HERBICIDAL SULFONAMIDES

Abstract: Sulfonylurea derivatives of the formula: wherein: R is H or CH₃; L is selected from various aromatic groups; X is a secondary or tertiary amino group; Y is a fluoroethoxy group; Z is CH or N; and their agricuituraily suitable salts, exhibit herbicidal ac­ tivity. Some also show a plant growth regulant effect. The compounds may be formulated for agricultural use in conventional manner. They may be made by a variety of synthetic routes, e.g. by reacting an appropriate aromatic sulfonyl isocyanate of formula LSO₂NCO with an appro­ priately substituted aminopyrimidine or aminotriazine.

Description: Title HERBICIDAL SULFONAMIDES Background of the Invention The present invention relates to a class of sulfonylurea compounds which are herbicidal sulfonamides, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. as well as for agriculturally suitable salts. U.S. 4,127,405 and U.S. 4.169,719 disclose herbicidal benzenesulfonylureas. U.S. 4,394.506 and U.S. 4.383,113 disclose ortho-alkoxycarbonylbenzenesulfonylureas U.S. 4.370,479 discloses herbicidal naphthalene sulfonylureas. U.S. 4,435.206 and EP-A-35.893 disclose herbicidal pyridylsulfonylureas. EP-A-30.142 discloses thiophene sulfonylureas which are useful as herbicides. U.S. 4,420,325 discloses herbicidal benzylsulfonylureas. Our EP-A-0,lO7,979 discloses the herbicidal sulfonylureas of the following general structure: EMI1.1 South African Patent Application 83/5165 filed by Ciba-Geigy (Swiss priority 16.07.82) discloses herbicidal benzo[b]furan sulfonylureas. South African Application No. 83/8416 (Swiss priority 12.11.82; published 12.05.84) discloses sulfonylureas of the general formula EMI2.1 wherein Z is 0 or S; E is N or CH; R1 is. inter alia, H, halogen, NO2, C1-C4 alkyl, etc.; R3 and R4 are independently H, C1-C4 alkyl, C1-C4 haloalkoxy, -NR5R6, etc.: U5 and R6 are H or C1-C4 alkyl: and A is an unsaturated or partially saturated 5 or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms. South African Application No. 84/2245 (Swiss priority 28.03.83; published 28.09.84) discloses herbicidal sulfonylureas of the formula EMI2.2 wherein A i6 C1-C6 haloalkyl; Z is 0 or S; E is CR or N: R1 is, inter alia. H. halogen. NO2, CN, etc.: R2 is, inter alia, H. halogen, C1-C4 alkyl, etc.: R3 and R4 are independently H. halogen, C1-C4 alkyl, C2-C4 haloalkoxy, -NR12R13, etc.: and R12 and R13 are independently H or C1-C4 alkyl. South African Application No. 84/2722 (Swiss priority 13.04.83; published 13.10.84) discloses sulfonylureas of the formula wherein EMI3.1 A is a radical of the formula -CR6R7XR8, CR9R10R11 or CHR7SCQR21; R1 is. inter alia. H. halogen, NO2, CN, etc.; R2 is, inter alia, H. halogen. C1-C4 alkyl. etc.: Z is O or S; R3 and R4 are independently H, halogen, C1-C4 haloalkoxy. NR19R20, etc.: R19 and R20 are independently H or C1-C4 alkyl; Rg is, inter alia. H, halogen, C1-C4 alkyl, etc.; R10 is H, halogen or CH3; and R11 is, inter alia, a radical C(O)R24 or a C-C4 alkyl group that is mono- or poly substituted by CN, NO2, OH. C1-C4 alkoxy. C1-C4 haloalkoxy, etc. South African Application No. 82/7439, published 13.04.83; discloses the following compounds of the formula EMI3.2 wherein R4 is H, CH3 or C2H5; R5 is H, C1-C4 alkyl, C1-C3 alkoxy, CH20CH3, CH2CN or CH2CH2CN: and R3 is H. C1-C4 alkyl. C1-C4 haloalkoxy etc. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops. Summary of the Invention This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and postemergent herbicides or as plant growth regulants, and their agriculturally suitable salts. EMI4.1 wherein B is H or CH3; EMI4.2 EMI5.1 R1 is C1-C4 alkyl, C1-C4 alkoxy, F. C1, Br. N02, CO2R10, SO2NR11R12, SO2N(OCH3)CH3, S(O)nR13, CH2OCH3, CH2OC2H5, C6H5 or Q; EMI5.2 R2 is H, F, Cl, Br, CF3, CH3, C2H5, OCH3, OC2H5, SCH3 or SC2H5: R3 is H, CH3, OCH3, F. C1, Br, S02N(CH3)2, OSO2CH3 or S(O)nCH3; R4 is CH3, C2H5, OCH3, OC2H5, F,Cl, Br, SO2NR11R12, SO2N(OCH3)CH3 or S(O)nR13; R5 is C1-C3 alkyl, F, C1, Br, NO2. CO2R10, SO2NR11R12, SO2N(OCH3)CH3 or S(O)nR13; R6 is CO2CH3, CO2C2H5, SO2N(CH3)2, OSO2CH3, S02CH3 or SO2CH2CH3; R7 is H, C1-C5 alkyl. CH2CH2F, CH2CH2CH2F, C3-C4 alkenyl, C3-C4 alkynyl, CH30CH2CH2 or C H OCH2CH2; R8 is H. C1. CH3 or OCH3: R9 is H or CH3 R10 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl, CH2CH=CH2 or CH2C=CH; R11 is H or C1 C alkyl; R12 is C1-C2 alkyl; R13 is C1-C3 alkyl; n is 0, 1 or 2; X is NR14R15; R14 is H or C1-C2 lakyl; R is C -C2 alkyl. OCH3, OC2H5 orCH2CN; Y is OCH2CH2F, OCH2CHF2 or OCH2CF3; and Z is CH or N; and their agriculturally suitable salts. Preferred for reasons of their higher herbicidal activity. greater plant growth regulant activity and/or more favorable ease of synthesis are: 1) Compounds of Formula I wherein L is L-l, L-8 or L-9; and R is H. 2) Compounds of Preferred 1 wherein R1 is C1-C3 alkyl, C1-C3 alkoxy, C1, NO2, CO2C1-C3 alkyl, S=2N(CH3)2, SO2CH3 or SO2C2H5; R14 is H; Z is N; and R2 is in the 5-position of the phenyl ring. 3) Compounds of Preferred 2 wherein L is L-l or L-8; and R7 is H, CH3 or C2H5, 4) Compounds of Preferred 3 wherein 15 is CH3; and R2 is H, Other compounds within the scope of Formula I are those disclosed in our U.S. Patent Applications Serial Nos. 618,412 and 731,261. Copies of these specifications are available for inspection on the file of the present Application Specifically preferred for their greatest herbicidal activity. greatest plant growth regulant activity and/or greatest ease of synthesis: 2-t[t4-(methylamino)-6-(2,2,2-trifluoroethoxy)- 1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]- benzoic acid, methyl ester. m.p. 195-1970C(d); and 2-[ [4-(methylamino)-6-(2.2,2-trifluoroethoxy)- 1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]- benzoic acid, ethyl ester. m.p. 181-183"C(d). Detailed Description of the Invention Synthesis The compounds of Formula I can be prepared by reacting an appropriate sulfonyl isocyanate II with the appropriately substituted aminoheterocycle III, as shown in Equation 1. R, X, Y, Z and L are as previously defined. Equation 1 EMI7.1 The reaction is best performed in an inert solvent such as methylene chloride or toluene at 25 to 100"C. for 1 to 24 hours. Isolation of the product can be achieved by concentrating the solution and trituration with an appropriate solvent such as butyl chloride. Alternatively, compounds of Formula I may be prepared by reacting the sulfonamides of Formula IV with the carbamates of Formula V (R'=CH3) in the presence of an excess of trimethylaluminum, as shown in Equation 2, where L, R. X, Y and Z are as previously defined, provided R1 is other than CO2R10. Equation 2 EMI8.1 The reactions are best performed in an inert solvent such as methylene chloride at the reflux point of the solution (400C) for 10 to 24 hours. Isolation of the product is best achieved by exposing the reaction mixture to acetic acid, separation of the layers and concentrating the organic layer to a solid. Alternatively. compounds of Formula I can be prepared by exposing a phenyl carbamate V (R'=Ph) to the sulfonamide IV in an appropriate solvent such as dioxane at 25 to 1000C in the presence of a strong base such as 1,8-diazabicyclot5.4.0]undec-7-ene; acid workup affords the desired product. See EPO Publication No. 44,807 for details. The required carbamates (V) can be prepared from the corresponding amines III and dimethyl or diphenyl carbonate or methyl or phenyl chloroformate and a suitable base such as sodium hydride. The sulfonyl isocyanates II used in the preparation of I are knbwn in the art and can be prepared by known methods. For example. isocyanates can be prepared by exposing an appropriate benzene or heterocyclic sulfonamide to phosgene in the presence of an alkyl isocyanate and an amine catalyst such as 1,4 diazabicyclo2.2.2Joctane at the reflux point of the solvent. 