WO1997003045A1

WO1997003045A1 - Herbicidal sulfonamides

Info

Publication number: WO1997003045A1
Application number: PCT/US1996/011345
Authority: WO
Inventors: Thomas Martin Stevenson; Kanu Maganbhai Patel
Original assignee: E.I. Du Pont De Nemours And Company
Priority date: 1995-07-10
Filing date: 1996-07-03
Publication date: 1997-01-30
Also published as: EP0850218A1; JPH11509202A; AU6483996A

Abstract

Compounds of formula (I), and their agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein Q is (Q-1) or (Q-2), and R1-R9 and q 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

HERBICIDAL SULFONAMIDES

BACKGROUND OF THE INVENTION

This invention relates to certain herbicidal sulfonamides, 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 551,650 A2 discloses heterocycles of Formula i as herbicides:

wherein, inter alia,

U^a taken together with -C(=O)CHC(=O)- forms a 5- or 6-membered carbocyclic ring;

W^a is CH;

R^1a, R^2a, and R^3a are independently halogen, alkoxy, nitro, alkyl or S(O)_0-2R; and R is alkyl, haloalkyl, or N(alkyl)₂.

The sulfonamides of the present invention are not disclosed therein.

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

or

R¹ and R² are each independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, halogen, cyano, or nitro;

R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, or C₁-C₆ alkoxy; or R³ is phenyl or benzyl, each optionally substituted on the phenyl ring with C₁-C₃ alkyl, halogen, cyano, or nitro;

R⁴ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, or C₃-C₆ haloalkynyl; or

R³ and R⁴ can be taken together as -CH₂CH₂-, -CH₂CH₂CH₂-,

-CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂-, or -CH₂CH₂OCH₂CH₂-, each optionally substituted with 1-2 C₁-C₃ alkyl;

R⁵ is OR¹⁰, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, or halogen; each R⁶ is independently C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio or halogen; or when two R⁴ are attached to the same carbon atom, then said R⁴ pair can be taken together to form -OCH₂CH₂O-, -OCH₂CH₂CH₂O-, -SCH₂CH₂S- or -SCH₂CH₂CH₂S-, each group optionally substituted with 1-4 CH₃;

R⁷ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkoxyalkyl, formyl, C₂-C₆

alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ haloalkylsulfonyl; or

R⁷ is benzoyl or phenylsulfonyl, each optionally substituted with C₁-C₃ alkyl, halogen, cyano, or nitro;

R⁸ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl; or R⁸ is phenyl or benzyl, each optionally substituted on the phenyl ring with C₁-C₃ alkyl, halogen, cyano, or nitro;

R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, halogen, cyano, or nitro;

R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkoxyalkyl, formyl, C₂-C₆

alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C6 alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ haloalkylsulfonyl; or R¹⁰ is benzoyl or phenylsulfonyl, each optionally substituted with C₁-C₃ alkyl, halogen, cyano, or nitro; and

q is 0, 1, 2, 3, or 4.

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, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl. "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 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 CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂,

CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. "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. For example, CH₃S(O), CH₃CH₂S(O),

CH₃CH₂CH₂S(O), (CH₃)₂CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH₃S(O)₂, CH₃CH₂S(O)₂, CH₃CH₂CH₂S(O)₂, (CH₃)₂CHS(O)₂ and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples.

The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. 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 F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms "haloalkoxy", "haloalkylthio", "haloalkylsulfonyl", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkoxy" include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O. Examples of

"haloalkylthio" include CCl₃S, CF₃S, CCl₃CH₂S and ClCH₂CH₂CH₂S. Examples of "haloalkylsulfonyl" include CF₃S(O)₂, CCl₃S(O)₂, CF₃CH₂S(O)₂ and CF₃CF₂S(O)₂.

The total number of carbon atoms in a substituent group is indicated by the " C_i-C_j" prefix where i and j are numbers from 1 to 7. For example, C₁-C₃ alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C₂ alkoxyalkyl designates

CH₃OCH₂; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; 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 CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. Examples of "alkylcarbonyl" include C(O)CH₃, C(O)CH₂CH₂CH₃ and C(O)CH(CH₃)₂. Examples of

"alkoxycarbonyl" include CH₃OC(=O), CH₃CH₂OC(=O), CH₃CH₂CH₂OC(=O), (CH3)₂CHOC(=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.

