HERBICIDAL O-ALKYLSULFONYLOXY- AND O-ALKYLSULFONYLAMINO-BENZENESULFONAMIDES

Abstract: A compound of the formula: where W is O or S; Q is O or NR₅; R₁, R₂, R₃ and R₄ are as defined in claim 1. A is X is NH₂, N(CH₃)₂, NHCH₃, C₁-C₄ alkyl, C₁-C₄ alkyl substi­ tuted with 1-3 atoms of F, Cl or Br, CH₂OCH₃, CH₂OCH₂CH₃, C₁-C₄ alkoxy, C₁-C₂ alkylthio, C₃-C₄ alkenyloxy, C₃-C₄ alkynyloxy, OCH₂CH₂OCH₃ or C₂-C₄ alkoxy substituted with 1-3 atoms of F, Cl or Br; n is 1 or 2; Y is H, CH₃, OCH₃ or Cl; X₁ is O or CH₂; Y₁ is H, CH₃, OCH₃ or Cl; X₂ and Y₂ are independently CH₃ or OCH₃; and Z is CH, N, CCH₃ CBr, CCl, CF, Cl, CC₂H₅, CCH₂CH₂Cl or CCH₂CH=CH₂; The compound may be formulated in compositions and may be used as general, as well as selective pre- and post emergence herbicides. The compounds may be prepared from novel intermediates of formula where Q, W, R₁, R₂ and R₃ are as defined above, and Z′ is CH or N).

Description: Herbicidal o-Alkylsulfonyloxy- and o-Alkylsulfonylaminobenzenesulfonamides This invention relates to ortho(sulfonyl)oxybenzene sulfonamides and their use as herbicides. Netherlands Patent 121,788, published September 15, 1966, teaches the preparation of compounds of Formula (I'),and their use as general or selective herbicides: EMI1.1 wherein R1 and R2 may independently be alkyl of 1-4 carbon atoms; and R3 and R4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. Compounds of Formula (II'),and their use as antidiabetic agents, are reported in'J. Drug Res. 6, 123 (1974): EMI1.2 wherein R is pyridyl. In U.S. Patent 4,127,405, compounds are disclosed of the general formula: EMI2.1 wherein R1 is EMI2.2 R3 and R6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH3S(O)n or CH3C2S(O)n; R4 is hydrogen, fluorine, chlorine, bromine or methyl; R5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; R7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; R8 is hydrogen, methyl, chlorine or bromine; R9 and R10 are independently hydrogen, methyl, chlorine or bromine; W and Q are independently oxygen or sulfur; n is 0, 1 or 2; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, tri fluoromethyl, CH3S- or CH3OCH2-; and Y is methyl or methoxy; or their agriculturally suitable salts; provided that: (a) when R5 is other than hydrogen, at least one of R3, R4, R6 and R7 is other than hydrogen and at least two of R3, R4, R6 and R7 must be hydrogen; (b) when R5 is hydrogen and all of R3, R4, R6 and R7 are other than hydrogen, then all of R3, R4, R6 and R7 must be either chlorine or methyl; and (c) when R3 and R7 are both hydrogen, at least one of R4, R5 or R6 must be hydrogen. In particular, the patent discloses orthosubstituted compounds wherein the substitution is C1-C4 alkyl. The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing.these crops. Preventing or minimizing theloss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops. We have now discovered novel compounds which may be used as general, as well as selective, preand post- emergence herbicides. Thus, in one aspect, the invention provides compounds of general formula I EMI5.1 where W is O or S; Q is O or NR5; R1 is C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, CH2CH2OCH3, CH2CH2CH2OCH3 or EMI5.2 R2 is H, F, C1, Br, OCH3, NO2 or C1-C2 alkyl; R3 is H, F, C1, Br or CH3; R4 is H, CH3 or OCH3; R5 is C1-C4 alkyl; R6 and R7 are independently H, F, C1, Br, CH3, CF3, NO2 or OCH3; A is EMI6.1 X is NH2, N(CH3)2, NHCH3, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, CH2OCH3, CH2OCH2CH3, C1-C4 alkoxy, C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH2OCH3 or C2-C4 alkoxy substituted with 1-3 atoms of F, Cl or Br; n n is 1 or 2; Y is H, CH3, OCH3 or C1; X1 is O or CH2; Y1 is H, CH3, OCH3 or C1; ; X2 and Y2 are independently CH3 or OCH3; and Z is CH, N, CCH3, CBr, CCl, CF, CI, CC2H5, CCH2CH2Cl or CCH2CH=CH2; provided that (1) when Y is Cl, then Z is other than N and X is NH2, NHCH3, N(CH3)2, CH3 or OCH3; (2) when Y is H, then X is OCH3, CH3 or CH2OCH3, and Z is other than N; and (3) when W is S, then R4 is H. Preferred for reasons of higher herbicidal activity and/or more favorable ease of synthesis are: (1) Compounds of the generic scope where R5 is CH3 W is 0, and R4 is H or CH3; (2) Compounds of Preferred (1) where R1 is C1-C4 alkyl, CF3, CH2CH2OCH3 or CH2CH2CH2OCH3; (3) Compounds of Preferred (2) where R2 is H; (4) Compounds qf Preferred (3) where R3 is H; (5) Compounds of Preferred (4) where R1 is C1-C3 alkyl or CF3; Q is O; A is EMI7.1 and Z is CH or N. -(6) Compounds of Preferred (5) where R4 is H; and (7) Compounds of Preferred (6) where X and Y are independently CH3 or OCH3, and R1 is CH3 Specifically preferred for particularly high herbicidal activity and/or particularly favorable ease of synthesis are: N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hy- droxybenzenesulfonamide, methanesulfonate; 2-hydroxy-N- t (4-methoxy-6-methylpyrimidin-2-yl) amino- carbonyl)benzenesulfonamide, methanesulfonate; and N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hy- droxybenzenesulfonamide, methanesulfonate. All of the above compounds show selectivity.on wheat. N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonylJ2- hydroxybenzenesulfonamide, methanesulfonate; 2-hydroxy-N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)- aminocarbonyl]benzenesulfonamide, methanesulfonate; N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2- hydroxybenzenesulfonamide, methanesulfonate; N-[(4,6-dimethoxy-l,3,5-triazin-2-yl) (methyl)aminocar- bonyl]-2-hydroxybenzenesulfonamide, methanesulfonate; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl3-2-hy- droxybenzenesulfonamide, 1-propanesulfonate, which shows selectivity on rice and corn; and 2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]benzenesulfonamide, 1-propanesulfonate, which shows selectivity on soybeans. This invention also relates to compounds of Formula II which are useful intermediates for the preparation of the herbicidal compounds of Formula I: EMI8.1 where W,Q,R1,R2 and R3 are as defined above. Preferred intermediates, for reasons of more favorable ease of synthesis and/or higher herbicidal activity of the compounds of Formula I, are: (1) Compounds of Formula II where Q is O, R2 and R3 are H, R1 is CH3 or CF3, and W is 0; and (2) Compounds of Formula II where Q is NCH3, R2 and R3 are H, R1 is CH3 or CF3, and w is O. This invention also relates to compounds of Formula VII which are useful intermediates for the preparation of the herbicidal compounds of Formula I: EMI10.1 where Q is O or NR5; R1 is C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, CH2CH2OCH3, CH2CH2CH2OCH3, or EMI10.2 R2 is H, F, C1, Br, OCH3, NO2 or C1-C2 alkyl; R3 is H, F, C1, Br or OCH3; R5 is C1-C4 alkyl; R6 and R7 are independently H, F, C1, Br, CH3, CF3, NO2 or OCH3; and Z is CH or N. Synthesis The compounds of this invention can be made as outlined below. The compounds of Formula (IV), (VI), (XII) or (XIV) can be prepared by reacting an appropriate 2-aminopyrimidine, 2-aminotriazine or 2-aminobicyclopyrimidine of Formula (III), (V), (XI) or (XIII) with an appropriately substituted sulfonylisocyanate or isothiocyanate, of Formula (II), where Q, R1, R2, R3, R4, X, Y, Z, X1, X2, Y1, Y2, W and n were previously defined. The reaction is best carried out in inert solvents such as methylene chloride and acetonitrile. The mode of addition is not critical,-however, it is often convenient to add a solution of the isocyanate or isothiocyanate of Formula (II) to a stirred suspension of the aminoheterocycle (III), (V), (XI) or (XItI) The reaction is generally exothermic. In some cases, the desired product is insoluble in the reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent and trituration of the residue with solvents such as diethyl ether, l-chlorobutane, or hexanes and filtration. EMI12.1 EMI13.1 Compounds of this invention may also be prepared by reacting a sulfonamide of Formula VIII with a 4,6dichloroheterocyclic isocyanate of Formula IX. EMI14.1 One or both of the halogen atoms on the heterocyclic ring of the compound of Formula VII can be displaced by an alkoxide of OR8, to give compounds of Formula X, where R8 is C1-C4 alkyl, C3-C4 alkyl, C3-C4 alkynyl, CH2CH2OCH3 or C2-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, and Y" is C1 or OCH3. EMI14.2 The process for the preparation of compounds of Formula X is described in our European Patent Specification No. 0030140, published 10 June 1981. Sulfonamides, prepared as described in Research Disclosure, pg. 52, (1978), may conveniently be converted to the corresponding isocyanates or isothiocyanates of Formula II by methods described in U.S. Patent No. 4,127,405. The synthesis of the heterocyclicamine derivatives has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published in Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series which are herein incorporated by reference. The preparation of amino bicyclopyrimidines are described in unexamined European Patent No. 15683. The aminoheterocyclic intermediates of Formula III, V, XI or XIII in which R4 is CH3, may be prepared by the following procedure, or by obvious modifications thereof. EMI15.1 A solution of the amine XV in concentrated hydrochloric acid is contacted with an aqueous sodium nitrite solution and the chloro compound XVI is isolated by filtration of the acidic solution (see for example, Bee and Rose, J. Chem. Soc. C., 2051 (1966) for the case in which Z is CH and X and Y are OCH3). Displacement of the chlorine may be accomplished by heating with an excess of methylamine in water to obtain the methylaminoheterocycle XVII. N-Methoxyamino heterocycles can be prepared by procedures reported on the literature [see, for example, Belgian Patent 618,563 and J. T. Shaw, et al., J. Orq. Chem., 27 4054 (1962)] and the procedure illustrated below. EMI16.1 Chloro compound XVI is reacted with hydroxylamine to form derivative XVIII which may be alkylated with methyl bromide to afford the N-methoxy heterocyclic amine XIX. This compound may alternately be prepared in one step by treatment of XVI and O-methyl hydroxylamine hydrochloride with an alkali metal hydroxide such as sodium hydroxide. The compounds of this invention and their preparation are further illustrated by the following examples, wherein temperatures are given in degrees centigrade and parts are by weight unless otherwise indicated. Example 1 2-Hydroxybenzenesulfonyl isocyanate, methanesulfonate To 10.0 g (.04 mole) 2-hydroxybenzenesulfonamide, methanesulfonate, suspended in 75 ml dry xylenes was added 4.0 g (.04 mole) N-butylisocyanate and a catalytic amount of 1,4-diazobicyclo[2.2.2]octane ("'.05 g). This mixture was rapidly heated to reflux temperature ("'l350C) and 4.0 ml of phosgene was slowly added (at such a rate as to keep the reaction temperature greater than 1280C). The phosgene addition required rl 1/2 hours. The reaction was cooled to room temperature, filtered under N2, and the solvent evaporated under reduced pressure. The infrared spectrum of the resultant oil was consistent for 2-hydroxybenzenesulfonyl isocyanate, methanesulfonate (2210 cm Example 2 N-[ (4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2- hydroxvbenzenesulfonamide, methanesulfonate To a suspension of .6 g 2-amino-4,6-dimethoxypyrimidine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms (210.C-290C) and is then stirred 1/2 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 1.2 g tan solid m.p. 165-1660C. The infrared spectrum shows absorption bands at 1740, 1615, 1590, 1360 cm Calc. for C-38.9, H-3.73, N-12.9 Found C-38.3, H-3.63, N-13.0. Example 3 2-Hydroxy-N-[ (4-methoxy-6-methylpyrimidin-2-yl)amino- carbonyl]benzenesulfonamide, methanesulfonate To a suspension of .6 g 2-amino-4-methoxy-6methylpyrimidine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for 1/2 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give .95 g white solid m.p. 189-1900C. The infrared spectrum shows absorption bands at 1700, 1615, 1560, 1370 cm-Ú. Calc. for C-40.4, H-3.87, N-13.4. Found C-40.2, H-3.77, N-13.6. Example 4 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2 hydroxvbenzenesulfonamide, methanesulfonate To a suspension of .6 g 2-amino-4,6-dimethoxy1,3,5-triazine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for about 1 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and 'filtered to give 1.4 g tan solid m.p. 163-1660C. The infrared spectrum shows absorption bands at 1715, 1600, 1550, 1350 cm Using the procedures similar to those of Examples 1-4, the following compounds can be prepared. Table I EMI19.1 EMI19.2 <tb> q <SEP> R2 <SEP> R3 <SEP> R4 <SEP> g <SEP> W <SEP> Y <SEP> X <SEP> Z <SEP> m.p.(OC) <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH,3 <SEP> CH <SEP> 165-166 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH <SEP> 3 <SEP> CH3 <SEP> CH <SEP> 189-190 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 204-205 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 163-166 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH <SEP> 3 <SEP> CH3 <SEP> N <SEP> 170-173 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> N <SEP> 181-184 <tb> <SEP> (CH2)3CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 0CH3 <SEP> 9CH3 <SEP> CH <SEP> 158-162 <tb> (CH2)2CH2Cl <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> CC13 <SEP> H <SEP> H <SEP> H <SEP> 0 <SEP> 0 <SEP> OCH <SEP> 3 <SEP> OCH3 <SEP> CH <tb> <SEP> < <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <SEP> 216-219 <tb> Cl <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH <SEP> CH3 <SEP> CH <tb> <SEP> C1 <tb> < <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> O,N <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CCK, <SEP> CK, <SEP> H <tb> CH, <tb> CH3 <tb> <SEP> CH3 <tb> CH3 <tb> <SEP> 3 <tb> Table I (continued) EMI20.1 <tb> RI <SEP> R2 <SEP> R3 <SEP> 4 <SEP> Q <SEP> W <SEP> Y <SEP> X <SEP> Z <SEP> m.p.(OC) <tb> CF <tb> CF3 <tb> <SEP> ss <SEP> H <SEP> H <SEP> O <SEP> O <SEP> COCK, <SEP> CH3 <SEP> CH <tb> <SEP> CF3 <tb> Br <tb> <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CCH3 <SEP> CH, <SEP> CH <tb> Br <SEP> H <SEP> H <SEP> H <SEP> 0 <SEP> 0 <SEP> OC1 <SEP> CH <SEP> CH <tb> OCH3 <tb> A <SEP> 3 <SEP> CH3 <SEP> CH <tb> C1 <tb> <SEP> F <tb> <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH, <SEP> CH <tb> <SEP> F <SEP> *4. <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <SEP> 174-176 <tb> CH3 <SEP> 6-CH, <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> CH3 <SEP> 5-F <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OH3 <SEP> CK, <SEP> CH <tb> 5N02 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> 3 <SEP> CH3 <tb> 5-Br <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH, <SEP> CH3 <SEP> CH <tb> CH3 <SEP> .5-OCH3 <SEP> H <SEP> O <SEP> O <SEP> CC; ;CH3 <SEP> CH <tb> <SEP> CH, <SEP> 5-CF3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH <SEP> CH3 <SEP> CH <tb> CH3 <SEP> 5-C1 <SEP> 4-C1 <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> <SEP> CH3 <SEP> 5-CH3 <SEP> 4-CH3 <SEP> H <SEP> O <SEP> O <SEP> CCH, <SEP> CH3 <SEP> CH <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> 0C <SEP> O¯H3 <SEP> N <SEP> 91-96 <tb> Table I (continued) EMI21.1 <tb> RI <SEP> 2 <SEP> R3 <SEP> R4 <SEP> Q <SEP> W <SEP> Y <SEP> X <SEP> Z <SEP> m.p.(OC) <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> - <SEP> -N-CH3 <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> -N(CH,)3 <SEP> 0 <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> Cl <SEP> OCH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> -(CH2)3CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -OCHCF3 <SEP> N <tb> <SEP> H <SEP> H <SEP> H <SEP> 0 <SEP> 0 <SEP> C <SEP> -OCHCC13 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -OCCBr3 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CCH2CH2C1 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> o <SEP> CH3 <SEP> H <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 3 <SEP> CH3 <SEP> 2)3 <SEP> 3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> C <SEP> 3 <SEP> CH2CH2C1 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -CH2CF3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> ,CH3 <SEP> -O(CH2)3CH3 <SEP> N <tb> H <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -CCH2CH=CH2 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -CCH2C=CH2 <tb> <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CCH2C=CH <SEP> N <tb> CH3 <SEP> -H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> 2C5CCH3 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> -CH20CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> 9CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> S(CH2)CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CBr <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CI <tb> CH <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> CH3 <SEP> CH3 <SEP> CF <tb> <SEP> 3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH <SEP> CH3 <SEP> CC1 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH3 <SEP> CH3 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> CH3 <SEP> CH3 <SEP> N <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> CH <SEP> CH3 <SEP> CH <tb> CH3 <SEP> 3-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> OCH3 <SEP> CH <SEP> 134-142 <tb> Table I (continued) R1 R2 R3 R4 Q W Y X Z m.p. ( C) CH3 3-Cl H H O O OCH3 OCH3 N 165-170 CH3 3-Cl 5-Cl H O O OCH3 CH3 N 210 (dec) CH3 3-Cl 5-Cl H O O OCH3 OCH3 N 200 (dec) CH3 H H H NCH2CH3 O OCH3 OCH3 CH CH3 H H H N(CH2)2CH3 O OCH3 OCH3 CH CH3 H H H NCH3 O OCH3 CH3 CH CH3 H H H NCH3 O CH3 CH3 CH CH3 H H H NCH3 O OCH3 CH3 N CH2CH3 H H H O O OCH3 OCH3 CH 189-191 CH2CH3 H H H O O OCH3 CH3 CH 160-162 CH2CH3 H H H O O CH3 CH3 CH 196-198 CH2CH3 n H H O 0 OCH3 OCH3 N CH2CH3 H H H O O OCH3 CH3 N %CH2CH3 H H H O O CH3 CH3 N CH2CH3 H H CH3 O 0 OCH3 OCH3 N (CH2)3CH3 H H H O O OCH3 CH3 CH (CH2)3CH3 H H H O O CH3 CH3 CH 201-202 (CH2)3CH3 H H H O O OCH3 OCH3 N 150-153 (CH2)3CH3 H H H O O OCH3 CH3 N 161-163 (CH2)3CH3 H H H O O CH3 CH3 N (CH2)3CH3 H H H O O H CH3 CCl 135-140 (CH2)2CH3 H H H O O OCH3 OCH3 CH 172-174 (CH2)2CH3 H H H O O OCH3 CH3 CH 183-186 (CYH2)2CH3 H H H O O CH3 CH3 CH 182-184 (CH2)2CH3 H H H O 0 OCH3 OCH3 N (CH2)2CH3 H H H O O OCH3 CH3 N 144-147 (CH2)2CH3 H H H O O CH3 CH3 N (CH2)2CH3 H H CH3 O O OCH3 OCH3 CH (CH2)2CH3 H H H O O H CH3 CCl 185-190 CF3 H H H O 0 OCH3 OCH3 CH 129-131 CH2CH2Br H H H O O OCH3 OCH3 CH CH2CH2OCH3 H H H O O OCH3 OCH3 CH CH2CH2OCH3 H H H O O OCH3 CH3 CH Table I (continued) R1 R2 R3 R3 O W Y X Z m.p.