CA2257196A1 - Herbicidal pyridinyl and pyrazolylphenyl ketones - Google Patents

Herbicidal pyridinyl and pyrazolylphenyl ketones Download PDF

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CA2257196A1
CA2257196A1 CA 2257196 CA2257196A CA2257196A1 CA 2257196 A1 CA2257196 A1 CA 2257196A1 CA 2257196 CA2257196 CA 2257196 CA 2257196 A CA2257196 A CA 2257196A CA 2257196 A1 CA2257196 A1 CA 2257196A1
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alkyl
compound
halogen
so2n
cyano
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French (fr)
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Morris Padgett Rorer
Kanu Maganbhai Patel
Chi-Ping Tseng
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EIDP Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compounds of Formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein Q is Q-1, Q-2, Q-3 or Q-4; and A, W, R1, R3-R11, and m 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

CA 022~7196 1998-11-30 TITLE
HERBTCnDAL PYRnDnNYL A ~ PYRAZOLYLPHENYL KETDNES
BACKGROUND OF THE INVENTION
This invention relates to certain phenyl ketones, their N-oxides, agriculturally5 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 10 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, 15 environmentally safer or have different modes of action.
WO 96/26200 discloses pyrazoles of Formula i as herbicides:

Q~ /z L

20 wherein, interalia Q represents a cyclohexane- 1 ,3-dione ring;
L and M are hydrogen, Cl-C6 alkyl, Cl-C4 alkoxy, halogen or nitro; and Z represents a five to six-membered heterocyclic saturated or unsaturated group.The phenyl ketones of the present invention are not disclosed in this publication.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula I including all geometric and. stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:

. .

CA 022~7196 1998-11-30 wo 97/46530 PCT/US97/09569 O (Rl)m Q ~ W
~ A

wherein Qis ~ ~RS

N ~ R
~ R8 or Rl]

Q-3 Q_4 s A is a five- to ten-membered monocyclic or fused bicyclic ring system, which maybe fully aromatic or partially saturated, containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 2 oxygens and no more than 2 sulfurs, and each ring system is optionally substituted with one to three R2, provided that when a nitrogen atom of a heterocyclic ring is substituted with R2, then R2 is other than halogen;
each Rl is independently H, Cl-C6 alkyl, C1-C6 haloalkyl, Cl-C6 alkoxy, Cl-C6 haloalkoxy, halogen, cyano, nitro, -(Y)t-S(O)nRIs or-(Y)t-C(O)RIs;
W is N or CH;
Y is O or NRI2;
R2 is Cl-C6 alkyl, Cl-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C~ -C6 alkoxy, C l-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, mercapto, Cl-C6 alkylthio, Cl-C3 CA 022~7196 1998-11-30 PCTrUS97/09569 haloalkylthio, C3-C6 alkenylthio, C3-C6 haloalkenylthio, C3-C6 alkynylthio, C2-Cs alkoxyalkylthio, C3-Cs acetylalkylthio, C3-C6 alkoxycarbonylalkylthio, C2-C4 cyanoalkylthio, Cl-C6 alkylsulfinyl, Cl-C6 haloalkylsulfinyl, Cl-C6 alkylsulfonyl, Cl-C6 haloalkylsulfonyl, arninosulfonyl, Cl-C2 alkylaminosulfonyl, C2-C4 dialkylarninosulfonyl, (CH2)rRI6~ NRI2Rl3, halogen, cyano or nitro; or R2 is phenyl or benzylthio, each optionally substituted on the phenyl ring with C1-C3 alkyl, Cl-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
R3 is oR14, SH, Cl-C6 alkylthio, Cl-C6 haloalkylthio, Cl-C6 alkylsulfinyl, Cl-C6haloalkylsulfinyl, Cl-C6 alkylsulfonyl, Cl-C6 haloalkylsulfonyl, halogen or NR12RI3; or R3 is phenylthio, phenylsulfonyl or -SCH2C(O)Ph, each optionally substituted with Cl-C3 alkyl, halogen, cyano or nitro;
each R4 is independently Cl-C3 alkyl, Cl-C3 alkoxy, Cl-C3 alkylthio or halogen;
or when two R4 are attached to the same carbon atom, then said R4 pair can be taken together to form -OCH2CH2O-, -OCH2CH2CH2O-, -SCH2CH2S-or -SCH2CH2CH2S-, each group optionally substituted with 1-4 CH3;
R5 is oRI4, SH, Cl-C6 alkylthio, Cl-C6 haloalkylthio, C]-C6 alkylsulfinyl, Cl-C6haloalkylsulfinyl, C1-C6 alkylsulfonyl, Cl-C6 haloalkylsulfonyl, halogen or NRI2Rl3; or R5 is phenylthio, phenylsulfonyl or -SCH2C(O)Ph, each optionally substituted with Cl-C3 alkyl, halogen, cyano or nitro;
R6 is H, Cl-C6 alkyl, Cl-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or -CH2CH2ORI2; or R6 is phenyl or benzyl, each optionally substituted on the phenyl ring with Cl-C3 alkyl, halogen, cyano or nitro;
R7 is H, Cl-C6 alkyl, Cl-C6 haloalkyl, Cl-C6 alkoxy, Cl-C6 haloalkoxy, halogen, cyano or nitro;
R8 is H, Cl-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;R9 is H, C2-C6 alkoxycarbonyl, C2-C6 haloalkoxycarbonyl, CO2H or cyano;
Rl~ is Cl-C6 alkyl, Cl-C6 haloalkyl, C3-C6 cycloalkyl optionally substituted with 1-4 Cl-C3 alkyl or C3-C6 halocycloalkyl;
Rl I is cyano, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, S(o)nRI3 or C(o)NR12R13;
each R12 is independently H or Cl-C6 alkyl;
R13 is Cl-C6 alkyl or Cl-C6 alkoxy; or R12 and Rl3 can be taken together as -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-,-CH2CH2CH2CH2CH2- or-CH2CH2OCH2CH2-;
Rl4 is H, Cl-C6 alkyl, Cl-C6 haloalkyl, C2-C6 alkoxyalkyl, forrnyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C(o)NRI2Rl3, Cl-C6 alkylsulfonyl or Cl-C6 haloalkylsulfonyl; or Rl4 is phenyl, benzyl, benzoyl, .. . . .

CA 022=,7196 1998-11-30 W O 97/46530 PCT~US97/09569 -CH2C(O)phenyl or phenylsulfonyl, each optionally substituted on the phenyl ring with Cl-C3 alkyl, halogen; cyano or nitro;
Rl5 is NR12R13, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkyl, Cl-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or C3-C6 cycloalkyl; or RlS is phenyl optionally substituted with Cl-C3 alkyl, Cl-C3 haloalkyl, Cl-C3 alkoxy, Cl-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
R16 is Cl-C3 alkoxy, C2-C4 alkoxycarbonyl, Cl-C3 alkylthio, Cl-C3 alkylsulfinyl or Cl-C3 alkylsulfonyl; or R16 is phenyl optionally substituted with Cl-C3 alkyl, C1-C3 haloalkyl, Cl-C3 alkoxy, Cl-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
misO, 1,20r3;
nisO, 1 or2;
p is 0, 1, 2, 3 or 4;
r is 1 , 2 or 3; and tisOor 1;
provided that when W is CH and A is in the meta position with respect to the group Q-C(O)- of Formula I, then m is 3 and Rl is other than H.
In the above recitations, the term "alkyl", used either alone or in compound words 20 such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl. "Alkenyl" includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.25 "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
"Alkynyl" includes straight-chain or branched alkynes such as l-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, 30 pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl.
Examples of "alkoxyalkyl" include CH30CH2, CH30CH2CH2, CH3CH20CH2, CH3CH2CH2CH20CH2 and CH3CH20CH2CH2. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylsulfinyl" includes both 35 enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O), CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(0)2, CH3CH2S(0)2, CH3CH2CH2S(0)2, (CH3)2CHS(0)2 and the different CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09S69 butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples.
"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. 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, CICH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the 10 like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl"
include (Cl)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC_CCHCl, CF3C-C, CCl3C-C and FCH2C_CCH2. Examples of "haloalkoxy"
include CF30, CCl3CH20, HCF2CH2CH20 and CF3CH20. Examples of "haloalkylthio" include CCl3S, CF3S, CCI3CH2S and ClCH2CH2CH2S. Examples of 15 "haloalkylsulfonyl" include CF3S(0)2, CC13S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2.The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 6. ~or example, Cl-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH30CH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH30CH2CH2 or 20 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 CH3CH20CH2CH2. Examples of "alkylcarbonyl"
include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH30C(=O), CH3CH20C(=O), CH3CH2CH20C(=O), 25 (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 group contains a substituent which can be hydrogen, for example R1 or 30 Rl4, 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 35 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, N-oxides and ... . . ...

CA 022~7196 1998-11-30 wo 97/46530 PCTIUS97/0g569 agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
Some compounds of this invention can exist as one or more tautomers. One skilled in the art will recognize, for example, that compounds of Forrnula Ia (Formula I
where Q is Q-1, R3 is oR14, and R14 is H) can also exist as the tautomers of Formulae Ib and Ic as shown below. One skilled in the art will recognize that said tautomers often exist in equilibrium with each other. As these tautomers interconvert under environmental and physiological conditions, they provide the same useful biological effects. The present invention includes mixtures of such tautomers as well as the individual tautomers of compounds of Formula I.

~ Ia ~,(Rl)m,J~f >~W(Rl)m ~4) ~ ~ - ~4) ~ ~ A

Ib Ic The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydloblolllic, hydrochloric, nitric, phosphoric, 15 sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group 20 such as a carboxylic acid or enol. Preferred salts include the lithium, sodium, potassium, triethylammonium, and quaternary ammonium salts of the compounds of the invention.
Preferred compounds for reasons of better activity and/or ease of synthesis are:

CA 022~7196 1998-11-30 - PCT/USg7/09569 Wo 97/46S30 Preferred 1. Compounds of Formula I, and N-oxides and agriculturally-suitable salts thereof, wherein:
A is selected from the group lH-pyrrolyl; furanyl; thienyl; lH-pyrazolyl;
lH-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl;
S lH-1,2,3-triazolyl; 2H-1,2,3-triazolyl; lH-1,2,4-triazolyl; 4H-1,2,4-triazolyl;
1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl;
1,2,3-thi~ 7.olyl; 1,2,4-thi~ 7.olyl; 1,2,5-thi~ 7Olyl; 1,3,4-thi~ olyl;
lH-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl;
1,3,5-triazinyl; 1,2,4-triazinyl; and A may optionally be substituted by one to three R2, provided that when a nitrogen atom of a heterocyclic ring is substituted with R2, then R2 is other than halogen;
Preferred 2. Compounds of Preferred l wherein:
Q is Q- l Preferred 3. Compounds of Preferred 2 wherein:
each Rl is independentiy Cl-C3 alkyl, Cl-C3 alkoxy, halogen or nitro;
R3 is oRl4; and Rl4 is H or Cl-C4 alkylsulfonyl; or Rl4 is benzoyl or phenylsulfonyl, each optionally substituted with Cl-C3 alkyl, halogen, cyano or nitro.
Preferred 4. Compounds of Preferred 3 wherein:
A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
R2 is -(Y)t-S(o)nRl5, CF3, OCF3, OCF2H or cyano;
Rl5 is Cl-C6 alkyl;
t is 0; and nis2.
Preferred 5. Compounds of Preferred 1 wherein:
Q is Q-2;
Preferred 6. Compounds of Preferred 5 wherein:
each Rl is independently Cl-C3 alkyl, Cl-C3 alkoxy, halogen or nitro;
R5 is ORl4;
Rl4 is H or Cl-C4 alkylsulfonyl; or Rl4 is benzoyl or phenylsulfonyl, each optionally substituted with Cl-C3 alkyl, halogen, cyano or nitro.
R6 is H, Cl-C6 alkyl, or C3-C6 alkenyl; and R7isH;
Preferred 7. Compounds of Preferred 6 wherein:
A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
R2 is -(Y)t-S(o)nRI5, CF3, OCF3, OCF2H or cyano;

CA 022~7196 1998-11-30 W O 97t46530 PCTAUS97/09569 R15 is Cl-C6 alkyl;
t is 0; and nis2.
Preferred 8. Compounds of Preferred 1 wherein:
Q is Q-3.
Preferred 9. Compounds of Preferred 8 wherein:
each Rl is independently Cl-C3 alkyl, Cl-C3 alkoxy, halogen or nitro;
R8 is H, Cl-C3 alkyl, or cyclopropyl; and R9 is H or C2-C3 alkoxycarbonyl.
Preferred 10. Compounds of Preferred 9 wherein:
A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
R2 is -(Y)t-S(o)nR15, CF3, OCF3, OCF2H or cyano;
Rl5 is Cl-C6 alkyl;
t is 0; and lS nis2.
Preferred l l. Compounds of Preferred 1 wherein:
QiSQ-4 Preferred 12. Compounds of Preferred 11 wherein:
each Rl is independently Cl-C3 alkyl, C1-C3 alkoxy, halogen or nitro;
R10 is C3-C6 cycloalkyl or C3-C6 halocycloalkyl, each optionally substituted with 1-4 Cl-C3 alkyl; and Rl l is cyano or C2-C6 alkoxycarbonyl.
Preferred 13. Compounds of Preferred 12 wherein:
A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
R2 is -(Y)t-S(o)nR15, CF3, OCF3, OCF2H or cyano;
Rl5 is C1-C6 alkyl;
t is 0; and nis2.
Most preferred are compounds of Formula Ia above, and sodium, potassium, and quaternary ammonium salts thereof, selected from the group:
a) 3-hydroxy-2-[[6-(trifluoromethyl)[2,4'-bipyridin]-3-yl]carbonyl]-2-cyclohexen- 1 -one;
b) 2-[2-chloro-4-(4-pyridinyl)benzoyl]-3-hydroxy-2-cyclohexen-1-one; and c) 2-[2,5-dimethyl-3-( 1 -methyl- lH-pyrazol-3-yl)-4-(methylsulfonyl)benzoyl]-3-hydroxy-2-cyclohexen- 1-one.
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 CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 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 5 compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds.
DETAILS OF THE INVENTION
The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-22. The definitions of W, Y, A,R1-RI6, m, n, p, r, and t in the compounds of Formulae 1-22 below are as defined above in the Summary of the Invention. Compounds of Formulae Ia-Ig are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Ig are as defined above for Formula I.
Compounds of General Formula Id can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1-14 of this section as well as by following the specific procedures given in Example l.

a~4)p ~A

Id Scheme 1 illustrates the preparation of compounds of Formula Id (R3 is ORl 7 andRl7 is the same as Rl4 as described in the Summary of the Invention excluding H)whereby a compound of Formula Id (R3 is OH) is reacted with a reagent of Formula 1 in the presence of a base wherein Xl is chlorine, bromine, fluorine, trifluorosulfonyloxy (OTf) or acetyloxy (OAc) and Rl7 is as previously defined. The coupling is carried out by methods known in the art (or by slight modification of these methods): for example, see K. Nakamura, et al., WO 95/04054.

.. .. . .. .. . .. . .. .. .. . . . ..

CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 Scheme 1 Id(R3isOH) + R17Xl ' Id (R3isoR17 Base wherein R17 is the same as R14 as described in the Summary of the Invention excluding H;
X l is chlorine, bromine, fluorine, trifluorosulfonyloxy (OTt) or acetyloxy (OAc) Scheme 2 illustrates the preparation of compounds of Formula Id (R3 is SOnRI8;
n is I or 2; and Rl8 is Cl-C6 alkyl or Cl-C6 haloalkyl) whereby a compound of 5 Formula Id (R3 is SR18) is reacted with an oxidizing reagent such as peroxyacetic acid, m-chloroperoxybenzoic acid, potassium peroxymonosulfate (e.g., Oxone~), available from Aldrich Chemical Company), or hydrogen peroxide (the reaction may be buffered with a base such as sodium acetate Qr sodium carbonate). The oxidation is carried out by methods known in the art (or by slight modification of these methods): for example, see B. M. Trost, et al., J. Org. Chem. (1988), 53, 532; B. M. Trost, et al., Tetrahedron Lett. (1981), 21, 1287; S. Patai, et al., The Chemistry of Sulphones and Sulphoxides, John Wiley & Sons, Protecting and deprotecting functional groups not compatible with the reaction condition may be necessary for compounds with such a functional group (for procedures, see T. W. Greene, et al., Protective Groups in Organic Synthesis, Second Edition, John Wiley & Sons, Inc.).

Scheme 2 Id (R3 is SRI 8) ~ Id (R3 is S(O)nR 18; n is I or 2) oxidizing agent wherein R18 is Cl-C6 alkyl or Cl-C6 haloalkyl Compounds of Formula Id (R3 is Nu; Nu is SR18or oRl9; R18 is as defined previously; Rl9 is Cl-C6 alkyl, Cl-C6 haloalkyl or C2-C6 alkoxyalkyl) can be prepared by one skilled in the art from a compound of Formula Id (R3 is halogen) by treatment with a nucleophile of Formula 2 (Nu is SR18or oR19; M is Na, K or Li) as shown in Scheme 3 using methods well documented in the literature (or slight modification of these methods): for example, see S. Miyano, et al., J. Chem. Soc., Perkin Trans. I
(1976), 1146.

CA 022~7196 1998-11-30 PCTrUS97/09569 Scheme 3 Id (R3 is halogen) + MNu ~ Id (R3 is SR 18 or oR19) wherein Nu is SR 18 or ORI 9; M is Na, K or Li;
and Rl9 is Cl-C6 alkyl, C1-C6 haloalkyl or C2-C6 alkoxyalkyl Compounds of Formula Id (R3 is halogen) can be prepared by reacting a compound of Formula Id (R3 is OH) with a halogenating reagent such as oxalyl 5 bromide or oxalyl chloride (Scheme 4). This conversion is carried out by methods known in the art (or by slight modification of these methods): for example see S. Muller, et al., WO 94/13619; S. Muller, et al., DE 4,241,999.

Scheme 4 Id (R3 is OH) ~ Id (R3 is halogen) Halogenating reagent (e.g., oxalyl bromide, oxalyl chloride) Scheme 5 illustrates the preparation of compounds of Formula Id (R3 iS OH).
whereby an enol ester of Formula 3 is reacted with a base such as triethylamine in the presence of a catalytic amount of cyanide source (e.g., acetone cyanohydrin or potassium cyanide). This rearrangement is carried out by methods known in the art 15 (or by slight modification of these methods): for example see W. J. Michaely, EP 369,803.

Scheme S
o R4)p bLo~ Base (e.g., triethyalmine)~ Id (R3 is OH) A cyanide source in catalytic ,~J amount (e.g., acetone cyano-~ hydrin or potassium cyanide) Enol esters of Formula 3 can be prepared by reacting a dione of Formula 4 with an 20 acid chloride of Formula 5 in the presence of a slight mole excess of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 ~C and 110 ~C (Scheme 6). This type of coupling is known in the art: for example, see W. J. Michaely, EP 369,803.

Scheme 6 (R4)p~ a~A triethylam;ne)~ 3 The acid chlorides of Formula 5 can be prepared by one skilled in the art by reacting an acid of Formula 6 with oxalyl chloride (or thionyl chloride) and a catalytic amount of dimethylformamide (Scheme 7). This chlorination is well known in the art:
for example, see W. J. Michaely, EP 369,803.

Scheme 7 O (Rl)m Jl ~ oxalyl chloride HO ~ ~ W (or thionyl chloride (catalytic amount of N,N-dimethyl-formamide) Enol esters of Formula 3a can also be prepared by directly reacting the acid of 15 Formula 6a with N-methyl-2-chloropyridinium iodide, followed by treatment of the formed intermediate with the dione of Formula 4 in the presence of a base such as triethylamine (Scheme 8). This coupling is carried out be methods known in the art (or by slight modification of these methods): for example, see E. Haslam Tetrahedron(1980), 36, 2409-2433.

- PCT/USg7/09569 Wo 97/46~30 Scheme 8 HO~ + ~ + ~4 6a CH3 Et3N (R4)p~Lo~X
R
3a Scheme 9 illustrates the preparation of acids of Formula 6 (Rl is S(O)nRI5 and n is 1 or 2) whereby an acid of Formula 6 (Rl is SRI5) is reacted with an oxidizing 5 reagent such as peroxyacetic acid, m-chloroperoxybenzoic acid, Oxone~, or hydrogen peroxide (the reaction may be buffered with a base such as sodium acetate or sodium carbonate). The oxidation is carried out by methods known in the art (or by slight modification of these methods): for example, see B. M. Trost, et al., J. Org. Chem.
(1988), 53, 532; B. M. Trost, et al., Tetrahedron Lett. (1981), 21, 1287; S. Patai, et al., 0 The Chemistry of Sulphones and Sulphoxides, John Wiley & Sons. For some acids of Formula 6 (Rl is SR15) with a functional group not compatible with the reaction conditions, the functional group may be protected before the oxidation and then be deprotected after the oxidation. The protecting and deprotecting procedures are well known in the literature: for example see T. W. Greene, et al., Protective Groups in 15 Organic Synthesis (Second Edition), John Wiley & Sons, Inc.
Scheme 9 O (Rl)m HO/~A ~ 6 Oxi~ii7in~ agent wherein Rl is S(o)nR15 and n is O wherein Rl is S(O)nR15 and n is I or 2 CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 Scheme 10 illustrates the preparation of acids of Formula 6 (n is 0 if Rl is S(O)nR1s) whereby a phenyl bromide of Formula 7 (n is 0 if Rl is S(~)n Rls) is treated with n-butyllithium (or m~nesium) and the lithium salt (or the Grignard reagent)generated in situ is then reacted with carbon dioxide followed by acidification with an 5 acid such as hydrochloric acid. This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see M. A. Ogliaruso, et al., Synthesis of Carboxylic Acids, Esters and Their Derivatives, pp 27-28, John Wiley & Sons; A. J. Bridges, et al., J. Org. Chem. (1990), 55, 773; C. Franke, et al., Angew.
Chem. Int. Ed. (1969), 8, 68. Protecting and deprotecting functional groups not 10 compatible with the reaction conditions may be necessary for compounds with such a functional group.

Scheme 10 (R1)m 1) n-BuLi (or Mg) ~ (Rl)m Br~w 2) C02 HOJ~W
~A 3) H+

wherein W is CH, and if R 1 is S(O)nR15, then n is 0 Many acids of Formula 6 can also be prepared, as shown in Scheme 11, whereby an ester of Formula 8 is saponified (for example, potassium hydroxide in methanol, then acidification with an acid such as hydrochloric acid), or, alternatively, hydrolyzed in acid (for example, 5N hydrochloric acid in acetic acid) by methods known in the art (or slight modification of these methods); see for example, M. A. Ogliaruso, et al.,20 Synthesis of Carboxylic Acids, Esters and Their Derivatives, John Wiley & Sons, (1991), pages 5-7.
Scheme 1 1 ~ / I) KOH in methanol R200'--~, 2) acid ~ 6 wherein R20 is CH3 or CH2CH3 W 097/46530 PCT~US97/09569 Esters of Formula 8 can be prepared using methods known in the art (or by slightmodification of these methods): for example, see A. R. Katritzky, et al., Comprehensive Heterocyclic Chemistry, volumes 2-6, Pergamon Press.
Esters of Formula 8a or 8b can also be prepared as shown in Scheme 12, whereby an ester of Formula 9a or 9b is contacted with an ap~ iate nucleophilic heterocycle Nul and a suitable base in an inert solvent. This reaction can be carried out by a variety of well-known methods, preferably with potassium carbonate or potassium tert-butoxide as the base with N,N-dimethylformamide as the solvent and at a reaction temperature range of from approximately 0 to 100 ~C.

Scheme 12 o x3 R200J~W R200J~W

9a (R1)m 8a (Rl) or K2C03 in DMF or R200~)x3 R200~A I

9a 8a wherein X3 is Cl, F or CF3S~2~; wherein A I is l~l-imidazole, IH-pyrazole, 1f~-1,2,4-triazole or 4H-1,2 4-triazole Nu I Is an Imldazole, pyrazole or trlazole Esters of Formula 9a and 9b are commercially available or can be prepared using methods known in the art (or by slight modification of these methods).
Scheme 13 illustrates the preparation of acids of Formula 6a whereby an aryl bromide of Formula 9c is treated with an aryl tin reagent in the presence of a palladium catalyst. This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see M. Fujta, et al., Tetrahedron Letters, (1995), 29, 5247-5250; Y. Yamamoto, et al., Heterocycles, (1996), 42, 189-194.
- 20 Saponification of the ester with a base such as sodium hydroxide provides the acids of Formula 6a.

. ~. . .

CA 022~7l96 l998-ll-30 W 097146530 PCTAUS97/09~69 Scheme 13 CH30 ~ I)A-Sn(Bu) Rl 2) NaOH,MeOH R
9c 6a Bromides of Formula 9c are either commercially available or can easily be prepared by methods known in the art (or by slight modification of these methods): for example, see T. Bryson, et al., J. Org. Chem., (1976),41,2066; Andrea, T. A. andLiang, P. H., U.S. 5,393,734. Aryl and heteroaryl organotin compounds can be prepared by methods known in the art (or by slight modification of these methods): for example, see D. Peters, et al., J. Heterocyclic Chem., (1990),27,2165.
Bromides of Formula 7 (n is O if Rl is S(~)n Rl5) can be prepared by one skilledin the art by using methods known in the art (or by slight modification of thesemethods): for example, see A. R. Katritzky, et al., Comprehensive Heterocyclic Chemistry, Volume 2-6, Pergamon Press; B. M. Lynch, et al., Tet. Lett. (1964), p. 617;
M. A. Kahn, et al., Rev. Latinoam. Quim. (1972),3,p.119; M. Kosugi, et al., Bull.
Chem. Soc. Jpn. (1986), 59 (2), p. 677.
Alternatively some of the bromides of Formula 7 (n is O if Rl is S(O)nRIs) can also be prepared by bromination of the corresponding substituted benzenes of Formula 8 (n is O if R1 is S(o)nRI5) with the bromine or other equivalent reagent in an inert organic solvent as shown in Scheme 14. This bromination is carried out by general methods known in the art; see, for exarnple, E. Campaigne, et al., J. Heterocycl. Chem.
(1969),6,p.517;~. Gilman, J. Am. Chem. Soc. (1955),77,p.6059;

Scheme 14 ~l)m (Rl)m H ~ ~ W Br2 or other equivalent Br~(/w I,.-.,.. ;.~li--~ rea~ent ~ ~A

The compounds of Formula 8 (n is O if Rl is S(o)nRI5) can be prepared by one skilled in the art by using methods known in the art (or by slight modification of these methods): for example, see A. R. Katritzky, et. al., Comprehensive Heterocyclic Chemistry, Volume 2-6, Pergamon Press; B. M. Lynch, et al., Tet. Lett. (1964), p. 617;

CA 022~7196 1998-11-30 WO 97/46s30 PCT/USg7/09569 M. A. Kahn, et al., Rev. Latinoam. Quim. (1972), 3, p. 119; M. Kosugi, et al., Bull.
Chem. Soc. Jpn. (1986), 59, (2), p. 677.
Compounds of General Forrnula Ie can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 15-17 of this section.

?~)m l6 Ie Scheme 15 illustrates the preparation of compounds of Formula Ie (Rl4 is Rl4a and Rl4a is the same as Rl4 as described in the Summary of the Invention excluding H) whereby a compound of Formula Ie ( Rl4 is H) is reacted with a reagent of Formula 9 in the presence of a base wherein x2 is chlorine, bromine, fluorine, OTf or OAc and Rl4a 10 is as previously defined. This coupling is carried out by methods known in the art (or by slight modification of these methods): for example, see K. Nakamura, et al., WO 95/04054.

