HERBICIDAL SULFONAMIDES

Abstract: Sulfonylurea derivatives of the formula wherein J is an aromatic group having a condensed ring; W is O or S; R is H or CH₃; and A is a cyclopropyl-substituted pyrimidinyl or triazinyl group; and their agriculturally suitable salts, exhibit pre-­ emergence and post-emergence herbicidal activity. Some also show plant growth regulant activity. The compounds may be formulated for agricultural use in conventional manner. They may be prepared by a variety of synthetic routes, e.g. by reacting an appropriate aromatic sulfonylisocyanate or sulfonylisothiocyanate with the appropriate aminopyrimidine or aminotriazine.

Description: Title HERBICIDAL SULFONAMIDES Backqround of the Invention This invention relates to novel sulfonylurea derivatives, methods for their production, agriculturally suitable compositions containing them, and their method-of- use as pre-emergent or post-emergent herbicides or plant growth regulants. U.S. 4.127.405 and U.S. 4.169.719 disclose herbicidal benzenesulfonylureas. EP-A-79.683. published May 25, 1983, discloses herbicidal sulfonamides of formula EMI1.1 where J is various benzofuran. benzothiophene. l-benzo pyran. l-benzothiopyran, l-benzoxepin and l-benzothiepin moiteties: X is H. CH3, OCH3 or C1: Y is CH3. OCH3. OCH2CH3. CH2OCH3. CH2CH3. NH2. NHCH3 or N(CH3)2: and Z is CH or N. EP-A-107.979. published-May 9, 1984. discloses herbicidal sulfonamides of formula EMI1.2 where J is. among other values EMI2.1 South African Patent Application 83/5165 filed by Ciba-Geigy (Swiss Priority 7/16/82) discloses herbicidal sulfonylureas of the general structure shown below: EMI2.2 wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom. forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the -SO- or s02-group. South African Patent Application 83/7434 discloses herbicidal sulfonamides of formula EMI2.3 where EMI3.1 R2 is halogen, C1-C3 alkyl. C1-C3 haloalkyl. C1-C3 alkoxy. C1-C3 haloalkoxy, amino. C1-C3 alkylamino. di(C1-C3 alkyl)amino, C3-C6 cycloalkyl or C2-C6 alkoxyalkyl. This invention results from efforts to obtain novel and improved herbicides and growth regulants to help serve the ever-increasing need for food supplies in the world. Summary of the Invention This invention relates to novel compounds of Formula I. agriculturally suitable compositions containing them, and their method-of-use as preemergent or post-emergent herbicides or plant growth regulants. EMI4.1 EMI5.1 EMI6.1 EMI6.2 EMI7.1 n is 0. 1 or 2; W is O or S; W1 is O or S; Q is O, S, SO or SO2: Q1 is O, S or SO2: R is H or CH3: R1 is H. F. Cl. Br. CH3. OCH3. CF3. SCH3 or OCF2H; R2 is H or C1-C4 alkyl: R3 and R4 are independently H, C1-C4 alkyl. Cl or Br; R5 is H or CH3; R6 is H or CH3: R7 is H or CH3; R8' is H, CH3, OCH3, Cl, Br, CO2R12, SO2R13, OSO2R14 or SO2NR15R16: R9 and R10 are independently H or C1-C3 alkyl; R11 is H or CH3: R12 is C1-C3 alkyl. CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl: R13 is C1-C3 alkyl; R14 is C1-C3 alkyl or CF3; R15 and R16 are independently C1-C2 alkyl; R17 is H or C1-C4 alkyl: R1@ is H or C1-C4 alkyl; R19 is H or CH3: R20 is H. Cl, CH3, CF3, OCH3, Br, F, SCH3 or OCF2H; R21 is H, CH3, OCH3, Cl, Br, NO2, CO2R24, SO2R25, OSO2R26, SO2NR27R28, F, CH3, SCH3. OCF2H or SO2N(OCH3)CH3; R22 is H. Cl. Br or C1-C4 alkyl; R23 is H, CH3, Cl or Br: R24 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2C1; R25 is C1-C3 alkyl; R26 is C1-C3 alkyl or CF3: R27 and R28 are independently C1-C2 alkyl: A is EMI8.1 Y is C1-C2 alkyl. C1-C2 alkoxy, C1 C2 alkoxy methyl, OCF2H. SCF2H. OCH2CH2F. OCH2CF3, CF3, OCH2CH=CH2, OCH2C=CH, NHCH3, N(CH3)2 or CH(OCH3)2: and Z is CH or N; and their agriculturally suitable salts; provided that a) when W is S, then B is H; b) the total number of carbon atoms in R3 and R4 is less than or equal to 4; c) when R5 is CH3. then n is 0; d) when J is J24, then R4 and R5 are not both H; e) the total number of carbon atoms in R9 and R10 is less than or equal to 3; f) in Formula J28. when R9 and R10 are other than H. then R11 is H; g) in Formula J29. when R9 is other than H. then B11 is H: h) when Q is S. then B8 is not SO2NR15R16: i) in Formulae J29 and J32, Q may not be 0; j) in Formula J33, R8 is not CH3: : k) in Formulae J36 and J 37. when R21 is NO2, then R22 is C1-C4 alkyl and R23 is CH3 1) in Formulae J34 and J35, when Q is SO, then W is O; m) when R20 is other than H. then R21 is H; n) R17 and R18 taken together are not more than four carbon atoms; o) when J is J27, J28, J29, J30, J31, or J32, then Q is 0. S or SO2; and p) when Y is OCF2H then Z is CH. Preferred Compounds 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 W is 0: R3 and R4 are independently H or C1-C3 alkyl; R17 is 2 or C1-C2 alkyl; R18 is H or CH3; R19 is H; R22 is H or C1-C2 alkyl; R23 is H; and R1 is bonded to the ortho or meta position of the ring relative to the sulfonylurea moiety. 2) Compounds of Preferred 1 where R is H: R1 is H. F, C1, Br. CH3, OCH3, CF3 or SCH3; R8 is H, CH3. OCH3 or Cl; R20 is H, Cl, CH3 or OCH3: and R21 is H. C1. CH3. OCH3. CO2R24 or SO2R25, 3) Compounds of Preferred 2 where R1 is H; R5 is H; R8 is H; B20 is H; R21 is H; and Y is CH3, OCH3 or CH2OCH3. 4) Compounds of Preferred 3 where J is J1 5) Compounds of Preferred 3 where J is J2 6) Compounds of Preferred 3 where J is 33 7) Compounds of Preferred 3 where J is J4 8) Compounds of Preferred 3 where J is J5. 9) Compounds of Preferred 3 where J is J6. 10) Compounds of Preferred 3 where J is J7. 11) Compounds of Preferred 3 where J is 12) Compounds of Preferred 3 where J is J9. 13) Compounds of Preferred 3 where J is J10 14) Compounds of Preferred 3 where J is j @11 15) Compounds of Preferred 3 where J is J1211 16) Compounds of Preferred 3 where J is J1312 17) Compounds of Preferred 3 where J is J14 18) Compounds of Preferred 3 where J is J15 19) Compounds of Preferred 3 where J is J16 20) Compounds of Preferred 3 where J is J17 21) Compounds of Preferred 3 where J is J18 22) Compounds of Preferred 3 where J is J19 23) Compounds of Preferred 3 where J is J20 24) Compounds of Preferred 3 where J is J21 25) Compounds of Preferred 3 where J is J22 26) Compounds of Preferred 3 where J is J23 27) Compounds of Preferred 3 where J is J24 28) Compounds of Preferred 3 where J is J25 29) Compounds of Preferred 3 where J is J26 30) Compounds of Preferred 3 where J is J27 31) Compounds of Preferred 3 where J is J28 32) Compounds of Preferred 3 where J is J29 33) Compounds of Preferred 3 where J is J30 34) Compounds of Preferred 3 where J is J31 35) Compounds of Preferred 3 where J is J32 36) Compounds of Preferred 3 where J is 333 37) Compounds of Preferred 3 where J is J34 38) Compounds of Preferred 3 where J is J35 39) Compounds of Preferred 3 where J is J36 40) Compounds of Preferred 3 where J is J37 Other: compounds of formula (I) are those disclosed and claimed in our U.S. Patent Applications Serial Nos. 607,990; 705,833; 612,659; 705,832; 617,608 and 706,961, copies of which are laid open on the file of the present Application DETAILED