HERBICIDAL SULFONAMIDES

Abstract: Sulfonamide derivatives of formulae wherein Q is selected from various 5 and 6-membered heterocyc­ lic groups, which are optionally substituted, Q′ is selected from various 6-membered nitrogen-­ containing heterocyclic groups, which are optionally substi­ tuted, R₁ is H, F, Cl, Br, CH₃, CF₃ or OCH₃, R₁₇ is H or CH₃, W is O or S, A is a substituted heterocyclic moiety, X is CH₃, OCH₃ or Cl, Y is amino or various organic groups, Z is CH or H; and their agriculturally suitable salts exhibit herbicidal and plant growth regulant effects. The compounds may be formulated for agricultural use in conventional manner. The compounds may be prepared by a variety of routes, e.g. by reacting an appropriately substituted benzene-­ sulfonamide having a Q or Q′ moiety in the 2-position with a methyl carbamate of the appropriate heterocylic amine, under catalytic conditions.

Description: Title Cognate Herbicidal Sulfonamides Background of the Invention The present invention relates to ortho-heterocyclic benzenesulfonylureas and, more particularly, to ortho-(mono, di or triazinyl)benzenesulfonylureas and to their use as pre- or post-emergent herbicides or as plant growth regulants. U.S. Patent 4,169,719 discloses and claims N (heterocyclicaminocarbonyl)arylsulfonamides, such as N ((4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesul- fonamide, which are useful as herbicides and as plant growth regulants. U.S. Patent 4,127,405 teaches that N-(l,3,5-tri- azin-2-ylaminocarbonyl)arylsulfonamides, such as N [(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, are useful as herbicides and as plant growth regulants. Our Es-A-44,209, published January 20, 1982, relates to a-substituted -o-methylbenzenesulfonamides of the general formula: EMI1.1 wherein, among other values, E can be CH or N; X and Y can be CH3 or OCH3; Z can be CH2SO2N(CH3)2, CH2WQ, EMI1.2 W' can be 0 or S; W can be 0, S, SO or S02; and Q can be C1-C4 alkyl. These compounds are useful as herbicides and as plant growth regulants. Our EP-A-44,211, published January 20, 1982 relates to N- (heterocyclicaminocarbonyl)-o-(hydrocarbyl)benzene- sulfonamides which are useful as herbicides and plant growth regulants. Compounds of the general formula: EMI2.1 are disclosed wherein R1 is H, F, C1, Br, NO2, CF3, C1-C4 alkyl, OCF3 or C1-C4 alkoxy; EMI2.2 n is O or 1; R2 and R3 are independently H or CH3; R4 and R5 can be, among other values, H or or CH3; and X and Y can be CH3, OCH3 or OCH2CH3. South African Patent Application No. 82/0465 t Nihon Tokushu Noyaku Seizo K.K. discloses and claims substituted phenylsulfonylurea derivatives of the formula: EMI2.3 wherein X is a phenyl or phenoxy group.and R represents a group: EMI3.1 wherein R1 and R2 are methyl or methoxy. The compounds are said to show a superior selective control effect, especially when employed as pre-germination soil treating agents or plant stems and leaves and soil treating agents for weeds in paddy rice fields. Summary of the Invention This invention relates to compounds of Formulae 1 or Ia, suitable agricultural compositions containing them, and their method-of-use as general and/or selective pre-emergence and/or post-emergence herbicides snd as plant growth regulants. EMI4.1 wherein Q is EMI4.2 EMI5.1 where Q' is EMI5.2 EMI6.1 W is O or S; W' is O or S; R is H, F, C1, CH3 or OCH3; R1 is H, F, C1, Br, CH3, CF3 or OCH3; R2, R3, R5, Rg, R10 , R11, R12 and R17 are independently H or CH3; R4, R6, R7 and R8 are independently H, CH3 or OCH3; R13, R14, R15 and R16 are independently CH3 or OCH3; R18 is H or CH3; Rl9 is H or CH3; R20 is H or CH3; R21 is H or CH3; R22 is H or CH3; R23 is H or CH3; R24 is H, CH3,, C2H5, C1, Br, OCH3 or OC2H5; R25 is H, CH3, C2H5, Cl, Br, OCH3 or OC2H5; R26 is H, CH3, C2H5, C1, Br, OCH3, OC2H5 or CO2CH3; R27 is H or CH3; R28 is H or CH3; EMI6.2 EMI7.1 X is CH3, OCH3 or C1; ; Y is CH3, C2H5, CH20CH3, OCH3, OC2H5, CH(OCH3)2, SCH3, CF3, NH2, NHCH3, N(CH3)2, OCH2CH20CH3, OCH2CF3 or EMI7.2 Y1 is CH3, C2H5, CH2OCH3, OCH3, OC2H5, CH(OCH3)2, NH2, NHCH3 or N(CH3)2; Z is CH or N; X1 is CH3, OCH3 or C1; G is O or CH2; X2 is C1-C3 alkyl or CH2CF3; Y2 is CH3O, C2H5O, CH3S or C2H5S; and their agriculturally suitable salts; provided that 1) when W is S, then R17 is H, EMI7.3 Y is CH3, OCH3, C2H5, CH20CH3, CH(OCH3)2 or EMI7.4 2) when Q, is EMI8.1 then R24 is H, CH3 or C2H5; R25 is H, CH3 or C2H5; and R26 is H, CH3, C2H5 or -C02CH3; 3) when one of R24, R25, R26 is other than H, then the other two substituents are H or CH3; 4) the total number of carbon atoms in R18, R19, R20, R212 R22 R23, R27 and R28 is less than or equal to 4; 5) when X is C1, then Z is CH and Y or Y1 is OCH3, NH2, OC2H3, NHCH3 or N(CH3)2; and 6) when R is CH3, then R is in the 3-, 4- or 5-position of the benzene ring. Preferred for their higher herbicidal activity and/or their more favorable ease of synthesis are: 1) Compounds of Formula I where W is O; 2) Compounds of Preferred (1) where R1 and R17 are H; 3) Compounds of Preferred (2) where R24 is H, CH3 or C2H5; R25 is H, CH3 or C2H5; and R26 is H, CH3, C2H5 or -CO2CH3; 4) Compounds of Preferred (3) where Y is CH3, CH2OC H3, OCH3, OC2H5, CH(OCH3)2 or EMI9.1 and A is EMI9.2 5) Compounds of Formula Ia where R and R17 are H; 6) Compounds of Preferred (5) where V1 is CH3, OCH3, CH20CH3 or N(CH3)2; 7) Compounds of Preferred (4) where Q is EMI9.3 8) Compounds of Preferred (4) where Q is EMI9.4 9) Compounds of Preferred (4) where Q is EMI9.5 10) Compounds of Preferred (4) where Q is EMI10.1 11) Compounds of Preferred (4) where Q is EMI10.2 12) Compounds of Preferred (4) where Q is EMI10.3 13) Compounds of Preferred (4) where Q is EMI10.4 14) Compounds of Preferred (4) where Q is EMI10.5 15) Compounds of Preferred (4) where Q is EMI11.1 16) Compounds of Preferred (4) where Q is EMI11.2 17) Compounds of Preferred (4) where Q is EMI11.3 18) Compounds of Preferred (4) where Q is EMI11.4 19) Compounds of Preferred (4) where Q is EMI11.5 20) Compounds of Preferred (4) where Q is EMI12.1 21) Compounds of Preferred (4) where Q EMI12.2 22) Compounds of Preferred (4) where Q EMI12.3 23) Compounds of Preferred (4) where Q EMI12.4 24) Compounds of Preferred (6) where Q' is EMI12.5 25) Compounds of Preferred (6) where Q' is EMI13.1 26) Compounds of Preferred (6) where Q' is EMI13.2 27) Compounds of Preferred (6) where Q' is EMI13.3 28) Compounds of Preferred (6) where Q' is EMI13.4 and 29) Compounds of Preferred (6) where Q' is EMI13.5 Specifically Preferred for reasons of their highest herbicidal activity or most favorable ease of synthesis are: : # N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 (tetrahydrofuran-2-yl)benzenesulfonamide; N-E(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 2-(tetrahydrofuran-2-yl )benzenesulfonamide; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide; # N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl] 2-(tetrahydrofuran-2-yl)benzenesulfonamide; # N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl] 2-(tetrahydrofuran-2-yl)benzenesulfonamide; N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl)-2-(tetrahydrofuran-2-yl)benzenesulfonamide; ; N-E(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)- 2-(2-pyridinyl)benzenesulfonamide; N-( (4, 6-dimethylpyrimidin-2-yl)aminocarbonyl)-2- (2- pyridinyl)benzenesulfonamide; # N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2 pyridinyl)benzenesulfonamide; and N-E(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 2-(2-pyrimidinyl)benzenesulfonamide. Detailed Description of the Invention Synthesis The ortho-heterocyclicbenzenesulfonylureas of Formula I can be prepared by reacting the appropriately substituted benzenesulfonamide II with an appropriate methyl heteroaryl carbamate III in the presence of an equimolar amount of trimethylaluminum according to the procedure of Equation 1. Unless indicated otherwise, all temperatures are in OC. Equation 1 EMI15.1 wherein R1, R17, Q and A are as previously defined, and W is 0. The reaction of Equation 1 is best carried out in methylene chloride at 250 to 400C for 24 to 96 hours under a nitrogen atmosphere. The product can be isolated by the addition of an aqueous acetic acid solution followed by extraction of the product into methylene chloride or direct filtration of a product of low solubility. The product can ordinarily be purified by trituration with solvents such as n-butyl chloride or ether or by column chromatography. Further details of this reaction and the preparation of the carbamates of Formula III can be found in U.S. Serial No. 337,934, laid open as a priority document in support of our copending European and British Patent Applications of6 January 1983 claiming priority therefrom. Equation la below illustrates the preparation of the required methylpyrimidinyl carbamates and methyltriazinyl carbamates of Formula (III) in Equation I above. Equation la EMI15.2 wherein A and R17 are as originally defined. According to Equation la, a heterocyclic amine of Formula (V) is reacted with two equivalents of sodium hydride and excess dimethylcarbonate to form III. The reac tion is run an inert solvent such as tetrahydrofuran at 25 C to reflux for 1 to 24 hours. The product is isolated by {a) adding about two equivalents of concentrated HC1 and water saturated with NaCl, and (b) separating out the organic phase and concentrating to dryness in vacuo. Literature references relating to the synthesis of heterocyclic amines such as V are given hereinafter. Compounds of Formula I, in which Q does not include Q-3, Q-4 or Q-5, may also be prepared by reacting the appropriately substituted benzenesulfonyl isocyanate or isothiocyanate with an appropriate aminoheterocycle, V, as shown in Equation 2. Equation 2 EMI17.1 wherein R1, R17, W and A are as previously defined, and Q is Q-1, Q-2, and Q-6 to Q-ll. The reaction of Equation 2 can best be carried out in an inert aprotic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at a temperature between 20 and 80b. A catalytic amount of 