Scheme 15 le (R14 is H) + R14aX~ Ie (R14 is R14a Scheme 16 illustrates the preparation of compounds of Formula Ie (Rl4 is H).
whereby an ester of Formula 10 is reacted with a base such as triethylamine in the presence of a catalytic amount of cyanide source (e.g., acetone cyanohydrin or potassium cyanide). This rearrangement is carried out by methods known in the art (or by slight modification of these methods): for example, see W. J. Michaely, EP 369,803.

Scheme 16 O (Rl)m oJ~w (e.g., triethylamine) ~ I ~A cyanide source in Ie (R14 is H) R7 ~ N ~/ catalytic amount N-- ~R6 (e.g., acetone cyanohydrin or potassium cyanide) CA 022~7l96 l998-ll-30 W 097/46S30 PCT~US97/09569 Esters of Formula 10 can be prepared by reacting a hydroxypyrazole of Formula 11 with an acid chloride of Formula 5 in the presence of a slight mole excess of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 ~C and 110 ~C (Scheme 17).
5 This type of coupling is carried out by methods known in the art (or by slightmodification of these methods): for example, see W. J. Michaely, EP 369,803.

Scheme 17 R7 base HO ~ (e.g.,triethylamine) Compounds of General Formula If can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 18-21 of this section.
R~)m Scheme 18 illustrates the preparation of compounds of Formula If whereby a compound of Formula 12 is reacted with a salt of hydroxylamine such as hydroxylamine 15 hydrochloride in the presence of a base or acid acceptor such as triethylamine or sodium acetate. The substituents of the immediate products may be further modified if ap~vlvpliate This cyclization is carried out by methods known in the art (or by slight modification of these methods): for example, see P. A. Cain, et al., EP 560,483; C. J.
Pearson, et al., EP 636,622.

W O 97/46530 PCT~US97/09569 Scheme 18 R9a ~ (Rl)m 11 / H2NO~ HCI
L~ ~ (or other salt of H2NOH) wherein L is a leaving ~roup such as C l-C4alkoxy (e.g. OC2H5) or N,N-dialkylamino (e.g. dimethyl amino) K9a is R9 or CONH2 Scheme 19 illustrates the preparation of compounds of Formula 12 whereby a compound of Formula 13 is reacted with a reagent of Formula 14 or Formula 15. This conversion is carried out by methods known in the art (or by slight modification of these 5 methods): for example, see P. A. Cain, et al., EP 560,483; C. J. Pearson, et al., EP 636,622.

Scheme 19 R8 , ~D ~ ~lAm OR21 12 R9a_~
13 \N--CH3 wherein R21 is Cl-C4alkyl CH3 Scheme 20 illustrates the preparation of compounds of Formula 13 whereby a 10 ester of Formula 16 is decarboxylated in the presence of a catalyst, such as p-toluenesulfonic acid, in an inert solvent such as toluene. This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see P. A. Cain, et al., EP 560,483; C. J. Pearson, et al., EP 636,622.

Scheme 20 R8 ~ ~ iw p-lol IPn~5ulfonic acid toluene t-Bu~

CA 022~7196 1998-11-30 WO 97/46530 PcT/uss7/09s69 Esters of Formula 16 can be prepared by reacting the metal salt of a compound ofFormula 17 with an acid chloride of Formula 5 (Scheme 21). This type of coupling is known in the art: for example see P. A. Cain, et al., EP 560,483; C. J. Pearson, et al., EP 636,622.

Scheme 21 o O
R8J~(}t-su + S ~ l6 Scheme 22 illustrates the preparation of compounds of Formula Ig whereby a compound of Formula 5 is reacted with a compound of Formula 18 in the presence of a base such as triethylamine, potassium carbonate, sodium hydride or Mg(OEt)2 in an 10 inert organic solvent such as diethyl ether, tetrahydrofuran, N,N-dimethylform~mi(lc, dichloromethane or acetonitrile.

Il I (Rl)m Rl~ /~W
Rll ~ A

Ig This conversion is carried out by methods known in the art (or slight modification of these methods); for example, see J. W. Ashmore, EP 213,892 and P. A. Caln, EP496,631 A1.

Scheme 22 S + RlOJ~ base Rll 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 CA 022~7196 1998-11-30 W 097/46~30 PCTrUS97/09569 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, 5 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 sequence10 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 20 for chromatographic solvent mixtures are by volume unless otherwise indicated.
IH 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.

25 Step A: Preparation of 3-~(2t5-dimethylphenyl~thiolpropanoic 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 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 30 portions keeping the temperature below 25 C. The mixture was warmed to room temperature, stirred for 2 hr under nitrogen, and was then washed with diethyl ether (3 x 500 mL). The aqueous layer was acidified with lN HCl and filtered to yield 112.79 g of the title compound of step A as a solid, m.p. 97-98 C.
1H NMR (CDCl3): o 2.3 (s, 3H), 2.34 (s, 3H), 2.68 (t, 2H), 3.1 (t, 2H), 6.9 (d, lH), 7.06-7.14 (2H).
Step B: Preparation of 2,3-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 CA 022~7196 1998-11-30 W 0 97/46530 PCTrUS97/09569 removed, the mixture was stirred for 1 hr and was then poured over crushed ice. The aqueous phase was extracted with a mixture of diethyl ether: hexane (1:9, 6 x 500 mL), dried (MgSO4), filtered, and evaporated to dryness to yield 11.75 g of the titlecompound of step B as an oil.
1H NMR (CDCl3): o 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-l-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) in 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 then refluxed for 10 minutes. The warm mixture was poured into 10 mL of concentrated hydrochloric acid containing 75 g of ice, stirred for 10 minutes, diluted with 50 mL of water, and extracted with diethyl ether (2 x 200 mL). The combined organic layers were washed with water (2 x 200 mL), dried (Na2SO4), filtered, and evaporated to dryness.
The crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate: hexane (5:95) to yield 2.62 g of the title compound of step C as a solid, m.p.
87-88 C.
1H NMR (CDCl3): o 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-5,8-dimethyl-4H-I-benzothiopvran-4-one 30 g (0.11 mol) of the title compound of step C and 8.95 mL (0. l l mol) of pyridine were added to 250 mL of methylene chloride. The solution was cooled to about 0 C and 14.76 g (0.11 mol) of N-chlorosuccinimide was added. The mixture was stirred overnight under nitrogen while warming to room temperature and then refluxed for 12 h. The reaction was evaporated to dryness, the residue was stirred in diethyl ether, and filtered. The filtrate was dried (MgSO4), filtered, and evaporated to dryness to yield 13.25 g of the title compound of step D as a solid, m.p. 123-124 C.
1H NMR (CDCl3): o 2.5 (s, 3H), 2.9 (s, 3H), 7.0 (d, lH), 7.7 (m, 2H).
Step E: Preparation of 3-~3-bromo-2,5-dimethyl-6-(methylthio)phenyll-1-methyl-lH-pyrazole 13.25 g (0.049 mol) of the title compound of step D and 2.88 mL (0.054 mol) of methylhydrazine (purchased from Aldrich Chemical Company) was added to 150 mL ofabsolute ethanol. After stirring at reflux under nitrogen for 5 hr the mixture was allowed to warm to room temperature and stir for 2.5 days. The mixture was refluxed for 3 hr after which time 0.5 rnL of acetic acid was added and the reaction was refluxed CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97/09569 overnight. After cooling to room temperature, 12.35 mL (0.054 mol) of sodium methoxide (25% in methanol) and 3.66 rnL (0.059 mol) of iodomethane were added and the reaction stirred for 2 hr. The mixture was evaporated to dryness. The residue was stirred in water, extracted with methylene chloride (250 mL), dried (MgSO4), filtered, 5 and evaporated to dryness. The crude product was chromatographed over silica gel eluting with methylene chloride to yield 5.97 g of the title compound of step E as an oil.
1H NMR (CDC13): ~ 2.0 (s, 3H), 2.1 (s, 3H), 2.5 (s, 3H), 3.6 (s, 3H), 6.2 (s, lH),7.6(m,2H).
Step F: Preparation of 2,5-dimethy]-3-(1-methyl-lH-pyrazol-3-yl)-4-(methylthio)benzoic acid 5.9 g (0.019 mol) of the title compound of step E was added to 100 mL of tetrahydrofuran and cooled to -70 C. 9.1 mL (0.023 mol) of 2.5M n-butyllithium (purchased from Aldrich Chemical Company) was added dropwise keeping the temperature below -65 C. Solid carbon dioxide was added in one portion and the mixture warmed to room temperature. 200 mL of hexane was added and the mixture was filtered. The solid collected was added to water and acidified to about pH 1 with concentrated hydrochloric acid. The aqueous was extracted with methylene chloride (3 x 100 mL), dried (MgS04), filtered, and evaporated to dryness to yield 3.13 g of the title compound of step F as a semi-solid.
1H NMR (CDC13): o 2.1 (s, 3H), 2.3 (s, 3H), 2.6 (s, 3H), 3.6 (s, 3H), 6.2 (m, IH), 7.6 (d, lH), 7.97 (s, lH).
Step G. Preparation of 2,5-dimethyl-3-(1-methyl-lH-pyrazol-3-yl)-4-(methylsulfonyl)benzoic acid 4.5 mL (0.046 mol) of hydrogen peroxide (35%) was added to 25 rnL of trifluoroacetic acid. The mixture was allowed to stir for 30 min under nitrogen and was then cooled to 0 C. A solution of 3.1 g (0.011 mol) of the title compound of step F in 25 mL of trifluoroacetic acid was added dropwise keeping the temperature below 10 C.
The mixture was warmed to room temperature and stirred for 3 days. 2 rnL of dimethylsulfide was added and the reaction stirred for 30 min. The mixture was then evaporated to dryness, and the residue was triturated with water and filtered. The collected solid was dissolved in methylene chloride, dried (MgSO4), filtered, and evaporated to dryness to yield 1.41 g of the title compound of step G as a solid, m.p.
60t C (dec.).
lH NMR (CDC13): ~ 2.2 (s, 3H), 2.8 (s, 3H), 3.0 (s, 3H), 3.7 (s, 3H), 6.2 (m, lH), 7.7 (m, lH), 8.0 (s, lH).

CA 022~7196 1998-11-30 Wo 97l46S30 PC~/USg7/09569 Step H: Preparation of 3-oxo-1-cylcohexen-1-yl 2,5-dimethyl-3-(1-methyl-lH-pyrazol-3-yl)-4-(methylsulfonyl)benzoate 1.39 g (0.0045 mol) of the title compound of step G, 1.18 mL (0.0135 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 2.5 hr and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and the solution was again evaporated to dryness. Another 50 mL of methylene chloride was added to the residue, and the solution was cooled to about 0 C. 0.56 g (0.0049 mol) of 1,3-cyclohexanedione (purchased from Aldrich Chemical Company) was added followed by 1.94 mL (0.0139 mol) of triethylamine, and the mixture wasstirred overnight while warming to room temperature. The mixture was evaporated to dryness and the crude product was chromatographed over silica gel eluting with amixture of ethyl acetate:hexane (6:4, then 7:3) to yield 0.47 g of the title compound of step H as a solid, m.p. 165 - 167 C.
1H NM~ (CDC13): ~ 2.1 - 2.2 (m, SH), 2.5 (m, 2H), 2.7 (m, 2H), 2.8 (s, 3H), 2.98 (s, 3H), 3.6 (s, 3H), 6.0 (s, lH), 6.1 (m, lH), 7.6 (m, lH), 7.9 (s, lH).
Step I: Preparation of 2-~2,5-dimethyl-3-(1-methyl-lH-pyrazol-3-yl)-4-(methylsulfonyl)benzoyll- 1,3-cyclohexanedione 0.47 g (0.0012 mol) of the title compound of step H, 1 drop of acetone cyanohydrin (purchased from Aldrich Chemical Company), and 0.29 rnL (0.0020 mol)of triethylamine were added to 25 mL of acetonitrile and allowed to stir overnight at room temperature under nitrogen. The mixture was evaporated to dryness, water was added to the residue, and the solution was acidified to pH 1 with concentrated hydrochloric acid. The aqueous was extracted with methylene chloride, dried (MgSO4), filtered, and evaporated to dryness to yield 0.27 g of the title compound of example 1, a compound of the invention, as a solid, m.p. 93 C (decomposed).
lH NMR (CDCl3): o 1.8 (s, 3H), 2.1 (m, 2H), 2.4 (m, 2H), 2.7 (s, 3H), 2.8 (m, 2H), 2.98 (s, 3H), 3.7 (s, 3H), 6.2 (s, lH), 7.1 (s, lH), 7.6 (s, lH).

Step A: Preparation of 2-~3-(trifluoromethyl)-1~-pyrazol-1-yllbenzoic acid To 100 mL of dimethylformamide was added sequentially 19.3 g (0.125 mol) of methyl 2-fluorobenzoate, 18.7 g (0.138 mol) of 3-(trifluoromethyl)pyrazole (purchased from Maybridge Chemical Company), and 19.0 g (0.138 mol) of potassium carbonate.The suspension was stirred and heated at about 100 ~C for 16 hours, then cooled to 25 ~C and poured into excess water. The aqueous suspension was extracted three times with 75 mL of diethyl ether and the combined ether layers were dried over magnesium sulfate and concentrated under reduced pressure. The residual oil was chromatographed over silica gel eluting with hexane:ethyl acetate (9.6:0.4, then 100% ethyl acetate) to CA 022~7196 1998-11-30 yield 15.3 g of crude methyl 2-[3-(trifluoromethyl)-lH-pyrazol-l-yl]benzoate as an oil.
14 g (0.052 mol) of this oil was added to a solution of 3.8 g (0.057 mol) of potassium hydroxide (85%) dissolved in 60 rnL of methanol. The solution was stirred at 25 ~C for one hour, refluxed for 5 hours, stirred at 25 ~C for 48 hours, and finally concentrated S under reduced pressure. 100 mL of water was added to the residue and the cloudy solution was extracted twice with 40 mL of diethyl ether. The clear aqueous layer was acidified with concentrated HCI and filtered. The collected solid was dissolved in dichloromethane, dried over magnesium sulfate, and the solvent was removed underreduced pressure to yield S.0 g of the title compound of Step A as a solid melting at 13~-144 ~C.
1H NMR (CDC13): o 6.95 (d, lH), 7.65 (m, 2H), 7.7 (m, lH), 7.85 (m, lH), 8.35 (d, lH), 13.15 (s, lH).
SteP B: Preparation of 3-oxo-1-c~lclohexen-1-yl 2-~3-(trifluoromethyl)-1~-pyrazol- l -yllbenzoate lS To 20 mL of oxalyl chloride was added portionwise 4.0 g of the title compound of Step A. The suspension was refluxed for about 3 hours and then concentrated under reduced pressure. The residue was azeotroped with dichloromethane (two times with 20 mL at 60 ~C) to yield an oil which solidified upon cooling and melted at 64-68 ~C.
2.0 g (0.0073 mol) of this acid chloride was added to 20 mL of dichloromethane, followed by the addition of 0.99 g (0.0088 mol) of 1,3-cyclohexanedione, and 2.2 g (0.022 mol) of triethylamine. The suspension was stirred overnight and then concentrated under reduced pressure. The residue was dissolved in diethyl ether and the solution was then extracted with water, dried over magnesium sulfate, and concentrated under reduced pressure to yield 2.0 g of the title compound of Step B as an oil.1H NMR (CDC13): ~ 2.0 (m, 2H), 2.35 (m, 2H), 2.5 (m, 2H), 5.85 (s, lH), 6.75 (d, lH), 7.5 (m, lH), 7.6 (m, lH), 7.7 (m, lH), 7.8 (d, lH), 8.0 (m, lH).
Step C: Preparation of 3-hydroxy-2-r2-r3-(trifluorometh~ll)-lH-pyrazol-l-yllbenzoyll-2-cvclohexen- 1 -one To 20 mL of acetonitrile was added sequentially 1.8 g (O.OOS mol) of the title compound of Step B, 1.0 g (0.01 mol) of triethylamine, and 8 drops of acetone cyanohydrin. The solution was stirred under a nitrogen atmosphere at 25 ~C overnight, and then diluted with 40 rnL of water and acidified by the addition of concentrated hydrochloric acid (red to litmus paper). The suspension was filtered, and the collected solid was washed three times with 20 mL of water, suction dried, and then recrystallized from 2-propanol to yield 0.97 g of the title compound of Step C, a compound of this invention, as a solid melting at 141-143 ~C.
1H NMR (CDC13): o 1.8 (m, 2H), 2.1 (m, 2H), 2.6 (m, 2H), 6.6 (d, 1~), 7.4-7.6 (m, 4H), 7.75 (d, lH), 16.6 (s, lH).

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 Step A: Preparation of methyl 6-(trifluoromethyl)~2,4'-bipyridinel-3-carboxylate To a stirred solution of 8.49 g (0.03 mol) of methyl 2-bromo-6-(trifluoromethyl)-3-pyridine carboxylate (prepared as described by Andrea T. A. and Liang P. H., U.S.
Patent 5,393,734) in 25 mL of N,N-dimethylformamide under a nitrogen atmosphere was added 0.5 g of tetrakis(triphenylphosphine)palladium(0) and the mixture was heated at 100 ~C for 30 minutes. 11 g ~0.03 mol) of 4-tributylstannylpyridine (prepared by a modification of the procedure described by A. Lee and W. Dai, Tetrahedron Letters (1996), 37, 495-498) was added and heating was continued at 100 ~C for 24 hours. The reaction mixture was cooled to room temperature and N,N-dimethylformamide was removed by distillation under high vacuum. The residue was purified by flash chromatography over silica gel utilizing dichloromethane:ethyl acetate (8:2) to provide 4.0 g of the title compound of Step A as a red oil.
IH NMR (CDC13): ~ 8.76 (d, 2H), 8.4 (d, lH), 7.8 (d, lH), 7.47 (m, 2H), 3.76 (s, 3H).
Step B: Preparation of 6-~trifluoromethyl)~2,4'-bipvridinel-3-carbox~lic acid To a solution of 1.7 g of the title compound of Step A in 20 mL of methanol was added 2 mL of 50% aqueous sodium hydroxide and the reaction was stirred at room temperature for 24 hours. The mixture was concentrated and acidified with 6N aqueous hydrochloric acid to pH 3 and extracted three times with 20 mL of ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated underreduced pressure to provide 1.6 g of title compound of Step B as a crude solid.
1H NMR (CD3)2SO): ~ 9.02 (d, 2H), 8.26 (d, lH), 8.22 (m, lH), 8.14 (d, 2H).
Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 6-(trifluoromethvl)~2,4'-bipyridinel-3-carboxylate To a suspension of 1.6 g (6 mmol) of the title compound of Step B in 100 mL of dichloromethane was added 0.78 g (7 mmol) of 1,3-cyclohexanedione followed by 2.4 mL (16 mmol) of triethylamine and 1.8 g (7 mmol) of 2-chloro-1-methylpyridinium iodide. The mixture was stirred at room temperature under nitrogen for 24 hours and then applied directly to a silica gel column and purified by flash chromatography using ethyl acetate/dichloromethane (2:8) to afford 1.34 g of the title compound of Step C as a tan solid melting at 49-56 ~C.
lH NMR (CDC13): ~ 8.78 (d, 2H), 8.6 (d, lH), 7.51 (d, 2H), 5.93 (s, lH), 2.2 (m,2H), 2.1 (m, 2H), 2.0 (m, 2H).
Step D: Preparation of 3-hydroxy-2-r~6-(trifluoromethyl)~2,4'-bipyridinl-3 yllcarbonyll-2-c~clohexen- 1 -one To a solution of 1.22 g (3.5 mmol) of the title compound of Step C in 25 mL of acetonitrile was added 1.16 mL (8.36 mmol) of triethylamine, followed by 2 drops of CA 022~7196 1998-11-30 Wo 97/46530 PCT/US97/09569 acetonecyanohydrin. The mixture was stirred under nitrogen for 18 hours. The mixture was then concentrated under reduced pressure, and the residual oil was acidified with aqueous lN hydrochloric acid and extracted three times with 20 mL of dichloromethane.
The combined organic layers were dried over magnesium sulfate and concentrated under S reduced pressure to afford 0.4 g of the title compound of Step D, a compound of this invention, as a white solid melting at 137-145 ~C.
1H NMR (CDCl3): o 8.66 (m, 2H), 7.79 (m, 2H), 7.45 (m, 2H), 2.8 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H).
By the procedures described herein together with methods known in the art, the 10 following compounds of Tables 1 to 20 can be prepared. The following abbreviations are used in the Tables which follow: NO2 = nitro and Ph = phenyl.

.. . . . . .. .. ... ..

CA 022~7196 1998-11-30 PCT~US97/09569 The following notations have been used in Tables 1-20:
A-1 = (1-methyl-lH-pyrazol-3-yl)- A-26 = (1-methyl-lH-imidazol-4-yl)-A-2 = (1-ethyl-lH-pyrazol-3-yl)- A-27 = (I-methyl-lH-imidazol-S-yl)-A-3 = (1-propyl- lH-pyrazol-3-yl)- A-28 = (4-methyl-2-oxazolyl)-A-4 = (IH-pyrazol-3-yl)- A-29 = (5-methyl-2-oxazolyl)-A-S = (I,S-dimethyl-lH-pyrazol-3-yl)- A-30 = (2-oxazolyl)-A-6 = (4-chloro-1-methyl-lH-pyrazol-3-yl)- A-31 = (2-methyl-S-oxazolyl)-A-7 = (IH-pyrazol-l-yl)- A-32 = (2-methyl-4-oxazolyl)-A-8 = (3-methyl-lH-pyrazol-l-yl)- A-33 = (4-methyl-2-thiazolyl)-A-9 = (3,5-dimethyl-lH-pyrazol-l-yl)- A-34 = (5-methyl-2-thiazolyl)-A- 10 = (3-isoxazolyl)- A-35 = (2-thiazolyl)-A- 11 = (5-methyl-3-isoxazolyl)- A-36 = (2-methyl-5-thiazolyl)-A- 12 = (3-methyl-5-isoxazolyl)- A-37 = (2-methyl-4-thiazolyl)-A- 13 = (S-isoxazolyl)- A-38 = (3-methyl-4-isothiazolyl)-A- 14 = ( I H-pyrrol-2-yl)- A-39 = (3-methyl-5-isothiazolyl)-A-IS = (I-methyl-lH-pyrrol-2-yl)- A-40 = (5-methyl-3-isothiazolyl)-A-16 = (lH-pyrrol-l-yl)- A-41 = (1-methyl-lH-1,2,3-triazol-4-yl)-A-17 = (1-methyl-lH-pyrrol-3-yl)- A-42 = (2-methyl-2H-1,2,3-triazol-4-yl)-A-18 = (2-furanyl)- A-43 = (4-methyl-2H-1,2.3-triazol-2-yl)-A-l9 = (5-methyl-2-furanyl)- A-44 = (1-methyl-lH-1,2,4-triazol-3-yl)-A-20 = (3-furanyl)- A-45 = (1,5-dimethyl-lH-1,2,4-triazol-3-yl)-A-21 = (5-methyl-2-thienyl)- A-46 = (3-methyl-lH-1,2,4-triazol-1-yl)-A-22 = (2-thienyl)- A-47 = (5-methyl-lH-1,2,4-triazol-1-yl)-A-23 = (3-thienyl)- A-48 = (4,5-dimethyl-4H- 1,2,4-triazol-3-yl)-A-24 = (1-methyl-lH-imidazol-2-yl)- A-49 = (4-methyl-4H-1,2,4-triazol-3-yl)-A-25 = (IH-imidazol-2-yl)- A-50 = (4H-1,2,4-triazol-4-yl)-CA 022~7196 1998-11-30 PCTrUS97/09569 A-Sl = (S-methyl-1,2,3-oxadiazol-4-yl)- A-77 = (3-pyridazinyl)-A-52 = (1,2,3-oxadiazol-4-yl)- A-78 = (4,6-dimethyl-2-pyrimidinyl)-A-53 = (3-methyl-1,2,4-oxadiazol-S-yl)- A-79 = (4-methyl-2-pyrimidinyl)-A-54 = (S-methyl- 1,2,4-oxadiazol-3-yl)- A-80 = (2-pyrimidinyl)-A-55 = (4-methyl-3-furazanyl)- A-81 = (2-methyl-4-pyrimidinyl)-A-56 = (3-furazanyl)- A-82 = (2-chloro-4-pyrimidinyl)-A-57 = (5-methyl-1,3,4-oxadiazol-2-yl)- A-83 = (2,6-dimethyl-4-pyrimidinyl)-A-58 = (S-methyl-1,2,3-thiadiazol-4-yl)- A-84 = (4-pyrimidinyl)-A-59 = (1,2,3-thiadiazol-4-yl)- A-85 = (2-methyl-S-pyrimidinyl)-A-60 = (3-methyl-1,2,4-thiadiazol-S-yl)- A-86 = (6-methyl-2-pyrazinyl)-A-61 = (S-methyl-1,2,4-thiadiazol-3-yl)- A-87 = (2-pyrazinyl)-A-62 = (4-methyl-1,2,5-thiadiazol-3-yl)- A-88 = (4,6-dimethyl-1,3,5-triazin-2-yl)-A-63 = (S-methyl- 1,3,4-thiadiazol-2-yl)- A-89 = (4,6-dichloro- 1,3,5-triazin-2-yl)-A-64 = (I-methyl-lH-tetrazol-S-yl)- A-90 = (1,3,5-triazin-2-yl)-A-65 = ( I H-tetrazol-S-yl)- A-91 = (4-methyl- 1,3,5-triazin-2-yl)-A-66 = (S-methyl-lH-tetrazol-l-yl)- A-92 = (3-methyl-1,2,4-triazin-S-yl)-A-67 = (2-methyl-2H-tetrazol-S-yl)- A-93 = (3-methyl- 1,2,4-triazin-6-yl)-A-68 = (2-ethyl-2H-tetrazol-S-yl)-A-69 = (S-methyl-2H-tetrazol-2-yl)-A-70 = (2H-tetrazol-2-yl)-A-71 = (2-pyridinyl)-A-72 = (6-methyl-2-pyridinyl)-A-73 = (4-pyridinyl)-A-74 = (3-pyridinyl)-A-75 = (6-methyl-3-pyridazinyl)-A-76 = (5-methyl-3-pyridazinyl)-. ..

CA 022~7196 1998-11-30 R15i-- CH3 A _ _ _ A _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15i~ CH2CH3 _ A _ _ A _ A A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-85 A-86 A-87 A-88 A-8~ A-90 A-91 A-92 A-93 R15i CH2CH2CH~
_ A A A A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 X ~

R15i~ CH3 A _ _ _ _ _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15 i CH2CH3 A _ _ _ _ _ A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 .

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97109569 R15 i- CH2CH2CH~
_ A A _ _ A A A A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-85 A-86 A-87 A-88 A-89 A-90 A-9] A-92 A-93 ~ S02R15 R15i CH3 nd R6 s CH3 A A _ _ A _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rl5 i~ CH2CH3 and R6 is CH3 A _ A A _ _ _ A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O97/46530 PCT~US97/09569 A-49 A-50 A-Sl A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-S9 A-60A-61 A-62 A-63 A-64 A-65 A-66 A-67 A-68 A-69 A-70 A-71 A-72 Rl5 i - CH2CH2CH~ and R6is CH3 A _ A _ _ _ A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-25 A-26 A-27 A-28 A-29 A-30 A-3] A-32 A-33 A-34 A-35 A-36 Rl5 i-- CH~ nd R6 s CH2CH3 A _ _ A A A _ A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rl5 i CH2CH3 and R6 is CH~H3 _ _ A _ A _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 .

