BICYCLIC HERBICIDES

Abstract: Compounds of Formula (I), and their agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetaion, wherein Q is (Q-1) or (Q-2); and A, Y, Z, R<1>-R<7>, q and r are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (I).

Description: TITLE BICYCLIC HERBICIDES BACKGROUND OF THE INVENTION This invention relates to certain bicyclic compounds, their agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action. EP 283,261 discloses cyclic diones of Formula i as herbicides: 1 wherein X, X 1 and X 2 are independently O or S; R 1 is a monocyclic or fused-bicyclic heterocyclic group containing up to ten ring atoms up to five of which may be selected from O, N and S, optionally substituted with one or more groups selected from, among others, oxo, halogen, nitro, cyano, alkyl, haloalkyl, haloalkoxy, alkoxy, alkylsulfonyl; and Y is, among others, C 2 -C 4 alkylene which is optionally substituted with one or more groups selected from, among others, halogen or alkyl. The bicyclic herbicides of the present invention are not disclosed in this publication. SUMMARY OF THE INVENTION This invention is directed to compounds of Formula I including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation: wherein Q is Q-l Q-2 A is -(CH 2 ) m -, -CH=CH-, -CH 2 CH=CH-, -CH=CHCH , -(CH 2 ) n -NR 9 -, -NR 9 -(CH 2 ) n -, -(CH 2 ) n -O- or -(CH 2 ) n -S(O) 2 -, each group optionally substituted with one to four R 8 , and the directionality of the A linkage is defined such that the moiety depicted on the left side of the linkage is bonded to Y and the moiety on the right side of the linkage is bonded to the phenyl ring; Y is O; NR 9 ; or CH 2 optionally substituted with one or two groups independently selected from Ci-Cg alkyl, Cι-C 6 haloalkyl and halogen; provided that when A is -NR 9 -(CH 2 ) π -, then Y is CH 2 ; Z is C(=X), O, or S(O) 2 ; provided that when Y is O or NR 9 , then Z is C(=X); X is O or S; R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano, nitro, S(O) 2 NR 10 R 11 , C r C 6 alkylsulfonyl, C r C 6 haloalkylsulfonyl, C 3 -C 6 alkenylsulfonyl, C 3 -C 6 haloalkenylsulfonyl, C 3 -C 6 alkynylsulfonyl, C3-C6 haloalkynylsulfonyl or C3-C6 cycloalkylsulfonyl; or R 1 is phenylsulfonyl optionally substituted with C1-C3 alkyl, -C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, 1-2 halogen, cyano or nitro; each R 2 is independently C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C 1 -C 6 haloalkoxy, halogen, cyano or nitro; R 3 is OR 12 , C r C 6 alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 haloalkylsulfinyl, -Cg alkylsulfonyl, C r C 6 haloalkylsulfonyl or halogen; each R 4 is independently C 1 -C3 alkyl, C 1 -C 3 alkoxy, C ] -C 3 alkylthio or halogen; or when two R 4 are attached to the same carbon atom, then said R 4 pair can be taken together to form -OCH 2 CH 2 O-, -OCH 2 CH 2 CH 2 O-, -SCH 2 CH 2 S- or -SCH 2 CH 2 CH 2 S-, each group optionally substituted with 1-4 CH 3 ; R 5 is H, -Cg alkyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 7 dialkylaminocarbonyl, Cj-C 6 alkylsulfonyl or C r C 6 haloalkylsulfonyl; or R 5 is benzoyl or phenylsulfonyl, each optionally substituted with C j -C 3 alkyl, halogen, cyano or nitro; R 6 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; or R6 is phenyl or benzyl, each optionally substituted on the phenyl ring with C1-C 3 alkyl, C r C 3 haloalkyl, C r C 3 alkoxy, C r C 3 haloalkoxy, 1-2 halogen, cyano or nitro; R 7 is H, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano or nitro; each R 8 is independently Cj-Cg alkyl, -Cg haloalkyl, C j -Cg alkoxy, C j -C 8 haloalkoxy, hydroxy or halogen; or two R 8 groups bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(=O) or C(=S); provided that when two R 8 groups are attached to a carbon atom which is attached to an O, NR 9 or S(O) 2 , then no more than one of said R 8 groups can be Cj-C 6 alkoxy, C j -Cg haloalkoxy, hydroxy or halogen; each R 9 is independently H; C r C 6 alkyl; C r C 6 haloalkyl; C 3 -C 6 alkenyl; C 3 -C 6 haloalkenyl; C 3 -C 6 alkynyl; C 3 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C r C 6 alkoxy; Cj-Cg haloalkoxy; C 2 -C 6 alkoxyalkyl; formyl; C 2 -C 6 alkylcarbonyl; C 2 -Cg alkoxycarbonyl; C 2 -Cg alkylaminocarbonyl; C3-C7 dialkylaminocarbonyl; or phenyl, benzyl or benzoyl, each optionally substituted on the phenyl ring with C r C 3 alkyl, Cj -C 3 haloalkyl, Cι-C 3 alkoxy, -C 3 haloalkoxy, 1-2 halogen, cyano or nitro; R 10 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl or C 1 -C 6 alkoxy; or R 10 is phenyl or benzyl, each optionally substituted on the phenyl ring with C ] -C 3 alkyl, C r C 3 haloalkyl, C r C 3 alkoxy, C r C 3 haloalkoxy, 1-2 halogen, cyano or nitro; R 11 is H, C r C 6 alkyl or C r C 6 haloalkyl; or R 10 and R 11 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -, each optionally substituted with 1-4 C1-C3 alkyl; R 12 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C -Cg alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C3-C 7 dialkylaminocarbonyl, Cj-Cg alkylsulfonyl or Ci-C haloalkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with C1-C 3 alkyl, halogen, cyano or nitro; mis 1, 2 or 3; n is 1 or 2; q is O, 1, 2, 3 or 4; and r is 0, 1 or 2; provided that (i) when Z is C(=X) or O; A is -(CH 2 ) m - optionally substituted with one to four R 8 ; and m is 1 or 2; then Q is Q-2; (ii) when Z is C(=X) or O; and A is -CH=CH- optionally substituted with one to two R 8 ; then Q is Q-2; (Hi) when Z is C(=X) or O; A is -(CH 2 ) n -NR 9 -, -NR 9 -(CH 2 ) n - or -(CH 2 ) n -O- each optionally substituted with one to four R 8 ; and n is 1 ; then Q is Q-2; (iv) when A is -(CH 2 ) n -NR 9 -, -(CH 2 ) n -O- or -(CH 2 ) n -S(O) 2 - each optionally substituted with one to four R 8 ; and Y is CH 2 optionally substituted with one or two groups independently selected from C r C 6 alkyl, C r Cg haloalkyl and halogen; then Z is O or S(O) 2 ; (v) when A is -(CH^-- ) - optionally substituted with one to four R 8 ; Y is CH 2 optionally substituted with one or two groups independently selected from C j -Cg alkyl, C r C 6 haloalkyl and halogen; and Z is O or S(O) 2 ; then each R 8 is independently Cj-Cg alkyl, C j -Cg haloalkyl, C ] -C 6 alkoxy, hydroxy or halogen provided that no more than one R 8 is C j -Cg alkoxy; and (vi) when A is -(CH 2 ) m - optionally substituted with one to four R 8 ; Y is CH 2 optionally substituted with one or two groups independently selected from C r Cg alkyl, C r Cg haloalkyl and halogen; Z is S(O) ; and m is 2; then Q is Q-l and each R 8 is independently C r C 6 alkyl, C r C 6 haloalkyl, hydroxy or halogen. In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, -propyl, or the different butyl, pentyl or hexyl isomers. The term "1-4 alkyl" indicates that one to four of the available positions for that substituent may be alkyl which are independently selected. The term "1-4 CH 3 " indicates that one to four of the available positions for that substituent may be methyl. "Alkenyl" includes straight-chain or branched alkenes such as 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 . The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1) 2 C=CHCH 2 and CF 3 CH 2 CH=CHCH 2 . Examples of "haloalkynyl" include HC≡CCHCl, CF 3 C≡C, CC1 3 C≡C and FCH 2 C≡CCH 2 . Examples of "haloalkoxy" include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O. Examples of "haloalkylthio" include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S. Examples of "haloalkylsulfinyl" include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O). Examples of "haloalkylsulfonyl" include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 . The total number of carbon atoms in a substituent group is indicated by the "C j -C;" prefix where i and j are numbers from 1 to 7. For example, CJ-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2 alkoxyalkyl designates CH 3 OCH 2 ; C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH3CH 2 OCH 2 ; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . Examples of "alkylcarbonyl" include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 . Examples of "alkoxycarbonyl" include CH 3 OC(=O), CH 3 CH 2 OC(=O), CH 3 CH 2 CH 2 OC(=O), (CH 3 ) 2 CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)j_;, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R 1 or R 12 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula I and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. Some compounds of this invention can exist as one or more tautomers. One skilled in the art will recognize, for example, that compounds of Formula la (Formula I where Q is Q-l, R 3 is OR 12 , and R 12 is H) can also exist as the tautomers of Formulae lb and Ic as shown below. One skilled in the art will recognize that said tautomers often exist in equilibrium with each other. As these tautomers interconvert under environmental and physiological conditions, they provide the same useful biological effects. The present invention includes mixtures of such tautomers as well as the individual tautomers of compounds of Formula I. la \ / lb Ic The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as an enol. Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and agriculturally suitable salts thereof, wherein: the A- Y-Z moiety is selected from combinations of A, Y and Z such that (i) when A is -(CH 2 ) m - optionally substituted with one to two R 8 and Y is O or NR 9 , then Z is C(=X); (ii) when A is -(CH 2 ) m - optionally substituted with one to two R 8 and Y is CH 2 optionally substituted with one or two groups independently selected from C j -Cg alkyl, Cι-C 6 haloalkyl and halogen, then Z is O; and (iii) when A is -(CH 2 ) m - or -(CH 2 ) π -NR 9 - optionally substituted with one to two R 8 and Y is CH 2 optionally substituted with one or two groups independently selected from C j -Cg alkyl, C j -Cg haloalkyl and halogen, then Z is S(O) 2 ; X is O; each R 4 is independently C 1 -C 3 alkyl; R 6 is H, C r C 6 alkyl or C 3 -C 6 alkenyl; R 7 is H, C r C 3 alkyl or C r C 3 haloalkyl; R 9 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 3 -C 6 cycloalkyl; R 12 is H, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C7 dialkylaminocarbonyl, C j -Cg alkylsulfonyl or C r C 6 haloalkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro; q is 0, 1 or 2; and r is O or l. Preferred 2. Compounds of Preferred 1 wherein: R 1 is H, methyl, halogen, S(0) 2 NR 1 °R 11 , C r C 4 alkylsulfonyl, C r C 4 haloalkylsulfonyl or C 3 -C5 cycloalkylsulfonyl; R 2 is methyl, halogen or nitro; R3 is OR 12 ; R 5 is H or Cj-C 3 alkylsulfonyl; or R 5 is benzoyl or phenylsulfonyl, each optionally substituted with C r C 3 alkyl, halogen, cyano or nitro; each R 8 is independently Cj-C 3 alkyl, C r C 3 alkoxy or halogen; or two R 8 groups bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(=O); R 10 is H, C 1 -C 4 alkyl, allyl or propargyl; R 1 1 is H or C r C 4 alkyl; and R 12 is H or C1-C 3 alkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with C r C 3 alkyl, halogen, cyano or nitro. Most preferred are compounds of Preferred 2 selected from the group: 2-( 1 , 1 -dimethylethyl)-5-[( l-ethyl-5-hydroxy- lH-pyrazol-4-yl)carbonyl]-8- (ethylsulfonyl)-3,4-dihydro- 1 (2H)-isoquinolinone; (2,3-dihydro-2,4,7-trimethylbenzo[Z>]thiophen-5-yl)( 1 -ethyl-5-hydroxy- 1H- pyrazol-4-yl)methanone 5,S-dioxide; (1 -ethyl-5-hydroxy- lH-pyrazol-4-yl)(2,3,4,5-tetrahydro-6,9-dimethyl- 1 - benzothiepin-7-yl)methanone 5,S-dioxide; 4-ethyl-6-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yl)carbonyl]-2H- 1 ,4-benzothiazin- 3(4H)-one 1,1-dioxide; 4-ethyl-6-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-5,8-dimethyl-2H-l,4- benzothiazin-3(4H)-one 1,1 -dioxide; and (2,3-dihydro-2,4,7-trimethylbenzo[b]thiophen-5-yl)(5-hydroxy-l-methyl-lH- pyrazol-4-yl)methanone S,5-dioxide. This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds. This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds. DETAILS OF THE INVENTION The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-31. The definitions of Q, A, Y, Z, X, R^R 12 , m, n, q and r in the compounds of Formulae 1-29 below are as defined above in the Summary of the Invention. Compounds of Formulae Ia-Ie are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Ie are as defined above for Formula I. Compounds of Formulae Id and Ie correspond to Formula I compounds wherein Q is Q-l and Q-2, respectively. Id Ie Scheme 1 illustrates the preparation of compounds of Formula Id (R 3 = OR 13 and R 13 is the same as R 12 as described in the Summary of the Invention excluding H) whereby a compound of Formula Id (R 3 = OH) is reacted with a reagent of Formula 2 in the presence of a base wherein X 1 is chlorine, bromine, fluorine, methylsulfonyloxy (OMs), trifluoromethylsulfonyloxy (OTf), p-toluenesulfonyloxy (OTs) or acetyloxy (OAc) and R 13 is as previously defined. The coupling is carried out by methods known in the art (or by obvious modifications of these methods): for example, see K. Nakamura, et al., WO 95/04054. Scheme 1 Id (R 3 = OH) Id (R3--OR 13 ) Scheme 2 illustrates the preparation of compounds of Formula Id (R = S(O) r R ,14. r = 1 or 2; and R 14 = Ci-Cg alkyl or Ci-Cg haloalkyl) whereby a compound of Formula Id (R 3 = SR 14 ) is reacted with an oxidizing reagent such as peroxyacetic acid, -chloroperoxybenzoic acid, peroxytrifluoroacetic acid, potassium peroxymonosulfate or hydrogen peroxide. The oxidation is carried out by methods known in the art (or by obvious modifications of these methods); for example, see S. Patai, et al., The Chemistry ofSulphones and Sulphoxides, John Wiley & Sons, 1988; pp 205-213, 235-253. Scheme 2 oxidizing reagent Id (R 3 = SR 14 ) Id (R 3 = S(0) r R 14 ) Compounds of Formula Id (R 3 = Nu; Nu = SR 14 or OR 15 ; R 14 is as defined previously; R 15 is Cj-Cg alkyl, Cj-Cg haloalkyl or C 2 -C 6 alkoxyalkyl) can be prepared from a compound of Formula Id (R 3 = halogen) by treatment with a nucleophile of Formula 3 (Nu = SR 14 or OR 15 ; M = Na, K or Li) as shown in Scheme 3 using methods well documented in the literature (or obvious modifications of these methods): for example, see P. H. Nelson, et al., Synthesis, (1992), 12, 1287-1291; and S. Miyano, et al., /. Chem. Soc. Perkin Trans, (1976), 1, 1146. Scheme 3 Id (R 3 = halogen)) Id (R 3 = Nu; Nu = SR 14 or OR 15 )) wherein X 2 = halogen Compounds of Formula Id (R 3 = halogen) can be prepared by reacting a compound of Formula Id (R 3 = OH) with a halogenating reagent such as oxalyl bromide or oxalyl chloride (Scheme 4). This conversion is carried out by methods known in the art (or by obvious modifications of these methods): for example, see S. Muller, et al., WO 94/13619; S. Muller, et al., DE 4,241,999. Scheme 4 Id (R 3 = halogen) wherein X 2 is halogen Scheme 5 illustrates the preparation of compounds of Formula Id (R 3 = OH) whereby an enol ester of Formula 4 is reacted with a base such as triethylamine in the presence of a catalytic amount of a cyanide source (e.g., acetone cyanohydrin or potassium cyanide). This rearrangement is carried out by methods known in the art (or by obvious modifications of these methods): for example, see W. J. Michaely, EP 369,803. Enol esters of Formula 4 can be prepared by reacting a dione of Formula 5 with an acid chloride of Formula 6 in the presence of a slight molar excess of a base such as triethylamine in an inert organic solvent such acetonitrile, methylene chloride or toluene at temperatures between 0 °C and 110 °C (Scheme 6). This type of coupling is known in the art: for example, see W. J. Michaely, EP 369,803. Scheme 6 Enol esters of Formula 4 can also be prepared by reacting a dione of Formula 5 with an acid of Formula 7 in the presence of a coupling agent such as 2-chloro-l- methylpyridinium iodide and a slight excess of base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 °C and 110 °C (Scheme 6A). This type of coupling is known in the art: for example, see T. Mukaiyama et al., Chem. Lett. (1975), 1045-1048. Scheme 6A The acid chlorides of Formula 6 can be prepared by reacting an acid of Formula 7 with a halogenating reagent (e.g., oxalyl chloride or thionyl chloride) and a catalytic amount of dimethylformamide (Scheme 7). This chlorination is well known in the art: for example, see W. J. Michaely, EP 369,803. Scheme 7 Scheme 8 illustrates the preparation of acids of Formula 7 whereby a ketone of Formula 8 is reacted with an oxidizing reagent such as NaOCl, NaOBr, NaOI or NaNO 2 . The oxidation is carried out by methods known in the art (or by obvious modifications of these methods): for example, see T. F. Braish, et al., Org. Prep. Proced. Int., (1991), 23, 655-658 and J. A. Skorcz, et al., Heterocycl. Chem., (1973), 10, 249. 14 Scheme 8 Oxidizing reagent (e.g.,NaOBr) (R^NRlOR 11 , Cj-C 6 alkyl, Cj-C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -Cg alkynyl, C3-C 6 haloalkynyl or C 3 -C 6 cycloalkyl; or phenyl optionally substituted) Scheme 9 illustrates the preparation of sulfones of Formula 8a whereby a sulfide of Formula 9 is reacted with an oxidizing reagent such as peroxyacetic acid, -chloroperoxybenzoic acid, peroxytrifluoroacetic acid, potassium peroxymonosulfate or hydrogen peroxide. The oxidation is carried out by methods known in the art (or by obvious modifications of these methods): for example, see S. Patai, et al., The Chemistry ofSulphones and Sulphoxides, John Wiley & Sons, 1988; pp 205-213, 235-253. For some sulfides of Formula 9 containing a functional group not compatible with the reaction conditions, the functional group may be protected before the oxidation and then be deprotected after the oxidation. The protection and deprotection procedures are well known in the literature: for example, see T. W. Greene, et. al., Protective Groups in Organic Synthesis (Second Edition), John Wiley & Sons, Inc., J. E. McMurry and T. Hoz, J. Org. Chem., (1975), 40, 3797 and references cited therein. Scheme 9 Oxidizing reagent (R 16 =NR 10 R 1 C j -Cg alkyl, C j -Cg haloalkyl, C r C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C3-C 6 haloalkynyl or C3-Cg cycloalkyl; or phenyl optionally substituted) Scheme 10 illustrates the preparation of ketones of Formula 9 whereby a sulfide of Formula 10 is reacted with an acylating reagent 11 such as acetyl chloride or acetic anhydride in the presence of a Lewis acid such as aluminum chloride in a solvent such as carbon disulfide, methylene chloride or 1,2-dichloroethane. This conversion is carried out using methods well known in the art: for example, see R. A. Cutler, J. Amer. Chem. Soc, (1952), 74, 5475. Scheme 10 The lactam of Formula 10a (X = O, Y = NR 9 , A = -(CH 2 ) m -, and m = 2) can be prepared by treating an amide of Formula 12 (Scheme 11) with a base such as potassium t-butoxide or sodium hydride in a solvent such as benzene, dimethylformamide or THF. This conversion is carried out using methods known in the art (or obvious modifications of these methods): for example, see R. N. Misra, et al., Bioorg. Med. Chem. Lett., (1991), 1, 295-298. Scheme 11 10a 12 (X 3 * = ha 1 lo 2 gen, OMs, OTs R 18 = HorR 8 R 2 is other than Br) The compounds of Formula 12 (Scheme 12) can be prepared from compounds of Formula 12a (X 3 = OH) by converting the alcohol to an appropriate leaving group such as a halogen, a mesylate or tosylate. For example, the reactions to prepare the mesylate or tosylate are carried with a sulfonyl chloride