1,4-diazabicyclo[2,2,230ctane (DABCO) may be used to accelerate the reaction. In cases in which the products are insoluble in the reaction solvent, they may be isolated by simple filtration. When the products are soluble, they may be isolated by evaporation of the solvent and trituration of the residue with solvents such as l-chlorobutane, ethyl ether or methanol and filtration. The benzenesulfonyl isocyanates of Formula IVa may be prepared as shown below in Equation 3, by phosgenation of the sulfonamide II in the presence of butyl isocyanate. The sulfonyl isocyanates of Formula IV may also be prepared, as shown in Equation 4, by phosgenation of the butyl ureas of Formula VI. Equation 3 EMI18.1 wherein R1 and Q are as defined in Equation 2. The above reaction can be carried out by heating a mixture of the appropriate sulfonamide (II), an alkyl isocyanate such as butyl isocyanate and a catalytic amount of a tertiary amine such as 1,4-diaza (2,2,23bicyclooctane (DABCO) in xylene, or other inert solvent of boiling point > 135 to approximately 135 C. Phosgene cathen be added to the mixture over a 1-6 hour period until an excess of phosgene is present as indicated by a drop in the boiling point to less than 130 C. The mixture is then cooled and filtered to remove a small amount of insoluble byproducts. The solvent and the alkyl isocyanate can be distilled off in vacuo leaving a residue of the crude sulfonyl isocyanate, IVa, which can be used without further purification. Equation 4 EMI18.2 wherein R1 and Q are as defined in Equation 2. The compounds of Formula VI can be prepared by stirring a mixture of the sulfonamides, II, anhydrous potassium carbonate, and n-butyl isocyanate in acetone or methyl ethyl ketone at 25-800 until all of the sulfonamide has reacted. The products can be isolated by quenching in dilute mineral acid and recrystallizing the solid product. The compounds VI are then treated with phosgene and a catalytic amount of DABCO in refluxing xylene or chlorobenzene in a manner analogous to that described in Equation 3. Sulfonylisothiocyanates of Formula IV where W=S can be prepared by treatment of sulfonamides with carbon disulfide and potassium hydroxide followed by the reaction of the dipotassium salt with phosgene according to the teaching of K. Hartke, Arch. Pharm., 299, 174 (1966). Alternatively, compounds of Formula Ib in which W is S may be prepared by the reaction of the appropriate sulfonamide of Formula II with a heterocyclic isothiocyanate of Formula Va as depicted in Equation 5. Equation 5 EMI19.1 wherein A, Q and R1 are as previously defined. The reaction of Equation 5 is best carried out by dissolving or suspending the sulfonamide and isothiocyanate in a polar solvent such as acetone, acetonitrile, ethyl acetate or methyl ethyl ketone, adding an equivalent of a base such as potassium carbonate and stirring the mixture at ambient temperature up to the reflux temperature for one to twenty-four hours. In some cases, the product precipitates from the reaction mixture and can be removed by filtration. The product is stirred in dilute mineral acid, filtered and washed with cold water. If the product does not precipitate from the reaction mixture it can be isolated by evaporation of the solvent, trituration of the residue with dilute mineral acid and filtering off the insoluble product. The heterocyclic isothiocyanates which are used in the procedure of Equation 5 are prepared, for example, according to the method of Japan patent Application Pub: Kokai 51-143686, June 5, 1976, or that of W. Abraham and G. Barnikow, Tetrahedron, 29, 691-7 (1973). The synthesis of heterocyclic amine derivatives such as those depicted by Formula V has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., New York and London, to which the reader is now referred for further information. Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series. The 5,6-dihydrofuro[2,3-d]pyrimidin-2-amines, the cyclopentaEd)pyrimidin-2-amines, and the 6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amines, are prepared as described in our EP-A-15,683. Synthesis of the furo(2,3-djpyrimidin-2-amines are described in our EP-A-46,677. The heterocyclic amines in which A is a triazole ring are disclosed in our European Patent Application No. 82303611.6. Pyrimidine and triazine amines in which Y is dimethoxymethyl or 1,3-dioxolan 2-yl are prepared as described in copending U.S. Application Serial No. 328,09 8. (European Patent Application No. 206492.8 and British Patent Application 8234702). Sulfonamides of Formula II, in which Q is Q-1 or Q-2, can be prepared by the sequence of reactions shown in Equation 6. Equation 6 EMI21.1 EMI22.1 wherein R1 and W are as previously defined; X' is C1, Br or HS04; R24 and R25 are H, CH3 or C2H5; and R26 is H, CH3, C2H5 or CO2CH3. Reaction (6a): In this reaction an o-nitrosubstituted phenyl diazonium halide or sulfate is coupled with an appropriately substituted thiophene or furan in the presence of a catalyst such as cupric chloride. The conditions necessary for this transformation are described in Gomberg and Bachmann, J. Am. Chem. Soc., 46, 2339 (1924)'; J. Johnson, J. Chem. Soc., 895 (1946); and in J. Pharm. Soc. (Japan), 90, 1150-1155 (1970). In cases where both the a- and the S-position of the thiophene or furan are available for coupling, both isomers are usually obtained with the a-coupled product being the predominent isomer. These isomers can be separated by fractional crystallization or chromatography and carried on through the remaining three reactions of Equation 6. Reaction (6b): The reduction described in step (6b) is accomplished by treating a solution of the compounds of Formula IX, in a solvent such as ethanol, ethy-l acetate, or DMF, in a pressure vessel, with 100-1000 pounds per square inch of hydrogen at 80.1500 in the presence of a hydrogenation catalyst such as 5-10% palladium absorbed on carbon. When the theoretical amount of hydrogen has been absorbed, the solution is then cooled and the catalyst is removed by filtration. The product is then isolated by evaporation of the solvent. Reaction (6c): The diazotization and coupling with sulfur dioxide, described in step 6c, is accomplished in the following manner. A solution of the aniline of Formula X in a mixture of concentrated hydrochloric acid and glacial acetic acid is treated with a solution of sodium nitrite in water at -5 to OOC. After stirring for 10-15 minutes at OOC to insure complete diazotization, this solution is added to a mixture of an excess of sulfur dioxide, and a catalytic amount of cuprous chloride in glacial acetic acid at 0.So. The temperature is kept at 0-5 for 1/4 to 1 hour then raised to 20-250 and held at that temperature for 2-4 hours. This solution is then poured into a large excess of ice water, and the sulfonyl chloride products, XI, is isolated by filtration or by extraction into a solvent such as ethyl ether or methylene chloride followed by evaporation of the solvent. Reaction (6d): The amination described in step (6d) is carried out by treating a solution of the sulfonyl chloride of Formula XI with an excess of. anhydrous ammonia in a solvent such as ethyl ether or methylene chloride at 0-250C. If the product sulfonamide, II, is insoluble, it may be isolated by filtration followed by washing out the salts with water. If the product sulfonamide is soluble in the reaction solution, it may be iso lated by filtering off the precipitated ammonium chloride and evaporation of the solvent. Sulfonamides of Formula IIa can be chlorinated or brominated on the thiophene or furan ring by procedures well known in the art. These halogenated sulfonamides may then be reacted with sodium methoxide in methanol or sodium ethoxide in ethanol to replace the halogen atom with a methoxy or ethoxy group. Alternatively, the substituted nitrobenzenes of Formula IX can be prepared by the procedure shown in Equation 7. Equation 7 EMI24.1 wherein R1, R24, R25, R26, and W' are as previously defined. In the reaction shown in Equation 7, a furyl- or thienyl copper compound of Formula XII is reacted with an iodonitrobenzerfe in a solvent such as pyridine or quinoline. The copper compounds of Formula XII are prepared by reacting the corresponding lithium compounds with cuprous iodide or cuprous bromide in a solvent such as diethyl ether. The detailed procedures for these types of reactions are described in the following references: M. Nilsson and C. Ullenius, Acta. Chem. Scand., 24, 2379-2388 (1970); C. Ullenius, Acta. Chem. Scand., 26, 3383-3386 (1972). Sulfonamides containing a tetrahydrofuran or tetrahydrothiophene group (Formula II, Q = Q-6 and Q-7) can be prepared by catalytic reduction of the corresponding furan or thiophene compounds as shown in Equation 8. Equation 8 EMI25.1 wherein R1, R27, R18, R20, and W' are as previously defined. Selective reductions of the type shown in Equation 8 are well known in the literature. The choice of catalyst, solvent, pressure and temperature for reduction of furans has been reviewed by Samuel Sevadesh in The Furans by A. P. Dunlop and F. N. Peters, Reinhold Publishing Corporation, New York, N.Y. 1953, pp. 674-713; and by P. N. Rylander in Catalytic Hydro genation in Organic Synthesis, Academic Press, 1979, pp. 227-234. The reduction of thiophenes is reviewed by H. D. Hartough in Thiophene and Its Derivatives, The Chemistry of Heterocyclic Compounds Series, Interscience Publishers, Inc., New York, N.Y. 1952, pp. 167-169. Sulfonamides containing a tetrahydrothiophene or tetrahydrothiopyran group can also be prepared by the sequence of reactions shown in Equation 9. Equation 9 EMI26.1 EMI27.1 wherein EMI27.2 1 27' R28, R187 R19, R20, R21, R22 and R23 are as previously defined. The general conditions used to carry out the reactions described in Reactions (9a) and (9b) are described by P. G. Gassman and G. D. Gruetzmacher, J. Am. Chem. Soc., 96, 5487-5495 (1974). The procedures shown in Reactions (9c) and (9d) are directly analogous to those described in