP> a <SEP> b <SEP> 6 <SEP> X <SEP> Y <SEP> m.p.("C) <tb> <SEP> CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> H <tb> <SEP> N-N <tb> CM3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> H <tb> <SEP> N-N <tb> AO)\H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> 3 <SEP> 3 <tb> <SEP> H <tb> N-N <tb> <SEP> CM3 <tb> <SEP> CM3 <SEP> <SEP> X <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> CH3 <tb> <SEP> N-N <tb> <SEP> CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> 3 <SEP> 3 <tb> <SEP> CM3 <tb> <SEP> NO <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> CM3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OcH3 <tb> <SEP> CM3 <SEP> 3 <SEP> M <SEP> 3 <SEP> 3 <tb> <SEP> CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> · <tb> <SEP> CM3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> Table 2 (continued) EMI47.1 <tb> R5 <SEP> Ra <SEP> Rb <SEP> R6 <SEP> X <SEP> Y <SEP> m.P.( C) <tb> O-N <tb> <SEP> CH, <SEP> CH, <SEP> H <SEP> OCH3 <SEP> OCH3 <tb> 4/ <SEP> 3 <SEP> 3 <SEP> H3 <SEP> OCH3 <tb> <SEP> N-N <tb> <SEP> AV <SEP> S <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> N=N <tb> <SEP> CM3 <SEP> 5 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> 3 <tb> <SEP> CM3 <SEP> CH3 <SEP> H <SEP> H3 <SEP> OCH3 <tb> CO2CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH2CH=CH2 <tb> COUCH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> SCH3 <tb> CO2CM3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> OCH2CCH <tb> COUCH, <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> CH2SCH3 <tb> CO2CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> SCF2H <tb> Table 3 EMI48.1 R7 Ra Rb X Y m.p.( C) H CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 SCH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 OSO2CH3 CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 H CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 SCH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 OSO2CH3 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 OCH3 C2H5 C2H5 CH3 CH3 CH3 C 2H5 CH3 CH3 CH3 F C2H5 C2H5 CH3 OCH3 Br C2H5 CH3 CH3 CH3 OCH3 C2H5 CH3 OCH3 OCH3 SMe C2H5 C2H5 CH3 OCH3 Cl C2H5 C2H5 CH3 CH3 Table 3 (continued) R7 Ra Rb X Y m.p.( C) OSO2CH3 C2H5 C2H5 CH3 CH3 SO2CH3 C2H5 C2H5 CH3 OCH3 H CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 F CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 OCH3 CH3 CH3 OCH3 OCH3 SCH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 OSO2CH3 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 Cl OCH3 Cl CH3 CH3 Cl OC2H5 Cl CH3 CH3 F OCH3 Cl CH3 CH3 Br OCH3 Cl CH3 CH3 OCF2H CH3 Cl CH3 CH3 CH2F OCH3 Cl CH3 CH3 CH3 CH2OCH3 Cl CH3 CH3 OCH3 CH2OCH3 Cl CH3 CH3 CH3 CH(OCH3)2 Cl CH3 CH3 OCH3 CH(OCH3)2 Cl CH3 CH3 CH3 CH(OCH2CH20) Cl CH3 CH3 OCH3 CH(OCH2CH20) Cl CH3 CH3 CF3 CH3 Cl CH3 CH3 CF3 OCH3 Cl CH3 CH3 OC2H5 CH3 Cl CH3 CH3 OC2H5 OCH3 Cl CH3 CH3 CH3 N(CH3)2 Cl CH3 CH3 OCH3 SCH3 Table 4 EMI50.1 R7 Ra Rb X Y m.p.( C) H CM3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 SCH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 OSO2CH3 CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 H CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 F CH3 CH3 CH3 OCH3 Br CH3 CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 SCH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 OSO2CH3 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 OCH3 C2H5 C2H5 CH3 CH3 CH3 C2H5 CH3 CH3 CH3 F C2H5 C2H5 CH3 OCH3 Br C2H5 CH3 CH3 CH3 OCH3 C2H5 CH3 OCH3 OCH3 SCH3 C2H5 C2H5 CH3 OCH3 Cl C2H5 C2H5 CH3 CH3 Table 4 (continued) R7 Ra Rb X Y m.p.( C) OSO2CH3 C2H5 C2H5 CH3 CH3 SO2CH3 C2H5 C2H5 CH3 OCH3 H CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 F CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 OCH3 CH3 CH3 OCH3 OCH3 SCH3 CH3 CH3 OCH3 OCH3. Cl CH3 CH3 OCH3 CH3 OSO2CH3 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 CH3 H Cl CH3 CH3 OCH3 H Cl CH3 CH3 CH3 C2H5 Cl CH3 CH3 OCH3 C2H5 Cl CH3 CH3 CH3 CH2OCH3 Cl CH3 CH3 OCH3 CH2OCH3 Cl CH3 CH3 CH3 CH(OCH3)2 Cl CH3 CH3 OCH3 CH(OCH3)2 Cl CH3 CH3 CH3 CH(OCH2CH2O) Cl CH3 CH3 OCH3 CH(OCH2CH2O) Cl CH3 CH3 CF3 CH3 Cl CH3 CH3 CF3 OCH3 Cl CH3 CH3 OC2H5 CH3 Cl CH3 CH3 OC2H5 OCH3 Cl CH3 CH3 CH3 OCH2CF3 Cl CH3 CH3 OCH3 OCH2CF3 Table 5 EMI52.1 R9 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 NO2 CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 CO2CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 Br CH3 CH3 CH3 OCH3 NO2 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 SO2N(CH3)2 CH3 CH3 CH3 OCH3 CO2CH3 CH3 CH3 CH3 OCH3 CO2CH3 C2H5 C2H5 OCH3 OCH3 CO2CH3 C2H5 CH3 CH3 CH3 Cl C2H5 CH3 OCH3 OCH3 Br C2H5 C2H5 OCH3 OCH3 NO2 C2H5 C2H5 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 SO2N(CH3)2 C2H5 C2H5 CH3 CH3 CO2CH3 C2H5 C2H5 CH3 CH3 Table 5 (continued) R9 Ra Rb X Y m.p.( C) F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 N02 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH3 C 2CH3 CH3 CH3 OCH3 OCH3 125-127 (d) CO2CH3 CH3 CH3 Cl OCH3 CO2CH3 CH3 CH3 F OCH3 CO2CH3 CH3 CH3 OCF2H CH3 CO2CH3 CH3 CH3 Br OCH3 CO2CH3 CH3 CH3 CH3 C2H5 CO2CH3 CH3 CH3 OCH3 C H CO2CH3 CH3 CH3 CH3 CH2OCH3 CO2CH3 CH3 CH3 OCH3 CH2OCH3 CO2CH3 CH3 CH3 CH3 CHtOCH3)2 CO2CH3 CH3 CH3 OCH3 CH(OCH3)2 CO2CH3 CH3 CH3 CH3 CH(OCH2CH2O) CO2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) CO2CH3 CH3 CH3 CF3 CH3 CO2CH3 CH3 CH3 CF3 OCH3 CO2CH3 CH3 CH3 OC2H5 CH3 CO2CH3 CH3 CH3 OC2H5 OCH3 CO2CH3 CH3 CH3 CH3 OCH2CF3 CO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 6 EMI54.1 R9 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 N02 CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 CO2CH3 CH3 CH3 CH3 CH3 110-115 (d) F CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 Br CH3 CH3 CH3 OCH3 NO2 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 SO2N(CH3)2 CH3 CH3 CH3 OCH3 CO2CH3 CH3 CH3 CH3 OCH3 98-100 C CO2CH3 C2H5 C2H5 OCH3 OCH3 CO2CH3 C2H5 CH3 CH3 CH3 Cl C2H5 CH3 OCH3 OCH3 Br C2H5 C2H5 OCH3 OCH3 NO2 C2H5 C2H5 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 S02N(CH3)2 C2H5 C2H5 CH3 CH3 CO2CH3 C2H5 C2H5 CH3 CH3 Table 6 (continued) R9 Ra Rb X Y m.p.( C) F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 NO2 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH CO2CH3 CH3 CH3 OCH3 OCH3 CO2CH3 CH3 CH3 CH2F CH3 CO2CH3 CH3 CH3 OCH2F OCH3 CO2CH3 CH3 CH3 CH3 C 2M5 CO2CH3 CH3 CH3 OCH3 C2H5 CO2CH3 CH3 CH3 CH3 CH2OCH3 CO2CH3 CH3 CH3 OCH3 CH2OCH3 CO2CH3 CH3 CH3 CH3 CH(OCH3)2 CO2CH3 CH3 CH3 OCH3 CH(OCH3)2 CO2CH3 CH3 CH3 CH3 CH(OCH2CH2O) C 2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) CO2CH3 CH3 CH3 CF3 CH3 CO2CH3 CH3 CH3 CF3 OCH3 CO2CH3 CH3 CH3 OC2H5 N(CH3)2 CO2CH3 CH3 CH3 OC2H5 SCH3 CO2CH3 CH3 CH3 CH3 OCH2CF3 CO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 7 EMI56.1 R9 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 NO2 CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 CO2CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 Br CH3 CH3 CH3 OCH3 N02 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 S02N(CH3)2 CH3 CH3 CH3 OCH3 CO2CH3 CH3 CH3 CH3 OCH3 CO2CH3 C2H5 C2H5 OCH3 OCH3 CO2CH3 C2H5 C2H5 CH3 CH3 Cl C2H5 C2H5 OCH3 OCH3 Br C2H5 C2H5 OCH3 OCH3 NO2 C2H5 C2H5 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 SO2N(CH3)2 C2H5 C2H5 CH3 CH3 SO2CH3 C2H5 C2H5 CH3 CH3 Table 7 (continued) R9 Ra Rb X Y m.p.( C) F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 N02 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH3 CO2CH3 CH3 CH3 OCH3 OCH3 CO2CH3 CH3 CH3 Cl OCH3 CO2CH3 CH3 CH3 Cl OC2H5 CO2CH3 CH3 CH3 Br OCH3 CO2CH3 CH3 CH3 F OCH3 CO2CH3 CH3 CH3 CH3 C2H5 CO2CH3 CH3 CH3 OCH3 C2H5 CO2CH3 CH3 CH3 CH3 CH2OCH3 CO2CH3 CH3 CH3 OCH3 CH2OCH3 CO2CH3 CH3 CH3 CH3 CH(OCH3)2 C 2CH3 CH3 CH3 OCH3 CH(OCH3)2 C 2CH3 CH3 CH3 CH3 CH(OCH2CH2O) CO2CH3 CH CH3 OCH3 CH(OCH2CH2O) CO2CH3 CH3 CH3 CF3 CH3 CO2CH3 CH3 CH3 CF3 OCH3 CO2CH3 CH3 CH3 OC2H5 N(CH3)2 CO2CH3 CH3 CH3 OC2H5 CH2SCH3 CO2CH3 CH3 CH3 CH3 OCH2CF3 CO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 8 EMI58.1 R9 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 CH3 NO2 CH3 CH3 CH3 CH3 SO 2 CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 CO2CH3 CH3 CH3 CH3 CH3 F CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 Br CH3 CH3 CH3 OCH3 N02 CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 SO2N(CH3)2 CH3 CH3 CH3 OCH3 CO2CH3 CH3 CH3 CH3 OCH3 CO2CH3 C2H5 C2G5 OCH3 OCH3 CO2CH3 C2H5 CH3 CH3 CH3 Cl C2H5 CH3 OCH3 OCH3 Br C2H5 C2H5 OCH3 OCH3 NO2 C2H5 C2H5 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 SO2N(CH3)2 C2H5 C2H5 CH3 CH3 CO2CH2 C2H5 C2H5 CH3 CH3 Table 8 (continued) R9 Ra Rb X Y m.p.( C) F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 Br CH3 CH3 OCH3 OCH3 N02 CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH3 CO2CH3 CH3 CH3 OCH3 OCH3 CO2CH3 CH3 CH3 CH2F CH3 CO2CH3 CH3 CH3 OCF2H OCH3 CO2CH3 CH3 CH3 CH3 C2H5 CO2CH3 CH3 CH3 OCH3 C H CO2CH3 CH3 CH3 CH3 CH2OCH3 CO2CH3 CH3 CH3 OCH3 CH20CH3 CO2CH3 CH3 CH3 CH3 CH(OCH3)2 CO2CH3 CH3 CH3 OCH3 CH(OCH3)2 CO2CH3 CH3 CH3 CH3 CH(OCH2CH2O) C 2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) CO2CH3 CH3 CH3 CF3 CH3 CO2CH3 CH3 CH3 CF3 OCH3 CO2CH3 CH3 CH3 OC2H5 CH3 CO2CH3 CH3 CH3 OC2H5 OCH3 CO2CH3 CH3 CH3 CH3 OCH2CF3 CO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 9 EMI60.1 R8 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 SO2N(CH3)2 CH3 CH3 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 CH3 C2H5 CH3 CH3 CH3 OCH3 C2H5 CH3 OCH3 OCH3 Cl C2H5 C2H5 OCH3 OCH3 SO2CH3 C2H5 CH3 CH3 CH3 SO2N(CH3)2 C2H5 C2H5 CH3 CH3 F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 OCH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH3 Table 9 (continued) R8 Ra Rb X Y m.p.( C) SO2CH3 CH3 CH3 Cl OCH3 SO2CH3 CH3 CH3 Cl OC2H5 SO2CH3 CH3 CH3 F OCH3 SO2CH3 CH3 CH3 Br OCH3 SO2CH3 CH3 CH3 CH3 C2H5 SO2CH3 CH3 CH3 OCH3 C2H5 SO2CH3 CH3 CH3 CH3 CH2OCH3 SO2CH3 CH3 CH3 OCH3 CH2OCH3 SO2CH3 CH3 CH3 CH3 CH(OCH3)2 SO2CH3 CH3 CH3 OCH3 CH(OCH3)2 SO2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) SO2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) SO2CH3 CH3 CH3 CF3 CH3 SO2CH3 CH3 CH3 CF2 OCH3 SO2CH3 CH3 CH3 OC2H5 CH3 SO2CH3 CH3 CH3 OC2H5 OCH3 SO2CH3 CH3 CH3 CH3 OCH2CF3 SO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 10 EMI62.1 R8 Ra Rb X Y m.p.( C) F CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 Cl CH3 CH3 CH3 CH3 SO2CH3 CH3 CH3 CH3 CH3 SO2N(CH3)2 CH3 CH3 CH3 CH3 Br CH3 CH3 CH3 OCH3 CH3 CH3 CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 Cl CH3 CH3 CH3 OCH3 SO2CH3 CH3 CH3 CH3 OCH3 SO2N(CH3)2 CH3 CH3 CH3 OCH3 SO2CH3 C2H5 C2H5 CH3 CH3 CH3 C2H5 CH3 CH3 CH3 OCH3 C2H5 CH3 OCH3 OCH3 Cl C2H5 C2H5 OCH3 OCH3 SO2CH3 C2H5 CH3 CH3 CH3 SO2N(CH3)2 C2H5 C2H5 CH3 CH3 F CH3 CH3 OCH3 OCH3 CH3 CH3 CH3 OCH3 OCH3 OCH3 CH3 CH3 OCH3 OCH3 Cl CH3 CH3 OCH3 OCH3 SO2CH3 CH3 CH3 OCH3 OCH3 SO2N(CH3)2 CH3 CH3 OCH3 OCH3 Table 10 (continued) R8 Ra Rb X Y m.p.( C) SO2CH3 CH3 CH3 OCF2H CH3 SO2CH3 CH3 CH3 OCH2F OCH SO2CH3 CH3 CH3 CH3 C2H5 SO2CH3 CH3 CH3 OCH3 C2H5 SO2CH3 CH3 CH3 CH3 CH2OCH3 S02CH3 CH3 CH3 OCH3 CH20CH3 SO2CH3 CH3 CH3 CH3 CH(OCH3)2 SO2CH3 CH3 CH3 OCH3 CH(OCH3)2 SO2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) SO2CH3 CH3 CH3 OCH3 CH(OCH2CH2O) SO2CH3 CH3 CH3 CF3 CH3 SO2CH3 CH3 CH3 CF3 OCH3 SO2CH3 CH3 CH3 OC2H5 CH3 SO2CH3 CH3 CH3 OC2H5 OCH3 SO2CH3 CH3 CH3 CH3 OCH2CF3 SO2CH3 CH3 CH3 OCH3 OCH2CF3 Table 11 EMI64.1 L Ra Rb X Y m.p.( C) L-6: R9=CO2CH3 CH3 CH3 CH3 CH3 L-6: R9=SO2N(CH3)2 CH3 CH3 CH3 CH3 L-6: R9=SO2CH3 CH3 CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 CH3 CH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 CH3 CH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 CH3 OCH3 L-6: R9=SO2N(CH3)2 CH3 CH3 CH3 OCH3 L-6: R9=SO2CH3 CH3 CH3 CH3 OCH3 L-7: R10=CO2CH3 CH3 CH3 CH3 OCH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 CH3 OCH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 CH3 OCH3 L-6: R9=CO2CH3 C2H5 C2H5 CH3 CH3 L-6: R9=SO2N(CH3)2 C2H5 CH3 CH3 CH3 L-6: R9=SO2CH3 C2H5 CH3 OCH3 OCH3 L-6: R9=CO2CH3 C2H5 C2H5 OCH3 OCH3 L-16: R17=H C2H5 CH3 CH3 CH3 L-17: R17=CH3; R18=H C2H5 C2H5 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 OCH3 OCH3 L-6: R9=SO2N(CH3)2 CH3 CH3 OCH3 OCH3 L-6: R9=SO2CH3 CH3 CH3 OCH3 OCH3 L-7: R10=CO2CH3 CH3 CH3 OCH3 OCH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 OCH3 OCH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 OCH3 OCH3 L-8: Q1=O; R11=R12=CH3; R13=H; m=0 CH3 CH3 OCH3 OCH3 Table 11 (continued) L Ra Rb X Y m.p.