( C) CH2CH2OCH3 H H H O O CH3 CH3 CH CH2CH2OCH3 H H H O O OCH3 CH3 N (CH2)2CH2OCH3 H H H O O OCH3 OCH3 CH CH3 H H H O O Cl NH2 CH CH3 H H H O O Cl NHCH3 CH CH3 H H H O O Cl N(CH3)2 CH CH3 H H H O O CH3 CH20CH3 CH CH2CH3 H H H O O CH3 CH2OCH3 CH (CH2)2CH3 H H H O O CH3 CH2CCH3 CH CH3 H H H O O CH3 CH2OCH2CH3 CH CH3 H H H O O CH3 CH2CH3 CH CH3 H H H O O CH3 CH2CH2CH3 CH CH3 H H H O O CH3 CH2CH2Br CH CH3 H H H O O CH3 OCH2CH3 CH CH3 H H H O O CH3 O(CH2)2CH3 CH CH3 H H H O O CH3 OCH2CH=CH2 CH CH3 H H H O O CH3 OCH2C=CH2 CH CH3 CH3 H H H O O CH3 OCH2C#CH CH CH3 H H H O O CH3 OCH2C#OCH3 CH CH3 H H H O O CH3 OCH2CH2OCH3 CH CH3 H H H H O O CH3 OCH2CH20CH3 N CH3 H H H O O CH3 OCH2(CH2)2Cl CH CH3 H H H O O CH3 OCH2(CH2)3Cl CH CH3 H H H O O H CH3 CC1 CH3 H H H O O Cl CH3 CCH2CH2Cl CH3 H H H O O OCH3 OCH3 CH3 CH3 H H. H O O OCH3 OCH3 CH2CH3 CH3 H H H O O OCH3 OCH3 CCH2CH=CH2 Table I (continued) EMI24.1 <tb> RI <SEP> R2- <SEP> R3 <SEP> R4 <SEP> Q <SEP> W <SEP> y <SEP> X <SEP> Z <SEP> m.p.( C) <tb> ¯ <SEP> <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <SEP> ¯ <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <SEP> 179-181 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 204-205 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 180-186 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 184-187 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> H <SEP> CH3 <SEP> CC1 <SEP> 210-211 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <SEP> 171-174 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> CH3 <SEP> CH <SEP> 181-188 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 180-183 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 159-161 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 178-181 <tb> CH3 <SEP> 5 < 3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> N <tb> CH3 <SEP> 5 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 133-136 <tb> CH3 <SEP> 5 < 2CH3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> CH <tb> H <SEP> H <SEP> iI <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <SEP> 221-223 <tb> -co > <SEP> H <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 182-186 <tb> 43 <SEP> H <SEP> H <SEP> O <SEP> 0' <SEP> O <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 184-186 <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 169-172 <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> <SEP> CH3 <SEP> CH3 <SEP> N <tb> H <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> H <SEP> CH3 <SEP> CC1 <SEP> 193-195 <tb> H <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 143-145 <tb> CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> Table I (continued) EMI25.1 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> Q <SEP> h' <SEP> Y <SEP> X <SEP> Z <SEP> m.p.(OC) <tb> <SEP> L <tb> rCH2-CH-CHCH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> CH <tb> <SEP> C1 <SEP> C1 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OC <SEP> CH3 <SEP> CH <SEP> 135-140 <SEP> (dec) <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH <SEP> CH3 <SEP> CA <SEP> 190-193 <SEP> (dec) <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OC <SEP> OCH3 <SEP> N <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> <SEP> OC?i <SEP> CH3 <SEP> N <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <SEP> N <SEP> 200 <SEP> (dec) <tb> CF3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> 0 <SEP> OCH3 <SEP> O-H3 <SEP> N <SEP> 144-148 <SEP> (dec) <tb> CF3 <SEP> r: <SEP> H <SEP> H <SEP> N; <SEP> O <SEP> H3 <SEP> OCH3 <SEP> CH <tb> <SEP> CH3 <tb> CF3 <SEP> H <SEP> H <SEP> N; <SEP> O <SEP> OCH3 <SEP> C3 <SEP> CH <tb> <SEP> CH <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> N <SEP> O <SEP> CH3 <SEP> CH3 <SEP> CA <tb> <SEP> Gi <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> N <SEP> O <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> N <SEP> O <SEP> CC" <SEP> CH3 <SEP> N <tb> <SEP> CH <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> Ii <SEP> - <SEP> H <SEP> N <SEP> O <SEP> G3 <SEP> CH <SEP> N <tb> <SEP> 3 <SEP> 3 <tb> <SEP> cH3 <tb> CF3 <SEP> H <SEP> H <SEP> Cr': :3 <SEP> N <SEP> O <SEP> OCH3 <SEP> CC;I3 <SEP> D; <tb> <SEP> 3 <tb> Table II EMI26.1 EMI26.2 <tb> RI <SEP> R2 <SEP> 3 <SEP> R4 <SEP> Q <SEP> W <SEP> 1 <SEP> Yl <SEP> n <SEP> m.c.( C) <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> H <SEP> 1 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> CH3 <SEP> 1 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> H <SEP> 2 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> O <SEP> CH3 <SEP> 2 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> O <SEP> CH3 <SEP> 2 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> -N- <SEP> O <SEP> O <SEP> 3 <SEP> 2 <tb> <SEP> CH3 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> CH3 <SEP> 1 <tb> CH3 <SEP> S-Cl <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 01 <SEP> OCH3 <SEP> 1 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH2 <SEP> CH3 <SEP> 1 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> CH2 <SEP> OCH3 <SEP> 1 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> CH3 <SEP> 2 <tb> <SEP> 3 <tb> CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 2 <tb> <SEP> (CH2)3OH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 0 <SEP> OCH3 <SEP> 3 <tb> (CH2) <SEP> 2CH2C1 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> cl <tb> 4 <SEP> H <SEP> H <SEP> H <SEP> 0 <SEP> O <SEP> O <SEP> OCH <SEP> 1 <tb> 02N <tb> <SEP> ¯ <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> O <SEP> CCH3 <SEP> 1 <tb> Table II (continued) EMI27.1 <tb> <SEP> R1 <SEP> R2 <SEP> R3 <SEP> Q <SEP> Q <SEP> W <SEP> X1 <SEP> Y1 <SEP> n <SEP> m,p. <SEP> (OC) <tb> <SEP> (CH2)2CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> <SEP> CH2CH2C1 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 0 <SEP> eXH3 <SEP> 1 <tb> <SEP> CH2CH2C1 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> CH3 <SEP> 1 <tb> <SEP> CH2CH2C1 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 2 <tb> <SEP> CH3 <SEP> 5-F <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 0 <SEP> OCC3 <SEP> 1 <tb> <SEP> S-Cl <SEP> 4-C1 <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> <SEP> CH3 <SEP> 6-CK, <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> OCH3 <SEP> 1 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H- <SEP> -N- <SEP> O <SEP> 0 <SEP> OCC3 <SEP> 2 <tb> <SEP> CH3 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> -N- <SEP> O <SEP> O <SEP> CH <SEP> 1 <tb> <SEP> 3 <tb> <SEP> CH3 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> O <SEP> OCH3 <SEP> 1 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> o <SEP> CH3 <SEP> 1 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> 0 <SEP> 0 <SEP> CH3 <SEP> 1 <tb> <SEP> 3 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> CH2 <SEP> CH3 <SEP> 1 <tb> <SEP> CF3 <SEP> H. <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> CH3 <SEP> 1 <tb> <SEP> CH2CH2CCH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> 0 <SEP> cm <SEP> 3 <SEP> 1 <tb> CH <SEP> 3 <SEP> H <SEP> H <SEP> OCH3 <SEP> O <SEP> 0 <SEP> o <SEP> CH3 <SEP> 1 <tb> <SEP> CH3 <SEP> H. <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH2 <SEP> OCH3 <SEP> 2 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> 0 <SEP> 00 <SEP> C1 <SEP> 1 <tb> <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> O <SEP> Cl <SEP> 2 <tb> Table III EMI28.1 EMI28.