Reactions (6c) and (6d). Other sulfonamides containing tetrahydrofuran or tetrahydropyran groups can be prepared by the sequence of reactions shown in Equation 10. Equation 10 EMI27.3 EMI28.1 wherein A', R1, R27, R28, R18, R19, R20, R21, R22 and R23 are as previously defined; and X" is Cl or Br. Reaction (lOa): In this reaction a tert-butyl sulfonamide of Formula XVII is treated with two equivalents of n-butyl lithium at -500 to -800 in tetrahydrofuran solution to give the dilithio salt XVIII. Reaction (lOb): The salt XVI II is then immediately treated with one equivalent of a chloro- or bromoaldehyde of Formula XXI at -700 to -800. The temperature is raised to 250 for 1 to 3 days, and the reaction is then quenched by the addition of an acid such as acetic acid. The pure product, XIX, is isolated by stripping off the solvent and chromatographing or recrystallizing the crude product. Reaction (lOc): In this step the tert-butyl group is removed from XIX by heating these compounds in trifluoroacetic acid at 720 for 1-6 hours. The sulfonamides of Formula IIg are isolated in pure form by stripping off the trifluoroacetic acid solvent. Sulfonamides of Formula IIj, which contain a dihydrofuran or a dihydropyran group, can be prepared by the method shown in Equation 11. Equation 11 EMI29.1 wherein EMI30.1 X" is C1 or Br; and R1' R272 R282 R18 R192 R20, R21, and R22 are as previously defined. Reaction (lla): In this reaction a sulfonamide of Formula IIh is treated with one equivalent of N-chlorosuccinimide or N-bromosuccinimide at 00.600 in a solvent such as carbon tetrachloride or chloroform for 2-24 hours. The by-product succinimide is removed by filtration and the solution carried directly on to the next step. Reaction (llb): The sulfonamides of Formula IIi are dehydrohalogenated in carbon tetrachloride or chloroform solution by treatment with at least one equivalent of an appropriate base such as triethylamine, DABCO, pyridine, sodium methoxide or anhydrous potassium carbonate at 0-600 for 1-6 hours. The products are isolated by washing the organic solution with water, drying, and stripping off the solvent. The sulfonamides of Formula IIj can be obtained in pure form by recrystallization from a solvent such as ethanol, l-chlorobutane, or acetonitrile, or by column chromatography. Sulfonamides containing a pyrrole group can be prepared by the sequence of reactions shown in Equation 12. Equation 12 EMI31.1 wherein Q' is EMI31.2 R1, R27, R28, R18, and R19 are as previously defined. Reaction (12a): The lithio compounds of Formula XXI are prepared from the bromo compounds of Formula XX by treatment with n-butyl lithium at -800 in either hexane/ether or hexane/tetrahydrofuran solvent systems. The details of this type of transmetallation are further described by M. E. K. Cartoon and G. W. H. Cheeseman in J. Organometallic Chemistry, 212, 1-9 (1981). Reaction (12b): The lithio compounds5 XXII, are immediately treated with at least one equivalent of sulfur dioxide at 0 to -500. After warming to 250, the lithium sulfinates of Formula XXIII are filtered off, and can be carried directly on to reaction (12c). Reaction (12c): In this step chloramine is prepared at 00 by the addition of aqueous sodium hypochlorite to a stirred mixture of 30% ammonium hydroxide solution and diethyl ether. The lithium sulfinates of Formula XXIII are added to this mixture at 0 and the resulting mixture stirred at room temperature for 2-24 hours. The product sulfonamides are isolated by extraction into a solvent such as ethyl acetate and evaporation of the solvent. The sulfonamides of Formula IIk may be purified by recrystallization from solvents such as ethanol, l-chlorobutane, or acetonitrile, or by column chromatography. The bromo compounds of Formula XX can be prepared by methods well known in the art, such as those reviewed by A. R. Jones and G. P. Bean in The Chemistry of Pyrroles, Academic Press, New York, N.Y., 1977. Sulfonamides of Formula II in which Q is Q-ll can be prepared by the sequence of reactions shown in Equation 13. Reaction (13a): The dilithio salt of Formula XVIII is prepared as described above in reaction (lOa) then treated with a ketone of Formula XXIV at -70 to -800. The temperature is raised to 250 for 1 to 3 days, and the reaction is then quenched by the addition of an acid such as acetic acid. The product, XXV, is isolated by evaporation of the solvent followed by chromatography or recrystallization. Equation 13 EMI33.1 EMI34.1 wherein R1, R27, R28, R18, R19, R20, R21, R22, R23 and W' are as previously defined and at least one of R27 R28, R18 or R19 is hydrogen. Reaction (13b): Removal of the tert-butyl group is accomplished by heating the above products, XXV, in trifluoroacetic acid at 720 for 1-6 hours. Dehydration of the tertiary hydroxyl group occurs simultaneously and the isomeric mixture of olefinic sulfonamides, XXVI, are isolated upon evaporation of the trifluoroacetic acid solvent. In reaction (13c), sulfonamides of Formula XXVII are produced upon hydrogenation of the olefins, XXVI, under standard conditions. The ortho-heterocyclicbenzenesulfonylureas of Formula Ia can be prepared by reacting the appropriately substituted benzenesulfonamide with an appropriate methyl pyrimidinyl carbamate or methyl triazinyl carbamate in the presence of an equimolar amount of trimethylaluminum according to the procedure of Equation 14. Unless indicated otherwise, all temperatures are in OC. Equation 14 EMI35.1 where in A, R1, R17, Q|, X, Y1 and Z are as previously defined. The reaction of Equation 14 is best carried out in methylene chloride at 250 to 400C for 24 to 96 hours under a nitrogen atmosphere. The product can be isolated by the addition of an aqueous acetic acid solution followed by extraction of the product into methylene chloride or direct filtration of a product of low solubility. The product can ordinarily be purified by trituration with solvents such as n-butyl chloride or ether or by column chromatography. Further details of this reaction and the preparation of the carbamates of Formula III can be found in U.S. Serial No. 337,934. Sulfonamides of Formula II may be prepared by the sequence of reactions outlined in Equation 15. Equation 15 EMI36.1 wherein R1 and Q are as previously defined. The compounds of Formula XXIX are prepared by analogy with the teaching of 3. G. Lombardino in 3. Org. Chem., 36, 1843. An N-t-butyl sulfonamide of Formula XXVII I is dissolved in an ethereal solvent, such as tetrahydrofuran, and two equivalents of n-butyllithium in hexane are added at 02So. After 1-5 hours at 0-25 , the compound of Formula XXIX is formed. This is not isolated, but one equivalent of a copper (I) salt is added at -20 to Oo', followed by 1-1.5 equivalents of an appropriately substituted heteroaromatic iodide (XXX). The reaction mixture is then heated at 40-700 for 1-3 days, concentrated, poured onto aqueous ammonia, and filtered to provide the compound of Formula XXXI. The reaction of Formula 15c is conducted by heating a compound of Formula XXXI with 2-10 equivalents of trifluoroacetic acid or aqueous HBr with or without an inert solvent at 30-700 for 1-3 days. The product II may be isolated as a trifluoroacetate or hydrobromide salt by evaporation of solvent and excess acid and trituration with ether. The free base may be obtained by neutralization of the salt with aqueous base, extraction into an organic solvent, and concentration of the organic extracts. The compounds of Formula XXX may be prepared according to methods known in the art, such as those reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London, the teachings of which are incorporated herein by reference. The iodopyridines are described in Vol. 14 of the above series, pp. 407-488. Iodopyrimidines are described by D. J. Brown and S. F. Mason in Vol. 16 of the above series. The preparation of iodopyrazines is taught by A. Hirschberg and P. E. Spoerri, J. Orq. Chem., 26, 1907 (1981) and iodopyridazines are described by D. L. Aldons and R. N. Castle in Vol. 28 of the Interscience series, pp. 240-241. The iodo1,3,5-triazines are described by E. M. Smolin and L. Rapoport, in Vol. 13 of the above series, and a method for preparing iodo-1,2,4-triazines is taught by A. Rykowski and H.C. van der Plas, in J. Org. Chem., 45, 881 (1980). 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 treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques. Detailed examples of such techniques are given in United States Patent 4,127,405, the disclosure of which is herein incorporated by reference. The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless otherwise indicated. Example 1 Methyl 5-± (2-aminosulfonyl)phenyl]furan-2-carboxylate To a solution of 65.1 g of methyl 5-(2-aminophenyl)furan-2-carboxylate in a mixture of 270 ml of concentrated hydrochloric acid and 75 ml of glacial acetic acid was added a solution of 25.8 g of sodium nitrite in 75 ml of water at -50 to 00 dropwise over a 30-minute period. The resulting solution was stirred an additional 10 minutes at 0 before being slowly added to a mixture of 6.0 g of cuprous chloride and 50 ml of sulfur dioxide in 375 ml of glacial acetic acid at -5 . This reaction mass was stirred at 0 for 1 hour and at 250 for 2 hours before being poured into 2.2 t of ice water. The intermediate sulfonyl chloride precipitated as an oil and was extracted into l-chlorobutane, washed with water, 5% sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The solution of the sulfonyl chloride in l-chlorobutane was cooled to 50 and treated with 13.5 ml of anhydrous ammonia at 5-100. After stirring for 30 minutes at 250, the reaction mass was filtered and the solid washed well with water and then l-chlorobutane. The solid was dried in vacuo at 600 to give 20.9 g of the title compound, mp = 3-86.5-188,50. NMR (DMSO-d6) 6 : 3.8 (s, 2.7 H, CO2CH3); 7.1-8.3 (m, 8.3 H, 6 aromatics + SO2NH2),. Example 2 2-(2-Carbomethoxyfur-5-yl)-N-(butylaminocarbonyl)- benzenesulfonamide A mixture of 16.9 g of the product