WO1998049159A1 - Herbicidal pyrazoles - Google Patents

Abstract

Compounds of formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein Q, A, and R1-R5 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 PYRAZOLES BACKGROUND OF THE INVENTION This invention relates to certain pyrazoles, 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.

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:

I wherein

A is -OC(=O)-, -OC(=O)O- or -OC(=O)S-, and the directionality of the A linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the pyrazole ring and the moiety on the right side of the linkage is bonded to Q;

Q is C C_jo alkyl optionally substituted with halogen, C2-Cg alkoxyalkyl, C₂-Cιo alkenyl or C3-C6 cycloalkyl; or Q is phenyl, benzyl, pyridyl, furanyl or thienyl, each optionally substituted with C1 -C3 alkyl, Cj-C₃ alkoxy, cyano, halogen, COOH or S(=O)₂OH; or

A together with Q is -OC(=O)NR⁶R⁷;

R¹ is C_rC₃ alkyl;

R² and R³ are each independently H, Ci -C₃ alkyl or halogen; R⁴ and R⁵ are taken together to form -O(CH₂)₂O-; or R⁴ and R⁵ are taken together with the carbon to which they are attached to form C(=O); R⁶ is C_j-C_β alkyl, C3-C4 alkenyl or phenyl optionally substituted with 1-3 Cj-C alkyl, C _j-C₃ alkoxy, halogen or cyano; R⁷ is C1-C3 alkyl or C3-C4 alkenyl; or

R⁶ and R⁷ are taken together to form -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂- or

-CH₂CH₂OCH₂CH₂-; provided that when A is -OC(=O)- and R⁴ and R⁵ are taken together to form -O(CH₂)₂O-, then Q is other than C_rC₂ alkyl. 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, «-propyl, /-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 which are independently selected. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 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 ethynyl, 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, rc-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "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. 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, C1CH₂, CF₃CH₂ and CF₃CC1₂. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl".

The total number of carbon atoms in a substituent group is indicated by the "Cj-C;" prefix where i and j are numbers from 1 to 10. 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. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to - these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

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. (RM, 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 R² or R³, 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.

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 a carboxylic acid or phenol.

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

R⁴ and R⁵ are taken together to form -O(CH₂)₂O-. Preferred 2. Compounds of Preferred 1 wherein

Q is C1-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C_j-C3 alkyl, C1-C3 alkoxy, cyano or halogen; and

R² and R³ are each independently C1-C3 alkyl. Preferred 3. Compounds of Preferred 2 wherein A is -OC(=O)O-. Preferred 4. Compounds of Formula I above, and agriculturally suitable salts thereof, wherein

R⁴ and R⁵ are taken together to form C(=O). Preferred 5. Compounds of Preferred 4 wherein Q is C1-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C_j-C3 alkyl, C1-C3 alkoxy, cyano or halogen; and R² and R³ are each independently C₁-C3 alkyl. Preferred 6. Compounds of Preferred 5 wherein A is -OC(=O)O-. Most preferred are compounds of Formula I selected from the group:

(^a) [4-[(2,3-dihydro-5,8-dimethylspiro[4H- 1 -benzothiopyran-4,2 '-[1 ,3]dioxolan]-6- yl)carbonyl]-l-ethyl-lH-pyrazol-5-yl] (1-methylethyl) carbonate S,S-dioxide;

(b) [4-[(3,4-dihydro-5,8-dimethyl- 1 , 1 -dioxido-4-oxo-2H- 1 -benzothiopyran-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] methyl carbonate; (c) [4-[(3 ,4-dihydro-5 ,8-dimethyl- 1 , 1 -dioxido-4-oxo-2H- 1 -benzothiopyran-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] (1-methylethyl) carbonate; (d) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-l-benzothiopyran-4,2'-[l,3]dioxolan]-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] ethyl carbonate S,S-dioxide;

(e) [5-(benzoyloxy)- 1 -ethyl- lH-pyrazol-4-yl](2,3-dihydro-5,8-dimethylspiro[4H- 1 - benzothiopyran-4,2'-[l,3]dioxolan]-6-yl)methanone S,S-dioxide;

(f) [4-[(3,4-dihydro-l,l-dioxido-4-oxo-5,8-dimethyl-2H-benzothiopyran-6- yl)carbonyl]- 1 -ethyl- 1 H-pyrazol-5-yl] cyclopropanecarboxylate; and

(g) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-l -benzothiopyran-4,2 '-[l,3]dioxolan]-6- yl)carbonyl]- 1 -ethyl- lH-pyrazol-5-yl] cyclopropanecarboxylate S,S-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 Scheme 1. The definitions of Q and R!-R⁷ in the compounds of Formulae 1-5 below are as defined above in the Summary of the Invention.

Scheme 1 illustrates the preparation of compounds of Formula I whereby a compound of Formula 1 is reacted with the appropriate reagent of Formula 2, 3, A, and 5 in the presence of a suitable base. This coupling method is carried out by general methods known in the art; see, for example, Nakamura, et al., WO 95/04054.

Scheme 1

Compounds of Formula 1 can be prepared by methods described in the art; see, for example, Tseng, WO 97/01550. Compounds of Formulae 2, 3, 4, and 5 are either commercially available or can be prepared by methods well-established in the art from commercially available starting materials.

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. ^lH 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 3-[(2,5-dimethylphenyl)thiolpropanoic acid

43.4 g (1.086 mol) of sodium hydroxide was added to 230 niL of water, 75.0 g (0.543 mol) of 2,5-dimethylthiophenol (purchased from Aldrich Chemical Company) was then added and the mixture was cooled to about 10 °C. 91.30 g (0.597 mol) of 3-bromopropionic acid (purchased from Aldrich Chemical Company) was added in portions while keeping the temperature below 25 °C. The mixture was warmed to room temperature, stirred for 2 h under nitrogen, and was then washed with diethyl ether (3 x 500 mL). The aqueous layer was acidified with IN HC1 and filtered to yield 112.79 g of the title compound of Step A as a solid melting at 97-98 °C. ^!H NMR (CDC1₃): δ 2.3 (s,3H), 2.34 (s,3H), 2.68 (t,2H), 3.1 (t,2H), 6.9 (d,lH), 7.06-7.14 (2H). Step B: Preparation of 2 ,3 -dihvdro-5 , 8-dimethyl-4H- 1 -benzopyran-4-one

530 mL of concentrated sulfuric acid was added to 24.91 g (0.1 19 mol) of the title compound of Step A while being cooled with an acetone/ice bath. The ice bath was removed, the mixture was stirred for 1 h and was then poured over crushed ice. The aqueous mixture was extracted with a 1 : 9 mixture of diethyl ether : hexane (6 x 500 mL), dried (MgSO4), filtered, and evaporated to dryness to yield 11.75 g of the title compound of Step B as an oil. ^lΗ NMR (CDCI3): δ 2.3 (s,3Η), 2.6 (s,3H), 2.97 (m,2H), 3.2 (m,2H), 6.9-7.1 (2H). Step C: Preparation of 6-bromo-2.3-dihvdro-5,8-dimethyI-4H- 1 -benzothiopyran-4-one

A solution of 4.07 g (0.021 mol) of the title compound of Step B in 25 mL of methylene chloride was added dropwise to a mixture of 7.07 g (0.053 mol) of aluminum chloride (purchased from Aldrich Chemical Company) and 25 mL of methylene chloride. The suspension was stirred for approximately 15 minutes, 1.14 mL (0.022 mol) of bromine (purchased from Janssen) was added dropwise, and the mixture was refluxed for 10 minutes. The warm mixture was poured into 10 mL of concentrated hydrochloric acid containing 75 g of ice, stirred for 10 minutes, diluted with 50 mL of water, and then extracted with diethyl ether (2 x 200 mL). The combined organic layers were washed with water (2 x 200 mL), dried (Na₂SO4), filtered, and evaporated to dryness. The crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate : hexane (5% : 95%) to yield 2.62 g of the title compound of Step C as a solid melting at 87-88 °C. ^!Η NMR (CDCI3): δ 2.3 (s,3H), 2.6 (s,3H), 3.0 (m,2H), 3.2 (m,2H), 7.45 (s,lH). Step D: Preparation of 6-bromo-2,3-dihvdro-5,8-dimethylspiro[4H-l-benzothiopyran-

4.2'-π.31dioxolanel 26.06 g (0.096 mol) of the title compound of Step C, 250 mL of ethylene glycol, 170 mL of trimethyl orthoformate (purchased from Aldrich Chemical Company), and 0.06 g of ?-toluenesulfonic acid monohydrate were stirred together at 80 °C under nitrogen overnight. The mixture was diluted with 400 mL of diethyl ether. The resulting mixture was washed with a 1 : 1 mixture of IN sodium hydroxide: saturated aqueous ΝaCl (2 x 600 mL) and then with saturated aqueous ΝaCl (1 x 600 mL). The organic layer was dried (Νa₂S0₄), filtered, and evaporated to dryness. The crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate : hexane (1 : 9) to yield 24.73 g of the title compound of Step D as a solid melting at 97 °C (dec). ^JH NMR (CDC1₃): δ 2.2 (s,3H), 2.3 (m,2H), 2.4 (s,3H), 3.0 (m,2H), 4.15 (m,2H), 4.3 (m,2H), 7.3 (s,lH).

Step E: Preparation of 2,3-dihydro-5, 8-dimethylspiro|^"4H-l -benzothiopyran-4.2'-

[T ,3^~|dioxolane1-6-carboxylic acid 24.73 g (0.078 mol) of the title compound of Step D was added to 150 mL of tetrahydrofuran. The solution was cooled to about -70 ° under nitrogen and 37.68 mL (0.094 mol) of 2.5M n-butyllithium in hexane was added dropwise while keeping the temperature below -65 °C. After stirring for 1 h, carbon dioxide was bubbled into the mixture for 2 h. The mixture was allowed to warm to room temperature, 300 mL of hexanes were added, and the resulting mixture was filtered. The resulting solid was added to a mixture of water : methylene chloride (400 mL : 400 mL), cooled to about 0 °C, and acidified to pΗ 1 with concentrated hydrochloric acid. The layers were separated and the aqueous layer was extracted with diethyl ether (2 x 300 mL). The combined organic layers were dried (MgSO₄), filtered, and evaporated to dryness to yield 4.73 g of the title compound of Step E as a solid melting at 207-208 °C. Η NMR (Me₂SO-^₆): δ 2.2 (m,5Η), 2.4 (s,3H), 3.0 (m,2H), 4.1-4.2 (m,4H), 7.4 (s,lH).

Step F: Preparation of 2,3-dihvdro-5,8-dimethylspirof4H-l-benzothiopyran-4,2'- π,3^~|dioxolane^"l-6-carboxylic acid 1,1 -dioxide 4.73 g (0.017 mol) of the title compound of Step E and 2.08 g (0.025 mol) of sodium acetate were added to 85 mL of methanol. The solution was cooled to about 0 °C, and a solution of 17.66 g (0.029 mol) of OXONE® (purchased from Aldrich Chemical Company) in 85 mL of water was added dropwise while keeping the temperature below 6 °C. The mixture was warmed to room temperature and stirred under nitrogen overnight. The mixture was diluted with 50 mL of water, cooled to about 0 °C, acidified to around pΗ 2 with concentrated hydrochloric acid, and then extracted with chloroform (3 x 150 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to dryness. The residue was triturated in diethyl ether : hexane (1 : 9) which was decanted to yield 4.18 g of the title compound of Step F as a solid melting at 185 °C (dec). ^lϊl NMR (Me₂SO-^): δ 2.35 (s,3H), 2.5 (m,2H), 2.6 (s,3H), 3.5 (m,2H), 4.16 (m,2H), 4.2 (m,2H), 7.6 (s,lH). Step G: Preparation of l-ethyl-lH-pyrazol-5-yl 2,3-dihvdro-5,8-dimethylspiror4H-l- benzothiopyran-4,2'-[T ,31dioxolane1-6-carboxylate 1 , 1 -dioxide 1.18 g (3.8 mmol) of the title compound of Step F, 0.99 mL (0.01 1 mol) of oxalyl chloride (purchased from Janssen), and 2 drops of N_^/V-dimethylformamide were added to 50 mL of methylene chloride. The mixture was refluxed under nitrogen for 2 h, and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and the resulting mixture was evaporated to dryness. Another 50 mL of methylene chloride was added to the residue, and the solution was cooled to about 0 °C. 0.51 g (4.5 mmol) of 1- ethyl-lH-pyrazol-5-ol was added followed by 1.63 mL (0.012 mol) of triethylamine, and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness and the crude product was chromatographed eluting with a mixture of ethyl acetate : hexane (6 : 4) to yield 0.24 g of the title compound of Step G as a semi-solid. ^JΗ NMR (CDC1₃): δ 1.4 (t,3H), 2.5 (s,3H), 2.6 (m,2H), 2.8 (s,3H), 3.5 (m,2H), 4.1-4.4 (m,6H), 6.26 (s,lH), 7.5-7.7 (2H).

Step H: Preparation of (2,3-dihvdro-5,8-dimethylspiror4H-l-benzothiopyran-4,2'-

I^" 1 ,31dioxolan1-6-yl)f 1 -ethyl-5-hvdroxy- lH-pyrazol-4-yl)methanone S.S- dioxide 0.24 g (0.59 mmol) of the title compound of Step G, 0.25 drops of acetone cyanohydrin (purchased from Aldrich Chemical Company), and 0.14 mL (1.0 mmol) of triethylamine were added to 25 mL of acetonitrile and the mixture was allowed to stir at room temperature under nitrogen for 1.5 h. About 0.06 g of potassium cyanide was added to the mixture which then was stirred at room temperature overnight. The mixture was evaporated to dryness and water was added to the residue. The resulting mixture was acidified to pΗ 1 with concentrated hydrochloric acid and extracted with methylene chloride (2 x 50 mL). The combined organic layers were dried (MgSO₄), filtered, and evaporated to dryness to yield 0.17 g of the title compound of Step Η as a solid melting at 111 °C (dec). ^!Η NMR (CDCI3): δ 1.46 (t,3H), 2.3 (s,3H), 2.6 (m,2H), 2.8 (s,3H), 3.5 (m,2H), 4.1 (q,2H), 4.2-4.3 (m,4H), 7.3 (2H).

Step I: Preparation of [4- \(2 ,3 -dihydro-5 , 8-dimethylspiro \4H- 1 -benzothiopyran.4,2 '- fl ,31dioxolanl-6-yl)carbonyl]-l -ethyl- lH-pyrazol-5-yll (1-methylethyl) carbonate S,S-dioxide 500 mg (1.23 mmol) of the title compound of Step Η and 1.50 ml (1.50 mmol) of isopropylchloroformate (1.0 solution in toluene; purchased from Aldrich Chemical Co.) were added to acetonitrile, followed by the addition of 0.220 ml (1.56 mmol) of triethylamine. The solution was stirred under nitrogen at room temperature overnight. The mixture was evaporated to dryness and chromatographed over silica gel, eluting with a mixture of 33% hexanes in ethyl acetate to yield 440 mg of the title compound of Step I, a compound of this invention, as a yellow solid melting at 168-170 °C. ^JH NMR (CDC1₃): δ 1.4 (m, 9H), 2.3 (s, 3H), 2.6 (m, 2H), 2.8 (s, 3H), 3.5 (m, 2H), 4.1 (m, 4H), 4.3 (m, 2H), 5.0 (q, 1H), 7.2 (s, 1H), 7.5 (s, 1H). EXAMPLE 2

Step A: Preparation of r4-F(2,3-dihvdro-5,8-dimethylspiror4H-l-benzothiopyran,4,2'-

[l,31dioxolanl-6-yl)carbonyl]-l-ethyl-lH-pyrazol-5-vn ethyl carbonate S,S- dioxide 400 mg (1.00 mmol) of the title compound of Step Η in Example 1 was added to acetonitrile and cooled to -78 °C. To the cooled solution was added 0.115 ml (1.20 mmol) of ethyl chloroformate (purchased from Aldrich Chemical Co.), followed by the addition of 0.175 ml (1.26 mmol) of triethylamine. The solution was allowed to warm to ambient temperature and stirred under nitrogen overnight. The mixture was concentrated to dryness under reduced pressure and chromatographed over silica gel, eluting with a mixture of 50% hexanes in ethyl acetate. The title compound of Step A, a compound of this invention, was isolated as a solid with a melting point of 201-203 °C. ^JΗ NMR (CDC1₃): δ 1.43 (m, 6H), 2.28 (s, 3H), 2.60 (m, 2H), 2.76 (s, 3H), 3.55 (m, 2H), 4.0- 4.4 (m, 8H), 7.20 (s, 1H), 7.56 (s, 1H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 4 can be prepared.

