EP0977760A1 - Herbicidal sulfonamides - Google Patents

Herbicidal sulfonamides

Info

Publication number
EP0977760A1
EP0977760A1 EP98919824A EP98919824A EP0977760A1 EP 0977760 A1 EP0977760 A1 EP 0977760A1 EP 98919824 A EP98919824 A EP 98919824A EP 98919824 A EP98919824 A EP 98919824A EP 0977760 A1 EP0977760 A1 EP 0977760A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
chc1
haloalkyl
compound
chloro
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.)
Withdrawn
Application number
EP98919824A
Other languages
German (de)
French (fr)
Inventor
Karlheinz Drauz
Wonpyo Hong
Balreddy Kamireddy
Anne Vogt
Christoph Helmut Weckbecker
Ingo Klement
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
Degussa Huels AG
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Degussa GmbH, Degussa Huels AG, EI Du Pont de Nemours and Co filed Critical Degussa GmbH
Publication of EP0977760A1 publication Critical patent/EP0977760A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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

Definitions

  • This invention relates to certain aryl sulfonamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • U.S. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula
  • X and Y are Br, Cl or F;
  • R is alkyl, haloalkyl or dialkylamino
  • R 1 is H, ⁇ a, lower alkyl or SO 2 R;
  • R 2 is alkyl, haloalkyl or lower alkoxy; and R 3 is halogen, alkyl or haloalkyl.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, TV-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
  • X is H, F or Cl
  • Y is F, Cl, Br, cyano, nitro, C*-C 3 haloalkyl, C r C 3 alkoxy, C ⁇ -C 3 haloalkoxy or C(S)NH 2 ;
  • R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C3-C6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C -C 6 haloalkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C3-C6 alkoxyalkylcarbonyl, C 2 -C6 haloalkoxycarbonyl, C3-C6 cycloalkyl, C3-C 6 halocycloalkyl, C4-C7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl
  • R 3 is H, C1-C3 alkyl or C r C3 haloalkyl; or R 3 is phenyl optionally substituted with
  • R 4 is H, C1-C3 alkyl or C1-C3 haloalkyl; or R 4 is phenyl optionally substituted with C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF 3 ;
  • R 5 is C j -C 3 alkyl or C - -C 3 haloalkyl; or
  • R 4 and R 5 are taken together as -CH-CH 2 -, -CH 2 CH 2 CH 2 -,
  • Z is CR6R7, O, S, S(O), S(O) 2 , N(C r C 4
  • R 6 is H, C C 6 alkyl, halogen, hydroxy, Cj-Cg alkoxy, C'-C ⁇ haloalkyl, C r C 6 haloalkoxy, C 2 -Cg alkylcarbonyloxy or C 2 -Cg haloalkylcarbonyloxy;
  • R 7 is H, C Cg alkyl, hydroxy or halogen; or when R 6 and R 7 are bonded to adjacent carbon atoms they can be taken together with
  • CH 2 A the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 C1-C3 alkyl;
  • R 8 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
  • R 9 is H, halogen, cyano, alkyl, C1-C3 alkoxy or C--C3 haloalkoxy;
  • R 1 1 is C r C 6 alkyl, C,-C 6 alkylthio, C r C 6 haloalkyl or N(CH 3 ) 2 ;
  • R 12 is H, halogen, C r C 6 alkyl, C r C 6 haloalkyl or C r C 6 alkoxy;
  • R 13 and R 14 are each independently H, C r C 6 alkyl or C r C 6 haloalkyl;
  • R 15 is H, C r C 6 alkyl or C r C 6 haloalkyl; each R 16 is independently H, C r C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl or C 2 -C 6 alkoxyalkyl; R 17 is C r C 6 alkyl, C r C 6 haloalkyl other than CF 3 , C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C6 cyanoalkyl, C*-C 6 nitroalkyl, C2-C 6 alkylthioalkyl,
  • each Q is independently O or S.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, rt-propyl, -propyl, or the different butyl, pentyl or hexyl isomers.
  • 1-2 alkyl indicates that one or two of the available positions for that substituent may be alkyl which are independently selected.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1 -propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, «-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 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.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group. Examples of
  • alkylsulfmyl 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.
  • 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 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
  • alkynylsulfonyl and the like, are defined analogously to the above examples.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Examples of “cycloalkylalkyl” include 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 cycloalkyl group substituted with one cyano group.
  • Examples of “cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl.
  • nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.
  • nitrogen containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • Synthetic methods for the preparation of /V-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary 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.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethydioxirane.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen which are independently selected. 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, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 G ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • haloalkylsulfinyl examples include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl examples include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • haloalkoxyalkoxy examples include CF 3 OCH 2 O, ClCH 2 CH 2 OCH 2 CH 2 O, Cl 3 CCH 2 OCH 2 O as well as branched alkyl derivatives.
  • C C 3 alkylsulfonyl designates 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
  • 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 CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • substituents When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)i_j, then the number of substituents may be selected from the integers between i and j inclusive.
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • 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.
  • 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.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • 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 salts thereof, wherein
  • R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C -C 6 haloalkoxyalkyl, C 2 -Cg alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C 2 -C6 haloalkylcarbonyl, C 2 -Cg alkoxycarbonyl, C 3 -C 6 alkoxyalkylcarbonyl, S(O) 2 R 17 , C(O)NR R5 or benzoyl.
  • 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; R 6 is H, halogen, C Cg alkoxy or C 2 -C6 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 r C 6 alkyl, C r C 6 haloalkyl or C 3 -C 6 alkenyl; R 9 is halogen, Cj-Cg alkyl, Cj-C 3 alkoxy or C ⁇ -C 3 haloalkoxy; R 10 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl or NH 2 ; and
  • Rl 1 is C r C 6 alkyl or C r C 6 haloalkyl.
  • R 1 is H, C -C 3 alkylcarbonyl or C 2 -C 3 alkoxycarbonyl; and R 2 is C r C 2 haloalkyl.
  • J is J-2.
  • Preferred 8 Compounds of Preferred 5 wherein 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:
  • 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.
  • 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.
  • 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 ⁇ -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 la-If are various subsets of the compounds of Formula I, and all substituents for Formulae la-If are as defined above for Formula I.
  • 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 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 la wherein R 1 is H.
  • Compounds of Formula la wherein R 1 is other than H can be prepared by treatment of the ⁇ H compound with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the corresponding capped compounds of Formula la.
  • 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.
  • Scheme 1
  • Scheme 2 illustrates the preparation of compounds of Formula lb.
  • 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. The Chemistry of Heterocyclic Compounds (1981), 37, 365-403; Lyga, J. W. Synthetic 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 Formula 1 1 , which are treated with an appropriate sulfonyl chloride to provide the compounds of Formula lb 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 lb wherein R l is other than H.
  • G is halide or sulfonate
  • R la is Rl excluding H lb (R- is other than H)
  • 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 a base such as sodium hydride, followed by acidification with dilute HC1 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.
  • R la is R- excluding H
  • 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 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 than H.
  • Step A 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 °C. -H NMR (Me 2 SO- ⁇ f 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 0
  • a solution of title compound of Step A (50 g, 0.214 mol) in 6NHC1 (200 mL) was heated at reflux for 6h.
  • Step D Preparation of 3- (4-chloro-2-fluoro-5-nitrophenv ⁇ imino1tetrahydro-lH H- f 1 ,3,41thiadiazolor3,4-a.1pyridazin- 1 -one
  • Step F Preparation of 1 -chloro-N-r2-chloro-4-fluoro-5-[ " (tetrahydro-3-oxo- 1H.3H- ri,3,41thiadiazolo[3_,4-q1pyridazin-l- ylidene)aminolphenynmethanesulfonamide
  • Step F a compound of this invention, was isolated by flash chromatography as a solid melting at 168 °C ( 1.40 g, 81%).
  • Step A Preparation of N-r2-chloro-4-fluoro-5-
  • pyridine 0.5 mL
  • methylene chloride 5 mL
  • dimethylaminopyridine 25 mg
  • isobutyryl chloride 110 mg
  • Step B Preparation of 3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-
  • Step B 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%).
  • Step E Preparation of 1 -chloro-N-r2-chloro-5-f 3 ,6-dihydro-3-methyl-2 ⁇ 6-dioxo-4- (trifluoromethyl (2H)-pyrimidinyl)-4-fluorophenyl1methanesulfonamide
  • Step A Preparation of N- f2 -chloro-5 - 3 ,6-dih vdro-3 -methyl-2 ,6-dioxo-4-

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Abstract

Compounds of Formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation. In said formula, J is (J-1), (J-2), (J-3), (J-4), (J-5), (J-6) and X, Y, Z, Q, R?1, R2, R6-R15¿, m and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (I).

Description

TITLE
HERBICIDAL SULFONAMIDES
BACKGROUND OF THE INVENTION
This invention relates to certain aryl sulfonamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
U.S. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula
wherein, inter alia
X and Y are Br, Cl or F;
R is alkyl, haloalkyl or dialkylamino;
R1 is H, Νa, lower alkyl or SO2R;
R2 is alkyl, haloalkyl or lower alkoxy; and R3 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 stereoisomers, TV-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
I wherein
X is H, F or Cl;
Y is F, Cl, Br, cyano, nitro, C*-C3 haloalkyl, CrC3 alkoxy, Cι-C3 haloalkoxy or C(S)NH2;
R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C6 alkoxyalkyl, C -C6 haloalkoxyalkyl, formyl, C2-C6 alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C -C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C6 alkoxyalkylcarbonyl, C2-C6 haloalkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, S(O)2R17, C(O)SR3, C(O)NR4R5 or benzoyl; R2 is Ci-Cg haloalkyl other than CF3, C2-Cg alkoxyalkyl, C -Cg haloalkoxyalkyl, C2-C cyanoalkyl, C nitroalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C3-C8 alkoxycarbonylalkyl or C3-C8 alkylcarbonyloxyalkyl;
R3 is H, C1-C3 alkyl or CrC3 haloalkyl; or R3 is phenyl optionally substituted with
C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF3; R4 is H, C1-C3 alkyl or C1-C3 haloalkyl; or R4 is phenyl optionally substituted with C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF3; R5 is C j -C3 alkyl or C - -C3 haloalkyl; or
R4 and R5 are taken together as -CH-CH2-, -CH2CH2CH2-,
-CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or -CH2CH2OCH2CH2-; J is
J-3
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;
Z is CR6R7, O, S, S(O), S(O)2, N(CrC4
R6 is H, C C6 alkyl, halogen, hydroxy, Cj-Cg alkoxy, C'-C^ haloalkyl, CrC6 haloalkoxy, C2-Cg alkylcarbonyloxy or C2-Cg haloalkylcarbonyloxy;
R7 is H, C Cg alkyl, hydroxy or halogen; or when R6 and R7 are bonded to adjacent carbon atoms they can be taken together with
CH2 A the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 C1-C3 alkyl;
R8 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl or C3-C6 alkynyl; R9 is H, halogen, cyano, alkyl, C1-C3 alkoxy or C--C3 haloalkoxy;
R10 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, HC(=O), C2-C5 alkylcarbonyl or N(R16)2; R1 1 is CrC6 alkyl, C,-C6 alkylthio, CrC6 haloalkyl or N(CH3)2; R12 is H, halogen, CrC6 alkyl, CrC6 haloalkyl or CrC6 alkoxy; R13 and R14 are each independently H, CrC6 alkyl or CrC6 haloalkyl;
R15 is H, CrC6 alkyl or CrC6 haloalkyl; each R16 is independently H, CrC6 alkyl, Cι-C6 haloalkyl, C3-C6 alkenyl or C2-C6 alkoxyalkyl; R17 is CrC6 alkyl, CrC6 haloalkyl other than CF3, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, C*-C6 nitroalkyl, C2-C6 alkylthioalkyl,
C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C3-Cg alkoxycarbonylalkyl or C3-C8 alkylcarbonyloxyalkyl; and 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, rt-propyl, -propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl which are independently selected. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1 -propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of
"alkylsulfmyl" include CH3S(O), CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2, CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2 and CH3CH(CN)CH2. "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 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 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; 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 /V-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary 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. N. Ley, Ed., 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 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. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC≡CCHCl, CF3C≡C, CC13C≡C and FCH2G≡CCH2. Examples of "haloalkoxy" include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of "haloalkylthio" include CC13S, CF3S, CC13CH2S and C1CH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2. Examples of "haloalkoxyalkoxy" include CF3OCH2O, ClCH2CH2OCH2CH2O, Cl3CCH2OCH2O as well as branched alkyl derivatives.