When a group contains a substituent which can be hydrogen, for example R² or

R⁸, 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 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-1, R⁵ is OR¹⁰, and R¹⁰ 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. The present invention includes mixtures of such tautomers as well as the individual tautomers of compounds of Formula I.

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:

R¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, halogen, cyano, or nitro;

R² is H or halogen;

R³ and R⁴ are each independently H, C₁-C₆ alkyl, C₃-C₆ alkenyl, or

C₃-C₆ alkynyl; or R³ and R⁴ can be taken together as -CH₂CH₂-, -CH₂CH₂CH₂-,

each R⁶ is independently C₁-C₃ alkyl;

R⁸ is H, C₁-C₆ alkyl, or C₃-C₆ alkenyl;

R⁹ is H; and

R¹⁰ is H, formyl, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ haloalkylsulfonyl; or R¹⁰ is benzoyl or phenylsulfonyl, each optionally substituted with C₁-C₃ alkyl, halogen, cyano, or nitro.

Preferred 2. Compounds of Preferred 1 wherein:

R³ and R⁴ are each independently H, C₁-C₄ alkyl, allyl, or propargyl; or R³ and R⁴ can be taken together as -CH₂CH₂-, -CH₂CH₂CH₂-,

R⁵ is OR¹⁰;

R⁷ is H; and

R¹⁰ is H.

Preferred 3. Compounds of Preferred 2 wherein:

Q is Q-1.

Preferred 4. Compounds of Preferred 2 wherein:

Q is Q-2.

Most preferred are compounds of Preferred 3 selected from the group:

5-chloro-2-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-N,N- dimethylbenzenesulf onamide;

5-chloro-N-ethyl-2-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-N- methylbenzenesulfonamide; and

2-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-N,N-dimethyl-5- (trifluoromethyl)benzenesulfonamide.

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 1-10. The definitions of Q, R¹-R¹⁰, and q in the compounds of Formulae I-XIV 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 Formula Id and le correspond to Formula I compounds wherein Q is Q-1 and Q-2 respectively.

Scheme 1 illustrates the preparation of compounds of Formula Id (R⁵ is OR¹⁰ and

R¹⁰ is the same as R⁷ as defined excluding H), whereby a compound of Formula Id

(R⁵ is OH) is reacted with a reagent of Formula II in the presence of a base wherein X¹ is chlorine, fluorine, bromine, acetyloxy (OAc), trifluoromethylsulfonyloxy (OTf), and

R¹⁰ is as previously defined.

Scheme 1

The coupling is carried out by the methods known in the art or by obvious

modifications. For example, see K. Nakumura, et al. WO 95/04054. Scheme 2 illustrates the preparation of compounds of Formula Id (R⁵ is SO₂R¹¹; r is 1 or 2 and R¹¹ is C₁-C₆ alkyl or C₁-C₆ haloalkyl) whereby a compound of

Formula Id (R⁵ is SR¹¹) is reacted with an oxidizing reagent such as m-chloroperoxybenzoic acid, peroxyacetic acid, hydrogen peroxide, peroxytrifluoroacetic acid or potassium peroxymonosulfate. The oxidation is carried out by methods known in the art or obvious modifications of these methods; for example, see S. Pateu, et al.,

The Chemistry of Sulphones and Sulphoxides, John Wiley & Sons.

Scheme 2

Compounds of Formula Id (R⁵ is Nu, Nu is SR¹¹ or OR¹², R¹¹ is as described previously, R¹² is C₁-C₆, haloalkyl or C₂-C₆ alkoxyalkyl) can be prepared by one skilled in the art from a compound of Formula Id (R⁵ is halogen) by treatment with a nucleophile of Formula III (Nu is SR_{1 1} or OR₁₂, M is Na, K or Li) as shown in Scheme 3 using methods documented in the literature or modifications thereof. For example, see P. H. Nelson, et al., Synthesis, (1992), 12, 1287-1291; and S. Miyano, et al, J. Chem.