of Formula 13 in the presence of a base such as pyridine, sodium hydride or triethylamine in a solvent such as pyridine or methylene chloride at temperatures between 0 °C and room temperature. This conversion is carried out using methods well known in the literature (or obvious modifications of these methods): for example, see R. N. Misra, et al., Bioorg. Med. Chem. Lett., (1991), 1, 295-298, Helv. Chim. Acta, (1947), 30, 1454 and L. F. Fieser and M. Fieser, Reagents for Organic Synthesis, Vol. 1, Wiley, New York, (1967), 1179. Scheme 12 R 19 =Me orp-MeCgH4 (X 3 = halogen, OMs, OTs) Compounds of Formula 12a (Scheme 13) can be prepared from an amide of Formula 14 by treatment with an excess of a base such as n-butyllithum and an electrophile such as an epoxide of Formula 15 in a solvent such as THF. This conversion is carried out using methods known in the literature (or obvious modifications of these methods): for example, see R. N. Misra, et al., Bioorg. Med. Chem. Lett., (1991), 1, 295-298 and B. H. Bhide, et al., Chem. andlnd., (1975), 519. Scheme 13 Compounds of Formula 14 (Scheme 14) can be prepared from an acid chloride of Formula 16 and an amine of Formula 17 in the presence of a base such as triethylamine or excess NH 2 R 9 in a solvent such as chloroform. This conversion is carried out using methods well known in the literature (or obvious modifications of these methods): for example, see A. D. Wolf, EP 196,786. Scheme 14 Scheme 15 illustrates the preparation of compounds of Formula 10b (X = O, Y = NR 9 ) whereby an olefin of Formula 10c is reacted with a reducing reagent such as hydrogen at 345 kPa (50 psi) in the presence of a catalyst such as palladium on carbon in a solvent such as ethanol. The reduction is carried out by methods well known in the art (or by obvious modifications of these methods): for example, R. D. Clark, et at., J. Med. Chem., (1993), 36, 2645-57 and C. Y. Cheng, J. Heterocyclic. Chem., (1995), 32, 73. Scheme 15 10c (A = -CH=CH-, -CH 2 CH=€H- 10b (A = CΑi) m -, m= 2 or 3) or-(-H=CHCH 2 -) Scheme 16 illustrates the preparation of compounds of Formula lOd (X = O, Y = NR 9 ) whereby an amide of Formula 18 is treated with an alkyllithium such as n-butyllithium in a solvent such as THF. The resulting dianion is treated with an electrophile such as DMF or an amide to give compounds of Formula lOd. The reaction is carried out by methods well known in the art (or by obvious modifications of these methods): for example, see R. D. Clark, et al., J. Med. Chem., (1993), 36, 2645-57. Scheme 16 Olefins of Formula lOe (X = O, Y = NR 9 , A = -CH=CH-, -CH 2 CH=CH- or -CH=CHCH 2 -) can also be prepared from the corresponding lactones lOf (Y = O) with a substituted amine of Formula 17 (Scheme 17). The reaction is carried out by methods well known in the art (or by obvious modifications of these methods): for example, see R. Singh, et. al., J. Indian Chem. Soc, (1991), 68, 276-80, M. Somei, Chem. Pharm. Bull., (1981), 29, 249, and N. Gilman, Synth. Commun., (1982), 12, 373-80. Scheme 17 lOf 17 lOe The preparation of lactones of Formula lOg (X = O, Y = O) (Scheme 18) is carried out by methods well known in the art (or by obvious modifications of these methods): for example, see R. M. Hauser, J. Org. Chem., (1988), 53, 4676-4681. Scheme 18 18(R 18 = HorR 8 ) 10g (R 18 = HorR 8 ) The preparation of compounds of Formula lOh (X _= O, Y = O, A = -(CH 2 ) m -, m = 2) is carried out by methods well known in the art (or by obvious modifications of these methods): for example, R. J. Pasteris, EP 166,516, A. D. Wolf, EP 196,786 and F. M. Hauser, J. Org. Chem., (1988), 53, 4676-4681. Scheme 19 The preparation of compounds of Formula lOi (X = O, Y = NR 9 , A = -(CH 2 ) m -, m = 1) is carried out by methods known in the art (or by obvious modifications of these methods): for exaftiple, see J. Epsztajn, et al., Tetrahedron, (1993), 49, 929-938 and R. J. Pasteris, EP 107,979 and EP 166,516. Scheme 20 14 10i(R 18 = HorR 8 ) The preparation of compounds of Formula lOj (X -= O, Y = O, A = -(CH 2 ) m -, m = 1) is carried out by methods known in the art (or by obvious modifications of these methods): for example, see R. Mali, et al., J. Chem. Res., Synop., (1993), 5, 184-185 and B. H. Bhide, Tetrahedron, (1971), 27, 6171. Scheme 21 14 10j(R 18 = HorR 8 ) Scheme 22 illustrates the preparation of compounds of Formula Ie (R 5 = R 5a and R 5a is the same as R 5 as described in the Summary of the Invention excluding H) whereby a compound of Formula Ie (R 5 = H) is reacted with a reagent of Formula 19 in the presence of a base wherein X 4 is chlorine, bromine, fluorine, OTf or OAc and R 5a is as previously defined. This coupling is carried out by methods known in the art (or by obvious modification of these methods): for example, see K. Nakamura, et al., WO 95/04054. Scheme 22 Ie (R 5a is other than H) wherein R 5a is the same as R 5 as described in the Summary of the Invention excluding H. Scheme 23 illustrates the preparation of compounds of Formula Ie (R 5 = H) whereby an ester of Formula 20 is reacted with a base such as triethylamine in the presence of a catalytic amount of a cyanide source (e.g., acetone cyanohydrin or potassium cyanide). This rearrangement is carried out by methods known in the art (or by obvious modification of these methods): for example, see W. J. Michaely, EP 369,803. Scheme 23 An ester of Formula 20 can be prepared by reacting a hydroxypyrazole of Formula 21 with an acid chloride of Formula 6 in the presence of a slight molar excess of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 °C and 110 °C (Scheme 24). This type of coupling is carried out by methods known in the art (or by obvious modification of these methods): for example, see W. J. Michaely, EP 369,803. Scheme 24 Scheme 25 illustrates the synthesis of compounds of the Formula 23 (R 8 = Cj-Cg alkyl) wherein a thioether of the Formula 22 is heated either neat or in the presence of a high boiling solvent such as dimethylaniline at temperature from 150 °C to 200 °C to provide the benzothiophenes 23 (Scheme 25). For a representative example see, W. K. Anderson et al., J. Chem. Soc. Perkin Transactions I (1986), 1-4. Scheme 25 22 23 Compounds of the Formula 25 which can serve as intermediates for the synthesis of compounds of the present invention can readily be prepared by acid catalyzed cyclization of an appropriately substituted carboxylic acid of the Formula 24 (Scheme 26). Acid catalysts that have been used to promote this reaction are sulfuric acid, hydrochloric acid, trifluoroacetic acid and polyphosphoric acid. For a general review see, B. Iddon and R. M. Scrowston, Advances in Heterocyclic Chemistry, Vol. 1, Academic Press, New York (1970), 177. Scheire 26 24 25 The preparation of compounds of the Formula 23a can be accomplished by treatment of compounds of the Formula 23 with triethylsilane in trifluoroacetic acid (Scheme 27). The reaction is best carried out at temperatures between 25 °C and 72 °C. For an example of this transformation see, E. N. Karaulova et al., Zur Russ. Fiz-Chim., (1960), 30, 3292. Scheme 27 23 23a Compounds of the Formula 25a can readily be prepared by treatment of compounds of the Formula 25 with triethylsilane in refluxing trifluoroacetic acid (Scheme 28). For a representative example, see, C. T. West et al., J. Org. Chem., (1963), 35, 2675-2681. Schema 28 Compounds of Formula 26 (A = -(CH 2 ) m -, Y = -CH 2 -) can be regioselectively brominated/κ-r-z to the thioether functionality giving structures of Formula 27 (Scheme 29). Typical conditions employed are the treatment of compounds of Formula 26 with one equivalent to a slight excess of bromine in an inert solvent such as dichloromethane or chloroform at temperatures from 20 °C up to the boihng point of the solvent. For a representative example see K. Nakamura et al., WO 95/04054. Scheire 29 26 27 Scheme 30 illustrates the preparation of carboxylic acids of the Formula 28 (A = -(CH 2 ) m -, Y = -CH 2 -) via halogen metal exchange followed by quenching of the resulting anion with carbon dioxide. This general method is carried out by the addition of n-butyl lithium to a solution of the compound of the Formula 27 in THF or diethyl ether at temperatures from 25 °C to -70 °C. Carbon dioxide is introduced to produce the resulting acid. This classical reaction is known to one skilled in the art. For a typical procedure see, R. L. Danheiser et al., J. Am. Chem. Soc, (1986), 108, 806-810. Scheme 30 27 28 Compounds of the Formula 29 (A = -(CH 2 ) m -, Y = -CH 2 -) (Scheme 31) can readily be prepared by oxidation of compounds of the Formula 28 using any one of a number of oxidants. Typical reagents used for this transformation are hydrogen peroxide, peroxyacetic acid, -chloroperoxybenzoic acid and potassium peroxymonosulfate. The oxidations can be carried out by methods known in the art or obvious modifications. For a general review see, S. Patai e.t.a., The Chemistry of Sulphones and Sulf oxides, John Wiley & Sons, 1988, pp. 205-213. Scheme 31 It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I. One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. J H NMR spectra are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, br s = broad singlet. EXAMPLE 1 Step A: Preparation of 2-(ethylthio)benzoic acid 73.5 g ( 1.84 mol) of sodium hydroxide was dissolved in 750 mL of ethanol. To this solution at 20 °C, 135 g (0.87 mol) of thiosalicylic acid and an additional 600 mL of ethanol was added. After stirring at room temperature for 1 h, the reaction mixture was cooled to 0 °C and 77 mL (0.97 mol) of ethyl iodide was added dropwise. The reaction mixture was then heated under reflux for 1 h, cooled to 10 °C and 1 N