The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 8. For example, C C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)i_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 R1 or R10, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula I, 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. The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally suitable salts thereof, wherein
X is F or Cl; and Y is F, Cl or Br. Preferred 2. Compounds of Preferred 1 wherein
R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C2-C6 alkoxyalkyl, C -C6 haloalkoxyalkyl, C2-Cg alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C3-C6 alkoxyalkylcarbonyl, S(O)2R17, C(O)NR R5 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 CR6R7, O or S; R6 is H, halogen, C Cg alkoxy or C2-C6 alkylcarbonyloxy;
R7 is H or halogen; m and n are each independently 1 or 2, provided that m + n is 2 or 3; R8 is CrC6 alkyl, CrC6 haloalkyl or C3-C6 alkenyl; R9 is halogen, Cj-Cg alkyl, Cj-C3 alkoxy or Cι-C3 haloalkoxy; R10 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl or NH2; and
Rl 1 is CrC6 alkyl or CrC6 haloalkyl. Preferred 5. Compounds of Preferred 4 wherein
R1 is H, C -C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; and R2 is CrC2 haloalkyl. 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 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-lH,3H,5H-pyrazolo[l,2-c][l,3,4]thiadiazol-l- 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) l-chloro-N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; (d) N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide; (e) methyl [2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenyl][(chloromethyl)sulfonyl]carbamate; (f) l-chloro-iV-[2-chloro-5-[3,6-dihydro-3,6-dioxo-3-(2-propenyl)-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide;
(g) l-chloro-Λ^-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-lH- 1 ,2,4-triazol- 1 -yl]-4-fluorophenyl]methanesulfonamide; and (h) N-[2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-lH-l,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 comprise the above preferred compounds.
This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds. DETAILS OF THE INVENTION
The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-6. The definitions of X, Y, Rϊ-R17, 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 la-If are various subsets of the compounds of Formula I, and all substituents for Formulae la-If are as defined above for Formula I.
Compounds of Formula la 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 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 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 la wherein R1 is H. Compounds of Formula la wherein R1 is other than H can be prepared by treatment of the ΝH compound with an alkyl halide, alkyl carbonyl chloride or alkyl sulfonyl chloride to give the corresponding capped compounds of Formula la.
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. Scheme 1
2 3
or la (R j is H) R • a is R ' excluding H
la (Rj is other than H)
Scheme 2 illustrates the preparation of compounds of Formula lb. 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. The Chemistry of Heterocyclic Compounds (1981), 37, 365-403; Lyga, J. W. Synthetic 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 Formula 1 1 , which are treated with an appropriate sulfonyl chloride to provide the compounds of Formula lb wherein R1 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 lb wherein Rl is other than H.
Scheme 2
R8-G reduction
G is halide or sulfonate
10
Rla is Rl excluding H lb (R- is other than H) 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 a base such as sodium hydride, followed by acidification with dilute HC1 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 wherein R1 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 R1 is other than H.
Scheme 3
is other than H) Rla is R- excluding H 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 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 R1 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 R1 is other than H.
Scheme 4
17
19
Id (Rl is H) Id (Rl is other than H) Compounds of Formula Ie 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. Compounds of Formula 21 can be deprotected with HCl, 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 Ie wherein Rl is other than H.
Scheme 5
C1SQ R2
Rl- s R-excluding H; Ie (R is other than H) G is halide or sulfonate Compounds of Formula If can be prepared by the methods shown in Scheme 6. Acetanilides of Formula 1 are reacted with IC1 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 method and the preparation of compounds of Formula 24 are known in the art: see, for example, Yamanaka et al. Heterocycles ( 1992), 55, 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
23 24
It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I. -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 0 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. !H NMR spectra are reported in ppm downfield from 5 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-chIoro-2-fluoro-5-nitrophenyl)acetamide
To a stirred solution of N-(4-chloro-2-fluorophenyl)acetamide (180.6 g, 0.96 mol) in 0 concentrated sulfuric acid (IL) was added a mixture of 175 mL of concentrated HΝO3 and 175 mL of concentrated sulfuric acid at 0 to 5 °C 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 5 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 °C. -H NMR (Me2SO-βf6) δ 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 0 A solution of title compound of Step A (50 g, 0.214 mol) in 6NHC1 (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 °C. Η NMR (CDC13): δ 7.38 (d, 1H), 7.17 (d, 1H), 4.11 (br s, 2H). 5 Step C: Preparation of l-chloro-5-fluoro-4-isothiocvanato-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 -dioxane (200 mL) at 0 °C was added triethylamine (6 mL) in ?-dioxane (30 mL) dropwise under nitrogen atmosphere during 30 min. The reaction mixture was first 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-nitrophenvπimino1tetrahydro-lH H- f 1 ,3,41thiadiazolor3,4-a.1pyridazin- 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 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 drop wise 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% ΗC1 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 °C (5.4g, 78%). Η NMR (CDC13): δ 7.63 (d, 1Η), 7.30 (d, 1Η), 3.80 (m, 4Η), 2.32 (m, 1H), 1.98 (m, 4H). Step E: Preparation of 3-[(5-amino-4-chloro-2-fluorophenyl)iminoltetrahydro-lH,3H- 1.3.4"lthiadiazolo|"3,4-α Ipyridazin- 1 -one
A mixture of the title compound of Step D (2.2 g, 6.37 mmol) and SnCl2.2Η2O (4.5 g, 20 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 temperature overnight. The reaction mixture then was filtered through a pad of celite, the 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%). 1H NMR (CDC13): δ 7.05 (d, 1H), 6.36 (d, 1H), 3.90 (bs, 2H), 3.74 (m, 4H), 1.98 (m, 4H).
Step F: Preparation of 1 -chloro-N-r2-chloro-4-fluoro-5-["(tetrahydro-3-oxo- 1H.3H- ri,3,41thiadiazolo[3_,4-q1pyridazin-l- ylidene)aminolphenynmethanesulfonamide
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 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 melting at 168 °C ( 1.40 g, 81%). Η NMR (CDC13): δ 7.32 (d, 1H), 7.23 (d, 1H), 6.92 (s, 1 H), 4.53 (s, 2H), 3.74 (m, 4H), 1.98 (m, 4H).
EXAMPLE 2 Step A: Preparation of N-r2-chloro-4-fluoro-5-|"(tetrahvdro-3-oxo- 1H3H- r 1 <3 ,41thiadiazolo 3.4-αlpyridazin- 1 -ylidene)aminolphenvn-N- f(chloromethyl)sulfonyl -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. The reaction mixture was stirred at room temperature for 2h and diluted with methylene chloride (5 mL), washed with water (5 mL) and 5% ΗC1 (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 °C (0.3 lg, 89%). Η NMR (CDCI3): δ 7.32 (d, 1Η), 7.16 (d, 1Η), 5. 41 (dd, 1Η), 4.84 (dd, 1Η), 3.80 (m, 4Η), 2.32 (m, 1H), 1.98 (m, 4H), 1.12 (d, 6H).
EXAMPLE 3 Step A: Preparation of l-chloro-5-fluoro-4-isocvanato-2 -nitrobenzene
To a stirred solution of diphosgene (4.75 g, 24 mmol) in 100 mL of/?-dioxane was added the title compound of Step B of Example 1 (3.8 g, 20 mmol) in 10 mL ofp-dioxane at room temperature. The reaction mixture was cooled to 10 °C and a solution of 5 ml of triethylamine in 25 mL of ?-dioxane was added dropwise at that temperature. The temperature was then raised to 70 °C 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. Step B: Preparation of 3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-