( C) L-8: Q1=S; R11=H; R12=CH3; R13=H, m=0 CH3 C2H5 CH3 OCH3 L-8: Q1=SO2; R11=CH3; R12=H; R13=H; m=0 CH3 CH3 OCH3 OCH3 L-8: Q1=SO2; R11=R12=CH3; R13=H; m=1 CH3 CH3 CH3 CH3 L-8: Q1=SO2; R11=H; R12=CH3, R13=H; m=0 CH3 CH3 OCH3 OCH3 L-12: m=O; R13=H CH3 CH3 CH3 CH3 L-13: m=l; R13=H CH3 CH3 CH3 CH3 L-14: R16=CH3 CH3 CH3 CH3 CH3 L-15: R17=H CH3 CH3 CH3 CH3 L-16: R17=H CH3 CH3 CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 CH3 CH3 L-12: m=O; R13=H CH3 CH3 CH3 OCH3 L-13: m=1; R13=H CH3 CH3 CH3 OCH3 L-14: R16=CH3 CH3 CH3 CH3 OCH3 L-15: R17=H CH3 CH3 CH3 OCH3 L-16: R17=H CH3 CH3 CH3 OCH3 L-17: R17=CH3; R18=H CH3 CH3 CH3 OCH3 L-7: R10=CO2CH3 CH3 C2H5 CH3 CH3 L-9: Q2=O; R14=CH3; R15=H C2H5 CH3 CH3 CH3 L-12: m=O; R13=H C2H5 CH3 OCH3 OCH3 L-13: m=1: R13=B C2H5 C2H5 OCH3 OCH3 L-14: R16=CH3 C2H5 CH3 CH3 CH3 L-15: R17=H C2H5 C2H5 CH3 CH3 L-12: m=0; R13=H CH3 CH3 OCH3 OCH3 L-13: m=1; R13=H CH3 CH3 OCH3 OCH3 L-14: R16=CH3 CH3 CH3 OCH3 OCH3 L-15: R17=H CH3 CH3 OCH3 OCH3 L-16: R17=H CH3 CH3 OCH3 OCH3 L-17: R17=CH3; R18=CH3 CH3 CH3 OCH3 OCH3 L-10: R13=H; R16=CH3; m=0 CH3 CH3 OCH3 OCH3 L-10: R13=H; R16=C2H5; m=0 CH3 C2H5 CH3 OCH3 L-10: R13=CH3; R16=CH3; m=0 C2H5 C2H5 CH3 CH3 Table 11 (continued) L Ra Rb X Y m.p.( C) L-11: R13=H; m=0 CH3 CH3 OCH3 OCH3 L-11: R13=H; m=1 CH3 CH3 Cl OCH3 L-11: R13=CH3; m=0 C2H5 CH3 CH3 CH(OCH3)2 Table 12 EMI67.1 L Ra Rb X Y m.p.( C) L-6: Rg=CO2CH3 CH3 CH3 CH3 CH3 L-6: R9=SO2N(CH3)2 CH3 CH3 CH3 CH3 L-6; R9=SO2CH3 CH3 CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 CH3 CH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 CH3 CH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 CH3 OCH3 L-6: R9=SO2N(CH3)2 CH3 CH3 CH3 OCH3 L-6: R9=SO2CH3 CH3 CH3 CH3 OCH3 L-7: R10=CO2CH3 CH3 CH3 CH3 OCH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 CH3 OCH3 L-9: W2=S; R14=CH3; R15=H CH3 CH3 CH3 OCH3 L-6: R9=CO2CH3 C2H5 C2H5 CH3 CH3 L-6: R9=SO2N(CH3)2 C2H5 CH3 CH3 CH3 L-6: R9=SO2CH3 C2H5 CH3 OCH3 OCH3 L-6: R9=CO2CH3 C2H5 C2H5 OCH3 OCH3 L-16: R17=H C2H5 CH3 CH3 CH3 L-17: R17=CH3; R18=H C2H5 C2H5 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 OCH3 OCH3 L-6: R9=SO2N(CH3)2 CH3 CH3 OCH3 OCH3 L-6: R9=SO2CH3 CH3 CH3 OCH3 OCH3 L-7: R10=CO2CH3 CH3 CH3 OCH3 OCH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 OCH3 OCH3 L-9: Q2=S; R14=CH3; R15=H CH3 CH3 OCH3 OCH3 L-8: Q1=O; R11=R12=CH3; R13=H; m=0 CH3 CH3 OCH3 OCH3 Table 12 (continued) L Ra Rb X Y m.p.( C) L-8: Q1=S; R11=H; R12=CH3; R13=H, m=O CH3 C2H5 CH3 OCH3 L-8: Q1=SO2; R11=CH3: R12=H; R13=H; m=0 CH3 CH3 OCH3 OCH3 L-8: Q1=SO2; R11=R12=CH3; R13=H; m=1 CH3 CH3 CH3 CH3 L-8: Q1=SO2; R11=H; R12=CH3, R13=H; m=O CH3 CH3 OCHF2 OCH3 L-12: m=O; R13=H CH3 CH3 CH3 CH3 L-13: m=1; R13=H CH3 CH3 CH3 CH3 L-14: R16=CH3 CH3 CH3 CH3 CH3 L-15: R17=H CH3 CH3 CH3 CH3 L-16: R17=H CH3 CH3 CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 CH3 CH3 L-12: m=O; R13=H CH3 CH3 CH3 OCH3 L-13: m=1; R13=H CH3 CH3 CH3 OCH3 L-14: R16=CH3 CH3 CH3 CH3 OCH3 L-15: R17=H CH3 CH3 CH3 OCH3 L-16: R17=H CH3 CH3 CH3 OCH3 L-17: R17CH3; R18=H CH3 CH3 CH3 OCH3 L-7: R10=CO2CH3 C2H5 C2H5 CH3 CH3 L-9: Q2=0; R14=CH3; R15=H C2H5 CH3 CH3 CH3 L-12: m=0; R13=H C2H5 CH3 OCH3 OCH3 L-13: m=1; R13=H C2H5 C2H5 OCH3 OCH3 L-14: R16=CH3 C2H5 C2H5 OCH3 OCH3 L-15: R17=H C2H5 CH3 CH3 CH3 L-12: m=0; R13=H CH3 CH3 OCH3 OCH3 L-13: m=l; R13=H CH3 CH3 OCH3 OCH3 L-14: R16=CH3 CH3 CH3 OCH3 OCH3 L-15: R17=H CH3 CH3 OCH3 OCH3 L-16: R17=H CH3 CH3 OCH3 OCH3 L-17: R17=CH3; R18=CH3 CH3 CH3 OCH3 OCH3 L-10: R13=H; R16=CH3; m=O CH3 CH3 OCH3 OCH3 L-10: R13=H; R16=C2H5; m=0 CH3 C2H5 CH3 OCH3 L-10: R13=CH3; R16=CH3; m=0 C2H5 C2H5 CH3 CH3 Table 12 (continued) L Ra Rb X Y m.p.( C) L-ll: R13=H; m=O CH3 CH3 OCH3 OCHF2 L-ll: R13=H; m=l CH3 CH3 CF3 OCH3 L-11: R13=CH3; m=0 C2H5 CH3 CH3 CH(OCH3)2 Table 13 EMI70.1 L Ra Rb L-1: R5=CO2CH3; R6=H C2H5 C2H5 L-1: R5=CO2CH3; R6=H CH3 C2H5 L-1: R5=CO2CH3; R6=H CH3 CH3 L-l: R5=CO2CH3: R6=5-OCH3 CH3 CH3 L-1: R5=SO2N(CH3)2: R6=H CH3 CH3 L-1: R5=SO2CH3; R6=H CH3 CH3 L-1: R5=Cl; R6=H CH3 CH3 L-1: R5=SO2CH2CH2CH3; R6=H CH3 CH3 L-2: R7=SO2CH3 CH3 CH3 L-3: R8=SO2N(CH3)2 CH3 CH3 L-4: R9=CO2CH3 CH3 CH3 L-5: Rg=CO2CH3 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 L-8: Q1=0; m=0; R11=CH3; R12=CH3; R13=H CH3 CH3 L-9: Q2= ; R14=CH3; R15=M CH3 CH3 L-10: m=0; R16=CH3; R13=H CH3 CH3 L-11: m=l; R13=H CH3 CH3 L-11: m=0; R13=H CH3 CH3 L-12: m=0; R13=H CH3 CH3 L-13: m=l; R13=H CH3 CH3 L-14: R16=CH3 CH3 CH3 L-15: R17=H CH3 CH3 L-16: R17=H CH3 CH3 L-17: R17=CH3: R18=H CH3 CH3 Table 14 EMI71.1 L Ra Rb L-1: R5=CO2CH3; R6=H C2H5 C2H5 L-l: R =C02CH3; R6=H CH3 C2H5 L-l: R5=CO2CM3; R6=H CH3 CH3 L-l: R5=CO2CH3; R6=5-OCH3 CH3 CH3 L-1: R5=SO2N(CH3)2; R6=H CH3 CH3 L-1: R5=S02CH3; R6=H CH3 CH3 L-l: R5=C1; R6=H CH3 CH3 L-1: R5=SO2CH2CH2CH3; R6=H CH3 CH3 L-2: R7=S02CH3 CH3 CH3 L-3: Ra=SO2N(CH3)2 CH3 CH3 L-4: Rg=CO2CH3 CH3 CH3 L-5: R9=CO2CH3 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 L-8: Q1=O; m=0; R11=CH3; R12=CH3; R13=H CH3 CH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 L-10: m=0; R16=CH3; R13=H CH3 CH3 L-11: m=1; R13=H CH3 CH3 L-11: m=0; R13=H CH3 CH3 L-12: m=0; R13=H CH3 CH3 L-13: m=l; R13=H CH3 CH3 L-14: R16=CH3 CH3 CH3 L-15: R17=H CH3 CH3 L-16: R17=H CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 Table 15 EMI72.1 L Ra Rb L-1: R5=CO2CH3; R6=H C2H5 C2H5 L-1: R5=CO2CH3; R6=H CH3 C2H5 L-1: R5=CO2CH3; R6=H CH3 CH3 L-1: R5=CO2CH3; R6=5-OCH3 CH3 CH3 L-1: R5=SO2N(CH3)2; R6=H CH3 CH3 L-1: R5=SO2CH3; R6=H CH3 CH3 L-1: R5=Cl; R6=H CH3 CH3 L-1: R5=SO2CH2CH2CH3; R6=H CH3 CH3 L-2: R7=SO2CH3 CH3 CH3 L-3: R8=SO2N(CH3)2 CH3 CH3 L-4: R9=C02CH3 CH3 CH3 L-5: Rg=CO2CH3 CH3 CH3 L-6: R9=CO2CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 L-8: Q1=0; m=O; R11=CH3; R12=CH3; R13=H CH3 CH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 L-10: m=O; R16=CH3; R13=H CH3 CH3 L-11: m=1: R13=H CH3 CH3 L-11: m=0: R13=H CH3 CH3 L-12: m=O; R13=H CH3 CH3 L-13: m=l; R13=H CH3 CH3 L-14: R16=CH3 CH3 CH3 L-15: R17=H CH3 CH3 L-16: R17=H CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 Table 16 EMI73.1 L Ra b L-1: R5=CO2CH3; R6=H C2H5 C2H5 L-1: R5=CO2CH3; R6=H CH3 C2H5 L-1: R5=CO2CH3; R6=H CH3 CH3 L-1: R5=CO2CH3: R6=5-OCH3 CH3 CH3 L-1: R5=SO2N(CH3)2: R6=H CH3 CH3 L-1: R5=SO2CH3; R6=H CH3 CH3 L-1: R5=Cl; R6=H CH3 CH3 L-1: R5=SO2CH2CH2CH3; R6=H CH3 CH3 L-2: R7=SO2CH3 CH3 CH3 L-3: R8=SO2N(CH3)2 CH3 CH3 L-4: R9=CO2CH3 CH3 CH3 L-5: R9=CO2CH3 CH3 CH3 L-6: Rg=CO2CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 L-8: Q1=O; m=0; R11=CH3; R12=CH3; R13=H CH3 CH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 L-10: m=0; R16=CH3; R13=H CH3 CH3 L-11: m=1; R13=H CH3 CH3 L-ll: m=O; R13=H CH3 CH3 L-12: m=0; R13=H CH3 CH3 L-13: m=l; R13=H CH3 CH3 L-14: R16=CH3 CH3 CH3 L-15: R17=H CH3 CH3 L-16: R17=H CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 Table 17 EMI74.1 L Ra Rb L-1: R5=CO2CH3; R6=H C2H5 C2H5 L-1: R5=CO2CH3; R6=H CH3 C2H5 L-1: R5=CO2CH3; R6=H CH3 CH3 L-1: R5=CO2CH3; R6=5-OCH3 CH3 CH3 L-1: R5=SO2N(CH3)2; R6=H CH3 CH3 L-1: R5=SO2CH3; R6=H CH3 CH3 L-1: R5=Cl; R6=H CH3 CH3 L-l: R5=SO2CH2CH2CH3; R6=H CH3 CH3 L-2: R7=S02CH3 CH3 CH3 L-3: R8=SO2N(CH3)2 CH3 CH3 L-4: Rg=C02CH3 CH3 CH3 L-5: R9=CO2CH3 CH3 CH3 L-6: Rg=CO2CH3 CH3 CH3 L-7: R10=CO2CH3 CH3 CH3 L-8: Q1=O; m=0; R11=CH3; R12=CH3; R13=H CH3 CH3 L-9: Q2=O; R14=CH3; R15=H CH3 CH3 L-10: m=0; R16=CH3; R13=H CH3 CH3 L-11: m=1; R13=H CH3 CH3 L-11: m=0; R13=H CH3 CH3 L-12: m=0; R13=H CH3 CH3 L-13: m=1; R13=H CH3 CH3 L-14: R16=CH3 CH3 CH3 L-15: R17=H CH3 CH3 L-16: R17=H CH3 CH3 L-17: R17=CH3; R18=H CH3 CH3 Table 18 EMI75.1 R5 R6 Rd R X Y m.p.( C) SCH2CH=CH2 3-Cl CH3 H OCH3 OCH3 SCH2CH=CH2 H C2H5 H OCH3 OC2H5 OSO2-n-C3H7 H CH3 CH3 CH3 CH2OCH3 OSO2-n-C3H7 H CH3 H CH3 SCH3 OSO2CH3 H CH3 H OCH3 CH3 OSO2CH3 H CH3 H OCH3 OCH3 CH2CH3 5-Br CH3 H CH3 OCH3 CH2CH3 H CH3 H CH3 CH3 n-C4H9 H n-C3H7 H OCH3 OCH3 i-C3H7 H CH3 CH3 OCH3 CH3 OS02N(CH3)2 H CH3 H CH3 CH(OCH2CH20) OCH2CH3 H CH3 H CH3 CH3 OCH2CH3 H CH3 H CH3 OCH3 O-i-C3H7 H CH3 H OCH3 OCH3 O-i-C3H7 H CH3 H OCH3 C2H5 O-n-C4Hg H CH3 H CH3 CH(OCH3)2 O-n-C4H9 H CH3 H CH3 OC2H5 SO2CF2H 5-CH3 CH3 H OCH3 OCH3 SO2CF2H H C2H5 H OCH3 OC2H5 SCF2H 6-SCH3 CH3 CH3 CH3 CH2OCH3 SCF2H H CH3 H CH3 SCH3 OCF3 H CH3 H OCH3 CH3 OCF3 H CH3 H OCH3 OCH3 CH2OCH3 H n-C3H7 H OCH3 OCH3 Table 18 (continued) R5 R6 Rd R X Y m.p.( C) CH2OCH3 H CH3 CH3 OCH3 CH3 CH2OCH2CH3 H CH3 H Cl OCH3 CH2OCH2CH3 H CH3 H Cl CH3 OCF2H H CH3 H OCH3 CH3 OCF2H H CH3 H OCH3 OCH3 OCF2H H CH3 H CH3 CH(OCH2CH2O) Table 19 EMI77.1 R5 R6 Rd R X Y m.p.( C) SO2CH2CH=CH2 H CH3 H OCH3 OCH3 SO2CH2CH=CH2 H CH3 H OCH3 C2H5 OSO2-n-C3H7 H CH3 CH3 CH3 CH20CH3 OSO2-n-C3H7 H CH3 H CH3 SCH3 OSO2CH3 H CH3 H OCH3 CH3 OSO2CH3 H CH3 H OCH3 OCH3 CH2CH3 3-Br CH3 H CH3 OCH3 CH2CH3 H CH3 H CH3 CH3 n-C4Hg H n-C3H7 H H3 OCH3 i-C3H7 H CH3 CH3 OCH3 CH3 OS02N(CH3)2 H CH3 H CH3 CH(OCH2CH20) OCH2CH3 H CH3 H CH3 CH3 OCH2CH3 H CH3 H CH3 OCH3 3H7 H CH3 H OCH3 OCH3 O-i-C3H7 H CH3 H OCH3 C2H5 H9 H CH3 H CH3 CH(OCH3)2 O-n-C4Hg H CH3 H CH3 OC2H5 SO2CF2H 6-SCH3 CH3 H OCH3 OCH3 SO2CF2H H C2H5 H OCH3 OC2H5 SCF2H H CH3 CH3 CH3 CH2OCH3 SCF2H H CH3 H CH3 SCH3 OCF3 H CH3 H OCH3 CH3 OCF3 H CH3 H OCH3 H3 CH2OCH3 H n-C3H7 H OCH3 OCH3 Table 19 (continued) R5 R6 Rd R X Y m.p.( C) CH2OCH3 H CH3 CH3 OCH3 CH3 CH2OCH2CH3 H CH3 H Cl OCH3 CH2OCH2CH3 H CH3 H Cl CH3 OCF2H H CH3 H OCH3 CH3 OCF2H H CH3 H OCH3 OCH3 OCF2H H CH3 H CH3 CH3 CH2CH2OC2H5 H CH3 H OCH3 CH3 Table 20 EMI79.1 EMI79.2 <tb> Rd <SEP> R <SEP> R5 <SEP> R6 <SEP> E <SEP> Y <SEP> z <SEP> (4c) <tb> CH3 <SEP> H <SEP> OCH2CH2OCH3 <SEP> H <SEP> CH3 <SEP> H <SEP> CH <tb> CH3 <SEP> H <SEP> OCH2CH=CH2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> CH3 <SEP> H <SEP> OCH2CH-CH <SEP> 6-OCH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> C6R5 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> CH3 <SEP> H <SEP> N-N <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> <SEP> 0H <tb> CH3 <SEP> H <SEP> N-N <SEP> R <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> <SEP> Il <tb> CH3 <SEP> H <SEP> e <SEP> H <SEP> OCH3 <SEP> OCH2C-CH <SEP> N <tb> <SEP> S <tb> CH3 <SEP> H <SEP> e <SEP> OCR3 <SEP> OCR2CR2OCR3 <SEP> N <tb> <SEP> 22, <tb> CH3 <SEP> H <SEP> C <SEP> H <SEP> H <SEP> OCH3 <SEP> OCF2K <SEP> CH <tb> CH3 <SEP> H <SEP> OCF3 <SEP> H <SEP> OCR3 <SEP> SCF2R <SEP> CH <tb> CH3 <SEP> H <SEP> 3 <SEP> 3-OCF2H <SEP> OCH3 <SEP> C(CH3)(OCH3)2 <SEP> CH <tb> CH3 <SEP> H <SEP> OCH2CH3 <SEP> H <SEP> OCR3 <SEP> CF3 <SEP> N <tb> CH3 <SEP> H <SEP> SO2CH2CH3 <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <SEP> CH <tb> CH3 <SEP> CH3 <SEP> S02CH2CH3 <SEP> H <SEP> OCR3 <SEP> C(CR3 <SEP> )(SCR3)2 <SEP> N <tb> CH3 <SEP> H <SEP> SO2CH2CH3 <SEP> H <SEP> OCF2H <SEP> CH(SCH2CH2S) <SEP> CR <tb> CH3 <SEP> H <SEP> SO2CH2CH3 <SEP> H <SEP> CF3 <SEP> CH2CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> SO2CH2CH3 <SEP> H <SEP> F <SEP> OCH3 <SEP> CH <tb> CH3 <SEP> H <SEP> SO2CH2CH3 <SEP> H <SEP> OC2H5 <SEP> C(CH3 <SEP> )(OCR2CR2O) <SEP> CH <tb> Table 21 EMI80.1 Rd R L X Y Z m.p.( C) CH3 H L2: :R7=Cl CH3 H CH CH3 H L2:R7=OCH3 CH3 CH3 CH CH3 H L2:R7=OCH3 CH3 CH3 CH CH3 H L2:R7=SO2N(CH3)2 CH3 CH3 CH CH3 H L3:R8=SO2N(CH3)2 CH3 CH3 CH CH3 H L3:R8=SO2CH3 CH3 OCH3 CH CH3 CH3 L3:R8=SO2CH2CH3 Cl OCH3 CH i-C3H7 H L4:R9=Br OCH3 OCH3 CH CH3 H L5:R9=C2H5 OCH3 OCH3CH=CH2 CH CH3 H L6:R9=Cl OCH3 OCH3C#CH N CH3 H L7:R10=CO2CH3 OCH3 OCH2CH3 N CH3 H L8:Q1=O, m=0, R11=R12=R13=CH3 OCH3 CH2SCH3 CH CH3 H L9:Q2=S, R14=R15=H OCH3 OCF2H CH CH3 H L10:m=0, R13=H, R16=CH3 OCH3 SCF2N CH CH3 H L11:m=0, R13=H OCH3 C(CH3) (OCH3)2 CH CH3 H L12:m=1, R13=CH3 OCH3 CH3 CH CH3 H L13:m=0, R13=H OCH3 N(CH3)2 CH CH3 CH3 L14:R16=CH2CH3 OCH3 C(CH3)(SCH3)2 CH CH3 H L15:R17=CH3 OCF2H CH(SCH2CH2S) CH CH3 H L16:R17=H CF3 CH2CH3 CH CH3 H L17:R17=R18=CH3 F OCH3 CH CH3 H L17:R17=R18=CH3 OC2H5 C(CH3)(OCH2CH2O) CH Table 22 EMI81.1 L Rd R A m.p.