HCl added until the mixture was pH 2. The resulting precipitate was collected by filtration and washed several times with water. The solid was dried to give 148 g of the title compound of Step A. *H NMR (CDC1 3 ) 6 1.40 (t,3H), 3.00 (q,2H), 7.20 (t,lH), 7.38 (d,lH), 7.50 (t,lH), 8.15 (d,lH). Step B: Preparation of N-( 1.1 -dimethylethyl)-2-(ethylthio)benzamide 296.4 g (1.63 mol) of the title compound of Step A, 300 mL (4.07 mol) of thionyl chloride and 600 mL of methylene chloride were heated at reflux for 4 h. After standing at room temperature overnight, an additional 25 mL of thionyl chloride was added and the reaction refluxed an additional 3 h. The reaction was concentrated under reduced pressure, chloroform was added, and the mixture was again concentrated to give 316 g of the acid chloride. A solution of the acid chloride in 550 mL of chloroform was added dropwise to a solution of 377 mL (3.58 mol) of t-butyl amine in 550 mL of chloroform at 0 °C. After the addition was complete, the reaction was heated at 40 °C and then allowed to stand at room temperature overnight. The reaction mixture was poured into water and extracted twice with methylene chloride. The combined organic extracts were washed twice with 1 Ν HCl, dried (MgSO_j) and concentrated. The crude oil was triturated with hexane to give 284 g of the title compound of Step B as a white solid (a sample prepared in a separate experiment provided material melting at 126-129 °C). An additional 44.6 g was obtained from the filtrate. ] H ΝMR (CDC1 3 ) δ 1.29 (t,3H), 1.48 (s,9H), 2.92 (q,2H), 6.52 (br s, IH), 7.21-7.40 (m,3H), 7.62 (dd,lH). Step C: Preparation of N-( 1.1 -dimethylethyl - 2-(e.hylthioy 6-(2- hydroxyethyDbenzamide 20.0 g (84.4 mmol) of the title compound of Step B was dissolved in 250 mL of dry THF and cooled to -45 °C. n-Butyl lithium (116 mL of a 1.6 M solution in hexanes, 186 mmol) was added dropwise to this mixture at -45 °C. The reaction was allowed to warm to 0 °C and kept at this temperature for 30 min. Ethylene oxide was then added rapidly at 0 °C and the reaction was kept below room temperature. After 1 h, saturated ammonium chloride was added and the reaction mixture was extracted twice with ether. The combined organic extracts were dried (Νa 2 Sθ 4 ) an ^ concentrated. The crude oil was triturated with w-butyl chloride to give 9.94 g of the title compound of Step C as a white solid melting at 113-117 °C. J H NMR (Me 2 SO-_i 6 ) δ 1.17 (t,3H), 1.32 (s,9H), 2.67 (t,2H), 2.87 (q,2H) 3.55-3.59 (m,2H), 4.62 (t,lH), 7.00-7.21 (m,3H), 7.84 (br s.lH). Step D: Preparation of N-( 1.1 -dimethylethylV2-(ethylthioV6-r2- [(methylsulfonyDoxylethyllbenzamide To a mixture of 16.67 g (59.32 mmol) of the title compound of Step C in 245 mL of pyridine at 0 °C was added dropwise 14 mL (178 mmol) of mesyl chloride at 0 °C. After 1 h at 0 °C, the reaction mixture was poured into ice water and the precipitate collected by filtration. The solid was washed with water and dried to give 15.14 g of the title compound of Step D (a sample prepared in a separate experiment provided material melting at 111-113 °C). *H ΝMR (Me 2 SO- 6 ) δ 1.20 (t,3H), 1.36 (s,9H), 2.93 (m,5H), 3.11 (s,3H), 4.38 (t,2H), 7.17 (dd,lH), 7.30 (m,2H), 8.00 (br s,lH). Step E: Preparation of 2-( 1. l-dimethylethylV8-(ethylthioV3.4-dihvdro- 1 (2H)- isoquinolinone To a mixture of 5.67 g (50.61 mmol) of potassium t-butoxide in 100 mL of dimethylformamide at 0 °C was added a solution of 15.14 g (42.17 mmol) of the title compound of Step D in 100 mL dimethylformamide at 0 °C. The reaction was allowed to warm to room temperature over 1 h and an additional 150 mL of dimethylformamide and 1 g of potassium t-butoxide added. After an additional 30 min, the reaction mixture was poured onto ice and 10% HCl was added to adjust the pH to 2. The reaction mixture was extracted three times with ethyl acetate. The combined organic phases were washed three times with water, then saturated aqueous ΝaCl, dried (MgSO 4 ) and concentrated to give 8.6 g of the title compound of Step E as an amber oil. ! H ΝMR (CDC1 3 ) δ 1.40 (t,3H), 1.55 (s,9H), 2.88 (m,4H), 3.50 (m,2H), 6.85 (d,lH), 7.18 (d,lH), 7.23 (m,2H). Step F: Preparation of 5-acetyl-2-(l .l-dimethylethvn-8-(ethylthio)-3.4-dihydro- 1 (2H)-isoquinolinone To a solution of 2.0 g (7.6 mmol) of the title compound of Step E and 32 mL of methylene chloride was added 1.0 g (7.5 mmol) of aluminum chloride. The reaction mixture was heated under reflux for 1 h and cooled to room temperature. A solution of 1.2 g (9.12 mmol) of aluminum chloride and 0.72 g (9.12 mmol) of acetyl chloride in 20 mL of methylene chloride was added and the reaction mixture was refluxed an additional 2 h. The reaction mixture was cooled and 20 mL of 1 Ν ΗC1 was added dropwise. The phases were separated and the aqueous phase was extracted two more times with methylene chloride. The combined organic phases were dried (MgSO 4 ) and concentrated to give 2.3 g of an oil. The residue was flash chromatographed on silica gel with ethyl acetate hexane to give 1.04 g of the title compound of Step F as a white solid (a sample prepared in a separate experiment provided material melting at 109-110 °C). J H NMR (Me 2 SO- 6 ) δ 1.25 (t,3H), 1.45 (s,9H), 2.55 (s,3H), 2.89 (q,2H), 3.00 (t,2H), 3.40 (t,2H), 7.33 (d,lH), 7.86 (d,lH). Step G: Preparation of 5-acetyl-2-(l.l-dimethylethyl)-8-(ethylsulfonyl -3.4- dihydro- 1 (2H)-isoquinolinone To a solution of 2.06 g (3.35 mmol) of Oxone® in 8 mL of water was added a solution of 0.41 g (1.34 mmol) of the title compound of Step Fin 3 mL of acetone. The reaction mixture was stirred at room temperature for 1.5 h and then diluted with water and ethyl acetate. The phases were separated and the aqueous phase was extracted again with ethyl acetate. The combined organic phases were dried (MgSO ) and concentrated to give 0.5 g of the title compound of Step G as a solid (a sample prepared in a separate experiment provided material melting at 139-142 °C). *Η NMR (Me 2 SO-rf 6 ) δ 1.18 (t,3H), 1.47 (s,9H), 2.62 (s,3H), 3.00(t,2H), 3,48 (t,2H), 3.85 (q,2H), 7.97 (d,lH,J=8.26 Hz), 8.08 (d,lH,J=8.26 Hz). Step H: Preparation of 2-( 1.1 -dimethylethyl)-8-(ethylsulfonyl)- 1.2.3.4-tetrahydro- l-oxo-5-isoquinolinecarboxylic acid To a 5 °C solution of 0.54 g (13.5 mmol) of sodium hydroxide in 1.25 mL of water was added 0.24 mL (4.65 mmol) of bromine and the reaction mixture was stirred until a clear yellow solution was obtained. To this solution was added 0.5 g (1.48 mmol) of the title compound of Step G dissolved in 1 mL of 1,4-dioxane and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water and adjusted to pH 2 with concentrated HCl. It was extracted three times with ethyl acetate and the combined organic extracts were dried (MgSO 4 ) and concentrated to give 0.53 g of the title compound of Step H as an amber oil. l H NMR (Me 2 SO-rf 6 ) δ 1.18 (t,3H), 1.48 (s,9H), 3.20 (t,2H), 3.51 (t,2H), 3.85 (q,2H), 7.95(d,lH,J=8.26 Hz), 8.06 (d,lH,J=8.26 Hz). Step I: Preparation of (l-ethyl-lH-pyrazol-5-yl. 2-(l.l-dimethylethylV8- (ethylsulfonyl)-1.2.3.4-tetrahydro-l-oxo-5-isoquinolinecarboxylate 0.5 g (1.45 mmol) of title compound of Step Η and 14 mL of thionyl chloride were combined and heated under reflux for 4 h. The reaction mixture was allowed to cool and was then concentrated. The residue was dissolved in methylene chloride and re-concentrated. The residue was dissolved in 6 mL of chloroform and 0.2 g (1.79 mmol) of l-ethyl-5-hydroxy-lH-pyrazole was added followed by 0.18 g (1.78 mmol) of triethylamine. The reaction mixture was heated at reflux for 1 h and then allowed to stir at room temperature overnight. The reaction mixture was poured into ice and 1 N ΗC1 and extracted three times with methylene chloride. The combined organic extracts were dried (MgSO 4 ) and concentrated to give 0.5 g of an oil. The residue was flash chromatographed on silica gel with ethyl acetate to give 90 mg of the title compound of Step I as a solid (a sample prepared in a separate experiment provided material melting at 158-161 °C with apparent decomposition). l H NMR (Me SO-<2 6 ) δ 1.20 (t,3H), 1.32 (t,3H), 1.49 (s,9H), 3.25 (m,2H), 3.56 (m,2H), 3.87 (q,2H) 4.09 (q,2H), 6.24 (d,lH), 7.47 (d,lH), 8.09 (d,lH), 8.38 (d,lH). Step J: Preparation of 2-(l.l-dimethylethyl)-5-f(l-ethyl-5-hydroxy-lH-pyrazol-4- yl)carbonyn-8-(ethylsulfonyl)-3.4-dihydro- 1 (2H)-isoquinolinone 0.28 g (0.65 mmol) of the title compound of Step I, 3.4 mL of dry methylene chloride, 0.16 mL (1.15 mmol) of triethylamine and one drop of acetone cyanohydrin were combined and stirred at room temperature over the weekend. The reaction mixture was diluted with ethyl acetate and 1 N ΗC1. The organic phase was then extracted three times with saturated aqueous sodium bicarbonate. The basic aqueous phase was adjusted to pΗ 2 and extracted four times with methylene chloride. The combined methylene chloride extracts were dried (MgSO 4 ) and concentrated to give 0.35 g. Trituration with ether hexane gave 0.15 g of the title compound of Step J, a compound of the invention, as a yellow solid melting at 164-167 °C. J Η NMR (Me 2 SO-d 6 ) δ 1.20 (t,3H), 1.27 (t,3H), 1.47 (s,9H), 2.82 (t,2H), 3.50 (t,2H), 3.87 (q,2H), 3.92 (q,2H), 7.48 (s,lH), 7.69 (d,lH), 7.97 (d,lH). EXAMPLE 2 Step A: Preparation of l-r(2-chloro-2-propenyDthiol-2.5-dimethylbenzene To a suspension of potassium carbonate 50.0 g (0.362 mol) in 600 mL of DMF at room temperature was added 50.0 g (0.362 mol) of 2,5-dimethylthiophenol dropwise. The temperature was allowed to rise to 29 °C with continued stirring for an additional 1 h. 40.1 g (0.362 mol) of 2,3-dichloropropene was added dropwise at room temperature and the reaction was allowed to stir overnight. The crude reaction mixture was poured into excess ice/water and the resulting solution was extracted twice with ethyl acetate. The combined organic phase was dried (MgSO 4 ) and concentrated to give a gold oil 76.1 g of the title compound of Step A which was used in the next step without further purification. J H NMR (CDC1 3 ) δ 2.30 (s,3H), 2.40 (s,3H), 3.64 (s,2H), 5.22 (d,2H), 6.95 (d,lH), 7.08 (d,lH), 7.13 (s,lH). Step B: Preparation of 2.4.7-trimethylbenzorfclthiophene To 230 mL of dimethylaniline at reflux was added dropwise a solution of 50.0 g (0.236 mol) of the title compound of Step A and 200 mL of dimethylaniline. The solution was heated overnight at reflux and then allowed to come to room temperature. The crude reaction mixture was diluted with excess ether and washed with IN HCl until dimethylaniline could no longer be detected. The ether layer was dried over MgSO 4 , filtered and concentrated to yield 38.1 g of the title compound of Step B as a brown oil. The compound was used without further purification in the next reaction. *H NMR (CDC1 3 ) δ 2.30 (s,3H), 2.55 (s,3H), 2.61 (s,3H), 6.95 (d,lH), 7.04 (d, IH), 7.10 (s,lH). Step C: Preparation of 2.3-dihydro-2 A7-trimethylbenzo l r frlt.