AU7252698A - Herbicidal sulfonamides - Google Patents

Herbicidal sulfonamides Download PDF

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Publication number
AU7252698A
AU7252698A AU72526/98A AU7252698A AU7252698A AU 7252698 A AU7252698 A AU 7252698A AU 72526/98 A AU72526/98 A AU 72526/98A AU 7252698 A AU7252698 A AU 7252698A AU 7252698 A AU7252698 A AU 7252698A
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AU
Australia
Prior art keywords
chc1
compound
pct
chloro
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
AU72526/98A
Inventor
Karlheinz Drauz
Wonpyo Hong
Balreddy Kamireddy
Ingo Klement
Anne Vogt
Christoph Helmut Weckbecker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
EIDP Inc
Original Assignee
Degussa GmbH
EI Du Pont de Nemours and Co
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Filing date
Publication date
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Publication of AU7252698A publication Critical patent/AU7252698A/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • 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
    • 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Description

WO 98/47904 PCT/US98/08002 TITLE HERBICIDAL SULFONAMIDES BACKGROUND OF THE INVENTION This invention relates to certain aryl sulfonamides, their N-oxides, agriculturally 5 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, environmentally safer or have .5 different modes of action. U.S. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula RI N"SO 2 R Y 0\ R2__ RN X .0 wherein, inter alia X and Y are Br, Cl or F; R is alkyl, haloalkyl or dialkylamino;
R
1 is H, Na, lower alkyl or SO 2 R;
R
2 is alkyl, haloalkyl or lower alkoxy; and 5 R 3 is halogen, alkyl or haloalkyl. The sulfonamides 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 0 stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation: WO 98/47904 PCT/US98/08002 2 RI\ N-S(0) 2
R
2 J0 Y x I wherein X is H, F or Cl; Y is F, Cl, Br, cyano, nitro, C 1
-C
3 haloalkyl, C 1
-C
3 alkoxy, C 1
-C
3 haloalkoxy or 5
C(S)NH
2 ;
R
1 is H, C 1
-C
6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 haloalkenyl, C 3
-C
6 alkynyl, C 3
-C
6 haloalkynyl, C 2
-C
6 alkoxyalkyl, C 2
-C
6 haloalkoxyalkyl, formyl,
C
2
-C
6 alkylcarbonyl, C 4
-C
7 cycloalkylcarbonyl, C 2
-C
6 haloalkylcarbonyl, C 2
-C
6 alkoxycarbonyl, C 3
-C
6 alkoxyalkylcarbonyl,
C
2
-C
6 haloalkoxycarbonyl,
C
3
-C
6 10 cycloalkyl, C 3
-C
6 halocycloalkyl, C 4
-C
7 cycloalkylalkyl, C 4
-C
7 halocycloalkylalkyl, S(O) 2
R
17 , C(O)SR 3 , C(O)NR 4
R
5 or benzoyl;
R
2 is C 1
-C
6 haloalkyl other than CF 3 , C 2
-C
6 alkoxyalkyl, C 2
-C
6 haloalkoxyalkyl,
C
2
-C
6 cyanoalkyl, C 1
-C
6 nitroalkyl, C 2
-C
6 alkylthioalkyl, C 2
-C
6 alkylsulfinylalkyl, C 2
-C
6 alkylsulfonylalkyl, C 3
-C
8 alkoxycarbonylalkyl or 15 C 3
-C
8 alkylcarbonyloxyalkyl;
R
3 is H, C 1
-C
3 alkyl or C 1
-C
3 haloalkyl; or R 3 is phenyl optionally substituted with
C
1
-C
3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C 1
-C
3 alkoxy or CF 3 ;
R
4 is H, C 1
-C
3 alkyl or C 1
-C
3 haloalkyl; or R 4 is phenyl optionally substituted with
C
1
-C
3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C 1
-C
3 alkoxy or CF 3 ; 20 R 5 is C 1
-C
3 alkyl or C 1
-C
3 haloalkyl; or
R
4 and R 5 are taken together as -CH-CH 2 -, -CH 2
CH
2
CH
2 -,
-CH
2
CH
2
CH
2
CH
2 -, -CH 2
CH
2
CH
2
CH
2
CH
2 - or -CH 2
CH
2
OCH
2
CH
2 -; J is N- O RIO R6 N R8 N R11 Q Z N- N R7 R N N Q J-1 J-2 Q J-3 WO 98/47904 PCTIUS98/08002 3 0 R13 R14
R
9 RS- N-_ R12QRI N-/ NAN/ R8 N' J-4 Q J-6 J-5 wherein the dashed line in J-1 indicates that the left-hand ring contains only single bonds or one bond in the ring is a carbon-carbon double bond; m and n are each independently 0, 1, 2 or 3, provided that m + n is 2 or 3; 5 (C1-C 4 alkyl) Z is CR 6
R
7 , O, S, S(0), S(0) 2 , N(C 1
-C
4 alkyl) or N0
R
6 is H, CI-C 6 alkyl, halogen, hydroxy, C 1
-C
6 alkoxy, C 1
-C
6 haloalkyl, C 1
-C
6 haloalkoxy, C 2
-C
6 alkylcarbonyloxy or C 2
-C
6 haloalkylcarbonyloxy;
R
7 is H, C -C 6 alkyl, hydroxy or halogen; or 0 when R 6 and R 7 are bonded to adjacent carbon atoms they can be taken together with
CH
2 the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 C 1
-C
3 alkyl;
R
8 is C 1
-C
6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl or C 3
-C
6 alkynyl; 5 R 9 is H, halogen, cyano, C 1
-C
6 alkyl, C 1
-C
3 alkoxy or C 1
-C
3 haloalkoxy;
R
10 is H, C 1
-C
6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 haloalkenyl, C 3
-C
6 alkynyl, C 3
-C
6 haloalkynyl, HC(=0), C 2
-C
5 alkylcarbonyl or N(R16)2;
R
11 is C 1
-C
6 alkyl, C 1
-C
6 alkylthio, C 1
-C
6 haloalkyl or N(CH 3
)
2 ;
R
12 is H, halogen, C 1
-C
6 alkyl, CI-C 6 haloalkyl or C 1
-C
6 alkoxy; 0 R 13 and R 14 are each independently H, C 1
-C
6 alkyl or C 1
-C
6 haloalkyl;
R
15 is H, C 1
-C
6 alkyl or C 1
-C
6 haloalkyl; each R 16 is independently H, CI-C 6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl or C2-C 6 alkoxyalkyl;
R
17 is C 1
-C
6 alkyl, CI-C 6 haloalkyl other than CF 3 , C 2
-C
6 alkoxyalkyl, C 2
-C
6 5 haloalkoxyalkyl, C 2
-C
6 cyanoalkyl, C -C 6 nitroalkyl, C 2
-C
6 alkylthioalkyl,
C
2
-C
6 alkylsulfinylalkyl, C 2
-C
6 alkylsulfonylalkyl, C 3
-C
8 alkoxycarbonylalkyl or C 3
-C
8 alkylcarbonyloxyalkyl; and WO 98/47904 PCT/US98/08002 4 each Q is independently O or S. In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" -5 indicates that one or two of the available positions for that substituent may be alkyl which are independently selected. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1 -propynyl, 2-propynyl and the 10 different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of"alkoxyalkyl" include CH 3
OCH
2 , CH 3
OCH
2
CH
2 , CH 3
CH
2
OCH
2 , CH 3
CH
2
CH
2
CH
2
OCH
2 and 15 CH 3
CH
2
OCH
2
CH
2 . "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH 3
SCH
2 , CH 3
SCH
2
CH
2 , CH 3
CH
2
SCH
2 , CH 3
CH
2
CH
2
CH
2
SCH
2 and CH 3
CH
2
SCH
2
CH
2 . "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. 20 "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH 3 S(O), CH 3
CH
2 S(O), CH 3
CH
2
CH
2 S(O), (CH 3
)
2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH 3
S(O)
2 , CH 3
CH
2
S(O)
2 , CH 3
CH
2
CH
2
S(O)
2 , (CH 3
)
2
CHS(O)
2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Cyanoalkyl" denotes 25 an alkyl group substituted with one cyano group. Examples of"cyanoalkyl" include NCCH 2 ,
NCCH
2
CH
2 and CH 3
CH(CN)CH
2 . "Alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl", and the like, are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of "cycloalkylalkyl" include 30 cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. "Alkylcycloalkyl" denotes alkyl substitution on a cycloalkyl moiety. Examples include 4-methylcyclohexyl and 3-ethylcyclopentyl. "Cyanocycloalkyl" denotes a 35 cycloalkyl group substituted with one cyano group. Examples of "cyanocycloalkyl" include 4-cyanocyclohexyl and 3-cyanocyclopentyl. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; WO 98/47904 PCTIUS98/08002 5 one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary 5 amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., 10 Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and 15 G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. 0 Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F 3 C, CICH 2 , CF 3
CH
2 and CF 3 CCl 2 . The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (Cl) 2
C=CHCH
2 and 5 CF 3
CH
2
CH=CHCH
2 . Examples of"haloalkynyl" include HC-CCHC1, CF 3 C-C, CCl 3 C-C and FCH 2
C=CCH
2 . Examples of"haloalkoxy" include CF 3 0, CCl 3
CH
2 0, HCF 2
CH
2
CH
2 0 and CF 3
CH
2 0. Examples of"haloalkylthio" include CCl 3 S, CF 3 S, CC1 3
CH
2 S and ClCH 2
CH
2
CH
2 S. Examples of"haloalkylsulfinyl" include CF 3 S(0), CCl 3 S (0),
CF
3
CH
2 S(O) and CF 3
CF
2 S(O). Examples of"haloalkylsulfonyl" include CF 3
S(O)
2 , 0 CCl 3
S(O)
2 , CF 3
CH
2
S(O)
2 and CF 3
CF
2
S(O)
2 . Examples of"haloalkoxyalkoxy" include
CF
3
OCH
2 0, ClCH 2
CH
2
OCH
2
CH
2 0, Cl 3
CCH
2
OCH
2 0 as well as branched alkyl derivatives. The total number of carbon atoms in a substituent group is indicated by the "Ci-C " prefix where i and j are numbers from 1 to 8. For example, C 1
-C
3 alkylsulfonyl designates 5 methylsulfonyl through propylsulfonyl; C 2 alkoxyalkyl designates CH 3
OCH
2 ; C 3 alkoxyalkyl designates, for example, CH 3
CH(OCH
3 ), CH 3
OCH
2
CH
2 or CH 3
CH
2
OCH
2 ; and C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including WO 98/47904 PCT/US98/08002 6
CH
3
CH
2
CH
2
OCH
2 and CH 3
CH
2
OCH
2
CH
2 . Examples of"alkylcarbonyl" include
C(O)CH
3 , C(O)CH 2 CH2CH 3 and C(O)CH(CH 3
)
2 . Examples of"alkoxycarbonyl" include
CH
3 OC(=O), CH 3
CH
2 OC(=O), CH 3
CH
2
CH
2 OC(=O), (CH 3
)
2 CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of 5 Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are 10 independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)_ j , then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R 1 or R 10, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said 15 group being unsubstituted. Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from 20 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 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. Z5 The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic 0 bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol. Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally suitable 5 salts thereof, wherein X is F or Cl; and Y is F, Cl or Br.
WO 98/47904 PCT/US98/08002 7 Preferred 2. Compounds of Preferred I wherein
R
1 is H, C 1
-C
6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl, C 3
-C
6 alkynyl, C 2
-C
6 alkoxyalkyl, C 2
-C
6 haloalkoxyalkyl, C 2
-C
6 alkylcarbonyl, C 4
-C
7 cycloalkylcarbonyl, C 2
-C
6 haloalkylcarbonyl, C 2
-C
6 alkoxycarbonyl, 5 C 3
-C
6 alkoxyalkylcarbonyl, S(O) 2 R 17, C(O)NR 4
R
5 or benzoyl. Preferred 3. Compounds of Preferred 2 wherein J is J-1, J-2, J-3 or J-6. Preferred 4. Compounds of Preferred 3 wherein Z is CR 6
R
7 , O or S; 0 R 6 is H, halogen, C 1
-C
6 alkoxy or C 2
-C
6 alkylcarbonyloxy;
R
7 is H or halogen; m and n are each independently 1 or 2, provided that m + n is 2 or 3;
R
8 is C 1
-C
6 alkyl, C 1
-C
6 haloalkyl or C 3
-C
6 alkenyl;
R
9 is halogen, C 1
-C
6 alkyl, C 1
-C
3 alkoxy or C 1
-C
3 haloalkoxy; 5 R 10 is C 1
-C
6 alkyl, C 1
-C
6 haloalkyl, C 3
-C
6 alkenyl or NH 2 ; and
R
11 is CI-C 6 alkyl or C 1
-C
6 haloalkyl. Preferred 5. Compounds of Preferred 4 wherein
R
1 is H, C 2
-C
3 alkylcarbonyl or C 2
-C
3 alkoxycarbonyl; and
R
2 is C 1
-C
2 haloalkyl. 0 Preferred 6. Compounds of Preferred 5 wherein J is J-1. Preferred 7. Compounds of Preferred 5 wherein J is J-2. Preferred 8. Compounds of Preferred 5 wherein 5 J is J-3. Preferred 9. Compounds of Preferred 5 wherein J is J-6. Most preferred are compounds of Preferred 5 selected from the group: (a) N-[2-chloro-5-[(dihydro-3-oxo- 1H,3H,5H-pyrazolo[1,2-c][1,3,4]thiadiazol- 1 0 ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide; (b) N-[2-chloro-5-[(dihydro-3-oxo-lH,3H,5H-pyrazolo[1,2-c][1,3,4]thiadiazol-1 ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]-2-methylpropanamide; (c) 1-chloro-N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl) 1(2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; 5 (d) N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- 1(2H) pyrimidinyl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide; (e) methyl [2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H) pyrimidinyl]-4-fluorophenyl][(chloromethyl)sulfonyl]carbamate; WO 98/47904 PCT/US98/08002 8 (f) 1-chloro-N-[2-chloro-5-[3,6-dihydro-3,6-dioxo-3-(2-propenyl)-4 (trifluoromethyl)- 1 ( 2
H
1 )-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; (g) 1-chloro-N-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- 1H 1,2,4-triazol- 1 -yl]-4-fluorophenyl]methanesulfonamide; and 5 (h) N-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- 1 H-1,2,4 triazol- 1 -yl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide. This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which 10 comprise the above preferred compounds. This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds. 15 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 1-6. The definitions of X, Y, R 1
-R
17 , J, Q, m, and n in the compounds of Formulae 1-25 below are as defined above in the Summary of the Invention. Compounds of Formulae Ia-If are various subsets of the compounds of Formula I, 20 and all substituents for Formulae Ia-If are as defined above for Formula I. Compounds of Formula Ia are prepared by the method described in Scheme 1 starting from the commercially-available acetanilides of Formula 1. Nitration of the compounds of Formula 1 with nitric acid gives the nitro compounds of Formula 2, which can be hydrolyzed in 6NHC1 to yield the amines of Formula 3. Treatment of the compounds of Formula 3 with 25 phosgene or thiophosgene, or their equivalents, provide the corresponding iso- or thiocyanates of Formula 4. Reaction of the compounds of Formula 4 with diamines of Formula 5 in an inert solvent such as tetrahydrofuran or toluene in the presence of a suitable base such as potassium carbonate, sodium carbonate or pyridine yields the urea intermediates; these urea intermediates are treated with phosgene or a phosgene equivalent 30 to give the compounds of Formula 6. Reduction of the nitro group with either tin chloride or iron in acetic acid gives the compounds of Formula 7. Condensation of the compounds of Formula 7 with a suitable sulfonyl chloride provides the compounds of Formula Ia wherein
R
1 is H. Compounds of Formula Ia wherein R 1 is other than H can be prepared by treatment of the NH compound with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride 5 to give the corresponding capped compounds of Formula Ia. Diamines of Formula 5 are either commercially available or can be prepared by methods known in the art; see, for instance, EP 075,267 and EP 457,151.
WO 98/47904 PCT/US98/08002 9 Scheme 1 NHAc NHAc
NI-H
2 HNO3 X HCI Cl2C=Q
H
2 SO4 02 02 Y Y Y 2 3 X NCQ R6x 1. Z f 5 N / \ X R7.. O m NH ' Y R6 N SnCl2 IQ or 02 2. phosgene Z N2 Fe/AcOH Q 4 6 X x NY N /\Y R6_)V_ N -Y CISO 2
R
2 R6 N Rla-G Z Q NHm 2 Z 'I Q N-S02R 2 1 R N G is halide or Q Q sulfonate; 7 Ia (RI is H) R l a is Rlexcluding H X R6
N--
Z I Q N-SO2R 2 R7,> N I rn R 1 Q Ia (R 1 is other than H) 5 Scheme 2 illustrates the preparation of compounds of Formula Ib. Anilines of Formula 3 are treated with sodium nitrite and reduced with tin chloride or iron in acetic acid to give the corresponding hydrazines of Formula 8. The hydrazines of Formula 8 are converted to triazolines of Formula 9 by reaction with an appropriate aldehyde, followed by potassium cyanate and bleach; these methods are known in the art: see, for example, Temple Jr., C. 0 The Chemistry ofHeterocyclic Compounds (1981), 37, 365-403; Lyga, J. W. Synthetic WO 98/47904 PCT/US98/08002 10 Communications (1986), 163; Ray, P. S. et al. Heterocyclic Chemistry (1990), 27, 2017; Theodoridis, G. et al. U.S. Patent 4,980,480. Alkylation of compounds of Formula 9 with an alkyl halide in the presence of a suitable base gives the compounds of Formula 10. The nitro group can then be reduced by the methods described in Scheme 1 to yield the compounds of 5 Formula 11, which are treated with an appropriate sulfonyl chloride to provide the compounds of Formula Ib wherein R 1 is H. Further functionalization can be accomplished by treatment with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the corresponding capped compounds of Formula Ib wherein R 1 is other than H. 10 Scheme 2
NH
2 NHNH 2 1. NaNO 2 1. R 9 -CHO 2. Reduction 2. KOCN/AcOH 02 02 3. NaOCI Y Y 3 8 O X O X H-_ N N Y R8-G R8, N T / reduction -N G is halide N R9NO 2 or sulfonate R9NO2 9 10 O X O X R8I N. CISO 2
R
2
R
8 _, N Y N/ 2R 1 a-G N/ R9 NH 2 R9N- SO2R 2 11 RI Rl a is R 1 excluding H Ib (RI is other than H) 15 WO 98/47904 PCT/US98/08002 11 Compounds of Formula Ic can be prepared by the methods shown in Scheme 3. Anilines of Formula 3 are converted the the corresponding isocyanates of Formula 12 by treatment with phosgene or a phosgene equivalent. The isocyanates of Formula 12 are then condensed with the appropriate substituted alkylcrotonates of Formula 13 in the presence of 5 a base such as sodium hydride, followed by acidification with dilute HCI to afford the compounds of Formula 14; this method is known in the art: see, for example, Satow, J. et al. EP 408,382-A2. Alkylation using a suitable alkyl halide and reduction with tin chloride or iron in acetic acid gives the compounds of Formula 16. The anilines of Formula 16 are then treated with an appropriate sulfonyl chloride to provide the compounds of Formula Ic 10 wherein R 1 is H. Further functionalization can be accomplished by treatment with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the corresponding capped compounds of Formula Ic wherein R 1 is other than H. Scheme 3 15 O Rll H NCO OEt phosgene ~ X 1. NaH, RI NH 2 13 0 " RIO-G I 2. dilute HCI X G is halide 02 or sulfonate Y 02 12 Y 14 Rll Rll Rll RIO RI0 RIO O' O Fe-AcOH O NX-O 1. R 2 O0 2 CI O or SO2CI X SnCI2 X 2. RIa-G X 02 H2 R 2
SO
2 - 1 y15 16 RI Y Ic (RI is other than H)
R
l a is RI excluding H 0 WO 98/47904 PCT/US98/08002 12 Compounds of Formula Id can be prepared by the methods shown in Scheme 4. The isocyanates of Formula 12 are treated with trimethylsilyl azide and water to afford the tetrazolinones of Formula 17; this method is known in the art: see, for example, Theodoridis, G. Pesticide Science (1990), 30, 259. Alkylation using a suitable alkyl halide 5- and reduction with tin chloride or iron in acetic acid gives the compounds of Formula 19. The anilines of Formula 19 are then treated with an appropriate sulfonyl chloride to provide the compounds of Formula Id wherein R 1 is H. Further functionalization can be accomplished by treatment with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the corresponding capped compounds of Formula Id wherein R 1 is other 0 than H. Scheme 4 O X 12 1. TMSN 3 H N N Y R 8 -G 2. H20 \ / N~N G is halide
NO
2 or sulfonate 17 O X O X R8, N- Y reduction. R 8 -. N . Y CISO 2
R
2 N-=N N-=N NO2
NIH
2 18 19 O X O X R8 NY Rla-G R8K N Y N N N=N N- S0 2
R
2 N- S0 2
R
2 RI Rla is R 1 excluding H R1 Id (RI is H) Id (RI is other than H) WO 98/47904 PCT/US98/08002 13 Compounds of Formula le are prepared by the method illustrated in Scheme 5. The nitro compounds of Formula 2 are reduced with hydrogen over a metal catalyst, or by treatment with tin chloride or iron in acetic acid to yield the anilines of Formula 20. Reaction with an appropriate sulfonyl chloride provides the acetanilides of Formula 21. 5 Compounds of Formula 21 can be deprotected with HC1, condensed with the cyclic anhydrides of Formula 22, and then capped by reaction with an appropriate alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the compounds of Formula le wherein R 1 is other than H. 0 Scheme 5 NHAc reduction X CISO 2
R
2 2 -1
H
2 Y 20 R1 2 NHAc 1. HCI R12 S X 2. R12 R14
R
2 SO2 R13 OO R14 X H Y 21 22 R 2 SO2 3. Rla-G
R
1 y
R
l a is Rlexcluding H; le (Rlis other than H) G is halide or sulfonate 5 WO 98/47904 PCT/US98/08002 14 Compounds of Formula If can be prepared by the methods shown in Scheme 6. Acetanilides of Formula 1 are reacted with ICI to give the iodo compounds of Formula 23. The iodides of Formula 23 are coupled with the pyrazole compounds of Formula 24 in the presence of a palladium catalyst to provide the compounds of Formula 25; this coupling 5 method and the preparation of compounds of Formula 24 are known in the art: see, for example, Yamanaka et al. Heterocycles (1992), 33, 813-818. Compounds of Formula 25 can be deprotected and capped as described in Scheme 5 to yield the compounds of Formula If. Scheme 6 10 I ICI X PdO AcOH R9 Ac R 1 5 Y R / SnBu 3 R8/ N 23 24 R9 X R9 X R15 R15 1. HCI N_ 2. R 2
SO