Table 1

Rl R^ E A Q

CH₃ H H -OC(=O)O- CH₃

CH₃ CH₃ H -OC(=O)O- CH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH-3

CH₃ CH₃ Cl -OC(=O)O- CH₃

CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₃ Cl Cl -OC(=O)O- CH₃

CH₃ H H -OC(=O)S- CH₃ CH₃ CH₃ H -OC(=O)S- CH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH₃

CH₃ CH₃ Cl -OC(=O)S- CH₃

CH₃ Cl CH₃ -OC(=O)S- CH₃

CH₃ Cl Cl -OC(=O)S- CH₃

CH₂CH₃ H H -OC(=O)O- CH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH₃

CH₂CH₃ H H -OC(=O)S- CH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH₃

CH₂CH₂CH₃ H H -OC(=O)O- CH₃

CH₂CH CH3 CH₃ H -OC(=O)O- CH₃

CH₂CH CH₃ CH₃ CH₃ -OC(=O)O- CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)O- CH₃

CH₂CH₂CH3 H H -OC(=O)S- CH₃

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₃

CH₂CH CH3 CH₃ Cl -OC(=O)S- CH₃

CH₂CH CH3 Cl CH₃ -OC(=O)S- CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)S- CH₃

CH₃ H H -OC(=O)O- CH₂CH₃

CH₃ CH₃ H -OC(=O)O- CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₃

CH₃ CH₃ Cl -OC(=O)O- CH₂CH₃

CH₃ Cl CH₃ -OC(=O)O- CH₂CH₃

CH₃ Cl Cl -OC(=O)O- CH₂CH₃

CH₃ H H -OC(=O)S- CH₂CH₃

CH₃ CH₃ H -OC(=O)S- CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₃ CH₃ CH₃ Cl -OC(=O)S- CH₂CH₃

CH₃ Cl CH₃ -OC(=O)S- CH₂CH₃

CH₃ Cl Cl -OC(=O)S- CH₂CH₃

CH₂CH₃ H H -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₃

CH₂CH₃ H H -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 H H -OC(=O)O- CH₂CH₃ H₂ H₂ H3 CH₃ H -OC(=O)O- CH₂CH₃

CH₂CH₂CH CH₃ CH₃ -OC(=O)O- CH₂CH₃ H H₂CH3 CH₃ Cl -OC(=O)O- CH₂CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₃

CH₂CH₂CH3 H H -OC(=O)S- CH₂CH₃ H₂ H₂ H3 CH₃ H -OC(=O)S- CH₂CH₃

CH CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH₂CH₃

CH CH₂CH3 Cl Cl -OC(=O)S- CH₂CH₃

CH₃ H H -OC(=O)O- CH₂CH₂CH3

CH₃ CH₃ H -OC(=O)O- CH₂CH₂CH3

CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₂CH

CH₃ CH₃ Cl -OC(=O)O- CH₂CH₂CH₃

CH₃ Cl CH₃ -OC(=O)O- CH₂CH₂CH3

CH₃ Cl Cl -OC(=O)O- CH₂CH₂CH3

CH₃ H H -OC(=O)S- CH₂CH₂CH3

CH₃ CH₃ H -OC(=O)S- CH₂CH₂CH3

CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₂CH3

CH₃ CH₃ Cl -OC(=O)S- CH₂CH₂CH

CH₃ Cl CH₃ -OC(=O)S- CH₂CH₂CH CH₃ Cl Cl -OC(=O)S- CH₂CH₂CH3

CH₂CH₃ H H -OC(=O)O- CH₂CH₂CH3

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH₂CH3

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH CH₂CH₃

CH₂CH₃ H H -OC(=O)S- CH₂CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH₂CH

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₂CH3

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH₂CH

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH₂CH₃

CH₂CH₂CH3 H H -OC(=O)O- CH₂CH₂CH₃

CH₂CH₂CH3 CH₃ H -OC(=O)O- CH₂CH₂CH

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- CH₂CH₂CH3

CH₂CH₂CH CH₃ Cl -OC(=O)O- CH₂CH₂CH3

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- CH₂CH₂CH3

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₂CH3

CH₂CH₂CH₃ H H -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH₂CH₂CH₃

CH₂CH CH3 CH₃ CH₃ -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH Cl CH₃ -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH₂CH3

CH₃ H H -OC(=O)O- cyc/t>-propyl

CH₃ CH₃ H -OC(=O)O- cyclo-propyl

CH₃ CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₃ Cl Cl -OC(=O)O- cyc/o-propyl

CH₃ H H -OC(=O)S- ςyc/o-propyl

CH₃ CH₃ H -OC(=O)S- cyc/o-propyl

CH₃ CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)S- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₃ Cl Cl -OC(=O)S- cyc/o-propyl

CH₂CH₃ H H -OC(=O)O- cyc/o-propyl CH₂CH₃ CH₃ H -OC(=O)O- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)O- cyc/o-propyl

CH₂CH₃ H H -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ H -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)S- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)S- cyc/o-propyl

CH₂CH₂CH3 H H -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- cyc/o-propyl

CH₂CH₂CH CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 Cl Cl -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 H H -OC(=O)S- cyc/o-propyl

CH₂CH₂CH₃ CH₃ H -OC(=O)S- cyc/o-propyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- cyc/o-propyl

CH CH₂CH3 Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₂CH₃ Cl Cl -OC(=O)S- cyc/o-propyl

CH₃ H H -OC(=O)O- CH=CH₂

CH₃ CH₃ H -OC(=O)O- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂

CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₃ Cl CH₃ -OC(=O)O- CH=CH₂

CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₃ H H -OC(=O)S- CH=CH₂

CH₃ CH₃ H -OC(=O)S- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)S- CH=CH₂

CH₃ CH₃ Cl -OC(=O)S- CH=CH₂

CH₃ Cl CH₃ -OC(=O)S- CH=CH₂

CH₃ Cl Cl -OC(=O)S- CH=CH₂

CH₂CH₃ H H -OC(=O)O- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)O- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂ CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₂CH₃ H H -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)S- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)S- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)S- CH=CH₂

CH₂CH₂CH₃ H H -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ CH₃ H -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ H H -OC(=O)S- CH=CH₂

CH CH₂CH3 CH₃ H -OC(=O)S- CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH=CH₂

CH CH₂CH3 CH₃ Cl -OC(=O)S- CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH=CH₂

CH CH CH₃ Cl Cl -OC(=O)S- CH=CH₂

CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₃ H H -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- C(=CH₂)CH₃ CH₂CH₃ Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH CH CH3 CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH CH₂CH3 Cl CH₃ -OC(=O)O- C(=CH₂)CH₃

CH CH CH3 Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH3 H H -OC(=O)S- C(=CH₂)CH₃

CH CH₂CH3 CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH CH₂CH3 CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₃ H H -OC(=O)O- CH₂CH=CH₂

CH₃ CH₃ H -OC(=O)O- CH₂CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH₃ CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₃ Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH₃ Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₃ H H -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH₃ Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₃ Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ H H -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ H H -OC(=O)S- CH₂CH=CH₂ CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH CH3 H H -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)O- CH₂CH=CH₂

CH CH₂CH3 CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH₃ H H -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₃ H H -OC(=O)O- CH=CHCH₃

CH₃ CH₃ H -OC(=O)O- CH=CHCH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH₃ CH₃ Cl -OC(=O)O- CH=CHCH₃

CH₃ Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₃ Cl Cl -OC(=O)O- CH=CHCH₃

CH₃ H H -OC(=O)S- CH=CHCH₃

CH₃ CH₃ H -OC(=O)S- CH=CHCH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH=CHCH₃

CH₃ CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₃ Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₃ Cl Cl -OC(=O)S- CH=CHCH₃

CH₂CH₃ H H -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CHCH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH=CHCH₃

CH₂CH₃ H H -OC(=O)S- CH=CHCH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH=CHCH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH=CHCH₃ CH₂CH₃ CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH=CHCH₃

CH₂CH₂CH3 H H -OC(=O)O- CH=CHCH₃

CH₂CH CH CH₃ H -OC(=O)O- CH=CHCH₃

CH₂CH₂CH CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH CH₂CH3 CH₃ Cl -OC(=O)O- CH=CHCH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₂CH3 Cl Cl -OC(=O)O- CH=CHCH₃

CH₂CH₂CH3 H H -OC(=O)S- CH=CHCH₃

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH=CHCH₃

CH₂CH₂CH CH₃ CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₂CH3 Cl Cl -OC(=O)S- CH=CHCH₃

CH₃ H H -OC(=O)O- phenyl

CH₃ CH₃ H -OC(=O)O- phenyl

CH₃ CH₃ CH₃ -OC(=O)O- phenyl

CH₃ CH₃ Cl -OC(=O)O- phenyl

CH₃ Cl CH₃ -OC(=O)O- phenyl

CH₃ Cl Cl -OC(=O)O- phenyl

CH₃ H H -OC(=O)S- phenyl

CH₃ CH₃ H -OC(=O)S- phenyl

CH₃ CH₃ CH₃ -OC(=O)S- phenyl

CH₃ CH₃ Cl -OC(=O)S- phenyl

CH₃ Cl CH₃ -OC(=O)S- phenyl

CH₃ Cl Cl -OC(=O)S- phenyl

CH₂CH₃ H H -OC(=O)O- phenyl

CH₂CH₃ CH₃ H -OC(=O)O- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)O- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)O- phenyl

CH₂CH₃ Cl Cl -OC(=O)O- phenyl

CH₂CH₃ H H -OC(=O)S- phenyl

CH₂CH₃ CH₃ H -OC(=O)S- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)S- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)S- phenyl CH₂CH₃ Cl Cl -OC(=O)S- phenyl

CH₂CH₂CH3 H H -OC(=O)O- phenyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- phenyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- phenyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- phenyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- phenyl

CH₂CH₂CH3 Cl Cl -OC(=O)O- phenyl

CH₂CH₂CH₃ H H -OC(=O)S- phenyl

CH₂CH₂CH CH₃ H -OC(=O)S- phenyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)S- phenyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O)S- phenyl

CH₂CH₂CH Cl CH₃ -OC(=O)S- phenyl

CH₂CH₂CH₃ Cl Cl -OC(=O)S- phenyl

CH₃ H H -OC(=O)O- 2-pyridinyl

CH₃ CH₃ H -OC(=O)O- 2-pyridinyl

CH₃ CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₃ Cl Cl -OC(=O)O- 2-pyridinyl

CH₃ H H -OC(=O)S- 2-pyridinyl

CH₃ CH₃ H -OC(=O)S- 2-pyridinyl

CH₃ CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₂CH₃ H H -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)O- 2-pyridinyl

CH₂CH₃ H H -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ H H -OC(=O)O- 2-pyridinyl CH CH₂CH₃ CH₃ H -OC(=O)O- 2-pyridinyl

CH₂CH₂CH CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH CH3 Cl Cl -OC(=O)O- 2-pyridinyl

CH₂CH₂CH3 H H -OC(=O)S- 2-pyridinyl

CH₂CH₂CH3 CH₃ H -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₂CH₂CH Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₃ H H -OC(=O)O- 2-furanyl

CH₃ CH₃ H -OC(=O)O- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)O- 2-furanyl

CH₃ CH₃ Cl -OC(=O)O- 2-furanyl

CH₃ Cl CH₃ -OC(=O)O- 2-furanyl

CH₃ Cl Cl -OC(=O)O- 2-furanyl

CH₃ H H -OC(=O)S- 2-furanyl

CH₃ CH₃ H -OC(=O)S- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)S- 2-furanyl

CH₃ CH₃ Cl -OC(=O)S- 2-furanyl

CH₃ Cl CH₃ -OC(=O)S- 2-furanyl

CH₃ Cl Cl -OC(=O)S- 2-furanyl

CH₂CH₃ H H -OC(=O)O- 2-furanyl

CH₂CH₃ CH₃ H -OC(=O)O- 2-furanyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-furanyl

CH₂CH₃ CH₃ Cl -OC(=O)O- 2-furanyl

CH₂CH₃ Cl CH₃ -OC(=O)O- 2-furanyl

CH₂CH₃ Cl Cl -OC(=O)O- 2-furanyl

CH₂CH₃ H H -OC(=O)S- 2-furanyl

CH₂CH₃ CH₃ H -OC(=O)S- 2-furanyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-furanyl

CH₂CH₃ CH₃ Cl -OC(=O)S- 2-furanyl

CH₂CH₃ Cl CH₃ -OC(=O)S- 2-furanyl

CH₂CH₃ Cl Cl -OC(=O)S- 2-furanyl

CH₂CH₂CH₃ H H -OC(=O)O- 2-furanyl

CH₂CH₂CH₃ CH₃ H -OC(=O)O- 2-furanyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-furanyl CH₂CH₂CH CH₃ Cl -OC(=O)O- 2-furanyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- 2-furanyl

CH CH₂CH Cl Cl -OC(=O)O- 2-furanyl

CH₂CH CH3 H H -OC(=O)S- 2-furanyl

CH₂CH₂CH3 CH₃ H -OC(=O)S- 2-furanyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- 2-furanyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- 2-furanyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- 2-furanyl

CH₂CH₂CH3 Cl Cl -OC(=O)S- 2-furanyl

CH₃ H H -OC(=O)O- 2-thienyl

CH₃ CH₃ H -OC(=O)O- 2-thienyl

CH₃ CH₃ CH₃ -OC(=O)O- 2-thienyl

CH₃ CH₃ Cl -OC(=O)O- 2-thienyl

CH₃ Cl CH₃ -OC(=O)O- 2-thienyl

CH₃ Cl Cl -OC(=O)O- 2-thienyl

CH₃ H H -OC(=O)S- 2-thienyl

CH₃ CH₃ H -OC(=O)S- 2-thienyl

CH₃ CH₃ CH₃ -OC(=O)S- 2-thienyl

CH₃ CH₃ Cl -OC(=O)S- 2-thienyl

CH₃ Cl CH₃ -OC(=O)S- 2-thienyl

CH₃ Cl Cl -OC(=O)S- 2-thienyl

CH₂CH₃ H H -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ H -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ Cl -OC(=O)O- 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O)O- 2-thienyl

CH₂CH₃ Cl Cl -OC(=O)O- 2-thienyl

CH₂CH₃ H H -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ H -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ Cl -OC(=O)S- 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O)S- 2-thienyl