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. Forest Ed. The sulfonamides IV used in the preparation of I are also known in the art and can be prepared by known methods. For example, exposure of a sulfonyl chloride to ammonium hydroxide results in the. formation of the corresponding sulfonamide, e.g., Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). The appropriate sulfonyl chlorides are prepared by several methods. For example, treatment of a substituted aromatic or heterocyclic ring with chlorosulfonic acid in carbon tetrachloride results in the formation of the sulfonyl chloride. See Clark et al., Orq. Synth. Coll., Vol. 1 2nd Ed. 1941, p. 85. An alternative method of preparation of sulfonyl chlorides can be achieved from an appropriate amine. Diazotization of an amine with sodium nitrite in acid, followed by exposure of the resulting diazonium salt to sulfur dioxide in the presence of cuprous chloride results in the formation of a sulfonyl chloride. See H. L. Yale and F. Sowinski, J. Orq. Chem., 25, 1824 (1960). The heterocyclic amines III, where X, Y. Z and R are as previously defined may be prepared as outlined in Equation 3. Equation 3 EMI10.1 Reaction of chloride VI with the appropriate secondary amine in acetone affords the aminated product VII. Subsequent exposure of VII with the appropriate alcohol in the presence of a suitable base such as potassium hydroxide affords the desired heterocycle III (where T is CF3. CHF2 or CH2F), The sLdrLing amine heterocycles VI are known in the art. For further details of their preparation see The Chemistry of Heterocyclic Compounds, "lnterscience Publ., New York and London: P. J. Brown, "The Pyrimi dines. Vol. XVI and-E. M. Smolin and L. Rapoport. "s-Triazines and Derivatives", Vol. XIII. The heterocyclic amines III where R is a methyl group may be prepared from the corresponding compounds where R is hydrogen by known methods. An example of this type of transformation is described in: J. Chem. Ssc. Perkin I, 1569 (1981). Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide or carbonate). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium. sodium or calcium salt. Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., P-toluenesulfonic acid. trichloroacetic acid or the like. The following examples teach the synthesis of some of the compounds contained within this invention in greater detail. Example 1 2-Amino-4-chloro-6-methylamino-1,3,5-triazine A solution of 2-amino-4,6-dichloro-1,3,5-triazine (0.2 mole) in 200 ml reagent grade acetone was cooled to 00C. Two equivalents of 40% aqueous methylamine were added dropwise keeping the temperature less than LOOC; solids precipitated during the addition. The reaction was then warmed to room temperature and stirred overnight under N2. The fixture was poured onto 800 ml of ice-water and the insolubles were filtered off and washed with distilled water. The solid was dried overnight over P205 in a vacuum dessicator. The resulting product named above had the following characteristics: m.p. 258-260 C (decomp.); NMR (CDC13, DMSO-d6): 6 2.8, d, (NHCH3): 6.8-7.65, mt, (NH2 + NHCH3). Example 2 2-Asino-4-methYlamino-6-trifluoroethoxv-1,3,5-triazine 2-Amino-4-chloro-6-methylamino-1,3,5-triazine (0.2 mole) was slurried in 80 ml of 2.2,2-trifluoroethanol at room temperature. Potassium hydroxide pellets (0.2 mole) were added portionwise and the mixture was stirred at room temperature overnight. The following day the reaction was heated at gentle reflux for 2 hours during which time the solids gradually dissolved. The solution was cooled and the solvent was removed under vacuum. The residue was washed with water and filtered to give 20.9 g shining off-white crystals of the product named above with the following characteristics: m.p. 204-2050C. NMR (DMSOd): 6 2.75, d, (NHCH3); 4.8, q, (OCH2CF3); 6.5-7.3. m, (NH2 + NHCH3), Example 3 2-[[[4-(Methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5triazin-2-yl]aminicarbonyl]aminosulfonyl]benzoic acid, methyl ester 2-Carbomethoxybenzenesulfonyl isocyanate (0.5 g) was dissolved in 5 ml of methylene chloride. The aminoheterocycle (0.46 g) prepared in Example 2 was added and the mixture was stirred overnight under nitrogen at room temperature. The resulting solids were filtered off, washed with methylene chloride and dried to give 0.54 g of -80% pure subject compound; m.p. 195-1970C decomp. No attempt was made at further purification. The resulting product named above had the following characteristics: IR (nujol) showed carbonyl bands at 1723 cm and 1740 cm NMR (CDC13, DMSO-d6): a 2.9, m. (NHCH3); 3.8, s, (CO2CH3); 4.9, m, (OCH2CF3); 7.7-8.4, m. (aromatic 's) plus -20% heterocycle. Using the procedures described above, the compounds in Tables 1-9 can be prepared by one skilled in the art. Table Ia EMI14.1 R1 R2 R R14 R15 Z m.p.( C) CH3 H H H CH3 CH CH2CH3 H H H CH3 CH CH2CH3 H H H CH3 N CH2CH2CH3 H H H CH3 N CH2CH2CH3 H H CH3 CH3 N OCH3 H H H CH3 N OCH3 H H CH2CH3 CH3 CH OCH2CH3 H H H CH3 N OCH2CH3 H H CH3 CH3 N OCH2CH3 H H H CH2CH3 CH OCH2CH2CH3 H H H CH3 N OCH2CH2CH3 H H H CH3 CH OCH2CH2CH3 H H H CH2CH3 N OCH2CH2CH2CH3 H H H CH3 N F H H H CH3 CH F H H H CH3 N F H H CH3 CH3 N F H H H CH2CH3 N F H H H CH2CH3 CH F H H CH2CH3 CH2CH3 N Cl H H H CH3 N Cl H H H CH3 CH Cl H H CH3 CH3 N Cl H H CH3 CH3 CH CL H H CH3 CH2CH3 N Table la (continued) R1 R2 R R14 R15 Z m.p.( C) Q-1 H H CH3 CH3 N Q-1 H H CH3 CH3 CH Br H H H CH3 N Br H H H CH3 CH Br H H CH3 CH3 N Br H H CH3 CH3 CH Br 6-OCH3 H H CH3 N NO2 H H H CH3 N NO2 H H H CH3 CH NO2 H H CH3 CH3 N NO2 H CH3 CH3 CH3 N NO2 F H H CH3 N C 2CH3 H H H CH3 N CO2CH3 H H H CH3 CH CO2CH3 H H H CH2CH3 CH CO2CH3 H H H CH2CH3 N C 2CH3 H H CH3 CH3 N CO2CH3 H H CH3 CH3 CH CO2CH3 H H CH3 CH2CH3 CH CO2CH3 H H CH3 CH2CH3 N CO2CH3 H H CH2CH3 CH2CH3 N CO2CH3 H H CH2CH3 CH2CH3 CH SO2N(CH3)2 H H H CH3 CH SO2N(CH3)2 H H H CH3 N SO2N(CH3)2 H H CH3 CH3 CH SO2N(CH3)2 H H CH3 CH3 N S02N(CH3)2 H H CH3 CH2CH3 CH CO2N(CH2CH3)CH3 H H H CH3 N SO2N(CH2CH3)CH3 H H H CH3 CH SO2N(CH2CH3)CH3 H H CH3 CH3 N SO2N(CH2CH3)2 H H H CH3 N SO2N(CH2CH3)2H H H CH3 CH Table la (continued) m.p. R1 R2 R R14 R15 Z ( C) SO2N(OCH3)CH3 H H H CH3 N SO2N(OCH3)CH3 H H H CH3 CH SO2N(OCH3)CH3 H H H CH2CH3 N SO2N(OCH3)CH3 H H CH3 CH3 N SO2CH3 H H H CH3 N SO2CH3 H H H CH3 CH SO2CH2CH3 H H H CH3 N SO2CH2CH2CH3 H H H CH3 N SO2CH2CH2CH3 H CH3 H CH3 N SCH2CH2CH3 5-OCH3 H H CH3 N Ph H H CH3 CH3 N Ph H H H CH3 N CH3 H H H CH2CN N CH3 H H H OCH3CH CH2CH3 H H H OCH3 N CH2CH2CH2CH3 H H H OCH3 N OCH3 5-SCH3 H H CH3 CH OCH2CH3 5-SCH3 H H CH3 N F H H H OCH3 N F H H CH3 OCH3 N Cl H H H OCH3 CH Cl 5-SCH3 H H CH3 N Br 5-SCH3 H H CH3 CH Br H H CH3 OCH3 N CO2CH3 H H CH3 OCH3 N CO2CH3 H H CH3 OCH3 CH CO2CH3 5-SCH3 H H CH3 N CO2CH3 H H H OCH3 N SO2N(CH3)2 H H CH3 OCH3 N SO2N(CH3)2 H H CH3 CH2CN N SO2N(CH3)H H H H CH3 CH Q-1 H H H CH3 CH Table la (continued) m.p. R1 R2 R R14 R15 Z ( C) Q-1 H H H CH3 N Q-2 H H H CH3 N Q-2 H H CH3 OCH3 N Q-3 H H H CH3 N CH3 H H CH3 OCH3 CH CH3 H H CH3 OCH3 N CH2CH3 H H CH3 OCH3 N Cl H H CH3 OCH3 N NO2 H H CH3 OCH3 N C 2CH3 5-OCH3 H CH3 OCH3 CH CO2CH3 5-CF3 H CH3 OCH3 CH CO2CH3 H CH3 CH3 OCH3 N CO2CH2CH3 H H CH3 OCH3 N CO2CH2CH=CH2 H H CH3 OCH3 N SO2N(CH3)2 H H CH3 OCH3 CH CH2OCH3 H H CH3 OCH3 N Table 1b EMI18.1 R1 R2 R R14 R15 Z m.p.( C) CH3 H H H CH3 CH CH2CH3 H H H CH3 CH CH2CH3 H H H CH3 N CH2CH2CH3 H H H CH3 N CH2CH2CH3 H H CH3 CH3 N OCH3 H H H CH3 N OCH3 H H CH2CH3 CH3 N OCH2CH3 H H H CH3 N OCH2CH3 H H CH3 CR3 N OCH2CH3 H H H CH2CH3 CH OCH2CH2CH3 H H H CH3 N OCH2CH2CH3 H H H CH3 CH OCH2CH2CH3 H H H CH2CH3 N OCH2CH2CH2CH3 H H H CH3 N F H H H CH3 CH F H H H CH3 N F H H CH3 CH3 N P H H H CH2CH3 N F H H H CH2CH3 CH F H H CH2CH3 CH2CH3 N Cl H H H CH3 N Cl H H H CH3 CH Cl H H CH3 CH3 N Cl H H CH3 CH3 CH Cl H H CH3 CH2CH3 N Table 1b (continued) R1 R2 R R14 R15 Z m.p. ( C) Br H H H CH3 N Br H H H CH3 CH Br H H CH3 CH3 N Br H H CH3 CH3 CH Br 6-OCH3 H H CH3 N NO2 H H H CH3 N NO2 H H H CH3 CH NO2 H H CH3 CH3 N NO2 H CH3 CH3 CH3 N NO2 F H H CH3 N CO2CH3 H H H CH3 N CO2CH3 H H H CH3 CH CO2CH3 H H H CH2CH3 CH CO2CH3 H H H CH2CH3 N CO2CH3 H H CH3 CH3 N CO2CH3 H H CH3 CH3 CH CO2CH3 H H CH3 CH2CH3 CH CO2CH3 H H CH3 CH2CH3 N C 2CH3 H H CH2CH3 CH2CH3 N CO2CH3 H H CH2CH3 CH2CH3 CH SO2N(CH3)2 H H H CH3 CH SO2N(CH3)2 H H H CH3 N SO2N(CH3) H H CH3 CH3 CH SO2N(CH3)2 H H CH3 CH3 N SO2N(CH3)2 H H CH3 CH2CH3 CH SO2N(CH2CH3)CH3 H H H CH3 N SO2N(CH2CH3)CH3 H H H CH3 CH SO2N(CH2CH3)CH3 H H CH3 CH3 N SO2N(CH2CH3)2 H H H CH3 N SO2N(CH2CH3)2 H H H CH3 CH SO2N(OCH3)CH3 H H H CH3 N SO2N(OCH3)CH3 H H H CH3 CH Table Ib (continued) R1 R2 R R14 R15 Z m.p.