HERBICIDAL HALOPYRIMIDINES

Abstract: Sulfonylurea derivatives of the formula wherein R is CH₃ or C₂H₅; L and J are aromatic groups of defined structure; and agriculturally acceptable salts thereof; exhibit herbicidal activity. Some also exhibit plant growth regulant activity. The compounds may be formulated for agricultural use in conventional manner. They may be made by a variety of syn­ thetic routes, e.g. by reacting an appropriate aromatic sulfonyl isocyanate with the appropriate aminoheterocycle.

Description: TITLE HERBICIDAL HALOPYRIMIDINES Background of the Invention The present invention relates to specific halopyrimidine compounds which are useful as general or selective preemergent or postemergent herbicides or as plant growth regulants. U.S. Patent 4.394.506, issued July 19. 1983 to Levitt discloses herbicidal N-(heterocyclicaminocarbonyl)arylsulfonamides of the formula EMI1.1 wherein. among other substituents. X may be OCH3 or OC H and Y may be F. C1. or Br. Netherlands Patent 121,788. published September 15. 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: EMI1.2 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. U*S. Patent 3.637.366 discloses compounds having the formula: EMI2.1 wherein R1 is hydrogen or lower saturated aliphatic acyl and R2 is hydrogen. 2-pyrinidinyl. pyridyl. asidino. acetyl or carbamoyl. The disclosed compounds are said to provide control of crabgrass, cress. endive, clover and Poa annua. French Pateat No. 1.468,747 discloses the following psra-substituted phenylsulfonamides as being useful as antidiabetic agents: EMI2.2 wherein R = H. halogen, CF3 or alkyl. Logeaann et al., Chem Ab.. 53. 18052g (1959). disclose a number of sulfonamides. including uracil derivatives and those having the formula: EMI2.3 wherein R is butyl. phenyl or EMI2.4 and R1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g). the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive. Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) (Chem. Ab.. 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: EMI3.1 U.S. Patent 4,127.405 teaches compounds which are useful for controlling weeds in wheat having the formula EMI3.2 wherein EMI3.3 R3 and R6 are independently hydrogen. fluorine. chlorine, bromine. iodine, alkyl of 2-4 carbon atoms. alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl. cyano, CH3S(O)n or CH3CH2S(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; 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, trifluoro- methyl, CH3S- or CH3OCH2-; and % is methyl or methoxy; or theier 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 lust be either chlorine or methyl; and (c) when R3 and R7 are both hydro gen. at least one of R4. R5 or R6 must be hydrogen. EP-A-79.683 discloses herbicidal benzofuran and benzothiophine sulfonylureas, wherein the pyrimidin heterocycle may be substituted with. among other values, F or C1. The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs. such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such 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. The need still exists however. for more effective, selective herbicides. Summary of the Invention This invention relates to novel compounds of Formulae I and Ia, agriculturally suitable compositions containing them, and their method-of-use as general or selective preemergent or postemergent herbicides of as plant growth regulants. EMI6.1 wherein R is CH3 or CH2CH3: EMI6.2 EMI7.1 EMI8.1 is i C1-C4 alkyl. C1-C4 alkoxy, oCH2CH2OCH3, F, Cl, Br, NO2, CF3, CO2R15, SO2NR16R17, C(O)R25, CR25(OR26), SO2N(OCH3)CH3, OSO2R18, S(O)nR19, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI8.2 R2 is H, F, Cl, Br, C1-C4 alkyl, C1-C4 alkoxy, C3-C4 alkenyloxy. C3-C4 alkynyloxy, C1-C4 haloalkoxy, C1-C4 haloalkyl, S(O)pC1-C4 alkyl, S(O)pC3-C4 alkenyl, S(O)pC3-C4 alkynyl or C1-C2 alkyl substituted with OCH3 or SCH R3 is H, CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3; R4 is CH3, CH2CH3, OCH3, OCH2CH3m F, Cl, Br, SO2NR16R17, SO2N(OCH3)CH3, S(O)nR19. C3-C4 alkenyloxy or C3-C4 alkynyloxy; R5 is C1-C3 alkyl, F, Cl, Br. NO2, CO2R15. SO2NR16R17, SO2N(OCH3)CH3 or S(O)nR19; R6 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3. OCH3 or OCH2CH3; R7 is H, CH3 or CH2CH3; R8 is H, CH3 or CH2CH3; R9 is H or CH3; R10 is H or CH3; R11 is H or CH3; R12 is H. C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, benzyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, CH2CN, CH2C(O)CH3, CH2CO2(C1-C2 alkyl), C1-C4 alkyl substituted with 0-3 F, 0-1 Cl, OH. OCH3 or OC2H5 or C3-C4 alkenyl sub stituted with 1-3 F or 1-3 C1; R13 is H or CH3; R14 is CH3 or C2H5; R15 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R16 is H. C1-C3 alkyl; R17 is C1-C3 alkyl; R18 is C1-C3 alkyl or N(CH3)2; R19 is C1-C3 alkyl or CH2CH=CH2; R20 is H, Cl or CH3; R21 is H, Cl, CH3 or OCH3; 122 is H or C1-c4 alkyl; R23 is H or CH3: R24 is H or CH3: 125 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl or C3-C6 cycloalkyl, R26 is C1-C2 alkyl: m is 0 or 1: n is O or 2; p is 0, 1 or Z, q is 1 or 2; Q1 is 0, S or SO2; Q2 is O or S; Q3 is 0. S, SO or SO2: and W is 0. S or SO ; provided that 1) the total number of carbon atoms of R16 and R17 is less than or equal to four; 2) when m is 1. then 19 is H; and 3) when R23 is CH3, then Q3 is SO2 and R22 is CH3; and their agriculturally suitable salts. Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are: 1) Compounds of Formula I where R is CH3. 2) Compounds of Preferred 1 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17; 3) Compounds of Preferred 2 where L is L-1; R1 is OCH3, OC2H5, Cl, NO2, CF3, CO2CH3, CO2C2H5, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R18. C(O)CH3, C(O)C2H5, S(O)nR19, OCF2H, SCF2H, OCH2CH=CH2, OCH2C#CH. EMI10.1 12 is H, F. Cl, Br, CH3, C2H5, S(O)pC1-C2 alkyl, S(O)pCH2CH=CH2, S(O)pCH2C#CH, C1-C3 alkoxy. OCH2CH=CH2, OCH2C=CH, C1-C2 halo alkoxy, C1-C2 haloalkyl, CH2OCH3 or CH2SCH3; R18 is C1-C3 alkyl; R19 is CH3 or C2H5; and n is 2. 4) Compounds of Preferred 3 where L is EMI11.1 and R2 is H. F, Cl, Br. CH3, CH2CH3. SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3. 5) Compounds of Preferred 2 where L is L-2; and 13 is Cl. CH3, OCH3, SCH3 or Br. 6) Compounds of Preferred 2 where L is L-3; and R4 is Cl, SO2CH3 or SO2N(CH3)2. 7) Compounds of Preferred 2 where L is L-5; R5 is CO2CH3 or CO2C2H5; and R20 is H. 8) Compounds of Preferred 2 where L is L-8; m is O; R2 is H. F. Cl, Br. CH3, CH2CH3, SCH3, SC2H5. OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3; and R9 is H. 9) Compounds of Preferred 2 where L is L-10; R2 is H, F, Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3, R9 is H; and R12 is H. C1-C4 alkyl, C1-C4 alkylcarbonyl. CH2F or C2-C3 alkyl substituted with 1 F or 1 Cl. 10) Compounds of Preferred 2 where L is L-11; R2 is H, F, Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3; and R9 is H. llr Compounds of Preferred 2 where L is L-16; and R2 is H, F, Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3. 12) Compounds of Preferred 2 where L is L-17; and B2 is H, F. Cl, Br, CH3. CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3 L3) Compounds of Formula Ia where J is J-1; R22 is H, CH3 or C2H5; and 123 is H. Specifically Preferred for reasons of their highest herbicidal activity, greatest growth regulant activity and/or most favorable ease of synthesis are: 2-[[(4-iodo-6-methoxypyrimidin-2-yl)amino carbonyl]aminosulfonyl]benzoic acid, methyl esterm m.p. 194-196 C(d); N'-[(4-iodo-6-methoxypyrimidin-2-yl)amino carbonyl]-N,N-dimethyl-1,2-benzenedisulfon amide, m.p. 231-232, 5 C; and 2-[[(4-iodo-6-methoxypyrimidin-2-yl)amino carbonyl]aminosulfonyl]-4-methylbenzoic acid. methyl ester, m.p. 185-1860C. N-[(4-bromo-6-methoxypyrimidin-2-yl)amino carbonyl]-2,3-dihydrobenzo[b]thiophene-7-sul fonamide, 1.1.dioxide, m.p. 238-240 C. N-[(4-bromo-6-methoxypyrimidin-2-yl)amino carbonyl]-2,3-dihydro-2-methylbenzo[b]thio phene-7-sulfonamide, 1.1.dioxide, m.p. 225-227 C. Detailed DescriPtion of the Invention Synthesis The compounds of Formula I can be prepared by one or more of the following methods described below in Equations 1. 4, 5 and 6. Reaction donditions are given by way of example only. As shown in Equation 1 below, compounds of Formula I can be prepared by reacting an appropriately substituted sulfonyl isocyanate of Formula II with an aminoheterocycle of Formula III where L and R are as previously defined. Equation 1 EMI13.1 The reaction is best carried out in inert aprotic organic solvents such as dichloromethane. 