CH₂CH₃ Cl Cl -OC(=O)S- 2-thienyl

CH₂CH₂CH₃ H H -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- 2-thienyl

CH₂CH CH3 Cl CH₃ -OC(=O)O- 2-thienyl CH₂CH₂CH₃ Cl Cl -OC(=O)O- 2-thienyl

CH₂CH₂CH₃ H H -OC(=O)S- 2-thienyl

CH₂CH CH₃ CH₃ H -OC(=O)S- 2-thienyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-thienyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- 2-thienyl

CH₂CH CH3 Cl CH₃ -OC(=O)S- 2-thienyl

CH₂CH₂CH3 Cl Cl -OC(=O)S- 2-thienyl

CH₃ H H -OC(=O)- CH₃

CH₃ CH₃ H -OC(=O)- CH₃

CH₃ CH₃ CH₃ -OC(=O)- CH₃

CH₃ CH₃ Cl -OC(=O)- CH₃

CH₃ Cl CH₃ -OC(=O)- CH₃

CH₃ Cl Cl -OC(=O)- CH₃

CH₂CH₃ H H -OC(=O)- CH₃

CH₂CH₃ CH₃ H -OC(=O)- CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₃

CH₂CH₃ CH₃ Cl -OC(=O)- CH₃

CH₂CH₃ Cl CH₃ -OC(=O)- CH₃

CH₂CH₃ Cl Cl -OC(=O)- CH₃

CH₂CH₂CH H H -OC(=O)- CH₃

CH₂CH₂CH₃ CH₃ H -OC(=O)- CH₃

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)- CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH₃

CH CH₂CH3 Cl Cl -OC(=O)- CH₃

CH₃ H H -OC(=O)- CH₂CH₃

CH₃ CH₃ H -OC(=O)- CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₃

CH₃ CH₃ Cl -OC(=O)- CH₂CH₃

CH₃ Cl CH₃ -OC(=O)- CH₂CH₃

CH₃ Cl Cl -OC(=O)- CH₂CH₃

CH₂CH₃ H H -OC(=O)- CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)- CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)- CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)- CH₂CH₃

CH₂CH₂CH3 H H -OC(=O)- CH₂CH₃ CH₂CH₂CH₃ CH₃ H -OC(=O)- CH₂CH₃

CH₂CH₂CH CH₃ CH₃ -OC(=O)- CH₂CH₃

CH₂CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- CH₂CH₃

CH₂CH₂CH₃ Cl Cl -OC(=O)- CH₂CH₃

CH₃ H H -OC(=O)- CH₂CH₂CH3

CH₃ CH₃ H -OC(=O)- CH₂CH₂CH3

CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₂CH3

CH₃ CH₃ Cl -OC(=O)- CH₂CH₂CH

CH₃ Cl CH₃ -OC(=O)- H₂CH₂CH3

CH₃ Cl Cl -OC(=O)- CH₂CH CH3

CH₂CH₃ H H -OC(=O)- CH₂CH₂CH

CH₂CH₃ CH₃ H -OC(=O)- CH₂CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₃ Cl Cl -OC(=O)- CH CH₂CH₃

CH₂CH₂CH3 H H -OC(=O)- CH₂CH₂CH3

CH₂CH₂CH3 CH₃ H -OC(=O)- CH₂CH₂CH3

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH₂CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH₂CH₂CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)- CH₂CH₂CH₃

CH₃ H H -OC(=O)- cyc/o-propyl

CH₃ CH₃ H -OC(=O)- cyc/o-propyl

CH₃ CH₃ CH₃ -OC(=O)- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)- cyc/o-propyl

CH₃ Cl Cl -OC(=O)- cyc/o-propyl

CH₂CH₃ H H -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ H -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)- cyc/o-propyl

CH₂CH₂CH3 H H -OC(=O)- cyc/o-propyl

CH₂CH CH CH₃ H -OC(=O)- cyc/o-propyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)- cyc/o-propyl CH₂CH₂CH CH₃ Cl -OC(=O)- cyc/o-propyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- cyc/o-propyl

CH₂CH CH₃ Cl Cl -OC(=O)- cyc/o-propyl

CH₃ H H -OC(=O)- CH=CH₂

CH₃ CH₃ H -OC(=O)- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)- CH=CH₂

CH₃ CH₃ Cl -OC(=O)- CH=CH₂

CH₃ Cl CH₃ -OC(=O)- CH=CH₂

CH₃ Cl Cl -OC(=O)- CH=CH₂

CH₂CH₃ H H -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)- CH=CH₂

CH₂CH₂CH3 H H -OC(=O)- CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)- CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- CH=CH₂

CH₂CH₂CH CH₃ Cl -OC(=O)- CH=CH₂ H₂ H₂CH3 Cl CH₃ -OC(=O)- CH=CH₂

CH₂CH CH3 Cl Cl -OC(=O)- CH=CH₂

CH₃ H H -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ Cl Cl -OC(=O)- C(=CH₂)CH₃

CH CH₂CH3 H H -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH CH₃ H -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH CH₂CH3 CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)- C(=CH₂)CH₃ o o o o o o o o o o o o ffi X X X )

a Ω Ω a a S a Ω Ω S S S a Ω Ω a a a a Ω G a a a a Ω Ω a a

a Ω a Ω a a a Ω a Ω a a a Ω a Ω a a a Ω a Ω a a a Ω a Ω a

oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo

II II II II II II II II II II II II II II II II II II II II II II II II II II II II II o o o o o o o o o o o o o o o o o o o o o o o o o o o o o

- Ω HH ΩHH ΩHH ΩHH ΩHH ΩHH Ω H ΩHH Ω HH Ω m ΩHH I- t-O t-O t_0 t- ) t- U- I-O t- -k. (

CH₃ CH₃ H -OC(=O)- phenyl

CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₃ CH₃ Cl -OC(=O)- phenyl

CH₃ Cl CH₃ -OC(=O)- phenyl

CH₃ Cl Cl -OC(=O)- phenyl

CH₂CH₃ H H -OC(=O)- phenyl

CH₂CH₃ CH₃ H -OC(=O)- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)- phenyl

CH₂CH₃ Cl Cl -OC(=O)- phenyl

CH₂CH₂CH3 H H -OC(=O)- phenyl

CH CH₂CH₃ CH₃ H -OC(=O)- phenyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)- phenyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- phenyl

CH₂CH₂CH₃ Cl Cl -OC(=O)- phenyl

CH₃ H H -OC(=O)- 2-pyridinyl

CH₃ CH₃ H -OC(=O)- 2-pyridinyl

CH₃ CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)- 2-pyridinyl

CH₃ Cl Cl -OC(=O)- 2-pyridinyl

CH₂CH₃ H H -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ H H -OC(=O)- 2-pyridinyl

CH₂CH₂CH3 CH₃ H -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ Cl Cl -OC(=O)- 2-pyridinyl

CH₃ H H -OC(=O)- 2-furanyl

CH₃ CH₃ H -OC(=O)- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)- 2-furanyl CH₃ CH₃ Cl -OC(=O) 2-furanyl

CH₃ Cl CH₃ -OC(=O) 2-furanyl

CH₃ Cl Cl -OC(=O) 2-furanyl

CH₂CH₃ H H -OC(=O) 2-furanyl

CH₂CH₃ CH₃ H -OC(=O) 2-furanyl

CH₂CH₃ CH₃ CH₃ -OC(=O) 2-furanyl

CH₂CH₃ CH₃ Cl -OC(=O) 2-furanyl

CH₂CH₃ Cl CH₃ -OC(=O) 2-furanyl

CH₂CH₃ Cl Cl -OC(=O) 2-furanyl

CH₂CH₂CH₃ H H -OC(=O) 2-furanyl

CH₂CH₂CH₃ CH₃ H -OC(=O) 2-furanyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O) 2-furanyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O) 2-furanyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O) 2-furanyl

CH₂CH₂CH Cl Cl -OC(=O) 2-furanyl

CH₃ H H -OC(=O) 2-thienyl

CH₃ CH₃ H -OC(=O) 2-thienyl

CH₃ CH₃ CH₃ -OC(=O) 2-thienyl

CH₃ CH₃ Cl -OC(=O) 2-thienyl

CH₃ Cl CH₃ -OC(=O) 2-thienyl

CH₃ Cl Cl -OC(=O) 2-thienyl

CH₂CH₃ H H -OC(=O) 2-thienyl

CH₂CH₃ CH₃ H -OC(=O) 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O) 2-thienyl

CH₂CH₃ CH₃ Cl -OC(=O) 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O) 2-thienyl

CH₂CH₃ Cl Cl -OC(=O) 2-thienyl

CH₂CH₂CH3 H H -OC(=O) 2-thienyl

CH₂CH₂CH3 CH₃ H -OC(=O) 2-thienyl

CH₂CH₂CH CH₃ CH₃ -OC(=O) 2-thienyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O) 2-thienyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O) 2-thienyl

CH₂CH₂CH Cl Cl -OC(=O) 2-thienyl Table 2

l S-: R A Q.

CH₃ H H -OC(=O)O- CH₃

CH₃ CH₃ H -OC(=O)O- CH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH₃

CH₃ CH₃ Cl -OC(=O)O- CH₃

CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₃ Cl Cl -OC(=O)O- CH₃

CH₃ H H -OC(=O)S- CH₃

CH₃ CH₃ H -OC(=O)S- CH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH₃

CH₃ CH₃ Cl -OC(=O)S- CH₃

CH₃ Cl CH₃ -OC(=O)S- CH₃

CH₃ Cl Cl -OC(=O)S- CH₃

CH₂CH₃ H H -OC(=O)O- CH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH₃

CH₂CH₃ H H -OC(=O)S- CH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH₃

CH₂CH₂CH3 H H -OC(=O)O- CH₃

CH₂CH₂CH CH₃ H -OC(=O)O- CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- CH₃ CH CH₂CH₃ Cl CH₃ -OC(=O)O- CH₃

CH₂CH₂CH Cl Cl -OC(=O)O- CH₃

CH₂CH₂CH H H -OC(=O)S- CH₃

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)S- CH₃

CH₃ H H -OC(=O)O- CH₂CH₃

CH₃ CH₃ H -OC(=O)O- CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₃

CH₃ CH₃ Cl -OC(=O)O- CH₂CH₃

CH₃ Cl CH₃ -OC(=O)O- CH₂CH₃

CH₃ Cl Cl -OC(=O)O- CH₂CH₃

CH₃ H H -OC(=O)S- CH₂CH₃

CH₃ CH₃ H -OC(=O)S- CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₃

CH₃ CH₃ Cl -OC(=O)S- CH₂CH₃

CH₃ Cl CH₃ -OC(=O)S- CH₂CH₃

CH₃ Cl Cl -OC(=O)S- CH₂CH₃

CH₂CH₃ H H -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₃

CH₂CH₃ H H -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH₃ H₂CH₂CH3 H H -OC(=O)O- CH₂CH₃

CH₂CH₂CH3 CH₃ H -OC(=O)O- CH₂CH₃

CH₂CH CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- CH₂CH₃ H₂CH₂CH3 Cl CH₃ -OC(=O)O- CH₂CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)O- CH₂CH₃ H₂ H₂ ri3 H H -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- CH₂CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH₂CH₃

CH₂CH₂CH Cl Cl -OC(=O)S- CH₂CH₃

CH₃ H H -OC(=O)O- CH₂CH₂CH₃

CH₃ CH₃ H -OC(=O)O- CH₂CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₂CH3

CH₃ CH₃ Cl -OC(=O)O- CH₂CH₂CH3

CH₃ Cl CH₃ -OC(=O)O- CH₂CH₂CH

CH₃ Cl Cl -OC(=O)O- CH₂CH₂CH3

CH₃ H H -OC(=O)S- CH CH₂CH3

CH₃ CH₃ H -OC(=O)S- CH₂CH₂CH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH CH₂CH3

CH₃ CH₃ Cl -OC(=O)S- CH₂CH₂CH3

CH₃ Cl CH₃ -OC(=O)S- CH₂CH₂CH3

CH₃ Cl Cl -OC(=O)S- CH₂CH₂CH3

CH₂CH₃ H H -OC(=O)O- CH₂CH₂CH

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH₂CH3

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₂CH3

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₂CH₃

CH₂CH₃ H H -OC(=O)S- CH₂CH₂CH3

CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH₂CH

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH₂CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH₂CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH₂CH

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH₂CH₃

CH₂CH₂CH₃ H H -OC(=O)O- CH₂CH₂CH

CH₂CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH₂CH₃

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH₂CH

CH₂CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH₂CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH₂CH₃

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH₂CH

CH₂CH₂CH₃ H H -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH₃ CH₃ H -OC(=O)S- H₂ H₂ H CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₂CH₂CH3

CH₂CH₂Cri3 CH₃ Cl -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH₂CH3

CH₂CH₂CH3 Cl Cl -OC(=O)S- CH₂CH₂CH3

CH₃ H H -OC(=O)O- cyc/o-propyl

CH₃ CH₃ H -OC(=O)O- cyc/o-propyl

CH₃ CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₃ Cl Cl -OC(=O)O- cyc/o-propyl

CH₃ H H -OC(=O)S- cyc/o-propyl

CH₃ CH₃ H -OC(=O)S- cyc/o-propyl

CH₃ CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)S- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₃ Cl Cl -OC(=O)S- cyc/o-propyl

CH₂CH₃ H H -OC(=O)O- cyc/o-propyl

CH₂CH₃ CH₃ H -OC(=O)O- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)O- cyc/o-propyl

CH₂CH₃ H H -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ H -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)S- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)S- cyc/o-propyl

CH₂CH₂CH3 H H -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 Cl Cl -OC(=O)O- cyc/o-propyl

CH₂CH₂CH3 H H -OC(=O)S- cyc/o-propyl

CH CH₂CH CH₃ H -OC(=O)S- cyc/o-propyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH CH₃ CH₃ Cl -OC(=O)S- cyc/o-propyl CH₂CH₂CH3 Cl CH₃ -OC(=O)S- cyc/o-propyl

CH₂CH₂CH Cl Cl -OC(=O)S- cyc/o-propyl

CH₃ H H -OC(=O)O- CH=CH₂

CH₃ CH₃ H -OC(=O)O- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂

CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₃ Cl CH₃ -OC(=O)O- CH=CH₂

CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₃ H H -OC(=O)S- CH=CH₂

CH₃ CH₃ H -OC(=O)S- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)S- CH=CH₂

CH₃ CH₃ Cl -OC(=O)S- CH=CH₂

CH₃ Cl CH₃ -OC(=O)S- CH=CH₂

CH₃ Cl Cl -OC(=O)S- CH=CH₂

CH₂CH₃ H H -OC(=O)O- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)O- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₂CH₃ H H -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)S- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)S- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)S- CH=CH₂

CH₂CH₂CH₃ H H -OC(=O)O- CH=CH₂

CH₂CH₂CH CH₃ H -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CH₂

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH=CH₂

CH₂CH₂CH3 H H -OC(=O)S- CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)S- CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH=CH₂

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH=CH₂

CH₂CH₂CH₃ Cl Cl -OC(=O)S- CH=CH₂ CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₃ H H -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₃ Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH₃ H H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH CH₃ H -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)O- C(=CH₂)CH₃

CH CH₂CH₃ CH₃ Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)O- C(=CH₂)CH₃

CH₂CH₂CH₃ H H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH₃ CH₃ H -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- C(=CH₂)CH₃

CH CH₂CH3 CH₃ Cl -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- C(=CH₂)CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)S- C(=CH₂)CH₃

CH₃ H H -OC(=O)O- CH₂CH=CH₂

CH₃ CH₃ H -OC(=O)O- CH₂CH=CH₂ CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH₃ CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₃ Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH₃ Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₃ H H -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₃ CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH₃ Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₃ Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ H H -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₃ H H -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH3 H H -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- CH₂CH=CH₂