ιiophene A solution of 38.0 g (0.215 mol) of the title compound of step B, 98.0 mL (0.429 mol) of triethylsilane in 280 mL of trifluoroacetic acid was heated overnight at reflux. The crude reaction mixture was concentrated, diluted with excess ether, and washed with saturated sodium bicarbonate until an aqueous test extraction was neutral. The ether phase was dried over MgSO 4 , filtered and concentrated to yield an orange oil. Chromatography on silica gel with hexane provided 20.4 g of the title compound of Step C as a pale yellow oil. J H NMR (CDC1 3 ) δ 1.48 (d,3H), 2.20 (s,6H), 2.90 (dd,lH), 3.38( dd,lH), 3.95-4.09 (m,lH), 6.78 (d,lH), 6.83 (d,lH). Step D: Preparation of 5-bromo-2,3-dihydro-2.4.7-trimethylbenzoffe1thiophene A solution of 10.3 g (58.0 mmol) of the title compound of Step C in 120 mL of dichloromethane was treated at room temperature with 9.3 g (58.0 mmol) of bromine dropwise. The solution was stirred an additional 3 h, diluted with excess ethyl acetate, washed with excess saturated sodium bisulfite solution and dried over MgSO . Filtration followed by concentration provided the crude product as a yellow oil. Chromatography on silica gel in hexanes provide 10.6 g of the title compound of Step D as a clear oil. *H NMR (CDC1 3 ) δ 1.46 (d,3H), 2.16 (s,3H), 2.29 (s,3H), 2.95 (dd.lH), 3.40 (dd,lH), 3.93-3.99 (m,lH), 7.15 (s,lH). Step E: Preparation of 2.3-dihydro-2.4.7-trimethylbenzorb]thiophene-5- carboxylic acid To a solution of 15.1 g (58.7 mmol) of the title compound of Step D in THF at -70 °C was added dropwise a solution of n-butyl lithium (24.7 mL of a 2.5 M solution in hexanes, 61.6 mmol). During the addition, the temperature was maintained below -60 °C. The reaction mixture was stirred an additional 30 min at -70 °C and then excess carbon dioxide gas was passed into the solution (15 min). The reaction mixture was allowed to slowly warm to room temperature and stir overnight. The reaction mixture was diluted with excess water, acidified with concentrated HCl to pH 2, and extracted with ethyl acetate several times. The combined organic phase was dried over MgSO 4 , filtered and concentrated to provide the crude acid as a green solid. The crude product was suspended in hexanes, collected by filtration, and air dried to yield 8.5 g of the title compound of Step E as a green solid. J H NMR (CDC1 3 ) δ 1.48(d,3H), 2.23(s,3H), 2.51(s,3H), 3.01(dd,lH), 3.47(dd,lH), 3.98-4.03(m,lH), 7.71(s,lH). Step F: Preparation of 2.3-dihydro-2.4.7-trimethylbenzo| " b].hiophene-5- carboxylic acid 1.1 -dioxide To a solution of 38.8 g (56.0 mmol) of Oxone® in 250 mL of water at room temperature was added dropwise a solution of 5.0 g (23.0 mmol) of the title compound of Step E in 50 mL of acetone. To the resulting solution was added portionwise 12.0 g (143 mmol) of sodium bicarbonate. The solution was stirred an additional 1.5 h at room temperature. To the solution was added IN HCl to bring the pH to 3. The solution was extracted with ethyl acetate and the combined organic phase was washed with saturated sodium bisulfite solution, dried over MgSO , filtered and concentrated to provide the title compound of Step F as a white solid melting at 186-189 °C. l H NMR (CDC1 3 ) δ 1.56 (d,3H), 2.52 (s,3H), 2.65 (s,3H), 2.82 (dd.lH), 3.40-3.61(m,2H), 7.83 (s,lH). Step G: Preparation of 1 -ethyl- l-H-pyrazol-5-yl 2.3-dihydro-2.4.7- trimethylbenzorfrl thiophene-5-carboxylate 1.1 -dioxide To a solution of 1.0 g (3.94 mmol) of the title compound of Step F in 35 mL of dichloromethane at room temperature was added 0.55 mL (6.30 mmol) of oxalyl chloride and a catalytic amount of dimethylformamide. The resulting solution was heated to reflux for 3 h and then stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo. The crude reaction mass was dissolved in 20 mL of dichloromethane and treated at room temperature successively with 0.89 mL (6.30 mmol) of triethylamine followed by 0.46 g (4.11 mmol) of l-ethyl-5-hydroxy-lH- pyrazole. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with excess ethyl acetate, washed with water and dried over MgSO 4 . Filtration followed by concentration afforded the crude product which was chromatographed on silica gel (elution with 1:1 ethyl acetate:hexanes) to afford 0.89 g of the title compound of Step G as a white solid. l H NMR (CDC1 3 ) δ 1.45 (t,3Η), 1.58 (d,3H), 2.54 (s,3H), 2.69 (s,3H), 2.85 (dd,lH), 3.47-3.59 (m,2H), 4.10 (q,2H), 6.24 (d,lH), 7.50 (d,lH), 7.86 (s,lH). Step H: Preparation of ( 2.3-dihydro-2.4.7-trimethylbenzorblthiophene-5-yl)( 1 - ethyl-5-hyόJOxy-lH-pyrazol-4-y methanone -S'.-?-dioxide To a solution of 0.89 g (2.56 mmol) of the title compound of Step G in 15 mL of acetonitrile at room temperature was added 4 drops of acetone cyanohydrin followed by 0.57 mL (4.09 mmol) of triethylamine. The solution was stirred at room temperature overnight, then diluted with excess water, acidified with IN ΗC1 to pΗ 3-5 and extracted with ethyl acetate. The organic phase was dried over MgSO , filtered and concentrated. The crude product was triturated with a 1:1 mixture of /i-butyl chloride±exanes to yield the title compound of Step Η, a compound of the invention, as a white solid melting at 152-157 °C. *Η NMR (CDCI3) δ 1.46 (t,3H), 1.57 (d,3H), 2.29 (s,3H), 2.66 (s,3H), 2.80 (dd,lH), 3.44 (dd,lH), 3.50-3.61 (m,lH), 4.08 (q,2H), 7.28 (s,lH), 7.35 (s.lH). EXAMPLE 3 Step A: Preparation of methyl 4-ι r (2-ethoxy-2-oxoethyl)thio]-3-nitrobenzoate 0.36 g (9 mmol) of 60% sodium hydride was suspended in anhydrous dimethylformamide and cooled to 0 °C. After the dropwise addition of 0.93 mL (8.5 mmol) of ethyl 2-mercaptoacetate, the reaction was warmed to room temperature and stirred for an additional 30 minutes. 1.8 g (8.3 mmol) of methyl 4-chloro-3- nitrobenzoate was added dropwise, keeping the reaction temperature below 10 °C. The reaction mixture was then slowly warmed to room temperature and poured into 150 mL of ice water. The precipitate was stirred vigorously for 20 minutes and then filtered. The solid was dried to give 2.3 g of the title compound of Step A as a yellow solid melting at 74-76 °C. J H NMR (CDC1 3 ) δ 8.88 (d,lH), 8.20 (d,lH), 7.6 (d,lH), 4.23 (q,2H), 3.97 (s,3H), 3.80 (s,2H), 1.28 (t,3H). Step B: Preparation of methyl 3,4-dihydro-3-oxo-2H-l,4-benzothiazine-6- carboxylate 10.0 g (35 mmol) of the title compound of Step A was dissolved in 160 mL of acetic acid and 20 mL of water was added. The solution was heated to 65 °C and 11.7 g (210 mmol) of iron powder was added in small portions. Vigorous stirring was continued for 10 minutes after the end of the iron addition, after which the reaction was filtered through Celite®. The solids were washed with acetic acid and the combined filtrates concentrated. The crude mixture was partitioned between ethyl acetate and sodium bicarbonate solution. The layers were separated and the organic phase was extracted three times with more ethyl acetate. The combined ethyl acetate layers were washed with sodium bicarbonate solution and saturated aqueous NaCl, dried over magnesium sulfate, and concentrated to yield 7.0 g of the title compound of Step B as a white solid melting at 178-180 °C. 1.3 NMR (CDC1 3 ) δ 8.68 (br s,lΗ), 7.67 (d,lH), 7.57 (s,lH), 7.38 (d,lH), 3.93 (s,3H), 3.49 (s,2H). Step C: Preparation of methyl 4-ethyl-3.4-dihydro-3-oxo-2H- 1.4-benzothiazine-6- carboxylate 10.0 g (45 mmol) of the title compound of Step B was dissolved in 50 mL of anhydrous dimethylformamide. 6.0 g (54 mmol) of potassium t-butoxide was added and the reaction was stirred for 15 minutes. 