( C) L1:R5=CO2CH3, R6=H CH3 H A4:X1=CH3, Y2=H L1: :R5=SO2CH3, R6=H CH3 H A5:X2=CH2CH3, Y3=SCH3 L1:R5=NO2, R6=H CH3 H A6:X3=OCH3 L1:R5=Br, R6=H CH3 H A3:X1=OCH3 L1:R5=Cl, R6=H CH3 H A5:X2=CH3, Y3=OC2H5 L1:R5=C2H5, R6=H CH3 H A2:X1=OCH3, Y1=O L1:R5=SCF3, R6=H C2H5 H A3:X1=OCF2H L17:R17=H, R18=CH3 CH3 H A2:X1=OCH3, Y1=CH2 L16:R17=CH3 CH3 H A3:X1=OCF2H L2:R7=SCH3 CH3 H A4:X1=CH3, Y2=CH3 L3:R8=F CH3 H A5:X2=CH2CH3, Y3=OCH3 L4:R9=i-C3H7 CH3 H A5:X2=CH3, Y3=CH2CH3 L5:R9=SO2CH3 CH3 H A6:X3=OCH3 L6:R9=SO2CH3 CH3 H A2:X1=OCH3, Y1=O L7:R10=OCH2CH3 CH3 H A3:X1=CH3 L8:Q1=S, R11=R12=CH3, m-1, R13=H CH3 H A6:X3=CH3 L9:Q2=O, R14=R15=CH3 CH3 H A4:X1=OCH3, Y2=CH3 L10:R16=C2H5, R13=CH3, m=0 CH3 H A5:X2=CH3, Y9=SCH3 L11:m=1, R13=H CH3 H A2:X1=CH3, Y1=CH2 L12:m=0, R13=CH3 CH3 H A2:X1=OCH3, Y1=CH2 L13:m=1, R13=H CH3 H A5:X2=CH2CF3, Y3=CH2CH3 L14:R16=CH3 CH3 H A4:X1=OCH3, Y2=H L15:R17=CH3 CH3 H A4: :X1=OCH3, Y2=H Table 23 EMI82.1 R5 R6 R Rc X Y m.p.( C) Cl H H H CH3 CH3 165-167 Cl H H H CH3 OCH3 121-128 Cl H H H OCH3 OC2H5 Cl H H H OCH3 OCH3 142-144 F H H H CH3 CH3 F H H H CH3 OCH3 Br H H H OCH3 CH3 Br H H H OCH3 OCH3 NO2 H H H CH3 CH(OCH2CH2O) NO2 H CH3 H CH3 C2H5 CF3 H H H OCH3 OC2H5 CF3 H H H OCH3 CH3 OCH3 H H H CH3 OCH3 OCH3 H H H CH3 CH(OCH3)2 OCH3 H H H Cl CH3 OCH3 H H H Cl OCH3 OC2H5 H H H CH3 CH2OCH3 OC2H5 H H H CH3 CH3 OC2H5 H CH3 H OCH3 OCH3 3H7 H H H OCH3 CH3 3H7 H H H CH3 OCH3 O-n-C3H7 H H H CH3 CH3 O-i-C4H9 H H H OCH3 OCH3 O-iC4H9 H H H OCH3 CH3 CO2CH3 H H H CH3 CH3 M+=379* CO2CH3 H H H CH3 OCH3 M+ = 395* Table 23 (continued) R5 R6 R Rc X Y m.p.( C) CO2CH3 H H H OCH3 OC2H SO2N(CH3)2 H H H OCH3 OCH3 S02N(CH3)2 H H H CH3 CH3 S02N(CH3)z H H H CH3 OCH3 166-1680 SO2N(CH3)2 H H H OCH3 OCH2CH3 S02N(CH3)2 H H H CH3 <RTI ID=83.2> CH(OCH2CH20) S02N(CH2CH3)2 H CH3 H CH3 C2H5 SO2N(CH2CH3)2 H H H OCH3 OC2H5 SO2N(CH2CH3)2 H H H OCH3 CH3 CO2CH2CH3 H H H CH3 OCH3 CO2CH2CH3 H H H CH3 CH(OCH3)2 CO2CH3 H H H Cl CH3 CO2CH3 H H H Cl OCH3 CO2CH3 H H H CH3 CH20CH3 CO2-i-C3H7 H H H CH3 CH3 CO2-i-C3H7 H CH3 H OCH3 OCH3 SO2N(OCH3)CH3 H H H OCH3 CH3 CO2CH2CH2OCH3 H H H CH3 OCH3 CO2CH2CH=CH2 H H H CH3 CH3 CO2CH2CH2Cl H H H OCH3 OCH3 CO2-n-C4H9 H H H OCH3 CH3 SO2CH3 H H H CH3 CH3 SO2CH3 H H H CH3 OCH3 SO2CH3 H H H OCH3 OC2H5 SO2CH3 H H H OCH3 OCH3 SO2CH2CH=CH2 H H H CH3 CH3 SO2CH2CH=CH2 H H H CH3 OCH3 SO2CH2CH2CH3 H H H OCH3 CH3 SCH2CH3 H H H OCH3 OCH3 SCF3 H H H CH3 CH(OCH2CH2O) SO2CHF2 H CH3 H CH3 C2H5 CH3 H H H OCH3 OC2H5 Table 23 (continued) R5 R6 R Rd X Y m.p.( C) i-C3H7 H H H OCH3 CH3 n-C4H9 H H H CH3 OCH3 OSO2N(CH3)2 H H H CH3 CH(OCH3)2 OSO2N(CH3)2 H H H Cl CH3 OSO2CH(CH3)2 H H H Cl OCH3 OS02C2H5 H H H CH3 CH20CH3 OSO2CH3 H CH3 H OCH3 OCH3 OSO2CH3 H H H OCH3 CH3 CH2OCH3 H H H CH3 OCH3 CH2CH2OCH3 H H H CH3 CH3 COF3 H H H OCH3 OCH3 SO2-i-C3H7 H H H OCH3 CH3 Cl H H CH3CO CH3 CH3 131-136 D Cl 5-CF3 H H CH3 OCH3 Cl H H CH3OCO OCH3 OC2H Cl 6-SCH3 H H OCH3 OCH3 F 5-SCH3 H CH3CO CH3 CH3 F 6-OCH3 H H CH3 OCH3 Br H H (CH3)2NCO OCH3 CH3 Br 3-OCH3 H H OCH3 OCH3 N02 H H CH3NHCO CH3 CH(OCH2CH2O) NO2 6-CH3 CH3 H CH3 C2H5 CF3 5-CH3 H CF3CO OCH3 OC2H5 CF3 6-Cl H C2H5CO OCH3 CH3 OCH3 H H C2H5OCO CH3 OCH3 OCH3 5-Cl H H CH3 CH(OCH3)2 OCH3 3-Cl H H Cl CH3 OCR3 H H CH3CO Cl OCH3 OC2H5 5-F H H CH3 CH2OCH3 OC2H5 5-F H Et2NCO CH3 CH3 OC2H5 3-Br CH3 H OCH3 OCH3 O-i-C3H7 H H EtOCO OCH3 CH3 Table 23 (continued) R5 R6 R Rc X Y m.p.( C) O-n-C3H7 H H n-C3H7CO CH3 OCH3 O-n-C3H7 6-CH3 H H CH3 CH3 O-i-C4H9 3-CF3 H CH3OCO OCH3 OCH3 O-i-C4H9 6-CF3 H H OCH3 CH3 CO2CH3 5-CF3 H H CH3 CH3 CO2CH3 6-CF3 H H CH3 OCH3 CO2CH3 H H CH3OCO OCH3 OC2H SO2N(CH3)2 6-SCH3 H H OCH3 OCH3 SO2N(CH3)2 5-SCH3 H CH3CO CH3 CH3 SO2N(CH3)2 6-OCH3 H H CH3 OCH3 S02N(CH3)2 H H (CH3)2NCO OCH3 OCH3 SO2N(CH3)2 3-OCH3 H H OCH3 OCH2CH3 SO2N(CH3)2 H H CH3NHCO CH3 CH(OCH2CH2O) SO2N(CH2CH3)2 3-CH3 CH3 H CH3 C2H5 S02N(CH2CH3)2 5-CH3 H CF3CO OCH3 OC2H5 SO2N(CH2CH3)2 6-Cl H C2H5CO OCH3 CH3 CO2CH2CH3 H H C2H5CO CH3 OCH3 CO2CH2CH3 5-Cl H H CH3 CH(OCH3)@ CO2CH3 6-Cl H H Cl CH3 CO2CH3 H H CH3OCO Cl OCH3 CO2CH3 5-F H H CH3 CH2OCH3 CO2-i-C3H7 5-F H (C2H5)2NCO CH3 CH3 CO2-i-C3H7 3-Br CH3 H OCH3 OCH3 SO2N(OCH3)CH3 H H n-C3H7CO OCH3 CH3 CO2CH2CH2OCH3 H H H CH3 OCH3 CO2CH2CH=CH2 6-CH3 H H CH3 CH3 CO2CH2CH2Cl 3-CF3 H H OCH3 OCH3 CO2-n-C4H9 6-CF3 H H OCH3 CH3 SO2CH3 5-CF3 H H CH3 CH3 SO2CH3 3-CF3 H H CH3 OCH3 SO2CH3 H H CH3OCO OCH3 OC2H5 SO2CH3 6-SCH3 H H OCH3 OCH3 Table 23 (continued) R5 R6 R Rc X Y m.p.( C) SO2CH2CH=CH2 5-SCH3 H CH3CO CH3 CH3 SO2CH2CH=CH2 6-OCH3 H H CH3 OCH3 SO2CH2CH2CH3 H H (CH3)2NCO OCH3 CH3 SCH2CH3 3-OCH3 H H OCH3 OCH3 SCF3 H H CH3NHCO CH3 CH(OCH2CH2O) SO2CHF2 3-CH3 CH3 H CH3 C2H5 CH3 5-CH3 H CF3CO OCH3 OC2H5 i-C3H7 6-C1 H H OCH CH3 n-C4H9 H H C2H5CO CH3 OCH3 OSO2N(CH3)2 6-Cl H H Cl CH3 OSO2N(CH3)2 H H CH3OCO Cl OCH3 OSO2CH(CH3)2 5-F H CH3CO CH3 CH2OCH3 OSO2CH3 3-Br CH3 H OCH3 OCH3 OSO2CH3 H H n-C3H7OCO OCH3 CH3 CH23OCH3 H H C3H7CO CH3 OCH3 CH2CH2OCH3 6-CH3 H H CH3 CH3 OCF3 3-CF3 H H OCH3 OCH3 SO2-i-C3H7 5-CF3 H H OCH3 CH3 CH2CH2OC2H5 H H H OCH3 CH3 * Data refer to molecular ion in electron-impact mass spectrum. Table 24 EMI87.1 R5 R6 R Rc X Y m.p.( C) Cl H H H CH3 CH3 Cl H H H CH3 OCH3 Cl H H H OCH3 OC2H5 Cl H H H OCH3 OCH3 137-140 F H H H CH3 CH3 F H H H CH3 OCH3 Br H H H OCH3 CH3 Br H H H OCH3 OCH3 N02 H H H CH3 CH(OCH2CH2O) N02 H CH3 H CH3 C2H5 CF3 H H H OCH3 OC2H5 CF3 H H H OCH3 CH3 OCH3 H H H CH3 OCH3 OCH3 H H H CH3 CH(OCH3)2 OCH3 H H H CH3 CH3 OCH3 H H H OCH3 OCH3 OC2H5 H H H CH3 CH2OCH3 OC2H5 H H H CH3 CH3 OC2H5 H CH3 H OCH3 OCH3 O-i-C3H7 H H H OCH3 CH3 O-n-C3H7 H H H CH3 OCH3 O-n-C3H7 H H H CH3 CH3 O-i-C4H9 H H H OCH3 OCH3 O-i-C4H9 H H H OCH3 CH3 CO2CH3 H H H CH3 CH3 Table 24 (continued) R5 R6 R Rc X Y m.p.( C) CO2CH3 H H H CH3 OCH3 CO2CH3 H H H OCH3 OC2H5 SO2N(CH3)2 H H H OCH3 OCH3 # 3.O and 4.0 (1: :1)** SO2N(CH3)2 H H H CH3 CH3 SO2N(CH3)2 H H H CH3 OCH3 SO2N(CH3)2 H H H OCH3 OCH2CH3 SO2N(CH3)2 H H H CH3 CH(OCH2CH2O) SO2N(CH2CH3)2 H CH3 H CH3 C2H5 SO2N(CH2CH3)2 H H H OCH3 OC2H5 SO2N(CH2CH3)2 H H H OCH3 CH3 CO2CH2CH3 H H H CH3 OCH3 CO2CH2CH3 H H H CH3 CH(OCH3)2 CO2CH3 H H H CH3 CH3 CO2CH3 H H H CH3 OCH3 CO2CH3 H H H CH3 CH2OCH3 CO2-i-C3H7 H H H CH3 CH3 CO2-I-C3H7 H CH3 H OCH3 OCH3 SO2N(OCH2)CH3 H H H OCH3 CH3 C02CH2CH20CH3 H H H CH3 OCH3 CO2CH2CH=CH2 H H H CH3 CH3 CO2CH2CH2Cl H H H OCH3 OCH3 CO2-n-C4H9 H H H OCH3 CH3 SO2CH3 H H H CH3 CH3 SO2CH3 H H H CH3 OCH3 SO2CH3 H H H OCH3 OC2H SO2CH3 H H H OCH3 OCH3 SO2CH2CH=CH2 H H H CH3 CH3 SO2CH2CH=CH2 H H H CH3 OCH3 SO2CH2CH2CH3 H H H OCH3 CH3 SCH2CH3 H H H OCH3 OCH3 SCF3 H H H CH3 CH(OCH2CH2O) SO2CHF2 H CH3 H CH3 C2H5 Table 24 (continued) R5 R6 R Rc X Y m.p.( C) CH3 H H H OCH3 OC2H5 i-C3H7 H H H OCH3 CH3 n-C4H9 H H H CH3 OCH3 OSO2N(CH3)2 H H H CH3 CH(OCH3)2 OSO2N(CH3)2 H H H CH3 CH3 OSO2CH(CH3)2 H H H CH3 OCH3 OSO2C2H5 H H H CH3 CH2OCH3 OSO2CH3 H CH3 H OCH3 OCH3 OSO2CH3 H H H OCH3 CH3 CH2OCH3 H H H CH3 OCH3 CH2CH2OCH3 H H H CH3 CH3 OCF3 H H H OCH3 OCH3 SO2-i-C3H7 H H H OCH3 CH3 Cl 3-CF3 H H CH3 CH3 Cl 5-CF3 H H CH3 OCH3 CL H H CH3OCO OCH3 OC2H5 Cl 6-SCH3 H H OCH3 OCH3 F 5-SCH3 H CH2CO CH3 CH3 F 6-OCH3 H H CH3 OCH3 Br H H (CH3)2NCO OCH3 CH3 Br 3-OCH2 H H OCH3 OCH3 NO2 H H CH3NHCO CH3 CH(OCH2CH2O) NO2 3-CH3 CH3 H CH3 C2H5 CF3 5-CH3 H CF3CO OCH3 OC2H5 CF3 6-Cl H C2H5CO OCH3 CH3 OCH3 H H C2H5OCO CH3 OCH3 OCH3 5-Cl H H CH3 CH(OCH3)2 OCH3 6-C1 H H CH3 CR3 OCH3 H H n-C3H7CO CH3 OCH3 OC2H5 5-F H H CH3 CH2OCH3 OC2H5 5-F H Et2NCO CH3 CH3 OC2H5 3-Br CH3 H OCH3 OCH3 Table 24 (continued) R5 R6 R Rc X Y m.p.( C) O-i-C3H7 H H EtOCO OCH3 CH3 O-n-C3H7 H H n-C3H7CO CH3 OCH3 O-n-C3H7 6-CH3 H H CH3 CH3 O-i-C4H9 3-CF3 H CH3OCO OCH3 OCH3 O-i-C4H9 5-CF3 H H OCH3 CH3 CO2CH3 3-CF3 H H CH3 CH3 CO2CH3 5-CF3 H H CH3 OCH3 CO2CH3 H H CH30CO OCH3 OC2H5 S02N(CH3)2 6-SCH3 H H OCR3OCH3 SO2N(CH3)2 5-SCH3 H CH3CO CH3 CH3 S02N(CH3)2 5-OCH3 H H CH3 OCH3 S02N(CH3)2 H H (CH3)2NCO OCH3 OCH3 SO2N(CH3)2 3-OCH3 H H OCH3 OCH2CH3 SO2N(CH3)2 H H CH3NHCO CH3 CH(OCH2CH2O) SO2N(CH2CH3)2 3-CH3 CH3 H CH3 C2H5 SO2N(CH2CH3)2 5-CH3 H n-C3H7CO OCH3 OC2H5 SO2N(CH2CH3)2 6-Cl H H OCH3 CH3 CO2CH2CH3 H H CF3CO CH3 OCH3 CO2CH2CH3 5-Cl H C2H5OCO CH3 CH(OCH3)2 CO2CH3 6-Cl H H CH3 CH3 CO2CH3 H H C2H5CO CH3 OCH3 CO2CH3 5-F H H CH3 CH2OCH3 CO2-i-C3H7 5-F H H CH3 CH3 CO2-i-C3H7 3-Br CH3 H OCH3 OCH3 SO2N(OCH3)CH3 H H Et2NCO OCH3 CH3 CO2CH2CH2OCH3 H H n-C3H7OCO CH3 OCH3 CO2CH2CH=CH2 6-CH3 H H CH3 CH3 CO2CH2CH2Cl H H CH3OCO OCH3 OCH3 CO2-n-C4H9 H H C2H5CO OCH3 CH3 SO2CH3 3-CF3 H H CH3 CH3 SO2CH3 5-CF3 H H CH3 OCH3 SO2CH3 H H CH3OCO OCH3 OC2H5 Table 24 (continued) R5 R6 R Rc X Y m.p.( C) SO2CH3 6-SCH3 H H OCH3 OCH3 SO2CH2CH=CH2 5-SCH3 H H CH3 CH3 SO2CH2CH2=CH2 6-OCH3 H (CH3)2NCO CH3 OCH3 SO2CH2CH2CH3 H H H OCH3 CH3 SCH2CH3 3-OCH3 H H OCH3 OCH3 SCF3 H H CH3NHCO CH3 CH(OCH2CH2O) SO2CHF2 3-CH3 CH3 H CH3 C2H5 CH3 5-CH3 H C2H5OCO OCH3 OC2H5 i-C3H7 6-Cl H H OCH3 CH3 n-C4H9 H H n-C3H7OCO CH3 OCH3 OSO2N(CH3)2 6-Cl H C2H5CO CH3 CH3 OSO2N(CH3)2 H H n-C3H7CO CH3 OCH3 OSO2CH3 5-F H H CH3 CH2OCH3 OSO2CH3 3-Br CH3 C2H5NHCO OCH3 OCH3 OSO2CH3 H H (C2H5)2NCO OCH3 CH3 CH2OCH3 H H CH3CO CH3 OCH3 CH2CH2OCH3 6-CH3 H H CH3 CH3 OCF3 H H C2H5OCO OCH3 OCH3 SO2-i-C3H7 H H n-C3H7NHCO OCH3 CH3 CH2CH2OC2H5 H H H OCH3 CH3 **Data refer to characteristic signals in NMR spectrum (CDC13) in ppm downfield from tetramethylsilane. Table 25 EMI92.1 EMI92.2 R <SEP> R <SEP> R <SEP> m.p. <tb> <SEP> c <SEP> R <SEP> 5 <SEP> 6 <SEP> X <SEP> y <SEP> Z <SEP> (4C) <tb> H <SEP> H <SEP> OCH2CH20CH3 <SEP> H <SEP> CH3 <SEP> H <SEP> CH <tb> H <SEP> H <SEP> OCH2CH=CH2 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> H <SEP> H <SEP> OCH2CHSCR <SEP> 6-OCH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> H <SEP> H <SEP> C6f'5 <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> H <SEP> H <SEP> N-N <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> <SEP> O <SEP> CH3 <tb> H <SEP> H <SEP> N-N, <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> <SEP> fi'0 <tb> H <SEP> H <SEP> C1 <SEP> H <SEP> OCH3 <SEP> OCH2C-CH <SEP> N <tb> CONHCH3 <SEP> H <SEP> C1 <SEP> H <SEP> OCH3 <SEP> OCH2CF3 <SEP> CH <tb> H <SEP> H <SEP> C1 <SEP> H <SEP> 2 <SEP> OCH2CR2 <SEP> OCR3 <SEP> N <tb> H <SEP> H <SEP> C1 <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <SEP> CH <tb> H <SEP> H <SEP> F <SEP> H <SEP> OCH3 <SEP> OCF2H <SEP> CH <tb> H <SEP> H <SEP> F <SEP> H <SEP> OCR3 <SEP> SCF2H <SEP> CH <tb> H <SEP> H <SEP> F <SEP> 3-OCF2H <SEP> OCH3 <SEP> C(CH3)(0CH3)2 <SEP> CH <tb> H <SEP> H <SEP> F <SEP> H <SEP> OCR3 <SEP> 3 <SEP> N <tb> H <SEP> H <SEP> Br <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <SEP> CH <tb> H <SEP> CR3 <SEP> Br <SEP> R <SEP> OCR3 <SEP> C(CR3)(5CR3)2 <SEP> N <tb> H <SEP> CR3 <SEP> Br <SEP> H <SEP> OCF2H <SEP> Cf'(SCR2CR2 <SEP> S) <SEP> CH <tb> H <SEP> Cm'3 <SEP> Br <SEP> H <SEP> CF3 <SEP> CH2CH3 <SEP> CH <tb> H <SEP> 3 <SEP> Br <SEP> H <SEP> F <SEP> OCH3 <SEP> CH <tb> 3 <SEP> CR3 <SEP> Br <SEP> H <SEP> OC2Hs <SEP> C(CH3)(0CH2CH20) <SEP> CH <tb> Table 25 (continued) EMI93.1 <tb> R <SEP> R <SEP> R <tb> c <SEP> R <SEP> 5 <SEP> 6 <SEP> x <SEP> y <SEP> Z <SEP> m.p.(0C) <tb> H <SEP> H <SEP> n <SEP> H <SEP> CH3 <SEP> H <SEP> CH <tb> <SEP> 3 <tb> H <SEP> H <SEP> -N <SEP> H <SEP> 3 <SEP> CR3 <SEP> CH <tb> H <SEP> H <SEP> P <SEP> N\ <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CR <tb> <SEP> NsNR <tb> COCF3 <SEP> H <SEP> O-n-C <SEP> H <SEP> OCR3 <SEP> OCR3 <SEP> CH <tb> H <SEP> H <SEP> O-n-C3H7 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH=CH2 <SEP> CH <tb> H <SEP> H <SEP> O-n-C3H7 <SEP> H <SEP> OCR3 <SEP> OCH2C=CH <SEP> N <tb> H <SEP> H <SEP> OCH3 <SEP> 5-Br <SEP> OCR3 <SEP> OCR <SEP> CF <SEP> N <tb> H <SEP> H <SEP> OCH3 <SEP> H <SEP> OCR3 <SEP> OCf'2CH2 <SEP> OCR3 <SEP> N <tb> H <SEP> H <SEP> OCH3 <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <SEP> CH <tb> H <SEP> H <SEP> N02 <SEP> H <SEP> OCH3 <SEP> OCF2H <SEP> CH <tb> H <SEP> H <SEP> NO <SEP> H <SEP> OCR3 <SEP> SCF2R <SEP> CH <tb> H <SEP> H <SEP> NO2 <SEP> H <SEP> OCR3 <SEP> C(CH3)(0CH3)2 <SEP> CH <tb> H <SEP> H <SEP> CF3 <SEP> H <SEP> OCR3 <SEP> CF3 <SEP> CH <tb> H <SEP> H <SEP> CF3 <SEP> H <SEP> OCH3 <SEP> N(CH3)2 <SEP> CH <tb> H <SEP> CR3 <SEP> 3 <SEP> H <SEP> OCR3 <SEP> C(CH3)(SCH3)2 <SEP> CH <tb> H <SEP> CH3 <SEP> C02CH3 <SEP> H <SEP> OCF2H <SEP> CH(SCH2CH2S) <SEP> CH <tb> H <SEP> CH3 <SEP> C02CH3 <SEP> H <SEP> CF3 <SEP> CH2CH3 <SEP> CH <tb> H <SEP> CH3 <SEP> C02CH3 <SEP> H <SEP> F <SEP> OCH3 <SEP> CH <tb> H <SEP> CH3 <SEP> C02CH3 <SEP> H <SEP> OC2H5 <SEP> C(CH3)(0CH2CH20) <SEP> CH <tb> H <SEP> H <SEP> 4 <SEP> H <SEP> CH3 <SEP> H <SEP> N <tb> <SEP> 0 <tb> H <SEP> H <SEP> 4 <SEP> H <SEP> CR3 <SEP> CR3 <SEP> N <tb> H <SEP> H <SEP> R <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> H <SEP> H <SEP> C02CH2CH=CH2 <SEP> H <SEP> OCR3 <SEP> OCH3 <SEP> CH <tb> H <SEP> H <SEP> C02CH2CH=CH2 <SEP> H <SEP> OCH3 <SEP> OCH2CH=CH2 <SEP> CH <tb> Table 25 (continued) EMI94.1 <tb> ssc <SEP> 85 <SEP> R6 <SEP> ¯ <SEP> Y <SEP> ¯¯¯¯¯¯¯ <tb> R <SEP> R <SEP> Z <SEP> X <SEP> Y <SEP> z <SEP> m.p.