CH CH₂CH3 Cl Cl -OC(=O)O- CH₂CH=CH₂

CH₂CH CH3 H H -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH CH₃ H -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH CH₃ Cl -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- CH₂CH=CH₂

CH₂CH₂CH₃ Cl Cl -OC(=O)S- CH₂CH=CH₂

CH₃ H H -OC(=O)O- CH=CHCH₃

CH₃ CH₃ H -OC(=O)O- CH=CHCH₃

CH₃ CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH₃ CH₃ Cl -OC(=O)O- CH=CHCH₃ CH₃ Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₃ Cl Cl -OC(=O)O- CH=CHCH₃

CH₃ H H -OC(=O)S- CH=CHCH₃

CH₃ CH₃ H -OC(=O)S- CH=CHCH₃

CH₃ CH₃ CH₃ -OC(=O)S- CH=CHCH₃

CH₃ CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₃ Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₃ Cl Cl -OC(=O)S- CH=CHCH₃

CH₂CH₃ H H -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ H -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CHCH₃

CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₃ Cl Cl -OC(=O)O- CH=CHCH₃

CH₂CH₃ H H -OC(=O)S- CH=CHCH₃

CH₂CH₃ CH₃ H -OC(=O)S- CH=CHCH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₃ CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₂CH₃ Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₃ Cl Cl -OC(=O)S- CH=CHCH₃

CH₂CH CH3 H H -OC(=O)O- CH=CHCH₃

CH₂CH₂CH3 CH₃ H -OC(=O)O- CH=CHCH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₂CH₃ CH₃ Cl -OC(=O)O- CH=CHCH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- CH=CHCH₃

CH₂CH₂CH₃ Cl Cl -OC(=O)O- CH=CHCH₃

CH₂CH₂CH₃ H H -OC(=O)S- CH=CHCH₃

CH₂CH₂CH₃ CH₃ H -OC(=O)S- CH=CHCH₃

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₂CH₃ CH₃ Cl -OC(=O)S- CH=CHCH₃

CH₂CH₂CH Cl CH₃ -OC(=O)S- CH=CHCH₃

CH₂CH₂CH3 Cl Cl -OC(=O)S- CH=CHCH₃

CH₃ H H -OC(=O)O- phenyl

CH₃ CH₃ H -OC(=O)O- phenyl

CH₃ CH₃ CH₃ -OC(=O)O- phenyl

CH₃ CH₃ Cl -OC(=O)O- phenyl

CH₃ Cl CH₃ -OC(=O)O- phenyl

CH₃ Cl Cl -OC(=O)O- phenyl CH₃ H H -OC(=O)S- phenyl

CH₃ CH₃ H -OC(=O)S- phenyl

CH₃ CH₃ CH₃ -OC(=O)S- phenyl

CH₃ CH₃ Cl -OC(=O)S- phenyl

CH₃ Cl CH₃ -OC(=O)S- phenyl

CH₃ Cl Cl -OC(=O)S- phenyl

CH₂CH₃ H H -OC(=O)O- phenyl

CH₂CH₃ CH₃ H -OC(=O)O- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)O- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)O- phenyl

CH₂CH₃ Cl Cl -OC(=O)O- phenyl

CH₂CH₃ H H -OC(=O)S- phenyl

CH₂CH₃ CH₃ H -OC(=O)S- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)S- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)S- phenyl

CH₂CH₃ Cl Cl -OC(=O)S- phenyl H₂ H₂ H3 H H -OC(=O)O- phenyl

CH₂CH₂CH₃ CH₃ H -OC(=O)O- phenyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- phenyl

CH₂CH CH3 CH₃ Cl -OC(=O)O- phenyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- phenyl

CH₂CH₂CH3 Cl Cl -OC(=O)O- phenyl

CH₂CH₂CH3 H H -OC(=O)S- phenyl

CH₂CH₂CH3 CH₃ H -OC(=O)S- phenyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)S- phenyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- phenyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)S- phenyl

CH₂CH₂CH3 Cl Cl -OC(=O)S- phenyl

CH₃ H H -OC(=O)O- 2-pyridinyl

CH₃ CH₃ H -OC(=O)O- 2-pyridinyl

CH₃ CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₃ Cl Cl -OC(=O)O- 2-pyridinyl

CH₃ H H -OC(=O)S- 2-pyridinyl

CH₃ CH₃ H -OC(=O)S- 2-pyridinyl CH₃ CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₂CH₃ H H -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)O- 2-pyridinyl

CH₂CH₃ H H -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ H H -OC(=O)O- 2-pyridinyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- 2-pyridinyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH CH3 CH₃ Cl -OC(=O)O- 2-pyridinyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)O- 2-pyridinyl

CH₂CH₂CH₃ Cl Cl -OC(=O)O- 2-pyridinyl

CH₂CH₂CH H H -OC(=O)S- 2-pyridinyl

CH₂CH CH₃ CH₃ H -OC(=O)S- 2-pyridinyl H₂ H₂ H3 CH₃ CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH CH3 CH₃ Cl -OC(=O)S- 2-pyridinyl

CH₂CH₂CH Cl CH₃ -OC(=O)S- 2-pyridinyl

CH₂CH₂CH₃ Cl Cl -OC(=O)S- 2-pyridinyl

CH₃ H H -OC(=O)O- 2-furanyl

CH₃ CH₃ H -OC(=O)O- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)O- 2-furanyl

CH₃ CH₃ Cl -OC(=O)O- 2-furanyl

CH₃ Cl CH₃ -OC(=O)O- 2-furanyl

CH₃ Cl Cl -OC(=O)O- 2-furanyl

CH₃ H H -OC(=O)S- 2-furanyl

CH₃ CH₃ H -OC(=O)S- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)S- 2-furanyl

CH₃ CH₃ Cl -OC(=O)S- 2-furanyl o o o o o o o o o o o o o o o o o o o o o o

- afJ Ua- UaJ WaWa-at-a a^{) (}-a a^j -a-⁾ a⁾

Ω Ω a a a a Ω Ω a a a a Ω Ω a a a a Ω Ω a a a a Ω Ω a a

Ω a Ω a a a Ω a Ω a a a Ω a Ω a a a Ω a Ω a a a Ω a Ω a

oo oo oo oo oo oo o o o o o o oo oo oo oo oo oo o o o o o o oo oo oo oo

5Γ /-

tθ θ to to to to tθ to to to to bθ M to to to to to to to to to to to to b

St St St St St St St St St St St St ? 2^s -I H^> E^> 2^s E? B⁵ ? 2^> S¹ 2

CD CD CD CD CD CD CD CD CD CD CD CD P 03 03 03 03 P P 03 P P 0. P P

3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 _< 3

% ^, -^3 ' 3: ι; v<: 3; '-3< 3; 3< s 3 3 3 3

CH₂CH₃ H H -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ H -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O)O- 2-thienyl

CH₂CH₃ CH₃ Cl -OC(=O)O- 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O)O- 2-thienyl

CH₂CH₃ Cl Cl -OC(=O)O- 2-thienyl

CH₂CH₃ H H -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ H -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-thienyl

CH₂CH₃ CH₃ Cl -OC(=O)S- 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O)S- 2-thienyl

CH₂CH₃ Cl Cl -OC(=O)S- 2-thienyl

CH₂CH₂CH₃ H H -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ H -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)O- 2-thienyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)O- 2-thienyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)O- 2-thienyl

CH₂CH₂CH₃ Cl Cl -OC(=O)O- 2-thienyl

CH₂CH₂CH₃ H H -OC(=O)S- 2-thienyl

CH₂CH₂CH3 CH₃ H -OC(=O)S- 2-thienyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)S- 2-thienyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)S- 2-thienyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)S- 2-thienyl

CH CH₂CH3 Cl Cl -OC(=O)S- 2-thienyl

CH₃ H H -OC(=O)- CH₂CH₂CH3

CH₃ CH₃ H -OC(=O)- CH₂CH₂CH3

CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₂CH₃

CH₃ CH₃ Cl -OC(=O)- CH CH₂CH3

CH₃ Cl CH₃ -OC(=O)- CH₂CH CH

CH₃ Cl Cl -OC(=O)- CH₂CH₂CH3

CH₂CH₃ H H -OC(=O)- CH₂CH₂CH3

CH₂CH₃ CH₃ H -OC(=O)- CH₂CH₂CH3

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH₂CH3

CH₂CH₃ Cl CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₃ Cl Cl -OC(=O)- CH₂CH₂CH₃

CH CH CH₃ H H -OC(=O)- CH₂CH₂CH₃

CH CH₂CH₃ CH₃ H -OC(=O)- CH₂CH₂CH₃ CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- CH₂CH₂CH

CH₂CH₂CH3 CH₃ Cl -OC(=O)- CH₂CH₂CH3

CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH₂CH₂CH3

CH₂CH₂CH3 Cl Cl -OC(=O)- CH₂CH₂CH3

CH₃ H H -OC(=O)- cyc/o-propyl

CH₃ CH₃ H -OC(=O)- cyc/o-propyl

CH₃ CH₃ CH₃ -OC(=O)- cyc/o-propyl

CH₃ CH₃ Cl -OC(=O)- cyc/o-propyl

CH₃ Cl CH₃ -OC(=O)- cyc/o-propyl

CH₃ Cl Cl -OC(=O)- cyc/o-propyl

CH₂CH₃ H H -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ H -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₃ CH₃ Cl -OC(=O)- cyc/o-propyl

CH₂CH₃ Cl CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₃ Cl Cl -OC(=O)- cyc/o-propyl

CH₂CH₂CH₃ H H -OC(=O)- cyc/o-propyl

CH₂CH₂CH₃ CH₃ H -OC(=O)- cyc/o-propyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)- cyc/o-propyl H₂ H₂ H3 Cl CH₃ -OC(=O)- cyc/o-propyl

CH₂CH₂CH3 Cl Cl -OC(=O)- cyc/o-propyl

CH₃ H H -OC(=O)- CH=CH₂

CH₃ CH₃ H -OC(=O)- CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)- CH=CH₂

CH₃ CH₃ Cl -OC(=O)- CH=CH₂

CH₃ Cl CH₃ -OC(=O)- CH=CH₂

CH₃ Cl Cl -OC(=O)- CH=CH₂

CH₂CH₃ H H -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)- CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)- CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)- CH=CH₂

CH₂CH₂CH3 H H -OC(=O)- CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)- CH=CH₂

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- CH=CH₂

CH₂CH₂CH3 CH₃ Cl -OC(=O)- CH=CH₂ CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH=CH₂

CH₂CH₂CH3 Cl Cl -OC(=O)- CH=CH₂

CH₃ H H -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ H -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH₃ CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₃ Cl CH₃ -OC(=O)- C(=CH₂)CH₃

CH₃ Cl Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ H H -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ H -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ Cl CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₃ Cl Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH H H -OC(=O)- C(=CH₂)CH₃

CH₂CH₂Cπ3 CH₃ H -OC(=O)- C(=CH₂)CH₃

CH CH₂CH3 CH₃ CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH₃ CH₃ Cl -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- C(=CH₂)CH₃

CH₂CH₂CH3 Cl Cl -OC(=O)- C(=CH₂)CH₃

CH₃ H H -OC(=O)- CH₂CH=CH₂

CH₃ CH₃ H -OC(=O)- CH₂CH=CH₂

CH₃ CH₃ CH₃ -OC(=O)- CH₂CH=CH₂

CH₃ CH₃ Cl -OC(=O)- CH₂CH=CH₂

CH₃ Cl CH₃ -OC(=O)- CH₂CH=CH₂

CH₃ Cl Cl -OC(=O)- CH₂CH=CH₂

CH₂CH₃ H H -OC(=O)- CH₂CH=CH₂

CH₂CH₃ CH₃ H -OC(=O)- CH₂CH=CH₂

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH₂CH=CH₂

CH₂CH₃ CH₃ Cl -OC(=O)- CH₂CH=CH₂

CH₂CH₃ Cl CH₃ -OC(=O)- CH₂CH=CH₂

CH₂CH₃ Cl Cl -OC(=O)- CH₂CH=CH₂

CH₂CH₂CH3 H H -OC(=O)- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ H -OC(=O)- CH₂CH=CH₂

CH CH₂CH3 CH₃ CH₃ -OC(=O)- CH₂CH=CH₂

CH₂CH₂CH3 CH₃ Cl -OC(=O)- CH₂CH=CH₂

CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH₂CH=CH₂

CH₂CH₂CH3 Cl Cl -OC(=O)- CH₂CH=CH₂ CH₃ H H -OC(=O)- CH=CHCH₃

CH₃ CH₃ H -OC(=O)- CH=CHCH₃

CH₃ CH₃ CH₃ -OC(=O)- CH=CHCH₃

CH₃ CH₃ Cl -OC(=O)- CH=CHCH₃

CH₃ Cl CH₃ -OC(=O)- CH=CHCH₃

CH₃ Cl Cl -OC(=O)- CH=CHCH₃

CH₂CH₃ H H -OC(=O)- CH=CHCH₃

CH₂CH₃ CH₃ H -OC(=O)- CH=CHCH₃

CH₂CH₃ CH₃ CH₃ -OC(=O)- CH=CHCH₃

CH₂CH₃ CH₃ Cl -OC(=O)- CH=CHCH₃

CH₂CH₃ Cl CH₃ -OC(=O)- CH=CHCH₃

CH₂CH₃ Cl Cl -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 H H -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 CH₃ H -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 CH₃ Cl -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 Cl CH₃ -OC(=O)- CH=CHCH₃

CH₂CH₂CH3 Cl Cl -OC(=O)- CH=CHCH₃

CH₃ H H -OC(=O)- phenyl

CH₃ CH₃ H -OC(=O)- phenyl

CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₃ CH₃ Cl -OC(=O)- phenyl

CH₃ Cl CH₃ -OC(=O)- phenyl

CH₃ Cl Cl -OC(=O)- phenyl

CH₂CH₃ H H -OC(=O)- phenyl

CH₂CH₃ CH₃ H -OC(=O)- phenyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₂CH₃ CH₃ Cl -OC(=O)- phenyl

CH₂CH₃ Cl CH₃ -OC(=O)- phenyl

CH₂CH₃ Cl Cl -OC(=O)- phenyl

CH₂CH₂CH₃ H H -OC(=O)- phenyl

CH₂CH₂CH CH₃ H -OC(=O)- phenyl

CH₂CH₂CH₃ CH₃ CH₃ -OC(=O)- phenyl

CH₂CH₂CH CH₃ Cl -OC(=O)- phenyl

CH₂CH₂CH Cl CH₃ -OC(=O)- phenyl

CH₂CH₂CH₃ Cl Cl -OC(=O)- phenyl

CH₃ H H -OC(=O)- 2-pyridinyl

CH₃ CH₃ H -OC(=O)- 2-pyridinyl CH₃ CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₃ CH₃ Cl -OC(=O)- 2-pyridinyl

CH₃ Cl CH₃ -OC(=O)- 2-pyridinyl

CH₃ Cl Cl -OC(=O)- 2-pyridinyl

CH₂CH₃ H H -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ H -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₃ CH₃ Cl -OC(=O)- 2-pyridinyl

CH₂CH₃ Cl CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₃ Cl Cl -OC(=O)- 2-pyridinyl

CH₂CH₂CH H H -OC(=O)- 2-pyridinyl

CH₂CH₂CH₃ CH₃ H -OC(=O)- 2-pyridinyl

CH₂CH₂CH3 CH₃ CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₂CH3 CH₃ Cl -OC(=O)- 2-pyridinyl

