HERBICIDAL SULFONAMIDES

Abstract: Compounds of the general formula wherein J is selected from certain carbocyclic and heterocyclic aryl groups, or is a 2-alkoxycarbonylbenzyl group; R is H or CH₃; A is a substituted 2-pyridyl or 4-pyrimidyl group; and their agriculturally suitable salts, exhibit potent herb­ icidal activity. Some also have plant growth regulant activity. The compounds may be formulated into herbicidal com­ positions in conventional manner. They may be prepared by reacting an appropriate arlysulfonyl isocyanate with an appropriately substituted 2-aminopyridine or 4- amino­ pyrimidine.

Description: Title HERBICIDAL SULFONAMIDES Background of the Invention This invention relates to novel N-[(pyridyl or pyrimidyl)aminocarbonyl)arylsulfonamides. to herbicidal compositions containing them and to methods of using them to control the growth of undesired vegetation. New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton. rice. corn. wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations. herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe. A number of different types of N-[(heterocyclic)- aminocarbonyl]arylsulfonamides are known as herbicides. Two of the first patents to issue on such compounds are U.S. Patents 4.169,719 and 4,127,405, issued on October 2, 1979 and November 28. 1978, respectively. These patents disclose compounds of the general formula EMI1.1 where R1 can be optionally substituted benzene, thiophene, pyrrole. furan or unsubstituted naphthalene. and Y is N or CH. Subsequent patents which have issued have disclosed related compounds with different N-heterocycles. For example, U.S. 4,293.330. issued on October 6, 1981. discloses pyridyl sulfonylureas. and U.S. 4.221.585. issued on September 9. 1980, disclose 4-pyrimidyl sulfonylureas. Nowhere in the art has there been any indication that N-(pyridyl or pyrimidyl)sulfonylurea derivatives, in which the pyridyl or pyrimidyl moiety is substituted ortho- to the sulfonylurea bridge with an electron-withdrawing group. would exhibit high herbicidal activity. Summary of the Invention This invention therefore relates to the novel compounds of Formula I. to herbicidal compositions containing them and to methods of using the novel compounds to control the growth of undesired vegetation. EMI2.1 wherein J is EMI2.2 EMI3.1 R1 is NO2, F, C1, Br, CF3, C1-C3 alkyl. C1-C2 alkyl substituted with OCH3 or OC2H5, C02R9. SO2N(CH3)R10. S(O)nR11l SCF2H, OR12, OSO2R11, CH2CH2Cl. EMI3.2 R2 is H, F, C1, Br, CH3, OCH3 or CF3; R3 is C1, S02CH3 or So2N(CH3)2; R4 is H or CH3; R5 is H or C1-C3 alkyl; R6 is C1-C3 alkyl, CO2R11, S(O)nR11. Cl or Br: R7 is OSO2R11, S(O)nR11, C1-C3 alkyl, C1-C3 alkoxy or C1; R8 is C1-C3 alkyl; R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2Cl or CH2CH2OCH3: R10 is C1-C3 alkyl or OCH3; R11 is C1-C3 alkyl: R12 is C1-C3 alkyl. CF2H, CR2CH2OCH3. C3-C4 alkenyl or C3-C4 alkynyl; R13 is H or CH3: m is O or 1; n is O, 1 or 2; Q is 0, S or SO2: R is H or CH3; A is EMI4.1 W is as CN, CO2CH3, CO2C2H5, NO2, S(O)R11, SO2R11 or CONR14R15; R14 and R15 are independently H or CH3; X is CH3, OCH3, OC2H5, CH2OCH3 or Cl; Y is CH3, OCH3, OC2H5 or C1; and Z is CH or N; provided that (a) X and Y cannot simultaneously be C1; (b) when either X or Y is Cl, then Z is CH and (c) when X and Y are both CH3 and Z is CH, then W is other than NO2; and their agriculturally suitable salts. Certain groups of compounds of this invention are preferred for reasons of their high herbicidal and/or plant growth regulant activity. and/or their favorable ease of synthesis. These groups, in order of increasing preference. are: 1) Compounds of Formula I where J is J-1, R is H and R2 is H. 2) Compounds of (1) above where X and Y are independently CH3 or OCH3 and W is CN, NO2 or CO2CH3 3) Compounds of (2) above where R1 is N02, CO2CH3, CO2C2H5, SO2N(CH3)2, SO2CH3 or OSO2CH3. 4) Compounds of (3) above where Z is CH. The following compounds are specifically preferred because of their high herbicidal and/or plant growth regulant activity and/or their favorable ease of synthesis: . Methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2 yl)aminocarbonyl]aminosulfonyl]benzoate, m.p. 158-162 C; . N'-[(3-cyano-4,6-dimethylpyridin-2-yl)amino carbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide, m.p. 163-165 C: . Methyl 2-[[N-(2,6-dimethoxy-5-nitropyrimidin-2 yl)aminocarbonyl]aminosulfonyl]benzoate, m.p. 150-152 C(d); and . Methyl 2-[[(2-dimethylaminosulfonylphenyl)sul fonylamino]carbonylamino]-4,6-dimethylpyridin 3-carboxylate, m.p. 198-2015C. Detailed DescriPtion of the Invention Synthesis The compounds of Formula I can be prepared by reacting an appropriate aminoheterocycle of Formula II with an appropriately substituted sulfonyl isocyanate of Formula III. as shown in in Equation 1. Equation 1 EMI5.1 wherein A, J and R are as previously defined. The reaction of Equation 1 is best carried out in inert organic solvents such as methylene chloride, tetrahydrofuran. or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical: however, it is often convenient to add the sulfonyl isocyanate to a stirred suspension or solution of the aminoheterocycle. Since such isocyanates usually are liquids, their additions can be easily controlled. The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as l-chlorobutane or ethyl ether. and filtration. The sulfonyl isocyanates III used as starting materials are generally known in the art and can be prepared by known methods. One method involves reacting an appropriate benzene or heterocyclic sulfonamide with phosgene in the presence of an alkyl isocyanate. such as n-butyl isocyanate, and a tertiary amine catalyst, such as l,4-diazabicyclo(2.2.2joctane. at reflux in a solvent such as xylene or chlorobenzene. See H. Ulrich and A. A. Y. Sayigh, Newer Methods of PreParative Organic Chemistrv.Vol. VI, p. 223-241. Academic Press. New York and London, W. Foerst Ed. The sulfonyl isocyanates III can also be prepared from sulfonamides by a two step procedure involving (a) reacting the sulfonamides with an alkyl isocyanate in the presence of a base such as K2C03 at reflux in an inert solvent such as 2-butanone. forming an alkylsulfonylurea. and (b) reacting this compound with phosgene and tertiary amine catalyst at reflux in xylene solvent. The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature, e.g. Crossley et al.. J. Am. Chem. Soc.. 60. 2223 (1938). Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene. naphthalene, or thiophene in carbon tetrachloride according to the teaching of H. T. Clarke et al., Org. Synth., Coll. Vol. 1. 2nd Ed. 1941. p. 85. Other sulfonyl chlorides can be made by diazotization of the appropriate amine with sodium nitrite in HCl. followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teachings of H. L. Yale and F. Sowinski. J. Orq. Chem. 25. 