(C) <tb> H <SEP> H <SEP> CO,CH,CH=CH, <SEP> 2 <SEP> 2 <SEP> OCH3 <SEP> OCH2CiSCH <SEP> N <tb> <SEP> 2 <tb> H <SEP> H <SEP> SQ2N(CH3)2 <SEP> H <SEP> OCH3 <SEP> OCH2CF3 <SEP> N <tb> H <SEP> K <SEP> SO,N(CH3)2 <SEP> H <SEP> OCf' <SEP> OCR <SEP> Cf' <SEP> OCR <SEP> N <tb> <SEP> 2 <SEP> 32 <SEP> 3 <SEP> 2 <SEP> 2 <SEP> 3 <tb> H <SEP> H <SEP> S02N(CH3)2 <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <SEP> N <tb> <SEP> 2 <SEP> 32 <SEP> 3 <SEP> 2 <SEP> 3 <tb> H <SEP> H <SEP> S02N(OCH3)CH3 <SEP> H <SEP> OCH3 <SEP> OCF2H <SEP> CH <tb> <SEP> 2 <SEP> 3 <SEP> 3 <SEP> 3 <SEP> 2 <tb> H <SEP> H <SEP> S 2N(CH3)C2H5 <SEP> H <SEP> OCH3 <SEP> SCF2H <SEP> CH <tb> H <SEP> H <SEP> SCF3 <SEP> H <SEP> OCR <SEP> C(CH3)(0CH3)2 <SEP> CH <tb> <SEP> SCF3 <SEP> 3 <SEP> 3 <SEP> 3 <SEP> 2 <tb> 2 <SEP> H <SEP> SO <SEP> 2CRF2 <SEP> R <SEP> OCH3 <SEP> CF3 <SEP> CH <tb> H <SEP> H <SEP> CO,CH,CH,C1 <SEP> H <SEP> 2 <SEP> OCH3 <SEP> N(CH3)2 <SEP> CH <tb> H <SEP> CR3 <SEP> CO2CR2CR3 <SEP> H <SEP> OCH3 <SEP> C(CH3)(SCH3)2 <SEP> CH <tb> H <SEP> H <SEP> C02CH2CH3 <SEP> H <SEP> OCF2H <SEP> CH(SCH2CH2S) <SEP> CH <tb> H <SEP> H <SEP> CO,CH,CH, <SEP> H <SEP> CF3 <SEP> CH2CH3 <SEP> CH <tb> H <SEP> H <SEP> S02CH3 <SEP> H <SEP> F <SEP> OCH3 <SEP> CH <tb> CO-i-C3H7 <SEP> H <SEP> SO2CR3 <SEP> H <SEP> OC2H5 <SEP> C(Cf'3)(OCH2Cf'2O) <SEP> CH <tb> H <SEP> H <SEP> e <SEP> H <SEP> CH3 <SEP> H <SEP> N <tb> <SEP> o,N <tb> H <SEP> f'; ;7\N-0 <SEP> H <SEP> Cf'3 <SEP> CR3 <SEP> N <tb> <SEP> N O <tb> H <SEP> H <SEP> / <SEP> N=N\ <SEP> 6CCF2H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> <SEP> S <tb> H <SEP> H- <SEP> N <SEP> H <SEP> OCR3 <SEP> OCR3 <SEP> CH <tb> <SEP> 0 <tb> H <SEP> H <SEP> OCH3 <SEP> H <SEP> OCH3 <SEP> OCH2C-CH <SEP> CH <tb> H <SEP> H <SEP> OCH3 <SEP> H <SEP> OCR3 <SEP> OCH2CF3 <SEP> CH <tb> H <SEP> H <SEP> OCH3 <SEP> H <SEP> OCR3 <SEP> OCR2CR2OCR3 <SEP> CH <tb> H <SEP> H <SEP> C2R5 <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <SEP> CH <tb> H <SEP> H <SEP> OC <SEP> H <SEP> 3-F <SEP> OCH3 <SEP> OCF2H <SEP> CH <tb> C02CH2CH3 <SEP> H <SEP> OC2H5 <SEP> H <SEP> OCR3 <SEP> SCF2R <SEP> CH <tb> H <SEP> H <SEP> CH3 <SEP> 3 <SEP> OCR3 <SEP> CCCR3)(OCR3)2 <SEP> N <tb> H <SEP> H <SEP> CH3 <SEP> H <SEP> OCR <SEP> CF3 <SEP> N <tb> <SEP> 3 <SEP> 3 <tb> Table 25 (continued) Rc R R5 R6 X Y Z m.p.( C) H H CH3 H OCH3 N(CH3)2 N H CH3 i-C3H7 H OCH3 C(CH3)(SCH3)2 CH H H i-C3H7 H OCF2H CH(SCH2CH2S) CH H H i-C3H7 H CF3 CH2CH3 CH H H i-C3H7 H F OCH3 CH H H n-C4H9 H OC2H5 C(CH3) (OCH2CH2O) N Table 26 EMI96.1 EMI96.2 <tb> <SEP> R <tb> R7 <SEP> R <SEP> Rc <SEP> x <SEP> y <SEP> Z <SEP> m.P.( C) <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <tb> <SEP> 3 <SEP> 3 <tb> CH3 <SEP> H <SEP> CON(CH3)2 <SEP> OCH3 <SEP> CH3 <SEP> N <tb> OCH3 <SEP> H <SEP> H <SEP> Cl <SEP> CH3 <SEP> CH <tb> F <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <tb> C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> Br <SEP> K <SEP> H <SEP> F <SEP> OCH3 <SEP> CH <tb> S02N(CH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> OCF2H <SEP> OCH3 <SEP> CH <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> Cf'2 <SEP> F <SEP> OC2H5 <SEP> CH <tb> H <SEP> CH3 <SEP> H <SEP> OCR <SEP> CR <SEP> CR <SEP> OCR3 <SEP> N <tb> <SEP> 23 <SEP> 2 <tb> CH3 <SEP> H <SEP> H <SEP> CF3 <SEP> N(CH3)2 <SEP> CH <tb> <SEP> 3 <SEP> 2 <tb> OCH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CF <SEP> CH <tb> <SEP> 3 <tb> F <SEP> H <SEP> C02CH2CH3 <SEP> CH3 <SEP> CH(OCH3)2 <SEP> CH <tb> C1 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCF2H <SEP> N <tb> Br <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2CH20CH3 <SEP> N <tb> N(CH <SEP> ) <SEP> H <SEP> R <SEP> 3 <SEP> CH2SCK3 <SEP> 2 <SEP> 3 <tb> <SEP> 3 <SEP> 2 <SEP> OCR <SEP> Cf' <SEP> SCR <SEP> N <tb> OSO <SEP> 2CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH2C-CH <SEP> CH <tb> SCH3 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> 0 <SEP> < <SEP> CH <tb> SUCK3 <SEP> H <SEP> H <SEP> 3 <SEP> 0 <SEP> ) <SEP> Cf' <tb> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> Table 27 EMI97.1 EMI97.2 <tb> R8 <SEP> R <SEP> R <SEP> m.p. <tb> P <SEP> R <SEP> c <SEP> X <SEP> y <SEP> Z <SEP> (0C) <tb> CH3 <SEP> H <SEP> CON(CH3)2 <SEP> OCH3 <SEP> N <tb> CH2CH3 <SEP> H <SEP> H <SEP> C1 <SEP> OCH3 <SEP> CH <tb> OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH20C2H5 <SEP> CH <tb> <SEP> 3 <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> OCR <SEP> CR <SEP> H <SEP> H <SEP> OCR3 <SEP> CR3 <SEP> CR <tb> <SEP> 23 <tb> F <SEP> H <SEP> H <SEP> F <SEP> CH3 <SEP> CH <tb> C1 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <tb> Br <SEP> H <SEP> H <SEP> OCF2H <SEP> CH3 <SEP> CH <tb> S02N(CH2CH3)2 <SEP> H <SEP> H <SEP> CR2F <SEP> OCH3 <SEP> CH <tb> S02N(CH3)2 <SEP> R <SEP> OCH2CH3 <SEP> OCH3 <SEP> N <tb> <SEP> 2 <SEP> 32 <tb> SO <SEP> N(OCH <SEP> )CH <SEP> H <SEP> H <SEP> CF <SEP> OCH3 <SEP> CH <tb> <SEP> 2 <SEP> 3 <SEP> 3 <SEP> 3 <tb> SCH2CH=CH2 <SEP> H <SEP> H <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> S02C2H5 <SEP> H <SEP> CO2CR2CR3 <SEP> CR3 <SEP> OCH3 <SEP> CH <tb> S-n-C3H7 <SEP> H <SEP> H <SEP> OCH3 <SEP> C <SEP> H <SEP> N <tb> S 2CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> OC2Hg <SEP> N <tb> SCH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> SCF2H <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> C(CH3)(SCH3)2 <SEP> CH <tb> F <SEP> H <SEP> H <SEP> OCR <SEP> 2CH3 <SEP> OCF9H <SEP> CH <tb> C1 <SEP> H <SEP> H <SEP> CH3 <SEP> CH(0C2R5)2 <SEP> CH <tb> Br <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> OCH3 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> N <tb> Table 28 EMI98.1 EMI98.2 <tb> L <SEP> 9 <SEP> R <tb> <SEP> R <SEP> R <SEP> C <SEP> X <SEP> Y <SEP> z <SEP> (0C) <tb> L4 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> L <SEP> F <SEP> H <SEP> CON(CH3)2 <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> L4 <SEP> N02 <SEP> H <SEP> H <SEP> C1 <SEP> OCR3 <SEP> CH <tb> 4 <SEP> CO <SEP> C <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> fi4 <SEP> CHg)2 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH2SCH3 <SEP> CH <tb> <SEP> N(CR <SEP> ) <SEP> H <SEP> H <SEP> 3 <SEP> 2 <SEP> 3 <tb> L4 <SEP> S-i-C3H7 <SEP> H <SEP> H <SEP> F <SEP> CH3 <SEP> CH <tb> L <SEP> n-C3H7 <SEP> H <SEP> H <SEP> CH3 <SEP> N(CH3)2 <SEP> CH <tb> L5 <SEP> Cl <SEP> H <SEP> H <SEP> OCF2H <SEP> CH20CH3 <SEP> CH <tb> L <SEP> Br <SEP> H <SEP> H <SEP> CH2F <SEP> CH20CH3 <SEP> CH <tb> 5 <SEP> 2 <SEP> 3 <SEP> 3 <SEP> 2 <SEP> CR <SEP> R <SEP> OCH2Cf'3 <SEP> CR2OCR3 <SEP> N <tb> 3 <tb> L5 <SEP> S02N(C2H5)2 <SEP> 2 <SEP> H <SEP> H <SEP> CF3 <SEP> CH3 <SEP> CH <tb> L5 <SEP> S02NtOCH3)CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> 5 <SEP> S02C2H5 <SEP> H <SEP> C02CH2CR3 <SEP> 2 <SEP> 3 <SEP> 3 <SEP> CH3 <SEP> CH <tb> fis <SEP> SCH,CH=CH, <SEP> H <SEP> 2 <SEP> H <SEP> H <SEP> OCR3 <SEP> CH3 <SEP> N <tb> 5 <SEP> 2 <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <SEP> S <SEP> > <SEP> N <tb> t6 <SEP> F <SEP> H <SEP> H <SEP> OCH3 <SEP> CH(OCH3)2 <SEP> CH <tb> L6 <SEP> C02-i-C3H7 <SEP> H <SEP> H <SEP> OCH2CH3 <SEP> OCH3 <SEP> CH <tb> L6 <SEP> S02CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> CH <tb> L6 <SEP> S02N(CH3)2 <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> 6 <SEP> Br <SEP> H <SEP> H <SEP> CH3 <SEP> OCH3 <SEP> N <tb> Table 29 EMI99.1 m.p. R10 R Rc X Y Z ( C) Cl H H CH3 CH3 CH NO2 H CON(CH3)2 OCH3 CH3 N CO2CH3 H H Cl CH3 CH CO2CH2CH3 H H CH3 CH3 CH SO2N(CH3)2 H H OCH3 CH3 CH OSO2CH3 H H F OCH3 CH SO2CH3 H H CH3 OCH3 CH S02CH2CH3 H H OCF2H OCH3 CH OCH3 H H CH2F OCH3 CH OCH2CH3 CH3 H OCH2CH3 OCH3 N OCH2CH3 H H CF3 CH2SCH3 CH OCH2CH3 H H OCH3 CF3 CH OCH3 H CO2CH2CH3 CH3 CH2CH3 CH S02CH2CH3 H H OCH3 OCH3 N SO2CH3 H H OCH3 SCF2H N OXO2CH3 H H OCH3 CH3 N CO2CH2CH3 H H OCH3 CH3 CH CO2CH3 H H OCH2CH3 CH3 CH CO2CH3 H H CH3 CH3 CH C 2CH3 H H CH3 OCH3 N NO2 H H CH3 OCH3 N Table 30 EMI100.1 m.p. Q1 R11 R12 R13 R RC X Y Z ( C) O H H H H H CH3 OCR3 S H H H H CON(CH3)2 OCH3 OCH3 N SO2 H H H H H Cl OCH3 NH H H H H H CH3 OCH3 CH NCH3 H H H H H OCH3 CH3 O CH3 CH3 H H H F CH3 CR S CH3 CH3 H H H CH3 CH3 CH SO2 CH3 CH3 H H H OCF2H CH3 CH NH CH3 CH3 H H H CH2F OCH2CH3 CH NCH3 CH3 CH3 CH3 CH3 H OCH2CH3 OCH2CH3 N O CH2CH3 CH3 H H H CF3 OCH2CH3 CH S CH2CH3 CH3 H H H OCH3 CF3 CH SO2 CH2CH3 CH2CH3 H H CO2CH2CH3 CH3 OCF2@ NH CH2CH3 CH3 H H H OCH3 OCH3 N NCH3 CH2CH3 CH3 H H H OCH3 OCH3 O H CH3 H H H OCH3 OCH3 N S H CH3 H H H OCH3 OCH3 CR SO2 H CH3 H H H OCH2CH3 OCH3 CH NH H CH3 H H H CH3 (C(cH2)@OCH@)@ NCH3 H CH3 H H H CH3 CH3 N O CH3 CH3 H H H CH3 CH3 Table 31 EMI101.1 m.p. Q2 R14 R15 R Rc X Y Z ( C) O H H H H CH3 CH3 CH O H CH3 H CON(CH3)2 OCH3 CH3 N O H H H H Cl CH3 CH O H CH3 H H CH3 CH3 CH O CH3 H H H OCH3 CH(OCH3)2 CH O CH3 CH3 H H F OCH3 CH O CH3 H H H CH3 OCH3 CH S H CH3 H H OCF2H OCH3 CH S H H H H CH2F OCH3 CH S H CH3 CH3 H OCH2CH3 CH2SCH3 N S H H H - H CF3 OCH2CH3 CH S CH3 CH3 H H OCH3 OCH3 CH S CH3 H H CO2CH2CH3 CH3 OCH3 CH S CH3 CH3 H H OCH3 OCH3 N NH H H H H OCH3 OCH3 N NH CH3 CH3 H H OCH3 OCH3 N NH H H H H OCH3 OCH3 CH NCH3 H CH3 H H OCH2CH3 CH3 CH NCH3 CH3 H H H CH3 CH3 CH NCH3 CH3 CH3 H H CH3 CH3 N NCH3 CH3 H H H CH3 CH3 N Table 32 EMI102.1 m.p. L m R13 R16 R Rc X Y Z ( C) L-10 0 H CH3 H H CH3 CH3 CH L-10 1 H CH3 H CON(CH3)2 OCH3 CH3 N L-10 0 H CH3 H H Cl CH3 CH L-ll O CH3 - H H CH3 CH3 CH L-11 0 CH3 - H H OCH3 CH(OCH3)2 CH L-ll O CH3 - H H F OCH3 CH L-ll O H - H H CH3 OCH3 CH L-12 1 H - H H OCF2H OCH3 CH L-12 0 H - H H CH2F OCH3 CH L-12 1 H - CH3 H OCH2CH3 CH2SCH3 N L-13 0 CH3 - H H CF3 OCH2CH3 CH L-13 1 H - H H OCH3 OCH3 CH L-13 0 H - H CO2CH2CH3 CH3 OCH3 CH L-13 1 H - H H OCH3 OCH3 N L-14 0 H - H H OCH3 OCH3 N L-14 1 H - H H OCH3 OCH3 N L-14 0 CH3 - H H OCH3 OCH3 CH L-10 1 H CH3 H H OCH2CH3 CH3 CH L-10 0 H C2H5 H H CH3 CH3 CH L-10 1 H C2H5 H H CH3 CH3 N L-10 0 H C2H5 H H CH3 CH3 N Table 33 EMI103.1 m.p. L R17 R18 R Rc X Y Z ( C) L15 H - H H CH3 CH3 CH L15 H - H CON(CH3)2 OCH3 CH3 N L15 H - H H Cl CH3 CH L15 H - H H CH3 CH3 CH L15 H - H H OCH3 CH(OCH3)2 CH L15 H - H H F OCH3 CH L15 H - H H CH3 OCH3 CH L15 CH3 - H H OCF2H OCH3 CH L15 CH3 - H H CH2F OCH3 CH L15 CH3 - CH3 H OCH2CH3 CH2SCH3 N L16 CH3 - H H CF3 OCH2CH3 CH L16 CH3 - H H OCH3 OCH3 CH L16 CH3 - H CO2CH2CH3 CH3 OCH3 CH L16 CH3 - H H OCH3 OCH3 N L16 H - H H OCH3 OCH3 N L16 H - H H OCH3 OCH3 N L16 H - H H OCH3 OCH3 CH L17 CH3 CH3 H H OCH2CH3 CH3 CH L17 CH3 H H H CH3 CH3 CH L17 CH3 CH3 H H CH3 CH3 N 17 CH3 CH3 R H CH3 CH3 N Table 34 EMI104.1 EMI104.2 R <SEP> R <SEP> R <tb> <SEP> 5 <SEP> 6 <SEP> R <SEP> c <SEP> A <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> A2 <SEP> YI=CH2; <SEP> 11=CR3 <tb> i-C3f'7 <SEP> H <SEP> H <SEP> H <SEP> A2: <SEP> Y1=0; <SEP> X1 <SEP> OCH3 <tb> OC2f'5 <SEP> H <SEP> H <SEP> H <SEP> A2: <SEP> Y1=Cf'2; <SEP> X1=OCF2R <tb> O-n-C4H9 <SEP> H <SEP> H <SEP> H <SEP> 1 <SEP> 3 <SEP> X1=Cf'3 <tb> F <SEP> 3-CF3 <SEP> H <SEP> CO2CH3 <SEP> A3: <SEP> X1=OCH2CH3 <tb> C1 <SEP> H <SEP> H <SEP> CO2CR3 <SEP> A4: <SEP> X1=OCH3; <SEP> 2 <tb> NO2 <SEP> H <SEP> CH3 <SEP> CO2CR3 <SEP> A4: <SEP> X1=CH3; <SEP> Y2=CH3 <tb> CF3 <SEP> H <SEP> H <SEP> C02CH3 <SEP> A5 <SEP> g2=CH3; <SEP> Y3=OCH3 <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> C02CH3 <SEP> A5: <SEP> X2=CH3; <SEP> Y3=SCH3 <tb> C02CH2CH3 <SEP> 3-CH3 <SEP> H <SEP> CO2 <SEP> Cf'3 <SEP> A5: <SEP> X2=CH3; <SEP> Y3=C2H5 <tb> S02N(CH3)2 <SEP> H <SEP> H <SEP> CO2CR3 <SEP> A6 <SEP> 13=cur3 <tb> S02N(C2H5)2 <SEP> H <SEP> H <SEP> 3 <SEP> 6 <SEP> 3 <SEP> 3 <SEP> 13=OCR3 <tb> OS02CH2CH3 <SEP> H <SEP> Cf'3 <SEP> CO2Cf'3 <SEP> 2 <SEP> Y1=O; <SEP> X1=OCH2CH3 <tb> SCH3 <SEP> 6-Cl <SEP> H <SEP> C 2CH3 <SEP> A2: <SEP> Y1=CH2; <SEP> 1 <SEP> 3 <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> H <SEP> A2: <SEP> Yl=O; <SEP> X1=Cf'3 <tb> OCHF2 <SEP> H <SEP> H <SEP> COCH3 <SEP> 3 <SEP> 11=OCF2R <tb> OCR2CR=CR2 <SEP> H <SEP> H <SEP> H <SEP> A3 <SEP> X1 <SEP> OCH3 <tb> C6H5 <SEP> H <SEP> H <SEP> H <SEP> A4: <SEP> X1=OCH3; <SEP> Y2=CR3 <tb> <SEP> H <SEP> H <SEP> H <SEP> H <SEP> A4: <SEP> X1=OCF2H; <SEP> Y2=H <tb> e <SEP> H <SEP> H <SEP> H <SEP> A5: <SEP> X2=CR2CF3; <SEP> Y3 <SEP> 3 <tb> <SEP> O <tb> CH;OCH <SEP> H <SEP> H <SEP> H <SEP> 