2,4(1 H,3H)-p yrimidinedione To a solution of dimethylformamide (30 mL) and NaΗ (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 argon atmosphere, then at room temperature for 12 h. The reaction mixture was then poured into a beaker containing ice (50 g) and concentrated ΗC1 (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%). Η NMR (DMSO-d6): δ 8.48 (d, 1Η), 8.15 (d, 1Η), 6.43(s, 1Η), 3.57 (s, 3Η), Step C: Preparation of 3-(4-chloro-2-fluoro-5-nitrophenyl)- 1 -methyl-6-
(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione 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 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 °C (1.6 g, 89%). Η NMR (CDC13): δ 8.03 (d, 1H), 7.50 (d, 1H), 6.39 (s, 1H), 3.57 (s, 3H), Step D: Preparation of 3-(5-amino-4-chloro-2-fluorophenyl)-l-methyl-6-
(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione A mixture of the title compound of Step C (1.5 g, 4.08 mmol) and SnCl2.2Η2O (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 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 °C (1.15 g, 84%). Η NMR (CDCI3): δ 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-r2-chloro-5-f 3 ,6-dihydro-3-methyl-2<6-dioxo-4- (trifluoromethyl (2H)-pyrimidinyl)-4-fluorophenyl1methanesulfonamide
To a solution of the title compound of Step D (1.1 g; 3.26 mmol) and pyridine (lmL) 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 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 °C (1.20 g, 83%). Η ΝMR (CDC13): δ 7.67 (d, 1Η), 7.38 (d, 1Η), 7.18 (br s, 1Η), 6.37 (s, 1Η), 4.55 (s, 3Η), 3.56 (s, 3H). EXAMPLE 4
Step A: Preparation of N- f2 -chloro-5 - 3 ,6-dih vdro-3 -methyl-2 ,6-dioxo-4-
(trifluoromethyl)- 1 (2H)-pyrimidinyl)-4-fluorophenvπ-N- lYchloromethvPsulfonvHacetamide To a solution of the title compound of Step E of Example 3 (0.25 g, 0.55 mmol), 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% ΗC1 (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 170 °C (0.25g, 93%). Η ΝMR (CDCI3): δ 7.52 (m, 2Η), 6.36 (d, 1H), 5.40 (dd, 1H), 4.90 (dd, 1H) 3.60 (s, 3H). 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
Ei R^ X Y R6
H CH2F F Cl H
H CH2F Cl Cl H
H CH2C1 F Cl H
H CH2C1 Cl Cl H
H CH2Br F Cl H
H CH2Br Cl Cl H
C(=O)CH3 CH2F F Cl H
C(=O)CH3 CH2F Cl Cl H
C(=O)CH3 CH2C1 F Cl H
C(=O)CH3 CH2C1 Cl Cl H
C(=O)CH3 CH2Br F Cl H
C(=O)CH3 CH2Br Cl Cl H
C(=O)CH(CH3)2 CH2F F Cl H
C(=O)CH(CH3)2 CH2F Cl Cl H
C(=O)CH(CH3)2 CH2C1 F Cl H
C(=O)CH(CH3)2 CH2C1 Cl Cl H
C(=O)CH(CH3)2 CH2Br F Cl H
C(=O)CH(CH3)2 CH2Br Cl Cl H
CO2CH3 CH2F F Cl H
CO2CH3 CH2F Cl Cl H
CO2CH3 CH2C1 F Cl H
CO2CH3 CH2C1 Cl Cl H
CO2CH3 CH2Br F Cl H CO2CH3 CH2Br Cl Cl H
H CH2F F Cl F
H CH2F Cl Cl F
H CH2C1 F Cl F
H CH2C1 Cl Cl F
H CH2Br F Cl F
H CH2Br Cl Cl F
C(=O)CH3 CH2F F Cl F
C(=O)CH3 CH2F Cl Cl F
C(=O)CH3 CH2C1 F Cl F
C(=O)CH3 CH2C1 Cl Cl F
C(=O)CH3 CH2Br F Cl F
C(=O)CH3 CH2Br Cl Cl F
C(=O)CH(CH3)2 CH2F F Cl F
C(=O)CH(CH3)2 CH2F Cl Cl F
C(=O)CH(CH3)2 CH2C1 F Cl F
C(=O)CH(CH3)2 CH2C1 Cl Cl F
C(=O)CH(CH3)2 CH2Br F Cl F
C(=O)CH(CH3)2 CH2Br Cl Cl F
CO2CH3 CH2F F Cl F
CO2CH3 CH2F Cl Cl F
CO2CH3 CH2C1 F Cl F
CO2CH3 CH2C1 Cl Cl F
CO2CH3 CH2Br F Cl F
CO2CH3 CH2Br Cl Cl F
,H CH2F F Cl Cl
H CH2F Cl Cl Cl
H CH2C1 F Cl Cl
H CH2C1 Cl Cl Cl
H CH2Br F Cl Cl
H CH2Br Cl Cl Cl
C(=O)CH3 CH2F F Cl Cl
C(=O)CH3 CH2F Cl Cl Cl
C(=O)CH3 CH2C1 F Cl Cl
C(=O)CH3 CH2C1 Cl Cl Cl
C(=O)CH3 CH2Br F Cl Cl
C(=O)CH3 CH2Br Cl Cl Cl
C(=O)CH(CH3)2 CH2F F Cl Cl C(=O)CH(CH3)2 CH2F Cl Cl Cl
C(=O)CH(CH3)2 CH2C1 F Cl Cl
C(=O)CH(CH3)2 CH2C1 Cl Cl Cl
C(=O)CH(CH3)2 CH2Br F Cl Cl
C(=O)CH(CH3)2 CH2Br Cl Cl Cl
CO2CH3 CH2F F Cl Cl
CO2CH3 CH2F Cl Cl Cl
CO2CH3 CH2C1 F Cl Cl
CO2CH3 CH2C1 Cl Cl Cl
CO2CH3 CH2Br F Cl Cl
CO2CH3 CH2Br Cl Cl Cl
TABLE 2
Rl R2 X Y R6 RZ
H CH2F F Cl H H
H CH2F Cl Cl H H
H CH2C1 F Cl H H
H CH2C1 Cl Cl H H
H CH2Br F Cl H H
H CH2Br Cl Cl H H
C(=O)CH3 CH2F F Cl H H
C(=O)CH3 CH2F Cl Cl H H
C(=O)CH3 CH2C1 F Cl H H
C(=O)CH3 CH2C1 Cl Cl H H
C(=O)CH3 CH2Br F Cl H H
C(=O)CH3 CH2Br Cl Cl H H
C(=O)CH(CH3)2 CH2F F Cl H H
C(=O)CH(CH3)2 CH2F Cl Cl H H
C(=O)CH(CH3)2 CH2C1 F Cl H H C(=O)CH(CH3)2 CH2C1 Cl Cl H H
C(=O)CH(CH3)2 CH2Br F Cl H H
C(=O)CH(CH3)2 CH2Br Cl Cl H H
CO2CH3 CH2F F Cl H H
CO2CH3 CH2F Cl Cl H H
CO2CH3 CH2C1 F Cl H H
CO2CH3 CH2C1 Cl Cl H H
CO2CH3 CH2Br F Cl H H
CO2CH3 CH2Br Cl Cl H H
H CH2F F Cl H F
H CH2F Cl Cl H F
H CH2C1 F Cl H F
H CH2C1 Cl Cl H F
H CH2Br F Cl H F
H CH2Br Cl Cl H F
C(=O)CH3 CH2F F Cl H F
C(=O)CH3 CH2F Cl Cl H F
C(=O)CH3 CH2C1 F Cl H F
C(=O)CH3 CH2C1 Cl Cl H F
C(=O)CH3 CH2Br F Cl H F
C(=O)CH3 CH2Br Cl Cl H F
C(=O)CH(CH3)2 CH2F F Cl H F
C(=O)CH(CH3)2 CH2F Cl Cl H F
C(=O)CH(CH3)2 CH2C1 F Cl H F
C(=O)CH(CH3)2 CH2C1 Cl Cl H F
C(=O)CH(CH3)2 CH2Br F Cl H F
C(=O)CH(CH3)2 CH2Br Cl Cl H F
CO2CH3 CH2F F Cl H F
CO2CH3 CH2F Cl Cl H F
CO2CH3 CH2C1 F Cl H F
CO2CH3 CH2C1 Cl Cl H F
CO2CH3 CH2Br F Cl H F
CO2CH3 CH2Br Cl Cl H F
H CH2F F Cl H Cl
H CH2F Cl Cl H Cl
H CH2C1 F Cl H Cl
H CH2C1 Cl Cl H Cl
H CH2Br F Cl H Cl H CH2Br Cl Cl H Cl
C(=O)CH3 CH2F F Cl H Cl
C(=O)CH3 CH2F Cl Cl H Cl
C(=O)CH3 CH2C1 F Cl H Cl
C(=O)CH3 CH2C1 Cl Cl H Cl
C(=O)CH3 CH2Br F Cl H Cl
C(=O)CH3 CH2Br Cl Cl H Cl
C(=O)CH(CH3)2 CH2F F Cl H Cl
C(=O)CH(CH3)2 CH2F Cl Cl H Cl
C(=O)CH(CH3)2 CH2C1 F Cl H Cl
C(=O)CH(CH3)2 CH2C1 Cl Cl H Cl
C(=O)CH(CH3)2 CH2Br F Cl H Cl
C(=O)CH(CH3)2 CH2Br Cl Cl H Cl
CO2CH3 CH2F F Cl H Cl
CO2CH3 CH2F Cl Cl H Cl
CO2CH3 CH2C1 F Cl H Cl
CO2CH3 CH2C1 Cl Cl H Cl
CO2CH3 CH2Br F Cl H Cl
CO2CH3 CH2Br Cl Cl H Cl
H CH2F F Cl Cl H
H CH2F Cl Cl Cl H
H CH2C1 F Cl Cl H
H CH2C1 Cl Cl Cl H
H CH2Br F Cl Cl H
H CH2Br Cl Cl Cl H
C(=O)CH3 CH2F F Cl Cl H
C(=O)CH3 CH2F Cl Cl Cl H
C(=O)CH3 CH2C1 F Cl Cl H
C(=O)CH3 CH2C1 Cl Cl Cl H
C(=O)CH3 CH2Br F Cl Cl H
C(=O)CH3 CH2Br Cl Cl Cl H
C(=O)CH(CH3)2 CH2F F Cl Cl H
C(=O)CH(CH3)2 CH2F Cl Cl Cl H
C(=O)CH(CH3)2 CH2C1 F Cl Cl H
C(=O)CH(CH3)2 CH2C1 Cl Cl Cl H
C(=O)CH(CH3)2 CH2Br F Cl Cl H
C(=O)CH(CH3)2 CH2Br Cl Cl Cl H
CO2CH3 CH2F F Cl Cl H CO2CH3 CH2F Cl Cl Cl H
CO2CH3 CH2C1 F Cl Cl H
CO2CH3 CH2C1 Cl Cl Cl H
CO2CH3 CH2Br F Cl Cl H
CO2CH3 CH2Br Cl Cl Cl H
H CH2F F Cl F H
H CH2F Cl Cl F H
H CH2C1 F Cl F H
H CH2C1 Cl Cl F H
H CH2Br F Cl F H
H CH2Br Cl Cl F H
C(=O)CH3 CH2F F Cl F H
C(=O)CH3 CH2F Cl Cl F H
C(=O)CH3 CH2C1 F Cl F H
C(=O)CH3 CH2C1 Cl Cl F H
C(=O)CH3 CH2Br F Cl F H
C(=O)CH3 CH2Br Cl Cl F H
C(=O)CH(CH3)2 CH2F F Cl F H
C(=O)CH(CH3)2 CH2F Cl Cl F H
C(=O)CH(CH3)2 CH2C1 F Cl F H
C(=O)CH(CH3)2 CH2C1 Cl Cl F H
C(=O)CH(CH3)2 CH2Br F Cl F H
C(=O)CH(CH3)2 CH2Br Cl Cl F H
CO2CH3 CH2F F Cl F H
CO2CH3 CH2F Cl Cl F H
CO2CH3 CH2C1 F Cl F H
CO2CH3 CH2C1 Cl Cl F H
CO2CH3 CH2Br F Cl F H
CO2CH3 CH2Br Cl Cl F H TABLE 3
El E5 X Y
H CH2F F Cl
H CH2F Cl Cl
H CH2C1 F Cl
H CH2C1 Cl Cl
H CH2Br F Cl
H CH2Br Cl Cl
C(=O)CH3 CH2F F Cl
C(=O)CH3 CH2F Cl Cl
C(=O)CH3 CH2C1 F Cl
C(=O)CH3 CH2C1 Cl Cl
C(=O)CH3 CH2Br F Cl
C(=O)CH3 CH2Br Cl Cl
C(=O)CH(CH3)2 CH2F F Cl
C(=O)CH(CH3)2 CH2F Cl Cl
C(=O)CH(CH3)2 CH2C1 F Cl
C(=O)CH(CH3)2 CH2C1 Cl Cl
C(=O)CH(CH3)2 CH2Br F Cl
C(=O)CH(CH3)2 CH2Br Cl Cl
CO2CH3 CH2F F Cl
CO2CH3 CH2F Cl Cl
CO2CH3 CH2C1 F Cl
CO2CH3 CH2C1 Cl Cl
CO2CH3 CH2Br F Cl
CO2CH3 CH2Br Cl Cl TABLE 4
Rl R . X Y R8 R9
H CH2F F Cl CH3 CH3
H CH2F Cl Cl CH3 CH3
H CH2C1 F Cl CH3 CH3
H CH2C1 Cl Cl CH3 CH3
H CH2Br F Cl CH3 CH3
H CH2Br Cl Cl CH3 CH3
C(=O)CH3 CH2F F Cl CH3 CH3
C(=O)CH3 CH2F Cl Cl CH3 CH3
C(=O)CH3 CH2C1 F Cl CH3 CH3
C(=O)CH3 CH2C1 Cl Cl CH3 CH3
C(=O)CH3 CH2Br F Cl CH3 CH3
C(=O)CH3 CH2Br Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2F F Cl CH3 CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CH3
C(-=O)CH(CH3)2 CH2C1 Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CH3
CO2CH3 CH2F F Cl CH3 CH3
CO2CH3 CH2F Cl Cl CH3 CH3
CO2CH3 CH2C1 F Cl CH3 CH3
CO2CH3 CH2C1 Cl Cl CH3 CH3
CO2CH3 CH2Br F Cl CH3 CH3
CO2CH3 CH2Br Cl Cl CH3 CH3
H CH2F F Cl CH3 CF3
H CH2F Cl Cl CH3 CF3
H CH2C1 F Cl CH3 CF3
H CH2C1 Cl Cl CH3 CF3 H CH2Br F Cl CH3 CF3
H CH2Br Cl Cl CH3 CF3
C(=O)CH3 CH2F F Cl CH3 CF3
C(=O)CH3 CH2F Cl Cl CH3 CF3
C(=O)CH3 CH2C1 F Cl CH3 CF3
C(=O)CH3 CH2C1 Cl Cl CH3 CF3
C(=O)CH3 CH2Br F Cl CH3 CF3
C(=O)CH3 CH2Br Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2F F Cl CH3 CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2Br F Cl CH3 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CF3
CO2CH3 CH2F F Cl CH3 CF3
CO2CH3 CH2F Cl Cl CH3 CF3
CO2CH3 CH2C1 F Cl CH3 CF3
CO2CH3 CH2C1 Cl Cl CH3 CF3
CO2CH3 CH2Br F Cl CH3 CF3
CO2CH3 CH2Br Cl Cl CH3 CF3
H CH2F F Cl CH2CH=CH2 CH3
H CH2F Cl Cl CH2CH=CH2 CH3
H CH2C1 F Cl CH2CH=CH2 CH3
H CH2C1 Cl Cl CH2CH=CH2 CH3
H CH2Br F Cl CH2CH=CH2 CH3
H CH2Br Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2F F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2F Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2C1 F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2C1 Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2Br F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2Br Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2F F Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH=CH2 CH3 CO2CH3 CH2F F Cl CH2CH-=CH2 CH3