2 Cl /N Y R81/- N 2 N-- N 3. R 1 a-G R8 N NHAc N-SO2R 2 25 Rla is R excluding H; RI G is halide or sulfonate If (R 1 is other than H) It is recognized that some reagents and reaction conditions described above for 5 preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in 0 Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in WO 98/47904 PCT/US98/08002 15 detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I. -5 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 10 description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1 H NMR spectra are reported in ppm downfield from 15 tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, dt = doublet of triplets, br s = broad singlet. EXAMPLE 1 Step A: Preparation of N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide To a stirred solution of N-(4-chloro-2-fluorophenyl)acetamide (180.6 g, 0.96 mol) in 20 concentrated sulfuric acid (1 L) was added a mixture of 175 mL of concentrated HNO 3 and 175 mL of concentrated sulfuric acid at 0 to 5 oC in 1.5 h. After the addition was finished, the reaction mixture was stirred for another 0.5 h. The solution was poured into 5 L of ice water. After the product precipitated, it was isolated by filtration and then was dissolved in 2.5 L of ethyl acetate. After separation of the water layer, the organic layer was dried over 25 sodium sulfate and then the solvent was evaporated. The crude product was triturated in diisopropyl ether (1.5 L), isolated by filtration, and dried under reduced pressure to afford the title compound of Step A (196.2 g, 87.6%) melting at 145-146 oC. 1 H NMR (Me 2 SO-d 6 ) 6 10.3-10.2 (s, 1H), 8.9 (d, 1H), 7.9-7.8 (d, 1H), 2.2-2.1 (s, 3H). Step B: Preparation of 4 -chloro-2-fluoro-5-nitrobenzenamine 30 A solution of title compound of Step A (50 g, 0.214 mol) in 6NHCI (200 mL) was heated at reflux for 6h. The reaction mixture was cooled and poured into a beaker containing ice. The precipitated solid was filtered, dissolved in ethyl acetate (500 mL) and removal of the solvent gave 39 g (95%) of the title compound of Step B as a light yellow solid melting at 102 oC. 'H NMR (CDCl 3 ): 8 7.38 (d, 1H), 7.17 (d, 1H), 4.11 (br s, 2H). 35 Step C: Preparation of 1-chloro-5-fluoro-4-isothiocyanato-2-nitrobenzene To a solution of the title compound of Step B (7.64 g, 40 mmol) and thiophosgene (4.6 g, 40 mmol) in p-dioxane (200 mL) at 0 oC was added triethylamine (6 mL) in p-dioxane (30 mL) dropwise under nitrogen atmosphere during 30 min. The reaction mixture was first WO 98/47904 PCTIUS98/08002 16 allowed to reach room temperature then heated at 70 'C for 3h. The precipitated triethylamine hydrochloride was filtered and the solvent was removed to give the title compound of Step C as an oil which was used directly in the following reaction. Step D: Preparation of 3-[(4-chloro-2-fluoro-5-nitrophenyl)iminoltetrahydro- IH,3H -5 F 1,3,4]thiadiazolo[3,4-a]pyridazin- 1-one To a solution of hexahydropyridazine hydroiodide (6.18 g,) and potassium carbonate (5 g) in tetrahydrofuran (150 mL) was added a solution of the title compound of Step C (9.32 g, 40 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at that temperature for 4h. The potassium carbonate was removed by filtration and 10 the solvent was removed under reduced pressure. A solution of this intermediate (6.38 g, 20 mmol) in methylene chloride (100 mL) in the presence of pyridine (5 mL) was added to a solution of triphosgene (2.91 g, 10 mmol) in methylene chloride (20 mL) at room temperature dropwise under a nitrogen atmosphere. The reaction mixture was stirred for 2h and diluted with methylene chloride (300 mL), washed with water (50 mL), and 5% HCI 15 solution (50 mL). The organic phase was separated, dried and the solvent was removed under reduced pressure. The title compound of Step D was isolated by flash chromatography as a solid melting at 151 oC (5.4g, 78%). 'H NMR (CDCl 3 ): 6 7.63 (d, 1H), 7.30 (d, 1H), 3.80 (mn, 4H), 2.32 (min, 1H), 1.98 (m, 4H). Ste E: Preparation of 3-[(5-amino-4-chloro-2-fluorophenvl)imino]tetrahydro- lH,3H 20 [ 1,3,41thiadiazolof3,4-a]pvridazin- 1-one A mixture of the title compound of Step D (2.2 g, 6.37 mmol) and SnCl 2 .2H 2 0 (4.5 g, 20 mmol) in ethyl acetate was heated at 70 oC for 3h. The reaction mixture was cooled to room temperature and sodium carbonate (5 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture then was filtered through a pad of celite, the 25 solvent was removed in vacuo and the the title compound of Step E was isolated as a solid by flash chromatography (1.72 g, 86%). 'H NMR (CDCI 3 ): 5 7.05 (d, 1H), 6.36 (d, 1H), 3.90 (bs, 2H), 3.74 (min, 4H), 1.98 (m, 4H). Step F: Preparation of 1-chloro-N-[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-lH,3H [1,3,4]thiadiazolo[3,4-a]pyridazin-1 30 vlidene)amino]phenvl]methanesulfonamide To a solution of the title compound of Step E (1.27 g; 4.03 mmol) and pyridine (lmL) in methylene chloride (20 mL) was added dropwise a solution of chloromethylsulfonyl chloride (0.75 g, 5.03 mmol) in methylene chloride under a nitrogen atmosphere at room temperature. The reaction mixture was stirred for additional 4h, transferred to a separatory 35 funnel, diluted with methylene chloride (50 mL) and washed with water (2 x 25 mL). Organic phase was separated, dried and solvent was removed in vacuo. The title compound of Step F, a compound of this invention, was isolated by flash chromatography as a solid WO 98/47904 PCT/US98/08002 17 melting at 168 oC (1.40 g, 81%). 'H NMR (CDCl 3 ): 8 7.32 (d, IH), 7.23 (d, 1H), 6.92 (s, 1H), 4.53 (s, 2H), 3.74 (m, 4H), 1.98 (m, 4H). EXAMPLE 2 Step A: Preparation of N-r2-chloro-4-fluoro-5-[(tetrahydro-3-oxo- 1H,3H -5 [ 1,3,4]thiadiazolor[3,4-a]pyridazin- 1 -ylidene)aminol]phenyll-N [(chloromethyl)sulfonvl]-2-methylpropanamide To a solution of the title compound of Step F of Example 1 (0.3 g, .70 mmol), pyridine (0.5 mL) in methylene chloride (5 mL) in the presence of dimethylaminopyridine (25 mg) was added isobutyryl chloride (110 mg) in methylene chloride (1 mL) at room temperature. 10 The reaction mixture was stirred at room temperature for 2h and diluted with methylene chloride (5 mL), washed with water (5 mL) and 5% HCI (5 mL). The organic phase was separated, dried, and the title compound of Step A, a compound of this invention, was isolated by flash chromatography as a solid melting at 183 oC (0.31g, 89%). 'H NMR (CDCl 3 ): 8 7.32 (d, 1H), 7.16 (d, 1H), 5. 41(dd, 1H), 4.84 (dd, 1H), 3.80 (m, 4H), 2.32 (m, 15 1H), 1.98 (m, 4H), 1.12 (d, 6H). EXAMPLE 3 Step A: Preparation of 1-chloro-5-fluoro-4-isocvanato-2-nitrobenzene To a stirred solution of diphosgene (4.75 g, 24 mmol) in 100 mL ofp-dioxane was added the title compound of Step B of Example 1 (3.8 g, 20 mmol) in 10 mL ofp-dioxane at 20 room temperature. The reaction mixture was cooled to 10 oC and a solution of 5 ml of triethylamine in 25 mL ofp-dioxane was added dropwise at that temperature. The temperature was then raised to 70 oC for 6 h. After cooling to room temperature, the reaction mixture was filtered and the solvent was removed under reduced pressure to give the title compound of Step A which was used directly in the next reaction. 25 Step B: Preparation of 3-(4-chloro-2-fluoro-5-nitrophenvl)-6-(trifluoromethyl) 2,4(1H,3H)-pyrimidinedione To a solution of dimethylformamide (30 mL) and NaH (60% suspension, 0.8 g) was added a solution of title compound of Step A (4.3 g, 19.8 mmol) dropwise at -78 C with stirring. The reaction mixture was stirred at that temperature for an additional 2 h under an 30 argon atmosphere, then at room temperature for 12 h. The reaction mixture was then poured into a beaker containing ice (50 g) and concentrated HCI (10 mL). The reaction mixture was extracted with ethyl acetate and the solvent was removed under reduced pressure to yield the title compound of Step B which was purified by flash chromatography to give a white solid (5.2 g, 74%). 'H NMR (DMSO-d 6 ): 8 8.48 (d, 1H), 8.15 (d, 1H), 6.43(s, 1H), 3.57 (s, 3H), 35 Step C: Preparation of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6 (trifluoromethyl)-2,4(1H,3H)-pvrimidinedione A mixture of the title compound of Step B (1.75 g, 4.94 mmol), potassium carbonate (0.7 g), dimethyl sulfate (0.63 g) in acetone was heated at reflux for 4h. After completion of WO 98/47904 PCT/US98/08002 18 the reaction, the potassium carbonate was filtered off, the solvent was removed under reduced pressure and the title compound of Step C was isolated by flash chromatography as a solid melting at 103 oC (1.6 g, 89%). 'H NMR (CDC1 3 ): 6 8.03 (d, 1H), 7.50 (d, IH), 6.39 (s, 1H), 3.57 (s, 3H), 5 Step D: Preparation of 3 -(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6 (trifluoromethyl)-2,4( lH,3H)-pyrimidinedione A mixture of the title compound of Step C (1.5 g, 4.08 mmol) and SnCI 2 .2H 2 0 (4.0 g, 16.6 mmol) in ethyl acetate was heated at 70 'C for 3h. The reaction mixture was cooled to room temperature and sodium carbonate (5 g) was added and the mixture was stirred at room 0 temperature overnight. The reaction mixture was filtered through a pad of celite, the solvent was removed under reduced pressure and the title compound of Step C was isolated as a solid by flash chromatography melting at 127 oC (1.15 g, 84%). 1H NMR (CDCl 3 ): 5 7.21 (d, 1H), 6.62 (d, 1H), 6.36 (s, 1H), 4.02 (br s, 2H), 3.55 (s, 3H). Step E: Preparation of 1-chloro-N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4 5 (trifluoromethyl)- 1 ( 2 HI)-pyrimidinyl)-4-fluorophenyllmethanesulfonamide To a solution of the title compound of Step D (1.1 g; 3.26 mmol) and pyridine (1 mL) in methylene chloride (20 mL) was added dropwise a solution of chloromethylsulfonyl chloride (0.70 g, 4.69 mmol) in methylene chloride in nitrogen atmosphere at room temperature. The reaction mixture was stirred for additional 4h, transferred to separatory 10 funnel, diluted with methylene chloride (50 mL) and washed with water (2 x 25 mL). The organic phase was separated, dried and solvent was removed under reduced pressure. The title compound of Step E, a compound of this invention, was isolated by flash chromatography as a solid melting at 92 oC (1.20 g, 83%). IH NMR (CDCl 3 ): 6 7.67 (d, 1H), 7.38 (d, 1H), 7.18 (br s, 1H), 6.37 (s, 1H), 4.55 (s, 3H), 3.56 (s, 3H). 5 EXAMPLE 4 Step A: Preparation of N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4 (trifluoromethyl)- 1 (2H)-pyrimidinyl)-4-fluorophenyl]-N [(chloromethvl)sulfonyl]acetamide To a solution of the title compound of Step E of Example 3 (0.25 g, 0.55 mmol), 0 pyridine (0.5 mL) in methylene chloride (4 mL) in the presence of dimethylaminopyridine (20 mg) was added acetyl chloride (90 mg) in methylene chloride (lmL) at room temperature. The reaction mixture was stirred at room temperature for 2h and diluted with methylene chloride (5 mL), washed with water (5 mL) and 5% HCI (5 mL). The organic phase was separated, dried, and the title compound of Step A, a compound of this invention, 5 was isolated by flash chromatography as a solid melting at 170 oC (0.25g, 93%). 'H NMR (CDC1 3 ): 8 7.52 (m, 2H), 6.36 (d, 1H), 5.40 (dd, 1H), 4.90 (dd, 1H) 3.60 (s, 3H).
WO 98/47904 PCT/US98/08002 19 By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 8 can be prepared. The following abbreviations are used in the Tables which follow: CN = cyano. TABLE 1 X N-K R S RI N-SO 2
R
2 0 R__I R 2 X Y R 6 H CH 2 F F Cl H H CH 2 F Cl Cl H H CH 2 CI F Cl H H CH 2 CI Cl Cl H H CH 2 Br F Cl H H CH 2 Br Cl Cl H
C(=O)CH
3
CH
2 F F Cl H
C(=O)CH
3
CH
2 F Cl Cl H
C(=O)CH
3
CH
2 C1 F Cl H
C(=O)CH
3
CH
2 CI Cl Cl H
C(=O)CH
3
CH
2 Br F Cl H
C(=O)CH
3
CH
2 Br Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 F F Cl H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl H
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl H
CO
2
CH
3
CH
2 F F Cl H
CO
2
CH
3
CH
2 F Cl Cl H
CO
2
CH
3
CH
2 Cl F Cl H
CO
2
CH
3
CH
2 Cl Cl Cl H
CO
2
CH
3
CH
2 Br F Cl H WO 98/47904 PCT/US98/08002 20
CO
2
CH
3
CH
2 Br Cl Cl H H CH 2 F F Cl F H CH 2 F Cl Cl F H CH 2 C1 F Cl F H CH 2 Cl Cl Cl F H CH 2 Br F Cl F H CH 2 Br Cl Cl F
C(=O)CH
3
CH
2 F F Cl F
C(=O)CH
3
CH
2 F Cl Cl F
C(=O)CH
3
CH
2 CI F Cl F
C(=O)CH
3
CH
2 CI Cl Cl F C(0)CH 3
CH
2 Br F Cl F C(0)CH 3
CH
2 Br Cl Cl F
C(=O)CH(CH
3
)
2
CH
2 F F Cl F
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl F
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl F
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl F C(0)CH(CH 3
)
2
CH
2 Br F Cl F
CQ=O)CH(CH
3
)
2
CH
2 Br Cl Cl F
CO
2
CH
3
CH
2 F F Cl F
CO
2
CH
3
CH
2 F Cl Cl F
CO
2
CH
3
CH
2 C1 F Cl F
CO
2
CH
3
CH
2 CI Cl Cl F
CO
2
CH
3
CH
2 Br F Cl F
CO
2
CH
3
CH
2 Br Cl Cl F
IHCH
2 F F Cl Cl H CH 2 F Cl Cl Cl H CH 2 CI F Cl Cl H CH 2 C1 Cl Cl Cl H CH 2 Br F Cl Cl H CH 2 Br Cl Cl Cl
C(=O)CH
3
CH
2 F F Cl Cl
C(=O)CH
3
CH
2 F Cl Cl Cl
C(=O)CH
3
CH
2 Cl F Cl Cl
C(=O)CH
3
CH
2 C1 Cl Cl Cl
C(=O)CH
3
CH
2 Br F Cl Cl C(0)CH 3
CH
2 Br Cl Cl Cl
C(=O)CH(CH
3
)
2
CH
2 F F Cl Cl WO 98/47904 PCT/US98/08002 21
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl Cl
C(=O)CH(CH
3
)
2
CH
2 CI F Cl Cl
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl Cl
C(=O)CH(CH
3
)
2
CH
2 Br F Cl Cl
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl Cl
CO
2
CH
3
CH
2 F F Cl Cl
CO
2
CH
3
CH
2 F Cl Cl Cl
CO
2
CH
3
CH
2 Cl F Cl Cl
CO
2
CH
3
CH
2 Cl Cl Cl Cl
CO
2
CH
3
CH
2 Br F Cl Cl
CO
2
CH
3
CH
2 Br Cl Cl Cl TABLE 2 x N-- S 2 R R6i 0 RI R2 X YR67 H CH 2 F F Cl H H H CH 2 F Cl Cl H H H CH 2 Cl F Cl H H H CH 2 C1 Cl Cl H H H CH 2 Br F Cl H H H CH 2 Br Cl Cl H H
C(=O)CH
3
CH
2 F F Cl H H
C(=O)CH
3
CH
2 F Cl Cl H H
C(=O)CH
3
CH
2 CI F Cl H H
C(=O)CH
3
CH
2 Cl Cl Cl H H
C(=O)CH
3
CH
2 Br F Cl H H
C(=O)CH
3
CH
2 Br Cl Cl H H
C(=O)CH(CH
3
)
2
CH
2 F F Cl H H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl H H
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl H H WO 98/47904 PCT/US98/08002 22 C(=O)CH(CH3)2 CH2Cl Cl Cl H H C(0)CH(CH 3
)
2
CH
2 Br F Cl H H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl H H
CO
2
CH
3
CH
2 F F Cl H H
CO
2
CH
3
CH
2 F Cl Cl H H
CO
2
CH
3
CH
2 C1 F Cl H H
CO
2
CH
3
CH
2 C1 Cl Cl H H
CO
2
CH
3
CH
2 Br F Cl H H
CO
2
CH
3
CH
2 Br Cl Cl H H H CH 2 F F Cl H F H CH 2 F Cl Cl H F H CH 2 Cl F Cl H F H CH 2 C1 Cl Cl H F H CH 2 Br F Cl H F H CH 2 Br Cl Cl H F
C(=O)CH
3
CH
2 F F Cl H F
C(=O)CH
3
CH
2 F Cl Cl H F
C(=O)CH
3
CH
2 CI F Cl H F
C(=O)CH
3
CH
2 C1 Cl Cl H F
C(=O)CH
3
CH
2 Br F Cl H F
C(=O)CH
3
CH
2 Br Cl Cl H F
C(=O)CH'(CH
3
)
2
CH
2 F F Cl H F
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl H F
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl H F
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl H F
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H F
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl H F
CO
2
CH
3
CH
2 F F Cl H F
CO
2
CH
3
CH
2 F Cl Cl H F
CO
2
CH
3
CH
2 C1 F Cl H F
CO
2
CH
3
CH
2 Cl Cl Cl H F
CO
2
CH
3
CH
2 Br F Cl H F
CO
2
CH
3
CH
2 Br Cl Cl H F H CH 2 F F Cl H Cl H CH 2 F Cl Cl H Cl H CH 2 Cl F Cl H Cl H CH 2 C1 Cl Cl H Cl H CH 2 Br F Cl H Cl WO 98/47904 PCTIUS98/08002 23 H CH 2 Br Cl Cl H Cl
C(=O)CH
3
CH
2 F F Cl H Cl
C(=O)CH
3
CH
2 F Cl Cl H Cl
C(=O)CH
3
CH
2 C1 F Cl H Cl
C(=O)CH
3
CH
2 CI Cl Cl H Cl
C(=O)CH
3
CH
2 Br F Cl H Cl
C(=O)CH
3
CH
2 Br Cl Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 F F Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 CI F Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H Cl
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl H Cl
CO
2
CH
3
CH
2 F F Cl H Cl
CO
2
CH
3
CH
2 F Cl Cl H Cl
CO
2
CH
3
CH
2 C1 F Cl H Cl
CO
2
CH
3
CH
2 C1 Cl Cl H Cl
CO
2
CH
3
CH
2 Br F Cl H Cl
CO
2
CH
3
CH
2 Br Cl Cl H Cl H CH 2 F F Cl Cl H H CH 2 F Cl Cl Cl H H CH 2 Cl F Cl Cl H H CH 2 C1 Cl Cl Cl H H CH 2 Br F Cl Cl H H CH 2 Br Cl Cl Cl H
C(=O)CH
3
CH
2 F F Cl Cl H
C(=O)CH
3
CH
2 F Cl Cl Cl H
C(=O)CH
3
CH
2 CI F Cl Cl H
C(=O)CH
3
CH
2 Cl Cl Cl Cl H
C(=O)CH
3
CH
2 Br F Cl Cl H
C(=O)CH
3
CH
2 Br Cl Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 F F Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 CI F Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl Cl H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl Cl H
CO
2
CH
3
CH
2 F F Cl Cl H WO 98/47904 PCTIUS98/08002 24
CO
2
CH
3
CH
2 F Cl CL Cl H
CO
2
CH
3
CH
2 C1 F Cl Cl H
CO
2
CH
3
CH
2 C1 Cl Cl Cl H
CO
2
CH
3
CH
2 Br F Cl Cl H
COCH
3
CH
2 Br Cl Cl Cl H H CH 2 F F Cl F H H CH 2 F Cl Cl F H H CH 2 C1 F Cl F H H CH 2 CI Cl Cl F H H CH 2 Br F Cl F H H CH 2 Br Cl Cl F H
C(=O)CH
3
CH
2 F F Cl F H
C(=O)CH
3
CH
2 F Cl Cl F H
C(=O)CH
3
CH
2 C1 F Cl F H
C(=O)CH
3
CH
2 Cl Cl Cl F H
C(=O)CH
3
CH
2 Br F Cl F H
C(=O)CH
3
CH
2 Br Cl Cl F H
C(=O)CH(CH
3
)
2
CH
2 F F Cl F H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl F H
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl F H
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl F H
C(=O)CH(CH
3
)
2
CH
2 B r F Cl F H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl F H
CO
2
CH
3
CH
2 F F Cl F H
CO
2
CH
3
CH
2 F Cl Cl F H
CO
2
CH
3
CH
2 C1 F Cl F H
CO
2
CH
3
CH
2 C1 Cl Cl F H
CO
2
CH
3
CH
2 Br F Cl F H
CO
2
CH
3
CH
2 Br Cl Cl F H WO 98/47904 PCT/US98/08002 25 TABLE 3 x N- Y sN- S0 2
R
2 0 __ R2 X Y H CH 2 F F Cl H CH 2 F Cl Cl H CH 2 CI F Cl H CH 2 C1 Cl Cl H CH 2 Br F Cl H CH 2 Br Cl Cl
C(=O)CH
3
CH
2 F F Cl
C(=O)CH
3
CH
2 F Cl Cl
C(=O)CH
3
CH
2 C1 F Cl
C(=O)CH
3
CH
2 C1 Cl Cl C(0)CH 3 ' CH 2 Br F Cl C(0)CH 3
CH
2 Br Cl Cl
C(=O)CH(CH
3
)
2
CH
2 F F Cl
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl C(0)CH(CH 3
)
2
CH
2 Br F Cl C(0)CH(CH 3
)
2
CH
2 Br Cl Cl
CO
2
CH
3
CH
2 F F Cl
CO
2
CH
3
CH
2 F Cl Cl
CO
2
CH
3
CH
2 C1 F Cl
CO
2
CH
3
CH
2 Cl Cl Cl
CO
2
CH
3
CH
2 Br F Cl
CO
2
CH
3
CH
2 Br Cl Cl WO 98/47904 PCT/US98/08002 26 TABLE 4 0 x R9' N N RI/N- SQ2R 2 R_ I R2X Y R8 R9 H CH 2 F F Cl CH 3
CH
3 H CH 2 F Cl Cl CH 3
CH
3 H CH 2 C1 F Cl CH 3
CH
3 H CH 2 Cl Cl Cl CH 3
CH
3 H CH 2 Br F Cl CH 3
CH
3 H CH 2 Br Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 F F Cl CH 3
CH
3
C(=O)CH
3
CH
2 F Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 C1 F Cl CH 3
CH
3
C(=O)CH
3
CH
2 C1 Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br F Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 F F Cl CH 3
CH
3
CO
2
CH
3
CH
2 F Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 C1 F Cl CH 3
CH
3
CO
2
CH
3
CH
2 CI Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Br F Cl CH 3
CH
3
CO
2
CH
3
CH
2 Br Cl Cl CH 3
CH
3 H CH 2 F F Cl CH 3
CF
3 H CH 2 F Cl Cl CH 3
CF
3 H CH 2 C1 F Cl CH 3
CF
3 H CH 2 Cl Cl Cl CH 3
CF
3 WO 98/47904 PCT/US98/08002 27 H CH 2 Br F Cl CH 3
CF
3 H CH 2 Br Cl Cl CH 3
CF
3
C(=O)CH
3
CH
2 F F Cl CH 3
CF
3
C(=O)CH
3
CH
2 F Cl Cl CH 3
CF
3
C(=O)CH
3
CH
9 Cl F Cl CH 3
CF
3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3
CF
3
C(=O)CH
3
CH
2 Br F Cl CH 3
CF
3
C(=O)CH
3
CH
2 Br Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 F F Cl CH 3
CF
3
CO
2
CH
3
CH
2 F Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 C1 F Cl CH 3
CF
3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 Br F Cl CH 3
CF
3
CO
2
CH
3
CH
2 Br Cl Cl CH 3
CF
3 H CH 2 F F Cl CH 2
CH=CH
2
CH
3 H CH 2 F Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 Cl F Cl CH 2
CH=CH
2
CH
3 H CH 2 Cl Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 Br F Cl CH 2
CH=CH
2
CH
3 H CH 2 Br Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 F F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 Cl F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2
CH=CH
2
CH
3 WO 98/47904 PCTJS98/08002 28
CO-,CH
3
CH
2 F F Cl CH-,CH=C H 2
CH
3
CO
9
CH
3
CH
2 F Cl CI CH 9
CH=CH
2
CH
3
CO-,CH
3
CH
2 C1 F Cl CHCHH- CH
CO
2
CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CH
3
CO
9
CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CH
3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 F F Cl CH 2
CH=CH
2
CF
3 H CH 2 F Cl Cl CH 2
CH=CH
2
CF
3 H CH 2 Cl F Cl CH 2
CH=CH
2
CF
3 H CH 2 C1 Cl Cl CH 2
CH=CH
2
CF
3 H CH 2 Br F Cl CH 2
CH=CH
2
CF
3 H CH 2 Br Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 F F CL CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Cl F Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 2
CH=CH
2
CF
3 C(0)CH(CH 3
)
2
CH
2 Br F Cl CH 2
CH=CH
2
CF
3 C(0)CH(CH 3
)
2
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 F F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 C1 F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 C1 Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3 H CH 2 F F Cl CH 2
CH
2
CH
2 F CH 3 H CH 2 F Cl Cl CH 2
CH
2
CH
2 F CH 3 H CH 2 Cl F Cl CH2CH 2
CH
2 F CH 3 H CH 2 C1 Cl Cl CH 2
CH
2
CH
2 F CH 3 H CH 2 Br F Cl CH 2
CH
2
CH
2 F CH 3 H CH 2 Br Cl Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CH 3 WO 98/47904 PCTIUS98/08002 29
C(=O)CH
3
CH
2 C1 F Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH
3
CH
2 CL Cl Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH
2 CH2F CH 3
C(=O)CH
3
CH
2 Br Cl Cl CH-,CH 2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CJI
2 Br F Cl CH 2
CH
2
CH
2 F CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2 CH2CH 2 F CH 3
CO
2
CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F CH 3
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CH 3
CO
2
CH
3
CH
2 C1 F Cl CH 2
CH
2
CH
2 F CH 3
CO
2
CH
3
CH
2 CI Cl Cl CH 2
CH
2
CH
2 F CH 3
CO
2
CH
3
CH
2 Br F Cl CH 2
CH
2
CH
2 F CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH
2
CH
2 F CH 3 H CH 2 F F Cl CH 2
CH
2
CH
2 F CF 3 H CH 2 F Cl Cl CH 2
CH
2
CH
2 F CF 3 H CH 2 C1 F Cl CH 2
CH
2
CH
2 F CF 3 H CH 2 Cl Cl Cl CH 2
CH
2
CH
2 F CF 3 H CH 2 Br F Cl CH1 2
CH
2
CH
2 F CF 3 H CH 2 Br Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 C1 F Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 Cl Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CH 2
CH
2
CH
2 F CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 2
CH
2
CH
2 F CF 3 C(0)CH(CH 3
)
2
CH
2 Br Cl Cl CH 2
CH
2
CH
2 F CF 3
CO
2
CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F CF 3
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F CF 3
CO
2
CH
3
CH
2 Cl F Cl CH 2
CH
2
CH
2 F CF 3
CO
2
CH
3
CH
2 C1 Cl Cl CH 2
CH
2
CH
2 F CF 3 WO 98/47904 PCT/US98/08002 30
CO
2
CH
3
CH
2 Br F Cl CH 2
CH
2
CH
2 F CF 3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH
2
CH
2 F CF 3 TABLE 5 NIO N 0 RV"N S0 2
R
2 H CH 2 F F Cl CH 3
CH
3 H CH 2 F Cl Cl CH 3
CH
3 H CH 2 Cl F Cl CH 3
CH
3 H CH 2 C1 Cl Cl CH 3
CH
3 H CH 2 Br F Cl CH 3
CH
3 H CH 2 Br Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 F F Cl CH 3
CH
3
C(=O)CH
3
CH
2 F Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 C1 F Cl CH 3
CH
3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br F Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 F F Cl CH 3
CH
3
CO
2
CH
3
CH
2 F Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Cl F Cl CH 3
CH
3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Br F Cl CH 3
CH
3 WO 98/47904 PCTIUS98/08002 31
CO
2
CH
3
CH
2 Br Cl Cl CH 3
CH
3 H CH 2 F F Cl CH 3
CF
3 H CH 2 F Cl Cl CH 3
CF
3 H CH 2 Cl F Cl CH 3
CF
3 H CH 2 CI Cl Cl CH 3
CF
3 H CH 2 Br F Cl CH 3
CF
3 H CH 2 Br Cl Cl CH 3
CF
3
C(=O)CH
3
CH
2 F F Cl CH 3
CF
3
C(=O)CH
3
CH
2 F Cl Cl CH 3
CF
3
C(=O)CH
3
CH
2 Cl F Cl CH 3
CF
3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3
CF
3
C(=O)CH
3
CH
2 Br F Cl CH 3
CF
3
C(=O)CH
3
CH
2 Br Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 F F Cl CH 3
CF
3
CO
2
CH
3
CH
2 F Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 Cl F Cl CH 3
CF
3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3
CF
3
CO
2
CH
3
CH
2 Br F Cl CH 3
CF
3
CO
2
CH
3
CH
2 Br Cl Cl CH 3
CF
3 H CH 2 F F Cl CH 2
CH=CH
2
CH
3 H CH 2 F Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 Cl F Cl CH 2
CH=CH
2
CH
3 H CH 2 CI Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 Br F Cl CH 2
CH=CH
2
CH
3 H CH 2 Br Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 F F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 F Cl Cl CH2CH=CH 2
CH
3
C(=O)CH
3
CH
2 Cl F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CH
3
C(=O)CH
3 CHBr Cl Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH=CH
2
CH
3 WO 98/47904 PCTIUS98/08002 32
C(=O)CH(CH
3
)
2
CH
2 F CI Cl CH-,CH=CH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 2
CH=CH
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl CI Cl CH-)CH=C H 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH,)CH=CH 2 ) CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH-)CH=CH 2
CH
3
CO
2
CH
3
CH
2 F F Cl CH 2
CH=CH
2
CH
3 '
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CH
3
CO
2
CH
3
CH
2 CI F Cl CH 2
CH=CH
2
CH
3
CO
2
CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CH
3
CO
2
CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CH
3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CH
3 H CH 2 F F Cl CH 2
CH=CH
2
CF
3 H CH 2 F Cl Cl CH 2
CH=CH
2
CF
3 H CH 2 C1 F Cl CH 2
CH=CH
2
CF
3 H CH 2 Cl Cl CI CH 2
CH=CH
2
CF
3 H CH 2 Br F Cl CH 2
CH=CH
2
CF
3 H CH 2 Br Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 F F Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Cl F Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Cl Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CF
3
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 2
CH=CH
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 F F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Cl F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Cl Cl Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CF
3
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
CF
3 H CH 2 F F Cl CH 2 C=-CH CH 3 H CH 2 F Cl Cl CH 2 C=-CH CH 3 H CH 2 C1 F Cl CH 2 C-=CH CH 3 WO 98/47904 PCT/US98/08002 33 H CH 2 CI Cl Cl CH2C=-CH CH 3 H CH 2 Br F Cl CH 2 C-=CH CH 3 H CH-)Br Cl Cl CH 2 C=CH CH 3
C(=O)CH
3
CH
2 F F Cl CH 2 C=-CH CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 2 C=-CH CH 3
C(=O)CH
3
CH
2 Cl F Cl CH 2 C=-CH CH 3
C(=O)CH
3
CH
2 Cl Cl Cl CH 2 C=-CH CH 3 C(0)CH 3
CH
2 Br F Cl CH 2 C=ECH CH 3
C(=O)CH
3
CH
2 Br Cl Cl CH 2 C-=CH CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2 C=-CH CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2 C=-CH CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 2 C=-CH CH 3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CH 2 C=-CH CH 3 C(0)CH(CH 3
)
2
CH
2 Br F Cl CH 2 C=-CH CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2 C=-CH CH 3
CO
2
CH
3
CH
2 F F Cl CH 2 C=-CH CH 3
CO
2
CH
3
CH
2 F Cl Cl CH 2 C=-CH CH 3
CO
2
CH
3
CH
2 CI F Cl CH 2 C-=CH CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 2 C=-CH CH 3
CO
2
CH
3
CH
2 Br F Cl CH 2 C=-CH CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 2 C=-CH CH 3 H CH 2 F F Cl CH 2 C=-CH CF 3 H CH 2 F Cl Cl CH 2 C=-CH CF 3 H CH 2 C1 F Cl CH 2 C-=CH CF 3 H CH 2 C1 Cl Cl CH 2 C-=CH CF 3 H CH 2 Br F Cl CH 2 C-=CH CF 3 H CH 2 Br Cl Cl CH 2 C=-CH CF 3
C(=O)CH
3
CH
2 F F Cl CH 2 C=-CH CF 3
C(=O)CH
3
CH
2 F Cl Cl CH 2 C=-CH CF 3
C(=O)CH
3
CH
2 C1 F Cl CH 2 C=-CH CF 3
C(=O)CH
3
CH
2 CI Cl Cl CH 2 C=-CH CF 3
C(=O)CH
3
CH
2 Br F Cl CH 2 C-=CH CF 3
C(=O)CH
3
CH
2 Br Cl Cl CH 2 C-=CH CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2 CE=CH CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2 C-=CH CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 2 C=-CH CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 2 C=-CH CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH,C=CH CF 3 WO 98/47904 PCT/US98/08002 34 C(=0)CH(CH 3
)
2
CH
2 Br Cl Cl CH2C-CH CF 3
CO
2
CH
3
CH
2 F F Cl CH 2 C-CH CF 3 CO2CH 3
CH
2 F Cl Cl CH2C-=CH CF 3
CO
2
CH
3
CH
2 C1 F Cl CH2C=-CH CF 3
CO
2
CH
3
CH
2 CI Cl Cl CH 2 C-CH CF 3 CO2CH 3
CH
2 Br F Cl CH 2 C-CH CF 3
CO
2
CH
3
CH
2 Br Cl Cl CH 2 CE-CH CF 3 H CH 2 F F Cl NH 2
CH
3 H CH 2 F Cl Cl NH 2
CH
3 H CH 2 CI F Cl NH 2
CH
3 H CH 2 Cl Cl Cl NH 2
CH
3 H CH 2 Br F Cl NH 2
CH
3 H CH 2 Br Cl Cl NH 2
CH
3
C(=O)CH
3
CH
2 F F Cl NH 2
CH
3
C(=O)CH
3
CH
2 F Cl Cl NH 2
CH
3
C(=O)CH
3
CH
2 Cl F Cl NH 2
CH
3
C(=O)CH
3
CH
2 CI Cl Cl NH 2
CH
3
C(=O)CH
3
CH
2 Br F Cl NH 2
CH
3
C(=O)CH
3
CH
2 Br Cl Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl NH 2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl NH 2
CH
3
CO
2
CH
3
CH
2 F F Cl NH 2
CH
3
CO
2
CH
3
CH
2 F Cl Cl NH 2
CH
3
CO
2
CH
3
CH
2 C1 F Cl NH 2
CH
3
CO
2
CH
3
CH
2 Cl Cl Cl NH 2
CH
3
CO
2
CH
3
CH
2 Br F Cl NH 2
CH
3
CO
2
CH
3
CH
2 Br Cl Cl NH 2
CH
3 H CH 2 F F Cl NH 2
CF
3 H CH 2 F Cl Cl NH 2
CF
3 H CH 2 CI F Cl NH 2
CF
3 H CH 2 Cl Cl Cl NH 2
CF
3 H CH 2 Br F Cl NH 2
CF
3 H CH 2 Br Cl Cl NH 2
CF
3
C(=O)CH
3
CH
2 F F Cl NH 2
CF
3 WO 98/47904 PCTIUS98/08002 35
C(=O)CH
3
CH
2 F Cl Cl NH 2 CF3
C(=O)CH
3
CH
2 CI F Cl NH 2
CF
3
C(=O)CH
3
CH
2 CI Cl Cl NH 2
CF
3
C(=O)CH
3
CH
2 Br F Cl NH 2
CF
3
C(=O)CH
3
CH
2 Br Cl Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl NH 2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl NH 2
CF
3
CO
2
CH
3
CH
2 F F Cl NH 2
CF
3
CO
2
CH
3
CH
2 F Cl Cl NH 2
CF
3
CO
2
CH
3
CH
2 Cl F Cl NH 2
CF
3
CO
2
CH
3
CH
2 Cl Cl Cl NH 2
CF
3
CO
2
CH
3
CH
2 Br F Cl NH 2
CF
3
CO
2
CH
3
CH
2 Br Cl Cl NH 2
CF
3 H CH 2 F F Cl N(CH 3
)
2
CH
3 H CH 2 F Cl Cl N(CH 3
)
2
CH
3 H CH 2 CI F Cl N(CH 3
)
2
CH
3 H CH 2 Cl Cl Cl N(CH 3
)
2
CH
3 H CH 2 Br F Cl N(CH 3
)
2
CH
3 H CH 2 Br Cl Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 F F Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 F Cl Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 CI F Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 Cl Cl Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 Br F Cl N(CH 3
)
2
CH
3
C(=O)CH
3
CH
2 Br Cl Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl N(CH 3
)
2
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl N(CH 3
)
2
CH
3
CO
2
CH
3
CH
2 F F Cl N(CH 3
)
2
CH
3
CO
2
CH
3
CH
2 F Cl Cl N(CH 3
)
2
CH
3
CO
2
CH
3
CH
2 Cl F Cl N(CH 3
)
2
CH
3 WO 98/47904 PCT/US98/08002 36
CO
2
CH
3
CH
2 C1 Cl Cl N(CH 3
)
2
CH
3
CO
2
CH
3
CH
2 Br F Cl N(CH 3
)
2
CH
3
CO
2
CH
3
CH
2 Br Cl Cl N(CH 3
)
2
CH
3 H CH 2 F F Cl N(CH 3
)
2
CF
3 H CH 2 F Cl Cl N(CH 3
)
2
CF
3 H CH 2 CI F Cl N(CH 3
)
2
CF
3 ' H CH 2 C1 Cl Cl N(CH 3
)
2
CF
3 H CH 2 Br F Cl N(CH 3
)
2
CF
3 H CH 2 Br Cl Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 F F Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 F Cl Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 C1 F Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 C1 Cl Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 Br F Cl N(CH 3
)
2
CF
3
C(=O)CH
3
CH
2 Br Cl Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl N(CH 3
)
2
CF
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 F F Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 F Cl Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 C1 F Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 Cl Cl Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 Br F Cl N(CH 3
)
2
CF
3
CO
2
CH
3
CH
2 Br Cl Cl N(CH 3
)
2
CF
3 WO 98/47904 PCTJUS98/08002 37 TABLE 6 0 x
R
8 1- N Rl/N- S0 2
R
2 H CH 2 F F Cl CH 3 H CH 2 F Cl Cl CH 3 H CH 2 C1 F Cl CH 3 H CH 2 CI Cl Cl CH 3 H CH 2 Br F Cl CH 3 H CH 2 Br Cl Cl CH 3
C(=O)CH
3
CH
2 F F Cl CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 3
C(=O)CH
3
CH
2 C1 F Cl CH 3
C(=O)CH
3
CH
2 C1 Cl Cl CH 3
C(=O)CH
3
CH
2 Br F Cl CH 3 C(0)CH 3
CH
2 Br Cl Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3
CO
2
CH
3
CH
2 F F Cl CH 3
CO
2
CH
3
CH
2 F Cl Cl CH 3
CO
2
CH
3
CH
2 Cl F Cl CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3
CO
2
CH
3
CH
2 Br F Cl CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 H CH 2 F F Cl CH 2
CH=CH
2 H CH 2 F Cl Cl CH 2
CH=CH
2 H CH 2 C1 F Cl CH 2
CH=CH
2 H CH 2 C1 Cl Cl CH 2
CH=CH
2 WO 98/47904 PCT/US98/08002 38 H CH 2 Br F CI CH 2
CH=CH
2 H CH 2 Br Cl Cl CH 2
CH=CH
2
C(=O)CH
3
CH
2 F F Cl CH-)CH=CH 2
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
C(=O)CH
3
CH
2 CI F Cl CH 2
CH=CH
2
C(=O)CH
3
CH
2 Cl Cl Cl CH 2
CH=CH
2 C(0)CH 3
CH
2 Br F Cl CH 2
CH=CH
2
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH=CH
2
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH=CH
2
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 2
CH=CH
2
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 2
CH=CH
2 C(0)CH(CH 3
)
2
CH
2 Br F Cl CH 2
CH=CH
2
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 F F Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 C1 F Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 CI Cl Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 Br F Cl CH 2
CH=CH
2
CO
2
CH
3
CH
2 Br Cl Cl CH 2
CH=CH
2 H CH 2 F F Cl CH 2
CH
2
CH
2 F H CH 2 F Cl Cl CH 2
CH
2
CH
2 F H CH 2 CI F Cl CH 2
CH
2
CH
2 F H CH 2 CL Cl Cl CH 2
CH
2
CH
2 F H CH 2 Br F Cl CH 2
CH
2
CH
2 F H CH 2 Br Cl Cl CH 2
CH
2
CH
2 F
C(=O)CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F
C(=O)CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F
C(=O)CH
3
CH
2 Cl F Cl CH 2
CH
2
CH
2 F
C(=O)CH
3
CH
2 C1 Cl Cl CH 2
CH
2
CH
2 F C(0)CH 3
CH
2 Br F Cl CH 2
CH
2
CH
2 F
C(=O)CH
3
CH
2 Br Cl Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 2
CH
2
CH
2 F
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 2
CH
2
CH
2
F
WO 98/47904 PCT/US98/08002 39
CO
2
CH
3
CH
2 F F Cl CH 2
CH
2
CH
2 F
CO
2
CH
3
CH
2 F Cl Cl CH 2
CH
2
CH
2 F
CO
2
CH
3
CH
2 CI F Cl CH 2
CH
2
CH
2 F
CO
2
CH
3
CH
2 C1 Cl Cl CH 2
CH
2
CH
2 F
CO
2
CH
3
CH
2 Br F Cl CH 2
CH
2
CH
2 F
CO
2
CH
3
CH
2 Br C1 C1l CH 2
CH
2
CH
2 F TABLE 7 R13 R14 N 0 1 Y R1 N SO 2
R
2
R__
1
R_
2 X Y R 12 R1__3 R14 H CH 2 F F Cl H H H H CH 2 F Cl Cl H H H H CH 2 Cl F Cl H H H H CH 2 C1 Cl Cl H H H H CH 2 Br F Cl H H H H CH 2 Br Cl Cl H H H
C(=O)CH
3
CH
2 F F Cl H H H
C(=O)CH
3
CH
2 F Cl Cl H H H
C(=O)CH
3
CH
2 CI F Cl H H H
C(=O)CH
3
CH
2 Cl Cl Cl H H H
C(=O)CH
3
CH
2 Br F Cl H H H
C(=O)CH
3
CH
2 Br Cl Cl H H H
C(=O)CH(CH
3
)
2
CH
2 F F Cl H H H
C(=O)CH(CH
3
)
2
CH
2 F Cl C1l H H H
C(=O)CH(CH
3
)
2
CH
2 C F Cl H H H
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl H H H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H H H
C(=O)CH(CH
3
)
2
CH
2 Br C1 C1l H H H
CO
2
CH
3
CH
2 F F Cl H H H WO 98/47904 PCT/US98/08002 40
CO
2
CH
3
CH
2 F Cl Cl H H H
CO
2
CH
3
CH
2 C1 F Cl H H H
CO
2
CH
3
CH
2 CI Cl Cl H H H
CO
2
CH
3
CH
2 Br F Cl H H H
CO
2
CH
3
CH
2 Br Cl Cl H H H H CH 2 F F Cl H H CH 3 H CH 2 F Cl Cl H H CH 3 H CH 2 C1 F Cl H H CH 3 H CH 2 Cl Cl Cl H H CH 3 H CH 2 Br F Cl H H CH 3 H CH 2 Br Cl Cl H H CH 3
C(=O)CH
3
CH
2 F F Cl H H CH 3
C(=O)CH
3
CH
2 F Cl Cl H H CH 3
C(=O)CH
3
CH
2 CI F Cl H H CH 3
C(=O)CH
3
CH
2 Cl Cl Cl H H CH 3
C(=O)CH
3
CH
2 Br F Cl H H CH 3
C(=O)CH
3
CH
2 Br Cl Cl H H CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl H H CH 3 C(=O)CH(CH3) 2
CH
2 F Cl Cl H H CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl H H CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl H H CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H H CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl H H CH 3
CO
2
CH
3
CH
2 F F Cl H H CH 3
CO
2
CH
3
CH
2 F Cl Cl H H CH 3 CO2CH 3
CH
2 C1 F Cl H H CH 3
CO
2
CH
3
CH
2 C1 Cl Cl H H CH 3
CO
2
CH
3
CH
2 Br F Cl H H CH 3
CO
2
CH
3
CH
2 Br Cl Cl H H CH 3 H CH 2 F F Cl H CH 3
CH
3 H CH 2 F Cl Cl H CH 3
CH
3 H CH 2 Cl F Cl H CH 3
CH
3 H CH 2 CI Cl Cl H CH 3
CH
3 H CH 2 Br F Cl H CH 3
CH
3 H CH 2 Br Cl Cl H CH 3
CH
3
C(=O)CH
3
CH
2 F F Cl H CH 3
CH
3
C(=O)CH
3
CH
2 F Cl Cl H CH 3
CH
3
C(=O)CH
3
CH
2 Cl F Cl H CH 3
CH
3 WO 98/47904 PCTAUS98/08002 41
C(=O)CH
3
CH
2 C1 Cl Cl H CH 3
CH
3
C(=O)CH
3
CH
2 Br F Cl H CH 3
CH
3
C(=O)CH
3
CH
2 Br Cl Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl H CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br C1 C1 H CH 3
CH
3
CO
2
CH
3
CH
2 F F Cl H CH 3
CH
3
CO
2
CH
3
CH
2 F Cl Cl H CH 3
CH
3
CO
2
CH
3
CH
2 C1 F Cl H CH 3
CH
3
CO
2
CH
3
CH
2 C1 Cl Cl H CH 3
CH
3
CO
2
CH
3
CH
2 Br F Cl H CH 3
CH
3
CO
2
CH
3
CH
2 Br Cl Cl H CH 3
CH
3 H CH 2 F F Cl Cl H H H CH 2 F Cl Cl Cl H H H CH 2 C1 F C1 Cl H H H CH 2 C1 1 Cl Cl Cl H H H CH 2 Br F C1 Cl H H H CH 2 Br Cl C1 C1 H H
C(=O)CH
3
CH
2 F F Cl Cl H H
C(=O)CH
3
CH
2 F Cl Cl Cl H H
C(=O)CH
3
CH
2 C1 F C1 C1l H H
C(=O)CH
3
CH
2 C1 C1 1 Cl Cl H H
C(=O)CH
3
CH
2 Br F Cl Cl H H
C(=O)CH
3
CH
2 Br Cl C1 C1l H H
C(=O)CH(CH
3
)
2
CH
2 F F C1 C1l H H
C(=O)CH(CH
3
)
2
CH
2 F C1 Cl Cl H H
C(=O)CH(CH
3
)
2
CH
2 CI F C1 C1 H H
C(=O)CH(CH
3
)
2
CH
2 C1 C1 1 Cl Cl H H
C(=O)CH(CH
3
)
2
CH
2 Br F C1 Cl H H
C(=O)CH(CH
3
)
2
CH
2 Br C1 C1l Cl H H
CO
2
CH
3
CH
2 F F C1 Cl H H
CO
2
CH
3
CH
2 F Cl Cl Cl H H
CO
2
CH
3
CH
2 C1 F Cl Cl H H
CO
2
CH
3
CH
2 Cl Cl Cl Cl H H
CO
2
CH
3
CH
2 Br F C1 Cl H H WO 98/47904 PCT/US98/08002 42
CO
2
CH
3 CH,)Br Cl Cl Cl H H H CH 2 F F Cl Cl H CH 3 H CH 2 F Cl Cl Cl H CH 3 H CH 2 C1 F Cl Cl H CH 3 H CH 2 CI Cl Cl Cl H CH 3 H CH 2 Br F Cl Cl H CH 3 H CH 2 Br Cl Cl Cl H CH 3
C(=O)CH
3
CH
2 F F Cl Cl H CH 3
C(=O)CH
3
CH
2 F Cl Cl Cl H CH 3
C(=O)CH
3
CH
2 C1 F Cl Cl H CH 3
C(=O)CH
3
CH
2 C1 Cl Cl Cl H CH 3
C(=O)CH
3
CH
2 Br F Cl Cl H CH 3
C(=O)CH
3
CH
2 Br Cl Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl Cl H CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl Cl H CH 3
CO
2
CH
3
CH
2 F F Cl Cl H CH 3
CO
2
CH
3
CH
2 F Cl Cl Cl H CH 3
CO
2
CH
3
CH
2 CI F Cl Cl H CH 3
CO
2
CH
3
CH
2 Cl Cl Cl Cl H CH 3
CO
2
CH
3
CH
2 Br F Cl Cl H CH 3
CO
2
CH
3
CH
2 Br Cl Cl Cl H CH 3 H CH 2 F F Cl Cl CH 3
CH
3 H CH 2 F Cl Cl Cl CH 3
CH
3 H CH 2 CI F Cl Cl CH 3
CH
3 H CH 2 C1 Cl Cl Cl CH 3
CH
3 H CH 2 Br F Cl Cl CH 3
CH
3 H CH 2 )Br Cl Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 F F Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 F Cl Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 CI F Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 Cl Cl Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br F Cl Cl CH 3
CH
3
C(=O)CH
3
CH
2 Br Cl Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl Cl CH 3
CH
3 WO 98/47904 PCT/US98/08002 43
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl Cl CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl Cl CH 3
CH
3 CO2CH 3
CH
2 F F Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 F Cl Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Cl F Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 C1 Cl Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Br F Cl Cl CH 3
CH
3
CO
2
CH
3
CH
2 Br Cl Cl Cl CH 3
CH
3 H CH 2 F F Cl F H H H CH 2 F Cl Cl F H H H CH 2 C1 F Cl F H H H CH 2 Cl Cl Cl F H H H CH 2 Br F Cl F H H H CH 2 Br Cl Cl F H H
C(=O)CH
3
CH
2 F F Cl F H H
C(=O)CH
3
CH
2 F Cl Cl F H H
C(=O)CH
3
CH
2 Cl F Cl F H H
C(=O)CH
3
CH
2 C1 Cl Cl F H H
C(=O)CH
3
CH
2 Br F Cl F H H
C(=O)CH
3
CH
2 Br Cl Cl F H H
C(=O)CH(CH
3
)
2
CH
2 F F Cl F H H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl F H H
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl F H H
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl F H H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl F H H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl F H H
CO
2
CH
3
CH
2 F F Cl F H H
CO
2
CH
3
CH
2 F Cl Cl F H H
CO
2
CH
3
CH
2 CI F Cl F H H
CO
2
CH
3
CH
2 C1 Cl Cl F H H
CO
2
CH
3
CH
2 Br F Cl F H H
CO
2
CH
3
CH
2 Br Cl Cl F H H H CH 2 F F Cl F H CH 3 H CH 2 F Cl Cl F H CH 3 H CH 2 CI F Cl F H CH 3 WO 98/47904 PCTIUS98/08002 44 H CH 2 CI Cl Cl F H CH 3 H CH 2 Br F Cl F H CH 3 H CH 2 Br Cl Cl F H CH 3
C(=O)CH
3
CH
2 F F Cl F H CH 3
C(=O)CH
3
CH
2 F Cl Cl F H CH 3
C(=O)CH
3
CH
2 Cl F Cl F H CH 3
C(=O)CH
3
CH
2 C1 Cl Cl F H CH 3 C(0)CH 3
CH
2 Br F Cl F H CH 3 C(0)CH 3
CH
2 Br Cl Cl F H CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl F H CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl F H CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl F H CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl F H CH 3 C(0)CH(CH 3
)
2
CH
2 Br F Cl F H CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl F H CH 3
CO
2
CH
3
CH
2 F F Cl F H CH 3
CO
2
CH
3
CH
2 F Cl Cl F H CH 3
CO
2
CH
3
CH
2 C1 F Cl F H CH 3
CO
2
CH
3
CH
2 Cl Cl Cl F H CH 3
CO
2
CH
3
CH
2 Br F Cl F H CH 3
CO
2
CH
3
CH
2 Br Cl Cl F H CH 3 H CH 2 F F Cl F CH 3
CH
3 H CH 2 F Cl Cl F CH 3
CH
3 H CH 2 Cl F Cl F CH 3
CH
3 H CH 2 C1 Cl Cl F CH 3
CH
3 H CH 2 Br F Cl F CH 3
CH
3 H CH 2 Br Cl Cl F CH 3
CH
3
C(=O)CH
3
CH
2 F F Cl F CH 3
CH
3
C(=O)CH
3
CH
2 F Cl Cl F CH 3
CH
3
C(=O)CH
3
CH
2 Cl F Cl F CH 3
CH
3
C(=O)CH
3 CHCI Cl Cl F CH 3
CH
3
C(=O)CH
3
CH
2 Br F Cl F CH 3
CH
3
C(=O)CH
3
CH
2 Br Cl Cl F CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F F Cl F CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl F CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl F CH 3
CH
3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl F CH 3
CH
3 C(0)CH(CH 3
)
2
CH
2 Br F Cl F CH 3
CH
3 WO 98/47904 PCT/US98/08002 45
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl F CH 3
CH
3
CO
2
CH
3
CH
2 F F Cl F CH 3
CH
3
CO
2
CH
3
CH
2 F Cl Cl F CH 3
CH
3
CO
2
CH
3
CH
2 CI F Cl F CH 3
CH
3
CO
2
CH
3
CH
2 C1 Cl Cl F CH 3
CH
3
CO
2
CH
3
CH
2 Br F Cl F CH 3
CH
3
CO
2
CH
3
CH
2 Br Cl Cl F CH 3
CH
3 TABLE 8 R9X R15 R8 N'N -_ N-SO2R2 R1 / R R2 X Y R 8
R
9 R15 H CH 2 F F Cl CH 3 Cl H H CH 2 F Cl Cl CH 3 Cl H H CH 2 C1 F Cl CH 3 Cl H H CH 2 C1 Cl Cl CH 3 C1l H H CH 2 Br F Cl CH 3 Cl H H CH 2 Br Cl Cl CH 3 Cl H
C(=O)CH
3
CH
2 F F Cl CH 3 Cl H
C(=O)CH
3
CH
2 F Cl Cl CH 3 Cl H
C(=O)CH
3
CH
2 C F C CH 3 C1l H
C(=O)CH
3
CH
2 C1 Cl C1l CH 3 C1l H
C(=O)CH
3
CH
2 Br F Cl CH 3 Cl H
C(=O)CH
3
CH