( C) SO2N(OCH3)CH3 H H H CH2CH3 N SO2N(OCH3)CH3 H H CH3 CH3 N SO2CH3 H H H CH3 N SO2CH3 H H H CH3 CH SO2CH2CH3 H H H CH3 N SO2CH2CH2CH3 H H H CH3 N SO2CH2CH2CH3 H CH3 H CH3 N SC2CH2CH3 6-OCH3 H H CH3 N Ph H H H CH3 CH Q-3 H H H CH2CH3 N CH3 H H H OCH3 N CH3 H H H CH2CN N CH2CH3 H H H OCH3 N CH2CH2CH2CH3 H H CH3 CH3 N CH2CH2CH2CH3 H H H OCH3 N OCH3 5-SCH3 H H CH3 N F H H CH3 OCH3 N F H H CH3 OCH2CH3 N Cl H H H OCH3 CH Cl 5-SCH3 H H CH3 N Br 5-SCH3 H H CH3 CH Br H H CH3 OCH3 N CO2CH3 H H CH3 OCH3 CH CO2CH3 5-SCH3 H H CH3 CH CO2CH3 H H H OCH3 N SO2N(CH3)2 5-SCH3 H H CH3 N SO2N(CE3)2 H H CH3 CH2CN N SO2N(CH3)H H H H CH3 N O-1 H H H CH3 CH Q-1 H H H CH3 N Q-2 H H H. CH3 N Q-2 H H CH3 OCH3 N Table 1b (continued) R1 R2 R R14 R15 Z Q-3 H H H CH3 N CH3 H H CH3 OCH3 N CH2CH3 H H CH3 OCH3 N Cl H H CH3 OCH3 N NO2 H H CH3 OCH3 N CO2CH3 5-OCH3 H CH3 OCH3 CH CO2CH3 H CH3 CH3 OCH3 N CO2CH2CH3 H H CH3 OCH3 N CO2CH2CH=CH2 H H CH3 OCH3 N SO2N(CH3)2 H H CH3 OCH3 CH CH2OCH3 H H CH3 OCH3 N Table Ic EMI22.1 R1 R2 R R14 R15 Z m.p.( C) CH3 H H H CH3 CH CH2CH3 H H H CH3 CH CH2CH3 H H H CH3 N CH2CH2CH3 H H H CH3 N CH2CH2CH3 H H CH3 CH3 N OCH3 H H H CH3 N 204-207(d) OCH3 H H CH2CH3 CH3 Ch OCH2CH3 H H H CH3 N OCH2CH3 H H CH3 CH3 N OCH2CH3 H H H CH2CH3 CH OCH2CH2CH3 H H H CH3 N OCH2CH2CH3 H H H CH3 CH OCH2CH2CH3 H H H CH2CH3 N OCH2CH2CH2CH3 H H H CH3 N CO2CH2CH3 H H H CH3 N 181-183(d) CF3 H H H CH3 N 210-211(d) F H H CH3 CH3 N F H H H CH2CH3 N F H H H CH2CH3 CH F H H CH2CH3 CH2CH3 N CI H H H CH3 N 210-212(d) Cl H H H CH3 CH Cl H H CH3 CH3 N Cl H H CH3 CH3 CH Cl H H CH3 CH2CH3 N Table ic (continued) R1 R2 R R14 R15 Z m.p.( C) Br H H H CH3 N Br H H H CH3 CH Br H H CH3 CH3 N Br H H CH3 CH3 CH Br 6-OCH3 H H CH3 N N02 H H H CH3 N N02 H H H CH3 CH 207-213(d) N02 H H CH3 CH3 N N02 H CH3 CH3 CH3 N N02 F H H CH3 N CO2CH3 H H H CH3 N 195-197(d) CO2CH3 H H H CH3 CH CO2CH3 H H H CH2CH3 CH CO2CH3 H H H CH2CH3 N 193-194(d) CO2CH3 H H CH3 CH3 N CO2CH3 H H CH3 CH3 CH C 2CH3 H H CH3 CH2CH3 CH CO2CH3 H H CH3 CH2CH3 N CO2CH3 H H CH2CH3 CH2CH3 N CO2CH3 H H CH2CH3 CH2CH3 CH SO2N(CH3)2 H H H CH3 CH SO2N(CH3)2 H H H CH3 N 190-205 SO2N(CH3)2 H H CH3 CH3 CH SO2N(CH3)2 H H CH3 CH3 N SO2N(CH3)2 H H CH3 CH2CH3 CH SO2N(CH2CH3)CH3 H H H CH3 N SO2N(CH2CH3)CH3 H H H CH3 CH SO2N(CH2CH3)CH3 H H CH3 CH3 N So2N(CH2CH3)2 H H H CH3 N SCH3 H H H CH3 N 200-201(d) SO2N(OCH3)CH3 H H H CH3 N SO2N(OCH3)CH3 H H H CH3 CH Table lc (continued) R1 R2 R R14 R15 Z m.p.( C) SO2N(OCH3)CH3 H H H CH2CH3 N SO2N(OCH3)CH3 H H CH3 CH3 N SO2CH2CH2CH3 5-OCH3 H H CH3 N SO2CH3 H H H CH3 N 164-165(d) SOCH3 H H H CH3 N SOCH2CH3 H H H CH3 CH CH3 H H H OCH3 N CH3 H H H CH2CN N CH2CH3 H H H OCH3 N CH2CH3 H H H OCH2CH3 N CH2CH2CH2CH3 H H H OCH3 N OCH3 S-SCH3 H H CH3 CH OCH2CH2CH3 5-SCH3 H H CH3 N P H H H OCH3 N F H H CH3 OCH2CH3 N Cl H H H OCH3 CH Cl H H CH3 CH2CN N 90-100 Cl 5-SCH3 H H CH3 N Br 5-SCH3 H H CH3 CH Br H K CH3 OCH3 N CO2CH3 H H CH3 OCH3 N CO2CH3 H H CH3 OCH3 CH CO2CH3 H H CH3 CH2CN N 181-183 CO2CH3 5-SCH3 H H CH3 N CO2CH3 H H H OCH3 N SO2N(CH3)2 H H CH3 OCH3 N SO2N(CH3)2 H H CH3 CH2CN N SO2N(CH3)H H H CH3 N Q-1 H H H CH3 CH Q-1 5-SCH3 H H CH3 N Q-2 H H H CH3 N Q-2 5-SCH3 H H CH3 N Table 1c (continued) m.p. R1 R2 R R14 R15 Z ( C) Q-3 H H H CH3 N CH3 H H CH3 OCH3 N CH2CH3 H H CH3 OCH3 N Cl H H CH3 OCH3 N NO2 H H CH3 OCH3 N CO2CH3 5-OCH3 H CH3 OCH3 CH CO2CH3 H CH3 CH3 OCH3 N CO2CH2CH3 H H CH3 OCH3 N SO2N(CH3)2 H H CH3 OCH3 CH CH2OCH3 H H CH3 OCH3 N Table 2a EMI26.1 R R3 R14 R15 Z m.p.( C) H H H CH3 N H CH3 H CH3 N H CR3 H CH3 CH H CH3 CH3 CH3 N H OCH3 H CH3 CH H OCH3 CH3 CH3 N H F HCH3 N H Cl H CH3 CH H Br H CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CE3)2 H CH3 N H SO2N(CH3)2 CH3 CH2CH3 CH H OSO2CH3 H CH3 CH H OSO2CH3 H CH3 N H OSO2CH3 H CH2CH3 CH H OSO2CH3 CH2CH3 CH2CH3 N H SO2CH3 H CH3 CH H SO2CH3 H CH3 N H SO2CH3 H CH2CH3 N H SO2CH2 CH3 CH3 CH H SO2CH3 CH3 CH3 N CH3 SO2CH2 CH3 CH3 N CH3 SO2CH3 H CH3 N H SCH3 H CH3 N H SOCH3 H CH3 N Table 2a (continued) R R3 R14 R15 Z H H CH3 OCH3 N H CH3 CH3 OCH3 CH H OCH3 CH3 OCH3 N H F CH3 OCH3 CH H F CH3 OCH3 N H Br CH3 OCH3 CH H SO2N(CH3)2 CH3 OCH3 CH H SO2N(CH3)2 CH3 OCH3 N H OSO2CH3 CH3 OCH3 CH H SO2CH3 CH3 OCH3 N CH3 SO2N(CH3)2 CH3 OCH3 CH H S02N(CH3)2 CH3 OCH2CH3 N H S02N(CH3)2 H CH2CN N H CH3 CH3 CH2CN N H Cl CH3 OCH2CH3 N Table 2b EMI28.1 R R3 R14 R15 Z m.p.( C) H H H CH3 N H CH3 H CH3 N H CH3 H CH3 CH H CH3 CH3 CH3 N H OCH3 H CH3 CH H OCH3 CH3 CH3 N H F H CH3 N H Cl H CH3 CH H Br H CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH2CH3 CH H OSO2CH3 H CH3 CH H OSO2CH3 H CH3 N H OSO2CH3 H CH2CH3 CH H OSO2CH3 CH2CH3 CH2CH3 N H SO2CH3 H CH3 CH H SO2CH3 H CH3 N H SO2CH3 H CH2CH3 N H SO2CH3 CH3 CH3 CH H SO2CH3 CH3 CH3 N CH3 SO2CH3 CH3 CH3 N CH3 SO2CH3 H CH3 N H SCH3 H CH3 N Table 2b (continued) R R3 R14 R15 Z m.p.( C) H H CH3 OCH3 N H CH3 CH3 OCH3 N H OCH3 CH3 OCH3 N H OCH3 CH3 OCH3 CH H F CH3 OCH3 N H Br CH3 OCH3 Ch H SO2N(CH3)2 CH3 OCH3 Ch H OS02CH3 CH3 OCH3 N H OSO2CH3 CH3 OCH3 CH H SO2CH3 CH3 OCH3 CH CH3 SO2N(CH3)2 CH3 OCH3 N H S02N(CH3)2 H CH2CN N H CH3 CH3 OCH2CH3 N H Cl CH3 OCH2CH3 N Table 2c EMI30.1 R R3 R14 R15 Z m.p.( C) H H H CH3 N H CH3 H CH3 N H CH3 H CH3 CH H CH3 CH3 CH3 N H OCH3 H CH3 CH H OCH3 CH3 CH3 N H F H CH3 N H Cl H CH3 CH H Br H CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH2CH3 CH H OSO2CH3 H CH3 CH H OSO2CH3 H CH3 N H OSO2CH3 H CH2CH3 CH H OSO2CH3 CH2CH3 CH2CH3 N H SO2CH3 H CH3 CH H SO2CH3 H CH3 N H SO2CH3 H CH2CH3 N H SO2CH3 CH3 CH3 CH H SO2CH3 CH3 CH3 N CH3 SO2CH3 CH3 CH3 N CH3 SO2CH3 H CH3 N Table 2c (continued) R R3 R14 R15 Z m.p.( C) H H CH3 OCH3 N H CH3 CH3 OCH3 CH H CH3 CH3 OCH3 N H OCH3 CH3 OCH3 CH H F CH3 OCH3 CH H Br CH3 OCH3 CH H Br CH3 OCH3 N H SO2N(CH3)2 CH3 OCH3 CH H OSO2CH3 CH3 OCH3 N H SO2CH3 CH3 OCH3 CH H S02N(CH3)2 H CH2CN N H CH3 CH3 OCH2CH3 N H Cl CH3 OCH2CH3 N Table 3a EMI32.1 R R4 R14 R15 Z m.p.( C) CH3 CH3 H CH3 N H CH3 H CH3 N H CH3 H CH3 CH H CH2CH3 H CR3 N H CH2CH3 H CH2CH3 CH H OCH3 H CH3 CH H OCH3 H CH3 N H OCH3 CH3 CH3 N H OCH2CH3 H CH3 N H F H CH3 N H Cl H CH3 CH H Br H CH3 CH H Br CH3 CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CR3 N H SO2N(CH3)2 CH3 CH3 Ch H SO2N(CH3)2 CH3 CH2CH3 N H SO2N(CH3)2 CH2CH3 CH2CH3 CH H SO2N(CH2CH3)2 H CH3 N H SO2N(OCH3)CH3 H CH3 N H SO2N(OCH3)CH3 H CH3 CH H SO2N(OCH3)CH3 CH3 CH3 N H SO2N(OCH3)CH3 CH3 CH3 CH H SO2CH3 H CH3 CH H SOCH3 H CH3 CH H 5CH3 H CH3 CH Table 3a (continued) R R4 R14 R15 Z m.p.( C) H SO2CH3 H CH3 N H SO2CH2CH3 H CH3 N CH3 CH3 CH3 OCH3 N H H CH3 OCH3 CH H H CH3 OCH3 N H CH3 CH3 OCH3 CH H CH3 CH2CH3 OCH3 N H OCH3 CH3 OCH3 CH H OCH3 CH3 OCH3 N H F CH3 OCH3 CH H Cl CH3 OCH3 CH H Cl CH3 OCH3 N H Br CH3 OCH3 CH H Br CH3 OCH3 N H SO2N(CH3)2 CH3 OCH3 CH H SO2N(CH3)H CH3 OCH3 N H SO2CH3 CH3 OCH3 Ch H SO2CH3 CH3 OCH3 N H SO2CH2CH3 CH2CH3 OCH2CH3 N H SO2CH3 H CH3 N H OCH2CH3 CH3 OCH3 N CH3 S02N(CH3)2 CH3 OCH3 N Table 3b EMI34.1 R R4 R14 R15 Z m.p.( C) CH3 CH3 H CH3 N H CH3 H CH3 N H CH3 H CH3 CH H CH2CH3 H CH3 N H CH2CH3 H CH2CH3 CH H OCH3 H CH3 CH H OCH3 H CH3 N H OCH3 CH3 CH3 N H OCH2CH3 H CH3 N H F H CH3 N H Cl H CH3 CH H Br H CH3 CH H Br CH3 CH3 N H SO2N(CH3)2 H CH3 CR H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 CH3 CH2CH3 N H SO2N(CH3)2 CH2CH3 CH2CH3 CH H SO2N(CH2CH3)2 H CH3 N H SO2N(OCH3)CH3 H CH3 N H SO2N(OCH3)CH3 H CH3 CH H SO2N(OCH3)CH3 CH3 CH3 N H SO2N(OCH3)CH3 CH3 CH3 CH H S 2CH3 H CH3 CH H SO2CH3 H CH3 N H SO2CH2CH3 H CH3 N Table 3b (continued) R R4 R14 R15 Z m.p.( C) CH3 CR3 CH3 OCH3 N H H CH3 OCH3 CH H H CH3 OCH3 N H CH3 H CH2CN N H CH3 CH2CH3 OCH3 N H OCH3 CH3 OCH3 N 3 3 H F CH3 OCH3 CH H Cl CH3 OCH3 CH H Cl CH3 OCH3 N H Cl CH3 OCH2CH3 N H Br CH3 OCH3 N H SO2N(CH3)2 CH3 OCH3 CH H S02N(CH3)H CH3 OCH3 N H SO2CH3 CH3 OCH3 CH H SO2CH3 CH3 OCH2CH3 N H SO2CH2CH3 CH3 OCH3 N H SO2CH3 H CH3 N CH3 SO2N(CH3)2 CH3 OCH3 N Table 3c EMI36.1 R R4 R14 R15 Z m.p.( C) CH3 CH3 H CH3 N H CH3 H CH3 N H CH3 H CH3 CH H CH2CH3 H CH3 N H CH2CH3 H CH2CH3 CH H OCH3 H CH3 Ch H OCH3 H CH3 N H OCH3 CH3 CH3 N H OCH2CH3 H CH3 N H <RTI ID=36.3> P H CH3 N H Cl H CH3 CH H Br H CH3 CH H Br CH3 CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 CH3 CH2CH3 N H SO2N(CH3)2 CH2CH3 CH2CH3 CH H SO2N(CH2CH3)2 H CH3 N H SO2N(OCH3)CH3 H CH3 N H SO2N(OCH3)CH3 H CH3 CH H SO2N(OCH3)CH3 CH3 CH3 N H SO2N(OCH3)CH3 CH3 CH3 CH H SO2CH3 H CH3 CH H SO2CH3 H CH3 N H SO2CH2CH3 H CH3 N Table 3c (continued) R R4 R14 R15 Z m.p.