DESCRIPTION OF THE INVENTION Synthesis The following discussion represents a general outline for the preparation of the compounds of this invention. All of the syntheses described below are multistep with one or more methods being taught for each step. This allows for a wide variety of possible synthetic pathways to prepare a particular compound of Formula I. The proper choice of the synthetic pathway and the best ordering of the reaction sequences for each individual compound will be known to one skilled in the art. The compounds of Formula I canwbe prepared by one or more of the methods described below in Equations 1 through 5. Reaction conditions are given by way of example only As shown in Equation 1. many of the compounds of Formula I where J is other than J6. J12' 322 and Jz3, and when Q = S or O, J is other than J28' JZg J31 and J32. can be prepared by reacting a sulfonylisocyanate (W = o) or a sulfonylisothiocyanate (W = S) of Formula II with an appropriate heterocyclic amine of Formula III. B. A and W are as previously defined. Equation 1 EMI11.1 The reaction is carried out at 25 to 100 C in an inert. aprotic solvent such as methylene chloride or xyLene for 0.5 to 24 hours as taught in U.S. Patent 4.127.405. Compounds of Formula I. where W is S and R is H, (Ia) can be prepared by reacting the appropriate sulfonamide of Formula IV with a heterocyclic isothiocyanate of Formula V. as shown in Equation 2. Equation 2 EMI12.1 The reaction is carried out at 250 to 80 C in an inert aprotic solvent such as acetone op acetonitrile in the presence of a base such as potassium carbonate for 0.5 to 24 hours. The required heterocyclic isothiocyanates V are prepared from the corresponding amines III as taught in EP-A-35893. Compounds of Formula I, where W is O (Ib). can be prepared by reacting a sulfonylcarbamate of Formula VI with an appropriate amine of Formula III. as shown in Equation 3. Equation 3 EMI12.2 The reaction is carried out at 50 to 100 C in a solvent such as dioxane for 0.5 to 24 hours as taught in EP-A-44807. The required carbamates VII are prepared by reacting the corresponding sulfonamides IV wit diphenylcarbonate in the presence of a strong base. Compounds of Formula Ib can also be prepared. as shown in Equation 4. by reacting a heterocyclic carbamate of Formula VII with an appropriate sulfonamide of Formula IV. Equation 4 EMI13.1 The reaction is carried out at 0 to 500C in a solvent such as acetonitrile or dioxane in the presence of a non-nucleophilic base such as DBU for 0.2 to 24 hours as taught in South African Patent Application 830441. The required phenylcarbamate VII are prepared by reacting the corresponding heterocyclic amines III with diphenylcarbonate or phenylchloroformate in the presence of a strong base. Compounds of Formula Ib where J is other than J4. J5. J10. J11. J16. J17. J21. J24 and J25 and when B8 is other than CO2B12 and R21 is other-than CO2R24 can be prepared by reacting the sulfonamides of Formula IV with an appropriate methylcarbamate of Formula VIII in the presence of an equimolar amount of trimethylaluminum. as shown in Equation 5. Eauation 5 EMI13.2 The reaction is carried out at 25µ to 40ec in a solvent such as methylene chloride for 10 to 96 hours under an inert atmosphere as taught in EP-A-84,244. The required carbamates VIII are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a strong base. The intermediate sulfonylisocyanates (W = O) and sulfonylisothiocyanates (W = S) of Formula II from Equation 1 can be prepared as shown in Equations 6 through 8. As shown in Equation 6, sulfonylisocyanates of Formula IIa where J is other than J J12. J22 and J23 can be prepared by the reaction of sulfonamides of Formula IV with phosgene, in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in a solvent such as xylene by the method of U.S. Patent 4.238,621. Equation 6 EMI14.1 The sulfonylisocyanates can also be prepared from the sulfonamides by a two step procedure involving (a) reacting the sulfonamides with n-butylisocyanate in the presence of a base such as K2CO3 at reflux in an inert solvent such as 2-butanone forming a n-butylsulfonylurea: and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent. The method is similar to a procedure taught by Ulrich and Sayigh. Newer Methods of PreParative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London. W. Foerst Ed. Alternatively, as shown in Equation 7, many of the sulfonylisocyanates of Formula IIa can be prepared by reacting the corresponding sulfonyl chlorides IX with cyanic acid salts. Equation 7 EMI15.1 The reaction is carried out at 250 to 100 C in 9n inert aprotic solvent such as acetonitrile for 0.5-24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium i.odide according to the teachings of Japanese Patent No. 76/26,816 (Chem. Abst.. 85:77892e (1976)). The sulfonylisothiocyanates of Formula IIb where J is other than J6. J12. J22 and J23 can be prepared. as shown in Equation 8. by contacting the sulfonamides of Formula IV with carbon disulfide in the presence of two equivalents of a strong base. The resulting salt is then reacted with phosgene according to the teachings of K. Hartke. Arch. Pharm.. 299, 174 (1966). Equation 8 EMI15.2 The sulfonamides of Formula IV with J values J1-J26 can be prepared as taught in EP-A-107,979. The sulfonamides of Formula IV with J values J27-J37 can be prepared as taught in EP-A-79.683. The preparation of compounds of Formula I where J is J1 to J12 and J22 and n=2 can be prepared using the procedures outlined above for the analogous compounds where n=l. The amines of Formula III in Equations 1 and 3 are also important intermediates for the preparation of the compounds of this invention. The amines can be prepared by the methods taught in South African Patent Application 837,434 or by suitable modification thereof as known to one skilled in the art. 2-Aminopyrimidines and 2-aminotriazines are well known in the art. For a review of the synthesis and reactions of 2-aminopyrimidines see The Chemistry of Heterocvclic Compounds, Vol. 16, John Wiley and Sons, New York (1962). For a review of the synthesis and reactions of 2-amino-s-triazines see The Chemist-ry of Heterocyclic Compounds, Vol. 13, John Wiley, New York (1959). F. C. Schaefer, U.S. Patent 3.154,547 and F. C. Schaefer and K. R. Huffman. J. Orq. Chem.. 28. 1812 (1*63). Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in 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 suffiiently basic anion (e.g.. hydroxide. alkoxide, carbonate or hydride). 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 contacting of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal 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. e.g., a copper salt. 