1824 (1960). More specifically. the compounds of this invention may be prepared as described above by the route illustrated below. EMI7.1 Reference to the following patents is suggested for further details regarding the preparation of the sulfonyl isocyanates III: U.S. Patent 4,169.719, U.S. Patent 4,127,405 and U.S. Patent 4,238,621. Appropriately substituted aminoheterocycles of Formula II, where R = H and A is a substituted 2-pyridyl or 4-pyrimidyl moiety are generally known in the art and are reviewed in The Chemistry of Heterocyclic Compounds, "Pyridine and its Derivatives", Vol. 14, Suppl. Parts I and III (1974), and "The Pyrimidines" (1962) and Suppl. 1 (1970). (John Wiley and Sons, Inc.. New York). Commonly used starting materials for the synthesis of such substituted heterocycles are malononitrile. cyanoacetates, cyanoacetamides, ethoxy methylene malononitriles. ammonia, urea, 8-diketones, A-ketoesters. malonates. alkylamidines and alkylsulfonylacetonitriles. Some literature techniques are illustrated below. Using these techniques or suitable modifications that would be apparent to one skilled in the art, the 2-aminopyridine and 4-aminopyrimidine intermediates can be readily prepared. Condensation of ethoxyethylidenemalononitrile and acetamidine yields the corresponding 4-aminopyrimidine-5-carbonitrile as reported, Chem. Ber.. 71. 87 (1938). EMI8.1 The following sequence of reactions is reported tJ- Med. Chem., 24. 382 (1981)) to yield chloro and alkoxy substituted 4-aminopyrimidine-5-carbonitriles. EMI9.1 Treatment of methyl cyanoacetate with ethanolic hydrogen chloride affords the imidate which is condensed with acetylacetone as described [Chem, Ber.. 73. 542 (1940)] to give the 2-aminopyridine-3-carboxylate. EMI9.2 Heterocyclic amines II in which W is a nitro group are prepared by nitration of the corresponding unsubstituted amine as is reported for 2-amino-4,5dimethyl-3-nitropyridine. Rocz. Chem.. 37, 385 (1963), them. Abstr., 59, 11486 (1963)). EMI10.1 Those intermediates of Formula II in which R is a methyl group may be readily prepared from the corresponding aminoheterocycles (R=H) by known methods for the monomethylation of heterocyclic amines: J. Chem. Soc. Perkin I, 1569 (1981). Agriculturally suitable salts of the compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. Suitable salts include alkali or alkaline earth metal salts1 e.g. calcium, potassium or sodium salts; quaternary amine salts: and acid addition salts, e.g., g-toluenesulfonic acid or trichloroacetic acid addition salts. The following examples teach the preparation of compounds of this invention in more detail. Unless otherwise indicated. all parts are by weight and temperatures in "C. Example 1 N-t(3-Cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]- 2-nitrobenzenesulfonamide (I; J=J-1, R1=NO2, R2=H; Z=CH, W=CN, X=Y=CH3, R=H) To a stirred suspension of 0.5 g (3.4 mmol) 2 amino-4.6-dimethyl-3-pyridinecarbonitrile lArchiv. Pharm., 288. 174 (1955)] in 20 ml of acetonitrile was added 1.3 g (5.7 mmol) o-nitrobenzenesulfonyl isocyanate. The mixture was then heated to reflux (80 ) for four hours followed by stirring at ambient temperature overnight. A crystalline product was collected, 0.5 g. m.p. 174-176 dec. An infrared spectrum (nujol mull) exhibited absorptions at 1700, 1720 and 2240 cm 1; and a proton magnetic resonance spectrum (90 MHz NMR) exhibited absorptions at 2.5 (s, 3H), 2.6 (s. 3H), 7.05 (s, 1H), 7.7 (s br, NH). 7.8 (m, 3H), 8.4 (m, 1H), 9.7 (s br, NH) ppm indicating the title compound. Example 2 2-Chloro-N-[(4,6-dimethyl-3-methoxycarbonylpyridin2-yl)aminocarbonyl]benzenesulfonamide (I; J=J-1, R1=Cl. R =H; Z=CH. W=CO2CH3, X=Y=CH3, R=H) A mixture of 0.5 g (2.8 mmol) methyl 2-amino-4,6dimethylpyridine-3-carboxylate [preparation analogous to ethyl ester: Chem. Ber., 73, 542 (1940)] and 0.78 g (3.6 mmol) o-chlorobenzenesulfonyl isocyanate were combined in 40 ml acetonitrile and stirred at ambient temperature for forty-eight hours. The homogeneous mixture was then evaporated and triturated with nchlorobutane to afford 1.04 g of product, m.p. 1751770. IR (nujol) 1670. 1710 cm 1; and NMR (CDCl3) 2.58 (s, 3H), 2.60 (s, 3H), 3.95 (s, 3H). 6.85 (s, 1H), 7.55 (m. 3H), 8.40 (m, 1H), 10.2 (s br, NH). 14.2 (s br. NH) ppm indicated the title compound. ExamPle 3 2,6-Dimethoxy-5-nitro-4-pyrimidinamine (II: Z=N. W=NO2. X=Y=OCH3) To a solution of 20 ml of concentrated nitric acid and 16 ml of concentrated sulfuric acid was added 3.9 g (0.025 mmol) of 2,6-dimethoxy-4-pyrimidinamine. The resulting solution was stirred at ambient temperature and pressure for thirty minutes and was then stirred at 50 for fifteen minutes. The solution was then cooled in an ice bath to ¯0 C. The solid was collected by filtration, washed with water and dried in an oven at 600C to afford 3.6 g of the title compound. m.p. 178-179 C. NMR (DMSO-d6)6: 3.96 (d, 6H) and 8.2 (broad s, 2H) ppm. Example 4 2-[[(2,6-Dimethoxy-5-nitropyrimidin-4-yl)amino carbonyl)aminosulfonyl]benzoic acid, methyl ester (I; J=J-l, R1=CO2CH3, R2=H: Z=N, W=NO2, g=Y=OCH3. R=H) A solution of 0.2 g (1.0 mmol) of 2,6-dimethoxy5-nitro-4-pyrimidinamine and 0.6 g (2.4 mmol) of 2carbomethoxybenzenesulfonyl isocyanate in 15 ml of methylene chloride was stirred at ambient temperature and pressure for 12 hours under anhydrous conditions. The solvent was then evaporated under reduced pressure. The residue was stirred in n-butyl chloride (70 ml). The solid was then collected by filtration. washed with ether and then dried in an oven to afford 0.4 g of the title compound. m.p. 150-152 dec. NMR (DMSO-d6)6: 3.9-4.1 (m, 9H, OCH3); 7.7-8.5 (m, 4H. ArH); and 10-12 (br. 2H. NH) ppm. Example 5 2-Chloro-N-[(5-cyano-2,6-dimethylpyrimidin-4-yl)- aminocarbonyl]benzenesulfonamide (I; J=J-1, Rl=Cl, R2=H; Z=N, W=CN, X=Y=CH3, R=H) 4.35 g of 2-Chlorobenzenesulfonyl isocyanate was dissolved in 10 ml xylenes and 25 ml methylene chloride. To this was added 2.96 g of 4-amino-2.6-dimethyl5-pyrimidine carbonitrile and a catalytic amount of 1,4-diazabicyclo[2.2.2]octane, The reaction was stirred under a CaSO4 drying tube for three days. The reaction was filtered to remove unreacted pyrimidine. and then the desired product was precipitated by addition of l-chlorobutane, filtered off, rinsed well with l-chlorobutane and dried in vacuo giving 5.2 g of the desired product, m.p. 125-127 . IR: 2240 cm-1 (C=N), -1 1730 cm (C=O); NMR (DMSO-d6)6: 2.6 (s, SH), 7.4-8.1 (m, 4H) ppm indicating the title compound. By using techniques analogous to those described in Examples 1 through 5 and/or the processes described above. the compounds of Tables I through II may be prepared. Table I EMI14.1 R1 R2 R W X Y Z m.p.