CO2CH3 CH2F Cl Cl CH2CH=CH2 CH3
CO2CH3 CH2C1 F Cl CH2CH=CH2 CH3
CO2CH3 CH2C1 Cl Cl CH2CH=CH2 CH3
CO2CH3 CH2Br F Cl CH2CH=CH2 CH3
CO2CH3 CH2Br Cl Cl CH2CH=CH2 CH3
H CH2F F Cl CH2CH=CH2 CF3
H CH2F Cl Cl CH2CH=CH2 CF3
H CH2C1 F Cl CH2CH=CH2 CF3
H CH2C1 Cl Cl CH2CH=CH2 CF3
H CH2Br F Cl CH2CH=CH2 CF3
H CH2Br Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2F F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2F Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2C1 F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2C1 Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2Br F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2Br Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2F F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2F F Cl CH2CH=-CH2 CF3
CO2CH3 CH2F Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2C1 F Cl CH2CH=CH2 CF3
CO2CH3 CH2C1 Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2Br F Cl CH2CH=CH2 CF3
CO2CH3 CH2Br Cl Cl CH2CH=CH2 CF3
H CH2F F Cl CH2CH2CH2F CH3
H CH2F Cl Cl CH2CH2CH2F CH3
H CH2C1 F Cl CH2CH2CH2F CH3
H CH2C1 Cl Cl CH2CH2CH2F CH3
H CH2Br F Cl CH2CH2CH2F CH3
H CH2Br Cl Cl CH2CH2CH2F CH3
C(=O)CH3 CH2F F Cl CH2CH2CH2F CH3
C(=O)CH3 CH2F Cl Cl CH2CH2CH2F CH3 C(=O)CH3 CH2C1 F Cl CH2CH2CH2F CH3
C(=O)CH3 CH2C1 Cl Cl CH2CH2CH2F CH3
C(=O)CH3 CH2Br F Cl CH2CH2CH2F CH3
C(=O)CH3 CH2Br Cl Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2F F Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH2CH2F CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH2CH2F CH3
CO2CH3 CH2F F Cl CH2CH2CH2F CH3
CO2CH3 CH2F Cl Cl CH2CH2CH2F CH3
CO2CH3 CH2C1 F Cl CH2CH2CH2F CH3
CO2CH3 CH2C1 Cl Cl CH2CH2CH2F CH3
CO2CH3 CH2Br F Cl CH2CH2CH2F CH3
CO2CH3 CH2Br Cl Cl CH2CH2CH2F CH3
H CH2F F Cl CH2CH2CH2F CF3
H CH2F Cl Cl CH2CH2CH2F CF3
H CH2C1 F Cl CH2CH2CH2F CF3
H CH2C1 Cl Cl CH2CH2CH2F CF3
H CH2Br F Cl CH2CH2CH2F CF3
H CH2Br Cl Cl CH2CH2CH2F CF3
C(=O)CH3 CH2F F Cl CH2CH2CH2F CF3
C(=O)CH3 CH2F Cl Cl CH2CH2CH2F CF3
C(=O)CH3 CH2C1 F Cl CH2CH2CH2F CF3
C(=O)CH3 CH2C1 Cl Cl CH2CH2CH2F CF3
C(=O)CH3 CH2Br F Cl CH2CH2CH2F CF3
C(=O)CH3 CH2Br Cl Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2F F Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH2CH2F CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH2CH2F CF3
CO2CH3 CH2F F Cl CH2CH2CH2F CF3
CO2CH3 CH2F Cl Cl CH2CH2CH2F CF3
CO2CH3 CH2C1 F Cl CH2CH2CH2F CF3
CO2CH3 CH2C1 Cl Cl CH2CH2CH2F CF3 CO2CH3 CH2Br F Cl CH2CH2CH2F CF3
CO2CH3 CH2Br Cl Cl CH2CH2CH2F CF3
TABLE 5
E R^ Y RIO Ell
H CH2F F Cl CH3 CH3
H CH2F Cl Cl CH3 CH3
H CH2C1 F Cl CH3 CH3
H CH2C1 Cl Cl CH3 CH3
H CH2Br F Cl CH3 CH3
H CH2Br Cl Cl CH3 CH3
C(=O)CH3 CH2F F Cl CH3 CH3
C(=O)CH3 CH2F Cl Cl CH3 CH3
C(=O)CH3 CH2C1 F Cl CH3 CH3
C(=O)CH3 CH2C1 Cl Cl CH3 CH3
C(=O)CH3 CH2Br F Cl CH3 CH3
C(=O)CH3 CH2Br Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2F F Cl CH3 CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CH3
CO2CH3 CH2F F Cl CH3 CH3
CO2CH3 CH2F Cl Cl CH3 CH3
CO2CH3 CH2C1 F Cl CH3 CH3
CO2CH3 CH2C1 Cl Cl CH3 CH3
CO2CH3 CH2Br F Cl CH3 CH3 CO2CH3 CH2Br Cl Cl CH3 CH3
H CH2F F Cl CH3 CF3
H CH2F Cl Cl CH3 CF3
H CH2C1 F Cl CH3 CF3
H CH2C1 Cl Cl CH3 CF3
H CH2Br F Cl CH3 CF3
H CH2Br Cl Cl CH3 CF3
C(=O)CH3 CH2F F Cl CH3 CF3
C(=O)CH3 CH2F Cl Cl CH3 CF3
C(=O)CH3 CH2C1 F Cl CH3 CF3
C(=O)CH3 CH2C1 Cl Cl CH3 CF3
C(=O)CH3 CH2Br F Cl CH3 CF3
C(=O)CH3 CH2Br Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2F F Cl CH3 CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CF3
C(=O)CH(CH3)2 CH2Br F Cl CH3 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CF3
CO2CH3 CH2F F Cl CH3 CF3
CO2CH3 CH2F Cl Cl CH3 CF3
CO2CH3 CH2C1 F Cl CH3 CF3
CO2CH3 CH2C1 Cl Cl CH3 CF3
CO2CH3 CH2Br F Cl CH3 CF3
CO2CH3 CH2Br Cl Cl CH3 CF3
H CH2F F Cl CH2CH=CH2 CH3
H CH2F Cl Cl CH2CH=CH2 CH3
H CH2C1 F Cl CH2CH=CH2 CH3
H CH2C1 Cl Cl CH2CH=CH2 CH3
H CH2Br F Cl CH2CH=CH2 CH3
H CH2Br Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2F F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2F Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2C1 F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2C1 Cl Cl CH2CH=CH2 CH3
C(=O)CH3 CH2Br F Cl CH2CH=CH2 CH3
C(=O)CH3 CH2Br Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2F F Cl CH2CH=CH2 CH3 C(=O)CH(CH3)2 CH2F Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH=CH2 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH=CH2 CH3
CO2CH3 CH2F F Cl CH2CH=CH2 CH3
CO2CH3 CH2F Cl Cl CH2CH=CH2 CH3
CO2CH3 CH2C1 F Cl CH2CH=CH2 CH3
CO2CH3 CH2C1 Cl Cl CH2CH=CH2 CH3
CO2CH3 CH2Br F Cl CH2CH=CH2 CH3
CO2CH3 CH2Br Cl Cl CH2CH=CH2 CH3
H CH2F F Cl CH2CH=CH2 CF3
H CH2F Cl Cl CH2CH=CH2 CF3
H CH2C1 F Cl CH2CH=CH2 CF3
H CH2C1 Cl Cl CH2CH=CH2 CF3
H CH2Br F Cl CH2CH=CH2 CF3
H CH2Br Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2F F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2F Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2C1 F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2C1 Cl Cl CH2CH=CH2 CF3
C(=O)CH3 CH2Br F Cl CH2CH=CH2 CF3
C(=O)CH3 CH2Br Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2F F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2Br F Cl CH2CH=CH2 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2F F Cl CH2CH=CH2 CF3
CO2CH3 CH2F Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2C1 F Cl CH2CH=CH2 CF3
CO2CH3 CH2C1 Cl Cl CH2CH=CH2 CF3
CO2CH3 CH2Br F Cl CH2CH=CH2 CF3
CO2CH3 CH2Br Cl Cl CH2CH=CH2 CF3
H CH2F F Cl CH2C≡CH CH3
H CH2F Cl Cl CH2C≡CH CH3
H CH2C1 F Cl CH2C≡CH CH3 H CH2C1 Cl Cl CH2C≡CH CH3
H CH2Br F Cl CH2C≡CH CH3
H CH2Br Cl Cl CH2C≡CH CH3
C(=O)CH3 CH2F F Cl CH2C≡CH CH3
C(=O)CH3 CH2F Cl Cl CH2C≡CH CH3
C(=O)CH3 CH2C1 F Cl CH2C≡CH CH3
C(=O)CH3 CH2C1 Cl Cl CH2C≡CH CH3
C(=O)CH3 CH2Br F Cl CH2C≡CH CH3
C(=O)CH3 CH2Br Cl Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2F F Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2Br F Cl CH2C≡CH CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH2G≡CH CH3
CO2CH3 CH2F F Cl CH2C≡CH CH3
CO2CH3 CH2F Cl Cl CH2C≡CH CH3
CO2CH3 CH2C1 F Cl CH2C≡CH CH3
CO2CH3 CH2C1 Cl Cl CH2C≡CH CH3
CO2CH3 CH2Br F Cl CH2C≡CH CH3
CO2CH3 CH2Br Cl Cl CH2C≡CH CH3
H CH2F F Cl CH2C≡CH CF3
H CH2F Cl Cl CH2C≡CH CF3
H CH2C1 F Cl CH2C≡CH CF3
H CH2C1 Cl Cl CH2G≡CH CF3
H CH2Br F Cl CH2C≡CH CF3
H CH2Br Cl Cl CH2C≡CH CF3
C(=O)CH3 CH2F F Cl CH2C≡CH CF3
C(=O)CH3 CH2F Cl Cl CH2C≡CH CF3
C(=O)CH3 CH2C1 F Cl CH2C≡CH CF3
C(=O)CH3 CH2C1 Cl Cl CH2C≡CH CF3
C(=O)CH3 CH2Br F Cl CH2C≡CH CF3
C(=O)CH3 CH2Br Cl Cl CH2C≡CH CF3
C(=O)CH(CH3)2 CH2F F Cl CH2C≡CH CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH2C≡CH CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH2C≡CH CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2C≡CH CF3
C(=O)CH(CH3)2 CH2Br F Cl CH2C≡CH CF3 C(=O)CH(CH3)2 CH2Br Cl Cl CH2C≡CH CF3
CO2CH3 CH2F F Cl CH2C≡CH CF3
CO2CH3 CH2F Cl Cl CH2C≡CH CF3
CO2CH3 CH2C1 F Cl CH2C≡CH CF3
CO2CH3 CH2C1 Cl Cl CH2C≡CH CF3
CO2CH3 CH2Br F Cl CH2C≡CH CF3
CO2CH3 CH2Br Cl Cl CH2C≡CH CF3
H CH2F F Cl NH2 CH3
H CH2F Cl Cl NH2 CH3
H CH2C1 F Cl NH2 CH3
H CH2C1 Cl Cl NH2 CH3
H CH2Br F Cl NH2 CH3
H CH2Br Cl Cl NH2 CH3
C(=O)CH3 CH2F F Cl NH2 CH3
C(=O)CH3 CH2F Cl Cl NH2 CH3
C(=O)CH3 CH2C1 F Cl NH2 CH3
C(=O)CH3 CH2C1 Cl Cl NH2 CH3
C(=O)CH3 CH2Br F Cl NH2 CH3
C(=O)CH3 CH2Br Cl Cl NH2 CH3
C(=O)CH(CH3)2 CH2F F Cl NH2 CH3
C(=O)CH(CH3)2 CH2F Cl Cl NH2 CH3
C(=O)CH(CH3)2 CH2C1 F Cl NH2 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl NH2 CH3
C(=O)CH(CH3)2 CH2Br F Cl NH2 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl NH2 CH3
CO2CH3 CH2F F Cl NH2 CH3
CO2CH3 CH2F Cl Cl NH2 CH3
CO2CH3 CH2C1 F Cl NH2 CH3
CO2CH3 CH2C1 Cl Cl NH2 CH3
CO2CH3 CH2Br F Cl NH2 CH3
CO2CH3 CH2Br Cl Cl NH2 CH3
H CH2F F Cl NH2 CF3
H CH2F Cl Cl NH2 CF3
H CH2C1 F Cl NH2 CF3
H CH2C1 Cl Cl NH2 CF3
H CH2Br F Cl NH2 CF3
H CH2Br Cl Cl NH2 CF3
C(=O)CH3 CH2F F Cl NH2 CF3 C(=O)CH3 CH2F Cl Cl NH2 CF3
C(=O)CH3 CH2C1 F Cl NH2 CF3
C(=O)CH3 CH2C1 Cl Cl NH2 CF3
C(=O)CH3 CH2Br F Cl NH2 CF3
C(=O)CH3 CH2Br Cl Cl NH2 CF3
C(=O)CH(CH3)2 CH2F F Cl NH2 CF3
C(=O)CH(CH3)2 CH2F Cl Cl NH2 CF3
C(=O)CH(CH3)2 CH2C1 F Cl NH2 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl NH2 CF3
C(=O)CH(CH3)2 CH2Br F Cl NH2 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl NH2 CF3
CO2CH3 CH2F F Cl NH2 CF3
CO2CH3 CH2F Cl Cl NH2 CF3
CO2CH3 CH2C1 F Cl NH2 CF3
CO2CH3 CH2C1 Cl Cl NH2 CF3
CO2CH3 CH2Br F Cl NH2 CF3
CO2CH3 CH2Br Cl Cl NH2 CF3
H CH2F F Cl N(CH3)2 CH3
H CH2F Cl Cl N(CH3)2 CH3
H CH2C1 F Cl N(CH3)2 CH3
H CH2C1 Cl Cl N(CH3)2 CH3
H CH2Br F Cl N(CH3)2 CH3
H CH2Br Cl Cl N(CH3)2 CH3
C(=O)CH3 CH2F F Cl N(CH3)2 CH3
C(=O)CH3 CH2F Cl Cl N(CH3)2 CH3
C(=O)CH3 CH2C1 F Cl N(CH3)2 CH3
C(=O)CH3 CH2C1 Cl Cl N(CH3)2 CH3
C(=O)CH3 CH2Br F Cl N(CH3)2 CH3