( C) CR3 CH3 CH3 OCH3 N H H CH3 OCH3 N H CH3 H CH2CN N H CH3 CH2CH3 OCH3 N H OCH3 CH3 OCH3 CH H F CH3 OCH3 CH H F H CH2CN N H Cl CH3 OCH3 N H Br CH3 OCH3 CH H S02N(CH3)2 CH3 OCH3 N H SO2N(CH3)H CH3 OCH3 N H SO2CH3 CH3 OCH3 Ch H SO2CH3 CH3 OCH2CH3 N H SO2CH2CH3 CH3 OCH3 N H S02CH3 H CH3 N H OCH2CH3 CH3 OCH3 Ch Table 4a EMI38.1 L R R5 R14 R15 Z m.p.( C) L-4 H CH3 H CH3 N L-4 H CH3 H CH3 CH L-4 H <RTI ID=38.2> CH2CH3 H CH3 CH L-4 H CH2CH2CH3 CH3 CH3 N L-4 H F H CH3 CH L-4 H F H CH2CH3 N L-4 H Cl CH3 CH3 Ch L-4 H Cl CH2CH3 CH3 N L-4 H Br H CH3 N L-4 H NO2 H CH3 N L-4 H NO2 CH3 CH3 CH L-4 H CO2CH3 H CH3 CH L-4 H CO2CH3 H CH3 N L-4 H CO2CH3 H CH2CH3 CH L-4 H CO2CH3 CH3 CH3 CH L-4 H CO2CH2CH3 H CH3 N L-4 H CO2CH2CH3 CH2CH3 CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH=CH2 H CH3 CH L-4 H CO2CH2CH=CH2 H CH3 N L-4 H SO2N(CH3)2 H CH3 CH L-4 H SO2N(CH3)2 H CH3 N L-4 H SO2N(CH3)2 CH3 CH3 N L-4 H SO2N(OCH3)CH3 H CH3 N L-4 H SCH3 H CH3 N Table 4a (continued) L R R5 R14 R15 Z m.p.( C) L-4 H CH3 CH3 OCH3 CH L-4 H CH2CH3 CH3 OCH3 N L-4 H CH3 CH3 CH2CN N L-4 H F CH3 OCH3 N L-4 H F H CH3 N L-4 H Cl CH3 OCH3 N L-4 H Br CH3 OCH3 N L-4 H NO2 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 N L-4 CH3 CO2CH2CH3 CH3 OCH3 N L-4 CH3 CO2CH2CH=CH2 CH3 OCH3 CH L-4 H CO2CH2C#CH H CH3 N L-4 CH3 SO2N(CH3)2 CH3 OCH3 N L-4 H SO2N(CH3)2 CH3 CH2CN N L-4 CH3 SO2N(CH2CH3)2 CH3 OCH3 N L-4 H SO2N(OCH3)CH3 CH3 OCH3 CH L-4 H S02N(CH3)H CH3 OCH3 N L-4 H SO2N(CH3)H CH3 OCH2CH3 N L-4 H SO2CH3 CH3 OCH3 CH L-4 CH3 SO2CH2CH3 CH3 OCH3 Ch L-4 H SO2CH2CH3 CH3 CH2CN N L-4 H S(O)CH3 H CH3 N Table 4b EMI40.1 L R R5 R14 R15 Z m.p.( C) L-4 H CH3 H CH3 N L-4 H CH3 H CH3 CH L-4 H CH2CH3 H CH3 CH L-4 H CH2CH2CH3 CH3 CH3 N L-4 H F H CH3 CH L-4 H F H CH2CH3 N L-4 H Cl CH3 CH3 CH L-4 H Cl CH2CH3 CH3 N L-4 H Br H CH3 N L-4 H NO2 H CH3 N L-4 H NO2 CH3 CH3 CH L-4 H CO2CH3 H CH3 CH L-4 H CO2CH3 H CH3 N L-4 H CO2CH3 H CH2CH3 CH L-4 H CO2CH3 CH3 CH3 CH L-4 H CO2CH2CH3 H CH3 N L-4 H CO2CH2CH3 CH2CH3 CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2OCH3 H CH3 N L-4 H CO2CH2CH2Cl H CH3 N L-4 H CO2CH2CH=CH2 H CH3 CH L-4 H CO2CH2CH=CH2 H CH3 N L-4 H SO2N(CH3)2 H CH3 CH L-4 H SO2N(CH3)2 H CH3 N L-4 H SO2N(CH3)2 CH3 CH3 CH L-4 H SOCH3 H CH3 N L-4 H SOCH3 H CH3 N Table 4b (continued) L R R5 R14 R15 Z m.p.( C) L-4 H CH3 CH3 OCH3 CH L-4 H CH2CH3 CH3 OCH3 N L-4 H CH3 CH3 CH2CN N L-4 H F CH3 OCH3 N L-4 H F H CH3 N L-4 H Cl CH3 OCH3 N L-4 H Br CH3 OCH3 N L-4 H NO2 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 N L-4 CH3 CO2CH2CH3 CH3 OCH3 N L-4 CH3 C 2CH2CHCH2 CH3 OCH3 CH L-4 CH3 S02N(CH3)2 CH3 OCH3 N L-4 CH3 S02N(CH3)2 CH3 OCH3 CH L-4 CH3 SO2N(CH2CH3)2 CH3 OCH3 N L-4 H S02N(OCH3)CH3 CH3 OCH3 N L-4 H SO2N(CH3)H CH3 OCH3 N L-4 CH3 SO2CH3 CH3 OCH3 N L-4 CH3 SO2CH2CH3 CH3 OCH3 CH L-4 CH3 S 2CH2CH2CH3 CH3 OCH3 CH L-4 H SCH3 CH3 CH2CN N Table 4c EMI42.1 L R R5 R14 R15 Z m.p.( C) L-4 H CH3 H CH3 N L-4 H CH3 H CH3 CH L-4 H CH2CH3 H CH3 CH L-4 CH2CH2CH3 CH3 CH3 N L-4 H F H CH3 CH L-4 H F H CH2CH3 N L-4 H Cl CH3 CH3 CH L-4 H Cl CH2CH3 CH3 N L-4 H Br H CH3 N L-4 H NO2 H CH3 N L-4 H NO2 CH3 CH3 CH L-4 CO2CH3 H CH3 CH L-4 CO2CH3 H CH3 N L-4 CO2CH3 H CH2CH3 CH L-4 H CO2CH3 CH3 CH3 CH L-4 H CO2CH2CH3 H CH3 N L-4 H CO2CH2CH3 CH2CH3 CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2CH3 H CH3 N L-4 H CO2CH2CH2Cl H CH3 N L-4 H CO2CH2CH=CH2 H CH3 CH L-4 H CO2CH2CH=CH2 H CH3 N L-4 H SO2N(CH3)2 H CH3 CH L-4 H SO2N(CH3)2 H CH3 N L-4 H SO2N(CH3)2 CH3 CH3 CH L-4 H SOCH3 H CH3 N Table 4c (continued) L R R5 R14 R15 Z m.p.( C) L-4 H CH3 CH3 OCH3 CH L-4 H CH3 CH3 OCH3 N L-4 H CH3 CH3 CH2CN N L-4 H F CH3 OCH3 N L-4 H Cl CH3 OCH3 CH L-4 H Cl CH3 OCH2CH3 N L-4 H Br CH3 OCH3 N L-4 H NO2 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 CH L-4 H CO2CH3 CH3 OCH3 N L-4 H CO2CH3 CH3 OCH2CH3 N L-4 CH3 CO2CH2CH3 CH3 OCH3 N L-4 CH3 C 2CH2CH=CH2 CH3 OCH3 N L-4 CH3 S02N(CH3)2 CH3 OCH3 N L-4 H SO2N(CH3)2 CH3 CH2CN N L-4 H SO2N(OCH3)CH3 CH3 OCH3 CH L-4 H SO2N(CH3)H H CH3 N L-4 H S02N(CH3)H CH3 OCH3 N L-4 H SO2CR3 CH3 OCH3 CH L-4 CH3 SO2NCH3 CH3 OCH3 N L-4 H SO2CH2CH3 CH3 CH2CN N L-4 H S(O)CH3 H CH3 N Table Sa EMI44.1 L R R5 R14 R15 Z m.p.( C) L-5 H CH3 H CH3 N L-5 H CH3 H CH3 CH L-5 H CH2CH3 H CH3 CH L-5 H CH2CH2CH3 CH3 CH3 N L-5 H F H CH3 CH L-5 H F H CH2CH3 N L-5 H Cl CH3 CH3 Ch L-5 H Cl CH2CH3 CH3 N L-5 H Br H CH3 N L-S H NO2 H CH3 N L-S H NO2 CH3 CH3 CH L-S H CO2CH3 H CH3 CH L-5 H CO2CH3 H CH3 N L-5 H CO2CH3 H CH2CH3 CH L-5 H CO2CH3 CH3 CH3 Ch L-5 H CO2CH2CH3 H CH3 N L-5 H CO2CH2CH3 CH2CH3 CH3 N L-S H CO2CH2CH2CH3 H CH3 N L-5 H CO2CH2CH2CH2CH3 H CH3 N L-5 H CO2CH2CH2CH3 H CH3 N L-5 H CO2CH2CH2Cl H CH3 N L-5 H CO2CH2CH=CH2 H CH3 CH L-5 H CO2CH2CH=CH2 H CH3 N L-5 H SO2N(CH3)2 H CH3 CH L-S H SO2N(CH3)2 H CH3 N L-5 H SO2N(CH3)2 CH3 CH3 Ch L-5 H CH3 H CH3 N L-5 H SOCH3 H CH3 N L-5 H SO2N(OCH3)CH3 H CH3 N Table 5a (continued) L R R5 R14 R15 Z m.p.( C) L-5 H CH3 CH3 OCH3 CH L-5 H CH3 CH3 OCH3 N L-5 H CH3 CH3 CH2CN N L-5 H F CH3 OCH3 N L-5 H F H CH3 N L-5 H Cl CH3 OCH3 N L-5 H Cl CH3 OCH2CH3 N L-5 H Br CH3 CH2CN N L-5 H NO2 CH3 OCH3 CH L-5 H CO2CH3 CH3 OCH3 N L-5 CH3 CO2CH3 CH3 OCH3 N L-5 CH3 C 2CH2CH=CH2 CH3 OCH3 CH L-5 CH3 C 2CH2CH=CH2 CH3 OCH3 N L-5 H CO2CH2C#CH CH3 OCH3 N L-5 CH3 S02N(CH3)2 CH3 OCH3 N L-5 H SO2N(CH3)2 CH3 CH2CN N L-5 H SO2N(CH3)CH2CH3 CH3 OCH3 CH L-5 H SO2N(OCH3)CH3 CH3 OCH3 CH L-5 H SO2N(CH3)H H CH3 N L-5 H SO2N(CH3)H CH3 OCH3 N L-5 H SO2CH3 CH3 OCH3 CH L-5 CH3 SO2CH3 CH3 OCH3 N L-5 H SO2CH2CH3 CH3 CH2CN N L-5 H SCH3 CH3 CH2CN N Table 5b EMI46.1 L R R5 R14 R15 Z m.p.( C) L-5 H CH3 H CH3 N L-5 H CH3 H CH3 Ch L-5 H CH2CH3 H CH3 Ch L-5 H Ch2CH2CH3 CH3 CH3 N L-S H F H CH3 CH L-5 H F H CH2CH3 N L-5 H Cl CH3 CH3 Ch L-5 H Cl CH2CH3 CH3 N L-5 H Br H CH3 N L-5 H NO2 H CH3 N L-5 H NO2 CH3 CH3 Ch L-S H CO2CH3 H CH3 CH L-5 H CO2CH3 H CH3 N L-5 H CO2CH3 H CH2CH3 CH L-5 H CO2CH3 CH3 CH3 CH L-5 H CO2CH2CH3 H CH3 N L-5 H CO2CH2CH3 CH2CH3 CH3 N L-5 H CO2CH2CH2CH3 H CH3 N L-5 H CO2CH2Ch2Ch2Ch3 H CH3 N L-S H CO2CH2Ch2OCH3 H CH3 N L-5 H CO2CH2CH2Cl H CH3 N L-5 H CO2CH2CH=CH2 H CH3 CH L-5 H CO2CH2CH=CH2 H CH3 N L-5 H SO2N(CH3)2 H CH3 CH L-5 H SO2N(CH3)2 H CH3 N L-5 H SO2N(CH3)2 CH3 CH3 CH L-5 H SCH3 H CH3 N L-5 H SOCH3 H CH3 N Table 5b (continued) L R r5 R14 R15 Z L-5 H CH3 CH3 OCH3 CH L-5 H CH2CH3 CH3 OCH3 N L-5 H CH2CH2CH3 CH3 OCH3 CH L-5 H F CH3 OCH3 N L-5 H Cl CH3 OCH3 CH L-5 H Br CH3 OCH3 N L-5 H Br CH3 CH2CN N L-5 H CO2CH3 CH3 OCH3 CH L-5 H CO2CH3 CH3 OCH3 N L-5 H CO2CH3 CH3 OCH2CH3 N L-5 CH3 Co2CH2CH3 CH3 OCH3 N L-5 CH3 C 2CH2CH=CH2 CH3 OCH3 N L-5 CH3 SO2N(CH3)2 CH3 OCH3 N L-5 CH3 SO2N(CH3)2 CH3 OCH3 CH L-5 H S 2N(CH3)CH2CH3 CH3 OCH3 CH L-5 H SO2(OCH3)CH3 CH3 OCH3 CH L-5 H SO2N(CH3)H H CH3 N L-5 H S02N(CH3)H CH3 OCH2CH3 N L-5 H SO2CH3 CH3 OCH3 CH L-5 CH3 SO2CH2CH3 CH3 OCH3 CH L-5 CH3 SO2CH2CH2CH3 CH3 OCH3 CH L-5 H SCH3 CH3 CH2CN N Table 5c EMI48.1 L R R5 R14 R15 Z m.p.( C) L-5 H CH3 H CR3 , N L-5 H CH3 H CH3 CH L-5 H CH2CH3 H CH3 CH L-5 H CH2CH2CH3 CH3 CH3 N L-5 H F H CH3 CH L-5 H F H CH2CH3 N L-5 H Cl CH3 CH3 Ch L-5 H Cl CH2CH3 CH3 N L-5 H Br H CH3 N L-5 H NO2 H CH3 N L-5 H NO2 CH3 CH3 Ch L-5 H CO2CH3 H CH3 Ch L-5 H CO2CH3 H CH3 N 211-212(d) L-5 H CO2CH3 H CH2CH3 CH L-5 H CO2CH3 CH3 CH3 CH L-5 H CO2CH2CH3 H CH3 N L-5 H CO2CH2CH3 CH2CH3 CH3 N L-5 H CO2CH2CH2CH3 H CH3 N L-5 H CO2CH2CH2CH2CH3 H CH3 N L-5 H CO2CH2CH2OCH3 H CH3 N L-5 H CO2CH2CH2Cl H CH3 N L-5 H CO2CH2CH=CH2 H CH3 CH L-S H CO2CH2CH=CH2 H CH3 N L-5 H SO2N(CH3)2 H CH3 CH L-5 H SO2N(CH3)2 H CH3 N L-5 H SO2N(CH3)2 CH3 CH3 CH L-5 H SOCH3 H CH3 N Table 5c (continued) L R R5 R14 R15 Z m.p.( C) L-5 H CH3 CH3 OCH3 N L-5 H CH3 CH3 CH2CN N L-5 H CH2CH2CH3 CH3 OCH3 CH L-5 H F H CH3 N L-5 H Cl CH3 OCH3 CH L-5 H Cl CH3 OCH2CH3 N L-5 H Br CH3 CH2CN N L-5 H <RTI ID=49.1> C 2CH3 CH3 OCH3 CH L-5 H CO2CH3 CH3 OCH3 N L-5 CH3 C02CH3 CH3 OCH3 N L-5 CH3 CO2CH2CH3 CH3 OCH3 N L-5 CH3 CO2CH2CH=CH2 CH3 OCH3 CH L-5 H CO2CH2C#CH H CH3 N L-5 H CO2CH2C#CH CH3 OCH3 N L-5 CH3 SO2N(CH3)2 CH3 OCH3 CH L-5 H SO2N(CH3)CH2CH3 CH3 OCH3 CH L-5 H SO2N(OCH3)CH3 CH3 OCH3 CH L-5 H S02N(CH3)H H CH3 N L-5 H SO2N(CH3)H CH3 OCH2CH3 N L-5 H SO2CH3 CH3 OCH3 CH L-5 CH3 SO2CH2CH3 CH3 OCH3 CH L-5 CH3 SO2CH2CH2CH3 CH3 OCH3 CH L-5 H SCH3 CH3 CH2CN N Table 6a EMI50.1 L R R5 R14 R15 Z m.p.