( C) NO2 H H CN CH3 CH3 CH 174-176(d) NO2 H H CN CH3 CH3 N 154(d) NO2 H H C02CH3 CH3 CH3 CH NO2 6-Cl H CO2CH3 OCH3 CH3 N F H H SO2CH3 CH3 CH3 CH F H H CO2CH(CH3)2 OCH3 CH3 CH P H H S(O)CH3 CH3 CH3 N Cl H H CN CH3 CH3 N 125-127 Cl H H CN SOCH3 CH3 N 187-190(d) Cl H H CN CH3 CH3 CH 175-178(d) Cl H H CO2CH3 CH3 CH3 CH 175-177(d) Cl H H H NO2 OCH3 OCH3 N 143-145(d) Cl 5-Cl H SO2CH3 CH3 CH3 N CF3 H H CN CH3 OCH3 CH CF3 H H CO2C2H5 CH3 CH3 N Br H H C02CH3 OCH3 CH3 CH CH3 H H C(O)NH2 CH3 CH3 N CH3 5-Cl H CN CH3 CH3 CH n-C H H H CN CH3 CH3 CH CH20CH3 H H CN CH3 CH3 N CH20CH3 H H S(O)CH3 CH3 CH3 N CH2CH2OCH3 H H CO2CH3 OCH3 CH3 CH SCF2H H H SO2CH3 CH3 CH3 N SCF2H H H N02 OCH3 CH3 CH SCF3H 5-CH3 H CN OCH3 CH3 N Cl H H CO2C2H5 CH3 CH3 CH 150-152 Table I (continued) R1 R2 R W X Y Z m.p. ( C) CO2CH3 H H C02C2H5 CH3 CH3 CH 150-153 SO2N(CH3)2 H H CO2C2H5 CH3 CH3 CH 165-167 OSO2CH3 H H CN CH3 CH3 N 138(d) OSO2CH3 H H CO2CH3 CH3 CH3 CH OSO2C3H7-n H H NO2 OCH3 OCH3 N OCF2H H H C 2CH3 OCH3 OCH3 N OCH3 H H CO2CH3 CH3 CH3 CH OC2H5 H H CN CH3 CH3 CH OC3H7-n H H CN OCH3 CH3 N OCH2CH2OCH3 H H S(O)CH3 CH3 CH3 CH C2H5 H H CO2CH3 Cl CH3 CH i-C3H7 H H CO2CH3 CH3 CH3 CH SCH3 H H CN CH3 CH3 CH SCH3 H CH3 NO2 OCH3 OCH3 CH SC2H5 H H CO2CH3 CH3 CH3 N SC3H7-n H H NO2 OCH3 CH3 CH SO2CH3 H H CN CH3 CH3 N 196-201 SO2CH3 H H CH CH3 CH3 CH 230-234(d) SO2CH3 H H CO2CH3 CH3 CH3 CH 187-189 SO2CH3 H H NO2 OCH3 OCH3 N 184-185(d) SO2CH3 H H S(O)CH3 CH3 CH3 CH SO2C3H7-n H H CO2CH3 CH3 CH3 CH SO2C2H5 H H NO2 CH3 OCH3 N SO2C3H7-n H H CN OCH3 OCH3 CH CO2CH3 H H CN CH3 CH3 N 167-168 CO2CH3 H H CN CH3 CH3 CH 158-162 CO2CH3 H H CN OCH3 CH3 N 170-172 CO2CH3 H H CO2CH3 CH3 CH3 CH 159-161 CO2CH3 H H NO2 OCH3 OCH3 N 150-152 CO2CH3 H H CN Cl CH3 CH CO2CH3 3-CH3 H S(O)CH3 CH3 CH3 CH CO2 2CH3 5-C1 H CN CH3 CH3 N Table I (continued) EMI16.1 <tb> R1 <SEP> R2 <SEP> R <SEP> W <tb> ¯ <SEP> 2 <SEP> R <SEP> W <SEP> x <SEP> y <SEP> z <SEP> m.(0C) <tb> Co2 <SEP> 3 <SEP> 3 <SEP> OCH <SEP> CH <SEP> N <tb> CH <SEP> 5-OCH3 <SEP> H <SEP> CN <SEP> OCH3 <SEP> CH3 <SEP> N <tb> C02CH3 <SEP> 5-F <SEP> H <SEP> 3 <SEP> CH3 <SEP> C1 <SEP> CH <tb> C02CH3 <SEP> 5-CF3 <SEP> H <SEP> S(O)C2H5 <SEP> CH3 <SEP> CH3 <SEP> Cii <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> CONHCH3 <SEP> OCH3 <SEP> CH3 <SEP> Cii <tb> Co2CH3 <SEP> H <SEP> H <SEP> CON(CH3)2 <SEP> CH3 <SEP> CH3 <SEP> N <tb> Co2CH3 <SEP> H <SEP> H <SEP> CON(CH3)2 <SEP> C1 <SEP> CH3 <SEP> CH <tb> CO2CH3 <SEP> H <SEP> CH3 <SEP> CO2CH3 <SEP> OC <SEP> H <SEP> CH3 <SEP> CH <tb> CO2CH3 <SEP> H <SEP> H <SEP> C 2CH3 <SEP> C1 <SEP> CH3 <SEP> Cii <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> CN <SEP> CH2OCH3 <SEP> CH3 <SEP> N <tb> CO2CH3 <SEP> 5-Br <SEP> H <SEP> CN <SEP> CH2OCH3 <SEP> OCH3 <SEP> CH <tb> Co2CH3 <SEP> H <SEP> H <SEP> NO2 <SEP> CH2OCH3 <SEP> CH3 <SEP> N <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> NO2 <SEP> C2B5 <SEP> 2 <SEP> N <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> SO2CH3 <SEP> C1 <SEP> OCH3 <SEP> CH <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> SO2C2H5 <SEP> OCH3 <SEP> C1 <SEP> CH <tb> C02C2H5 <SEP> H <SEP> CH3 <SEP> cN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> CO2C3H7-n <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 148-150 <tb> CO2C2H5 <SEP> H <SEP> H <SEP> S 2CH3 <SEP> CH3 <SEP> CH3 <SEP> N <tb> Co2CH2CH=CH2 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <SEP> 134-137 <tb> Co <SEP> 2CH2CH2 <SEP> Cl <SEP> H <SEP> H <SEP> NO2 <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> CO2Cii2 <SEP> CH2OCH3 <SEP> H <SEP> H <SEP> CO <SEP> 2CH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> <SEP> H <SEP> O <SEP> > <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> CH3 <tb> <SEP> 3 <tb> <SEP> 4 <SEP> ,O <SEP> H <SEP> H <SEP> CO <SEP> 2CH3 <SEP> CH3 <SEP> CH3 <SEP> Cii <tb> <SEP> CO, <SEP> H <SEP> H <SEP> S 2CH3 <SEP> CH3 <SEP> 3 <tb> Table I (continued) EMI17.1 <tb> R1 <SEP> R2 <SEP> R <SEP> W <SEP> X <SEP> Y <SEP> Z <SEP> m-P <SEP> (-C) <tb> gV\N=N5 <SEP> H <SEP> ii <SEP> NO2 <SEP> OCH3 <SEP> 0CH3 <SEP> N <tb> A: <SEP> H <SEP> H <SEP> N02 <SEP> OCH, <SEP> OCH3 <SEP> N <tb> <SEP> 2 <SEP> 3 <SEP> 5-C1 <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> Cii <SEP> 192-195(d) <tb> SO2N(CH3)2 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> N <SEP> 82 <tb> SO2N(CH3)2 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> Cii <SEP> 163-165 <tb> S02N(CH3)2 <SEP> H <SEP> H <SEP> CN <SEP> OCH3 <SEP> CH3 <SEP> N <SEP> 193-195 <tb> S02N(CH3)2 <SEP> H <SEP> ii <SEP> H <SEP> C 2CH3 <SEP> CH3 <SEP> CH3 <SEP> Cii <SEP> 198-201 <tb> SO2N( <SEP> 2 <SEP> 3 <SEP> 3 <SEP> 3 <tb> S02N(CH3)2 <SEP> H <SEP> H <SEP> NO2 <SEP> OCH3 <SEP> OCH3 <SEP> N <SEP> 130-131(d) <tb> <SEP> 32 <tb> S02N(CH3)2 <SEP> H <SEP> H <SEP> S(O)CH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> <SEP> 3 <tb> SO2N(CH3)2 <SEP> H <SEP> H <SEP> S02CH3 <SEP> CH3 <SEP> CH3 <SEP> N <tb> SO2N(Cii3)C2R5 <SEP> ii <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> N <tb> SO2N(CH3)2 <SEP> H <SEP> Cii3 <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> SO2NCH(CH3 <SEP> 2 <SEP> 5-C1 <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> <SEP> CH3 <tb> SO2N(CH3)OCH3 <SEP> H <SEP> H <SEP> C 2CH3 <SEP> CH3 <SEP> CH3 <SEP> Cii <tb> CH2OCH2CH3 <SEP> H <SEP> H <SEP> C02CH3 <SEP> CH3 <SEP> CH3 <SEP> Cii <tb> CH2OCH2CH3 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> CR(CH3)0CR3 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> N <tb> CH2CH20C2H5 <SEP> H <SEP> H <SEP> NO2 <SEP> OCH3 <SEP> OCH3 <SEP> N <tb> CH(CH3)OC2H5 <SEP> H <SEP> H <SEP> S(O)CR3 <SEP> CR3 <SEP> CR3 <SEP> CR <tb> OCH2CH=CH2 <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> OCH <SEP> C-CH <SEP> H <SEP> H <SEP> C 2CH3 <SEP> CH3 <SEP> CH3 <SEP> CH <tb> OCH2CH=CHCH3 <SEP> H <SEP> H <SEP> N02 <SEP> OCR3 <SEP> OCH3 <SEP> N <tb> OCH <SEP> C-C-CH <SEP> H <SEP> H <SEP> CN <SEP> CH3 <SEP> CH3 <SEP> CH <tb> C1 <SEP> H <SEP> H <SEP> S 2CH3 <SEP> OCR3 <SEP> OCH3 <SEP> N <SEP> 170-173(d) <tb> COUCH <SEP> H <SEP> H <SEP> S 2CH3 <SEP> OCii3 <SEP> 0CR3 <SEP> N <SEP> 180-182(d) <tb> SO,N(CH <SEP> )2 <SEP> H <SEP> H <SEP> SO <SEP> CR <SEP> ocii <SEP> OCH <SEP> N <SEP> 188-190(d) <tb> <SEP> 2 <SEP> 32 <SEP> 2 <SEP> 3 <SEP> 3 <SEP> 3 <tb> C1 <SEP> H <SEP> H <SEP> S(O)CH3 <SEP> OCii3 <SEP> OCR3 <SEP> N <SEP> 191-193(d) <tb> 2 <SEP> 3 <SEP> H <SEP> H <SEP> S(O)CH3 <SEP> 0CR <SEP> OCH3 <SEP> N <SEP> 185-188(d) <tb> <SEP> 3 <SEP> 3 <SEP> 3 <tb> SO2N(CH3)2 <SEP> H <SEP> H <SEP> S(O)CH3 <SEP> OCR3 <SEP> OCH3 <SEP> N <SEP> 193-196(d) <tb> Table II-a EMI18.1 wherein J2 is as defined above J R R3 w X Y Z m.p.( C) J-2 H Cl CN CH3 CH3 N J-2 H Cl CN CH CH CH 178-180(d) 3 3 J-2 H SO2CH3 CO2CH3 CH3 CH3 CH J-2 H SO2N(CH3)2 NO2 OCH3 OCH3 N J-2 H SO2CH3 SO2CH3 CH3 CH3 N J-2 H SO2N(CH3)2 CN OCH3 CH3 N Table II-b EMI18.2 wherein J3 is as defined above J R R4 R5 Q W X Y Z m.p.