4.0 mL (50 mmol) of ethyl iodide was added dropwise and the reaction was stirred for 2 h. The reaction mixture was poured into 350 mL of cold water and extracted three times with diethyl ether. The combined ether extracts were washed three times with water, twice with saturated aqueous NaCl, and were then dried over magnesium sulfate and concentrated to a crude oil. Chromatography with ethyl acetate and hexane yielded 3.7 g of the title compound of Step C. J Η NMR (CDC1 3 ) δ 7.80 (s,lH), 7.70 (d,lH), 7.42 (d,lH), 4.09 (q,2H), 3.94 (s,3H), 3.41 (s,2H), 1.30 (t,3H). Step D: Preparation of methyl 4-ethyl-3.4-dihydro-3-oxo-2H-l .4-benzothiazine-6- carboxylate 1.1 -dioxide To a mixture of 2.0 g (8.0 mmol) of the title compound of Step C in 50 mL of methylene chloride was added 5.0 mL (24 mmol) of 32% peracetic acid dropwise over a period of 20 minutes. The reaction mixture was stirred at room temperature for 48 h, diluted further with methylene chloride, washed once with water, twice with sodium sulfite solution, and once with sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated to afford 2.05 g of the title compound of Step D as a yellow solid. *H NMR (CDC1 3 ) δ 8.05 (d,lH), 7.99 (m,2H), 4.26 (s,2H), 4.18 (q,2H), 4.00 (s,3H), 1.37 (t,3H). Step E: Preparation of 4-ethyI-3.4-dihydro-3-oxo-2H- 1.4-benzothiazine-6- carboxylic acid 1.1 -dioxide To a mixture of 2.05 g (7.2 mmol) of the title compound of Step D in 15 mL of methanol was added dropwise a solution of 1.2 g (29 mmol) of sodium hydroxide in 5 mL of water. The reaction mixture was stirred at room temperature for 1 h, diluted with water, and cooled in an ice/water bath. Slow acidification with IN ΗC1 to pΗ 2 yielded a precipitate which was isolated by filtration to give 1.45 g of the title compound of Step E as a white solid. *Η NMR (Me 2 SO-d 6 ) δ 13.8 (s,lH), 8.02 (d,lH), 7.96 (d,lH), 7.91 (d,lH), 4.91 (s,2H), 4.11 (q,2H), 1.20 (t,3H). Step F: Preparation of 3-oxo-l -cyclohexen- 1-yl 4-ethyl-3.4-dihydro-3-oxo-2H- 1.4-benzothiazine-6-carboxylate 1.1 -dioxide To a mixture of 500 mg (1.86 mmol) of the title compound of Step E and 570 mg (2.23 mmol) of N-methyl-2-chloropyridinium iodide in 2 mL of methylene chloride was added 310 μL (2.25 mmol) of triethylamine and the reaction mixture was stirred for 15 minutes. A solution of 212 mg (1.9 mmol) of 1,3-cyclohexanedione and 310 μL (2.25 mmol) of triethylamine in 2 mL of methylene chloride was then added dropwise. After stirring overnight at room temperature, the reaction mixture was concentrated and the crude residue was chromatographed in ethyl acetate and hexane to give 210 mg of the title compound of Step F as a white solid. J Η ΝMR (CDC1 3 ) δ 8.1 (d,lH), 8.02 (s,lH), 8.0 (d,lH), 6.08 (s,lH), 4.28 (s,2H), 4.2 (q,2H), 2.7 (t,2H), 2.5 (t,2H), 2.2 (m,2H), 1.38 (t,3H). Step G: Preparation of 4-ethyl-6-|ϊ2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yPcarbonyl]- 2H- 1.4-benzothiazin-3(4H)-one 1.1 -dioxide 80 mg (0.22 mmol) of the title compound of Step F, 56 μL (0.40 mmol) of triethylamine, and 1 drop of acetone cyanohydrin were dissolved in 6 mL of dry acetonitrile and stirred for 12 h. A catalytic crystal of potassium cyanide was added to the reaction mixture and stirring was continued for another 24 h. The reaction mixture was then concentrated and the residue was dissolved in water. The aqueous mixture was washed once with diethyl ether, acidified to pΗ 2 with IN ΗC1, and extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over magnesium sulfate and concentrated to yield 60 mg of the title compound of Step G, a compound of the invention, as an oil which crystallized to a solid melting at 158-165 °C. *Η ΝMR (CDC1 3 ) δ 7.96 (d,lH), 7.37 (s,lH), 7.33 (d,lH), 4.26 (s,2H), 4.12 (q,2H), 2.8 (br s,2H), 2.5 (br s,2H), 2.1 (m,2H), 1.36 (t,3H). By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 30 can be prepared. The following abbreviations are used in the Tables which follow: t = tertiary, n = normal, i = iso, Me = methyl, Et = ethyl, Pr = propyl, i-Pr = isopropyl, Bu = butyl, Ph = phenyl, OMe = methoxy, OEt = ethoxy, CN = cyano, NO = nitro, CHO = formyl, CO 2 Et = ethoxycarbonyl, SO 2 Me = methylsulfonyl, SO 2 Et = ethylsulfonyl, and SO 2 Ph = phenylsulfonyl. S0 2 Me H Et S0 2 Et H Et S0 2 NMe 2 Me Me S0 2 Me H /-Bu S0 Et Me /-Bu S0 2 NMe 2 Me Et S0 2 Me Me H S0 2 Et Me Me S0 2 NMe 2 Cl /-Bu S0 Me Me Me S0 2 Et Me Et S0 2 NMe Cl Et S0 2 Me Me Et S0 2 Et Cl /-Bu S0 2 Et H OMe S0 2 Me Cl H S0 2 Et Cl Me S0 2 Et Me OMe S0 2 Me Cl Me S0 2 Et Cl Et S0 2 -n-Pr H Me S0 2 Me Cl Et S0 NMe 2 H /-Bu S0 2 -π-Pr H /-Bu S0 2 Et H H S0 2 NMe 2 H Et Table 3 Table 5 Table 6 Table 7 S0 2 NHCgH 4 -3-CF 3 S0 2 NHCgH 4 -3-CN S0 2 NHC 6 H 4 -3-N0 2 S0 2 NHCgH 3 -2,4-diCl S0 -azetidinyl S0 2 -pyrrolidinyl S0 2 -piperdinyl S0 -2,6-dimethyl orpholinyl S0 2 - -Pr S0 2 -/-Bu S0 2 -π-C 5 H n S0 2 -n-CgHι 3 S0 2 CH 2 CH 2 CF 3 S0 2 CH 2 C≡CH S0 -cyclopropyl S0 2 -cyclohexyl S0 2 C 6 H 5 S0 2 CgH 4 -2-Me S0 2 C 6 H 4 -3-CF 3 S0 2 CgH 4 -2-OMe S0 2 CgH 4 -3-OCF 3 S0 2 CgH 3 -2,4-diCl S0 2 CgH 4 -3-CN S0 2 CgH 4 -3-N0 2 S0 2 NHMe S0 2 NHEt Table 8 Table 9 Table 10 Table 12 Table 13 Table 17 Table 22 Table 23 Table 24 Table 25 Table 26 Table 27 H CH 3 H Table 28 Me Me Et Me Me j-Bu Formulation/Utility Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight. Weight Percent High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxyprσpylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4- methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, 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; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-E. Example A High Strength Concentrate Compound 20 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%. Example B Wettable Powder Compound 22 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium sUicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example C Granule Compound 20 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example D Extruded Pellet Compound 22 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth. Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butylate, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyraUd, clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, 2-[4,5-dihydro-4-methyl-4-( 1 -methylethyl)-5-oxo- 1H- imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfiuralin, ethametsulfuron-methyl, ethofumesate, ethyl α,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- IH- 1 ,2,4-triazol- 1 -yl]- 4-fluorobenzenepropanoate (F8426), fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, fiazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, fluridone, flurochloridone, fluroxypyr, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox (AC 299263), imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole (RPA 201772), lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methyl [[2- chloro-4-fluoro-5-[(tetrahydro-3-oxo- lH,3H-[ 1 ,3,4]thiadiazolo[3,4--z]pyridazin- 1 - ylidene)amino]phenyl]thioacetate (KIΗ 9201), methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[l-[5-[2-chloro-4- (trifluoromemyl)phenoxy]-2-nitrophenyl]-2-memoxyethyUdene]amino]oxy]acetate (AKΗ-7088), me yl 5-[[[[(4,6-d-memyl-2-pyrimicUnyl)ammo]carbonyl]amino]sulfonyl]- l-(2-pyridinyl)-lH-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, 3-oxetanyl 2-[[[[(4,6-dimemyl-2-pyrimidinyl)amino]c-irbonyl]amino]sulfonyl]benzoate (CGA 277476), oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuiyl, rimsulfuron, sethoxydim, siduron, simazine, sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vernolate. In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. Preferred for better control of undesired vegetation (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group atrazine, chlorimuron-ethyl, cyanazine, glyphosate (and its isopropylammonium, sesquisodium and trimesium salts), imazaquin (and its ammonium salt), imazethapyr (and its ammonium salt), nicosulfuron, primisulfuron-methyl, rimsulfuron and thifensulfuron-methyl. Specifically preferred mixtures (compound numbers refer to compounds in Index Tables A-E) are selected from the group: compound 1 and atrazine; compound 1 and chlorimuron-ethyl; compound 1 and cyanazine; compound 1 and glyphosate; compound 1 and imazaquin; compound 1 and imazethapyr; compound 1 and nicosulfuron; compound 1 and primisulfuron-methyl; compound 1 and rimsulfuron; compound 1 and thifensulfuron-methyl; compound 20 and atrazine; compound 20 and chlorimuron-ethyl; compound 20 and cyanazine; compound 20 and glyphosate; compound 20 and imazaquin; compound 20 and imazethapyr; compound 20 and nicosulfuron; compound 20 and primisulfuron-methyl; compound 20 and rimsulfuron; compound 20 and t-_dfensulfuron-methyl; compound 21 and atrazine; compound 21 and chlorimuron-ethyl; compound 21 and cyanazine; compound 21 and glyphosate; compound 21 and imazaquin; compound 21 and imazethapyr; compound 21 and nicosulfuron; compound 21 and primisulfuron-methyl; compound 21 and rimsulfuron; compound 21 and thifensulfuron-methyl; compound 22 and atrazine; compound 22 and chlorimuron-ethyl; compound 22 and cyanazine; compound 22 and glyphosate; compound 22 and imazaquin; compound 22 and imazethapyr; compound 22 and nicosulfuron; compound 22 and primisulfuron-methyl; compound 22 and rimsulfuron; compound 22 and thifensulfuron-methyl; compound 41 and atrazine; compound 41 and chlorimuron-ethyl; compound 41 and cyanazine; compound 41 and glyphosate; compound 41 and imazaquin; compound 41 and imazethapyr; compound 41 and nicosulfuron; compound 41 and primisulfuron-methyl; compound 41 and rimsulfuron; and compound 41 and thifensulfuron-methyl. A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control. The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions. The following abbreviations are used in the Index Tables which follow: t = tertiary, n = normal, i = iso, Me = methyl, Et = ethyl, Pr = propyl, Bu = butyl, Ph = phenyl, OMe = methoxy, MeSO 2 = methylsulfonyl, EtSO 2 = ethylsulfonyl, PhSO 2 = phenylsulfonyl, and PhC(O) = benzoyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. INDEX TABLE A wherein R 23 is H or R 2 and R^ and K*b are independently H or l *See Index Table E for lH NMR data. INDEX TABLE B *See Index Table E for J H NMR data. INDEX TABLE C wherein R 23 is H or R 2 *See Index Table E for i H NMR data. INDEX TABLE D a Compound contains approximately 43% by weight of 7-(ethylsulfonyl)-l,3-dihydro-l- oxo-4-isobenzofurancarboxylic acid. *See Index Table E for *H NMR data. INDEX TABLE E Cmpd No. i H NMR Data (CDC1 3 solution unless indicated otherwise) 3 4 δ 0.94 (d,6H), 2.05 (m,lH), 2.11 (m,2H), 2.51 (t,2H), 2.82 (t,2H), 3.96 (d,2H), 4.26 (s,2H), 7.35 (s,lH), 7.35 (d,lH), 7.98 (d,lH). 