2 Br C1 C1l CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 C Cl Cl CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Cl H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 C1l H
CO
2
CH
3
CH
2 F F CI CH 3 C1l H
CO
2
CH
3
CH
2 F Cl C1 CH 3 C1 H WO 98/47904 PCT/US98/08002 46
CO
2
CH
3
CH
2 CI F Cl CH 3 Cl H
CO
2
CH
3
CH
2 CI Cl Cl CH 3 Cl H
CO
2
CH
3
CH
2 Br F Cl CH 3 Cl H
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Cl H H CH 2 F F Cl CHC1 2 Cl H H CH 2 F Cl Cl CHC1 2 Cl H H CH 2 Cl F Cl CHC1 2 Cl H H CH 2 CI Cl Cl CHC1 2 Cl H H CH 2 Br F Cl CHC1 2 Cl H H CH 2 Br Cl Cl CHC1 2 Cl H
C(=O)CH
3
CH
2 F F Cl CHC1 2 Cl H
C(=O)CH
3
CH
2 F Cl Cl CHC1 2 Cl H
C(=O)CH
3
CH
2 C1 F Cl CHC1 2 Cl H
C(=O)CH
3
CH
2 C1 Cl Cl CHC1 2 Cl H
C(=O)CH
3
CH
2 Br F Cl CHC1 2 Cl H C(0)CH 3
CH
2 Br Cl Cl CHC1 2 Cl H
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 Cl H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHC1 2 Cl H
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CHC1 2 Cl H
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CHC1 2 Cl H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 Cl H
C(=O)CHI(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 F F Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 C1 F Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 CI Cl Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 Br F Cl CHC1 2 Cl H
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 Cl H H CH 2 F F Cl CH 3 Br H H CH 2 F Cl Cl CH 3 Br H H CH 2 CI F Cl CH 3 Br H H CH 2 Cl Cl Cl CH 3 Br H H CH 2 Br F Cl CH 3 Br H H CH 2 Br Cl Cl CH 3 Br H C(0)CH 3
CH
2 F F Cl CH 3 Br H C(0)CH 3
CH
2 F Cl Cl CH 3 Br H C(0)CH 3
CH
2 C1 F Cl CH 3 Br H C(0)CH 3
CH
2 Cl Cl Cl CH 3 Br H WO 98/47904 PCT/US98/08002 47
C(=O)CH
3
CH
2 Br F Cl CH 3 Br H
C(=O)CH
3
CH
2 Br Cl Cl CH 3 Br H
C(=O)CH(CH
3
)
2 CH2F F Cl CH 3 Br H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Br H
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 3 Br H
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CH 3 Br H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Br H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 Br H
CO
2
CH
3
CH
2 F F Cl CH 3 Br H
CO
2
CH
3
CH
2 F Cl Cl CH 3 Br H
CO
2
CH
3
CH
2 CI F Cl CH 3 Br H
CO
2
CH
3
CH
2 Cl Cl Cl CH 3 Br H
CO
2
CH
3
CH
2 Br F Cl CH 3 Br H
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Br H H CH 2 F F Cl CHCl 2 Br H H CH 2 F Cl Cl CHC1 2 Br H H CH 2 Cl F Cl CHC1 2 Br H H CH 2 CI Cl Cl CHCl 2 Br H H CH 2 Br F Cl CHC1 2 Br H H CH 2 Br Cl Cl CHCl 2 Br H
C(=O)CH
3
CH
2 F F Cl CHCl 2 Br H
C(=O)CH
3
CH
2 F Cl Cl CHC1 2 Br H
C(=O)CH
3
CH
2 Cl F Cl CHC1 2 Br H
C(=O)CH
3
CH
2 Cl Cl Cl CHC1 2 Br H
C(=O)CH
3
CH
2 Br F Cl CHCl 2 Br H
C(=O)CH
3
CH
2 Br Cl Cl CHC1 2 Br H
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 Br H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHC1 2 Br H
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CHC1 2 Br H
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CHCl 2 Br H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 Br H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Br H
CO
2
CH
3
CH
2 F F Cl CHC1 2 Br H
CO
2
CH
3
CH
2 F Cl Cl CHCl 2 Br H
CO
2
CH
3
CH
2 CI F Cl CHC1 2 Br H
CO
2
CH
3
CH
2 Cl Cl Cl CHCl 2 Br H
CO
2
CH
3
CH
2 Br F Cl CHCl 2 Br H
CO
2
CH
3
CH
2 Br Cl Cl CHCl 2 Br H WO 98/47904 PCT/US98/08002 48 H CH 2 F F Cl CH 3 CN H H CH 2 F Cl Cl CH 3 CN H H CH 2 C1 F Cl CH 3 CN H H CH 2 Cl Cl Cl CH 3 CN H H CH 2 Br F Cl CH 3 CN H H CH 2 Br Cl Cl CH 3 CN H
C(=O)CH
3
CH
2 F F Cl CH 3 CN H
C(=O)CH
3
CH
2 F Cl Cl CH 3 CN H
C(=O)CH
3
CH
2 CI F Cl CH 3 CN H
C(=O)CH
3
CH
2 Cl Cl Cl CH 3 CN H
C(=O)CH
3
CH
2 Br F Cl CH 3 CN H
C(=O)CH
3
CH
2 Br Cl Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 CN H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 CN H
CO
2
CH
3
CH
2 F F Cl CH 3 CN H
CO
2
CH
3
CH
2 F Cl Cl CH 3 CN H
CO
2
CH
3
CH
2 CI F Cl CH 3 CN H
CO
2
CH
3
CH
2 CI Cl Cl CH 3 CN H
CO
2
CH
3
CH
2 Br F Cl CH 3 CN H
CO
2
CH
3
CH
2 Br Cl Cl CH 3 CN H H CH 2 F F Cl CHC1 2 CN H H CH 2 F Cl Cl CHCl 2 CN H H CH 2 CI F Cl CHC1 2 CN H H CH 2 Cl Cl Cl CHC1 2 CN H H CH 2 Br F Cl CHCl 2 CN H H CH 2 Br Cl Cl CHCl 2 CN H
C(=O)CH
3
CH
2 F F Cl CHC1 2 CN H
C(=O)CH
3
CH
2 F Cl Cl CHCl 2 CN H
C(=O)CH
3
CH
2 CI F Cl CHCI 2 CN H
C(=O)CH
3
CH
2 C1 Cl Cl CHC1 2 CN H
C(=O)CH
3
CH
2 Br F Cl CHCl 2 CN H
C(=O)CH
3
CH
2 Br Cl Cl CHCl 2 CN H
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHCl 2 CN H
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHCl 2 CN H WO 98/47904 PCT/US98/08002 49
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CHC1 2 CN H
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CHC1 2 CN H
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 CN H
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 CN H
CO.
2
CH
3
CH
2 F F Cl CHC1 2 CN H
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 CN H
CO
2
CH
3
CH
2 CI F Cl CHC1 2 CN H
CO
2
CH
3
CH
2 C1 Cl Cl CHC1 2 CN H
CO
2
CH
3
CH
2 Br F Cl CHC1 2 CN H
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 CN H H CH 2 F F Cl CH 3 Cl CH 3 H CH 2 F Cl Cl CH 3 Cl CH 3 H CH 2 C1 F Cl CH 3 Cl CH 3 H CH 2 Cl Cl Cl CH 3 Cl CH 3 H CH 2 Br F Cl CH 3 Cl CH 3 H CH 2 Br Cl Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 F F Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 Cl F Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 Br F Cl CH 3 Cl CH 3
C(=O)CH
3
CH
2 Br Cl Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 F F Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 F Cl Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 C1 F Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 Br F Cl CH 3 Cl CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Cl CH 3 H CH 2 F F Cl CHC1 2 Cl CH 3 H CH 2 F Cl Cl CHC1 2 Cl CH 3 H CH 2 C1 F Cl CHC1 2 Cl CH 3 H CH 2 Cl Cl Cl CHC1 2 Cl CH 3 WO 98/47904 PCT/US98/08002 50 H CH 2 Br F Cl CHC1 2 Cl CH 3 H CH 2 Br Cl C1l CHCI 2 C1l CH 3
C(=O)CH
3
CH
2 F F Cl CHC1 2 Cl CH 3
C(=O)CH
3
CH
2 F Cl Cl CHC1 2 Cl CH 3
C(=O)CH
3
CH
2 CI F C1 CHC1 2 Cl CH 3
C(=O)CH
3
CH
2 CI Cl Cl CHC1 2 Cl CH 3
C(=O)CH
3
CH
2 Br F Cl CHC1 2 Cl CH 3
C(=O)CH
3
CH
2 Br C1 Cl CHC1 2 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHC1 2 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CHCl 2 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CHC1 2 C1 CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHCl 2 Cl CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Cl CH 3
CO
2
CH
3
CH
2 F F Cl CHCl 2 Cl CH 3
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 Cl CH 3
CO
2
CH
3
CH
2 C1 F Cl CHC1 2 C1l CH 3
CO
2
CH
3
CH
2 C1 Cl Cl CHC1 2 C1 CH 3
CO
2
CH
3
CH
2 Br F Cl CHC1 2 C1l CH 3
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 Cl CH 3 H CH 2 F F Cl CH 3 Br CH 3 H CH 2 F Cl Cl CH 3 Br CH 3 H CH 2 C1 F Cl CH 3 Br CH 3 H CH 2 CI Cl Cl CH 3 Br CH 3 H CH 2 Br F Cl CH 3 Br CH 3 H CH 2 Br Cl Cl CH 3 Br CH 3
C(=O)CH
3
CH
2 F F Cl CH 3 Br CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 Br CH 3
C(=O)CH
3
CH
2 Cl F Cl CH 3 Br CH 3
C(=)CH
3
CH
2 C1 Cl Cl CH 3 Br CH 3
C(=O)CH
3 CH2Br F C CH 3 Br CH 3
C(=O)CH
3
CH
2 Br C1 Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 Br C1 Cl CH 3 Br CH 3 WO 98/47904 PCTIUS98/08002 51
CO
2
CH
3
CH
2 F F Cl CH 3 Br CH 3
CO
2
CH
3
CH
2 F CI Cl CH 3 Br CH 3
CO
2
CH
3
CH
2 C1 F Cl CH 3 Br CH 3
CO
2
CH
3
CH
2 CI Cl Cl CH 3 Br CH 3
CO
2
CH
3
CH
2 Br F Cl CH 3 Br CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Br CH 3 H CH 2 F F Cl CHC1 2 Br CH 3 H CH 2 F Cl Cl CHC1 2 Br CH 3 H CH 2 CI F Cl .CHC1 2 Br CH 3 H CH 2 C1 Cl Cl CHC1 2 Br CH 3 H CH 2 Br F Cl CHC1 2 Br CH 3 H CH 2 Br Cl Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 F F Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 F Cl Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 C1 F Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 Cl Cl Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 Br F Cl CHC1 2 Br CH 3 C(0)CH 3
CH
2 Br Cl Cl CHC1 2 Br CH 3 C(0)CH(CH 3
)
2
CH
2 F F Cl CHC1 2 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHC1 2 Br CH 3 C(=o)CH(CH 3
)
2
CH
2 C1 F Cl CHC1 2 Br CH 3 C(0)CH(CH 3
)
2
CH
2 Cl' Cl Cl CHC1 2 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 Br CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 F F Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 CI F Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 Br F Cl CHC1 2 Br CH 3
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 Br CH 3 H CH 2 F F Cl CH 3 CN CH 3 H CH 2 F Cl Cl CH 3 CN CH 3 H CH 2 Cl F Cl CH 3 CN CH 3 H CH 2 C1 Cl Cl CH 3 CN CH 3 H CH 2 Br F Cl CH 3 CN CH 3 H CH 2 Br Cl Cl CH 3 CN CH 3
C(=O)CH
3
CH
2 F F Cl CH 3 CN CH 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 CN CH 3 WO 98/47904 PCTJUS98/08002 52
C(=O)CH
3
CH
2 CI F Cl CH 3 CN CH 3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3 CN CH 3
C(=O)CH
3
CH
2 Br F Cl CH 3 CN CH 3
C(=O)CH
3
CH
2 Br Cl Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 CN CH 3
CO
2
CH
3
CH
2 F F Cl CH 3 CN CH 3
CO
2
CH
3
CH
2 F Cl Cl CH 3 CN CH 3 C0 2
CH
3
CH
2 CI F Cl CH 3 CN CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3 CN CH 3
CO
2
CH
3
CH
2 Br F Cl CH 3 CN CH 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 CN CH 3 H CH 2 F F Cl CHC1 2 CN CH 3 H CH 2 F Cl Cl CHC1 2 CN CH 3 H CH 2 C1 F Cl CHC1 2 CN CH 3 H CH 2 C1 Cl Cl CHC1 2 CN CH 3 H CH 2 Br F Cl CHC1 2 CN CH 3 H CH 2 Br Cl Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 F F.- Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 F Cl Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 CI F Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 C1 Cl Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 Br F Cl CHC1 2 CN CH 3
C(=O)CH
3
CH
2 Br Cl Cl CHC1 2 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHC1 2 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CHC1 2 CN CH 3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CHC1 2 CN CH 3
CQ=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 CN CH 3 C(0)CH(CH 3
)
2
CH
2 Br Cl Cl CHC1 2 CN CH 3
CO
2
CH
3
CH
2 F F Cl CHC1 2 CN CH 3
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 CN CH 3
CO
2
CH
3
CH
2 CI F Cl CHC1 2 CN CH 3
CO
2
CH
3
CH
2 Cl Cl Cl CHC1 2 CN CH 3 WO 98/47904 PCT/US98/08002 53
CO
2
CH
3
CH
2 Br F CI CHCI 2 CN CH 3 CO2CH 3
CH
2 Br Cl Cl CHC1 2 CN CH 3 H CH 2 F F Cl CH 3 Cl CF 3 H CH 2 F Cl Cl CH 3 Cl CF 3 H CH 2 C1 F Cl CH 3 Cl CF 3 H CH 2 C1 Cl Cl CH 3 Cl CF 3 H CH 2 Br F Cl CH 3 Cl CF 3 H CH 2 Br Cl Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 F F Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 CI F Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 Cl Cl Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 Br F Cl CH 3 Cl CF 3
C(=O)CH
3
CH
2 Br Cl Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 F F Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 F Cl Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 C1 F Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 Br F Cl CH 3 Cl CF 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Cl CF 3 H CH 2 F F Cl CHC1 2 Cl CF 3 H CH 2 F Cl Cl CHCI 2 Cl CF 3 H CH 2 CI F Cl CHC1 2 Cl CF 3 H CH 2 C1 Cl Cl CHCl 2 Cl CF 3 H CH 2 Br F Cl CHC1 2 Cl CF 3 H CH 2 Br Cl Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 F F Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 F Cl Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 CI F Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 CI Cl Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 Br F Cl CHC1 2 Cl CF 3
C(=O)CH
3
CH
2 Br Cl Cl CHCl 2 Cl CF 3 WO 98/47904 PCT/US98/08002 54
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHCl 2 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CHC1 2 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CHC1 2 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHCl 2 Cl CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Cl CF 3
CO
2
CH
3
CH
2 F F Cl CHCl 2 Cl CF 3
CO
2
CH
3
CH
2 F Cl Cl CHC1 2 Cl CF 3
CO
2
CH
3
CH
2 Cl F Cl CHCl 2 Cl CF 3
CO
2
CH
3
CH
2 CI Cl Cl CHCl 2 Cl CF 3
CO
2
CH
3
CH
2 Br F Cl CHCl 2 Cl CF 3
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 Cl CF 3 H CH 2 F F Cl CH 3 Br CF 3 H CH 2 F Cl Cl CH 3 Br CF 3 H CH 2 C1 F Cl CH 3 Br CF 3 H CH 2 CI Cl Cl CH 3 Br CF 3 H CH 2 Br F Cl CH 3 Br CF 3 H CH 2 Br Cl Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 F F Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 C1 F Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 C1 Cl Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 Br F Cl CH 3 Br CF 3
C(=O)CH
3
CH
2 Br Cl Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 Cl Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 F F Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 F Cl Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 C1 F Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 C1 Cl Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 Br F Cl CH 3 Br CF 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 Br CF 3 H CH 2 F F Cl CHC1 2 Br CF 3 H CH 2 F Cl Cl CHCl 2 Br CF 3 WO 98/47904 PCT/US98/08002 55 H CH 2 CI F Cl CHC1 2 Br CF 3 H CH 2 CI Cl Cl CHC1 2 Br CF 3 H CH 2 Br F Cl CHCl 2 Br CF 3 H CH 2 Br Cl Cl CHC1 2 Br CF 3
C(=O)CH
3
CH
2 F F Cl CHC1 2 Br CF 3
C(=O)CH
3
CH
2 F Cl Cl CHCl 2 Br CF 3
C(=O)CH
3
CH
2 Cl F Cl CHC1 2 Br CF 3
C(=O)CH
3
CH
2 C1 Cl Cl CHCl 2 Br CF 3
C(=O)CH
3
CH
2 Br F Cl CHCl 2 Br CF 3
C(=O)CH
3
CH
2 Br Cl Cl CHC1 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHC1 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHCl 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 C1 F Cl CHCl 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 CI Cl Cl CHC1 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHCl 2 Br CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 Br CF 3
CO
2
CH
3
CH
2 F F Cl CHC1 2 Br CF 3
CO
2
CH
3
CH
2 F Cl Cl CHCl 2 Br CF 3
CO
2
CH
3
CH
2 C1 F Cl CHC1 2 Br CF 3
CO
2
CH
3
CH
2 Cl Cl Cl CHC1 2 Br CF 3
CO
2
CH
3
CH
2 Br F Cl CHCl 2 Br CF 3
CO
2
CH
3
CH
2 Br Cl Cl CHCl 2 Br CF 3 H CH 2 F F Cl CH 3 CN CF 3 H CH 2 F Cl Cl CH 3 CN CF 3 H CH 2 CI F Cl CH 3 CN CF 3 H CH 2 CI Cl Cl CH 3 CN CF 3 H CH 2 Br F Cl CH 3 CN CF 3 H CH 2 Br Cl Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 F F Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 F Cl Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 CI F Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 C1 Cl Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 Br F Cl CH 3 CN CF 3
C(=O)CH
3
CH
2 Br Cl Cl CH 3 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CH 3 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CH 3 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Cl F Cl CH 3 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CH 3 CN CF 3 WO 98/47904 PCT/US98/08002 56
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CH 3 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CH 3 CN CF 3
CO
2
CH
3
CH
2 F F Cl CH 3 CN CF 3
CO
2
CH
3
CH
2 F Cl Cl CH 3 CN CF 3
CO
2
CH
3
CH
2 Cl F Cl CH 3 CN CF 3
CO
2
CH
3
CH
2 Cl Cl Cl CH 3 CN CF 3 CO2CH 3
CH
2 Br F Cl CH 3 CN CF 3
CO
2
CH
3
CH
2 Br Cl Cl CH 3 CN CF 3 H CH 2 F F Cl CHCl 2 CN CF 3 H CH 2 F Cl Cl CHCl 2 CN CF 3 H CH 2 Cl F Cl CHCl 2 CN CF 3 H CH 2 CI Cl Cl CHCl 2 CN CF 3 H CH 2 Br F Cl CHCI 2 CN CF 3 H CH 2 Br Cl Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 F F Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 F Cl Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 Cl F Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 CI Cl Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 Br F Cl CHCl 2 CN CF 3
C(=O)CH
3
CH
2 Br Cl Cl CHCl 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 F F Cl CHCl 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 F Cl Cl CHCl 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 CI F Cl CHCl 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Cl Cl Cl CHCl 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Br F Cl CHC1 2 CN CF 3
C(=O)CH(CH
3
)
2
CH
2 Br Cl Cl CHC1 2 CN CF 3
CO
2
CH
3
CH
2 F F Cl CHCl 2 CN CF 3
CO
2
CH
3
CH
2 F Cl Cl CHCl 2 CN CF 3
CO
2
CH
3
CH
2 Cl F Cl CHC1 2 CN CF 3
CO
2
CH
3
CH
2 C1 Cl Cl CHC1 2 CN CF 3
CO
2
CH
3
CH
2 Br F Cl CHCl 2 CN CF 3
CO
2
CH
3
CH
2 Br Cl Cl CHC1 2 CN CF 3 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 WO 98/47904 PCT/US98/08002 57 environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, 5 powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used 10 at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight. Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders. Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.01-99 5-99.99 0-15 High Strength Compositions 90-99 0-10 0-2 15 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. 20 Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl 25 sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, WO 98/47904 PCT/US98/08002 58 diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, 5 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 .0 hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, 5 and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. :0 For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, 5 pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-C. 0 Example A High Strength Concentrate Compound 3 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
WO 98/47904 PCT/US98/08002 59 Example B Wettable Powder Compound 5 65.0% dodecylphenol polyethylene glycol ether 2.0% 5 sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example C Granule 10 Compound 7 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example D Extruded Pellet 15 Compound 17 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. 20 Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around 25 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 30 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. 35 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 WO 98/47904 PCT/US98/08002 60 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, 0 azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIAO500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlomrnitrofen, chlorotoluron, chlorpropham, chlorsulfuron, 5 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, 0 dimethylamnmonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, 2-[4,5-dihydro-4-methyl-4-(1 -methylethyl)-5-oxo- 1H-imidazol-2-yl]-5-methyl-3 pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, 5 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, 0 fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, 5 ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and WO 98/47904 PCT/US98/08002 61 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)- 1 H-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, 5 metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram, picloramin-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, simazine, sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, 15 triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vemrnolate. 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. .0 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 "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. :5 WO 98/47904 PCT/US98/08002 62 INDEX TABLE A F N- Cl | S N- SO 2
CH
2 CI z N
R
1 / o 0 Cmd Z RI mp (C) 1 (Ex. 1) CH 2 H 168 2 CH 2
C(=O)CH
3 130 3 (Ex. 2) CH 2
C(=O)CH(CH
3
)
2 183 4 CH 2
SO
2
CH
2 C1 136 5 O H * * see Index Table D for 1 H NMR data INDEX TABLE B R10 I N O Y RI
N
' SO2CH2CI Cmd X Y RI RIO Rl my (C) 6 Cl Cl SO 2
CH
2 Cl CH 3
CF
3 * 7 Cl Cl H CH 3
CF
3 90 8 (Ex. 3) F Cl H CH 3
CF
3 92 9 F Cl SO 2
CH
2 Cl CH 2
CH=CH
2
CF
3 * 10 F Cl H CH 2
CH=CH
2
CF
3 * 11 F Cl H CH 2 C-CH CF 3
*
WO 98/47904 PCT/US98/08002 63 12 F Cl CH 3
CH
3
CF
3 177 13 F Cl CH 2
CH
3
CH
3
CF
3 225 14 (Ex. 4) F Cl C(=O)CH 3
CH
3
CF
3 170 15 F Cl SO 2
CH
2 C1 CH 3
CF
3 112 16 F Cl CO 2
CH
3
CH
3
CF
3 110 17 F Cl CH 2 C-CH CH 3
CF
3 138 * see Index Table D for 1 H NMR data INDEX TABLE C Cmvd Structure mp (C) 18 CH 3 205 I
CF
3 O "Y C N 0 C1CH2CH 2
CH
2 SO2 N SO 2
CH
2
CH
2
CH
2 C1 19 CH 2 C- CH 185-188
CF
3 N 0 F Cl HN SO2CHC12 INDEX TABLE D Cmpd No. 1 H NMR Data (CDCl 3 solution unless indicated otherwise)a 5 8 7.3 (d, 1H), 7.2 (d, 1H), 6.9 (br s, 1H), 5.1 (s, 2H), 4.6 (s, 2H), 4.0 (m, 2H), 3.8 (m, 2H). 6 8 7.48 (s, 1H), 6.64 (s, 1H), 6.40 (s, 1H), 4.55 (s, 4H), 3.57 (s, 3H). 9 8 7.68 (d, 1H), 7.44 (d, 1H), 6.36 (s, 1H), 5.86 (m, 1H), 5.30 (m, 2H), 5.28 and 4.86 (q, 4H), 4.56 (m, 2H).