CH₂CH₂CH3 Cl CH₃ -OC(=O)- 2-pyridinyl

CH₂CH₂CH3 Cl Cl -OC(=O)- 2-pyridinyl

CH₃ H H -OC(=O)- 2-furanyl

CH₃ CH₃ H -OC(=O)- 2-furanyl

CH₃ CH₃ CH₃ -OC(=O)- 2-furanyl

CH₃ CH₃ Cl -OC(=O)- 2-furanyl

CH₃ Cl CH₃ -OC(=O)- 2-furanyl

CH₃ Cl Cl -OC(=O)- 2-furanyl

CH₂CH₃ H H -OC(=O)- 2-furanyl

CH₂CH₃ CH₃ H -OC(=O)- 2-furanyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- 2-furanyl

CH₂CH₃ CH₃ Cl -OC(=O)- 2-furanyl

CH₂CH₃ Cl CH₃ -OC(=O)- 2-furanyl

CH₂CH₃ Cl Cl -OC(=O)- 2-furanyl

CH₂CH₂CH3 H H -OC(=O)- 2-furanyl

CH₂CH₂CH₃ CH₃ H -OC(=O)- 2-furanyl

CH₂CH₂CH CH₃ CH₃ -OC(=O)- 2-furanyl

CH CH₂CH₃ CH₃ Cl -OC(=O)- 2-furanyl

CH₂CH CH₃ Cl CH₃ -OC(=O)- 2-furanyl

CH₂CH₂CH3 Cl Cl -OC(=O)- 2-furanyl

CH₃ H H -OC(=O)- 2-thienyl

CH₃ CH₃ H -OC(=O)- 2-thienyl

CH₃ CH₃ CH₃ -OC(=O)- 2-thienyl

CH₃ CH₃ Cl -OC(=O)- 2-thienyl CH₃ Cl CH₃ -OC(=O)- 2-thienyl

CH₃ Cl Cl -OC(=O)- 2-thienyl

CH₂CH₃ H H -OC(=O)- 2-thienyl

CH₂CH₃ CH₃ H -OC(=O)- 2-thienyl

CH₂CH₃ CH₃ CH₃ -OC(=O)- 2-thienyl

CH₂CH₃ CH₃ Cl -OC(O)- 2-thienyl

CH₂CH₃ Cl CH₃ -OC(=O)- 2-thienyl

CH₂CH₃ Cl Cl -OC(=O)- 2-thienyl

CH₂CH₂CH H H -OC(=O)- 2-thienyl

CH₂CH₂CH₃ CH₃ H -OC(=O)- 2-thienyl

CH₂CH₂CH CH₃ CH₃ -OC(=O)- 2-thienyl

CH₂CH₂CH₃ CH₃ Cl -OC(=O)- 2-thienyl

CH₂CH₂CH₃ Cl CH₃ -OC(=O)- 2-thienyl

CH₂CH₂CH3 Cl Cl -OC(=O)- 2-thienyl

Table 3

R¹ is CHoCH,, R2 and R³ are CH^

l

-OC(=O)O- 5-CH₃-2-furanyl -OC(=O)- 2-CH₃-phenyl

-OC(=O)S- 5-CH₃-2-furanyl -OC(=O)- 3-CH₃-phenyl

-OC(=O)O- 5-Cl-2-furanyl -OC(=O)- 4-CH₃-phenyl

-OC(=O)S- 5-Cl-2-furanyl -OC(=O)- 2,6-diCH₃-phenyl

-OC(=O)O- 3-pyridinyl -OC(=O)- 2-Cl-phenyl

-OC(=O)S- 3-pyridinyl -OC(=O)- 3-Cl-phenyl

-OC(=O)O- 4-pyridinyl -OC(=O)- 4-Cl-phenyl

-OC(=O)S- 4-pyridinyl -OC(=O)- 2-OCH₃-phenyl

-OC(=O)O- 6-CH3 -2 -pyridinyl -OC(=O)- 3 OCH₃-phenyl

-OC(=O)S- 6-CH₃-2-pyridinyl -OC(=O)- 4-OCH₃-phenyl

-OC(=O)O- 6-Cl-2-pyridinyl -OC(=O)- 2,6-diCl-phenyl

-OC(=O)S- 6-Cl-2-pyridinyl -OC(=O)- 2,5-diCl-phenyl

-OC(=O)O- 2-CH₃-phenyl -OC(=O)- 2,4-diCl-phenyl

-OC(=O)S- 2 -CH3 -phenyl

-OC(=O)O- 3-CH₃-phenyl

-OC(=O)S- 3-CH₃-phenyl

-OC(=O)O- 4-CH₃-phenyl

-OC(=O)S- 4-CH₃-phenyl

-OC(=O)O- 2,6-diCH₃-phenyl

-OC(=O)S- 2,6-diCH3-phenyl

-OC(=O)O- 2-Cl-phenyl

-OC(=O)S- 2-Cl-phenyl

-OC(=O)O- 3-Cl-phenyl

-OC(=O)S- 3-Cl-phenyl

-OC(=O)O- 4-Cl-phenyl

-OC(=O)S- 4-Cl-phenyl

-OC(=O)O- 2-OCH₃-phenyl

-OC(=O)S- 2-OCH₃-phenyl

-OC(=O)O- 3 OCH₃-phenyl

-OC(=O)S- 3 OCH3 -phenyl

-OC(=O)O- 4-OCH₃-phenyl

-OC(=O)S- 4-OCH₃-phenyl

-OC(=O)O- 2,6-diCl-phenyl

-OC(=O)S- 2,6-diCl-phenyl

-OC(=O)O- 2,5-diCl-phenyl

-OC(=O)S- 2,5-diCl-phenyl

-OC(=O)O- 2,4-diCl-phenyl

-OC(=O)S- 2,4-diCl-phenyl

Table 4

R¹ is CH CH, R² and R³ are CH

-OC(=O)O- 3-CH₃-phenyl -OC(=O)S- 3-CH₃-phenyl -OC(=O)O- 4-CH₃-phenyl -OC(=O)S- 4-CH₃-phenyl -OC(=O)O- 2,6-diCH₃-phenyl -OC(=O)S- 2,6-diCH₃-phenyl -OC(=O)O- 2-Cl-phenyl -OC(=O)S- 2-Cl-phenyl -OC(=O)O- 3-Cl-phenyl -OC(=O)S- 3-Cl-phenyl -OC(=O)O- 4-Cl-phenyl -OC(=O)S- 4-Cl-phenyl -OC(=O)O- 2-OCH₃ -phenyl -OC(=O)S- 2-OCH₃-phenyl -OC(=O)O- 3 OCH₃-phenyl -OC(=O)S- 3 OCH₃-phenyl -OC(=O)O- 4-OCH₃-phenyl -OC(=O)S- 4-OCH₃-phenyl -OC(=O)O- 2,6-diCl-phenyl -OC(=O)S- 2,6-diCl-phenyl -OC(=O)O- 2,5-diCl-phenyl -OC(=O)S- 2,5-diCl-phenyl -OC(=O)O- 2,4-diCl-phenyl -OC(=O)S- 2,4-diCl-phenyl

Table 5

Rl R^ R3 R6 RZ

CH₂CH₃ CH₃ CH₃ CH₃ CH₃

CH₂CH₃ CH₃ CH₃ CH₂CH₃ CH₂CH₃

CH₂CH₃ CH₃ CH₃ CH₃ phenyl

CH₂CH₃ CH₃ CH₃ -CH₂CH₂CH₂CH₂-

CH₂CH₃ CH₃ CH₃ -CH₂CH₂OCH₂CH₂-

Table 6

Rl R^ E R6 EZ

CH₂CH₃ CH₃ CH₃ CH₃ CH₃

CH₂CH₃ CH₃ CH₃ CH₂CH₃ CH₂CH₃

CH₂CH₃ CH₃ CH₃ CH₃ phenyl

CH₂CH₃ CH₃ CH₃ -CH₂CH₂CH₂CH -

CH₂CH₃ CH₃ CH₃ -CH₂CH₂OCH₂CH₂-

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

Active

Ingredient Diluent Surfactant

Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.

Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates)

Dusts 1-25 70-99 0-5

Granules and Pellets 0.01-99 5-99.99 0-15

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, NN-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 emulsifϊable 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 Table A.

Example A High Strength Concentrate

Compound 14 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.

Example B Wettable Powder

Compound 29 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%> montmorillonite (calcined) 23.0%.

Example C Granule

Compound 30 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 40 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.

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.

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, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, 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-(l-methylethyl)-5-oxo-lH-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, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, fiamprop-M-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluridone, flurochloridone, fluroxypyr, fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[l-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2- methoxyethylidene]amino]oxy] acetate (AKΗ-7088), methyl 5-[[[[(4,6-dimethyl-2- pyrimidinyl)amino]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, oxasulfuron, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl, 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, triaziflam, 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.

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 following abbreviations are used in the Index Tables which follow: Ph = phenyl. 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.

INDEX TABLE A

R¹ is CHoCHi

Cmpd A Q Rl R5 mp (°C)

1 OC(=0) C(=CH₂)CH₃ c=o 63 (dec)

2 OC(=0) Ph c=o 70 (dec)

3 OC(=0) CH(CH₃)₂ C=0 62-63 (dec)

4 OC(=0) 2,5-diCl-6-OCH₃Ph c=o oil *

5 OC(=0) 4-CH₃Ph C=0 81 (dec)

6 OC(=0) cyclopropyl C=0 77 (dec)

7 OC(=0) 3,6-diCl-pyridin-2-yl c=o 215-217

8 OC(=0) furan-2-yl C=0 70 (dec)

9 OC(=0) 2-CH₃Ph c=o 201-203

10 OC(=0) 2-FPh C=0 153-155

11 OC(=0) 4-FPh C=0 158-160

12 OC(=0) 4-BrPh c=o 98 (dec)

13 OC(=0) C(=CH₂)CH₃ -OCH₂CH₂0- 175-177 (dec)

14 OC(=0) Ph -OCH₂CH₂0- 179-180 15 OC(=0) CH(CH₃)₂ -OCH₂CH₂0- 73 (dec)

16 OC(=0) 2,5-diCl-6-OCH₃Ph -OCH₂CH₂0- 198-200

17 OC(=0) cyclopropyl -OCH₂CH₂0- 215-217

18 OC(=0) 3,6-diCl-pyridin-2-yl -OCH₂CH₂0- 228-230

19 OC(=0) fiιran-2-yl -OCH₂CH₂0- 201-203

20 OC(=0) 4-FPh -OCH₂CH₂0- 237-239

21 OC(=0) C(CH₃)₃ -OCH₂CH₂0- >200 *

23 OC(=0)0 CH(CH₃)₂ c=o 58-60 (dec)

24 OC(=0)0 CH₂CH₃ C=0 58 (dec)

25 OC(=0)0 CH₂CH=CH₂ C-0 oil*

26 OC(=0)0 CH₃ C=0 135-137

27 OC(=0)0 Ph c=o 68 (dec)

28 OC(=0)0 CH₂CH₂CH₃ c=o 68 (dec)

(Ex. 1) OC(=0)0 CH(CH₃)₂ -OCH₂CH₂0- 168-170

(Ex. 2) OC(=0)0 CH₂CH₃ -OCH₂CH₂0- 201-203

31 OC(=0)0 CH₃ -OCH₂CH₂0- 191-193

32 OC(=0)0 CH₂CH=CH₂ -OCH₂CH₂0- 72-74

33 OC(=0)0 CH₂CH₂CH₃ -OCH₂CH₂0- 74 (dec)

34 OC(=0)0 Ph -OCH₂CH₂0- 215

35 OC(=0)0 CH₂CH(CH₃)₂ -OCH₂CH₂0- 65-67 (dec)

36 OC(=0)0 CH₂CH₂CH₂CH₃ -OCH₂CH₂0- 62 (dec)

37 OC(=0)0 CH₂CH₂OCH₃ -OCH₂CH₂0- 113 (dec)

38 OC(=0)0 CH₂CH₂CH₂CH₂CH₃ -OCH₂CH₂0- 58 (dec)

39 OC(=0)0 (CH₂)₅CH₃ -OCH₂CH₂0- 48 (dec)

40 OC(=0)0 CH₂Ph -OCH₂CH₂0- 171

41 OC(=0)0 (CH₂)₇CH₃ -OCH₂CH₂0- 47 (dec)

42 OC(=0)0 CH₂C1 -OCH₂CH₂0- 61-62 (dec)

43 OC(=0)0 CH₂CH₂CH₂CH₂C1 -OCH₂CH₂0- 48-50 (dec)

44 OC(=0)0 CH₂CH₂C1 -OCH₂CH₂0- 169-171 (dec)

45 OC(=0)0 CH₂CH₂Br -OCH₂CH₂0- 170-172 (dec)

46 OC(=0)0 4-BrPh -OCH₂CH₂0- 85-98

47 OC(=0)0 4-ClPh -OCH₂CH₂0- 78-90

48 OC(=0)0 4-OCH₃Ph -OCH₂CH₂0- 160-163

49 OC(=0)0 4-CH₃Ph -0CH₂CH₂O 176-182

50 OC(=0)N(CH₃)₂ -OCH₂CH₂0- 239-241

51 OC(=0)N(CH₂CH₃)₂ -OCH₂CH₂0- oil *

53 OC(=0)N(CH₃)Ph OCH₂CH₂0- 98-102 54 OC(=0)N(CH(CH₃)₂)₂ OCH₂CH₂0- 107-112 55 OCH₂CH₂0- semi-solid *

56 OC(=0)S CH₂CH₃ OCH₂CH₂0- 173-174 57 OC(=0)S CH₃ OCH₂CH₂0- 172-175 58 OC(=0)S Ph OCH₂CH₂0- 170-171 59 OC(=0)S 4-ClPh OCH₂CH₂0- 176-177

*See Index Table B for *H NMR data.

R¹ is CH_?

Cmpd A Q. Rl R mp (°C)

60 OC(=0)0 CH₂CH₃ -OCH₂CH₂0- 155-157

61 OC(=0)0 CH₂CH₂CH₃ -OCH₂CH₂0- 160-162

62 OC(=0)0 CH₂Ph -OCH₂CH₂0- 85-87

INDEX TABLE B

Cmpd No. ^!H NMR Data (CDC1₃ solution unless indicated otherwise)³

4 δ 1.5 (t, 3H), 2.48 (s, 3H), 2.76 (s, 3H), 3.34 (m, 2H), 3.74 (m, 2H), 4.05

(s, 3H), 4.21 (q, 2H), 7.24 (d, IH), 7.43 (s, IH), 7.51 (m, 2H). 21 δ 1.22 (s, 9H), 1.31 (t, 3H), 2.17 (s, 3H), 2.45 (m, 2H), 2.63 (s, 3H), 3.39

(m, 2H), 3.88 (q, 2H), 3.9-4.19 (m, 4H), 7.08 (s, IH), 7.44 (s, IH). 25 δ 1.46 (t, 3H), 2.43 (s, 3H), 2.76 (s, 3H), 3.35 (m, 2H), 3.75 (m, 2H), 4.10

(m, 2H), 4.78 (d, 2H), 5.4 (m, 2H), 6.0 (m, IH), 7.37 (s, IH), 7.51 (s, IH). 51 δ 1.172 (t, 3H), 1.196 (t, 3H), 1.453 (t, 3H), 2.279 (s, 3H), 2.55 (m, 2H),

2.733 (s, 3H), 3.2 (q, 2H), 3.3 (q, 2H), 3.5 (m, 2H), 4.0 (q, 2H), 4.15 (m,

2H), 4.25 (m, 2H), 7.2 (s, IH), 7.7 (s, IH). 55 δ 1.460 (t, 3H), 2.280 (s, 3H), 2.6 (m, 2H), 2.741 (s, 3H), 3.5 (m, 6H),

3.75 (m, 4H), 4.0 (q, 2H), 4.2 (m, 2H), 4.3 (m, 2H), 7.191 (s, 1H0, 7.65 (s,

IH). ^{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, (dt)-doublet of triplets, (br s)-broad singlet. BIOLOGICAL EXAMPLES OF THE INVENTION Test A

Seeds of broadleaf signalgrass (Brachiaria decumbens), barley (Hordeum vulgare), bamyardgrass (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 (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Retα 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 included a surfactant. A sprayed paddy pot was treated with some designated compounds. This paddy contained rice, bamyardgrass, smallflowered flatsedge (Cyperus difformis) and duck salad (Heteranthera limosa) as the target species and was sprayed alongside the other crop and weed species.