C(=O)CH3 CH2Br Cl Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2F F Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2F Cl Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2C1 F Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2Br F Cl N(CH3)2 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl N(CH3)2 CH3
CO2CH3 CH2F F Cl N(CH3)2 CH3
CO2CH3 CH2F Cl Cl N(CH3)2 CH3
CO2CH3 CH2C1 F Cl N(CH3)2 CH3 CO2CH3 CH2C1 Cl Cl N(CH3)2 CH3
CO2CH3 CH2Br F Cl N(CH3)2 CH3
CO2CH3 CH2Br Cl Cl N(CH3)2 CH3
H CH2F F Cl N(CH3)2 CF3
H CH2F Cl Cl N(CH3)2 CF3
H CH2C1 F Cl N(CH3)2 CF3
H CH2C1 Cl Cl N(CH3)2 CF3
H CH2Br F Cl N(CH3)2 CF3
H CH2Br Cl Cl N(CH3)2 CF3
C(=O)CH3 CH2F F Cl N(CH3)2 CF3
C(=O)CH3 CH2F Cl Cl N(CH3)2 CF3
C(=O)CH3 CH2C1 F Cl N(CH3)2 CF3
C(=O)CH3 CH2C1 Cl Cl N(CH3)2 CF3
C(=O)CH3 CH2Br F Cl N(CH3)2 CF3
C(=O)CH3 CH2Br Cl Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2F F Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2F Cl Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2C1 F Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2Br F Cl N(CH3)2 CF3
C(=O)CH(CH3)2 CH2Br Cl Cl N(CH3)2 CF3
CO2CH3 CH2F F Cl N(CH3)2 CF3
CO2CH3 CH2F Cl Cl N(CH3)2 CF3
CO2CH3 CH2C1 F Cl N(CH3)2 CF3
CO2CH3 CH2C1 Cl Cl N(CH3)2 CF3
CO2CH3 CH2Br F Cl N(CH3)2 CF3
CO2CH3 CH2Br Cl Cl N(CH3)2 CF3
TABLE 6
El El Y EU
H CH2F F Cl CH3
H CH2F Cl Cl CH3
H CH2C1 F Cl CH3
H CH2C1 Cl Cl CH3
H CH2Br F Cl CH3
H CH2Br Cl Cl CH3
C(=O)CH3 CH2F F Cl CH3
C(=O)CH3 CH2F Cl Cl CH3
C(=O)CH3 CH2C1 F Cl CH3
C(=O)CH3 CH2C1 Cl Cl CH3
C(=O)CH3 CH2Br F Cl CH3
C(=O)CH3 CH2Br Cl Cl CH3
C(=O)CH(CH3)2 CH2F F Cl CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3
CO2CH3 CH2F F Cl CH3
CO2CH3 CH2F Cl Cl CH3
CO2CH3 CH2C1 F Cl CH3
CO2CH3 CH2C1 Cl Cl CH3
CO2CH3 CH2Br F Cl CH3
CO2CH3 CH2Br Cl Cl CH3
H CH2F F Cl CH2CH=CH2
H CH2F Cl Cl CH2CH=CH2
H CH2C1 F Cl CH2CH=CH2
H CH2C1 Cl Cl CH2CH=CH2 H CH2Br F Cl CH2CH=CH2
H CH2Br Cl Cl CH2CH=CH2
C(=O)CH3 CH2F F Cl CH2CH=CH2
C(=O)CH3 CH2F Cl Cl CH2CH=CH2
C(=O)CH3 CH2C1 F Cl CH2CH=CH2
C(=O)CH3 CH2C1 Cl Cl CH2CH=CH2
C(=O)CH3 CH2Br F Cl CH2CH=CH2
C(=O)CH3 CH2Br Cl Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2F F Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2Br F Cl CH2CH=CH2
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH=CH2
CO2CH3 CH2F F Cl CH2CH=CH2
CO2CH3 CH2F Cl Cl CH2CH=CH2
CO2CH3 CH2C1 F Cl CH2CH=CH2
CO2CH3 CH2C1 Cl Cl CH2CH=CH2
CO2CH3 CH2Br F Cl CH2CH=CH2
CO2CH3 CH2Br Cl Cl CH2CH=CH2
H CH2F F Cl CH2CH2CH2F
H CH2F Cl Cl CH2CH2CH2F
H CH2C1 F Cl CH2CH2CH2F
H CH2C1 Cl Cl CH2CH2CH2F
H CH2Br F Cl CH2CH2CH2F
H CH2Br Cl Cl CH2CH2CH2F
C(=O)CH3 CH2F F Cl CH2CH2CH2F
C(=O)CH3 CH2F Cl Cl CH2CH2CH2F
C(=O)CH3 CH2C1 F Cl CH2CH2CH2F
C(=O)CH3 CH2C1 Cl Cl CH2CH2CH2F
C(=O)CH3 CH2Br F Cl CH2CH2CH2F
C(=O)CH3 CH2Br Cl Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2F F Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2F Cl Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2C1 F Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2C1 Cl Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2Br F Cl CH2CH2CH2F
C(=O)CH(CH3)2 CH2Br Cl Cl CH2CH2CH2F CO2CH3 CH2F F Cl CH2CH2CH2F
CO2CH3 CH2F Cl Cl CH2CH2CH2F
CO2CH3 CH2C1 F Cl CH2CH2CH2F
CO2CH3 CH2C1 Cl Cl CH2CH2CH2F
CO2CH3 CH2Br F Cl CH2CH2CH2F
CO2CH3 CH2Br Cl Cl CH2CH2CH2F
TABLE 7
El R2 X Y Rl2 Ell R14
H CH2F F Cl H H H
H CH2F Cl Cl H H H
H CH2C1 F Cl H H H
H CH2C1 Cl Cl H H H
H CH2Br F Cl H H H
H CH2Br Cl Cl H H H
C(=O)CH3 CH2F F Cl H H H
C(=O)CH3 CH2F Cl Cl H H H
C(=O)CH3 CH2C1 F Cl H H H
C(=O)CH3 CH2C1 Cl Cl H H H
C(=O)CH3 CH2Br F Cl H H H
C(=O)CH3 CH2Br Cl Cl H H H
C(=O)CH(CH3)2 CH2F F Cl H H H
C(=O)CH(CH3)2 CH2F Cl Cl H H H
C(=O)CH(CH3)2 CH2C1 F Cl H H H
C(=O)CH(CH3)2 CH2C1 Cl Cl H H H
C(=O)CH(CH3)2 CH2Br F Cl H H H
C(=O)CH(CH3)2 CH2Br Cl Cl H H H
CO2CH3 CH2F F Cl H H H CO2CH3 CH2F Cl Cl H H H
CO2CH3 CH2C1 F Cl H H H
CO2CH3 CH2C1 Cl Cl H H H
CO2CH3 CH2Br F Cl H H H
CO2CH3 CH2Br Cl Cl H H H
H CH2F F Cl H H CH3
H CH2F Cl Cl H H CH3
H CH2C1 F Cl H H CH3
H CH2C1 Cl Cl H H CH3
H CH2Br F Cl H H CH3
H CH2Br Cl Cl H H CH3
C(=O)CH3 CH2F F Cl H H CH3
C(=O)CH3 CH2F Cl Cl H H CH3
C(=O)CH3 CH2C1 F Cl H H CH3
C(=O)CH3 CH2C1 Cl Cl H H CH3
C(=O)CH3 CH2Br F Cl H H CH3
C(=O)CH3 CH2Br Cl Cl H H CH3
C(=O)CH(CH3)2 CH2F F Cl H H CH3
C(=O)CH(CH3)2 CH2F Cl Cl H H CH3
C(=O)CH(CH3)2 CH2C1 F Cl H H CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl H H CH3
C(=O)CH(CH3)2 CH2Br F Cl H H CH3
C(=O)CH(CH3)2 CH2Br Cl Cl H H CH3
CO2CH3 CH2F F Cl H H CH3
CO2CH3 CH2F Cl Cl H H CH3
CO2CH3 CH2C1 F Cl H H CH3
CO2CH3 CH2C1 Cl Cl H H CH3
CO2CH3 CH2Br F Cl H H CH3
CO2CH3 CH2Br Cl Cl H H CH3
H CH2F F Cl H CH3 CH3
H CH2F Cl Cl H CH3 CH3
H CH2C1 F Cl H CH3 CH3
H CH2C1 Cl Cl H CH3 CH3
H CH2Br F Cl H CH3 CH3
H CH2Br Cl Cl H CH3 CH3
C(=O)CH3 CH2F F Cl H CH3 CH3
C(=O)CH3 CH2F Cl Cl H CH3 CH3
C(=O)CH3 CH2C1 F Cl H CH3 CH3 ,Q Ω,
'r T, TΓ IT IT TΓ
O O O O ^ ^ l O o O ^ -^ ^ ^ O O ^ ^ ^ ^ O ^ ^ l O o O O to tO f_ l tO tO to tO . *1 .T1 tO tO tO tO j tO tO tO tO f tO tO tO tO ^ 10 o o ^ ^ « o o ^ ^ o o ^ ^ a o o ' j τj o o t j tτj
τj θ τj θ τj θ τι Q τι G ^ Q ^ Q ^ G ^ Q ^ G ^ Q ^ G ^ Q ^ Q '^ 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
oo o o o o o o o o o o o o o o o o o o o o o ffi ffi a a a a
W Λ W W MM Λ μ-H a M HH a a HH a a w w a a a s-i a a a a a a
HH MM MH MH I O O O O
MH MM MM MM p^ μ ^ Q μQ ) <J vp ) W i_o
CO2CH3 CH2Br Cl Cl Cl H H
H CH2F F Cl Cl H CH3
H CH2F Cl Cl Cl H CH3
H CH2C1 F Cl Cl H CH3
H CH2C1 Cl Cl Cl H CH3
H CH2Br F Cl Cl H CH3
H CH2Br Cl Cl Cl H CH3
C(=O)CH3 CH2F F Cl Cl H CH3
C(=O)CH3 CH2F Cl Cl Cl H CH3
C(=O)CH3 CH2C1 F Cl Cl H CH3
C(=O)CH3 CH2C1 Cl Cl Cl H CH3
C(=O)CH3 CH2Br F Cl Cl H CH3
C(=O)CH3 CH2Br Cl Cl Cl H CH3
C(=O)CH(CH3)2 CH2F F Cl Cl H CH3
C(=O)CH(CH3)2 CH2F Cl Cl Cl H CH3
C(=O)CH(CH3)2 CH2C1 F Cl Cl H CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl Cl H CH3
C(=O)CH(CH3)2 CH2Br F Cl Cl H CH3
C(=O)CH(CH3)2 CH2Br Cl Cl Cl H CH3
CO2CH3 CH2F F Cl Cl H CH3
CO2CH3 CH2F Cl Cl Cl H CH3
CO2CH3 CH2C1 F Cl Cl H CH3
CO2CH3 CH2C1 Cl Cl Cl H CH3
CO2CH3 CH2Br F Cl Cl H CH3
CO2CH3 CH2Br Cl Cl Cl H CH3
H CH2F F Cl Cl CH3 CH3
H CH2F Cl Cl Cl CH3 CH3
H CH2C1 F Cl Cl CH3 CH3
H CH2C1 Cl Cl Cl CH3 CH3
H CH2Br F Cl Cl CH3 CH3
H CH2Br Cl Cl Cl CH3 CH3
C(=O)CH3 CH2F F Cl Cl CH3 CH3
C(=O)CH3 CH2F Cl Cl Cl CH3 CH3
C(=O)CH3 CH2C1 F Cl Cl CH3 CH3
C(=O)CH3 CH2C1 Cl Cl Cl CH3 CH3
C(=O)CH3 CH2Br F Cl Cl CH3 CH3
C(=O)CH3 CH2Br Cl Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2F F Cl Cl CH3 CH3 C(=O)CH(CH3)2 CH2F Cl Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2C1 F Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br F Cl Cl CH3 CH3
C(=O)CH(CH3)2 CH2Br Cl Cl Cl CH3 CH3
CO2CH3 CH2F F Cl Cl CH3 CH3
CO2CH3 CH2F Cl Cl Cl CH3 CH3
CO2CH3 CH2C1 F Cl Cl CH3 CH3
CO2CH3 CH2C1 Cl Cl Cl CH3 CH3
CO2CH3 CH2Br F Cl Cl CH3 CH3
CO2CH3 CH2Br Cl Cl Cl CH3 CH3
H CH2F F Cl F H H
H CH2F Cl Cl F H H
H CH2C1 F Cl F H H
H CH2C1 Cl Cl F H H
H CH2Br F Cl F H H
H CH2Br Cl Cl F H H
C(=O)CH3 CH2F F Cl F H H
C(=O)CH3 CH2F Cl Cl F H H
C(=O)CH3 CH2C1 F Cl F H H
C(=O)CH3 CH2C1 Cl Cl F H H
C(=O)CH3 CH2Br F Cl F . H H
C(=O)CH3 CH2Br Cl Cl F H H
C(=O)CH(CH3)2 CH2F F Cl F H H
C(=O)CH(CH3)2 CH2F Cl Cl F H H
C(=O)CH(CH3)2 CH2C1 F Cl F H H
C(=O)CH(CH3)2 CH2C1 Cl Cl F H H
C(=O)CH(CH3)2 CH2Br F Cl F H H
C(=O)CH(CH3)2 CH2Br Cl Cl F H H
CO2CH3 CH2F F Cl F H H
CO2CH3 CH2F Cl Cl F H H
CO2CH3 CH2C1 F Cl F H H
CO2CH3 CH2C1 Cl Cl F H H
CO2CH3 CH2Br F Cl F H H
CO2CH3 CH2Br Cl Cl F H H
H CH2F F Cl F H CH3
H CH2F Cl Cl F H CH3
H CH2C1 F Cl F H CH3 H CH2C1 Cl Cl F H CH3
H CH2Br F Cl F H CH3
H CH2Br Cl Cl F H CH3
C(=O)CH3 CH2F F Cl F H CH3
C(=O)CH3 CH2F Cl Cl F H CH3
C(=O)CH3 CH2C1 F Cl F H CH3
C(=O)CH3 CH2C1 Cl Cl F H CH3
C(=O)CH3 CH2Br F Cl F H CH3
C(=O)CH3 CH2Br Cl Cl F H CH3
C(=O)CH(CH3)2 CH2F F Cl F H CH3
C(=O)CH(CH3)2 CH2F Cl Cl F H CH3
C(=O)CH(CH3)2 CH2C1 F Cl F H CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl F H CH3
C(=O)CH(CH3)2 CH2Br F Cl F H CH3
C(=O)CH(CH3)2 CH2Br Cl Cl F H CH3
CO2CH3 CH2F F Cl F H CH3
CO2CH3 CH2F Cl Cl F H CH3
CO2CH3 CH2C1 F Cl F H CH3
CO2CH3 CH2C1 Cl Cl F H CH3
CO2CH3 CH2Br F Cl F H CH3
CO2CH3 CH2Br Cl Cl F H CH3
H CH2F F Cl F CH3 CH3
H CH2F Cl Cl F CH3 CH3
H CH2C1 F Cl F CH3 CH3
H CH2C1 Cl Cl F CH3 CH3
H CH2Br F Cl F CH3 CH3
H CH2Br Cl Cl F CH3 CH3
C(=O)CH3 CH2F F Cl F CH3 CH3
C(=O)CH3 CH2F Cl Cl F CH3 CH3
C(=O)CH3 CH2C1 F Cl F CH3 CH3
C(=O)CH3 CH2C1 Cl Cl F CH3 CH3
C(=O)CH3 CH2Br F Cl F CH3 CH3
C(=O)CH3 CH2Br Cl Cl F CH3 CH3
C(=O)CH(CH3)2 CH2F F Cl F CH3 CH3
C(=O)CH(CH3)2 CH2F Cl Cl F CH3 CH3
C(=O)CH(CH3)2 CH2C1 F Cl F CH3 CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl F CH3 CH3
C(=O)CH(CH3)2 CH2Br F Cl F CH3 CH3 C(=O)CH(CH3)2 CH2Br Cl Cl F CH3 CH3
CO2CH3 CH2F F Cl F CH3 CH3
CO2CH3 CH2F Cl Cl F CH3 CH3
CO2CH3 CH2C1 F Cl F CH3 CH3
CO2CH3 CH2C1 Cl Cl F CH3 CH3
CO2CH3 CH2Br F Cl F CH3 CH3
CO2CH3 CH2Br Cl Cl F CH3 CH3
TABLE 8
El El x Y R8 R? E!