( C) L-6 H CH3 H CH3 N L-6 H CR3 H CH3 CH L-6 H CH2CH3 H CH3 CH L-6 H CH2CH2CH3 CH3 CH3 N L-6 H F H CH3 CH L-6 H F H CH2CH3 N L-6 H Cl CH3 CH3 CH L-6 H Cl CH2CH3 Ch3 N L-6 H Br H CH3 N L-6 H NO2 H CH3 N L-6 H NO2 CH3 CH3 Ch L-6 H CO2CH3 H CH3 CH L-6 H C02CR3 H CH3 N L-6 H CO2CH3 H CH2CH3 CH L-6 H CO2CH3 CH3 CH3 CH L-6 H CO2CH2CH3 H CH3 N L-6 H CO2CH2CH3 CH2CH3 CH3 N L-6 H CO2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2OCH3 H CH3 N L-6 H CO2CH2CH2Cl H CH3 N L-6 H CO2CH2CH=CH2 H CH3 CH L-6 H CO2CH2CH=CH2 H CH3 N L-S H SO2N(CH3)2 H CH3 CH L-6 H SO2N(CH3)2 H CH3 N L-6 H SO2N(CH3)2 CH3 CH3 CH L-6 H SCH3 H CH3 N L-6 H SOCH3 H CH3 N L-6 H SO2N(OCH3)CH3 H CH3 N Table 6a (continued) L R R5 R14 R15 Z m.p.( C) L-6 H CH3 CH3 OCH3 CH L-6 H CH3 CH3 OCH3 N L-6 H CH3 CH3 CH2CN N L-6 H F CH3 OCH3 N L-6 H F H CH3 N L-6 H Cl CH3 OCH3 N L-6 H Cl CH3 OCH2CH3 N L-6 H Br CH3 CH2CN N L-6 H NO2 CH3 OCH3 CH L-6 H CO2CH3 CH3 OCH3 N L-6 CH3 CO2CH3 CH3 OCH3 N L-6 H CO2CH3 CH3 OCH2CH3 N L-6 CH3 C02CH2CH=CH2 CH3 OCH3 CH L-6 H CO2CH2C#CH CH3 OCH3 N L-6 CH3 SO2N(CH3)2 CH3 OCH3 CH L-6 H SO2N(OCH3)CH3 CH3 OCH3 CH L-6 H S02N(CH3)H H CH3 N L-6 H SO2N(CH3)H CH3 OCH2CH3 N L-6 CH3 SO2CH3 CH3 OCH3 N L-6 H SO2CH2CH3 CH3 CH2CN N L-6 CH3 SO2CH2CH2CH3 CH3 OCH3 N L-6 H S(O)CH3 H CH3 N Table 6b EMI52.1 L R R5 R14 R15 Z m.p.( C) L-6 H CH3 H CH3 N L-6 H CH3 H CH3 CH L-6 H CH2CH3 H CH3 CH L-6 H CH2CH2CH3 CH3 CH3 N L-6 H P H CH3 CH L-6 H F H CH2CH3 N L-6 H Cl CH3 CH3 CH L-6 H Cl CH2CH3 CH3 N L-6 H Br H CH3 N L-6 H NO2 H CH3 N L-6 H NO2 CH3 CH3 CH L-6 H CO2CH3 H CH3 CH L-6 H CO2CH3 H CH3 N L-6 H CO2CH3 H CH2CH3 CH L-6 CO2CH3 CH3 CH3 CH L-6 H CO2CH2CH3 H CH3 N L-6 H CO2CH2CH3 CH2CH3 CH3 N L-6 H CO2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2Cl H CH3 N L-6 H CO2CH2CH=CH2 H CH3 CH L-6 H CO2CH2CH=CH2 H CH3 N L-6 H SO2N(CH3)2 H CH3 CH L-6 H SO2N(CH3)2 H CH3 N L-6 H SO2N(CH3)2 CH3 CH3 CH L-6 H SCH3 H CH3 N Table 6b (continued) <RTI ID=53.1> L R R5 R14 R15 Z m.p.( C) L-6 H CH3 CH3 OCH3 CH L-6 H CH3 CH3 CH2CN N L-6 H F CH3 OCH3 N L-6 H Cl CH3 OCH3 CH L-6 H Cl CH3 OCH2CH3 N L-6 H Br CH3 OCH3 N L-6 H NO2 CH3 OCH3 CH L-6 H CO2CH3 CH3 OCH3 N L-6 CH3 CO2CH3 CH3 OCH3 N L-6 CH3 CO2CH2CH3 CH3 OCH3 N L-6 CH3 CO2CH2CH=CH2 CH3 OCH3 CH L-6 H CO2CH2C#CH H CH3 N L-6 CH3 S02N(CH3)2 CH3 OCH3 N L-6 H 502N(CH3)2 CH3 CH2CN N L-6 H SO2N(CH3)CH2CH3 CH3 OCH3 CH L-6 H SO2N(OCH3)CH3 CH3 OCH3 CH L-6 H SO2N(OCH3)CH3 CH3 OCH3 N L-6 H S02N(CH3)H CH3 OCH3 N L-6 H SO2N(CH3)H CH3 OCH2CH3 N L-6 CH3 SO2CH3 CH3 OCH3 N L-6 H SO2CH2CH3 CH3 CH2CN N L-6 CH3 SO2CH2CH2CH3 CH3 OCH3 N L-6 H S(O)CH3 H CH3 N Table 6c EMI54.1 L R R5 R14 R15 Z m.p.( C) L-6 H CH3 H CH3 N L-6 H CH3 H CH3 CH L-6 H CH2CH3 H CH3 CH L-6 H CH2CH2CH3 CH3 CH3 N L-6 H P H CH3 CH L-6 H F H CH2CH3 N L-6 H Cl CH3 Ch3 CH L-6 H Cl CH2CH3 CH3 N L-6 H Br H CH3 N L-6 H NO2 H CH3 N L-6 H NO2 CH3 CH3 CH L-6 H CO2CH3 H CH3 CH L-6 H CO2CH3 H CH3 N L-6 H CO2CH3 H CH2CH3 CH L-6 H CO2CH3 CH3 CH3 CH L-6 H CO2CH2CH3 H CH3 N L-6 H CO2CH2CH3 CH2CH3 CH3 N L-6 H CO2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2CH2CH3 H CH3 N L-6 H CO2CH2CH2OCH3 H CH3 N L-6 H CO2CH2CH2Cl H CH3 N L-6 H CO2CH2CH=CH2 H CH3 CH L-6 H CO2CH2CH=CH2 H CH3 N L-6 H SO2N(CH3)2 H CH3 CH L-6 H SO2N(CH3)2 H CH3 N L-6 H SO2N(CH3)2 CH3 CH3 CH Table 6c (continued) L R R5 R14 R15 Z m.p.( C) L-6 H CH3 CH3 OCH3 CH L-6 H CH3 CH3 OCH3 N L-6 H CH3 CH3 CH2CN N L-6 H F CH3 OCH3 N L-6 H Cl CH3 OCH3 CH L-6 H Cl CH3 OCH3 N L-6 H Br CH3 OCH3 N L-6 H Br CH3 CH2CN N L-6 H CO2CH3 CH3 OCH3 CH L-6 H C 2CH3 CH3 OCH3 N L-6 H CO2CH3 CH3 OCH2CH3 N L-6 CH3 CO2CH2CH3 CH3 OCH3 N L-6 CH3 CO2CH2CH=CH2 CH3 OCH3 N L-6 CH3 SO2N(CH3)2 CH3 OCH3 N L-6 H SO2N(CH3)2 CH3 CH2CN N L-6 CH3 SO2N(CH2CH3)2 CH3 OCH3 N L-6 H SO2N(OCH3)CH3 CH3 OCH3 CH L-6 H SO2N(CH3)H H CH3 N L-6 H SO2N(CH3)H CH3 OCH2CH3 N L-6 H SO2CH3 CH3 OCH3 CH L-6 H SO2CH2CH3 CH3 CH2CN N L-6 CH3 SO2CH2CH2CH3 CH3 OCH3 N L-6 H SCH3 CH3 CH2CN N L-6 H S(O)CH3 H CH3 N Table 7a EMI56.1 R R6 R14 R15 Z m.p.( C) CH3 CO2CH3 H CH3 N H CO2CH3 H CH3 CH H CO2CH3 H CH3 N H CO2CH3 CH3 CH3 CH H CO2CH3 CH2CH3 CH3 N H CO2CH2CH3 H CH3 CH H CO2CH2CH3 H CH3 N H CO2CH2CH3 CH3 CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 CH3 CH3 N H OSO2CH3 H CH3 N H SO2CH3 H CH3 N H SO2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 N H CO2CH3 CH3 OCH3 N H CO2CH3 CH3 OCHzCH3 N H CO2CH3 CH3 CH2CN N H SO2N(CH3)2 CH3 OCH3 N H SO2N(CH3)2 CH3 CH2CN N H OSO2CH3 CH3 OCH3 CH H SO2CH3 CH3 OCH3 CH H SO2CH3 CH3 CH2CN N H SO2CH2CH3 CH3 OCH3 CH H SO2CH2CH3 CH2CH3 OCH3 N Table 7b EMI57.1 R R6 R14 R15 Z m.p.( C) CH3 CO2CH3 H CH3 N H CO2CH3 H CH3 CH H CO2CH3 H CH3 N H CO2CH3 CH3 CH3 CH H CO2CH3 CH2CH3 CH3 N H C02CH2CH3 H CH3 CH H CO2CH2CH3 H CH3 N H CO2CH2CH3 CH3 CH3 N H S02N(CH3)2 H CH3 CH H S02N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 CH3 CH3 N H OSO2CH3 H CH3 N H SO2CH3 H CH3 N H SO2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 N CH3 CO2CH3 CH3 OCH3 CH H CO2CH3 CH3 OCH3 N H CO2CH3 CH3 CH2CN N H CO2CH2CH3 CH3 OCH3 CH H SO2N(CH3)2 CH3 OCH3 CH H SO2N(CH3)2 CH3 CH2CN N H OSO2CH3 CH3 OCH2CH3 N H SO2CH3 CH3 OCH3 N H SO2CH3 CH3 CH2CN N H SO2CH2CH3 CH3 OCH3 N Table 7c EMI58.1 R R6 R14 R15 Z m.p.( C) CH3 CO2CH3 H CH3 N H CO2CH3 H CH3 CH H CO2CH3 H CH3 N 220-225 H CO2CH3 CH3 CH3 CH H CO2CH3 CH2CH3 CH3 N H CO2CH2CH3 H CH3 CH H CO2CH2CH3 H CH3 N H CO2CH2CH3 CH3 CH3 N H SO2N(CH3)2 H CH3 CH H SO2N(CH3)2 H CH3 N H SO2N(CH3)2 CH3 CH3 CH H SO2N(CH3)2 CH3 CH3 N H OSO2CH3 H CH3 N H SO2CH3 H CH3 N H SO2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 CH H SO2CH2CH2CH3 H CH3 N CH3 CO2CH3 CH3OCH3 CH H CO2CH3 CH3 OCH3 N H CO2CH3 CH3 CH2CN N H SO2N(CH3)2 CH3 OCH3 N H SO2N(CH3)2 CH3 OCH3 CH H OSO2CH3 CH3 OCH2CH3 N H SO2CH3 CH3 OCH3 N H SO2CH3 CH3 OCHzCH3 N H SO2CH2CH3 CH3 OCH3 CH Table 8a EMI59.1 R R7 R8 R14 R15 Z m.p.( C) CH3 H H H CH3 N H H H H CH3 CH H H H H CH3 N H H H CH3 CH3 N H H H CH3 CH3 CH H CH3 H H CH3 N H CH3 H H CH3 CH H CH3 H CH3 CH3 N H CH3 H CH3 CH3 CH H CH3 H CH3 CH2CH3 N H CH2CH3 H H CH3 CH H CH2CH3 H H CH3 N H CH2CH3 H CH3 CH3 Ch H CH2CH2CH3 H H CH3 N H CH2CH2CH3 H H CH3 CH H CH(CH3)2 H H CH3 N H CH(CH3)2 H H CH3 CH H CH2CH2CH2CH3 H H CH3 CH H CH2CH2CH2CH3 H H CH3 N H CH2CH=CH2 H H CH3 CH H CH2CH=CH2 H H CH3 N H CH2CH2CH=CH2 H H CH3 N H CH2C#CH H H CH3 CH H CH2C#CH H H CH3 N H CH3OCH2CH2 H H CH3 N Table 8a (continued) m.p. R R7 R8 R14 R15 Z ( C) H CH2CH2OCH2CH3 H H CH3 N OCH3 H H H CH3 N CH3 H H CH3 OCH3 N H H H CH3 OCH3 N H H H CH3 CH2CN N H CH3 H CH3 OCH3 N H CH3 H CH2CH3 OCH N H CH2CH2CH3 H CH3 OCH2 N H CH2CH2CH3 H CH2CH3 OCH2CH3 N H CH2CH2CH2CH3 H CH3 CH2CN N H CH2CH2CH2CH2CH3 H CH3 OCH3 N H CH2CH=CH2 H CH3 OCH3 N H CH2CH2CH=CH2 H CH3 OCH3 CH H CH2C#CH H CH2CH3 OCH2CH3 N H CH2CH2OCH3 H CH3 OCH3 CH H CH2CH2OCH3 H CH3 OCH3 N H CH3 6-Cl CH3 OCH2CH3 N H CH2CH2CH3 5-OCH3 CH3 OCH3 CH H CH2CH=CH2 6-Cl CH2CH3 OCH2CH3 N CH3 CH2C#CH 6-OCH3 CH3 OCH3 CH H CH2CH2F H CH3 CH3 N H CH2CH2CH2F H H CH3 CH Table 8b EMI61.1 R R7 R8 R14 R15 Z m.p.( C) CH3 H H H CH3 N H H H H CH3 CH H H H H CH3 N H H H CH3 CH3 N H H H CH3 CH3 CH H CH3 H H CH3 N H CH3 H H CH3 CH H CH3 H CH3 CH3 N H CH3 H CH3 CH3 CH H CH3 H CH3 CH2CH3 N H CH2CH3 H H CH3 CH H CH2CH3 H H CH3 N H CH2CH3 H CH3 CH3 CH H CH2CH2CH3 H H CH3 N H CH2CH2CH3 H H CH3 CH H CH(CH3)2 H H CH3 N H CH(CH3)2 H H CH3 CH H CH2CH2CH2CH3 H H CH3 CH H CH2CH2CH2CH3 H H CH3 N H CH2CH=CH2 H H CH3 CH H CH2CH=CH2 H H CH3 N H CH2CH2CH=CH2 H H CH3 N H CH2C#CH H H CH3 CH H CH2C#CH H H CH3 N H H 6-C1 H CH3 N Table 8b (continued) R R7 R8 R14 R15 Z ( C) CH3 H H CH3 OCH3 N H H H CH3 OCH3 N H H H CH3 CH2CN N H CH3 H CH3 OCH3 N H CH3 H CH2CH3 OCH3 N H CH2(CH3)2 H CH3 OCH3 CH H CH2CH2CH3 H CH2CH3 OCH2CH3 N H CH2CH2CH2CH3 H CH3 OCH3 CH H CH2CH2CH2CH3 H H OCH3 N H CH2CH2CH2CH2CH3 H CH3 OCH3 N H CH2CH2CH=CH2 H CH3 OCH3 N H CH2CH2CH=CH2 H CH3 OCH3 CH H CH2C#CH H CH3 OCH3 N H CH2CH2OCH3 H CH3 OCH3 CH H CH3 6-C1 CH3 OCH2CH3 N H CH2CH2CH3 5-OCH3 OCH3 CH H CH2CH=CH2 6-Cl CH2CH3 OCH2CH3 N H CH2C#CH 6-OCH3 CH3 OCH2CH3 N H CH2CH2F H H CH3 N H CH2CH2CH2F H H CH3 CH Table 8c EMI63.1 R R7 R8 R14 R15 Z m.p.