1,2-dichloroethane, tetrahydrofuran, or acetonitrile, at a temperature between 200 and 850C. The order of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate or a solution of it in the reaction solvent to a stirred solution of the amine. In some cases. the desired product is insoluble in the reaction solvent at ambient temperature and crystallizes from it in pure form. Products soluble in the reaction solvent are isolated by evaporation of the solvent. Compounds of Formula I then may be purified by trituration of the evaporation residue with solvents such as l-chlorobutane or ethyl ether and filtration, by recrystallization from mixtures of solvents such as 1.2-dichloroethane, l-chlorobutane and heptane or by chromatography on silica gel. Sulfonylisocyanates of Formula II are known in the art and are prepared from the corresponding sul fonamides (IV) by one of the following two general methods5 equation 2 EMI14.1 The sulfonamide IV and an alkyl isocyanate (e.g., n-butyl isocyanate) in xylene or other solvent boiling above 135 C are mixed in the presence or absence of a catalytic amount of 1,4-diaza[2.2.2]- bicyclooctane (DABCO) and heated to 135-140 C. After 5-60 minutes phosgene is slowly added to the heated mixture at such a rate that the temperature remains between 133 and 1350C. When the consumption of phosgene has ceased, the mixture is cooled and filtered to remove insoluble material. Finally. the solvent, alkyl isocyanate, and excess phosgene are evaporated. leaving the sulfonyl isocyanate (II). If desired, the alkyl isocyanate-sulfonamide adduct can be made and isolated before reaction with the phosgene. In this case the sulfonamide (IV), alkyl isocyanate, and anhydrous base (e.g., K2CO3) in a polar. aprotic solvent (e.g.. acetone, butanone. Or acetonitrile) are mixed and heated under reflux for 1 to 6 hours. The reaction mixture is then diluted with water, and the pH is adjusted to about 3 with acid (e.g., HCl, H2S04). The adduct is filtered out and dried, and then reacted with phosgene as described above. This procedure modification is especially useful when sulfonamide (IV) is high melting and has low solubility in the phosgenation solvent. Sulfonyl isocyanates (II) can also be prepared by the following method. Equation 3 EMI15.1 The sulfonamide (IV) is heated at reflux in an excess of thionyl chloride. The reaction is continued until the sulfonamide protons are no longer detectable in the proton magnetic resonance spectrum. From 16 hours to 5 days is typically sufficient for complete conversion to the thionylamide (V) (Equation 3a). The thionyl chloride is evaporated and the residue is treated with an inert solvent (e.g., toluene) containing at least one equivalent (typically 2-3 equivalents) of phosgene. A catalytic amount of pyridine (typically 0.1 equivalent) is added, and the mixture is heated to about 60-140"C. with 80-100 preferred. Conversion to the isocyanate (II) is usually substantially complete within 15 minutes to 3 hours (Equation 3b). The mixture is then cooled and filtered, and the solvent is evaporated, leaving the sulfonyl isocyanate (II). Many of the compounds of Formula I can be prepared by the procedure shown in Equation 4. Equation 4 EMI16.1 The reaction shown in Equation 4 is carried out by contacting phenylcarbarates of Formula VI with aminoheterocycles of Formula III in an inert organic solvent such as dioxane or tetrahydrofuran at temperatures of about 20-1000C for a period of about one-half to twenty-four hours. The product can be isolated by evaporation of the reaction solvent and purified by methods previously described. Phenyl carbamates of Formula VI can be prepared by the methods described. or modifications thereof known to those skilled in the art. in European Patent Application 81810282.4 (Publ. No. 44,808). published January 27. 1982; or South African Patent Application 825042. Alternatively. many of the compounds of Formula I can be prepared by the method described in Equation 5. Equation 5 EMI16.2 The reaction of Equation 5 can be carried out by contacting equimolar amounts of a sulfonamide of Formula IV with a heterocyclic phenylcarbamate of Formula VII in the presence of a base such as 1,8 diazabicyclo(5.4.O)undec-7-ene (DBU), by methods analagous to those described in South African Patent Application 830441. The phenyl carbamates of Formula VII can be prepared by methods, or modifications thereof known to those skilled in the art, described in South African Patent Application 825671 and South African Patent Application 825045. Rarely, a sulfonamide of Formula IV may not be of sufficient stability to be useful as a starting material in any of the above procedures. In these cases, as well as others. the sulfonyl isocyanate of Formula II can be prepared as an unisolated intermediate by treating the corresponding sulfonyl chloride (VIII) with isocyanate anion in the presence of the heterocyclic amine of Formula III as shown in Equation 6. Equation 6 EMI17.1 The reaction is best carried out by adding over one to six hours a solution of at least one equivalent of a tetraalkylammonium isocyanate, such as tetra-nbutylammonium isocyanate, in a suitable aprotic organic solvent, such as dichloromethane or tetrahydrofuran, to a well-stirred mixture of one equivalent of sulfonyl chloride of Formula VIII and at least one equivalent of heterocyclic amine of Formula III in a similar suitable organic solvent at 20-400C. The reaction mixture is then diluted with dichloromethane. washed with 1N sulfuric acid, and dried over sodium sulfate. Rotary evaporation of the solvent leaves the product of Formula I in crude form. This may be purified as has already been described for Equation 1. Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene. naphthalene, or thiophene in tetrachlororethane according to the teachings of H. T. Clarke et al., Ora. 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 hydrochloric acid, followed by reaction of the diazonium salt with sulfur dioxide and cuprous or cupric chloride in acetic acid according to the teachings of H. L. Yale and F. Sowinski. J. Org. Chem.. 25. 1824 (1960) and of H. Meerwein et al.. Chem. Ber.. 90, 841 (1957). Reference to the following patents is suggested for further details regarding the preparation of the sulfonamides (IV) and sulfonyl isocyanates (II): U.S. Patent 4,169,719; U.S. Patent 4,127,405; U.S. Patent 4,394,506; and E.P.-A-79,683. Iodopyrimidines of Formula III can be prepared by the procedure shown in Equation 7. Equation 7 EMI18.1 Treatment of a 2-amino-4-chloro-6-alkoxypyrimi- dines of Formula IX with 57% aqueous hydroiodic acid according to procedures found in J. Chem. Soc. C, 1204 (1967) gives the lodopyrimidines of Formula III. The chioropyrimidines of Formula IX are known in the art. Compounds of Formula Ia may be prepared utilizing the procedures of Equations 1-6, the corresponding sulfonylisocyanates of formula JSO2NCO or the sulfonamides of formula JSO2NH2 and the corresponding aminoheterocycle 2-amino-4-bromo-6methoxypyrimidine. For the preparation of 2-amino4-bromo-6-methoxypyrimidine see T. Hirayama. et al.. Heterocvcles, 2, 461 (1974). Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g.. hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g.. alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble. Acid addition salts. useful in this invention. can be obtained by reacting a compound of Formula I with a suitable acid. e.g.. g-toluenesulfonic acid. trichloroacetic acid or the like. The synthetic routes described above are equally applicable, mutatis mutandis,to the preparation of compounds of formula Ia and their agriculturally suitable salts. The following examples further illustrate the synthesis of this invention. Example 1 2-Amino-4-iodo-6-methoxypyrimidine 18.0 g of 2-Amino-4-chloro-6-methoxypyrimidine was added to 65 IL of 57S aqueous hydroiodic acid with ice bath cooling. The resulting thick mixture was kept at ambient temperature for 65 hours. diluted with water and neutralized with potassiun carbonate. The solid was collected and recrystallized from aqueous ethanol to give 5.0 g of white crystals. m.p. 141.5-1440C. NMR(CDCl3): 3.82 (s, 3H, OCH3): 5.3 (br s, 2H, NH2); and 6.54 (s, 1H, pyr CS-H). Example 2 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. To a solution of 0.25 g of 2-amino-4-iodo-6methoxypyrimidine in 5 mL of dry methylene chloride was added 0.30 g 2-carbomethoxybenzenesulfonyl isocyanate. The resulting solution was allowed to stand for 20 hours at ambient temperature. The solution was cooled in an ice bath and crystallization induced with scratching. The crystals were collected, washed with n-butylchloride and dried to afford 0.10 g of the title compound. m.p. 194-1960C (dec). IR (nujol) 178 cm-1 (ester) and 1705 cm-1 (sulfonylurea). NMR (CDCl 3.94 (s, 3H. CO2CH3); 4.06 (s, 3H. OCH3): 6.95 (s, 1H, pyr. C5-H); 7.4 (br s, 1H, NH); 7.75 (m, 3H, aromatics); 8.4 (1, 1H. aromatic); and 12.15 (br s, 1H, NH). ExamPle 3 N-((4-Bromo-6-methoxypyrimidin-2-yl)aminocarbonyl)- 2,3-dihydrobenzo[b]thiophene-7-sulfonamide, 1,1-dioxide A suspension of 5.0 g (20 mmol) of 2,3-dihydro benzotb]thiophene-7-sulfonamide-1,1-dioxide in 50 mL of thionyl chloride was refluxed for 40 hours. cooled. diluted with 100 mL of dry toluene and fractionally distilled to remove excess thionyl chloride. The cooled toluene solution was contacted with 2 drops of pyridine and 3 mL of liquified phosgene and the mixture was refluxed for 3 hours, cooled and concentrated in vacuo to give 5.8 g of 2,3-dihydrobenzo[b]thio- phene-7-sulfonylisocyanate-1,l-dioxide as a brown powder whose IR spectrum exhibited a strong band at 2250 cm A solution of 1.4 g (5 mmol) of the crude isocyanate and 0.82 g (4 mmol) of 2-amino-4-bromo-6methoxypyrimidine in 20 mL of dry methylene chloride was heated to reflux for 5 minutes and stirred at room temperature for 16 hours. The resulting precipitate was filtered, washed with dry methylene chloride and anhydrous ether and air dried to give 1.6 g of the title compound as a white powder, m.p. 238-240 C. 200 MHz 1H NMR (DMSO-d6): 6 12.2 (br. 1H. NH); 10.9 (b, 1H. NH); 8.1 (m, 1H. arom); 7.9 (m. 2H. arom); 7.0 (5. 