H CH2F F Cl CH3 Cl H
H CH2F Cl Cl CH3 Cl H
H CH2C1 F Cl CH3 Cl H
H CH2C1 Cl Cl CH3 Cl H
H CH2Br F Cl CH3 Cl H
H CH2Br Cl Cl CH3 Cl H
C(=O)CH3 CH2F F Cl CH3 Cl H
C(=O)CH3 CH2F Cl Cl CH3 Cl H
C(=O)CH3 CH2C1 F Cl CH3 Cl H
C(=O)CH3 CH2C1 Cl Cl CH3 Cl H
C(=O)CH3 CH2Br F Cl CH3 Cl H
C(=O)CH3 CH2Br Cl Cl CH3 Cl H
C(=O)CH(CH3)2 CH2F F Cl CH3 Cl H
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Cl H
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Cl H
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Cl H
C(=O)CH(CH3)2 CH2Br F Cl CH3 Cl H
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Cl H
CO2CH3 CH2F F Cl CH3 Cl H
CO2CH3 CH2F Cl Cl CH3 Cl H CO2CH3 CH2C1 F Cl CH3 Cl H
CO2CH3 CH2C1 Cl Cl CH3 Cl H
CO2CH3 CH2Br F Cl CH3 Cl H
CO2CH3 CH2Br Cl Cl CH3 Cl H
H CH2F F Cl CHC12 Cl H
H CH2F Cl Cl CHC12 Cl H
H CH2C1 F Cl CHC12 Cl H
H CH2C1 Cl Cl CHC12 Cl H
H CH2Br F Cl CHC12 Cl H
H CH2Br Cl Cl CHC12 Cl H
C(=O)CH3 CH2F F Cl CHC12 Cl H
C(=O)CH3 CH2F Cl Cl CHC12 Cl H
C(=O)CH3 CH2C1 F Cl CHC12 Cl H
C(=O)CH3 CH2C1 Cl Cl CHC12 Cl H
C(=O)CH3 CH2Br F Cl CHC12 Cl H
C(=O)CH3 CH2Br Cl Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2F F Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Cl H
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Cl H
CO2CH3 CH2F F Cl CHC12 Cl H
CO2CH3 CH2F Cl Cl CHC12 Cl H
CO2CH3 CH2C1 F Cl CHC12 Cl H
CO2CH3 CH2C1 Cl Cl CHC12 Cl H
CO2CH3 CH2Br F Cl CHC12 Cl H
CO2CH3 CH2Br Cl Cl CHC12 Cl H
H CH2F F Cl CH3 Br H
H CH2F Cl Cl CH3 * Br H
H CH2C1 F Cl CH3 Br H
H CH2C1 Cl Cl CH3 Br H
H CH2Br F Cl CH3 Br H
H CH2Br Cl Cl CH3 Br H
C(=O)CH3 CH2F F Cl CH3 Br H
C(=O)CH3 CH2F Cl Cl CH3 Br H
C(=O)CH3 CH2C1 F Cl CH3 Br H
C(=O)CH3 CH2C1 Cl Cl CH3 Br H C(=O)CH3 CH2Br F Cl CH3 Br H
C(=O)CH3 CH2Br Cl Cl CH3 Br H
C(=O)CH(CH3)2 CH2F F Cl CH3 Br H
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Br H
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Br H
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Br H
C(=O)CH(CH3)2 CH2Br F Cl CH3 Br H
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Br H
CO2CH3 CH2F F Cl CH3 Br H
CO2CH3 CH2F Cl Cl CH3 Br H
CO2CH3 CH2C1 F Cl CH3 Br H
CO2CH3 CH2C1 Cl Cl CH3 Br H
CO2CH3 CH2Br F Cl CH3 Br H
CO2CH3 CH2Br Cl Cl CH3 Br H
H CH2F F Cl CHC12 Br H
H CH2F Cl Cl CHC12 Br H
H CH2C1 F Cl CHC12 Br H
H CH2C1 Cl Cl CHC12 Br H
H CH2Br F Cl CHC12 Br H
H CH2Br Cl Cl CHC12 Br H
C(=O)CH3 CH2F F Cl CHC12 Br H
C(=O)CH3 CH2F Cl Cl CHC12 Br H
C(=O)CH3 CH2C1 F Cl CHC12 Br H
C(=O)CH3 CH2C1 Cl Cl CHC12 Br H
C(=O)CH3 CH2Br F Cl CHC12 Br H
C(=O)CH3 CH2Br Cl Cl CHC12 Br H
C(=O)CH(CH3)2 CH2F F Cl CHC12 Br H
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Br H
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 Br H
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Br H
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Br H
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Br H
CO2CH3 CH2F F Cl CHC12 Br H
CO2CH3 CH2F Cl Cl CHC12 Br H
CO2CH3 CH2C1 F Cl CHC12 Br H
CO2CH3 CH2C1 Cl Cl CHC12 Br H
CO2CH3 CH2Br F Cl CHC12 Br H
CO2CH3 CH2Br Cl Cl CHC12 Br H H CH2F F Cl CH3 CN H
H CH2F Cl Cl CH3 CN H
H CH2C1 F Cl CH3 CN H
H CH2C1 Cl Cl CH3 CN H
H CH2Br F Cl CH3 CN H
H CH2Br Cl Cl CH3 CN H
C(=O)CH3 CH2F F Cl CH3 CN H
C(=O)CH3 CH2F Cl Cl CH3 CN H
C(=O)CH3 CH2C1 F Cl CH3 CN H
C(=O)CH3 CH2C1 Cl Cl CH3 CN H
C(=O)CH3 CH2Br F Cl CH3 CN H
C(=O)CH3 CH2Br Cl Cl CH3 CN H
C(=O)CH(CH3)2 CH2F F Cl CH3 CN H
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CN H
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CN H
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CN H
C(=O)CH(CH3)2 CH2Br F Cl CH3 CN H
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CN H
CO2CH3 CH2F F Cl CH3 CN H
CO2CH3 CH2F Cl Cl CH3 CN H
CO2CH3 CH2C1 F Cl CH3 CN H
CO2CH3 CH2C1 Cl Cl CH3 CN H
CO2CH3 CH2Br F Cl CH3 CN H
CO2CH3 CH2Br Cl Cl CH3 CN H
H CH2F F Cl CHC12 CN H
H CH2F Cl Cl CHC12 CN H
H CH2C1 F Cl CHC12 CN H
H CH2C1 Cl Cl CHC12 CN H
H CH2Br F Cl CHC12 CN H
H CH2Br Cl Cl CHC12 CN H
C(=O)CH3 CH2F F Cl CHC12 CN H
C(=O)CH3 CH2F Cl Cl CHC12 CN H
C(=O)CH3 CH2C1 F Cl CHC12 CN H
C(=O)CH3 CH2C1 Cl Cl CHC12 CN H
C(=O)CH3 CH2Br F Cl CHC12 CN H
C(=O)CH3 CH2Br Cl Cl CHC12 CN H
C(=O)CH(CH3)2 CH2F F Cl CHC12 CN H
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 CN H C(=O)CH(CH3)2 CH2C1 F Cl CHC12 CN H
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 CN H
C(=O)CH(CH3)2 CH2Br F Cl CHC12 CN H
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 CN H
CO2CH3 CH2F F Cl CHC12 CN H
CO2CH3 CH2F Cl Cl CHC12 CN H
CO2CH3 CH2C1 F Cl CHC12 CN H
CO2CH3 CH2C1 Cl Cl CHC12 CN H
CO2CH3 CH2Br F Cl CHC12 CN H
CO2CH3 CH2Br Cl Cl CHC12 CN H
H CH2F F Cl CH3 Cl CH3
H CH2F Cl Cl CH3 Cl CH3
H CH2C1 F Cl CH3 Cl CH3
H CH2C1 Cl Cl CH3 Cl CH3
H CH2Br F Cl CH3 Cl CH3
H CH2Br Cl Cl CH3 Cl CH3
C(=O)CH3 CH2F F Cl CH3 Cl CH3
C(=O)CH3 CH2F Cl Cl CH3 Cl CH3
C(=O)CH3 CH2C1 F Cl CH3 Cl CH3
C(=O)CH3 CH2C1 Cl Cl CH3 Cl CH3
C(=O)CH3 CH2Br F Cl CH3 Cl CH3
C(=O)CH3 CH2Br Cl Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2F F Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3 Cl CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Cl CH3
CO2CH3 CH2F F Cl CH3 Cl CH3
CO2CH3 CH2F Cl Cl CH3 Cl CH3
CO2CH3 CH2C1 F Cl CH3 Cl CH3
CO2CH3 CH2C1 Cl Cl CH3 Cl CH3
CO2CH3 CH2Br F Cl CH3 Cl CH3
CO2CH3 CH2Br Cl Cl CH3 Cl CH3
H CH2F F Cl CHC12 Cl CH3
H CH2F Cl Cl CHC12 Cl CH3
H CH2C1 F Cl CHC12 Cl CH3
H CH2C1 Cl Cl CHC12 Cl CH3 H CH2Br F Cl CHC12 Cl CH3
H CH2Br Cl Cl CHC12 Cl CH3
C(=O)CH3 CH2F F Cl CHC12 Cl CH3
C(=O)CH3 CH2F Cl Cl CHC12 Cl CH3
C(=O)CH3 CH2C1 F Cl CHC12 Cl CH3
C(=O)CH3 CH2C1 Cl Cl CHC12 Cl CH3
C(=O)CH3 CH2Br F Cl CHC12 Cl CH3
C(=O)CH3 CH2Br Cl Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2F F Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Cl CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Cl CH3
CO2CH3 CH2F F Cl CHC12 Cl CH3
CO2CH3 CH2F Cl Cl CHC12 Cl CH3
CO2CH3 CH2C1 F Cl CHC12 Cl CH3
CO2CH3 CH2C1 Cl Cl CHC12 Cl CH3
CO2CH3 CH2Br F Cl CHC12 Cl CH3
CO2CH3 CH2Br Cl Cl CHC12 Cl CH3
H CH2F F Cl CH3 Br CH3
H CH2F Cl Cl CH3 Br CH3
H CH2C1 F Cl CH3 Br CH3
H CH2C1 Cl Cl CH3 Br CH3
H CH2Br F Cl CH3 Br CH3
H CH2Br Cl Cl CH3 Br CH3
C(=O)CH3 CH2F F Cl CH3 Br CH3
C(=O)CH3 CH2F Cl Cl CH3 Br CH3
C(=O)CH3 CH2C1 F Cl CH3 Br CH3
C(=O)CH3 CH2C1 Cl Cl CH3 Br CH3
C(=O)CH3 CH2Br F Cl CH3 Br CH3
C(=O)CH3 CH2Br Cl Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2F F Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3 Br CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Br CH3 CO2CH3 CH2F F Cl CH3 Br CH3
CO2CH3 CH2F Cl Cl CH3 Br CH3
CO2CH3 CH2C1 F Cl CH3 Br CH3
CO2CH3 CH2C1 Cl Cl CH3 Br CH3
CO2CH3 CH2Br F Cl CH3 Br CH3
CO2CH3 CH2Br Cl Cl CH3 Br CH3
H CH2F F Cl CHC12 Br CH3
H CH2F Cl Cl CHC12 Br CH3
H CH2C1 F Cl CHC12 Br CH3
H CH2C1 Cl Cl CHC12 Br CH3
H CH2Br F Cl CHC12 Br CH3
H CH2Br Cl Cl CHC12 Br CH3
C(=O)CH3 CH2F F Cl CHC12 Br CH3
C(=O)CH3 CH2F Cl Cl CHC12 Br CH3
C(=O)CH3 CH2C1 F Cl CHC12 Br CH3
C(=O)CH3 CH2C1 Cl Cl CHC12 Br CH3
C(=O)CH3 CH2Br F Cl CHC12 Br CH3
C(=O)CH3 CH2Br Cl Cl CHC12 Br CH3
C(=O)CH(CH3)2 CH2F F Cl CHC12 Br CH3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Br CH3
C(-=O)CH(CH3)2 CH2C1 F Cl CHC12 Br CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Br CH3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Br CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Br CH3
CO2CH3 CH2F F Cl CHC12 Br CH3
CO2CH3 CH2F Cl Cl CHC12 Br CH3
CO2CH3 CH2C1 F Cl CHC12 Br CH3
CO2CH3 CH2C1 Cl Cl CHC12 Br CH3
CO2CH3 CH2Br F Cl CHC12 Br CH3
CO2CH3 CH2Br Cl Cl CHC12 Br CH3
H CH2F F Cl CH3 CN CH3
H CH2F Cl Cl CH3 CN CH3
H CH2C1 F Cl CH3 CN CH3
H CH2C1 Cl Cl CH3 CN CH3
H CH2Br F Cl CH3 CN CH3
H CH2Br Cl Cl CH3 CN CH3
C(=O)CH3 CH2F F Cl CH3 CN CH3
C(=O)CH3 CH2F Cl Cl CH3 CN CH3 C(=O)CH3 CH2C1 F Cl CH3 CN CH3