3 <SEP> X3=OCR3 <tb> CR2OCR3 <SEP> H <SEP> H <SEP> H <SEP> 3 <SEP> 3 <tb> Table 35 EMI105.1 R L R c A L-2: R7=S02N(CH3)2 H H A2: Y1=CH2; X1-CH3 L-2; R7=OXO2CH3 H H A2: Y1=O: X1=OCH3 L-2: R7=C1 H H A2: Y1=CH2; X1=OCF2H L-2: R7=Br H H A3: X1=CH3 L-3: R8=CH3 H CO2CH3 A3: X1=OCH2CH3 L-3: R8=OCH3 H CO2CH3 A4: X1=OCH3; Y2=H L-3: R8=SO2CH2CH3 CH3 CO2CH3 A4: X1=CH3; Y2=CH3 L-4: R9=CO2CH3 H CO2CH3 A5: X2=CH3; Y3=OCH3 L-5: R9=CO2-1-C3H7 H CO2CH3 A5: X2=CH3; Y3=SCH3 L-6: R9=Cl H CO2CH3 A5: X2=CH3; Y3=C2H5 L-4: R9=NO2 H CO2CH3 A6: X3=CH3 L-5: R9=SO2N(CH3)2 H CO2CH3 A6: X3=OCH3 L-6: R9=C2H5 CH3 CO2CH3 A2: Y1=O; X1=OCH2CH3 L-7: R10=CO2CH3 H CO2CH3 A1: Y1=CH2; X1=OCH3 L-7: R10=SO2N(CH3)2 H H A2: Y1=O; X1=CH3 L-7: R10=OSO2CH3 H COCH3 A3: X1=OCF2H L-8: R11=R12=R13=CH3; m-0; Q1=S H H A3: X1=OCH3 L-9: R14=CH3; R15=H; Q2=NCH3 H H A4: X1=OCH3; Y2=CH3 L-10: R16=C2H5; R13=H; m=l H H A4: X1=OCF2H; Y2=H L-li: R13=H; m=O H H A5: X2=C2H5; Y3=OC2H5 L-12: R13=CH3: m=O H H A5: X2=CH2CF3; Y3=CH3 L-13: R13=CH3; m=O H H A5: X2=CH3; Y3=C2H5 L-14: R16=CH3 H H A6:X3=OCH3 L-15: R17=H H H A2: Y1=CH2; X1=CH3 L-15: R17=H H H A2: Y1=O; X1=OCH3 L-15: R17=H H H A2: Y1=CH2, X1=OCF2H Table 35 (continued) L R RÚ A L-16: R17=CH3 H H A3: X1=CH3 L-16: R17=CH3 H CO2CH3 A3: X1=OCH2CH3 L-16: R17=CH3 H CO2CH3 A3:X1=OCH3; Y2=H L-17: R17=H; R18=CH3 CH3 CO2CH3 A4: X1=CH3; Y2=CH3 L-17: R17=H; R18=CH3 H CO2CH3 A5: X2=CH3; Y3=OCH3 L-17: R17=H; R18=CH3 H CO2CH3 A5: X2=CH3; Y3=SCH3 L-8: R11=R12=R13=H; m=1; Q1=SO2 H CO2CH3 A5: X2=CH3; Y3=C2H5 L-8: R11=R12=R13=H; m=1; Q1=SO2 H CO2CH3 A6: X3=CH3 L-8: R11=R12=R13=H; m-1; Q1=SO2 H CO2CH3 A6: X3=OCH3 L-9: R14=R15=H; Q2=S CH3 CO2CH3 A2: Y1=O; X1=OCH2CH3 L-9: R14=R15=H; Q2=S H CO2CH3 A2: Y1=CH2; X1=OCH3 L-9: R14=R15=H; Q2=S H H A2: Y1=O; X1=CH3 L-10: R13=R16=CH3; m=0 H COCH3 A3: X1=OCF2H L-10: R13=R16=CH3; m=0 H H A3: X1=OCH3 L-10: R13=R16=CH3; m=0 H H A4: X1=OCH3; Y2=CH3 L-11: R13=CH3; m=0 H H A4: X1=OCF2H; Y2=H L-11: R13=CH3; m=0 H H A5: X2=C2H5; Y3=OC2H5 L-11: R13=CH3; m=0 H H A5: X2=CH2CF3; Y3=CH3 L-12: R13=H; m=1 H H A5: X2=CH3; Y3=C2H5 L-13: R13=H; m=1 H H A6: X3=OCH3 L-14: R16=H H H A6: X3=CH3 Formulations Useful formulations of the compounds of Formulas I-III can be prepared in conventional ways. They include dusts, granules. pellets. solutions, suspensions. emulsions. wettable powders. emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations. broadly. contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically. they will contain these ingredients in the following approximate proportions: Table 36 Weight Percent* Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden. "Solvents Guides 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separa tion at OOC. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, '1Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147ff. and "Perry1s Chemical Engineer's Handbook", 5th Ed., McGraw-Hill. New York 1973, PP 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14. 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8. 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Hand book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples. all parts are by weight unless otherwise indicated. Example 10 Wettable Powder N-t(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- dimethyiaminosuifonylbenzenesulfonamide. dimethyl sulfonium inner salt 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example 11 Wettable Powder N-t(4,6-dimethoxypyrimidin-2-l)aminocarbonylj-2- dimethylaminosulfonylbenzenesulfonamide, dimethyl sulfonium inner salt 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 12 Granule Wettable Powder of Example 11 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 13 Extruded Pellet 2-[[(4,6-dimethoxypytimidin-2-yl)aminocarbonyl]-2 dimethylaminosulfonyllbenzoic acid methyl ester, dimethylsulfonium inner salt 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying. or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. Example 14 Oil Suspension N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2 dimethylaminosulfonylbenzenesulfonamidea dimethyl sulfonium inner salt 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 15 Wettable Powder 2-( ((4 a 6-dimethoxypyrimidin-2-yi)aminocarbonyl)-2 dimethylaminosulfonyl]benzoic acid methyl ester, dimethylsulfonium inner salt 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example 16 Low Strength Granule N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 dimethylaminosulfonylbenzenesulfonamide, dimethyl sulfonium inner salt 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed. the blender is allowed to run for a short period and then the granules are pack- aged. Example 17 Aqueous Suspension N-t(4.6-dimethoxypyrimidin-2-ylEaminocarbonyl3-2- dimethylaminosulfonylbenzenesulfonamidea dimethyl sulfonium inner salt 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 18 High Strenqth Concentrate N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin-2 yl)amino]-l-(hydroxyimino)methyl]-1,2-benzenedi- sulfonamide 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 19 Wettable Powder N',N'-dimethyl-N-[[1-(4,6-dimethyl-1,3,5-triazin-2-yl) amino]-l-(hydroxyimino)methyl3-1.2-benzenedisulfon- amide 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. Example 20 Wettable Powder 2-((l-(4,6-dimethylpyrimidin-2-yi)aminoj-i-(hydroxy- imino)methyl3aminosulfonyl]benzoic acid, methyl ester 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended a coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 21 Oil Suspension N',N'-dimethyl-N-[tl-(dimethyl-1,3,5-triazin-2-yl)- amino]-l-(hydroxyimino)methyl]-1,2-benzenedisulfon- amide 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 598 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 22 Dust 2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1 (hydroxyimino)methyl)aminosulfonylibenzoic acid, methyl ester 10% attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example 23 Emulsifiable Concentrate N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin-2- yl)amino]-l-(hydroxyimino)methyl3-1,2-benzenedi- sulfonamide 20% chlorobenzene 74% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. Utility The compounds of the present invention are active- herbicides. They have utility for broadspectrum pre-and/or post-emergence weed control in areas where complete control of all vegetation is de sires, such as around fuel storage tanks. ammunition depots. industrial storage areas, parking lots, drive in theaters, around billboards, highway and railroad structures. Alternatively. the subject compounds are useful for the selective pre- or post-emergence weed control in crops, such as wheat, rice, and barley. The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected. mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.03 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine. triazole, uracil, urea, amide, diphenylether, carbamate -and bipyridylium types. The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. Test A Seeds of crabgrass (Diqitaria spp.), barnyardgrass (Echinochloa crusqalli), wild oats (Avena fatua) sicklepod (Cassia obtusifolia), morningglory (Ipomoea spy.), cocklebur (Xanthium pensylvanicum)1 sorghum, corn, soybean, sugar beet, rice, wheat, and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment, The ratings. summarized in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis; E = emergence inhibition; G = growth retardation; H = formative effect; U = unusual pigmentation; and 6Y= abscised buds or flowers. Note that compounds tested are highly active herbicides at the low rates of application selected for this test. Compounds Compound 1 EMI117.1 Compound 2 EMI117.2 Compound 3 EMI117.3 Compound 4 EMI117.4 Compounds (continued) Compound 5 EMI118.1 Compound 6 EMI118.2 Compound 7 EMI118.3 Compound 8 EMI118.4 Compounds (continued) Compound 9 EMI119.1 Compound 10 EMI119.2 Compound 11 EMI119.3 Compound 12 EMI119.4 Compounds (continued) Compound 13 EMI120.1 Compound 14 EMI120.2 Compound 15 EMI120.3 Compound 16 EMI120.4 Compounds (continued) Compound 17 EMI121.1 Compound 18 EMI121.2 Compound 19 EMI121.3 Compound 20 EMI121.4 Compound 21 EMI121.5 Compounds (continued) Compound 22 EMI122.1 Compound 23 EMI122.2 Compound 24 EMI122.3 Compound 25 EMI122.4 Compound 26 EMI122.5 Compounds (continued) Compound 27 EMI123.1 Table A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate kg/ha 0.4 0.4 0.4 0.4 POST-EMERGENCE Bush bean 9C 9C 9C 7C,9G,6Y Cotton 7C,9G 9C 5C,9G 5C,9G Morningglory lOC lOC 9C lOC Cocklebur lOC 9C 2C,7G 5C,9G Sicklepod 9C lOC lOC 6C,9G Nutsedge 9C 9C lOC 1C, 9G Crabgrass 9C 9C 4C,7G 1C, 7G Barnyardgrass 9C 9C 9C 9C Wild Otas 9C 5C,9G 1C,2G 1C,9G Wheat 6C,9G 5U,9G 1C,3G 2C,9G Corn lOC 9C 7U,1OC 2C,9G Soybean 9C 9C 9C 4C,9G Rice 9C 9C 6C,9G 5C,9G Sorghum lOC lOC 9C 3C.9G Sugar beet - PRE-EMERGENCE Morningglory 2C,9G 9C 8G 9G Cocklebur 9H 9H 9H 9H Sicklepod 2C,9G 9G 2C,8G 9G Nuts edge lOE lOE 8G lOE Crabgrass 6C,9G 3C,8G 2C,5G 1C,4G Barnyardgrass 6C,9H 5C,9H 6C,9H 4C,9H Wild Oats 4C,9H 5C,9H 2C,8G 2C,9G Wheat lOE 6C,9H 2C,9G 1C,9H Corn 10E 9H 4C,8G 2C,9G Soybean 9H 9H 1C,4H 9H Rice 10E lOE lOE 9H sorghum 10H 5C,9H 3C,8G 5C,9H Sugar beet Table A (continued) Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Rate kg/ha 0.4 0.4 0.4 0.4 POST-EMERGENCE Bush bean 6C,9G,6Y 9D,SG,6Y 9C 8D,8G,6Y Cotton 4C,9G 1C,5G 9C 6C,9G Morningglory 1C,4G 1C,5G 9C 3C,7G Cocklebur 3C,8H 2C,9H 10C 3C,9H Sicklepod 3C,9G 2C,6G 9C 6C,9G Nutsedge 7C,9G 3C,8G 5C,9G lOC Crabgrass 2G 3H 6C,9G 5C,9G Barnyardgrass 2C,7H 3C,9H 9C 6C,9H Wild Oats O 0 9C 1C Wheat O 0 5C,9G 1C,9H Corn 2C,7H 2H,9G 5U,9C 3U,9G Soybean 3H 2C,2H 9C 9C Rice 7G 2C,9G 6C,9G 6C,9G Sorghum 3C,9G 2C,9H lOC 6C,9G Sugar beet - PRE-EMERGENCE Morningglory 8G 2C,5H 9C 7G Cocklebur - 9H 9H 9H Sicklepod 2C,9G 1C,4G 9G 1C,8G Nutsedge 1C,5G 2C,8G 10E 1C,7G Crabgrass 1C 1C 3C,9G 3C,4G Barnyardgrass 3C,5H 2C 5C,9H 6C,9H Wild Oats 1C O 5C,9G 3C,9G Wheat O 0 5C,9H 2C,9G Corn 3C,7G 2C,7G 9H 5C,8G Soybean 1C O 9H 2C,6G Rice 3C,6G 3C,8G lOE lOE Sorghum 1C,3G 1C 8C,9H 2C,9H Sugar beet - - - - Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Rate kg/ha 0.4 0.4 0.4 0.4 POST-EMERGENCE Bush bean 6C,9G,6Y 9C 4C,8G,6Y 3C.7G.6Y Cotton 6C,9G 9C 3C,3H,9G 2C,8G Morningglory 9C 9C 5C,8G 2C.7G Cocklebur lOC 4C,9G 4G 7G Sicklepod 9C 9C 3C,9G 2C Nutsedge lOC 3C,8G SC,9G lOC Crabgrass 7C,9G 2C,8G 0 5C.8G Barnyardgrass 9C 9C 0 4C,6H Wild Oats 3C,9G 2C,9G 0 0 Wheat 1C,9G 4C,9G 0 0 Corn 3U,9C 4U,9C 2C,5G 1U,8H Soybean 4C,9G 5C,9G 5C,9G 1C,7H Rice 6C,9G 5C,9G 2G 2C,9G Sorghum 9C 4C,9G 2G 1C,6H Sugar beet PRE-EMERGENCE Morningglory 9G 9G 1C,7G 1C,7G Cocklebur 9H 9H 5C,9H 2C,9H Sicklepod 2C,9G 9G 3C,9G 2C,8G Nuts edge lOE SG lOE 8G Crabgrass 2C,7G 1C,4G 3C 1C,4G Barnyardgrass 1C,9H 9H 5C,6H 6C,7H Wild Oats 2C,9G 9G 0 7G Wheat 2C,9G 9G 0 4G Corn lOE 4C,9G 3C,5G 2C,7G Soybean 3C.9H 3C,8H 2C,3H 2C,4H Rice lOE lOE SC,8H 3C,9H Sorghum 7C,9H 3C,9H 0 2C,5G Sugar beet - - Table A (continued) Cmpd. 13 Cmpd. 14 Cmpd. 15 Cmpd. 16 Rate kg/ha 0.4 0.4 0.4 0.4 POST-EMERGENCE Bush bean 4C,8G,6Y 2C,6G,6Y 7C,9G,6Y 7C,9G,6Y Cotton 3C,7G 5C,9G 6C,9G 9C Morningglory 2C,8G 2C,8G 2C,7G 5C,9G Cocklebur SG 2C 5C,9G 6C,9G Sicklepod 3G 6C,9G 1C 1C,1H Nutsedge SG 5C,9G 9C 2C,9G Crabgrass 3G 0 2C,9H 5C,9G Barnyardgrass 7H 0 5C,9H 6C,9H Wild Oats 2G O 1C 5C,9H Wheat 3G 0 2C,9G lOC Corn 2C,9H 3C,8H 1U,9H 3C,9G Soybean 2H,6G 3C,9H 3G 1H,3G Rice 9G 0 3C,9G 5C,9G Sorghum 2C,9H 0 4C,9H 2C,9G Sugar beet PRE-EMERGENCE Morningglory 9G 9G 8G 5C,9G Cocklebur 9H 9H 9H 9H Sicklepod 9G 9G 3G 5G Nutsedge 8G 8G 2C,8G 9G Crabgrass 2G 2C 2C,7G 2C,8G Barnyardgrass 5C,9G 2C,3H 9H 3C,9H Wild Oats 2C,7G 0 2C,6G 8G Wheat 4G 0 9H 3C,9H Corn 2C,8H 2C,6G 9H 2C,9H Soybean 2C,6G 2C 2G 1C,6H Rice 8H 4G 10E 10E Sorghum 2C,5H 1C 3C,9H 2C,9H Sugar beet - - Table A (continued) Cmpd. 17 Cmpd. 18 Rate kg/ha 0.4 0.4 POST-EMERGENCE Bush bean lC,lH 9C Cotton @C,3H,8G 7C,9G Morningglory 1C,3G 9C Cocklebur 4G 6C,9G Sicklepod 2C 9C Nutsedge 2C,4G lOC Crabgrass 0 9C Barnyardgrass 2C,7H 9C Wild Oats C 9C Wheat 0 5C,9G Corn 2C,7H 5U,9G Soybean 4H 5C,9G Rice 6G 6C,9G Sorghum 2C,9G lOC Sugar beet PRE-EMERGENCE Morningglory 2C,5G 3C,9G Cocklebur 9H 2C,9H Sicklepod 2C 5C,9H Nutsedge 2C,8G lOE Crabgrass 2C 2C,9G Barnyardgrass 