CA2281904A1 - 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:

v O SO

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 Ct-Ctp alkyl optionally substituted with halogen, C2-C~ alkoxyalkyl, C2-Clo alkenyl or C3-C6 cycloalkyl; or Q is phenyl, benzyl, pyridyl, furanyl or thienyl, each optionally substituted with C1-C3 alkyl, C~-C3 alkoxy, cyano, halogen, COOH or S(=O)20H; or A together with Q is -OC(=O)NR6R7;
R 1 is C t-C3 alkyl;
R2 and R3 are each independently H, C1-C3 alkyl or halogen;

R4 and RS are taken together to form -O(CH2)20-; or R~ 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, C~-C3 alkoxy, halogen or cyano;
R~ is C1-C3 alkyl or C3-C4 alkenyl; or R6 and R~ are taken together to form -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or -CH2CH20CH2CH2-;
provided that when A is -OC(=O)- and R4 and RS are taken together to form -O(CH2)20-, then Q is other than C1-C2 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, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl"
indicates that one or two of the available positions for that substituent may be alkyl 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, n-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 "C;-C~"
prefix where i and j are numbers from 1 to 10. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH30CH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH30CH2CH2 or CH3CH20CH2;
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 CH3CH2CH20CH2 and CH3CH~OCH2CH2. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH30C(=O), CH3CH20C(=O), CH3CH2CH~OC(=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. (R); ~, 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, malefic, 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 RS are taken together to form -O(CH2)20-.
Preferred 2. Compounds of Preferred 1 wherein Q is C~-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C1-C3 alkyl, Ci-C3 alkoxy, cyano or halogen; and R2 and R3 are each independently C~-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 RS are taken together to form C(=O).
Preferred 5. Compounds of Preferred 4 wherein Q is CI-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C1-C3 alkyl, Cl-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]-yl)carbonyl]-1-ethyl-1H-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]-1-ethyl-IH-pyrazol-5-yl] methyl carbonate;
(c) [4-[(3,4-dihydro-5,8-dimethyl-l,l-dioxido-4-oxo-2H I-benzothiopyran-6-yl)carbonyl]-1-ethyl-1H pyrazol-S-yl] (I-methylethyl) carbonate;
(d) [4-[(2,3-dihydro-5,8-dimethylspiro[4H 1-benzothiopyran-4,2'-[1,3]dioxolan]-yl)carbonyl]-1-ethyl-IH pyrazol-5-yl] ethyl carbonate S,S-dioxide;
(e) [5-(benzoyloxy)-1-ethyl-1H pyrazol-4-yl](2,3-dihydro-5,8-dimethylspiro[4H

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]-1-ethyl-IH pyrazol-5-yl] cyclopropanecarboxylate; and (g) [4-[(2,3-dihydro-5,8-dimethylspiro[4~1 I-benzothiopyran-4,2'-[1,3]dioxolan]-6-yl)carbonyl]-1-ethyl-IH 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 RI-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, 4, 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 I

i/ / ~ base and I
N ~ \ QC(=O)Cl (2) or Rl~ OH ~ S~ QOC(=O)Cl (3) or R3 O O Q SC(=O)Cl (4) or R~R7NC{=O)Cl (5) 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. 1H NMR spectra are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m =
multiplet, dd = doublet of doublets, dt = doublet of triplets, br s = broad singlet.

Step A: Preparation of 3-f(2,5-dimethylphen 1)~ thio)pro~anoic acid 43.4 g (1.086 mol) of sodium hydroxide was added to 230 mL of water, 75.0 g (0.543 mol) of 2,5-dimethylthiophenol (purchased from Aldrich Chemical Company) was then I O 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 1N HCl and filtered to yield 112.79 g of the title compound of Step A as a solid melting at 97-98 °C. 1H NMR {CDCl3): 8 2.3 (s,3H), 2.34 (s,3H), 2.68 (t,2H), 3.1 (t,2H), 6.9 (d, l H), 7.06-7.14 (2H).
Step B: Preparation of 2,3-dihydro-5,8-dimethyl-4H 1-benzopyran-4-one 530 mL of concentrated sulfuric acid was added to 24.91 g (0.119 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 (MgS04), filtered, and evaporated to dryness to yield 11.75 g of the title compound of Step B
as an oil. 1H NMR (CDC13): 8 2.3 (s,3H), 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-dihydro-5,8-dimethyl-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 I 0 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 (Na2S04), 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. 1H NMR
(CDC13): b 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-dihydro-5 8-dimethylspiro(4~1 1-benzothionvran-4 2'-( 1,3ldioxolanel 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 p-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 1N sodium hydroxide: saturated aqueous NaCI (2 x 600 mL) and then with saturated aqueous NaCI ( 1 x 600 mL). The organic layer was dried {Na2S04), 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). tH NMR (CDC13): 8 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~j4H I-benzothiopyran 4 2' j 1,3ldioxolane]-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 stirnng 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 pH 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 (MgS04), 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. 1H NMR (Me2S0-d6): 8 2.2 (m,SH), 2.4 (s,3H), 3.0 (m,2H), 4. I -4.2 (m,4H), 7.4 (s, l H).
Step F: Preparation of 2,3-dihydro-5 8-dimeth ~~lspiroj4H 1-ben~othio~yran-4 2'-(1,31dioxolanel-6-carboxylic acid 1 I-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 pH 2 with concentrated hydrochloric acid, and then extracted with chloroform {3 x 150 mL). The combined organic layers were dried (MgS04), 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). 1H NMR
(Me2S0-d6): S
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 1-ethyl-1~1 pyrazol-5-yl 2,3-dihydro-5,8-dimethylspirof4H 1 benzothiopyran-4,2'-f 1,31dioxolane)-6-carboxylate 1,1-dioxide 1.18 g (3.8 mmol) of the title compound of Step F, 0.99 mL (0.011 mol) of oxalyl chloride (purchased from Janssen), and 2 drops of N,N 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 SO 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-1~1-pyrazol-5-0l 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.
1H NMR (CDCl3): 8 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-dih~dro-5,8-dimethylspirof4H 1-benzothiopyran-4,2'-j1,31dioxolanl-6-yl)(I-ethyl-5-hydrox -y l~l-nyrazol-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 ( I .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 pH 1 with concentrated hydrochloric acid and extracted with methylene chloride (2 x 50 mL). The combined organic layers were dried (MgS04), filtered, and evaporated to dryness to yield 0.17 g of the title compound of Step H as a solid melting at 111 °C (dec).
1H NMR (CDC13): 8 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 f4-[(2,3-dihydro-5,8-dimethylspiro(4H 1-benzothio~yran,4,2'-(1,31dioxolanl-6-yl)carbonyl]'~-1-ethyl-IH pyrazol-5-yll (I-methylethyl) carbonate S,S-dioxide 500 mg (1.23 mmol) of the title compound of Step H and 1.50 ml (1.50 mmol) of isopropylchloroformate (1.0 M 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. ~H
NMR (CDC13): S
I .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, IH), 7.5 (s, IH).

Step A: Preparation of f4-f(2,3-dihydro-5 8-dimethylspirof4H I-ben~othiopyran 4 2'-f 1,31dioxolanl-6-yl)carbonyl}-I-ethyl-lHwrazol-5-yll ethyl carbonate SS-dioxide 400 mg ( 1.00 mmol) of the title compound of Step H 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 chromatog~raphed 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. ~H NMR (CDC13):
8 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, IH).
By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 4 can be prepared.
Table I
R

CH3 H H -OC(=O)O- CH3 CH3 CH3 H -OC{=O)O- CH3 CH3 CH3 CH3 -OC(=O)O- CH3 CH3 CH3 CI -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 Q