Soc, Perkin Trans 1, (1976), 1146.

Scheme 3 l

Compounds of Formula Id (R⁵ is halogen) can be prepared by reacting a compound of Formula Id (R⁵ is OH) with a halogenating reagent such as oxalyl chloride or oxalyl bromide (Scheme 4). This conversion is carried out by methods known in the literature or modifications thereof. For example, see S. Muller, et al., WO 94/13619; S.

Muller, et al., DE 4241999-A1.

Scheme 4

Similarly, compounds of Formula le can be prepared by the above methods or obvious modifications of these methods.

Scheme 5 illustrates the preparation of compounds of Formula I, whereby an enol ester of Formula IVa or IVb is reacted with a base such as triethylamine, a catalytic amount of a cyanide source (e.g., acetone cyanohydrin or potassium cyanide), and a catalytic amount of an organic base such as 4-dimethylaminopyridine,

4-pyrrolidinopyridine, 4-methoxypyridine, 4-(4-methylpiperidine)pyridine,

1,5-diazabicyclo[4,3-0]non-5-ene (DBN), 1,8-diazabicyclo[5,4,0]undec-]-ene (DBU) or

1,4-diazabicyclo[2,2,2]octane. This reaction can be carried out in an inert organic solvent such as dichloromethane, acetonitrile or tetrahydrofuran at 20 to 50 °C, preferably at 20 °C.

Scheme 5

Enol esters of Formula IVa can be prepared by reacting an acid of Formula VI with 2-chloro-1-methylpyridinum iodide (VII) and a dione of Formula Va in the presence of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 and 110 °C (Scheme 6). Enol esters of Formula IVb can be prepared by an anlogous manner from acid VI and hydroxypyrazole Vb. This type of reaction is known in the art. For example, see E. Itaslam, Tetrahedron (1976), 36, 2409-2433. Scheme 6

wherein Q is Q-1

wherein Q is Q-2

Scheme 7 illustrates the preparation of acids of Formula VI, whereby an ester of Formula VIII is treated with a base such as sodium hydroxide, lithium hydroxide or potassium hydroxide in water and an alcohol such as methanol or ethanol at temperatures between 0 and 100 °C, to provide the salt of the acid which can then be converted to the carboxylic acid by acidification. Scheme 7

The compounds of Formula VIII can be prepared from substituted saccharin derivatives (IX). Scheme 8 illustrates the preparation of esters of Formula VIII, whereby a saccharin derivative of Formula IX is reacted with a reagent of Formula X in the presence of sodium methoxide, wherein X² is chlorine, bromine or SO₄R⁴.

Scheme 8

The Scheme 9 illustrates the preparation of compounds of Formula IX, whereby a compound of Formula XI is reacted with a reagent of Formula XII in the presence of a base wherein X³ is chlorine, bromine or SO4R³.

Scheme 9

XI

The synthesis of the compounds of Formula XI (saccharin derivatives are well documented in the art; for example, see Engberts et al., Jour. Am. Chem. Soc. (1979), 101, 6981-6992; D.J. Hlasta et al., Tetrahedron (1991); Letters 32 7179-7182. The saccharin derivatives can be prepared by following these methods or obvious modifications thereof.

The compounds of Formula XIII wherein R³ and R⁴ are taken together as described in the Summary of the Invention can be prepared as illustrated in Scheme 10. A compound of Formula XIV can be reacted with a cyclic secondary amine such as aziridine, azetidine, pyrrolidine, morpholine or piperidine.

Scheme 10

The compounds of Formula XIV can be prepared by methods known in the art (or by obvious modifications of these methods). For example, see W.S. Saari and J.E. Schwering (1986), J. Heterocyclic Chem. 23, 1253-1255.

The compounds of Formula le can be prepared by one skilled in the art by the methods described above (or by obvious modifications of these methods).

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.

1H NMR spectra are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, dt = doublet of triplets, br s = broad singlet.