C(=O)CH3 CH2C1 Cl Cl CH3 CN CH3
C(=O)CH3 CH2Br F Cl CH3 CN CH3
C(=O)CH3 CH2Br Cl Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2F F Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2Br F Cl CH3 CN CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CN CH3
CO2CH3 CH2F F Cl CH3 CN CH3
CO2CH3 CH2F Cl Cl CH3 CN CH3
CO2CH3 CH2C1 F Cl CH3 CN CH3
CO2CH3 CH2C1 Cl Cl CH3 CN CH3
CO2CH3 CH2Br F Cl CH3 CN CH3
CO2CH3 CH2Br Cl Cl CH3 CN CH3
H CH2F F Cl CHC12 CN CH3
H CH2F Cl Cl CHC12 CN CH3
H CH2C1 F Cl CHC12 CN CH3
H CH2C1 Cl Cl CHC12 CN CH3
H CH2Br F Cl CHC12 CN CH3
H CH2Br Cl Cl CHC12 CN CH3
C(=O)CH3 CH2F F Cl CHC12 CN CH3
C(=O)CH3 CH2F Cl Cl CHC12 CN CH3
C(=O)CH3 CH2C1 F Cl CHC12 CN CH3
C(=O)CH3 CH2C1 Cl Cl CHC12 CN CH3
C(=O)CH3 CH2Br F Cl CHC12 CN CH3
C(=O)CH3 CH2Br Cl Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2F F Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 CN CH3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 CN CH3
CO2CH3 CH2F F Cl CHC12 CN CH3
CO2CH3 CH2F Cl Cl CHC12 CN CH3
CO2CH3 CH2C1 F Cl CHC12 CN CH3
CO2CH3 CH2C1 Cl Cl CHC12 CN CH3 CO2CH3 CH2Br F Cl CHC12 CN CH3
CO2CH3 CH2Br Cl Cl CHC12 CN CH3
H CH2F F Cl CH3 Cl CF3
H CH2F Cl Cl CH3 Cl CF3
H CH2C1 F Cl CH3 Cl CF3
H CH2C1 Cl Cl CH3 Cl CF3
H CH2Br F Cl CH3 Cl CF3
H CH2Br Cl Cl CH3 Cl CF3
C(=O)CH3 CH2F F Cl CH3 Cl CF3
C(=O)CH3 CH2F Cl Cl CH3 Cl CF3
C(=O)CH3 CH2C1 F Cl CH3 Cl CF3
C(=O)CH3 CH2C1 Cl Cl CH3 Cl CF3
C(=O)CH3 CH2Br F Cl CH3 Cl CF3
C(=O)CH3 CH2Br Cl Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2F F Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2Br F Cl CH3 Cl CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Cl CF3
CO2CH3 CH2F F Cl CH3 Cl CF3
CO2CH3 CH2F Cl Cl CH3 Cl CF3
CO2CH3 CH2C1 F Cl CH3 Cl CF3
CO2CH3 CH2C1 Cl Cl CH3 Cl CF3
CO2CH3 CH2Br F Cl CH3 Cl CF3
CO2CH3 CH2Br Cl Cl CH3 Cl CF3
H CH2F F Cl CHC12 Cl CF3
H CH2F Cl Cl CHC12 Cl CF3
H CH2C1 F Cl CHC12 Cl CF3
H CH2C1 Cl Cl CHC12 Cl CF3
H CH2Br F Cl CHC12 Cl CF3
H CH2Br Cl Cl CHC12 Cl CF3
C(=O)CH3 CH2F F Cl CHC12 Cl CF3
C(=O)CH3 CH2F Cl Cl CHC12 Cl CF3
C(=O)CH3 CH2C1 F Cl CHC12 Cl CF3
C(=O)CH3 CH2C1 Cl Cl CHC12 Cl CF3
C(=O)CH3 CH2Br F Cl CHC12 Cl CF3
C(=O)CH3 CH2Br Cl Cl CHC12 Cl CF3 C(=O)CH(CH3)2 CH2F F Cl CHC12 Cl CF3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Cl CF3
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 Cl CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Cl CF3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Cl CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Cl CF3
CO2CH3 CH2F F Cl CHC12 Cl CF3
CO2CH3 CH2F Cl Cl CHC12 Cl CF3
CO2CH3 CH2C1 F Cl CHC12 Cl CF3
CO2CH3 CH2C1 Cl Cl CHC12 Cl CF3
CO2CH3 CH2Br F Cl CHC12 Cl CF3
CO2CH3 CH2Br Cl Cl CHC12 Cl CF3
H CH2F F Cl CH3 Br CF3
H CH2F Cl Cl CH3 Br CF3
H CH2C1 F Cl CH3 Br CF3
H CH2C1 Cl Cl CH3 Br CF3
H CH2Br F Cl CH3 Br CF3
H CH2Br Cl Cl CH3 Br CF3
C(=O)CH3 CH2F F Cl CH3 Br CF3
C(=O)CH3 CH2F Cl Cl CH3 Br CF3
C(=O)CH3 CH2C1 F Cl CH3 Br CF3
C(=O)CH3 CH2C1 Cl Cl CH3 Br CF3
C(=O)CH3 CH2Br F Cl CH3 Br CF3
C(=O)CH3 CH2Br Cl Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2F F Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2Br F Cl CH3 Br CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 Br CF3
CO2CH3 CH2F F Cl CH3 Br CF3
CO2CH3 CH2F Cl Cl CH3 Br CF3
CO2CH3 CH2C1 F Cl CH3 Br CF3
CO2CH3 CH2C1 Cl Cl CH3 Br CF3
CO2CH3 CH2Br F Cl CH3 Br CF3
CO2CH3 CH2Br Cl Cl CH3 Br CF3
H CH2F F Cl CHC12 Br CF3
H CH2F Cl Cl CHC12 Br CF3 H CH2C1 F Cl CHC12 Br CF3
H CH2C1 Cl Cl CHC12 Br CF3
H CH2Br F Cl CHC12 Br CF3
H CH2Br Cl Cl CHC12 Br CF3
C(=O)CH3 CH2F F Cl CHC12 Br CF3
C(=O)CH3 CH2F Cl Cl CHC12 Br CF3
C(=O)CH3 CH2C1 F Cl CHC12 Br CF3
C(=O)CH3 CH2C1 Cl Cl CHC12 Br CF3
C(=O)CH3 CH2Br F Cl CHC12 Br CF3
C(=O)CH3 CH2Br Cl Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2F F Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 Br CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 Br CF3
CO2CH3 CH2F F Cl CHC12 Br CF3
CO2CH3 CH2F Cl Cl CHC12 Br CF3
CO2CH3 CH2C1 F Cl CHC12 Br CF3
CO2CH3 CH2C1 Cl Cl CHC12 Br CF3
CO2CH3 CH2Br F Cl CHC12 Br CF3
CO2CH3 CH2Br Cl Cl CHC12 Br CF3
H CH2F F Cl CH3 CN CF3
H CH2F Cl Cl CH3 CN CF3
H CH2C1 F Cl CH3 CN CF3
H CH2C1 Cl Cl CH3 CN CF3
H CH2Br F Cl CH3 CN CF3
H CH2Br Cl Cl CH3 CN CF3
C(=O)CH3 CH2F F Cl CH3 CN CF3
C(=O)CH3 CH2F Cl Cl CH3 CN CF3
C(=O)CH3 CH2C1 F Cl CH3 CN CF3
C(=O)CH3 CH2C1 Cl Cl CH3 CN CF3
C(=O)CH3 CH2Br F Cl CH3 CN CF3
C(=O)CH3 CH2Br Cl Cl CH3 CN CF3
C(=O)CH(CH3)2 CH2F F Cl CH3 CN CF3
C(=O)CH(CH3)2 CH2F Cl Cl CH3 CN CF3
C(=O)CH(CH3)2 CH2C1 F Cl CH3 CN CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CH3 CN CF3 C(=O)CH(CH3)2 CH2Br F Cl CH3 CN CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CH3 CN CF3
CO2CH3 CH2F F Cl CH3 CN CF3
CO2CH3 CH2F Cl Cl CH3 CN CF3
CO2CH3 CH2C1 F Cl CH3 CN CF3
CO2CH3 CH2C1 Cl Cl CH3 CN CF3
CO2CH3 CH2Br F Cl CH3 CN CF3
CO2CH3 CH2Br Cl Cl CH3 CN CF3
H CH2F F Cl CHC12 CN CF3
H CH2F Cl Cl CHC12 CN CF3
H CH2C1 F Cl CHC12 CN CF3
H CH2C1 Cl Cl CHC12 CN CF3
H CH2Br F Cl CHC12 CN CF3
H CH2Br Cl Cl CHC12 CN CF3
C(=O)CH3 CH2F F Cl CHC12 CN CF3
C(=O)CH3 CH2F Cl Cl CHC12 CN CF3
C(=O)CH3 CH2C1 F Cl CHC12 CN CF3
C(=O)CH3 CH2C1 Cl Cl CHC12 CN CF3
C(=O)CH3 CH2Br F Cl CHC12 CN CF3
C(=O)CH3 CH2Br Cl Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2F F Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2F Cl Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2C1 F Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2C1 Cl Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2Br F Cl CHC12 CN CF3
C(=O)CH(CH3)2 CH2Br Cl Cl CHC12 CN CF3
CO2CH3 CH2F F Cl CHC12 CN CF3
CO2CH3 CH2F Cl Cl CHC12 CN CF3
CO2CH3 CH2C1 F Cl CHC12 CN CF3
CO2CH3 CH2C1 Cl Cl CHC12 CN CF3
CO2CH3 CH2Br F Cl CHC12 CN CF3
CO2CH3 CH2Br Cl Cl CHC12 CN CF3
Formulation/Utilitv
Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
Weight Percent
Active Ingredient Diluent Surfactant
Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.
Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates)
Dusts -25 70-99 0-5
Granules and Pellets 0.01 -99 5-99.99 0-15
High Strength Compositions 90-99 0-10 0-2
Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N V-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, NN-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For further information regarding the art of formulation, see U. S. 3 ,235 ,361 , Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-C. Example A
High Strength Concentrate
Compound 3 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%. Example B
Wettable Powder
Compound 5 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%,
Example C
Granule Compound ? 10.0% attapulgite granules (low volatile matter,
0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
Example D Extruded Pellet Compound 17 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%. Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth. A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichloφrop, diclofop-methyl, 2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo-lH-imidazol-2-yl]-5-methyl-3- pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, 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, fiurochloridone, fluroxypyr, fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[l-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2- methoxyethylidene]amino]oxy]acetate (AKH-7088), methyl 5-[[[[(4,6-dimethyl-2- pyrimidinyl)amino]carbonyl]amino]sulfonyl]-l-(2-pyridinyl)-lH-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefiiryl, rimsulfuron, sethoxydim, siduron, simazine, sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vernolate.
In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-D for compound descriptions. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.