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- CHI

CH2CH3 CH3 CH3 -OC(=O)S- CH3 CH2CH3 CH3 Cl -OC(=O)S- CH3 CH2CH3 Cl CH3 -OC(=O}S- CH3 CH2CH3 Cl CI -OC(=O)S- CH3 CH2CH~CH3 H H -OC(=O)O- CH3 CH~CH2CH3 CH3 H -OC(=O)O- CH3 CH2CH2CH3 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 CHZCH2CH3 H H -OC{=O)S- CH3 CH2CH2CH3 CH3 H -OC(=O)S- CH3 CH2CH2CH3 CH3 CH3 -OC(=O)S- CH3 CH~CH~CH3 CH3 Cl -OC(=O)S- CH3 CH2CH2CH3 Cl CH3 -OC(=O)S- CH3 CH2CH~CH3 C1 Cl -OC(=O)S- CH3 CH3 H H -OC(=O)O- CH~CH3 CH3 CH3 H -OC(=O)O- CH2CH3 CH3 CH3 CH3 -OC(=O)O- CH2CH3 CH3 CH3 Cl -OC{=O)O- CH2CH3 CH3 C1 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 CI -OC(=O)S- CH2CH3 CH3 CI 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 CI -OC(=O)O- CH2CH3 CH2CH3 H H -OC(=O)S- CH~CH3 CH2CH3 CH3 H -OC(=O)S- CH2CH3 CH2CH3 CH3 CH3 -OC(=O)S- CH2CH3 CH2CH3 CH3 Cl -OC(=O)S- CH2CH3 CH2CH3 C1 CH3 -OC(=O)S- CH2CH3 CH2CH3 CI CI -OC(=O)S- CH2CH3 CH2CH2CH3 H H -OC(=O)O- CH2CH3 CH2CH2CH3 CH3 H -OC(=O)O- CH2CH3 CH2CH~CH3 CH3 CH3 -OC(=O)O- CH2CH3 CH2CH2CH3 CH3 CI -OC(=O)O- CH2CH3 CH2CH2CH3 CI CH3 -OC(=O)O- CH2CH3 CH2CH2CH3 Cl CI -OC(=O)O- CH2CH3 CH2CH2CH3 H H -OC(=O)S- CH2CH3 CH2CH2CH3 CH3 H -OC(=O)S- CH2CH3 CH2CH2CH3 CH3 CH3 -OC(=O)S- CH~CH3 CH2CH2CH3 CH3 C1 -OC(=O)S- CH~CH3 CHzCH2CH3 CI CH3 -OC(=O)S- CH2CH3 CH2CH2CH3 Cl CI -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 CI -OC(=O)O- CH2CH2CH3 CH3 CI CH3 -OC(=O)O- CH2CH2CH3 CH3 Cl Cl -OC(=O)O- CH2CH~CH3 CH3 H H -OC(=O)S- CH2CH2CH3 CH3 CH3 H -OC(=O)S- CH2CH2CH3 CH3 CH3 CH3 -OC(=O)S- CH2CH~CH3 CH3 CH3 Ci -OC(=O)S- CH2CH2CH3 CH3 Cl CH3 -OC(=O)S- CH2CH2CH3 CH3 C1 C1 -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 C1 -OC(=O)O- CH2CH2CH3 CH2CH3 Cl CH3 -OC(=O)O- CH2CH2CH3 CHZCH3 Cl Cl -OC(=O)O- CH2CH2CH3 CH2CH3 H H -OC(=O)S- CH2CH2CH3 CH2CH3 CH3 H -OC(=O)S- CH2CH2CH3 CH2CH3 CH3 CH3 -OC(=O)S- CH2CH2CH3 CH2CH3 CH3 Cl -OC(=O)S- CH2CH2CH3 CH2CH3 Cl CH3 -OC(=O)S- CH2CH2CH3 CH2CH3 C1 Cl -OC(=O)S- CH2CH2CH3 CH2CH2CH3 H H -OC(=O)O- CH2CH2CH3 CH2CH2CH3 CH3 H -OC(=O)O- CH2CH2CH3 CH2CH2CH3 CH3 CH3 -OC(=O)O- CH2CH~CH3 CH2CH2CH3 CH3 Cl -OC(=O)O- CH~CHZCH3 CH2CH2CH3 Cl CH3 -OC(=O)O- CH~CH~CH3 CH2CH2CH3 CI Cl -OC(=O)O- CH~CH~CH3 CH2CH2CH3 H H -OC(=O)S- CH2CH2CH3 CHZCH2CH3 CH3 H -OC(=O)S- CH~CH2CH3 CH2CHZCH3 CH3 CH3 -OC(=O)S- CH2CH2CH3 CH~CH2CH3 CH3 C1 -OC(=O)S- CH2CH2CH3 CH2CH2CH3 Cl CH3 -OC(=O)S- CH2CH2CH3 CH2CH2CH3 Cl Cl -OC(=O)S- CH2CH2CH3 CH3 H H -OC(=O)O- cyclo-propyl CH3 CH3 H -OC(=O)O- cyclo-propyl CH3 CH3 CH3 -OC(=O}O- cyclo-propyl CH3 CH3 Cl -OC(=O)O- cvclo-propyl CH3 Cl CH3 -OC(=O)O- cyclo-propyl CH3 Cl Cl -OC(=O)O- cyclo-propyl CH3 H H -OC(=O)S- cyclo-propyl CH3 CH3 H -OC(=O)S- cyclo-propyl CH3 CH3 CH3 -OC(=O)S- cyclo-propyl CH3 CH3 Cl -OC(=O)S- cyclo-propyl CH3 CI CH3 -OC(=O)S- cyclo-propyl CH3 Cl Cl -OC(=O)S- cvclo-propyl CH2CH3 H H -OC(=O)O- cyclo-propyl WO 98/49159 PCT/US98i07978 CH2CH3 CH3 H -OC(=O)O- cyclo-propyl CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl CH2CH3 CH3 CI -OC(=O)O- cyclo-propyl CH~CH3 CI CH3 -OC(=O)O- cyclo-propyl CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl CH2CH3 H H -OC(=O)S- cyclo-propyl CHZCH3 CH3 H -OC(=O)S- cyclo-propyl CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl CH2CH3 CH3 Cl -OC(=O)S- cyclo-propyl CH2CH3 Cl CH3 -OC(=O)S- cyclo-propyl CH2CH3 Cl Cl -OC(=O)S- cyclo-propyl CH2CH2CH3 H H -OC(=O)O- cyclo-propyl CH~CH2CH3 CH3 H -OC(=O)O- cyclo-propyl CH2CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl CH2CH2CH3 CH3 CI -OC(=O)O- cyclo-propyl CH2CH2CH3 CI CH3 -OC(=O)O- cyclo-propyl CH2CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl CH~CH2CH3 H H -OC(=O)S- cyclo-propyl CH2CH2CH3 CH3 H -OC(=O)S- cyclo-propyl CH2CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl CH2CH~CH3 CH3 Cl -OC(=O)S- cyclo-propyl CH2CH2CH3 Cl CH3 -OC(=O)S- cyclo-propyl CH2CH2CH3 Cl Cl -OC(=O)S- cyclo-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=CHI

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 CI CH3 -OC(=O)S- CH=CH2 CH3 Cl C1 -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=CHZ

CH2CH3 CH3 CI -OC(=O)O- CH=CH2 CH2CH3 CI 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 CI -OC(=O)S- CH=CH2 CH2CH3 CI CH3 -OC{=O)S- CH=CH2 CHzCH3 CI CI -OC{=O)S- CH=CH2 CHZCH2CH3 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 CI -OC(=O)O- CH=CH2 CH2CH2CH3 CI CH3 -OC(=O)O- CI-I=CHI

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 CH.,CH2CH3 CH3 CI -OC(=O)S- CH=CHI

CH2CH'CH3 CI CH3 -OC(=O)S- CH=CH2 CH~CH2CH3 C1 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 CI-I3 -OC(=O)O- C(=CH2)CH3 CH3 CH3 CI -OC(=O)O- C(=CH2)CH3 CH3 Cl CH3 -OC(=O)O- C(=CH2)CH3 CH3 CI CI -OC(=O)O- C(=CH2)CH3 CH3 H H -OC(=O)S- C(=CH~)CH3 CH3 CH3 H -OC(=O)S- C(=CH2)CH3 CH3 CH3 CH3 -OC(=O)S- C(=CH~)CH3 CH3 CH3 CI -OC(=O)S- C(=CH2)CH3 CH3 CI CH3 -OC(=O)S- C(=CH2)CH3 CH3 CI CI -OC(=O)S- C(=CH')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 CI CH3 -OC(=O)O- C(=CH2)CH3 CH2CH3 C1 C1 -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 CH2CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3 CH2CH2CH3 CH3 CH3 -OC(=O)O- C(=CH2)CH3 CH2CH2CH3 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 CH2CH2CH3 CH3 Cl -OC(=O)S- C(=CH2)CH3 CHZCHZCH3 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- CHZCH=CH2 CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2 CH3 CH3 CI -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- CH~CH=CH2 CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2 CH3 CH3 C1 -OC(=O)S- CH2CH=CH2 CH3 C1 CH3 -OC(=O)S- CH~CH=CH' CH3 CI CI -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- CH~CH=CH2 CH2CH3 Cl CH3 -OC(=O)O- CH2CH=CHI

CH2CH3 Cl Cl -OC(=O)O- CH2CH=CH' CH2CH3 . H H -OC(=O)S- CH~CH=CH2 CH2CH3 CH3 H -OC(=O)S- CH2CH=CH2 CHZCH3 CH3 CH3 -OC{=O)S- CH2CH=CH2 CH2CH3 CH3 CI -OC(=O)S- CH2CH=CH2 CH2CH3 C1 CH3 -OC(=O)S- CH2CH=CH2 CH~CH3 CI 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 CI -OC(=O)O- CH2CH=CH2 CH2CH2CH3 CI CH3 -OC(=O)O- CH2CH=CH2 CH2CH2CH3 CI Cl -OC(=O)O- CH2CH=CH2 CH2CH2CH3 H H -OC(=O)S- CH2CH=CH2 CH2CH~CH3 CH3 H -OC(=O)S- CH2CH=CH2 CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2 CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH=CH2 CH2CH2CH3 C1 CH3. -OC(=O)S- CH2CH=CH2 CH2CH2CH3 C1 CI -OC(=O)S- CH2CH=CHZ