CA 022~7196 1998-11-30 W O97/46530 PCTrUS97/09569 Rlsi~- CH2CH2CH and ~6is C~-2CH3 A _ _ _ A A A _ _ _ A A
A-] A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 o CH3 H~[~502R15 R15i CH3 nd R6 s CH3 A A A A _ A A _ _ A
A-] A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15i~- CH2CH~and R6is CH3 _ _ _ _ _ _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97/09569 Rl5 i-- CH2CH2CH- and P6is C~3 _ A _ _ _ A _ A A _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15i CH3 - nd R6 s CH2CH3 _ A _ A L - - - - - A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15 i~- CH2CH3 and R6 is CH2C~ 3 _ A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 R15 i- CH2CH~ and p6iS CH2CH3 _ A _ _ _ _ _ A _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49A-SO A-Sl A-52 A-53 A-54 A-S5 A-56 A-57 A-58 A-59 A-60 H ~ 502R15 Rl5 i CH3 _ _ _ _ _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15i' CH2CH3 _ A _ A _ A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 WO 97/46530 PCTrUS97/09569 RlS i~ CH2CH2CH
_ _ _ _ _ _ A _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-73 A-74 A-75 A-76 A-77 A-78 A-?9 A-80 A-81 A-82 A-83 A-84 H~,502R]5 Rls i-- CH3 _ _ _ _ _ _ A _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 R 15 j- CH2CH3 _ A L _ L _ _ _ A L - L
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R15i CH2CH2CH~
_ _ _ A _ L _ A _ _ L A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 o o Rla = Rlc Rlb A Rlc Rla Rlb A Rlc Rl~ Rlb A-lSO2CH3 NO2 CH3 A-2 SO2CH3 NO2 CH3 A-lSO2CH3 Cl CH3 A-2 SO2CH3 Cl CH3 A-l SO2CH3 Cl Cl A-2 SO2CH3 Cl Cl A-l SO2CH2CH3 Cl CH3 A-2 SO2CH2CH3 Cl CH3 A-l SO2CH2CH3 Cl Cl A-2 SO2CH2CH3 Cl Cl CA 022~7196 1998-11-30 A-l SO2CH2CH2CH3 Cl CH3 A-2 SO2CH2CH2CH3 Cl CH3 A-l SO2CH2CH2CH3 Cl Cl A-2 SO2CH2CH2CH3 Cl Cl A- I SO2N(CH3)2 CH3 CH3 A-2 SO2N(CH3)2 CH3 CH3 A-l SO2N(CH3)2 Cl CH3 A-2 SO2N(CH3)2 Cl CH3 A-l SO2N(CH3)2 Cl Cl A-2 SO2N(CH3)2 Cl Cl A-l SO2CF3 Cl CH3 A-2 SO2CF3 Cl CH3 A-l SO2CF3 Cl Cl A-2 SO2CF3 Cl Cl A- ] SO20CH2CF3 CH3 CH3 A-2 SO20CH2CF3 CH3 CH3 A-l SO2OCH2CF3 Cl CH3 A-2 SO2OCH2CF3 Cl CH3 A-l SO2OCH2CF3 Cl Cl A-2 SO2OCH2CF3 Cl Cl A-l CF3 CH3 CH3 A-2 CF3 CH3 CH3 A-l CF3 Cl CH3 A-2 CF3 Cl CH3 A-l CF3 Cl Cl A-2 CF3 Cl Cl A-l OCH3 CH3 CH3 A-2 OCH3 CH3 CH3 A- I OCH3 Cl CH3 A-2 OCH3 Cl CH3 A-] OCH3 Cl Cl A-2 OCH3 Cl Cl A- 1 NO2 CH3 CH3 A-2 N~2 CH3 CH3 A-l NO2 Cl CH3 A-2 N ~2 Cl CH3 A-l NO2 Cl Cl A-2 N ~2 Cl Cl A-5 SO2CH3 NO2 CH3 A-7 S02CH3 N~2 CH3 A-5 SO2CH3 Cl CH3 A-7 SO2CH3 Cl CH3 A-5 SO2CH3 Cl Cl A-7 SO2CH3 Cl Cl A-5 SO2CH2CH3 Cl CH3 A-7 SO2CH2CH3 Cl CH3 A-5 SO2CH2CH3 Cl Cl A-7 SO2CH2CH3 Cl Cl A-5 SO2CH2CH2CH3 Cl CH3 A-7 SO2CH2CH2CH3 Cl CH3 A-5 SO2CH2CH2CH3 Cl Cl A-7 SO2CH2CH2CH3 Cl Cl A-5 So2N(cH3)2 CH3 CH3 A-7 SO2N(CH3)2 CH3 CH3 A-5 SO2N(CH3)2 Cl CH3 A-7 SO2N(CH3)2 Cl CH3 A-5 SO2N(CH3)2 Cl Cl A-7 SO2N(CH3)2 Cl Cl A-5 SO2CF3 Cl CH3 A-7 SO2CF3 Cl CH3 A-5 SO2CF3 Cl Cl A-7 SO2CF3 Cl Cl A-5 SO2OCH2CF3 Cl CH3 A-7 SO2OCH2CF3 Cl CH3 A-5 sO2OCH2CF3 Cl Cl A-7 SO2OCH2CF3 Cl Cl A-5 CF3 Cl CH3 A-7 CF3 Cl CH3 CA 022~7196 1998-11-30 A-5 CF3 Cl Cl A-7 CF3 Cl Cl A-5 OCH3 Cl CH3 A-7 OCH3 Cl CH3 A-5 OCH3 Cl Cl A-7 OCH3 Cl Cl A-5 NO2 Cl CH3 A-7 NO2 Cl CH3 A-5 NO2 Cl Cl A-7 NO2 Cl Cl A-8 SO2CH3 Cl CH3 A-9 SO2CH3 Cl CH3 A-8 SO2CH3 Cl Cl A-9 SO2CH3 Cl Cl A-8 SO2CH2CH3 C1 CH3 A-9 SO2CH2CH3 Cl CH3 A-8 SO2CH2CH3 Cl Cl A-9 SO2CH2CH3 Cl Cl A-8 SO2CH2CH2CH3 Cl CH3 A-9 SO2CH2CH2CH3 Cl CH3 A-8 SO2CH2CH2CH3 Cl Cl A-9 SO2CH2CH2cH3 Cl Cl A-8 SO2N(CH3)2 CH3 CH3 A-9 SO2N(CH3)2 CH3 CH3 A-8 So2N(cH3)2 Cl CH3 A-9 SO2N(CH3)2 Cl CH3 A-8 SO2N(CH3)2 Cl Cl A-9 SO2N(CH3)2 Cl Cl A-8 SO2CF3 Cl CH3 A-9 SO2CF3 Cl CH3 A-8 SO2CF3 Cl Cl A-9 SO2CF3 Cl Cl A-8 SO2OCH2CF3 Cl CH3 A-9 SO2OCH2CF3 Cl CH3 A-8 SO2OCH2CF3 Cl Cl A-9 SO2OCH2CF3 Cl Cl A-8 CF3 Cl CH3 A-9 CF3 Cl CH3 A-8 CF3 Cl Cl A-9 CF3 Cl Cl A-8 OCH3 Cl CH3 A-9 OCH3 Cl CH3 A-8 OCH3 Cl Cl A-9 OCH3 Cl Cl A-8 NO2 Cl CH3 A-9 NO2 Cl CH3 A-8 N~2 Cl Cl A-9 N~2 Cl Cl A-24 SO2CH3 Cl CH3 A-33 SO2CH3 Cl CH3 A-24 SO2CH3 Cl Cl A-33 SO2CH3 Cl Cl A-24 SO2CH2CH3 Cl CH3 A-33 SO2CH2CH3 Cl CH3 A-24 SO2CH2CH3 Cl Cl A-33 SO2CH2CH3 Cl Cl A-24 SO2CH2CH2CH3 Cl CH3 A-33 SO2CII2CH2CH3 Cl CH3 CA 022~7196 1998-ll-30 A-24 SO2CH2CH2CH3 Cl Cl A-33 SO2CH2CH2CH3 Cl Cl A-24 SO2N(CH3)2 CH3 CH3 A-33 SO2N(CH3)2 CH3 CH3 A-24 SO2N(CH3)2 Cl CH3 A-33 SO2N(CH3)2 Cl CH3 A-24 SO2N(CH3)2 Cl Cl A-33 SO2N(CH3)2 Cl Cl A-24 SO2CF3 Cl CH3 A-33 SO2CF3 Cl CH3 A-24 SO2CF3 Cl Cl A-33 SO2CF3 Cl Cl A-24 SO2OCH2CF3 Cl CH3 A-33 SO2OCH2CF3 Cl CH3 A-24 SO2OCH2CF3 Cl Cl A-33 SO2OCH2CF3 Cl Cl A-24 CF3 Cl CH3 A-33 CF3 Cl CH3 A-24 CF3 Cl Cl A-33 CF3 Cl Cl A-24 OCH3 Cl CH3 A-33 OCH3 Cl CH3 A-24 OCH3 Cl Cl A-33 OCH3 Cl Cl A-24 NO2 Cl CH3 A-33 NO2 Cl CH3 A-24 NO2 Cl Cl A-33 NO2 Cl Cl A-42 SO2CH3 Cl CH3 A-44 SO2CH3 Cl CH3 A-42 SO2CH3 Cl Cl A-44 SO2CH3 Cl Cl A-42 SO2CH2CH3 Cl CH3 A-44 SO2CH2CH3 Cl CH3 A-42 SO2CH2CH3 Cl Cl A-44 SO2CH2CH3 Cl Cl A-42 SO2CH2CH2CH3 Cl CH3 A-44 SO2CH2CH2CH3 Cl CH3 A-42 SO2CH2CH2CH3 Cl Cl A-44 SO2CH2CH2CH3 Cl Cl A-42 SO2N(CH3)2 CH3 CH3 A-44 SO2N(CH3)2 CH3 CH3 A-42 SO2N(CH3)2 Cl CH3 A-44 SO2N(CH3)2 Cl CH3 A-42 SO2N(CH3)2 Cl Cl A-44 SO2N(CH3)2 Cl Cl A-42 SO2CF3 Cl CH3 A-44 SO2CF3 Cl CH3 A-42 SO2CF3 Cl Cl A-44 SO2CF3 Cl Cl A-42 SO2OCH2CF3 Cl CH3 A-44 SO2OCH2CF3 Cl CH3 A-42 SO2OCH2CF3 Cl Cl A-44 SO2OCH2CF3 Cl Cl A-42 CF3 Cl CH3 A-44 CF3 Cl CH3 A-42 CF3 Cl Cl A-44 CF3 Cl Cl CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 A-42 OCH3 Cl CH3 A-44 OCH3 Cl CH3 A-42 OCH3 Cl Cl A-44 OCH3 Cl Cl A-42 NO2 CH3 CH3 A-44 N~2 CH3 CH3 A-42 NO2 Cl CH3 A-44 NO2 Cl CH3 A-42 NO2 Cl Cl A-44 NO2 Cl Cl A-45 SO2CH3 Cl CH3 A-67 SO2CH3 Cl CH3 A-45 SO2CH3 Cl Cl A-67 SO2CH3 Cl Cl A-45 S~2CH2CH3 Cl CH3 A-67 SO2CH2CH3 Cl CH3 A-45 SO2CH2CH3 Cl Cl A-67 SO2CH2CH3 Cl Cl A-45 SO2CH2CH2CH3 Cl CH3 A-67 SO2CH2CH2CH3 Cl CH3 A-45 SO2CH2CH2CH3 Cl Cl A-67 SO2CH2CH2CH3 Cl Cl A-45 So2N(cH3)2 CH3 CH3 A-67 SO2N(CH3)2 CH3 CH3 A-45 So2N(cH3)2 Cl CH3 A-67 SO2N(CH3)2 Cl CH3 A-45 SO2N(CH3)2 Cl Cl A-67 SO2N(CH3)2 Cl Cl A-45 SO2CF3 Cl CH3 A-67 SO2CF3 Cl CH3 A-45 SO2CF3 Cl Cl A-67 SO2CF3 Cl Cl A-45 SO20CH2CF3 Cl CH3 A-67 SO20CH2CF3 Cl CH3 A-45 so2ocH2cF3 Cl Cl A-67 SO20CH2CF3 Cl Cl A-45 CF3 Cl CH3 A-67 CF3 Cl CH3 A-45 CF3 Cl Cl A-67 CF3 Cl Cl A-45 OCH3 Cl CH3 A-67 OCH3 Cl CH3 A-45 OCH3 Cl Cl A-67 OCH3 Cl Cl A-45 NO2 CH3 CH3 A-67 N~2 CH3 CH3 A-45 NO2 Cl CH3 A-67 NO2 Cl CH3 A-45 NO2 Cl Cl A-67 NO2 Cl Cl A-68 SO2CH3 Cl CH3 A-71 SO2CH3 Cl CH3 A-68 SO2CH3 Cl Cl A-71 SO2CH3 Cl Cl A-68 SO2CH2CH3 Cl CH3 A-71 SO2CH2CH3 Cl CH3 A-68 sO2CH2CH3 Cl Cl A-71 SO2CH2CH3 Cl Cl A-68 SO2CH2CH2CH3 Cl CH3 A-71 SO2CH2CH2CH3 Cl CH3 A-68 SO2CH2CH2CH3 Cl Cl A-71 SO2CH2CH2CH3 Cl Cl CA 022~7196 1998-11-30 A-68 SO2N(CH3)2 CH3 CH3 A-71 SO2N(CH3)2 CH3 CH3 A-68 SO2N(CH3)2 Cl CH3 A-71 SO2N(CH3)2 Cl CH3 A-68 SO2N(CH3)2 Cl Cl A-71 SO2N(CH3)2 Cl Cl A-68 SO2CF3 Cl CH3 A-71 SO2CF3 Cl CH3 A-68 SO2CF3 Cl Cl A-71 SO2CF3 Cl Cl A-68 SO2OCH2CF3 Cl CH3 A-71 SO2OCH2CF3 Cl CH3 A-68 SO2OCH2CF3 Cl Cl A-71 SO2OCH2CF3 Cl Cl A-68 CF3 Cl CH3 A-71 CF3 Cl CH3 A-68 CF3 Cl Cl A-71 CF3 Cl Cl A-68 OCH3 Cl CH3 A-71 OCH3 Cl CH3 A-68 OCH3 Cl Cl A-71 OCH3 Cl Cl A-68 NO2 Cl CH3 A-71 NO2 Cl CH3 A-68 NO2 Cl Cl A-71 NO2 Cl Cl A-78 SO2CH3 Cl CH3 A-91 SO2CH3 Cl CH3 A-78 SO2CH3 Cl Cl A-91 SO2CH3 Cl Cl A-78 S~2CH2CH3 Cl CH3 A-91 SO2CH2CH3 Cl CH3 A-78 S~2CH2CH3 Cl Cl A-91 SO2CH2CH3 Cl Cl A-78 SO2CH2CH2CH3 Cl CH3 A-91 SO2CH2CH2CH3 Cl CH3 A-78 SO2CH2CH2CH3 Cl Cl A-91 SO2CH2CH2CH3 Cl Cl A-78 SO2N(CH3)2 CH3 CH3 A-91 SO2N(CH3)2 CH3 CH3 A-78 SO2N(CH3)2 Cl CH3 A-91 SO2N(CH3)2 Cl CH3 A-78 SO2N(CH3)2 Cl Cl A-91 SO2N(CH3)2 Cl Cl A-78 SO2CF3 Cl CH3 A-91 SO2CF3 Cl CH3 A-78 SO2CF3 Cl Cl A-91 SO2CF3 Cl Cl A-78 SO,,OCH2CF3 Cl CH3 A-91 SO20CH2CF3 Cl CH3 A-78 SO2OCH2CF3 Cl Cl A-91 SO2OCH2CF3 Cl Cl A-78 CF3 Cl CH3 A-91 CF3 Cl CH3 A-78 CF3 Cl Cl A-91 CF3 Cl Cl CA 022~7196 1998-11-30 A-78 OCH3 Cl CH3 A-9 1 OCH3 Cl CH3 A-78 OCH3 Cl Cl A-9 1 OCH3 Cl Cl A-78 NO2 Cl CH3 A-9 I NO2 Cl CH3 A-78 NO2 Cl Cl A-9 I NO2 Cl Cl O Rla H~[ ~RIc CH2CH3 Rlb A RlC Rla Rlb A Rlc Rla Rlb -A- 1 SO2CH3 Cl CH3 A-2 SO2CH3 Cl CH3 A- I SO2CH3 Cl Cl A-2 SO2CH3 Cl Cl A- I SO2CH2CH3 Cl CH3 A-2 SO2CH2CH3 Cl CH3 A- I SO2CH2CH3 Cl Cl A-2 SO2CH2CH3 Cl Cl A- I SO2CH2CH2CH3 Cl CH3 A-2 SO2CH2CH2CH3 Cl CH3 A- I SO2CH2CH2CH3 Cl Cl A-2 SO2CH2CH2CH3 Cl Cl A- I SO2N(CH3)2 CH3 CH3 A-2 SO2N(CH3)2 CH3 CH3 A- I SO2N(CH3)2 Cl CH3 A-2 SO2N(CH3)2 Cl CH3 A- 1 So2N(cH3)2 Cl Cl A-2 so2N(cH3)2 Cl Cl A- I SO2CF3 Cl CH3 A-2 SO2CF3 Cl CH3 A- I SO2CF3 Cl Cl A-2 SO2CF3 Cl Cl A- I SO2OCH2CF3 Cl CH3 A-2 SO2OCH2CF3 Cl CH3 A- I SO2OCH2CF3 Cl Cl A-2 SO2OCH2CF3 Cl Cl A- I CF3 Cl CH3 A-2 CF3 Cl CH3 A- ] CF3 Cl Cl A-2 CF3 Cl Cl A- I OCH3 Cl CH3 A-2 OCH3 Cl CH3 A- I OCH3 Cl Cl A-2 OCH3 Cl Cl CA 022~7196 1998-11-30 A- I NO2 CH3 CH3 A-2 N~2 CH3 CH3 A- I NO2 Cl CH3 A-2 N~2 Cl CH3 A- I NO2 Cl Cl A-2 NO2 Cl Cl A-S SO2CH3 Cl CH3 A-7 S02CH3 Cl CH3 A-S SO2CH3 Cl Cl A-7 SO2CH3 Cl Cl A-S SO2CH2CH3 Cl CH3 A-7 SO2CH2CH3 Cl CH3 A-S SO2CH2CH3 Cl Cl A-7 SO2CH2CH3 Cl Cl A-S SO2CH2CH2cH3 Cl CH3 A-7 SO2CH2CH2CH3 Cl CH3 A-S SO2CH2CH2CH3 Cl Cl A-7 SO2CH2CH2CH3 Cl Cl A-S So2N(cH3)2 CH3 CH3 A-7 SO2N(CH3)2 CH3 CH3 A-S SO2N(CH3)2 Cl CH3 A-7 SO2N(CH3)2 Cl CH3 A-S SO2N(CH3)2 Cl Cl A-7 SO2N(CH3)2 Cl Cl A-S SO2CF3 Cl CH3 A-7 S02CF3 Cl CH3 A-S SO2CF3 Cl Cl A-7 SO2CF3 Cl Cl A-5 SO20CH2CF3 Cl CH3 A-7 SO20CH2CF3 Cl CH3 A-5 SO20CH2CF3 Cl Cl A-7 SO20CH2CF3 Cl Cl A-S CF3 Cl CH3 A-7 CF3 Cl CH3 A-5 CF3 Cl Cl A-7 CF3 Cl Cl A-5 OCH3 Cl CH3 A-7 OCH3 Cl CH3 A-S OCH3 Cl Cl A-7 OCH3 Cl Cl A-5 NO2 CH3 CH3 A-7 N~2 CH3 CH3 A-5 NO2 Cl CH3 A-7 N~2 Cl CH3 A-S NO2 Cl Cl A-7 NO2 Cl Cl A-8 SO2CH3 Cl CH3 A-9 S02CH3 Cl CH3 A-8 SO2CH3 Cl Cl A-9 SO2CH3 Cl Cl A-8 SO2CH2CH3 Cl CH3 A-9 SO2CH2CH3 Cl CH3 A-8 SO2CH2CH3 Cl Cl A-9 SO2CH2CH3 Cl Cl A-8 SO2CH2CH2CH3 Cl CH3 A-9 SO2CH2CH2CH3 Cl CH3 A-8 SO2CH2CH2CH3 Cl Cl A-9 S02CH2CH2CH3 Cl Cl A-8 SO2N(CH3)2 CH3 CH3 A-9 SO2N(CH3)2 CH3 CH3 A-8 So2N(cH3)2 Cl CH3 A-9 SO2N(CH3)2 Cl CH3 A-8 SO2N(CH3)2 Cl Cl A-9 SO2N(CH3)2 Cl Cl CA 022~7196 1998-11-30 A-8 SO2CF3 Cl CH3 A-9 SO2CF3 Cl CH3 A-8 SO2CF3 Cl Cl A-9 SO2CF3 Cl Cl A-8 SO20CH2CF3 Cl CH3 A-9 SO20CH2CF3 Cl CH3 A-8 SO20CH2CF3 Cl Cl A-9 SO20CH2CF3 Cl Cl A-8 CF3 Cl CH3 A-9 CF3 Cl CH3 A-8 CF3 Cl Cl A-9 CF3 Cl Cl A-8 OCH3 Cl CH3 A-9 OCH3 Cl CH3 A-8 OCH3 Cl Cl A-9 OCH3 Cl Cl A-8 NO2 CH3 CH3 A-9 N~2 CH3 CH3 A-8 NO2 Cl CH3 A-9 . N~2 Cl CH3 A-8 NO2 Cl Cl A-9 NO2 Cl Cl A-24 SO2CH3 Cl CH3 A-33 SO2CH3 Cl CH3 A-24 SO2CH3 Cl Cl A-33 SO2CH3 Cl Cl A-24 SO2CH2CH3 Cl CH3 A-33 SO2CH2CH3 Cl CH3 A-24 SO2CH2CH3 Cl Cl A-33 SO2CH2CH3 Cl Cl A-24 SO2CH ,CH2CH3 Cl CH3 A-33 SO~CH2CH2CH3 Cl CH3 A-24 SO2CH2CH2CH3 Cl Cl A-33 SO2CH2CH2CH3 Cl Cl A-24 SO2N(CH3)2 CH3 CH3 A-33 SO2N(CH3)2 CH3 CH3 A-24 so2N(cH3)2 Cl CH3 A-33 SO2N(CH3)2 Cl CH3 A-24 SO2N(CH3)2 Cl Cl A-33 So2N(cH3)2 Cl Cl A-24 SO2CF3 Cl CH3 A-33 SO2CF3 Cl CH3 A-24 SO2CF3 Cl Cl A-33 SO2CF3 Cl Cl A-24 SO~OCH2CF3 Cl CH3 A-33 SO20CH2CF3 Cl CH3 A-24 SO20CH2CF3 Cl Cl A-33 SO20CH2CF3 Cl Cl A-24 CF3 Cl CH3 A-33 CF3 Cl CH3 A-24 CF3 Cl Cl A-33 CF3 Cl Cl A-24 OCH3 Cl CH3 A-33 OCH3 Cl CH3 A-24 OCH3 Cl Cl A-33 OCH3 Cl Cl A-24 NO2 CH3 CH3 A-33 N~2 CH3 CH3 CA 022~7196 1998-11-30 PCTrUS97/09569 A-24 NO2 Cl CH3 A-33 N~2 Cl CH3 A-24 NO2 Cl Cl A-33 NO2 Cl Cl A-42 SO2CH3 Cl CH3 A-44 SO2CH3 Cl CH3 A-42 SO2CH3 Cl Cl A-44 S02CH3 Cl Cl A-42 SO2CH2CH3 Cl CH3 A-44 SO2CH2CH3 Cl CH3 A-42 SO2CH2CH3 Cl Cl A-44 sO2CH2CH3 Cl Cl A-42 SO2CH2CH2CH3 Cl CH3 A-44 SO2CH2C~2CH3 Cl CH3 A-42 SO2CH2CH2CH3 Cl Cl A-44 So2cH2cH2cH3 C~ Cl A-42 SO2N(CH3)2 CH3 CH3 A-44 SO2N(CH3)2 CH3 CH3 A-42 So2N(cH3)2 Cl CH3 A-44 SO2N(CH3)2 Cl CH3 A-42 SO2N(CH3)2 Cl Cl A-44 SO2N(CH3)2 Cl Cl A-42 SO2CF3 Cl CH3 A-44 SO2CF3 Cl CH3 A-42 SO2CF3 Cl Cl A-44 SO2CF3 Cl Cl A-42 SO20CH2CF3 Cl CH3 A-44 SO20CH2CF3 Cl CH3 A-42 SO20CH2CF3 Cl Cl A-44 SO20CH2CF3 Cl Cl A-42 CF3 Cl CH3 A-44 CF3 Cl CH3 A-42 CF3 Cl Cl A-44 CF3 Cl Cl A-42 OCH3 Cl CH3 A-44 OCH3 Cl CH3 A-42 OCH3 Cl Cl A-44 OCH3 Cl Cl A-42 NO2 Cl CH3 A-44 NO2 Cl CH3 A-42 NO2 Cl Cl A-44 NO2 Cl Cl A-4S SO2CH3 Cl CH3 A-67 SO2CH3 Cl CH3 A-45 SO2CH3 Cl Cl A-67 SO2CH3 Cl Cl A-45 sO2CH2CH3 Cl CH3 A-67 SO2CH2CH3 Cl CH3 A-45 sO2CH2CH3 Cl Cl A-67 SO2CH2CH3 Cl Cl A-45 SO2CH2CH2CH3 Cl CH3 A-67 SO2CH2CH2CH3 Cl CH3 A-45 SO2CH2CH2CH3 Cl Cl A-67 SO2CH2CH2CH3 Cl Cl A-45 SO2N(CH3)2 CH3 CH3 A-67 SO2N(CH3)2 CH3 CH3 A-45 SO2N(CH3)2 Cl CH3 A-67 SO2N(CH3)2 Cl CH3 A-45 SO2N(CH3)2 Cl Cl A-67 SO2N(CH3)2 Cl Cl , CA 022~7196 1998-11-30 A-45 SO2CF3 Cl CH3 A-67 SO2CF3 Cl CH3 A-45 SO2CF3 Cl Cl A-67 SO2CF3 Cl Cl A-45 SO2OCH2CF3 Cl CH3 A-67 SO2OCH2CF3 Cl CH3 A-45 sO2OCH2CF3 Cl Cl A-67 SO2OCH2CF3 Cl Cl A-45 CF3 Cl CH3 A-67 CF3 Cl CH3 A-45 CF3 Cl Cl A-67 CF3 Cl Cl A-45 OCH3 Cl CH3 A-67 OCH3 Cl CH3 A-45 OCH3 Cl Cl A-67 OCH3 Cl Cl A-45 NO2 Cl CH3 A-67 NO2 Cl CH3 A-45 NO2 Cl Cl A-67 NO2 Cl Cl A-68 SO2CH3 Cl CH3 A-71 SO2CH3 Cl CH3 A-68 SO2CH3 Cl Cl A-71 SO2CH3 Cl Cl A-68 SO2CH2CH3 Cl CH3 A-71 SO2CH2CH3 Cl CH3 A-68 SO2CH2CH3 Cl Cl A-71 SO2CH2CH3 Cl Cl A-68 SO2CH2CH2CH3 Cl CH3 A-71 SO2CH2CH2CH3 Cl CH3 A-68 SO2CH2CH2CH3 Cl Cl A-71 SO2CH2CH2CH3 Cl Cl A-68 SO2N(CH3)2 CH3 CH3 A-71 SO2N(CH3)2 CH3 CH3 A-68 SO2N(CH3)2 Cl CH3 A-7 ~ SO2N(CH3)2 Cl CH3 A-68 SO2N(CH3)2 Cl Cl A-71 So2N(cH3)2 Cl Cl A-68 SO2CF3 Cl CH3 A-71 SO2CF3 Cl CH3 A-68 SO2CF3 Cl Cl A-71 SO2CF3 Cl Cl A-68 SO2OCH2CF3 Cl CH3 A-71 SO2OCH2CF3 Cl CH3 A-68 SO2OCH2CF3 Cl Cl A-71 SO2OCH2CF3 Cl Cl A-68 CF3 Cl CH3 A-71 CF3 Cl CH3 A-68 CF3 Cl Cl A-71 CF3 Cl Cl A-68 OCH3 Cl CH3 A-71 OCH3 Cl CH3 A-68 OCH3 Cl Cl A-71 OCH3 Cl Cl A-68 NO2 Cl CH3 A-71 NO2 Cl CH3 CA 022~7196 1998-11-30 A-68 NO2 Cl Cl A-71 NO2 Cl Cl A-78 SO2CH3 Cl CH3 A-91 SO2CH3 Cl CH3 A-78 SO2CH3 Cl Cl A-91 SO2CH3 Cl Cl A-78 SO2CH2CH3 Cl CH3 A-91 SO2CH2CH3 Cl CH3 A-78 SO2CH2CH3 Cl Cl A-91 SO2CH2CH3 Cl Cl A-78 SO2CH2CH2CH3 Cl CH3 A-91 SO2CH2CH2CH3 Cl CH3 A-78 SO2CH2CH2CH3 Cl Cl A-91 SO2CH2CH2CH3 Cl Cl A-78 SO2N(CH3)2 CH3 CH3 A-91 SO2N(CH3)2 CH3 CH3 A-78 SO2N(CH3)2 Cl CH3 A-91 SO2N(CH3)2 Cl CH3 A-78 SO2N(CH3)2 Cl Cl A-91 SO2N(CH3)2 Cl Cl A-78 SO2CF3 Cl CH3 A-91 SO2CF3 Cl CH3 A-78 SO2CF3 Cl Cl A-91 SO2CF3 Cl Cl A-78 SO2OCH2CF3 Cl CH3 A-91 SO2OCH2CF3 Cl CH3 A-78 SO2OCH2CF3 Cl Cl A-91 SO2OCH2CF3 Cl Cl A-78 CF3 Cl CH3 A-91 CF3 Cl CH3 A-78 CF3 Cl Cl A-91 CF3 Cl Cl A-78 OCH3 Cl CH3 A-91 OCH3 Cl CH3 A-78 OCH3 Cl Cl A-91 OCH3 Cl Cl A-78 NO2 Cl CH3 A-91 NO2 Cl CH3 A-78 NO2 Cl Cl A-91 NO2 Cl Cl O Rla H~RIC