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> g <SEP> W <SEP> X2 <SEP> Y2 <SEP> m.P. <SEP> ( C) <tb> <SEP> 4 <SEP> L <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH <SEP> OCH <tb> <SEP> 3 <SEP> 3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> 0 <SEP> OCH3 <SEP> CH3 <tb> CH3 <SEP> * <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH3 <SEP> OCH3 <tb> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> 0 <SEP> OCH3 <SEP> OCH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> 0 <SEP> CH3 <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> N <SEP> O <SEP> OCH <SEP> OCH <tb> <SEP> CH3 <tb> <SEP> CH <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <tb> CH2CH2OCH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH <tb> <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH <SEP> 3 <SEP> OCH <tb> CH3 <SEP> 5-Cl <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CC <SEP> 3\ <tb> CH3 <SEP> 5CH3 <SEP> H <SEP> H <SEP> 0 <SEP> 0 <SEP> OCH3 <SEP> <tb> CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> 0 <SEP> O <SEP> OCH3 <SEP> w <tb> Table IV EMI29.1 EMI29.2 <tb> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> g <SEP> w <SEP> X2 <SEP> Y2 <tb> 4 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> ¯ <SEP> ¯ <SEP> ¯¯ <SEP> 2 <SEP> m.D. <SEP> (0C) <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> 0CH3 <SEP> OCH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> o <SEP> O <SEP> SOCH3 <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> S <SEP> OCH <SEP> 3 <SEP> OCH3 <tb> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> O <SEP> O <SEP> CH3 <SEP> CH3 <tb> CH3 <SEP> H <SEP> H <SEP> H <SEP> N <SEP> O <SEP> OCH3 <SEP> OCH3 <tb> <SEP> CH3 <tb> <SEP> 3 <tb> CF3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> C <SEP> 3 <SEP> OCH3 <tb> CH2CH2OCH3 <SEP> H <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> CH3 <tb> H <SEP> H <SEP> - <SEP> - <SEP> - <SEP> H <SEP> - <SEP> 0 <SEP> <SEP> OCH3 <SEP> OCH3 <tb> -CH3 <SEP> 5-C1 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <tb> CH3 <SEP> 5-CH3 <SEP> H <SEP> H <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <tb> CH3 <SEP> H <SEP> H <SEP> OCH3 <SEP> O <SEP> O <SEP> OCH3 <SEP> OCH3 <tb> As indicated above, the compounds of general formula I according to the invention exhibit herbicidal properties. Thus, in another aspect, the invention provides a composition suitable for controlling the growth of undesired vegetation which comprises at least one compound of formula I according to the invention in association with at least one of the following: surfactant, solid diluent and liquid diluent. 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 998 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 proportins: Table V 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 0 C. -"McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood,-New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in q 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 & 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 5 Wettable Powder N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- hydroxybenzenesulfonamide, methanesulfonate 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 and then reblended. Example 6 Wettable Powder 2-hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)amino carbonyl]benzenesulfonamide, methanesulfonate 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 7 Granule Wettable Powder of Example 6 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 8 Extruded Pellet 2-hydroxy-N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)- aminocarbonyllbenzenesulfonamide, methane sulfonate 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 9 Oil Suspension N-( (4,6-dimethylpyrimidin-2-yl)aminocarbonyl)-2- hydroxybenzenesulfonamide, methanesulfonate 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 10 Wettable Powder N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2 hydroxybenzenesulfonamide, methanesulfonate 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 11 Low Strength Granule N-[ (A)6-dimethoxy-l,3,5-triazin-2-yl) (methyl) amino- carbonyl] -2-hydroxybenzenesulfonamide methanesulfonate 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example 12 Aqueous Suspension N-1(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2- hydroxybenzenesulfonamide, methanesulfonate 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5 disodium phosphate 1% monosodium. phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. Example 13 Solution N-[ (4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2- hydroxybenzenesulfonamide, methanesulfonate, 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 14 Low Strength Granule 2-hydroxy-N-{(4-methoxy-6-methylpyrimidin-2-yl)amino- carbonyl]benzenesulfonamide, methanesulfonate 0.18 attapulgite granules 99.9% (U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged. Example 15 Granule N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonylJ-2- hydroxybenzenesulfonamide, methanesulfonate 80% wetting agent 18 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 16 High Strength Concentrate N-[ (4,6-dimethoxy-l,3,S-triazin-2-yl)aminocarbonyli -2- hydroxybenzenesulfonamide, methanesulfonate 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 17 Wettable Powder 2-hydroxy-N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)- aminocarbonyl] benzenesulfonamide, methanesulfonate 90% - dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. Example 18 Wettable Powder N-(4,6-dimethyl-1,3,5-triazin-2-yl)amin hydroxybenzenesulfonamide; methanesulfonate 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 19 Oil Suspension 2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]benzenesulfonamide, l-propanesulfonate 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 20 Dust N-[ (4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2- hydroxybenzenesulfonamide, l-propanesulfonate 108 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 active herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate, time and method of application, compounds of this invention may also be used to modify plant growth beneficially, and also to selectively control weeds in crops such as wheat, barley, rice, corn and soybeans. The precise amount of the compounds of Formula I to be used in any given situation will vary according to the par-ticular end result desired, the amount of foliage present, the weeds to be controlled, the crop species -involved, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for alL situations. Broadly speaking, the compounds of this invention are used at levels of about 0.001 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where-extended persistence in soil is desired. The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with the ureas: such as 3-(3,4-dichlorophenyl)l,l-dimethylurea (diuron) ; the triazines: such as 2 chloro-4- (ethylamino) -6- (isopropylamino) -5-triazine (atrazine); the uracils: such as 5-bromo-3-sec-butyl6-methyluracil (bromacil); N-(phosponomethyl)glycine (glyphosate); 3-cyclohexyl-l-methyl-6-dimethylamino s-triazine-2,4(1H,3H)-dione (hexazinone) ; -N1N-dimethyl 2,2-diphenylacetamide (diphenamid); 2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate (barban) ; S--(2,3-dichloroallyl)-di-isopropylthiocar- bamate (diallate); S-(2,3,3-trichloroallyl)-diisopropylthiocarbamate (triallate); 1,2-dimethyl-3,5diphenyl-lH-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy) phenoxyGpropanoate (diclofop methyl); 4-amino-6tert-butyl-3-(methylthio)-1,2,4-triazin-5-(4H)-one (metribuzin); 3-(3,4-dichlorophenyl)-1-methoxy-1- methylurea (linuron); 3-isopropyl-lH-2,1,3-benzo- thiodiazin-4(3H)-one-2,2-dioxide (bentazon); #,#,#- trifluoro-2,6-dinitro-N,N-dipropyl-2-toluidine (trifluralin); l,l'-dimethyl-4,4'-bipyridinium ion (paraquat) ; monosodium methanearsonate (MSMA); 2-chloro-2',6'-diethyl (methoxymethyl)acetanilide (alachlor);p 1,1-dimethyl-3-(#,#,#-trifluoro-m-tolyl)- urea (fluometuron); and 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, methyl ester (acifluorfen-methyl). The activity of the compounds of formula I was investigated in a number of greenhouse tests. The tests are described and data resulting from them are shown below. Test A Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua) , cassia (Cassia tora) , morningglory (Ipomoea sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated preemergence with the chemicals dissolved in a non-phytotoxic solvent solution of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones) , bush beans with the third trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledona-ry leaves, rice with three leaves, wheat with one leaf, and nutsedge with threefive leaves were sprayed with a non-phytotoxic 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 non-phytotoxic solvent so as to provide a solvent control. -A set of untreated control plants was also included for comparison. Pre-emergence and post-emergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plant were compared with their respective