( C) J-3 H H H O CN CH3 CH3 CH J-3 H H CH3 O CO2CH3 CH3 CH3 N J-3 H CH3 CH3 O CN CH3 CH3 N J-3 H CH3 CH3 S CO2CH3 CH3 CH3 CH J-3 H H H S CN OCH3 CH3 N J-3 H H CH3 S CN OCH3 OCH3 CH J-3 H CH3 CH3 SO2 CO2CH3 CH3 CH3 CH J-3 H CH3 H SO2 CN CH3 CH3 N J-3 H CH3 H SO2 NO2 OCH3 OCH3 N J-3 H H C3H7 SO2 CN CH3 CH3 CH J-3 H CH3 H O CN CH3 CH3 CH 180-183 J-3 H CH3 CH3 O CN CH3 CH3 CH 185-187 Table II-c EMI19.1 wherein J4 is as defined above J R W X Y Z m.p.( C) J-4 H CN CH3 CH3 CH 168-170 J-4 H CO2CH3 CH3 CH3 N J-4 H NO2 OCH3 OCH3 CH J-4 H CN CH3 CH3 N J-4 H CO2CH3 CH3 CH3 CH Table II-d EMI19.2 wherein J5 and J6 are as defined above J R R6 W X Y Z m.p.( C) J-5 H CO CH CN CH CH CH 196-200(d) 23 3 3 J-5 H CO2CH3 CO2CH3 CH3 CH3 CH J-6 H Br CN CH3 CH3 N J-5 H Br SO2CH3 CH3 CH3 N J-5 H Cl CN OCH3 OCH3 N J-6 H SO2CH3 NO2 OCH3 OCH3 N J-5 H SCH3 CO2CH3 CH3 OCH3 N J-5 H SO2C3H7-n CN CH3 CH3 CH J-5 H CO2C3H7-i CN CH3 CH3 CH J-6 H CO2CH3 CN CH3 CH3 N J-6 H CO2CH3 CO2CH3 CH3 CH3 CH Table II-e EMI20.1 wherein J7 is as defined above J R R7 w X Y Z J-7 H CH3 CN CH3 CH3 CH J-7 H C2H7-n CN CH3 CH3 N J-7 H OCH3 CO2CH3 CH3 CH3 CH J-7 H OC3H7-i CO2CH3 CH3 CH3 N J-7 H SO2CH3 SO2CH3 CH3 CH3 N J-7 H SC H NO2 OCH3 OCH3 N J-7 H OSO2C3H7-n CN CH3 CH3 CH J-7 H Cl CN OCH3 CH3 CH J-7 H Cl CO2CH3 CH3 CH3 CH Table II-f EMI20.2 wherein J8 is as defined above J R m W X Y Z m.p.( C) J-8 H O CN CH3 CH3 CH J-8 H O CN CH3 CH3 N J-8 H O CO2CH3 CH3 CH3 N J-8 H O CN OCH3 CH3 N J-8 H O NO2 OCH3 OCH3 CH J-8 H l NO2 CH3 CH3 N Table II-f (continued) J R m W X Y Z m.p.( C) J-8 H 1 <RTI ID=21.2> S 2CH3 OCH3 CH3 CH J-8 H 1 CN CH3 CH3 CH 212-215(d) J-8 H l SO2CH3 CH3 CH3 N J-8 H l NO2 OCH3 OCH3 N J-8 H l NO2 Cl OCH3 CH J-8 H 1 CN CH3 CH3 N J-8 H l CO2CH3 CH3 CH3 CH Table II-q EMI21.1 wherein J9 is as defined above J R R8 W X Y Z m.p.( C) J-9 H CH3 CN CH3 CH3 CH J-9 H CH3 CN CH3 CH3 N J-9 H C2H5 CO2CH3 CH3 CH3 CH J-9 H CH3 CN OCH3 CH3 N J-9 H CH3 NO2 OCH3 OCH3 N J-9 H CH2CH2CH3 CH CH3 CH3 J-9 H CH3 CN CH3 OCH3 CH 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 III Weight Percents Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can. of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable. and are achieved by incorporation into the formulation or by tank mixing. Typical solid diluents are described in Watkins. et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured. may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed.. Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates: solution concentrates are preferably stable against phase separation at OOC. "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 Cho., 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 Hand book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 6 Wettable Powder Methyl 2-( ( (2-dimethylaminosulfonylphenyl)- sulfonylamino]carbonylj-4, 6-dimethylpyridin- 3-carboxylate 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 7 Wettable Powder N-[(3-cyano-4,6-dimethylpyridin-2-yl)- aminocarbonyl]-N,N-dimethyl-1,2-benzene- disulfonamide 508 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 8 Granule Wettable Powder of Example 7 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 9 Extruded Pellet Methyl 2- [ (N- (2, 6-dimethyl-5-nitropyrimidine- 4-yl)aminocarbonyl)aminosulfonyl]benzoate 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 10 Oil Suspension Methyl 2-[(N-(3-cyano-4,6-dimethylpyridin-2-yl) aminocarbonyl)aminosulfonylibenzoate 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 11 Wettable Powder Methyl 2-[tN-(2.6-dimethyl-5-nitropyrimidine-4- yl)aminocarbonyl]aminosulfonyl3benzoate 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 12 Low Strength Granule Methyl 2-[[N-(3-cyano-4.6-dimethylpyridin-2-yl) aminocarbonyl]aminosulfonyl]benzoate 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 13 Aqueous Suspension N'-t(3-cyano-4,6-dimethylpyridin-2-yl)aminocar- bonyl]-N,N-dimethyl-1,2-benzenedisulfonamide 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 14 Solution Methyl 2-[t(2-dimethylaminosulfonylphenyl)sulfonyl- amino]carbonylamino)-4 a 6-dimethylpyridin-3- carboxylate, 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 15 Low Strength Granule Methyl 2-L[N-(2,6-dimethyl-5-nitropyrimidine-4-yl) aminocarbonyl]aminosulfonyl]benzoate 0.1% 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 16 Granule N' -[ (3-cyano-4,6-dimethylpyridin-2-yl)aminocar- bonyl)-N,N-dimethyl-l,2-benzenedisulfonamide 80t wetting agent ¯ 1t 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 a 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 17 High Strength Concentrate Methyl 2-t[(2-dimethylaminosulfonylphenyl)sul- fonylaminoZcarbonylamino]-4,6-dimethylpyridin- 3-carboxylate 99% silica aerogel 0.5% synthetic amorphous silica o.5t 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 18 Wettable Powder Methyl 2-11(2-dimethylaminosulfonylphenyl)sul- fonylamino]carbonylamino]-4,6-dimethylpyridin 3-carboxylate 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 19 Wettable Powder Methyl 2-[tN-(3-cyano-4,6-dimethylpyridin-2-yl)- aminocarbonyl]aminosulfonyl]benzoate 40% sodium ligninsulfonate 20% montmorillonite clay 40% The ingredients are thoroughly blended a coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example 20 Oil Suspension Nl-t(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]- N,N-dimethyl-1,2-benzenedisulfonamide 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 21 Dust Methyl 2-I[N-(3-cyano-4,6-dimethylpyridin-2-yl) aminocarbonylaminosulfonylbenzoate 10t 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 Test results indicate that the compounds of the present invention are active herbicides. They appear to have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired a such as around fuel storage tanks, ammunition depots, industrial storage areas parking lots, drive-in theaters, around billboards, highway and railroad structures. In addition, test results indicate that certain compounds are useful for selective pre- and post-emergence weed control in sugar beets. Alternatively, the subject compounds are useful for plant growth modification. The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or herbicides, the species involved, the types of weeds to be controlled, weather and climate, formulations selected. mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.06 to 10 kg/ha, the lower rates being suggested for use as selective pre- and post-emergent herbicides in sugar beets a for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil. urea, amide. diphenylether. carbamate and bipyridylium types and mefluidide. The herbicidal and plant growth modifying properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. Test