A RlC Rla Rlb A RlC Rla Rlb CA 022~7196 1998-11-30 A- I SO2CH3 Cl CH3 A-2 SO2CH3 Cl CH3 A- I SO2CH3 Cl Cl A-2 SO2CH3 Cl Cl A- I SO2CH2CH3 Cl CH3 A-2 SO2CH2CH3 Cl CH3 A- I SO2CH2CH3 Cl Cl A-2 SO2CH2CH3 Cl Cl A- I SO2CH2CH2CH3 Cl CH3 A-2 SO2CH2CH2CH3 Cl CH3 A- I SO2CH2CH2CH3 Cl Cl A-2 So2cH2cH2cH3 Cl Cl A- I So2N(cH3)2 CH3 CH3 A-2 SO2N(CH3)2 CH3 CH3 A- 1 SO2N(CH3)2 Cl CH3 A-2 SO2N(CH3)2 Cl CH3 A- ] SO2N(CH3)2 Cl Cl A-2 So2N(cH3)2 Cl Cl A- 1 SO2CF3 Cl CH3 A-2 SO2CF3 Cl CH3 A- I SO2CF3 Cl Cl A-2 SO2CF3 Cl Cl A- I SO2OCH2CF3 Cl CH3 A-2 SO2OCH2CF3 Cl CH3 A- I SO2OCH2CF3 Cl Cl A-2 SO2OCH2CF3 Cl Cl A- I CF3 Cl CH3 A-2 CF3 Cl CH3 A- I CF3 Cl Cl A-2 CF3 Cl Cl A- I OCH3 Cl CH3 A-2 OCH3 Cl CH3 A- I OCH3 Cl Cl A-2 OCH3 Cl Cl A- I NO2 C] CH3 A-2 NO2 Cl CH3 A- I NO2 Cl Cl A-2 NO2 Cl Cl A-5 SO2CH3 Cl CH3 A-7 SO2CH3 Cl CH3 A-S SO2CH3 Cl Cl A-7 SO2CH3 Cl Cl A-S SO2CH2CH3 Cl CH3 A-7 SO2CH2CH3 Cl CH3 A-5 SO2CH2CH3 Cl Cl A-7 SO2CH2CH3 Cl Cl A-5 SO2CH2CH2CH3 Cl CH3 A-7 SO2CH2CH2CH3 Cl CH3 A-S SO2CH2CH2CH3 Cl Cl A-7 SO2CH2CH2CH3 Cl Cl A-5 SO2N(CH3)2 CH3 CH3 A-7 SO2N(CH3)2 CH3 CH3 A-S SO2N(CH3)2 Cl CH3 A-7 SO2N(CH3)2 Cl CH3 A-5 So2N(cH3)2 Cl Cl A-7 SO2N(CH3)2 Cl Cl A-S SO2CF3 Cl CH3 A-7 SO2CF3 Cl CH3 A-5 SO2CF3 Cl Cl A-7 SO2CF3 Cl Cl CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 A-S SO20GH2CF3 Cl CH3 A-7 SO20CH2CF3 Cl CH3 A-5 SO20CH2CF3 Cl Cl A-7 SO20CH2CF3 Cl Cl A-S CF3 Cl CH3 A-7 CF3 Cl CH3 A-S CF3 Cl Cl A-7 CF3 Cl Cl A-S OCH3 Cl CH3 A-7 OCH3 Cl CH3 A-S OCH3 Cl Cl A-7 OCH3 Cl Cl A-S NO2 CH3 CH3 A-7 N~2 CH3 CH3 A-5 NO2 Cl CH3 A-7 N~2 Cl CH3 A-S NO2 Cl Cl A-7 NO2 Cl Cl A-8 SO2CH3 Cl CH3 A-9 SO2CH3 Cl CH3 A-8 SO2CH3 Cl Cl A-9 SO2CH3 Cl Cl A-8 sO2CH2CH3 Cl CH3 A-9 SO2CH2CH3 Cl CH3 A-8 SO2CH2CH3 Cl Cl A-9 SO2CH2CH3 Cl Cl A-8 SO2CH2CH2CH3 Cl CH3 A-9 SO2CH2CH2CH3 Cl CH3 A-8 SO2CH2CH2CH3 Cl Cl A-9 SO2CH2CH2CH3 Cl Cl A-8 SO2N(CH3)2 CH3 CH3 A-9 SO2N(CH3)2 CH3 CH3 A-8 SO2N(CH3~2 Cl CH3 A-9 SO2N(CH3)2 Cl CH3 A-8 So2N(cH3)2 Cl Cl A-9 SO2N(CH3)2 Cl Cl A-8 SO2CF3 Cl CH3 A-9 SO2CF3 Cl CH3 A-8 SO2CF3 Cl Cl A-9 SO2CF3 Cl Cl A-8 SO20CH2CF3 Cl CH3 A-9 SO20CH2CF3 Cl CH3 A-8 SO20CH2CF3 Cl Cl A-9 SO20CH2CF3 Cl Cl A-8 CF3 Cl CH3 A-9 CF3 Cl CH3 A-8 CF3 Cl Cl A-9 CF3 Cl Cl A-8 OCH3 Cl CH3 A-9 OCH3 Cl CH3 A-8 OCH3 Cl Cl A-9 OCH3 Cl Cl A-8 NO2 CH3 CH3 A-9 N~2 CH3 CH3 A-8 NO2 Cl CH3 A-9 N~2 Cl CH3 A-8 NO2 Cl Cl A-9 NO2 Cl Cl A-24 SO2CH3 Cl CH3 A-33 SO2CH3 Cl CH3 CA 022~7196 1998-11-30 WO97/46530 PCTrUS97109569 A-24 SO2CH3 Cl Cl A-33 SO2CH3 Cl Cl A-24 SO2CH2CH3 Cl CH3 A-33 SO2CH2CH3 Cl CH3 A-24 SO2CH2CH3 Cl Cl A-33 SO2CH2CH3 Cl Cl A-24 SO2CH2CH2CH3 Cl CH3 A-33 SO2CH2CH2CH3 Cl CH3 A-24 SO2CH2CH2CH3 Cl Cl A-33 SO2CH2CH2CH3 Cl Cl A-24 So2N(cH3)2 CH3 CH3 A-33 SO2N(CH3)2 CH3 CH3 A-24 So2N(cH3)2 Cl CH3 A-33 SO2N(CH3)2 Cl CH3 A-24 SO2N(CH3)2 Cl Cl A-33 so2N(cH3)2 Cl Cl A-24 SO2CF3 Cl CH3 A-33 SO2CF3 Cl CH3 A-24 SO2CF3 Cl Cl A-33 SO2CF3 Cl Cl A-24 SO2OCH2CF3 Cl CH3 A-33 SO~OCH2CF3 Cl CH3 A-24 SO2OCH2CF3 Cl Cl A-33 SO2OCH2CF3 Cl Cl A-24 CF3 Cl CH3 A~33 CF3 Cl CH3 A-24 CF3 Cl Cl A-33 CF3 Cl Cl A-24 OCH3 Cl CH3 A-33 OCH3 Cl CH3 A-24 OCH3 Cl Cl A-33 OCH3 Cl Cl A-24 NO2 CH3 CH3 A-33 N~2 CH3 CH3 A-24 NO2 Cl CH3 A-33 NO2 Cl CH3 A-24 NO2 Cl Cl A-33 NO2 Cl Cl A-42 SO2CH3 Cl CH3 A-44 SO2CH3 Cl CH3 A-42 SO2CH3 Cl Cl A-44 SO2CH3 Cl Cl A-42 SO2CH2CH3 Cl CH3 A-44 SO2CH2CH3 Cl CH3 A-42 SO2CH2CH3 Cl Cl A-44 SO2CH2CH3 Cl Cl A-42 SO2CH2CH2CH3 Cl CH3 A-44 SO2CH2CH2CH3 Cl CH3 A-42 SO2CH2CH2CH3 Cl Cl A-44 SO2CH2CH2CH3 Cl Cl A-42 So2N(cH3)2 CH3 CH3 A-44 SO2N(CH3)2 CH3 CH3 A-42 SO2N(CH3)2 Cl CH3 A-44 SO2N(CH3)2 Cl CH3 A-42 So2N(cH3)2 Cl Cl A-44 SO2N(CH3)2 Cl Cl A-42 SO2CF3 Cl CH3 A-44 SO2CF3 Cl CH3 A-42 SO2CF3 Cl Cl A-44 SO2CF3 Cl Cl A-42 SO2OCH2CF3 Cl CH3 A-44 SO2OCH2CF3 Cl CH3 .

CA 022~7196 1998-11-30 W O 97/46~30 A-42 SO2OCH2CF3 Cl Cl A-44 SO2OCH2CF3 Cl Cl A-42 CF3 Cl CH3 A-44 CF3 Cl CH3 A-42 CF3 Cl Cl A-44 CF3 Cl Cl A-42 OCH3 Cl CH3 A-44 OCH3 Cl CH3 A-42 OCH3 Cl Cl A-44 OCH3 Cl Cl A-42 NO2 Cl CH3 A-44 NO2 Cl CH3 A-42 NO2 Cl Cl A-44 NO2 Cl Cl A-45 SO2CH3 Cl CH3 A-67 SO2CH3 Cl CH3 A-45 SO2CH3 Cl Cl A-67 SO2CH3 Cl Cl A-45 SO2CH2CH3 Cl CH~ A-67 SO2CH2CH3 Cl CH3 A-45 SO2CH2CH3 Cl Cl A-67 SO2CH2CH3 Cl Cl A-45 SO2CH2CH2CH3 Cl CH3 A-67 SO2CH2CH2CH3 Cl CH3 A-45 SO2CH2CH2CH3 Cl Cl A-67 SO2CH2CH2CH3 Cl Cl A-45 so2N(cH3)2 CH3 CH3 A-67 SO2N(CH3)2 CH3 CH3 A-45 SO2N(CH3)2 Cl CH3 A-67 SO2N(CH3)2 Cl CH3 A-45 So2N(cH3)2 Cl Cl A-67 SO2N(CH3)2 Cl Cl A-45 SO2CF, CH3 CH3 A-67 SO2CF3 CH3 CH3 A-45 SO2CF3 Cl CH3 A-67 SO2CF3 Cl CH3 A-45 SO2CF~ Cl Cl A-67 SO2CF3 Cl Cl A-45 SO2OCH2CF3 Cl CH3 A-67 SO2OCH2CF3 Cl CH3 A-45 SO2OCH2CF3 Cl Cl A-67 SO20CH2CF3 Cl Cl A-45 CF3 Cl CH3 A-67 CF3 Cl CH3 A-45 CF3 Cl Cl A-67 CF3 Cl Cl A-45 OCH3 Cl CH3 A-67 OCH3 Cl CH3 A-45 OCH3 Cl Cl A-67 OCH3 Cl Cl A-45 NO2 CH3 CH3 A-67 N~2 CH3 CH3 A-45 NO2 Cl CH3 A-67 NO2 Cl CH3 A-45 NO2 Cl Cl A-67 N02 Cl Cl A-6B SO2CH3 Cl CH3 A-71 SO2CH3 Cl CH3 A-68 SO2CH3 Cl Cl A-71 SO2CH3 Cl Cl ~ . . .

CA 022~7196 1998-11-30 A-68 SO2CH2CH3 Cl CH3 A-71 SO2CH2CH3 Cl CH3 A-68 SO2CH2CH3 Cl Cl A-71 SO2CH2CH3 Cl Cl A-68 SO2CH2CH2CH3 Cl CH3 A-71 SO2CH2CH2CH3 Cl CH3 A-68 SO2CH2CH2CH3 Cl Cl A-71 SO2CH2CH2CH3 Cl Cl A-68 SO2N(CH3)2 CH3 CH3 A-71 SO2N(CH3)2 CH3 CH3 A-68 SO2N(CH3)2 Cl CH3 A-71 SO2N(CH3)2 Cl CH3 A-68 SO2N(CH3)2 Cl Cl A-71 SO2N(CH3)2 Cl Cl A-68 SO2CF3 Cl CH3 A-71 SO2CF3 Cl CH3 A-68 SO2CF3 Cl Cl A-71 SO2CF3 Cl Cl A-68 SO2OCH2CF3 Cl CH3 A-71 SO2OCH2CF3 Cl CH3 A-68 SO2OCH2CF3 Cl Cl A-71 SO2OCH2CF3 Cl Cl A-68 CF3 Cl CH3 A-71 CF3 Cl CH3 A-68 CF3 Cl Cl A-71 CF3 Cl Cl A-68 OCH3 Cl CH3 A-71 OCH3 Cl CH3 A-68 OCH3 Cl Cl A-71 OCH3 Cl Cl A-68 N02 CH3 CH3 A-71 N~2 CH3 CH3 A-68 NO2 Cl CH3 A-71 NO2 Cl CH3 A-68 NO2 Cl Cl A-71 NO2 Cl Cl A-78 SO2CH3 Cl CH3 A-91 SO2CH3 Cl CH3 A-78 SO2CH3 Cl Cl A-91 SO2CH3 Cl Cl A-78 SO2CH2CH3 Cl CH3 A-91 SO2CH2CH3 Cl CH3 A-78 SO2CH2CH3 Cl Cl A-91 SO2CH2CH3 Cl Cl A-78 SO2CH2CH2CH3 Cl CH3 A-91 SO2CH2CH2CH3 Cl CH3 A-78 SO2CH2CH2CH3 Cl Cl A-91 SO2CH2CH2CH3 Cl Cl A-78 SO2N(CH3)2 CH3 CH3 A-91 SO2N(CH3)2 CH3 CH3 A-78 SO2N(CH3)2 Cl CH3 A-91 SO2N(CH3)2 Cl CH3 A-78 SO2N(CH3)2 Cl Cl A-91 SO2N(CH3)2 Cl Cl A-78 SO2CF3 Cl CH3 A-91 SO2CF3 Cl CH3 A-78 SO2CF3 Cl Cl A-91 SO2CF3 Cl Cl A-78 SO2OCH2CF3 Cl CH3 A-91 SO2OCH2CF3 Cl CH3 A-78 SO2OCH2CF3 Cl Cl A-91 SO2OCH2CF3 Cl Cl CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97/09569 A-78 CF3 Cl CH3 A-91 CF3 Cl CH3 A-78 CF3 Cl Cl A-91 CF3 Cl Cl A-78 OCH3 Cl CH3 A-91 OCH3 Cl CH3 A-78 OCH3 Cl Cl A-91 OCH3 Cl Cl A-78 NO2 CH3 CH3 A-91 N~2 CH3 CH3 A-78 NO2 Cl CH3 A-91 N~2 Cl CH3 A-78 NO2 Cl Cl A-91 NO2 Cl Cl O O Rla Rlc Rlb A RlC Rla Rlb A RlC Rla Rlb A- I SO2CH3 NO2 CH3 A-2 SO~CH3 N~2 CH3 A- I SO2CH3 Cl CH3 A-2 SO2CH3 Cl CH3 A- ] SO2CH3 Cl Cl A-2 SO2CH3 Cl Cl A- I SO2CH2CH3 Cl CH3 A-2 SO2CH2CH3 Cl CH3 A- I SO2CH2CH3 Cl Cl A-2 SO2CH2CH3 Cl Cl A- I SO2CH2CH2CH3 Cl CH3 A-2 SO,,CH2CH2CH3 Cl CH3 A- I SO2CH2CH2CH3 Cl Cl A-2 So2cH2cH2cH3 C~ Cl A- I So2N(cH3)2 CH3 CH3 A-2 SO2N(CH3)2 CH3 CH3 A- I SO2N(CH3)2 Cl CH3 A-2 SO2N(CH3)2 Cl CH3 A- I SO2N(CH3)2 Cl Cl A-2 SO~N(CH3)2 Cl C]

A- I SO2CF3 Cl CH3 A-2 SO2CF3 Cl CH3 A- I SO2CF3 Cl Cl A-2 SO2CF3 Cl Cl A- I SO20CH2CF3 CH3 CH3 A-2 SO,OCH2CF3 CH3 CH3 A- I SO20CH2CF3 Cl CH3 A-2 SO20CH2CF3 Cl CH3 A- I SO20CH2CF3 Cl Cl A-2 SO20CH2CF3 Cl Cl A- I CF3 Cl CH3 A-2 CF3 Cl CH3 CA 022~7196 1998-11-30 A- 1 CF3 Cl Cl A-2 CF3 Cl Cl A- 1 OCH3 Cl CH3 A-2 OCH3 Cl CH3 A- I OCH3 Cl Cl A-2 OCH3 Cl Cl A- I NO2 Cl CH3 A-2 NO2 Cl CH3 A- I NO2 Cl Cl A-2 NO2 Cl Cl A-5 SO2CH3 Cl CH3 A-7 SO2CH3 Cl CH3 A-5 SO2CH3 Cl Cl A-7 SO2CH3 Cl Cl A-5 SO2CH2CH3 Cl CH3 A-7 SO2CH2CH3 Cl CH3 A-5 SO2CH2CH3 Cl Cl A-7 sO2CH2CH3 Cl Cl A-5 SO2CH2CH2CH3 Cl CH3 A-7 SO2CH2CH2CH3 Cl CH3 A-5 SO2CH2CH2CH3 Cl Cl A-7 SO2CH2CH2CH3 Cl Cl A-5 SO2N(CH3)2 CH3 CH3 A-7 SO2N(CH3)2 CH3 CH3 A-5 SO2N(CH3)2 Cl CH3 A-7 SO2N(CH3)2 Cl CH3 A-5 SO2N(CH3)2 Cl Cl A-7 sO2N(CH3)2 Cl Cl A-5 SO2CF3 Cl CH3 A-7 SO2CF3 Cl CH3 A-5 SO2CF3 Cl Cl A-7 SO2CF3 Cl Cl A-5 SO2OCH2CF3 Cl CH3 A-7 SO2OCH2CF3 Cl CH3 A-5 SO2OCH2CF3 Cl Cl A-7 SO2OCH2CF3 Cl Cl A-5 CF3 Cl CH3 A-7 CF3 C] CH3 A-5 CF3 Cl Cl A-7 CF3 Cl Cl A-5 OCH3 Cl CH3 A-7 OCH3 Cl CH3 A-5 OCH3 Cl Cl A-7 OCH3 Cl Cl A-5 NO2 Cl CH3 A-7 NO2 Cl CH3 A-5 NO2 Cl Cl A-7 NO2 Cl Cl A-8 SO2CH3 Cl CH3 A-9 SO2CH3 Cl CH3 A-8 SO2CH3 Cl Cl A-9 SO2CH3 Cl Cl A-8 SO2CH2CH3 Cl CH3 A-9 SO2CH2CH3 Cl CH3 A-8 SO2CH2CH3 Cl Cl A-9 SO2CH2CH3 Cl Cl A-8 SO2CH2CH2CH3 Cl CH3 A-9 SO2CH2CH2CH3 Cl CH3 CA 022~7196 1998-11-30 WO 97/46~30 A-8 SO2CH2CH2CH3 Cl Cl A-9 SO2CH2CH2cH3 Cl Cl A-8 SO2N(CH3)2 CH3 CH3 A-9 SO2N(CH3)2 CH3 CH3 A-8 SO2N(CH3)2 Cl CH3 A-9 SO2N(CH3)2 Cl CH3 A-8 SO2N(CH3)2 Cl Cl A-9 SO2N(CH3)2 Cl Cl A-8 SO2CF3 Cl CH3 A-9 SO2CF3 Cl CH3 A-8 SO2CF3 Cl Cl A-9 SO2CF3 Cl Cl A-8 SO2OCH2CF3 Cl CH3 A-9 SO2OCH2CF3 Cl CH3 A-8 SO2OCH2CF3 Cl Cl A-9 SO2OCH2CF3 Cl Cl A-8 CF3 Cl CH3 A-9 CF3 Cl CH3 A-8 CF3 Cl Cl A-9 CF3 Cl Cl A-8 OCH3 Cl CH3 A-9 OCH3 Cl CH3 A-8 OCH3 Cl Cl A-9 OCH3 Cl Cl A-8 NO2 Cl CH3 A-9 NO2 Cl CH3 A-8 NO2 Cl Cl A-9 NO2 Cl Cl A-24 SO2CH3 Cl CH3 A-33 SO2CH3 Cl CH3 A-24 SO2CH3 Cl Cl A-33 SO2CH3 Cl Cl A-24 SO2CH2CH3 Cl CH3 A-33 SO2CH2CH3 Cl CH3 A-24 SO2CH2CH3 Cl Cl A-33 SO2CH2CH3 Cl Cl A-24 SO2CH2CH2CH3 Cl CH3 A-33 SO2CH2CH2CH3 Cl CH3 A-24 SO,CH2CH2CH3 Cl Cl A-33 SO2CH2CH2CH3 Cl Cl A-24 SO2N(CH3)2 CH3 CH3 A-33 SO2N(CH3)2 CH3 CH3 A-24 SO2N(CH3)2 Cl CH3 A-33 SO2N(CH3)2 Cl CH3 A-24 So2N(cH3)2 Cl Cl A-33 so2N(cH3)2 Cl Cl A-24 SO2CF3 Cl CH3 A-33 SO2CF3 Cl CH3 A-24 SO2CF3 Cl Cl A-33 SO2CF3 Cl Cl A-24 SO2OCH2CF3 Cl CH3 A-33 SO2OCH2CF3 Cl CH3 A-24 SO2OCH2CF3 Cl Cl A-33 SO2OCH2CF3 Cl Cl A-24 CF3 Cl CH3 A-33 CF3 Cl CH3 A-24 CF3 Cl Cl A-33 CF3 Cl Cl CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 A-24 OCH3 Cl CH3 A-33 OCH3 Cl CH3 A-24 OCH3 Cl Cl A-33 OCH3 Cl Cl A-24 NO2 Cl CH3 A-33 NO2 Cl CH3 A-24 NO2 Cl Cl A-33 NO2 Cl Cl A-42 SO2CH3 Cl CH3 A-44 SO2CH3 Cl CH3 A-42 SO2CH3 Cl Cl A-44 SO2CH3 Cl Cl A-42 SO2CH2CH3 Cl CH3 A-44 SO2CH2CH3 Cl CH3 A-42 SO2CH2CH3 Cl Cl A-44 SO2CH2CH3 Cl Cl A-42 SO2CH2CH2CH3 Cl CH3 A-44 SO2CH2CH2CH3 Cl CH3 A-42 SO2CH2CH2CH3 Cl Cl A-44 SO2CH2CH2cH3 Cl Cl A-42 So2N(cH3)2 CH3 CH3 A-44 . SO2N(CH3)2 CH3 CH3 A-42 SO2N(CH3)2 Cl CH3 A-44 SO2N(CH3)2 Cl CH3 A-42 So2N(cH3)2 Cl Cl A-44 SO2N(CH3)2 Cl Cl A-42 SO2CF3 Cl CH3 A-44 SO2CF3 Cl CH3 A-42 SO2CF3 Cl Cl A-44 SO2CF3 Cl Cl A-42 SO20CH2CF3 Cl CH3 A-44 SO20CH2CF3 Cl CH3 A-42 SO20CH2CF3 Cl Cl A-44 so2ocH2cF3 Cl Cl A-42 CF3 Cl CH3 A-44 CF3 Cl CH3 A-42 CF3 Cl Cl A-44 CF3 Cl Cl A-42 OCH3 Cl CH3 A-44 OCH3 Cl CH3 A-42 OCH3 Cl Cl A-44 OCH3 Cl Cl A-42 NO2 CH3 CH3 A-44 N~2 CH3 CH3 A-42 NO2 Cl CH3 A-44 NO2 Cl CH3 A-42 NO2 Cl Cl A-44 NO2 Cl Cl A-45 SO2CH3 Cl CH3 A-67 SO2CH3 Cl CH3 A-45 SO2CH3 Cl Cl A-67 SO2CH3 Cl Cl A-45 SO2CH2CH3 Cl CH3 A-67 SO2CH2CH3 Cl CH3 A-45 SO2CH2CH3 Cl Cl A-67 SO2CH2CH3 Cl Cl A-45 SO2CH2CH2CH3 Cl CH3 A-67 SO2CH2CH2CH3 Cl CH3 A-45 SO2CH2CH2CH3 Cl Cl A-67 SO2CH2CH2CH3 Cl Cl CA 022~7196 1998-11-30 PCTrUS97/09569 A-45 SO2N(CH3)2 CH3 CH3 A-67 SO2N(CH3)2 CH3 CH3 A-45 SO2N(CH3)2 Cl CH3 A-67 SO2N(CH3)2 Cl CH3 A-45 SO2N(CH3)2 Cl Cl A-67 SO2N(CH3)2 Cl Cl A-45 SO2CF3 Cl CH3 A-67 SO2CF3 Cl CH3 A-45 SO2CF3 Cl Cl A-67 SO2CF3 Cl Cl A-45 SO20CH2CF3 Cl CH3 A-67 SO20CH2CF3 Cl CH3 A-45 SO20CH2CF3 Cl Cl A-67 SO20CH2CF3 Cl Cl A-45 CF3 Cl CH3 A-67 CF3 Cl CH3 A~45 CF3 Cl Cl A-67 CF3 Cl Cl A-45 OCH3 Cl CH3 A-67 OCH3 Cl CH3 A-45 OCH3 Cl Cl A-67 OCH3 Cl Cl A-45 NO2 CH3 CH3 A-67 N~2 CH3 CH3 A-45 NO2 Cl CH3 A-67 NO2 Cl CH3 A-45 NO2 Cl Cl A-67 NO2 Cl Cl A-68 S02CH~, Cl CH3 A-71 S02CH3 Cl CH3 A-68 SO2CH3 Cl Cl A-71 SO2CH3 Cl Cl A-68 SO2CH2CH3 Cl CH3 A-7] SO2CH2CH3 Cl CH3 A-68 SO2CH2CH3 Cl Cl A-71 SO2CH2CH3 Cl Cl A-68 SO2CH2CH2CH3 Cl CH3 A-71 SO2CH2CH2CH3 Cl CH3 A-68 SO2CH2CH2CH3 Cl Cl A-71 SO2CH2CH2CH3 Cl Cl A-68 SO2N(CH3)2 CH3 CH3 A-71 SO2N(CH3)2 CH3 CH3 A-68 SO2N(CH3)2 Cl CH3 A-71 SO2N(CH3)2 Cl CH3 A-68 SO2N(CH3)2 Cl Cl A-71 SOzN(CH3)2 Cl Cl A-68 SO2CF3 Cl CH3 A-71 SO2CF3 Cl CH3 A-68 SO2CF3 Cl Cl A-71 SO2CF3 Cl Cl A-68 SO20CH2CF3 Cl CH3 A-71 SO20CH2CF3 Cl CH3 A-68 so2ocH2cF3 Cl Cl A-71 SO20CH2CF3 Cl Cl A-68 CF3 Cl CH3 A-71 CF3 Cl CH3 A-68 CF3 Cl Cl A-71 CF3 Cl Cl CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 A-68 OCH3 Cl CH3 A-71 OCH3 Cl CH3 A-68 OCH3 Cl Cl A-71 OCH3 Cl Cl A-68 NO2 CH3 CH3 A-71 N~2 CH3 CH3 A-68 NO2 Cl CH3 A-71 NO2 Cl CH3 A-68 NO2 Cl Cl A-71 NO2 Cl Cl A-78 SO2CH3 Cl CH3 A-91 SO2CH3 Cl CH3 A-78 SO2CH3 Cl Cl A-91 SO2CH3 Cl Cl A-78 SO2CH2CH3 Cl CH3 A-91 SO2CH2CH3 Cl CH3 A-78 SO2CH2CH3 Cl Cl A-91 SO2CH2CH3 Cl Cl A-78 SO2CH2CH2CH3 Cl CH3 A-91 SO2CH2CH2CH3 Cl CH3 A-78 SO2CH2CH2CH3 Cl Cl A-91 SO2CH2CH2CH3 Cl Cl A-78 SO2N(CH3)2 CH3 CH3 A-91 SO2N(CH3)2 CH3 CH3 A-78 SO2N(CH3)2 Cl CH3 A-91 SO2N(CH3)2 Cl CH3 A-78 SO2N(CH3)2 Cl Cl A-91 SO2N(CH3)2 Cl Cl A-78 SO2CF3 Cl CH3 A-91 SO2CF3 Cl CH3 A-78 SO2CF3 Cl Cl A-91 SO2CF3 Cl Cl A-78 SO20CH2CF3 Cl CH3 A-91 SO20CH2CF3 Cl CH3 A-78 SO20CH2CF3 Cl Cl A-91 SO20CH2CF3 Cl Cl A-78 CF3 Cl CH3 A-91 CF3 Cl CH3 A-78 CF3 Cl Cl A-91 CF3 Cl Cl A-78 OCH3 Cl CH3 A-91 OCH3 Cl CH3 A-78 OCH3 Cl Cl A-91 OCH3 Cl Cl A-78 NO2 CH3 CH3 A-91 N~2 CH3 CH3 A-78 NO2 Cl CH3 A-91 N~2 Cl CH3 A-78 NO2 Cl Cl A-91 NO2 Cl Cl CA 022~7196 1998-ll-30 W O 97/46530 PCTrUS97/09569 5(o)2Rls A Rls R14 A Rl5 R14 A- I CH3 PhC(=0) A-2 CH3 PhC(=0) A- I CH3 4-CH3PhC(=0) A-2 CH3 4-CH3PhC(=0) A- 1 CH3 CH3S(0)2 A-2 CH3 CH3S(0)2 A- I CH3 CH3CH2S(0)2 A-2 CH3 CH3CH2S(0~2 A- ] CH3 CH3CH2CH2S(0)2 A-2 CH3 CH3CH2CH2s(0)2 A- I CH3 PhS(0)2 A-2 CH3 PhS(0~2 A- I CH3 4-CH3PhS(0)2 A-2 CH3 4-CH3PhS(0)2 A- 1 CH3 Na A-2 CH3 Na A-3 CH3 PhC(=0) A-33 CH3 PhC(=0) A-3 CH3 4-CH3PhC(=0) A-33 CH3 4-CH3PhC(=0) A-3 CH3 CH3S(0)2 A-33 CH3 CH3S(0)2 A-3 CH3 CH3CH2S(0)2 A-33 CH3 CH3CH2S(0)2 A-3 CH3 CH3CH2CH2S(0)2 A-33 CH3 CH3CH~CH2s(0)2 A-3 CH3 PhS(0)2 A-33 CH3 PhS(0)~
A-3 CH3 4-CH3PhS(0)2 A-33 CH3 4-CH3PhS(0)2 A-3 CH3 Na A-33 CH3 Na A-67 CH3 PhC(=0) A-71 CH3 PhC(=0) A-67 CH3 4-CH3PhC(=0) A-71 CH3 4-CH3PhC(=0) A-67 CH3 CH3S(0)2 A-71 CH3 CH3S(0)2 A-67 CH3 CH3cH2s(o)2 A-71 CH3 CH3CH2S(0)2 A-67 CH3 CH3CH2CH2S(0)2 A-71 CH3 CH3CH2CH2s(0)2 .
A-67 CH3 PhS(0)2 A-71 CH3 PhS(0)2 A-67 CH3 4-CH3PhS(0)2 A-71 CH3 4-CH3PhS(0)2 A-67 CH3 Na A-71 CH3 Na A- I CH2CH3 PhC(=0) A-2 CH2CH3 PhC(=0) ~ . .. .