controls and rated visually for response to treatment. The following rating system was used: 0 = no effect 10 = maximum effect C = chlorosis or necrosis D = defoliation E = emergence inhibition G = growth retardation H = formative effects U = unusual pigmentation 6Y = abscised buds or flowers P = terminal bud kill B = burn Compound 1 EMI43.1 Compound 2 EMI43.2 Compound 3 EMI43.3 Compound 4 EMI43.4 Compound 5 EMI44.1 Compound 6 EMI44.2 Compound 7 EMI44.3 Compound 8 EMI44.4 Compound 9 EMI45.1 Compound 10 EMI45.2 Compound 11 EMI45.3 Compound 12 EMI45.4 Compound 13 EMI46.1 Compound 14 EMI46.2 Compound 15 EMI46.3 Compound 16 EMI46.4 Compound 17 EMI47.1 Compound 18 EMI47.2 Compound 19 EMI47.3 Compound 20 EMI47.4 Compound 21 EMI48.1 Compound 22 EMI48.2 EMI48.3 EMI48.4 EMI49.1 EMI50.1 Compound 30 EMI50.2 Compound 31 EMI50.3 Compound 32 EMI50.4 Compound 33 EMI51.1 Compound 34 EMI51.2 Compound 35 EMI51.3 Compound 36 EMI51.4 Compound 37 EMI52.1 Compound 38 EMI52.2 Compound 39 EMI52.3 Compound 40 EMI52.4 Compound 41 EMI53.1 Compound 42 EMI53.2 Compound 43 EMI53.3 Compound 44 EMI53.4 Table A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate kg/ha 0.1 0.1 0.1 0.1 POST-EMERGENCE Bush bean 9C 9C 9C 9C Cotton 10C 9C 10C 9C Morningglory 10C 10C 10C 10C Cocklebur 10C 10C 9C 10C Cassia 9C 9C 9C 9C Nutsedge 9C 9C 9C 1C,5G Crabgrass 9C 9C 9C 4C,9G Barnyardgrass 10C 10C 10C 4C,9H Wild Oats 2C,9G 4C,9G 5C,9G 0 Wheat 1C,2G 5C,9G 5C,9G 0 Corn 5C,9G 9C 9C 4U,9G Soybean 9C 9C 9C 9C Rice 9C 9C 9C 9C Sorghum 9C 10C 9C 2C,9H PRE-EMERGENCE Morningglory 9G 9G 9C 9C Cocklebur 9H 9H 9H 9H Cassia 9C 5C,9G 6C,9G 6C,9G Nutsedge 10E 10E 10E 1C,7G Crabgrass 9C 6C,9G 2C,8G 2C,5G Barnyardgrass 5C,9H 9C 3C,9H 7C,9H Wild Oats lU,9G 5C,9H 4C,9H 8G Wheat 5G 5C,9H lC,9H 3G Corn 2U,9G 10E 10E 3C,9H Soybean 9H 9H 9H 9H Rice 10E 10E 10E 10E Sorghum 7C,9H 6C,9H 10H lC,9G Table A (continued) Cmpd. 5 Cmpd. 6 Cmpd. 7 Rate kg/ha 0.1 0.1 0.1 POST-EMERGENCE Bush bean 9C 9C 1C,2G Cotton 9C 9C 9C Morningglory 10C 10C 9C Cocklebur 9C 9C 9C Cassia 9C 6C,9G 5C,9G Nutsedge 5G 1C,5G 2C,5G Crabgrass 2C,9G 9C 3G Barnyardgrass 5C,9H 9C 0 Wild Oats 1C,4G 3C,9G 0 Wheat 0 1C 0 Corn 6C,9G 6C,9H 3C,9H Soybean 9C 9C 9C Rice 9C 9C 6G Sorghum 2C,9H 6C,9G 1C,3G PRE-EMERGENCE Morningglory 9C 9C 1C,3G Cocklebur 9H. 9H 8H Cassia 6C,9G 6C,9G 2C,2H Nutsedge 1C,6G 6G 0 Crabgrass 2C,6G 1C,6G 0 Barnyardgrass 2C,9H 7C,9H 0 Wild Oats 1C,7G 3C,9G 0 Wheat 0 8G 0 Corn 9H 9H 3G Soybean 9H 9H 1C,2H Rice 10E 10E 1C Sorghum SC,9H 7C,9H 0 Table A (continued) Cmpd. 8 Cmpd. 9 Cmpd. 10 Cmpd. 11 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 10G,9C 9G,3H,6C 7G,3H,7C 2C,2H Cotton 10G,9C 10G,8C 10G,8C 3C,2H,6G Sorghum 10G,4C 10C 10G,9C 0 Corn 7G,SH 10G,8C 10G,3H 0 Soybean 10G,7C 10G,8C 7G,7C 2H,6G Wheat 0 3C,2C 3G,2C 0 Wild Oats 0 9G,3C 10G,6C 0 Rice 8G,3C 10C 10C 1C Barnyardgrass 10G,6C 10C 10G,9C 2H Crabgrass 0 8G,3C 0 0 Morningglory 10G,9C 7G,9C 10G,5C 9C Cocklebur 10G,9C 10C 10G,7C 3C,9G Cassia 10C 10G,8C 10G,8C 0 Nutsedge 10G,7C 10G,6C 10G,7C 0 PRE-EMERGENCE Sorghum 8G,5G 95,9C 9G,9C 0 Corn 6G 9G 9G,9C 0 Soybean 8G,5H 9G,5H 8G,5C 0 Wheat 0 7G 7G 0 Wild Oats 5G,3H 8G,3C 7G,5H 0 Rice 8G,6C 8G,8C 10E 3G Barnyardgrass 8G,5H 9G,6C 8G,5H 0 Crabgrass 3G 5G,3H 3G 0 Morningglory 8G,5C 8G,9C 8G,9C 7G Cocklebur 8G,3H 9G,9P 9G,9P 5H Cassia 9G,5C 9G,9C 8C,9G 0 Nutsedge 10E 10E 10E 0 Table A (continued) Cmpd. 12 Cmpd. 13 Cmpd. 14 Rate kg/ha 0.05 0.05 0.05 POST-EMERGENCE Bush bean 1C,2H 6C,9G,6Y 6C,9G,6Y Cotton 1C 3C,3H,9G 3C,3H,9G Sorghum 6H 0 0 Corn 0 0 0 Soybean 1H 2H,6G 2H,5G Wheat 0 0 0 Wild Oats 0 0 0 Rice 0 0 0 Barnyardgrass 0 0 0 Crabgrass 0 0 0 Morningglory 1C,5G 4C,9H 3C,9H Cocklebur 1C 4C,9H 2C,8G Cassia 0 3C 1C Nutsedge 0 0 PRE-EMERGENCE Sorghum 0 0 0 Corn 0 0 0 Soybean 0 0 0 Wheat 0 0 0 Wild Oats 0 0 0 Rice 0 0 Barnyardgrass 0 0 0 Crabgrass 0 0 0 Morningglory 0 3C,9G 4C,9G Cocklebur 0 8H,3C 7H,3C Cassia 0 2C 0 Nutsedge 0 0 0 Table A (continued) Cmpd. 17 Cmpd. 18 Cmpd. 19 Rate kg/ha 0.05 0.05 0.05 POST-EMERGENCE Bush bean 7C,5G,6Y 9C,7G 6C,7G,6Y Cotton 7C,6G 8C,7G 9C,6G Sorghum 3C,4G 2C,4G 2C,4G Corn 4C,3U,4G 5C,6G 0 Soybean 6C,7G 10C 7C,6G Wheat 0 0 2C,2G Wild Oats 2C 3C,4G 3G Rice 2C,3G 3C,4G 3C,SG Barnyardgrass 10C 7C,6G 2C,3G Crabgrass 2C,3G 0 0 Morningglory 10C 5C,4G 10C Cocklebur 10C 8C,7G 10C Cassia 8C,7G 3C,4G 3C,4G Nutsedge 10C 6C,4G SC,4G PRE-EMERGENCE Sorghum 3C,6G 5C,8G 7C,7G Corn 3C,6G 7C,6G 0 Soybean 7C,8G 7C,8G 7C,6G Wheat 0 3C,5G 0 Wild Oats 2C 7C,6G 2C,6G Rice ' 10E 8C,8G 8C,7G Barnyardgrass 7C,8G 7C,7G 7C,SG Crabgrass 2C,2G 3G,2C 0 Morningglory 7C,7G 10C 7C,6G Cocklebur 8C,7G 3C,5G 5C,6G Cassia 8C,8G 7C,6G 5C,4G Nutsedge 10E 10E 10E Table A (continued) Cmpd. 20 Cmpd. 21 Cmpd. 30 Rate kg/ha 0.05 0.05 0.05 POST-EMERGENCE Bush bean 2G 9C,6G,6Y 3C,9G,6Y Cotton SC,4G 9C,5G SG,9G Sorghum 4C,5G 6C,SG 10C Corn 10C 7C,6G 10C Soybean 4C,5G 5C,6G 2C,9G Wheat 0 2C,3G 9C Wild Oats 4C,5G 8C,7G 2C,8G Rice 3C,4G 2C,3G 10C Barnyardgrass 7C,6G 10C 10C Crabgrass 2C,2G 7C,6G 6C,9G Morningglory 10C 10C 9C Cocklebur 10C 10C 9C Cassia 2C 5C,3G 9C Nutsedge 0 3C,4G 9C PRE-EMERGENCE Sorghum 7C,8G 7C,8G lC,9H Corn 7C,8G 8C,8G lC,9G Soybean 6C,7G 7C,6G lC,9G Wheat 0 0 9G Wild Oats 2C,5G 5C,6G 8G Rice 10E 10E 10E Barnyardgrass 7C,7G 8C,8G 5C,9H Crabgrass 4C,5G 5C,7G 2C,8G Morningglory 10C 10C 9G Cocklebur 10C 10C 9H Cassia 5G,6C 7C,6G 2C,9G Nutsedge 0 7C,SG 10E Table A (continued) Cmpd. 31 Cmpd. 32 Cmpd. 33 Cmpd. 34 Rate kg/ha 0.05 0.05 0.05 0.05 POST-EMERGENCE Bush bean 9C 9D,9G,6Y 9D,9G,6Y 4C,6G,6Y Cotton 6C,9G 3H,6C,9G 6C,9G 3H,6C,9G Sorghum 2C,9G 9C 3C,9G lC,6H Corn 7U,9G 1C,9G 3U,9G 1C,5G Soybean 4C,9G 5C,9G 3C,9G 2C,9G Wheat 2C,7G 9C 1C,3G 0 Wild Oats 1C,8G 9C 1C,2G 0 Rice 3C,9G 9C 2C,9G 8G Barnyardgrass 9C 10C 10C 3C,7H Crabgrass 6G 2C,5G 1C,3G 1C,3G Morningglory 10C 10C 3C,9G 9C Cocklebur 10C 9C 6C,9G 6C,9G Cassia 9C 9C 3C,7G 3C,5G Nutsedge 1C,9G 4C,9G 2C,7G 1C,3G PRE-EMERGENCE Sorghum 4C,9G 3C,9H 2C,9G 2C,7G Corn 2C,9G 2C,9H 1C,9G 1C,8G Soybean 8H 3C,7H 9H 1C,9H Wheat 9G 3C 0 0 Wild Oats 2C,9H lC,9G 1C,5G 0 Rice 2C,9H 10E 9H 2C,SG Barnyardgrass 2C,9H 2C,9H 3C,8H 1C,5H Crabgrass 2C,9G lC,3G 1C,3G 0 Morningglory 9C 9G lC,9H 2C,9G Cocklebur 9H .9H 9H 9H Cassia 2C,9G 2C,9G 9G,3C 6C,9G Nutsedge 10E 10E 1C,9G 3G Table A (continued) Cmpd. 35 Cmpd. 36 Cmpd. 37 Cmpd. 38 Rate kg/ha 0.1 0.05 0.05 0.05 POST-EMERGENCE Bush bean 2G 5C,9G,6Y 9C 4C,9G,6Y Cotton 3C,3H,7G 9C 9C 5C,9G Sorghum 1C,3G 9C 3U 10C Corn 0 1C,2G 2C 2C,4G Soybean 2C,9G 2C,8G 2C 1H,6G Wheat 0 0 0 0 Wild Oats 0 2G 1C 5G Rice 0 4C,9G 2C 7G Barnyardgrass 0 3C,9H 10C 3C,7H Crabgrass 0 2C,4G 3C 2C,SG Morningglory 6C,9G 9C 9C 2C,9G Cocklebur 4C,9G 10C 10C 9C Cassia 2C 5C,9G 5G Nutsedge 1C,2G 9G 1C 8G PRE-EMERGENCE Sorghum 0 2C,9H 2C,9H 2C,9H Corn 0 2C,SG 2C,8H 2C,7H Soybean 0 lC,4H 2C,5G 2G Wheat 0 0 3G 0 Wild Oats 0 1C,6G 1C,8G 1C,6G Rice 0 3C,9H 2C,8H 2C,6G Barnyardgrass 0 2C,8H 2C,9H 3C,SG Crabgrass 0 1C 1C,3G 1C Morningglory 0 9G 9G 1C,6G Cocklebur 0 9H 9H 9H Cassia 0 2C,8G 2C,8H 1C Nutsedge O 9G 9G 5G Table A (continued) Cmpd. 39 Cmpd. 40 Rate kg/ha 0.05 0.4 POST-EMERGENCE Bush bean 9C 0 Cotton 9C 1C Sorghum 1C 4G Corn 1C 0 Soybean 1H 0 Wheat O 0 Wild Oats 2G 0 Rice 0 2G Barnyardgrass 2G 0 Crabgrass 1C 5G Morningglory 9C 3G Cocklebur 10C 3G Cassia 0 Nutsedge 2G 3G PRE-EMERGENCE Sorghum 1C,7G 0 Corn 1C,3G 0 Soybean 1C 1H Wheat O 0 Wild Oats 0 0 Rice 2C 0 Barnyardgrass 1C,4H 0 Crabgrass 1C 2G Morningglory .9G 3G Cocklebur 9H 5H Cassia 2C,9H 0 Nutsedge 2G 0 Table A (continued) Cmpd. 26 Cmpd. 27 Rate kg/ha 0.05 0.05 POST-EMERGENCE Bush bean 3C,9G,6Y 1C,2G,6Y Cotton 2C 1C Sorghum 0 3G Corn 2C,3G 1C Soybean 2H 2H Wheat 0 0 Wild Oats 0 0 Rice 0 4G .Barnyardgrass 0 , 0 Crabgrass 0 1C Morningglory 2C,6H 1C Cocklebur 2C,6G 3C,6H Cassia Nutsedge 0 1C PRE-EMERGENCE Sorghum 0 0 Corn 0 0 Soybean. 0 0 Wheat Q O Wild Oats 0 0 Rice 0 0 Barnyardgrass 0 0 Crabgrass 0 0 Morningglory 0 0 Cocklebur 0 9H Cassia 0 0 Nutsedge 0 0 Table A (continued) Cmpd. 41 Cmpd. 42 Rate kg/ha 0.4 0.4 POST-EMERGENCE Bush bean 9C 9C Cotton 10C 4C,3H,9G Sorghum 6U,9G 2C,9G Corn 2U,9H 5U,9G Soybean 9C 9C Wheat 2G 0 Wild Oats 1C,8G 0 Rice 6C,9G 6C,9G Barnyardgrass 5C,9H 1C,6G Crabgrass 2C,6G 4G Morningglory 6C,9G 6C,9G Cocklebur 10C 9C Cassia 9C 4C,7H Nutsedge 2C,8G 2C,5G PRE-EMERGENCE Sorghum 5C,9H 5C,9G Corn 2U,9G 2C,9G Soybean 9H 4C,8H Wheat BG 2C,8G Wild Oats 4C,8G 2C,8G Rice 10E 10E Barnyardgrass 4C,9H 4C,9G Crabgrass 5G 1C,4G Morningglory 9C 9C Cocklebur 9H 9H Cassia 4C,9G 3C,7G Nutsedge lC,9G 8G Table A (continued) Compound 43 Compound 44 Rate kg/ha 2 6 2 6 POST-EMERGENCE Bush bean 0 3C 0 0 Cotton 0 3C 0 2C Sorghum 0 0 0 2C Corn 0 0 0 0 Soybean <RTI ID=65.4> 0 1C 0 3G Wheat 0 0 0 0 Wild Oats 0 -0 0 0 Rice O 0 0 0 Barnyardgrass 0 1C 0 0 Crabgrass 0 0 0 0 Morningglory 0 0 0 1C,3G Cocklebur 0 0 0 0 Cassia 0 1C 0 0 Nutsedge 0 0 0 0 PRE-EMERGENCE Sorghum 0 1C,5G 0 2C Corn 0 2C,5G 0 1C,2G Soybean 0 0 0 0 Wheat 0 0 - 0 0 Wild Oats 0 lC,4G 0 0 Rice 0 1C 0 1C Barnyardgrass 0 5C,8H 0 5C Crabgrass 0 2G 0 0 Morningglory 0 3C 0 2C Cocklebur 0 2C,8H 0 5H Cassia 0 3G 0 5G Nutsedge 0 0 0 0 Test B Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua) , johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention. Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Table B PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound 1 Compound 2 Rate kg/ha 0.03 0.12 0.03 0.12 Crabgrass 7G,2H 8G,3H 7G,3H 8G,3H Barnyardgrass 8G,3H 9G,9C 9G,8C 10C Sorghum 9G,9C 10C 10C 10E Wild Oats 6G 10C 8G,5C 9G,9C Johnsongrass 8G,7C 10C 9G,9C 10C Dallisgrass 7G 9G,9C 8G,3H 8G,3H Giant foxtail 6G,3C 8G,5C 5G,3C 10C Ky. bluegrass 8G,9C 10C 85,9C 10C Cheatgrass 8G,9C 9G,9C 10E 10E Sugarbeets 10C 10C 10C 10C Corn SG,3U 8G,SH 7G,5H 10C Mustard 10C 10C 10C 10C Cocklebur 6G 5G 10C Pigweed 10C 10E 7G 10E Nutsedge 10E 10E 6G 10E Cotton 8G 9G,5C 6G,3H 9G,8C Morningglory 5G 9G,9C 7G 9G.8C Cassia 8G,8C 10C 7G,4C 9G,9C Teaweed 6G 9G,8C 6G,3H 8G,6C Velvetleaf 9G,8C 10C 8G,8C 9G,9C Jimsonweed 7G,3C 9G,8C 9G,9C 9G,9C Soybean 8G,5H 9G,8C 7G,5H 9G,8C Rice 8G,3H 10E 8G,7C 10E Wheat 0 3G 5G 8G,9C Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound 3 Rate kg/ha 0.007 0.015 0.03 0.12 Cr abgrass 0 0 SG 6G Barnyardgrass 2G 2G 8G,3H 9G,9C Sorghum 2G 4G 10C 10E Wild Oats 0 0 10C 10C Johnsongrass 0 3G 10C 10C Dallisgrass 0 3G 6G 8G,3H Giant foxtail 0 3G 3C 7G,3C Ky. bluegrass 0 2G 10C 8G,8C Cheatgrass 0 - 10E 10E Sugarbeets - 4G 10C 10C Corn 0 0 10C 10C Mustard 5G 7G,3C 10C 10C Cocklebur 0 0 7G 8G,5H Pigweed 0 10E 9G,9C 10C Nutsedge 0 0 10E 10E Cotton 0 0 8G,3C 9G,7C Morningglory 3G 3G 8G 9G,7C Cassia 0 0 9G,8C 9G,8C Teaweed - 0 4G 10C Velvetleaf 0 0 8G,5E 9G,8C Jimsonweed 0 0 8G,8C 9G,9C Soybean 0 0 8G,5H 9G,8C Rice 3G 6G,3H 10E 10E Wheat 0 0 5G 7G,3C Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM Compound 36 Compound 39 Rate kg/ha 0.06 0.25 0.06 0.25 Crabgrass 2G 4G 2G 2G Barnyardgrass 4G 6G,5H 4G 5G Sorghum 6G 8G,5H 4G 4G,2H Wild Oats 4G 4G 3G 3G Johnsongrass 4G,3H 6G,3H 4G 3G Dallisgrass 4G 5G 3G 0 Giant foxtail 4G 6G,3H 0 2G Ky. bluegrass 6G 7G 2G 4G Cheatgrass 6G 7G 0 3G Sugarbeets 6G,6C 8G,9C 9G,8C 10C Corn 3G 4G 2G 4G Mustard 10E 10E 8G,8C 8G,9C Cocklebur - 8G,7C 8G,5H 10C Pigweed 5G,5C 9G,9C 4G 6G,4C Nutsedge 7G 10E 4G 6G Cotton 4G 8G,3H 8G,3H 9G,5C Morningglory 4G 8G,9C 9G 9G,3C Cassia 6G 8G,8C 5G,3C 7G,8C Teaweed 5G,3C 6G,3C 6G,2C 6G,3C Velvetleaf 5G,3H 8G,8C 7G,3H 8G,9C .Jimsonweed 3G 5G,5C 7G,3C 8G,5C Soybean 2G 5G,3H 3G 4G Rice 3G 5G 0 0 Wheat 0 0 0 0 Test C The high herbicidal activity of two of the compounds from within the scope of the invention is evident from the results obtained in this test. The experiment concerned pre-emergence applications on soil. The containers used were 25 cm diameter plastic pots filled with Fallsington silt loam. One set of pots was planted to weeds, the seeds of which were uniformly mixed with the top 1.2 cm layer of soil. The species selected were: johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), velvetleaf (Abutilon theophrasti), jimsonweed (Datura stramonium), mustard (Brassica arvensis), and pigweed (Amaranthus retroflexus). Another set of pots was panted to the following crops with from one to four species per pot: corn (planting depth 3.7 cm), cotton, soybeans, sunflower, Clinton oats, wheat, Black Valentine beans, rice, sorghum, peas, flax, and peanuts (all at 2.5 cm depth), cucumbers, cabbage, alfalfa, safflower, sugarbeets, tomato, spinach, barley, and Kentucky bluegrass (all at 1.2 cm depth). Immediately after planting, the test chemical was applied to the soil surfaces dissolved in a nonphytotoxic solvent. One pot from the weed phase and one of each of the crop species were left untreated for the purpose of comparison. The treated and untreated pots were promptly watered with approximately 4 mm of simulated rainfall and then held in a greenhouse for several weeks. Visual weed and crop response ratings were made 28 days after treatment utilizing the rating system as described above for Test A. The data are given in Table C. Table C PRE-EMERGENCE ON FALLSINGTON SILT LOAM SOIL Compound 1 Rate kg/ha 0.0035 0.0075 0.0150 0.03 Corn 5G,3C Cotton 7G,3H Soybean 4G,2H Peanut 6G Sunflower 5G Oats 4G Wheat 2G Sorghum 7G,5H Sugarbeet 9G,9C Pea 10E Flax 6G Alfalfa 8G,6C Bean O Spinach 8G,SH Cabbage 8G,6C Tomato 4G Rice 6G Safflower 7G,4C Cucumber 5G Ky. bluegrass 7G Barley 3G Broadleaves 3G 4G 6G,2H Grasses 0 0 2G Table C (continued) PRE-EMERGENCE ON FALLSINGTON SILT LOAM SOIL Compound 2 Rate kg/ha 0.0075 0.015 0.030 0.06 Corn 9G,9C Cotton 10E Soybean 9G,5H Peanut 8G,3H Sunflower 9G,5H Oats 6G,2C Wheat SG Sorghum 10E Sugarbeet 10E Pea 10E Flax 10E Alfalfa 8G,6C Bean 8G, 5H Spinach 9G,9C Cabbage 8G,7C Tomato 5C,8G Rice 10E Safflower 8G,7C Cucumber 9G,5H Ky. bluegrass 6G,5H Barley 8G,7C Broadleaves 5G,3C 7G,5C 9G,8C Grasses 6G,3C 8G,4C 9G,6C Test D Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropvron repens), Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus). The other pan was planted with seeds of Russian thistle (Salsola kale), tansy mustard (Descuraina pinnata),'smartweed (Polygonum pensylvanicum), tumble mustard (Sisymbrium altissium) kochia (Kochia scoparia), shepherd's purse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum nigrum), yellow rocket (Barbarea vulgaris), wild mustard (Brassica kaber) and wild buckwheat (Polyqonum convolvulus). The above two pans were treated pre-emergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species. The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. The recorded. data, presented in Table D, indicate that certain compounds from within the scope of the invention have utility for pre- and/or post-emergence weed control in cereal crops such as wheat and barley. Table D Compound 1 Rate kg/ha 0.002 0.008 0.008 0.015 Pre-Emergence wheat 0 0 0 0 barley 0 0 0 1C,6G wild oats 0 0 0 3C,7G downy brome 3G 2C,5G 1G 5C,7G cheatgrass 5G 4C,7G 3G 10C blackgrass 3G 5C,6G 2G 10C annual bluegrass 5G 2C,6G 1C,2G 7C,8G green foxtail 0 2G 3C,4G 3C,5G quackgrass 3G 3C,5G 0 8G Italian ryegrass 0 3C,5G 0 4G ripgut brome 2G 2C,4G 0 2C,5G Russian thistle 0 0 1G 8C,7G tansy mustard 6G 8C,8G 8C,8G 10C smartweed - - - tumble mustard 3C,8G 10C 7C,7G 10C kochia 1G 5G 3G 9C,8G shepherd's purse 3C,5G 8C,8G 9C,8G 10C Matricaria inodora black nightshade 2C,4G 4C,6G 6C,7G 8G yellow rocket 2C,7G 4C,8G 7C,7G 10C wild mustard 5C,6G 8C,8G 7C,7G 10C wild buckwheat 3G 2C,4G 1C,2G 3C,6G Table D (continued) Compound 1 Rate kg/ha 0.002 0.008 0.008 0.015 Post-Emergence wheat 0 0 0 0 barley 0 0 0 1C,5G wild oats 0 1C 0 3C,2G downy brome 3G 5C,7G 4C,SG 3G cheatgrass 4C,7G 8C,7G 8C,7G 10C blackgrass 6G 4C,5G 7C,7G 10C annual bulegrass 3G 3C,6G 3C,5G 5C,4G green foxtail 4G 7C,7G 7C,7G 3C,4G quackgrass 3G 6G 2C,3G 6C,5G Italian ryegrass 2G 2G 0 3G ripgut brome 2G 5G 0 2G Russian thistle 2C,3G 10C 9C,7G 10C tansy mustard 10C 10C 10C 10C smartweed - - - tumble mustard 4C,6G 10C 10C 10C kochia 3GC 4G 10C 8C,7G shepherd's purse 10C 10C 10C 10C Matricaria inodora 7C,7G 10C 9C,7G 10C black nightshade 4G 4C,6G lC,lG Q Yellow rocket 3G 10C 10C 10C Wild mustard 10C 10C 10C 10C wild buckwheat 2C,4G 5C,5G 6C,5G 10C Table D (continued) Compound 1 Pre-Emergence Post-Emergence Rate kg/ha 0.03 0.06 0.03 0.06 wheat 0 2C,3G 0 1C,2G barley lC,lG 6C,8G 2C,2G 7C,6G wild oats 0 8C,8G 2G 3C,3G downy brome 2C,7G 10C 7C,7G 3C,4G cheatgrass 5C,8G 10C 10C 10C blackgrass 3C,7G 10C 10C 10C annual bluegrass 5C,7G 10C 6C,7G 10C green foxtail 7C,7G 9C,8G 7C,8G 7C,6G quackgrass 2C,3G 10C 3C,6G 7C,6G Italian ryegrass 1C,3G 4C,7G 2C,4G 4C,5G ripgut brome 0 5C,7G 2C,3G 3C,5G Russian thistle 2C,3G 8C,8G 10C 10C tansy mustard 10C 10C 10C 10C smartweed - - - tumble mustard 10C 10C 10C 10C kochia 7C,8G 10C 10C 10C shepherd's purse 10C 10C 10C 10C Matricaria inodora 7C,8G 10C 9C,8G 10C black nightshade 7C,7G 3C,8G 3C,7G 4C,5G yellow rocket 8C,9G 10C 10C 10C wild mustard 8C,8G 10C 10C 10C wild buckwheat 3C,4G 4C,8G 7C,6G 10C Table D (continued) Compound 2 Rate kg/ha 0.002 0.008 0.008 0.015 Pre-Emergence wheat 0 0 0 2C,2G barley 0 3G 3C,4G 5C,7G wild oats 0 2C,5G 2G 8C,8G downy brome 6G 7C,7G 3C,7G 10C cheatgrass 5C,7G 10C 5C,8G 10C blackgrass 3C,6G 7C,7G 3C,7G 10C annual bluegrass 1C,6G 7C,7G 2C,5G 10C green foxtail 0 4C,5G 2C,4G 6C,7G quackgrass 4G 3C,6G 4G 8C,9G Italian ryegrass 3G 5C,7G 5C,7G 9C,9G ripgut brome 5G 6G 3C,4G 9C,9G Russian thistle 0 1C,1G 3C,4G 9C,9G tansy mustard 3C,8G 8C,9G 7C,8G 10C smartweed tumble mustard 7C,8G 10C 10C 10C kochia 2G 5G 7C,8G 8C,9G shepherd's purse 8C,8G 8C,8G 10C 10C Matricaria inodora 5C,8G 