( C) CH3 H H H CH3 N H H H H CH3 CH H H H H CH3 N H H H CH3 CH3 N H H H CH3 CH3 CH H CH3 H H CH3 N H CH3 H H CH3 CH H CH3 H CH3 CH3 N H CH3 H CH3 CH3 CH H CH3 H CH3 CH2CH3 N H CH2CH3 H H CH3 CH H CH2CH3 H H CH3 N H CH2CH3 H CH3 CH3 Ch H CH2CH2CH3 H H CH3 N H CH2CH2CH3 H H CH3 CH H CH(CH3)2 H H CH3 N H CH(CH3)2 H H CH3 CH H CH2CH2CH2CH3 H H CH3 CH H CH2CH2CH2CH3 H H CH3 N H CH2CH=CH2 H H CH3 CH H CH2CH=CH2 H H CH3 N H CH2CH2CH=CH2 H H CH3 N H CH2C#CH H H CH3 CH H CH2C#CH H H CH3 N H CH2CH2OCH3 H H CH3 N Table 8c (continued) m.p. R R7 R8 R14 R15 Z ( C) CH3 H H CH3 OCH3 N H H H CH3 OCH3 N H R H CH3 OCH2CH3 N H CH3 H CH3 OCH3 N H CH3 H CH3 OCH3 CH H CH2(CH3)2 H CH3 OCH3 CH H CH2CH2CH3 H CH3 OCH3 N H CH2CH2CH3 H CH2CH3 OCH2CH3 N H CH2CH2CH2CH3 H CH3 CH2CN N H CH2CH=CH2 H CH3 OCH3 N H CH2CH2C#CH H CH3 OCH3 CH H CH2C#CH H CH3 OCH3 N H CH2CH2OCH3 H CH3 OCH3 CH H CH2CH2OCH2CH3 H CH3 OCH3 N H CH3 6-Cl CH3 OCH2CH3 N H CH2CH=CH2 6-Cl CH2CH3 OCH2CH3 N CH3 CH2C#CH 6-OCH3 CH3 OCH3 CH H CH2C#CH 6-Cl CH3 CH2CN N H CH2CH2F H H CH3 N H CH2CH2CH2F H H CH2CH3 CH Table 9a EMI65.1 R R7 R8 R9 R14 R15 Z m.p.( C) CH3 CH3 H H H CH3 N H H H H H CH3 N H H H H H CH3 CH H H H H CH3 CH3 N H H H CH3 H CH3 CR H H H CH3 CH3 CH3 Ch H CH2CH3 H H H CH3 CH H CH2CH3 H H H CH3 N H CH2CH3 H H CH3 CH3 N H CH2CH3 H H CH2CH3 CH3 N H CH2CH3 H CH3 H CH3 N H CH(CH3)2 H H H CH3 CH H CH(CH3)2 H H H CH3 N H CH2CH2CH3 H H H CH3 N H CH2CH2CH3 H H H CH3 CH H CH2CH2CH3 H H CH3 CH3 CH H CH2CH2CH2CH3 H H H CH3 CH H CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH3 H CH3 H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 N H CH2CH2CH2CH2CH3 H CH3 CH3 CH3 CH Table 9a (continued) m.p. R R7 R8 R9 R14 R15 Z ( C) H CH-CH=CE2 H H H CH3 N H CH-C#CH H H H CH3 N <RTI ID=66.4> H CH2CH2-OCH3 H H H CH3 N H CH2CH2-OCH2CH3 H H H CH3 N H CH3 H H CH3 CH2CN N H H H H CH3 OCH3 N H CH3 H CH3 CH3 OCH3 N H CH3 H H CH3 OCH3 N H CH3 H H CH2CH3 OCH2CH3 N H CH2CH3 H H CH3 OCH3 N H CH(CH3)2 H H CH3 OCH3 CH H CH2CH2CH3 H CH3 CH3 OCH3 N H CH2CH2CH3 H CH3 CH2CH3 OCH3 N H CH2CH2CH2CH3 H CH3 CH3 OCH3 N H CH2CH2CH2CH3 H CH3 CH3 CH2CN N H CH2CH2CH2CH2CH3 H CH3 CH3 CH2CN N H CH2CH=CH2 H H CH3 OCH3 N H CH2C#CH H H CH3 OCH3 CH H CH2CH2OCH3 H H CH3 OCH2CH3 N H CH3 6-CH3 H CH3 OCH3 N H CH3 7-CH3 CH3 CH3 OCH3 CH H CH2CH2CH3 7-Cl CH3 CH3 OCH3 CH H CH2CH=CH2 6-OCH3 H CH3 OCH3 CH H CH2CH=CH2 7-Cl CH3 Ch3 OCH3 N Table 9b EMI67.1 m.p. R R7 R8 R9 R14 R15 Z ( C) CH3 CH3 H H H CH3 N H H H H H CH3 N H H H H H CH3 CH H H H H CH3 CH3 N H H H CH3 H CH3 CH H H H CH3 CH3 CH3 CH H CH2CH3 H H H CH3 CH H CH2CH3 H H H CH3 N H CH2CH3 H H CH3 CH3 N H 2 3 H H CH2CH3 CH3 N H CH2C 3 H CH3 H CH3 N H CH(CH3)2 H H H CH3 CH H CH(CH3)2 H H H CH3 N H CH2CH2CH3 H H H CH3 N H CH2CH2CH3 H H H CH3 CH H CH2CH2CH3 H CH3 CH3 CH3 CH H CH2CH2CH2CH3 H H H CH3 CH H CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 N H CH2CH2CH2CH2CH3 H CH3 CH3 CH3 CH Table 9b (continued) m.p. R R7 R8 R9 R14 R15 Z ( C) H CH3 6-OCH3 H H CH3 N CH3 CH3 H H CH3 OCH3 N H H H H CH3 OCH3 N H CH3 H CR3 CH3 OCH3 N H CH3 H H CH3 OCH3 N H CH3 H H CH2CH3 OCH2CH3 N H CH2CH3 H H CH3 OCH3 N H CH2CH3 H H CH3 CH2CN N H CH(CH3)2 H H CH3 OCH3 CH H CH2CH2CH3 H CH3 CH3 OCH3 N H CH2CH2CH3 H CH3 CH2CH3 OCH3 N H CH2CH2CH2CH3 H CH3 CH3 OCH3 N H CH2CH=CH2 H H CH3 OCH3 CH H CH2C#CH H H CH3 OCH3 CH H CH2CH2C#CH H CH3 CH3 OCH3 N H CH2CH2OCH3 H H CH3 OCH2CH3 N R CH3 6-CH3 H CH3 OCH3 N H CH3 7-CH3 H CH3 OCH2CH3 N H CH2CH2CH3 7-Cl CH3 CH3 OCH3 CH H CH2CH2CH2 6-OCH3 H CH3 OCH3 N H CH2CH=CH2 7-Cl CH3 CH3 OCH3 N Table 9c EMI69.1 m.p. R R7 R8 R9 R14 R15 Z ( C) CH3 CR3 H H H CH3 N H H H H H CH3 N H H H H H CH3 CH H H H H CH3 CH3 N H H H CH3 H CH3 CR H H H CH3 CH3 CH3 CH H CH2CH3 H H H CH3 CH H CH2CH3 H H H CH3 N H CH2CH3 H H CH3 CH3 N H CH2CH3 H H CH2CH3 CH3 N H CH2CH3 H CH3 H CH3 N H CH(CH3)2 H H H CH3 CH H CH(CH3)2 H H H CH3 N H CH2CH2CH3 H H H CH3 N H CH2CH2CH3 H H H CH3 CH H CH2CH2CH3 H H CH3 CH3 CH H CH2CH2CH2CH3 H H H CH3 CH H CH2CH2Ch2Ch3 H H H CH3 N H CH2CH2CH2CH3 H CH3 H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 N H CH2CH2CH2CH2CH3 H H H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 CH H CH2CH2CH2CH2CH3 H CH3 H CH3 N H CH2CH2CH2CH2CH3 H CH3 CH3 CH3 Ch Table 9c (continued) R R7 R8 R9 R14 R15 Z ( C) CH3 CH3 H H CH3 OCH3 N H CH3 H H CH3 CH2CN N H H H H CH3 OCH3 CH H CH3 H CH3 CH3 OCH3 N H CH3 H H CH3 OCH3 CH H CH3 H H CH2CH3 OCH2CH3 N H CH2CH3 H H CH3 OCH3 CH H CH2CH3 H H CH3 CH2CN N H CH2CH2CH3 H H CH3 OCH3 N H CH2CH2CH3 H CH3 CH3 OCH3 N H CH2CH2CH3 H CH3 H OCH3 N H CH2CH2CH2CH3 H H CH3 OCH3 CH H CH2CH2CH2CH3 H CH3 CH3 CH2CN N H CH2CH=CH2 H H CH3 OCH3 CH H CH2C#CH H H CH3 OCH3 CH H CH2C#CH H H CH3 OCH3 N H CH2CH2CH3 H H CH3 OCH3 N H CH2CH2CH3 H H CH3 OCH2CH3 N H CH2CH2CH2CH3 H H CH2CH3 OCH2CH3 N H CH3 6-CH3 H CH3 OCH3 N H CH3 7-CH3 H CH3 OCH2CH3 N H CH2CH2CH3 7-Cl CH3 CH3 OCH3 CH H CH2CH=CH2 7-Cl H CH3 OCH2CH3 N Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets. solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Table 10 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 Guide," 2nd Ed., Interscience. New York, 1950. Solubility under 0.1% is preferred for suspension concentrates: solution concentrates are preferably stable against phase separation at OOC. "cCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Bidgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents1, 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 "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill. New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux. U.S. Patent 3,235,361, 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 Handbook", 5th Ed.. Blackwell Scientific Publications, Oxford. 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 4 Wettable Powder 2-[[[4-(methylamino)-6-(22,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl)benzoic acid. methyl ester 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 5 Wettable Powder 2-[[[4-(methylamino)-6-(2,2,22-trifluoroethoxy)-1,3,5 triazin -2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 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 6 Granule Wettable Powder of Example 4 5% attapulgite granules 95% (U.5.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 7 Extruded Pellet 2-r ((4-(methylamino)-6- (2,2, 2-trifluoroethoxy)-i, 3,5- triazin -2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 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 8 Oil Suspension 2-[([4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5- triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 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 9 Wettable Powder 2- (4-(methylamino)-6-(2.2.2-trifluoroethoxy)-1,3,5- triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 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 10 Low Strenqth Granule 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 1% N,N-dimethylformamide 9% attapulgite granules 90 (U.S.S. 20-40 sieve; 0.84-0.42mm) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. ExamPle 11 Aqueous Suspension 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyllaminosulfonyl]benzoic acid, methyl ester 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disedius phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0t 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 12 Solution 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester, sodium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. Example 13 Low Strenqth Granule 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5- triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 0.1% attapulgite granules 99.9% (U.S.S. 20-40 mesh; 0.84-0.42mm) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged. Example 14 Granule 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20% of the natural sugars) attapulgite clay 9% The ingredients are blended and milled to pass through a 100 mash screen (149 m crons). . This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level. generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns). and packaged for use. Example 15 High Strength Concentrate 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 99% silica aerogel 0.5t 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 16 Wettable Powder 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 