WO 98/47904 PCT/US98/08002 64 10 8 7.68 (d, 1H), 7.39 (d, 1H), 7.04 (s, 1H), 6.37 (s, 1H), 5.90 (m, 1H), 5.28 (m, 2H), 4.56 (m, 2H), 4.50 (s, 2H). 11 68 8.0 (s, IH), 7.65 (d, 1H), 7.38 (d, 1H), 6.4 (s, 1H), 4.71 (d, 2H), 4.55 (s, 2H), 2.4 (m, 1H). a 1 H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet. 5 BIOLOGICAL EXAMPLES OF THE INVENTION Test A Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), 10 cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild 15 buckwheat (Polygonum convolvulus), wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 20 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. 25 Table A COMPOUND Rate 20.0 g/ha 6 7 12 13 14 15 16 18 19 POSTEMERGENCE Barley 9 9 3 3 10 10 8 0 0 Barnyardgrass 9 9 5 7 10 10 10 1 1 Bedstraw 10 10 9 8 10 10 10 0 6 Blackgrass 2 4 3 2 8 8 8 0 2 Chickweed 5 8 10 10 10 10 10 0 3 Cocklebur 10 10 10 10 10 10 10 0 3 WO 98/47904 PCT/US98/08002 65 Corn 9 9 4 6 8 7 8 0 2 Cotton 10 10 10 10 10 10 10 2 8 Crabgrass 2 3 4 5 7 6 5 1 2 Downy brome 5 9 2 1 5 6 6 0 0 Giant foxtail 9 9 4 6 8 5 7 1 2 Lambsquarters 9 10 10 10 10 10 10 5 6 Morningglory 10 10 10 10 10 10 10 1 5 Nutsedge 3 2 5 2 9 6 10 0 Rape 10 10 10 8 10 10 10 0 2 Rice 9 10 5 5 10 10 10 0 2 Sorghum 8 9 8 9 - 9 8 1 2 Soybean 10 10 8 8 9 10 9 2 4 Sugar beet 10 10 10 10 10 10 10 0 3 Velvetleaf 10 10 10 8 10 10 10 1 6 Wheat 9 9 5 3 10 9 10 0 0 Wild buckwheat 10 10 10 10 10 10 10 1 6 Wild oat 9 9 3 4 6 5 7 0 2 Table A COMPOUND Rate 200 g/ha 6 7 12 13 14 15 16 18 19 PREEMERGENCE Barley 7 7 4 3 5 4 6 - 0 Barnyardgrass 3 8 9 10 9 9 10 0 0 Bedstraw 10 10 10 10 10 10 10 - 0 Blackgrass 3 3 6 6 9 9 10 - 0 Chickweed 6 6 10 10 10 10 10 - 0 Cocklebur 9 10 10 10 10 10 10 0 0 Corn 3 2 7 7 3 2 3 0 0 Cotton 6 9 9 10 10 10 10 0 0 Crabgrass 1 1 9 10 8 7 8 0 0 Downy brome 9 7 5 2 10 10 8 - 0 Giant foxtail 6 9 7 10 8 9 9 0 0 Lambsquarters 10 10 10 10 10 10 10 - 0 Morningglory 10 10 10 10 10 10 10 0 0 Nutsedge 4 0 6 4 7 4 10 0 Rape 9 10 10 9 10 10 10 - 0 Rice 7 9 8 7 9 9 8 0 0 Sorghum 0 2 6 7 5 6 0 0 0 WO 98/47904 PCT/US98/08002 66 Soybean 4 9 9 10 10 10 6 0 0 Sugar beet 10 10 10 10 10 10 10 - 0 Velvetleaf 8 10 10 10 10 10 10 0 0 Wheat 8 9 7 6 8 6 6 - 0 Wild buckwheat 5 5 10 10 10 10 10 - 0 Wild oat 9 9 7 9 9 9 9 - 0 Table A COMPOUND Table A COMPOUND Rate 100 g/ha 17 Rate 100 g/ha 17 POSTEMERGENCE PREEMERGENCE Barley 4 Barley 0 Barnyardgrass 10 Barnyardgrass 9 Bedstraw - Bedstraw 10 Blackgrass - Blackgrass 4 Chickweed 7 Chickweed 10 Cocklebur 9 Cocklebur 4 Corn 8 Corn 4 Cotton 10 Cotton 5 Crabgrass 2 Crabgrass 8 Downy brome 4 Downy brome 3 Giant foxtail 5 Giant foxtail 6 Lambsquarters 10 Lambsquarters 10 Morningglory 10 Morningglory 10 Nutsedge - Nutsedge 3 Rape 10 Rape 10 Rice 4 Rice 7 Sorghum 8 Sorghum 6 Soybean 8 Soybean 9 Sugar beet 10 Sugar beet 10 Velvetleaf 10 Velvetleaf 10 Wheat 3 Wheat 0 Wild buckwheat 10 Wild buckwheat 10 Wild oat 4 Wild oat 10 Table A COMPOUND Rate 50 g/ha 1 2 3 4 5 6 7 8 9 10 12 13 14 15 16 18 19 POSTEMERGENCE Barley 5 3 4 3 3 5 7 7 2 3 3 3 3 5 7 0 0 WO 98/47904 PCT/US98/08002 67 Barnyardgrass 5 3 2 4 3 8 9 10 3 4 1 3 10 10 10 1 1 Bedstraw 7 8 9 7 6 9 10 9 8 9 8 8 9 10 10 0 4 Blackgrass 2 2 2 2 3 1 3 4 2 3 2 1 4 3 7 0 1 Chickweed 7 6 4 5 4 4 6 10 3 7 7 9 10 10 10 0 2 Cocklebur 10 9 10 10 1 0 10 10 6 6 7 8 10 10 10 0 2 Corn 7 8 7 1 8 7 9 7 2 1 2 2 8 1 7 0 2 Cotton 10 10 10 10 10 10 10 10 9 10 10 10 10 10 10 1 4 Crabgrass 2 2 2 1 2 2 1 4 3 4 3 3 5 3 3 0 1 Downy brome 4 3 3 3 3 5 8 4 2 2 2 1 4 3 4 0 0 Giant foxtail 3 2 2 1 2 9 9 4 2 2 3 4 6 4 3 1 1 Lambsquarters 9 9 9 9 9 9 9 10 7 8 9 9 10 10 10 6 6 Morningglory 9 7 10 10 8 10 10 10 7 8 10 8 10 10 10 1 2 Nutsedge 1 1 1 1 1 - 2 4 2 1 2 2 7 5 10 - Rape 8 8 9 9 7 7 8 10 7 6 6 6 10 10 10 0 2 Rice 3 2 3 2 2 7 9 9 4 4 4 4 8 9 8 0 1 Sorghum 5 2 1 2 6 7 9 8 4 3 2 - 7 3 4 1 1 Soybean 2 2 2 2 2 9 7 6 5 3 8 7 9 9 9 1 3 Sugar beet 10 10 10 10 10 9 10 10 8 9 10 10 10 10 10 0 3 Velvetleaf 10 10 10 10 10 10 10 10 6 8 6 6 10 10 10 1 2 Wheat 4 3 3 2 4 8 9 9 2 3 3 1 8 6 8 0 0 Wild buckwheat 10 10 10 10 10 9 10 10 6 9 10 10 10 10 10 0 3 Wild oat 3 3 2 2 3 5 9 4 1 3 2 1 3 2 3 0 1 Table A COMPOUND Rate 50 g/ha 1 2 3 4 5 6 7 8 9 10 12 13 14 15 16 18 19 PREEMERGENCE Barley 0 0 0 0 0 3 4 1 0 2 0 0 0 0 2 0 0 Barnyardgrass 0 0 0 0 0 0 0 3 3 0 2 7 6 5 8 0 0 Bedstraw 1 9 8 7 7 7 6 10 0 8 9 10 10 10 10 0 0 Blackgrass 1 0 0 0 1 0 0 7 0 0 0 1 6 9 5 0 0 Chickweed 0 0 0 0 4 3 3 10 1 9 10 10 10 10 10 0 0 Cocklebur 0 9 0 0 0 3 8 10 0 0 7 10 10 10 10 0 0 Corn 0 0 0 0 0 0 0 0 0 0 3 4 0 0 0 0 0 Cotton 0 10 0 0 0 0 3 10 3 0 8 8 10 10 10 0 0 Crabgrass 1 0 0 0 0 0 0 7 3 0 4 9 3 3 0 0 0 Downy brome 0 0 0 0 0 5 5 8 0 0 4 2 7 5 5 0 0 Giant foxtail 0 0 0 0 0 2 5 3 3 0 3 5 0 0 5 0 0 Lambsquarters 9 10 10 10 10 9 9 10 6 9 10 10 10 10 10 0 0 WO 98/47904 PCT/US98/08002 68 Morningglory 0 2 3 1 0 8 8 10 0 0 6 10 10 10 10 0 0 Nutsedge 0 4 0 0 0 - 0 8 0 0 6 2 6 3 4 0 Rape 0 5 0 0 7 0 4 10 0 0 8 7 10 10 10 0 0 Rice 0 0 0 0 0 0 0 5 0 0 5 6 5 3 6 0 0 Sorghum 0 0 0 0 0 0 0 1 4 0 0 3 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 6 3 0 9 6 9 0 6 0 0 Sugar beet 9 10 10 9 10 7 9 10 9 4 10 10 10 10 10 0 0 Velvetleaf 10 10 10 10 10 4 10 10 3 0 10 10 10 10 10 0 0 Wheat 0 0 0 0 0 4 6 1 0 0 0 2 3 0 3 0 0 Wild buckwheat 0 0 0 0 7 2 3 10 0 3 10 10 10 10 10 0 0 Wild oat 0 0 0 0 1 6 9 6 0 0 5 4 6 4 7 0 0 Table A COMPOUND Table A COMPOUND Rate 20 g/ha 17 Rate 20 g/ha 17 POSTEMERGENCE PREEMERGENCE Barley 3 Barley 0 Barnyardgrass 3 Barnyardgrass 5 Bedstraw - Bedstraw 10 Blackgrass - Blackgrass 2 Chickweed 6 Chickweed 0 Cocklebur 7 Cocklebur 3 Corn 2 Corn 0 Cotton 9 Cotton 0 Crabgrass 2 Crabgrass 1 Downy brome 4 Downy brome 1 Giant foxtail 2 Giant foxtail 1 Lambsquarters 9 Lambsquarters 10 Morningglory 10 Morningglory 10 Nutsedge - Nutsedge Rape 10 Rape 9 Rice 3 Rice 2 Sorghum 4 Sorghum 0 Soybean 8 Soybean 0 Sugar beet 10 Sugar beet 10 Velvetleaf 3 Velvetleaf 10 Wheat 3 Wheat 0 Wild buckwheat 10 Wild buckwheat 10 Wild oat 3 Wild oat 4 WO 98/47904 PCT/US98/08002 69 Table A COMPOUND Rate 10 g/ha 1 2 3 4 5 8 9 10 POSTEMERGENCE Barley 3 2 3 3 3 3 1 2 Barnyardgrass 3 2 1 2 2 3 2 2 Bedstraw 6 7 5 7 6 8 6 9 Blackgrass 2 1 2 1 1 3 0 1 Chickweed 3 3 3 4 3 10 2 4 Cocklebur 8 7 8 8 10 10 6 2 Corn 1 1 1 1 1 1 2 1 Cotton 10 10 10 10 10 10 7 10 Crabgrass 1 1 1 1 1 2 1 2 Downy brome 3 2 2 2 3 3 1 1 Giant foxtail 2 1 1 1 1 2 1 2 Lambsquarters 9 9 9 9 9 9 3 4 Morningglory 4 8 8 10 3 10 6 6 Nutsedge 1 1 0 0 1 1 0 1 Rape 3 5 7 6 5 10 3 1 Rice 2 2 1 2 1 7 3 2 Sorghum 2 1 1 1 2 1 2 2 Soybean 2 2 2 2 1 6 3 2 Sugar beet 10 10 10 10 10 10 8 4 Velvetleaf 10 10 10 10 10 10 6 5 Wheat 2 1 2 2 2 4 1 2 Wild buckwheat 9 10 8 10 8 9 4 7 Wild oat 3 2 2 2 2 3 1 2 Table A COMPOUND Rate 10 g/ha 1 2 3 4 5 8 9 10 PREEMERGENCE Barley 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 Bedstraw - 4 0 5 6 10 0 3 Blackgrass 0 0 0 0 0 0 0 0 Chickweed 0 0 0 0 3 9 0 0 Cocklebur 0 0 0 0 0 10 - 0 Corn 0 0 0 0 0 0 0 0 WO 98/47904 PCT/US98/08002 70 Cotton 0 0 0 0 0 0 3 0 Crabgrass 0 0 0 0 0 0 2 0 Downy brome 0 0 0 0 0 3 0 0 Giant foxtail 0 0 0 0 0 0 2 0 Lambsquarters 4 9 9 9 9 10 0 7 Morningglory 0 0 0 0 0 10 0 0 Nutsedge 0 2 0 0 0 2 - 0 Rape 0 0 0 0 4 10 0 0 Rice 0 0 0 0 0 1 0 0 Sorghum 0 0 0 0 0 0 3 0 Soybean 0 0 0 0 0 2 2 0 Sugar beet 3 0 3 0 10 10 0 0 Velvetleaf 10 10 3 10 10 10 0 0 Wheat 0 0 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 3 9 0 0 Wild oat 0 0 0 0 0 0 0 0 Test B The compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedlings 5 emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one- to four-leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood application. Water depth was approximately 2.5 cm for the flood application and was maintained at this level for the duration of the test. 10 Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), winter barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn 1 (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), johnsongrass 15 (Sorghum halpense), lambsquarters (Chenopodium album), late watergrass (Echinochloa oryzicola), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), Italian 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 (Avenafatua). 20 All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test WO 98/47904 PCT/US98/08002 71 consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass 1 (Echinochloa crus-galli) to the 2 leaf stage for testing. All plant species were grown using normal greenhouse practices. Visual evaluations of 5 injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response to the test compound is summarized in Table B, recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table B COMPOUND Rate 62 g/ha 1 2 3 4 7 8 17 POSTEMERGENCE Barley (winter) 60 35 30 40 50 55 30 Barnyardgrass 100 100 100 90 50 100 95 Barnyardgrass 1 - 25 30 35 10 90 30 Bedstraw 60 85 100 100 75 100 100 Blackgrass 30 10 10 0 40 85 45 Chickweed 80 60 65 60 70 100 100 Cocklebur 100 100 100 100 100 100 100 Corn 1 80 85 70 30 85 100 55 Cotton 100 100 100 100 100 100 100 Crabgrass 60 50 30 40 40 85 20 Downy brome 60 75 35 20 30 45 0 Ducksalad - 0 0 0 - 55 30 Giant foxtail 70 60 45 40 90 95 60 Italn. ryegrass 30 20 10 25 30 45 40 Johnsongrass 90 80 50 45 75 - 95 Lambsquarter 100 100 100 100 95 100 100 Late watergrass - 40 40 35 10 90 Morningglory 100 100 100 100 100 100 100 Rape 100 100 100 100 100 100 100 Redroot pigweed 100 100 100 100 95 100 100 Rice japonica - 0 25 35 35 70 40 Soybean 90 35 50 60 65 90 65 Speedwell 100 100 100 100 100 100 Sugar beet 100 100 100 100 100 100 100 Umbrella sedge - 0 0 0 0 90 90 Velvetleaf 100 100 100 100 100 100 100 WO 98/47904 PCT/US98/08002 72 Wheat 40 30 35 35 40 65 30 Wild buckwheat 100 90 100 100 90 100 100 Wild oat 60 40 30 45 65 60 35 Table B COMPOUND Rate 62 g/ha 1 2 3 4 7 8 17 PREEMERGENCE Barley (winter) 0 0 0 0 35 20 40 Barnyardgrass 0 0 0 0 20 90 90 Bedstraw 30 10 100 0 100 100 100 Blackgrass 0 0 0 0 0 85 60 Chickweed 0 25 0 10 55 100 100 Cocklebur 0 0 0 0 0 100 Corn 1 0 0 0 0 0 0 35 Cotton 100 0 0 0 70 100 90 Crabgrass 0 0 0 20 10 60 95 Downy brome 0 0 0 0 30 30 60 Giant foxtail 0 10 0 0 95 100 90 Italn. ryegrass 0 0 0 10 30 60 85 Johnsongrass 0 0 10 0 30 60 90 Lambsquarter 100 100 100 100 100 100 100 Morningglory 40 60 20 30 80 100 100 Rape 90 85 10 20 0 100 90 Redroot pigweed 100 70 60 100 0 - 100 Soybean 0 0 0 0 0 100 35 Speedwell 100 100 100 100 25 100 100 Sugar beet 100 100 100 25 10 100 100 Velvetleaf 100 100 100 100 100 100 100 Wheat 0 0 0 0 0 0 30 Wild buckwheat 10 0 20 0 25 100 100 Wild oat 0 0 0 0 40 50 80 Table B COMPOUND Rate 31 g/ha 1 2 3 4 5 7 8 11 16 17 POSTEMERGENCE Barley (winter) 50 35 30 40 25 40 50 25 20 25 Barnyardgrass 90 100 90 70 95 - 100 85 80 85 Barnyardgrass 1 - 25 25 25 0 10 85 0 0 20 WO 98/47904 PCT/US98/08002 73 Bedstraw 40 30 90 100 55 - 100 55 90 100 Blackgrass 30 0 10 0 0 35 70 10 35 40 Chickweed 70 20 20 0 25 40 100 85 100 Cocklebur 100 100 100 100 100 100 100 100 100 100 Corn 1 80 60 70 25 30 75 100 40 30 20 Cotton 100 100 100 100 100 100 100 100 100 100 Crabgrass 60 50 30 40 50 35 65 40 35 20 Downy brome 40 40 20 10 35 20 45 0 0 0 Ducksalad - 0 0 0 0 0 35 0 40 20 Giant foxtail 60 50 45 30 40 70 85 60 30 35 Italn. ryegrass 20 20 10 10 0 20 40 0 10 0 Johnsongrass 80 70 50 35 90 50 - 65 80 85 Lambsquarter 100 95 100 100 100 95 100 95 90 100 Late watergrass - 35 30 30 - 10 80 - - Morningglory 100 - 95 100 85 100 100 100 100 100 Rape 100 100 60 95 100 90 100 100 100 100 Redroot pigweed 95 100 100 100 80 80 100 100 80 100 Rice japonica - 0 20 20 0 25 50 0 0 35 Soybean 80 30 35 60 35 50 90 35 60 65 Speedwell 100 100 100 100 100 90 100 100 100 Sugar beet 100 100 100 100 100 100 100 100 100 100 Umbrella sedge - 0 0 0 0 0 - 0 50 90 Velvetleaf 100 100 100 100 100 100 100 100 100 100 Wheat 30 30 35 30 35 30 55 25 30 30 Wild buckwheat 100 90 - 85 100 90 100 85 100 100 Wild oat 50 30 30 45 25 30 40 20 30 25 Table B COMPOUND Rate 31 g/ha 1 2 3 4 5 7 81116 17 PREEMERGENCE Barley (winter) 0 0 0 0 0 30 10 0 0 35 Barnyardgrass 0 0 0 0 0 10 75 0 60 90 Bedstraw 0 0 100 0 0 90 100 45 100 90 Blackgrass 0 0 0 0 10 0 80 0 10 50 Chickweed 0 0 0 10 90 55 100 90 - 95 Cocklebur 0 0 0 0 10 0 100 0 90 30 Corn 1 0 0 0 0 0 0 0 0 0 25 Cotton 100 0 0 0 0 20 100 0 35 50 WO 98/47904 PCT/US98/08002 74 Crabgrass 0 0 0 20 0 0 60 0 10 60 Downy brome 0 0 0 0 0 10 - 0 0 40 Giant foxtail 0 0 0 0 0 80 100 20 30 80 Italn. ryegrass 0 0 0 0 20 30 30 0 0 40 Johnsongrass 0 0 0 0 10 0 30 20 10 90 Lambsquarter 100 95 100 100 100 100 100 95 100 100 Morningglory 30 20 0 - 0 75 100 90 100 100 Rape 90 0 0 0 0 0 100 0 30 70 Redroot pigweed 100 70 40 90 - 0 - 80 100 100 Soybean 0 0 0 0 0 0 100 10 20 10 Speedwell 100 95 100 100 0 0 100 100 100 100 Sugar beet 100 100 100 10 100 10 100 70 - 100 Velvetleaf 100 100 100 100 35 90 100 80 100 100 Wheat 0 0 0 0 25 0 0 0 0 30 Wild buckwheat 10 0 10 0 0 0 100 85 100 100 Wild oat 0 0 0 0 25 25 30 0 0 35 Table B COMPOUND Rate 16 g/ha 1 2 3 4 5 7 8 9 10 11 12 14 15 16 17 POSTEMERGENCE Barley (winter) 40 30 30 40 25 30 40 20 20 25 15 25 35 20 10 Barnyardgrass 70 85 50 40 70 40 100 50 40 65 20 65 50 60 75 Barnyardgrass 1 0 0 10 10 0 0 40 10 0 0 0 0 0 0 10 Bedstraw 40 30 60 90 .50 60 100 40 85 50 100 95 90 70 100 Blackgrass 20 0 10 0 0 20 40 10 10 0 0 10 15 35 40 Chickweed 30 0 10 0 0 30 100 70 95 85 70 95 95 100 100 Cocklebur 100 100 100 100 100 90 100 20 30 100 70 100 100 100 100 Corn 1 60 40 35 20 20 35 70 20 30 40 20 20 25 15 0 Cotton 100 100 100 100 100 100 100 90 90 100 100 100 100 100 100 Crabgrass 50 40 20 30 30 30 65 30 30 40 70 60 20 25 20 Downy brome 30 10 10 10 30 20 45 20 10 0 0 20 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 30 10 Giant foxtail 50 50 35 30 30 35 70 30 30 50 60 60 20 25 35 Italn. ryegrass 20 0 10 0 0 20 40 20 10 0 0 0 0 10 0 Johnsongrass 70 50 50 25 75 40 - 40 30 55 35 40 20 50 65 Lambsquarter 100 95 100 100 90 90 100 40 10 95 100 100 100 80 100 Late watergrass 0 25 20 20 - 10 60 10 10 - - - - Morningglory 100 100 95 100 60 95 100 80 70 100 90 100 100 100 100 WO 98/47904 PCT/US98/08002 75 Rape 100 100 60 95 90 70 100 35 70 95 60 100 100 90 60 Redroot pigweed 95 100 100 100 70 80 100 50 70 100 100 100 90 70 100 Rice japonica 35 0 20 20 0 25 30 10 10 0 0 0 0 0 20 Soybean 70 30 30 40 25 45 75 35 50 30 50 65 40 - 65 Speedwell 100 100 100 90 100 70 100 10 70 70 - 100 100 100 Sugar beet 100 100 100 100 100 100 100 95 95 90 100 100 100 100 100 Umbrella sedge 0 0 0 0 0 - 40 0 0 0 0 0 0 40 50 Velvetleaf 100 100 100 100 100 100 100 50 75 85 100 100 100 100 100 Wheat 20 25 25 30 30 20 40 15 20 25 0 25 30 20 25 Wild buckwheat 100 - 100 - 95 90 100 80 95 85 100 100 95 100 100 Wild oat 40 20 20 45 0 - 40 25 15 20 25 10 25 0 10 Table B COMPOUND Rate 16 g/ha 1 2 3 4 5 7 8 9101112 14 15 16 17 PREEMERGENCE Barley (winter) 0 0 0 0 0 0 10 0 0 0 0 0 0 0 30 Barnyardgrass 0 0 0 0 0 0 70 0 0 0 0 10 0 30 40 Bedstraw 0 0 20 0 0 60 100 25 25 0 90 45 35 0 40 Blackgrass 0 0 0 0 10 0 45 10 25 0 0 0 0 0 40 Chickweed 0 0 0 10 - 50 100 35 25 35 0 25 85 - 95 Cocklebur 0 0 0 0 0 0 100 10 30 0 0 100 30 70 10 Corn 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 Cotton 70 0 0 0 0 0 100 0 0 0 30 70 40 25 30 Crabgrass 0 0 0 0 0 0 50 0 10 0 0 0 0 0 30 Downy brome 0 0 0 0 0 0 30 0 0 0 0 0 0 0 30 Giant foxtail 0 0 0 - 0 60 100 0 0 0 0 0 0 10 40 Italn. ryegrass 0 0 0 0 0 10 20 0 0 0 0 0 0 0 0 Johnsongrass 0 0 0 0 0 0 20 0 20 0 0 0 0 0 50 Lambsquarter 95 95 95 100 100 100 100 25 25 95 100 100 100 100 100 Morningglory 20 0 0 0 0 20 100 50 40 10 100 100 100 100 100 Rape 20 0 0 0 - 0 100 0 0 0 25 100 65 30 70 Redroot pigweed 100 25 10 70 - - - 10 20 60 60 95 50 100 100 Soybean 0 0 0 0 0 0 100 10 0 0 10 0 0 0 0 Speedwell 95 - 100 100 - 0 100 0 0 100 100 100 100 100 100 Sugar beet 95 100 100 10 100 0 100 10 20 10 100 100 100 - 100 Velvetleaf 100 100 100 100 0 70 100 10 20 60 100 100 90 100 100 Wheat 0 0 0 0 25 0 0 0 0 0 0 0 0 0 30 Wild buckwheat 0 0 0 0 0 0 90 10 25 0 95 55 25 100 100 WO 98/47904 PCT/US98/08002 76 Wild oat 0 0 0 0 25 10 20 0 0 0 0 0 0 0 25 Table B COMPOUND Rate 8 g/ha 1 2 3 4 5 7 8 9 10 11 12 14 15 16 POSTEMERGENCE Barley (winter) 30 30 30 40 25 20 35 20 20 20 15 25 25 10 Barnyardgrass 60 75 50 20 70 30 100 30 30 35 15 60 30 30 Barnyardgrass 1 0 0 0 0 0 0 15 0 0 0 0 0 0 0 Bedstraw 30 10 50 85 35 50 90 40 20 40 40 90 75 70 Blackgrass 10 0 10 0 0 15 35 0 10 0 0 10 10 20 Chickweed 20 0 0 0 0 30 100 0 35 55 50 90 95 95 Cocklebur 90 100 100 90 100 75 100 20 30 50 60 100 90 90 Corn 1 30 30 25 15 15 30 35 20 20 30 20 15 20 10 Cotton 100 100 100 100 100 90 100 80 80 95 90 100 100 100 Crabgrass 30 30 20 30 30 20 65 20 20 30 50 50 15 15 Downy brome 20 10 10 10 0 10 35 10 10 0 0 20 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Giant foxtail 30 30 35 25 30 25 55 20 20 50 40 60 15 20 Italn. ryegrass 10 0 10 0 0 0 35 20 10 0 0 0 0 0 Johnsongrass 70 35 40 25 55 30 - 40 20 50 25 40 10 10 Lambsquarter 100 30 80 100 70 85 100 40 0 0 0 100 100 50 Late watergrass 0 25 0 20 - 0 40 0 0 - - - - Morningglory 95 100 95 85 - 95 100 70 - 85 80 100 90 100 Rape 95 90 50 95 80 60 100 30 50 70 50 100 95 75 Redroot pigweed 95 100 95 95 - 80 100 40 30 90 100 100 80 60 Rice japonica 20 0 0 20 0 20 15 10 10 0 0 0 0 0 Soybean 70 25 - 30 15 45 75 35 50 25 40 55 40 50 Speedwell 100 100 100 90 100 35 100 0 20 70 90 100 100 80 Sugar beet 100 100 100 100 100 100 100 30 65 0 100 100 100 100 Umbrella sedge 0 0 0 0 0 0 25 0 0 0 0 0 0 20 Velvetleaf 100 100 100 100 100 90 100 40 50 85 80 100 100 100 Wheat 10 25 20 30 25 10 30 10 15 20 0 20 20 10 Wild buckwheat 100 90 100 85 95 90 100 80 95 70 30 80 95 100 Wild oat 30 20 10 45 0 25 35 20 15 20 25 10 10 0 5 WO 98/47904 PCT/US98/08002 77 Table B COMPOUND Rate 8 g/ha 1 2 3 4 5 7 8 9 10 11 12 14 15 16 PREEMERGENCE Barley (winter) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 35 0 0 0 0 0 0 0 Bedstraw 0 0 0 0 0 30 100 0 25 0 10 10 10 Blackgrass 0 0 0 0 0 0 35 0 20 0 0 0 0 0 Chickweed 0 0 0 10 30 40 100 35 25 35 0 25 - Cocklebur 0 0 0 0 0 0 100 0 10 0 0 20 20 50 Corn 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cotton 30 0 0 0 0 0 100 0 0 0 10 30 20 10 Crabgrass 0 0 0 0 0 0 40 0 10 0 0 0 0 0 Downy brome 0 0 0 0 0 0 30 0 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 0 70 0 0 0 0 0 0 0 Italn. ryegrass 0 0 0 0 0 0 20 0 0 0 0 0 0 0 Johnsongrass 0 0 0 0 0 0 20 0 20 0 0 0 0 0 Lambsquarter 10 90 95 100 100 0 100 10 10 - 100 100 100 100 Morningglory 10 0 0 0 0 0 100 0 0 - 60 100 20 100 Rape 0 0 0 0 0 0 100 0 0 0 0 20 0 10 Redroot pigweed 80 25 - 30 - 0 - 10 - 50 40 80 30 80 Soybean 0 0 0 0 0 0 0 10 0 0 10 0 0 0 Speedwell 95 - 100 100 0 0 100 - 0 100 95 100 - 0 Sugar beet 95 100 70 10 0 0 100 10 20 0 100 100 95 Velvetleaf 100 100 90 70 0 30 100 0 20 20 70 100 70 100 Wheat 0 0 0 0 25 0 0 0 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 0 0 80 0 20 0 0 10 0 0 Wild oat 0 0 0 0 25 0 - 0 0 0 0 0 0 0 Table B COMPOUND Rate 4 g/ha 1 5 9 10 11 12 14 15 16 POSTEMERGENCE Barley (winter) 0 25 15 15 20 10 25 0 0 Barnyardgrass 70 50 30 30 20 10 50 20 20 Barnyardgrass 1 0 0 0 0 0 0 0 0 0 Bedstraw 0 30 30 20 30 40 50 60 20 Blackgrass 0 0 0 10 0 0 0 0 10 Chickweed 0 0 0 35 45 40 80 70 80 Cocklebur 90 65 10 20 30 50 100 70 90 WO 98/47904 PCT/US98/08002 78 Corn 1 15 10 10 20 25 15 15 15 10 Cotton 100 100 70 60 95 90 100 90 100 Crabgrass 10 20 10 10 30 30 40 10 10 Downy brome 0 0 0 10 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 10 Giant foxtail 20 15 15 10 35 40 40 15 10 Italn. ryegrass 0 0 0 0 0 0 0 0 0 Johnsongrass 20 40 20 20 20 15 30 10 0 Lambsquarter 10 70 30 0 0 0 100 95 Late watergrass 0 - 0 0 - - - - Morningglory 90 50 60 70 85 50 100 90 100 Rape 85 30 0 30 60 30 100 90 40 Redroot pigweed 90 60 40 20 80 70 100 70 60 Rice japonica 0 0 0 0 0 0 0 0 0 Soybean 20 10 30 40 25 30 45 30 40 Speedwell 70 100 0 0 40 70 100 80 80 Sugar beet 100 100 10 60 0 90 95 100 90 Umbrella sedge 0 0 0 0 0 0 0 0 10 Velvetleaf 100 90 30 30 50 60 100 90 100 Wheat 0 25 0 0 20 0 0 0 10 Wild buckwheat 40 90 70 85 70 15 70 85 60 Wild oat 0 0 10 10 15 25 10 0 0 Table B COMPOUND Rate 4 g/ha 1 5 9 10 11 12 14 15 16 PREEMERGENCE Barley (winter) 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 Bedstraw 0 0 0 25 0 10 0 10 0 Blackgrass 0 0 0 0 0 0 0 0 0 Chickweed 0 30 35 25 35 0 25 85 Cocklebur 0 0 0 10 0 0 0 10 20 Corn 1 0 0 0 0 0 0 0 0 0 Cotton 0 0 0 0 0 0 20 20 10 Crabgrass 0 0 0 0 0 0 0 0 0 Downy brome 0 0 0 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 0 0 0 0 Italn. ryegrass 0 0 0 0 0 0 0 0 0 WO 98/47904 PCT/US98/08002 79 Johnsongrass 0 0 0 0 0 0 0 0 0 Lambsquarter - 100 10 0 85 0 100 100 100 Morningglory 0 0 0 0 0 60 50 0 95 Rape 0 0 0 0 0 0 20 0 0 Redroot pigweed 0 - 0 0 50 0 80 30 30 Soybean 0 0 0 0 0 0 0 0 0 Speedwell 60 0 0 0 40 95 100 100 Sugar beet 10 0 10 20 0 20 25 10 Velvetleaf 100 0 0 0 20 30 100 10 60 Wheat 0 25 0 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 0 0 0 0 0 Wild oat 0 20 0 0 0 0 0 0 0 Table B COMPOUND Rate 2 g/ha 1 9 10 12 14 15 POSTEMERGENCE Barley (winter) 0 10 15 0 0 0 Barnyardgrass 35 20 20 10 20 10 Barnyardgrass 1 0 0 0 0 0 0 Bedstraw 0 20 0 40 30 60 Blackgrass 0 0 10 0 0 0 Chickweed 0 0 30 40 70 70 Cocklebur 35 0 0 20 90 50 Corn 1 10 0 10 10 .10 10 Cotton 100 30 30 80 100 90 Crabgrass 10 0 0 20 40 10 Downy brome 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 Giant foxtail 10 10 10 25 40 10 Italn. ryegrass 0 0 0 0 0 0 Johnsongrass 15 - 10 10 10 0 Lambsquarter 0 30 0 0 95 55 Late watergrass 0 0 0 - - Morningglory 80 30 40 50 90 70 Rape 0 0 0 30 40 60 Redroot pigweed 30 30 20 50 80 40 Rice japonica 0 0 0 0 0 0 Soybean 10 25 35 20 30 30 WO 98/47904 PCT/US98/08002 80 Speedwell 30 0 0 70 75 70 Sugar beet 100 10 0 90 95 100 Umbrella sedge 0 0 0 0 0 0 Velvetleaf 100 15 20 50 100 70 Wheat 0 0 0 0 0 0 Wild buckwheat 20 50 80 15 70 20 Wild oat 0 0 10 20 0 0 Table B COMPOUND Rate 2 g/ha 1 9 10 12 14 15 PREEMERGENCE Barley (winter) 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 Bedstraw 0 0 25 0 0 0 Blackgrass 0 0 0 0 0 0 Chickweed 0 25 - 0 0 85 Cocklebur 0 0 0 0 0 0 Corn 1 0 0 0 0 0 0 Cotton 0 0 0 0 - 0 Crabgrass 0 0 0 0 0 0 Downy brome 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 0 Italn. ryegrass 0 0 0 0 0 0 Johnsongrass 0 0 0 0 0 0 Lambsquarter 90 10 0 0 100 100 Morningglory 0 0 0 10 0 0 Rape 0 0 0 0 0 0 Redroot pigweed 0 0 0 0 65 20 Soybean 0 0 0 0 0 0 Speedwell 60 0 0 0 70 100 Sugar beet 0 10 20 0 - 0 Velvetleaf 10 0 0 0 20 0 Wheat 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 0 0 Wild oat 0 0 0 0 0 0 WO 98/47904 PCT/US98/08002 81 Table B COMPOUND Table B COMPOUND Rate 1 g/ha 1 9 10 Rate 1 g/ha 1 9 10 POSTEMERGENCE PREEMERGENCE Barley (winter) 0 0 0 Barley (winter) 0 0 0 Barnyardgrass 10 10 20 Barnyardgrass 0 0 0 Barnyardgrass 1 0 0 0 Bedstraw 0 0 20 Bedstraw 0 20 0 Blackgrass 0 0 0 Blackgrass 0 0 0 Chickweed 0 - 25 Chickweed 0 0 20 Cocklebur 0 0 0 Cocklebur 30 0 0 Corn 1 0 0 0 Corn 1 10 0 0 Cotton 0 0 0 Cotton 100 30 20 Crabgrass 0 0 0 Crabgrass 10 0 0 Downy brome 0 0 0 Downy brome 0 0 0 Giant foxtail 0 0 0 Ducksalad 0 0 0 Italn. ryegrass 0 0 0 Giant foxtail 10 0 0 Johnsongrass 0 0 0 Italn. ryegrass 0 0 0 Lambsquarter 10 10 0 Johnsongrass 10 0 10 Morningglory 0 0 0 Lambsquarter 0 30 0 Rape 0 0 0 Late watergrass 0 0 0 Redroot pigweed 0 0 0 Morningglory 65 15 30 Soybean 0 0 0 Rape 0 0 0 Speedwell 60 0 0 Redroot pigweed 30 30 10 Sugar beet 0 10 20 Rice japonica 0 0 0 Velvetleaf 0 0 0 Soybean 0 20 30 Wheat 0 0 0 Speedwell 20 0 0 Wild buckwheat 0 0 0 Sugar beet 100 0 0 Wild oat 0 0 0 Umbrella sedge 0 0 0 Velvetleaf 95 0 10 Wheat 0 0 0 Wild buckwheat 0 20 20 Wild oat 0 0 10 Test C Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunao, cassia (Cassia obtusifolia), cocklebur 5 (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), corn (Zea mays designated 'Corn 5'), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum WO 98/47904 PCT/US98/08002 82 (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morning-glory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), smartweed (Polygonum -5 pensylvanicum), soybean (Glycine max designated 'Soybean 1 '), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a clay loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one- to four-leaf 10 stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Pots receiving preemergence treatments were planted immediatley prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse 15 approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table C, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. Table C COMPOUND Table C COMPOUND Table C COMPOUND Rate 17 g/ha 2 3 Rate 8 g/ha 2 3 Rate 4 g/ha 2 3 POSTEMERGENCE POSTEMERGENCE POSTEMERGENCE Barnyardgrass 70 40 Barnyardgrass 30 40 Barnyardgrass 30 10 Bindweed 100 100 Bindweed 100 100 Bindweed 100 80 Blk nightshade 100 100 Blk nightshade 100 100 Blk nightshade 60 70 Cassia 0 0 Cassia 0 0 Cassia 0 0 Cocklebur 100 80 Cocklebur 100 80 Cocklebur 80 70 Cotton 100 100 Cotton 100 100 Cotton 100 100 Crabgrass 50 50 Crabgrass 30 30 Crabgrass 5 15 Corn 5 5 5 Corn 5 5 5 Corn 5 0 0 Fall panicum 5 5 Fall panicum 0 5 Fall panicum 0 5 Giant foxtail 20 30 Giant foxtail 5 10 Giant foxtail 5 5 Green foxtail 45 30 Green foxtail 30 30 Green foxtail 10 15 Jimsonweed 100 100 Jimsonweed 100 100 Jimsonweed 100 100 Johnsongrass 40 40 Johnsongrass 40 40 Johnsongrass 30 20 Lambsquarters 100 100 Lambsquarters 60 85 Lambsquarters 60 70 Morningglory 100 100 Morningglory 100 100 Morningglory 100 100 Nutsedge 0 5 Nutsedge 0 0 Nutsedge 0 0 Pigweed 100 100 Pigweed 100 100 Pigweed 100 80 WO 98/47904 PCT/US98/08002 83 Prickly sida 100 100 Prickly sida 100 100 Prickly sida 100 100 Ragweed 70 70 Ragweed 60 60 Ragweed 10 10 Shattercane 70 30 Shattercane 50 10 Shattercane 40 10 Smartweed 50 60 Smartweed 50 60 Smartweed 10 10 Soybean 1 10 10 Soybean 1 5 10 Soybean 1 5 5 Sunflower 80 80 Sunflower 20 50 Sunflower 10 20 Velvetleaf 100 100 Velvetleaf 100 100 Velvetleaf 100 100 Wild proso 5 50 Wild proso 5 - Wild proso 5 50 Woolly cupgrass 10 10 Woolly cupgrass 5 5 Woolly cupgrass 5 5 Yellow foxtail 10 5 Yellow foxtail 5 5 Yellow foxtail 5 5 Table C COMPOUND Table C COMPOUND Rate 2 g/ha 2 3 Rate 1 g/ha 2 3 POSTEMERGENCE POSTEMERGENCE Barnyardgrass 10 5 Barnyardgrass 0 5 Bindweed 100 60 Bindweed 60 10 Blk nightshade 100 100 Blk nightshade 70 10 Cassia 0 0 Cassia 0 0 Cocklebur 60 60 Cocklebur 30 45 Cotton 95 90 Cotton 90 90 Crabgrass 5 5 Crabgrass 5 0 Corn 5 0 0 Corn 5 0 0 Fall panicum 0 0 Fall panicum 0 0 Giant foxtail 0 0 Giant foxtail 0 0 Green foxtail 5 5 Green foxtail 5 5 Jimsonweed 80 70 Jimsonweed 70 50 Johnsongrass 10 20 Johnsongrass 5 20 Lambsquarters 20 30 Lambsquarters 10 10 Morningglory 100 100 Morningglory 100 90 Nutsedge 0 0 Nutsedge 0 0 Pigweed 100 50 Pigweed 5 50 Prickly sida 90 80 Prickly sida 70 0 Ragweed 5 5 Ragweed 5 5 Shattercane 40 - Shattercane 5 5 Smartweed 10 5 Smartweed 0 5 Soybean 1 0 5 Soybean 1 0 0 Sunflower 10 10 Sunflower 0 10 Velvetleaf 100 100 Velvetleaf 80 100 WO 98/47904 PCT/US98/08002 84 Wild proso 5 50 Wild proso 0 30 Woolly cupgrass 5 5 Woolly cupgrass 0 5 Yellow foxtail 0 5 Yellow foxtail 0 0 Test D Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were grown for various periods of time 5 before treatment (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include arrowleaf sida (Sida rhombifolia), 10 barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosia elatior), corn 1 (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum), field bindweed (Convolvulus arvensis), Florida beggarweed (Desmodium tortuosum), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), 15 johnsongrass (Sorghum halepense), ladysthumb smartweed (Polygonum persicaria), lambsquarters (Chenopodium album), large crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean 1 (Glycine max), surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (Euphorbia heterophylla). 20 Treated plants and untreated controls were maintained in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table D, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A dash response (-) means no test result. 25 Table D COMPOUND Rate 17 g/ha 1 2 4 5 14 16 17 POSTEMERGENCE Arrowleaf sida 100 95 95 0 70 100 100 Barnyardgrass 30 20 30 70 15 20 20 Cocklebur 100 100 90 100 80 100 80 Common ragweed 55 50 65 50 100 100 100 Corn 1 20 15 15 15 15 10 10 Cotton 100 100 100 100 100 100 90 E. blacknightsh 100 95 100 65 100 100 100 WO 98/47904 PCT/US98/08002 85 Fall panicum 15 15 20 20 60 5 5 Field bindweed 100 85 100 95 100 100 80 Fl. beggarweed 100 35 85 10 100 100 80 Giant foxtail 30 25 25 45 20 10 15 H. beggarticks 50 25 25 85 100 100 100 I. morningglory 100 75 95 80 100 100 100 Johnsongrass 30 15 25 40 20 10 10 Ladysthumb 45 100 70 40 100 100 100 Lambsquarters 95 80 85 100 100 100 90 Large crabgrass 15 25 15 50 20 0 10 Purple nutsedge 15 10 15 5 10 10 Redroot pigweed 95 100 100 65 100 100 100 Soybean 1 40 25 40 15 30 50 30 Surinam grass 15 20 25 25 15 20 10 Velvetleaf 100 100 100 100 100 100 100 Wild poinsettia 100 100 100 100 100 100 100 Table D COMPOUND Rate 17 g/ha 1 2 4 14 PREEMERGENCE Arrowleaf sida 45 10 - 90 Barnyardgrass 0 0 0 0 Cocklebur 0 0 0 75 Common ragweed 10 0 0 100 Corn 1 0 0 0 10 Cotton - 0 0 80 E. blacknightsh - - - 85 Fall panicum 0 0 10 0 Field bindweed 0 0 0 100 Fl. beggarweed - - - 30 Giant foxtail 10 0 10 0 H. beggarticks 25 0 10 60 I. morningglory 0 0 0 85 Johnsongrass 0 0 0 5 Ladysthumb - - - 85 Lambsquarters - 0 - 100 Large crabgrass 15 0 20 10 Purple nutsedge - 0 - 0 WO 98/47904 PCT/US98/08002 86 Redroot pigweed 25 0 - 100 Soybean 1 10 10 0 35 Surinam grass 0 0 0 0 Velvetleaf 100 0 10 100 Wild poinsettia 25 0 30 100 Table D COMPOUND Rate 8 g/ha 1 2 4 5 8 14 16 17 POSTEMERGENCE Arrowleaf sida 100 75 90 0 100 70 100 10 Barnyardgrass 15 15 25 30 75 10 10 10 Cocklebur 80 100 85 80 100 70 70 100 Common ragweed 40 40 60 0 100 100 75 50 Corn 1 15 10 15 15 25 15 5 10 Cotton 100 100 100 90 100 100 100 90 E. blacknightsh 95 75 95 65 100 100 100 50 Fall panicum 10 10 15 5 35 30 0 5 Field bindweed 100 65 100 90 100 100 75 60 Fl. beggarweed 40 25 55 5 100 90 50 10 Giant foxtail 15 15 25 20 40 15 5 10 H. beggarticks 35 20 25 30 100 90 100 20 I. morningglory 60 65 70 75 100 100 100 100 Johnsongrass 20 10 20 20 35 15 0 10 Ladysthumb 30 60 35 10 95 100 100 100 Lambsquarters 75 70 70 100 95 80 100 80 Large crabgrass 15 15 15 15 25 15 0 10 Purple nutsedge 10 5 - 0 20 0 10 Redroot pigweed 90 95 100 65 100 100 100 60 Soybean 1 25 10 35 10 90 25 50 20 Surinam grass 10 15 15 10 25 15 20 5 Velvetleaf 100 100 100 100 100 100 100 100 Wild poinsettia 100 95 100 90 100 100 100 100 Table D COMPOUND Rate 8 g/ha 1 2 4 8 14 PREEMERGENCE Arrowleaf sida 25 0 0 95 80 Barnyardgrass 0 0 0 15 0 WO 98/47904 PCT/US98/08002 87 Cocklebur 0 0 0 75 55 Common ragweed 0 0 0 90 100 Corn 1 0 0 0 10 0 Cotton 10 0 0 50 70 E. blacknightsh - - - - 85 Fall panicum 0 0 0 40 0 Field bindweed 0 0 0 15 100 Fl. beggarweed 0 0 - - 30 Giant foxtail 0 0 10 10 0 H. beggarticks 0 0 0 20 60 I. morningglory 0 0 0 25 60 Johnsongrass 0 0 0 0 0 Ladysthumb - - - - 85 Lambsquarters 0 0 - 85 100 Large crabgrass 10 0 15 60 0 Purple nutsedge - - - - 0 Redroot pigweed 10 0 10 95 70 Soybean 1 0 0 0 0 20 Surinam grass 0 0 0 15 0 Velvetleaf 25 0 0 80 100 Wild poinsettia 10 0 15 40 100 Table D COMPOUND Rate 4 g/ha 1 2 4 8 14 16 17 POSTEMERGENCE Arrowleaf sida 100 60 65 80 60 100 60 Barnyardgrass 10 10 15 35 10 10 10 Cocklebur 65 90 70 100 60 50 75 Common ragweed 30 35 40 100 100 100 65 Corn 1 10 5 10 20 15 5 10 Cotton 100 100 100 100 100 100 85 