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 CI CH3 -OC(=O)O- CH=CHCH3 CH3 CI CI -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 CI -OC{=O)S- CH=CHCH3 CH3 CI CH3 -OC{=O)S- CH=CHCH3 CH3 CI 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 CI CI -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 CI Cl -OC(=O)S- CH=CHCH3 CH2CH2CH3 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 CI CH3 -OC(=O)O- CH=CHCH3 CH2CH2CH3 Cl C1 -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 CH2CH2CH3 CI 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 CI 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 CI -OC(=O)S- phenyl CH3 Cl CH3 -OC(=O)S- phenyl CH3 CI Cl -OC(=O)S- phenyl CH2CH3 H H -OC(=O)O- phenyl CH2CH3 CH3 H -OC(=O)O- phenyl CH~CH3 CH3 CH3 -OC(=O)O- phenyl CHZCH3 CH3 Cl -OC(=O)O- phenyl CH2CH3 Cl CH3 -OC(=O)O- phenyl CH2CH3 Cl CI -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 CHZCH3 Cl C1 -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 CH2CH~CH3 CH3 H -OC(=O)S- phenyl CH2CH2CH3 CH3 CH3 -OC(=O)S- phenyl CH2CH2CH3 CH3 Cl -OC(=O)S- phenyl CH2CH~CH3 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 CI 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 CH~CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl CH2CH3 CH3 Cl -OC(=O)O- 2-pyridinyl CH2CH3 CI 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 CH~CH3 Cl CH3 -OC(=O)S- 2-pyridinyl CH~CH3 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 CH2CH2CH3 CH3 C1 -OC(=O)O- 2-pyridinyl CH2CH2CH3 Cl CH3 -OC(=O)O- 2-pyridinyl CH2CH2CH3 CI Cl -OC(=O)O- 2-pyridinyl CH2CH2CH3 H H -OC(=O)S- 2-pyridinyl CH2CH2CH3 CH3 H -OC(=O)S- 2-pyridinyl CH2CH~CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl CH2CH2CH3 CH3 Cl -OC(=O)S- 2-pyridinyl CH2CH2CH3 C1 CH3 -OC(=O)S- 2-pyridinyl CH2CH2CH3 CI 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 CHI -OC(=O)S- 2-furanyl CH3 CH3 CI -OC(=O)S- 2-furanyl CH3 CI CH3 -OC(=O)S- 2-furanyl CH3 Cl C1 -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 CH~CH3 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 C1 Cl -OC(=O)S- 2-furanyl CH2CH2CH3 H H -OC(=O)O- 2-furanyl CH2CH2CH3 CH3 H -OC(=O)O- 2-furanyl CH2CH~CH3 CH3 CH3 -OC(=O)O- 2-furanyl CH2CH2CH3 CH3 C1 -OC(=O)O- 2-furanyl CH2CH2CH3 Cl CH3 -OC(=O)O- 2-furanyl CH2CH2CH3 Cl Cl -OC(=O)O- 2-furanyl CH2CH2CH3 H H -OC(=O)S- 2-furanyl CH2CH~CH3 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 C1 -OC(=O)O- 2-thienyl CH3 Cl CH3 -OC(=O)O- 2-thienyl CH3 CI 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 C1 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 CI -OC(=O)O- 2-thienyl CH~CH3 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 CI -OC(=O)S- 2-thienyl CH2CH3 C1 CH3 -OC(=O)S- 2-thienyl CH2CH3 Cl C1 -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 CH2CHZCH3 CH3 Cl -OC(=O)O- 2-thienyl CH2CHZCH3 Cl CH3 -OC(=O)O- 2-thienyl CH2CH2CH3 C1 Cl -OC(=O)O- 2-thienyl CHZCH2CH3 H H -OC(=O)S- 2-thienyl CH2CH~CH3 CH3 H -OC(=O)S- 2-thienyl CH2CHZCH3 CH3 CH3 -OC(=O)S- 2-thienyl CH2CH~CH3 CH3 Cl -OC(=O)S- 2-thienyl CH2CH2CH3 Cl CH3 -OC(=O)S- 2-thienyl CH,CH2CH3 C1 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 C1 CH3 -OC(=O)- CH3 CH3 CI CI -OC(=O)- CH3 CH2CH3 H H -OC(=O)- CH3 CH2CH3 CH3 H -OC(=O)- CH3 CHZCH3 CH3 CH3 -OC(=O)- CH3 CH2CH3 CH3 CI -OC(=O)- CH3 CH~CH3 CI CH3 -OC(=O)- CH3 CH2CH3 CI CI -OC(=O)- CH3 CH2CH2CH3 H H -OC(=O)- CH3 CH2CH~CH3 CH3 H -OC(=O)- CH3 CH2CH2CH3 CH3 CHI -OC(=O)- CH3 CH2CH~CH3 CH3 C1 -OC(=O)- CH3 CH2CH2CH3 Cl CH3 -OC(=O)- CH3 CH2CH~CH3 Cl Cl -OC(=O)- CH3 CH3 H H -OC(=O)- CH2CH3 CH3 CH3 H -OC(=O)- CH~CH3 CH3 CH3 CH3 -OC(=O}- CH2CH3 CH3 CH3 C1 -OC(=O)- CH~CH3 CH3 Cl CHI -OC(=O)- CH2CH3 CH3 C1 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 CI CH3 -OC(=O)- CH2CH3 CH2CH3 C1 C1 -OC(=O)- CI-12CH3 CH2CHZCH3 H H -OC(=O)- CH~CH3 CH2CH2CH3 CH3 H -OC(=O)- CH2CH3 CH2CH2CH3 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)- CHZCH2CH3 CH3 CH3 CH3 -OC(=O)- CH2CH2CH3 CH3 CH3 CI -OC(=O)- CH2CH2CH3 CH3 Cl CH3 -OC(=O)- CH2CH2CH3 CH3 Cl Cl -OC(=O)- CH2CH2CH3 CH2CH3 H H -OC(=O)- CH2CH2CH3 CH2CH3 CH3 H -OC(=O)- CH2CH2CH3 CH2CH3 CH3 CH3 -OC(=O)- CH~CH2CH3 CH2CH3 CH3 Cl -OC(=O)- CH2CH2CH3 CH2CH3 C1 CH3 -OC(=O)- CHzCH2CH3 CH2CH3 Cl C1 -OC(=O)- CH2CH2CH3 CH~CH2CH3 H H -OC(=O)- CH~CH2CH3 CH2CH2CH3 CH3 H -OC(=O)- CH~CH2CH3 CH2CHZCH3 CH3 CH3 -OC(=O)- CH~CH2CH3 CH2CH2CH3 CH3 C1 -OC(=O)- CH2CH2CH3 CH2CH2CH3 C1 CH3 -OC(=O)- CH2CH~CH3 CH2CH2CH3 CI C1 -OC(=O)- CH2CH2CH3 CH3 H H -OC(=O)- cyclo-propyl CH3 CH3 H -OC(=O)- cyclo-propyl CH3 CH3 CH3 -OC(=O)- cyclo-propyl CH3 CH3 Cl -OC(=O)- cyclo-propyl CH3 Cl CH3 -OC{=O)- cyclo-propyl CH3 Cl Cl -OC(=O)- cyclo-propyl CH2CH3 H H -OC(=O)- cyclo-propyl CH2CH3 CH3 H -OC(=O)- cyclo-propyl CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl CH2CH3 C1 CH3 -OC(=O)- cyclo-propyl CH2CH3 Cl Cl -OC(=O)- cyclo-propyl CH2CH2CH3 H H -OC(=O)- cyclo-propyl CH2CH2CH3 CH3 H -OC{=O)- cyclo-propyl CH2CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl CH2CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl CH2CHZCH3 Cl CH3 -OC{=O)- cyclo-propyl CH2CH2CH3 CI Cl -OC(=O)- cyclo-propyl CH3 H H -OC(=O)- CH=CH2 CH3 CH3 H -OC(=O)- CH=CH2 CH3 CH3 CH3 -OC(=O)- CH=CH2 CH3 CH3 CI -OC(=O)- CH=CH2 CH3 Cl CH3 -OC(=O)- CH=CH2 CH3 CI CI -OC(=O)- CH=CH2 CH2CH3 H H -OC(=O)- CH=CH2 CH,CH3 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 CI CI -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 CH~CH2CH3 CI CH3 -OC(=O}- CI-I=CH2 CH2CH2CH3 CI CI -OC(=O)- CH=CHI

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 CI -OC(=O)- C(=CH2)CH3 CH2CH3 H H -OC(=O)- C(=CH2)CH3 CH2CH3 CH3 H -OC(=O)- C(=CHZ)CH3 CH2CH3 CH3 CH3 -OC(=O)- C(=CHZ)CH3 CH2CH3 CH3 CI -OC(=O)- C(=CH2)CH3 CH2CH3 Cl CH3 -OC(=O)- C(=CH2)CH3 CH2CH3 Cl C1 -OC(=O)- C(=CH2)CH3 CH~CH2CH3 H H -OC(=O)- C(=CH2)CH3 CH2CH2CH3 CH3 H -OC(=O)- C(=CH2)CH3 CH2CH2CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3 CH2CH~CH3 CH3 Cl -OC(=O)- C(=CH2)CH3 CH2CH~CH3 C1 CH3 -OC(=O)- C(=CH2)CH3 CH2CH~CH3 CI C1 -OC(=O)- C(=CH2)CH3 CH3 H H -OC(=O)- CHZCH=CH2 CH3 CH3 H -OC(=O)- CH2CH=CHI

CH3 CH3 CH3 -OC(=O)- CH2CH=CH2 CH3 CH3 Cl -OC(=O)- CH2CH=CHI

CH3 Cl CH3 -OC(=O)- CH2CH=CH2 CH3 C1 Cl -OC(=O)- CHZCH=CH2 CH2CH3 H H -OC(=O)- CH2CH=CH2 CH~CH3 CH3 H -OC{=O)- CHZCH=CH2 CH2CH3 CH3 CH3 -OC(=O}- CH2CH=CH2 CH~CH3 CH3 Cl -OC(=O)- CH~CH=CH2 CH2CH3 C1 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 CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CH2 CH~CH'CH3 CH3 CI -OC(=O}- CH2CH=CH2 CH2CH~CH3 Cl CH3 -OC(=O)- CH2CH=CH2 CH~CH2CH3 Cl Cl -OC{=O)- CH2CH=CHI