CA 022~7196 1998-11-30 A- I CH2CH3 4-CH3PhC(=O) A-2 CH2CH3 4-CH3PhC(=O) A-l CH2CH3 CH3S(o)2 A-2 CH2CH3 CH3S(0)2 A- I CH2CH3 CH3CH2S(0)2 A-2 CH2CH3 CH3CH2S(0)2 A- I CH2CH3 CH3CH2CH2S(0)2 A-2 CH2CH3 CH3CH2cH2s(0)2 A- I CH2CH3 PhS(0)2 A-2 CH2CH3 PhS(0)2 A- I CH2CH3 4-CH3PhS(0)2 A-2 CH2CH3 4-CH3PhS(0)2 A-l CH2CH3 Na A-2 CH2CH3 Na A-3 CH2CH3 PhC(=O) A-33 CH2CH3 PhC(=O) A-3 CH2CH3 4-CH3PhC(=O) A-33 CH2CH3 4-CH3PhC(=O) A-3 CH2CH3 CH3S(o)2 A-33 CH2CH3 CH3S(0)2 A-3 CH2CH3 CH3CH2S(0)2 A-33 CH2CH3 CH3CH2S(0)2 A-3 CH2CH3 CH3CH2CH2S(0)2 A-33 CH2CH3 CH3CH2CH2s(0)2 A-3 CH2CH3 PhS(0)2 A-33 CH2CH3 PhS(0)2 A-3 CH2CH3 4-CH3PhS(0)2 A-33 CH2CH3 4-CH3PhS(0)2 A-3 CH2CH3 Na A-33 CH2CH3 Na A-67 CH2CH3 PhC(=O) A-71 CH2CH3 PhC(=O) A-67 CH2CH3 4-CH3PhC(=O) A-7] CH2CH3 4-CH3PhC(=O) A-67 CH2CH3 CH3S(0)2 A-71 CH2CH3 CH3S(0)2 A-67 CH2CH3 CH3CH2S(0)2 A-71 CH2CH3 CH3CH2S(0)2 A-67 CH2CH3 CH3cH2cH2s(o)2 A-71 CH2CH3 CH3CH2CH2s(0)2 A-67 CH2CH3 PhS(0)2 A-71 CH2CH3 PhS(0)2 A-67 CH2CH3 4-CH3PhS(0)2 A-71 CH2CH3 4-CH3PhS(0)2 A-67 CH2CH3 Na A-71 CH2CH3 Na A- I CH2CH2CH3 PhC(=O) A-2 CH2CH2CH3 PhC(=O) A- I CH2CH2CH3 4-CH3PhC(=O) A-2 CH2CH2CH3 4-CH3PhC(=O) A- I CH2CH2CH3 CH3S(~)2 A-2 CH2CH2CH3 CH3S(0)2 A- I CH2CH2CH3 CH3CH2S(~)2 A-2 CH2CH2CH3 CH3CH2S(~)2 A- 1 CH2CH2CH3 CH3CH2CH2S(0)2 A-2 CH2CH2CH3 CH3CH2CH2S(0)2 A- I CH2CH2CH3 PhS(~)2 A-2 CH2CH2CH3 PhS(~)2 A- I CH2CH2CH3 4-CH3PhS(0)2 A-2 CH2CH2CH3 4-cH3Phs(o)2 A- I CH2CH2CH3 Na A-2 CH2CH2CH3 Na A-3 CH2CH2CH3 PhC(=O) A-33 CH2CH2CH3 PhC(=O) A-3 CH2CH2CH3 4-CH3PhC(=O) A-33 CH2CH2CH3 4-CH3PhC(=O) A-3 CH2CH2CH3 CH3S(~)2 A-33 CH2CH2CH3 CH3S(O)~

CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 A-3 CH2CH2CH3 CH3CH2S(~)2 A-33 CH2CH2CH3 CH3CH2S(0)2 A-3 CH2CH2CH3 CH3CH2CH2S(0)2 A-33 CH2CH2CH3 CH3CH2CH2S(0)2 A-3 CH2CH2CH3 PhS(~)2 A-33 CH2CH2CH3 PhS(~)2 A-3 CH2CH2CH3 4-cH3Phs(o)2 A-33 CH2CH2CH3 4-cH3Phs(o)2 A-3 CH2CH2CH3 Na A-33 CH2CH2CH3 Na A-67 CH2CH2CH3 PhC(=O) A-71 CH2CH2CH3 PhC(=O) A-67 CH2CH2CH3 4-CH3PhC(=O) A-71 CH2CH2CH3 4-CH3PhC(=O) A-67 CH2CH2CH3 CH3S(0)2 A-71 CH2CH2CH3 CH3S(0)2 A-67 CH2CH2CH3 CH3CH2S(~)2 A-71 CH2CH2CH3 CH3CH2S(0)2 A-67 CH2CH2CH3 CH3CH2CH2S(0)2 A-71 CH2CH2CH3 CH3CH2CH2S(0)2 A-67 CH2CH2CH3 PhS(0)2 A-71 CH2CH2CH3 PhS(0)2 A-67 CH2CH2CH3 4-CH3PhS(0)2 A-71 CH2CH2CH3 4-CH3PhS(0)2 A-67 CH2CH2CH3 Na A-7 ~ CH2CH2CH3 Na S¢O)2RIS

A Rls R14 A Rls R14 A- I CH3 PhC(=O) A-2 CH3 PhC(=O) A-l CH3 4-CH3PhC(=O) A-2 CH3 4-CH3PhC(=O) A-l CH3 CH3S(0)2 A-2 CH3 CH3S(0)2 A- I CH3 CH3CH2S(0)2 A-2 CH3 CH3CH2S(0)2 A- I CH3 CH3CH2CH2S(0)2 A-2 CH3 CH3CH2CH2S(0)2 A-l CH3 PhS(0)2 A-2 CH3 PhS(~)2 A- I CH3 4-CH3PhS(0)2 A-2 CH3 4-CH3PhS(0)2 A- I CH3 Na A-2 CH3 Na A-3 CH3 PhC(=O) A-33 CH3 PhC(=O) A-3 CH3 4-CH3PhC(=O) A-33 CH3 4-CH3PhC(=O) A-3 CH3 CH3S(o)2 A-33 CH3 CH3S(0)2 . .

CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 A-3 CH3 CH3CH2s(0)2 A-33 CH3 CH3CH2S(0)2 A-3 CH3 CH3CH2CH2S(0)2 A-33 CH3 CH3CH2CH2S(0)2 A-3 CH3 PhS(0)2 A-33 CH3 PhS(0)2 A-3 CH3 4-CH3PhS(0)2 A-33 CH3 4-CH3PhS(0)2 A-3 CH3 Na A-33 CH3 Na A-67 CH3 PhC(=0) A-71 CH3 PhC(=0) A-67 CH3 4-CH3PhC(=0) A-71 CH3 4-CH3PhC(=0) A-67 CH3 CH3S(0)2 A-71 CH3 CH3S(0)2 A-67 CH3 CH3CH2S(0)2 A-71 CH3 CH3CH2S(0)2 A-67 CH3 CH3CH2CH2S(0)2 A-71 CH3 CH3CH2CH2S(0)2 A-67 CH3 PhS(0)2 A-71 CH3 PhS(0)2 A-67 CH3 4-CH3PhS(0)2 A-71 CH3 4-CH3PhS(0)2 A-67 CH3 Na A-71 CH3 Na A-l CH2CH3 PhC(=0) A-2 CH2CH3 PhC(=0) A-l CH2CH3 4-CH3PhC(=0) A-2 CH2CH3 4-CH3PhC(=0) A-l CH2CH3 CH3S(o)2 A-2 CH2CH3 CH3S(0)2 A-l CH2CH3 CH3CH2S(0)2 A-2 CH2CH3 CH3CH2S(0)2 A-l CH2CH3 CH3CH2cH2s(0)2 A-2 CH2CH3 CH3CH2CH2s(0)2 A-l CH2CH3 PhS(0)2 A-2 CH2CH3 PhS(0)2 A-l CH2CH3 4-CH3PhS(0)2 A-2 CH2CH3 4-CH3PhS(0)2 A-l CH2CH3 Na A-2 CH2CH3 Na A-l CH2CH3 K A-2 CH,CH3 K
A-3 CH2CH3 PhC(=0) A-33 CH2CH3 PhC(=0) A-3 CH2CH3 4-CH3PhC(=O) A-33 CH2CH3 4-CH3PhC(=0) A-3 CH2CH3 CH3S(0)2 A-33 CH2CH3 CH3S(o)2 A-3 CH2CH3 CH3CH2s(o)2 A-33 CH2CH3 CH3CH2S(0)2 A-3 CH2CH3 CH3CH2CH2S(0)2 A-33 CH2CH3 CH3CH2CH2s(0)2 A-3 CH2CH3 PhS(0)2 A-33 CH2CH3 PhS(0)2 A-3 CH2CH3 4-CH3PhS(0)2 A-33 CH2CH3 4-CH3Phs(0)2 A-3 CH2CH3 Na A-33 CH2CH3 Na A-67 CH2CH3 PhC(=0) A-71 CH2CH3 PhC(=0) A-67 CH2CH3 4-CH3PhC(=0) A-71 CH2CH3 4-CH3PhC(=0) A-67 CH2CH3 CH3S(o)2 A-71 CH2CH3 CH3S(0)2 A-67 CH2CH3 CH3CH2S(0)2 A-71 CH2CH3 CH~CH2S(0)2 A-67 CH2CH3 CH3CH2cH2s(0)2 A-71 CH2CH3 CH3CH2CH2S(0)2 CA 022~7196 1998-11-30 W O97/46530 PCTrUS97/09569 A-67 CH2CH3 PhS(O)2 A-71 CH2CH3 PhS(O)2 A-67 CH2CH3 4-CH3PhS(O)2 A-71 CH2CH3 4-CH3PhS(O)2 A-67 CH2CH3 Na A-71 CH2CH3 Na A-l CH2CH2CH3 PhC(=O) A-2 CH2CH2CH3 PhC(=0) A-l CH2CH2CH3 4-CH3PhC(=0) A-2 CH2CH2CH3 4-CH3PhC(=0) A-l CH2CH2CH3 CH3S(O)2 A-2 CH2CH2CH3 CH3S(~)2 A-l CH2CH2CH3 CH3CH2S(~)2 A-2 CH2CH2CH3 CH3CH2S(O)2 A-l CH2CH2CH3 CH3CH2CH2S(O)2 A-2 CH2CH2CH3 cH3cH2cH2s(o)2 A-l CH2CH2CH3 PhS(~)2 A-2 CH2CH2CH3 PhS(~)2 A-l CH2CH2CH3 4-CH3PhS(O)2 A-2 CH2CH2CH3 4-CH3PhS(O)2 A-l CH2CH2CH3 Na A-2 CH2CH2CH3 Na A-l CH2CH2CH3 K A-2 CH2CH2CH3 K
A-3 CH2CH2CH3 PhC(=0) A-33 CH2CH2CH3 PhC(=O) A-3 CH2CH2CH3 4-CH3PhC(=0) A-33 CH2CH2CH3 4-CH3PhC(=0) A-3 CH2CH2CH3 CH3S(~)2 A-33 CH2CH2CH3 CH3S(~)2 A-3 CH2CH2CH3 CH3CH2S(~)2 A-33 CH2CH2CH3 CH3CH2S(O)2 A-3 CH2CH2CH3 CH3CH2CH2S(O)2 A-33 CH2CH2CH3 CH3CH2CH2S(~)2 A-3 CH2CH2CH3 PhS(O)2 A-33 CH2CH2CH3 PhS(O)2 A-3 CH2CH2CH3 4-cH3Phs(o)2 A-33 CH2CH2CH3 4-CH3PhS(0)2 A-3 CH2CH2CH3 Na A-33 CH2CH2CH3 Na A-67 CH2CH2CH3 PhC(=0) A-71 CH2CH2CH3 PhC(=0) A-67 CH2CH2CH3 4-CH3PhC(=0) A-71 CH2CH2CH3 4-CH3PhC(=0) A-67 CH2CH2CH3 CH3S(O)2 A-71 CH2CH2CH3 CH3S(O)2 A-67 CH2CH2CH3 CH3CH2S(O)2 A-71 CH2CH2CH3 CH3CH2S(~)2 A-67 CH2CH2CH3 CH3CH2CH2S(O)2 A-71 CH2CH2CH3 CH3CH2CH2S(O)2 A-67 CH2CH2CH3 PhS(~)2 A-71 CH2CH2CH3 PhS(~)2 A-67 CH2CH2CH3 4-CH3PhS(O)2 A-71 CH2CH2CH3 4-cH3Phs(o)2 A-67 CH2CH2CH3 Na A-71 CH2CH2CH3 Na A-67 CH2CH2CH3 K A-7] CH2CH2CH3 K