1H. CH) 4.0 (s. 3H. OCH3); 3.7 (m. 2H, CH2); and 3.4 (m, 2H, CH2) ppm. IR (nujol): 3380, 1730. 1710 cm 1. Using the procedures and examples shown above. the compounds in Tables 1-19 can be prepared. General Structures for Tables General Structure 1 EMI22.1 General Structure 2 EMI22.2 General Structure 3 EMI22.3 General Structure 4 EMI22.4 EMI22.5 General Structures for Tables (continued) General Structure 6 EMI23.1 General Structure 7 EMI23.2 General Structure 8 EMI23.3 General Structure 9 EMI23.4 General Structures for Tables (continued) General Structure 10 EMI24.1 General Structure 11 EMI24.2 General Structure 12 EMI24.3 General Structure 13 EMI24.4 General Structures for Tables (continued) General Structure 14 EMI25.1 General Structure 15 EMI25.2 General Structure 16 EMI25.3 General Structure 17 EMI25.4 General Structures for Tables (continued) General Structure 18 EMI26.1 General Structure EMI26.2 Table 1 General Structure 1 R R1 R2 m.p. ( C) CH3 CH3 H CH3 CH2CH3 H CH3 CH2CH2CH3 H CH3 CH2(CH3)2 H CH3 CH(CH3)CH2CH3 H CH3 OCH3 H CH3 OCH2CH3 H CH3 OCH2CH2CH3 H CH3 OCH(CH3)2 H CH3 OCH2CH2CH2CH3 H CH3 OCH2CH2CH3 H CH3 F H CH3 Cl H 197-200 (dec) CH3 Br H CH3 NO2 H 223.5-225 (dec) CH3 CF3 H 217-220 (dec) CH3 CO2CH3 H 194-196 (dec) CH3 CO2CH3 5-F CH3 CO2CH3 3-Cl CH3 CO2CH3 5-Cl CH3 CO2CH3 6-Cl CH3 CO2CH3 5-Br CH3 SO2CH3 5-CF3 148-150 CH3 CO2CH3 5-CH3 185-187 CH3 CO2CH3 5-OCH3 195-197 CH3 CO2CH3 5-OCH2CH3 CH3 CO2CH3 5-SCH3 CH3 CO2CH3 5-OCF2H CH3 CO2CH3 3-CH3 CH3 CO2CH2CH3 H 186-187.5 (dec) CH3 CO2CH2CH3 3-Cl Table 1 (continued) R R1 R2 m.p. ( C) CH3 CO2CH2CH3 5-Cl CH3 CO2CH2CH3 6-Cl CH3 CO2CH2CH3 5-CF3 CH3 CO2CH2CH3 3-CH3 CH3 CO2CH2CH3 5-CH3 CH3 CO2CH2CH3 5-OCH3 CH3 CO2CH2CH3 5-SCH3 CH3 CO2CH2CH3 5-OCF2H CH3 CO2CH2CH3 5-OCH2CH3 CH3 CO2CH(CH3)2 3-Cl CH3 CO2CH(CH3)2 5-Cl CH3 CO2CH(CH3)2 6-Cl CH3 CO2CH(CH3)2 5-CF3 CH3 CO2CH(CH3)2 3-CH3 CH3 CO2CH(CH3)2 5-CH3 CH3 CO2CH(CH3)2 5-OCH3 CH3 CO2CH(CH3)2 5-OCF2H CH3 CO2CH2CH2CH3 H CH3 CO2CH2CH2CH3 5-OCH3 CH3 CO2CH2CH2CH3 5-CH3 CH3 CO2CH2CH(CH3)2 H CH3 CO2CH(CH3)CH2CH3 H CH3 CO2CH2CH2CH3 H CH3 CO2CH2CH2OCH3 H CH3 CO2CH2CH2OCH3 5-CF3 CH3 CO2CH2CH2OCH3 5-Cl CH3 CO2CH2CH2OCH3 5-OCH3 CH3 CO2CH2CH2Cl 5-CH3 CH3 CO2CH2CH2Cl H CH3 CO2CH2CH2Cl 5-OCH3 CH3 CO2CH2CH=CH2 H CH3 CO2CH2CH=CH2 5-CF3 Table 1 (continued) R 1 R2 m.p. ( C) CH3 CO2CH2CH=CH2 5-OCH3 CH3 SO2N(CH3)2 H 231-232.5 (dec) CH3 SO2N(CH3)2 3-Cl CH3 SO2N(CH3)CH2CH3 H CH3 S02N(CH2CH3)2 H CH3 S02N(CH3)CH(CH3)2 H CH3 SO2N(CH3)CH2CH2CH3 H CH3 OSO2CH3 H 217-219 (dec) CH3 OSO2CH3 5-Cl CH3 OSO2CH2CH3 H CH3 OSO2CH(CH3)2 H CH3 OSO2CH2CH2CH3 H CH3 OSO2N(CH3)2 H CH3 SCH3 H 116-120 CH3 SCH2CH3 H CH3 SCH2CH2CH3 H CH3 SCH(CH3)2 H CH3 SCH2CH=CH2 H CH3 SOH3 H CH3 SOCH2CH3 H CH3 SO2CH3 H 239-241 (dec) CH3 SO2CH2CH3 H CH3 SO2CH2CH2CH3 H CH3 SO2CH(CH3)2 H CH3 SO2CH2CH=CH2 H CH3 SCF3 H CH3 SO2CF3 H CH3 OCF3 H CH3 SCF2H H CH3 SO2CF2H H CH3 OCF2H H CH3 OCH2CH=CH2 H EMI30.1 <tb> <SEP> Table <SEP> 1 <SEP> (continued) <tb> H <SEP> R1 <SEP> R2 <SEP> m..(0C) <tb> CR3 <SEP> 0CH2CH¯CHCH3 <SEP> H <tb> cH3 <SEP> OCE(CE3)CH=CH2 <SEP> H <tb> CR3 <SEP> OCR2 <SEP> CECH <SEP> H <tb> CR3 <SEP> OCR2CECCR3 <SEP> H <tb> CR3 <SEP> OCR(CR3)CECR <SEP> H <tb> 3 <SEP> CR2OCR3 <SEP> H <tb> CR3 <SEP> CR2OCR2CR3 <SEP> H <tb> 3 <SEP> CR2 <SEP> CR2 <SEP> OCR3 <SEP> H <tb> CH3 <SEP> CR(CH3)OCR3 <SEP> H <tb> CH3 <SEP> C6H5 <SEP> H <tb> <SEP> 11 <tb> CR3 <SEP> PI <SEP> Y\ <SEP> R <tb> <SEP> / <SEP> 0 <SEP> cm3 <tb> <SEP> N-N <tb> CR3 <SEP> A <SEP> O <SEP> t <SEP> H <tb> <SEP> 0 <tb> 3 <SEP> S <SEP> p <SEP> n <SEP> H <tb> CH <SEP> 2 <SEP> H <tb> <SEP> sr--N <tb> CH3 <SEP> 4\ <SEP> H <tb> <SEP> U <tb> Clef3 <SEP> 5-Cl <tb> <SEP> aVD <tb> CR3 <SEP> < \ <SEP> H <tb> <SEP> I <tb> CR3 <SEP> H <tb> <SEP> ICX, <tb> 3 <SEP> t <SEP> ; <SEP> H <tb> <SEP> o <tb> Table 1 (continued) EMI31.1 <tb> R <SEP> 1 <SEP> 2 <SEP> m..(0C) <tb> CH3 <SEP> oN <SEP> O <SEP> H <tb> <SEP> w <tb> CR3 <SEP> H <tb> CH3 <SEP> 4 <SEP> H <tb> CH3 <SEP> <SEP> H <tb> CH3 <SEP> 'im <SEP> H <tb> CR3 <SEP> B <SEP> H <tb> CH3 <tb> CR2 <SEP> CR3 <SEP> CH3 <SEP> H <tb> CH2CH3 <SEP> CH2CH3 <SEP> H <tb> CH2CH3 <SEP> CH2CH2CH3 <SEP> H <tb> CR2CH3 <SEP> CH(CH3)2 <SEP> H <tb> CR2CH3 <SEP> CH(CH3)CH2CH3 <SEP> H <tb> CH2CH3 <SEP> OCH3 <SEP> H <tb> CR2CR3 <SEP> OCR2CH3 <SEP> H <tb> CH2CH3 <SEP> OCR2 <SEP> CR2 <SEP> CR3 <SEP> H <tb> CR2CR3 <SEP> OCH(CH3)2 <SEP> 2 <SEP> H <tb> CR2 <SEP> CR3 <SEP> OCH2CR2CR2CR3 <SEP> H <tb> CH2CH3 <SEP> OCH2CH20CH3 <SEP> H <tb> CHzCH3 <SEP> F <SEP> H <tb> Tabel 1 (continued) R R1 R2 m.p. ( C) CH2CH3 Cl H CH2CH3 Br H CH2CH3 NO2 H CH2CH3 CF3 H CH2CH3 CO2CH3 H CH2CH3 CO2CH3 5-F CH2CH3 CO2CH3 3-Cl CH2CH3 CO2CH3 5-Cl CH2CH3 CO2CH3 6-Cl CH2CH3 CO2CH3 5-Br CH2CH3 CO2CH3 5-CF3 CH2CH3 CO2CH3 5-CH3 CH2CH3 CO2CH3 5-OCH3 CH2CH3 CO2CH3 5-OCH2CH3 CH2CH3 CO2CH3 5-SCH3 CH2CH3 CO2CH3 5-OCF2H CH2CH3 CO2CH3 3-CH3 CH2CH3 CO2CH2CH3 H CH2CH3 CO2CH2CH3 3-Cl CH2CH3 CO2CH2CH3 5-Cl CH2CH3 CO2CH2CH3 6-Cl CH2CH3 CO2CH2CH3 5-CF3 CH2CH3 CO2CH2CH3 3-CH3 CH2CH3 CO2CH2CH3 5-CH3 CH2CH3 CO2CH2CH3 5-OCH3 CH2CH3 CO2CH2CH3 5-SCH3 CH2CH3 CO2CH2CH3 5-OCF2H CH2CH3 CO2CH2CH3 5-OCH2CH3 CH2CH3 CO2CH(CH3)2 3-Cl CH2CH3 CO2CH(CH3)2 5-Cl CH2CH3 CO2CH(CH3)2 6-Cl CH2CH3 CO2CH(CH3)2 5-CF3 Table 1 (continued) R R1 R2 m.p. ( C) CH2CH3 CO2CH(CH3)2 3-CH3 CH2CH3 CO2CH(CH3)2 5-CH3 CH2CH3 CO2CH(CH3)2 5-OCH3 CH2CH3 CO2CH(CH3)2 5-OCF2H CH2CH3 CO2CH2CH2CH3 H CH2CH3 CO2CH2CH2CH3 5-OCH3 CH2CH3 CO2CH2CH2CH3 5-CH3 CH2CH3 CO2CH2CH(CH3)2 H CH2CH3 CO2CH(CH3)CH2CH3 H CH2CH3 CO2CH2CH2CH2CH3 H CH2CH3 CO2CH2CH2OCH3 H CH2CH3 CO2CH2CH2OCH3 5-CF3 CH2CH3 CO2CH2CH2OCH3 5-Cl CH2CH3 CO2CH2CH2OCH3 5-OCH3 CH2CH3 CO2CH2CH2Cl 5-CH3 CH2CH3 CO2CH2CH2Cl H CH2CH3 CO2CH2CH2Cl 5-OCH3 CH2CH3 CO2CH2CH=CH2 H CH2CH3 CO2CH2CH=CH2 5-CF3 CH2CH3 CO2CH2CH=CH2 5-OCH3 CH2CH3 SO2N(CH3)2 H CH2CH3 SO2N(CH3)2 3-Cl CH2CH3 SO2N(CH3)CH2CH3 H CH2CH3 SO2N(CH2CH3)2 H CH2CH3 SO2N(CH3)CH2(CH3)2 H CH2CH3 SO2N(CH3)CH2CH2CH3 H CH2CH3 OSO2CH3 H CH2CH3 OSO2CH3 5-Cl CH2CH3 OSO2CH2CH3 H CH2CH3 OS02CH(CH3)2 H CH2CH3 OSO2CH2CH2CH3 H CH2CH3 OSO2N(CH3)2 H Table 1 (continued) EMI34.1 <tb> <SEP> H <SEP> H <tb> <SEP> H <SEP> 1 <SEP> 2 <SEP> m.P. <SEP> ( C) <tb> CH2CH3 <SEP> SCH3 <SEP> H <tb> CR2CR3 <SEP> SCH2CR3 <SEP> H <tb> CHZCH3 <SEP> SCH2CH2CH3 <SEP> H <tb> 2 <SEP> 3 <SEP> SCH(CR3)2 <SEP> H <tb> CH2CH3 <SEP> SCH2CH=CH2 <SEP> H <tb> 2 <SEP> 3 <SEP> SOCH3 <SEP> H <tb> CH2CH3 <SEP> SOCR2CH3 <SEP> H <tb> Z <SEP> 3 <SEP> 2 <SEP> 3 <SEP> SO2CR3 <SEP> H <tb> CH2CH3 <SEP> SO2CR2CR3 <SEP> H <tb> CR2 <SEP> CR3 <SEP> 2 <SEP> 2 <SEP> 2 <SEP> 3 <SEP> H <tb> CR2CR3 <SEP> S02CH(CH3)2 <SEP> H <tb> 2 <SEP> 3 <SEP> 2 <SEP> 2 <SEP> SO <SEP> CRCR=CR <SEP> H <tb> <SEP> 22 <SEP> 2 <tb> 2 <SEP> 3 <SEP> SCF3 <SEP> H <tb> CR2CH3 <SEP> 2 <SEP> CF3 <SEP> H <tb> CH2CH3 <SEP> OC?3 <SEP> H <tb> CH2CH3 <SEP> SC?2H <SEP> H <tb> CH2CH3 <SEP> SO2CF2R <SEP> H <tb> CH2CH3 <SEP> OCF2H <SEP> H <tb> CH2CH3 <SEP> OCH2CH=CH2 <SEP> H <tb> CR2CR3 <SEP> OCH2CH=CHCH3 <SEP> H <tb> CH2CH3 <SEP> OCR(CR3)CR=CR2 <SEP> H <tb> CR2CH3 <SEP> OCH2C=CH <SEP> H <tb> CH2CH3 <SEP> OCH2CiCCH3 <SEP> H <tb> CE2CH3 <SEP> OCR(CR3)C=CH <SEP> H <tb> CR2CR3 <SEP> CEzOCH3 <SEP> H <tb> Z <SEP> 3 <SEP> u2 CH2cH3 <SEP> H <tb> CR2CR3 <SEP> CR2CH2OCR3 <SEP> H <tb> CH2CH3 <SEP> CH(CH3)OCH3 <SEP> H <tb> CH2CH3 <SEP> C <SEP> 6H5 <SEP> H <tb> <SEP> 'p- <tb> CR2CR3 <SEP> R,X <SEP> H <tb> <SEP> 3 <tb> CH2CH3 <SEP> 4 <SEP> 0 <SEP> H <tb> Table 1 (continued) EMI35.1 <tb> <SEP> R <SEP> 1 <SEP> R2 <SEP> m.P. <SEP> ( C) <tb> CR2 <SEP> CR3 <SEP> H <tb> CH2CH3 <SEP> X <SEP> N <SEP> H <SEP> R <tb> C <SEP> R2 <SEP> CR3 <SEP> H <tb> <SEP> 2 <tb> CH2CH3 <SEP> 4 <SEP> H <tb> <SEP> 2 <SEP> JJS <tb> CH2CH3 <SEP> 5-C1 <tb> <SEP> S <tb> CH2CH3 <SEP> 4 <SEP> O <SEP> H <tb> CH2CH3 <SEP> N,NCH3 <SEP> H <tb> CH2CH3 <SEP> H <tb> <SEP> N <tb> CR2 <SEP> CR3 <SEP> H <tb> CR2 <SEP> CR3 <SEP> H <tb> CR2 <SEP> CR3 <SEP> H <tb> CH2CH3 <SEP> H <tb> Table 1 (continued) EMI36.1 <tb> <SEP> H <SEP> 1 <SEP> H2 <SEP> r,D. <SEP> (OC) <tb> CR2CR3 <SEP> R <tb> 2CH3 <SEP> <SEP> H <tb> CR2 <SEP> CR3 <SEP> H <tb> CH2CH3 <SEP> t) <SEP> H <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-CR2CR3 <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-CR2CR2CR2CR3 <tb> CH3 <SEP> COUCH3 <SEP> 5-QCH <SEP> CH <SEP> CR2CR3 <tb> CR3 <SEP> 2 <SEP> CR3 <SEP> 5-oCH2CH=CH2 <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-oCH2C-CH <tb> CR3 <SEP> cO2CR3 <SEP> 5-OCH2CHClCH2CH3 <tb> 3 <SEP> 2 <SEP> 3 <SEP> 5-SOCH3 <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-SCHzCH=CH2 <tb> CH3 <SEP> 2 <SEP> 3 <SEP> 5-SCR2C=CR <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-5CH2CH2C-CH <tb> 3 <SEP> CO2CR3 <SEP> 5-CR2OCR3 <tb> CR3 <SEP> 2 <SEP> 3 <SEP> 5-CR2SCR3 <tb> CH3 <SEP> 2 <SEP> 3 <SEP> 5-CH2CH2CH3 <tb> CH3 <SEP> 2 <SEP> 3 <SEP> 5-OCH2CHzCH3 <tb> CR3 <SEP> COUCH3 <SEP> 5-OCR2CR2CH=CR2 <tb> a3 <SEP> CO2CR3 <SEP> 5-OCH2CH2C=CH <tb> CH3 <SEP> 2 <SEP> 3 <SEP> 5-OCF2CF2R <tb> CR3 <SEP> CO2CR3 <SEP> 5-SO2CH3 <tb> Table 1 (continued) R R1 R2 m.p. ( C) CH3 CO2CH3 5-SCH2CH12CH=CH2 CH3 CO2CH3 5-CH2CH2OCH3 CH3 CO2CH3 5-SO2CH2CH3 CH3 CO2CH3 5-SO2CH2CH2CH2CH3 CH3 CO2CH3 5-SO2CH2CH=CH2 CH3 CO2CH3 5-SO2CH2C#CH Table 2 General Structure 2 R R3 m.p. ( C) CH3 