17 δ 1.4 (s,6H), 1.9-2.1 (m,2H), 2.3-2.5 (m,4H), 2.6 (t,2H), 2.75 (br t,lH), 3.3-3.4 (m,2H), 7.5-7.7 (m,3H), 8.4 (br s,lH). 18 δ 1.65 (s,6H), 2.0-2.1 (m,2H), 2.3-2.6 (m,4H), 2.6 (t,J=6.9 Hz, IH), 2.8 (t,J=6.3 Hz,lH), 3.2-3.4 (m,2H), 7.6-7.7 (m,2H) (acidic hydrogen not observed). 30 5 1.32 (d, J=7.24 Hz,3H), 1.47 (t,J=7.24 Hz,3H), 2.22 (s,3H), 2.52 (s,3H), 3.10 (d,J=13.25 Hz,lH), 3.33 (dd,J=13.25, 8.07 Hz,lH), 4.06 (q,J=7.24 Hz,2H), 7.14 (s,lH), 7.50-7.55 (m,2H), 7.68-7.74 (m,lH), 7.85 (s,lH), 7.89-7.95 (m,2H). 34 δ 1.32 (s,9H), 2.31 (s,3H), 2.63 (s,3H), 3.09 (dd,J=16.20, 10.02 Hz,lH), 3.23 (dd,J=16.2, 8.18 Hz,lH), 3.39 (dd,J=10.02, 8.18 Hz,lH), 3.72 (s,3H), 7.25 (s,lH), 7.34 (s.lH). 38 (Me 2 SO--i 6 ) 5 1.13 (t,J=7.5 Hz,3H), 1.29 (t,J=7.2 Hz,3H), 3.74 (q,J=7.5 Hz,2H), 4.03 (q,J=7.5 Hz,2H), 5.76 (s.lH), 7.80 (s.lH), 8.22 (d,J=7.8 Hz,lH), 8.42 (d,J=7.8 Hz,lH). a ] H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (br s)-broad singlet, (br t)-broad triplet. BIOLOGICAL EXAMPLES OF THE INVENTION TEST A Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galU), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrastϊ), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. 61 62 The compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test. Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrastϊ), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-gallϊ) and Late watergrass (Echinochloa oryzicola) grown to the 2 leaf stage for testing. All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response this ratings, summarized in Table B, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. 69 TABLE B COMPOUND Rate 62 g/ha 5 18 20 21 24 37 41 43 POSTEMERGENCE Barley Igri 70 30 30 Barnyard Flood Barnyardgrass Bedstraw Blackgrass Chickweed Cocklebur Corn Cotton Crabgrass Downy Brome Duck salad Giant foxtail Italn. Ryegrass Johnsongrass Lambsquarter Morningglory Rape Redroot Pigweed Rice Japonica Soybean Speedwell Sugar beet Umbrella sedge Velvetleaf Watergrass 2 Wheat Wild buckwheat Wild oat TABLE B COMPOUND Rate 8 g/ha 9 10 21 22 25 26 44 POSTEMERGENCE Barley Igri 0 0 0 0 0 0 0 0 Barnyard Flood 0 0 0 0 Barnyardgrass 80 60 70 90 70 75 95 60 Bedstraw 80 30 40 80 85 20 30 0 Blackgrass 10 0 0 20 0 0 0 0 Chickweed 85 50 70 85 70 90 70 65 Cocklebur 70 90 90 90 80 90 90 90 Corn 0 0 0 0 0 0 0 0 Cotton 90 50 90 50 80 40 80 50 Crabgrass 70 40 60 80 70 65 80 30 Downy Brome 10 0 0 0 0 0 0 0 Duck salad 0 0 0 0 Giant foxtail 0 10 10 60 50 70 70 0 Italn. Ryegrass 10 0 0 0 0 0 0 0 Johnsongrass 30 10 10 10 20 25 40 10 Lambsquarter 95 85 85 95 90 90 90 20 Morningglory 85 80 90 90 90 30 20 80 Rape 30 70 60 80 90 60 20 70 Redroot Pigweed 70 40 30 30 70 30 40 20 Rice Japonica 0 0 0 - 10 Soybean 80 60 70 80 65 70 60 30 Speedwell 90 40 50 70 85 50 - 50 Sugar beet 90 70 50 80 95 60 90 95 Umbrella sedge 0 0 0 0 Velvetleaf 90 90 90 80 90 90 90 60 Watergrass 2 Wheat 10 20 0 0 0 0 20 0 Wild buckwheat 60 10 10 85 90 10 10 0 Wild oat 0 10 0 0 0 25 20 0 Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Convolvulus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setariafaberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Panicum miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a sandy loam or clay loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one to four leaf stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Pots receiving preemergence treatments were planted immediately prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table C, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedhngs emerged (preemergence application) and to plants that were grown for various periods of time before treatment (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include American black nightshade (Solanum americanum), arrowleaf sida (Sida rhombifolia), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common lambsquarters (Chenopodium album), common ragweed (Ambrosia artemisiifolia), corn (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum), field bindweed (Convolvulus arvensis), Florida beggarweed (Desmodium purpureum), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb (Polygonum persicaria), large crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean (Glycine max), Surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (Euphorbia heterophylla). Treated plants and untreated controls were maintained in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table D, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A dash response (-) means no test result. TEST E Seeds, tubers, or plant parts of alexandergrass (Brachiaria plantaginea), alfalfa (Medicago sativa), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria plantyphylla), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hirsutum), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanuts (Arachis hypogaea), pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), Surinam grass (Brachiaria decumbens) and texas panicum (Panicum Texas) were planted into greenhouse pots of flats containing greenhouse planting medium. Plant species were grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury 13 to 21 days after herbicide application. Plant response ratings, summarized in Table E, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response means no test result. TABLE E COMPOUND TABLE E COMPOUND TABLE E COMPOUND Rate 32 g/ha 20 Rate 32 g/ha 20 POSTEMERGENCE PREEMERGENCE Alexandergrass 100 Alexandergrass 50 Bermudagrass 80 Bermudagrass 95 Brdlf Sgnlgrass 75 Brdlf Sgnlgrass 0 Cmn Purslane 98 Cmn Purslane 90 Cmn Ragweed 60 Cmn Ragweed 30 Cotton 100 Cotton 0 Dallisgrass 80 Dallisgrass 20 Goosegrass 65 Goosegrass 0 Guineagrass 20 Guineagrass 0 Itchgrass 20 Itchgrass 0 Johnson grass 25 Johnson grass 0 Large Crabgrass 90 Large Crabgrass 30 Peanuts 60 Peanuts 40 Pit Morninglory 90 Pit Morninglory 30 Purple Nutsedge 80 Purple Nutsedge 0 Sandbur 95 Sourgrass 98 Sourgrass 80 Surinam grass 0 Surinam grass 65 TABLE E COMPOUND Rate 16 g/ha 20 POSTEMERGENCE Alexandergrass 100 Bermudagrass 60 Brdlf Sgnlgrass 0 Cmn Purslane 98 Cmn Ragweed 90 Cotton 80 Dallisgrass 80 Goosegrass 50 Guineagrass 5 Itchgrass 5 Johnson grass 10 Large Crabgrass 90 Peanuts 10 Pit Morninglory 75 Purple Nutsedge 30 Sandbur 70 Sourgrass 75 Surinam grass 50 TEST F Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), black nightshade (Solanum nigra), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Gahum aparine), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), little seed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), ryegrass (Lolium multiflorum), scentless chamomile (Matricaria inodora), speedwell (Veronica persica), spring barley (Hordeum vulgare cv. 'Klages 1 ), spring wheat (Triticum aestivum cv. 'ERA'), sugar beet (Beta vulgaris cv. 'USl'), sunflower (Helianthus annuus cv. 'Russian Giant"), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), windgrass (Apera spica-venti), winter barley (Hordeum vulgare cv. Igri 1 ) and winter wheat (Triticum aestivum cv. Talent"). Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table F, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result. TABLE F COMPOUND Rate 125 g/ha 21 22 POSTEMERGENCE Annual Bluegrass 100 100 Blackgrass 30 20 Blk Nightshade 30 20 Chickweed 100 100 Deadnettle 100 100 Downy brome 100 100 Field violet 0 5 Galium 100 100 Green foxtail 60 70 Ivy Speedwell 100 100 Jointed Goatgr. 10 10 Kochia 70 100 Lambsquarters 100 100 LS Canarygrass 30 30 Redroot Pigweed 100 100 Russian Thistle 70 80 Ryegrass 5 20 Scentless Cham. 100 100 Spring Barley 20 10 Wheat (Spring) 30 25 Wheat (Winter) 30 15 Wild buckwheat 70 75 Wild mustard 100 100 Wild oat 50 70 Windgrass 20 5 Winter Barley 20 15 Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture and applied to the surface of the water which was contained in each pot. Individual containers of barnyardgrass (Echinochloa oryzicola), small flower umbrella sedge (Cyperus difformis), common falsepimpernel (Lindernia procumbens), monochoria (Monochoria vaginalis) and bulrush (Scirpus juncoides) were seeded and allowed to grow until the 1.5 to 2.5 leaf stage of development. A Sultama clay loam soil was used for this propagation. Japonica rice (Oryza sativa) was transplanted at 0 and 2 cm depth five days before application of the test compound to the water surface. An early and late stage of each weed species was treated, the stage of development being related to the concurrent planting of Scirpus juncoides which was then treated at the 1.5 (early) and the 2.5 (late) leaf stage. Treated plants and untreated controls were maintained under greenhouse conditions for twenty to thirty days at which time treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) indicated that no test result was recorded. TABLE G COMPOUND TABLE G COMPOUND Rate 1000 g/ha 37 Flood Saita soil barnyard early 100 barnyard late 70 C. difformis early 100 C. difformis late 60 Japoni rice 0cm 85 Japoni rice 2cm 80 L. procumben early 100 L. procumben early 100 100 L. procumben late 100 L. procumben late 100 100 M. vaginalis early 80 M. vaginalis early 80 65 M. vaginalis late 65 M. vaginalis late 75 70 S. juncoides early 80 S. juncoides early 45 60 S. juncoides late 55 S. juncoides late 55 50 TABLE G COMPOUND TABLE G COMPOUND Rate 250 g/ha 18 37 38 Rate 125 g/ha 18 37 38 Flood Saita soil Flood Saita soil barnyard early 40 65 20 barnyard early 35 10 20 barnyard late 50 50 20 barnyard late 35 0 30 C. difformis early 40 65 20 C. difformis early 20 20 20 C. difformis late 70 40 20 C. difformis late 30 10 40 Japoni rice 0cm 85 10 25 Japoni rice 0cm 45 0 5 Japoni rice 2cm 60 0 15 Japoni rice 2cm 5 10 15 L. procumben early 100 100 60 L. procumben early 100 70 20 L. procumben late 100 100 40 L. procumben late 100 100 50 M. vaginalis early 65 75 30 M. vaginalis early 70 30 10 M. vaginalis late 70 55 50 M. vaginalis late 55 30 40 S. juncoides early 45 40 20 S. juncoides early 35 10 30 S. juncoides late 50 30 30 S. juncoides late 40 0 40 TABLE G COMPOUND TABLE G COMPOUND Rate 64 g/ha 18 38 Rate 32 g/ha 38 Flood Saita soil Flood Saita soil barnyard early 30 20 barnyard early 10 barnyard late 30 10 barnyard latete 20 C. difformis early 0 20 C. difformis early 30 C. difformis late 10 10 C. difformis late 10 Japoni rice 0cm 25 10 Japoni rice 0cm 5 Japoni rice 2cm 0 0 Japoni rice 2cm 5 L. procumben early 100 50 L. procumben early 20 L. procumben late 100 20 L. procumben late M. vaginalis early 60 10 M. vaginalis early 20 M. vaginalis late 60 30 M. vaginalis late 40 S. juncoides early 20 30 S. juncoides early 30 Ξ. juncoides late 20 20 S. juncoides late 30