CA 022~7196 1998-ll-30 W O 97/46530 PCTrUS97/09569 O O A

~~~Rla Rlb Rlai' CF3,RIbis H, and W isN
_ _ _ A _ _ A A A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CF3,F'IbisH,andWisC~:I
_ A A A _ _ A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,RIbisH,andWisN
_ A A L A A A A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O97146S30 PCTnUS97/09569 Rlai-Cl~RlbisH,andWisCH
A _ _ _ _ _ _ _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai-CH~,RIbisH,andWisN
A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-73 A-74 A-75 A-76 A-77 A-78 A-79 A-80 A-8] A-82 A-83 A-84 Rlai-CH3,RlbisH,andWisCH
_ _ _ _ A _ A A A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 .. . .. ..

CA 022~7196 1998-11-30 W O 97/46530 rcTrusg7/og569 Rla i~ S02CH3, Rlb is H, and W s N
_ A A _ _ _ _ A _ _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai S02CH3,RIbisH,-ndW sCH
_ _ _ A A _ _ A _ A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-lS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i~ SO2C:I2CH?~, Rlb i H, an- W is ~
A A A A A A A A _ _ _ _ A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i S02C'I2CH-. RIb i-- H. and W is CH
A _ _ _ A _ _ A A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97/09569 Rlai- CF~,RIbisCN,andWisN
_ _ _ _ _ _ A A A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-73 A-74 A-75 A-76 A-77 A-78 A-79 A-80 A-8] A-82 A-83 A-84 Rlai- CF3,RIbisCN,andWisCH
A _ A _ _ A A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ Cl,RIbisCN,andWisN
A _ A _ _ _ _ A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 .. . ...

CA 022~7196 1998-11-30 Rla i-- Cl, Rlb is CN, and W is CH
A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai- CH3,~1bisCN,an- WisN
A _ A _ _ A A _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ CH3,RIbisCN,an~ WisCH
A _ _ _ _ _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 W O 97/46530 PCTtUS97tOgS69 Rlai~ S02C~,RlbisCN,andWisN
A _ A A _ A _ _ A A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai S02CI3,RIbisCN,andWisCH
A _ A A A _ _ A A A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rla i~- SO2C-I2CH~, Rlb i CN, and W i N
_ A _ A A _ _ _ A A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rla i~- S02CH2CH, Rlb i~ CN, and W i~ CH
_ _ _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 CA 022~7196 1998-11-30 Rlai CF3,P.lbisCl,andWisN
_ B A A A A A _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-50 A-51 A-52 A-53 A-54 A-55. A-56 A-57 A-58 A-S9 A-60 Rlai~ CF3,PIbisCl,andWisC.~
_ A A _ _ A _ A A _ A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,Rlbis Cl and W is N
_ _ A _ _ A _ A _ _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97109569 Rlai--Cl~RlbisCl andWisCH
_ A A _ _ _ A _ _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai CH3,RIbisSO2C~andWisN
A _ A A _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai~ CH3,~1bisSO2CH~andWisCH
_ A _ _ A A _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 ... . . ..

CA 022~7196 1998-11-30 ~ ~ ~ Rla CH2CH3 Rlb Rlai CF3,PIbisE~',and~'isN
A _ _ _ _ A _ A A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ CF3,RlbisH,and~isCH
A _ A _ _ _ _ _ _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai~-Cl,RIbisH,andWisN
_ A _ _ _ _ A _ A A _ _ A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 CA 022~7196 1998-11-30 R~ai Cl,RlbisH,andWisCH
_ _ A _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ CH~,RIbisH,andWisN
A _ _ A A A A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai--CH3,RIbis I,andWisCI
_ _ A _ _ A _ _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 WO 97/46530 PCTrUS97/09S69 Rlai SO2C;_3,RIbisH~ ndW sN
_ _ _ _ A _ A _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rla i S02CH3, Rlb is H, - nd W .s CH
A _ _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla j S02CH2CH~, Rlb i~ H, an- W is ~I
A _ _ A A A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-50 A-S l A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-59 A-60 Rla i SO2C-I2CH" Rlb i~ H, an- W is CH
A _ _ _ _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 Rlai~ CF~RIbisCN,andWisN
A _ _ _ _ A _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai--CF3~P.IbisCN,andWisCH
_ _ _ _ A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CI~RlbisCI'~,and~isN
_ _ _ A A A _ _ _ A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 ~ A-37 A-38 A-39 A-40 A-41 A-42 A-43 A-44 A-45 A-46 A-47 A-48 ... ~ .. .. . .

W O97/46530 PCTrUS97/09569 Rlai C~,RIbisCN,andWisCH
A A _ A _ A _ L A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CH3,RlbisCN,andWisN
_ _ A A _ A _ _ _ _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ CH3,RIbisCN,an- WisCH
_ _ A _ _ A A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 . .

CA 022~7196 1998-11-30 w o 97/46530 PcTruss7lo9569 Rlai S02CH3,RlbisCN,and~isN
A _ _ A A A A _ A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-Sl A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-S9 A-60 Rlai- S 02C H3, RlbiS C N, and ~is C H
_ _ _ A _ _ A A A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-lS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-Sl A-52 A-53 A-54 A-SS A-56 A-57 A-58 A-S9 A-60 Rlai- S O2C:~2C H ~ Rlbi- C N, and W i N
A _ A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-Sl A-52 A-53 A-54 A-SS A-56 A-57 A-58 A-S9 A-60 Rlai~- S O2C _2C H , Rlbi C N, and W i C H
A _ _ A A B A _ A A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O97/46530 PCT~US97/09569 Rlai--CF3,RIbisCl,andWisN
A _ _ _ A _ A _ _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ CF3,RlbisCl,andWisC~
A A A _ _ _ A A _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rl~i-Cl,RlbisCl andWisN
A A A A A A A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 W 097/46530 PCT~US97/09569 Rlai-CI,RlbiSCI andWisCH
A A A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i CH3, Rlb iS SO2CH~ and W iS N
A A A _ A _ A A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai--CH3, RlbisSO2C~,andWisC-~
A _ A _ _ A _ A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-85 A-86 A-8? A-88 A-89 A-90 A-91 A-92 A-93 CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09~69 o o Rla A
Rlb Rlai~ CF3,Rlbis~:.,and'~isN
_ A _ A _ A A _ A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 R~ai CF3,RlbisE~,and~isCH
_ A A _ A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-]7 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,RIbisH,andWisN
_ A A A A A _ _ _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 Rlai Cl,RlbisH~andWisCH
_ A _ _ _ _ _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-85 A-86 A-87 A-88 A-89A-90 A-91 . A-92 A-93 Rla i CH3, Rlb is I, and W is N
A _ _ A _ _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-73 A-74 A-75 A-76 A-77 A-78 A-79 A-80 A-8] A-82 A-83 A-84 A-85 A-86 A-87 A-88 A-89 A-90 A-9] A-92 A-93 Rlai CH3,RIbisH,andWisC-:~
_ A _ _ _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 ... .. . .

CA 022~7196 1998-11-30 W O97/46530 PCTrUS97/09569 Rlai--S02C-I3,RlbisH, ndW-sN
_ A _ A _ A A _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ SO2C-_3,RIbis H, ndW:sCH
_ _ A A _ _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai S02C~ ,Rlbi~ H,andWis~
_ _ A A A _ A _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 ,4-73 A-74 A-75 A-76 A-77 A-78 A-79 A-80 A-81 A-82 A-83 A-84 Rla i~ SO2CH2CH~, Rlb i- H, and W is CH
_ A _ A _ A A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 .

CA 022~7196 1998-11-30 W O97/46530 PCT~US97/09569 Rlai-CF3,RlbisCN,andWisN
A _ _ A _ A _ _ A _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CF3,RlbisCN,andWisCH
A A _ A A A A _ A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai Cl,RIbisCN,andWisN
A _ A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 W O 97/46530 PCT~US97/09569 Rlai--Cl,RIbisCl~~,andWisCH
_ _ _ A _ _ A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai--CH3,RIbisCN,an~ WisN
_ _ A _ _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai- CH3,RIbisCN,andWisCH
_ _ _ _ _ A _ A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 CA 022~7196 1998-11-30 W O97/46530 rCT~US97/09569 Rlai~ SO2C ~3~RIbis CN, and W is N
_ _ A _ A A A A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i- SO2C_3, Rlb is CN, and W is CH
A _ A A _ A A A A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i~ SO2C~2CH-, Rlb i- CN, and W i - N
A A A _ A _ A A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i S02CH2~. Rlb i~ CN, and W i- CH
_ _ A _ _ A _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 A-49 A-50 A-Sl A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-59 A-60 Rlai~-CF3,Plbis Cl, and W is N
A _ _ _ _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-50 A-51 A-52 A-53 A-54 A-55 . A-56 A-57 A-58 A-S9 A-60 Rlai~ CF3,P.lbisCl,andWisC~~
_ _ _ _ _ A _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,RlbisCI andWisN
_ _ _ _ A A _ _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 W O 97/46530 PCTrUS97/09569 Rla i - CL Rlb is Cl and W is CH
A _ _ _ _ _ _ _ _ _ _ A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai--CH3,RIbisSO2CH3, and W is N
_ A _ _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CH3,RIbisSO2C~-3, and W is C H
A _ A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 ..... ~ . , CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97/09569 O Rla H~A
I H2CH3 Rlb Rlai- CF3,F'lbis~,and~isN
A _ A _ A _ A A _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CF3,RIbisH,andWisCH
A A A A _ A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,RIbisH,andWisN
A A A _ A A _ A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-S l A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-59 A-60 CA 022~7196 1998-11-30 Rlai~ Cl,RIbisH,andWisCH
A _ _ A _ A _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-85 A-86 A-87 A-88 A-89A-90 A-91 . A-92 A-93 Rlai CH3,RIbis~:I,andWisN
A _ _ _ _ _ _ _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai CH3,RIbisH,andWisC~I
_ A A A _ A _ _ A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 CA 022~7196 1998-ll-30 W O 97/46530 PCTrUS97/09569 Rla i- SO2CH3, Rlb is H, nd W s N
_ _ _ A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-11 A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-Sl A-52 A-53 A-54 A-55 A-56 A-57 A-58 A-59 A-60 Rlai-S02CH~,RIbisH, .ndW-sCH
_ A _ _ A A A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai~ SO2_H2CH~,RIbi H,andWis~
_ _ A _ A _ A A _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i~ SO2CH2CH~, Rlb i-- H, and W is CH
_ A _ _ _ _ A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O 97/46530 PCTrUS97109569 Rla i CF3~ Rlb is CN, and W is N
A _ _ _ _ A A _ _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai-CF3,RlbisCN,an- WisCH
_ A _ _ A _ A _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai--Cl,RIbisCN,andWisN
A _ _ _ A A _ A _ _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 Rlai Cl,RIbisC~~,andWisCH
A _ A _ A _ _ _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14A-15. A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CH~ IbisCN,an- WisN
A A A _ _ A _ _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 Rlai--CH3,RIbisCN,andWisCH
A _ A _ A A _ _ _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 Rla i-- SO2CH3, Rlb is CN, and W is N
_ _ _ A A A A A _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i S02C :~3, Rlb iS CN. and ~ is CH
_ _ _ _ _ _ _ A _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-S0 A-Sl A-52 A-53 A-54 A-SS A-56 A-57 A-58 A-S9 A-60 Rla i-- SO2CH2CH~, Rlb i - CN, and W i- N
A _ _ _ _ A _ _ A A A A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i SO2_ 2CH~, RIb i CN, and W i-- CH
_ A A A _ _ _ A A A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 .. . .. . _ ~ . , .

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 RlaisCF3.RIbisCl,andWisN
A _ _ _ A _ A A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 A-49 A-50 A-51 A-52 A-53A-54 A-55 . A-56 A-57 A-58 A-59 A-60 Rlai CF~RlbisCl,andWisC~I
_ _ A _ A A _ A A A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai Cl,RIbisCl andWisN
A A _ _ _ A A _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 Rla i- Cl, Rlb is Cl and W is CH
_ _ A A _ _ _ A _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rlai CH3,~lbisSO2C~3,andWisN
A _ A _ _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-l l A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Rla i~- CH~, Rlb is SO2CH3, and W is C-I
A _ _ A A _ A _ _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 W O97/46530 PCTrUS97/0956g O O A
~W

W is CH
_ _ A _ _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 wis:~
_ A _ _ _ A _ _ _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 ~l J~
~W

W is CH
_ _ _ _ _ A _ A A _ A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 WiS~
_ _ A _ _ A _ _ _ A _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-ll-30 ~ O ~ A

W is C~
_ _ _ A _ A _ _ _ A A A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 W is ~
A A _ _ A _ A _ _ A
A-l A-2 A-3 A-4 A-S A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 CA 022~7196 1998-11-30 WO 97/46530 PCT/USg7/09569 ~ A

W is CH
A A A _ _ _ _ A _ A _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-IS A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 Wis~
_ _ _ _ A A _ _ A _ _ A
A-l A-2 A-3 A-4 A-5 A-6 A-7 A-8 A-9 A-10 A-ll A-12 A-13 A-14 A-15 A-16 A-17 A-18 A-l9 A-20 A-21 A-22 A-23 A-24 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 5 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 environm~nt~l factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including em~ ifi~ble concentrates), suspensions, CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 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 5 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 lO0 percent by weight.
Weight Percent Active In~redient Diluent Surfactant Water-Dispersible and Water-soluble 5-90 (}94 1-15 Granules, Tablets and Powders.
Suspensions, Emulsions, Solutions 5-50 4~95 ~15 (inçlll(ling F.m~ ifi~hle Concentrates) Dusts 1-25 7~99 ~5 Granules and Pellets 0.01-99 5-99 99 ~15 High Strength Compositions 9~99 ~}10 ~2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ.
Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological 20 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, n~ph~h~lene sulfonate formaldehyde condensates, polycarboxylates, and 25 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 CA 022~7l96 l998-ll-30 W O 97/46S30 PCT~US97/09569 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 h~mmer mill or fluid-energy mill. Suspensions are usually prepared by wet-rnilling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active 10 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, 15 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 20 Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
Klingm~n, 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 ScientificPublications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-C.
Example A
High Stren,eth Concentrate Compound 1 98.5%
silica aerogel o.5%
synthetic amorphous fine silica 1.0%.

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 Example B
Wettable Powder Compound 15 65.0%
dodecylphenol polyethylene glycol ether 2.0%
sodiumligninsulfonate 4.0 %
sodium silicoalllmin~te 6.0%
montmorillonite (calcined) 23.0%.
Example C
Granule Compound 25 10.0%
attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-S0 sieves) 9o.o%.
Example D
Extruded Pellet Compound 26 25.0%
anhydrous sodium sulfate 10.0%
crude calcium ligninsulfonate 5.0%
sodium alkylnaphthalenesulfonate1.0%
calcium/magnesium bentonite 59 0%
Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, inclll~tri~l storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be 5 used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control:
acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, 10 azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, 15 chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, 20 dimethylarnmonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, 2-[4,5-dihydro-4-methyl-4-~ 1 -methylethyl)-5-oxo- lH-imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, 25 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, 30 fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, im~7~m-othabenz-methyl, im~7~mox, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, 35 ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium andsodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and CA 022~7196 1998-11-30 Wo 97/46530 PCTtUS97/09569 disodium salts, methyl [[[1-[5-[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)- lH-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pebulate, pen-iim~thalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, 10 pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, .~im~7ine, sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, 15 tri~7iflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vernolate.
In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds.
Preferred for better control of undesired vegetation (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group nicosulfuron, rimsulfuron, nicosulfuron in combination with rimsulfuron, imazethapyr, sethoxydim, glyphosate, and glufosinate.
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-D for compound descriptions. The abbreviation "dec." indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which 30 example the compound is prepared.

CA 02257196 1998-ll-30 ~VO 97/46530 PCT~US97/09569 DNDEX TABLE A

O O Rl R4a ~ A
R4b CmpdR4a R4bR3 Rl W A m.p. (~C) H H OH Cl CH4-pyridyl oil 2 CH3 CH3O-Et3NH+ Cl CH4-pyridyl oil 3 CH3 CH3OH Cl CH4-pyridyl oil*
4 CH3 HO-Et3NH+ Cl CH4-pyridyl oil CH3 H OH Cl CH4-pyridyl oil*
6 H HO-Et3NH+ Cl CH3-CF3- l H-pyrazol- l -yl oil 7 H H OH Cl CH3-CF3- 1 ~-pyrazol- 1 -yl97-108 8 H HO-Et3NH+ Cl CH4-pyridyl oil 9 H HO-Et3NH+ Cl CH2-pyridyl oil H HO-Et3NH+ CH3 CH2-thiazolyl oil I l H H OH CH3 CH2-thiazolyl oil*
12 H HO-Et3NH+ Cl CH3-pyridyl oil*
13 H H OH Cl CH3-pyridyl 110-115 *See Index Table D for lH NMR data.

.. . . .

INDEX TABLE B

O O A

R~ Rl Cmpd R4a R4b R3 R I W A m.p.

14 H HO-Et3NH+ CF3 N4-pyridyl oil 15 (Ex. 3) H H OH CF3 N 4-pyridyl 137-145 19 H HO-Et3NH+(CH3)2CHCH2CH2 N4-pyridyl oil H H OH CF3 N2-pyridyl 126-131 21 CH3 CH3 OH CF3 N2-pyridyl oil 22 H H OH CF3 N3-pyridyl oil 23 (Ex. 2) H H OH H CH 3-CF3-lH- 141-143 pyrazol- 1 -yl pyrazol- I -yl *See Index Table D for lH NMR data.

INDEX TABLE C

CmpdNo.Structure m.p. (~C) 25 (Ex. 1) /CH3 93 (dec-) ,~

OH ~S~CH3 CH3 ~ ~

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 26 ~CH3 oil // \\
CH3 ~ ~

27 ~CH3 oil OH ~S~cH2cH3 CH3 ~ O
28 ~CH390-91 29 O ~ oil*

CH3~N

O O N~
~ ~3 ~ N02 *See Index Table D for lH NMR data.

. .. .

CA 022~7196 1998-11-30 INDEX TABLE D
Cmpd No. IH NMR Data (CDC13 solution unless indicated otherwise)a ~ 9.7 (m, 2H), 7.63(m, 2H), 7.62 (m,IH), 7.6(s,IH), 7.37 (m,IH), 2.8(m, 2H), 2.5(m, 2H), 2.08(m, 2H).
2 ~ 8.65 (d, 2H),7.6(d,lH), 7.5 (m, 3H), 7.27(m,IH), 3.13 (m, 6H), 2.32(s, 4H), 1.3 (m, 9H), 1.04 (s, 6H).
3 ~8.8(m,2H),7.84(m,2H),7.69(m,2H),7.38(d,IH),2.4(m,2H), 1.2(m, 2H), 1.04 (d, 6H).
4 ~ 8.62 (d, 2H), 7.6(s,lH), 7.5(m, 3H), 7.28 (d, lH), 3.17 (m, 6H), 2.5 (d, 2H), 2.2 (d, lH), 1.7(m,lH), 1.31(m, 9H), 1.03 (d, 3H).
~ 8.72(m, 2H), 7.65 (m, 3H), 7.5 (d, IH), 7.3 (d, lH), 2.6-2.0(m, 4H), 1.6 (m,IH), 1.13 (d, 6H).
6 ~7.9(s,IH), 7.7 (s,IH), 7.5 (d, lH), 7.28 (d, lH), 6.8(s, 1H), 3.18(m, 6H), 2.42(m,4H), 1.98(m, 2H), 1.29(m, 9H).
8 ~ 8.63 (d, 2H), 7.48(s,IH), 7.46(m, 3H), 7.2 (d, IH), 3.15 (m, 6H), 2.43 (m, 4H), 1.98(m, 2H), 1.29 (m, 9H).
9 ~ 8.7(m,IH), 8.0(s,IH), 7.8 (d, IH), 7.72(m,lH), 7.70 (m,IH), 7.26(m, lH), 3.14(m, 6H), 2.45 (m, 4H),I.99(m, 2H), 1.26(m, 9H).
~ 7.8 (d, IH), 7.77 (s,IH), 7.6(d,IH), 7.3 (m,IH), 7.18(d,IH), 3.09(m, 6H), 2.45(m, 4H), 2.34 (s, 3H),I.99(m, 2H), 1.26(m, 9H).
Il ~ 7.88(m, 2H), 7.85 (m,IH), 7.33(s,IH), 7.16(d,lH), 2.71(m, 2H), 2.4 (m, 2H), 2.33(s, 3H), 2.0 (m, 2H).
12 ~ 8.8(s,IH), 8.6 (d, IH), 7.8 (dd, IH), 7.5 (s,lH), 7.4 (d, IH), 7.35 (m, lH), 7.24 (d, IH),3.21(m, 6H), 2.45(m, 4H),I.99(m, 2H), 1.28(m, 9H).
14 ~ 8.6 (d, IH), 8.55 (d, IH), 7.8 (d, IH), 7.5 (m, 3H), 3.0(m, 6H), 2.33(m, 4H), 1.8(m, 2H), 1.16(m, 9H).
19 ~ 8.6(m, 2H), 7.7(m,IH), 7.65(m,IH), 7.5(m,IH), 7.2(m,lH), 2.95(m, 6H), 2.9(m,lH), 2.3(m, 2H), 1.6(m, 2H), 1.13 (m, 9H), 0.95 (m, 6H).
21 ~ 8.47(m,lH), 8.44 (m,lH),7.8(m,IH), 7.73(m,lH), 7.7 (m,lH), 7.25 (m,IH), 2.6 (m,lH), 2.02(m, 2H), 0.92(m, 6H).
22 ~ 8.6(m, 2H), 8.0(m,IH), 7.77 (m,IH), 7.6(m,IH),7.4 (m,IH), 3.2-1.8 (m, 6H).
26 ~7.57 (d, IH), 7.1(s,lH), 6.1 (d,IH), 3.67 (s, 3H), 3.2-2.1(m,IOH), 1.73 (s, 3H), 1.29(t, 3H), 1.13 (d, 3H).
27 ~ 7.56(d,IH), 7.1(s,IH), 6.11(d,IH), 3.67 (s, 3H), 3.2-3.0(m, 2H), 2.82 (t, 2H), 2.74 (s, 3H), 2.42 (t, 2H), 2.14-2.0(m, 2H),1.74 (s, 3H), 1.29(t, 3H).

CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 29 ~8.7(m,2H),7.7-7.4(m,5H~,7.09(s,lH),3.9(q,2H),3.24(m,6H),1.35 (m,12H).

a IH NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (dd)-doublet of doublets, (t)-triplet, (q)-quartet, (m)-multiplet.

BIOLOGICAL EXAMPLES OF THE INVENTION
TEST A
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa ~rus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), 10 crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), 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 rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant.
At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and 20 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.

CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 Table A COMPOUND Table A COMPOUND
Rate 2000 g/ha 27 Rate 1000 g/ha 20 21 Preemergence Postemergence Barley 0 Barley 0 2 Barnyardgrass 0 Barnyardgrass 4 5 Bedstraw 0 Bedstraw 9 3 Blackgrass 0 Blackgrass 3 Chickweed 0 Chickweed 7 7 Cocklebur 0 Cocklebur 8 7 Corn 0 Corn Cotton 0 Cotton 9 3 Crabgrass 0 Crabgrass 2 3 Downy brome0 Downy brome 1 0 Giant foxtail 0 Giant foxtail 2 Lambsquarter 4 Lambsquarter 8 9 Morningglory 0 Morningglory 9 9 Nutsedge 0 Nutsedge - 0 Rape 0 Rape 9 9 Rice 0 Rice 0 2 Sorghum 0 Sorghum 3 0 Soybean 0 Soybean 8 5 Sugar beet 0 Sugar beet 7 10 Velvetleaf 0 Velvetleaf 9 10 Wheat 0 Wheat 0 Wild buckwheat 0 Wild buckwheat 2 5 Wild oat 0 Wild oat 0 0 CA 02257l96 l998-ll-30 W O 97/46S30 PCT~US97/09S69 Table A COMPOUND
Rate 1000 g/ha 20 21 Preemergence Barley 0 0 Barnyardgrass 0 0 Bedstraw 3 0 Blackgrass 1 0 Chickweed 3 5 Cocklebur 3 0 Corn 0 0 Cotton 2 0 Crabgrass 0 0 Downy brome0 0 Giant foxtail 0 0 Lambsquarter 9 10 Morningglory 6 2 Nutsedge 0 0 Rape 3 5 Rice 0 ~
Sorghum 0 0 Soybean 0 0 Sugar beet8 l0 Velvetleaf 8 7 Wheat 0 0 Wild buckwheat 0 0 Wild oat 0 0 CA 022~7l96 l998-ll-30 Table A COMPOUND
Rate 400 g/ha 12345678910111213141519222627 Postemergence Barley 2 8 855003100580101000 Barnyardgrass 910101010101096 8 9 9 9 9 lo 61091 Bedstraw 6 8 8 9 676 8 9 9 9 8 7 9 8 610 - 0 Blackgrass 36623121224350301020 Chickweed 7 8 9 7 8 4 5 7 8 7 8 8 9 9 9 9 lo 20 Cocklebur 9999 8 7 79688 8 9 lo 9 8 lo 30 Corn 46533033121320001011 Cotton 10647 8 45109 8 9 lC 9 9 lo 8931 Crabgrass 9109910559358993531050 Downy brome 06634002112 7 7 o 1 o 10 1 o Giant foxtail 9 7 7 8 8 30 8 24699332940 Lambsquarter 99999 7 8 9 9 9 9 9 9 9 9 8 lo 8 Morningglory 999 7 7 5 7 9 9 9 9 9 9 9 lo 9 lo 31 Nutsedge 3 ~ 20 - 325 7 8 - 8 o o Rape 99 8 7 7 8 lo 9 8 7 8 6 6 9 9 8 lo o Rice 9999920 8 259 8 lo 440940 Sorghum 7 8 8 6 443 8 433791201021 Soybean 5677423736 8 577 - 6722 Sugar beet 910101010699910910101010910101 Velvetleaf 10 8 9 9 9 891010101010101010101030 Wheat 37844003002680001030 Wild buckwheat 26876 5 8 9 6 7 7 lo 9 9 9 7 lo 70 Wild oat 3 8 9 4670434 5 4 5 0 o o lo 30 CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 Table A COMPOUND