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. In this method. the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g.. a potassium, sodium or calcium salt. Acid addition salts. useful in this invention. can be obtained by reacting a compound of Formula I with a suitable acid. e.g., P-toluenesulfonic acid, trichloroacetic acid or the like. Example 1 N-[(4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-yl) aminocarbonyl)-2, 3-dihydro-2-methylbenzothiophene- 7-sulfonamide, l.l-dioxide To a mixture of 0.3 g of 2,3-dihydro-2-methyl benzothiophene-7-sulfonamide. l.l-dioxide and 0.33 g of 2-amino-4-cyclopropyl-6-methoxytriazine phenylcarbamate in 20 mL of dry acetronitrile was added 0.18 mL of DBU. After stirring for 2 hours1 the resulting solution was poured into 25 mL of water and acidified to pH 2 with 1N HC1. The water was decanted from the organic layer, methylene chloride was added and the solution was dried over magnesium sulfate. This solution was filtered. The volatiles were removed by rotary evaporation and the residue was triturated with l-chlorobutane to give 0.2 g of a white solid. m.p. 205-2100C (d). 'H NMR (CDC13) 6 1.2-1.8 (m. 4H, cyclopropyl) 1.55 (d, 3H. CH3) 2.2 (m, lHr cyclopropyl) 3.2 (m. 1H. CH) 3.6 (m. 2H. CH2) 4.1 (s. 3H. OCH3) 7.5-7.9 (m. 3H, arom and NH) 8.4 (m, 1H, arom) 12.7 (broad. 1H. NH) IR (Nujol) 1710 cm (C=O) Using the procedures outlined herein. compounds of Tables I-VI may be prepared. Table I EMI18.1 W n R R1 R2 R5 Y Z m.p.( C) O O H H CH3 H CH3 CH O O H H CH3 -H CH2CH3 CH O O H H CH3 H OCH3 CH O O H H CH3 H OCH2CH3 CH O O H H CH3 H CH2OCH3 CH O O H H CH3 H OCF2H CH O O H H CH3 H SCF2H CH O O H H CH3 H OCH2CF3 CH O O H H CH3 H CF3 CH O O H H CH3 H OCH2CH=CH2 CH O O H H CH3 H OCH2C#CH CH O O H H CH3 H NHCH3 CH O O H H CH3 H N(CH3)2 CH O O H H CH3 H CH(OCH3)2 CH O O H H CH3 H CH3 N O O H H CH3 H CH2CH3 N O O H H CH3 H OCH3 N O O H H CH3 H OCH2CH3 N O O H H CH3 H CH2OCH3 N O O H H CH3 H OCF2H N O O H H CH3 H SCF2H N O O H H CH3 H OCH2CF3 N O O H H CH3 H CF3 N 0 O H H CH3 H OCH2CH=CH2 N Table I (continued) W n R R1 R2 R5 Y Z m.p.( C) O O H H CH3 H OCH2CECH N O O H H CH3 H NHCH3 N O O H H CH3 H N(CH3)2 N O O H H CH3 H CH(OCH3)2 N O O H H CH2CH3 H OCH3 N 152-166 O O H H CH2CH2CH3 H OCH3 N O O H H CH(CH3)2 H OCH3 N O O H H CH2CH2CH2CH3 H OCH3 N O O H H CH2CH(CH3)2 H OCH3 N 138-144 O O H H CH(CH3)CH2CH3 H OCH3 N O O H H C(CH3)3 H OCH3 N O O H H H H OCH3 N O O H H CH3 CH3 OCH3 N O O CH3 H CH3 H OCH3 N S O H H CH3 H OCH3 N O 1 H H CH3 H OCH3 N O 1 H H CH2CH3 H OCH3 N O 1 H H CH2CH2CH3 H OCH3 N O 1 H H CH(CH3)2 H OCH3 N O 1 H H CH2CH2CH2CH3 H OCH3 N O 1 H H CH2CH(CH3)2 H OCH3 N O 1 H H CH(CH3)CH2CH3.H OCH3 N O 1 H H C(CH3)3 H OCH3 N O 1 H H H H OCH3 N O O H o-F CH3 H OCH3 N O O H m-F CH3 H OCH3 N O O H o-Cl CH3 H OCH3 N O O H m-Cl CH3 H OCH3 N 163-167(d) O O H o-Br CH3 H OCH3 N O O H m-Br CH3 H OCH3 N O O H o-CH3 CH3 H OCH3 N O O H m-CH3 CH3 H OCH3 N Table I (continued) W n R1 R2 R5 Y Z m.p.( C) 0 O H o-OCH3 CH3 H OCH3 N O O H m-OCH3 CH3 H OCH3 N 0 O H o-CF CH3 H OCH3 N O O H m-CF3 CH3 H OCH3 N O O H o-SCH3 CH3 H OCH3 N O O H m-SCH3 CH3 H OCH3 N O O H o-OCF2H CH3 H OCH3 N O O H m-OCF2H CH3 H OCH3 N O O H p-F CH3 H OCH3 N O O H p-Cl CH3 H OCH3 N 0 2 H H CH3 H OCH3 N Table II EMI21.1 m.p. J W n W1 R R1 R2 R5 R6 R7 Y Z ( C) J-2 0 0 - H H - H - - OCH3 N J-2 0 1 - H H - H - - OCH3 N J-3 0 O - H H CH3 H - - OCH3 N J-3 0 1 - H H CH3 H - - OCH3 N J-4 0 O - H H - H - - OCH3 N 159-164 J-4 0 O - H o-Cl - H - - OCH3 N J-4 0 O - H m-Cl - H - - OCH3 N J-4 O O - H p-Cl - H - - OCH3 N J-4 0 O - H m-CH3 - H - - OCH3 N J-4 0 O - H o-OCH3 - H - - OCH3 N J-4 0 1 - H H - H - - OCH3 N J-4 O 1 - H o-Cl - H - - OCH3 N J-4 0 1 - H m-Cl - H - - OCH3 N J-4 O 1 - H p-Cl - H - - OCH3 N J-4 0 1 - H m-CH3 - H - - OCH3 N J-4 0 1 - H o-OCH3 - H - - OCH3 N J-5 0 O - H H - H - - OCH3 N J-5 0 1 - H H - H - - OCH3 N J-7 0 O - H H CH3 H - - OCH3 N J-7 0 1 - H H CH3 H - - OCH3 N J-8 0 O - H H - H - - OCH3 N J-8 0 1 - H H - H - - OCH3 N J-9 0 O -- H H CH3 H - - OCH3 N J-9 0 1 - H H CH3 H - - OCH3 N J-8 0 1 - H m-Br - H - - OCH3 N 174-179 Table II (continued) m.p. J W n W1R R1 R2 R5 R6 R7 Y Z ( C) J-10 0 0 O H H - H - - OCH3 N J-10 0 O S H H - H - - OCH3 N J-10 0 1 O H H - H - - OCH3 N J-10 0 1 S H H - H - - OCH3 N J-11 0 0 O H H - H - - OCH3 N J-11 0 0 O H H - H CH3 - OCH3 N J-11 0 0 O H H - H CH3 CH3 OCH3 N J-11 0 O S H H - H H H OCH3 N J-11 0 1 O H H - H H H OCH3 N J-11 0 1 S H H - H H H OCH3 N J-12 0 0 O H H - H H H OCH3 N J-12 0 1 O H H - H H H OCH3 N J-13 0 - - H H CH3 - - - OCH3 N J-14 0 - - H H - - - - OCH3 N J-15 O - - H H CH3 - - - OCH3 N J-17 0 - - H H - - - - OCH3 N J-18 O - - H H CH3 - - - OCH3 N J-19 O - - H H - - - - OCH3 N J-20 O - - H H CH3 - - - OCH3 N J-25 0 - O H H - - H H OCH3 N J-25 0 - S H H - - H H OCH3 N J-26 0 - O H H CH3 - H H OCH3 N J-26 0 - S H H CH3 - H H OCH3 N J-4 0 O - H H - H - - OCH3 CH J-4 0 O - H H - H - - CH3 CH J-4 O O - H H - H - - OCH2CH3 N J-4 0 1 - H H - H - - OCH3 CH J-4 0 1 - H H - H - - CH3 CH J-4 0 1 - H H - H - - OCH2CH3 N Table III EMI23.1 W n W1 R R1 R3 R4 R5Y Z ( C) J-6 0 O - H H H H H OCH3 N J-6 O O - H H CH3 H H OCH3 N J-6 0 O - H H CH2CH3 H H OCH3 N J-6 0 O - H H CH2CH2CH3 H H OCH3 g J-6 0 O - H H CH(CH3)2 H H OCH3 N J-6 O O - H H CH2CH2CH2CH3 H H OCH3 N J-6 O O - H H CH2CH(CH3)2 H H OCH3 N J-6 O O - H H CH(CH3)CH2CH3 H H OCH3 N J-6 O O - H H Cl H H OCH3 N J-6 O O - H H Cl Cl H H OCH3 N J-6 0 O - H H Br Br H OCH3 N J-6 0 O - H H H H H OCH3 U J-6 O 1 - H H H H H OCH3 N J-6 O O - H H CH3 CH3 H OCH3 N J-16 0 - - H H - H - OCH3 N J-16 O - - H H - CH3 - OCH3 N J-16 0 - - H H - CH2CH3 - OCH3 N J-16 0 - - H H - CH2CH2CH3 - OCH3 N J-16 O - - - H H - CH2CH2CH2CH3 - OCH3 N J-16 0 - - H m-Cl - H - OCH3 N J-16 0 - - H o-Cl - H - OCH3 N J-16 O - - H -C1 - H - OCH3 N J-21 O - - H H H - - OCH3 U J-21 0 - - H H CH3 - - OCH3 N J-22 0 0 O H H H H - OCH3 N Table III (continued) J W n W1 R R1 R3 R4 R5 Y Z ( C) J-22 0 O S H H H H - OCH3 N J-22 0 1 O H H H H - OCH3 N J-23 0 - - H H H - - OCH3 g J-24 O - - H H - CH3 CH3 OCH3 N J-24 0 - - H H - CH3 H OCH3 N 182-185 J-24 O - - H H - CH2CH3 H OCH3 N J-24 0 - - H H - CH2CH2CH3 H OCH3 N J-24 - - H H - CH(CH3)2 H OCH3 N J-24 - - H H - CH2CH2CH2CH3 H OCH3 N J-24 0 - - H H - CH2CH(CH3)2 H OCH3 g J-24 O - - H H - CH(CH3)CH2CH3 H OCH3 g J-24 0 - - H H - C(CH3)3 H OCH3 g J-24 0 - - H H - Cl H OCH3 g J-24 0 - - H H - Br H OCH3 N J-24 O - - H o-Cl - CH3 H OCH3 N J-24 O - - H m-Cl - CH3 H OCH3 N J-24 O - - H p-Cl - CH3 H OCH3 N J-24 O - - H m-Cl - CH3 H OCH3 N J-24 O - - H m-Cl - CH3 H OCH3 N J-24 O - - H H - H - OCH3 CH J-16 O - - H H - H - CH3 CH J-16 O - - H H - H - OCH2CH3N J-24 O 1 - H H - CH3 H OCH3 CH J-24 O 1 - H H - CH3 H CH3 CH J-24 O 1 - H H - CH3 H OCH2CH3 N Table IV EMI25.1 wherein W is O. R R R R m.p. J 9 H 8 9 10 11 Y Z ( C) J27 O H H CH3 H H CH3 g J27 O H H CH3 H H OCH3 N J27 O H H CH3 H H OCH2CH3 N J27 O H H CH3 H H CH20CH3 N J27 O H H CH3 H H NHCH3 N J27 0 H H CH3 H H N(CH3)2 N J27 O H H CH3 H H CH3 CH J27 O H H CH3 H H OCH3 CH J27 0 H H CH3 H H OCH2CH3 OH J27 O H H CH3 H H CH2OCH3 CH J27 O H H CH3 H H NHCH3 CH J27 O H H CH3 H H N(CH3)2 CH J27 O CH3 H CH3 H H OCH3 N J27 O CH3 H CH3 H H OCH3 CH J27 O H CH3 CH3 H H OCH3 N J27 O H CH3 CH3 H H OCH2CH3 N J27 O H CH3 CH3 H H OCH2CH3 N J27 O H OCH3 CH3 H H OCH3 N J27 O H OCH3 CH3 H H OCH2CH3 N J27 O H Cl CH3 H H OCH3 N