EXAMPLE 1

Step A: Preparation of 6-chloro-2-ethyl- 1,2-benzisothiazol-3(2H)-one 1,1- dioxide

Sodium hydride (7.5 g, 50% in oil) was added in portions over 30 minutes to a solution of 5-chlorosaccharin (32.61 g) dissolved in dimethylformamide (150 mL). After 30 minutes at 20 °C, iodoethane (15 mL) was added in portions and the mixture was heated at 60 °C for 5 hours and then allowed to stir at room temperature for 18 hours. Water (500 mL) was added and the resulting solids were collected, washed with water (200 mL), and dried to yield 33 g of the title compound of Step A.

1H NMR (400 MHz, CD₃SOCD₃): δ1.34 (t,3H), 3.8 (q,2H); 8.0 (m,2H), 8.6 (s,1H). Step B: Preparation of methyl 4-chloro-2-[(ethylmethylamino)sulfonynbenzoate

A solution of 9.25 g of the title compound of Step A was dissolved in

dimethylformamide (100 mL) and cooled to 5 °C (ice bath). A solution of sodium methoxide in methanol (23.5 mL, 1 M in methanol) was added dropwise and the reaction was allowed to stir at 5 °C for an additional 15 minutes. Dimethylsulfate ( 11.4 mL) was added dropwise and the mixture was stirred at 25 °C for 2 hours. Cold water (500 mL) was added and the resulting solids were collected by filtration. The solids were washed with water and hexane (100 mL each) and air dried to provide 9 grams of the title compound of Step B melting at 85-91 °C.

1H NMR (400 MHz, CDCl₃): δ 1.2 (t,3H), 2.87 (s,3H), 3.29 (q,2H), 3.94 (s,3H), 7.46 (d,1H), 7.56 (d,1H), 7.8 (s,1H).

Step C: Preparation of 4-chloro-2[(ethylmethylamino)sulfonyl]benzoic acid

To a suspension of 6 grams of the title compound of Step B in 50 mL of methanol was added 10 mL of a 50% aqueous solution of sodium hydroxide. The mixture became clear and stirring was continued at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in 20 mL of water, acidified with concentrated hydrochloric acid, and extracted with 3 × 10 mL of ethyl acetate. The ethyl acetate extracts were combined, dried over MgSO₄ and concentrated under reduced pressure to give 4.5 grams of the title compound of Step C as a solid melting at 115-121 °C.

¹H NMR (400 MHz, CDCl₃): δ 1.17 (t,3H); 2.89 (s,3H), 3.32 (q,2H); 7.62 (m,2H),

7.9 (s,1H).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 4-chloro-2- [(ethylmethylamino)sulfonyl]benzoate

To a solution of 2.77 g of the title compound of Step C in 100 mL of

dichloromethane was added 3.1 g of 2-chloro-1-methylpyridinium iodide, 1.4 g of cyclohexanedione, and 5 mL of triethylamine. The mixture was stirred at room temperature for 18 hours, then 20 mL of 1M hydrochloric acid was added, and the mixture was extracted with 2 × 50 mL of dichloromethane. The dichloromethane extracts were combined, dried over MgSO₄ and concentrated under reduced pressure.

The residue was flash chromatographed on silica gel using hexane:ethyl acetate (1:1) to provide 1.33 g of title compound of Step D as a yellow oil.

1H NMR (400 MHz, CDCl₃): δ 1.16 (t,3H), 2.2 (m,2H), 2.5 (m,2H), 2.8 (m,2H), 2.89

(s,3H), 3.3 (q,2H), 6.09 (s,1H), 7.6 (m,2H), 7.8 (s, 1H).

Step E: Preparation of 5-chloro-N-ethyl-2-[2(hydroxy-6-oxo-1-cyclohexen-1- yl)carbonyl]-N-methylbenzenesulfonamide

To a solution of 1.12 g of the title compound of Step D in 20 mL of acetonitrile was added 0.9 mL of triethylamine, 0.045 g of 4-pyrrolidinopyridine, and 3 drops of acetone cyanohydrin and the mixture was stirred under a nitrogen atmosphere for

14 hours. The mixture was concentrated under reduced pressure and the residue was suspended in 10 mL of 1M ΝaOH and extracted with 2 x 10 mL of diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with 2 × 25 mL dichloromethane. The dichloromethane extracts were combined, dried over

MgSO₄, filtered, and concentrated under reduced pressure to provide 0.8 g of the title compound of Step E as a oil.