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 2 to 18 cm (1- to 4-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.

Table A COMPOUND

Rate 50 g/ha 1 2 3 4 5 6 7 8 13 14 15 16 17 18 19 23 24 25 26 29 30 31 32

POSTEMERGENCE

B. signalgrass 7 6 - 7 9 6

Barley 0 0 1 1 0 2 0 1 2 2 1 2 3 0 3 0 1 - - 2 - - -

Bamyardgrass 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 - - 9 - - -

Bedstraw 9 8 9 9 10 9 9 9 9 9 9 9 9 9 9 8 9 8 8 9 9 9 9

Blackgrass 1 4 4 5 6 6 2 6 2 7 6 4 8 2 5 6 6 5 5 7 5 3 3

Chickweed 9 9 10 9 9 9 9 9 9 10 10 9 10 9 9 10 10 - - 10 - - -

Cocklebur 9 9 9 9 9 9 8 9 9 9 9 9 9 9 9 9 9 10 10 9 10 10 9

Corn 0 1 0 0 0 0 0 0 2 3 1 2 1 0 2 0 0 0 0 2 3 4 2

Cotton 9 9 9 9 9 9 9 9 8 9 9 10 9 8 9 10 9 - - 10 - - -

Crabgrass 9 9 9 9 9 9 8 9 9 9 9 9 9 7 9 9 9 8 9 9 9 9 9

Downy brome 0 0 2 0 4 0 0 0 0 3 5 2 3 0 2 1 0 - - 3 - - -

Giant foxtail 9 9 9 9 9 9 8 9 9 9 9 9 9 7 9 9 9 10 10 9 9 9 8

Lambsquarters 9 9 9 9 9 9 9 9 9 10 9 9 10 8 9 9 9 - - 9 - - -

Morningglory 9 9 8 8 8 8 8 8 9 9 9 9 9 8 9 9 8 8 8 9 9 9 9

Nutsedge 0 0 0 0 0 0 0 0 4 0 - 0 3 0 6 9 0 0 0 7 5 6 4

Rape 7 7 8 9 8 9 8 10 9 9 8 8 9 5 8 9 8 10 9 10 9 8 9

Redroot pigweed 9 9 - 9 9 9

Rice 9 9 10 10 10 10 8 10 9 10 10 9 9 9 9 10 9 - - 10 - - -

Sorghum 3 6 6 7 6 7 5 6 7 8 9 9 9 6 9 9 7 - - 9 - - -

Soybean 7 9 9 8 9 7 9 8 9 8 6 9 8 9 8 8 8 9 9 9 8 8 9

Sugar beet 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Velvetleaf 9 9 9 9 8 7 8 9 9 10 9 9 9 9 9 10 9 9 10 9 9 10 10

Wheat 2 4 5 3 6 5 1 4 3 5 5 5 9 1 7 5 8 4 4 8 4 5 4

Wild buckwheat 5 2 8 8 8 8 7 6 7 9 8 8 9 7 8 8 7 - - 8 - - -

Wild oat 1 0 3 3 4 3 0 2 6 7 7 8 7 2 9 4 2 4 3 8 10 9 5

Table A C OM:

Rate 50 g/ha 1 2 3 13 14 15 16 17 18 19 23 24 25 26 29 30 31 32

PREEMERGENCE B. signalgrass - - - - - - 2 - - 5 5 1

Barley 0 0 0 o o o o o o o o 0 0 0 0 0 0 - - 0 - - -

Bamyardgrass 0 0 1 0 3 3 2 2 5 8 3 0 4 2 8 2 4 - - 1 - - -

Bedstraw 1 - 1 0 7 2 0 0 1 10 - 0 0 0 0 0 0 0 0 0 0 0 0 8 8 0 0 0 0 5 5 3 3 0 0 <-

Blackgrass 0 0 0 o o o o o o o o 0 0 0 1 1 0 0 0 0 0 0 0

Chickweed 5 8 7 6 7 6 6 6 6 6 5 5 6 4 6 7 7 - - 5 - - -

Cocklebur 0 0 0 4 0 0 9 0 0 0 0 0 0 9 0 0 0 10 0 0 0 9 7

Corn 0 0 0 o o o o o o o o 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 2 0 0 0 0 0 4 0 0 - 0 0 0 0 0 0 0 0 - - 0 - - -

Crabgrass 3 2 2 2 3 3 1 3 2 6 1 2 2 6 6 6 6 3 3 0 0 3 3 2 2 7 7 4 4 6 6 5 5 0 0

Downy brome 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0^" - - 0 - - -

Giant foxtail 0 1 1 2 5 3 2 2 1 2 0 1 1 2 2 2 2 3 3 2 2 2 2 7 7 1 1 3 3 5 5 5 5 0 0

Lambsquarters 8 10 8 9 9 9 8 9 9 10 9 9 9 9 9 1 100 1 100 9 9 9 9 - - - - 9 9 - - - - - -

Morningglory 0 0 0 0 0 0 3 1 0 2 0 0 0 0 7 1 0 1 4 4 1 4 0 0

Nutsedge 0 0 0 0 0 0 0 - 0 0 - 6 0 0 - 0 0 0 - 0 0 0 0

Rape 0 1 2 0 7 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 6 6 4

Redroot pigweed 6 0 - 8 8 6

Rice 0 0 0 0 0 2 2 1 2 2 1 0 2 0 2 2 1 - - 0 - - -

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Soybean 1 0 0 4 0 0 8 0 1 0 0 0 0 8 2 0 0 0 0 0 0 0 0

Sugar beet 7 6 3 0 4 7 0 4 6 6 6 2 4 2 3 3 3 9 8 0 4 10 9

Velvetleaf 0 0 0 2 0 2 3 2 0 6 2 8 3 6 2 0 0 7 5 4 10 10 8

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 4 3 0 0 0 - - 1 - - -

Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 1 0

Table A COMPOUND o

Rate 10 g/ha 1 2 3 4 5 6 7 8 14 15 16 17 18 19 23 24 25 26 29 30 31 32

POSTEMERGENCE

B. signalgrass 0 2 - 5 3 3

Barley 0 0 0 0 0 0 0 0 0 0 0 2 0 1 0 0 - - 0 - - -

Ba yardgrass 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 - - 9 - - -

Bedstraw 6 6 9 9 9 8 8 8 8 8 9 9 7 7 7 8 8 7 8 6 6 7

Blackgrass 0 1 0 1 4 2 1 1 2 0 0 1 0 1 2 1 0 1 1 0 1 0

Chickweed 8 8 9 9 9 9 7 7 10 9 9 8 8 8 8 8 - - 8 - - -

Cocklebur 5 8 8 8 9 7 8 8 9 8 8 9 9 9 8 9 9 9 9 10 10 8

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0

Cotton 8 4 2 8 8 8 6 9 8 6 6 8 6 9 9 9 - - 9 - - -

Crabgrass 5 8 8 8 7 8 6 8 8 8 8 4 7 9 9 8 8 9 8 9 9 9

Downy brome 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Giant foxtail 3 7 7 7 7 7 6 7 8 8 7 8 7 9 9 9 4 9 8 9 9 8 ambsquarters 9 7 9 9 9 - 7 9 9 9 9 9 8 9 9 9 - - 8 - - -

Morningglory 2 9 6 8 1 1 3 7 6 8 8 8 7 8 6 6 7 8 8 8 8 6

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 2 2 0 0

Rape 2 3 0 6 5 5 7 3 4 4 0 4 4 2 7 5 5 6 4 0 3 1

Redroot pigweed 9 7 - 6 9 8

Rice 8 9 9 9 9 9 7 8 9 9 9 9 7 8 10 8 - - 8 - - -

Sorghum 0 0 0 1 0 1 0 2 4 2 1 5 2 6 2 2 - - 8 - - -

Soybean 4 3 5 6 5 6 8 6 5 6 8 6 6 6 7 7 8 7 6 6 6 7

Sugar beet 9 9 9 9 9 9 9 9 10 10 9 10 9 10 10 9 9 9 10 9 9 9 s

Velvetleaf 7 7 6 7 8 6 6 6 9 9 9 9 9 9 10 8 7 9 9 9 9 9

Wheat 0 0 0 0 0 2 0 1 0 0 0 2 0 1 0 0 0 2 1 0 1 0

Wild buckwheat 5 1 6 7 6 6 4 2 1 6 7 2 3 7 5 4 - - 4 - - -

Wild oat 0 0 1 0 4 1 0 0 1 2 0 3 1 2 0 2 0 2 3 3 2 1

Table A COMPOUND

Rate 10 g/ha 1 2 3 4 5 6 7 8 14 15 16 17 18 19 23 24 25 26 29 30 31 32

PREEMERGENCE

B. signalgrass 0 0 - 1 0 0

Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Barnyardgrass 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 - - 1 - - -

Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Chickweed 3 0 0 0 0 0 3 3 0 0 0 0 0 0 0 0 - - 0 - - -

Cocklebur 0 0 0 0 0 0 6 0 0 0 0 0 6 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 - - 0 - - -

Crabgrass 0 0 0 0 0 0 0 0 1 0 0 1 1 1 0 1 1 0 1 3 0 0

Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 1 0 0

Lambsquarters 4 6 0 4 3 4 7 7 8 0 3 7 2 8 6 4 - - 2 - - -

Morningglory 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 - 0 0 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Redroot pigweed 3 0 - 0 0 1

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Soybean 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 3 0 0 0 0 3 0 3 0 0 0 0 0 0 3 0 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 - - -

Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A COMPOUND Table A COMPOUND

Rate 50 g/ha 25 26 30 31 32 Rate 10 g/ha 25 26 30 31 32 SPRAYED PADDY SPRAYED PADDY

Bamyardgrass 10 10 10 9 10 Bamyardgrass 10 10 10 7 10

Ducksalad 6 5 6 3 6 Ducksalad 4 4 2 0 4

Rice 10 9 10 10 10 Rice 8 6 9 5 9

S. flatsedge 7 9 6 6 8 S. flatsedge 4 6 2 4 5

Test B

Seeds of broadleaf signalgrass (Brachiaria decumbens), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cocklebur (Xanthium strumarium), com (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea hederacea), rape (Brassica napus), pigweed (Amaranthus retroflexus), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), 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 included 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 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Plant species in the flood test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad

(Heteranthera limosa) and bamyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. 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 B, 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.

Table B COMPOUND

Rate 62 g/ha 17 19 23 25 29 60 61 62

Postemergence

B. signalgrass 10 9 5 6 9 3 4

Ba yardgrass 9 5 9 0 9 0 2

Bedstraw 10 9 9 9 9 9 2

Blackgrass 6 5 3 3 5 1 3

Cocklebur 10 10 9 9 10 10 9

Corn 7 6 1 0 6 0 6

Crabgrass 10 10 9 9 10 9 9 Ducksalad 2 1 1 0 2 0 0 0

Giant foxtail 10 10 9 9 10 5 9 -

Morningglory 10 10 8 5 10 9 9 -

Nutsedge 8 3 0 0 8 0 - -

Rape 9 10 8 9 9 10 9 -

Redroot pigweed 10 9 9 9 10 9 9 -

Rice 6 3 7 2 4 0 0 0

S. Flatsedge 5 3 5 3 4 0 4 0

Soybean 10 10 9 10 10 9 9 -

Sugarbeets 10 10 9 9 10 10 10 -

Velvetleaf 10 10 9 9 10 10 10 -

Wheat 7 6 3 3 5 1 1 -

Wild oats 9 10 1 1 7 2 4 -

Table B COMPOUND

Rate 62 g/ha 17 19 23 25 29 60 61

Preemergence

B. signalgrass 8 8 0 - 8 0 0

Bedstraw 7 5 2 0 7 0 -

Blackgrass 1 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 1

Crabgrass 9 8 6 4 9 2 2

Giant foxtail 8 8 7 5 9 1 1

Morningglory 0 0 0 1 6 0 1

Nutsedge 0 0 0 0 0 - 0

Rape 0 6 0 1 0 0 0

Redroot pigweed 9 9 9 0 9 0 4

Soybean 0 0 0 0 0 0 0

Sugarbeets 9 10 8 9 10 3 0

Velvetleaf 10 9 3 2 10 3 9

Wheat 0 0 0 0 0 0 0

Wild oats 0 0 0 0 0 0 0 Table B COMPOUND

Rate 31 g/ha 9 10 11 12 17 19 20 21 23 25 27 28 29 33 34 35 36 37 38 39 40 41 42 43 44 45 60 61 62

Postemergence

B. signalgrass 1 2 8 2 8 8 9 - 5 3 2 2 9 5 2 6 - - 3 2 2

Ba yardgrass 3 0 0 0 5 3 0 0 6 0 0 0 3 2 0 0 2 0 0 0 0 9 0 0 0 3 0 2 0

Bedstraw 8 7 8 7 9 8 7 8 9 9 7 7 9 6 9 9 8 8 9 5 9 8 6 7 5 4 4 - 8

Blackgrass 1 1 3 2 3 5 3 6 1 1 2 2 3 2 4 4 4 5 5 5 5 2 0 4 5 3 0 1 1

Cocklebur 9 10 9 9 10 10 9 10 9 9 9 9 10 9 10 9 9 10 10 9 10 10 9 10 9 10 9 9 8

Corn 0 0 0 0 5 5 1 3 0 0 0 0 5 1 2 0 3 3 3 2 1 2 0 1 2 2 0 3 5

Crabgrass 4 9 8 7 9 9 9 9 9 7 5 8 9 9 9 10 9 9 9 10 9 10 6 5 9 7 9 7 7

Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 0 2 0 3 0 0 0

Giant foxtail 8 9 9 7 10 10 9 9 9 7 7 6 10 9 9 10 9 9 9 10 10 10 9 10 10 10 4 6 6 o

Morningglory 8 8 9 3 9 10 9 9 8 0 1 7 9 9 8 8 9 9 8 8 9 8 8 9 8 9 8 9 9

Nutsedge 0 0 0 0 5 2 3 4 0 0 0 0 3 3 3 9 8 5 5 8 5 6 0 4 9 7 - 3 -

Rape 8 9 9 9 9 8 10 7 8 7 9 9 8 8 7 8 8 7 8 6 8 8 8 8 8 9 10 5 6

Redroot pigweed 9 9 8 9 10 10 9 9 8 4 9 8 10 9 9 9 9 9 9 9 8 8 8 10 9 9 8 9 9

Rice 2 0 0 0 1 0 0 0 5 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0

S. Flatsedge 7 0 0 0 4 2 0 0 2 2 0 0 3 6 0 0 - 0 0 3 0 3 0 5 0 3 0 2 0

Soybean 8 7 8 6 10 9 7 9 8 10 8 7 10 3 8 9 9 9 9 9 9 9 8 8 9 9 9 8 7

Sugarbeets 9 10 10 10 10 10 10 10 10 9 10 9 10 10 10 10 9 10 10 10 10 10 10 10 9 10 10 10 10