INDEX TABLE A
Cmpd Z Rl mo (°0
1 (Ex. 1) CH2 H 168
2 CH2 C(=O)CH3 130
3 (Ex. 2) CH2 C(=O)CH(CH3)2 183
4 CH2 SO2CH2Cl 136
5 O H *
* see Index Table D for -H NMR data
INDEX TABLE B
Cmpd X Y El RIO Eli mo (°C)
6 Cl Cl SO2CH2Cl CH3 CF3 *
7 Cl Cl H CH3 CF3 90 (Ex. 3) F Cl H CH3 CF3 92
9 F Cl SO2CH2Cl CH2CH=CH2 CF3 *
10 F Cl H CH2CH=CH2 CF3 *
1 1 F Cl H CH2C≡CH CF3 * 12 F Cl CH3 CH3 CF3 177
13 F Cl CH2CH3 CH3 CF3 225
14 (Ex. 4) F Cl C(=O)CH3 CH3 CF3 170
15 F Cl SO2CH2Cl CH3 CF3 112
16 F Cl CO2CH3 CH3 CF3 110
17 F Cl CH2C≡CH CH3 CF3 138
* see Index Table D for *H NMR data
INDEX TABLE C
Cmpd Structure mp (°C)
INDEX TABLE D
Cmpd No. *H NMR Data (CDC13 solution unless indicated otherwise)*1 δ 7.3 (d, IH), 7.2 (d, IH), 6.9 (br s, IH), 5.1 (s, 2H), 4.6 (s,
2H), 4.0 (m, 2H), 3.8 (m, 2H). δ 7.48 (s, IH), 6.64 (s, IH), 6.40 (s, IH), 4.55 (s, 4H), 3.57 (s,
3H). δ 7.68 (d, IH), 7.44 (d, IH), 6.36 (s, IH), 5.86 (m, IH), 5.30
(m, 2H), 5.28 and 4.86 (q , 4H), 4.56 (m, 2H). 10 δ 7.68 (d, IH), 7.39 (d, IH), 7.04 (s, IH), 6.37 (s, IH), 5.90 (m, IH), 5.28 (m, 2H), 4.56 (m, 2H), 4.50 (s, 2H).
1 1 δ 8.0 (s, IH), 7.65 (d, IH), 7.38 (d, IH), 6.4 (s, IH), 4.71 (d, 2H), 4.55 (s, 2H), 2.4 (m, lH).
a *H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet.
BIOLOGICAL EXAMPLES OF THE INVENTION Test A
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-gallϊ), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avenafatua) and puφle nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm ( 1 - to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
Table A COMPOUND
Rate 200 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 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 Soybean 4 9 9 10 10 10 6 0 0
Sugar beet 1 100 10 10 10 10 10 10 - 0
Velvetleaf 8 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 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 10 10 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 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 7 10 10 10 0 0
Rice 0 0 0 0 0 0 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 00 99 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 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 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 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
TestB
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 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. 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 (Setaria faberii), johnsongrass (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). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera 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 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 j aponica - 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 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 1 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 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 8 11 16 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 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 0 20 30 30 0 0 40
Johnsongrass 0 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 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 9 10 11 12 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 Wild oat 0 0 0 0 25 10 20 0 0 0 0 0 0 0
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 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 C 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 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 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
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 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 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
TestC
Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), com (Zea mays designated 'Com 5'), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiβorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), smartweed (Polygonum 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 puφle nutsedge (Cyperus rotundus) tubers were planted into a clay loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one- to four-leaf stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Pots receiving preemergence treatments were planted immediatley prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Nisual 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 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 Yellow foxtail
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
Morningg1ory 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 Wild proso 5 50 Wild proso 0 30 Woolly cupgrass 5 5 Woolly cupgrass 0 5 Yellow foxtail 0 5 Yellow foxtail 0 0
TestD
Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were grown for various periods of time before 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), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common ragweed (Ambrosia elatior), com 1 (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiβorum), field bindweed (Convolvulus arvensis), Florida beggarweed (Desmodium tortuosum), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosά), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladysthumb smartweed (Polygonum persicaria), lambsquarters (Chenopodium album), large crabgrass (Digitaria sanguinalis), puφle nutsedge (Cyperus rotundus), redroot pigweed (Amaranthus retroflexus), soybean \(Glycine max), Surinam grass (Brachiaria decumbens), velvetleaf (Abutilon theophrasti) and wild poinsettia (Euphorbia heterophylla). 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.
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 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 COM POTO ID
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 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 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 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 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 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 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 20 Arrowleaf sida 25
Barnyardgrass 0 0 Barnyardgrass 10
Cocklebur 0 0 Cocklebur 70
Common ragweed 0 55 Common ragweed 50
Corn 1 0 0 Corn 1 10
Cotton - 15 Cotton 100
E. blacknightsh - 45 E. blacknightsh 80
Fall panicum 0 0 Fall panicum 10
Field bindweed 0 60 Field bindweed 35
Fl . beggarweed 0 20 Fl . beggarweed 35
Giant foxtail 0 0 Giant foxtail 10
H. beggarticks 0 15 H. beggarticks 25
I. morningglory 0 15 I. morningglory 90
Johnsongrass 0 0 Johnsongrass 10
Ladysthumb - 45 Ladysthumb 35
Lambsquarters 0 80 Lambsquarters 50
Large crabgrass 0 0 Large crabgrass 10
Purple nutsedge 0 0 Purple nutsedge 0
Redroot pigweed 0 45 Redroot pigweed 90
Soybean 1 0 0 Soybean 1 35
Surinam grass 0 0 Surinam grass 5
Velvetleaf 0 15 Velvetleaf 70
Wild poinsettia 0 15 Wild poinsettia 80
TestE
Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied to plants that were in the 1- to 4-leaf stage (postemergence application). A mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), blackgrass 2 (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed (Stellaria media), 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 (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 (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 (-) 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 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 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 - - . 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 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 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
Windςjrass 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
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 Wild oat (2) 0 Wild oat (2) Windgrass 0 70 Windgrass
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 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 (Alisma plantago-aquatica), ducksalad (Heteranthera limosa), early watergrass
(Echinochloa oryzoides), gooseweed (Sphenoclea zeylanica), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryztcø/α),monochoria (Monochoria vaginalis), river bullrush (Scirpus fluviatikis), redstem (Ammania species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis), tighthead sprangletop (Leptochloa fasicularis) 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 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 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 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 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 . f latsedge 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 Redstem 30
Rice flatsedge 10
Rice indica 1 10
Rice indica 3 10
S. flatsedge 0
T. sprangletop 10
Water-clover -
TESTG
Seeds, tubers, or plant parts of alexandergrass (Brachiaria plantaginea), broadleaf signalgrass (Brachiaria decumbens), bermudagrass (Cynodon dactylon), common purslane (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 morningglory (Ipomoea lacunosa), peanuts (Arachis hypogaea), puφle nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis) and Surinam grass (Brachiaria decumbens) were planted into greenhouse pots of flats containing greenhouse planting medium. Plant species were grown 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). 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 (-) 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 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 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 . morning1ory 90 P. morninglory 80
Peanuts 50 Peanuts 10 Peanuts 20
Purple nutsedge 10 Purple nutsedge 100 Purple nutsedge 0
Sandbur - Sandbur 35 Sandbur - 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
TestH
Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture and applied to the surface of the water which was contained in each pot. Individual containers of barnyardgrass (Echinochloa oryzicola), small flower flatsedge (Cyperus difformus), common falsepimpernel (Lindernia procumbens), monochoria (Monochoria vaginalis) and bulrush (Scirpus juncoides) were seeded and allowed to grow until the leaf stage of development was reached. A Sultama clay loam soil was used for this propagation. 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 Sciφus juncoides which was then treated at the 1.5 (early (1)) and the 2.5 (late (2)) leaf stage. 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 (-) 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
Falsepimpernel1 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

CLAIMS What is claimed is: L A compound selected from Formula I, N-oxides and agriculturally suitable salts thereof,
I wherein
X is H, F or Cl;
Y is F, Cl, Br, cyano, nitro, CrC3 haloalkyl, CrC3 alkoxy, CrC3 haloalkoxy or
C(S)ΝH2; R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, CyC6 haloalkynyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, formyl,
C -C6 alkylcarbonyl, C -C7 cycloalkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C6 alkoxyalkylcarbonyl, C2-Cg haloalkoxycarbonyl, C3-C6 cycloalkyl, C3-Cg halocycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, S(O)2R17, C(O)SR3, C(O)NR R5 or benzoyl; R2 is C rC6 haloalkyl other than CF3, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl,
C2-C6 cyanoalkyl, Cj-C6 nitroalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-Cg alkylsulfonylalkyl, C3-Cg alkoxycarbonylalkyl or C3-C8 alkylcarbonyloxyalkyl; R3 is H, C]-C3 alkyl or Cj-C3 haloalkyl; or R3 is phenyl optionally substituted with CrC3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, CrC3 alkoxy or CF3;
R4 is H, C*-C3 alkyl or CrC3 haloalkyl; or R4 is phenyl optionally substituted with
Cj-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C╬╣-C3 alkoxy or CF3; R5 is CrC3 alkyl or CrC3 haloalkyl; or R4 and R5 are taken together as -CH-CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or -CH2CH2OCH2CH2-; J is
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;
alkyl)
Z is CR6R7, O, S, S(O), S(O)2, N(CrC4 alkyl)
R6 is H, Ci-Cg alkyl, halogen, hydroxy, Cj-Cg alkoxy, C^-Cg haloalkyl, C╬╣-C6 haloalkoxy, C -Cg alkylcarbonyloxy or C -Cg haloalkylcarbonyloxy; R7 is H, Cj-Cg alkyl, hydroxy or halogen; or when R6 and R7 are bonded to adjacent carbon atoms they can be taken together with
CH2
A the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 Cj-C3 alkyl;
R8 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl or C3-C6 alkynyl;
R9 is H, halogen, cyano, C^Cg alkyl, C C3 alkoxy or C1-C3 haloalkoxy;
R10 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, HC(=O), C2-C5 alkylcarbonyl orN(Rl6)2; R11 is CrC6 alkyl, CrC6 alkylthio, CrC6 haloalkyl orN(CH3)2; R12 is H, halogen, C C6 alkyl, CrC6 haloalkyl or CrC6 alkoxy; R13 and R14 are each independently H, C Cg alkyl or CrC6 haloalkyl;
R15 is H, CrC6 alkyl or CrC6 haloalkyl; each R16 is independently H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl or C2-C6 alkoxyalkyl; R17 is CrC6 alkyl, CrC6 haloalkyl other than CF3, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, CrC6 nitroalkyl, C2-C6 alkylthioalkyl,
C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C3-C8 alkoxycarbonylalkyl or C3-Cg alkylcarbonyloxyalkyl; and each Q is independently O or S.
2. A compound of Claim 1 wherein X is F or Cl; and Y is F, Cl or Br.
3. A compound of Claim 2 wherein
R1 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-Cg alkoxyalkylcarbonyl, S(O)2R17, C(O)NR4R5 or benzoyl.
4. A compound of Claim 3 wherein J is J-1, J-2, J-3 or J-6.
5. A compound of Claim 4 wherein Z is CR6R7, O or S;
R6 is H, halogen, Cj-Cg alkoxy or C2-Cg alkylcarbonyloxy; R7 is H or halogen; m and n are each independently 1 or 2, provided that m + n is 2 or 3; R8 is CrC6 alkyl, CrC6 haloalkyl or C3-C6 alkenyl; R9 is halogen, C Cg alkyl, Cj-C3 alkoxy or C1-C3 haloalkoxy;
R10 is CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl or NH2; and R1 * is CrC6 alkyl or CrC6 haloalkyl.
6. A compound of Claim 5 wherein R1 is H, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; and
R2 is CrC2 haloalkyl.
7. A compound of Claim 6 wherein J is J-1.
8. A compound of Claim 6 wherein ~5 J is J-2.
9. A compound of Claim 6 wherein J is J-3.
10 10. A compound of Claim 6 wherein
J is J-6.
11. The compound of Claim 6 which is selected from the group:
(a) N-[2-cmoro-5-[(dihydro-3-oxo-lH,3H,5H-pyrazolo[l,2-c][l,3,4]thiadiazol-l- 15 ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide;
(b) N-[2-chloro-5-[(dihydro-3-oxo-lH,3H,5H-pyrazolo[l,2-c][l,3,4]thiadiazol-l- ylidene)amino]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]-2-methylpropanamide;
(c) l-chloro-N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenyl]methanesulfonamide; 0 (d) N-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide;
(e) methyl [2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenyl][(chloromethyl)sulfonyl]carbamate;
(f) l-chloro-N-[2-chloro-5-[3,6-dihydro-3,6-dioxo-3-(2-propenyl)-4- 5 (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- IH- 1 ,2,4- triazol-l-yl]-4-fluorophenyl]-N-[(chloromethyl)sulfonyl]acetamide. 0
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.
13. A method for controlling the growth of undesired vegetation comprising 5 contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.
EP98919824A 1997-04-22 1998-04-20 Herbicidal sulfonamides Withdrawn EP0977760A1 (en)

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BR9808688A (en) 2000-07-11
AU7252698A (en) 1998-11-13
CA2285293A1 (en) 1998-10-29
WO1998047904A1 (en) 1998-10-29

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