CH3 CH2CH3 CH3 CH3 OCH3 C2CH3 OCH3 CH3 F CH3 H CH3 Cl CH2CH3 Cl CH3 Br CH2CH3 Br CH3 SO2N(CH3)2 CH3 OSO2CH3 CH3 SCH3 CH3 SOCH3 CH3 SO2CH3 Table 3 General Structure R R4 m.p. ( C) CH3 CH3 CH3 CH2CH3 CH3 OCH3 CH2CH3 OCH3 CH3 OCH2CH3 CH3 F CH3 Cl CH2CH3 Cl CH3 Br CH3 SO2N(CH3)2 CH3 SO2N(CH2CH3)2 CH3 SO2N(OCH3)CH3 CH3 SO2CH3 CH3 SCH3 CH3 SOCH3 CH3 SCH2CH3 CH3 SO2CH2CH3 CH3 SO2CH2CH(CH3)2 CH3 SO2CH2CH2CH3 CH3 SCH2CH=CH2 CH3 SO2CH2CH=CH2 CH3 OCH2CH=CH2 CH2CH3 OCH2CH=CH2 CH3 OCH(CH3)CH=CH2 CH3 OCH2C#CH CH3 OCH2C#CCH3 Table 4 General Structure 4 R R5 R20 m.p. ( C) CH3 CH3 H CH3 CH2CH3 H CH3 CH2CH2CH3 H CH3 CH(CH3)2 5-Cl CH3 F H CH3 Cl H CH3 Br H CH3 NO2 H CH3 CO2CH3 H CH3 CO2CH2CH3 H CH3 CO2CH(CH3)2 H CH3 CO2CH2CH2CH3 H CH3 CO2CH(CH3)CH2CH3 H CH3 CO2CH2CH2OCH3 H CH3 CO2CH2CH2Cl H CH3 CO2CH2CH=CH2 H CH2CH3 CO2CH3 H CH2CH3 C02CH2CH3 5-CH3 CH3 SO2N(CH3)2 H CH3 SO2N(CH2CH3)2 H CH3 SO2N(OCH3)CH3 H CH3 SCH3 H CH3 SOCH3 H CH3 SO2CH3 H CH3 SCH2CH3 H CH3 SCH2CH2CH3 H CH3 SCH2CH=CH2 H Table 5 General Structure 5 R R5 R20 m.p. ( C) CH3 CH3 H CH3 CH2CH3 H CH3 CH2CH2CH3 H CH3 CH(CH3)2 5-Cl CH3 F H CH3 Cl H CH3 Br H CH3 NO2 H CH3 CO2CH3 H CH3 CO2CH2CH3 H CH3 CO2CH(CH3)2 H CH3 CO2CH2CH2CH3 H CH3 CO2CH(CH3)CH2CH3 H CH3 CO2CH2CH2OCH3 H CH3 CO2CH2CH2Cl H CH3 CO2CH2CH=CH2 H CH2CH3 CO2CH3 H CH2CH3 CO2CH2CH3 5-CH3 CH3 SO2N(CH3)2 H CH3 SO2N(CH2CH3)2 H CH3 SO2N(OCH3)CH3 H CH3 SCH3 H CH3 SOCH3 H CH3 SO2CH3 H CH3 SCH2CH3 H CH3 SCH2CH2CH3 H CH3 SCH2CH=CH2 H Table 6 General Structure 6 R R5 R20 m.p. ( C) CH3 CH3 H CH3 CH2CH3 H CH3 CH2CH2CH3 H CH3 CH(CH3)2 2-C1 CH3 F H CH3 Cl H CH3 Br H CH3 NO2 H CH3 CO2CH3 H CH3 CO2CH2CH3 H CH3 CO2CH(CH3)2 H CH3 CO2CH2CH2CH3 H CH3 C02CH(CH3)CH2CH3 H CH3 CO2CH2CH2OCH3 H CH3 CO2CH2CH2Cl H CH3 CO2CH2CH=CH2 H CH2CH3 CO2CH3 H CH2CH3 CO2CH2CH3 2-CH3 CH3 SO2N(CH3)12 H CH3 S02N(CH2CH3)2 H CH3 SO2N(OCH3)CH3 H CH3 SCH3 H CH3 SOCH3 H CH3 SO2CH3 H CH3 SCH2CH3 H CH3 SCH2CH2CH3 H CH3 SCH2CH=CH2 H Table 7 General Structure 7 R R6 m.p. ( C) CH3 Cl CH3 NO2 CH3 CO2CH3 CH2CH3 CO2CH3 CH3 CO2CH2CH3 CH2CH3 CO2CH2CH3 CH3 SO2N(CH3)2 CH3 OSO2CH3 CH3 SO2CH3 CH3 SO2CH2CH3 CH3 OCH3 CH3 OCH2CH3 Table 8 General Structure 8 R R2 R7 R8 R9 m Q1 m.p. ( C) CH3 H H H H O O CH3 H CH3 H H O O CH3 H CH3 CH3 H O O CH3 H R H CH3 O 0 CH3 H H CH3 H 1 O CH3 H CH3 CH3 H 1 O CH3 H CH3 H H O S CH3 H CH3 CH3 H O S CH3 H H H CH3 O S CH3 H CH3 H H 1 S CH3 H CH3 CH3 H 1 S CH3 H H H H O SO2 CH3 H CH3 H H O SO2 CH2CH3 H CH3 H H O SO2 CH3 H CH3 CH3 H O SO2 CH2CH3 H CH3 CH3 H O SO2 CH3 H CH3 H CH3 O SO2 CH3 H CH3 H H 1 SO2 CH3 H CH3 CH3 H 1 SO2 CH3 H CH2CH3 H H O SO2 CH3 H CH2CH3 H H 1 SO2 CH3 6-Cl CH3 H H O S02 CH3 7-Cl CH3 H H 1 SO2 CH3 5-Br CH3 H H O 0 CH3 6-CH3 CH3 H H O SO2 CH3 7-C1 CH3 H H 1 S CH3 6-Cl CH3 CH3 H O SO2 Table 9 General Structure 9 R R2 R10 R11 Q2 m.p. ( C) CH3 H H H O CH3 H CH3 H O CH3 H CH3 CH3 O CH2CH3 H H H O CH2CH3 H CH3 H O CH2CH3 H CH3 CH3 O CH3 H H H S CH3 H CH3 H S CH3 H CH3 CH3 S CH2CH3 H H H S CH2CH3 H CH3 H S CH2CH3 H CH3 CH3 S Table 10 General Structure 10 R R2 R10 R11 Q2 m.p. ( C) CH3 H H CH3 0 CH3 H CH3 CH3 0 CH3 H H CH3 1 CH2CH3 H H CH3 0 CH2CH3 H CH3 CH3 0 CH2CH3 H H CH3 1 CH3 H H CH2CH3 0 CH3 H H CH2CH2CH3 0 CH3 H H CH(CH3)2 0 CH3 H H CH2CH2CH2CH3 0 CH3 H H CH(CH3)CH2CH3 0 CH3 H H CH2CH(CH3)2 0 CH3 H H CH2CH3 1 CH3 H H CH(CH3)2 1 Table 10 (continued) R R2 R9 R12 m m.p. ( C) CH3 H CH2CH2CH3 1 CH3 6-Cl H CH3 0 CH3 H H CH2CH2F O CH3 H H CH2CH2OCH3 0 CH3 H H CH2CH=CH2 0 CH3 H H CH2C#CH 0 CH3 H H CH2C6H5 0 CH3 H H C(O)CH3 0 CH3 H H C(O)CH2CH2CH3 1 CH3 H H CO2CH3 0 CH3 H H CH2CN O CH3 H H CH2C(O)CH3 0 CH3 H H CH2CO2CH3 0 CH3 H H CH2CF=CF2 1 CH3 H H CH2CH=CCl2 0 CH3 H H CH2CH2F O CH3 H H CH2OCH3 0 Table 11 General Structure 11 R R2 R9 m m.p. ( C) CH3 H H 0 CH3 H CH3 0 CH3 H H 1 183-186 CH2CH3 H H O CH2CH3 H CH3 0 CH2CH3 H H 1 CH3 6-C1 H O CH3 7-C1 H 1 CH3 6-C1 H 1 CH3 6-CH3 H 1 Table 12 General Structure 12 R R2 R9 m m.p. ( C) CH3 H H O CH3 H CH3 1 CR3 H H 1 CR2CR3 H H O CH2CH3 H CH3 0 CH2CH3 H H 1 Table 13 General Structure 13 R R2 R9 m m.p. ( C) CH3 H H O CH3 H CH3 0 CH3 H H 1 CH2CH3 H H O CH2CH3 H CH3 0 CH2CH3 H H 1 Table 14 General Structure 14 R R2 R12 m.p. ( C) CH3 H CH3 CH2CH3 H CH3 CH3 H CH2CH3 CH2CH3 H CH2CH3 CH3 H CH2CH2CH3 CH3 H CH(CH3)2 CH3 H CH2H2CH2CH3 CH3 H CH(CH3)CH2CH3 CH3 H CH2CH(CH3)2 Table 15 General Structure 15 R R2 13 m.p. ( C) CH3 H H CH3 H CH3 CH2CH3 H H CH2CH3 H CH3 Table 16 General Structure 16 R R2 R13 m.p. ( C) CH3 H H CH3 H CH3 CH2CH3 H H CH2CH3 H CH3 Table 17 General Structure 17 R R2 R13 R14 m.p. ( C) CH3 H H CH3 CH3 H H CH2CH3 CH3 H CH3 CH3 CH3 H CH3 CH2CH3 CH2CH3 H H CH3 CH2CH3 H H CH2CH3 CH2CH3 H CH3 CH3 CH2CH3 H CH3 CH2CH3 CH3 6-Cl H CH3 CH3 6-CH3 H CH3 CH3 6-C1 CH3 CH3 CH3 7-C1 H CH3 Table 18 General Structure 18 q V3 N21 N22 R23 m.p. ( C) 1 O H H H 197-201 1 O H CH3 H 1 O H CH2CH3 H 1 O H CH2CH2CH3 H 1 O E CH2CH2CH2CH3 H 1 O H CH(CH3)2 H 1 0 H CH(CH3)2CH2CH3 H 1 O H CH2CH(CH3)2 H 1 O o-Cl H H 1 O o-Cl CH3 H 1 O o-Cl CH2CH3 H 1 O o-Cl CH2CH2CH3 H 1 O o-Cl CH2CH2CH2CH3 H 1 O o-Cl CH(CH3)2 H 1 O o-Cl CH(CH3)CH2CH3 H 1 O o-Cl C2CH(CH3)2 H 1 O s-C1 H H 1 O m-Cl CH3 H 208-211 1 O m-Cl CH2CH3 H 1 O m-Cl CH2CH2CH3 H 1 O m-Cl CH2CH2CH2CH3 H 1 O m-Cl CH(CH3)2 H 1 O m-Cl CH(CH3)CH2CH3 H 1 O m-Cl CH2CH(CH3)2 H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 0 o-CH3 H H 1 0 o-CH3 CH3 H 1 0 o-CH3 CH2CH3 H 1 0 o-CH3 CH2CH2CH3 H 1 O o-CH3 CH32CH2CH2CH3 H 1 0 o-CR3 CH(CH3)2 H 1 O o-CH3 CH(CH3)CH2CH3 H 1 O o-CH3 CH2CH(CH3)2 H 1 O m-CH3 H H 1 O m-CH3 CH3 H 1 O m-CH3 CH2CH3 H 1 O m-CH3 CH2CH2CH3 H 1 O m-CH3 CH2CH2CH2CH3 H 1 O m-CH3 CH(CH3)2 H 1 O m-CH3 CH(CH3)CH2CH3 H 1 O m-CH3 CH2CH(CH3)2 H 1 O o-OCH3 H H 1 O o-OCH3 CH3 H 1 O o-OCH3 CH2CH3 H 1 O o-OCH3 CH2CH2CH3 H 1 O o-OCH3 CH2CH2CH2CH3 H 1 O o-CH3 CH(CH3)2 H 1 O o-CH3 CH(CH3)CH2CH3 H 1 O o-OCH3 CH2CH(CH3)2 H 1 O m-CH3 H H 1 O m-CH3 CH3 H 1 O m-CH3 CH2CH3 H 1 O m-CH3 CHCH2CH3 H 1 O m-CH3 CH2CH2CH2CH3 H 1 O m-CH3 CH(CH3)2 H 1 O m-CH3 CH(CH3)CH2CH3 H 1 O m-CH3 CH2CH(CH3)2 H Table 18 (continued) Q3 R21 R22 R23 m.p.( C) 1 S H H H 1 S H CH3 H 1 S H CH2CH3 H 1 S H CH2CH2CH3 H 1 S H CH2CH2CH2CH3 H 1 S H CH(CH3)2 H 1 S H CH(CH3)CH2CH3 H 1 S H CH2CH(CH3) H 1 S o-Cl H H 1 S o-Cl CH3 H 1 S o-Cl CH2CH3 H 1 S o-Cl CH2CH2CH3 H 1 S o-Cl CH2CH2CH2CH3 H 1 S o-Cl CH(CH3)2 H 1 S o-Cl CH(CH3)CH2CH3 H 1 S o-Cl CH2CH(CH3)2 H 1 S m-Cl H H 1 S m-Cl CH3 H 1 S m-Cl CH2CH3 H 1 S m-Cl CH2CH2CH3 H 1 S m-Cl CH2CH2CH2CH3 H 1 S m-Cl CH(CH3)2 H 1 S m-Cl CH(CH3)CH2CH3 H 1 S m-Cl CH2CH(CH3)2 H 1 S o-CH3 H H 1 S o-CH3 CH3 H 1 S o-CH3 CH2CH3 H 1 S o-CH3 CH2CH2CH3 H 1 S o-CH3 CH2CH2CH2CH3 H 1 S o-CH3 CH(CH3)2 H 1 S o-CH3 CH(CH3)CH2CH3 H 1 S o-CH3 CH2CH(CH3)2 H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 S m-CH3 H H 1 S m-CH3 CH3 H 1 S m-CH3 CH2CH3 H 1 S m-CH3 CH2CH2CH3 H 1 S m-CH3 CH2CH2CH2CH3 H 1 S m-CH3 CH(CH3)2 H 1 S m-CH3 CH(CH3)CH2CH3 H 1 S m-CH3 CH2CH(CH3)2 H 1 S o-OCH3 H H 1 S o-OCH3 CH3 H 1 S o-OCH3 CH2CH3 H 1 S o-OCH3 CH2CH2CH3 H 1 S o-OCH3 CH2CH2CH2CH3 H 1 S o-OCH3 CH(CH3)2 H 1 S o-OCH3 CH(CH3)CH2CH2CH3 H 1 S o-OCH3 CH2CH(CH3)2 H 1 S m-OCH3 H H 1 S m-OCH3 CH3 H 1 S m-OCH3 CH2CH3 H 1 S m-OCH3 CH2CH2CH3 H 1 S m-OCH3 CH2CH2CH2CH3 H 1 S m-OCH3 CH(CH3)2 H 1 S m-OCH3 CH(CH3)CH2CH3 H 1 S m-OCH3 CH2CH(CH3)2 H 1 SO H H H 1 SO H CH3 H 1 SO H CH2CH3 H 1 SO H CH2CH2CH3 H 1 SO H CH2CH2CH2CH3 H 1 SO H CH(CH3)2 H 1 SO H CH(CH3)CH2CH3 H 1 SO H CH2CH(CH3)2 H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 SO o-Cl H H 1 SO o-Cl CH3 H 1 SO o-Cl CH2CH3 H 1 SO o-Cl CH2CH2CH3 H 1 SO o-Cl CH2CH2CH2CH3 H 1 SO o-Cl CH(CH3)2 H 1 SO o-Cl CH(CH3)CH2CH3 H SO o-Cl CH2CH(CH3)2 H 1 SO m-Cl H H I SO m-Cl CH3 H 1 SO m-Cl CH2CH3 H 1 SO m-Cl CH2CH2CH3 H 1 SO m-Cl CH2CH2CH2CH3 H 1 SO m-Cl CH(CH3)2 H 1 SO m-Cl CH(CH3)CH2CH3 H 1 SO s-C1 CH2CH(CH3)2 H 1 SO o-CH3 H H 1 SO o-CH3 CH3 H 1 SO o-CH3 2 3 H 1 SO o-CH3 CH2CH2CH3 H 1 SO o-CH3 CH2CH2CH2CH3 H 1 SO o-CH3 CH(CH3)2 H 1 SO o-CH3 CH(CH3)CH2CH3 H 1 SO o-CH3 CH2CH(CH3)2 H 1 SO o-CH3 H H 1 SO m-CH3 CH3 H 1 SO m-CH3 CH2CH3 H 1 SO m-CH3 CH2CH2CH3 H 1 SO m-CH3 CH2C2CH2CH3 H 1 SO m-CH3 CH(CH3)2 H 1 SO m-CH3 CH(CH3)CH2CH3 H 1 SO m-CH3 CH2CH(CH3)2 H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 SO o-CH3 H H 1 SO o-OCH3 CH3 H 1 SO o-OCH3 CH2CH2 H 1 SO o-OCH3 CH2CH2CH3 H 1 SO o-OCH3 CH2CH2CH2CH3 H 1 SO o-CH3 CH(CH3)2 H 1 SO o-OCH3 CH(CH3)CH2CH3 H 1 SO o-CH3 CH2CH(CH3)2 H 1 SO m-OCH3 H H 1 SO m-OCH3 CH3 H 1 SO m-OCH3 CH2CH3 H 1 SO m-OCH3 CH2CH2CH3 H 1 SO m-OCH3 CH2CH2CH2CH3 H 1 SO m-OCH3 CH(CH3)2 H 1 SO m-OCH3 CH(CH3)CH2CH3 H 1 SO m-OCH3 CH2CH(CH3)2 H 1 S02 H H H 238-240 1 S02 H CH3 H 225-227 1 SO2 H CH3 CH3 235-237 1 S02 H CH2CH3 H 1 S02 H CH2CH2CH3 H 1 SO2 H C2CH2CH2CH3 H 1 SO2 H CH(CH3)2 H 1 S02 H CH(CH3)CH2CH3 H 1 SO2 H CH2CH(CH3)2 H 1 SO2 o-Cl H H 1 SO2 o-Cl CH3 H 1 SO2 o-Cl CH3 CH3 1 SO2 o-Cl CH2CH3 H 1 SO2 o-Cl CH2CH2CH3 H 1 SO2 o-Cl CH2CH2CH2CH3 H 1 SO2 o-Cl CH(CH3)2 H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 SO2 o-Cl CH(CH3)CH2CH3 H 1 SO2 o-Cl CH2CH(CH3)2 H 1 S02 m-Cl H H 1 SO2 m-Cl CH3 H 1 SO2 m-Cl CH3 CH3 1 SO2 m-Cl CH2CH3 H 1 SO2 m-Cl CH2CH2CH3 H 1 SO2 m-Cl CH2CH2CH2CH3 H 1 SO2 m-Cl CH(CH3)2 H 1 SO2 m-Cl CH(CH3)CH2CH3 H 1 SO2 s-C1 CH2CH(CH3)2 H 1 S02 o-CH3 H H 1 S02 o-CH3 CH3 H 1 SO2 o-CH3 CH3 CH3 1 S02 o-CH3 CH2CH3 H 1 SO2 o-CH3 CH2CH2CH3 H 1 S02 o-CH3 CH2CH2CH2CH3 H 1 SO2 o-CH3 CH8CH3)2 H 1 SO2 o-CH3 CH(CH3)CH2CH3 H 1 SO2 o-CH3 CH2CH(CH3)2 H 