Rate 400 g/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 19 22 26 27 Preemergence Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Barnyardgrass 1 0 0 0 0 0 3 0 0 0 2 0 2 1 8 2 8 0 0 Bedstraw - 0 5 0 0 0 0 0 0 0 4 0 1 6 7 0 9 - 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 9 o 0 Chickweed 0 0 4 0 0 0 0 2 0 1 0 2 0 8 9 4 9 0 0 Cocklebur 0 0 0 0 0 - 6 0 6 0 0 0 0 6 8 0 10 0 0 Corn 0 0 0 0 0 0 0 0 0 0 C 0 0 0 o 0 5 0 o Cotton 0 0 0 0 0 0 0 - 0 C 0 0 0 0 5 0 9 0 0 Crabgrass 7 9 3 3 4 6 4 6 0 1 0 5 4 3 3 0 10 0 0 Downy brome 0 0 0 0 0 0 0 3 0 0 0 0 3 0 3 0 9 0 0 Giant foxtail 1 0 0 0 0 0 0 1 0 0 0 0 0 0 0 2 2 0 0 Lambsquarter 7 9 9 9 9 6 5 9 8 7 8 9 9 10 10 8 10 6 0 Morningglory 0 0 0 0 0 0 0 2 0 0 0 0 2 7 8 0 10 0 0 Nutsedge 0 3 0 2 0 2 0 0 0 0 0 - 0 - 2 0 8 0 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 9 9 1 8 0 0 Rice 1 0 0 0 0 0 0 0 0 0 0 2 0 0 4 0 10 0 0 Sorghum 1 0 1 0 0 0 0 0 0 0 o 0 0 0 0 C 9 0 0 Soybean 0 0 0 0 0 0 0 3 o 0 0 0 C 0 3 0 9 o 0 Sugar beet 0 0 3 0 0 0 0 0 0 0 5 3 5 10 10 3 10 0 0 Velvetleaf 6 0 0 0 0 0 6 7 6 2 2 7 8 10 10 4 10 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 0 Wild buckwheat 0 0 0 3 0 0 0 2 0 0 0 0 0 7 8 0 7 0 0 Wild oat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 o 9 0 0 CA 022~7l96 l998-ll-30 W O 97/46530 PCTrUS97/09569 Table A COMPOUND Table A COMPOUND
Rate 200 g/ha 20 21 23 24 25 Rate 200 g/ha 20 21 23 24 25 Postemergence Preemergence Barley 0 0 9 9 10 Barley 0 0 1 2 0 Barnyardgrass 2 1 9 9 10 Barnyardgrass 0 0 9 10 9 Bedstraw 6 2 - - 9 Bedstraw 0 0 8 5 8 Blackgrass 0 0 7 10 10 Blackgrass 0 0 2 4 2 Chickweed 4 7 9 9 9 Chickweed 0 0 9 9 9 Cocklebur 8 6 10 10 9 Cocklebur - 0 4 5 5 Corn l 0 4 8 9 Corn 0 0 0 2 0 Cotton 7 2 10 10 9 Cotton 0 0 0 7 4 Crabgrass 2 0 9 9 10 Crabgrass 0 0 10 10 10 Downy brome 0 0 9 9 9 Downy brome 0 0 7 10 6 Giant foxtail 1 0 9 9 10 Giant foxtail 0 0 3 6 8 Lambsquarter 8 8 9 10 9 Lambsquarter 8 9 10 10 9 Morningglory 8 7 9 10 9 Morningglory 1 0 3 6 3 Nutsedge - 0 4 9 4 Nutsedge - - 0 0 7 Rape 4 8 10 10 10 Rape 0 0 5 7 8 Rice 0 0 9 9 10 Rice 0 0 6 9 6 Sorghum 1 0 9 9 10 Sorghum 0 0 7 9 3 Soybean 4 2 10 10 9 Soybean 0 0 5 9 4 Sugar beet 2 10 10 10 10 Sugar beet 0 0 10 10 10 Velvetleaf 9 8 10 7 9 Velvetleaf 1 2 9 10 10 Wheat 0 0 9 9 10 Wheat 0 0 3 5 Wild buckwheat 2 4 9 8 9 Wild buckwheat 0 0 0 2 0 Wild oat 0 0 10 10 10 Wild oat 0 0 8 7 8 CA 022~7l96 l998-ll-30 W O 97/46530 PCT~US97/09569 Table A COMPOUND
Rate 100 g/ha 123456789101112131415192226 Postemergence Barley 154000020002100090 BarnyardgrasS 8889109884489989199 Bedstraw 476842368876787290 Blackgrass 231210010112201092 Chickweed 5676504474577896102 Cocklebur 5973756556467997102 Corn 343010011111000050 Cotton 9545533692699993102 Crabgrass 798963572269922091 Downy brome 033120010014401090 Giant foxtail 344461061248711252 Lambsquarter 6999775988898996107 Morningglory 88865239999899107102 Nutsedge 021000 - 10 - 00065070 Rape 288567723471589780 Rice 6885800421322230102 Sorghum 4563200511223000 Soybean 355542232263554392 Sugar beet 31010895659883910109109 Velvetleaf 108856779991010109109101 Wheat 251020020004500090 Wild buckwheat 244154471158689395 Wild oat 246110022322201091 CA 022~7l96 l998-ll-30 ~able A COMPOUND
Rate 100 g/ha l 2 3 4 5 6 7 8 9 10 11 12 13 14 15 19 22 26 Preemergence Barley 0 0 0 0 G 0 0 0 0 0 0 0 o 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 2 9 0 Bedstraw - 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 9 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 0 Chickweed 0 0 2 0 0 0 0 0 0 1 0 0 0 7 9 C 9 0 Cocklebur 0 0 0 0 0 0 3 0 4 0 0 0 0 1 7 0 7 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cotton C 0 0 C 0 0 C C 0 o 0 0 0 C 0 0 3 o Crabgrass 2 0 0 0 0 0 1 2 0 0 0 0 2 0 1 0 10 0 Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 9 0 Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 Lambsquarter 6 8 8 7 7 0 0 9 0 4 6 0 8 10 10 8 10 4 Morningglory 0 0 0 0 0 - 0 0 0 0 0 0 0 6 2 0 8 0 Nutsedge - 0 0 0 0 0 - 0 0 0 0 - 0 - 0 0 1 0 Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 6 8 0 2 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 7 0 Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 Soybean 0 0 0 0 0 0 0 o 0 0 0 0 0 3 0 0 7 0 Sugar beet 0 0 0 0 0 0 0 0 0 0 0 0 2 10 10 0 10 0 Velvetleaf 0 0 0 0 0 0 0 6 3 0 0 0 3 9 10 4 10 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 6 0 Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 CA 022~7196 1998-11-30 W O 97/46530 PCT~US97/09569 Table A COMPOUND Table A COMPOUND
Rate 50 g/ha23 24 25 Rate S0 g/ha 23 24 25 Postemergence Preemergence Barley 78 8 Barley 0 0 0 Barnyardgrass9 9 10Barnyardgrass 3 3 2 Bedstraw 87 9 Bedstraw 6 - 1 Blackgrass 58 8 Blackgrass 1 1 0 Chickweed 89 8 Chickweed7 9 7 Cocklebur 9 109 Cocklebur0 - 0 Corn 27 8 Corn 0 0 0 Cotton 91010 Cotton 0 0 0 Crabgrass 49 9 Crabgrass1010 6 Downy brome 57 8 Downy brome 2 7 0 Giant foxtail7 8 9Giant foxtail 1 1 2 Lambsquarter 9 9 9Lambsquarter 9 9 9 Morningglory 9 9 9Morningglory 1 4 Nutsedge 28 1 Nutsedge - 0 Rape 97 10 Rape 3 4 7 Rice 99 9 Rice 0 3 2 Sorghum 99 10 Sorghum 0 2 0 Soybean 99 8 Soybean 0 7 0 Sugar beet 101010 Sugar beet 10 10 3 Velvetleaf 99 9 Velvetleaf 8 8 Wheat 79 9 Wheat 0 2 0 Wild buckwheat 2 3 2Wild buckwheat 0 1 0 Wild oat 84 10 Wild oat 2 3 0 ~ , . .

CA 022~7l96 l998-ll-30 W O 97146530 PCT~US97/09569 TEST B
The compounds evaluated in this test were form~ tecl in a non-phytotoxic solventmixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood 5 application)~ and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.
Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays v.Pioneer 3394), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). Additionally, two 10.3 cm pots each containing two plant of corn (Zea mays) of the varieties Ml7 and B73 were treated in 20 addition to the normal compliment of crop species.
All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of a~ropl.ate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus diJj~ormis), duck salad 25 (Heteranthera limosa), barnyardgrass2 (Echinochloa crus-galli) and Late watergrass (Echinochloa oryzicola grown to the 2 leaf stage for testing.
All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant 30 response ratings, summarized in Table B, were recorded on a 0 to lO0 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

. .

CA 022~7196 1998-11-30 Table B COMPOUND Table B COMPOUND
Rate 500 g/ha 1Rate 500 g/ha POSTEMERGENCE PREEMERGENCE
Barley Igri 0Barley Igri 0 Barnyard 265 Barnyardgrass 60 Barnyardgrass 90 Bedstraw 50 Bedstraw 80 Blackgrass0 Blackgrass20 Chickweed30 Chickweed90 Cocklebur 0 Cocklebur70 Corn 0 Corn 0 Cotton 0 Corn (B73) - Crabgrass80 Corn (M17) - Downy Brome 0 Cotton 50 Giant foxtail 50 Crabgrass90 Italn. Rygrass 0 Downy Brome 10Johnsongrass 0 Duck salad60 Lambsquarter 90 Giant foxtail 90Morningglory 0 Italn. Rygrass 10 Rape 20 Johnsongrass 60 Redroot Pigweed 0 Lambsquarter 90 Soybean 0 Morningglory 90 Speedwell60 Rape 70 Sugar beet30 Redroot Pigweed 70 Velvetleaf90 Rice Japonica 25 Wheat 0 Soybean 40 Wild buckwheat 0 Speedwell 70 Wild oat 0 Sugar beet 70 Umbrella sedge 80 Velvetleaf 90 Wheat 30 Wild buckwheat 50 Wild oat 50 CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 Table B COMPOUND Table B COMPOUND
Rate 250 g/ha 1 5 6 26 Rate 250 g/ha 1 5 POSTEMERGENCE PREEMERGENCE
Barley Igri0 15 - - Barley Igri0 0 Barnyard 245 20 10 0 Barnyardgrass 20 0 Barnyardgrass 80 95 - -Bedstraw 0 0 Bedstraw70 90 - - Blackgrass0 0 Blackgrass20 15 - - Chickweed0 10 Chickweed80 90 - - Cocklebur0 20 Cocklebur70 70 - - Corn 0 0 Corn 0 15 - - Cotton 0 0 Corn (B73)- 65 _ _ Crabgrass60 35 Corn ~M17)- 60 - - Downy Brome0 0 Cotton50 50 - - Giant foxtail 20 10 Crabgrass90 90 - - Italn. Rygrass 0 0 Downy Brome0 15 - - Johnsongrass 0 0 Duck salad50 20 0 0 Lambsquarter 70 80 Giant foxtail 80 80 - -Morningglory 0 0 Italn. Rygrass 0 0 - - Rape 0 0 Johnsongrass 60 50 - -Redroot E~gweed 0 40 Lambsquarter 90 90 - -Soybean 0 0 Morningglory 80 40 - -Speedwell 50 10 Rape 60 50 - - Sugar beet0 60 Redroot Pigweed 70 90 - -Velvetleaf 70 20 Rice Japonica 10 0 0 0Wheat 0 0 Soybean40 40 - - Wild buckwheat 0 0 Speedwell- 10 - - Wild oat 0 0 Sugar beet70 90 Umbrella sedge 70 30 30 0 Velvetleaf90 80 Wheat 20 10 Wild buckwheat 50 70 Wild oat 30 20 CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table B COMPOUND
Rate 125 g/ha 1 5 6 12 13 14 15 22 23 26 POSTEMERGENCE
Barley Igri0 0 - 0 0 00 100 70 Barnyard 220 10 0 0 10 00 95 20 0 Barnyardgrass70 90 - 90 9080 90 100 90 Bedstraw 30 80 -20 98 5070 95 85 Blackgrass10 10 - 0 10 100 95 60 Chickweed 70 80 -10 40 60 95 100 100 Cocklebur 50 60 -70 70 80 90 100 100 Corn 0 10 - 0 0 0 0 30 0 Corn (B73) - 40 -60 60 10 5 Corn (M17) - 30 - 0 25 0 5 - - -Cotton 40 40 -70 90 30 90 100 90 Crabgrass 70 80 -90 90 35 5090 100 Downy Brome0 10 - 0 98 0 0 - 50 Duck salad40 0 050 40 50 7080 90 0 Giant foxtail70 50 - 75 70 40 50 90 100 Italn. Rygrass0 0 - 0 0 0 30 85 70 Johnsongrass 30 30 - 50 50 0 70 100 100 Lambsquarter 70 90 - 90 90 90 100 100 100 Morningglory 80 40 - 70 80 90 90 100 90 Rape 30 20 -30 0 90 100 - 100 Redroot Pigweed 7090 - 70 70 90 95 100 100 Rice Japonica 0 0 0 10 0 0 10 95 30 0 Soybean 20 30 -50 50 40 50 90 90 Speedwell 50 0 - 0 20 80 90 100 Sugar beet30 80 -20 - 90 90 100 Umbrella sedge601020 60 70 50 60 50 85 0 Velvetleaf90 60 - 1009090 100 100 95 Wheat 0 0 - 0 00 0 100 80 Wild buckwheat20 40- 60 98 90 90 70 50 Wild oat 30 0 - 0 00 0 100 80 . _ . . ....

CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table B COMPOUND
Rate 125 g/ha 1 512 13 14 15 22 23 PREEMERGENCE
Barley Igri0 0 0 0 10 10 0 0 Barnyardgrass 0 0 0 0 020 100 50 Bedstraw 0 0 -20 3035 10050 Blackgrass 0 0 0 0 00 30 20 Chickweed 0 0 070 7090 10080 Cocklebur 0 0 0 0 030 90 30 Corn o 0 0 0 00 0 o Cotton 0 0 10 0 0 100 90 50 Crabgrass 35 0 7060 030 100 100 Downy Brome0 0 0 0 1020 100 0 Giant foxtail10 035 20 0 10 35 75 Italn. Rygrass0 0 0 0 0 0 80 10 Johnsongrass 0 030 0 0 40 100 60 Lambsquarter 40 40 3095 100 95 100 100 Morningglory 0 010 0 10 20 100 60 Rape 0 0 0 0 3080 0 35 Redroot Pigweed 030 30 10 60 70 - 95 Soybean 0 0 0 0 010 80 30 Speedwell 50 0 7070 90 100 100 100 Sugar beet 0 60 30 10 100 100 100 100 Velvetleaf40 030 100 100 100 100 100 Wheat 0 00 0 15 0 0 0 Wild buckwheat0 0 0 0 0 60 40 0 Wild oat 0 00 10 0 10 0 10 .

CA 022~7l96 l998-ll-30 W 097/46530 PCT~US97/09569 Table B COMPOUND
Rate 62 g/ha 1 5612 13 14 1522 2324 26 POSTEMERGENCE
Barley Igri0 0 - 0 0 0 0 8560 50 Barnyard 210 0 00 0 0 0 3510 100 Barnyardgrass60 80 - 70 90 50 70 100 90 100 Bedstraw 3070 - 098 3070 85 - 75 Blackgrass1010 - 0 0 00 95 50 70 Chickweed 6070 - 030 60 90 100 100 90 Cocklebur 2060 -2070 8090 10095 90 Corn 0 0 - 0 0 00 20 0 55 Corn (B73~ -15 -4050 5 5 - - - -Corn (M17) -20 - 0 5 0 0 Cotton 030 -3030 2080 10090 95 Crabgrass 5080 -9080 15 3090 100 95 Downy Brome0 0 - 0 0 0 095 40 60 Duck salad10 0 -20 0 30 4070 80 90 0 Giant foxtail40 40 - 50 50 0 30 65 100 90 Italn. Rygrass 00 - 0 0 0 0 60 50 60 ~ohnsongrass10 20 - - 30 0 50 100 100 90 Lambsquarter30 80 - 80 90 90 95 100 90 95 Morningglory40 30 - 30 40 90 90 100 90 90 Rape 20 0 - 0 0 70 90 - 100 100 Redroot Plgweed 5080 - 50 30 90 90 100 90 90 Rice Japonica0 00 0 0 0 0 95 20 30 0 Soybean 030 -4035 4040 90 90 90 Speedwell 50 0 - 020 5080 100 80 100 Sugar beet 070 - 0 - 9090 100 - 90 Umbrella sedge 20 0 0 30 20 30 50 50 70 80 0 Velvetleaf8050 - 100 80 9090 100 95 95 Wheat 0 0 - 0 o 00 9o 70 70 Wild buckwheat 10 0- 10 98 70 80 70 40 70 Wild oat 20 0 - 0 0 00 100 60 60 . . ~ . .

CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table B COMPOUND
Rate 62 g/ha 1 512 13 1415 22 23 24 PREEMERGENCE
Barley Igri0 0 0 0 10 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 70 20 50 Bedstraw 0 0 0 0 020 10040 85 Blackgrass 0 0 0 0 00 30 0 20 Chickweed 0 0 0 - 2070 10080 100 Cocklebur 0 0 0 0 0- 5030 30 Corn 0 0 0 o 00 o 0 0 Cotton 0 0 o 0 050 9030 30 Crabgrass 20 0 5040 020 100 100 100 Downy Brome0 0 0 0 00 100 0 25 Giant foxtail 0 025 0 0 0 15 60 70 Italn. Rygrass0 0 0 0 0 0 70 10 10 Johnsongrass 0 020 0 0 10 50 60 60 Lambsquarter 40 20 3010 100 95 100 100 100 Morningglory 0 0 0 0 010 80 50 70 Rape 0 0 0 0 030 00 10 Redroot Pigweed 020 20 0 30 40 - 90 100 Soybean 0 0 0 0 0o 700 30 Speedwell - 0 50 - 8090 10060 100 Sugar beet 0 20 .00 100 100 100 100 100 Velvetleaf20 0 2030 40 100 100 100 100 Wheat 0 0 00 10 0 0 0 20 Wild buckwheat0 0 0 0 0 30 30 0 10 Wild oat 0 0 0 0 0 0 0 0 10 CA 022~7l96 l998-ll-30 WO 97/46530 ~CT/US97/09569 Table B COMPOUND
Rate 31 g/ha 1 56 12 1314 15 22 2324 25 26 POSTEMERGENCE
Barley Igri - 0 - o 0 0 C 75 50 400 Barnyard 2 00 00 0 0 0 0 0 1030 0 Barnyardgrass - 70 - 6070 20 50 100 90 95 90 Bedstraw -30 - 0 - 1050 80 60 7560 Blackgrass - 0 - o 0 0 0 75 30 7030 Chickweed -50 - 0 20 6080100 - 9090 Cocklebur -40 - - 20 8085100 95 9090 Corn - 0 - ~ ~ ~ ~ ~ ~ 4030 Corn (B73) -10 -10 5 5 5 - - _30 Corn (M17) -10 - 0 0 0 o - - -30 Cotton -20 -10 20 050 95 90 90100 Crabgrass -60 -80 70 1030 90 90 9090 Downy Brome - 0 - 0 0 0 0 75 30 600 Duck salad 00 00 0 010 45 60 7020 0 Giant foxtail - 40 - 3530 0 20 5090 80 90 Italn. Rygrass - 0 - 0 0 0 0 6040 50 0 Johnsongrass - 15 - -20 0 30 80100 90 80 Lambsquarter - 70 - 8080 90 90 100 90 95 90 Morningglory - 30 - 2040 70 90 9090 90 go Rape - 0 - 0 0 7080 - 80 9090 Redroot Pigweed -80 - 3020 80 90 9590 90 100 Rice Japonica0 00 0 0 0 0 15 1020 0 0 Soybean -15 -20 30 3535 90 80 9070 Speedwell - 0 - 0 0 5080100 80 90100 Sugar beet -70 - 0 98 8080100 - 9090 Umbrella sedge 00 0 10 0 0 30 5050 70 20 0 Velvetleaf -30 -90 80 8090100 90 9080 Wheat - 0 - 0 0 0 0 85 50 6020 Wild buckwheat - 0 - 098 70 50 6030 70 10 Wild oat - 0 - 0 0 0 0 7040 40 90 CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table B COMPOUND
Rate 31 g/ha 5 1213 14 1522 23 24 25 PREEMERGENCE
Barley Igri0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 015 0 10 0 Bedstraw 0 0 0 0 0 6030 70 30 Blackgrass 0 0 0 0 0 20 0 10 0 Chickweed 0 0 102070 10040 95 50 Cocklebur 0 0 0 0- 10 10 0 Corn 0 0 0 00 0 o 0 o Cotton 0 - 0 030 60 30 20 0 Crabgrass 0 30 10 010 100- 100 40 Downy Brome0 0 0 00 0 0 0 20 Giant foxtail 0 10 0 0 0 0 0 30 10 Italn. Rygrass0 0 0 0 0 40 0 0 0 Johnsongrass 0 10 0 0 0 20 30 40 0 Lambsquarter 0 20 0 100 95 100 100 100 100 Morningglory 0 0 0 0 0 30 50 60 0 Rape 0 0 0 020 - 0 0 0 Redroot Pigweed 1010 0 0 20 - 70 85 0 Soybean 0 0 0 00 600 30 0 Speedwell 0 - 60 -90 10060 10020 Sugar beet20 10 070 100 100 70 90 70 Velvetleaf 0 10 100 40 10070 90 0 Wheat 0 0 010 0 0 0 0 0 Wild buckwheat0 0 00 0 0 0 0 0 Wild oat 0 0 0 0 0 00 0 0 CA 022~7l96 l998-ll-30 Table B COMPOUND
Rate 16 g/ha 12 1314 15 22 2324 25 POSTEMERGENCE
Barley Igri0 0 0 0 45 30 30 0 Barnyard 2 0 0 0 0 0 0 020 Barnyardgrass40 20 0 30 90 9095 90 Bedstraw 0 - 1040 75 60 4060 Blackgrass 0 0 0 0 70 30 3520 Chickweed 0 0 5060100 80 8080 Cocklebur 10 0 7080 95 90 9080 Corn 0 0 0 0 0 0 2510 Corn (B73) 0 0 5 5 - - - 20 Corn (M17) 0 0 0 0 - - - 10 Cotton 10 0 030 95 80 8550 Crabgrass 60 70 020 80 80 8590 Downy Brome0 0 0 0 70 30 30 0 Duck salad 0 0 0 0 25 10 50 0 Giant foxtail30 20 0 0 40 8060 85 Italn. Rygrass0 0 0 0 40 3050 0 Johnsongrass - 20 0 30 70 8080 60 LambscIuarter50 6080 80100 8590 70 Morningglory 10 2050 80 90 gO90 go Rape 0 0 4070 - 60 5090 Redroot Pigweed 020 70 80 9090 80 80 Rice Japonica 0 0 0 0 0 010 0 Soybean 20 20 3020 90 80 9060 Speedwell 0 0 -50 95 50 7070 Sugar beet 0 98 8080100 - 9080 Umbrella sedge0 0 0 10 15 3560 0 Velvetleaf80 80 8090100 90 9070 Wheat 0 0 0 0 70 35 5010 Wild buckwheat0 9840 50 45 2020 0 Wild oat 0 0 0 0 60 20 3060 .. . . .. .

CA 022~7l96 l998-ll-30 W 097/46530 PCT~US97/09569 Table B COMPOUND
Rate 16 g/ha 12 1314lS 2223 24 25 PREEMERGENCE
Barley Igri0 0 00 0 0 0 0 Barnyardgrass 0 00 0 C 0 0 0 Bedstraw 0 0 00 20 20S0 0 Blackgrass 0 0 00 20 0 0 0 Chickweed 0 10 0 60 10020 90 40 Cocklebur 0 0 0 - o 0 0 0 Corn 0 0 0 o 0 0 0 0 Cotton 0 0 0 20 30 10 - 0 Crabgrass 20 0 0 10 100 80 70 40 Downy Brome 0 0 0 0 0 0 0 0 Giant foxtail 0 0 0 0 o 0 0 Italn. Rygrass 0 0 0 0 0 0 0 0 Johnsongrass 10 0 0 0 10 0 10 0 ~ambsquarter 0 0 80 9S 100 30 9S 60 Morningglory 0 0 0 0 30 - 50 0 Rape 0 0 0 o - 0 o 0 Redroot Pigweed 0 0 010 -S0 70 0 Soybean 0 0 00 40 0 0 0 Speedwell 30 608090 100 090 20 Sugar beet 0 03090 10050 0 40 Velvetleaf 0 0 030 1006070 0 Wheat 0 0 00 0 0 C 0 Wild buckwheat 0 0 0 0 0 0 0 0 Wild oat 0 0 0 0 0 0 0 0 CA 022~7l96 l998-ll-30 Table BCOMPOUND Table B COMPOUND
Rate 8 g/ha24 25 Rate 8 g/ha 24 25 POSTEMERGENCE PREEMERGENCE
Barley Igri30 0 Barley Igri 0 0 Barnyard 20 0 Barnyardgrass 0 0 Barnyardgrass 90 85Bedstraw 0 0 Bedstraw - 40 Blackgrass0 0 Blackgrass35 20 Chickweed80 0 Chickweed70 80 Cocklebur0 0 Cocklebur90 80 Corn 0 0 Corn 15 0 Cotton 20 0 Corn (B73)l0 Crabgrass50 20 Corn (Ml7)- 0 Downy Brome 0 0 Cotton 70 40 Giant foxtail 0 0 Crabgrass75 80 Italn. Rygrass 0 0 Downy Brome30 0 Johnsongrass 0 0 Duck salad20 0 Lambsquarter 95 40 Giant foxtail 40 75Morningglory l0 0 Italn. Rygrass 40 0 Rape 0 C
Johnsongrass 70 60Redroot Pigweed 70 0 Lambsquarter 60 70Soybean 0 0 Morningglory 85 90Speedwell 90 0 Rape 40 80 Sugar beet0 0 Redroot Pigweed 60 60Velvetleaf 40 0 Rice Japonica l0 0 Wheat o 0 Soybean90 60 Wild buckwheat 0 0 Speedwell70 70 Wild oat0 0 Sugar beet90 70 Umbrella sedge 40 0 Velvetleaf 75 40 Wheat 35 0 Wild buckwheat l0 0 Wild oat 20 40 ~ . .

CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table B COMPOUND Table B COMPOUND
Rate 4 g/ha 25 Rate 4 g/ha 25 POSTEMERGENCE PREEMERGENCE
Barley Igri0 Barley Igri 0 Barnyard 2 0 Barnyardgrass 0 Barnyardgrass 80 Bedstraw 0 Bedstraw 30 Blackgrass 0 Blackgrassl0 Chickweed 0 Chickweed 70 Cocklebur 0 Cocklebur 75 Corn 0 Corn 0 Cotton 0 Corn (B73)l0 Crabgrass 0 Corn (Ml7) 0 Downy Brome 0 Cotton 30 Giant foxtail 0 Crabgrass 70 Italn. Rygrass 0 Downy Brome0 Johnsongrass 0 Duck salad 0 Lambsquarter 30 Giant foxtail 60 Morningglory 0 Italn. Rygrass 0 Rape 0 Johnsongrass 30 Redroot Pigweed 0 Lambsquarter 65 Soybean 0 Morningglory 70 Speedwell 0 Rape 80 Sugar beet 0 Redroot Pigweed 60 Velvetleaf 0 Rice Japonica 0 Wheat 0 Soybean 40 Wild buckwheat 0 Speedwell 60 Wild oat 0 Sugar beet60 Umbrella sedge 0 Velvetleaf30 Wheat 0 Wild buckwheat 0 Wild oat l0 CA 022~7l96 l998-ll-30 W O 97146530 PCT~US97/09569 TEST C
Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica Rice (Oryza sativa) seed or seedlings at the 2.0 to 3.5 leaf stage; seeds, tubers 5 or plant parts selected from arrowhead (Sagi~taria rigida), barn~ardgrass (Echinochloa crus-galli), (l~lck~ d (Heteranthera limosa), early watergrass (Echinochloa oryzoides), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola), redstem (Ammania species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis) and tighthead sprangletop (Leptochloa fasicularis), were planted into this soil. Plantings and 10 waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the two leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied directly to the paddy water, by pipette, or to the plant foliage, by an ~ir-pressure assisted, 15 calibrated belt-conveyer spray system.
Treated plants and controls were maintained in a greenhouse for approximately 21days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table C COMPOUND Table C COMPOUND
Rate 375 g/ha 13 15 Rate 250 g/ha 13 15 PD/TA PD/TA
ducksalad 85 98 ducksalad 70 95 early watergras - 20 early watergras 20 20 junglerice 15 20 junglerice 10 25 late watergrass 0 0 late watergrass 0 redstem 100 100 redstem 95 100 rice flatsedge 80 80 rice flatsedge 75 45 smallflower fla 80 95 smallflower fla 75 95 tighthead spran 95 20 tighthead spran 95 30 2 LF barnyard g 30 15 2 LF barnyard g 15 15 2 LF direct see 10 15 2 LF direct see 0 15 2 LF transp. in 15 15 2 LF transp. in 0 15 ~ .

CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table C COMPOUND Table C COMPOUND
Rate 125 g/ha13 15 23 25 Rate 64 g/ha13 1523 25 PD/TA PD/TA
ducksalad 65 85 100 85 ducksalad 75 7598 85 early watergras 015 - 25early watergras 0 15 - 15 junglerice 0 4075 10 junglerice 0 1030 0 late watergrass 020 0 10late watergrass 0 - 0 10 redstem 95 9898 98 redstem 85 8560 90 rice flatsedge 7035 60 65rice flatsedge 75 35 20 40 smallflower fla 70 85 100 95smallflower fla 75 75 100 85 tighthead spran 90 25 98 75tighthead spran 80 40 95 65 2 LF barnyard g 0 15 0 102 LF barnyard g 0 15 0 0 2 LF direct see 0 15 100 252 LF direct see 0 15 10 10 2 LF transp. in 10 10 60 302 LF transp. in 0 0 10 25 Table C COMPOUND Table C COMPOUND
Rate 32 g/ha1315 23 25 Rate 16 g/ha23 25 PD/TA PD/TA
ducksalad 650 8 20 ducksalad 95 10 early watergras 0 0 - 0 early watergras - 0 junglerice 0 0 15 0 junglerice 25 0 late watergrass 0 0 0 0 late watergrass 0 0 redstem 200 30 20 redstem 30 20 rice flatsedge 60 35 10 40rice flatsedge 5 40 smallflower fla60 0 100 10smallflower fla 95 10 tighthead spran80 40 95 75tighthead spran 95 60 2 LF barnyard g 0 0 0 02 LF barnyard g 0 0 2 LF direct see 0 10 0 152 LF direct see 0 10 2 LF transp. in 0 0 o 202 LF transp. in C 10 CA 022~7l96 l998-ll-30 W O 97/46530 PCTrUS97/09569 Table C COMPOUND
Rate 8 g/ha 23 25 PD/TA
ducksalad 0 0 early watergras - 0 junglerice 0 0 late watergrass 0 0 redstem 0 20 rice flatsedge 0 0 smallflower fla 10 0 tighthead spran 40 0 2 LF barnyard g 0 0 2 LF dlrect see 0 10 2 LF transp. in 0 0 TEST D
Seeds, tubers, or plant parts of alexandergrass (Brachiaria plantaginea), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria platyphylla), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hirsutum), dallisgrass (Paspalum dilnt~ n), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (~ottboellia eYaltat(7), johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanuts (Arachis hypogaea), pitted morningglory 10 (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), and surinam grass (Brachiaria decumbens) were planted into greenhouse pots of flats containing greenhouse planting medium. Plant species were grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part. Postemergence applications were applied 15 when the plants were in the two to four leaf stage (three to twenty cm).
Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury 13 to 21 days after herbicide application. Plant response ratings, summarized in Table D, are 20 based on a 0 to 100 scale where 0 is no injury and lO0 is complete control. A dash (-) response means no test result.

CA 022~7196 1998-11-30 Table D COMPOUND Table D COMPOUND
Rate 250 g/ha 22 23 25 Rate 250 g/ha 22 23 25 POSTEMERGENCE PREEMERGENCE
Alexandergrass80 75 95Al~n~rgrass 100 100 100 BermudagraSS 80 60 80Bermudagrass 100 100 100 Brdlf Sgnlgrass g0 95 100 Brdlf Sgnlgrass 100 100 10 Cmn Purslane 80 60 75Cmn Purslane 100 100 100 Cmn Ragweed 50 - 60 Cmn Ragweed - - 100 Cotton 9040 - Cotton100 40 10 Dallisgrass 857535 Dallisgrass 100 98 70 Goosegrass 805095 Goosegrass 100 - 100 Guineagrass 809075 Guineagrass 100 100 50 Itchgrass 10 - 35 Itchgrass40 - 5 Johnson grass 90 95 100Johnson grass 98 100 75 Large Crabgrass65 100 25 Large Crabgrass 100 100 100 Peanuts 65 - 90 Peanuts50 20 55 Pit Morninglory 80 90 30 Pit Morninglory 95 100 10 Purple Nutsedge 75 50 20 Purple Nutsedge 75 0 0 Sandbur 607520 Sandbur98 80 45 Sourgrass 805075 Sourgrass100 100 100 Surinam grass80 75 90 Surinam grass 100 100 98 CA 022~7l96 l998-ll-30 W 097/46530 PCTrUS97/09569 Table D COMPOUND Table D COMPOUND
Rate 125 g/ha 22 23 25 Rate 125 g/ha 22 23 25 POSTEMERGENCE PREEMERGENCE
Alexandergrass 80 75 95 Alexandergrass 100 90 35 Bermudagrass 85 60 85 Bermudagrass 98 100 100 Brdlf Sgnlgrass 80 98 100 Brdlf Sgnlgrass 98 95 0 Cmn Purslane 70 30 75 Cmn Purslane 60 100 100 Cmn Ragweed 50 - - Cmn Ragweed - - 100 Cotton 95 350 Cotton 6510 10 Dallisgrass85 750 Dallisgrass10098 0 Goosegrass85 35 - Goosegrass100- 100 Guineagrass80 9575 Guineagrass9898 40 Itchgrass 5 350 Itchgrass 35 - 5 Johnson grass 80 90 100 Johnson grass 65 100 10 Large Crabgrass70 100 - Large Crabgrass 100 100 100 Peanuts 65 5090 Peanuts - - 10 Pit Morninglory 80 90 30 Pit Morninglory 80 90 10 Purple Nutsedge 75 30 10 Purple Nutsedge - 0 0 Sandbur 40 7520 Sandbur 98 95 0 Sourgrass 80 6020 Sourgrass 100 100 100 Surinam grass 9075 90 Surinam grass 100 90 45 CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 Table DCOMPOUND Table D COMPOUND
Rate 64 g/ha 22 23 25Rate 64 g/ha 22 23 25 POSTEMERGENCE PREEMERGENCE
Alexandergrass 80 65 l00Al~ndergrass 40 0 0 Bermudagrass 75 50 75Bermudagrass l00 l00 75 Brdlf Sgnlgrass 95 95 80Brdlf Sgnlgrass 95 0 0 Cmn Purslane 65 30 75Cmn Purslane 40 65 l00 Cmn Ragweed- - - Cmn Ragweed - - 98 Cotton90 35 0 Cotton25 0 0 DallisgraSS85 75 0 Dallisgrass 98 50 0 Goosegrass70 35 90 Goosegrass- - l00 Guineagrass75 80 35 Guineagrass 65 35 0 Itchgrass0 0 0 Itchgrass0 0 5 Johnson grass 80 80 l00Johnson grass - l0 0 Large Crabgrass 60 50 0 Large Crabgrass l00 80 l00 Peanuts 35 65 75 Peanuts l00 0 5 Pit Morninglory75 90 30Pit Morninglory 65 75 0 Purple Nutsedge75 20 l0Purple Nutsedge 20 0 0 Sandbur 20 0 20 Sandbur 30 0 0 Sourgrass 70 40 20Sourgrass l0098 98 Surinam grass8065 -Surinam grass9835 0 CA 022~7196 1998-11-30 W 097/46530 PCT~US97/09569 Table DCOMPOUND Table D COMPOUND