J27 O H Cl CH3 H H OCH2CH3 N J27 O H Br CH3 H H OCH3 N J27 0 H C02CH3 CH3 H H OCH3 N J27 0 H <RTI ID=25.9> S 2CH3 CH3 H H OCH3 N J27 O H SO2CH2CH3 CH3 H H OCH3 N J27 0 H OSO2CH3 CH3 H H OCH3 N J27 O H OSO2CH2CH3 CH3 H H OCH3 N J27 O H SO2N(CH3)2 CH3 H H OCH3 N J27 O H H H H H OCH3 N 188-191 TABLE IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J27 O H H H H H OCH2CH3 N J27 O H H H H H OCH3 CH J27 O H H CH3 CH3 H OCH3 N J27 O H H CH3 CH3 H OCH2CH3 N J27 0 H H CH3 CH3 H OCH3 CH J27 O H H CH2CH3 H H OCH3 N J27 O H H CH2CH2CH3 H H OCH3 N J27 O H H CH2CH2 CH3 H OCH3 N J27 O H OCH3 CH3 CH3 H OCH3 N J27 O H Cl CH3 CH3 H OCH3 N J27 O H H CH3 H CH3 OCH3 N J27 O H H CH3 H CH3 OCH3 CH J27 O H H CH2CH3 H CH3 OCH3 N J27 0 H Cl CH3 H CH3 OCH3 N J27 S H H CH3 H H CH3 N J27 S H H CH3 H H OCH3 N J27 S H H CH3 H H OCH2CH3 N J27 S H H CH3 H H CH2OCH3 N J27 S H H CH3 H H NHCH3 N J27 S H H CH3 H H N(CH3)2 N J27 S H H CH3 H H CH3 CH J27 S H H CH3 H H OCH3 CH J27 S H H CH3 H H OCH2CH3 CH J27 S H H CH3 H H CH2OCH3 CH J27 S H H CH3 H H NCH3 CH J27 S H H CH3 H H N(CH3)2 CH J27 S CH3 H CH3 H H OCH3 N J27 S CH3 H CH3 H H OCH3 CH J27 S H CH3 CH3 H H OCH3 N J27 S H CH3 CH3 H H OCH2CH3 N J27 S H OCH3 CH3 H H OCH3 N J27 S H OCH3 CH3 H H OCH2CH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J27 S H Cl CH3 H H OCH3 N J27 S H Cl CH3 H H OCH2CH3 N J27 S H Br CH3 H H OCH3 N J27 S H CO2CH3 CH3 H H OCH3 N J27 S H SO2CH3 CH3 H H OCH3 N J27 S H SO2CH2CH3 CH3 H H OCH3 N J27 S H OSO2CH3 CH3 H H OCH3 N J27 S H OSO2CH2CH3 CH3 H H OCH3 N J27 S H H H H H OCH3 N J27 S H H H H H OCH2CH3 N J27 S H H H H H OCH3 CH J27 S H H CH3 CH3 H OCH3 N J27 S H H CH3 CH3 H OCH2CH3 N J27 S H H CH3 CH3 H OCH3 CH J27 S H H CH2CH3 H H OCH3 N J27 S H H CH2CH2CH3 H H OCH3 N J27 S H H CH2CH2 CH3 H OCH3 N J27 S H OCH3 CH3 CH3 H OCH3 N J27 S H Cl CH3 CH3 H OCH3 N J27 S H H CH3 H CH3 OCH3 N J27 S H H CH3 H CH3 OCH3 CH J27 S H H CH2CH3 H CH3 OCH3 N J27 S H Cl CH3 H CH3 OCH3 <RTI ID=27.9> N J27 SO2 H H CH3 H H CH3 N J27 SO2 H H CH3 H H OCH3 N J27 SO2 H H CH3 H H OCH2CH3 N J27 SO2 H H CH3 H H CH20CH3 N J27 SO2 H H CH3 H H NHCH3 N J27 SO2 H H CH3 H H N(CH3)2 N J27 SO2 H H CH3 H H CH3 CH J27 SO2 H H CH3 H H OCH3 CH J27 SO2 H H CH3 H H OCH2CH3 CH Table IV (continued) wherein W is O. R R8 R9 R10 R11 Y J27 SO2 H H CH3 H H CH20CH3 CH J27 SO2 H H CH3 H H NHCH3 CH J27 SO2 H H CH3 H H N(CH3)2 CH J27 SO2 CH3 H CH3 H H OCH3 N J27 SO2 C3H H CH3 H H OCH3 CH J27 SO2 H CH3 CH3 H H OCH3 N J27 SO2 H CH3 CH3 H H OCH2CH3 g J27 SO2 H OCH3 CH3 H H OCH3 g J27 SO2 H OCH3 CH3 H H OCH2CH3 X J27 SO2 H Cl CH3 H H OCH3 X J27 SO2 H Cl CH3 H H OCH2CH3 N J27 S 2 H Br CH3 H H OCH3 g J27 SO2 H CO2CH3 CH3 H H OCH3 N J27 SO2 H SO2CH3 CH3 H H OCH3 N J27 SO2 H SO2CH2CH3 CH3 H H OCH3 N J27 SO2 H OSO2CH3 CH3 H H OCH3 N J27 SO2 H OSO2CH2CH3 CH3 H H OCH3 N J27 SO2 H H H H H OCH3 N J27 802 H H H H H H OCH2CH3 N J27 SO2 H H H H H OCH3 CH J27 SO2 H H CH3 CH3 H OCH3 N J27 SO2 H H CH3 CH3 H OCH2CH3 N J27 SO2 H H CH3 CH3 H OCH3 CH J27 SO2 H H CH2CH3 H H OCH3 N J27 SO2 H H CH2CH2CH3 H H OCH3 N J27 SO2 H H CH2CH2 CH3 H OCH3 N J27 SO2 H OCH3 CH3 CH3 H OCH3 N J27 SO2 H Cl CH3 CH3 H OCH3 B J27 SO2 H H CH3 H CH3 OCH3 N J27 SO2 H H CH3 H CH3 OCH3 CH J27 SO2 H H CH2CH3 H CH3 OCH3 N J27 SO2 H Cl CH3 H CH3 OCH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J30 O H H CH3 H - CH3 N J30 O H H CH3 H - OCH3 N J30 O H H CH3 H - OCH2CH3 N J30 O H H CH3 H - CH2OCH3 N J30 O H H CH3 H - NHCH3 N J30 O H H CH3 H - N(CH3)2 N J30 O H H CH3 H - CH3 CH J30 O H H CH3 H - OCH3 CH J30 O H H CH3 H - OCH2CH3 CH J30 O H H CH3 H - CH2OCH3 CH J30 O H H CH3 H - NHCH3 CH J30 O H H CH3 H - N(CH3)2 CH J30 O CH3 H CH3 H - OCH3 N J30 O CH3 H CH3 H - OCH3 CH J30 O H CH3 CH3 H - OCH3 N J30 O H CH3 CH3 H - OCH2CH3 N J30 O H OCH3 CH3 H - OCH3 N J30 O H OCH3 CH3 H - OCH2CH3 N J30 O H Cl CH3 H - OCH3 N J30 O H Cl CH3 H - OCH2CH3 N J30 O H Br CH3 H - OCH3 N J30 O H CO2CH3 CH3 H - OCH3 N J30 O H SO2CH3 CH3 H - OCH3 N J30 O H SO2CH2CH3 CH3 H - OCH3 N J30 O H OSO2CH3 CH3 H - OCH3 N J30 O H OSO2CH2CH3 CH3 H - OCH3 N J30 O H SO2N(CH3)2 CH3 H - OCH3 N J30 O H H H H - OCH3 N J30 O H H H H - OCH2CH3 N J30 O H H H H - OCH3 CH J30 O H H CH3 CH3 - OCH3 N J30 O H H CH3 CH3 - OCH2CH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J30 O H H CH3 CH3 - OCH3 CH J30 O H H CH2CH3 H - OCH3 N J30 O H H CH2CH2CH3 H - OCH3 N J30 O H H CH2CH2 CH3 - OCH3 N J30 O H OCH3 CH3 CH3 - OCH3 N J30 O H Cl CH3 CH3 - OCH3 N J30 S H H CH3 H - CH3 N J30 S H H CH3 H - OCH3 N J30 S H H CH3 H - OCH2CH3 N J30 S H H CH3 H - CH2OCH3 N J30 S H H CH3 H - NHCH3 N J30 S H H CH3 H - N(CH3)2 N J30 S H H CH3 H - CH3 CH J30 S H H CH3 H - OCH3 CH J30 S H H CH3 H - OCH2CH3 CH J30 S H H CH3 H - CH2OCH3 CH J30 S H H CH3 H - CHCH3 CH J30 S H H CH3 H - N(CH3) CH J30 S H H CH3 H - N(CH3)2 CH J30 S CH3 H CH3 H - OCH3 N J30 S CH3 H CH3 H - OCH3 CH J30 S H CH3 CH3 H - OCH3 N J30 S H CH3 CH3 H - OCH2CH3 N J30 S H OCH3 CH3 H - OCH3 N J30 S H OCH3 CH3 H - OCH2CH3 N J30 S H Cl CH3 H - OCH3 N J30 S H Cl CH3 H - OCH2 CH3N J30 S H Br CH3 H - OCH3 N J30 S H CO2CH3 CH3 H - OCH3 N <RTI ID=30.3> J30 S H SO2CH3 CH3 H - OCH3 N J30 S H SO2CH2CH3 CH3 H - OCH3 N J30 S H OSO2CH3 CH3 H - OCH3 X J30 S H OSO2CH2CH3 CH3 H - OCH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J30 S H H H H - OCH3 U J30 S H H H H - OCH2CH3 N J30 S H CH3 CH3 H - OCH3 CH J30 S H H CH3 CH3 - OCH3 N J30 S H H CH3 CH3 - OCH2CH3 N J30 S H H CH3 CH3 - OCH3 CH J30 S H H CH2CH3 H - OCH3 N J30 S H H CH2CH2CH3 - OCH3 N J30 S H H CH2CH2 CH3 - OCH3 N J30 S H OCH3 CH3 CH3 - OCH3 N J30 S H Cl CH3 CH3 - OCH3 N J30 SO2 H H CH3 H - CH3 N J30 SO2 H H CH3 H - OCH3 N J30 SO2 H H CH3 H - OCH2CH3 N J30 SO2 H H CH3 H - CH2OCH3 N J30 SO2 H H CH3 H - NHCH3 N J30 SO2 H H CH3 H - N(CH3)2 N J30 SO2 H H CH3 H - CH3 CH J30 SO2 H H CH3 H - OCH3 CH J30 SO2 H H CH3 H - OCH2CH3 CH J30 SO2 H H CH3 H - CH2OCH3 CH J30 SO2 H H CH3 H - NHCH3 CH J30 SO2 H H CH3 H - N(CH3)2 CH J30 SO2 CH3 H CH3 H - OCH3 N J30 SO2 CH3 H CH3 H - OCH3 CH J30 SO2 H CH3 CH3 H - OCH3 N J30 SO2 H CH3 H - OCH2CH3 N J30 SO2 H OCH3 CH3 H - OCH3 N J30 SO2 H OCH3 CH3 H - OCH2CH3 N J30 SO2 H Cl CH3 H - OCH3 N J30 SO2 H Cl CH3 H - OCH2CH3 N J30 SO2 H Br CH3 H - OCH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J30 SO2 H CO2CH3 CH3 H - OCH3 N J30 SO2 H SO2CH3 CH3 H - OCH3 N J30 SO2 H SO2CH2CH3 CH3 H - OCH3 N J30 SO2 H OSO2CH3 CH3 H - OCH3 N J30 SO2 H OSO2CH2CH3 CH3 H - OCH3 N J30 SO2 H SO2N(CH3)2 CH3 H - OCH3 N J30 SO2 H H H H - OCH3 N J30 SO2 H H H H - OCH2CH3 N J30 SO2 H H H H - OCH3 CH J30 SO2 H H CH3 CH3 - OCH3 g J30 SO2 H H CH3 CH3 - OCH2CH3 N J30 SO2 H H CH3 CH3 - OCH3 CH J30 SO2 H H CH2CH3 H - OCH3 N J30 SO2 H H CH2CH2CH3 H - OCH3 N J30 SO2 H H CH2CH2 CH3 - OCH3 N J30 SO2 H OCH3 CH3 CH3 - OCH3 n J30 SO2 H Cl CH3 CH3 - OCH3 N J28 O H H H H H OCH3 N J28 0 H H CH3 H H OCH3 N J28 O H H CH3 H H OCH2CH3 N J28 0 H H CH3 CH3 H OCH3 N J28 O H H CH3 CH3 H OCH2CH3 N J28 0 H H CH3 CH3 H OCH3 CH J28 O H Cl CH3 CH3 H OCH3 N J28 O H OCH3 CH3 CH3 H OCH3 N J28 0 CH3 H CH3 CH3 H OCH3 N J28 0 H H H H CH3 OCH3 N J28 O H H CH2CH3 CH3 H OCH3 N J31 O H H H H - OCH3 