1 SO2 m-CH3 H H 1 SO2 m-CH3 CH3 H 1 SO2 m-CH3 CH3 CH3 1 S02 a-CH3 CH2CH3 H 1 SO2 m-CH3 C2CH2CH3 H 1 SO2 m-CH3 CH2CH2CH2CH3 H 1 SO2 m-CH3 CH(CH3)2 H 1 SO2 m-CH3 CH(CH3)CH2CH3 H 1 SO2 m-CH3 CH2CH(CH3)2 H 1 SO2 o-OCH3 H H 1 SO2 o-CH3 CH3 H 1 SO2 o-CH3 CH3 CH3 Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 1 SO2 o-CH3 CH2CH H 1 SO2 o-CH3 CH2CH2CH3 H 1 SO2 o-CH3 CH2CH2CH2CH3 H 1 SO2 o-OCH3 CH(CH3)2 H 1 SO2 o-CH3 CH(CH3)CH2CH3 H 1 SO2 o-CH3 CH2CH(CH3)2 H 1 SO2 M-CH3 H H 1 502 m-OCH3 CH3 H 1 SO2 m-OCH3 CH3 CH3 1 SO2 m-OCH3 CH2CH3 H 1 SO2 m-OCH3 CH2CH2CH3 H 1 SO2 m-OCH3 CH2CH2CH3 H 1 SO2 m-OCH3 CH(CH3)2 H 1 SO2 m-OCH3 CH(CH3)CH2CH3 H 1 SO2 m-CH3 CH2H(CH3)2 H 2 0 H H H 2 0 H CH3 H 2 0 H CH2CH3 H 2 0 H CH2CH2CH3 H 2 0 H CH2CH2CH2CH3 H 2 0 H CH(CH3)2 H 2 0 H CH(CH3)CH2CH3 H 2 0 H CH2CH(CH3)2 H 2 0 o-Cl H H 2 0 o-Cl CH3 H 2 0 o-Cl CH2CH3 H 2 0 o-Cl CH2CH2CH3 H 2 0 o-Cl CH2CH2CH2CH3 H 2 0 o-Cl CH(CH3)2 H 2 0 o-Cl CH(CH3)CH2CH3 H 2 O o-Cl CH2CH(CH3)2 H 2 0 m-Cl H H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 2 O m-Cl CH3 H 2 O m-Cl CH2CH3 H 2 O m-Cl CH2CH2CH3 H 2 O m-Cl CH2CH2CH2CH3 H 2 O m-Cl CH(CH3)2 H 2 O m-Cl CH(CH3)CH2CH3 H 2 O m-Cl CH2CH(CH3)2 H 2 0 o-CH3 H H 2 O o-CH3 CH3 H 2 O o-CH3 CH2CH3 H 2 0 o-CH3 CH2CH2CH3 H 2 O o-CH3 CH2CH2CH2CH3 H 2 O o-CH3 CH(CH3)2 H 2 O o-CH3 CH(Ch3)CH2CH3 H 2 O o-CH3 CH2CH(CH3)2 H 2 0 m-CH3 H H 2 0 m-CH3 cH3 H 2 O m-CH3 CH2CH3 H 2 O m-CH3 CH2CH2CH3 H 2 O m-CH3 CH2CH2CH2CH3 H 2 O m-CH3 CH(CH3)2 H 2 0 m-CH3 CH(CH3)CH2CH3 H 2 O m-CH3 CH2CH(CH3)2 H 2 0 o-CH3 H H 2 O o-CH3 CH3 H 2 O o-CH3 CH2CH3 H 2 O o-CH3 CH2CH2CH3 H 2 0 o-CH3 CH2CH2CH2CH3 H 2 O o-CH3 CH(CH3)2 H 2 0 o-CH3 CH(CH3)CH2CH3 H 2 O o-CH3 CH2CH(CH3)2 H 2 O m-CH3 H H Table 18 (continued) q Q3 R21 R22 R23 m.p.( C) 2 O m-OCH3 CH3 H 2 0 m-OCH3 CH2CH3 H 2 0 -OCH3 CH2CH2CH3 H 2 O m-OCH3 CH2CH2CH2CH3 H 2 0 -OCH3 CH(CH3)2 H 2 0 m-OCH3 CH(CH3)CH2CH3 H 2 0 m-OCH3 CH2CH(CH3)2 H 2 S H H H 2 5 H CH3 H 2 S H CH2CH3 H 2 S H CH2CH2CH3 H 2 5 H CH2CH2CH2CH3 H 2 S H CH(CH3)2 H 2 S H CH(CH3)CH2CH3 H 2 S H CH2CH(CH3)2 H 2 S o-Cl H H 2 S o-Cl CR3 H 2 S o-Cl CH2CH3 H 2 S o-Cl CH2CH2CH3 H 2 S o-Cl CH2CH2CH2CH3 H 2 S o-Cl (CH(CH3)2 H 2 S o-Cl CH(CH3)Ch2CH3 H 2 S o-Cl CH2CH(CH3)2 H 2 5 m-Cl H H 2 S m-Cl CR3 H 2 S m-Cl CH2CH3 H 2 S m-Cl CH2CH2CH3 H 2 S m-Cl CH2CH2CH2CH3 H 2 S m-Cl CH(CH3)2 H 2 S m-Cl CH(CH3)CH2CH3 H 2 S m-Cl H2CH(CH3)2 H 2 S o-CH3 H H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 2 S o-Cl CH3 2 S o-CH3 CH2CH3 H 2 S o-CH3 CH2CH2CH3 H 2 S o-CH3 CH2CH2CH2CH3 H 2 S o-CH3 CH(CH3)2 H 2 S o-CH3 CH(CH3)CH2CH3 H 2 S o-CH3 CH2CH(CH3)2 H 2 S -CH3 H H 2 S m-CH3 CH3 H 2 S m-CH3 CH2CH3 H 2 S m-CH3 CH2CH2CH3 H 2 S m-CH3 CH2CH2CH2CH3 H 2 S m-CH3 CH(CH3)2 H 2 S m-CH3 CH(CH3)CH2CH3 H 2 S m-CH3 CH2CH(CH3)2 H 2 S o-OCH3 H H 2 S o-CH3 CH3 H 2 S o-OCH3 CH2CH3 H 2 S o-CH3 CH2CH2CH3 H 2 S o-OCH3 CH2CH2CH2CH3 H 2 S o-OCH3 CH(CH3)2 H 2 S o-OCH3 CH(CH3)CH2CH3 H 2 S o-CH3 CH2CH(CH3)2 H 2 S m-OCH3 H H 2 S m-OCH3 CH3 H 2 S m-OCH3 CH2CH3 H 2 S m-OCH3 CH2CH2CH3 H 2 S m-OCH3 CH2CH2CH2CH3 H 2 S m-OCH3 CH(CH3)2 H 2 S m-OCH3 CH(CH3)CH2CH3 H 2 S m-OCH3 CH2CH(CH3)2 H 2 SO H H H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 2 SO H CH3 H 2 SO H CH2CH3 H 2 SO H CH2CH2CH3 H 2 SO H CH2CH2CH2CH3 H 2 SO H CH(CH3)2 H 2 SO H CH(CH3)CH2CH3 H 2 SO H CH2CH(CH3)2 H 2 SO o-Cl H H 2 SO o-Cl CH3 H 2 SO o-Cl CH2CH3 H 2 SO o-Cl CH2CH2CH3 H 2 SO o-Cl CH2CH2CH2CH3 H 2 SO o-Cl CH(CH3)2 H 2 SO o-Cl CH(CH3)CHzCH3 H 2 SO o-Cl CH2CH(CH3)2 H 2 SO m-Cl H H 2 SO m-Cl CH3 H 2 SO m-Cl CH2CH3 H 2 SO m-Cl CH2CH2CH3 H 2 SO m-Cl CH2CH2CH2CH3 H 2 SO m-Cl CH(CH3)2 H 2 SO m-Cl CH(CH3)CH2CH3 H 2 SO m-Cl CH2CH(CH3)2 H 2 SO o-CH3 H H 2 SO o-CH3 CH3 H 2 SO o-CH3 CH2CH3 H 2 SO o-CH3 CH2CH2CH3 H 2 SO o-CH3 CH2CH2CH2CH3 H 2 SO o-CH3 CH(CH3)2 H 2 SO o-CH3 CH(CH3)CH2CH3 H 2 SO o-CH3 CH2CH(CH3)2 H 2 SO m-CH3 H H Table 18 (continued) q Q3 R21 R22 R23 m.p. ( C) 2 SO m-CH3 CH3 H 2 SO m-CH3 CH2CH3 H 2 SO m-CH3 CH2CH2CH3 H 2 SO m-CH3 CH2CH2CH2CH3 H 2 SO m-CH3 CH(CH3)2 H 2 SO m-CH3 CH(CH3)CH2CH3 H 2 SO m-CH3 CH2CH(CH3)2 H 2 SO o-CH3 H H 2 SO o-CH3 CH3 H 2 SO o-CH3 CH2CH3 H 2 SO o-OCH3 CH2CH2CH3 H 2 SO o-CH3 CH2CH2CH2CH3 H 2 SO o-OCH3 CH(CH3)2 H 2 SO o-OCH3 CH(CH3)CH2CH3 H 2 SO o-OCH3 CH2CH(CH3)2 H 2 SO n-OCR3 H H 2 50 m-OH3 CH3 H 2 SO m-OCH3 CH2CH3 H 2 SO m-CH3 CH2CH2CH3 H 2 SO m-CH3 CH2CH2CH2CH3 H 2 SO m-CH3 CH(CH3)2 H 2 SO m-CH3 CH(CH3)CH2CH3 H 2 SO m-OCH3 CR2CH(CH3)2 H 2 SO2 H H H 2 SO2 H CH3 H 2 SO2 H CH3 CH3 2 SO2 H CH2CH3 H 2 SO H CH2CH2CH3 H 2 SO H CH2CH2CH2CH3 H 2 SO2 H CH(CH3)2 H 2 SO2 H CH(CH3)CH2CH3 H 2 SO2 H CH2CH(CH3)2 H Table 18 (continued) a Q3 R21 R22 R23 m.p. ( C) 2 SO2 o-Cl H H 2 SO2 o-Cl CH3 H 2 SO2 o-Cl CH3 CH3 2 SO2 o-Cl CH2CH3 H 2 SO2 o-Cl CH2CH2CH3 H 2 SO2 o-Cl CH2CH2CH2CH3 H 2 SO2 o-Cl CH(CH3)2 H 2 SO2 o-Cl CH(CH3)CH2CH3 H 2 SO2 o-Cl CH2CH(CH3)2 H 2 S02 m-Cl H H 2 S02 m-Cl CH3 H 2 S02 m-Cl CH3 CH3 2 SO2 m-Cl CH2CH3 H 2 SO2 m-Cl CH2CH2CH3 H 2 SO2 m-Cl CH2CH2CH2CH3 H 2 S02 m-Cl CH(CH3)2 H 2 S02 m-Cl CH(CH3)CH2CH3 H 2 SO2 m-Cl CH2CH(CH3)2 H 2 SO2 o-CH3 H H 2 S02 o-CH3 CH3 H 2 SO2 o-CH3 CH3 CH3 2 S02 o-CH3 CH2CH3 H 2 S02 o-CH3 CH2CH2CH3 H 2 S02 o-CH3 CH2CH2CH2CH3 H 2 S02 o-CH3 CH(CH3)2 H 2 SO2 o-CH3 CH(CH3)CH2CH3 H 2 S02 o-CH3 <RTI ID=61.12> CH2CH(CH3)2 H 2 S02 m-CH3 H H 2 S02 m-CH3 CH3 H 2 SO2 m-CH3 CH3 CH3 2 SO2 m-CH3 CH2CH3 H 2 S02 m-CH3 CH2CH2CH3 H Table 18 (continued) q O3 R21 R22 R23 m.p.( C) 2 SO2 m-CH3 CH2CH2CH2CH3 H 2 SO2 m-CH3 CH(CH3)2 H 2 SO2 m-CH3 CH(CH3)CH2CH3 H 2 SO2 m-CH3 CH2CH(CH3)2 H 2 SO2 o-OCH3 H H 2 SO2 o-OCH3 CH3 H 2 SO2 o-OCH3 CH3 CH3 2 SO2 o-OCH3 CH2CH3 H 2 SO2 o-OCH3 CH2CH2CH3 H 2 5 2 o-OCH CH2CH2CH2CH3 H 2 SO2 o-OCH3 CH(CH3)2 H 2 SO2 o-OCH3 CH(CH3)CH2CH3 H 2 SO2 o-OCH3 CH2CH(CH3)2 H 2 SO2 m-OCH3 H H 2 SO2 m-OCH3 CH3 H 2 SO2 m-OCH3 CH3 CH3 2 SO2 m-OCH3 CH2CH3 H 2 SO2 m-OCH3 CH2CH2CH3 H 2 SO2 m-OCH3 CH2CH2CH2CH3 H 2 SO2 m-OCH3 CH(CH3)2 H 2 S02 m-OCH3 CH(CH3)CH2CH3 H 2 SO2 m-OCH3 CH2CH(CH3)2 H Table 19 General Structure 19 R21 R24 H H H CH3 o-Cl H o-Cl CH3 m-Cl H m-Cl CH3 o-CH3 H o-CH3 CH3 m-CH3 H m-CH3 CH3 o-OCH3 H o-OCH3 CH3 m-OCH3 H m-OCH3 CH3 Formulations Useful fornulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions. suspensions, emulsions1 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 fron 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 19 to 99.9% solid or liquid inert diluent(s). More specifically. they will contain these ingredients in the following approximate proportions: : Table 20 Weight Percent* Active Ingredient Diluent (5) Surfactant (5) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Bsulsifiable 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 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. LOUT, U.S. Patent 3.235.361, February 15, 1966, Col. 6. line 16 through Col. 7. line 19 and Examples 10. through 41: R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967. Col. 5. line 43 through Col. 7, line 62 and Examples 8, 12, 15. 39, 41. 52, 53. 58. 132, 138-140. 162-164. 166, 167 and 169-182; H. Gysin and E. Knusli. U.S. Patent 2.891.855 June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "Weed Control as a Science". John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans. "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 4 Wettable Powder 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid. methyl ester 80% sod jut alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example 5 Wettable Powder 2-[((4-iodo-6-methoxypyrimidin-2-yl)arninocarbonyl)- aminosulfonyl]benzoic acid. methyl ester 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. ExamPle 6 Granule Wettable Powder of Example 3 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 while tumbling in a double-cone blender. The granules are dried and packaged. ExamPle 7 Extruded Pellet 2-( ( (4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]- aminosulfonyl]benzoic acid, methyl ester 25% anhydrous sodium sulfate 108 crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. Example 8 Oil susPension 2-[[(4-iodo-6-methoxypyrimdin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid, methyl ester 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand nill 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. ErasPle 9 Wettable Powder N'-[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] N,N-dimethyl-1,2-benzenedisulfonamide 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 fl opening) and packaged. Example 10 Low Strength Granule 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid, methyl ester 19 N,N-dinethylfornanide 9% attapulgite granules 90S (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 11 Aqueous SusPension 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl)benzoic acid, methyl ester 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1.0% 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 12 Solution 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid, methyl ester, sodium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution. which may then be packaged for use. ExamPle 13 Low Strength Granule 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl)benzoic acid, methyl ester 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 14 Granule N'-[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] N,N-dimethyl-1,2-benzenedisulfonamide 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20% of