Rate 32 g/ha 22 25Rate 32 g/ha 22 25 POSTEMERGENCE PREEMERGENCE
Al~n~ergrass 40 90 Alexandergrass 0 0 Bermudagrass 65 50 Bermudagrass 50 0 Brdlf Sgnlgrass 80 35 Brdlf Sgnigrass 0 0 Cmn Purslane 30 75Cmn Purslane 20 70 Cmn Ragweed- - Cmn Ragweed - l0 Cotton 75 0 Cotton 25 0 Dallisgrass70 0 Dallisgrass 60 0 Goosegrass40 90 Goosegrass- 40 Guineagrass65 20 Guineagrass l0 5 Itchgrass 0 - Itchgrass0 0 Johnson grass 75 l00Johnson grass 90 0 Large Crabgrass 65 0Large Crabgrass 65 40 Peanuts35 50 Peanutsl00 5 Pit Morninglory 75 20Pit Morninglory 65 l00 Purple Nutsedge 65 0 Purple Nutsedge - 0 Sandbur 20 l0 Sandbur 0 0 Sourgrass 60 - Sourgrass 98 85 Surinam grass 65 75Surinam grass 0 0 CA 022~7l96 l998-ll-30 W O 97/46530 PCT~US97/09569 Table DCOMPOUND Table D COMPOUND
Rate 16 g/ha 22Rate 16 g/ha 22 POSTEMERGENCE PREEMERGENCE
Alexandergrass 35 Alexandergrass 0 Bermudagrass 50 Bermudagrass 50 Brdlf Sgnlgrass 40 Brdlf Sgnlgrass 0 Cmn Purslane 30Cmn Purslane 0 Cmn Ragweed - Cmn Ragweed Cotton 70 Cotton 0 Dallisgrass35 Dallisgrass 50 Goosegrass30 Goosegrass Guineagrass35 Guineagrass 0 Itchgrass 20 Itchgrass 0 Johnson grass 35Johnson grass 30 Large Crabgrass 50 Large Crabgrass 20 Peanuts 0 Peanuts 0 Pit Morninglory 65 Pit Morninglory 0 Purple Nutsedge 5 Purple Nutsedge 0 Sandbur 0 Sandbur 0 Sourgrass 35 Sourgrass 90 Surinam grass 35Surinam grass 0 CA 022~7196 1998-11-30 W O 97146530 PCTrUS97109569 Table DCOMPOUND Table D COMPOUND
Rate 8 g/ha 22 Rate 8 g/ha 22 POSTEMERGENCE PREEMERGENCE
Alexandergrass 35 Alexandergrass 0 Bermudagrass 40 Bermudagrass 0 Brdlf Sgnlgrass 70 Brdlf Sgnlgrass 0 Cmn Purslane 35Cmn Purslane 0 Cmn Ragweed - Cmn Ragweed Cotton 0 Cotton 0 Dallisgrass20 Dalllsgrass 50 Goosegrass30 Goosegrass Guineagrass35 Guineagrass 0 Itchgrass 0 Itchgrass0 Johnson grass 35Johnson grass Large Crabgrass 35 Large Crabgrass 0 Peanuts 0 Peanuts 0 Pit Morninglory 35 Pit Morninglory 0 Purple Nutsedge 0 Purple Nutsedge 0 Sandbur 0 Sandbur 0 Sourgrass 35 Sourgrass 90 Surinam grass 35Surinam grass 0 CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 TEST E
Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black night.ch~de (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), corn (Zea mays v.
S Pioneer 3394), corn2 (Zea mays v. IMR Ciba 4393), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), 10 signalgrass (Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), soybean (Glycine max v. Williams 95) and soybean2 (Glycine max v. Asgrow 3304), sunflower (~lelianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a sandy loam or clay loam soil. These crops and 15 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 treated in this fashion were placed in the greenhouse and m~int~ined according to routine greenhouse procedures.
Treated plants and untreated controls were maintained in the greenhouse 20 approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table E, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control.

CA 022~7l96 l998-ll-30 Table E COMPOUND Table E COMPOUND
Rate 140 g/ha 23 Rate 70 g/ha 23 POSTEMERGENCE POSTEMERGENCE
Barnyardgrass 80 Barnyardgrass 100 Bindweed 70 Bindweed 60 Blk Nightshade 100 Blk Nightshade 100 Cassia 55 Cassia 50 Cocklebur100 Cocklebur100 Corn 15 Corn 10 Corn2 20 Corn2 15 Cotton 70 Cotton 60 Crabgrass70 Crabgrass60 Fall Panicum 90Fall Panicum 80 Giant Foxtail 65Giant Foxtail 60 Green Foxtail 55Green Foxtail 55 Jimsonweed100 Jimsonweed 85 Johnson Grass 85Johnson Grass 85 Lambsquarter 90Lambsquarter 85 Morningglory 90Morningglory 85 Nutsedge 25 Nutsedge 0 Pigweed 75 Pigweed 70 Prickly Sida 50Prickly Sida 30 Ragweed 100 Ragweed100 Shattercane 80Shattercane 70 Signalgrass 85Signalgrass 80 Smartweed100 Smartweed100 Soybean 85 Soybean 85 Soybean2 80 Soybean280 Sunflower100 Sunflower100 Velvetleaf85 Velvetleaf 75 Wild Proso85 Wild Proso 85 Woolly cupgrass 65 Woolly cupgrass 60 Yellow Foxtail 65 Yellow Foxtail 55 CA 022~7l96 l998-ll-30 Table E Table E Table E
COMPOUND COMPOUND CO~POUND
Rate 35 g/ha 23Rate 17 g/ha 23Rate 8 g/ha 23 POSTEMERGENCE POSTEMERGENCE POSTEMERGENCE
Barnyardgrass 75Barnyardgrass 35Barnyardgrass 20 Bindweed 50 Bindweed 50 Bindweed 50 Blk Nightshade 100Blk Nightshade 100 Blk Nightshade 65 Cassia 45 Cassia 15 Cassia 10 Cocklebur100 Cocklebur75 Cocklebur 45 Corn 0 Corn 0 Corn 0 Corn2 15 Corn2 15 Corn2 0 Cotton 60 Cotton 55 Cotton 55 Crabgrass60 Crabgrass55 Crabgrass 55 Fall Panicum 70Fall Panicum 65Fall Panicum 55 Giant Foxtail 55Giant Foxtail 30Giant Foxtail 25 Green Foxtail 40Green Foxtail 20Green Foxtail 0 Jimsonweed80 Jimsonweed70 Jimsonweed45 Johnson Grass 80Johnson Grass 80Johnson Grass 55 Lambsquarter 85Lambsquarter 80Lambsquarter 75 Morningglory 85Morningglory 75Morningglory 60 Nutsedge 0 Nutsedge 0 Nutsedge 0 Pigweed 60 Pigweed 60 Pigweed 15 Prickly Sida 20Prickly Sida 15Prickly Sida 15 Ragweed 85 Ragweed 80 Ragweed 65 Shattercane 50Shattercane 30Shattercane 0 Signalgrass 80Signalgrass 75Signalgrass 65 Smartweed100 Smartweed75 Smartweed 60 Soybean 80 Soybean 75 Soybean 65 Soybean2 80 Soybean2 80 Soybean2 75 Sunflower85 Sunflower70 Sunflower 55 Velvetleaf70 Velvetleaf60 Velvetleaf55 Wild Proso75 Wild Proso65 Wild Proso60 Woolly cupgrass 55 Woolly cupgrass 45 Woolly cupgrass 40 Yellow Foxtail 50Yellow Foxtail 0Yellow Foxtail 0 CA 022~7196 1998-ll-30 TEST F
Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were grown for various periods of time before tre~tm~nt (postemergence application). A mixture of sandy loam soil 5 and greenhouse potting rnix in a 60:40 ratio was used for the postemergence test.
Plantings of these crops and weed species were adjusted to produce plants of applopliate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include arrowleaf sida (Sida rhombifolia), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common 10 lambsquarters (Chenopodium album), corn (Zea mays), cotton (Gossypium hirsutum), eastern black night~h~ e (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum), field bindweed (Convolvulus arvensis), Florida beggarweed (Desmodium purpureunl), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb (Polygonum persicaria), large 15 crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean (Glycine max), surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (l~uphorbia heterophylla).Treated plants and untreated controls were m~int~ined in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated 20 controls and visually evaluated. Plant response ratings, summarized in Table F, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A dash response (-) means no test result.

CA 022~7l96 l998-ll-30 WO 97/46530 ~CTIUS97/09569 Table F COMPOUND Table F COMPOUND
Rate 140 g/ha 1522 23 Rate 70 g/ha 15 22 23 POSTEMERGENCE POSTEMERGENCE
Arrowleaf Sida90 100 90 Arrowleaf Sida 80 90 90 Barnyardgrass70 100 95Barnyardgrass30 100 95 Cocklebur90 85 95 Cocklebur85 85 95 Common Ragweed100 100 95Common Ragweed90 100 95 Corn 0 40 5 Corn 0 20 5 Cotton100 100 85 Cotton100 90 80 Estrn Blknight 100 100 100 Estrn Blknight 100 100 100 Fall Panicum 80 90 95Fall Panicum70 85 95 Field Bindweed80 85 90Field Bindweed80 65 90 Fl Beggarweed - 100 95Fl Beggarweed- 100 95 Giant Foxtail 0 95 95Giant Foxtail0 80 95 Hairy Beggartic80 60 85Hairy Beggartic 60 60 80 Ivyleaw Mrnglry95 100 90Ivyleaw Mrnglry 90 90 80 Johnsongrass 0 100 95Johnsongrass0 85 90 Ladysthumb 100 100 100 Ladysthumb 80 100 100 Lambs~uarters100 85 90Lambsquarters100 80 90 Large Crabgrass30 100 95Large Crabgrass 0 100 90 Purple Nutsedge90 80 80Purple Nutsedge 5 75 20 Redroot Pigweed 100 100 95Redroot Pigweed 90 100 95 Soybean 50 100 90 Soybean50 100 90 Surinam Grass 20 90 90Surinam Grass0 85 90 Velvetleaf 100 100 90Velvetleaf100 100 80 Wild Poinsettia 100 100 85 Wild Poinsettia 90 90 85 CA 022~7l96 l998-ll-30 W O 97/46530 PCT~US97/09569 Table F COMPOUND Table F COMPOUND
Rate 35 g/ha 1522 23Rate 17 g/ha 15 22 23 POSTEMERGENCE POSTEMERGENCE
Arrowleaw Sida 80 60 70 Arrowleaw Sida 10 55 0 Barnyardgrass 3090 90Barnyardgrass 0 85 80 Cocklebur 80 85 95Cocklebur 8080 90 Common Ragweed80 100 90Common Ragweed70 85 90 Corn 0 15 0 Corn 0 150 Cotton 85 85 80 Cotton 60 8070 Estrn Blknight 100 100 100 Estrn Blknight 100 90 90 Fall Panicum 50 80 90Fall Panicum 40 75 80 Field Bindweed80 60 85Field Bindweed80 50 85 Fl Beggarweed - 100 80F1 Beggarweed- 100 60 Giant Foxtail 0 75 85Giant Foxtail0 65 50 Hairy Beggartic40 50 70Hairy Beggartic 40 45 60 Ivyleaw Mrnglry90 80 70Ivyleaw Mrnglry 85 75 60 Johnsongrass 0 80 85Johnsongrass0 70 50 Ladysthumb60 10090 Ladysthumb- 100 90 Lambsquarters95 80 90Lambsquarters95 75 85 Large Crabgrass0 90 90Large Crabgrass 0 85 70 Purple Nutsedge0 60 0Purple Nutsedge0 45 0 Redroot Pigweed90 100 90Redroot Pigweed 80 90 85 Soybean40 95 85 Soybean 40 8585 Surinam Grass 0 80 80Surinam Grass 0 75 60 Velvetleaf100 10080 Velvetleaf100 100 70 Wild Poinsettia80 75 80Wild Poinsettia 80 70 80 .. .... .

CA 02257l96 l998-ll-30 W O 97/46S30 PCTrUS97/09569 Table F COMPOUND
Rate 8 g/ha 15 22 23 POSTEMERGENCE
Arrowleaw Sida 0 l0 0 Barnyardgrass 0 75 40 Cocklebur 80 80 80 Common Ragweed 70 70 90 Corn 0 l0 0 Cotton 60 70 55 Estrn Blknight l00 90 90 Fall Panicum 40 70 60 Field Bindweed 50 30 70 Fl Beggarweed - 80 50 Giant Foxtail 0 50 40 Hairy Beggartic 20 40 50 Ivyleaw Mrnglry 85 65 60 Johnsongrass 0 60 l0 Ladysthumb 30 90 80 Lambsquarters 90 65 80 Large Crabgrass 0 65 60 Purple Nutsedge 0 35 0 Redroot Pigweed 80 85 85 Soybean 20 80 80 Surinam Grass 0 70 30 Velvetieaf l00 75 50 Wild Poinsettia 80 65 80 CA 022~7196 1998-11-30 W 097/46530 PCTrUS97/09569 TEST G
Compounds evaluated in this test were form~ ted in a non-phytotoxic solvent mixture which includes a surfactant and applied to plants that were grown for various periods of time before treatment (postemergence application). A mixture of sandy loam soil and 5 greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied 13 days after the last postemergence planting.
Plantings of these crops and weed species were adjusted to produce plants of appropliate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include bristly starbur (Acanthospermun hispidum) alexandergrass (Brachiaria plantaginea), american black night~h~-~e (Solanum americanum), apple-of-Peru (Nicandra physaloides), arrowleaf sida (Sida rhombifolia), Brazilian sicklepod (Cassia tora Brazilian), Surinam grass (Brachiaria decumbens), capim-colchao (Digitaria horizontalis), Crist. soybean (Glycine max v. Cristalina), florida beggarweed (Desmodium purpureum), hairy beggarticks (Bidens pilosa), slender amaranth (Amaranthus viridis), southern sandbur (Cenchrus echinatus), tall morningglory (Ipomoea purpurea), tropical spiderwort (Commelina benghalensis), W20 Soybean (Glycine max v.
W20), W4-4 Soybean (Glycine max v. W4-4), corn (Zea mays v. Pioneer 3394) and wild pointsettia (Eupohorbia heterophylla).
Treated plants and untreated controls were maintained in a greenhouse for 20 approximately 13 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.

CA 022~7l96 l998-ll-30 W 097/46530 PCT~US97/09569 Table G COMPOUND Table G COMPOUND
Rate 140 g/ha 23 Rate 70 g/ha 23 POSTEMERGENCE POSTEMERGENCE
Acanthospermum 100 Acanthospermum 100 Alexandergrass 100 Alexandergrass 100 Apple-of-Peru 100 Apple-of-Peru 80 Arrowleaf Sida 80 Arrowleaf Sida 70 Surinam grass 100 Surinam grass 100 Bl. Nightshade 100 Bl. Nightshade 100 Braz Sicklepod 80 Braz Sicklepod 65 Capim-Colch 100 Capim-Colch 100 Corn 20 Corn 15 Crist. Soybean 100 Crist. Soybean 100 Fl. Beggarweed 100 Fl. Beggarweed 85 H. Beggarticks 85 H. Beggarticks 75 Morningglory 90 Morningglory 80 Sl. Amaranth 100 Sl. Amaranth 90 Southern Sandur 85 Southern Sandur 80 Tr. Spiderwort 100 Tr. Spiderwort 90 Wld Pointsettia 100 Wld Pointsettia 85 W20 Soybean 100 W20 Soybean 100 W4-4 Soybean 100 W4-4 Soybean 100 CA 022~7l96 l998-ll-30 Table G COMPOUND Table G COMPOUND Table G COMPOUND
Rate 35 g/ha 23 Rate 17 g/ha 23 Rate 8 g/ha 23 POSTEMERGENCE POSTEMERGENCE POSTEMERGENCE
Acanthospermum 100 Acanthospermum 100 Acanthospermum 55 Alexandergrass 100 Al~n~ergrass 100 Alexandergrass 85 Apple-of-Peru 80 Apple-of-Peru 75 Apple-of-Peru 65 Arrowleaf Sida 65 Arrowleaf Sida 60 Arrowleaf Sida 40 Surinam grass 100 Surinam grass 90 Surinam grass 80 Bl. Nightshade 100 Bl. Nightshade 100 Bl. Nightshade 85 Braz Sicklepod 60 Braz Sicklepod 35 Braz Sicklepod 10 Capim-Colch 100 Capim-Colch 65 Capim-Colch 60 Corn 0 Corn 0 Corn o Crist. Soybean 100 Crist. Soybean 90 Crist. Soybean 85 Fl. Beggarweed 85 Fl. Beggarweed 85 Fl. Beggarweed 100 H. Beggarticks 70 H. Beggarticks 80 H. Beggarticks 75 Morningglory 70 Morningglory 65 Morningglory 60 Sl. Amaranth 80 Sl. Amaranth 80 Sl. Amaranth 75 Southern Sandur 50 Southern Sandur 45 Southern Sandur 45 Tr. Spiderwort 80 Tr. Spiderwort 70 Tr. Spiderwort 65 Wld Pointsettia 85 Wld Pointsettia 70 Wld Pointsettia 70 W20 Soybean 90 W20 Soybean 80 W20 Soybean 75 W4-4 Soybean 100 W4-4 Soybean 100 W4-4 Soybean 90 -... . . ...

CA 022~7l96 l998-ll-30 TEST H
Compounds evaluated in this test were form~ ted in a non-phytotoxic solvent rnixture which includes a surfactant and applied to plants that were in the one-to four 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.
Plantin~s of these crops and weed species were adjusted to produce plants of ap~ropliate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), black night~h~-le (Solanum nigra), chickweed (Stellaria media), comrnon poppy (Papaver rhoeas), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), Russian thistle (Salsola kali), ryegrass (Lolium multiflorum), scentless chamomile (Matricaria inodora), spring barley (Hordeum vulgare), sugar beet (Beta vulgaris), sunflower (Helianthus annuus), ivyleaf speedwell (Veronica hederaefolia), spring wheat (Triticum aestivum), winter wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), windgrass (Apera spica-venti) and winter barley (Hordeum vulgare).
Treated plants and untreated controls were m~in~ined in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table H, are based upon a 0 to lO0 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result.

CA 022~7l96 l998-ll-30 W O 97/46S30 PCTrUS97/09569 Table H COMPOUND Table H COMPOUND
Rate 125 g/ha 15Rate 62 g/ha13 15 22 25 POSTEMERGENCE POSTEMERGENCE
Annual Bluegras 0Annual Bluegras 10 0 100 65 Blackgrass 0 Blackgrass50 30 55 Blk Nightshade 75Blk Nightshade 60 75 100 100 Chickweed 85 Chickweed4575 100 100 Common poppy 55Common poppy10 50 - 100 Deadnettle75 Deadnettle9070 100 100 Downy brome0 Downy brome 20 10 60 60 Field violet 75Field violet100 75 70 100 Galium 30 Galium 40 50 40 60 Green foxtail 30Green foxtail 65 30 60 100 Jointed Goatgra 0Jointed Goatgra 5 0 30 50 Kochia 85 Kochia 8060 100 60 Lambsquarters 75Lambsquarters 85 80 100 100 LS Canarygrass 0LS Canarygrass 15 0 100 100 Rape 85 Rape 3070 - 100 Redroot Pigweed 75Redroot Pigweed 30 70 100 75 Russian Thistle 10Russian Thistle 50 0 100 50 Ryegrass 0 Ryegrass 50 35 10 Scentless Chamo 60Scentless Chamo 0 60 100 70 Spring Barley 0Spring Barley10 0 40 5 Sugar beet100 Sugar beet 85 100 - 100 Sunflower 55 Sunflower 5 50 - 95 Veronica hedera 40Veronica hedera 55 30 - 60 Wheat (Spring) 0Wheat ~Spring) 10 0 90 65 Wheat (Winter) 0Wheat (Winter) 10 0 100 50 Wild buckwheat 75Wild buckwheat 60 65 70 30 Wild mustard 95Wild mustard 65 100 100 100 Wild oat 0 Wild oat5 0 20 95 Windgrass 0 Windgrass20 0 70 30 Winter Barley 0Winter Barley 10 0 40 10 . , . . ... ~ . ~ ..

CA 022~7l96 l998-ll-30 W O 97/46530 PCTrUS97/09569 Table H COMPOUND Table H COMPO~ND
Rate 31 g/ha 15 22 25 Rate 16 g/ha 13 22 25 POSTEMERGENCE POSTEMERGENCE
Annual Bluegras - 50 60 Annual Bluegras 5 40 50 Blackgrass 0 20 30 Blackgrass0 20 20 Blk Nightshade - 100 85 Blk Nightshade 35 100 100 Chickweed - 100 85 Chickweed15 100 75 Common poppy - - 100 Common poppy 5 - 60 Deadnettle - 100 100 Deadnettle60 100 100 Downy brome - 40 45 Downy brome 050 10 Field violet - 65 75 Field violet 60 50 Galium - 20 55 Galium 10 20 50 Green foxtail 0 30 100 Green foxtail 30 20 85 Jointed Goatgra - 40 45 Jointed Goatgra 0 20 0 Kochia - 85 45 Kochia 60 70 35 La~bsquarters - 100 100 Lambsquarters 50 100 100 LS Canarygrass - 65 65 LS Canarygrass 10 60 60 Rape - - 85 Rape 30 - 70 Redroot Pigweed - 100 75 Redroot Pigweed 20 100 70 Russian Thistle - 90 30 Russian Thistle 40 80 30 Ryegrass 0 20 10 Ryegrass 2 20 5 Scentless Chamo - 100 70 Scentless Chamo 0 100 60 Spring Barley 0 20 65 Spring Barley 5 30 2 Sugar beet - - 100 Sugar beet20 - 75 Sunflower - - 70 Sunflower 0 - 65 Veronica hedera - - 40 Veronica hedera 30 - 55 Wheat (Spring) 0 30 55 Wheat (Spring) 5 30 25 Wheat (Winter) 0 60 30 Wheat (Winter) 5 30 20 Wild buckwheat - 35 30 Wild buckwheat 30 50 5 Wild mustard - 100 100 Wild mustard 45 100 100 Wild oat 0 10 40 Wild oat 0 0 50 Windgrass - 40 40 Windgrass 10 30 30 Winter Barley 0 20 5 Winter Barley 0 20 5 Table H COMPOUND
Rate 8 g/ha 25 POSTEMERGENCE
Annual Bluegras 30 Blackgrass 10 Blk Nightshade 75 Chickweed60 Common poppy 50 Deadnettle60 Downy brome 15 Field violet 50 Galium 50 Green foxtail 50 Jointed Goatgra 0 Kochia 45 Lambsquarters 100 LS Canarygrass 50 Rape 60 Redroot Pigweed 70 Russian Thistle 10 Ryegrass 2 Scentless Chamo 50 Spring Barley 0 Sugar beet 50 Sunflower 60 Veronica hedera 50 Wheat (Spring) 10 Wheat (Winter) 20 Wild buckwheat 0 Wild mustard 70 Wild oat 10 Windgrass30 Winter Barley 2 , .. . . .. . .

Claims (17)

156What is claimed is:
1. A compound selected from the formula and N-oxides and agriculturally suitable salts thereof, wherein Q is , , or ;

A is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be fully aromatic or partially saturated, containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 2 oxygens and no more than 2 sulfurs, and each ring system is optionally substituted with one to three R2, provided that when a nitrogen atom of a heterocyclic ring is substituted with R2, then R2 is other than halogen;
each R1 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, halogen, cyano, nitro, -(Y)t-S(O)n R15 or -(Y)t-C(O)R15;
W is N or CH;

Y is O or NR12;
R2 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, mereapto, C1-C6 alkylthio, C1-C3 haloalkylthio, C3-C6 alkenylthio, C3-C6 haloalkenylthio, C3-C6 alkynylthio, C2-C5 alkoxyalkylthio, C3-C5 acetylalkylthio, C3-C6 alkoxyearbonylalkylthio, C2-C4 cyanoalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, aminosulfonyl, C1-C2 alkylaminosulfonyl, C2-C4 dialkylaminosulfonyl, (CH2)r R16, NR12R13, halogen, eyano or nitro; or R2 is phenyl or benzylthio, each optionally substituted on the phenyl ring with C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
R3 is OR14, SH, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, halogen or NR12R13; or R3 is phenylthio, phenylsulfonyl or -SCH2C(O)Ph, each optionally substituted with C1-C3 alkyl, halogen, cyano or nitro;
each R4 is independently C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio or halogen; or when two R4 are attached to the same carbon atom, then said R4 pair can be taken together to form -OCH2CH2O-, -OCH2CH2CH2O-, -SCH2CH2S- or -SCH2CH2CH2S-, each group optionally substituted with 1-4 CH3;
Rs is OR14, SH, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, halogen or NR12R13; or R5 is phenylthio, phenylsulfonyl or -SCH2C(O)Ph, each optionally substituted with C1-C3 alkyl, halogen, cyano or nitro;
R6 is H, C1-C6 alkyl, Cl-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or -CH2CH2OR12; or R6 is phenyl or benzyl, each optionally substituted on the phenyl ring with C1-C3 alkyl, halogen, cyano or nitro;
R7 is H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, halogen, cyano or nitro;
R8 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;R9 is H, C2-C6 alkoxyearbonyl, C2-C6 haloalkoxycarbonyl, CO2H or cyano;
R10 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cyeloalkyl optionally substituted with 1-4 C1-C3 alkyl or C3-C6 halocycloalkyl;
R11 is cyano, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, S(O)n R13 or C(O)NR12R13;
each R12 is independently H or C1-C6 alkyl;
R13 is C1-C6 alkyl or C1-C6 alkoxy; or R12 and R13 ean be taken together as -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-,-CH2CH2CH2CH2CH2-or-CH2CH2OCH2CH2-;

R14 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkoxyalkyl, forrnyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C(O)NR12R13, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl; or R14 is phenyl, benzyl, benzoyl, -CH2C(O)phenyl or phenylsulfonyl, each optionally substituted on the phenyl ring with C1-C3 alkyl,halogen, cyano or nitro;
R15 is NR12R13, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or C3-C6 cycloalkyl; or R15 is phenyl optionally substituted with C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
R16 is C1-C3 alkoxy, C2-C4 alkoxycarbonyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl; or R16 is phenyl optionally substituted with C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, 1-2 halogen, cyano or nitro;
m is 0, 1, 2 or 3;
n is 0, 1 or 2;
p is 0, 1, 2, 3 or 4;
r is 1, 2 or 3; and t is 0 or 1;
provided that when W is CH and A is in the meta position with respect to the group Q-C(O)- of Formula I, then m is 3 and R1 is other than H.
2. A compound of Claim 1 wherein A is selected from the group 1H-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl;
1H-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; 1H-1,2,3-triazolyl;
2H-1,2,3-triazolyl; 1H-1,2,4-triazolyl; 4H-1,2,4-triazolyl; 1,2,3-oxadiazolyl;
1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl;
1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; 1H-tetrazolyl;
2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl;
1,2,4-triazinyl; and A may optionally be substituted by one to three R2, provided that when a nitrogen atom of a heterocyclic ring is substituted with R2, then R2 is other than halogen.
3. A compound of Claim 2 wherein Q is Q-1 .
4. A compound of Claim 3 wherein each R1 is independently C1-C3 alkyl, C1-C3 alkoxy, halogen or nitro;
R3 is OR14; and R14 is H or Cl-C4 alkylsulfonyl; or R14 is benzoyl or phenylsulfonyl, each optionally substituted with C1-C3 alkyl, halogen, cyano or nitro.
5. A compound of Claim 4 wherein A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
R2 is -(Y)t-S(O)n R15, CF3, OCF3, OCF2H or cyano;
R15 is C1-C6 alkyl;
t is 0; and n is 2.
6. A compound of Claim 2 wherein:
Q is Q-2.
7. A compound of Claim 6 wherein:
each R1 is independently C1-C3 alkyl, C1-C3 alkoxy, halogen or nitro;
R5 is OR14;
R14 is H or C1-C4 alkylsulfonyl; or R14 is benzoyl or phenylsulfonyl, each optionally substituted with C1-C3 alkyl, halogen, cyano or nitro.
R6 is H, C1-C6 alkyl, or C3-C6 alkenyl; and R7 is H.
8. A compound of Claim 7 wherein A is pyridinyl, pyridazinyl, pyrimidinyl or 1H-pyrazolyl;
R2 is -(Y)t-S(O)n R15, CF3, OCF3, OCF2H or cyano;
R15 is C1-C6 alkyl;
t is 0; and n is 2.
9. A compound of Claim 2 wherein Q is Q-3.
10. A compound of Claim 9 wherein each R1 is independently C1-C3 alkyl, C1-C3 alkoxy, halogen or nitro;
R8 is H, C1-C3 alkyl, or cyclopropyl; and R9 is H or C2-C3 alkoxycarbonyl.
11. A compound of Claim 10 wherein A is pyridinyl, pyridazinyl, pyrirnidinyl or 1H-pyrazolyl;

R2 is -(Y)t-S(O)n R15, CF3, OCF3, OCF2H or cyano;
R15 is C1-C6 alkyl;
t is 0; and n is 2.
12. A compound of Claim 2 wherein Q is Q-4.
13. A compound of Claim 12 wherein each R1 is independently C1-C3 alkyl, C1-C3 alkoxy, halogen or nitro;
R10 is C3-C6 cycloalkyl or C3-C6 halocycloalkyl, each optionally substituted with 1-4 C1-C3 alkyl; and R11 is cyano or C2-C6 alkoxycarbonyl.
14. A compound of Claim 13 wherein A is pyridinyl, pyridazinyl, pyrimidinyl or 1H-pyrazolyl;
R2 is -(Y)t-S(O)n R15, CF3, OCF3, OCF2H or cyano;
R15 is C1-C6 alkyl;
t is 0; and n is 2.
15. The compound of Claim 5 which is selected from the group a) 3-hydroxy-2-[[6-(trifluoromethyl)[2,4'-bipyridin]-3-yl]carbonyl]-2-cyclohexen-1-one;
b) 2-[2-chloro-4-(4-pyridinyl)benzoyl]-3-hydroxy-2-cyclohexen-1-one; and c) 2-[2,5-dimethyl-3-(1-methyl-1H-pyrazol-3-yl)-4-(methylsulfonyl)benzoyl]-3-hydroxy-2-cyclohexen-1-one.
16. 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.
17. 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.
CA 2257196 1996-06-06 1997-06-02 Herbicidal pyridinyl and pyrazolylphenyl ketones Abandoned CA2257196A1 (en)

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