90% dioctyl sodium sulfosuccinate 0.1S synthetic fine silica 9.9S 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 (0.3mm opening) and then packaged. Example 17 Wettable Powder 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-nil led and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 18 Oil Suspension [[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1.3,5- triazin-2-yl)aminocarbonyl]aminosulfonyl)benzoic acid, methyl ester 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly. extended with oils. or emulsified in water. Example 19 Dust 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoic 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 20 Emulsifiable Concentrate 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5 triazin2-yl]aminocarbonyl)aminosulfony13benzoic acid, ethyl ester 10% chlorobenzene 84% 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 Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/ or postemergence weed control in areas where complete control of all vegetation is desired. such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat. Alternatively, the subject compounds are useful to modify plant growth. The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as 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 0.01 to 10 kg/ha. the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification 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, aside, diphenylether, carbamate and bipyridylium types. The herbicidal properties of the subject com- pounds were discovered in a number of greenhouse tests. The test procedures and results follow. Compounds Compound 1 EMI81.1 Compound 2 EMI81.2 Compound 3 EMI81.3 Compound 4 EMI81.4 Compound 5 EMI81.5 Compounds (continued) Compound 6 EMI82.1 Compound 7 EMI82.2 Compound 8 EMI82.3 Compound 9 EMI82.4 Compound 10 EMI82.5 Compounds (continued) Compound 11 EMI83.1 Compound 12 EMI83.2 Test A Seeds of crabgrass (Diqitaria spp.). barnyardgrass (Echinochloa crusqalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia). morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugar beet, cotton, 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 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 O = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: B = burn; C = chlorosis/necrosis: D = defoliation: E = emergence inhibition; G = growth retardation: H = formative effect; U = unusual pigmentation; X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers. Table A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 10C 6C,9G 9C 10C Cocklebur 9C 6C,9G 10C 5C,9G Sicklepod 5C,9G 4C,8G 9C 5C,9G Nutsedge 2C,8G 2C,5G 4G 4G Crabgrass 2C,6G 3C,8G 5G 2C,5G Barnyardgrass 5C,9H 5C,9H 3C,5G 3C,9H Wild Oats 5C,9G 5C,9G 3C,8G 3C,9G Wheat 7G 8G 0 2C,8G Corn 9G 9G 5C,9G 4C.9H Soybean 5C,9G 5C,9H 5C,9H 3C,5H Rice 9C 5C,9G 5C,9G 5C,9G Sorghum 5C,9H 4C,9G 6C,9H 4C,8H Sugar beet 9C 9C 9C 9C Cotton 4C,9G 2C,8H 3C,8H 3C,7H PRE-EMERGENCE Morningglory 9G 9G 9G 9G Cocklebur 9H 8H 9H 8H Sicklepod 4C.9G 8G 5C,9G 3C Nutsedge 10E 5G 9G 3C,7G Crabgrass 2C,8G 2G 5G 2G Barnyardgrass 3C,9H 3C,9H 6G 3C,9H Wild Oats 5C,9H 5C,9H 2C,9G 3C,8G Wheat 3C,9H 5C,9H 6G 2C,9G Corn 2C,9G 5C,9H 2C,9G 9G Soybean 9H 9H 9H 2C,2H Rice 10E 10E 10E 5C,9H Sorghum 5C,9H 5C,9H 5C,9H 4C,9G Sugar beet 5C,9G 5C,9G 5C,9G 4C,9G Cotton 8G 2C,7G 8G 2C Table A (continued) Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory lOC lOC 4C,9G 2C,6H Cocklebur 9C 2C,9G 5C,9G 2C,8H Sicklepod 5C,9G 5C,9G 3C,5G 4C,9G Nutsedge O 0 SG 4G Crabgrass 0 3G 2G 0 Barnyardgrass 3C,4H 3C,9H 2C 2C,3H Wild Oats O 3C,8H 3G 2C,5G Wheat 0 0 3G 0 Corn 3C,8H 9G 0 3C,9H Soybean 3C,8H 4C,9G 0 3C,6H Rice 3C,8G 5C,9G 6G 5G Sorgum 3C,5H 3C,9H 2C,5H 2C,5G Sugar beet 9C 9C 1OC 5C,9G Cotton 0 2C,9G 2C,8H 4C,9H PRE-EMERGENCE Morningglory 9G 9G 9G 8G Cocklebur 2C 8H 8H 5G Sicklepod 4C,9G 9C 0 3C,9G Nutsedge 3G 8G 0 5G Crabgrass 0 5G 0 0 Barnyardgrass SG 3C,9H 2G 3C,7H Wild Oats 2C,6G 3C,8G 2C,5G 2C,5G Wheat 3G 6G 6G 3G Corn 2C,9G 3C,9G ZC,5G 3C,7G Soybean 3C,8H 3C,8H 1H 2C,2H Rice 3C,8G 9H 7G 4C,8H Sorghum 2C,'4G 4C,9H 2C,8G 4C,9H Sugar beet 4C,9G 4C,8G 5C,9G 4C,9G Cotton 3G SG 2G 0 Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Rate kg/ha 0.05 0.05 0.1 0.1 POST-EMERGENCE Morningglory 10C 9C 4C,9G 4C,9G Cocklebur 5C,9G 9C 5C,9G 2C,8G Sicklepod 5C,9G 5C,9G Nutsedge 5G 9G 5C,9G 3G Crabgrass 8G 2G 3C,7G 0 Barnyardgrass 2C,9H 3C,8H 3C,9H 3C,6H Wild Oats 4C,9G 5C,9G 2C.9G 0 Wheat 2C,8G 2G 2C,9G 0 Corn 3C,9H 3C,9H 9G 2C,7H Soybean 4C,8H 5C,9H 3C,9G 9G Rice 5C,9G 6C,9G 9C 8G Sorghum 3C,8H 3C,9H 2C,9H 4G Sugar beet 9C 9C 10C 9C Cotton 4C,9G 5C,9H 3C,9G 3C,6H Cheatgrass - - 2C,6G 0 Velvetleaf - - 9C 3C,8H PRE-EMERGENCE Morningglory 2C,9G 9G 9G 8G Cocklebur 7H 9H - Sicklepod 4C,9G 4C.SG - - Nutsedge 2G 10E 9G 0 Crabgrass 2C,5G 2G 2C 0 Barnyardgrass 3C,9H 8G 3C,9H 3G Wild Oats 3C,8G 4C.9G 7C.9G 0 Wheat 2C,9G 5G 9H 0 Corn 3C,9G 4C,9G 3C,9H 2C.8G Soybean 3C,5G 9H 3C,6G 4C,4H Rice 9H 10E 10E 3C,5G Sorghum 3C,8H 4C,9H 4C,9H 3C,5G Sugar beet 4C,9G 5C,9G 9C 9C Cotton 2C,5G 7G 2C,7H 0 Cheatgrass - - lOH 5G Velvetleaf - - 3C,8H 4G Test B Postererqence Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass (Alopecurus myosuroides), sugar beets, nutsedge (Cyperus rotundus) tubers, crabgrass (Diqitaria sanquinalis), sicklepod (Cassia obtusifolia). teaweed (Sida spinosa), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), and giant foxtail (Setaria faberii). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua), cocklebur (Xantium pensyl vanicum), morningglory (IPomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusqalli). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic solvent. Preemergence Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass (Alopecurus myosuroides), sugar beets, nutsedge, crabgrass, sicklepod, teaweed, jissonweed, velvetleaf, and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybeans. wild oats, cocklebur. morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent. Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response. Besponse ratings are based on a scale of O to 100: where 0 = no effect, and lOO = complete control. A dash (-) response means no test. Response ratings are contained in Table B. Table B Compound 1 POSTEMERGENCE Rate g/ha 62 16 4 Corn 100 70 40 Wheat 0 0 0 Rice 100 90 70 Soybean 90 80 20 Cotton 90 70 20 Sugar beet 100 90 80 Rape 20 0 0 Crabgrass 40 20 0 Johnsongrass 60 20 0 Blackgrass 90 80 20 Barnyardgrass 90 30 0 Nutsedge 80 50 20 Giant Foxtail 80 20 0 Wild Oats 90 50 0 Cocklebur 80 40 0 Morningglory 90 70 40 Teaweed 80 50 0 Sicklepod 80 60 0 Jimsonweed 90 80 60 Velvetleaf 90 90 60 PREEMERGENCE Rate g/ha 250 62 16 4 Corn 100 80 30 0 Wheat 40 20 0 0 Rice 100 100 90 70 Soybean 90 80 30 0 Cotton 90 70 20 0 Sugar beet 100 80 60 20 Rape 90 50 20 0 Crabgrass 70 60 20 0 Johnsongrass 90 90 80 20 Blackgrass 100 100 90 80 Barnyardgrass 90 80 50 0 Nutsedge 90 90 50 0 Giant Foxtail 100 90 80 20 Wild Oats 100 90 50 20 Cocklebur 80 50 0 0 Morningglory 90 80 40 0 Teaweed 90 90 60 0 Sicklepod 80 60 20 0 Jimsonweed 100 90 70 0 Velvetleaf 90 90 60 20 Table B (continued) Compound 2 POSTEMERGENCE Rate g/ha 62 16 4 Corn 100 80 20 Wheat o 0 0 Rice 90 80 30 Soybean 90 90 50 Cotton 30 0 0 Sugar beet 90 90 50 Rape O 0 0 Crabgrass 0 0 0 Johnsongrass 90 40 0 Blackgrass 90 60 20 Barnyardgrass 90 40 0 Nutsedge 0 0 0 Giant Foxtail 60 20 0 Wild Oats 60 0 0 Cocklebur 90 30 0 Morningglory 90 80 0 Teaweed O 0 0 Sicklepod 0 0 0 Jimsonweed 80 60 40 Velvetleaf 90 70 30 PREEMERGENCE Rate g/ha 250 62 16 Corn 90 70 20 Wheat 40 0 0 Rice 100 90 70 Soybean 50 30 0 Cotton 40 0 0 Sugar beet 90 70 20 Rape O 0 0 Crabgrass 60 20 0 Johnsongrass 90 90 50 Blackgrass 100 80 50 Barnyardgrass 70 40 0 Nut sedge 60 20 0 Giant Foxtail 90 70 20 Wild Oats 80 40 0 Cocklebur O 0 0 Morningglory 50 30 0 Teaweed 70 30 0 Sicklepod 40 0 0 Jimsonweed 80 30 0 Velvetleaf 90 20 0 Table B (continued) Compound 3 POSTEMERGENCE Rate g/ha 62 16 4 Corn 100 90 30 Wheat 0 0 0 Rice 100 90 50 Soybean 90 90 70 Cotton 20 0 0 Sugar beet 100 90 50 Rape 20 0 0 Crabgrass 50 0 0 Johnsongrass 90 80 20 Blackgrass 100 80 50 Barnyardgrass 0 0 0 Nutsedge 30 0 0 Giant Foxtail 0 0 0 