5C,7H 2C,9H Wild Oats 0 5C,9H Wheat 2C 5C,9H Corn 2C,7G 2C,9H Soybean 0 3C,9H Rice 10E 10E Sorghum 6G 6C,9H Sugar beet Table A (continued) Cmpd. 19 Cmpd. 19 Cmpd. 20 Cmpd. 21 Rate kg/ha .05 0.4 .05 .05 POST-EMERGENCE Bush bean 3C,7H,6Y 9C 9C 9C Cotton 5C,7H 6C,9G 4C,9G 3C,9G Morningglory 3C 4C,8G 2C.9G 3C,8H Cocklebur 3G 8G 3C,9G 3C,8M Sicklepod 2C 3C,8G 2C,8G 4C,9G Nutsedge 2C,6G lOC 4C,9G 9C Crabgrass 0 2C,8G 1C,3H 2C,3G Barnyardgrass 2C,6H 9C 5C,9H 2C,9H Wild Oats 1C 1C,7G 0 2C,4G Wheat 1C 1C,9G 0 3G Corn 2U,8H 6U,9G 3U,9G 2U,9G Soybean 1C,3H 4C,9G 2C,9H 3C,9H Rice 2C,8H 5C,9G 3C,9G 4C,9G Sorghum 1U,9G 5U,9G 2C,9G 2C,9G Sugar beet PRE-EMERGENCE Morningglory 3C 8G 9G 9G Cocklebur 2C,7H 8H 9H Sicklepod 2C,5G 3C,9G 2C,8G 9G Nutsedge 5G 3C,9G 2C,5G 10E Crabgrass 0 3C 1C,3G 1C,5G Barnyardgrass 3C.6H 3C.9H 5C,9H 9H Wild Oats 0 2C,7G 5C,9G 8G Wheat 3G 2C,8G 4C,9G 2C,8G Corn 2C,6G 1C,9G 2C,9G 2C,9H Soybean 2C 3C,6G 3C.8H 7H Rice 4C,6G lOE 5C,9G lOE Sorghum 2C,7H 3C,9H 4C,9G 1C,9H Sugar beet - - - Table A (continued) Cmpd. 22 Cmpd. 23 Cmpd. 24 Cmpd. 25 Rate kg/ha ,05 .05 .05 .05 POST-EMERGENCE Bush bean 1C 5C,9G,6Y 3C,6H,6Y 9C Cotton 4C,8G 4C,8H 2C,5G 5C,9G Morningglory 3C,8G 3C,5G 3G 2C,7G Cocklebur 2C 5G 4G 4C,9H Sicklepod 5C,9G 1C, 3G 9C Nutsedge 0 3C,8G 7C,9G lOC Crabgrass 3C 2H lOC 4C,9G Barnyardgrass 2C,5H 3C,8H 4H 9C Wild Oats o 2C 0 5C,9H Wheat O 1C O 5C,9G Corn 2G 3C,8H 2C,8H 5C,9G Soybean 3C,8G 2C,7H 2C,2H SC,9G Rice 3G 3C,9H 2C,8H 5C,9G Sorghum 3G 3C,9G 2C,9H 4U,9G Sugar beet - - 2C lOC PRE-EMERGENCE Morningglory 9G 3C 2C,4G 8H Cocklebur 9H 9H 9H 8H Sicklepod 9G 3C,8H 2C,5G 2C,9G Nutsedge 9G 3C,8G 2C,5G lOE Crabgrass 3G 2C 1C 2C Barnyardgrass 2C,5G 5C,9H 2H 4C,9H Wild Oats 1C 2C,8G 2C,8G 3C,9G Wheat 1C 3C,9G 9G 2C,9G Corn 2C,8G 4C,9H 9G 3C,9H Soybean 8H 3C,5H 4C,7G 3C,7H Rice 6G 5C,9H 3C,8H 10E Sorghum 2C,5G 4C,9H 2C,9H 2C,9G Sugar beet - - 2C.9G 9C Table A (continued) Cmpd. 26 Cmpd. 27 Rate kg/ha .05 .05 POST-EMERGENCE Bush bean 5C,9G,6Y 5C,9G,6Y Cotton 9C Morningglory 5C,9G 5C,9G Cocklebur 4C,9G 4C,9G Sicklepod 3C,8G 4C,3H Nutsedge 2C,7G SG Crabgrass 2C,9G 2C,8G Barnyardgrass 2C,9H 5C,9H Wild Oats 2C,8G 0 Wheat 5C,9G 0 Corn 3U,9H 9C Soybean 2C,9H 9C Rice 5C,9G 5C,9G Sorghum , 2C,9G 9C Sugar beet 3C,9G 9C PRE-EMERGENCE Morningglory 9C 9C Cocklebur 9H Sicklepod 5C,9G 2C.9G Nuts edge lOE 6G Crabgrass 3C,9G 2C,6G Barnyardgrass 4C.9H 3C,9H Wild Oats 3C.9G 3C, 9G Wheat 10C 1C,6G Corn 9G 5C,9H Soybean 3C,9H 9H Rice lOE lOE Sorghum 5C,9H 5C,9H Sugar beet 5C.9G 9C Several of the compounds of this invention were further tested in a pre-emergence herbicide screen as described in Test B. Test B Two plastic bulb pans were filled with fertilized and limed Woodstown sandy loam. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusqalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (IPomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinoza), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four containers were treated preemergence with several test compounds within the scope of the invention. Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data is summarized in Table B. Table B PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 1 Rate kg/ha 0.03 0.12 0.008 Crabgrass 7G 9G,5H 2G Barnyardgrass 8G,9C 9G,9C 6G,3C Sorghum - @ 9G Wild Oats 8G,8C lOC 7G Johnsongrass 9G,8C lOC 7G Dallisgrass 9G.3H 9G,3H 6G Giant foxtail 8G,5H uG,9C 2G Ky. bluegrass 10E 10E lOC Cheatgrass lOC lOC 9G Sugar beets 7G,7C lOC 8G Corn lOC lOC lOC Mustard 9G,9C lOC 8G Cocklebur 7G,3H 8G,SH 6G Pigweed lOE lOE - Nutsedge lOE lOE lOC Cotton 9G,5H 9G,SH 6G Morningglory 7G 9G,8C 5G Sicklepod 6G 8G,5C 4G Teaweed 7G,3C 8G,5C 8G Velvetleaf 6G,3H 9G,9C Jimsonweed 6G lOC 5G Soybean 7G,5H 9G,8C 6G Rice 10E 10E 10C Wheat 8G,8C 10E 3G Table B (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 19 Compound 20 Rate kg/ha 0.120 0.500 0.030 0.120 Crabgrass 2G SG 2G 4G Barnyardgrass 8G,3H lOC 7G,3H 9G,5H Sorghum - - 7G,5H 9G,SH Wild Oats 2G 5G 4G 5G Johnsongrass 5G,3H 8G,3H 4G,3H 6G,2H Dallisgrass 6G 8G,5H 2G 4G Giant foxtail 6G,5H 8G,5H 4G 6G,3H Ky. bluegrass 8G,8C lOC 6G 7G Cheatgrass 6G,3C lOC 8G,8C 8G,9C Sugar beets 8G,8C lOC 8G,8C lOC Corn 7G,5H 9G,8C 6G,3H 7G,3H Mustard 9G,9C lOC 9G,8C 9G,9C Cooklebur 6G 7G,3H 6G 5G Pigweed 8G lOC Nutsedge 7G 10E 7G 7G Cotton 3G 8G 3G 5G,3H Morningglory 0 6G,5H 4G 9G,5C Sicklepod 6G 7G 7G 8G,3H Teaweed 5G 8G,3H 5G 10C Velvetleaf 6G,5H 9G,9C 5G,5H 8G,9C Jimsonweed 6G 7G 7G 8G,8C Soybean 3G 6G,5H 3G,3H 6G,5H Rice 9G,9C lOC 7G,8C lOC Wheat 4G 6G 0 4G Table B (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 21 Compound 22 Rate kg/ha 0.030 0.120 0.007 0.030 Crabgrass 0 6G 0 0 Barnyardgrass 6G,2H 8G,5H 0 3G Sorghum 6G,3H 9G,5H 0 0 Wild Oats 3G 6G 0 0 Johnsongrass 4G,2H 7G,5H 0 0 Dallisgrass 0 5G 0 0 Giant foxtail 3G 7G,3H 0 0 Ky. bluegrass 5G,3H 7G,3H 4G 0 Cheatgrass 8G,8C 8G,9C 0 0 Sugar beets lOC lOC 6G 8G Corn 5G,3H 7G,3H 2G 3G Mustard 9G,SH 9G,9C 9G 9G,9C Cocklebur 0 3G 0 2G Pigweed lOE lOE - Nutsedge 9G,9E lOE 0 5G Cotton 2G 4G 2G 5G Morningglory 3G 3G 0 7G Sicklepod 8G 8G 5G 6G Teaweed 7G 8G 6G 9G Velvetleaf 7G,5H 9G,8C 5G,5H 8G Jimsonweed 5G 6G 0 4G Soybean 3G 6G,5H SG 8G Rice 8G,8C 10E 0 5G Wheat 2G 4G 0 0 Table B (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 23 Rate kg/ha 0.030 0.120 Crabgrass O 0 Barnyardgrass 2G 3H,8G Sorghum 2G 3H,8G Wild Oats 0 2G Johnsongrass 0 2H,4G Dallisgrass 4G 8G Giant foxtail 3H,4G 5H,8G Ky. bluegrass 6G 10E Cheatgrass SG 8G Sugar beets SG 8G Corn 3G 3H,7G Mustard 9G,9C 9G,9C Cocklebur 2G 2G Pigweed Nuts edge 2G 6G Cotton 3G SG Morningglory 2G 2G Sicklepod 2G 5G Teaweed O 0 Velvetleaf 0 5G Jimsonweed 0 4G Soybean 3G 3G Rice 8G 9G,9C Wheat 2G 3G A number of compounds were also tested to more accurately define their utility in post-emergence applications. Test C The test chemicals, dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. One day after treatment, plants were observed for rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Sicklepod (Cassia obtusifolia), morningglory (IPomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Diqitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, and mustard. All plants were sprayed approximately 14 days after planting. Additional plant species, such as johnsongrass and field bindweed, are sometimes added to this standard test in order to evaluate unusual selectivity. Again, Compound 1 appeared to be one of the most active compounds when applied post-emergence. All of the compounds tested, however, were shown to be highly active post-emergence herbicides. Some of the compounds, for example, Compounds 3, 4, 6 and 15, show potential utility for selective post-emergence weed control in wheat. Table C Over-the-Top Soil/Foliage Treatment Compound 1 Rate kg/ha 0.25 0.06 0,015 0.004 Soybeans lOC lOC lOC 8G Velvetleaf lOC lOC 7G,8C 2G Sesbania lOC lOC lOC 9G Sicklepod lOC lOC 9G 8G Cotton lOC lOC - - Morningglory 10C 10C 1G 1G Alfalfa lOC lOC 4G,4C SG,4C Jimsonweed 10C 9G - 9G Cocklebur 10C 9G 8G 7G Sunflower 10C 9G,8C 4G 2G Mustard 9G,8C - 7G,1C 4G Sugar beets 10C 10C 4C,7G 5G,3C Corn 10C 10C 10C 10C Crabgrass 8G 9G 10C 5G,4C Rice 9G,6C 9G,4C 3G,2C 4G Nutsedge 10C 9G 5G,4C 3G Barnyardgrass 10C 9G,8C 8G 7G Wheat 8G,6C 7G 7G,4C 8G,7C Giant Foxtail 9G,6C 9G,5C - 4G Wild Oats 7G,6C 8G,6C 4G 4G Sorghum 8G,8C 8G,8C 8G,9C 8G Johnsongrass 10C 10C 10C 7C Field Bindweed 9G,4C 9G,5C 2C 4G Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 20 Compound 23 Rate, kg/ha 0.015 0.004 0.06 0.015 Soybeans 8G,6C 6G 3G 0 Velvetleaf O 0 4G 0 Sesbania O - 0 0 Sicklepod O 0 0 0 Cotton 3G 3G 3G 3G Morningglory 2G 0 4G 3G Alfalfa 7G 5G 4G 3G Jimsonweed 3G 0 0 0 Cocklebur 0 - 2G 3G Sunflower 2G 0 3G 1G Rape 2G 0 SG 0 Sugar beets 2G 0 Corn 2G 0 1C O Crabgrass 4G 0 0 0 Rice 6G 2G 6G 6G Nutsedge O 0 0 0 Barnyardgrass 0 3G 0 0 Wheat O 0 0 0 Giant Foxtail 2G 4G 0 0 Wild Oats O 0 0 0 Sorghum 3G SG 8G 6G Johnsongrass O 0 0 0 Field Bindweed 3G 0 0 0 Test D Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Woodstown sandy loam soil. One pan was planted with seeds of wheat (Triticum aestivum). barley (Hordeum vul gare), wild oats (Avena fatua). downy brome (Bromus tectorum). cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides). annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (AaroPyron repens), Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus risidus). The other pan was planted with seeds of Russian thistle (Salsola kali), tansy mustard (Descuraina pinnata), cleavers (Galium aParine) tumble mustard (Sisymbrium altis siam), kochia (Kochia scoparia), shepherd's purse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum nigrum), yellow rocket (Barbarea vulgaris), rapeseed (Brassica napus), and wild buckwheat (Poyqonum convolvulus). The above two pans were treated preemergence. At the same time, two pans in which the above plant species were growing were treated postemergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species. The compounds applied were diluted with a nonphytotoxic solvent and sprayed over the top of the pans. An untreated control and a solvent-alone control were included for comparison. All treatments were maintained in the greenhouse for 19-21 days at which time the treatments were compared to the controls and the effects visually rated. The recorded data are presented in Table D. Some of the compounds tested have utility for selective weed control in cereal crops such as wheat and barley. Table D Compound 3 Pre-Emergence Post-Emergence Rate kg/ha 0.12 wheat 0 0 barley 0 0 wild oats 0 0 downy brome 0 2G cheatgrass 2G 2C,5G blackgrass 4G 1C,4G annual bluegrass 4G 4G green foxtail 0 SG quackgrass 2G 7G Italian ryegrass 3G 3G ripgut brome 3G- 3G Russian thistle 0 0 tansy mustard 9G 2C,4G Galium aparine 2G 0 tumble mustard 6G 7C,9G kochia 0 3G shepherd's purse 8G 3C,8G Matricaria inodora 7G 3C,sG black nightshade SG 4G yellow rocket SG 2C,6G wild mustard 4G lOC wild buckwheat 3G 3G Table D (continued) Compound 20 Pre-Emergence Post-Emergence Rate kg/ha 0.060 0.015 0.060 0.015 wheat 7G 2G 6G 3G barley 1C,7G 2G 6G 3G wild oats 1C,7G 5G SG 2G downy brome 2C,9G 8G 8G 7G cheatgrass lC; ;9G 8G 8G 7G blackgrass 2C,8G 7G 5G 3G annual bluegrass SG 7G 7G 3G green foxtail 2C,8G 2C,4G 2C,9G 4G quackgrass 9G 8G 8G 6G Italian ryegrass 1C,8G 7G 4C,8G 7G ripgut brome 8G 8G 2C,8G 7G Russian thistle 2C,3G 2G 8C,8G 4C,SG tansy mustard 2C,9G 9G 8C,8G 5C,7G Galium aparine 6G 8G 7G 4G tumble mustard 1C,8G 9G 10C 7G kochia 7G SG 3C,8G 4G shepherds purse 2C,9G 9G 4C,9G 7G Matricaria inodora 7G 7G 8C,8G 2C,7G black nightshade 8G 5G 6G 6G yellow rocket 9G 8G 7G SG rapeseed 2C,9G 9G lOC 2C,8G wild buckwheat 7G 6G 7G 4G Table D (continued) Compound 21 Pre-Emergence Post-Emergence Rate kg/ha 0.060 0.015 0.060 0.015 wheat 3G 0 3G 0 barley 3G 0 SG 0 wild oats SG 0 4G 0 downy brome 9G 8G 9G 7G cheatgrass 2C,9G 7G 8G 6G blackgrass 7G 6G 6G 3G annual bluegrass 7G 6G 2C,8G 3G green foxtail 2C,6G 3G 2C,6G 6G quackgrass 9G 8G 8G 7G Italian ryegrass 8G 8G 2C,8G 6G ripgut brome 8G 6G 7G 6G Russian thistle 1C,2G 0 8C,8G 0 tansy mustard 9G 9G lOC 9G Galium aparine 10E 8G 6G 5G tumble mustard 2C,9G 9G lOC 9G kochia 8G 2C,5G 2C,8G 5G shepherd's purse 9C,9G 9C,9G lOC 2C,8G Matricaria inodora 8G 9G 8C,8G 8C,8G black nightshade 6G 3G 7G 6G yellow rocket 9G 7G 8C,8G 8C,8G rapeseed 3C,9G 9G lOC lOC wild buckwheat 6G 4G 2C,8G 7G Table D (continued) Compound 23 Pre-Emergence Post-Emergence Rate kg/ha 0.060 0.250 0.060 0.250 wheat 1C,2G SG 2G 7G barley 6G 2C,8G 3G 7G wild oats SG 7G 3G SG downy brome SG 8G 5G 6G cheatgrass 6G 8G 5G 7G blackgrass 5G 1C,7G 6G 2C,7G annual bluegrass 6G 1C,8G 4G 3C,8G green foxtail 0 2C,6G 0 2C,5G quackgrass 4G 8G 2G 6G Italian ryegrass 8G 2C,9G 2C,6G 2C,8G ripgut brome 6G 1C,8G 5G 7G Russian thistle 0 2C,5G 0 lOC tansy mustard 8G 2C,9G 5G 8G Galium aparine 9G 10E 0 3G tumble mustard 7G 9G 0 6G kochia - - - 0 Shepherd's purse 2C,9G 10C 5G 10C Matricaria inodora 8G 9G 3G 9G black nightshade 0 5G 0 4G yellow rocket 8G 9G 0 6G rapeseed 2C,8G 9G 7G 9C,9G wild buckwheat 0 6G 0 3G A final test was designed to evaluate the potential utility of compounds from within the scope of the invention for selective weed control in rice. Test E The crop was transplanted into simulated paddies containing soil and propagules of barnyardgrass (Echinochloa sp.), water chestnut (Eleocharis sp.), and arrowhead (Sagittaria sp.). Three days after transplanting, the test chemicals were applied to the paddy water in a non-phytotoxic solvent at the rates shown in Table E. The paddies were maintained in a greenhouse. and plant response ratings were taken several weeks after application utilizing the rating system as described for Test A. Compounds 11 and 14 appear to have utility for weed control in transplanted rice. Table E Compound 11 Rate, grams/hectare 100 Rice lG Barnyardgrass 9C Water Chestnut 10C Arrowhead 6G,5H Compound 14 Rate, grams/hectare 25 100 Rice 0 0 Barnyardgrass 7C 8C Water Chestnut 0 0 Arrowhead O 0