7C,8G 7C,7G 10C black nightshade 3C,4G 3C,4G 5C,6G 2C,7G yellow rocket 8G 2C,9G 7C,7G 10C wild mustard 7C,8G 8C,8G 7C,8G 10C wild buckwheat 2C,1G 3C,4G 3C,2G 3C,4G Table D (continued) Compound 2 Rate kg/ha 0.002 0.008 0.008 0.015 Post-Emergence wheat 0 1G 1G 5C,5G barley 0 3G 2C,3G 7C,6G wild oats 0 2C,5G 5G 7C,7G downy brome 3C,5G 7C,7G 7C,7G 7C,7G cheatgrass 6C,7G 10C 10C 10C blackgrass 2C,6G 7C,7G 7C,7G 10C annual bluegrass 5C,6G 10C 6C,5G 10C green foxtail 3C,5G 4C,5G 7C,8G 6C,6G quackgrass lC,6G 4C,6G 6G 7C,6G Italian ryegrass 1C,5G 3C,6G 3C,6G 10C ripgut brome 4G 1C,7G 3G 4C,6G Russian thistle 5C,4G 8C,7G 10C 10C tanzy mustard 10C 10C 10C 10C smartweed - - - tumble mustard 7C,8G 8C,8G 10C 10C kochia 5G 10C 10C 7C,6G shyepherd's purse 10C 10C 10C 10C Matricaria inodora 10C 10C 7C,7G 10C black nightshade 2G 3C,5G lC,lG .0 yellow rocket 10C 10C 8C,8G 10C wild mustard 10C 10C 10C 10C wild buckwheat 2C,2G 3C,5G 6C,6G 10C Table D (continued) Compound 2 Pre-Emergence Post-Emergence Rate kg/ha 0.03 0.06 0.03 0.06 wheat 2C,4G 4C,6G lC,2G 7C,7G barley 6C,7G 8C,8G 4C,6G 10C wild oats 7C,6G 9C,8G 5C,6G 8C,7G downy brome 7C,8G 10C 8C,7G 10C cheatgrass 10C 10C 10C 10C blackgrass 8C,7G 10C 10C 10C annual bluegrass 5C,6G 10C 10C 10C green foxtail 4C,6G 9C,9G 8C,8G 7C,7G quackgrass 7C,7G 9C,9G 4C,6G 10C Italian ryegrass 7C,8G 10C 5C,7G 10C ripgut brome 6C,7G 9C,9G 4C,4G 9C,8G Russian thistle 5C,6G 10C 10C 10C tansy mustard 9C,9G 10C 10C 10C smartweed - - - tumble mustard 10C 10C 10C 10C kochia 9C,8G 9C,9G 10C 10C -shepherd's purse 10C 10C 10C 10C Matricaria inodora 7C,8G 10C 8C,7G 10C black nightshade 7C,6G 5C,8G 3C,4G 2G yellow rocket 10C 10C 10C 10C wild mustard 9C,8G 10C 10C 10C wild buckwheat 4C,SG 5C,6G 7C,8G 10C Table D (continued) Compound 3 Pre-Emergence Post-Emergence Rate kg/ha 0.008 0.03 0.008 0.03 wheat 0 1C,2G 0 1C,2G barley 2G 7C,6G 0 4C,6G wild oats 1G 7C,7G 0 7C,5G downy brome 4G 10C 6C,7G 7C,7G cheatgrass 2C,5G 10C 7C,7G 10C blackgrass 7C,7G 10C 4C,5G 10C annual bluegrass 3C,4G 5C,6G 4C,6G 5C,7G green foxtail 2C,3G 5C,4G 2C,4G 6C,7G quackgrass 0 3C,4G 2C,3G 4C,6G Italian ryegrass 3G 7C,7G 3C,6G 5C,6G ripgut brome 0 10C lC,2G 3C,4G Russian thistle 0 7C,7G 3C,2G 10C tansy mustard 4C,5G 9C,9G 8C,7G 10C smartweed - - - tumble mustard 7G 10C 10C 10C kochia 6G 10C 4G 10C shepherd's purse 7C,7G 10C 9C,8G 10C Matricaria inodora 6C,7G 7C,7G 6C,5G 9C,8G black nightshade 3C,4G 5C,6G 4G 8C,8G yellow rocket 7G 7C,7G 2C,5G 10C wild mustard 5C,7G 7C,8G 10C 10C wild buckwheat 0 2C,3G 2C,2G 5C,6G Table D (continued) Compound 36 Pre-Emergence Post-Emergence Rate kg/ha 0.015 0.06 0.015 0.06 wheat 0 0 0 barley 0 0 0 0 wild oats 0 0 0 0 downy brome 3G 6G 0 3G cheatgrass 7G 10C 1G 3C,SG blackgrass 6G 3C,7G 2G 5C,4G annual bluegrass 6G 7C,7G 2G 3G green foxtail 2G 3C,5G 1G 2G quackgrass 0 2G 0 0 Italian ryegrass 1G 3G 0 0 ripgut brome 2G 2C,7G 0 2G Russian thistle 0 1G C. 2G tansy mustard 2G 2C,5G 5C,4G 7C,8G smartweed - - - tumble mustard 5G 3C,7G 10C 10C kochia 0 SC,6G 0 0 shepherd's purse 7G 3C,8G 7C,8G 10C Matricaria inodora 3C,8G 7C,8G 7C,7G 9C,8G black nightshade 4G 1C,5G 2G 4C,5G yellow rocket 3C,8G 10C 7C,7G 10C wild mustard 7C,8G 10C 10C 10C wild buckwheat 3G 1C,4G 1C,2G 5C,4G Test E Test samples were formulated and applied directly to the paddy water three days after transplantin of rice. The test was maintained in a greenhouse, and plant response ratings were taken at the stated intervals after application. The data indicate: Compound 1 barnyard- water Rate Rice Rice grass* Chestnut+* a/ha 4 Days 4 Weeks 4 Week- 4 Weeks 1 0 0 0 4 0 O C 8G 8 0 0 0 9G Compound 36 Barnyard- water Arrow Rate, Rice Rice grass Chestnut** head*** g/ha 1 Week 8 Weeks 8 Weeks 8 Weeks 8 Weeks 25 0 0 0 10* 0 100 0 0 0 10C - 0 *Echinochloa spp. **Eleocharis spp. ***Sagittaria spp. It may be seen that compounds from within the scope of the invention can be used for selective weed control in rice. Test F The test 'chemicals, dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. One day after treatment, plants were observed for rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data ark presented in Table F. All plant species were seeded in Woods tow sandy loam'soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea heder acea) ,- jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugarbeets, and mustard. All plants were sprayed approximately 14 days after planting. Some of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat. Compound 39 has utility for the post-emergence control of weeds in soybeans. Table F Over-the-Top Soil/Foliage Treatment Compound 1 Rate kg/ha 0.06 0.015 0.007 0.003 Soybeans - 10G,7C 10G,7C 9G,5C 9G,5C Velvetleaf 10G,7C 8G,3C 9G,9C 10G,9C Sesbania 9C 9C 10C 10C Cassia 10G,7C 8G,2C 9G,SC 10G,5C Cotton 10G,7C 7G,3C iOG,9C 10C Morningglory 10G,5C 9G,4C lOG,8C lOG,8C Alfalfa 9C 5C 6G,2C 6G,2C Jimsonweed 9C 7G,3C 0 0 Cocklebur 10G,7C 9G,3C 7G 5G Corn 10C 9G,7C 8G,2H 9G,1H Crabgrass 8G,4C 2C 5G 0 Rice 8G,3C 3G,1C 8G,5C 7G,2C Nutsedge 10C 10C 5G 3G Barnyardgrass- 10C 10C 9G,4C 9G,2C Wheat 0 0 0 1G Giant foxtail 10G,3C 7G,3C 5G 5G Wild Oats 6G 3G 3G 3G Sorghum 10C 9C 8G,3C 7G,4U mustard - - 10C 10C Sunflower - - 10C 10C Sugarbeets - - 10C 9G,9C Table F (continued) Over-the-Top Soil/Foliage Treatment Compound 2 Rate kg/ha 0.06 0.015 Soybeans 9C 10G,8C Velvetleaf 10G,4C 5G Sesbania 10C 9C Cassia 10G,7C 7G,3C Cotton 10G,6C 7G,3C Morningglory 10C 8G,2C Alfalfa 10C 7C Jimsonweed 10C Cocklebur 10G,8C lOG,7C Corn 10C 10G,7U Crabgrass 10C 6G,1C Rice 10C 6G,3C Nutsedge 10C 2C Barnyardgrass 10C 6G,3C Wheat 9C 1C Giant foxtail 10C Wild Oats 10C 5C,3C Sorghum 10C 8G,5C Mustard Sunflower - Sugarbeets Table F (continued) Over-the-Top Soil/Foliage Treatment Compound 3 Rate kg/ha 0.06 0.015 0.007 0.003 Soybeans 10G,6C 10G,4C 9G,7C 10G,SC Velvetleaf 7G,2C 5G 8G,8C 7G Sesbania 9C 9C 8G,5C 9G,8C Cassia 10G,7C 5G,3C 10G,5C 8G,4C Cotton 10G,6C 10G,6C 10C 8G,2C Morningglory 9G,4C 9G,3C 10G,8C 7G,1H Alfalfa 9C 8C 7G 6G,2C Jimsonweed 9G,3C - - 0 Cocklebur 10G,7C 10G,7C 4G,5C 3G Corn 10C 9G,6C 9G 9G,1H Crabgrass 7G,4C 0 5G,1C 0 Rice 8G,5C 7G,3C 9G,7C 9G,7C Nutsedge 9G,4C 9G,3C 7G 5G Barnyardgrass 10C 9C . 9G,4C 9G,2C Wheat 8C 1C 6G 3G Giant foxtail - - 0 0 Wild Oats 10C 7G,3C 5G 4G Sorghum 10C 9C 7G,3U 9G,6U Mustard - - 10C 9G,9C Sunflower - - 10C 10G,9C Sugarbeets - - 10C 9G,9C Table F (continued) Over-the-Top Soil/Foliage Treatment Compound 36 Rate kg/ha 0.12 0.06 0.015 Soybeans 10C 9G,9C 9G,7C Velvetleaf 10C 10C 8G,7C Sesbania 10C 10C 10C Cassia 10C 9G,3C 8G,3C Cotton 9G,9C 8G,8C 4G,4C Morningglory <RTI ID=87.4> 10C 10C 8G,4C Alfalfa 9G 5G,3C 7G Jimsonweed C 0 0 Cocklebur 10C 10C 10C Corn 2G,1C lG,2C lG,lC Crabgrass 5G 0 0 Rice 5G 4G 2G Nutsedge 7G,5C 7G,5C 0 Barnyardgrass 9G,5C 8G,5C 6G,2C Wheat 2G 0 0 Giant foxtail 3G,2C 2C 0 Wild Oats 3G 0 0 Sorghum 7G,3C 5G,2C 2G,2C Mustard 10C 10C 10C Sunflower 10C 10C 10C Sugarbeets 9G,3C 9G,5C 8G Table F (continued) Over-the-Top Soil/Foliage treatment Compound 39 Rate kg/ha 0.12 0.06 0.03 0.015 0.015 0.015 0.007 Soybeans 10G,7C 9G,9C 4G 0 0 3G 0 Velvetleaf 9G,7C 8G,5C lOG,5C 8G,4C 8G,3C 8G,3C 7G,3C Sesbania lOC 9G,4C 10G,7C 8G,6C 9G,4C 5G,4C 7G,4C Cassia 9G,7C 5G,5C 8G,5C 5G,5C 8G,4C 4G,6C SG,3C Cotton 9G,7C 9G,6C 9G,5C 8G,4C 8G,4C 8G,4C 6G,3C Morningglory 9G,8C 9G,5C 9G,4C 9G,5C 9G,4C lOG,3C 9G,6C Alfalfa 9G,8C 10C 9G,5C 5G,2C 9G,5C 7G 7G,3C Jimsonweed 0 - - - 8G 2C Cocklebur 10G,7C 10G,5C 10G,5C 9G,5C 10G,5C 10G,4C 9G,4C Corn C 0 3G,2C 0 lG,2C 0 2G Crabgrass C 0 0 0 0 0 O Rice C 0 4G 1G 3G 0 2G Nutsedge 1G 0 3G 0 0 0 5G Barnyardgrass C 0 3G 0 0 0 2G Wheat 0 0 0 0 0 0 0 Giant Foxtail 0 0 2G 0 2G 0 1G Wild Oats C 0 2G C 1G 2G 0 Sorghum C C SG C 4G 5G 3G Mustard 10C 10C 10G,5C 10G,5C 10G,5C 9G 10G,5C Sunflower 10C 10C 10G,8C 10G,8C 10G,8C 10C 10G,8C Sugarbeets 10G,5C 10C 9G,3C 10G,5C 9G,3C 9G 10G,4C Test G This test demonstrates the broadleaf herbicidal properties of compound 39. Approximately 12 soybean plants were grown in a 25 cm. diameter plastic pot. In another pot of equal size the following broadleaf plant species were grown: sugarbeets, velvetleaf, Sesbania, Cassia, mustard, morningglory, alfalfa, jimsonweed, and cocklebur. The plant foliage and surrounding soil were treated with the test chemical dissolved in a non-phytotoxic solvent as an overall spray at the rate of 0.015 kg/ha, when the plants were 17 days old. Visual ratings of herbicidal effects were made 22 days after treatment utilizing the rating system described for Test A. Table G Rate 0.015 Soybeans C Sugarbeets 9G Velvetleaf 9G,9C Sesbania 8G,8C Cassia 7G,4C Mustard 10C Morningglory 9G,9C Alfalfa 8G,4C Jimsonweed C Cocklebur 10P,2C The data indicate that the compound tested pro vides excellent post-emergence control of broadleaved ;weeds in soybeans.