Wild Oats 0 0 0 Cocklebur 70 0 0 Morningglory 90 80 70 Teaweed 70 30 0 Sicklepod 60 20 0 Jimsonweed 90 70 40 Velvetleaf 100 90 50 PREEMERGENCE Rate g/ha 250 62 16 Corn 90 80 20 Wheat 0 0 0 Rice 100 100 60 Soybean 90 80 20 Cotton 0 0 0 Sugar beet 100 90 30 Rape 80 20 0 Crabgrass 40 0 0 Johnsongrass 90 90 60 Blackgrass 100 90 80 Barnyardgrass 60 30 0 Nutsedge 90 30 0 Giant Foxtail 90 60 0 Wild Oats 70 20 0 Cocklebur 0 0 0 Morningglory 90 70 20 Teaweed 90 70 20 Sicklepod 70 20 0 Jimsonweed 90 70 20 Velvetleaf 90 80 30 Table B (continued) Compound 4 Compound 5 POSTEMERGENCE Bate g/ha 62 16 62 16 Corn 80 20 50 30 Wheat O 0 0 0 Rice 90 60 30 0 Soybean 80 50 90 70 Cotton 70 20 20 0 Sugar beet 80 50 100 80 Bape 20 0 0 0 Crabgrass O 0 0 0 Johnsongrass 40 0 0 0 Blackgrass 80 40 40 0 Barnyardgrass 70 20 0 0 Nutsedge O 0 0 0 Giant Foxtail 60 0 0 0 Wild Oats O 0 0 0 Cocklebur O 0 30 0 Morningglory 80 40 60 30 Teaweed O 0 20 0 Sicklepod 0 0 30 0 Jimsonweed 70 30 80 60 Velvetleaf 60 20 80 50 PREEMERGENCE Rate g/ha 250 62 250 62 Corn 30 0 50 20 Wheat 50 0 0 0 <RTI ID=92.4> Bice 80 70 70 50 Soybean 40 0 60 20 Cotton 0 0 0 0 Sugar beet 60 0 80 30 Rape O 0 0 0 Crabgrass 70 0 20 0 Johnsongrass 90 70 30 0 Blackgrass 90 80 70 50 Barnyardgrass 90 40 70 0 Nutsedge O 0 30 0 Giant Foxtail 90 70 60 0 Wild Oats 70 50 50 0 Cocklebur 20 0 0 0 Morningglory 30 0 60 20 Teaweed 40 0 30 0 Sicklepod O 0 20 0 Jinsonweed 20 0 40 0 Velvetleaf 20 0 80 20 Table B (continued) Compound 6 POSTEMERGENCE Rate g/ha 62 16 4 Corn 90 80 50 Wheat 0 0 0 Rice 90 80 50 Soybean 90 90 80 Cotton 80 60 20 Sugar beet 100 90 80 Rape 0 0 0 Crabgrass O 0 0 Johnsongrass 70 60 20 Blackgrass 40 20 0 Barnyardgrass 80 60 20 Nutsedge 0 0 0 Giant Foxtail 80 50 0 Wild Oats 20 0 0 Cocklebur 80 60 0 Morningglory 80 30 0 Teaweed 40 0 0 Sicklepod 40 20 0 Jimsonweed 80 70 30 Velvetleaf 90 80 70 PREEMERGENCE Rate g/ha 250 62 16 Corn 90 50 20 Wheat 20 0 0 Rice 100 80 50 Soybean 80 50 20 Cotton 80 50 20 Sugar beet 90 80 30 Rape 0 0 0 Crabgrass 50 30 0 Johnsongrass 90 80 50 Blackgrass 90 70 40 Barnyardgrass 90 70 40 Nutsedge 30 0 0 Giant Foxtail 100 70 30 Wild Oats 90 50 0 Cocklebur 80 20 0 Morningglory 80 40 0 Teaweed 90 60 20 Sicklepod 60 30 0 Jimsonweed 90 40 0 Velvetleaf 90 80 30 Table B (continued) Compound 7 POSTEMERGENCE Bate g/ha 62 16 4 1 Corn O 0 0 0 Wheat 0 0 0 0 Rice 20 0 0 0 Soybean O 0 0 0 Cotton 50 30 0 0 Sugar beet 100 100 90 50 Rape O 0 0 0 Crabgrass O 0 0 0 Johnsongrass O O Q O Blackgrass 40 0 0 0 -Barnyardgrass 0 0 0 0 Nutsedge 20 0 0 0 Giant Foxtail O 0 0 0 Wild Oats O 0 0 0 Cocklebur 90 30 0 0 Morningglory 40 0 0 0 Teaweed 30 0 0 0 Sicklepod O 0 0 0 Jimsonweed 60 20 0 0 Velvetleaf 100 40 20 0 PREEMERGENCE Rate g/ha 250 62 Corn 0 0 Wheat 0 0 Rice 60 0 Soybean 0 0 Cotton 20 0 Sugar beet 90 20 Rape O 0 Crabgrass 0 0 Johnsongrass 70 0 Blackgrass 70 40 Barnyardgrass o 0 Nutsedge 0 0 Giant Foxtail 60 0 Wild Oats 0 0 Cocklebur 20 0 Morningglory 70 0 Teaweed 50 0 Sicklepod 20 0 Jimsonweed 40 20 Velvetleaf 60 0 Table B (continued) Compound 8 POSTEMERGENCE Rate g/ha 62 16 4 Corn 40 20 0 Wheat 0 0 0 Rice 30 0 0 Soybean 80 30 0 Cotton 20 0 0 Sugar beet 100 90 50 Rape 0 0 0 Crabgrass 50 20 0 Johnsongrass 0 0 0 Blackgrass <RTI ID=95.4> 0 0 0 Barnyardgrass 0 0 0 Nutsedge 30 0 0 Giant Foxtail 0 0 0 Wild Oats 0 0 0 Cocklebur 0 0 0 Morningglory 0 0 0 Teaweed 20 0 0 Sicklepod 0 0 0 Jimsonweed 30 0 0 Velvetleaf 20 0 0 PREEMERGENCE Rate g/ha 250 62 Corn 0 0 Wheat 0 0 Rice 20 0 Soybean 0 0 Cotton 0 0 Sugar beet 30 0 Rape 0 0 Crabgrass 20 0 Johnsongrass 30 0 Blackgrass 80 40 Barnyardgrass 30 0 Nutsedge 0 0 Giant Foxtail 30 0 Wild Oats 0 0 Cocklebur 0 0 Morningglory 0 0 Teaweed 30 0 Sicklepod 20 0 Jimsonweed 20 0 Velvetleaf 0 0 Table B (continued) Compound 9 POSTEMERGENCE Rate g/ha 62 16 4 1 Corn 70 50 0 0 Wheat o 0 0 0 Rice 90 80 30 0 Soybean 90 90 80 30 Cotton 70 40 20 0 Sugar beet 100 95 90 50 Rape 20 0 0 0 Crabgrass 50 0 0 0 Johnsongrass 20 0 0 0 Blackgrass 80 50 20 0 Barnyardgrass 60 20 0 0 Nutsedge 20 0 0 0 Giant Foxtail 50 20 0 0 Wild Oats 20 0 0 0 Cocklebur 80 70 30 0 Morningglory 90 90 30 0 Teaweed 40 30 0 0 Sicklepod 40 0 0 0 Jimsonweed 30 0 0 0 Velvetleaf 80 40 0 0 PREEMERGENCE Bate g/ha 250 62 16 Corn 90 50 20 Wheat 40 0 0 Rice 90 80 30 Soybean 80 40 0 Cotton 70 40 20 Sugar beet 90 80 20 Rape 40 20 0 Crabgrass 70 20 0 Johnsongrass 70 50 0 Blackgrass 90 80 50 Barnyardgrass 90 60 0 Nutsedge 0 0 0 Giant Foxtail 90 70 0 Wild Oats 80 60 20 Cocklebur 70 40 0 Morningglory 90 80 30 Teaweed 80 60 20 Sicklepod 60 30 0 Jimsonweed 70 30 0 Velvetleaf 70 40 20 Table B (continued) Compound 10 POSTEMERGENCE Rate g/ha 62 16 4 1 Corn 70 20 0 0 Wheat 0 0 0 0 Rice 100 100 80 50 Soybean 100 100 90 60 Cotton B0 50 20 0 Sugar beet 100 100 90 50 Rape 20 0 0 0 Crabgrass O 0 0 0 Johnsongrass 0 0 0 0 Blackgrass 90 70 60 20 Barnyardgrass 0 0 0 0 Nutsedge 40 30 0 0 Giant Foxtail 0 0 0 0 Wild Oats 0 0 0 0 Cocklebur 100 100 50 0 Morningglory 95 90 30 0 Teaweed 50 30 20 0 Sicklepod 50 40 20 0 Jimsonweed 90 80 40 30 Velvetleaf 95 70 20 0 PREEMERGENCE Rate g/ha 250 62 16 Corn 80 20 0 Wheat 0 0 0 Rice 100 90 40 Soybean 90 40 0 Cotton 60 0 0 Sugar beet 90 80 30 Rape 60. 30 0 Crabgrass 90 60 20 Johnsongrass 90 40 0 Blackgrass 100 80 80 Barnyardgrass 80 30 0 Nutsedge 90 30 0 Giant Foxtail 70 20 0 Wild Oats 80 40 0 Cocklebur 90 40 0 Morningglory 90 50 20 Teaweed 80 20 0 Sicklepod 80 50 0 Jimsonweed 90 60 0 Velvetleaf 90 70 30

Claims: Claims: 1. A compound of the formula: EMI98.1 wherein EMI98.2 R1 is C1-C4 alkyl, C1-C4 alkoxy. F. Cl, Br, NO2, CO2R10, SO2NR11R12, SO2N(OCH3)CH3,S(O)nR13, CH2OCH3, CH2OC2H5, C6H5 or Q: Q is EMI99.1 R2 is H, F, Cl, Br, CF3, CH3, C2H5, OCH3, OC2H5, SCH3 or SC2H5; R3 is H, Ch3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or s(o)nCH3; R4 is CH3, C2H5, OCH3, OC2H5, F, Cl, Br, SO2NR11R12, SO2N(OCH3)CH3 or s(o)nR13; R5 is C1-C3 alkyl, F. Cl, Br, NO2, CO2R10, SO2NR11R12, SO2N(OCH3)CH3 or s(o)nR13; R6 is CO2CH3, CO2C2H5, SO2N(CH3)2, OSO2CH3, S02CH3 or SO2CH2CH3; R7 is H, C1-C5 alkyl, CH2CH2F, CH2CH2CH2F, C3-C4 alkenyl, C3-C4 alkynyl, CH3OCH2CH2 or C2H5OCH2CH2; H8 is H, C1 CH3 or OCH3; R9 is H or CH R10 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2C1. CH2CH=CH2 or CH2C-CH; R11 is H or C1-C2 alkyl; R12 is C1-C2 alkyl; R13 is C1-C3 alkyl; n is O, 1 or 2; X is NR14R15; R14 is H or C1-C2 alkyl; R15 is C1-C2 alkyl, OCH3, OC2H5 or CH2CN: Y is OCH2CH2F, OCH2CRF2 or OCH2CF3; and Z is CH or N; and their agriculturally suitable salts. 2. Compounds of Claim 1 wherein L is L-l, L-8 or L-9; and R is H. 3. Compounds of Claim 2 wherein R1 is C1-C3 alkyl, C1-C3 alkoxy. Cl, NO2, CO2C1-C3 alkyl. SO2N(CH3)2, SO2CH3 or SO2C2u5; B14 is H: Z is N: and R2 is in the 5-position of the phenyl ring. 4. Compounds of Claim 3 wherein L is L-1 or L-8; and B7 is H, CH3 or C2H5. 5. Compounds of Claim 4 wherein R15 is CH3; and R2 is H. 6. The compound of Claim 1 which is 2-t[[4- (methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, and agriculturally suitable salts thereof. 7. The compound of Claim 1 which is 2-([[4- (methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, and agriculturally suitable salts thereof. 8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of any of claims 1 to 7 and at least one of the following: surfactant, solid or liquid diluent, 9. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of any of claims 1 to 7. 10. A method for regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant selected from compounds of any of claims 1 to 7. 11. A process for the production of a compound of claim 1 which comprises: (a) reacting a sulfonyl isocyanate of formula LSO2NCO (II) wherein L fs as defined in claim 1, with an appropriately substituted aminohetrocycle of formula EMI101.1 wherein R, X, Y and Z are as defined in claim 1; or (b) reacting a sulfonamide of formula 2NH2 (IV) wherein L is as defined in claim 1, provided that R1 is other than C02R10, with a carbamate of formula EMI101.2 wherein R, X, Y and Z are as defined in claim 1 and R' is CH3 or phenyl.

Inventors: BOLINSKI, MARTHA MAE, DUMAS, DONALD JOSEPH
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1985
Main classification: C07D251
IPC codes: C07D521, A01N47, C07D251