1H ΝMR (400 MHz, CDCl₃): 6 1.14 (t,3H), 2.0 (m,2H), 2.4 (m,2H), 2.69 (m,2H),

2.7 (s,3H), 3.19 (q,2H), 7.2 (d,1H), 7.6 (d,1H), 7.75 (s,1H).

EXAMPLE 2

Step A: Preparation of methyl 4-chloro-2-ri(pyrrolidinyl)sulfonyl]benzoate

A 10 g suspension of methyl 4-chloro-2-thiobenzoate (e.g., L. Katz, et al., J. Org.

Chem. (1953) 1380-1395) in 80 mL of propionic acid and 2 mL water was cooled to

0 °C; 12.6 mL of condensed chlorine was added dropwise with stirring over 30 minutes. After stirring at 0 °C for 30 minutes, the mixture was poured onto 300 mL of ice cold water, and the resulting oil was collected, dissolved in 50 mL of

dichloromethane, and cooled to -30 °C. 10 mL of pyrrolidine was added dropwise and the reaction was allowed to stir for 30 minutes. Water (100 mL) was added and the mixture was extracted with 2 × 25 mL dichloromethane. The dichloromethane extracts were combined, dried over MgSO₄ and concentrated under reduced pressure to give

6.2 g of title compound of Step A as a solid melting at 109-111 °C.

¹H NMR (400 MHz, CDCl₃): 6 1.9 (m, 4H); 3.41 (m,4H), 3.94 (s,3H), 7.46 (d,1H), 7.55 (d,1H), 7.87 (s,1H).

Step B: Preparation of 4-chloro-2-[(1-pyrrolidinyl)sulfonyl]benzoic acid

A solution of 4.93 g of the title compound of Step A in 50 mL methanol was treated with 9 mL of a 50% aqueous sodium hydroxide solution and refluxed for 5 hours. The reaction was cooled to room temperature, 100 mL water was added, and the solution was acidified with concentrated hydrochloric acid and extracted with 3 x 25 mL dichloromethane. The dichloromethane extracts were combined, dried over MgSO₄, filtered, and the filtrate was concentrated under reduced pressure to leave 4.0 g of title compound of Step B as a solid melting at 158-160 °C.

IH NMR (400 MHz, CDCl₃): δ 1.9 (m,4H), 3.4 (m,4H); 6.8 (b,s1H), 7.6 (m,2H), 7.95 (s,1H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 4-chloro-2-[1- (pyrrolidinyl)sulfonyl]benzoate

To a solution of 3.78 g of the title compound of Step B in 50 mL dichloromethane was added 3.98 g of 2-chloro-1-methylpyridinium iodide. After 5 minutes, 4.4 mL of triethylamine and 1.75 g of cyclohexane-dione were added and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue was flash chromatographed using ethyl acetate as a solvent to provide 3.13 g of the title compound of the Step C as a solid melting at 82-86 °C.

¹H NMR (400 MHz, CDCl3): δ 1.9 (m,4H), 2.2 (m,2H), 2.4 (m,2H), 2.8 (m,2H), 3.39 (m,4H), 6.12 (s,1H), 7.6 (m,2H), 7.95 (s,1H).

Step D: Preparation of 1-[[5-chloro-2-[(2-hydroxy-6-oxo-1-cyclohexen-1- yl)carbonyl]phenyl]sulfonyl]pyrrolidine

To a 1.5 g solution of compound of the Step C in 15 mL of acetonitrile were added

1.3 mL of triethylamine, 0.06 g of 4-pyrrolidinopyridine, and 3 drops of acetone cyanohydrin. The mixture was then stirred under nitrogen for 15 hours. An additional 0.04 g of 4-pyrrolidinopyridine and 1 drop of acetone cyanohydrin were added and the reaction was stirred for another 15 hours. The mixture was concentrated under reduced pressure and the residue was flash chromatographed using silica gel and ethyl acetate as a solvent to provide 0.6 g of title compound of Step D as a oil.