Claims: CLAIMS What is claimed is: 1. A compound selected from Formula I, and agriculturally suitable salts thereof, wherein Q is Q-l Q-2 A is -(CH 2 ) m -, -CH=CH-, -CH 2 CH=CH-, -CH=CHCH 2 -, -(CH 2 ) n -NR9. ) -NR 9 -(CH 2 ) n -, -(CH 2 ) n -O- or -(CH 2 ) n -S(O) 2 -, each group optionally substituted with one to four R 8 , and the directionality of the A linkage is defined such that the moiety depicted on the left side of the linkage is bonded to Y and the moiety on the right side of the linkage is bonded to the phenyl ring; Y is O; NR 9 ; or CH optionally substituted with one or two groups independently selected from C ] -C 6 alkyl, C^Cg haloalkyl and halogen; provided that when A is -NR 9 -(CH 2 ) n -, then Y is CH 2 ; Z is C(=X), O, or S(O) 2 ; provided that when Y is O or NR 9 , then Z is C(=X); X is O or S; R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 1 -C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano, nitro, S(O) 2 NR 10 R π , C r C 6 alkylsulfonyl, C r C 6 haloalkylsulfonyl, C3-C6 alkenylsulfonyl, C 3 -C 6 haloalkenylsulfonyl, C 3 -C6 alkynylsulfonyl, CyC haloalkynylsulfonyl or C 3 -C 6 cycloalkylsulfonyl; or R 1 is phenylsulfonyl optionally substituted with C 1 -C 3 alkyl, C j -C 3 haloalkyl, C 1 -C3 alkoxy, C 1 -C3 haloalkoxy, 1-2 halogen, cyano or nitro; each R 2 is independently Cj-Cg alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano or nitro; R 3 is OR 12 , C r C 6 alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 haloalkylsulfinyl, C r C 6 alkylsulfonyl, C r C 6 haloalkylsulfonyl or halogen; each R 4 is independently C 1 -C 3 alkyl, C ! -C 3 alkoxy, C 1 -C 3 alkylthio or halogen; or when two R 4 are attached to the same carbon atom, then said R 4 pair can be taken together to form -OCH 2 CH 2 O-, -OCH 2 CH 2 CH 2 O-, -SCH 2 CH 2 S- or -SCH 2 CH 2 CH 2 S-, each group optionally substituted with 1-4 CH3; R 5 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 7 dialkylaminocarbonyl, C r C 6 alkylsulfonyl or C r C 6 haloalkylsulfonyl; or R 5 is benzoyl or phenylsulfonyl, each optionally substituted with C r C 3 alkyl, halogen, cyano or nitro; R 6 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; or R 6 is phenyl or benzyl, each optionally substituted on the phenyl ring with -C3 alkyl, C r C 3 haloalkyl, C r C 3 alkoxy, C r C 3 haloalkoxy, 1-2 halogen, cyano or nitro; R 7 is H, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano or nitro; each R 8 is independently C r C 6 alkyl, C r C 6 haloalkyl, C j -Cg alkoxy, C r C6 haloalkoxy, hydroxy or halogen; or two R 8 groups bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(=O) or C(=S); provided that when two R 8 groups are attached to a carbon atom which is attached to an O, NR 9 or S(O) 2 , then no more than one of said R 8 groups can be Cj-Cg alkoxy, C C^ haloalkoxy, hydroxy or halogen; each R 9 is independently H; C r C 6 alkyl; C r C 6 haloalkyl; C 3 -C 6 alkenyl; C 3 -C 6 haloalkenyl; C 3 -C 6 alkynyl; C 3 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 6 alkoxy; C r C 6 haloalkoxy; C 2 -C 6 alkoxyalkyl; formyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; C 2 -C 6 alkylaminocarbonyl; C 3 -C7 dialkylaminocarbonyl; or phenyl, benzyl or benzoyl, each optionally substituted on the phenyl ring with Cj-C 3 alkyl, C1-C 3 haloalkyl, -C 3 alkoxy, C 1 -C3 haloalkoxy, 1-2 halogen, cyano or nitro; R 10 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl or C r C 6 alkoxy; or R 10 is phenyl or benzyl, each optionally substituted on the phenyl ring with C1-C 3 alkyl, C r C 3 haloalkyl, C]^ alkoxy, C 1 -C 3 haloalkoxy, 1-2 halogen, cyano or nitro; R 1 ! is H, C r C 6 alkyl or C j -C 6 haloalkyl; or R 10 and R 11 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -, each optionally substituted with 1-4 C J -C 3 alkyl; R 12 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 7 ώ-ύkylaminocarbonyl, Cj-C 6 alkylsulfonyl or C r C 6 haloalkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with C ] -C 3 alkyl, halogen, cyano or nitro; m is 1, 2 or 3; n is 1 or 2; q is O, 1, 2, 3 or 4; and r is 0, 1 or 2; provided that (i) when Z is C(=X) or O; A is -(CH 2 ) m - optionally substituted with one to four R 8 ; and m is 1 or 2; then Q is Q-2; (ii) when Z is C(=X) or O; and A is -CH=CH- optionally substituted with one to two R 8 ; then Q is Q-2; (iii) when Z is C(=X) or O; A is -(CH 2 ) n -NR 9 -, -NR 9 -(CH 2 ) n - or -(CH 2 ) π -O- each optionally substituted with one to four R 8 ; and n is 1; then Q is Q-2; (iv) when A is -(CH 2 ) n -NR 9 -, -(CH 2 ) n -O- or -(CH 2 ) n -S(O) 2 - each optionally substituted with one to four R 8 ; and Y is CH 2 optionally substituted with one or two groups independently selected from Cj-Cg alkyl, C j -Cg haloalkyl and halogen; then Z is O or S(O) ; (v) when A is -(CH 2 ) m - optionally substituted with one to four R 8 ; Y is CH 2 optionally substituted with one or two groups independently selected from C r C6 alkyl, -Cg haloalkyl and halogen; and Z is O or S(O) 2 ; then each R 8 is independently C]-Cg alkyl, Cj-Cg haloalkyl, C j -Cg alkoxy, hydroxy or halogen provided that no more than one R 8 is C j -Cg alkoxy; and (vi) when A is -(CH 2 ) m - optionally substituted with one to four R 8 ; Y is CH 2 optionally substituted with one or two groups independently selected from C j -Cg alkyl, Cj-Cg haloalkyl and halogen; Z is S(O) 2 ; and m is 2; then Q is Q- 1 and each R 8 is independently C] -C 6 alkyl, C] -C 6 haloalkyl, hydroxy or halogen. 2. A compound of Claim 1 wherein: the A- Y-Z moiety is selected from combinations of A, Y and Z such that (i) when A is -(CH 2 ) m - optionally substituted with one to two R 8 and Y is O or NR 9 , then Z is C(=X); (ii) when A is -(CH 2 ) m - optionally substituted with one to two R 8 and Y is CH 2 optionally substituted with one or two groups independently selected from Cj-Cg alkyl, C r C 6 haloalkyl and halogen, then Z is O; and (iii) when A is -(CH 2 ) m - or -(CH 2 ) n -NR 9 - optionally substituted with one to two R 8 and Y is CH 2 optionally substituted with one or two groups independently selected from C r Cg alkyl, C r Cg haloalkyl and halogen, then Z is S(O) 2 ; X is O; each R 4 is independently C1-C 3 alkyl; R 6 is H, C 1 -C 6 alkyl or C 3 -C 6 alkenyl; R 7 is H, C r C 3 alkyl or C r C 3 haloalkyl; R 9 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 3 -C 6 cycloalkyl; R 12 is H, formyl, C -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -Cg alkylaminocarbonyl, C 3 -C7 dialkylaminocarbonyl, C j -Cg alkylsulfonyl or C Cg haloalkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro; q is 0, 1 or 2; and r is O or 1. 3. A compound of Claim 2 wherein: R 1 is H, methyl, halogen, S(O) 2 NR 10 R 1 J , C r C 4 alkylsulfonyl, C r C 4 haloalkylsulfonyl or C 3 -C5 cycloalkylsulfonyl; R 2 is methyl, halogen or nitro; R 3 is OR* 2 ; R 5 is H or C 1 -C 3 alkylsulfonyl; or R 5 is benzoyl or phenylsulfonyl, each optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro; each R 8 is independently C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halogen; or two R 8 groups bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(=O); R 10 is H, C r C 4 alkyl, allyl or propargyl; R 1 1 is H or C r C 4 alkyl; and R 12 is H or C r C 3 alkylsulfonyl; or R 12 is benzoyl or phenylsulfonyl, each optionally substituted with Cj-C 3 alkyl, halogen, cyano or nitro. 4. The compound of Claim 3 which is selected from the group: 2-( 1 , 1 -dimethylethyl)-5-[( 1 -ethyl-5-hydroxy- lH-pyrazol-4-yl)carbonyl]-8- (ethylsulfonyl)-3,4-dihydro- 1 (2H)-isoquinolinone; (2,3-dihydro-2,4,7-trimethylbenzo[b]thiophen-5-yl)( 1 -ethyl-5-hydroxy- 1H- pyrazol-4-yl)methanone S,5-dioxide; (l-ethyl-5-hydroxy-lH-pyrazol-4-yl)(2,3,4,5-tetrahydro-6,9-dimethyl-l- benzothiepin-7-yl)methanone 5',5-dioxide; 4-ethyl-6-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yl)carbonyl]-2H- 1 ,4-benzothiazin- 3(4H)-one 1,1 -dioxide; 4-ethyl-6-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-5,8-dimethyl-2H-l,4- benzothiazin-3(4H)-one 1,1 -dioxide; and (2,3-dihydro-2,4,7-trime-hylbenzo[fc]thiophen-5-yl)(5-hydroxy-l-methyl-lH- pyrazol-4-yl)methanone 5,5-dioxide. 5. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a Uquid diluent. 6. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.

Inventors: GEE STEPHEN KENNETH, HANAGAN MARY ANN, HONG WONPYO, KUCHARCZYK ROMAN, GEE, STEPHEN, KENNETH, HANAGAN, MARY, ANN, HONG, WONPYO, KUCHARCZYK, ROMAN
Applicants: DU PONT, GEE STEPHEN KENNETH, HANAGAN MARY ANN, HONG WONPYO, KUCHARCZYK ROMAN, E.I. DU PONT DE NEMOURS AND COMPANY, GEE, STEPHEN, KENNETH, HANAGAN, MARY, ANN, HONG, WONPYO, KUCHARCZYK, ROMAN
Application year: 1996
Main classification: C07D335
IPC codes: A01N43, C07D279, C07D333, C07D335, C07D401, C07D403, C07D405, C07D409