A Seeds of crabgrass (Digitaria sp.). barnyardgrass (Echinochloa crusgalli). wild oats (Avena fatua), sicklepod (Cassia obtusifolia). morningglory (Ipomoea sp.), cocklebur (Xanthium Pensylvanicum). sorghum, corn, soybean. sugar beet, rice, wheat, cotton. and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated with a soil/foliage application. At the time of treatment a the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days. after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis or necrosis; D = defoliation; E = emergence inhibition; G = growth retardation; H = formative effects; U = unusual pigmentation; X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers. The data indicate that at the low rates of application selected for these evaluations, most of the compounds tested are highly active herbicides. Additionally, they often possess plant growth modifying properties, such as causing growth retardation or axillary stimulation. Compounds Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 EMI33.1 Compounds (continued) Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 EMI34.1 Compounds (continued) Compound 11 EMI35.1 Compound 12 EMI35.2 Compound 13 EMI35.3 Compound 14 EMI35.4 Compounds (continued) Compound 15 Compound 16 Compound 17 EMI36.1 Compound 18 EMI36.2 Compound 19 EMI36.3 Compounds - (continued) Compound 20 Compound 21 Compound 22 Compound 23 Compound 24 EMI37.1 Compounds (continued) Compound 25 EMI38.1 Compound 26 EMI38.2 Compound 27 Compound 28 Compound 29 EMI38.3 Compounds (continued) Compound 30 Compound 31 EMI39.1 Compound 32 EMI39.2 Compound 33 Compound 34 EMI39.3 Compounds (continued) Compound 35 Compound 36 Compound 37 EMI40.1 Compounds (continued) Compound 38 Compound 39 EMI41.1 Table A Compound 1 Compound 2 Rate g/ha 50 400 50 400 POST-EMERGENCE Bush bean 1C,1H 4C,8G,6Y 5C,9G,6Y 5C,9G,6Y Cotton 0 2C,3G 4C,9G 4C,9G Morningglory 2C,3G 3C,5H 4C,8H 5C,9G Cocklebur O 1C 4C,8H 5C,9G Sicklepod 0 2C 2C,3H 5C,9H Nutsedge 0 2C,8G 0 2C,7G Crabgrass 1C,3G 2C,8G 2C,5H 2C,9H Barnyardgrass 2C,6H 4C,9H 5C,9H 9C Wild Oats 2C,6G 4C,9H 3C,9G 5C,9G Wheat 2C,9G 4C,9H 3C,9G 5U.9G Corn 3C,9H 5C,9G 2U,9H lOC Soybean 1C,2H 2C,6G 3C,9G,6X 5C,9G Rice 2C,8G SC. 9G 5C,9G 6C,9G Sorghum 5C,9H 5C,9G 5C,9G 9C Sugar beet 0 2C,5H 4C,8G 5C,9G PRE-EMERGENCE Morningglory 2C,2H 2C,3H 2C,2H 2C,8G Cocklebur 0 2C 0 2C,8H Sicklepod 0 0 0 2C,3G Nutsedge 0 0 0 0 Crabgrass 0 0 0 2C Barnyardgrass 0 0 0 2C,6G Wild Oats 2G 5G 4G 3C,7G Wheat 2G 8G 4G 3C,8H Corn 0 2C,6H 3C,8G 5C,9H Soybean 0 1C 1C 3C,5H Rice 0 2C,4G 3C,6H 10E Sorghum 3C,6G 5C,9G 5C,9H 10H Sugar beet 0 0 2C,5H 3C,8G Cotton Table A (continued) Compound 3 Compound 4 Rate g/ha 50 400 50 400 POST-EMERGENCE Bush bean 5C,9G,6Y 6C.9G.6Y 3C,8G,6Y 4C,9G,6Y Cotton 5C,8G 5C,9G 2C,4G 4C,8H Morningglory 4C,9G 5C,9G 3C,7G 4C,8H Cocklebur 3C,7G 5C.9G 0 5C,9H Sicklepod 4C,7H 4C,9H 1C 3C,5G Nutsedge 2C,9G 3C,9G 2C,5G 3C,8G Crabgrass 2C,7H 4C,9G 2G 3C,8H Barnyardgrass 5C.9H 9C 2C,7H 5C,9H Wild Oats 2C,9H 6C,9G 2C,6G 5C,9G Wheat 1C,9G 5U,9G 2C,3G 3C.9G Corn 5C,9G 5C,9G 3C,8H 5C,9G Soybean 3C,9G,5X 5C,9G 2C,3H 4C,9H Rice 9C 9C 5C,9G 5C,9G Sorghum 4C.9G 9C 2C,8H 2C,9G Sugar beet 5C,9G 9C 3C,6H 4C,9G PRE-EMERGENCE Moningglory 3C,6H 5C,9G 2C,3H 9C Cocklebur 0 4C,7H 2C 3C.3H Sicklepod 2C 5C,6H 2C,9H 3C Nutsedge 2G 2C,7G 0 2C.5G Crabgrass 0 2C,4G 2G 3C,6G Barnyardgrass 2C 3C,8H 1C 3C,3H Wild Oats 4C.8G 4C,9H 2C,9H 5C,9G Wheat 2C,9H 4C,9G 2C,9H 4C,9G Corn 3C,9H 4C,9H 5C,9H 5C,9G Soybean 3C,5H 4C,6H 2C 4C.8H Rice 3C,7H 10E 2C,7H 5C,9H Sorghum 7C,9H 7C,9H 5C,9H 5C,9H Sugar beet 2C,2H 5C,9G 2C,2H 3C,8H Cotton Table A (continued) Compound 5 Compound 6 Rate g/ha 50 400 50 400 POST-EMERGENCE Bush bean 2C,2G,6Y 6C,9G,6Y 6Y 2C,6G,6Y Cotton 1C 5C,7H 1C,1H 2C,2H Morningglory 3C,5G 4C,7H 1H 2C,5H Cocklebur 0 2G 2C,8G 2C,8G Sicklepod 0 1C 2C 2C,5G Nutsedge 7G 9G 0 2C.6G Crabgrass o 1C,5G 4G 2C,7G Barnyardgrass 0 2C,7H 2C,5H 5C,9H Wild Oats 2C.5G 2C,9G 2G 2C,8G Wheat 2C,5H 3C,9G 0 4G Corn 3C,7H 3C.9G 2C,8H 2U,9G Soybean 2C,4H 3C,9G 1C,2H 1C.5H Rice 2C,8G 5C,9G 2C,6G 5C,9G Sorghum 3C,5H 5C,9H 2C,5H 3C,9G Sugar beet 1C 4C,8G 2C,6H 2C,9G PRE-EMERGENCE Morningglory 3C,3H 3C,5H 2G 9G Cocklebur 0 1H - - Sicklepod 1C 2C 1C 2C,7G Nutsedge 0 0 10E 10E Crabgrass 0 1C 0 0 Barnyardgrass <RTI ID=44.9> 0 1C 0 2C,4H Wild Oats 1C,2G 3C,7G 0 2C,8G Wheat 1C,2G 2C,9H 3G 2C,9G Corn 2C,5G 5C,9H 2C,4G 2C,9G Soybean 2C,3G 3C,4H 0 1H Rice 2C 2C,4G 0 9H Sorghum 2C,6G 5C,9H 2C 2C,9G Sugar beet 0 0 0 0 Cotton Table A (continued) Cmpd. 6 Compound 7 Cmpd. 8 Rate g/ha 2,000 50 400 50 POST-EMERGENCE Bush bean 5S,9D,6Y 5C,9G,6Y 9C 4C,8G,6Y Cotton 5C,9G 5C,9G 6C,9G 4C,8H Morningglory 10C 4C,7G 4C,9G 4C,9G Cocklebur 4C,9G 5C,9G 10C 9C Sicklepod 5C,9G 4C,8G 6C,9G 3C,5G Nutsedge 9G 9C 10C 3C,6G Crabgrass 3C,6G 4C,8G 9C 3C.9G Barnyardgrass 2C,9H 9C 9C 5C,9G Wild Oats 2C.9G 6C,9G 9C 4C.9G Wheat 2C,9G 9C 9C 2C,9G Corn @ 9G 9C 10C 9C Soybean 2C,8G 5C,9G 9C 5C,9G Rice 4C,9G 5C,9G 5C,9G 5C,9G Sorghum 9G 9C 10C 9C Sugar beet - 9C 9C 3C.5H PRE-EMERGENCE Morningglory 9G 2C.7G 9C 9G Cocklebur - 9C - 8H Sicklepod 2C,4G 3C.3H 9C 0 Nutsedge 10E 1C,9G 10E 0 Crabgrass 3C.8G 1C 5G 0 Barhyardgrass 3C,9H 2C,7H 5C,9H 4H Wild Oats 3C,7G 2C,9H 3C,9H 1C Wheat 2c,9H 2C,9G 3C,9H 2C,8H Corn 9G 5C.9G 10H 2C,8H Soybean 3C.5H SH 9H 1C Rice 10E 10E 10E 2C,8G Sorghum 2C,9H 7C,9H 6C,9H 2C,9H Sugar beet - 4C.9G 5C,9G BG Cotton Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Rate g/ha 50 50 50 50 POST-EMERGENCE Bush bean 2C 1C 1C,1H 1C Cotton 2C,2H 1C 4C,5H 2C Morningglory 3C,6G 2C 2C,5G 2C Cocklebur 2C 0 4C,9G 2C Sicklepod 2C 0 3C,5G 1C Nutsedge 2G 0 5C.9G 0 Crabgrass 2C.5G 0 6H 0 Barnyardgrass 2C,8H 2C,3H 5C,9H 0 Wild Oats 2C 0 2C,5G 0 Wheat 2C,8G 0 1C,2G 0 Corn 2C,9G 1C 2C,9G 2C,6H Soybean 2C,8G IC 2C,9G 1C Rice 2C,8G 0 5C,9G 1C,8G Sorghum 2C,9G 2C.8H 3C,9H 0 Sugar beet 2C 2C 5C,9G 2C,5H PRE-EMERGENCE Morningglory 0 0 8G 3C Cocklebur - 0 2C,8H 0 Sicklepod 0 0 2H 1C Nutsedge 0 0 9G 0 Crabgrass <RTI ID=46.6> 0 O 1C 0 Barnyardgrass 0 0 2C,3H 0 Wild Oats 0 0 2C,7G 0 Wheat 0 0 2C,8G 0 Corn 5G 0 2C,9G 2C,5G Soybean 1C 1C 3C,5H 1C Rice 0 0 10E 2C Sorghum 3G 5G 3C.8H 0 Sugar beet 1C 1C 6C,9G 0 Cotton - - - Table A (continued) Compound 13 Rate g/ha 50 400 POST-EMERGENCE Bush bean 3C,6G,6Y 5C,9G,6Y Cotton 4C,6H 5C,8H Morningglory 2C.4G 4C.8H Cocklebur 3C,9G 5C,9G Sicklepod 2C,4H 4C,8G Nuteedge 2C,9G 4C,9G Crabgrass 2C 3C,7G Barnyardgrass 3C,8H 5C,9H Wild Oats 1C 2C. 8G Wheat 1C,2G 1C,7G Corn 1C,9G 5U,9G Soybean 2C,8H 4C.9G Rice 2C,9G 9C Sorghum 3C.7H 2C.9G Sugar beet 4C.9G 9C PRE-EMERGENCE Morningglory 2C,4G 2C,9G Cocklebur 2C 2C,9H Sicklepod 0 2C,9G Nutsedge 5G 10E Crabgrass 1C 2C,4G Barnyardgrass 1C 2C.8H Wild Oats 4G 2C,8G Wheat 5G 2C,8G Corn 2C.9H 2C.9H Soybean 2C,5G 2C,7H Rice 2C,7G 2C,8G Sorghum 2C,5G 2C,7G Sugar beet 4C,9G 5C,9G Cotton Table A (continued) Cmpd. 14 Cmpd. 15 Rate g/ha 50 50 POST-EMERGENCE Bush bean 2C,3H,6Y 1C Cotton 2C,5G 1C,4G Morningglory 2C,6H 1C Cocklebur 2C 1C,5H Sicklepod O 0 Nutsedge O 0 Crabgrass O 0 Barnyardgrass O 0 Wild Oats O 0 Wheat O 0 Corn O 0 Soybean 0 1C,7G,7X Rice O 2H Sorghum 0 1C,3H Sugar beet 3C,6G 1C,2H PRE-EMERGENCE Morningglory 1C.5H Cocklebur 2H 0 Sicklepod 2H 0 Nutsedge O 0 Crabgrass 2G 0 Barnyardgrass. 