of Example 1, 7.5 g of n-butyl isocyanate, and 10.4 g of anhydrous potassium carbonate in 150 ml of 2-butanone was stir- red at 800 for 3 hours. The reaction mixture was cooled to 250, poured into 550 ml of ice water and acidified to pH=l with concentrated hydrochloric acid. The precipitated solid was filtered, washed with water, and dried at 600 in vacuo to give 22.5 g of the title compound, mp = 145-148 . NMR (DMSO-d6) 6 : 0.7-1.5 (m, 7.5 H, 7 butyl's); 2.8-3.1 (m, 3.0 H, 2 butyl's); 3.9 (s, 2.8 H, CO2CH3); 6.2-6.5 (t, 0.9 H, NH); 7.0-7.5 (m, 1.9 H, 2 furan's); 7.6-8.5 (m, 4.2 H, 4 aromatics); -10.3 (broad singlet, 0.7 H, NH). Example 3 2-(2-Carbomethoxyfur-5-y1)benzenesulfonyl isocyanate A solution of 19.0 g of the product of Example 2 and 0.1 g of l,4-diazabicycloE2.2.2.]octane (DABCO) in 90 ml of dry xylenes was heated to reflux temperature (1390). To this solution was added 3.6 ml of liquid phosgene over a period of about 2 hours, keeping the temperature between 1250 and 1360 by adjusting the rate of phosgene addition. The reaction mixture was cooled to 250, and filtered under nitrogen to remove DABCO hydrochloride. The filtrate was concentrated in vacuo to give the title compound as a viscous, moisture-sensitive oil. This material was carried on to the desired products without further purification. IR (neat) = 2280 cm 1 (S02NCO); 1760 cm 1 (-CO2CH3). Example 4 2-(2-Carbomethoxyfur-5-yl)-N-[(4,6-dimethoxypyrimidin- 2-yl)aminocarbonyl3benzenesulfonamide Under a nitrogen atmosphere, a mixture of 2.5 g of the product of Example 3, 0.9 g of 2-amino-4,6-dimethoxypyrimidine, and a few crystals of DABCO in 15 ml of dry acetonitrile was heated at 50-55 for 1 hour, then stirred at 250 overnight. The solid was filtered off, washed with acetonitrile and l-chlorobutane, and dried at 600 in vacuo to give 2.5 g of the title compound, mp = 215-2170(d). NMR (DMSO-d6) 6 : 3.6, 3.8 (two singlets, 8.4 H, 3 CH30's); 5.9 (s, 1.2 H, Het-H); 6.9-8.4 (m, 6.2 H, 6 aromatics); 10.7 (s, 1.0 H, NH); 12-13 (broad, 1.1 H, NH). Anal. Calcd. for C19H18N4O8S: C, 49.4; H, 3.9; N, 12.1. Found: C, 49.6; H, 4.0; N, 12.4; 49.8; 4.1; 12.7. Example 5 N- (1, 1-dimethylethyl)-2-C2-pyridinyl)benzenesulfonamide To a solution of 30 g of N-(l,l-dimethylethyl)-2 (2-pyridinyl)benzenesulfonamide in 600 ml of tetrahydrofuran was added 190 ml of 1.6M butyllithium in hexane at -10 to 100. The reaction mixture was allowed to stir at 250 for 1 hour, then cooled to -10 and 28 g of cuprous iodide was added. After 15 minutes stirring at 00, 35 g of 2-iodopyridine was added and the mixture was heated to reflux for 16 hours. After cooling to 250, 25 ml of acetic acid was added and solvent was removed in vacuo. A cold solution of aqueous ammonia was added and the precipitate was filtered. The solid was digested with methylene chloride and filtered. The filtrate was concentrated, triturated with n-chlorobutane, and the solid was filtered to afford 36 g (78%) of product, m.p. 147-1500. NMR(8DC13)6: 1.3 (s, 9), 7.1-8.7 (m, 9). Example 6 2-(2-pyridinyl)benzenesutfonamide A solution of 14.8 g of the sulfonamide from Example 5 and 10 ml of 48% hydrobromic acid in 100 ml of methanol was heated at 40-450 for 16 hours, concentrated, and neutralized with aqueous sodium bicarbonate. The solid was filtered, washed with ice-water, and air-dried to afford 6.0 g of product, m.p. 186-1900. NMR(CDCl3/DMSO-d6)#: 7.5 (m, 7), 8.1 (m, 2) , 8.6 (d, 1). lR(Nujol) 3300, 3260 cm m/e M+ 234. Example 7 N-E(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- (2-pyridinyl)benzenesulfonamide A solution of 1.2 g of the compound from Example 6 and 1.3 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)- carbamate in 50 ml of methylene chloride was stirred under nitrogen and 3.4 ml of a 2N solution of trimethylaluminum in toluene was added. After heating at reflux for 4 days, the solution was cooled to 00, 3 ml of 2N HC1 (aq.) was added, the mixture was partitioned between methylene chloride and water. The organic layer was concentrated and the residue was chromatographed on silica gel to afford 0.9 g of the product, m.p. 175-176 . NMR (DMSO-d6)6: 3.8 (s, 6), 6.0 (s, 1), 7.2-8.3 (m). m/e (M+ +1) 416. IR 1700 cm 1. Using the procedures described in the equations and Examples 1-7 above, the compounds described in the following Tables I-XXV can be prepared. Table I EMI43.1 R1 R2 R3 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH 171-174 H H H H CH3 OCH3 CH 180-184 H H H H OCH3 OCH3 CH 175-176 H H H H CH3 CH3 N H H H H CH3 OCH3 N 160-173 H H H H OCH3 OCH3 N 172-205 H H H H CH3 CH2OCH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCH3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 4'-CH3 H H CH3 CH3 CH H 4'-CH3 6'-CH3 H CH3 OCH3 CH H 5'-CH3 H H OCH3 OCH3 N H 3'-CH3 H H OCH3 OCH3 CH H 3'-CH3 5'-CH3 H CH3 OCH3 CH H 6'-CH3 H H OCH3 CH3 N H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table I (continued) R1 R2 R3 R17 X Y Z m.p.( C) H 6'-CH3 H H CH3 CH3 N H 4'-CH3 H H OCH3 CH2OCH3 N H 5'-CH3 H H CH3 CH3 CH H H H H OCH3 CH(OCH3)2 CH 3-F H H H CH3 CH3 N 3-F H H H OCH3 CH3 N 3-F H H H CH3 N(CH3)2 CH 3-F H H H Cl OCH3 CH 3-F H H CH3 OCH3 NH2 N 3-F H H H CH3 OCH3 N 4-C1 H H H OCH3 CH3 CH 4-Cl H H H CH3 OC2H5 CH 4-C1 H H H OCH3 C2H5 N 4-Cl 6'-CH3 H H Cl CH2OCH3 N 4-C1 H H H OCH3 OCH3 CH 4-C1 H H CH3 CH3 OCH3 CH 5-CH3 H H H OCH3 NHCH3 N 5-CH3 H H H CH3 C2H5 N 5-CH3 H H H OCH3 CH3 CH 5-CH3 H H H CH3 CH3 CH 5-CH3 H H H OCH3 CH3 N 4-OCH3 H H H CH3 OCH3 N 4-OCH3 H H H OCH3 OCH3 CH 4-OCH3 H H H CH3 CH3 CH 4-OCH3 H H H OCH3 OCH3 N Table II EMI45.1 R1 R2 R3 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH H H H H CH3 OCH3 CH H H H H OCH3 OCH3 CH H H H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH20CH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCR3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 2'-CH3 H H OCH3 CH3 CH H 5'-CH3 6'-CH3 H OCH3 CH3 N H 6'-CH3 H H CH3 CH3 CH H 5'-CH3 H H CH3 OCH3 CH H 4'-CH3 6'-CH3 H OCH3 OCH3 CH H 2'-CH3 H H OCH3 OCH3 N H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table II (continued) R1 R2 R3 R17 X Y Z m.p.( C) H 6'-CH3 H H CH3 CH3 N H H H H OCH3 CH20CH3 N H 4'-CH3 H H CH3 CH3 CH H H H H OCH3 CH(OCH3)2 CH 6-F H H R CH3 CH3 N 6-F H H H OCH3 CH3 N 6-F H H H CH3 N(CH3)2 CH 6-F H H H Cl OCH3 CH 6-F H H CH3 OCH3 NH2 N 6-F H H H CH3 OCH3 N 3-Cl H H H OCH3 CH3 CH 3-Cl H H H CH3 OC2H5 CH 3-C1 H H H OCH3 C2H5 N 3-C1 H H H Cl CH20CH3 N 3-C1 H H H OCH3 OCH3 CH 3-Cl H H CH3 OCH3 CH 4-CH3 H H H OCH3 NHCH3 N 4-CH3 5'-CH3 H H CH3 C2H5 N 4-CH3 H H H OCH3 CH3 CH 4-CH3 H H H CH3 CH3 CH 4-CH3 H H H OCH3 CH3 N 5-OCH3 H H H CH3 OCH3 N 5-OCH3 H H H OCH3 OCH3 CH 5-OCH3 H H H CH3 CH3 CH 5-OCH3 H H H OCH3 OCH3 N Table III EMI47.1 R1 R2 R3 R17 X Y z m.p.( C) H H H H CH3 CH3 CH H H H H CH3 OCH3 CH H H H H OCH3 OCH3 CH H H H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH2OCH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCH3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 2'-CH3 H H CH3 OCH3 N H 2'-CH3 6'-CH3 H CH3 OCH3 CH H 3'-CH3 H H CH3 CH3 CH H 2'-CH3 H H OCH3 OCH3 N H 3'-CH3 6'-CH3 H OCH3 OCH3 CH H 2'-CH3 H H CH3 OCH3 CH H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table III (continued) R1 R2 R3 R17 X Y Z m.p.( C) H 2'-CH3 H H CH3 CH3 N H H H H OCH3 CH20CH3 N H 3'-CH3 H H CH3 CH3 CH H H H H OCH3 CH(OCH3)2 CH 5-F H H H CH3 CH3 N 5-F H H H OCH3 CH3 N 5-F H H H CH3 N(CH3)2 CH 5-F H H H Cl OCH3 CH 5-F H H CH3 OCH3 NH2 N 5-F H H H CH3 OCH3 N 4-C1 H H H OCH3 CH3 CH 4-Cl H H H CH3 OC2H5 CH 4-C1 H H H OCH3 C2H5 N 4-Cl H H H Cl CH2OCH3 N 4-Cl H H H OCH3 OCH3 CH 4-Cl 2'-CH3 6'-CH3 CH3 OCH3 CH 3-CH3 H H H OCH3 NHCH3 N 3-CH3 H H H CH3 C2H5 N 3-CH3 H H H OCH3 CH3 CH 3-CH3 H H H CH3 CH3 CH 3-CH3 H H H OCH3 CH3 N 3-CH3 H H H CH3 OCH3 N 3-CH3 H H H CH3 OCH3 CH 3-CH3 H H H CH3 CH3 CH 3-CH3 H H H OCH3 OCH3 N Table IV EMI49.1 R1 R4 R5 R6 R17 X Y Z m.p.( C) H H H H H CH3 CH3 CH H H H H H CH3 OCH3 CH 178-185 H H H H H OCH3 OCH3 CH 197-210 H H H H H CH3 CH3 N H H H H H CH3 OCH3 N H H H H H OCH3 OCH3 N H H H H H CH3 CH2OCH3 CH H H H H H CH3 CH(OCH3)2 CH H H H H H CH3 N(CH3)2 OCH3 H H H H H CH NH2 CH H H H H H OCH3 NRCH3 CHN H H H H H OCH3 CH(OCH3)2 CH H H H H H Cl OCH3 CH H H H H H CH3 CH2OCH3 N H H H H H OCH3 N(CH3)2 N H H H H H CH3 CH(OCH3)2 N H H H H H OCH3 CH2OCH3 N H CH3 H H H CH3 OCH3 N H CH3 H CH3 H OCH3 OCH3 N H OCH3 H CH3 H CH3 CH(OCH3)2 N H OCH3 H H H CH3 CH(OCH3)2 N 3-C1 H H H H CH3 OCH3 CH 4-C1 H H H H OCH3 OCH3 N Table IV (continued) R1 R4 R5 R6 R17 X Y Z m.p.( C) 4-C1 H H H H CH3 OCH3 N 4-C1 CH3 H CH3 H CH3 CH3 CH 4-Cl OCH3 H OCH3 H OCH3 OCH3 CH 4-C1 H H H H OCh3 OCH3 N 4-C1 H CH3 H H OCH3 OCH3 CH 5-C1 H H H CH3 CH3 OCH3 CH 3-CH3 H H H H CH3 CH3 CH 5-CH3 H H H H OCH3 CH20CH3 N 4-CH3 H H H H CH3 CH(OCH3)2 CH 4-CH3 H H H H CH3 N(CH3)2 N 4-CH3 H H H H OCH3 OCH3 CH 4-CH3 CH3 CH3 OCH3 H OCH3 CH3 CH 4-OCH3 H H H CH3 CH3 CH3 N 3-OCH3 CH3 CH3 H H OCH3 OCH3 N 6-OCH3 H H H H OCH3 OCH N 6-OCH3 H H H H CH3 OCH3 CH 6-OCH3 H H H H CH3 CH3 CH 6-F H H H H OCH3 OCH3 N 5-F H H H H CH3 OCH3 N 3-F H H H H CH3 Ch2OCh3 CH 3-F H H H H OCH3 CH(OCH3)2 CH 3-F H H H H CH3 N(CH3)2 N 3-F H H H CH CH3 OCH3 CH 3-F OCH3 CH3 OCH3 H CH3 OCH3 N Table V EMI51.1 R1 R7 R8 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH HH H H CH3 OCH3 CH H H H H OCH3 OCH3 CH HH H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH20CH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCH3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 2'-CH3 H H CH3 CH3 CH H 2'-CH3 6'-OCH3 H CH3 OCH3 N H 2'-OCH3 H H OCH3 OCH3 N H 5'-CH3 H H OCH3 OCH3 CH H 2'-OCH3 5'-CH3 H CH3 CH3 CH H 6'-CH3 H H OCH3 CH3 CH H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table V (continued) R1 R7 R8 R17 X Y Z m.p.