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 CI 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 C1 Cl -OC(=O)- CH=CHCH3 CH2CH2CH3 H H -OC(=O)- CH=CHCH3 CH2CH~CH3 CH3 H -OC(=O}- CH=CHCH3 CH2CH2CH3 CH3 CH3 -OC(=O)- CH=CHCH3 CH2CH2CH3 CH3 Cl -OC(=O)- CH=CHCH3 CH~CH~CH3 Cl CHI -OC(=O)- CH=CHCH3 CH2CH~CH3 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 CI -OC(=O)- phenyl CH3 CI CH3 -OC(=O)- phenyl CH3 Cl C1 -OC(=O)- phenyl CH2CH3 H H -OC(=O)- phenyl CH2CH3 CH3 H -OC(=O)- phenyl CH~CH3 CH3 CH3 -OC(=O)- phenyl CH2CH3 CH3 C1 -OC(=O)- phenyl CH2CH3 C1 CH3 -OC(=O)- phenyl CH2CH3 Cl Cl -OC(=O)- phenyl CHZCH2CH3 H H -OC(=O)- phenyl CH2CH~CH3 CH3 H -OC(=O)- phenyl CH2CH2CH3 CH3 CH3 -OC(=O)- phenyl CH2CH2CH3 CH3 CI -OC(=O)- phenyl CH~CH~CH3 Cl CH3 -OC(=O)- phenyl CH2CH2CH3 C1 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 CI -OC(=O)- 2-pyridinyl CH3 CI CH3 -OC(=O)- 2-pyridinyl CH3 CI C1 -OC(=O)- 2-pyridinyl CH2CH3 H H -OC(=O)- 2-pyridinyl CH~CH3 CH3 H -OC(=O)- 2-pyridinyl CH2CH3 CH3 CH3 -OC(=O)- 2-pyridinyl CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl CH2CH3 C1 CH3 -OC(=O)- 2-pyridinyl CH2CH3 C1 C1 -OC(=O)- 2-pyridinyl CH~CH2CH3 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 CI CH3 -OC(=O)- 2-pyridinyl CH2CH2CH3 C1 CI -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 CI -OC(=O)- 2-furanyl CH2CH3 H H -OC(=O)- 2-furanyl CH~CH3 CH3 H -OC(=O)- 2-furanyl CH2CH3 CH3 CH3 -OC(=O)- 2-furanyl CHzCH3 CH3 CI -OC(=O)- 2-furanyl CH~CH3 Cl CH3 -OC(=O)- 2-furanyl CH2CH3 CI 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 CH~CH2CH3 C1 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 CI CH3 -OC(=O)- 2-thienyl CH3 C1 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 CI -OC(=O)- 2-thienyl CH2CH3 C1 CH3 -OC(=O}- 2-thienyl CHZCH3 C1 CI -OC(=O)- 2-thienyl CH~CH2CH3 H H -OC(=O)- 2-thienyl CH2CH2CH3 CH3 H -OC(=O)- 2-thienyl CH2CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl CH~CH2CH3 CH3 C1 -OC(=O)- 2-thienyl CH2CH2CH3 C1 CH3 -OC(=O)- 2-thienyl CH2CH2CH3 CI Cl -OC(=O)- 2-thienyl Table 2 R
~r CH3 H H -OC(=O)O- CH3 CH3 CH3 H -OC(=O)O- CH3 CH3 CH3 CH3 -OC(=O)O- CH3 CH3 CH3 CI -OC(=O)O- CH3 CH3 CI CH3 -OC(=O)O- CH3 CH3 CI CI -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 C1 CH3 -OC(=O)S- CH3 CH3 CI 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 CI -OC(=O)O- CH3 CH2CH3 Cl CH3 -OC(=O)O- CH3 CH2CH3 CI Cl -OC(=O)O- CH3 CHZCH3 H H -OC(=O)S- CH3 CH2CH3 CH3 H -OC(=O)S- CH3 CH2CH3 CH3 CH3 -OC(=O)S- CH3 CH2CH3 CH3 CI -OC(=O)S- CH3 CH2CH3 Cl CH3 -OC(=O)S- CH3 CH2CH3 CI Cl -OC(=O)S- CH3 CH2CH2CH3 H H -OC(=O)O- CH3 CH2CH2CH3 CH3 H -OC(=O)O- CH3 CH2CH2CH3 CH3 CH3 -OC(=O)O- CH3 CH2CH2CH3 CH3 Cl -OC(=O)O- CH3 CH2CH2CH3 CI CH3 -OC(=O)O- CH3 CH2CH2CH3 C1 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 CH2CH2CH3 CH3 CI -OC(=O)S- CH3 CH2CH2CH3 Cl CH3 -OC(=O)S- CH3 CH2CH2CH3 CI 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- CH~CH3 CH3 CH3 CI -OC(=O)O- CH2CH3 CH3 CI CH3 -OC(=O)O- CH2CH3 CH3 Cl CI -OC(=O)O- CH2CH3 CH3 H H -OC(=O)S- CHZCH3 CH3 CH3 H -OC(=O}S- CH2CH3 CH3 CH3 CH3 -OC(=O)S- CH~CH3 CH3 CH3 C1 -OC(=O}S- CH2CH3 CH3 CI CH3 -OC(=O)S- CH2CH3 CH3 CI CI -OC(=O)S- CH2CH3 CH2CH3 H H -OC(=O)O- CH2CH3 CH2CH3 CH3 H -OC(=O)O- CH2CH3 CH2CH3 CH3 CH3 -OC(=O)O- CH~CH3 CH2CH3 CH3 Cl -OC(=O)O- CH~CH3 CH2CH3 CI CH3 -OC(=O)O- CH2CH3 CH2CH3 CI Cl -OC(=O)O- CH2CH3 CH2CH3 H H -OC(=O}S- CH~CH3 CH2CH3 CH3 H -OC(=O)S- CH2CH3 CH2CH3 CH3 CH3 -OC(=O)S- CH~CH3 CH2CH3 CH3 CI -OC(=O)S- CH2CH3 CH2CH3 CI CH3 -OC(=O)S- CH~CH3 CH2CH3 Cl CI -OC(=O)S- CHZCH3 CH-,CH2CH3 H H -OC(=O)O- CH2CH3 CH2CH2CH3 CH3 H -OC(=O)O- CH2CH3 CH~CH2CH3 CH3 CH3 -OC(=O)O- CH2CH3 CH2CH2CH3 CH3 Cl -OC(=O)O- CH,CH3 CH2CH2CH3 CI CH3 -OC(=O)O- CH~CH3 CH2CH2CH3 CI C1 -OC(=O)O- CH~CH3 CH2CH2CH3 H H -OC(=O)S- CH2CH3 CHZCH2CH3 CH3 H -OC(=O)S- CH2CH3 CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH3 CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH3 CH2CH2CH3 CI CH3 -OC(=O)S- CH2CH3 CH2CH2CH3 CI CI -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- CH2CH2CH3 CH3 CI CI -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 CI -OC(=O)S- CH2CH2CH3 CH3 Cl CH3 -OC(=O)S- CH2CH2CH3 CH3 CI Cl -OC(=O)S- CH2CH2CH3 CH2CH3 H H -OC(=O)O- CH2CH2CH3 CH2CH3 CH3 H -OC{=O)O- CH2CH~CH3 CH2CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3 CH2CH3 CH3 Cl -OC(=O)O- CH~CH2CH3 CH2CH3 Cl CH3 -OC(=O)O- CH2CH2CH3 CH2CH3 C1 CI -OC(=O)O- CH~CH2CH3 CH2CH3 H H -OC(=O)S- CH~CH2CH3 CH2CH3 CH3 H -OC(=O)S- CH2CH~CH3 CH2CH3 CH3 CH3 -OC(=O)S- CH~CH2CH3 CH2CH3 CH3 CI -OC(=O)S- CH2CH~CH3 CH~CH3 CI CH3 -OC(=O)S- CH2CH2CH3 CH2CH3 CI Cl -OC(=O)S- CI-12CH2CH3 CH~CH2CH3 H H -OC(=O)O- CH2CH2CH3 CH2CH2CH3 CH3 H -OC{=O)O- CH2CH2CH3 CH~CH2CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3 CH2CH2CH3 CH3 CI -OC(=O)O- CH2CH2CH3 CH2CH2CH3 Cl CH3 -OC(=O)O- CH~CH2CH3 CH2CH2CH3 C1 CI -OC(=O)O- CH2CH2CH3 CH2CH2CH3 H H -OC(=O)S- CH2CH2CH3 CH,CH2CH3 CH3 H -OC(=O)S- CH2CH~CH3 .

CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH2CH3 CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH2CH3 CH2CH~CH3 Cl CH3 -OC(=O)S- CH~CH2CH3 CH2CH2CH3 Cl C1 -OC(=O)S- CH2CH2CH3 CH3 H H -OC(=O)O- cyclo-propyl CH3 CH3 H -OC(=O)O- cyclo-propyl CH3 CH3 CH3 -OC(=O)O- cvclo-propyl CH3 CH3 Cl -OC(=O}O- cyclo-propyl CH3 Cl CH3 -OC(=O)O- cyclo-propyl CH3 CI C1 -OC(=O)O- cyclo-propyl CH3 H H -OC(=O)S- cyclo-propyl CH3 CH3 H -OC(=O)S- cyclo-propyl CH3 CH3 CH3 -OC(=O)S- cvclo-propyl CH3 CH3 Cl -OC(=O)S- cyclo-propyl CH3 CI CH3 -OC(=O)S- cyclo-propyl CH3 Cl C1 -OC(=O)S- cyclo-propyl CH2CH3 H H -OC(=O)O- cyclo-propyl CH2CH3 CH3 H -OC(=O)O- cyclo-propyl CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl CH2CH3 CH3 Cl -OC(=O)O- cyclo-propyl CH2CH3 CI CH3 -OC(=O}O- cyclo-propyl CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl CH2CH3 H H -OC(=O)S- cyclo-propyl CH2CH3 CH3 H -OC(=O)S- cyclo-propyl CH~CH3 CH3 CH3 -OC(=O)S- cvclo-propyl CH2CH3 CH3 Cl -OC{=O)S- cyclo-propyl CH2CH3 CI CH3 -OC(=O)S- cyclo-propyl CH2CH3 Cl Cl -OC(=O)S- cvclo-propyl CH2CH2CH3 H H -OC(=O)O- cyclo-propyl CH2CH2CH3 CH3 H -OC{=O)O- cyclo-propyl CH2CH2CH3 CH3 CH3 -OC{=O)O- cyclo-propyl CH2CH2CH3 CH3 C1 -OC(=O)O- cyclo-propyl CH2CH2CH3 C1 CH3 -OC(=O)O- cyclo-propyl CH2CH2CH3 C1 C1 -OC(=O)O- cyclo-propyl CHZCH2CH3 H H -OC(=O)S- cyclo-propyl CH~CH2CH3 CH3 H -OC(=O)S- cyclo-propyl CH~CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl CH2CH2CH3 CH3 Cl -OC(=O)S- cyclo-propyl _ CH2CH2CH3 C1 CH3 -OC(=O)S- cvclo-propyl CH2CH2CH3 CI Cl -OC(=O)S- cyclo-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 CI 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 CI 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 CI -OC(=O)O- CH=CH2 CH2CH3 CI CH3 -OC(=O)O- CH=CH2 CH~CH3 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- CI-I=CH2 CH2CH3 CH3 CI -OC(=O)S- CH=CH2 CH2CH3 Cl CH3 -OC(=O)S- CH=CH2 CH2CH3 C1 CI -OC{=O)S- CH=CHI