5G 1C Wild Oats O 0 Wheat 0 0 Corn 0 0 Soybean 0 0 Rice 3G 1C Sorghum 2G 1H Sugar beet 0 5G Cotton Table A (continued) Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Rate g/ha 50 50 50 50 POST-EMERGENCE Bush bean Cotton 2C,8G 6C,9G 2C,5G 3C,8G Morningglory 2C 4C,8H 2C.3H 4C.8H Cocklebur 3C,9H 10C 4C,9G 4C,8H Sicklepod 2C 10C 2C,2H 4C,5G Nutsedge 8G 9C 5G 3G Crabgrass 2G 8G 4G 5G Barnyardgrass 1H 9H 5H 2C.5H Wild Oats 0 2C,9G 3G 3C,9G Wheat 0 3C,9G 6G 3C,9G Corn 1C,3G 3U,9G 2C,8H 2C,7H Soybean 5C,9G 5C,9G 3C,9G 4C,9G Rice 9G 4C,9G 9G 5C.9G Sorghum 2G 9G 3C.8H 4C.9G Sugar beet 3C.8G 5C.9G 2C,2G 3C,8H PRE-EMERGENCE Morningglory 2G 7H 9G 2C. 8H Cocklebur 3G 8H 2C,5G Sicklepod 4G 9G 2C 2C Nutsedge 10E 10E 0 2C Crabgrass 2G 5G 2G 2G Barnyardgrass 1H 2C,8G 1H 2C,2H Wild Oats 0 2C,8G 2G 2C.5G Wheat 0 2C.8H 2G 7G Corn 2G 2C.9H 3C.6G 2C,8G Soybean 2H 2C.2H 0 2H Rice 6G 10E 9H 9H Sorghum 3G 3C,9H 2C,7G 3C,9G Sugar beet 4G 3C,8G 1C 2C Cotton 3G 2C,8G 0 2G Table A (continued) Cmpd 20 Cmpd. 21 Cmpd. 22 Cmpd. 23 Rate g/ha 400 400 400 400 POST-EMERGENCE Bush bean 2C 4C,9G,6Y 1C,3H,6Y 2C,7G,6Y Cotton 2C 3C,6H 3C,5G 2C,5H Morningglory 2C,5G 3C,8G 4C,9G 3C,8G Cocklebur 5C,9G 9C 8H 4C,9G Sicklepod 3G 3C,5G 1C,2H 3C,5G Nutsedge 3G 2C,7G 3G 4G Crabgrass O 2C,7G 2C,9G 3C,8G Barnyardgrass 2H 3C.8H 2C,5H 3C,9H Wild Oats 0 3C.9H 2C,9H 2C,4G Wheat 0 2C,9G 2C,9G 4G Corn 2G 3C,9G 2C.8H 2C,8H Soybean 1C 3C,8H 1C,5H 3C,8G,5X Rice 6G 5C,9G 5C,9G 4C,9G Sorghum 1B 3C,9G 2C,9G 9G Sugar beet 4B 3C.8H 3G 4C,8H PRE-EMERGENCE Morningglory 3C.9G 5C,9G 2C,6H 3C.9G Cocklebur 9H 9H 6H 9H Sicklepod 8G 9G 2C,4G 7G Nutsedge 2C,8G 4G 0 5G Crabgrass 0 2G 2C,5G 1C Barnyardgrass 1C 2C,9H 5H 2C,8H Wild Oats 0 3C,9G 2C.9G 2C.7G Wheat <RTI ID=50.7> 0 9H 9H 8G Corn 6G 2C,9H 2C,9G 2C,9H Soybean 1C 3C,7H lC.lH 2C.3H Rice 3C,8H 10E 10E 10E Sorghum 0 5C,9H 3C,9H 5C,9G Sugar beet 9G 9G 8G SC. 9G Cotton - - - Table A (continued) Compound 24 Compound 25 Rate g/ha 400 400 POST-EMERGENCE Morningglory 1C,1H 1C,1H Cocklebur 3C,4G 4C,9H Sicklepod 3C,5G 3C Nutsedge 0 0 Crabgrass 0 0 Barnyardgrass 0 0 - Wild Oats 0 0 Wheat 0 0 Corn 2G 0 Soybean ZC,2H 3C,3H Rice 2G 1C Sorghum 1C 0 Sugar beet 2C,6H 3C,7G Cotton 2C,4G 2C,4G PRE-EMERGENCE Morninggloy 1C 1C,1H Cocklebur 0 2C,2H Sicklepod 0 0 Nutsedge 0 0 Cragrass 0 0 Barnyardgrass 2G 2H Wild Oats 0 0 Wheat 0 0 Corn 2G 0 Soybean 0 Rice 0 0 Sorghum 2G 3G Sugar beet 5H 0 Cotton 0 0 Table A (continued) Compound 26 Compound 27 Rate g/ha 400 50 400 50 POST-EMERGENCE Morningglory 5C,9G 1C,2G 3C,6G 3G Cocklebur 5C,9G 3C,9H 4C,9H 3C,7G Sicklepod 4C,5G 2C 3C,3G 3C,5G Nutsedge 3G 0 0 0 Crabgrass 4G 0 0 0 Barnyardgrass 3C,7H 2H 0 0 Wild Oats 3C,9G 3G 0 0 Wheat 8G 2G 0 0 Corn 1H 0 0 0 Soybean 5C,9G 2C,2H 3C,3G 0 Rice 4C,9G 2C,5G 0 0 Sorghum 3C,7H 2H 3C,4G 0 Sugar beet 4C,8G 3C,6H 3C,6G 3C,6H Cotton 3C,9H 2C,5H 3C,6H 2G PRE-EMERGENCE Morningglory 2C,2H 0 3C,5H 0 Cocklebur 2C,3H 1H 4C.7G 0 Sicklepod 2C,5H 0 2C,5G 0 Nutsedge 0 0 0 0 Crabgrass 0 0 0 0 Barnyardgrass 1H 0 0 0 Wild Oats 0 0 0 0 Wheat 0 0 2G 0 Corn 5G <RTI ID=52.7> ZC,3G 2C,5G 0 Soybean 2C 0 2C 0 Rice 2C 0 2C 0 Sorghum 2C,3G 5G 2C,4G 0 Sugar beet 3C.7G 2C,7H 2C,6H 0 Cotton 2C,7G 0 2G 0 Table A (continued) Compound 28 Compound 29 Rate g/ha 400 50 400 50 POST-EMERGENCE Morningglory 5C,9G 3C,8H 5C,9G 3C,6G Cocklebur 10C 3C,9G 9C 4C,9G Sicklepod 6C,9G 4C,7G 5C,9G 4C,8H Nutsedge 9G 2C,6G 5G 2G Crabgrass 4C,9G 3G 7G 3G Barnyardgrass 9C 5C,8H 3C,8H 4H Wild Oats 3C,8G 3G 3C,7G 0 Wheat 5G 0 5G 6G Corn 3C,9G 2C,8H 3C,7H 2C,4H Soybean 5C,9G 3C,9G 5C,9G 3C,9G,7X Rice 6C,9G 6C,9G 5C.9H 2C,9G Sorghum 6C,9G 3C,9G 3C,9H 3C,7H Sugar beet 9C 5C,9G 5C,9G 3C,8H Cotton 5C,9G 2C,9G 5C,9G 2C,9H PRE-EMERGENCE Morningglory 9G 3C,7H 8G 2C,6G Cocklebur 9H 9H 9H 3C,7G Sicklepod 3C,8G 4C,5G 3C,7G 2C,5G Nutsedge 2C,5G 0 0 0 Crabgrass 2C 1C 0 0 Barnyardgrass 3C,9H 2C,3H 3C,6G 0 Wild Oats 3C,8G 1C 3C,6G 1C Wheat 2C,7G 1C 6G 0 Corn 10H 3C,9H 3C,8G 2C,6G Boybean 8H 2C,5H 3C,6H 2C,4G Rice 10E 3C,5G 4C,7G 2C,5G Sorghum 5C,9H 2C,9G 3C,9H 3C,7G Sugar beet 5C,9G 3C,8G 5C,9G 2C,8G Cotton 9G 3C,7G 8G 2C,6G Table A (continued) Cmpd. 30 Cmpd. 31 Cmpd. 32 Cmpd. 33 Rate g/ha 50 50 50 50 POST-EMERGENCE Morningglory 1C 2C,4G 1C,2H 2G Cocklebur 2C,8H 4C,9G 3C,9H 2C,8H Sicklepod 2C 5C,9G 3C,8H 0 Nutsedge 3C,9G 2C,9G 2C,8G 0 Crabgrass 0 0 3G 0 Barnyardgrass 0 2G 2C,4H 2C,7H Wild Oats 0 2C,9H 0 2C,5G Wheat 0 9C 7G 2C,5G Corn 0 5C,9G 3C,8H 3C,9H Soybean 1H 4C,9G 3C,8H Rice 6G 5C,9G 9G 9G Sorghum 0 2C,9H 3C,9H 2C,9G Sugar beet 9C 9C 2C,3G 3C,6G Cotton 7G,2C 9C 5C,9G - 2G PRE-EMERGENCE Morningglory 2H 0 2G 0 Cocklebur 2H 2C,7H 2C,5H 0 Sicklepod 2G 2C 0 0 Nutsedge 5C,9G 10E 2C,5G 0 Crabgrass 2C 0 2G 0 Barnyardgrass 1C 1C 2C 0 Wild Oats 0 2C,8G 2C 0 Wheat 0 2C,8G 4G 0 Corn 5G 2C,9H 3C,8H 3G Soybean 0 2C - 0 Rice 0 3C,8H 3C,5G 0 Sorghum 0 2C,9G 3C,6G 2G Sugar beet 5C,9G 5C,9G 8G 7H Cotton 6G 8G 5G Table A (continued) Cmpd. 34 Cmpd. 35 Cmpd. 36 Cmpd. 37 Rate g/ha 50 50 50 50 POST-EMERGENCE Morningglory 2G 2C,3G 1C 2G Cocklebur 3C,8H 3C,9G 9C Sicklepod 0 2C 3C,7G 0 Nutsedge 5G 3C,8G 3C,7G 0 Crabgrass 1C 4G 6G 0 Barnyardgrass 2C,5H 3C,9H 9C 6H Wild Oats 0 2C,8G 9C 0 Wheat 0 1C,7G 6C,9G 0 Corn 2C,8H 1C,9G 3C,9G 1H Soybean lC,lH 2C,9G 5C,9G 3H Rice 2C,8G 5C,9G 5C,9G 4G Sorghum 2C,8H 3C,9H 5C,9G 2C,6G Sugar beet 3C,6G 2C,4G 5C,8G 1H Cotton 3C,8H 2C,8G 2C,9G 2G PRE-EMERGENCE Morningglory 0 2G 3C,6G 0 Cocklebur 0 8H 9H 2H Sicklepod 0 2G 5G 1C Nutsedge 0 3G 2G 0 Crabgrass 0 0 0 0 Barnyardgrass 0 4H 5G 0 Wild Oats 0 2G 3C,9G 0 Wheat 0 0 2C,5G 0 Corn 2G 2C.SG 2C,9G 0 Soybean 0 2C,2H 1C,1H 1H Rice 0 3C,8H 5C,9H 0 Sorghum 0 3C,6G 5C,9H 0 Sugar beet 7H 7G 9H 0 Cotton 0 5G 9G 2G Table A (continued) Cmpd. 38 Cmpd.39 Rate g/ha 50 50 POST-EMERGENCE Morningglory 3C,6H 2C,5G Cocklebur 2C,6H 3C,8G Sicklepod 3G 3C,SG Nutsedge 0 3G Crabgrass 0 2G Barnyardgrass 5H 3C,6H Wild Oats 0 2C,5G Wheat 2G 2C,8G Corn 2C,7H 2C,6H Soybean 2C,2H 2C,2H Rice 2C,8G 2C,5G Sorghum 2H 1C Sugar beet 2C,6H 2C,7G Cotton 2G 2G PRE-EMERGENCE Morningglory 7H 0 Cocklebur 2G 0 Sicklepod 0 0 Nutsedge 0 0 Crabgrass 0 0 Barnyardgrass 2H 0 Wild Oats 0 0 Wheat 0 0 Corn 2G 0 Soybean 1H 0 Rice 5G 0 Sorghum 0 0 Sugar beet 0 0 Cotton 0 0 The following test was performed to better define the pre-emergence activity of the claimed compounds. Test B Two plastic bulb pans were filled with fertilized and limed Woodstown sandy loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanquinalis). 