Velvetleaf 8 9 9 8 10 10 9 10 9 9 8 9 10 9 9 10 9 10 10 9 10 10 9 10 10 10 9 9 8

Wheat 0 2 2 1 4 4 2 3 1 1 0 2 5 1 3 3 2 4 5 1 4 2 0 4 1 2 1 1 4

Wild oats 0 1 2 2 5 5 6 6 0 1 1 1 6 3 5 6 4 5 7 4 6 4 0 7 2 5 1 2 3

Table B COMPOUND Rate 31 g/ha 9 10 11 12 17 19 20 21 23 25 27 28 29 33 34 35 36 37 38 39 40 41 42 43 44 45 60 61 62

Preemergence

B. signalgrass 0 0 0 0 2 1 0 - 0 - 0 3 3 0 - - - - - - - 0 0 0 - 2 0 0 0

Bedstraw 0 0 3 1 3 2 4 0 2 0 4 4 6 4 0 1 0 1 0 0 0 0 0 0 0 2 0 - 0

Blackgrass 0 2 0 0 0 1 0 0 0 0 2 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 4 0 0 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 1 0

Crabgrass 1 1 3 2 6 5 8 6 6 1 0 2 8 4 6 3 6 9 6 3 4 8 1 1 3 6 0 1 1

Giant foxtail 2 3 6 2 5 3 2 2 4 2 0 3 3 0 1 2 3 1 0 1 2 0 0 0 4 0 0 0 1

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 0 5 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 - 0 0 6 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 σ

Rape 0 0 0 0 0 6 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 3 0 0 0 0

Redroot pigweed 0 0 4 4 8 6 0 0 2 0 0 0 8 2 5 2 0 3 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0

Sugarbeets 6 2 7 2 9 9 3 6 7 6 6 2 9 3 0 0 0 6 0 6 5 0 2 0 0 0 0 0 0

Velvetleaf 4 4 7 5 10 10 8 10 0 0 4 6 10 7 0 6 6 6 6 6 6 0 0 7 5 0 0 3 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0

Table B COMPOUND

Rate 16 g/ha 9 10 11 12 17 19 20 21 23 25 27 28 29 33 34 35 36 37 38 39 40 41 42 43 44 45 60 61 62

Postemergence

B. signalgrass 1 1 2 1 8 7 2 - 2 2 1 1 9 2 2 4 - - 0 0 1

Bamyardgrass 0 0 0 0 2 1 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 3 0 0 0 1 0 0 0

Bedstraw 7 6 5 7 9 8 1 8 8 9 6 7 9 6 9 8 8 8 8 4 9 8 5 7 2 3 4 - 7

Blackgrass 0 0 0 1 2 2 1 3 1 0 0 1 1 2 3 2 2 3 2 5 2 2 0 1 3 2 0 0 1

Cocklebur 9 9 9 8 9 10 9 10 9 9 8 8 10 9 9 9 9 10 10 9 9 9 8 9 9 10 8 9 8

Corn 0 0 0 0 4 4 1 2 0 0 0 0 0 1 1 0 1 2 2 1 1 1 0 0 1 1 0 0 4

Crabgrass 3 8 4 3 7 8 7 9 9 6 5 8 8 6 9 9 9 9 9 9 9 9 4 5 9 7 8 7 7

Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 2 0 2 0 0 0

Giant foxtail 8 7 4 3 9 7 3 9 9 3 4 6 10 7 9 10 9 5 4 9 9 7 4 9 9 10 4 5 4

8 7 8 8 9 8 9 9 σ

Morningglory 3 0 2 3 9 9 8 8 7 0 1 6 10 5 7 8 5 8 8 8 8

Nutsedge 0 0 0 0 5 1 0 3 0 0 0 0 3 2 - 6 2 5 - 0 - 2 0 4 3 3 0 - -

Rape 8 7 7 6 5 6 3 7 7 6 7 5 7 6 4 3 6 6 4 5 1 5 8 6 1 6 2 1 6

Redroot pigweed 9 9 8 9 9 9 9 8 5 3 8 8 10 9 9 7 9 9 9 6 7 8 6 7 8 9 8 6 7

Rice 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

S. Flatsedge 0 0 0 0 3 1 0 0 1 0 0 0 2 2 0 0 0 0 0 0 0 2 0 3 0 2 0 0 0

Soybean 8 6 7 4 9 9 5 8 7 8 4 5 9 3 8 8 9 8 8 8 8 9 8 8 8 9 - 7 6

Sugarbeets 9 10 9 9 10 10 10 10 9 9 10 9 10 10 9 10 9 9 10 9 9 9 9 10 9 10 10 9 9

Velvetleaf 7 7 3 7 10 10 9 10 9 9 5 8 10 9 9 10 9 10 9 9 10 10 9 8 9 10 9 9 8

Wheat 0 0 0 0 2 1 0 3 1 0 0 0 1 1 1 1 1 2 1 0 1 2 0 1 0 1 0 0 3

Wild oats 0 0 1 1 4 3 2 3 0 0 0 0 3 2 4 3 2 3 3 3 3 3 0 0 2 3 0 1 1

Table B COMPOUND

Rate 16 g/ha 9 10 11 12 17 19 20 21 23 25 27 28 29 33 34 35 36 37 38 39 40 41 42 43 44 45 60 61 62

Preemergence

B. signalgrass 0 0 0 0 0 0 0 - 0 - 0 0 0 0 - - - - - - - 0 0 0 - 0 0 0 0

Bedstraw 0 0 0 0 0 0 0 0 1 0 0 - 3 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0

Crabgrass 1 1 1 0 3 3 3 3 4 0 0 1 5 2 2 1 2 6 6 3 0 6 0 0 2 1 0 0 0

Giant foxtail 2 1 0 0 0 2 1 1 2 0 0 1 2 0 0 0 0 1 0 0 0 0 0 0 1 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

(T

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Redroot pigweed 0 0 0 0 7 0 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sugarbeets 2 0 0 2 7 0 1 0 7 2 2 0 5 1 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0

Velvetleaf 2 0 2 3 1 3 6 8 0 0 2 1 6 5 0 5 1 3 5 2 0 0 0 6 5 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oats 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table B COMPOUND

Rate 8 g/ha 9 10 11 12 17 19 20 21 23 25 27 28 29 33 34 35 36 37 38 39 40 41 42 43 44 45 60 61 62

Postemergence

B. signalgrass 0 0 0 0 3 7 1 - 2 1 0 0 2 2 1 2 - - 0 0 0

Bamyardgrass 0 0 0 0 1 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Bedstraw 7 1 5 6 7 8 1 8 8 8 3 3 5 5 4 8 3 7 8 3 7 4 5 4 2 2 - 1 -

Blackgrass 0 0 0 0 0 0 0 1 0 0 0 0 0 1 2 2 2 1 1 1 2 2 0 0 2 2 0 0 0

Cocklebur 8 6 7 6 10 10 9 9 8 8 5 7 10 9 9 9 9 10 10 9 8 9 7 9 9 10 8 8 7

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0

Crabgrass 3 2 3 2 3 8 5 8 7 6 3 3 8 6 7 8 9 9 9 9 8 5 3 4 6 7 4 7 4

Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Giant foxtail 3 4 4 1 9 2 2 3 9 3 4 3 9 7 1 9 3 5 4 8 3 4 4 7 8 10 1 5 1

Morningglory 0 0 0 0 9 9 5 3 2 0 1 1 10 5 7 6 5 6 7 8 7 8 2 1 7 9 6 8 8 σ

Nutsedge 0 0 0 0 2 0 0 3 0 0 0 0 0 1 - - 0 3 - 0 - 0 0 0 3 2 - 0 -

Rape 5 2 3 2 2 0 2 2 7 2 3 4 0 4 2 2 4 2 2 2 0 0 2 0 0 0 0 0 0

Redroot pigweed 7 8 7 5 9 8 8 7 2 2 7 7 8 9 8 7 8 9 7 6 7 8 6 6 8 8 2 - 7

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

S. Flatsedge 0 0 0 0 2 1 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0

Soybean 5 4 3 3 8 7 4 8 6 7 2 2 8 3 7 7 8 8 6 8 7 7 4 8 7 8 6 6 5

Sugarbeets 9 9 9 9 10 10 10 9 9 9 8 9 10 9 9 10 9 9 9 9 9 8 8 9 9 9 10 9 9

Velvetleaf 5 2 1 1 10 10 9 9 8 7 4 3 10 9 5 9 9 10 9 9 9 9 4 8 9 10 9 9 4

Wheat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 1 0 0 0 0 0 1 0 0 0 0 0 0 3

Wild oats 0 0 0 0 2 1 0 2 0 0 0 0 2 1 2 3 1 2 0 2 1 2 0 0 0 2 0 0 0

Table B COMPOUND

Rate 4 g/ha 9 10 11 12 20 21 27 28 33 34 35 36 37 38 39 40 41 42 43 44 45 62

Postemergence

B. signalgrass 0 0 0 0 1 - 0 0 1 1 1 - - 0

Bamyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -

Bedstraw 6 1 4 1 1 8 3 3 5 4 8 3 7 7 2 6 0 2 4 1 0 0

Blackgrass 0 0 0 0 0 0 0 0 0 1 2 1 0 0 1 0 0 0 0 0 0 0

Cocklebur 8 3 4 5 9 9 3 6 8 8 8 7 8 9 8 6 6 4 8 8 8 7

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 2 1 1 1 3 4 2 1 3 5 8 8 5 8 7 3 3 1 2 6 3 4

Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -

Giant foxtail 2 2 1 1 1 3 2 2 2 1 9 1 4 2 2 0 3 0 2 8 7 0 o

Morningglory 0 0 0 0 1 3 0 0 4 6 5 0 5 1 3 4 5 0 0 3 3 3

Nutsedge 0 0 0 0 0 0 0 0 0 - - 0 - - 0 0 0 0 0 - 2 -

Rape 3 0 0 0 0 0 2 2 1 2 0 1 1 0 1 0 0 0 0 0 0 0

Redroot pigweed 7 2 7 5 8 7 5 7 8 8 5 7 6 7 6 6 6 2 6 7 7 7

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -

S. Flatsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 -

Soybean 2 2 3 1 2 7 1 2 2 5 5 7 7 6 6 4 6 3 7 4 6 5

Sugarbeets 9 8 8 7 9 9 8 8 9 9 10 9 9 8 9 9 4 8 9 9 9 9

Velvetleaf 1 1 1 1 8 9 0 2 9 - 9 9 9 9 9 7 9 2 8 9 10 4

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3

Wild oats 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0

Test C

Seeds of bamyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), varieties of com (Zea mays designated 'Com 2' and 'Com 5'), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), 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), varieties of soybean (Glycine max designated 'Soybean 1 ' and 'Soybean 2'), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a 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 immediatley 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.

Table C COMPOUND

Rate 70 g/ha 1 2 3 6 7 8 13 14 15 24 29 30 POSTEMERGENCE

Bamyardgrass 100 85 100 100 80 85 100 100 100 85 100

Bindweed 85 85 85 90 70 80 85 100 100 80 100 80

Blk nightshade 80 100 100 100 - 100 85 85 95 70 100 90

Cassia 25 30 60 75 50 30 50 20 20 35 50 5

Cocklebur 100 100 100 100 80 100 100 100 100 100 100 95

Corn 2 60 75 70 60 0 65 40 0 0 90 0 20

Corn 5 10 0 0 0 0 10 35 5 10 45 0 10

Cotton 100 100 100 100 80 80 100 100 100 85 100 95

Crabgrass 90 80 90 100 100 100 100 100 100 100 100 100

Fall panicum 100 100 100 100 100 100 100 100 100 100 100 100 Giant foxtail 100 95 100 100 100 100 100 100 100 100 100 100 Green foxtail 100 100 100 100 100 100 100 100 100 100 100 100 Jimsonweed 100 100 100 100 100 100 100 100 100 100 100 100 Johnsongrass - 40 100 100 100 100 100 100 95 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 95 Morningglory 100 100 100 100 100 100 100 100 100 100 100 90 Nutsedge 0 0 0 90 25 15 20 55 30 20 30 35 Pigweed 100 100 100 100 40 60 100 100 100 100 100 85 Prickly sida 20 55 70 75 25 70 100 100 100 85 85 100 Ragweed 85 100 100 100 80 60 100 100 100 65 100 95 Shattercane 85 70 70 100 20 10 100 100 100 100 100 95 Signalgrass 100 100 30 100 70 90 100 85 80 100 70 90 Smartweed Soybean 1 100 100 100 100 100 100 100 100 100 85 100 90 Soybean 2 100 100 100 100 100 75 100 100 100 85 100 95 Sunflower 100 100 100 100 100 100 100 100 100 100 100 95 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 Wild proso 100 100 100 100 100 100 - 100 - 100 100 100 Woolly cupgrass 65 85 75 85 65 85 100 100 100 85 100 100 Yellow foxtail 100 100 100 100 100 100 100 100 100 100 100 100

Table C COMPOUND

Rate 35 g/ha 1 2 3 6 8 13 14 15 24 29 30

POSTEMERGENCE

Bamyardgrass 100 85 100 100 80 80 100 100 100 80 100 100

Bindweed 80 85 75 70 60 70 85 100 75 75 80 70

Blk nightshade 80 80 85 75 50 50 80 80 80 50 80 90

Cassia 25 30 60 60 25 20 20 20 20 25 50

Cocklebur 100 100 90 85 70 100 100 100 100 80 100 90

Corn 2 50 50 25 25 0 0 15 0 0 15 0 5

Corn 5 50 25 20 - 0 10 15 5 5 10 0 0

Cotton 100 100 100 100 75 70 100 100 100 50 100 90

Crabgrass 85 80 85 100 100 80 85 100 100 85 100 95

Fall panicum 100 100 100 100 100 100 100 100 100 100 100 100

Giant foxtail 90 90 100 100 100 100 100 100 100 80 100 100

Green foxtail 100 100 100 100 100 100 100 100 100 75 100 100

Jimsonweed 100 100 100 100 100 100 100 100 100 100 100 100

Johnsongrass - 25 80 100 100 100 80 30 90 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 90 Morningglory 80 75 100 80 70 70 100 100 100 100 100 90 Nutsedge 0 0 0 0 15 15 15 30 25 15 25 30 Pigweed 80 85 80 90 20 60 100 100 100 50 100 50 Prickly sida 20 55 35 40 10 25 100 85 85 10 80 100 Ragweed 70 70 85 100 80 60 100 100 100 60 100 95 Shattercane 45 70 75 100 45 75 100 75 100 70 100 90 Signalgrass 0 40 20 100 55 85 100 45 80 55 70 90 Smartweed Soybean 1 100 100 100 100 100 100 100 100 85 65 100 90 Soybean 2 100 70 100 100 100 75 100 100 100 60 100 80 Sunflower 100 100 100 100 100 100 100 100 100 80 100 90 Velvetleaf 100 100 100 100 100 100 100 100 100 80 100 100 Wild proso 100 100 100 100 100 100 - 100 - 100 100 100 Woolly cupgrass 55 70 70 85 65 75 75 85 85 75 85 100 Yellow foxtail 100 100 90 100 80 100 100 100 100 80 95 100