CH2CH2CH3 H H -OC(=O)O- CH=CHI

CH2CH~CH3 CH3 H -OC(=O)O- CH=CH2 CH2CH2CH3 CH3 CH3 -OC(=O)O- CH=CH2 CH2CH2CH3 CH3 C1 -OC(=O)O- CH=CH2 CHZCH2CH3 Cl CH3 -OC(=O)O- CH=CH2 CH2CH2CH3 CI Cl -OC(=O)O- CH=CHI

CH2CH~CH3 H H -OC(=O)S- CH=CH' CH2CH~CH3 CH3 H -OC(=O)S- CH=CH2 CH2CH2CH3 CH3 CH3 -OC(=O)S- CH=CH2 CH2CH2CH3 CH3 C1 -OC(=O)S- CH=CHI

CH2CH2CH3 CI CH3 -OC(=O)S- CH=CH2 CH2CH~CH3 CI CI -OC(=O)S- CH=CHI

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 CI -OC(=O)O- C(=CH2)CH3 CH3 CI CH3 -OC(=O)O- C(=CH2)CH3 CH3 CI CI -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 CI CH3 -OC(=O)S- C(=CH2)CH3 CH3 CI 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 CI -OC(=O)O- C(=CH2)CH3 CH2CH3 Cl CH3 -OC(=O)O- C(=CH~)CH3 CH2CH3 Cl CI -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 CI CH3 -OC(=O)S- C(=CH2)CH3 CH2CH3 CI Cl -OC(=O}S- C(=CH2)CH3 CH2CH2CH3 H H -OC(=O)O- C(=CH2)CH3 CH2CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3 CH2CHZCH3 CH3 CH3 -OC(=O)O- C(=CH2)CH3 CH2CH2CH3 CH3 CI -OC(=O}O- C(=CH2)CH3 CH2CH2CH3 Cl CH3 -OC(=O)O- C(=CH2)CH3 CH2CH2CH3 Cl CI -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 CH2CH2CH3 CH3 CI -OC(=O)S- C(=CH2)CH3 CH2CH2CH3 CI CH3 -OC(=O)S- C(=CH2)CH3 CH2CH2CH3 CI CI -OC(=O)S- C(=CH2)CH3 CH3 H H -OC(=O)O- CH~CH=CH2 CH3 CH3 H -OC(=O)O- CH2CH=CH2 CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2 CH3 CH3 CI -OC(=O)O- CH2CH=CH2 CH3 CI CH3 -OC(=O)O- CH2CH=CH2 CH3 C1 CI -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 CI -OC(=O)S- CH2CH=CH2 CH3 CI CH3 -OC(=O)S- CH2CH=CHZ

CH3 CI Cl -OC(=O)S- CH2CH=CH2 CH2CH3 H H -OC(=O)O- CH2CH=CH2 CH~CH3 CH3 H -OC(=O)O- CH2CH=CH2 CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CHI

CH2CH3 CH3 CI -OC(=O)O- CH2CH=CH2 CH2CH3 Cl CH3 -OC(=O)O- CH2CH=CH2 CH2CH3 Cl CI -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 CI -OC(=O)S- CH~CH=CH2 CH2CH2CH3 H H -OC(=O)O- CH2CH=CH2 CH2CH2CH3 CH3 H -OC(=O)O- CHZCH=CH2 CH2CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CHI

CH2CH2CH3 CH3 CI -OC{=O)O- CHZCH=CH2 CH2CH~CH3 Cl CH3 -OC(=O)O- CH2CH=CH2 CH2CH~CH3 CI CI -OC(=O)O- CH2CH=CH2 CH2CH2CH3 H H -OC(=O)S- CH2CH=CH2 CH2CH~CH3 CH3 H -OC(=O)S- CH2CH=CHI

CH2CH2CH3 CH3 CH3 -OC(=O)S- CH'CH=CH2 CH2CH2CH3 CH3 CI -OC(=O)S- CH2CH=CH2 CH2CH2CH3 CI CH3 -OC(=O)S- CH2CH=CHI

CH2CH2CH3 CI CI -OC{=O)S- CH~CH=CHI

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 CI 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 CI -OC{=O)S- CH=CHCH3 CH3 Cl CH3 -OC(=O)S- CH=CHCH3 CH3 CI 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 CI -OC(=O)O- CH=CHCH3 CH2CH3 CI 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 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 CI CH3 -OC(=O)O- CH=CHCH3 CH2CH2CH3 CI CI -OC(=O)O- CH=CHCH3 CH2CH2CH3 H H -OC(=O)S- CH=CHCH3 CH2CH2CH3 CH3 H -OC(=O)S- CH=CHCH3 CH~CH2CH3 CH3 CH3 -OC(=O)S- CH=CHCH3 CH2CH2CH3 CH3 C1 -OC(=O)S- CH=CHCH3 CH2CH2CH3 Cl CH3 -OC(=O)S- CH=CHCH3 CH,CH2CH3 CI 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 CI -OC(=O)O- phenyl CH3 Cl CH3 -OC(=O)O- phenyl CH3 CI CI -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 CI -OC(=O)O- phenyl CH2CH3 CI CH3 -OC(=O)O- phenyl CH~CH3 Cl Cl -OC(=O)O- phenyl CH2CH3 H H -OC(=O)S- phenyl CHZCH3 CH3 H -OC(=O)S- phenyl CH2CH3 CH3 CH3 -OC(=O)S- phenyl CH2CH3 CH3 CI -OC(=O)S- phenyl CH2CH3 CI CH3 -OC{=O)S- phenyl CH2CH3 C1 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 C1 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 CH2CHZCH3 CH3 CH3 -OC(=O)S- phenyl CH2CH2CH3 CH3 Cl -OC(=O)S- phenyl CH2CH2CH3 C1 CH3 -OC(=O)S- phenyl CH2CH2CH3 CI 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 CI -OC(=O)O- 2-pyridinyl CH3 C1 CH3 -OC(=O)O- 2-pyridinyl CH3 C1 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 C1 CH3 -OC(=O)S- 2-pyridinyl CH3 C1 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 C1 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 CI CH3 -OC(=O)S- 2-pyridinyl CH2CH3 Cl CI -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 CH2CH2CH3 CH3 Cl -OC(=O)O- 2-pyridinyl CH2CH2CH3 C1 CH3 -OC(=O)O- 2-pyridinyl CH2CH2CH3 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 CH~CH2CH3 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 CI -OC(=O)O- 2-furanyl CH3 Cl CH3 -OC(=O)O- 2-furanyl CH3 CI 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 CI 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 CI -OC(=O)O- 2-furanyl CH2CH3 CI CH3 -OC(=O)O- 2-furanyl CH2CH3 Cl C1 -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 CI -OC(=O)S- 2-furanyl CH2CH3 Cl CH3 -OC(=O)S- 2-furanyl CH2CH3 C1 Cl -OC(=O)S- 2-furanyl CHZCH2CH3 H H -OC(=O)O- 2-furanyl CH2CH2CH3 CH3 H -OC(=O)O- 2-furanyl CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-furanyl CH2CH2CH3 CH3 Cl -OC(=O)O- 2-furanyl CH2CH2CH3 C1 CH3 -OC(=O)O- 2-furanyl CH2CH~CH3 Cl Cl -OC(=O)O- 2-furanyl CH2CH2CH3 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 CH,CH2CH3 CI CH3 -OC{=O)S- 2-furanyl CH2CHZCH3 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 CI CH3 -OC(=O)O- 2-thienyl CH3 C1 Cl -OC(=O)O- 2-thienyl CH3 H H -OC(=O)S- 2-thienyl CH3 CH3 H -OC(=O)S- 2-thienyl CHg CH3 CH3 -OC(=O)S- 2-thienyl CH3 CH3 CI -OC(=O)S- 2-thienyl CH3 C1 CH3 -OC(=O)S- 2-thienyl CH3 CI CI -OC(=O)S- 2-thienyl CH~CH3 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 C1 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 CH2CHzCH3 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 CH~CH2CH3 CH3 Cl -OC(=O)S- 2-thienyl CH2CH2CH3 Cl CH3 -OC(=O)S- 2-thienyl CH2CH2CH3 Cl Cl -OC(=O)S- 2-thienyl CH3 H H -OC(=O)- CH2CH2CH3 CH3 CH3 H -OC(=O)- CHZCH~CH3 CH3 CH3 CH3 -OC{=O)- CH2CH~CH3 CH3 CH3 Cl -OC(=O)- CH2CH2CH3 CH3 Cl CH3 -OC(=O)- CH~CH2CH3 CH3 CI Cl -OC(=O)- CH~CH2CH3 CH2CH3 H H -OC(=O)- CH2CH~CH3 CH2CH3 CH3 H -OC(=O)- CH2CH2CH3 CH2CH3 CH3 CH3 -OC(=O)- CH2CH2CH3 CH~CH3 CH3 Cl -OC(=O)- CH2CH2CH3 CH2CH3 Cl CH3 -OC(=O)- CH~CH~CH3 CH2CH3 Cl Cl -OC(=O)- CH2CH2CH3 CH2CH2CH3 H H -OC(=O)- CH~CH2CH3 CH2CH2CH3 CH3 H -OC(=O)- CH2CH~CH3 CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH~CH3 CH2CH2CH3 CH3 Cl -OC(=O)- CH2CH2CH3 CH2CH2CH3 Cl CH3 -OC(=O)- CH2CH2CH3 CH2CH2CH3 C1 C1 -OC(=O)- CH2CH2CH3 CH3 H H -OC(=O)- cyclo-propyl CH3 CH3 H -OC(=O)- cyclo-propyl CH3 CH3 CH3 -OC(=O)- cyclo-propyl CH3 CH3 Cl -OC(=O)- cyclo-propyl CH3 CI CH3 -OC(=O)- cyclo-propyl CH3 Cl Cl -OC(=O)- cvclo-propyl CH2CH3 H H -OC(=O)- cyclo-propyl CH2CH3 CH3 H -OC(=O)- cyclo-propyl CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl CH2CH3 Cl CH3 -OC(=O)- cyclo-propyl CH2CH3 C1 Cl -OC(=O)- cyclo-propyl CH2CH2CH3 H H -OC(=O)- cyclo-propyl CH2CH2CH3 CH3 H -OC(=O)- cyclo-propyl CHZCHZCH3 CH3 CH3 -OC(=O)- cyclo-propyl CH2CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl CH2CH2CH3 CI CH3 -OC(=O)- cyclo-propyl CH2CH2CH3 CI Cl -OC(=O)- cyclo-propyl CH3 H H -OC(=O)- CH=CH2 CH3 CH3 H -OC(=O}- CH=CH2 CH3 CH3 CH3 -OC(=O)- CH=CHI