Claims: CLAIMS: 1. A compound of the formula: EMI147.1 wherein Ra is CH3 or CH2CH3; Rb is CH3 or CH2CH3; L is EMI147.2 EMI147.3 EMI148.1 R5 is C1-C4 alkyl. C1-C4 alkoxy. OCH2CH2OCM3, F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI148.2 EMI148.3 R6 is H, F, Cl, Br, CF3, CM3, OCH3, SCH3 or 0CF2H; R7 is H. CH3, OCH3, F, C1, Br, OSO2CH3, S02N(CH3)2 or S(O)nCH3; R8 iS CH3, CH2CH3, OCH3, OCH2CH3, F, C1, Br, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R9 is C1-C3 alkyl, F, C1, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R10 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; R11 is H, CH3 or CH2CH3; R12 is H, CH3 or CH2CH3; R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyi; R18 is H or CH3; R19 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R20 is C1-C3 alkyl; R21 is C1-C3 alkyl; R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=CH2; m is 0 or 1; n is 0 or 2; Q1 is O, S, SO2 or NR17; is is O, s or NR17; and W is O, S or SO2; EMI149.1 EMI150.1 x is CH3, OCH3, OCH2CH3. Cl, F, Br, OCF2H, CH2F or CF3; Y iS H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3. OCF2H, SCF2H, CR24(OCH3)2, EMI150.2 EMI150.3 or CR24(QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O; X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 -is H or CH3; X2 is CH3, CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3: X3 is CH3 or OCH3; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1, then R13 is H; 3) when L is L-17, then R17 and R18 are not simultaneously H; 4) when X is Cla F or Br, then Z is CH and Y is OCH3, OCM2CH3, N(CH3)2 or OCF2H. 2. A compound of Claim 1 where A is A-1. 3. A compound of Claim 2 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3, OCH3, C1 or CF3. 4. A compound of Claim 3 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-ll, L-16 or L-17. 5. A compound of Claim 4 where L is L-1; R5 is OCH3, OCH2CH3, Cl, NO2, CF3, CO2CH3, CO2CH2CH3, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF2H, SCF2H, OCH2CH=CH2, OCH2C=CH, EMI151.1 EMI151.2 R22 is C1-C3 alkyl; R23 is CH3 and n is 2. 6. Compounds of Claim 4 where L is L-2 and R7 is Cl, CH3, OCH3, SCH3 or Br. 7. Compounds of Claim 4 where L is L-3 and R8 is Cl, SO2CH3 or SO2N(CH3)2. 8. Compounds of Claim 4 where L is L-5 and R9 is CO2CH3 or CO2CH2CH3. 9. The compound of Claim 1 which is 2-fE(4- methoxy-6-methylpyrimidin-2-yl)aminocarcarbonyl]amino- sulfonyl]benzoio acid methyl ester1 dimethylsulfonium inner salt. 10. The compound of Claim 1 which is 2-[[(4,6- dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester, dimethylsulfonium inner salt. 11. The compound of Claim 1 which is N-((4,6- dimethylpyrimidin-2-yl ) aminocarbonyl 1 -2-methylsulfonyl- benzenesulfonamide, dimethylsulfonium inner salt. 12. The compound of Claim 1 which is 2-[[(4,6- dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester, dimethylsulfonium inner salt. 13. The compound of Claim 1 which is N-((4,6- dimethoxypyrimdin-2-yl)aminocarbonyl]-2-dimethyl aminosulfonylbenzenesulfonamide. dimethylsulfonium inner salt. 14. A compound having the formula: EMI152.1 wherein R is H or CH3; Rc is H, C(O)R1, C(O)NR2R3 or CO2R4: R1 is C1-C3 alkyl or CF3; R2 is H, CH3 or C2H5; R3 is C1-C3 alkyl; R4 is C1-C3 alkyl; L is EMI152.2 EMI152.3 EMI153.1 R5 is C1-C4 alkyl, C1-C4 alkoxy, OCH2CH2OCH3, F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI153.2 EMI153.3 EMI154.1 R6 is H, F, Cl, Br, CF3, CH3, OCH3, SCH3 or OCF2H; R7 iS H, CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3 ; R8 is CH3. CH2CH3, OCH3, OCH2CH3, F, C1, Br, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; ; R9 is C1-C3 alkyl, F, C1, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R10 iS Cl, NO2, CO2CH3, CO2CH3CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 oR OCH2CH3; R11 iS H, CH3 or CH2CH3; R12 iS H, CH3 or CH2CH3; R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl; R18 is H or CH3; R19 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R20 is C1-C3 alkyl; R21 is C1-C3 alkyl; R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=CH2; m is 0 or 1; n is O or 2; Q1 is O, S. SO2 or NR17; Q2 is is O, S or NR17; and W is O, S or SO2; EMI155.1 X is CH3, OCH3, OCH2CH3, C1, F, Br, OCF2H, CH2F or CF3; Y iS H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24(QCH3)2, EMI155.2 EMI155.3 or CR24(QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or 0; X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 is H or CH3; X2 is CM31 CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH@, CH3 or CH2CH3; X3 is CH3 or OCH3; and their agriculturally suitable salts; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1, then R13 is H; 3) when L is L-17, then R17 and R18 are not simultaneously H; and 4) when X is Cl, F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2H, 15. A compound of Claim 14 where R is H, Rc is H and A is A-1. 16. A compound of Claim 15 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3, OCH3, Cl or CF3, 17. A compound of Claim 16 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17. 18. A compound of Claim 17 where L is L-1, R5 is OCH3, OCH2CH3, Cl, NO2, CF3, CO2CH3, CO2CH2CH3, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF2H, SCF2H, OCH2CH=CH2, OCH2C=CH, EMI156.1 EMI156.2 R22 is C1-C3 alkyl; R23is CH3 and n is 2. 19. A compound of Claim 17 where L is L-2 and R7 is Cl, CH3, OCH3, SCH3 or Br. 20. A compound of Claim 17 where L is fl-3 and R8 is Cl, SO2CH3 or SO2N(CH3)2, 21. A compound of Claim 17 where L is L-5 and R9 is CO2CH3 or CO2CH2CH3, 22. A compound of Claim 14 which is 2-((1-(4,6- dimethylpyrimidin-2-yl)amino]-1-(hydroxyimino)methyl] aminosulfonyl)benzoic acid methyl ester. 23. A compound of Claim 14 which is 2-([l-(4- methoxy-6-methylpyrimidin-2-yl)amino)-1-(hydroxyimino)- methyl]aminosulfonyl]benzoic acid methyl ester. 24. A compound of Claim 14 which is N',N'-di- methyl-N-[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)amino]1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide. 25. A compound of Claim 14 which is N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide. 26. A compound having the formula: EMI157.1 wherein Rd is C1-C3 alkyl; R is H or CH3; L is EMI157.2 EMI157.3 EMI158.1 R5 is C1-C4 alkyl, C1-C4 alkoxy, OCH2CH2OCH3, F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH2, C6H5, EMI159.1 EMI159.2 R6 is H, F, Cl, Br, CF3, CH3. OCH3, SCH3 or OCF2H; R7 is H, CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3; R8 is CH3, CH2CH3, OCH3, OCH2CH3, F, C1, Br, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23: R9 is C1-C3 alkyl. F, C1, Br, NO2, CO2R19, SO2NR20R21, SO2N(CH3)CH3 or S(O)nR23; R10 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; 3 R11 is H. CH3 or CH2CH3; R12 is H, CH3 or CH2CH3: R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; 17 is H or C1-C4 alkyl; R18 is H or CH3; Rl9 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2C1 or CH2CH=CH2; R20 is C1-C3 alkyl; R21 is C1-C3 alkyl; R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=CH2; m is 0 or 1: n is O or 2; Q1 is O, S. SO2 or NR17; Q2 is O, S or NR17; and W is O, S or SO2; A is EMI160.1 EMI160.2 X is CH3. OCH3, OCH2CH3. C1, F, Br, OCF2H, CH2F or CF3; Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24(QCH3)2, EMI160.3 EMI160.4 or CR24(QCH2CH3)2: Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O; X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 is H or CH3; X2 is CH3, CH2CH3 or CH2CF3 ; Y3 is OCH3. OCH2CH3, SCH3, CH3 or CH2CH3; X3 is CH3 or OCH3; and their agriculturally suitable salts; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1, then R13 is H; 3) when L is L-17. then R17 and R18 are not simultaneously H: 4) when X is C1, F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2M; ; 5) when L is L-l and A is A-1, R5 is C2-C4 alkyl, C2-C4 alkoxy, OCH2CH2OCH3, OSO2R22, S(O)nCH2CH=CH2, WCF2, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI161.1 EMI161.2 6) when L is L-1 and A is A-2 or A-3, then R5 is C2-C4 alkyl, C2-C4 alkoxy, OCH2CH2OCH3, OSO2R22, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI162.1 EMI162.2 7) when L is L-3 and A is A-1, A-2 cr A-3, then R8 is SO2NR20R21, SO2N(OCH3)CH3 or SO2R23: 8) when L is L-4, L-5 or L-6 and A is A-1, A-2 and A-3, then R9 is C1-C3 alkyl, F. Cl. Br, NO2, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23: and 9) when L is L-2, then A is A-5 or A-6. 27. A compound of Claim 26 where R is H and A iS A-1. 28. A compounds of Claim 27 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2 and X is CH3, OCH3, Cl or CH3. 29. A compound of Claim 28 where L is L-l and R5 is OSO2R22, SO2CH2CH=CH2, OCF2H, SCF2H, OCH2CH=CH2, OCH2C=CH, EMI162.3 EMI162.4 3Q. A compound 9f claim. 1 wherein; L is L-1, L-2, L-3, L-4, L-5, L-8, L-10, L-11 or L-17; R5 is C1-C4 alkyl, C1-C4 alkoxy, F, C1, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF3, OCHF2, C3-C4 alkenyloxy, CH2CH2OCH3, CH2CH2OC2H5, EMI163.1 R6 is H, F, C1, Br, CF3, CH3 or OCH3; R7 is H, CH3, OCH3, Cl, OS02CH3 or S(O)nCH3; R8 is CH3, OCH3, Cl, SO2NR20R21 or SO2N(OCH3)CH3; R9 is CH3, C1, Br, NO2, C02R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR13; R11 is H or CH3; R12 is H or CH3; R13 is H; R17 and R18 are H; R22 is C1-C3 alkyl; Q1 is 0, S or SO2; A is A-i; X is CH3 or OCH3; or may be Cl when Y is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2CH3, CF3' -OCH2CF3, CH(OCH3)2; and Ra, Rb, R16, R19, R20, R21, R23, m, n and Z are as defined in claim 1. 31. A compound of claim 14 wherein: is H or cH3, Rc is as defined in claim 14; L is L-l; R5 is C1-C4 alkyl, C1-C4 alkoxy, F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, or C1-C2 alkyl substituted with OCH3 or OC2H5; R6 is H, F, C1, Br, CF3, CH3, OCH3 or SCH3; R19, R20, R21 R23 and W are as defined in claim 14; R22 is C1-C3 alkyl; A is A-i; X is CH3, OCH3 or C1; Y is CH3, C2H5, OCH3, OC2H5, CH2OCH3, CH(OCH3)2 or EMI164.1 and Z is as defined in clam 14. 32. A composition suitable for controlling the growth of undesired vegetation or for regulating the growth of plants which. comprises an effective amount of a herbicidal compound or plant growth regulant compound and at least one'of the following: surfactant, solid or liquid diluent, characterized in that said herbicidal compound or plant growth regulant compound comprises a compound of any of claims 1-31. 33. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound characterized in that said herbicidal compound comprises a compound of any of claim 1 to 31. 34. A method for regulating the growth of plants by applying to the locus of said plants an effective but subutantially non-phytotoxic amount of a plant growth regulant, characterized in that said plant regulant comprises a compound of any of claims 1 to 31. 35. A method for the preparation of a compound of claim 1 which comprises reacting a sulfonyl isocyanate of formula LSO2NCO (IV) wherein L is as defined in claim 1, with an S,S-dialkyl-N-(heterocyclic)sulfilimine of formula EMI164.2 wherein Ra, % and A are as defined in claim 1. 36. A method for the preparation of a compound of claim 14 which comprises reacting an isothiourea derivative of formula EMI165.1 wherein L, R, Rd and A are as defined in claim 26, with hydroxylamine, to obtain a compound of claim 14 wherein Rc is H, and optionally reacting the product with RcCl or R3NCO, wherein Rc..i5 C(O)R1, C(O)NR2R3 or CO2R4 and R1, R2, R3 and R4 are as defined in claim 14. 