( C) H 2'-CH3 H H CH3 CH3 N H H H H OCH3 CH2OCH3 N H 6'-CH3 H H CH3 CH3 CH H H H H OCH3- CH(OCH3)2 CH 4-F H H H CH3 CH3 N 4-F H H H OCH3 CH3 N 4-F H H H CH3 N(CH3)2 CH 4-F H H H Cl OCH3 CH 4-F H H CH3 OCH3 NH2 N 4-F H H H CH3 OCH3 N 5-Cl H H H OCH3 CH3 CH 5-Cl H H H CH3 OC2H5 CH 5-Cl H H H OCH3 C2H5 N 5-Cl H H H Cl CH2OCH3 N 5-Cl H H H OCH3 CH3 CH 5-C1 H H CH3 CH3 OCH3 CH 3-CH3 H H H OCH3 NHCH3 N 3-CH3 H H H CH3 C2H5 N 3-CH3 H H H OCH3 CH3 CH 3-CH3 2'-CH3 H H CH3 CH3 CH 3-CH3 H H H OCH3 CH3 N 4-OCH3 H H H CH3 OCH3 N 4-OCH3 H H H OCH3 OCH3 CH 4-OCH3 H H H CH3 CH3 CH 4-OCH3 H H H OCH3 OCH3 N Table VI EMI53.1 R1 R7 R8 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH H H H H CH3 OCH3 CH H H H H OCH3 OCH3 CH H H H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH20CH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCH3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH)OCH3)2 N H 2'-OCH3 H H CH3 CH3 CH H 2'-CH3 4'-CH3 H CH3 OCH3 N H 4'-OCH3 H H CH3 CH3 CH H 2'-CH3 H H OCH3 OCH3 CH H 4'-CH3 6'-CH3 H OCH3 OCH3 N H 2'-CH3 H H OCH3 OCH3 N H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table VI (continued) R1 R7 R8 R17 X Y Z m.p.( C) H 2'-CH3 H H CH3 CH3 N H H H H OCH3 CH2OCH3 N H 4'-CH3 6'-CH3 H CH3 CH3 CH H H H H OCH3 CH(OCH3)2 CR 5-F H H H CH3 CH3 N 5-F H H H OCH3 CH3 N 5-F H H H CH3 N(CH3)2 CH 5-F H H H Cl OCH3 CH 5-F H H CH3 OCH3 NH2 N 5-F H H H CH3 OCH3 N 3-C1 H H H OCH3 CH3 CH 3-Cl H H H CH3 OC2H5 CH 3-Cl H H H OCH3 C2H5 N 3-Cl H H H Cl CH2OCH3 N 3-Cl H H H OCH3 OCH3 CH 3-Cl H H CH3 CH3 OCH3 CH 4-CH3 H H H OCH3 NHCR3 N 4-CH3 H H H CH3 C2H5 N 4-CH3 H H H OCH3 CH3 CH 4-CR3 H H H CH3 CH3 CH 4-CH 2'-CH H H OCH3 CH3 N 5-OCH3 H H H CH3 OCH3 N 5-OCH3 H H H OCH3 OCH3 CH 5-OCH3 H H H CH3 CH3 CH 5-OCH3 H H H OCH3 OCH3 N Table VII EMI55.1 R1 R9 R10 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH 212-217 d H H H H CH3 OCH3 CH 178 H H H H OCH3 OCH3 CH 178-179 H H H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH2OCH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H Cl OCH3 CH H H H H OCH3 NHCR3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 3'-CH3 H H CH3 OCH3 CH H 5'-CH3 6'-CH3 H CH3 OCH3 CH H 5'-CH3 H H CH3 CH3 CH H 6'-CH3 H H OCH3 OCH3 N H 3'-CH3 6'-CH3 H OCH3 CH3 N H 3'-CH3 H H OCH3 OCH3 CH H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table VII (continued) m.p. R1 R2 R3 R17 X Y Z ( C) H 6'-CH3 H H CH3 CH3 N H H H H OCH3 CH2OCH3 N H 5'-CH3 6'-CH3 H CH3 CH3 CH H H H H OCH3 CH(OCH3)2 CH 3-F H H H CH3 CH3 N 3-F H H H OCH3 CH3 N 3-F H H H CH3 N(CH3)2 CH 3-F H H H Cl OCH3 CH 3-F H H CH3 OCH3 NH2 -N 3-F H H H CH3 OCH3 N 4-Cl H H H OCH3 CH3 CH 4-Cl H H H CH3 OC2H5 CH 4-C1 H H H OCH3 C2H5 N 4-C1 H H H Cl CH20CH3 N 4-C1 6'-CH3 H H OCH3 OCH3 CH 4-Cl H H CH3 CH3 OCH3 CH 5-CH3 H H H OCH3 NHCH3 N 5-CH3 H H H CH3 C2H5 N 5-CH3 H H H OCH3 CH3 CH 5-CH3 H H H CH3 CH3 N 5-CH3 H H H OCH3 CH3 N 6-OCH3 H H H CH3 OCH3 N 6-OCH3 H H H OCH3 OCH3 CH 6-OCH3 H H H CH3 CH3 CH 6-OCH3 H H H OCH3 OCH3 N Table VIII EMI57.1 R1 R11 R12 R17 X Y Z m.p.( C) H H H H CH3 CH3 CH H H H H CH3 OCH3 CH H H H H OCH3 OCH3 CH H H H H CH3 CH3 N H H H H CH3 OCH3 N H H H H OCH3 OCH3 N H H H H CH3 CH2OCH3 CH H H H H CH3 CH(OCH3)2 CH H H H H OCH3 N(CH3)2 N H H H H OCH3 NH2 CH H H H H CL OCH3 CH H H H H OCH3 NHCH3 CH H H H H CH3 CH2OCH3 N H H H H Cl CH3 CH H H H H OCH3 CH(OCH3)2 N H 6'-CH3 H H CH3 OCH3 N H 4'-CH3 6'-CH3 H OCH3 OCh3 CH H 6'-CH3 H H OCH3 OCH3 N H 5'-CH3 H H CH3 CH3 N H 4'-CH3 5'-CH3 H OCH3 CH3 CH H 6'-CH3 H H CH3 OCH3 CH H H H CH3 CH3 CH3 CH H H H CH3 OCH3 OCH3 CH Table VIII (continued) R1 R2 R3 R17 X Y Z m.p.( C) H 6'-CH3 H H CH3 CH3 N H H H H OCH3 CH2OCH3 N H 4'-CH3 H H CH3 CH3 CH H H H H OCH3 CHtOCH3)2 CH 6-F H H H CH3 CH3 N 6-F H H H OCH3 CH3 N 6-F H H H CH3 N(CH3)2 CH 6-F H H H Cl OCH3 CH 6-F H H CH3 OCH3 NH2 N 6-F H H H CH3 OCH3 N 5-C1 H H H OCH3 CH3 CH 5-Cl H H H CH3 OC2H5 CH 5-Cl 6'-CH3 H H OCH3 C2H5 N 5-Cl H H H Cl CH2OCH3 N 5-C1 H H H OCH3 OCH3 CH 5-C1 H H CH3 CH3 OCH3 CH 3-CH3 H H H OCH3 NHCH3 N 3-CH3 H H H CH3 C2H5 N 3-CH3 H H H OCH3 CH3 CH 3-CH3 H H H CH3 CH3 CH 3-CH3 H H H OCH3 CH3 N 4-OCH3 H H H CH3 OCH3 N 4-OCH3 H H H OCH3 OCH3 CH 4-OCH3 H H H CH3 CH3 CH 4-OCH3 H H H OCH3 OCH3 N Table IX EMI59.1 R1 R11 R12 R17 X Y z m.p.( C) H HC3 CH3 H CH3 CH3 CH H CH3 CH3 H CH3 OCH3 CH H CH3 CH3 H OCH3 OCH3 CH H CH3 CH3 H CH3 CH3 N H CH3 CH3 H CH3 OCH3 N H CH3 CH3 H OCH3 OCH3 N H OCH3 OCH3 H CH3 CH3 CH H OCH3 OCH3 H Cl OCH3 CH H OCH3 OCH3 H OCH3 OCH3 CH H OCH3 OCH3 H CH3 CH3 N H OCH3 OCH3 H CH3 OCH3 N H OCH3 OCH3 H OCH3 OCH3 N H OCH3 CH3 H CH3 CH3 CH H OCH3 CH3 H CH3 OCH3 CH H OCH3 CH3 H OCH3 OCH3 CH H OCH3 CH3 H CH3 CH3 N H OCH3 CH3 H CH3 OCH3 N H OCH3 CH3 H OCH3 OCH3 N H OCH3 CH3 H CH3 CH20CH3 CH H OCH3 CH3 H CH3 N(CH3)2 CH H OCH3 CH3 CH3 OCH3 CH3 CH H OCH3 CH3 CH3 CH3 CH(OCH3)2 CH H OCH3 CH3 CH3 CH3 CH3 CH Table IX (continued) R1 R11 R12 R17 X Y Z m.p.( C) 3-C1 CH3 CH3 H CH3 CH3 CH 3-Cl CH3 CH3 H CH3 OCH3 CH 3-Cl CH3 CH3 H OCH3 CH2OCH3 CH 4-Cl CH3 CH3 H CH3 CH3 N <RTI ID=60.1> 5-C1 CH3 CH3 H CH3 OCH3 N 5-C1 CH3 CH3 H OCH3 CH(OCH3)2 N 5-Cl OCH3 OCH3 H CH3 OCH3 CH 4-CH3 OCH3 OCH3 H Cl CH3 CH 3-CH3 OCH3 OCH3 H OCH3 OCH3 CH 6-F OCH3 OCH3 H CH3 CH3 CH 5-OCH3 OCH3 OCH3 H CH3 CH3 CH H OCH3 OCH3 H OCH3 N(CH3)2 CH H OCH3 CH3 H CH3 NH2 CH H OCH3 CH3 H CH3 NHCH3 CH H OCH3 CH3 H OCH3 CH20CH3 CH H OCH3 CH3 H CH3 CH(OCH3)2 N H OCH3 CH3 H CH3 NHCH3 N H OCH3 CH3 H OCH3 CH2OCH3 N H OCH3 CH3 H CH3 CH(OCH3)2 CR H OCH3 CH3 H CH3 N(CH3)2 CH H OCH3 CH3 CH3 OCH3 OCH3 CH H OCH3 CH3 CH3 CH3 CH3 CH H OCH3 CH3 CH3 CH3 OCH3 CH Table X EMI61.1 R1 R13 R14 R17 X Y Z m.p.( C) H CH3 CH3 H CH3 CH3 CH H CH3 CH3 H CH3 OCH3 CH H CH3 CH3 H OCH3 OCH3 CH H CH3 CH3 H CH3 CH3 N H CH3 CH3 H CH3 OCH3 N H CH3 CH3 H OCH3 OCH3 N H OCH3 CH3 H CH3 CH3 CH H OCH3 CH3 H CH3 OCH3 CH H OCH3 CH3 H OCH3 OCH3 CH H OCH3 CH3 H CH3 CH3 N H OCH3 CH3 H CH3 OCH3 N H OCH3 CH3 H OCH3 OCH3 N H OCH3 CH3 H CH3 CH2OCH3 CH H OCH3 OCH3 H CH3 CH3 CH H OCH3 OCH3 H OCH3 CH2OCH3 CH H OCH3 OCH3 H CH3 OCH3 N H OCH3 OCH3 H OCH3 OCH3 N H OCH3 OCH3 H Cl OCH3 CH H OCH3 OCH3 H OHC3 OCH3 CH H CH3 CH3 CH3 CH3 CH3 CH H CH3 OCH3 CH3 CH3 OCH3 CH H OCH3 OCH3 CH3 OCH3 CH3 N H CH3 CH3 CH3 OCH3 OCH3 N Table X (continued) R1 R13 R14 R17 X Y Z m.p.( C) 5-CH3 CH3 CH3 H CH3 CH3 CH 4-C1 CH3 CH3 H CH3 OCH3 CH 4-Cl CH3 CH3 H OCH3 OCH3 CH 4-C1 CH3 CH3 H CH3 CH3 N 6-C1 CH3 CH3 H CH3 OCH3 N 3-Cl CH3 CH3 H OCH3 OCH3 N 5-F OCH3 CH3 H CH3 CH3 CH 5-F OCH3 CH3 H CH3 OCH3 CH 5-F OCH3 CH3 H OCH3 OCH3 CH 3-CH3 OCH3 CH3 H CH3 CH3 N 3-CH3 OCH3 CH3 H CH3 OCH3 N3-CH3 OCH3 CH3 H OCH3 OCH3 N 4-OCH3 OCH3 CH3 H CH3 CH2OCH3 CH 4-OCH3 OCH3 OCH3 H CH3 CH3 CH 4-OCH3 OCH3 OCH3 H OCH3 CH2OCH3 CH 3-F OCH3 OCH3 H CH3 OCH3 N 3-F OCH3 OCH3 H OCH3 OCH3 N 3-F OCH3 OCH3 H Cl OCH3 CH 4-CH3 OCH3 OCH3 H OCH3 OCH3 CH 4-CH3 CH3 CH3 CH3 CH3 CH3 CH 4-CH3 CH3 OCH3 CH3 CH3 OCH3 CH H OCH3 OCH3 CH3 OCH3 CH3 N R CH3 CH3 CH3 OCH3 OCH3 N Table XI EMI63.1 R1 W R24 R25 R17 R26 W' Z X Y m.p.( C) H O H H H -CO2CH3 O CH CH3O CH3O 215-217(d) H O H H H -CO2CH3 O N CH3O CH3O 210-212(d) H O H H H -CO2CH3 O CH CH3O CH3 200-202(d) H O H H H -CO2CH3 O CH CH3O CH3O 215-217(d) H O H H H -CO2CH3 O CH CH3 CH3 197-199(d) H 0 H H H -C02CH3 0 N CH3 CH3 205-207(d) H O H H H H O CH CH3O CH3O 168-183(d) H O H H H H O N CH3O CH3O 175(d) H O H H H H O CH CH3O CH3O 215-217(d) H S H H H H O N CH3O CH3 H S H H H H O CH CH3 CH3 H O H H H H O N CH3 CH3 H O H H CH3 H O N CH30 CH30 H O H H H H S CH CH3O CH3O 193-196 (d) H O H H H H S CH CH3O CH3 218-219 (d) H O H H H H S CH CH3 CH3 211-215 (d) H O H H H H S N CH3O CH3O < 260 H O H H H H S N CH30 CH3 190-1960d H O H H H H S N CH3 CH3 H O H H H H O N CH30 CH3 165-186(d) 5-F O H H H H O N CH3O CH3 5-Cl O H H H H O N CH3O CH3 5-Br O H H H H O N CH3O CH3 5-CF3 O H H H H O N CH3O CH3 H O H H H H O CH CH3 CH3 162-178(d) Table XI (continued) R1 W R24 R25 R17 R26 W' Z X Y m.p.( C) 5-CH3 O H H H H O N CH30 CH3 5-CH3O O H H H H O N CH3O CH3 3-C1 O H H H H N CH30 CH3 4-Cl O H H H H O N CH3O CH3 6-Cl O H H H H O N CH3O CH3 H O CH3 H H H O N CH3O CH3 H O C2H5 H H H O N CH3O CH3 H O Cl H H H O N CH3O CH3 H O Br H H H O N CH3O CH3 H O CH30 H H H O N CH30 CH3 H O C2H5O H H H O N CH3O CH3 H O H CH3 H H O N CH3O CH3 H O H Cl H H O N CH3O CH3 H O H CH3O H H O N CH3O CH3 H O CH3 CH3 H CH3 O N CH3O CH3 H S H H H CH3 O N CH30 CH3 H O H H H C2H5 O N CH3O CH3 H O H H H Cl <RTI ID=64.6> O N CH30 CH3 H O H H H Br O N CH30 CH3 H O H H H CH3O O N CH3O CH3 H O H H H C2H3O O N CH3O CH3 H O H H H H O N CH3O CH3 H O H H H H O CH Cl CH3 H O H H H H O CH Cl NH2 H O H H H H O CH CH3 -CH2OCH3 H O H H H H O CH CH3 C2H5O H O H H H H O CH CH3 CH(OCH3)2 H O H H H H O CH CH3O C2H5 H O H H H H 9 N CH30 NH2 H O H H H H O N CH3O NHCH3 H O H H H H O N CH30 N(CH3)2 H O H H H H O CH CH3 CH(-OCH2CH2O-) Table XI (continued) R1 W R24 R25 R17 R26 W' Z X Y m.p.( C) H O H H H H O CH CH3 OCH2CF3 H O H H H H O CH OCH3 CF3 H O H H H H O CH CH3 OCH2CH2OCH3 H O H H H H O N CH3 SCH3 Table XII EMI66.1 R1 W R24 R25 R17 R26 W' Z X Y m.p.( C) H O H H H H O CH CH3O CH3O H O H H H H O CH CH3O CH3 H O H H H H O CH CH3 CH3 H O H H H H O N CH3O CH3O H O H H H H O N CH3O CH3 H O H H H H O N CH3 CH3 H O H H H H S N CH3O CH3 H O H H H H S N CH30 CH3O H 0 H H H H S CH CH3O CH30 H S H H H H S CH CH3O CH3 H O H H H H S CH CH3 CH3 H O H H CH3 H O N CH3O CH3O 5-Cl O H H H H O N CH3O CH3O 5-Br O H H H H O N CH3O CH3 5-CH3 O H H H H O N CH3O CH3 6-Cl O H H H H O N CH3O CH3 6-CH3 O H H H H O N CH3O CH3 H O CH3 H H H O N CH3O CH3 H O C2H5 H H H O N CH3O CH3 H O CH3 CH3 H CH3 O N CH3O CH3 H O H CH3 H H O N CH3O CH3 H S H H H C2H5 O N CH3O CH3 H O H H H CO2CH3 O N CH3O CH3 H O H H H H O N CH3O CH3O Table XII (continued) R1 W R24 R25 R17 R26 W' Z X Y m.p.( C) H O H H H H O CH CH30 CH3O H O H H H H O . CH CH30 CH3 H O H H H H O CH Cl CH30 H O H H H H O CH CH3 CH2OCH3 H S H H H H O CH CH3 CH(OCH3)2 H O H H H H O N CH30 NH2 H O H H H H O N CH30 NHCH3 H O H H H H O N CH3O N(CH3)2 H O H H H H O CH oH3 0CH2CF3 H O H H H H O CH OCH3 CH(-OCH2CH2O-) Table XIII EMI68.1 R1 W R27 R28 R17 R18 R19 z X Y m.p.( C) H O H H H H H CH CH3O CH30 H O H - H H H H CH CH30 CH3 H 0 H H H H H CH CH3 CH3 H S H H H H H N CH30 CH30 H O H H H H H N CH30 CH3 H O H H H H H N CH3 CH3 H O CH3 H H H CH3 CH CH3O CH3O H O CH3 H H H CH3 CH CH3O CH3 H O CH3 H H H CH3 CH CH3 CH3 H O CH3 H H H CH3 N CH3 CH3O H O CH3 H H H CH3 N CH3O CH3 H O H H CH3 H H N CH30 CR30 5-Cl O H H H H H N CH3O CH3O S-F O H H H H H N CH30 CH3 5-Br O H H H H H N CH3O CH3 5-CH3 O H H H H H N CH3O CH3 5-CF3 O H H H H H N CH30 CH3 5-OCH3 O H H H H H N CH3O CH3 3-C1 O H H H H H N CH30 CH3 4-C1 O H H H H H N CH3O CH3 6-C1 O H H H H H N CH3O CH3 H O CH3 CH3 H CH3 CH3 N CH3O CH3 H O CH3 H H H H N CH3O CH3 Table XIII (continued) R1 W R27 R28 R17 R17 R18 R19 Z X Y m.p.