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

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 CI CH3 -OC(=O)- CH=CH2 CH~CH3 Cl Cl -OC(=O)- CH=CH2 CH2CH2CH3 H H -OC(=O)- CH=CH2 CH~CH2CH3 CH3 H -OC(=O)- CH=CH2 CH~CH2CH3 CH3 CH3 -OC(=O)- CH=CH2 CH2CH2CH3 CH3 C1 -OC(=O)- CH=CH2 CH2CH2CH3 C1 CH3 -OC(=O)- CH=CH2 CH2CH~CH3 CI CI -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 CI -OC(=O)- C{=CH2)CH3 CH3 Cl CH3 -OC(=O)- C{=CH2)CH3 CH3 Cl CI -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 CI -OC(=O)- C(=CH2)CH3 CH2CH3 Cl CH3 -OC(=O)- C(=CH2)CH3 CH2CH3 CI Cl -OC(=O}- C(=CH')CH3 CH2CH2CH3 H H -OC(=O)- C(=CH2)CH3 CH2CH2CH3 CH3 H -OC(=O)- C(=CH2)CH3 CH2CH2CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3 CH2CHZCH3 CH3 CI -OC(=O)- C(=CHZ)CH3 CH2CH2CH3 CI CH3 -OC(=O)- C(=CH2)CH3 CH2CH~CH3 CI CI -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 C1 -OC(=O)- CH2CH=CH2 CH3 CI CH3 -OC(=O)- CH2CH=CHI

CH3 Cl CI -OC(=O)- CH2CH=CH2 CH2CH3 H H -OC(=O)- CH2CH=CH2 CH2CH3 CH3 H -OC(=O)- CH2CH=CH2 CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CHI

CH2CH3 CH3 CI -OC(=O)- CH2CH=CHZ

CH2CH3 CI CH3 -OC(=O)- CH2CH=CHI

CH2CH3 C1 CI -OC(=O)- CH2CH=CH2 CH2CH2CH3 H H -OC(=O)- CH2CH=CH2 CH2CH2CH3 CH3 H -OC(=O)- CH2CH=CH2 CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CH2 CH2CH2CH3 CH3 CI -OC(=O)- CH2CH=CH2 CH2CH2CH3 CI CH3 -OC(=O)- CH2CH=CH2 CH2CH~CH3 CI 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 CI -OC(=O)- CH=CHCH3 CH3 Cl CH3 -OC(=O)- CH=CHCH3 CH3 CI 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 CHZCH2CH3 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 CH~CH2CH3 CH3 H -OC(=O)- phenyl CH2CH2CH3 CH3 CH3 -OC(=O)- phenyl CH2CH2CH3 CH3 Cl -OC(=O)- phenyl CH2CHZCH3 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 CI 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 CI CH3 -OC(=O)- 2-pyridinyl CH2CH3 Cl CI -OC(=O)- 2-pyridinyl CH2CH2CH3 H H -OC(=O)- 2-pyridinyl CH2CH2CH3 CH3 H -OC(=O)- 2-pyridinyl CH2CHZCH3 CH3 CH3 -OC(=O)- 2-pyridinyl CH~CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl CH2CH2CH3 Cl CH3 -OC{=O)- 2-pyridinyl CHZCH2CH3 Cl CI -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 CI CH3 -OC(=O)- 2-furanyl CH3 Cl C1 -OC(=O)- 2-furanyl CH2CH3 H H -OC(=O)- 2-furanyl CH2CH3 CH3 H -OC(=O)- 2-furanyl CH2CHg CH3 CH3 -OC(=O)- 2-furanyl CH2CH3 CH3 Cl -OC(=O)- 2-furanyl CH2CH3 Cl CH3 -OC{=O)- 2-furanyl CH2CH3 Cl CI -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 CI CH3 -OC(=O)- 2-furanyl CH2CH2CH3 CI 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 CI -OC(=O)- 2-thienyl CH3 Cl CH3 -OC(=O)- 2-thienyl CH3 CI CI -OC(=O)- 2-thienyl CHzCH3 H H -OC(=O)- 2-thienyl CH2CH3 CH3 H -OC(=O)- 2-thienyl CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl CHZCH3 CH3 Cl -OC(=O)- 2-thienyl CH2CH3 Cl CH3 -OC(=O)- 2-thienyl CH2CH3 Cl Cl -OC(=O)- 2-thienyl CH2CH~CH3 H H -OC(=O}- 2-thienyl CH2CH2CH3 CH3 H -OC(=O)- 2-thienyl CH2CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl CH2CH2CH3 CH3 Cl -OC(=O)- 2-thienyl CH2CHZCH3 Cl CH3 -OC(=O}- 2-thienyl CH2CH2CH3 Cl CI -OC(=O)- 2-thienyl Table 3 H O Rz O
N \
RI/ I O s O

R1 is CH2CH~, R2 and R3 are CH3 A- Q -A Q

-OC(=O)O- CH(CH3)2 -OC(=O}- CH(CH3)2 -OC(=O)S- CH(CH3)2 -OC(=O)- cyclo-butyl -OC(=O)O- cyclo-butyl -OC(=O)- cyclo-pentyl -OC(=O)S- cyclo-butyl -OC(=O)- cyclo-hexyl -OC(=O)O- cyclo-pentyl -OC(=O}- 5-CH3-2-thienyl -OC(=O)S- cyclo-pentyl -OC(=O}- S-Cl-2-thienyl -OC(=O)O- cyclo-hexyl -OC(=O)- S-CH3-2-furanyl -OC(=O)S- cyclo-hexyl -OC(=O)- S-Cl-2-furanyl -OC(=O)O- S-CH3-2-thienyl -OC(=O)- 3-pyridinyl -OC(=O)S- S-CH3-2-thienyl -OC(=O)- 4-pyridinyl -OC(=O)O- S-Cl-2-thienyl -OC(=O)- 6-CH3-2-pyridinyl -OC(=O)S- S-Cl-2-thienyl -OC(=O)- 6-Cl-2-pyridinyl -OC(=O}O- S-CH3-2-furanyl -OC(=O)- 2-CH3-phenyl -OC(=O)S- S-CH3-2-furanyl -OC(=O)- 3-CH3-phenyl -OC(=O)O- S-Cl-2-furanyl -OC(=O)- 4-CH3-phenyl -OC(=O)S- S-CI-2-furanyl -OC(=O}- 2,6-diCH3-phenyl -OC(=O)O- 3-pyridinyl -OC(=O)- 2-CI-phenyl -OC(=O)S- 3-pyridinyl -OC(=O)- 3-Cl-phenyl -OC(=O}O- 4-pyridinyl -OC(=O)- 4-CI-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-CI-2-pyridinyl -OC(=O)- 2,S-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-CI-phenyl -OC(=O)O- 3-Cl-phenyl -OC{=O)S- 3-CI-phenyl -OC(=O)O- 4-CI-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,S-diCl-phenyl -OC(=O)S- 2,S-diCl-phenyl -OC(=O)O-.2,4-diCl-phenyl -OC(=O)S- 2,4-diCl-phenyl Table 4 R
R1 is CH2CH3, RZ and R3 are CH3 A SZ A Q

-OC(=O)O- CH(CH3)2 -OC(=O)- CH(CH3)2 -OC(=O)S- CH(CH3)2 -OC(=O)- cyclo-butyl -OC(=O)O- cyclo-butyl -OC(=O)- cvclo-pentyl -OC(=O)S- cyclo-butyl -OC(=O)- cyclo-hexyl -OC(=O)O- cyclo-pentyl -OC(=O)- 5-CH3-2-thienyl -OC(=O)S- cyclo-pentyl -OC(=O)- 5-Cl-2-thienyl -OC(=O)O- cyclo-hexyl -OC(=O)- 5-CH3-2-furanyl -OC(=O)S- cvclo-hexyl -OC(=O)- 5-Cl-2-furanyl -OC(=O)O- S-CH3-2-thienyl -OC(=O)- 3-pyridinyl -OC(=O)S- 5-CH3-2-thienyl -OC(=O)- 4-pyridinyl -OC(=O)O- 5-C1-2-thienyl -OC(=O)- 6-CH3-2-pyridinyl -OC(=O)S- 5-C1-2-thienyl -OC(=O)- 6-Cl-2-pyridinyl -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-CI-2-furanyl -OC(=O)- 4-CH3-phenyl -OC(=O)S- 5-C1-2-furanyl -OC(=O)- 2,6-diCH~-phenyl -OC(=O)O- 3-pyridinyl -OC(=O)- 2-C1-phenyl -OC(=O)S- 3-pyridinyl -OC(=O)- 3-Cl-phenyl -OC(=O)O- 4-pyridinyl -OC(=O)- 4-CI-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-C1-2-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-C1-phenyl -OC(=O)S- 3-Cl-phenyl -OC(=O)O- 4-Cl-phenyl -OC(=O)S- 4-C1-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-OCH~-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 T.,1.1,~ C