1H NMR (400 MHz, CDCl₃): d 1.82 (m,4H), 2.0 (m,2H), 2.4 (m,2H), 2.8 (m,2H),

3.4 (m,4H), 7.2 (m,1H), 7.35 (m,1H), 7.87 (s,1H). By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 5 can be prepared. The following abbreviations are used in the Tables which follow: Ph = phenyl and CN = cyano.

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.

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/polyoxypropylene 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 and B.

Example A

Example B

Example C

Example D

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, clopyralid, 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, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethyl α,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-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, flazasulfuron, 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 299 263), 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-1H,3H-[1,3,4]thiadiazolo[3,4-α]pyridazin-1-ylidene)amino]phenyl]thioacetate (KIΗ 9201), methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate (AKΗ-7088), methyl 5-[[[[(4,6-dimethyl-2-pyrirmdinyl)amino]carbonyl]amino]sulfonyl]-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin,

metsulfuron-mefhyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, 3-oxetanyl 2-[[[[(4,6-dimethyl-2-pyrirmidinyl)amino]carbonyl]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-tefuryl, 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.

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 and B for compound

descriptions. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.

BIOLOGICAL EXAMPLES OF THE INVENTION

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), 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 (-) indicates no test result.

TEST B

The compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and was 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) and/or to water that covered the soil surface (flood 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 (Xαnthium 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 hede raced), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutϊlon theophrasti), 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 limosd), barnyardgrass (Echinochloa crus-galli) and Late watergrass (Echinochloa oryzicola) grown to the 2 leaf (2 If) 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 to the test compound is summarized in Table B, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) indicates no test result.

Claims

CLAIMS What is claimed is:

1. A compound selected from Formula I, and agriculturally suitable salts thereof,

wherein

Q is

R or

R³ and R⁴ can be taken together as -CH₂CH₂-, -CH₂CH₂CH₂-,

-CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂-, or -CH₂CH₂OCH₂CH₂-, each optionally substituted with 1-2 C₁-C₃ alkyl; R⁵ is OR¹⁰, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, or halogen; each R⁶ is independently C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio or halogen; or when two R⁴ are attached to the same carbon atom, then said R⁴ pair can be taken together to form -OCH₂CH₂O-, -OCH₂CH₂CH₂O-, -SCH₂CH₂S- or -SCH₂CH₂CH₂S-, each group optionally substituted with 1-4 CH₃;

alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ haloalkylsulfonyl; or R⁷ is benzoyl or phenylsulfonyl, each optionally substituted with C₁-C₃ alkyl, halogen, cyano, or nitro;

R⁹ is H, C₁-C₆ alkyl, C₁-C6 haloalkyl, halogen, cyano, or nitro;

alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-CG alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ haloalkylsulfonyl; or R¹⁰ is benzoyl or phenylsulfonyl, each optionally substituted with C₁-C₃ alkyl, halogen, cyano, or nitro; and

q is 0, 1, 2, 3, or 4.

2. A compound of Claim 1 wherein:

-CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂-, or

-CH₂CH₂OCH₂CH₂-, each optionally substituted with 1-2 C₁-C₃ alkyl;

R⁵ is OR¹⁰;

R⁷ is H; and

R¹⁰ is H.

3. A compound of Claim 2 wherein:

Q is Q-l.

4. A compound of Claim 2 wherein:

Q is Q-2.

5. A compound of Claim 3 which is selected from the group:

5-chloro-2-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-N,N- dimethylbenzenesulfonamide; 5-chloro-N-ethyl-2-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-N- methylbenzenesulfonamide; and

6. 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 liquid diluent.

7. 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.

8. A process for the preparation of compounds of Formula I which comprises contacting compounds of Formula IVa or Formula IVb

with a base, a catalytic amount of a cyanide source, and a catalytic amount of an organic base chosen from the group 4-dimethylaminopyridine, 4-pyrrolidinopyridine,

4-methoxypyridine, 4-(4-methylpiperidine)pyridine, 1,5-diazabicyclo[4,3-0]non-5-ene (DBN), 1,8-diazabicyclo[5,4,0]undec-]-ene (DBU), and 1,4-diazabicyclo[2,2,2]octane.