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), morningglory (Ipomoea hederacea) sicklepod (Cassia obtusifolia), 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 sugar beets. 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. Results for several of the more active compounds are presented in Table B. Almost all of the compounds tested showed pre-emergence activity on a number of species at rates as low as 31 g/ha; some were active at even lower rates. At higher rates, e.g. 125 g/ha, most compounds exhibited broad spectrum pre-emergence activity. Table B PRE-EMERGENCE ON WOODS TOWN SANDY LOAM Compound 7 Compound 8 Rate g/ha 8 62 31 250 Crabgrass 0 0 0 7G Barnyardgrass 0 7G 0 5G Sorghum 6G 9G 8G 9G Wild Oats 0 2G 0 0 Johnsongrass 5G 9G 4G 8G Dallisgrass 0 4G 0 5G Giant foxtail 0 0 0 7G Ky. bluegrass 0 5G 2G 9G Cheatgrass 0 9G 0 7G Sugar beets 5G 9G 5G 7G Corn 7G 8G 3G 7G Mustard 9G 9G 8G 9G Cocklebur 0 8G - 8G Nutsedge 0 9G 0 6G Cotton 3G 3G 3G 5G Morningglory 0 2G 0 0 Sicklepod 0 3G 2G 3G Teaweed 3G 6G 0 0 Velvetleaf 0 2G 0 2G Jimsonweed 2G 4G 0 0 Soybean 0 7G,7H 0 2G Rice 6G 10C 5G 10C Wheat 0 6G 0 8G Table B (continued) PRE-EMERGENCE ON WOODSTOWN SANDY LOAM Compound 21 Rate g/ha 31 125 Crabgrass 0 3G Barnyardgrass 0 3G Sorghum 9G 10C Wild Oats 0 3G Johnsongrass 4G 5G Dallisgrass 0 7G Giant foxtail 3G 8G Ky. bluegrass 6G 10C Chestgrass 7G 10C Sugar beets 6G 8G Corn 3G 9G Mustard 8G 9G Cocklebur 7G 7G Nutsedge 2G 4G Cotton 2G 8G Morningglory 2G 2G Sicklepod 0 2G Teaweed 0 0 Velvetleaf 2G 4G Jimsonweed 2G 7G Soybean 0 3G Rice 10C 10C Wheat 0 2G The following test was performed to better define the post-emergence activity of the claimed compounds. Test C The test chemicals. dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. One day after treatment, plants were observed for rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theoPhrasti) sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), morningglory (lpomoea hederacea), jimsonweed (Datura stramonium). cocklebur (Xanthium pensylvanicum), crabgrass (Diqitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusqalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, and mustard, All plants were sprayed approximately 14 days after planting. Additional plant species are sometimes added to this standard test in order to evaluate unusual selectivity. Results for two of the most active compounds tested in this screen are presented in Table C. Many of the other compounds also showed post-emergence activity at rates as low as 4 or 16 g/ha. Table C Over-the-Top Soil/Foliage Treatment Compound 7 Rate g/ha 4 16 61 Soybeans 10C 10C 10C Velvetleaf 7G,7C 9C 10C Sesbania 7G 9G 9G Sicklepod 7G 9G 9G Cotton 9G 10C 10C Morningglory 7G,5C 8G 8G Alfalfa 7G,6C 7C,8G 8C,9G Jimsonweed 4G 6G 9G Cocklebur 8G 9G 9G Sunflower 8C,7G 10C 10C Mustard 6G 8G 10C Sugar beets 8G 10C 10C Corn 10C 10C 10C Crabgrass 6G 3G 6G Rice 9C 8C,8G 9C Nutsedge 7G 7G 7G Barnyardgrass 10C 10C 10C Wheat 6C,7G 6G 6C,7G Giant foxtail 9G 6G 9G Wild Oats 8G 8G 8G Sorghum 9G 9G 9G Johnsongrass 9G 9G,9C 9G Field Bindweed 7G 5G 7G Table C (continued) Over-the-Top Soil/Foliage Treatment Compound 8 Rate g/ha 4 16 61 Soybeans 8G,9C 10C 10C Velvetleaf 6G 9G,7C 10C Sesbania 8G 9G 9G Sicklepod 4G 8G 9G Cotton 9G 9G 10C Morningglory 7G 7G,6C 8G,7C Alfalfa 2G,1C 7G.6C 10C Jimsonweed 0 4G 6G Cocklebur 8G 9G 10C Sunflower 8G 10C 10C Mustard 7G 8G 9G Sugar beets 7G 8G 10C Corn 6G 7G 7G Crabgrass 4G 7G 9G Rice 6G 9C 10C Nutsedge 0 2G 4G Barnyardgrass 7G 9C,7G 10C Wheat 6G 7G 8G Giant foxtail 3G 6G 8G Wild Oats 5G 7G 8G Sorghum 8G 9G 9G Johnsongrass 8G 9C 9C Field Bindweed 0 2G 4G Test D Two 25-cm in diameter plastic pans lined with polyethylene liners were filled with prepared Sassafras loamy sand soil. One pan was planted with seeds of wheat (Triticum aestivum). barley (Hordeum vulgar), wild oats (Avena fatua), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis) and Italian ryegrass (Lolium multiflorum). The other pan was planted with seeds of wild radish (Raphanus naphanistrum), kochia (Kochia scoparia), Matricaria inodoraa black nightshade (Solanum niqrum), wild mustard (Brassica kaber), wild buckwheat (Polvaonum convolvulus), Galium apafine. Veronica persica and sugar beets (Beta vulgaris). 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 test compound was diluted with a non-phytotoxic 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 21 days at which time the treatments were compared to the controls and the effects visually rated utilizing the rating system as described in Test A. The recorded data are presented in Table D. The data indicate that the compound tested has utility for selective weed control in sugar beets. Table D Compound 18 Pre-Emergence Rate g/ha 4 16 64 125 250 wheat 0 0 0 - barley 0 0 0 - wild oats 0 0 0 - - ryegrass 0 0 4G - - annual bluegrass 0 1G 4G - - blackgrass 0 3G 2G - green foxtail 0 0 0 - - Matricaria inodora 1G 5G 6G - Galium aparine 4G.3C 4G,3C 7G - - kochia 0 0 0 0 0 black nightshade 5G,4C 4G,7C 8G,9C 8G,7C 9G speedwell 3G 10C 10C - wild buckwheat 0 5G.3C 7G 8G,8C 10C wild mustard 0 5G,4C 9G,9C 9G 10C wild radish 3G 9G 9G - sugar beets 0 0 0 1G 1G Post-Emergence Rate g/ha 4 16 64 125 250 wheat 0 0 3G - barley 0 0 3G - wild oats 0 0 2G - ryegrass 0 0 1G - annual bluegrass 0 0 0 blackgrass 0 0 0 green foxtail 0 0 0 Matricaria inodora 1C lG,3C 4G.3C Galium aparine 2G 9G - kochia - 0 3G 0 0 black nightshade lG,lC 3C 3C 5G,3C 9G,8C speedwell 7G,5C 7G,4C 8G - wild buckwheat 9G,7C 9G,8C 9G 4G 10C wild mustard 9G,8C 9G,7C 10C 3G 10C wild radish 10C 10C 10C - sugar beets 0 0 3G 4G,3C 8G,8C

Claims: Claims 1. A compound of the formula: EMI65.1 wherein J is EMI65.2 R1 is NO2, F, Cl, Br, CF3, C1-C3 alkyl, C1-C2 alkyl substituted with OCH3 or OC2H5, CO2Rg, SO2N(CH3)R10, S(O)nR11, SCF2H, OR12, OSO2R11, CH2CH2Cl. EMI65.3 EMI66.1 R2 is H. F, C1, Br. CH3 OCH3 or CF3; R3 is C1. SO2CH3 or SO2N(CH3)2; R4 is H or CH3; R5 is H or C1-C3 alkyl: R6 is C1-C3 alkyl, CO2R11, S(O)nR11, Cl or Br: R7 is OSO2R11, S(O)nR11, C1-C3 alkyl, C1-C3 alkoxy or C1; R8 is C1-C3 alkyl: R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2Cl or CH2CH2OCH3: R10 is C1-C3 alkyl or OCH3: R11 is C1-C3 alkyl: R12 is C1-C3 alkyl, CF2H, CH2CH2OCH3, C3-C4 alkenyl or C3-C4 alkynyl; R13 is H or CH3; m is 0 or 1; n is 0, 1 or 2; Q is O, S or SO2 R is H or CH3; A is EMI66.2 W is CN, CO2CH3, CO2C2H5, NO2, S(O)R11, SO2R11 or CONR14R15: R14 and R15 are independently H or CH3: X is CH3, OCH3, OC2H5, CH2OCH3, or Cl; Y is CH3, OCH3. OC2H5 or C1; and Z is CH or N: provided that (a) X and Y cannot simultaneously be C1; (b) when either X or Y is Cla then Z is CH and (c) when X and Y are both CH3 and Z is CH, then W is other than NO2; and their agriculturally suitable salts. 