E. blacknightsh 85 60 40 100 85 100 50 Fall panicum 5 5 5 20 30 0 5 Field bindweed 100 50 55 100 100 50 60 Fl. beggarweed 35 25 30 100 80 50 10 Giant foxtail 15 10 15 35 15 0 10 H. beggarticks 20 15 20 100 80 50 20 I. morningglory 45 55 25 100 100 100 95 WO 98/47904 PCT/US98/08002 88 Johnsongrass 20 5 10 30 15 0 10 Ladysthumb 25 20 25 75 - 100 20 Lambsquarters 65 65 55 85 80 80 65 Large crabgrass 10 10 10 20 15 0 10 Purple nutsedge 10 - 0 10 0 5 Redroot pigweed 85 90 95 100 100 100 50 Soybean 1 15 5 30 90 25 40 15 Surinam grass 10 15 10 20 10 10 5 Velvetleaf 100 100 100 100 100 100 70 Wild poinsettia 100 85 70 100 100 85 100 Table D COMPOUND Rate 4 g/ha 1 2 4 8 14 PREEMERGENCE Arrowleaf sida 10 0 0 30 70 Barnyardgrass 0 0 0 10 0 Cocklebur 0 - 0 35 30 Common ragweed 0 0 0 50 65 Corn 1 0 0 0 0 0 Cotton 0 0 0 0 55 E. blacknightsh - - - - 70 Fall panicum 0 0 0 30 0 Field bindweed 0 0 0 - 100 Fl. beggarweed 0 0 - - 30 Giant foxtail 0 0 0 0 0 H. beggarticks 0 0 0 0 55 I. morningglory 0 0 0 15 40 Johnsongrass 0 0 0 0 0 Ladysthumb - - Lambsquarters 0 0 100 90 100 Large crabgrass 0 0 15 15 0 Purple nutsedge - - 0 - 0 Redroot pigweed 0 0 0 35 70 Soybean 1 0 0 0 0 15 Surinam grass 0 0 0 0 0 Velvetleaf 0 0 0 25 70 Wild poinsettia 0 0 0 25 100 WO 98/47904 PCT/US98/08002 89 Table D COMPOUND Rate 2 g/ha 1 2 4 8 14 16 17 POSTEMERGENCE Arrowleaf sida 70 50 30 75 50 30 0 Barnyardgrass 5 10 10 25 10 5 5 Cocklebur 55 50 50 100 50 20 60 Common ragweed 25 25 35 100 70 20 10 Corn 1 5 0 5 15 15 5 10 Cotton 90 100 100 100 90 80 70 E. blacknightsh 50 45 35 100 75 100 10 Fall panicum 0 0 0 15 30 0 5 Field bindweed 75 25 40 100 75 100 20 Fl. beggarweed 20 20 25 100 70 10 10 Giant foxtail 10 0 10 30 10 0 5 H. beggarticks 20 15 15 80 70 40 10 I. morningglory 15 20 20 100 100 90 80 Johnsongrass 10 0 5 25 15 0 10 Ladysthumb 15 15 15 70 75 10 10 Lambsquarters 65 45 40 75 70 50 20 Large crabgrass 10 10 5 15 15 0 5 Purple nutsedge 0 0 0 0 0 0 Redroot pigweed 80 65 90 100 85 90 20 Soybean 1 10 0 25 85 20 25 15 Surinam grass 5 10 0 15 10 10 5 Velvetleaf 85 65 100 100 100 100 40 Wild poinsettia 90 50 45 100 70 50 100 Table D COMPOUND Rate 2 g/ha 1 2 4 8 14 PREEMERGENCE Arrowleaf sida 0 0 0 15 55 Barnyardgrass 0 0 0 0 0 Cocklebur 0 0 - 20 20 Common ragweed 0 0 0 15 Corn 1 0 0 0 0 0 Cotton 0 0 - 0 40 E. blacknightsh - - - - 60 Fall panicum 0 0 - 0 0 WO 98/47904 PCT/US98/08002 90 Field bindweed 0 0 - - 100 Fl. beggarweed 0 - Giant foxtail 0 0 0 0 0 H. beggarticks 0 0 0 0 15 I. morningglory 0 - 0 10 30 Johnsongrass 0 0 0 0 0 Ladysthumb - 0 - - 45 Lambsquarters - 0 85 45 100 Large crabgrass 0 0 10 0 0 Purple nutsedge - - - - 0 Redroot pigweed 0 0 0 0 55 Soybean 1 0 0 0 0 15 Surinam grass 0 0 0 0 0 Velvetleaf 0 0 0 0 25 Wild poinsettia 0 0 0 0 45 Table D COMPOUND Rate 1 g/ha 1 2 4 8 14 16 17 POSTEMERGENCE Arrowleaf sida 60 45 25 75 0 50 0 Barnyardgrass 5 0 0 20 10 5 5 Cocklebur 25 40 35 80 55 15 50 Common ragweed 15 20 20 60 70 0 10 Corn 1 0 0 5 15 10 0 10 Cotton 90 90 90 100 85 75 40 E. blacknightsh 20 25 25 85 10 100 10 Fall panicum 0 0 0 10 20 0 0 Field bindweed 45 20 30 90 65 50 10 Fl. beggarweed 20 15 20 55 60 0 Giant foxtail 5 0 5 15 10 0 5 H. beggarticks 10 10 10 35 20 40 10 I. morningglory 5 0 15 100 80 60 50 Johnsongrass 5 0 0 15 10 0 0 Ladysthumb 10 10 10 45 0 5 10 Lambsquarters 30 30 35 70 60 25 10 Large crabgrass 5 5 5 15 15 0 0 Purple nutsedge - 0 0 0 0 0 Redroot pigweed 70 50 80 95 70 60 20 WO 98/47904 PCT/US98/08002 91 Soybean 1 5 0 20 40 10 20 10 Surinam grass 0 0 0 10 10 5 5 Velvetleaf 80 40 60 90 100 60 10 Wild poinsettia 50 35 25 95 65 40 50 Table D COMPOUND Table D COMPOUND Rate 1 g/ha 1 2 4 8 14 Rate .50 g/ha 8 PREEMERGENCE POSTEMERGENCE Arrowleaf sida 0 0 0 0 20 Arrowleaf sida 25 Barnyardgrass 0 0 0 0 0 Barnyardgrass 10 Cocklebur 0 - 0 0 0 Cocklebur 70 Common ragweed 0 0 0 0 55 Common ragweed 50 Corn 1 0 0 0 0 0 Corn 1 10 Cotton 0 0 0 - 15 Cotton 100 E. blacknightsh - - - - 45 E. blacknightsh 80 Fall panicum 0 0 0 0 0 Fall panicum 10 Field bindweed 0 - 0 0 60 Field bindweed 35 Fl. beggarweed - - 0 0 20 Fl. beggarweed 35 Giant foxtail 0 0 0 0 0 Giant foxtail 10 H. beggarticks 0 0 - 0 15 H. beggarticks 25 I. morningglory 0 0 0 0 15 I. morningglory 90 Johnsongrass 0 0 0 0 0 Johnsongrass 10 Ladysthumb 0 - - - 45 Ladysthumb 35 Lambsquarters 0 - 0 0 80 Lambsquarters 50 Large crabgrass 0 0 0 0 0 Large crabgrass 10 Purple nutsedge - 0 - 0 0 Purple nutsedge 0 Redroot pigweed 0 0 - 0 45 Redroot pigweed 90 Soybean 1 0 0 0 0 0 Soybean 1 35 Surinam grass 0 0 0 0 0 Surinam grass 5 Velvetleaf 0 0 0 0 15 Velvetleaf 70 Wild poinsettia 0 0 0 0 15 Wild poinsettia 80 Test E Compounds evaluated in this test were formulated in a non-phytotoxic solvent 5 mixture which included a surfactant and applied to plants that were in the 1- to 4-leaf stage (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
WO 98/47904 PCT/US98/08002 92 Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), blackgrass 2 (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed -5 (Stellaria media), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium 2 (Galium aparine), green foxtail (Setaria viridis), ryegrass (Lolium multiflorum), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), lentil (Lens culinaris), littleseed canarygrass (Phalaris minor), rape 1 (Brassica napus), redroot pigweed (Amaranthus retroflexus), Russian thistle 10 (Salsola kali), 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 1 or wild oat 2 representing the 1.5 or 2 leaf stage of development respectively, (Avenafatua), windgrass 15 (Apera spica-venti) and winter barley (Hordeum vulgare). Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) 20 means no test result. Table E COMPOUND Table E COMPOUND Rate 31 g/ha 16 Rate 31 g/ha 8 12 13 14 POSTEMERGENCE PREEMERGENCE Annual bluegras 20 Annual bluegras - - - Barley (winter) 30 Barley (winter) 10 20 20 10 Blackgrass (2) 20 Blackgrass (2) - - - Blk nightshade 100 Blk nightshade 100 100 70 65 Chickweed 100 Chickweed 100 65 60 100 Deadnettle 100 Deadnettle 60 65 60 100 Downy brome 20 Downy brome - - - Field violet 100 Field violet 20 30 30 30 Galium (2) 100 Galium (2) 100 100 70 100 Green foxtail 65 Green foxtail - - - I. Ryegrass 30 I. Ryegrass Jointed goatgra 30 Jointed goatgra Kochia 100 Kochia 70 100 70 55 Lambsquarters 100 Lambsquarters 65 100 85 60 WO 98/47904 PCT/US98/08002 93 LS canarygrass 50 LS canarygrass Rape (1) 100 Rape (1) Redroot pigweed 100 Redroot pigweed 50 80 50 40 Russian thistle 100 Russian thistle 65 100 100 65 Scentless chamo 100 Scentless chamo 75 55 70 100 Speedwell - Speedwell - - - Spring Barley 20 Spring Barley 10 10 10 10 Sugar beet 100 Sugar beet - - - Sunflower 100 Sunflower - - - Veronica hedera - Veronica hedera 100 75 100 100 Wheat (spring) 30 Wheat (spring) 5 20 20 0 Wheat (winter) 20 Wheat (winter) 10 5 20 20 Wild buckwheat 100 Wild buckwheat 100 100 65 85 Wild mustard 100 Wild mustard - - - Wild oat (1) 30 Wild oat (1) - - Wild oat (2) - Wild oat (2) - - - Windgrass 10 Windgrass - - - Table E COMPOUND Table E COMPOUND Rate 16 g/ha 1 9 10 16 Rate 16 g/ha 1 12 13 14 POSTEMERGENCE PREEMERGENCE Annual bluegras 10 - - 30 Annual bluegras 50 - - Barley (winter) 20 20 20 30 Barley (winter) 0 10 10 20 Blackgrass (2) 10 - - 20 Blackgrass (2) 20 - - Blk nightshade 100 70 100 100 Blk nightshade 40 60 55 50 Chickweed 55 50 60 100 Chickweed 0 35 50 100 Deadnettle 40 30 50 60 Deadnettle 0 60 30 70 Downy brome 20 - - 40 Downy brome 0 - - Field violet - 40 40 100 Field violet 20 20 20 20 Galium (2) 30 50 50 100 Galium (2) 20 100 40 100 Green foxtail 60 - - 100 Green foxtail 5 - - I. Ryegrass 10 - - 30 I. Ryegrass 10 - - Jointed goatgra 25 - - 30 Jointed goatgra 10 - - Kochia 100 35 60 100 Kochia 50 60 50 50 Lambsquarters 70 40 60 100 Lambsquarters 85 75 70 60 LS canarygrass 30 - - 30 LS canarygrass 10 - - Rape (1) 100 - - 100 Rape (1) 35 - - Redroot pigweed 100 45 50 100 Redroot pigweed 30 30 40 30 WO 98/47904 PCT/US98/08002 94 Russian thistle - - - 100 Russian thistle - 100 35 55 Scentless chamo - 20 30 100 Scentless chamo 70 75 100 70 Speedwell 100 30 55 - Speedwell 50 - - Spring Barley 25 20 20 20 Spring Barley 0 0 0 10 Sugar beet 100 - - 100 Sugar beet 65 - - Sunflower 100 - - 100 Sunflower 20 - Veronica hedera - - - 100 Veronica hedera - 70 100 100 Wheat (spring) 20 20 30 30 Wheat (spring) 0 10 20 0 Wheat (winter) 20 20 20 20 Wheat (winter) 0 0 10 0 Wild buckwheat 100 70 100 100 Wild buckwheat 10 60 60 75 Wild mustard 100 - - 100 Wild mustard 65 - - Wild oat (1) - - - 65 Wild oat (1) - - Wild oat (2) 20 - - - Wild oat (2) 0 - Windgrass 0 - - 20 Windgrass 0 - - Table E COMPOUND Table E COMPOUND Rate 8 g/ha 1 9 10 14 16 17 Rate 8 g/ha 1 12 13 14 POSTEMERGENCE PREEMERGENCE Annual bluegras - - - - 30 20 Annual bluegras - - - Barley (winter) 20 20 20 30 40 20 Barley (winter) 0 30 0 10 Blackgrass (2) 10 - - - 20 20 Blackgrass (2) 10 - Blk nightshade 100 - 100 100 100 100 Blk nightshade 20 30 10 10 Chickweed 10 40 50 100 80 65 Chickweed 0 30 20 60 Deadnettle 30 30 30 100 .60 45 Deadnettle 0 10 10 30 Downy brome 10 - - - 30 50 Downy brome 0 - - Field violet - 20 40 100 100 100 Field violet 50 10 0 20 Galium (2) 15 30 55 100 60 70 Galium (2) 0 65 0 100 Green foxtail 10 - - - 100 60 Green foxtail 5 - - I. Ryegrass 10 - - - 20 20 I. Ryegrass 0 Jointed goatgra 20 - - - 20 40 Jointed goatgra 0 Kochia 100 40 50 100 100 100 Kochia 40 45 10 45 Lambsquarters 65 30 40 100 100 100 Lambsquarters 55 65 - 50 LS canarygrass 15 - - - 35 20 LS canarygrass 10 Rape (1) 50 - - - 100 100 Rape (1) 35 Redroot pigweed 60 - 55 100 100 100 Redroot pigweed 20 20 30 35 Russian thistle - - - 100 100 100 Russian thistle - 20 50 45 Scentless chamo - 20 20 70 70 70 Scentless chamo 65 60 100 75 Speedwell 65 40 50 - - - Speedwell 60 - - - WO 98/47904 PCT/US98/08002 95 Spring Barley 40 10 10 30 20 20 Spring Barley 10 0 0 0 Sugar beet 100 - - - 100 100 Sugar beet 30 - Sunflower 100 - - - 100 20 Sunflower 10 - Veronica hedera - - - 100 100 100 Veronica hedera - 30 100 60 Wheat (spring) 20 20 20 30 50 25 Wheat (spring) 0 20 10 0 Wheat (winter) 10 10 20 20 20 15 Wheat (winter) 0 0 0 0 Wild buckwheat 60 55 50 100 100 100 Wild buckwheat 0 50 - 55 Wild mustard - - - - 100 100 Wild mustard - - Wild oat (1) - - - - 30 30 Wild oat (1) - Wild oat (2) 20 - - - - - Wild oat (2) 0 Windgrass - - - - 10 20 Windgrass 0 Table E COMPOUND Rate 4 g/ha 1 8 9 10 12 13 14 16 17 POSTEMERGENCE Annual bluegras 10 - - - - - - 20 10 Barley (winter) 20 10 10 10 20 15 20 50 10 Blackgrass (2) 10 - - - - - - 20 15 Blk nightshade 100 100 65 70 70 70 100 70 100 Chickweed 5 65 30 30 20 30 60 60 50 Deadnettle 10 65 30 30 30 30 100 50 20 Downy brome 10 - - - - - - 20 20 Field violet - 100 10 40 100 70 100 100 70 Galium (2) 10 100 30 30 50 50 50 55 55 Green foxtail 10 - - - - - - 30 20 I. Ryegrass 5 - - - - - - 10 10 Jointed goatgra 10 - - - - - - 20 10 Kochia 100 100 10 20 60 100 100 100 100 Lambsquarters 60 100 10 30 60 60 100 100 65 LS canarygrass 10 - - - - - - 30 20 Rape (1) 40 - - - - - - - 70 Redroot pigweed 35 100 10 50 100 100 100 100 100 Russian thistle - 100 - - 100 100 100 100 100 Scentless chamo - 100 10 10 50 30 70 60 60 Speedwell 50 - 20 20 - - - - Spring Barley 20 15 5 10 10 10 20 20 10 Sugar beet 100 - - - - - - - 100 Sunflower 80 - - - - - - - 20 WO 98/47904 PCT/US98/08002 96 Veronica hedera - 100 - - 20 20 100 60 20 Wheat (spring) 20 10 5 10 10 10 20 30 20 Wheat (winter) 10 10 5 10 15 10 30 20 10 Wild buckwheat 40 100 45 60 50 60 100 100 100 Wild mustard 65 - - - - - - 100 70 Wild oat (1) - - - - - - - 20 20 Wild oat (2) 10 Windgrass 0 - - - - - - 10 10 Table E COMPOUND Table E COMPOUND Rate 4 g/ha 1 8 17 Rate 2 g/ha 1 12 13 14 16 17 PREEMERGENCE POSTEMERGENCE Annual bluegras 10 - 60 Annual bluegras 10 - - - 10 10 Barley (winter) 0 5 0 Barley (winter) 10 20 10 10 20 10 Blackgrass (2) 10 - 10 Blackgrass (2) 10 - - - 10 10 Blk nightshade 20 50 20 Blk nightshade 65 65 60 100 60 65 Chickweed 0 50 70 Chickweed 2 30 20 65 50 20 Deadnettle 10 70 70 Deadnettle 10 30 30 100 30 20 Downy brome 0 - 0 Downy brome 0 - - - 10 10 Field violet 10 10 0 Field violet - 50 60 100 100 20 Galium (2) 0 100 100 Galium (2) 15 40 30 35 45 20 Green foxtail 0 - 40 Green foxtail 5 - - - 10 10 I. Ryegrass 0 - 0 I. Ryegrass 0 - - - 10 10 Jointed goatgra 10 - 0 Jointed goatgra 5 - - - 10 10 Kochia 30 30 70 Kochia 100 40 50 100 100 50 Lambsquarters 10 30 50 Lambsquarters 40 50 60 100 100 65 LS canarygrass 10 - 40 LS canarygrass 10 - - - 20 10 Rape (1) 0 - 0 Rape (1) 40 - - - - 60 Redroot pigweed 0 10 40 Redroot pigweed 10 70 100 100 100 60 Russian thistle - 55 0 Russian thistle - 60 55 100 100 100 Scentless chamo 70 70 60 Scentless chamo - 30 20 60 60 40 Speedwell 55 - - Speedwell 65 - - - - Spring Barley 0 0 0 Spring Barley 20 10 10 10 10 10 Sugar beet 0 - 40 Sugar beet 100 - - - - 100 Sunflower 0 - 10 Sunflower 10 - - - - 20 Veronica hedera - 100 55 Veronica hedera - 10 20 100 30 10 Wheat (spring) 0 0 0 Wheat (spring) 5 10 10 10 20 10 Wheat (winter) 0 0 0 Wheat (winter) 2 10 10 10 15 10 WO 98/47904 PCT/US98/08002 97 Wild buckwheat 0 85 30 Wild buckwheat 30 55 60 100 70 100 Wild mustard 50 - 50 Wild mustard 35 - - - 100 70 Wild oat (1) - - 20 Wild oat (1) - - - - 20 10 Wild oat (2) 0 - - Wild oat (2) 10 Windgrass 0 - 65 Windgrass 0 - - - 10 10 Table E COMPOUND Table E COMPOUND Rate 2 g/ha 1 17 Rate 1 g/ha 8 12 13 14 17 PREEMERGENCE POSTEMERGENCE Annual bluegras 0 40 Annual bluegras - - - - 0 Barley (winter) 0 0 Barley (winter) 10 10 10 10 10 Blackgrass (2) 0 0 Blackgrass (2) - - - - 10 Blk nightshade 10 20 Blk nightshade 100 25 60 70 50 Chickweed 0 70 Chickweed 50 10 30 20 40 Deadnettle 0 40 Deadnettle 45 20 30 20 10 Downy brome 0 0 Downy brome - - - - 5 Field violet 0 - Field violet 100 40 50 100 30 Galium (2) 0 30 Galium (2) 40 30 20 30 20 Green foxtail 0 30 Green foxtail - - - - 10 I. Ryegrass 0 0 I. Ryegrass - - - - 0 Jointed goatgra 0 10 Jointed goatgra - - - - 0 Kochia 40 - Kochia 75 35 30 70 Lambsquarters - 65 Lambsquarters 100 55 55 70 40 LS canarygrass 30 10 LS canarygrass - - - - 10 Rape (1) 0 0 Rape (1) - - - - 10 Redroot pigweed 0 0 Redroot pigweed 100 40 100 70 Russian thistle - 50 Russian thistle 100 50 50 50 100 Scentless chamo 35 30 Scentless chamo 55 20 30 55 10 Speedwell 0 - Speedwell - - - - Spring Barley 0 0 Spring Barley 10 10 10 10 10 Sugar beet 0 20 Sugar beet - - - - 65 Sunflower 0 10 Sunflower - - - - 10 Veronica hedera - 55 Veronica hedera 55 5 20 40 0 Wheat (spring) 0 0 Wheat (spring) 10 10 10 10 10 Wheat (winter) 0 0 Wheat (winter) 10 5 5 10 10 Wild buckwheat 0 20 Wild buckwheat 100 35 55 60 55 Wild mustard 40 10 Wild mustard - - - - 35 Wild oat (1) - 10 Wild oat (1) - - - - 10 WO 98/47904 PCT/US98/08002 98 Wild oat (2) 0 - Wild oat (2) Windgrass 0 70 Windgrass - - - - 5 Table E COMPOUND Rate 1 g/ha 17 PREEMERGENCE Annual bluegras Barley (winter) 0 Blackgrass (2) 10 Blk nightshade 10 Chickweed 70 Deadnettle 70 Downy brome 0 Field violet 0 Galium (2) 10 Green foxtail 30 I. Ryegrass 10 Jointed goatgra 0 Kochia 70 Lambsquarters 50 LS canarygrass 0 Rape (1) 0 Redroot pigweed 0 Russian thistle 30 Scentless chamo 70 Speedwell Spring Barley 0 Sugar beet 10 Sunflower 0 Veronica hedera Wheat (spring) 0 Wheat (winter) 0 Wild buckwheat 20 Wild mustard 0 Wild oat (1) 10 Wild oat (2) Windgrass 70 WO 98/47904 PCTIUS98/08002 99 Test F 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-leaf stage, seeds, tubers or plant parts selected from barnyardgrass (Echinochloa crus-galli), common water plantain 5 (Alisma plantago-aquatica), ducksalad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), gooseweed (Sphenoclea zeylanica), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola),monochoria (Monochoria vaginalis), river bullrush (Scirpusfluviatikis), redstem (Ammania species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis), tighthead sprangletop (Leptochloafasicularis) 10 and water-clover (Marsilea quadrifolia) were planted into this soil. The various rice seed types and methods are designated as: Rice indica 1 (2 leaf direct seeded indica type rice), Rice indica 3 (2 leaf transplanted indica type rice), Plantings and waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the 2 leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level 5 throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied directly to the paddy water by pipette, or to the plant foliage by an air pressure-assisted, calibrated belt-conveyer spray system. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant !0 response ratings, summarized in Table F, 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 F COMPOUND Table F COMPOUND Table F COMPOUND Rate 1000 g/ha 2 Rate 750 g/ha 2 Rate 600 g/ha 2 Paddy / silt lo Paddy / silt lo Paddy / silt lo Barnyardgrass 2 - Barnyardgrass 2 - Barnyardgrass 2 40 C. waterplantai 100 C. waterplantai 100 C. waterplantai Ducksalad - Ducksalad 60 Ducksalad 65 E. watergrass - E. watergrass - E. watergrass Gooseweed 100 Gooseweed 100 Gooseweed Junglerice - Junglerice - Junglerice 35 L. watergrass - L. watergrass - L. watergrass 10 Monochoria 100 Monochoria 100 Monochoria R. bulrush 100 R. bulrush 100 R. bulrush Redstem - Redstem 95 Redstem 100 Rice flatsedge 100 Rice flatsedge 100 Rice flatsedge 75 Rice indica 1 40 Rice indica 1 40 Rice indica 1 25 Rice indica 3 40 Rice indica 3 40 Rice indica 3 25 WO 98/47904 PCT/US98/08002 100 S. flatsedge - S. flatsedge 55 S. flatsedge 10 T. sprangletop 25 T. sprangletop 25 T. sprangletop 40 Water-clover 100 Water-clover 100 Water-clover Table F COMPOUND Table F COMPOUND Table F COMPOUND Rate 500 g/ha 2 Rate 450 g/ha 2 Rate 375 g/ha 2 Paddy / silt lo Paddy / silt lo Paddy / silt lo Barnyardgrass 2 60 Barnyardgrass 2 55 Barnyardgrass 2 C. waterplantai 100 C. waterplantai - C. waterplantai 100 Ducksalad 75 Ducksalad 85 Ducksalad 40 E. watergrass 45 E. watergrass - E. watergrass Gooseweed 100 Gooseweed - Gooseweed 100 Junglerice 80 Junglerice 55 Junglerice L. watergrass 45 L. watergrass 10 L. watergrass Monochoria 95 Monochoria - Monochoria 85 R. bulrush 100 R. bulrush - R. bulrush 90 Redstem 100 Redstem 100 Redstem Rice flatsedge 80 Rice flatsedge 70 Rice flatsedge Rice indica 1 15 Rice indica 1 25 Rice indica 1 Rice indica 3 10 Rice indica 3 25 Rice indica 3 S. flatsedge 45 S. flatsedge 55 S. flatsedge T. sprangletop 60 T. sprangletop 40 T. sprangletop Water-clover 100 Water-clover - Water-clover 95 Table F COMPOUND Table F COMPOUND Table F COMPOUND Rate 300 g/ha 2 Rate 250 g/ha 2 Rate 150 g/ha 2 Paddy / silt lo Paddy / silt lo Paddy / silt lo Barnyardgrass 2 30 Barnyardgrass 2 30 Barnyardgrass 2 10 C. waterplantai - C. waterplantai 100 C. waterplantai Ducksalad 75 Ducksalad 75 Ducksalad 40 E. watergrass - E. watergrass 10 E. watergrass Gooseweed - Gooseweed 100 Gooseweed Junglerice 0 Junglerice 55 Junglerice 0 L. watergrass 20 L. watergrass 10 L. watergrass 10 Monochoria - Monochoria 85 Monochoria R. bulrush - R. bulrush 75 R. bulrush Redstem 100 Redstem 98 Redstem 98 Rice flatsedge 70 Rice flatsedge 0 Rice flatsedge 65 WO 98/47904 PCT/US98/08002 101 Rice indica 1 25 Rice indica 1 0 Rice indica 1 20 Rice indica 3 20 Rice indica 3 0 Rice indica 3 15 S. flatsedge 25 S. flatsedge 35 S. flatsedge 20 T. sprangletop 55 T. sprangletop 30 T. sprangletop 10 Water-clover - Water-clover 90 Water-clover Table F COMPOUND Table F COMPOUND Table F COMPOUND Rate 125 g/ha 2 Rate 75 g/ha 2 Rate 64 g/ha 2 Paddy / silt lo Paddy / silt lo Paddy / silt lo Barnyardgrass 2 20 Barnyardgrass 2 10 Barnyardgrass 2 10 C. waterplantai - C. waterplantai - C. waterplantai Ducksalad 65 Ducksalad 0 Ducksalad 35 E. watergrass 10 E. watergrass - E. watergrass 15 Gooseweed - Gooseweed - Gooseweed Junglerice 60 Junglerice 0 Junglerice 0 L. watergrass 15 L. watergrass 0 L. watergrass 10 Monochoria - Monochoria - Monochoria R. bulrush - R. bulrush - R. bulrush Redstem 75 Redstem 85 Redstem 35 Rice flatsedge 85 Rice flatsedge 70 Rice flatsedge 35 Rice indica 1 15 Rice indica 1 10 Rice indica 1 10 Rice indica 3 15 Rice indica 3 10 Rice indica 3 15 S. flatsedge 20 S. flatsedge 25 S. flatsedge 0 T. sprangletop 20 T. sprangletop 10 T. sprangletop 10 Water-clover - Water-clover - Water-clover Table F COMPOUND Rate 32 g/ha 2 Paddy / silt lo Barnyardgrass 2 10 C. waterplantai Ducksalad 20 E. watergrass 15 Gooseweed Junglerice 10 L. watergrass 10 Monochoria R. bulrush WO 98/47904 PCT/US98/08002 102 Redstem 30 Rice flatsedge 10 Rice indica 1 10 Rice indica 3 10 S. flatsedge 0 T. sprangletop 10 Water -clover TEST G Seeds, tubers, or plant parts of alexandergrass (Brachiaria plantaginea), broadleaf signalgrass (Brachiaria decumbens), bermudagrass (Cynodon dactylon), common purslane 5 (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hiratum), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), pitted morning-glory (Ipomoea lacunosa), peanuts (Arachis hypogaea), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass 10 (Trichachne insularis) and surinam grass (Brachiaria decumbens) were planted into greenhouse pots of flats containing greenhouse planting medium. Plant species were grown grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). 15 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 G, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) 20 response means no test result. Table G COMPOUND Table G COMPOUND Rate 250 g/ha 1 8 17 Rate 250 g/ha 1 8 17 POSTEMERGENCE PREEMERGENCE Alexandergrass 0 100 35 Alexandergrass 5 100 50 B. signalgrass 10 100 65 B. signalgrass 0 100 70 Bermudagrass 0 70 25 Bermudagrass 0 100 80 C. purslane 100 100 100 C. purslane 100 100 100 C. ragweed 100 100 100 C. ragweed 0 100 100 Cotton 100 100 100 Cotton 0 100 70 Dallisgrass 0 70 75 Dallisgrass 0 50 95 WO 98/47904 PCT/US98/08002 103 Goosegrass 0 90 30 Goosegrass - 100 100 Guineagrass 30 70 65 Guineagrass - 100 95 Itchgrass 20 50 95 Itchgrass 0 65 80 Johnsongrass 75 100 75 Johnsongrass 0 70 85 Large crabgrass 20 75 0 Large crabgrass 0 20 100 P. morninglory 95 100 100 P. morninglory 10 80 90 Peanuts 40 65 90 Peanuts 0 75 50 Purple nutsedge 0 100 80 Purple nutsedge 0 75 25 Sandbur 0 100 - Sandbur 25 - 50 Sourgrass 15 90 30 Sourgrass 0 100 100 Surinam grass 0 90 50 Surinam grass 0 100 80 Table G COMPOUND Table G COMPOUND Rate 125 g/ha 1 8 17 Rate 125 g/ha 1 8 17 POSTEMERGENCE PREEMERGENCE Alexandergrass 0 100 35 Alexandergrass 5 0 50 B. signalgrass 10 100 40 B. signalgrass 0 85 30 Bermudagrass 0 60 25 Bermudagrass 0 0 65 C. purslane 100 100 100 C. purslane 100 100 100 C. ragweed 85 100 100 C. ragweed 0 100 100 Cotton 100 100 100 Cotton 0 90 25 Dallisgrass 0 75 20 Dallisgrass 0 30 95 Goosegrass 0 70 20 Goosegrass - 90 100 Guineagrass 30 60 15 Guineagrass - 65 75 Itchgrass 10 50 50 Itchgrass 0 30 80 Johnsongrass 65 100 50 Johnsongrass 0 30 75 Large crabgrass - 75 0 Large crabgrass 0 30 80 P. morninglory 70 100 100 P. morninglory - 65 65 Peanuts 35 65 30 Peanuts 0 40 50 Purple nutsedge 0 100 - Purple nutsedge 0 10 Sandbur 0 80 40 Sandbur 0 - 0 Sourgrass 15 75 15 Sourgrass 0 98 100 Surinam grass 0 90 50 Surinam grass 0 30 65 Table G COMPOUND Table G COMPOUND Table G COMPOUND Rate 64 g/ha 8 17 Rate 64 g/ha 8 17 Rate 32 g/ha 8 POSTEMERGENCE PREEMERGENCE POSTEMERGENCE WO 98/47904 PCT/US98/08002 104 Alexandergrass 100 35 Alexandergrass 0 30 Alexandergrass 75 B. signalgrass 100 30 B. signalgrass 0 10 B. signalgrass 75 Bermudagrass 60 25 Bermudagrass 0 10 Bermudagrass 65 C. purslane 100 95 C. purslane 100 100 C. purslane 100 C. ragweed 100 95 C. ragweed 100 100 C. ragweed 100 Cotton 100 100 Cotton 70 10 Cotton 100 Dallisgrass 50 0 Dallisgrass 40 65 Dallisgrass 50 Goosegrass 65 5 Goosegrass 90 90 Goosegrass 60 Guineagrass 60 0 Guineagrass 25 35 Guineagrass 50 Itchgrass 50 50 Itchgrass 0 30 Itchgrass 65 Johnsongrass 100 15 Johnsongrass 40 35 Johnsongrass 75 Large crabgrass 75 0 Large crabgrass 0 65 Large crabgrass 65 P. morninglory 98 85 P. morninglory 75 30 P. morninglory 100 Peanuts 60 30 Peanuts 20 - Peanuts 50 Purple nutsedge 100 - Purple nutsedge 10 - Purple nutsedge 75 Sandbur 75 - Sandbur - 0 Sandbur 75 Sourgrass 75 10 Sourgrass 0 70 Sourgrass 40 Surinam grass 75 50 Surinam grass 20 50 Surinam grass 80 Table G COMPOUND Table G COMPOUND Table G COMPOUND Rate 32 g/ha 8 Rate 16 g/ha 8 Rate 16 g/ha 8 PREEMERGENCE POSTEMERGENCE PREEMERGENCE Alexandergrass 0 Alexandergrass 20 Alexandergrass 0 B. signalgrass 0 B. signalgrass 50 B. signalgrass 0 Bermudagrass 0 Bermudagrass 0 Bermudagrass 0 C. purslane 100 C. purslane 100 C. purslane 100 C. ragweed 100 C. ragweed 100 C. ragweed 100 Cotton 70 Cotton 100 Cotton 100 Dallisgrass 20 Dallisgrass 10 Dallisgrass 0 Goosegrass 0 Goosegrass 60 Goosegrass 0 Guineagrass 25 Guineagrass 0 Guineagrass 0 Itchgrass 0 Itchgrass 0 Itchgrass 0 Johnsongrass 20 Johnsongrass 65 Johnsongrass 30 Large crabgrass 0 Large crabgrass 65 Large crabgrass 0 P. morninglory 50 P. morninglory 90 P. morninglory 80 Peanuts 50 Peanuts 10 Peanuts 20 Purple nutsedge 10 Purple nutsedge 100 Purple nutsedge 0 Sandbur - Sandbur 35 Sandbur WO 98/47904 PCT/US98/08002 105 Sourgrass 0 Sourgrass 40 Sourgrass 0 Surinam grass 20 Surinam grass 10 Surinam grass 0 Table G COMPOUND Table G COMPOUND Rate 8 g/ha 8 Rate 8 g/ha 8 POSTEMERGENCE PREEMERGENCE Alexandergrass - Alexandergrass 0 B. signalgrass 0 B. signalgrass 0 Bermudagrass 0 Bermudagrass 0 C. purslane 40 C. purslane 100 C. ragweed 10 C. ragweed 100 Cotton 80 Cotton 70 Dallisgrass 0 Dallisgrass 0 Goosegrass 0 Goosegrass 0 Guineagrass 0 Guineagrass 0 Itchgrass 0 Itchgrass 0 Johnsongrass 0 Johnsongrass 10 Large crabgrass 50 Large crabgrass 0 P. morninglory 75 P. morninglory 80 Peanuts 5 Peanuts 20 Purple nutsedge 0 Purple nutsedge 0 Sandbur 35 Sandbur Sourgrass 0 Sourgrass 0 Surinam grass 0 Surinam grass 0 Test H Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture 5 and applied to the surface of the water which was contained in each pot. Individual containers of barnyardgrass (Echinochloa oryzicola), small flower flatsedge (Cyperus diffonnrmus), common falsepimpernel (Lindernia procumbens), monochoria (Monochoria vaginalis) and bulrush (Scirpusjuncoides) were seeded and allowed to grow until the leaf stage of development was reached. A Sultama clay loam soil was used for this propagation. 0 Japonica rice (Oryza sativa) was transplanted at 0 and 2 cm depth (designated Rice japonica 1 and Rice japonica 2 respectively) five days before application of the test compound to the water surface. An early and late stage of each weed species was treated, the stage of development being related to the concurrent planting of Scirpus juncoides which was then treated at the 1.5 (early (1)) and the 2.5 (late (2)) leaf stage.
WO 98/47904 PCT/US98/08002 106 Treated plants and untreated controls were maintained under greenhouse conditions for twenty to thirty days at which time treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table H, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) -5 indicated that no test result was recorded. Table H COMPOUND Table H COMPOUND Rate 250 g/ha 2 4 9 10 16 Rate 125 g/ha 2 4 9 10 16 Flood Saita soi Flood Saita soi Barnyardgrass 1 60 40 40 70 100 Barnyardgrass 1 50 30 30 30 100 Barnyardgrass 2 35 35 35 30 100 Barnyardgrass 2 35 20 35 40 100 Falsepimpernell 100 100 100 100 100 Falsepimpernell 100 100 100 100 100 Falsepimpernel2 100 100 100 100 100 Falsepimpernel2 100 100 100 100 100 Monochoria 1 100 100 80 100 100 Monochoria 1 95 100 70 80 100 Monochoria 2 70 70 65 50 100 Monochoria 2 50 - 40 65 100 Rice japonica 1 75 100 60 70 90 Rice japonica 1 40 20 40 40 90 Rice japonica 2 30 15 45 45 80 Rice japonica 2 10 0 25 25 75 S. flatsedge 1 100 90 100 100 100 S. flatsedge 1 100 100 100 100 100 S. flatsedge 2 80 45 90 60 100 S. flatsedge 2 45 30 55 70 100 Scirpus 1 75 85 40 60 100 Scirpus 1 60 80 40 35 100 Scirpus 2 50 40 50 30 100 Scirpus 2 40 20 40 40 100 Table H COMPOUND Table H COMPOUND Rate 64 g/ha 2 4 9 10 16 Rate 32 g/ha 2 4 9 10 16 Flood Saita soi Flood Saita soi Barnyardgrass 1 35 40 40 35 100 Barnyardgrass 1 20 10 20 0 80 Barnyardgrass 2 30 25 40 20 90 Barnyardgrass 2 30 10 30 10 60 Falsepimpernell 100 100 100 100 100 Falsepimpernell 90 60 100 100 100 Falsepimpernel2 100 100 100 100 100 Falsepimpernel2 100 100 100 100 100 Monochoria 1 75 80 80 60 100 Monochoria 1 60 65 50 30 100 Monochoria 2 .60 55 50 30 100 Monochoria 2 30 35 35 35 70 Rice japonica 1 55 15 15 30 85 Rice japonica 1 0 10 0 10 70 Rice japonica 2 0 0 10 15 70 Rice japonica 2 5 0 0 15 55 S. flatsedge 1 55 100 60 85 100 S. flatsedge 1 30 20 50 20 100 S. flatsedge 2 45 20 55 70 100 S. flatsedge 2 30 20 35 30 100 Scirpus 1 50 70 30 40 95 Scirpus 1 40 40 30 0 85 Scirpus 2 30 20 40 30 90 Scirpus 2 20 20 10 0 85

Claims (10)

  1. 2. A compound of Claim 1 wherein X is F or Cl; and Y is F, Cl or Br. 15 3. A compound of Claim 2 wherein R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkylcarbonyl, C 4 -C 7 cycloalkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkoxyalkylcarbonyl, S(0) 2 R 17 , C(0)NR 4 R 5 or benzoyl. 20
  2. 4. A compound of Claim 3 wherein J is J-1, J-2, J-3 or J-6.
  3. 5. A compound of Claim 4 wherein 25 Z is CR 6 R 7, O or S; R 6 is H, halogen, C I-C 6 alkoxy or C 2 -C 6 alkylcarbonyloxy; R 7 is H or halogen; m and n are each independently 1 or 2, provided that m + n is 2 or 3; R 8 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 3 -C 6 alkenyl; 30 R 9 is halogen, C 1 -C 6 alkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; R 10 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or NH 2 ; and R 1 1 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.
  4. 6. A compound of Claim 5 wherein 35 RI is H, C 2 -C 3 alkylcarbonyl or C 2 -C 3 alkoxycarbonyl; and R 2 is C 1 -C 2 haloalkyl. WO 98/47904 PCT/US98/08002 110
  5. 7. A compound of Claim 6 wherein J is J-1.
  6. 8. A compound of Claim 6 wherein -5 J is J-2.
  7. 9. A compound of Claim 6 wherein J is J-3. 10 10. A compound of Claim 6 wherein J is J-6.
  8. 11. The compound of Claim 6 which is selected from the group: (a) N-[2-chloro-5-[(dihydro-3-oxo- 1H,3H,5H-pyrazolo[1,2-c][1,3,4]thiadiazol- 1 15 ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide; (b) N-[2-chloro-5-[(dihydro-3-oxo- 1H,3H,5H-pyrazolo[1,2-c][1,3,4]thiadiazol-1 ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]-2-methylpropanamide; (c) 1-chloro-N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl) 1(2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; 20 (d) N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H) pyrimidinyl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide; (e) methyl [2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H) pyrimidinyl]-4-fluorophenyl][(chloromethyl)sulfonyl]carbamate; (f) 1-chloro-N-[2-chloro-5-[3,6-dihydro-3,6-dioxo-3-(2-propenyl)-4 25 (trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; (g) 1-chloro-N-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- 1H 1,2,4-triazol- 1 -yl]-4-fluorophenyl]methanesulfonamide; (h) N-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- 1H-1,2,4 triazol-1-yl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide. 30
  9. 12. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent.
  10. 13. A method for controlling the growth of undesired vegetation comprising 35 contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.
AU72526/98A 1997-04-22 1998-04-20 Herbicidal sulfonamides Abandoned AU7252698A (en)

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