( C) H O H CH3 H H H N CH3 CH3 H O H CH3 H CH3 H N CH3O CH3 H O CH3 CH3 H H H N CH3O CH3 H O H H H H H CH CH3 C2H5O H S H H H H H CH CH3 CH2OCH3 H O H H H H H CH CH3 CH(OCH3)2 H O H H H H H CH Cl CH30 H O H H H H H N CH3O N(CH3)2 H O H H H H H N CH3O NH2 Table XIV EMI70.1 R1 W R27 R28 R17 R18 Z X Y m.p.( C) H 0 H H H H CR CH3O CH3O H O H H H H CH CH3O CH3 H O H. H H H CH CH3 CH H O H H H H N CH3O CH3O H 0 H H H H N CH3O CH3 H O H H H H CH3 CH3O CH3O H O H H H H CH3 CH3O CH3 H S H H H CH3 N CH3O CR3O H O H H H CH3 N CH3O CH3 H O CH3 CH3 H CH, N CH3O CH3 H O CH3 CH3 H H N CH3O CH3 H S CH3 H H H N CH3O CH3 H O H CH3 H H N CH3O CH3 H O H H CH3 H N CH3O CH3O 5-F O H H H H N CH3O CH3O 5-Br O H H H H N CH3O CH30 5-CH3 O H H H H N CH3O CH3O 5-CH3O O H H H H N CH3O CH3O 5-CF3 O H H H H N CH3O CH3O 5-C1 O H H H H N CH30 CR3O H O H H H H CH Cl CH3O H O H H H H CH CH3 CH2OCH3 H O H H H H CH CH3 CH(OCH3)2 Table XIV (continued) R1 W R27 R28 R17 R18 Z X Y m.p.( C) H O H H H H N CH3 C2H50 H O H H H H N CH30 N(CH3)2 H O H H H H CH Cl NH2 Table XV EMI72.1 R1 W R27 R28 R17 R18 Z X Y m.p.( C) H O H H H H CH CH3O CH3O H 0 H H H H CH CH3O CH3 H O H H H H CH CH3 CH3 H O H H H H N CH3O CH3O H O H H H H N CH3O CH3 H O CH3 H H CH3 CH CH3O CH3O H O CH3 H H CH3 CH CH3O CH3 H S CH3 H H CH3 N CH3O CH3O H S CH3 H H CH3 N CH3O CH3 H O CH3 CH3 H CH3 N CH3O CH3 H O H H CH3 H N CH3O CH30 H O H CH3 H H N CH30 CH3 H O H H H CH3 N CH3O CH3 5-F O H H H H N CH3O CH3 3-Br O H H H H N CH3O CH3 4-CH3 O H H H H N CH3O CH3 6-Cl O H H H H N CH3O CH3 5-CF3 O H H H H N CH3O CH3 5-CH3O O H H H H N CH3O CH3 H O H H H H CH Cl CH3O H O H H H H CH CH3 CH(OCH3)2 H O H H H H CH CH3O CH2OCH3 H O H H H H N CH3O N(CH3)2 Table XV (continued) R1 W R27 R28 R17 R18 Z X Y m.p.( C) H O H H H H N CH3 NHCH3 H O H H H H N CH30 NH2 H S H H H H CH CH3 CH(-OCH2CH2O-) H O H H H H CH OCH3 CF3 Table XVI EMI74.1 R1 W R17 R27 R28 R19 R20 R21 W' Z X Y m.p.( C) H O H H H H H H O CH CH3O CH3O H O H H H H H H H O CH CR3O CH3 H O H H H H H H H O CH CH3 CH3 H O H H H H H H O N CH3O CH3O H O H H H H H H H O N CH30 CH3 H O H H H H H H O N CH3 CH3 H O H H H H H H S CH CH3O CH3O H O H H H H H H S CH CH3O CH3 H O H H H H H H S CH CH3 CH3 H O H H H H H H S N CH3O CH3O H S H H H H H H H S N CH3O CH3 H O H H H H H H S N CH3 CH3 H O CH3 H H H H H O N CH3O CH3O H O H CH3 CH3 H H H O N CH3O CH3 H O H H H CH3 CH3 H H O N CH30 CH3 H O H H H H CH3 CH3 O N CH3O CH3 H O H CH3 H CH3 H CH3 H N CH3O CH3 H O H CH3 H H H H H O N CH3O CH3 H O H H H CH3 H H H O N CH30 CH3 H O H H H H CH3 H O CH CH3O CH3 H O H CH3 H CH3 H CH3 O N CH3O CH3 5-F O H H H H H H O N CH3O CH3 Table XVI (continued) R1 W R17 R27 R28 R18 R19 R20 R21 W' Z X Y m.p.( C) 3-Br O H H H H H H H O N CH30 CH3 4-CH3 O H H H H H H H O N CH3O CH3 6-C1 O H H H H H H H O N CH3O CH3 5-CF3 O H H H H H H H O N CH30 CH3 5-CH3 O H H H H H H H O N CH3O CH3 5-CH3O O H H H H H H H O N CH3O CH3 5-C1 O H H H H H H H O N CH3O CH3 H O H H H H H H H O CH Cl CH3O H O H H H H H H H O CH CH3 CH(OCH3)2 H S H H H H H H H O CH CH3O -CH20CH3 H O H H H H H H H O N CH3O N(CH3)2 H O H H H H H H H O N CH3O NHCH3 H O H H H H H H H O N CH3 NH2 H O H H H H H H H O N CH3 C2H50 H O H H H H H H H O N CH3O C2H5 H O H H H H H H H O CH CH3 OCH2CH2OCH3 Table XVII EMI76.1 R1 W R17 R27 R28 R18 R19 R20 R21 W' Z X Y m.p.( C) H O H H H H H H H O CH CH3O CH3O 183-185 H O H H H H H H H O CH CH3O CH3 185-186 H S H H H H H H H O CH CH3 CH3 H O H H H H H H H O N CH3O CH3O 171-180 H O H H H H H H H O N CH3O CH3 181-186 (d) H O H H H H H H H O N CH3 CH3 H O CH3 H H H H H H O N CH3O CH3 H O H H H H H H H S CH CH3O CH3O H O H H H H H H H S CH CH3O CH3 H S H H H H H H H S CH CH3 CH3 H O H H H H H H H S N CH30 CH30 H OH H H H H H H S N CH30 CH3 H O H H H H H H H S N CH3 CH3 H OH CH3 CH3 H H H H O N CH30 CH3 H O H H H H H CH3 CH3 O N CH3O CH3 H O H CH3 H CH3 H CH3 H O N CH3O CH3 H O H CH3 CH3 H H CH3 CH3 O N CH3O CH3 5-F O H H H H H H H O N CH3O CH3 5-Br O H H H H H H H O N CH30 CH3 5-CH3 O H H H H H H H O N CH3O CH3 5-CF3 O H H H H H H H O N CH3O CH3 5-Cl O H H H H H H H O N CH3O CH3 H O H H H H H H H O CH CH3 CH3 184-1870 Table XVII (continued) m.p. R1 W R17 R27 R28 R18 R19 R20 R21 W' Z X Y ( C) 5-CH3O O H H H H H H H O N CH3O CH3 3-C1 O H H H H H H H O N CH30 CH3 4-Cl O H H H H H H H O N - CH3O CH3 6-Cl O H H H H H H H O N CH30 CH3 H O H H H H H H H O CH Cl CH30 H O H H H H H H H O CH CH3O CH2OCH3 H O H H H H H H H O CH CH3O CH(OCH3)2 H O H H H H H H H O N CH3O N(CH3)2 H O H H H H H H H O N CH3 NHCH3 H O H H H H H H H O N CH3O NH2 H O H H H H H H H O N CH3 C2H5O H O H H H H H H H O N CH3O C2H5 H O H H H H H H H O N CH3 OCH2CF3 Table XVIII EMI78.1 R1 W R17 R27 R28 R18 R19 R20 Z X Y m.p.( C) H O H H H H H H CH CH30 CH30 H O H H H H H H CH CR3O CH3 H O H H H H H O CH CH3 CH3 H O H H H H H O N CH3O CH3O H O H H H H H O N CH3O CH3 H O H H H H H O N CH3 CH3 H O CH3 H H H H H N CH30 CH3 H S H CH3 H H H H N CH3O CH3 H O H CH3 CH3 H H H N CH3O CH3 H O H H CH3 CH3 H H N CH3O CH3 H O H H H H CH3 CH3 N CH3O CH3 H O H CH3 H CH3 CH3 H N CH3O CHO H O H H CH3 CH3 CH3 CH3 N CH3O CH3 H O H CH3 CH3 H H CH3 N CH3O CH3 5-F O H H H H H H N CH3O CH3 5-Cl O H H H H H H N CH3O CH3 5-CH3 O H H H H H H N CH3O CH3 5-Br O H H H H H H N CH3O CH3 5-CF3 O H H H H H H N CH3O CH3 5-CH3 O H H H H H H N CH3O CH3 3-Cl O H H H H H H N CH3O CH3 4-Cl O H H H H H H N CH3O CH3 Table XVIII (continued) R1 W R17 R27 R28 R18 R19 R20 R21 W' Z X Y m.p.( C) 6-Cl 0 H H H H H H H O N CH3O CH3 H O H H H H H H H O CH Cl CH3O H O H H H H H H H O CH Cl NH2 H O H H H H H H H O CH CH3 CH2OCH3 H O H H H H H H H O CH CH3O CH(OCH3)2 H O H H H H H H H O N CH3O N(CH3)2 H O H H H H H H H O N CH3 NH2 H O H H H H H H H O N CH30 C2H50 H S H H H H H H H O N CH3O C2H H O H H H H H H H O N CH30 NH(CH3)2 Table XIX EMI80.1 R1 W R17 R27 R28 R18 R19 R20 R21 R22 Z X Y m.p.( C) H O H H H H H H H H CH CH3O CH30 H S H H H H H H H H CH CH3O CH3 H O H H H H H H H H H CH CH3 CH3 H O H H H H H H H H N CH3O CH3O H O H H H H H H H H N CH3O CH3 H O H H H H H H H H N CH3 CH3 H O CH3 H H H H H H H N CH3O CH3O H O H CH3 H H H H H H N CH3O CH3 H O H H CH3 CH3 H H H H N CH3O CH3 H O H H H H CH3 CH3 H H N CH3O CH3 H O H H H H H H CH3 CH3 N CH30 CH3 H O H CH3 H H H H CH3 CH3 N CH30 CH3 H S H CH3 CH3 H CH3 H CH3 H N CH3O CH3 5-Cl O H H H H H H H H N CH3O CH3 5-F O H H H H H H H H N CH3O CH3 5-CH3 O H H H H H H H H N CH3O CH3 5-Br O H H H H H H H H N CH30 CH3 5-CF3 O H H H H H H H H N CH3O CH3 5-CH30 O H H H H H H H H N CK3O CH3 3-Cl O H H H H H H H H N CH3O CH3 4-Cl O H H H H H H H H N CH3O CH3 6-C1 O H H H H H H H H N CH3O CH3 H O H H H H H H H H CH Cl CH3O Table XIX (continued) R1 W R17 R27 R28 R18 R19 R20 R21 R22 Z X Y m.p.( C) H O H H H H H H H H CH Cl NH2 H O H H H H H H H H CH CH3 CH2OCH3 H O H H H H H H H H CH CH3 CH(OCH3)2 H O H H H H H H H H N CH3O N(CH3)2 H O H H H H H H H H N CH3 NH2 H O H H H H H H H H N CH3O NHCH3 H O H H H H H H H H N CH30 C2H50 H O H H H H H H H H N CH3O C2H5 H O H H H H H H H H CH CH3 SCH3 Table XX EMI82.1 R1 W W' R27 R28 R17 R18 R19 R20 R22 R23 Z X Y m.p.( C) H O O H H H H H H H H H CH CH3 CH3 H O O H H H H H H H H H CH CH3 OCH3 H O O H H H H H H H H H CH OCH3 OCH3 H O O H H H H H H H H H N OCH3 OCH3 H S O H H H H H H H H H N OCH3 OCH3 H O O H H H H H H H H H N OCH3 OCH3 H O S H H CH3 H H H H H H N CH3 OCH3 H S S H H H H H H H H H CH Cl OCH3 H O S H H H H H H H H H CH OCH3 CF3 H O S H H H H CH3 H H H H CH CH3 SCH3 H O O CH3 CH3 H H H H H H H N CH3 OCH2CF3 H O O CH3 H H CH3 H H H H H N OCH3 OC2H3 H O O H H H H H CH3 H H H N OCH3 CH3 H O O CH3 CH3 H H H H H CH3 CH3 CH OCH3 OCH3 H O O H H H H H H CH3 H H CH OCH3 CH3 H O O H H H H H H H CH3 H CH CH3 CH3 H O O H H H H H H H H H N OCH3 OCH2CH2OCH3 H O S H H H H H H H H H N CH3 OCH3 H O S H H H H H H H H H N OCH3 CH(-OCH2CH2O-) 5-Cl O O H H H H H H H H H CH OCH3 CH3 5-CH3 O O H H H H H H H H H CH Cl OCH3 6-C1 0 O H H H H H H H H H CH OCH3 CH2OCH3 4-CH3 O O H H H H H H H H H CH CH3 OCH3 Table XXI EMI83.1 R1 W W' R27 R28 R17 R18 R19 R20 R21 R22 R23 Z X Y m.p.( C) H O O H H H H H H H H H CH CH3 CH3 H O O H H H H H H H H H CH CH3 OCH3 H O O H H H H H H H H H CH OCH3 OCH3 H O O H H H H H H H H H N CH3 OCH3 H S O H H H H H H H H H N OCH3 OCH3 H O O H H H H H H H H H N OCH3 OCH3 H O S H H CH3 H H H H H H N CH3 OCH3 H S S H H H H H H H H H CH Cl OCH3 H O S H H H H H H H H H CH OCH3 CF3 H O S H H H H CH3 H H H H CH CH3 SCH3 H O O CH3 CH3 H H H H K H H N CH3 OCH2CF3 H O O CH3 H H CH3 H H H H H N OCH3 OC2H5 H O O H H H H H CH3 H H H N OCH3 CH3 H O O CH3 CH3 H H H H H CH3 CH3 CH CH3 C2H5 H O O H H H H H H CH3 H H CH OCH3 CH3 H O O H H H H H H H CH3 H CH CH3 CH3 H O O H H H H H H H H H H N OCH3 OCH2CH2OCH3 H O S H H H H H H H H H N CH3 OCH3 H O S H H H H H H H H H N CH3 CH(-OCH2CH2O-) 5-C1 0 O H H H H H H H H H CH OCH3 CH3 5-CH3 O O H H H H H H H H H CH Cl OCH3 6-C1 0 0 H H H H H H H H H CH OCH3 CH20CH3 4-CH3 0 0 H H H H H H H H H CH CH3 OCH3 Table XXII EMI84.1 EMI84.2 <tb> 4 <SEP> R1 <SEP> R17 <SEP> X1 <SEP> G <SEP> m.p,(OC) <tb> <SEP> 4 <SEP> H <SEP> H <SEP> CH3 <SEP> CH2 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> O <tb> <SEP> K <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> -N <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> 3 <tb> <SEP> e <SEP> H <SEP> H <SEP> OCH3 <SEP> 0 <tb> <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> OCH3 <SEP> CH2 <tb> <SEP> CH3 <tb> <SEP> S-Cl <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> K <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> R <SEP> H <SEP> CH3 <SEP> CH3 <SEP> 0 <tb> Table XXII (continued) EMI85.1 <tb> R1 <SEP> R17 <SEP> X1 <SEP> G <SEP> m.p.