R l~ O ~ O v0 O~ R3 S

Rt R2 R3 R~

CH2CH3 CH3 CH3 CH~CH3 CHZCH3 CH2CH3 CH3 CH3 CH3 phenyl CH2CH3 CH3 CH3 -CH~CH20CH~CH2-Table 6 R
~6R7 CH2CH3 CH3 CH3 CH~CH3 CH2CH3 CH2CH3 CH3 CH3 CH3 phenyl CH2CH3 CH3 CH3 -CH2CH~CH2CH2-CH2CH3 CH3 CH3 -CH2CHZOCH~CH2-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 In reg diem 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 4-5 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 oflnsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ.
Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N dimethylformamide, dimethyl sulfoxide, N alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer :s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as taught in U.S.
4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S.
5,180,587, U.S.
5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S.
3,299,566.
For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through I S 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 I-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 9g,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%
montmorilIonite (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%
5 crude calcium ligllinsulfonate 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 10 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 15 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, 20 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, 25 amount and type of vegetation present, growing conditions, etc. In general, a herbicidalIy 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 30 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, 35 ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsuIfuron, 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, ciopyralid, 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,S-dihydro-4-methyl-4-(I-methylethyl)-5-oxo-1H imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibrornide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, 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, malefic 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 [[[1-[S-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate (AKH-7088), methyl 5-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino] sulfonyl]-1-(2-pyridinyl)-1 H-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

R1/ ~ ~3 O S O
Q
R1 is CH2CH3 Cmnd A Q R4 RS mt~ (C) I OC(=O) C(=CH2)CH3 C=O 63 (dec) 2 OC(=O) Ph C=O 70 (dec) 3 OC(=O) CH(CH3)2 C=O 62-63 (dec) 4 OC(=O) 2,5-diCl-6-OCH3Ph C=O oil 5 OC(=O) 4-CH3Ph C=O 81 (dec) 6 OC(=O) cyclopropyl C=O 77 (dec) 7 OC(=O) 3,6-diCl-pyridin-2-ylC=O 21 S-217 8 OC(=O) furan-2-yl C=O 70 (dec) 9 OC(=O) 2-CH3Ph C=O 201-203 10 OC(=O) 2-FPh C=O 153-155 I 1 OC(=O) 4-FPh C=O I 58-160 12 OC(=O) 4-BrPh C=O 98 (dec) 13 OC(=O) C(=CH2)CH3 -OCH2CH20- 175-177 (dcc) 14 OC(=O) Ph -OCH2CH20- 179-180 15 OC(=O) CH(CH3)2 -OCH2CH20- 73 (dec) 16 OC(=O) 2,5-diCl-6-OCH3Ph -OCI-I2CH20- 198-200 17 OC(=O) cyclopropyl -OCH2CH20- 215-217 18 OC(=O) 3,6-diCl-pyridin-2-yl-OCH2CH20- 228-230 19 OC(=O) furan-2-yl -OCH2CH20- 201-203 20 OC(=O) 4-FPh -OCH2CH20- 237-239 21 OC(=O) C(CH3)3 -OCH2CH20- >200 23 OC(=O)O CH(CH3)2 C=O 58-60 (dec) 24 OC(=O)O CH2CH3 C=O 58 (dec}

25 OC(=O)O CH2CH=CH2 C=O oil*

26 OC(=O)O CH3 C=O 135-137 27 OC(=O)O Ph C=O 68 (dec) 28 OC(=O)O CH2CH2CH3 C=O 68 (dec) 29 (Ex.OC(=O)O CH(CH3)2 -OCH2CH20- 168-170 1) 30 (Ex.OC(=O)O CH2CH3 -OCH2CH20- 201-203 2) 31 OC(=O)O CH3 -OCH2CH20- 191-193 32 OC(=O)O CH2CH=CH2 -OCH2CH20- 72-74 33 OC(=O)O CH2CH2CH3 -OCH2CH20- 74 (dec) 34 OC(=O)O Ph -OCH2CH20- 215 35 OC(=O)O CH2CH(CH3)2 -OCH2CH20- 65-67 (dec) 36 OC(=O)O CH2CH2CH2CH3 -OCH2CH20- 62 (dec) 37 OC(=O)O CH2CI-I20CH3 -OCH2CH20- 113 (dec) 38 OC(=O)O CH2CH2CH2CH2CH3 -OCH2CH20- 58 {dec) 39 OC(=O)O (CH2)SCH3 -OCH2CH20- 48 (dec) 40 OC{=O)O CH2Ph -OCH2CH20- 171 41 OC(=O)O (CH2)7CH3 -OCH2CH20- 47 (dec) 42 OC(=O}O CH2C1 -OCH2CH20- 61-62 (dec) 43 OC(=O)O CH2CH2CH2CH2Cl -OCH2CH20- 48-50 (dec) 44 OC(=O)O CH2CH2Cl -OCH2CH20- 169-171 (dec) 45 OC(=O)O CI-i2CH2Br -OCH2CH20- 170-172 (dec) 46 OC(=O)O 4-BrPh -OCH2CH20- 85-98 47 OC(=O)O 4-CIPh -OCH2CH20- 78-90 48 OC(=O)O 4-OCH3Ph -OCH2CH20- 160-163 49 OC(=O)O 4-CH3Ph -OCH2CH20- 176-182 50 OC(=O)N(CH3)2 -OCH2CH20- 239-241 51 OC(=O)N(CH2CH3)2 -OCH2CH20- oil OC(=O)N

53 OC(=O)N(CH3)Ph -OCH2CH20- 98-102 54 OC(=O)N(CH(CH3)2)2 -OCH2CH20- 107-112 55 ~ -OCH2CH20- semi-solid OC(=O)N\
~
/

OC(=O)S

57 OC{=O)S CH3 -OCH2CH20- 172-175 58 OC(=O)S Ph -OCH2CH20- 170-171 59 OC(=O)S 4-CIPh -OCH2CH20- i76-177 *See Table B for 1H NMR
Index data.

R1 is CH3 Cmpd A Q R4 R5 mp (°C) 60 OC(=O)O CH2CH3 -OCH2CH20- 155-157 61 OC(=O)O CH2CH2CH3 -OCH2CH20- 160-162 62 OC(=O)O CH2Ph -OCH2CH20- 85-87 INDEX TABLE B
Cmpd No. 1H NMR Data (CDC1~ solution unless indicated otherwise)a 4 8 1.5 (t, 3H), 2.48 {s, 3H), 2.76 (s, 3Ii), 3.34 (m, 2H), 3.74 (m, 2H), 4.05 (s, 3H), 4.21 (q, 2H), 7.24 (d, 1H), 7.43 (s, 1H), 7.51 (m, 2H).
21 8 1.22 (s, 9H), 1.31 (t, 3II), 2.17 (s, 3H), 2.45 (m, 2H), 2.63 (s, 3H), 3.39 (m, 2H), 3.88 (q, 2tI), 3.9-4.19 (m, 4H), 7.08 (s, 1H), 7.44 (s, 1H).
25 8 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, 1H), 7.37 (s, 1H), 7.51 (s, 1H).
51 8 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, 2II), 4.15 (m, 2H), 4.25 (m, 2H), 7.2 (s, 1H), 7.7 (s, IH).
55 8 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, 1 H0, 7.65 (s, 1 H).
a 1H 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), 5 barnyardgrass (Echinochloa crux-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 10 retroJlexa~s), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat {Avena fatua) and purple nutsedge (Cyperus rotundas) 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 15 treated with some designated compounds. This paddy contained rice, barnyardgrass, 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 20 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.

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Rate 50 g/ha25 2630 31 32 Rate 10 g/ha 2526 30 31 SPRAYED PADDY SPRAYED PADDY

Barnyardgrass10 1010 9 10 Barnyardgrass 1010 10 7 Ducksalad 6 5 6 3 6 Ducksalad 4 4 2 0 Rice 10 9 10 10 10 Rice 8 6 9 5 S. flatsedge7 9 6 6 8 S. flatsedge 4 6 2 4 Test B
Seeds of broadleaf signalgrass (Brachiaria decumbens), bedstraw (Galium aparine), bIackgrass (Alopecurus myosuroides), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitar-ia sanguinalis), giant foxtail (Setaria.faberii), morningglory (Ipomoea hederacea), rape (Brassica napus), pigweed (Amaranthus retroJlexus), soybean (Glvcine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Ti-iticum 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 1 S consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (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 -Barnyardgrass 9 5 9 0 9 0 2 0 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 b2 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 IO
Velvetleaf 10 10 9 9 10 10 20 -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 N N o ao ~ co m r o ~ a~ ' ~ o~ o o t~ o 0o d~ M
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ro m v v v c'~o ~ -.-~ >, 3 v ~' v ~ ~ ~n ~ o -°~ ro ~ w u~ s~ ~n ~ x ~ n~ v ~ ro cn s~ ro ~d 3 ro ~ m ro O ~ v m v v m v ~ s~ ro s-~ p ro ~ w tr tr ~ ~ G v ,~ ro E ~ ro ~ ~ v ~ ro G ~ o ro ro .a .u o v v-.~>,.~x~ ~m~-~v o ~v~v.u v y m ~ ~n v x a si .x G ~ m v s~ v r=. .n ro > ro ~o ~o ro v ~ ro v ro s~ ~ cz zs v >, tr ~ v ro o . ro v ~ o o s.~ ~ -.~ o ~ ro v -.~ . o ~ v E.rx.woommwvv~a~zzxxx~nmcn Test C
Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur S (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), varieties of corn {Zea mays designated 'Corn 2' and 'Corn S'), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiJlorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sor~~hum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroJlexus), prickly sida (Silo spinosa), shattercane (Sorghum vulgar°e), 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 (Setarla lutescens) and purple nutsedge (Cyperus 1 S 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, sununarized 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
Barnyardgrass 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 100 100 100 100 100 100 200 100 100 100 100 100 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 V~ild 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 7 8 13 14 15 24 29 30 POSTEMERGENCE
Barnyardgrass 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 I00 100 100 100 100 Johnsongrass - - - - 25 80 100 100 100 80 30 90 Lambsquarters100 100100100 100100100 100100100 10090 Morningglory 80 75 10080 70 70 100 100100100 10090 Nutsedge 0 0 0 0 15 15 15 30 25 15 25 30 Pigweed 80 85 80 90 20 60 100 10010050 10050 Prickly sida 20 55 35 40 10 25 100 85 85 10 80 100 Ragweed 70 70 85 100 80 60 100 10010060 10095 Shattercane 45 70 75 100 45 75 100 75 10070 10090 Signalgrass 0 40 20 100 55 85 100 45 80 55 70 90 Smartweed - - - - - - - - - - - -Soybean 1 100 100100100 100100100 10085 65 10090 Soybean 2 100 70 100100 10075 100 10010060 10080 Sunflower 100 100100100 100100100 10010080 10090 Velvetleaf 100 100100100 100100100 10010080 100100 Wild proso 100 100100100 100100- 100- 100 100100 Woolly cupgrass55 70 70 85 65 75 75 85 85 75 85 100 Yellow foxtail100 10090 100 80 100100 10010080 95 100 Table C COMPOUND