the natural sugars) attapulgite clay 9% The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator. the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped. but fluidization is continued, optionally with heat. until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example 15 High Strength Concentrate 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid. methyl ester 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hasser-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. ExamPle 16 Wettable Powder 2-( ( (4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl]- aminosulfonylabenzoic acid, methyl ester 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 17 Wettable Powder 2-[((4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl- aminosulfonyl]benzoic acid, methyl ester 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 18 Oil Suspension 2-[[(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl) aminosulfonyl]benzoic acid, methyl ester 35% blend of polyalcohol carboxylic esters 6% and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water. Example 19 Dust [(4-iodo-6-methoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid, methyl ester 10% attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example 20 High Strength Concentrate N-[(4-bromo-6-methoxypyrimidin-2-yl)aminocarbonyl] 2,3-dihydrobenzo[b]thiophene-7-sulfonamide, 1,1 dioxide 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 nay be formulated further if necessary. Example 21 Wettable Powder N-[(4-bromo-6-methoxypyrimidin-2-yl)aminocarbonyl] 2,3-dihydrobenzo[b]thiophene-7-sulfonamide, 1,1 dioxide 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9,99 The ingredients are blended and ground in a hauser-sill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. ExamPle 22 Wettable Powder N-[(4-bromo-6-methoxypyrimidin-2-yl)aminocarbonyl] 2,3-dihydro-2-methylbenzotb]thiophene-7-sulfonamide, l,l-dioxide 40% sodium ligninsulfonate 20S 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. Utility Test results indicate that 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, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as rice. wheat, barley, cotton, corn and soybeans. Alternatively, the subject compounds are useful to modify plant growth. The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled. weather and climate, formulations selected, node of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 5 kg/ha. the lower rates being suggested for use on lighter soils and/or those having a low organic matter content. for selective weed control or for situations where only short-term persistence is required. The compounds of the invention may be used in combination with any other commercial herbicide: examples of which are those of the triazine, triazole, uracil, urea. amid. diphenylether, carbamate and bipyridylium types. The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. Compounds Compound 1 EMI75.1 Compound 2 EMI75.2 Compound 3 EMI75.3 Compound 4 EMI75.4 Compound 5 EMI75.5 Compounds (Cont'd) Compound 6 EMI76.1 Compound 7 EMI76.2 Compound 8 EMI76.3 Compound 9 EMI76.4 Compound 10 EMI76.5 Compounds (Cont'd) Compound 11 EMI77.1 Compound 12 EMI77.2 Compound 13 EMI77.3 ComPound 14 EMI77.4 TEST A Seeds of crabgrass (Diaitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea spp.). cocklebur (Xanthium pensslvanicum). sorghum, corn, soybean. sugar beet, cotton, rice, wheat, and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same tire. these crop and weed species were treated with a soil/foliage application. At the time of treatment. the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in greenhouse for sixteen days. after which all species were compared to controls and visually rated for response to treatment. The ratings. summarized in Table A. are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis B = burn D = defoliation E = emergence inhibition G = growth retardation H = formative effect U = unusual pigmentation x = axilliary stimulation S = albinism 6Y = abscised buds or flowers Table A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate (kg/ha) 0.05 0.05 0.05 0.05 POSTEMERGENCE Morningglory 2C SC, 9G 1C, 4G 4C,9G Cocklebur 9C lOC lOC lOC Cassia 2C 6C, 9G 2C,6G 4C,8G Nutsedge 2C 3C, 8G 7G 2C, 5G Crabgrass 0 2C. 6G 2G 4G Barnyardgrass 0 3C, 9H 2C.9H 3C,9H Wild Oats 0 2C, 6G 2G 0 Wheat 0 2C, 4G 2G 1C, 4G Corn 3G 1U, 7H 2C,6H 3H Soybean 0 3C, 5G 3G 1C, 1H Rice 2G 3C, 8G 2C,8G 2C.8G Sorghum 0 2C, 8G 9G 7H Sugar Beets 5C.9G 4C, 9G 3C,8G 3C,5G Cotton 2C.4G 9C 5C,9G 5C, 9G PREEMERGENCE Morningglory 2C,8G 9G 5G 7G Cocklebur 9H 5G 7H 8G Cassia 6G 5G 0 5G Nutsedge 0 2G 7G lOE Crabgrass 0 0 0 0 Barnyardgrass 1C 3G 4G 5G Wild Oats 0 5G 3G 0 Wheat 0 3G 0 0 Corn 2C,6G 6G 4G 5G Soybean O 0 0 0 Rice 4G 8G 9G 2C.7H Sorghum 3G 7G 5G 6G Sugar Beets 9G 7G 8G 6G Cotton 9G 8G 4G lOE Table A (continued) Capd. 5 Cmpd. 6 Cmpd. 7 Cnpd. 8 Rate (kgSha) 0.05 0.05 0.05 0.05 POSTEMERGENCE Morningglory 5C,9G 5C, 9G 3C,8H 2C,8G Cocklebur 9C 9C 9C lOC Cassia 5C, 9G 3C, 5G 3C, 8H 4C, 9G Nutsedge 2C,9G 2C,9G 2C,8G 9C Crabgrass 4G 3G 2C, 5G 2C,4G Barnyardgrass 9H 3C, 8G 3C,9H 3C,8H Wild Oats 1C 2C 2G 2G Wheat O 0 2G 2G Corn 2C, 9H 3C, 6G 2C, 8H 2C, 5G Soybean 3C, 7G 3C, 5G 2C, 2H 3H Rice 3C, 8G 2C,8G 4C,9G 2C,7G Sorghum 9G 5G 1C,9G 5G Sugar Beets 4C,8G 4C, 8G 3C,7G 9C Cotton 9C 6C, 9G lOC lOC PREEMERGENCE Morningglory 9G 9G 9G 9G Cocklebur 9H - 8H Cassia 7G 8G 8G 7G Nutsedge 10E 0 lOE 5G Crabgrass 5G 2G 7G 0 Barnyardgrass 4G 3C,3H 2C,8G 0 Wild Oats 2C, 4G 2C, 3G 5G 0 Wheat O 0 0 2G Corn 2C,7G 3C,6G 8G 1C,6G Soybean 2C,4H 2C,3H 3H 2H Rice 7G 3C,7G lOE 5G Sorghum 8G 2C,6G 2C,9G 3G Sugar Beets 9G 9G 8G 8G Cotton 9G 8G 9G 9G Table A (continued) Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Rate (kg/ha) 0.05 0.05 0.05 0.05 POSTEMERGENCE Morningglory 9C 5C, 9G 5C,9G 2C Cocklebur lOC 9C lOC 5C,9G Cassia 9C 9C 4C,9G 1C Nutsedge 2C.9G 5C, 9G 9C 2C,5G Crabgrass 5C,9G 5C,8G 3C,8G 2G Barnyardgrass 9C 5C,9H 3C.7H 2C,2G Wild Oats 5C.9H 1C 3G 0 Wheat 9C 0 2G 0 Corn 9C 2C,8H 9H 0 Soybean 2C,4H 3C,8G 4C,9G 1H Rice 5C, 9G 9G 2C,8G 0 Sorghum 5C,9G 2C,9G 3C.8H 0 Sugar Beets lOC 9C 5C.9G 3C,7G Cotton lOC 9C 5C.9G 3C,7G PREEMERGENCE Morningglory 9G 9G 9G 6G Cocklebur 8G - 9G 9H Cassia 8G 7G 8G 6G Nutsedge 9G 10E 5G 0 Crabgrass 3C,8G 3G 2G 0 Barnyardgrass 2C,8G 2C,7G 3G 0 Wild Oats 5G 2C 2C.6G 0 Wheat 4G 0 4G 0 Corn 2C,8G 3C,8G 2C.8G 2C,5G Soybean 2H 0 3C,6G 0 Rice 10E 2C, 7G 6G 0 Sorghum 2C, 9G 2C, 9H 8G 0 Sugar Beets 4C,9G 2C.8G 9G 3G Cotton 9G 9G 9G 7G Table A (continued) Cnpd. 13 Cmpd. 14 Rate kg/ha 0.05 0.05 POSTEMERGENCE Morningglory 3C,6G 5C,9G Cocklebur lOC 6C,9G Sicklepod 1C,2H 3C,7G Nutsedge 3C,8G 2C,8G Crabgrass 4C,8G 6C,9G Barnyardgrass lOC lOC Wild Oats 0 0 Wheat 0 2G Corn lOC 3C,9G Soybean 2H,3G 5G Rice 5C,9G 5C,9G Sorghum lOC 9C Sugar beet 9C 5C,9G Cotton 4C,9G 2C,9G PREEMERGENCE Morningglory 9G 8G Cocklebur 8G 9H Sicklepod 2C,7G 9G Nutsedge 10E 9G Crabgrass 2G 2C,8G Barnyardgrass 4C,8H 3C,9H Wild Oats 1C 1C Wheat 2G 2G Corn 2C,8G lOE Soybean 1C, 3G Rice lOE lOE Sorghum 3C,9G 3C,9H Sugar beet 10E 9G Cotton 9G 8G TEST B Postemergence Two round pans (25 cm diameter by 12.5 cm deep) were filled with sassafras sandy loam soil. One pan was planted with blackgrass (AloPecurus myosuroides), sugar beets, nutsedge (Cyperus rotundus) tubers, crabgrass, (Diaitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinoza) jimsonweed (Datura stramonium), velvetleaf (Abutilon theoPhrasti) and giant foxtail (Setaria faverii). The other pan was planted with wheat, cotton. rice. corn, soybean, wild oats (Avena fatua), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), johnsongrass (Sorghum halePense) and barnyardgrass (Echinochloa crusqalli). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic solvent. Preemerqence Two round pans (25 cm diameter by 12.5 cm deep) were filled with sassafras sandy loam soil. One pan was planted with blackgrass, sugar beets, nutsedge, crabgrass, sicklepod, teaweed. jimsonweed, velvetleaf, and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent. Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response. The response rating system was described for Test A. Response ratings are contained in Table B. Table B Compound 2 Compound 4 Hate (g/ha) 62 16 04 250 62 16 04 POSTEMERGENCE Corn 5G 0 0 3G 2G 0 0 Wheat O 0 0 0 0 0 0 Rice 9G 5G 2G 9G 8G 5G 0 Soybean 2G 0 0 2G 0 0 0 Cotton 9G 7G 2G 9G 8G 6G 2G Sugar beet 9G 8G 2G 9G 7G 3G 0 Crabgrass 7G 3G 0 9G 9G 8G 4G Johnsongrass 8G 7G 3G 9G 7G 5G 0 Blackgrass 8G 7G 2G LOG 9G 5G 0 Barnyardgrass 9G 8G 4G 9G 8G 4G 0 Nutsedge 9G 4G 0 9G 8G 5G 2G Giant Foxtail 6G 2G 0 8G 6G 2G 0 Wild Oats 4G 0 0 0 0 0 0 Cocklebur 9G 7G 0 10G 9G 4G 0 Morningglory 9G 8G 2G 10G 7G 3G 0 Teaweed 9G 5G 0 9G 9G 8G 2G Cassia 9G 5G 0 9G 9G 6G 2G Jimsonweed 9G 7G 3G 10G 8G 6G 2G Velvet leaf 9G 7G 4G 9G 9G 7G 3G Rate (g/ha) 250 62 16 250 62 PREEXERGENCE Corn 3G 0 0 0 0 Wheat 3G 0 <RTI ID=84.8> 0 0 0 Rice 9G 9G 8G 9G 8G Soybean 3G 0 0 0 0 Cotton 6G 3G 0 2G 0 Sugar beet 8G 7G 3G 5G 3G Crabgrass 8G 7G 2G 9G 3G Johnsongrass 9G 8G 3G 8G 6G Blackgrass 9G 9G 8G 9G 9G Barnyardgrass 9G 7G 3G 9G 7G Nutsedge 9G 8G 0 9G 8G Giant Foxtail lOE 7G 2G 9G 8G Wild Oats 6G 4G 0 0 0 Cocklebur 7G 3G 0 6G 0 Morningglory 8G 4G 0 7G 0 Teaweed 9G 9G 4G 9G 7G Cassia 8G 6G 2G 7G 2G Jimsonweed 9G 7G 4G 9G 9G Velvetleaf 9G 8G 4G 7G 5G Table B (continued) ComPound 5 Compound 6 Rate (g/ha) 62 16 04 250 62 16 POSTEMERGENCE Corn 4G 0 0 0 0 0 Wheat O 0 0 0 0 0 Rice 5G 0 0 7G 3G 0 Soybean O 0 0 2G 0 0 Cotton 7G 4G 0 6G 2G 0 Sugar beet 7G 2G 0 9G 7G 3G Crabgrass 6G 2G 0 6G 2G 0 Johnsongrass 8G 3G 0 5G 2G 0 Blackgrass 2G 0 0 4G 0 0 Barnyardgrass 7G 3G 0 7G 2G 0 Nutsedge 9G 4G 0 6G 0 0 Giant Foxtail 9G 2G 0 4G 0 0 Wild Oats 0 0 0 0 0 0 Cocklebur 9G 5G 0 9G 6G 0 Morningglory 9G 4G 0 lOG 9G 2G Teaweed 9G 7G 2G 9G 7G 2G Cassia lOG 9G 3G 9G 8G 3G Jimsonweed lOG 5G 0 9G 9G 2G Velvetleaf 9G 4G 0 9G 8G 3G Rate (g/ha) 250 62 16 250 62 PREEMERGENCE Corn 5G 2G 0 0 0 Wheat O 0 0 0 0 Rice 9G 6G 4G 9G 7G Soybean O 0 0 0 0 Cotton 5G 2G 0 2G 0 Sugar beet 6G 3G 0 7G 3G Crabgrass 7G 3G 0 0 0 Johnsongrass 8G 6G 2G 3G 0 Blackgrass 8G 6G 2G 8G 6G Barnyardgrass 8G 4G 0 6G 2G Nuts edge 9G 9G 3G 2G 0 Giant Foxtail 8G 3G 0 8G 2G Wild Oats 0 0 0 0 0 Cocklebur 6G 3G 0 6G 0 Morningglory 7G 3G 0 3G 0 Teaweed 8G 5G 0 8G 3G Cassia 7G 2G 0 4G 0 Jimsonweed 9G 8G 3G 9G 7G Velvetleaf 8G 4G 0 8G 6G Table B (continued) Compound 7 Compound 10 Rate (g/ha) 250 62 16 62 04 POSTEMERGENCE Corn 8G 3G 0 2G 0 Wheat O 0 0 0 0 Rice 9G 5G 2G 5G 0 Soybean 4G 2G 0 0 0 Cotton 9G 7G 3G 7G 0 Sugar beet 7G 0 0 9G 6G Crabgrass 9G 3G 0 6G 2G Johnsongrass 10G 9G 9G LOG 5G Blackgrass 8G 4G 0 4G 0 Barnyardgrass 9G 8G 7G 8G 2G Nutsedge 9G 8G 3G 9G 4G Giant Foxtail 9G 9G 6G 8G 0 Wild Oats o 0 0 0 0 Cocklebur 9G 9G 3G 10G 5G Morningglory 8G 4G 0 10G 2G Teaweed 10G 6G 2G 9G 4G Cassia 9G 5G 3G 10G 5G Jimsonweed 10G 8G 6G 9G 3G Velvetleaf 10G 9G 3G 9G 6G Rate (g/ha) 250 62 16 250 62 PREEMERGENCE Corn 7G 5G 0 2G 0 Wheat O 0 0 0 0 Rice 9G 9G 8G 9G BG Soybean O 0 0 4G 0 Cotton 3G 0 0 5G 0 Sugar beet 3G 0 0 7G 3G Crabgrass 9G 4G 2G 9G 5G Johnsongrass 9G 9G 4G 10G 9G Blackgrass 9G 9G 6G 8G 7G Barnyardgrass 9G 8G 4G 9G 7G Nutsedge 10E 9G 3G 9G 8G Giant Foxtail 8G 7G 3G 9G 7G Wild Oats O 0 0 2G 0 Cocklebur O 0 0 9G 6G Morningglory 3G 0 0 8G 5G Teaweed 9G 6G O 9G 8G Cassia 4G 0 0 7G 0 Jimsonweed 9G 8G 7G 9G 7G Velvetleaf 7G 0 0 9G 7G Table B (continued) Compound 11 Rate (g/ha) 62 16 04 01 POSTEMERGENCE Corn 7G 3G 0 0 Wheat 0 0 0 0 Rice 2G 0 0 0 Soybean 8G 3G 0 0 Cotton 10C lOC 8G 0 Sugar beet 10C 9G 5G 2G Crabgrass 3G 0 0 0 Johnsongrass 6G 2G 0 0 Blackgrass 2G 0 0 0 Barnyardgrass 5G 0 0 0 Nutsedge 5G 2G 0 0 Giant Foxtail 3G 0 0 0 Wild Oats 0 0 0 0 Cocklebur 10C 8G 6G 2G Morningglory 10G 10G 4G 0 Teaweed 8G 7G 4G 2G Cassia 10C 9G 7G 5G Jimsonweed 10C 9G BG 3G Velvetleaf 10C 7G 5G 0 Rate (g/ha) 250 62 16 PREEMERGENCE Corn 3G 0 0 Wheat 0 0 0 Riee 8G 4G 0 Soybean 3G 0 0 Cotton 6G 2G 0 Sugar beet 10G 10G 6G Crabgrass 5G 2G 0 Johnsongrass 5G 0 0 Blackgrass 8G 6G 2G Barnyardgrass 4G 0 0 Nutsedge 8G 3G 0 Giant Foxtail 5G 0 0 Wild Oats 0 0 0 Cocklebur 4G 2G 0 Morningglory 5G 2G 0 Teaweed 10G 8G 5G Cassia 10G 9G 4G Jimsonweed 10G 9G 3G Velvet leaf 10G 9G 3G Table B (continued) Compound 13 POSTEMERGENCE Rate g/ha 62 16 4 1 Corn lOU lOU 9G 7G Wheat O 0 0 0 Rice lOC 9G 6G 4G Soybean 6G 4G 3G 2G Cotton lOC 8G 4G 2G Sugar beet lOC 10G 9G 9G Crabgrass 10G 9G 5G 2G Johnsongrass lOC 9G 7G 3G Blackgrass 9C 8G 2G 0 Barnyardgrass lOC 9G 5G 2G Nutsedge 4G 2G 0 0 Giant Foxtail 9G 6G 4G 0 Wild Oats 0 0 0 0 Cocklebur 8G 6G 3G 0 Morningglory 9G 8G 6G 2G Teaweed 10G 7G 5G 2G Sieklepod 7G 4G 4G 0 Jinsonweed 10G 5G 3G 2G Velvet leaf lOC 6G 6G 4G PREEMEGENCE Rate g/ha 250 62 16 4 Corn 10G 7G 3G 0 Wheat 0 0 0 0 Rice 10G 10G 8G 4G Soybean 5G 2G 0 0 Cotton 8G 3G 0 0 Sugar beet 8G 6G 2G 0 Crabgrass 10G 9G 3G 0 Johnsongrass 10G 10G 8G 3G Blackgrass 10G 10G 8G 3G Barnyardgrass 10G 10G 7G 2G Nutsedge 10G 9G 3G 0 Giant Foxtail Wild Oats 2G 0 0 0 0 Cocklebur 7G 3G 0 0 Morningglory 9G 6G 3G 0 Teaweed 9G 8G 4G 0 Sicklepod 10G 8G 4G 0 Jimsonweed 10G 10G 8G 3G Velvetleaf 9G 8G 3G 0 Table B (continued) Compound 14 POSTEMERGENCE Rate g/ha 62 16 4 1 Corn lOG lOG 9G 7G Wheat O 0 0 0 Rice lOG 10G 9G 7G Soybean 3G 1G O 0 Cotton 9G 6G 3G 0 Sugar beet 10G 7G 2G 0 Crabgrass 10G 10G 8G 3G Johnsongrass 10G 9G 9G 6G Blackgrass 10G 9G 6G 2G Barnyardgrass 10G 10G 7G 4G Nutsedge O 0 0 0 Giant Foxtail 10G 9G 7G 4G Wild Oats O 0 0 0 Cocklebur 10G 6G 2G 0 Morningglory 10G 6G 2G 0 Teaweed 8G 4G 0 0 Sicklepod 4G 2G 0 0 Jimsonweed 10G 7G 2G 0 Velvetleaf 10G 6G 3G 0 PREEMERGENCE Rate g/ha 250 62 16 4 Corn 10G 9G 4G 0 Wheat 8G 2G 0 0 Rice 10G 10G 10G 8G Soybean 6G 1G O 0 Cotton 9G 7G 2G 0 Sugar beet 10G 9G 3G 0 Crabgrass 10G 9G BG 3G Johnsongrass 10G 10G 9G 8G Blackgrass 10G 10G 8G 7G Barnyardgrass 10G 9G 9G 5G Nutsedge 10G 9G 7G 3G Giant Foxtail - - - Wild Oats 4G 0 0 0 Cocklebur 6G 2G 0 0 Morningglory 8G 3G 0 0 Teaweed 10G 9G 8G 2G Sicklepod 9G 7G 4G 0 Jimsonweed 10G 9G 7G 2G Velvetleaf 10G 8G 5G 2G Test C Three 25-cm diameter plastic pots were filled with a light soil. One pan was planted to short rows of corn, soybeans, and cotton. planting depth 2.5 cm. The other two pots were planted to the following weed species, 8 or 9 species per pot: crabgrass (Digitaria sp.). johnsongrass, (Sorghum halePense), barnyardgrass (Echinochloa crusQalli), nutsedge (Cyperus rotundus), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), cocklebur (Xanthium Pensylvanicum) norningglory (Ipomoea hederacea). teaweed (Sida spin osa). sicklepod (Cassia obtusifolia). jimsonweed (Datura stramonium), velvetleaf (Abutilon theo phrasti), bindweed (Convolvulus arvensis), coffeeweed (Sesbania exaltata), lambsquarters (ChenoPodium album), pigweed (Amaranthus retroflexus). and purslane (Portulaca oleracea). All of the foregoing weed species were planted at a depth of 0.5 to 1.0 cm, except for cocklebur and nutsedge which were planted at a depth of 2.5 cm. The plantings were treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time. the same crops and weed species, from plantings made 10 to 21 days previously, were treated with a soil/foliage application. Treated plants and controls were maintained in a greenhouse for 3 to 4 weeks after which all species were compared to controls and visually rated for response to treatment with 0 indicating no injury and 100 indicating that the plants were dead. The data are summarized in Table C. Table C Compound 13 Rate gm/ha 250 125 62 31 16 8 4 POSTEMERGENCE Corn 100 100 100 100 90 85 80 Cotton Soybean 55 40 35 30 25 20 20 Crabgrass 100 100 95 85 75 65 40 Johnsongrass 100 100 100 100 100 100 80 Barnyardgrass 100 100 100 95 80 75 50 Nutsedge 100 95 80 75 55 35 30 Giant foxtail 100 100 100 95 85 80 70 Green foxtail 100 100 100 95 85 85 70 Cocklebur - 100 100 85 85 65 40 Morningglory - 95 90 80 75 55 35 Teaweed - 90 85 80 80 60 40 Sicklepod - 90 85 80 65 50 40 Jimsonweed - 85 80 85 75 50 40 Velvetleaf 95 90 85 80 65 40 30 Bindweed 85 60 40 35 25 15 0 Coffeeweed 100 100 100 85 80 65 45 Lambsquarter 100 95 90 90 70 60 35 Pigweed 100 100 100 100 85 75 40 Purslane 100 100 95 85 75 65 50 PREEMERGENCE Corn 100 100 95 85 75 45 20 Cotton 100 100 85 75 35 15 0 Soybean 75 40 25 0 0 0 0 Crabgrass 100 100 100 100 85 60 20 Johnsongrass 100 100 100 100 100 95 75 Barnyardgrass 100 100 100 100 95 85 35 Nutsedge 100 100 100 100 95 85 45 Giant foxtail 100 100 100 95 90 30 0 Green foxtail 100 100 95 95 80 15 0 Cocklebur 100 100 85 55 35 25 0 Morningglory 100 100 95 90 85 35 0 Teaweed 100 100 100 85 75 45 15 Sicklepod 100 100 95 85 65 45 15 Jimsonweed 100 100 100 95 90 60 20 Velvetleaf 100 100 95 95 80 65 15 Bindweed 100 100 90 85 75 55 25 Coffeeweed 100 100 85 80 60 35 15 Lambsquarter 100 100 100 100 90 75 50 Pigweed 100 100 100 100 90 75 50 Purslane 100 100 100 100 100 80 50 Table C (continued) Compound 14 Rate gm/ha 250 125 62 31 16 8 4 POSTEMERGENCE Corn 100 100 100 100 90 85 75 Cotton - - - - - - Soybean 45 40 30 25 20 15 0 Crabgrass 100 95 95 85 75 50 35 Johnsongrass 100 100 100 100 100 95 85 Barnyardgrass 100 100 100 90 85 80 65 Nutsedge 95 85 80 75 50 20 0 Giant foxtail 100 100 95 90 85 80 70 Green foxtail 100 100 100 90 90 85 70 Cocklebur 100 90 85 70 65 40 20 Morningglory 95 85 80 70 70 50 30 Teaweed 100 90 90 65 60 50 35 Sicklepod 100 95 85 70 55 25 15 Jimsonweed 100 90 80 50 40 20 15 Velvetleaf 95 85 75 75 55 25 20 Bindweed 70 60 60 45 40 25 15 Coffeeweed 100 100 90 65 60 35 25 Lanbsquarter 100 100 95 90 80 40 15 Pigweed 100 100 100 100 95 80 45 Purslane 100 100 100 85 85 40 35 PHEEMERGENCE Corn 100 100 95 80 60 20 0 Cotton 100 90 70 25 15 0 0 Soybean 50 35 20 0 0 0 0 Crabgrass 100 100 100 100 85 75 55 Johnsongrass 100 100 100 100 100 90 85 Barnyardgrass 100 100 100 100 90 85 55 Nutsedge 100 100 100 95 75 45 25 Giant foxtail 100 100 100 90 85 80 20 Green foxtail 100 100 100 90 90 55 15 Cocklebur - - - - - - - Morningglory 100 100 100 85 60 20 0 Teaweed 100 100 95 85 55 25 15 Sicklepod 100 90 90 75 40 20 15 Jinsonweed 100 100 100 100 100 90 75 Velvetleaf 100 95 90 80 50 25 15 Bindweed 100 95 90 85 80 60 45 Coffeeweed 100 90 90 80 45 30 20 Lanbsquarter 100 100 100 100 90 80 75 Pigweed 100 100 100 100 90 80 75 Purslane 100 100 100 100 100 85 80 Test D Two plastic pans lined with polyethylene liners were filled with prepared Woodstown sandy loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgar), wild oats (Avena fatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum) and rapeseed (Brassica napus). The other pan was planted with seeds of Russian thistle (Salsola kali), cleavers (Galium aparine). speedwell (Veronica Persia) kochia (Kochia scoparia). shepherdspurse (CaPsella bursa-Pastoris) Matricaria inodora, black nightshade (Solanum niqrum). wild buckwheat (Polygonum convolvulus) and sugar beets (Beta vulparis). The above two pans were treated preemergence. At the same time two pans in which the above plant species were already growing were treated postemergence. Plant height at the time of treatment ranged from 1-20 cm depending on plant species. The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 19-22 days at which time the treatments were compared to the controls and the effects visually rated utilizing the same rating system as described for Test A. The recorded data are presented in Table D. Table D Compound 13 Rate kg/ha .125 .06 .03 .015 .008 .004 .002 .001 POSTEMERGENCE wheat 2G 0 0 0 0 0 0 0 barley 8G 5G 4G 3G 2G 0 0 0 wild oats 0 0 0 0 0 0 0 0 cheatgrass 6G 5G 3G 0 0 0 0 0 blackgrass 10C 9G 7G 5G 3G 0 0 annual bluegrass lOC 9G 9G 4G 4G 0 0 green foxtail 10C 10C 10C 10C 8G 6C 4G Italian ryegrass 10C 8G 8G 5G 3G 3G 2G rapesed 10C 10C 10C 10C 10C 9G 7G Matricaria inodora - - - - - - - Gallium aparine - - - - - - - Russian thistle - - - - - - - shepherdspurse - - - - - - - - kochia - - - - - - - black nightshade - - - - - - - speedwell lOC 10C 10C 3G 0 0 0 0 wild buckwheat 10C 5G 2G 0 - 2G 2G 0 sugar beets 10C 9G 9G 4G 5G 3G 3G 3G PREEMERGENCE wheat 0 0 0 0 0 0 0 0 barley 6G 0 2G 0 0 0 0 0 wild oats 0 0 0 0 0 0 0 0 cheatgrass 5G 2G 0 0 0 0 0 0 blackgrass 8G 8G BG 8G 7G 3G 2G 0 annual bluegrass 9G 9G 9G 8G 8G 7G SG 3G green foxtail 9G 8G 5G 2G 0 0 0 0 Italian ryegrass 8G 8G 7G 4G 4G 3G 3G 0 rapeseed 9G 9G 9G 8G 7G 4G 4G 2G Matricaria inodora 9G 9G 8G 8G 8G 6G 6G 5G Galium sparine 10C 9G 9G 5G 5G 4G 4G 0 Russian thistle 8G 8G 3G 2G 2G 2G 0 0 shepherdspurse 10C 10C 9G 9G 9G 7G 6G 0 kochia 10C 10C 10C 10C 8G 8G 4G 4G black nightshade 9G 9G 9G 8G 8G 6G 3G 0 speedwell 10C 10C 10C 10C 9G 7G 5G 0 wild buckwheat 8G 8G 7G 2G 0 0 0 0 sugar beets 10C 10C 10C 10C 8G 8G 6G 6G Table D (continued) Compound 13 Rate kg/ha .125 .06 .03 .015 .008 .004 .002 .001 POST EMERGENCE wheat 0 0 0 0 0 0 0 0 barley 6G 5G 4G 4G 5G 2G 2G 0 wild oats 0 0 0 0 0 0 0 0 cheatgrass 6G 4G 4G 2G 0 0 0 0 blackgrass 9G 9G 8G 5G 3G 0 0 annual bluegrass lOC 9G 8G 5G 2G 2G 0 green foxtail lOC 10C lOC lOC 8G 7G 5G Italian ryegrass 9G 6G 5G 3G 2G 0 0 rapeseed 10C 10C 10C 10C 9G 8G 5G Hatricaria inodora - - - - - - - Gallium aparine - - - - - - - Russian thistle - - - - - - - shepherdspurse - - - - - - - kochia - - - - - - - black nightshade - - - - - - - speedwell 7G 0 0 0 0 0 0 0 wild buckwheat 7G 2G 2G - 0 0 0 0 sugar beets lOC 10C 10C 4G 3G 3G 0 0 PREEMERGENCE wheat 0 0 0 0 0 0 0 0 barley 8G 7G 7G 7G 3G 3G 0 0 wild oats 0 0 0 0 0 0 0 0 cheatgrass 7G 3G 0 0 0 0 0 0 blackgrass 9G 8G 8G 7G 6G 4G 2G 1G annual bluegrass 9G 9G 9G 8G 5G 5G 3G 2G green foxtail 9G 7G 7G 6G 4G 2G 0 0 Italian ryegrass 8G 7G 6G 5G 4G 2G 2G 2G rapeseed 9G 9G 9G 7G 5G 2G 2G 2G Hatricaria inodora 8G 7G 7G 7G 6G 5G 4G 3G Galium aparine 9G 8G 9G 6G 5G 0 0 0 Russian thistle 6G 6G 3G 0 0 0 0 0 shepherdspurse 10C 10C 9G 9G 8G 6G 5G 3G kochia 10C 10C 10C 9G 7G 6G 6G 3G black nightshade 9G 9G 9G 8G 8G SG 6G 4G speedwell 9G 6G 3G 0 0 0 0 0 wild buckwheat 8G 5G - 0 0 0 0 0 sugar beets 9G 9G 9G 9G 7G 8G 5G 5G

Claims: Claims 1. A coapound of the formula EMI96.1 wherein R is CH3 or CH2CH3; EMI96.2 EMI97.1 EMI98.1 R1 is C1-C4 alkyl, C1-C4 alkoxy, OCH2CH2OCH3, F, Cl, Br, NO2, CF3, CO2R15, SO2NR16R17, C(O)R25, CR25(OR26), SO2N(OCH3)CH3, OSO2R18, S(O)nR19, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy. C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, EMI98.2 R2 is H, F, Cl, Br, C1-C4 alkyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy. C1-C4 haloalkoxy, C1-C4 haloalkyl, S(O)p C1-C4 alkyl, S(O)p C3-C4 alkenyl, S(O)p C3-C4 alkynyl or C1-C2 alkyl substituted with OCH3 or SCH3: R3 is H, CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3; R4 is CH3, CH2CH3, OCH3, OCH2CH3, F, Cl, Br, SO2NR16R17, SO2N(OCH3)CH3, S(O)nR19, C3-C4 alkenyloxy or C3-C4 alkynyloxy; H5 is C1-C3 alkyl. F, C1, Br. NO2, CO2R15, SO2MR16R17, SO2N(OCH3)CH3 or S(O)nR19 R6 is Cl, NO2, CO2CH3, CO2CH3CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; R7 is H, CH3 or CH2CH3; R8 is H, CH3 or CH2CH3; R9 is H or CH3; R10 is H or CH3; R is H or CH3; R12 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, benzyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, CH2CN, CH2C(O)CH3, CH2CO2(C1-C2 alkyl), C1-C4 alkyl substituted with 0-3 F. 0-1 Cl, OH, OCH3 or OC2H5 or C3-C4 alkenyl sub stituted with 1-3 F or 1-3 C1; R13 is H or CH3; R14 is CH3 or C2H5; R15 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R1 is H. C1-C3 alkyl; R17 is C1-C3 alkyl; R18 is C1-C3 alkyl or N(CH3)2; R19 is C1-C3 alkyl or CH2CH=CH2; R20 is H, Cl or CH3; R21 is H. C1, CH3 or OCH3; R22is H or C1-C4 alkyl; R23 is H or CH3; R24 is H or CH3; R25 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl or C3-C6 cycloalkyl. R26 is C1-C2 alkyl; m is O or 1; n is 0 or 2. p is o, 1 or 2: q is 1 or Z: Q1 is O, s or SO2; Q2 is or S; Q3 ie O, S, sO or SO2; and N is O, S or SO2; provided that 1) the total number of carbon atoms of H16 and R17 is less than or equal to four 2) when 1 is 1, then R9 is H; and 3) when R23 is CH3, then Q3 is SO2 and R22 is CH3; and their agriculturally suitable salts. 2. A compound of Claim 1 where H is CH3. 3. A conpound of Claim 2 where L is L-1, L-2. L-3. L-5. L-8, L-10, L-ll. L-16 or L-17. 4. A compound of Claim 3 where L is L-1: R1 is OCH3 OC2H5, Cl, NO2, CF3, CO2CH3, CO2C2H5, SO2N(CH3)2, SO2N(OCH3)CH3, OSO2R18, C(O)CH3, C(O)C2H5, S(O)nR19, OCF2H, SCF2H, OCH2CH=CH2, OCH2C#CH, EMI100.1 R2 is H, F, Cl, Br, CH3, C2H5, S(O)pC1-C2 alkyl, S(O)pCH2CH=CH2, S(O)pCH2C#CH, C1-C3 alkoxy, OCH2CH=CH2, OCH2C#CH, C1-C2 haloalkoxy, C1-C2 haloalkyl, CH2OCH3 or CH2SCH3; R18 is C1-C3 alkyl; R19 is CH3 or C2H5; and n is 2. 5. A compound of Claim 4 where L is EMI100.2 and R2 is H, F, Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3. 6. A compound of Claim 3 where L is L-2; and R3 is Cl, CH3, OCH3. SCH3 or Br. 7. A compound of Claim 3 where L is L-3: and R4 is Cl, SO2CH3 or SO2N(CH3)2, 8. A compound of Claim 3 where L is L-5; H5 is CO2CH3 or CO2C2H5; and H20 is H. 9. A compound of Claim 3 where L is L-8: m is O; R2 is H, F, C1, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3; and R9 is H. 10. A compound of Claim 3 where L is L-10; R2 is H. F, C1, Br. CH3, CH2CH3, SCH3, SC2H5. OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3; R9 is H; and R12 is H, C1-C4 alkyl. C1-C4 alkylcarbonyl. CH2F or C2-C3 alkyl substituted with 1 F or 1 C1. 11. A compound of Claim 3 where L is L-ll; R2 is H, F, Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3; and R9 is H. 12. A compound of Claim 3 where L is L-16: and R2 is H, F. Cl, Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3. 13. A compound of Claim 3 where L is L-17: and R2 is H, F, Cl. Br, CH3, CH2CH3, SCH3, SC2H5, OCH3, OC2H5, CF3, CH2OCH3 or CH2SCH3. 14. A compound of Claim 1 which is 2-[[(4-iodo- 6-methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 15. A compound of Claim 1 where J is J-1, R22 is H. CH3 or C2H5 and R23 is H. 16. A compound of Claim 1 which is N'-[(4-iodo- 6-methoxypyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl1.2-benzenedisulfonamide. 17. A compound of Claim 1 which is 2-tt(4-iodo- 6-methoxypyrimdin-2-yl)aminocarbonyl]aminosulfonyl] 4-sethylbenzoic acid. methyl ester. 18. A compound of Claim 1 which is N-((4-bromo- 6-methoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydrobenzo[b]thiophene-7-sulfonamide, 1,1-dioxide. 19. A compound of Claim 1 which is N-((4-bromo- 6-methoxypyìmidin-2-ylaminocarbonyl]-2,3-dihydro-2- methylbenzo[b]thiophene-7-sulfonamide, 1,1-dioxide. 20. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of any of claims 1 to 19 and at least one of the following: surfactant, solid or liquid diluent. 21. A method for controlling the growth of undesirec vegetation which comprises applying to the locus to be protected an effective amount of the compound of any of claims 1 to 19. 22. A method for regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant selected from compounds of any of clams 1 to 19. 23. A process for the production of a compound of claim t which comprises: (a) reacting an appropriately substituted sulfonyl isocyanate of formula LSO2NCO or JSO2NCO (II) (IIa) with an aminoheterocycle of formula EMI102.1 respectively, wherein L, J and R are as defined in claim 1; or (b) reacting a phenylcarbamate of formula EMI103.1 with said aminoheterocycle of formula (III) or (IIIa) respectively; wherein L and J are as defined in claim 1; or (c) reacting a sulfonamide of formula LSO2NH2 or JSO2NH2 (IV) (IVa) with a heterocyclic phenylcarbamate of formula EMI103.2 respectively wherein L, J and R are as defined in claim 1. 24. Iodopyrimidines of formula EMI103.3 and phenylcarbamates thereof; wherein R is CH3 or C2 H5.

Inventors: BROWN, HUGH MALCOLM, PASTERIS, ROBERT JAMES
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1985
Main classification: C07D239
IPC codes: C07D521, A01N47, C07D239