37. A method for the preparation of a compound of claim 26 which comprises: (a) reacting a compound of formula EMI165.2 wherein L, A and R are as defined in claim 26 and X is C1 or Br, with MSRd, wherein M is Na, K or Li and Rd is as defined in clam 26; (E)) reacting a compound of formula EMI165.3 wherein L and Rd are as defined in claim 26, with the lithium salt of a 2-aminoheterocycle of formula EMI165.4 wherein A and L are as defined in claim 26; or (c) reacting a sulfonyl halide of formula LSO2Cl wherein L is as defined in claim 26, with an S-alkyl isothiourea of formula EMI166.1 wherein Rd, A and R are as defined in claim 26. Claigns: 1. A process for the preparation of a compound of the formula EMI167.1 wherein Ra is CH3 or CH2CH3; Rb is CH3 or CH2CH3; L is EMI167.2 EMI167.3 EMI168.1 R5 is C1-C4 alkyl, C1-C4 alkoxy, OCH2CH2OCH3, F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Cl-Cz alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI168.2 EMI168.3 R6 is H, F, CI, Br, CF3, CH3, OCH3, SCH3 or OCF2H; R7 is H. CH3, OCH3, F, C1, Br, OSO2CH3, SO2N(CH3)2 or S(O)nCH3; R8 is CH3, CH2CH3, OCH3, OCH2CH3, F, C1, Br. SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R9 is C1-C3 alkyl, F, Cl, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R10 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; R11 is H, CH3 or CH2CH3; R12 is H, CH3 or CH2CH3; R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl; R18 is H or CH3; R19 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2C1 or CH2CH=CH2: R20 is C1-C3 alkyl: R21 is C1-C3 alkyl: R22 is C1-C3 alkyl or N(CH3)2: R23 is C1-C3 alkyl or CH2CH=CH2; m is O or 1; n is O or 2; Q1 is O, S, SO2 or NR17; Q2 is O, S or NR17; and W is O, S or SO2; A is EMI169.1 EMI170.1 X is CH3, OCH3, OCH2CH3, Cl, F, Br, OCF2H. CH2F or CF3; Y is H, CM3, OCH3, OCH2CH3. CH2OCH3. CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH3, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24(QCH3)2, EMI170.2 EMI170.3 or CR24(QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O; X1 is CM3, OCH3, OCH2CH3 or OCF2H: Y2 is H or CH3; X2 is CH3, CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3; X3 is CH3 or OCH3; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four: 2) when m is 1. then R13 is H: 3) when L is L-17, then R17 and R18 are not simultaneously H: 4) when X is Cl. F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2H, which comprises reacting a sulfonyl isocyanate of formula LSO2NCO (IV) wherein L is as defined above, with an S,S-dialkyl-N-(heterocyclic)sulfilimine of formula EMI171.1 wherein Ra, Rb and A are as defined above, 2. A process of claim 1 wherein: L is L-1, L-2, L-3, L-4, L-5, L-8, L-10, L-ll or L-17; R5 is C1-C4 alkyl, C1-C4 alkoxy, F, C1, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF3, OCHF2, C3-C4 alkenyloxy, CH2CH2OCH3, CH2CH2OC2H5, EMI171.2 R6 is H, F, C1, Br, CF3, CH3 or OCH3; R7 is H, CH3, OCH3, C1, OSO2CH3 or S(O)nCH3; R8 is CH3, OCH3, Cl, SO2NR20R21 or SO2N(OCH3)CH3; R9 is CH3, Cl, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR13; R11 is H or CH3; R12 is H or CH3; R13 is H; R17 and R18 are H; R22 is C 1-C3 alkyl; Q1 is O, S or S02; A is A-1; X is CH3 or OCH3; or may be Cl when Y is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2CH3, CF3, OCH2CF3, CH(OCH3)2; and Rat Rb, R15, Rlgt R20, R21, R23, m, n and Z are as defined in claim 1. 3. A process of claim 1 where A is A-1. 4. A process of claim 3 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2; X is CH3, OCH3, Cl or CF3; and L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17. 5. A process of Claim 4 where L is L-1; R5 is OCH3, OCH2CH3, Cl, nO2, CF3, CO2CH3, CO2CH2CH3, SO2N(CH3)2, SON(OCH3)CH3, OSO2R22, S(O)nR23, OCF2H, SCF2H, OCH2CH=CH2, OCH2CiCH, EMI172.1 EMI172.2 R22 is C1-C3 alkyl; R23 is CH3 and n is 2. 6. A process of Claim 4 where L is L-2 and R7 is Cl, CH3, OCH3, SCH3 or Br; or where L is L-3 and R8 is C1, S02CH3 or SO2N(CH3)2; or where L is L-5 and R9 is CO2CM3 or CO2CH2CM3. 7. A process of claim 1 or 2 wherein the product is a compound selected from 2- ( ( (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl3 amino- sulfonyllbenzoic acid methyl ester, dimethylsulfonium inner salt; 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester, dimethylsulfonium inner salt; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methylsulfonylbenzenesulfonamide, dimethylsulfonium inner salt; 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester, dimethylsulfonium inner salt; and N-t(4,6-dimethoxypyrimidin-2-yl)aminocarbonyll-2-dimethyl- aminosulfonylbenzenesulfonamide, dimethylsulfonium inner salt. 8. A process for the preparation of a compound having the formula; EMI172.3 wherein R is H or CH3: Rc is H, C(O)R1, C(O)NR2R3 or CO2R4; R1 is C1-C3 alkyl or CF3; R2 is H, CH3 or C2H5: R3 is C1-C3 alkyl; R4 is C1-C3 alkyl: L is EMI173.1 EMI173.2 EMI174.1 R5 is C1-C4 alkyl, C1-C4 alkoxy, OCH2CH2OCH3. F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5. EMI174.2 EMI174.3 R6 is H, F, Cl, Br, CF3, CH3, OCH3, SCH3 or OCF2H; R7 is H. CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3; R8 iS CH3, CH2CH3, OCH3, OCH2CH3, F, Cl, Br, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R9 is C1-C3 alkyl, F, Cl, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23: R10 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; R11 is H, CH3 or CH2CH3; R12 is H, CH3 or CH2CH3; R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl; R18 is H or CH3; R19 is C1-C4 alkyl. CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R20 is C1-C3 alkyl: R21 is C1-C3 alkyl: R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=CH2; m is 0 or 1; n is 0 or 2; Q1 is O, S, SO2 or NR17; Q2 is o. s or NR17; and W is 0. S or SO2; A is EMI175.1 EMI176.1 X is CH3, OCH3, OCM2CH3, C1, F, Br, OCF2H, CH2F or CF3; Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24(QCH3)2, EMI176.2 EMI176.3 or CR24(QCH2CH3)2 Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O; X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 is H or CH3; X2 is CH3, CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3; X3 is CH3 or OCH3; and their agriculturally suitable salts: provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1. then R13 is H; 3) when L is L-17, then R17 and R18 are not simultaneously H; and 4) when X is Cl, F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2H; which' comprises reacting an isothiourea derivative of formula EMI177.1 wherein L, R, Rd and A are as defined above, with hydroxylamine, to obtain a compound of formula (II) wherein Rc is H, and optionally reacting the product with RcCl or R3NCO, wherein Rc is C(O)R1, C(O)NR2R3 or CO2R4 and R1, R2, R3 and R4 are as defined above. 9. A process of claim 8 wherein: R is H or CH3; Rc is as defined in claim 8; L is L-l; R5 is C1-C4 alkyl, C1-C4 alkoxy, F, C1, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, or C1-C2 alkyl substituted with OCH3 or OC2M5; R6 is H, F, C1, Br, CF3, CH3, OCH3 or SCH3; R191 R20, R21, R23 and W are as defined in claim 8; R22 is C1-C3 alkyl; A is A-l; X is CH3, OCH3 or Cl; Y is CH3, C2H5, OCH3, OC2H5, CH2OCH3, CH(OCH3)2 or EMI177.2 and Z is as defined in claim 8. .1Q. A process of claim 8 or 9 where R is H, Rc is H and A is A-1. 11. A process of claim 10 where Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CH(OCH3)2; X is CH3, OCH3, Cl or CF3; and L is L-1, L-2, L-3, L-5, L-8, L-10, L-il, L-16 or L-17. 12. A process of Claim 11 where L is L-l. R5 is OCH3, OCH2CH3, Cl, NO2, CF3, CO2CH3, CO2CH3CH3, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, OCF2H, SCF2H, OCH2CH=CH2, OCH2C=CH, EMI178.1 EMI178.2 R22 is C1-C3 alkyl; R23is CH3 and n is 2. 13. A process of claim 11 where L is L-2 and R7 is Cl, CM3, OCH3, SCH3 or Br; or where L is L-3 and R8 is C1 SO2CH3 or SO2N(CH3)2; or where L i L-5 and Rg is CO2CH3 or CO2CM2CH3. 14. A process of claim 8 of 9 wherein the product is a compound selected from 2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxyimino) methyl]-aminosulfonyl]benzoic acid methyl ester; 2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1 (hydroxyimino)-methyl]aminosulfonyl]benzoic acid methyl ester; N',N'-dimethyl-N-[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)amino]1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide; and N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin-2-yl) amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide. 15. A process for the preparation of a compound haying the formula: EMI178.3 wherein Rd is C1-C3 alkyl: R is H or CH3: L is EMI178.4 EMI179.1 R5 is C1-C4 alkyl. C1-C4 alkoxy, OCH2CH2OCH3. F, Cl, Br, NO2, CF3, CO2R19, SO2NR20R21, SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI180.1 EMI180.2 R6 is H. F. Cl, Br. CF3, CH3, OCH3, SCH3 or OCF2H: R7 is H, CH3, OCH3. F, Cl. Br. SO2N(CH3)2, OSO2CH3 or S(O)nCH3: R8 is CH3, CH2CH3. OCH3. OCH2CH3. F. Cl, Br, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23: R9 is C1-C3 alkyl. F, Cl, Br, NO2, CO2R19, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; R10 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 oR OCH2CH3; R11 is H. CH3 or CH2CH3; R12 is H, CH3 or CH2CH3: R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl; R18 is H or CH3; R19 is C1-C4 alkyl, CH2CH2OCH3 CH2CH2C1 or CH2CH=CH2; R20 is C1-C3 alkyl; R21 is C1-C3 alkyl: R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=CH2: m is 0 or 1; n is 0 or 2: Q1 is O, S, SO2 or NR17: Q2 is O, S or NR17; and W is O, s or SO2 A is EMI181.1 EMI181.2 X is CH3, OCH3, OCH2CH3, C1, F, Br. OCF2H, CH2F or CF3: Y iS H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH3, OCH2CH=CH2, OCH2C=CH, OCH2CF3, OCH2CH2OCH3, CH25CH3. OCF2H, SCF2H, CR24(QCH3)2, EMI181.3 EMI182.1 or CR24(QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O: X1 is CH3, OCH3, OCH2CH3 or OCF2H: Y2 is H or CH3; X2 iS CH3, CH2CH3 or CH2CF3: Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3: X3 is CH3 or OCH3; and their agriculturally suitable salts; provided that 1) the total number of carbon atoms of R20 and R21 is less than or equal to four; 2) when m is 1, then R13 is H; 3) when L is L-17, then R17 and R18 are not simultaneously H: 4) when X is Cl, F or Br, then Z is CH and Y is OCH3, OCH2CH3, N(CH3)2 or OCF2H; 5) when L is L-1 and A is A-l, R5 is C2-C4 alkyl, C2-C4 alkoxy, OCH2CH2OCH3, OSO2R22, S(O)nCH2CH=CH3, WCF2, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI182.2 EMI182.3 EMI183.1 6) when L is L-1 and A is A-2 or A-3, then H5 is C2-C4 alkyl, C2-C4 alkoxy, OCH2CH2OCH3, OSO2R22, WCF3, WCHF2, C3-C4 alkenyloxy, C3 -C4 alkynyloxy. C1-C2 alkyl substituted with OCH3 or OCH2CH3. C6H5, EMI183.2 EMI183.3 7) when L is L-3 and A is A-1, A-2 cr A-3, then R8 iS SO2NR20R21, SO2N(OCH3)CH3 or SO2R23: 8) when L is L-4, L-5 or L-6 and A is A-1, A-2 and A-3, then R9 is C1-C3 alkyl. F. Cl, Br, NO2, SO2NR20R21, SO2N(OCH3)CH3 oR S(O)nR23; and 9) when L is L-2, then A is A-5 or A-6; which comprises: (a) reacting a compound of formula EMI183.4 wherein L, A and R are as defined above and X' is Cl or Br, with MSRd, wherein M is Na, K or Li and Rd is as defined above, (b) reacting a compound of formula EMI184.1 wherein L and Rd are as defined above1 with the lithium salt of a 2-aminoheterocycle of formula EMI184.2 wherein A and L are as defined above; or (c) reacting a sulfonyl halide of formula LSO2Cl wherein L is as defined above, with an S-alkyl isothiourea of formula EMI184.3 wherein Rd, A and R are as defined above. 16. A process of claim 15 where R is H and A is A-l; Y is CH3, OCH3, OCH2CH3, CH2OCH3, OCH2CF3 or CM(OCM3)2; X is CH3, OCH3, Cl or CF3; and where L is L-1 and R5 is OS02R22, SO2CH2CH=CH2, OCF2H, SCF2H, OCH2CH=CH2. OCH2C=CH, EMI184.4 EMI184.5 17. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound characterized in that said herbicidal compound comprises a compound of formulae (I), (II) or (III) as defined in any of claims 1 to 16. 18. A meth.od for regulating the growth of plants by applying to the locus of said plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterized in that said plant growth regulant comprises a compound of formulae (I), (II) or (III) as defined in any of claims 1 to 16.

Inventors: SHAPIRO, RAFAEL, TSENG, CHI-PING
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1984
Main classification: C07D239
IPC codes: C07D251, A01N47, C07D239, C07D521