Rate 17 g/ha 1 2 3 6 7 8 13 14 15 24 29 30 POSTEMERGENCE

Barnyardgrass100 85 90 100 80 - 100 10080 80 85 100 Bindweed 60 70 65 70 50 60 85 75 75 40 75 70 Blk nightshade80 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 100100 10090 70 10090 Corn 2 0 0 0 0 0 0 5 0 0 10 0 0 Corn 5 3 0 0 0 0 5 5 0 0 0 0 0 Cotton 100 80 75 100 50 70 100 10010040 10080 Crabgrass 70 55 75 80 50 85 80 85 80 50 80 90 Fall panicum 90 10060 80 100100100 10085 100 10090 Giant foxtail85 90 100100 85 100100 10080 80 100100 Green foxtail100 100100100 60 85 100 10010070 10095 Jimsonweed 100 100100100 80 100100 100100100 100100 Johnsongrass - - - - 25 15 80 10025 30 15 70 Lambsquarters100 100100100 85 100100 100100100 10070 Morningglory 70 75 80 70 60 65 100 90 80 100 10080 Nutsedge 0 0 0 0 15 10 10 15 15 15 15 10 Pigweed 85 80 65 80 20 50 200 85 10020 10050 Prickly sida 15 20 25 40 10 15 75 80 10010 80 70 Ragweed 70 80 - 85 50 40 100100 10040 10090 Shattercane 15 55 30 30 45 50 45 65 60 65 65 50 Signalgrass 20 20 15 90 55 85 10040 35 15 BO 50 Smartweed - - - - - - - - - - - -Soybean 1 100100100 10080 60 10070 70 60 10090 Soybean 2 100100100 80 65 75 10075 10030 85 70 Sunflower 100100100 100100 60 10070 80 75 75 80 Velvetleaf 100100100 10085 70 100100 10060 100100 Wild proso 100100100 100100 200- 95 - 100 100100 Woolly cupgrass25 25 35 55 55 40 70 75 65 65 80 80 Yellow foxtail85 10085 10075 80 100100 75 75 95 90 Table C COMPOUND

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

Barnyardgrass 10085 100 10075 80 10090 75 75 85 95 Bindweed 60 55 60 60 40 55 70 80 75 10 75 50 Blk nightshade80 75 75 75 - 20 80 75 80 40 80 80 Cassia 0 15 15 20 - - 20 20 20 - 10 -Cocklebur 75 10080 75 50 65 85 100 90 60 10090 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 10020 100100 10085 85 100100 10080 Giant foxtail 80 90 100 10085 85 80 85 85 70 80 90 Green foxtail 100100100 50 55 70 65 70 85 40 85 Jimsonweed 100100100 100100 10080 85 10065 10090 Johnsongrass - - - - 0 55 70 40 0 15 10 30 Lambsquarters 100100100 10080 30 100100 10060 10060 Morningglory 70 70 65 65 60 60 10085 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 10050 Ragweed 70 80 - 50 50 25 85 100 10040 10090 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 Smartweed - - - - - - - - - - - -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 100 200 100 100 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 mvosuroides), 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 mailtijllorum), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape 1 (Brassica napus), redroot pigweed (Amaranthus retroJlexus), Russian thistle (Salsola kali), scentless chamomile (Matricaria inodor-a), 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 (PolygTonum convolvulus), wild mustard (Sinapis arvensis), stages of wild oat (Avena fatua, designated 1 or 2 based upon the leaf stage of the wild oat at the time of treatment), windgrass (Apera spica-vend) and winter barley (Hordeum vulgare).
Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 2$ 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/ha4 5 Rate 62 g/ha 4 5 16 23 29 POSTEMERGENCE POSTEMERGENCE

Annual bluegras20 45 Annual bluegras 10 30 20 35 60 Barley (winter)5 10 Barley (winter) 0 5 10 2 10 Blackgrass 20 20 Blackgrass (2) 10 15 10 20 50 (2) Blk nightshade100 100 Blk nightshade 10090 10090 100 Chickweed 90 100 Chickweed 10 75 100100100 Common poppy 85 100 Common poppy 90 100 90 75 100 Deadnettle 100 100 Deadnettle 100100 100100100 Downy brome 0 0 Downy brome 0 0 0 0 20 Field violet 100 100 Field violet 100100 100100100 Galium (2) 65 70 Galium (2) 60 60 60 70 60 Green foxtail100 100 Green foxtail 100100 100100100 I. Ryegrass 10 40 I. Ryegrass 5 20 5 20 10 Jointed goatgra0 10 Jointed goatgra 0 5 0 5 0 Kochia 85 85 Kochia 75 80 10080 100 Lambsquarters80 95 Lambsquarters 75 80 10080 100 LS canarygrass10 30 LS canarygrass 10 10 70 15 60 Rape (1) 85 75 Rape (1) 75 90 10080 85 Redroot pigweed85 90 Redroot pigweed 65 75 80 85 100 Russian thistle60 200 Russian thistle 60 80 80 - 80 Scentless 70 85 Scentless chamo 65 65 60 70 85 chamo Spring Barley5 5 Spring Barley 0 0 0 2 5 Sugar beet 200 100 Sugar beet 100100 100100100 Sunflower 70 75 Sunflower 60 70 90 75 100 Veronica hedera100 90 Veronica hedera 10080 10090 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 buckwheat85 85 Wild buckwheat 60 55 70 85 75 Wild mustard 85 90 Wild mustard 85 85 100100100 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 20 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 I00 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 (oxtail 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 26 g/ha 16 23 29 30 40 Rate 8 g/ha 29 30 40 POSTEMERGENCE POSTEMERGENCE

Annual bluegras5 10 20 20 5 Annual bluegras5 10 5 Barley (winter)0 10 5 0 20 Barley (winter)5 5 20 Blackgrass 10 10 10 5 10 Blackgrass (2) 10 0 5 (2) Blk nightshade80 70 80 70 65 Blk nightshade 60 60 55 Chickweed 100 75 100 85 85 Chickweed 50 60 50 Common poppy 6 7 7 10 8 Common poppy 5 7 7 Deadnettle 100 100100 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 foxtail100 70 100 85 85 Green foxtail 70 60 70 I. Ryegrass 0 5 10 2 5 I. Ryegrass 2 0 10 Jointed goatgra10 0 0 5 5 Jointed goatgraIO 5 2 Kochia - 60 55 50 55 Kochia 45 45 35 Lambsquarters80 75 90 100100 Lambsquarters 85 80 100 LS canarygrass30 5 50 30 30 LS canarygrass 10 20 15 Rape (1) 40 60 60 30 50 Rape (1) 30 25 55 Redroot pigweed60 60 85 75 85 Redroot pigweed70 60 75 Russian thistle60 - 80 50 60 Russian thistle10 30 50 Scentless 55 50 70 - - Scentless chamo10 100-chamo Spring Barley10 0 0 0 0 Spring Barley 0 0 20 Sugar beet 100 100100 100100 Sugar beet 100100100 Sunflower 70 55 75 50 50 Sunflower 40 30 30 Veronica hedera75 70 70 75 70 Veronica hedera10 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 buckwheat50 50 75 65 50 Wild buckwheat 55 30 30 Wild mustard 100 65 85 100100 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 (10)

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 C1-C10 alkyl optionally substituted with halogen, C2-C6 alkoxyalkyl, C2-alkenyl or C3-C6 cycloalkyl; or Q is phenyl, benzyl, pyridyl, furanyl or thienyl, each optionally substituted with C1-C3 alkyl, C1-C3 alkoxy, cyano, halogen, COOH or S(=O)2OH; or A together with Q is -OC(=O)NR6R7;
R1 is C1-C3 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 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 C1-C2 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 C~-C3 alkyl, C 1-C3 alkoxy, cyano or halogen; and R2 and R3 are each independently C1-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 C1-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C1-C3 alkyl, C1-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-1-benzothiopyran-4,2'-[1,3]dioxolan]-yl)carbonyl]-1-ethyl-1H 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]-1-ethyl-1H 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-1H-pyrazol-5-yl](1-methylethyl) carbonate;
(d) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolan]-yl)carbonyl]-1-ethyl-1H-pyrazol-5-yl] ethyl carbonate S,S-dioxide;
(e) [5-(benzoyloxy)-1-ethyl-1H-pyrazol-4-yl](2,3-dihydro-5,8-dimethylspiro[4H-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]-1-ethyl-1H-pyrazol-5-yl] cyclopropanecarboxylate; and (g) [4-[(2,3-dihydro-5,8-dimethylspiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolan]-yl)carbonyl]-1-ethyl-1H-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.