Claims: CLAIMS: 1. A compound of the formula: EMI90.1 where W is O or S; Q is O or NR5; R1 is C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, CH2CH2OCH3, CH2CH2CH2OCH3 or EMI90.2 R2 is H, F, C1, Br, OCH3, NO2 or C1-C2 alkyl; R3 is H, F, C1, Br or CH3; R4 is H, CH3 or OCH3; R5 is C1-C4 alkyl; R6 and R7 are independently H, F, C1, Br, CH3, CF3, NO2 or OCH3; A is EMI91.1 X is NH2, N(CH3)2, NHCH3, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, C1 or Br, CH2OCH3, CH2OCH2CH3, C1-C4 alkoxy, C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH2OCH3 or C2-C4 alkoxy substituted with 1-3 atoms of F, Cl or Br; n is 1 or 2; Y is H, CH3, OCH3 or C1; X1 is O or CH2; Y1 is H, CH3, OCH3 or C1; ; X2 and Y2 are independently CH3 or OCH3; and Z is CH, N, CCH3, CBr, CC1, CF, CI, CC2H5, CCH@CH@Cl or CCH2CH=CH2; provided that (1) when Y is C1, then Z is other than N and X is NH2, NHCH3, N(CH3)2, CH3 or OCH3; (2) when Y is H, then X is OCH3, CH3 or CH2OCH3, and Z is other than N; and (3) when W is S, then R4 is H. 2. A compound of Claim 1 where R5 is CH3, W is 0, and R4 is H or CH3. 3. A compound of Claim 2 where R1 is C1-C4 alkyl, CF3, CH2CH2OCH3 or CH2CH2CH2OCH3. 4. A compound of Claim 3 where R2 is H. 5. A compound of Claim 4 where R3 is H. 6. A compound of Claim 5 where R1 is C1-C3 alkyl or CF3; Q is O; A is EMI92.1 and Z is CH or N. 7. A compound of Claim 6 where R4 is H. 8. A compound of Claim 7 where X and Y are independently CH3 or OCH3, and R1 is CH3. 9. The compound of: Claim 1 whicJl is iN-[(4,6- dimethoxy-pyrimidin-2-yl) aminocarbonyl] -2 -hydroxybenzene- sulfonamide, methanesulfonate. 10. The compound of Claim 1 which is 2-hydroxy N- [ (4-methoxy-6-methylpyrimidin-2-yl) aminocarbony] benzene-sulfonamide, methanesulfonate. 11. The compound of Claim 1 which is N-[(4,6dimethyl-pyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate. 12. The compound of claim 1 which is N-[(4,6 dimethOxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxy- benzenesulfonamide, methanesulfonate. 13. The compound of Claim 1 which is 2-hydroxy N-[(4-methOxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- benzenesulfonamide, methanesulfonate. 14. The compound of claim 1 which is N-[(4,6dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate. 15. The compound of Claim 1 which is N-[(4,6 dimethOxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2- hydroxy-benzenesulfonamide, methanesulfonate. 16. The compound of Claim 1 which is N-[(4,6dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, l-propanesulfonate. 17. The compound of Claim 1 which is 2-hydroxy N-f(4-methOxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- benzenesulfonamide, l-propanesulfonate. 18. A process for the preparation of compounds of general formula I as defined in claim 1 which comprises reacting a compound of formula EMI93.1 (wherein Q,W,R1,R2 and R3 are as defined in claim 1) with a compound of formula EMI93.2 (wherein A and R4 are as defined above). 19. A composition suitable for controlling the growth of undesired vegetation which comprises at least one compound of formula I as defined in claim 1 in association with at least one of the following: surfactant, solid diluent and liquid diluent. 20. A composition according to claim 19 wherein the compound of formula I is a compound as defined in any one of claims 2 to 17. 21. A method for controlling the growth of undesired vegetation in a locus which comprises applying to the locus an effective amount of at least one compound of formula I as defined in claim 1. 22. A method according to claim 21 wherein the compound of formula I is a compound as defined in any one of claims 2 to 17. 23. A compound of formula EMI94.1 (where W,Q,R1,R2 and R3 are as defined in claim 1). 24. A compound of claim 23 where Q is O, R2 and R3 are H, R1 is CH3 or CF3, and W is O. 25. A compound of claim 23 where Q is NCH3, R2 and R3 are H, R1 is CH3 or CF3, and W is O. 26. A compound of formula EMI95.1 where Q is O or NR5; R1 is C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH2CH2OCH3; CH2CH2CH2OCH3, or EMI95.2 R2 is H, F, C1, Br, OCH3, NO2 or C1-C2 alkyl; R3 is H, F, C1, Br or OCH3; R5 is C1-C4 alkyl; R6 and R7 are independently H, F, Cl, Br, CH3, CF3, NO2 or OCH3; and Z is CH or N. AUSTRIAN CLAIMS 1. A process for the preparation of a compound of formula: EMI96.1 where W is O or S; Q is O or NR5; R1 is C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH2CH2OCH3, CH2CH2CH2OCH3 or EMI96.2 R2 is H, F, C1, Br, OCH3, NO2 or C1-C2 alkyl; R3 is H, F, C1, Br or CH3; R4 is H, CH3 or OCH R5 is C1-C4 alkyl; R6 and R7 are independently H, F, C1, Br, CH3, CF3, NO2 or OCH3; A is EMI97.1 X is NH2, N(CH3)2, NHCH3, C1-C4 alkyl, C1-C4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH2OCH3, CH2OCH2CH3, C1-C4 alkoxy,. C1-C2 alkylthio, C3-C4 alkenyloxy, C3-C4 alkynyloxy, OCH2CH2OCH3 or C2-C4 alkoxy substituted with 1-3 atoms of F, Cl or Br; n is 1 or 2; Y is H, CH3, OCH3 or C1; X1 is O or CH2; Y1 is H, CH3, OCH3 or Cl; X2 and Y2 are independently CH3 or OCH3; and Z is CH, N, CCH3, CBr, CC1, CF, CI, CC2H5, CCH2CH2C1 or CCH2CH=CH2; ,provided that (1) when Y is Cl, then Z is other than N and X is NH2, NHCH3, N(CH3)2, CH3 or OCH3; (2) when Y is H, then X is OCH3, CH3 or CH2OCH3, and Z is other than N; and (3) when W is S, then R4 is H which comprises reacting a compound of formula EMI98.1 (wherein Q,W,R1,R2 and R3 are as defined above) with a compound of formula EMI98.2 (wherein A and R4 are as defined above). 2. A process according to claim 1 wherein A in the compound of formula EMI98.3 is EMI98.4 (wherein X,Y and Z are as defined in claim 3. A process according to claim 1 wherein A in the compound of formula EMI98.5 (wherein X11Y1 and n are as defined in claim 1). 4. A process according to claim 1 wherein A in the compound of formula EMI98.6 (wherein X2 and Y2 are as defined in clairi. 1). 5. A process according to claim 1 wherein A in the compound of formula EMI99.1 (wherein X2 and Y2 are as defined in claim 1) 6. A process according to any one of claims 1 to 5 for the preparation of a compound of formula I in which R5 is CH3, W is 0 and R4 is H or CH. 7. A process according to claim 6 for the preparation of a compound of formula I in which R1 is C1-C4 alkyl, CF3, CH2CH2OCH3 or CH2CH2CH2OCH3. 8. A process according to claim 7 for the preparation of a compound of formula I in which R2 is H. 9. A process according to claim 8 for the preparation of a compound of formula I in which R3 is H. 10. A process according to claim 9 for the preparation of a compound of formula I in which R1 is C1-C3 alkyl or CF3, Q is 0, and A is EMI99.2 (in which X and Y are as defined in claim 1, and Z is CH or N). 11. A process according to claim 10 for the preparat-ion of a compound of formula I in which R4 is H. 12. A process according to claim 11 for the preparation of a compound of formula I in which X and Y are independently CH3 or OCH3, and R1 is CH3. 13. A process according to claim 1 for the preparation of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 2-hydroxybenzenesulfonamide, methanesulfonate. 14. A process according to claim 1 for the preparation of 2-hydroxy-N- [ (4-methoxy-6-methylpyrimidin-2-yl) - aminocarbonyl]benzenesulfonamide, methanesulfonate. 15. A process according to claim 1 for the preparation of N-[ (4,6-dimethylpyrimidin-2-yl)aminocarbonyl]- 2-hydroxybenzenesulfonamide, methanesulfonate. 16. A process according to claim 1 for the preparation of N- [(4 ,6-dimethoxy-l '3, 5-trjazin-2-yl) amino- carbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate. 17. A process according to claim 1 for the preparation of 2-hydroxy-N-[(4-methoxy-6-methyl1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamide, methanesulfonate. 18. A process according to claim 1 for the preparation of N-[ (4,6-dimethyl-l,3,5-triazin-2- yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate. 19. A process according to claim 1 for the preparation of N-[(4,6-dimethoxy-1,3,5-triazin2-yl) (methyl) aminocarbonyl] -2-hydroxybenzenesulfonamide, methanesulfonate. 20. A process according to claim 1 for the preparation of N-F(4,5-dimethoxypyrimidin-2-yl)- aminocarbonyl]-2-hydroxybenzenesulfonamide, 1-propanesulfonate. 21. A process according to claim 1 for the preparation of 2-hydroxy-N- [(4 -methoxy-6-methyl- 1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamide, 1-propanesulfonate. 22. A composition suitable for controlling the growth of undesired vegetation which comprises at least one compound of formula I as defined in Claim 1 in association with at least one of the following: surfactant, solid diluent and liquid diluent. 23. A composition according to claim 22 wherein the compound of formula I is a compound as defined in any one of claims 6 to 21. 24. A method for controlling the growth of undesired vegetation in a locus which comprises applying to the locus an effective amount of at least one compound of formula I as defined in Claim 1. 25. A method according to claim 24 wherein the compound of formula I is-a compound as defined in any one of claims 6 to 21.

Inventors: REAP, JAMES JOHN
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1981
Main classification: C07D239
IPC codes: A01N47, C07D521, C07D491, C07D251