(oC) <tb> <SEP> H <SEP> H <SEP> H <SEP> C1 <SEP> 0 <tb> <SEP> X <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> X <SEP> R <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH2 <tb> CK3 <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> 4 <SEP> C 2CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> 4 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> <SEP> a <SEP> H <SEP> H <SEP> CH3 <SEP> 0 <tb> Table XXIII EMI86.1 EMI86.2 <tb> <SEP> R1 <SEP> R17 <SEP> X1 <SEP> m.p.(OC) <tb> <SEP> 4 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> ¯ <SEP> K <SEP> K <SEP> H <SEP> CH3 <tb> <SEP> KR <SEP> CH3 <tb> <SEP> K <SEP> H <SEP> H <SEP> CH3 <tb> -N <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> K <SEP> H <SEP> H <SEP> OCH <tb> <SEP> CHa <tb> <SEP> H <SEP> H <SEP> H <SEP> OCH <tb> <SEP> CH3 <tb> <SEP> S-Cl <SEP> H <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> R <SEP> H <SEP> CH3 <SEP> CH3 <tb> Table XXIII (continued) EMI87.1 <tb> Q <SEP> R1 <SEP> R17 <SEP> X1 <SEP> m.p.(oC) <tb> <SEP> K <SEP> H <SEP> H <SEP> C1 <tb> <SEP> R <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> R <SEP> H <SEP> H <SEP> CH3 <tb> 4 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 4 <SEP> C02CH3 <SEP> H <SEP> H <SEP> CH3 <tb> CR3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> Table XXIV EMI88.1 EMI88.2 <tb> Q <SEP> R1 <SEP> R17 <SEP> X1 <SEP> m.p.(0C) <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> -C3 <tb> <SEP> S <SEP> H <SEP> K <SEP> CH3 <tb> <SEP> K <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> CH3 <tb> ky <SEP> 3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> K <SEP> H <SEP> H <SEP> H <SEP> SOCH3 <tb> <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> OCH3 <tb> <SEP> CH3 <tb> <SEP> h <SEP> 5-C1 <SEP> H <SEP> CH3 <tb> <SEP> 4 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 4 <SEP> K <SEP> CH3 <SEP> CR3 <tb> Table XXIV (continued) EMI89.1 <tb> R1 <SEP> R17 <SEP> X1 <SEP> m.p.( C) <tb> <SEP> H <SEP> H <SEP> H <SEP> C1 <tb> <SEP> X <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> CR3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 4 <SEP> C 2CH3 <SEP> H <SEP> H <SEP> H <SEP> CH3 <tb> 4 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <tb> <SEP> 3 <tb> <SEP> a <SEP> H <SEP> H <SEP> CH3 <tb> Table XXV EMI90.1 EMI90.2 <tb> g <SEP> R1 <SEP> X2 <SEP> Y2 <SEP> m.p.( C <tb> <SEP> 4 <SEP> H <SEP> CH3 <SEP> OCH3 <tb> <SEP> H <SEP> C <SEP> 2R5 <SEP> OCH3 <tb> <SEP> K <SEP> H <SEP> CR3 <SEP> SCH3 <tb> <SEP> H <SEP> H <SEP> C2R5 <SEP> SCH3 <tb> <SEP> q <tb> <SEP> H <SEP> S <SEP> H <SEP> CH2CF3 <SEP> SC2H5 <tb> <SEP> , <SEP> CHzCF3 <SEP> SC2H5 <tb> <SEP> CH3 <tb> <SEP> 5-F <SEP> CH3 <SEP> SCH3 <tb> <SEP> H <SEP> CH2CH2CH3 <SEP> OC2H5 <tb> <SEP> a <SEP> CH3 <SEP> C <SEP> 2R5 <SEP> OCH3 <tb> <SEP> 3 <tb> Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, 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 XXVI 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 O.1X is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0 C "McCutcheon's Detergents and Emulsifiers Annuals, MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are 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 8 Wettable Powder 2-(2-Carbomethoxyfur-S-yl)-N-E (4, 6-dimethoxypyrimidin- 2-yl)aminocarbonyl]benzenesulfonamide 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 9 Wettable Powder N-( (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl )-2- (tetrahydrofuran-2-yl)benzenesulfonamide 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 10 Granule Wettable Powder of Example 9 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 11 Extruded Pellet N-E(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide 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 12 Oil Suspension N-E (4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to. under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 13 Wettable Powder N-t(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide 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 14 Low Strength Granule N-L(4, 6-dimethylpyrimidin-2-yl)aminocarbonyl]-2 (tetrahydrofuran-2-yl)benzenesulfonamide 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted gran ules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 15 Aqueous Suspension N-E (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)-2- (tetrahydrofuran-2-yl)benzenesulfonamide 40% polyacrylic acid thickener 0.3X dodecylphenol polyethylene glycol ether 0.5X 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 16 Solution N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar- bonyl)-2-(tetrahydrofuran-2-yl)benzenesulfonamide, 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 17 Low Strength Granule g N-( (4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyli-2- (tetrahydrofuran-2-yl)benzenesulfonamide 0.1% attapulgite granules 99.9% (U.5.5. 20-40 mesh) The active ingredient is dissolved in -a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evapbr-ate the solvent. The material is allowed to cool and then packaged. Example 18 Granule N-[ (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2 (tetrahydrofuran-2-yl)benzenesulfonamide 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 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example 19 High Strength Concentrate 2-(2-Carbomethoxyfur-5-yl)-N-F(4,6-dimethyl-l,3,S- triazin-2-ylaminocarbony1]benzenesulfonamide 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 20 Wettable Powder N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2 (tetrahydrofuran-2-yl)benzenesulfonamide 90% dioctyl sodium sulfosuccinate O.1X 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 21 Wettable Powder N-( (4, 6-dimethylpyrimidin-2-y1 )aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide . 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 22 Oil Suspension N-E(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl)benzenesulfonamide 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 23 Dust N-t(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- (tetrahydrofuran-2-yl )benzenesulfonamide 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. Utility The compounds of the present invention are highly active herbicides. They can be used for broadspectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial,storage areas, parking lots, drivein theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds are useful for plant growth modification, particularly in retarding the growth of undesired vegetation. Rates of application for the compounds of this invention are ordinarily determined by a number of factors, including their use as either herbicides or plant growth modifiers, the types of weeds to be controlled, weather and climate, the formulation to be used, the mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.001 to 5 kg/ha, lower rates being preferred for lighter soils and/or those having a low organic matter content, for situations where only short-term persistence is required, or for plant growth modification. 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 and plant growth modifying pro perries of the subject compounds were discovered in a number of greenhouse tests, the results of which may be seen in the following examples. Compounds Compound 1 EMI101.1 Compound 2 EMI101.2 Compound 3 EMI101.3 Compound 4 EMI101.4 Compounds (continued) Compound 5 EMI102.1 Compound 6 EMI102.2 Compound 7 EMI102.3 Compound 8 EMI102.4 Compounds (continued) Compound 9 EMI103.1 Compound 10 EMI103.2 Compound 11 EMI103.3 Compound 12 EMI103.4 Compounds (continued) Compound 13 EMI104.1 Compound 14 EMI104.2 Compound 15 EMI104.3 Compound 16 EMI104.4 Compounds (continued) Compound 17 EMI105.1 Compound 18 EMI105.2 Compound 19 EMI105.3 Compound 20 EMI105.4 Compounds (continued) Compound 21 EMI106.1 Compound 22 EMI106.2 Compound 23 EMI106.3 Compound 24 EMI106.4 Compounds (continued) Compound 25 EMI107.1 Test A Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with a nonphytotoxic solvent solution of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild oats with two leaves, sicklepod with three leaves (including cotyledonary ones), morningglory with four leaves (including the cotyledonary ones), cocklebur with four leaves (including the cotyledonary ones), sorghum with four leaves, corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed with a nonphytotoxic solvent solution of the compounds of Table A. Other containers of the above mentioned weeds and crops were treated pre- or post-emergence with the same nonphytotoxic solvent so as to provide a solvent control. A set of untreated control plants was also included for comparison. Preemergence and post-emergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment. Several of the compounds tested were essentially innocuous to wheat but, at the same rate of application, provided effective weed control. The following rating system was ased: 0 = no effect; 10 = maximum effect; C = chlorosis or necrosis; E = emergence inhibition; G = growth retardation; H = formative effects; S = albinism; U = increased chlorophyl; X = axillary stimulation; and 6Y = abscised buds or flowers. The test data are summarized in Table A. Table A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate kg/ha 2 2 2 2 POST-EMERGENCE Bush bean 1H,5G 4S,8G,6Y 6C,9G,6Y 6C,9G,6Y Cotton 5C,9G 3C,3H,8G 5C,9G 5C,9G Morningglory 1C,4G 1C 3C,9G 4C,9G Cocklebur 3C,7H 2C,7H 5C,9G 9C Sicklepod 2C 2C 4C 4C Nutsedge 2C,9G 2C,5G,5X 9G 2C,9G Crabgrass 6G 2C 2C,9G 1C,2G Barnyardgrass 9H 1C 3C,9H 2C,5H Wild Oats O 0 2C,8G,5X 0 Wheat O 0 3C,9G 2G Corn 0 1C,3G 2C,9G 2C,9H Soybean 1C,3G 1C,1H 4C,8G 4C,8G Rice 2C,9G 0 5C,9G 5G Sorghum 2C,7G 1C,4G 1C,9G 3C,8H PRE-EMERGENCE Morningglory 1C 2C 8G 8G Cocklebur 8H 9H - 9H Sicklepod 1C 2C 9C 2C,7H Nutsedge 9G 10E lOE lOE Crabgrass 2C 3C 2C,6G 2C Barnyardgrass 5G 3C 3C,8H 5C Wild Oats 2G 2G 3C,9G 1C,6G Wheat .2G 2G 3C,9G 4G Corn 2C,6G 2C,8G 9G 2U,9G Soybean O lC,lH 5H 7H Rice 3C,7H 2C,3G lOE 2C,8G Sorghum 2C,7G 2C,7G 5C,9H 2C,9H Table A (continued) Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Rate kg/ha 2 2 0.05 0.05 POST-EMERGENCE Bush bean 5C,9G,6Y 1C,2G 5C,9G,6Y 6C,9G,6Y Cotton 6C,9G 2C,3H 