X J31 O H H CH3 H - OCH3 N J31 O H H CH3 H - OCH2CH3 N J31 O H H CH3 H - OCH3 CH Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J31 O H H CH3 H - CH3 CH J31 O H Cl CH3 H - OCH3 N J31 O H H CH3 CH3 - CH3 N J31 O H Cl CH3 CH3 - OCH3 N J31 O H OCH3 CH3 CH3 - OCH3 N J28 S H H H H H OCH3 N J28 S H H CH3 H H OCH3 N J28 S H H CH3 H H OCH2CH3 N J28 S H H CH3 CH3 H OCH3 N J28 S H H CH3 CH3 H OCH2CH3 N J28 S H H CH3 CH3 H OCH3 CH J28 S H Cl CH3 CH3 H OCH3 U J28 S H OCH3 CH3 CH3 H OCH3 N J28 S CH3 H CH3 CH3 H OCH3 N J28 S H H H H CH3 OCH3 N J28 S H H CH2CH3 CH3 H OCH3 N J31 S H H H H - OCH3 N J31 S H H CH3 H - OCH3 N J31 S H H CH3 H - OCH2CH3 N J31 S H H CH3 H - OCH3 CH J31 S H H CH3 H - CH3 CH J31 S H H CH3 H - OCH3 N J31 S H H CH3 CH3 - OCH3 N J31 S H Cl CH3 CH3 - OCH3 X J31 S H OCH3 CH3 CH3 - OCH3 N J28 SO2 H H H H H OCH3 U J28 SO2 H H CH3 H H OCH3 U J28 SO2 H H CH3 H H OCH2CH3 N J28 SO2 H H CH3 CH3 H OCH3 N J28 SO2 H H CH3 CH3 H OCH2CH3 N J28 SO2 H H CH3 CH3 H OCH3 CH J28 SO2 H Cl CH3 CH3 H OCH3 N Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J28 SO2 H OCH3 CH3 CH3 H OCH3 N J28 SO2 CH3 H CH3 CH3 H OCH3 N J28 SO2 H H H H CH3 OCH3 N J28 SO2 H H CH2CH3 CH3 H OCH3 N J31 SO2 H H H H - OCH3 N J31 SO2 H H CH3 H - OCH3 N J31 SO2 H H CH3 H - OCH2CH3 N J31 SO2 H H CH3 H - OCH3 CH J31 SO2 H H CH3 H - CH3 CH J31 SO2 H Cl CH3 H - OCH3 N J31 SO2 H H CH3 CH3 - OCH3 N J31 SO2 H Cl CH3 CH3 - OCH3 g J31 SO2 H OCH3 CH3 CH3 - OCH3 N J33 - H H H - - OCH3 N J33 - H H H - - OCH3 CH J33 - H H CH3 - - OCH3 N J33 - H Cl CH3 - - OCH3 N J33 - H H CH2CH3 - - OCH3 N J33 - H H CH2CH2CH3 - - OCH3 N J29 S H H CH3 - H OCH3 g J29 S H H H - H OCH3 N J29 S H H CH3 - H OCH2CH3 N J29 S H H CH3 - H OCH3 CH J29 S H H CH3 - H CH2OCH3 CH J29 S H H CH2CH3 - H OCH3 N J29 S H H CH(CH3)2 - H OCH3 N J29 S H Cl CH3 - H OCH3 N J29 S H OCH3 CH3 - H OCH3 N J29 S H H H - CH3 OCH3 n J32 S H H H - - OCH3 N J32 S H H H - - OCH2CH3 N J32 S H H H - - OCH3 CH Table IV (continued) wherein W is O. J Q R R8 R9 R10 R11 Y Z J32 S H H CH3 - - NHCH3 N J32 S H H CH3 - - NH(CH3)2 N J32 S H H CH3 - - OCH3 N J32 S H H CH3 - - OCH2CH3 N J32 S H Cl CH3 - - OCH3 N J32 S H CH3 CH3 - - OCH3 - N J32 S H H CH2CH3 - - OCH3 N J32 S H H CH(CH3)2 - - OCH3 N J32 S H H CH2CH2CH2 - - OCH3 N J29 SO2 H H CH3 - H OCH3 N J29 SO2 H H 3 - H OCH3 N J29 SO2 H H H - H OCH3 N J29 SO2 H H CH3 - H OCH2CH3 N J29 SO2 H H CH3 - H OCH3 CH J29 SO2 H H CH3 - H CH2OCH3 CH J29 SO2 H H CH2CH3 - H OCH3 N J29 SO2 H H CH(CH3)2 - H OCH3 N J29 SO2 H Cl CH3 - H OCH3 N J29 SO2 H OCH3 CH3 - H OCH3 N J29 SO2 H H H - CH3 OCH3 N J32 SO2 H H H - - OCH3 N J32 SO2 H H H - - OCH2CH3 N J32 SO2 H H H - - OCH3 CH J32 SO2 H H CH3 - - NHCH3 N J32 SO2 H H CH3 - - NH(CH3)2 N J32 SO2 H H CH3 - - OCH3 N J32 SO2 H H CH3 - - OCH2CH3 N J32 SO2 H Cl CH3 - - OCH3 N J32 SO2 H CH3 CH3 - - OCH3 N J32 SO2 H H CH2CH3 - - OCH3 N J32 SO2 H H CH(CH3)2 - - OCH3 N J32 SO2 H H CH2CH2CH2 - - OCH3 N Table IV (continued) wherein W is 0; unless *, where W is S. J g R R8 R9 R10 R11 Z J27 O H CO2CH2CH2CH3 CH3 H H OCH3 N J27 O H CO2CH2CH=CH2 CH3 H H OCH3 N J27 0 H C 2CH2CH20CH3 CH3 H H OCH3 N J27 O H CO2CH2CH2Cl CH3 H H OCH3 N J27 0 H SO2CH2CH2CH3 CH3 H H OCH3 N J27 0 H S02CH(CH3)2 2 CH3 H H OCH3 N J27 O H OSOCH2CH2CH3 CH3 H H OCH3 N J27 O H OSO2CH(CH3)2 CH3 H H OCH3 N J27 O H SO2N(CH3)CH2CH3 CH3 H H OCH3 3 J27 O H SO2(N(CH2CH3)2 2 CH3 H H OCH3 g J27 O H OSO2CF3 CH3 H H OCH3 N J27 SO2 H CO2CH2CH2CH3 CH3 H H OCH3 N J27 SO2 H CO2CH2CH=CH2 CH3 H H OCH3 N J27 SO2 H Co2CH2CH2OCH3 CH3 H H OCH3 <RTI ID=36.14> N J27 SO2 H CO2CH2CH2Cl CH3 H H OCH3 N J27 SO2 H SO2CH2CH2CH3 CH3 H H OCH3 N J27 SO2 H SO2CH(CH3)2 CH3 H H OCH3 N J27 SO2 H OSO2CH2CH2CH3 CH3 H H OCH3 N J27 SO2 H OSO2 CH(CH3)2 CH3 H H OCH3 N J27 SO2 H SO2N(CH3)CH2CH3 CH3 H H OCH3 N J27 SO2 H SO2N(CH2CH3)2 CH3 H H OCH3 N J27 SO2 H OSO2CF3 CH3 H H OCH3 N J27 O H H CH3 H H CH3 N * J27 0 H H CH3 H H OCH3 CH * Table V EMI37.1 J R17 R18 R19 R20 R21 R W Q Y Z ( C) J34 H H H H H H O O CH3 CH J34 H H H H H H O 0 C2H5 CH J34 H H H H H H O O CH2OCH3 CH J34 H H H H H H O 0 CH20C2H5 CH J34 H H H H H H O O OCH3 CH J34 H H H H H H O 0 OCH2H5 CH J34 H H H H H H O 0 OCF2H CH H H H H H H O O SCF2H CH 34 H H H H H- H H O O OCH2CH3 CH J34 H H H H H H H O O OCH2CH2F CH H H H H H H O O OCH2CH=CH2 CH H H H H H H O O OCH2C#CH CH J34 H H H H H H O O NHCH3 CH J34 H H H H H H O O N(CH3)2 CH J34 H H H H H H O O CH(OCH3)2 CH J34 CH3 H H H H H O O CH3 CH J34 CH3 H H H H H O O C2H% CH J34 CH3 H H H H H O O CH2OCH3 CH J34 H CH3 H H H H O O CH2OC2H5 CH J34 H CH3 H H H H O O OCH3 CH J34 H CH3 H H H H O O OC2H5 CH J34 H CH3 H H H H O O OCF2H CH J34 H CH3 H H H H O O SCF2H CH Table V Continued J R17 R18 R19 R20 R21 R W Q Y Z ( C) J34 CH3 H H H H H O O OCH2CF3 CH J34 CH3 H H H H H O O OCH2CH2F CH J34 CH3 H H H H H O O OCH2CH=CH2 CH J34 CH3 H H H H H O 0 OCH2C#CH CH J34 CH3 H H H H H O O NHCH3 ch J34 CH3 H H H H H O O N(CH3)2 2 CH J34 CH3 H H H H H O O CH(OCH3)2 CH J34 CH3 CH3 H H H H O O CH3 CH J34 CH3 CH3 H H H H O O C2H5 CH J34 CH3 Ch3 H H H H O O CH2OCH3 CH J34 CH3 Ch3 H H H H O O OCH3 CH J34 CH3 Ch3 H H H H O O OC2H5 CH J34 CH3 CH@ H H H H O O OCF2H CH J34 CH3 CH3 H H H H O O OCH2CH3 CH J34 CH3 CH3 H H H H O O OCH2CH2F CH J34 CH3 CH3 H H H H O O OCH2CH=CH2 CH J34 CH3 CH3 H H H H O O OCHC#CH CH J34 CH3 CH3 H H H H O O NHCH3 CH J34 CH3 CH3 H H H H O O N(CH3)2 CH J34 CH3 CH3 H H H H O O CH(OCH3)2 CH J34 CH3 CH3 H H H H O O CH3 CH J34 H CH3 CH3 H H H O O C2H5 CH J34 H CH3 CH3 H H H O O CH2OCH3 CH J34 CH3 H CH3 H H H O 0 OCH3 CH J34 CH3 H CH3 H H H O 0 OC2H5 CH J34 CH3 H CH3 H H H O O OCF2H CH J34 CH3 H CH3 H H H O O OCH2CF3 CH J34 CH3 H CH3 H H H O O OCH2CH2F CH J34 CH3 H CH3 H H H O O OCH2=CH2 CH J34 CH3 H CH3 H H H O O CH(OCH3)2 CH J34 C2H5 H H H H H O O CH3 CH J34 n-C3H7 H H H H H O O CH3 CH Table V Continued m.p. J R17 R18 R19 R20 R21 R w Q Y Z ( C) J34 CH(CH3)2 H H H H H O O CH3 CH J34 H H H Cl CH H 0 O CH3 - CH J34 H H H Cl H H O O OCH3 CH J34 CH3 H H Cl H H O O OCH3 CH J34 H H H Cl H H O O OC2H5 CH J34 H H H Cl H H O O OCF2H CH J34 H H H Cl H H O O OCF2CF3 CH J34 H CH3 H Cl H H O O OCH2CH2F CH J34 H H H Cl H H O O CH(OCH3)2 CH J34 CH3 H H Br H H O O CH3 CH J34 H CH3 H Br H H O O C2 H5 CH J34 CH3 H H Br H H O O OCH3 CH J34 H H H Br H H O O OCH3 CH J34 H H H Br H H O O OCF2H CH J34 CH3 H H Br H H O O OCH2CF3 CH J34 CH3 H H Br H H O O OCH2CH2F CH J34 CH3 H H Br H H O O CH(OCH3)2 CH J34 CH3 H H CH3 H H O O CH3 CH J34 CH3 H H CH3 H H O O OCH3 CH J34 CH3 H H OCH3 H H O O CH3 CH J34 CH3 H H OCH3 H H O O OCH3 CH J34 H CH3 H CF3 H H O O OCH3 CH J34 H CH3 H CF3 H H O O CH3 CH J34 H H H H H H O SO2 CH3 CH J34 H H H H H H O SO2 C2H5 CH J34 H H H H H H O SO2 OCH3 CH J34 H H H H H H O SO2 OC2H5 CH J34 H H H H H H O SO2 OCF2H CH J34 H H H H H H O SO2 OCH2CF3 CH J34 H H H H H H O SO2 OCH2CH2F CH J34 CH3 H H H H H O SO2 CH3 CH Table V Continued m.p. J R17 R18 R19 R20 R21 R W Q Y Z ( C) J34 CH3 H H H H H O SO2 C2H5 CH J34 CH3 H H H H H O S02 CH2OCH3 CH J34 CH3 H H H H H O S02 CH2OC2H5 CH J34 CH3 H H H H H O SO2 OCH3 CH J34 CH3 H H H H H O SO2 OC2H5 CH J34 CH3 H H H H H O SO2 OCF2H