Table C COMPOUND

Rate 17 g/ha 1 2 3 6 8 13 14 15 24 29 30

POSTEMERGENCE

Bamyardgrass 100 85 90 100 80 100 100 80 80 85 100

Bindweed 60 70 65 70 50 60 85 75 75 40 75 70

Blk nightshade 80 80 80 80 50 40 80 80 80 50 80 85

Cassia 15 25 25 25 20 20 20 20 0

Cocklebur 75 75 85 85 50 100 100 100 90 70 100 90

Corn 2 0 0 0 0 0 0 5 0 0 10 0 0

Corn 5 30 0 0 0 0 5 5 0 0 0 0 0

Cotton 100 80 75 100 50 70 100 100 100 40 100 80

Crabgrass 70 55 75 80 50 85 80 85 80 50 80 90

Fall panicum 90 100 60 80 100 100 100 100 85 100 100 90

Giant foxtail 85 90 100 100 85 100 100 100 80 80 100 100

Green foxtail 100 100 100 100 60 85 100 100 100 70 100 95

Jimsonweed 100 100 100 100 80 100 100 100 100 100 100 100

Johnsongrass 25 15 80 100 25 30 15 70

Lambsquarters 100 100 100 100 85 100 100 100 100 100 100 70

Morningglory 70 75 80 70 60 65 100 90 80 100 100 80

Nutsedge 0 0 0 0 15 10 10 15 15 15 15 10

Pigweed 85 80 65 80 20 50 100 85 100 20 100 50 Prickly sida 15 20 25 40 10 15 75 80 100 10 80 70

Ragweed 70 80 - 85 50 40 100 100 100 40 100 90

Shattercane 15 55 30 30 45 50 45 65 60 65 65 50

Signalgrass 20 20 15 90 55 85 100 40 35 15 80 50

Smartweed

Soybean 1 100 100 100 100 80 60 100 70 70 60 100 90

Soybean 2 100 100 100 80 65 75 100 75 100 30 85 70

Sunflower 100 100 100 100 100 60 100 70 80 75 75 80

Velvetleaf 100 100 100 100 85 70 100 100 100 60 100 100

Wild proso 100 100 100 100 100 100 - 95 - 100 100 100

Woolly cupgrass 25 25 35 55 55 40 70 75 65 65 80 80

Yellow foxtail 85 100 85 100 75 80 100 100 75 75 95 90

Table C COMPOUND

Rate 8 g/ha 1 2 3 6 7 8 13 14 15 24 29 30

POSTEMERGENCE

Bamyardgrass 100 85 100 100 75 80 100 90 75 75 85 95

Bindweed 60 55 60 60 40 55 70 80 75 10 75 50

Blk nightshade 80 75 75 75 - 20 80 75 80 40 80 80

Cassia 0 15 15 20 - - 20 20 20 - 10 -

Cocklebur 75 100 80 75 50 65 85 100 90 60 100 90

Corn 2 0 0 0 0 0 0 0 0 0 10 0 0

Corn 5 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 65 70 100 85 15 70 80 80 70 20 85 75

Crabgrass 50 45 45 50 25 30 80 75 70 15 80 80

Fall panicum 90 100 20 100 100 100 85 85 100 100 100 80

Giant foxtail 80 90 100 100 85 85 80 85 85 70 80 90

Green foxtail 100 100 100 50 55 70 65 70 85 40 85 -

Jimsonweed 100 100 100 100 100 100 80 85 100 65 100 90

Johnsongrass - - - - 0 55 70 40 0 15 10 30

Lambsquarters 100 100 100 100 80 30 100 100 100 60 100 60

Morningglory 70 70 65 65 60 60 100 85 80 60 80 80

Nutsedge 0 0 0 0 15 10 0 10 5 15 10 0

Pigweed 65 75 50 65 70 60 80 85 85 20 80 50

Prickly sida 15 20 15 15 10 15 75 65 75 5 100 50

Ragweed 70 80 - 50 50 25 85 100 100 40 100 90

Shattercane 0 0 15 15 20 40 55 20 55 65 45 50

Signalgrass 0 15 0 25 50 25 50 20 20 0 20 30 Smartwee_d - - - - - - - - - - - -

Soybean 1 85 65 100 100 40 50 80 75 70 20 85 70

Soybean 2 100 65 60 80 45 50 75 70 50 30 75 70

Sunflower 100 100 100 100 25 45 60 65 60 20 70 75

Velvetleaf 100 70 100 70 10 50 100 100 100 45 100 100

Wild proso 100 100 100 100 85 85 - 80 - 65 90 95

Woolly cupgrass 15 15 15 15 15 55 70 70 55 65 65 60

Yellow foxtail 80 100 85 70 75 75 75 60 65 70 90 80

Test D

Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were in the 1- to 4-leaf stage (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence 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), blackgrass 2 (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed (Stellaria media), common poppy (Papaver rhoeas), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium 2 (Galium aparine), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape 1 (Brassica napus), redroot pigweed

(Amaranthus retroflexus), Russian thistle (Salsola kali), scentless chamomile (Matricaria inodora), spring barley (Hordeum vulgare), sugar beet (Beta vulgaris), sunflower (Helianthus annuus), ivyleaf speedwell (Veronica hederaefolia), wheat (Triticum aestivum), spring wheat (Triticum aestivum), winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), stages of wild oat (Avenafatua, designated 1 or 2 based upon the leaf stage of the wild oat at the time of treatment), windgrass (Apera spica-ventϊ) and winter barley (Hordeum vulgare).

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 D, 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 D COMPOUND Table D COMPOUND

Rate 125 g/ha 4 5 Rate 62 g/ha 4 5 16 23 29 POSTEMERGENCE POSTEMERGENCE

Annual bluegras 20 45 Annual bluegras 10 30 20 35 60

Barley (winter) 5 10 Barley (winter) 0 5 10 2 10

Blackgrass (2) 20 20 Blackgrass (2) 10 15 10 20 50

Blk nightshade 100 100 Blk nightshade 100 90 100 90 100

Chickweed 90 100 Chickweed 10 75 100 100 100

Common poppy 85 100 Common poppy 90 100 90 75 100

Deadnettle 100 100 Deadnettle 100 100 100 100 100

Downy brome 0 0 Downy brome 0 0 0 0 20

Field violet 100 100 Field violet 100 100 100 100 100

Galium (2) 65 70 Galium (2) 60 60 60 70 60

Green foxtail 100 100 Green foxtail 100 100 100 100 100

I. Ryegrass 10 40 I. Ryegrass 5 20 5 20 10

Jointed goatgra 0 10 Jointed goatgra 0 5 0 5 0

Kochia 85 85 Kochia 75 80 100 80 100

Lambsquarters 80 95 Lambsquarters 75 80 100 80 100

LS canarygrass 10 30 LS canarygrass 10 10 70 15 60

Rape (1) 85 75 Rape ( 1 ) 75 90 100 80 85

Redroot pigweed 85 90 Redroot pigweed 65 75 80 85 100

Russian thistle 60 100 Russian thistle 60 80 80 - 80

Scentless chamo 70 85 Scentless chamo 65 65 60 70 85

Spring Barley 5 5 Spring Barley 0 0 0 2 5

Sugar beet 100 100 Sugar beet 100 100 100 100 100

Sunflower 70 75 Sunflower 60 70 90 75 100

Veronica hedera 100 90 Veronica hedera 100 80 100 90 100 Wheat Wheat - - - - -

Wheat (spring) 20 30 Wheat (spring) 10 20 20 20 25

Wheat (winter) 10 20 Wheat (winter) 0 10 10 10 10

Wild buckwheat 85 85 Wild buckwheat 60 55 70 85 75

Wild mustard 85 90 Wild mustard 85 85 100 100 100

Wild oat (1) 10 30 Wild oat (1) 10 10 30 15 60 Wild oat (2) Wild oat (2) - - - - -

Windgrass 0 10 Windgrass 0 10 10 0 20 Table D COMPOUND

Rate 31 g/ha 4 5 16 23 29 30 40 POSTEMERGENCE

Annual bluegras 10 20 10 20 20 40 30

Barley (winter) 0 5 10 2 10 5 10

Blackgrass (2) 10 10 10 20 20 10 10

Blk nightshade 100 80 90 85 65 80 70

Chickweed 85 75 100 100 85 80 100

Common poppy 85 85 80 75 85 100 100

Deadnettle 100 75 100 100 95 80 65

Downy brome 0 0 0 0 20 0 10

Field violet 100 85 80 100 60 40 85

Galium (2) 55 60 60 65 50 60 60

Green foxtail 60 85 85 80 90 90 95

I. Ryegrass 10 10 0 10 10 5 20

Jointed goatgra 0 0 10 0 20 10 10

Kochia 60 70 100 70 75 70 85

Lambsquarters 75 75 100 80 100 100 100

LS canarygrass 10 20 60 10 30 50 60

Rape (1) 60 75 75 80 60 60 50

Redroot pigweed 60 75 - 70 75 100 90

Russian thistle 50 60 70 - 50 60 70

Scentless chamo 60 65 - 60 100 - 70

Spring Barley 0 0 0 0 10 0 0

Sugar beet 90 100 100 100 100 100 100

Sunflower 50 60 75 65 60 60 60

Veronica hedera 100 80 100 75 70 80 95

Wheat - -

Wheat (spring) 10 10 10 15 15 10 15

Wheat (winter) 0 5 0 5 10 10 0

Wild buckwheat 40 70 70 55 30 30 65

Wild mustard 80 75 100 75 98 100 100

Wild oat (1) 0 10 20 20 55 40 40

Wild oat (2) - - - - - - -

Windgrass 0 0 0 5 0 10 20 Table D COMPOUND Table D COMPOUND

Rate 16 g/ha 16 23 29 30 40 Rate 8 g/ha 29 30 40

POSTEMERGENCE POSTEMERGENCE

Annual bluegras 5 10 20 20 5 Annual bluegras 5 10 5

Barley (winter) 0 10 5 0 20 Barley (winter) 5 5 20

Blackgrass (2) 10 10 10 5 10 Blackgrass (2) 10 0 5

Blk nightshade 80 70 80 70 65 Blk nightshade 60 60 55

Chickweed 100 75 100 85 85 Chickweed 50 60 50

Common poppy 60 70 70 100 85 Common poppy 50 70 70

Deadnettle 100 100 100 70 60 Deadnettle 60 65 45

Downy brome 0 0 0 0 0 Downy brome 2 0 0

Field violet 70 75 100 55 60 Field violet 40 15 60

Galium (2) 55 60 55 50 50 Galium (2) 50 40 30

Green foxtail 100 70 100 85 85 Green foxtail 70 60 70

I. Ryegrass 0 5 10 2 5 I. Ryegrass 2 0 10

Jointed goatgra 10 0 0 5 5 Jointed goatgra 10 5 2

Kochia - 60 55 50 55 Kochia 45 45 35

Lambsquarters 80 75 90 100 100 Lambsquarters 85 80 100

LS canarygrass 30 5 50 30 30 LS canarygrass 10 20 15

Rape (1) 40 60 60 30 50 Rape (1) 30 25 55

Redroot pigweed 60 60 85 75 85 Redroot pigweed 70 60 75

Russian thistle 60 - 80 50 60 Russian thistle 10 30 50

Scentless chamo 55 50 70 - - Scentless chamo 10 100 -

Spring Barley 10 0 0 0 0 Spring Barley 0 0 20

Sugar beet 100 100 100 100 100 Sugar beet 100 100 100

Sunflower 70 55 75 50 50 Sunflower 40 30 30

Veronica hedera 75 70 70 75 70 Veronica hedera 10 50 70

Wheat - - - - - Wheat - - -

Wheat (spring) 0 10 10 5 10 Wheat (spring) 0 0 20

Wheat (winter) 0 0 5 10 10 Wheat (winter) 0 0 10

Wild buckwheat 50 50 75 65 50 Wild buckwheat 55 30 30

Wild mustard 100 65 85 100 100 Wild mustard 50 70 60

Wild oat (1) 10 10 25 20 30 Wild oat (1) 10 10 20

Wild oat (2) - - - - - Wild oat (2) - - -

Windgrass 2 0 5 10 0 Windgrass 0 5 20

Claims

CLAIMS What is claimed is:

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

wherein

A is -OC(=O)-, -OC(=O)O- or -OC(=O)S-, and the directionality of the A linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the pyrazole ring and the moiety on the right side of the linkage is bonded to Q; Q is C Cjo alkyl optionally substituted with halogen, C₂-C6 alkoxyalkyl, C₂-C╬╣₀ alkenyl or C₃-C₆ cycloalkyl; or Q is phenyl, benzyl, pyridyl, furanyl or thienyl, each optionally substituted with C_j-C3 alkyl, C╬╣-C₃ alkoxy, cyano, halogen, COOH or S(=O)₂OH; or

A together with Q is -OC(=O)NR⁶R⁷; R¹ is C_rC₃ alkyl;

R² and R³ are each independently H, C1-C3 alkyl or halogen; R⁴ and R⁵ are taken together to form -O(CH₂)₂O-; or R⁴ and R⁵ are taken together with the carbon to which they are attached to form C(=O);

R⁶ is C1-C3 alkyl, C3-C4 alkenyl or phenyl optionally substituted with 1-3 C₁-C3 alkyl,

C1-C3 alkoxy, halogen or cyano; R⁷ is C_rC₃ alkyl or C3-C4 alkenyl; or

R⁶ and R⁷ are taken together to form -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂- or -CH₂CH₂OCH₂CH₂-; provided that when A is -OC(=O)- and R⁴ and R⁵ are taken together to form -O(CH₂)₂O-, then Q is other than C_rC₂ alkyl.

2. A compound of Claim 1 wherein

R⁴ and R⁵ are taken together to form -O(CH₂)₂O-

3. A compound of Claim 2 wherein

Q is C₁-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C1-C3 alkyl, C C3 alkoxy, cyano or halogen; and R² and R³ are each independently C C3 alkyl.

4. A compound of Claim 3 wherein A is -OC(=O)O-.

5. A compound of Claim 1 wherein

R⁴ and R⁵ are taken together to form C(=O).

6. A compound of Claim 5 wherein

Q is C C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C_j-C3 alkyl, C_j-C3 alkoxy, cyano or halogen; and

R² and R³ are each independently C₁-C3 alkyl.

7. A compound of Claim 6 wherein A is -OC(=O)O-.

8. The compound of Formula I which is selected from the group:

(^a) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-l-benzothiopyran-4,2'-[l,3]dioxolan]-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] (1-methylethyl) carbonate S,S-dioxide;

(b) [4-[(3,4-dihydro-5,8-dimethyl- 1 , 1 -dioxido-4-oxo-2H- 1 -benzothiopyran-6- yl)carbonyl]-l-ethyl-lH-pyrazol-5-yl] methyl carbonate;

(c) [4- [(3 ,4-dihydro-5 ,8-dimethyl- 1 , 1 -dioxido-4-oxo-2H- 1 -benzothiopyran-6- yl)carbonyl]- 1 -ethyl- lH-pyrazol-5-yl] ( 1 -methylethyl) carbonate;

(d) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-l-benzothiopyran-4,2'-[l,3]dioxolan]-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] ethyl carbonate S,S-dioxide; (e) [5-(benzoyloxy)- 1 -ethyl- 1 H-pyrazol-4-yl] (2 ,3 -dihydro-5 ,8-dimethylspiro[4H- 1 - benzothiopyran-4,2 '-[ 1 ,3]dioxolan]-6-yl)methanone S,S-dioxide;

(f) [4-[(3,4-dihydro- 1 , 1 -dioxido-4-oxo-5,8-dimethyl-2H-benzothiopyran-6- yl)carbonyl]-l-ethyl-lH-pyrazol-5-yl] cyclopropanecarboxylate; and

(g) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-l -benzothiopyran-4,2 '-[l,3]dioxolan]-6- yl)carbonyl]-l -ethyl- lH-pyrazol-5-yl] cyclopropanecarboxylate S,S-dioxide.

9. 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.

10. 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.