4C,9G 5C,9G Morningglory 2C,6G 1C lOC lOC Cocklebur 5C,9G 3C,6H lOC lOC Sicklepod 1C,2G 0 4C,6G 4C,8G Nutsedge 1C,9G 2G 2C,8G 2C,9G Crabgrass 2C,8G 1C,3G 2C,6G 2C,9G Barnyardgrass 2C,8H 0 5C,9H 5C,9H Wild Oats 2C,6G 0 4C,9G 5C,9G Wheat 3C,9G 0 3U,9G 4C9G Corn 2C,9G 3C,7G 5U,9G 5U,9G Soybean 2C,4H 2C,5G 6C,9G 5C,9G Rice 3C,9G 2C,7G 5C,9G 5C,9G Sorghum 2C,9G 2C,9G 3C,9G 3C,9H Sugar beet - - 3C,9H 9C PRE-EMERGENCE Morningglory 8G 1C,3G 5C,9G Cocklebur 9H <RTI ID=111.2> 9H 9H 9H Sicklepod 1C,5G 2C 9G 9G Nutsedge lOE 9G 9G lOE Crabgrass 3C 0 2G 3C,6G Barnyardgrass 3C,6H 3C 2C,9H 5C,9H Wild Oats 2C,9H 2C,8G 2C,9G 5C,9G Wheat 4C,9H 5G 2C,9G 4C,9H Corn 10E 2C,8G 9G 4C,9G Soybean 8H 1C 2C,5H 9H Rice lOE 9H lOE lOE Sorghum 10E 3C,9G 5C,9H 5C,9H Sugar beet 9G lOE Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 5C,9G,6Y 6C,9G,6Y 5C,9G,6Y 5C,9G,6Y Cotton 6C,9G 4C,8G 5C,9G 0 Sorghum 4C,9G 2C,9G 9G 2C,9G Corn 6U,9G 2U,9G 1U,9H 2C,9G Soybean 10C 9C 4C,8G 5C,9H Wheat 3C,9G 2C,9G 1C 7G Wild Oats 4C,9G 2C,9G 1C,5G 2C,9G Rice 6C,9G 9C 9C 6C,9G Barnyardgrass 5C,9H 5C,9H 2C,9H 5C,9H Crabgrass 4C,9G 2C,8G 1C,3G 2C,5G Morningglory 4C,7H 5C,8H 10C 5G Cocklebur lOC lOC lOC 2C,8H Sicklepod 5C,9G 3C,8H 3C,5H 2C,5G Nutsedge 5C,9G 3C,8G 3G 2C,7G Sugar beet 9C 9C 9C 2C,7H PRE-EMERGENCE Sorghum 5C,9H 5C,9H 5C,9H 3C,9H Corn 2C,9H 2C,9G 2C,9H 3C,9G Soybean 9H 9H 2C,5H 5H Wheat 1C,9G 2C,9G 0 2C,9G Wild Oats 3C,9G 4C,9G 5H 3C,7G Rice lOE lOE lOE 2C,9H Barnyardgrass 5C,9H 5C,9H 2C,7H 5C,9H Crabgrass 2C,9G 2C,8G 0 2C Morningglory 9G 9C 9C 8G Cocklebur - - <RTI ID=112.3> 9H 9H Sicklepod 9G 9G 3C,9G 9G Nutsedge 10E 5C,9G 0 2C,9G Sugar beet lOE lOE lOE 9G Table A (continued) Cmpd. 13 Cmpd. 14 Cmpd. 15 Cmpd. 16 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 6C,9G,6Y 5C,9G,6Y 3C,9G,6Y 5C,9G,6Y Cotton 2C,3G 2C,5G 3C,6G 2C,5G Sorghum 2C,9G 9G lC,9G 0 Corn 2C,9G 2C,9G 2C,9G 0 Soybean 5C,9G 9C 9C 9C Wheat 2C,7G 0 1C,6G 0 Wild Oats 2C,7G 0 1C,6G 0 Rice 5C,9G 5C,9G 6C,9G 0 Barnyardgrass 5C,8H 5C,9H 2C,9H 1H Crabgrass 2C,4G 1C,6G 2C,6G 0 Morningglory 3C,5G 2C,7G 2C,8G 5C,9G Cocklebur 3C,9H 3C,8H 3C,8H 4G Sicklepod 3C,6G 3C,9H 2C,6G 2C,8H Nutsedge 5G 9G 1C,8G 5G Sugar beet 10C 5C,9G 2C,9H 4C,9G PRE-EMERGENCE Sorghum 5C,9G 5C,9H 9H 2G Corn 3C,9H 2C,9G 9G 1C,6G Soybean 8H 8H 9H 8H Wheat 2C,9G 1C,6G 2C,9G 0 Wild Oats 3C,8G 1C,3G 3C,8G 2C Rice lOE 9H 9H 2G Barnyardgrass 5C,9H 5C,9H 5C,9H 2C Crabgrass 2C,4G 2C,6G 4C,8G 0 Morningglory 9G 7G 8G 9G Cocklebur 9H 9H 9H 9H Sicklepod 8G 9G 9G 8G Nutsedge 10E 10E 10E 5G Sugar beet lOE lOE lOE lOE Table A (continued) . Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 5C,8G,6Y 5S,9G,6Y 5C,9G,6Y 9C Cotton 3C,5G 4C,4H,8G 6C,9G 6C,9G Sorghum 2C,8H 3C,9H 9H 2G Corn 2C,6H 3C,8H 2C,9G 2G Soybean 4C,9G 3C,9G 3C,9G 5C,9G Wheat 1H 1C 3G 0 Wild Oats 1K 2C 3G 0 Rice 2C,8G 2C,8G 2C,7G 0 Barnyardgrass 2C,6H 5C,9H 9C 2H Crabgrass 1C 5G 2C,4G 0 Morningglory 5C,9G 3C,8G 3C,9H 10C Cocklebur 2C,5G 2C,8H 5C,9H 9C Sicklepod 3C 2C,4G 5C,8H 4C,5G Nutsedge 2C,6G 3C,7G 2C,8G 5G Sugar beet PRE-EMERGENCE Sorhum 4G 3C,9H 4C,9H 2G Corn 3C,6G 2C,8H 9G 1C,4G Soybean 1C 3C,8H 9H 9H Wheat 5G 8G 7G 0 Wild Oats 2C,4G 2C,8G 2C,8G 0 Rice 0 3C,6G 10E 1C,4G Barnyardgrass 3G 3C,9H 3C,9H 2G Crabgrass 3G 2C,5G 3C,8G 2G Morningglory 5G 8H 9G 9G Cocklebur 8H 9H 9H 9H Sicklepod 8G 9G 9G 9G Nutsedge 2G 8G 10E 3G Sugar beet - - - Table A (continued) Cmpd. 21 Rate kg/ha 0.05 POST-EMERGENCE Bush bean 9C Cotton 3C,9G Sorghum 2C Corn O Soybean 5C,9G Wheat O Wild Oats 0 Rice O Barnyardgrass O Crabgrass 2C Morning glory 9C Cocklebur lOC Sicklepod 3C,4H Nutsedge 0 Sugar beet PRE-EMERGENCE Sorghum o Corn O Soybean O Wheat O Wild Oats O Rice O Barnyardgrass O Crabgrass 2G Morningglory 8G Cocklebur 9H Sicklepod 9G Nutsedge O Sugar beet Table A (continued) Cmpd. 22 Cmpd. 23 Cmpd. 24 Cmpd. 25 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 4C,9G,6Y 4H,6Y 6C,9G,6Y 9C Cotton 4C,9G 5C,7H 5C,9G 4C,9G Morningglory 9C 4C,8H 5C,9G lOC Cocklebur 9C 4C,8H 4C,9G lOC Sicklepod 5C,7H 2H 3C,9G 9C Nutsedge 2C,9G 3C,8G 2C,9G 6C,9G Crabgrass 3C,8G 2C,4H 2C,8H 6C,9G Barnyardgrass 3C,9H 3C,8H 5C,9H 9C Wild Oats 3C,9G 3C,8H 2C,9G 9C Wheat 2C,9G 2C,3H 2C,7G 9C Corn 3C,9G 4C,9H 3C,9G 10C Soybean 5C,9G 3C,9G 5C,9G 9C Rice 5C,9G 6C,9G 5C,9G 6C,9G Sorghum 3C,9H 5C,9H 2C,9H 6C,9G Sugar beet 4C,8G 2C,4G 2C,9G 9C PRE-EMERGENCE Morningglory 9C 2C,6H 9C 3C,9H Cocklebur 9H 5H,2C 9H Sicklepod 9C 3H 2C,9G 2C,9G Nutsedge 3G 0 lOE lOE Crabgrass 1C,2H 4G 2C,5G 3C,7G Barnyardgrass 5C,9H 2C,4G 4C,9H 3C,9G Wild Oats 5C,9G 2C,5G 2C,9G 3C,9H Wheat 3C,9G 2C,3G 2C,9G 3C,9H Corn 3C,9G 3C,3G 3C,9H 10E Soybean 4C,7H 2C 3C,9H 9H Rice 5C,9H 3C,5G 10E 10E Sorghum 5C,9H 3C,7H 5C,9H 5C,9H Sugar beet 5C,9G 3C,5H 9G 10E

Claims: Claims: 1. A compound of the formula: EMI117.1 wherein Q is EMI117.2 EMI118.1 where Q' is EMI118.2 EMI119.1 W is O or S; W' is O or S; R is H, F, C1, CH3 or OCH3; R1 is H, F, C1, Br, CH3, CF3 or OCH3; R2, R3, R5, R9, R10, R11, R12 and R17 are independently H or CH3; R4, R6, R7 and R8 are independently H, CH3 or OCH3; R13, R14, R15 and R16 are independently CH3 or OCH3; R18 is H or CH3; R19 is H or CH3; R20 is H or CH3; R21 is H or CH3; R22 is H or CH3; R23 is H or CH3; R24 is H, CH3, C2H5, Cl, Br, OCH3, or OC2H5; R25 is R, CH3, C2H5, C1, Br, OCH3 or OC2H5; R26 is H, CH3, C2H5, Cl, Br, OCH3, OC2H5 or CO2CH3; R27 is H or CH3; R28 is H or CH3; EMI119.2 EMI120.1 X is CH3, OCH3 or C1; ; Y is CH3, C2H5, CH2OCH3, OCH3, OC2H5, CH(OCH3)2, SCH3, CF3, NH2, NHCH3, N(CH3)2, OCH2CH2OCH3, OCH2CF3 or EMI120.2 Y1 is CH3, C2H5, CH2OCH3, OCH3, OC2H5, CH(OCH3)2, NH2, NHCH3 or N(CH3)2; Z is CH or N; X1 is CH3, OCH3 or C1; G is O or CH2; X2 is C1-C3 alkyl or CH2CF3; Y2 is CH3O, C2H5O, CH3S or C2H5S; and their agriculturally suitable salts; provided that 1) when W is S, then R17 is H, A is EMI120.3 Y is CH3, OCH3, C2H5, CH2OCH3, CH(OCH3)2 or EMI120.4 2) when Q is EMI121.1 then R24 is H, CH3 or C2H5; R25 is H, CH3 or C2H5; and R26 is H, CH3, C2H5 or -CO2CH3; 3) when one of R24, R25, R26 is other than H, then the other two substituents are H or CH3; 4) the total number of carbon atoms in R18, R19, R20, R21, R22, R23, R27 and R28 is less than or equal to 4; 5) when X is C1, then Z is CH and Y or Y1 is OCH3, NH2, OC2H5, NHCH3 or N(CH3)2; and 6) when R is CH3, then R is in the 3-, 4- or 5-position of the benzene ring. 2. Compounds of Claim 1, Formula I, where W is 0. 3. Compounds of Claim 2 where R1 and R17 are H. 4. Compounds of Claim 3 where, R24 is H, CH3 or C2H5; R25 is H, CH3 or C2H5; and R26 is H, CH3, C 2R5 or -C02CH3; 5. Compounds of Claim 4 where Y is CH3, CHçOCH3, OCH3, OC2H5, CH(OCH3)2 or EMI121.2 and A is EMI121.3 6. Compounds of Claim 1, Formula Ia, where R and R17 are H. 7. Compounds of Claim 6 where Y1 is CH3, OCH3, CH20CH3 or N(CH3)2. 8. Compounds of Claim 4 where W' = 0. 9. Compounds of Claim 4 where El = S. 10. Compounds of Claim 7 where QÚ is a substituted pyridine. 11. Compounds of Claim 7 where Q' is a substituted pyrimidine. 12. Compounds of Claim 7 where Q' is a substituted pyrazine. 13. Compounds of Claim 7 where QÚ is a substi- tuted triazine. 14. A compound of Claim 1 selected from N [(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide; N-[(4-methoxy-6 methylpyrimidin-2-yl aminocarbonyll -2- (tetrahydrofuran- 2-yl)benzenesulfonamide, N-[4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide; N-lC4-chloro-6-methoxvpyrimidin-2-yl)aminocarbonyl3-2 (tetrahydrofuran-2-yl)benzenesulfonamide; N-[(4,6 dimethoxy-1,3,5-triazin-2-ylEaminocarbonyl]-2-ttetra- hydrofuran-2-yl)benzenesulfonamide; N-[(4-methoxy-6methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide; or an agriculturally suitable salt thereof. 15. A compound of Claim 1 selected from N-1(4- methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(2pyridinyl)benzensulfonamide; N-[(4,6-dimethylpyrimidin 2-yllaminocarhonyl3-2-(2-pyridinyllbenzenesulfonamide; N-tC4,6-dimethoxy-pyrimidin-2-ylXaminocarbonyl]-2-(2- pyridinyllbenzenesulfonamide; or an agriculturally suitable salt thereof. 16.. A compound of Claim 1 which is N-[(4-methoxy 6-methylpyrimidin-2-yllaminocarbonyll-2-t2-pyrimidinyl) benzenesulfonamide; or an agriculturally suitable salt thereof. 17. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a herbicidal compound and at least one of the following: surfactant, solid or liquid diluent, characterised in that said herbicidal compound comprises a compound of any of claims 1 te 16. 18. A method for controlling the growth'of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound characterised in that said herbicidal compound comprises a compound of any of claims 1 to 16. 19. A method for regulating the growth of plants by applying to the locus of such. plants an effective but substantially non-phytotoxic amount of a plant growth regulant characterised in that said plant growth regulant comprises a compound of any of claims 1 to 16. 20. A method for the preparation of a compound of . claim 1 which comprises Cal reacting a benzenesulfonamide of formula EMI123.1 with a methyl heteroaryl carbamate of formula EMI123.2 under catalytic conditions, to obtain a compound of formula (I1 wherein R1, R17, Q and A are as defined in claim 1 and W is O; or (b) reacting a benzenesulfonyl isocyanate or isothiocyanate of formula EMI124.1 with an aminoheterocycle of formula EMI124.2 wherein R1, R171 W and A are as defined in claim 1 and Q is selected from Q-1, 0-2 or Q-6 to Q-ll; or Cc reacting said sulfonamide of formula (II1 with a heterocyclic isothiocyanate of formula SCN-A (Va) wherein A is as defined in claim 1; or (d) reacting a sulfonamide of formula EMI124.3 with a methyl pyrimidinyl carbamate or methyl triazinyl carbamate of formula EMI124.4 under catalytic conditions, wherein R1, R17, Q', X, Y and Z are as defined in claim 1, to obtain a product of formula (Ia).

Inventors: SAUERS, RICHARD FRANK, SHAPIRO, RAFAEL
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1983
Main classification: C07D405
IPC codes: C07D521, C07D403, C07D409, A01N47, C07D239, C07D401, C07D405, C07D213, C07D307, G03G21