CH J34 H CH3 H H H H O SO2 SCF2H CH J34 H CH3 H H H H O SO2 OCH2CH3 CH J34 H CH3 H H H H O SO2 OCH2CH2F CH J34 H CH3 H H H H O SO2 OCH2=CH2 CH J34 H CH3 H H H H O SO2 OCH2#CH CH J34 H CH3 H H H H O SO2 NHCH3 CH J34 H CH3 H H H H O SO2 N(CH3)2 CH J34 H CH3 H H H H O SO2 CH(OCH3)2 CH J34 CH3 CH3 H H H H O SO2 CH3 CH J34 CH3 CH3 H H H H O SO2 OCH3 CH J34 CH3 CH3 H H H H O SO2 OC2H5 CH J34 CH3 CH3 H H H H O SO2 OCF2H CH J34 CH3 CH3 H H H H O SO2 C2H5 CH J34 C2H5 H H H H O SO2 CH3 CH J34 n-C3H7 H H H H H O SO2 CH3 CH J34 H H CH3 H H H O SO2 CH3 CH J34 H H H H H H O S CH3 CH J34 CH3 H H H H H O S OCH3 CH J34 CH3 H H H H H O S CH3 CH J34 CH3 CH3 H H H H O S OCH3 CH J34 CH3 CH3 H H H H O S CH3 CH J34 C2H5 H H H H H O S CH3 CH J34 n-C3H7 H H H H H O S CH3 CH J34 CH3 H CH3 H H H O S CH3 CH J34 CH3 H H CH3 H H O SO2 CH3 CH Table V Continued m.p. J R17 R18 R19 R20 R21 R W Q Y Z ( C) J34 CH3 H H H H CH3 O O CH3 CH J34 CH3 H H H H CH3 O SO2 CH3 CH J34 CH3 H H H H H S O CH3 OH J34 CH3 H H H H H S SO2 CH3 CH J34 CH3 H H H CH3 H O SO2 CH3 CH J34 CH3 H H H OCH3 H O O OCH3 CH J34 CH3 CH3 H H Cl H O S OCH3 CH J34 CH3 H H H Cl H O O OCH3 N J34 CH3 H H H NO2 H O 9 CH3 CH J34 CH3 H H H CO2CH3 H O O OC2H5 N J34 CH3 H H H CO2C2H5 H O SO2 CH3 CH J34 CH3 H H H C 2CH2CH2CH3 H O O CH3 CH J34 CH3 CH3 H H CO2CH(CH3)2 H O S OCH3 CH J34 CH3 H H H C02CH2CH=CH2 H O O CH3 CH J34 CH3 H H H CO2CH2CH2OCH3 H O O CH3 CH J34 CH3 H H H C 2CH2CH2Cl H O O OCH3 CH J34 CH3 CH3 H H SO2CH3 H O O OCF2H N J34 CH3 CH3 H H SO2C2H5 H O O CH3 CH J34 CH3 H H H SO2CH2CH2CH3 H O O OCH3 CH J34 CH3 H H H SO2CH2(CH3)2 H O O CH3 CH J34 H CH3 H H OSO2CH3 H O SO2 CH3 CH J34 CH3 H H H OSO2C2H5 H O O CH3 CH J34 CH3 H H H OSO2CH2CH2CH3 H O O CH3 CH J34 CH3 H H H OSO2CH(CH3)2 H O S CH3 CH J34 CH3 CH3 H H OSO2CH3 H O O OCH3 N J34 CH3 H H H SO2N(CH3)2 H O O CH3 CH J34 CH3 H H H SO2N(CH3)C2H5 H O O CH3 CH J34 H H H H H H O O CH3 N J34 H H H H H H O O OCH3 E J34 H H H H H O O OC2H5 N J34 H H H H H O O OCF2H N Table V Continued J R17 R18 R19 R20 R21 R W O Y Z ( C) J34 H H H H H H O O SCF2H H J34 H H H H H H O O OCH2CF3 N J34 H H H H H H O O OCH2CH2F N J34 H H H H H H O O OCH2CH=CH2 N J34 H H H H H H O O OCH2C#CH N J34 CH3 H H H SO2N(OCH3)CH3 H O O OCH3 CH J34 H H H H H H O O NHCH3 N J34 H H H H H H O O NH(CH3)2 N J34 H H H H H H O O CH(OCH3)2 N J34 CH3 H H H H H O O OCH3 N J34 CH3 H H H H H O O OCH2H5 N J34 CH3 H H H H H O O OCF2H N J34 H CH3 H H H H O O OCH2CF3 N J34 H CH3 H H H H O O OCH2CH2F N J34 H CH3 H H H H O O OCH2CH=CH2 N J34 CH3 CH H H H H O O OCH3 N J34 CH3 CH3 H H H H O O OC2H5 N J34 CH3 H CH3 H H H O O OCH3 N J34 H CH3 CH3 H H H O O OC2H5 N J34 C2H5 H H H H H O SO2 OCH3 N J34 CH(CH3)2 H H H H H O O OCH3 N J34 n-propyl H H H H H O O OCH3 N J34 CH3 H H Cl H H O O OCH3 N J34 H H H Cl H H O O OC2H5 N J34 CH3 H H Br H H O O OCH3 N J34 H H H Cl H H O O OCH3 N J34 CH3 H H CH3 H H O O OCH3 N J34 CH3 H H OCH3 H H O O OCH3 N J34 CH3 H H CF3 H H O O OCH3 N J34 H H H H H H O SO2 OCH3 N 234-236(d) Table V Continued m.p. J R17 R18 R19 R20 R21 R W Q Y Z J34 H H H H H H O SO2 OC2H5 N J34 CH3 H H H H H O SO2 CH3 N J34 CH3 H H H H H O 502 OCH3 N 205-210(d) J34 CH3 H H H H H O SO2 OC2H5 N J34 CH3 H H H H H O SO2 C2H5 n J34 CH3 H H H H H O S02 OCF2H N J34 CH3 H H H H H O SO2 SCF2H N J34 H CH3 H H H H O SO2 OCH2CF3 N J34 H CH3 H H H H O SO2 OCH2CH2F N J34 H CH3 H H H H O SO2 OCH2CH=CH2 N J34 H CH3 H H H H O SO2 OCH2C#CH N J34 H CH3 H H H H O SO2 NHCH3 N J34 H CH3 H H H H O SO2 N(CH3)2 N J34 CH3 CH3 H H H H O SO2 OCH3 N J34 C2H5 H H H H H O SO2 OCH3 N J34 n-C3H7 H H H H H O SO2 OCH3 N J34 H H CH3 H H H O SO2 OCH3 N J34 H H H H H H O 5 OCH3 N J34 CH3 H H H H H O S OCH3 N J34 CH3 CH3 H H H H O S OCH3 N J34 C2H5 H H H H H O 5 OCH3 N J34 n-C3H7 H H H H H O S OCH3 N J34 CH3 H H CH3 H H O SO2 OCH3 N J34 CH3 H H H H CH3 O SO2 OCH3 N J34 CH3 H H H Cl H O SO2 OCH3 N J34 CH3 H H H CH3 H O SO2 OCH3 N J34 CH3 H H H H H S O OCH3 N J34 CH3 H H H Cl H O SO2 OC2H5 N J34 CH3 H H H CH4 H O SO2 OC2H5 N J34 CH3 H H H H H O SO OCH3 CH J34 n-butyl H H H H H O S02 OCH3 N Table V Continued m.p. J R17 R18 R19 R20 R21 R W Q Y Z ( C) J34 H C2H5 H H H H O O OCH3 N J34 H n-propyl H H H H O SO2 OCH3 N J34 H CH(CH3)2 H H H H O SO2 OCH3 N J34 H n-butyl H H H H O O OCH3 N J34 CH3 H H F H H O O OCH3 N J34 CH3 H H SCH3 H H O O OCH3 N J34 CH3 H H OCF2H H H O O OCH3 N J34 CH3 H H H F H O O OCH3 N J34 CH3 H H H CFH3 H O O OCH3 N J34 CH3 H H H SCH3 H O O OCH3 N J34 CH3 H H H OCF2H H O O OCH3 N J34 CH3 H H H H H O O CH3 N J34 H H H Br H H O O OCH3 N J34 CH3 H H H Cl H O SO2 OCH3 N Table VI EMI45.1 J R17 R18 R19 R20 R21 R W Q Y Z J35 H H H H H H O O OCH3 CH J35 H H H H H H O O OCH3 N J35 CH3 H CH3 H H H O SO2 OCH3 CH J35 H H H H H H O S OCH3 CH J35 H H H H H H S O OCH3 CH J35 H CH3 CH3 H H H O SO2 OCH3 N J35 H H H H CH3 H O O OCH3 CH m.p. J R20 R21 R22 R23 R W Q1Y Z ( C) J36 H H H H H O O OCH3 CH a36 H H H H H O 0 OCH3 N J36 H H CH3 H H O O OCH3 CH J36 H H CH3 H H O O OCH3 N J36 H H CH3 H H O O OC2H5 N J36 H H CH3 CH3 H O SO2 OCH3 CH J36 H H C2H5 H H O O OCH3 CH J36 H H n-C3H7 H H O O OC2H5 N J36 H H Cl CH3 H O O OCH3 CH J36 H H Br CH3 H O O OCH3 CH J36 H H CH3 Cl H O O OCH3 N J36 H HCH3 Br H O O OCH3 CH J36 H H CH3 CH3 H O S OCH3 CH J36 Cl H CH3 H H O O OCH3 CH J36 CH3 H CH3 H H O O OCH3 CH J36 H Cl CH3 H H O O OCH3 CH J36 H H n-butyl H H O O OCH3 CH Table VI (continued) m.p. J R21 R22 R23 R W A1 Y Z ( C) J37 H H CH3 H O O OCH3 CH J37 H CH3 CH3 H O O OCH3 CH J37 H H H H O S OCH3 CH J37 H H CH3 H O SO2 OCH3 CH J37 H H CH3 H O O OCH3 N J37 H H CH3 H O SO2 OCH3 N Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules. pellets. solutions, suspensions, emulsions. wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1S 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 VII Active Weight Percent* Ingredient Diluent(s) Surfactant 16 ) 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 some times 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 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, Litter. 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 Engineers Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3.235,361. February 15, 1966. Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3.309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8. 12, 15, 39, 41. 52, 53, 58, 132, 138-140, 162-164, 166. 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891.855, June 23. 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, ."Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples. all parts are by weight unless otherwise indicated. Example 2 Wettable Powder N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino carbonyl]-3.4-dihydro-2H-1-benzothiopyran-8-sulfon amide, l,l-dioxide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3S kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. Example 3 Wettable Powder N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino carbonyl]-3,4-dihydro-2H-l-benzothiopyran-8-sulfon- amide, l,l-dioxide 50% sodium alkylnaphthalenesulfonate 2t 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 4 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 258 solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. ExamPle 5 Extruded Pellet N-t(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino- carbonyl]-3,4-dihydro-2H-1-benzothiopyran-8-sulfon amide, l.l-dioxide 25t 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 6 Oil Suspension N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino carbonyl]-3,4-dihydro-2H-1-benzothiopyran-8-sulfon amide, 1,1,-dioxide 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 oilE or emulsified in water. Example 7 Wettable Powder N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)- aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benziso- thiazole-7-sulfonamide, l,l-dioxide 80% sodium alkylnaphthalenesulfonate 29 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 8 Low Strength Granule N-t(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)- aminocarbonyl]-2,3-dihydro-2-methyl-2,2-benziso thiazole-7-sulfonamide, 1,1-dioxide 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20-40 sieve) The active ingredient is dissolved in the sol- vent 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 9 Aqueous Suspension N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl) aminocarbonyl3-2,3-dihydro-2-methyl-1,2-benziso- thiazole-7-sulfonamide, l.l-dioxide 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0S 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 10 Solution N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino carbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole- 7-sulfonamide, l,l-dioxide, 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 11 Thigh Strength Concentrate N- r ( 4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)- aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzoiso thiazole-7-6ulfonamide, l,l-dioxide 99S silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. Example 12 Oil Suspension N-[(4-cyclopropyl-6-methylpyramid-2-yl)amino carbonyl )2, 3-dihydro-2-2-dirnethyl-7-benzofuran- sulfonamide 25S polyoxyethylene sorbitol hexaoleate 5t highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. Example 13 Low Strength Granule N-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-7-benzothiophenesulfonamide 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-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)amino carbonyl ) -2, 3-dihydro-22-dimethyl-7-benzothiophene sulfonamide 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 N-t(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)- aminocarbonylj-2, 3-dihydro-7-benzothiophene- sulfonamide-l,l-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 may be formulated further if necessary. Utility The compounds of the present invention are effective herbicides. They have utility for broadspectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drivein theaters, around billboards, highway and railroad structures, or on fallow land. The rates of application for the compounds of the invention are determined by a number of factors, including 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 0.005 to 5 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, 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, carbamat. acetanilide, bipyridylium, dinitroaniline and phenolic types. The herbicidal properties of the subject compounds were observed in greenhouse tests. The test procedures follow. Compounds Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 EMI56.1 Test A Seeds of crabgrass (Digitaria sp.), barnyardgrass tEchinochloa crusgalli), wild oats (Avena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theoPhrasti), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, sugar beet, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the 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. 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 con- trols and visually rated for response to treatment. The ratings are based on a numerical scale extending from O a no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis; E = emergence inhibition; G = growth retardation; H = formative effects; U = unusual pigmentation: X = axillary stimulation; and 6Y = abscised buds or flowers. TABLE A Cmpd. 1 Rate (kg/ha) 0.05 POSTEMERGENCE Morningglory 3G Cocklebur 4C,8H Velvetleaf 2C Nuts edge o Crabgrass o Barnyardgrass O Cheatgrass o Wild Oats 0 Wheat O Corn 0 Soybean 1H Rice 8G Sorghum 2C,7H Sugar Beets 3C,7G Cotton 0 PREEMERGENCE Morningglory 4G Cocklebur O Velvetleaf 0 Nutsedge 0 Crabgrass O Barnyardgrass O Cheatgrass 0 Wild Oats 0 Wheat 0 Corn 6G Soybean O Rice 7G Sorghum 8H Sugar Beets 7G Cotton 0 Table A (Continued) Cmpd. 2 Cmpd. 3 Cmpd. 4 Rate kg/ha 0.05 0.05 0.05 POST-EMERGENCE Morningglory loc lOC 5C,9G Cocklebur 9C lOC 5C,9H Velvetleaf 9C 9C 4C,8G Nutsedge 3C,5G 5C,9G 3G Crabgrass o 0 0 Barnyardgrass 3H 0 0 Cheatgrass 5G 0 0 Wild Oats 0 4C,9H 3G Wheat . 0 0 0 Corn 3C,9H 9C 4C,9G Soybean 3C,8H 5C,9G 3H,9G Rice 4C,9G 9C 8G Sorghum 3C,9H 9C 4C,9G Sugar beet 3C,9H 100 5C,9H Cotton 3C,9H 5C,9H 9H PRE-EMERGENCE Morningglory 3C,8H 9G 8H Cocklebur 3C,5H 9H 0 Velveatlaef 8G 3C,6H 0 Nutsedge 0 5G 0 Crabgrass O 0 0 Barnyardgrass 0 2H 0 Cheatgrass 5G 5G 4G Wild Oats O 5C,9H 3C,7G Wheat O 0 0 Corn 3C,7H 5C,9G 3C,8H Soybean 3C,3H 3C,6G 2C,4H Rice 3C.9H 10E 3C,7G Sorghum 3C,8H 5C,9H 4C,9G Sugar beet 4C,9G 9C 4C,9G Cotton 7G 6G 3G Table A (Continued) Cmpd. 5 Rate (kg/ha) 0.05 POSTEMERGENCE Morningglory 3C,8H Cocklebur 5C,9G Velvetleaf 9C Nutsedge 3G Crabgrass 0 Barnyardgrass 5G Cheatgrass O Wild Oats 0 Wheat O Corn 3C,9H Soybean 3C,9H Rice 5C,9G Sorghum 4C.9H Sugar Beets 2C,7G Cotton 5C,9G PREEMERGENCE Morningglory 3C,5H Cocklebur 2C,5H Velvetleaf 5C,9G Nutsedge 0 Crabgrass o Barnyardgrass 2C Cheatgrass 3G Wild Oats 3G Wheat 3G Corn 4C,7G Soybean 0 Rice 8H Sorghum 3C,8H Sugar beets 4C,9G Cotton 5G 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 moosuroides), sugar beets. nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), jimsonweed (Datura stramonium). velvetleaf (Abutilon theoPhrasti), giant foxtail (Setaria faberii) and rape (Brassica napus). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua). cocklebur (Xantiutn Densolvanicum), morningglory (IPomoea hederacea), johnsongrass (Sorghum halePense) and barnyardgrass (Echinochloa crusgalli). The plants were grown for approximately fourteen days, then sprayed post-emergence with the chemicals dissolved in a non-phytotoxic solvent. Preemergence 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, giant foxtail and rape. The other pan was planted with wheat. cotton, rice, corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass. and barnyardgrass. The two pans were sprayed pre-emergence 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 utilizing the rating system as described for Test A. The response is rated on a scale of 0-100 with 0 = no injury and 100 - complete control. Response ratings are contained in Table B. Table B SASSAFRAS SANDY LOAM Compound 2 POST-EMERGENCE Rate g/ha 250 62 16 4 Corn 100 100 30 0 Wheat O 0 0 0 Rice 100 100 60 20 Soybean 100 70 20 0 Cotton 100 80 30 0 Sugar beet 100 100 90 70 Rape 100 100 90 50 Crabgrass 20 0 0- 0 Johnsongrass 80 40 0 0 Blackgrass 100 70 30 0 Barnyardgrass o 0 0 0 Nutsedge 40 0 0 0 Giant Foxtail O 0 0 0 Wild Oats 20 0 0 0 Cocklebur 100 60 20 0 Morningglory 100 70 20 0 Teaweed 100 50 0 0 - Sicklepod 40 0 0 0 Jimsonweed 90 70 30 0 Velvetleaf 100 100 20 0 PRE-EMERGENCE Rate g/ha 250 62 Corn 100 40 Wheat 20 0 Rice 100 60 Soybean 80 20 Cotton 60 0 Sugar beet 100 60 Rape 80 20 Crabgrass 40 0 Johnsongrass 50 40 Blackgrass 80 30 Barnyardgrass O 0 Nuts edge O 0 Giant Foxtail 30 0 Wild Oats 0 0 Cocklebur 50 0 Morningglory 50 0 Teaweed 60 20 Sicklepod 50 20 Jimsonwed 80 20 Velvetleaf 90 40 62 Table B (Continued) ComPound 3 POST-EMERGENCE Rate g/ha 250 62 16 4 Corn 100 100 100 90 Wheat o 0 0 0 Rice 100 100 90 30 Soybean 100 100 90 50 cotton 80 40 0 0 Sugar beet 100 100 100 90 Rape 100 100 100 50 Crabgrass o 0 0 0 Johnsongrass 100 100 60 30 Blackgrass 100 100 100 40 Barnyardgrass 100 100 100 70 Nutsedge 100 100 40 0 Giant Foxtail O 0 0 0 Wild Oats 100 70 30 0 Cocklebur 100 100 90 30 Morningglory 100 100 90 50 Teaweed 90 80 20 0 Sicklepod 100 90 40 0 Jimsonweed 100 100 70 0 Velvetleaf 100 100 70 PRE-EMERGENCE Rate g/ha 250 62 16 Corn 100 90 30 Wheat o 0 0 Rice 100 100 90 Soybean 70 30 0 Cotton O 0 0 Sugar beet 100 100 80 Rape 100 90 30 Crabgrass 90 40 0 Johnsongrass 100 100 100 Blackgrass 100 100 80 Barnyardgrass 100 40 0 Nutsedge 100 100 40 Giant Foxtail o 0 0 Wild Oats 90 70 20 Cocklebur 70 30 0 Morningglory 100 50 30 Teaweed 100 20 0 Sicklepod 80 30 0 Jimsonweed 100 90 20 Velvetleaf 90 60 0 Table B (Continued) ComPound 4 POST-EMERGENCE Rate g/ha 62 16 4 Corn 100 90 20 Wheat o 0 0 Rice 50 0 0 Soybean 100 70 20 Cotton 80 20 0 Sugar beet 100 100 50 Rape 100 90 40 Crabgrass O 0 0 Johnsongrass 90 90 40 Blackgrass 50 20 0 Barnyardgrass O 0 0' Nutsedge o 0 0 Giant Foxtail O 0 0 Wild Oats 0 0 0 Cocklebur 70 20 0 Morningglory 80 40 0 Teaweed O 0 0 Sicklepod 40 0 0 Jimsonweed 70 50 20 Velvetleaf 70 30 ¯ O 0 PRE-EMERGENCE Rate g/ha 62 16 Corn O 0 Wheat O 0 Rice 70 0 Soybean O 0 Cotton o 0 Sugar beet 0 0 Rape o 0 Crabgrass 20 0 Johnsongrass 80 0 Blackgrass 90 30 Barnyardgrass O 0 Nutsedge O 0 Giant Foxtail O 0 Wild Oats 30 0 Cocklebur 20 0 Morningglory 20 0 Teaweed o 0 Sicklepod O 0 Jimsonweed 30 0 Velvetleaf o 0

Claims: Claims: 1. A compound of the formula: EMI65.1 wherein EMI65.2 EMI66.1 EMI67.1 EMI67.2 EMI67.3 EMI67.4 EMI68.1 n is 0, 1 or 2: W is O or S; W1 is O or S; Q is O, S, SO or SO2; Q1 is O, S or SO2: R is H or CH3: R1 is H. F, C1, Br. CH3, OCH3, CF3. SCH3 or OCF2H; R2 is H or C1-C4 alkyl; R3 and R4 are independently H, C1-C4 alkyl, Cl or Br: R5 is H or CH3: R6 is H or CH3: R@ is H or CH3; R8 is H, CH3, OCH3, Cl, Br, CO2R12, SO2R13, OSO2R14 or SO2NR15R16: R9 and R10 are independently H or C1-C3 alkyl: R@ is H or CH3; R12 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl: R13 is C1-C3 alkyl; B14 is C1-C3 alkyl or CF3; R15 and R16 are independently C1-C2 alkyl; R17 is H or C1-c4 alkyl: R18 is H or C1-C4 alkyl: B19 is H or CH3: R20 is H, Cl, CH3, CF3, OCH3, Br, F, SCH3 or OCF2H: : R21 is H, CH3, OCH3, Cl, Br, NO2, CO2R24, SO2R25, OSO2R26, SO2NR27R28, F, CF3, SCH3, OCF2H or SO2N(OCH3)CH3: R22 is H, C1, Br or C1-C4 alkyl; R23 is H. CH3. Cl. or Br: R24 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl: R25 is C1-C3 alkyl: R26 is C1-C3 alkyl or CF3: R27 and R28 are independently C1-C2 alkyl: EMI69.1 Y is C -C alkyl. C1-C2 alkoxy, C1-C2 alkoxy methyl, OCF2H, SCF2H, OCH2CH2F, OCH2CF3, CF3, OCH2CH=CH2, OCH2C#CH, NHCH3, N(CH3)2 or CH(OCH3)2: and Z is CH or N; and their agriculturally suitable salts; provided that a) when W is S, then R is H; b) the total number of carbon atoms in R3 and R4 is less than or equal to 4; c) when B5 is CH3, then n is 0; d) when 3 is J24. then R4 and R5 are not both H: e) the total number of carbon atoms in R9 and R10 is less than or equal to 3: f) in Formula J28, when R9 and R10 are other than H. then R11 is H: g) in Formula J29, when R9 is other than H. then R11 is H: h) when 0 is S, then R8 is not SO2NR15R16: i) in Formulae J29 and J32' Q may not be 0: j) in Formula J33. R8 is not CH3: k) in Formulae J 36 and J37, when R21 is NO2, then R22 is cl-C4 alkyl and R23 is CH3: 1) in Formulae J34 and J35, when Q is SO, then W is O: m) when R20 is other than H, then R21 is H: n) R17 and R18 taken together are not more than four carbon atoms; o) when J is J27, J28, J29, J30, J31 or J32, then Q is 0, S or SO2: and p) when Y is OCF2H then Z is CH. 2. A compound of Claim 1 where W is O; R3 and B4 are independently H or C1-C3 alkyl; R17 is H or C1-C2 alkyl: R18 is H or CH3: R19 is H: R22 is H or C1-C2 alkyl; R23 is H: and R1 is bonded to the ortho or meta position of the ring relative to the sulfonylurea moiety. 3. A compound of Claim 2 where R is H: B1 is H, F. Cl, Br, CH3, OCH3, CF3 or SCH3: R8 is H. CH3. OCH3 or C1; R20 is N, C1, CH3 or OCH3: and R21 is H, Cl, CH3, OCH3, CO2R24 or SO2R25. 4. A compound of Claim 3 where R1 is H; R5 is H; R8 is H. R20 is H: R21 is H: and Y is CH3. OCH3 or CH2OCH3. 5. A compound of Claim 4 where J is J 7 or J34 6. A compound of Claim 1 wherein J is J34, J35, J36 or J37. 7. A compound of Claim 1 wherein J is selected from J1-J26. 8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of any of Claims 1 to 7 and at least one of the following: surfactant, solid or liquid diluent. 9. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of any of claims 1 to 7. 1Q. 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 as claimed in any of claims 1 to 7. 11. A process for the production of a compound of claim 1 which comprises: (a').' reacting a sulfonylisocyanate or sulfonylisothiocyanate of formula JuS02NCW (11) wherein J is as defined in claim 1 other than J6, J12' J22 or J23 and when 0 is S or 0, J is other than J28, J29' J31 or J32; and W is, as defined in claim 1, with an appropriate heterocyclic amine of formula EMI71.1 wherein R and A are as defined in claim 1; or (b) reacting a sulfonamide of formula J02NH2 (IV) wherein J is as defined in claim 1, with a heterocyclic isothiocyanate of formula SCN-A wherein A is as defined in claim 1, to obtain a compound of claim 1 wherein W is S and R is H; or (c) reacting a sulfonylcarbamate of formula EMI71.2 wherein J is as defined in claim 1, with said heterocyclic amine (III) defined above; or (d) reacting said sulfonamide (IV) defined above with a heterocyclic carbamate of formula EMI72.1 wherein A and R are as defined in claim 1; or (e) reacting said sulfonamide (IV) wherein J is as defined in claim 1 other than J4, J5, J10, J11, J16, J17' J21, J24 or J25 and R8 is other than C02R12 and R21 is other than CO2R24, with a methylcarbamate of formula EMI72.2 wherein A and R are as defined in claim 1.

Inventors: PASTERIS, ROBERT JAMES, RORER, MORRIS PADGETT
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY (A DELAWARE CORPORATION)
Application year: 1985
Main classification: C07D409
IPC codes: C07D521, A01N47