2. A compound of the formula: EMI67.1 wherein J is EMI67.2 R1 is NO2, F, Cl, Br, CF3, C1-C3 alkyl, CH2CH2OCH3, CH2OCH3, CO2R9, SO2N(CH3)R10, S(O)nR11, SCF2H, OR12, OSO2R11, EMI67.3 EMI68.1 R2 is H, F. C1, Br. CM3, OCH3 or CF3: R3 is Cl, SO2CH3 or SO2N(CH3)2: R4 is H or CH3; R5 is H or C1 C3 alkyl; R6 is C1-C3 alkyl a CO2R11, S(O)nR11, Cl or Br: R7 is S(O)nR11, OSO2R11, C1-C3 alkyl, C1-C3 alkoxy or Cl; R8 is C1-C3 alkyl: R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2Cl or CH2CH2OCH3; 10 is C1-C3 alkyl or OCH3: 11 is C1-C3 alkyl: R12 is C1-C3 alkyl, CF2H or CH2CH2OCH3: R13 is H or CH3: n is 0 or 2: Q is O, S or SO2; R is H or CH3; A is EMI68.2 W is CN, CO2CH3, CO2C2H5, NO2, SO2R11 or CONR14R15; R14 and R15 are independently H or CH3: X is CH3, OCH3, OC2H5, CH2OCH3, or Cl: Y is CH3, OCH3, OC2H5 or Cl; and Z is CH or N: provided that (a) X and Y cannot simultaneously be Cl; (b) when either X or Y is C1, then Z is CH and (c) when X and Y are both CH3 and Z is CH. then W is other than NO2: and their agriculturally suitable salts. 3. A compound of Claim 1 where J is EMI69.1 4. A compound of Claim 3 where R is H and R2 is H. 5. A compound of Claim 4 where X and Y are independently CH3 or OCH3 and W is CN, NO2 or CO2CH3 6. A compound of Claim 5 where R1 is NO2, CO2CH3, CO2C2H5, SO2N(CH3)2, SO2CH3 or OSO2CH3, 7. A compound of Claim 6 where 2 is CH. 8. The compound of Claim 1 which is methyl 2 [[N-(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl] aminosulfonyl ) benzoate. 9. The compound of Claim 1 which is N1-((3- cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-N,N dimethyl-1,2-benzenedisulfonamide. 10. The compound of Claim 1 which is methyl 2 [[N-(2,6-dimethoxy-5-nitropyrimidin-4-yl)aminocar bonyl)aminosulfonyl)benzoate. 11. The compound of Claim 1 which is methyl 2 [[(2-dimethylaminosulfonylphenyl)sulfonylamino]car bonylamino]-4.6-dimethylpyridin-3-carboxylate. 12. An herbicidal composition comprising an herbicidally effective amount of a compound of any of claims 1 to 11 and at least one of (a) a surfactant and (b) a solid or liquid diluent. 13. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of any of claims 1 to 11. 14. A method of regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant selected from compounds of any of claims 1 to 11. 15. A process for the production of a compound of claim 1, which comprises reacting an appropriate aminoheterocycle of formula R-NH-A (II) wherein R and A are as defined in claim 1, with an appropriately substituted sulfonyl isocyanate of formula JSO2NCO (III) wherein J is as defined in claim 1. Claims 1. A process for the preparation of a compound of the formula: EMI71.1 wherein J is EMI71.2 R1 is NO2, F, Cl, Br, CF3, C1-C3 alkyl, C1-C2 alkyl substituted with OCH3 or OC2H5, CO2R9, SO2N(CH3)R10, S(O)nR11, SCF2H, OR12, OSO2R11, CH2CH2Cl, EMI71.3 EMI72.1 R2 is H. F. C1. Br, CH3, OCH3 or CF3: R3 is C1, SO2CH3 or SO2N(CH3)2; R4 is H or CH3; R5 is H or C1-C3 alkyl: R6 iS C1-C3 alkyl, CO2R11, S(O)nR11, Cl or Br: R7 is OSO2R11, S(O)nR11, C1-C3 alkyl, C1-C3 alkoxy or C1; R8 is C1-C3 alkyl: R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2Cl or CH2CH2OCH3; R10 is C1-C3 alkyl or OCH3: R11 is C1-C3 alkyl: R12 is C1-C3 alkyl, CF2H, CH2CH2OCH3, C3-C4 alkenyl or C3-C4 alkynyl: R13 is H or CH3; m is 0 or 1; n is 0, 1 or 2; Q is O. S or SO2; R is H or CH3; A is EMI72.2 W is CN, CO2CH3, CO2C2H5, NO2, S(O)R11, SO2R11 or CONR14R15; R14 and R15 are independently H or CH3: X is CH3, OCH3, OC2H5, CH2OCH3, or Cl: Y is CH3. OCH3, OC2H5 or C1; and Z is CH or N; provided that (a) X and Y cannot simultaneously be C1; (b) when either X or Y is C1, then Z is CH and (c) when X and Y are both CH3 and Z is CH, then W is other than NO2; or an agriculturally suitable salt thereof; which comprises reacting an appropriate aminoheterocycle of formula R-NH-A (II) with an appropriately substituted sulfonyl isocyanate of formula JSO2NCO (III) wherein R, A and J are as defined above. 2. A process for the preparation of a compound of the formula: EMI73.1 wherein J is EMI73.2 EMI74.1 R1 is NO2, F, Cl, Br, CF3, C1-C3 alkyl, CH2CH2OCH3, CH2OCH3, CO2R9, SO2N(CH3)R10, S(O)nR11, SCF2H, OR12, OSO2R11, EMI74.2 EMI74.3 R2 is H, F, Cl, Br, CH3, OCH3 or CF3; R3 is C1, SO2CH3 or SO2N(CH3)2: R4 is H or CH3; R is H or C1-C3 alkyl: R6 is C1-C3 alkyl. CO2R11, S(O)nR11, Cl or Br; R7 is S(O)nR11, OSO2R11, C1-C3 alkyl, C1-C3 alkoxy or Cl: R8 is C1-C3 alkyl; R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2Cl or CH2CH2OCH3; R10 is C1-C3 alkyl or OCH3: R11 is C1-C3 alkyl; R12 is C1-C3 alkyl, CF2H or CH2CH2OCH3; R13 is H or CH3: n is 0 or 2; Q is O, S or SO2; R is H or CM3;' A is EMI75.1 W is CN, CO2CH3, CO2C2H5, NO2, SO2R11 or CONR14R15: R14 and R15 are independently H or CM3; X is CH3, OCH3, OC2H5, CH2OCH3 or Cl: Y is CH3, OCH3, OC2H5 or C1; and Z is CH or N; provided that (a) X and Y cannot simultaneously be C1; (b) when either X or Y is C1, then Z is CH and (c) when X and Y are both CH3 and Z is CH, then W is other than NO2; or an agriculturally suitable salt thereof; which comprises reacting an appropriate aminoheterocycle of formula R-NH-A (II) with an appropriately substituted sulfonyl isocyanate of formula JSO2NCO (III) wherein R, A and J are as defined above. 3. A process of Claim 1 where J is EMI75.2 4. A process of Claim 3 where R is H and R2 is H. 5. A process of Claim 4 where X and Y are independently CH3 or 0CH3 and W is CN, NO2 or CO2CH3. 6. A process of Claim 5 where R1 is NO2, CO2CM3. C02C2H,, SO2N(CH3)2, SO2CH3 or OS02CH3. 7. A process of Claim 6 where Z is CH. 8. The process of Claim 1 wherein the product is a compound selected from: Methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2-yl)amino carhanyl]ammosulfonylljenzoate; N'-[(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-N,Ndimethyl-1,2-benzenedisulfonamide; Methyl 2-[[N-(2,6-dimethoxy-5-nitropyrimidin-4-yl)amino carbonyli aminosulfonyl] benzoate; and Methyl 2-[[(2-dimethylamìnosulfonylphenyl)sulfonylamino carbonylamino]-4,6-dimethylpyridin-3-carboxylate. 9. An herbicidal composition comprising an herbicidally effective amount of a compound of formula (I) as defined in any of claims 1 to 8 and at least one of (a) a surfactant and (b) a solid or liquid diluent. 10. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of formula (I) as defined in any of claims 1 to 8. 11. A method for regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant selected from compounds of formula (I) as defined in any of claims 1 to 8.

Inventors: HOLYOKE, CALEB WILLIAM, JR., TSENG, CHI-PING, ZIMMERMAN, WILLIAM THOMAS
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1984
Main classification: C07D213
IPC codes: A01N47, C07D213, C07D521