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WO1996031517A1 - Anilides herbicides heteroaryl-substitues - Google Patents

Anilides herbicides heteroaryl-substitues Download PDF

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Publication number
WO1996031517A1
WO1996031517A1 PCT/US1996/003803 US9603803W WO9631517A1 WO 1996031517 A1 WO1996031517 A1 WO 1996031517A1 US 9603803 W US9603803 W US 9603803W WO 9631517 A1 WO9631517 A1 WO 9631517A1
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methyl
compound
formula
compounds
chem
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Inventor
Wallace Christian Petersen
Michael Anthony Pifferitti
Thomas Martin Stevenson
Chi-Ping Tseng
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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 heteroaryl-substituted anilides, their N-oxides, agriculturally-suitable salts of the anilides 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, com (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.
  • WO 93/11097 discloses anilides of Formula i as herbicides:
  • Q is, among others, Q-1
  • R is, among others, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, C 1 -C 2 haloalkylthio,
  • Y is ⁇ R 7 C(O)XR 3 ;
  • X is a single bond, O, S or NR 4 ;
  • R 1 is, among others, H, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 2 -C 3
  • alkoxyalkyl C 2 -C 3 alkylthioalkyl, halogen, NO 2 , CN, NHR 5 or NR 5 R 6 ; and R 3 is, among others, C 1 -C 5 alkyl optionally substituted with C 1 -C 2 alkoxy, OH, 1-3 halogen, or C 1 -C 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's; C 2 -C 4 alkenyl; or C 2 -C 4 haloalkenyl.
  • the heteroaryl-substituted anilides of the present invention are not disclosed therein.
  • This invention is directed to compounds of Formula I, geometric isomers, stereoisomers, N-oxides, and agriculturally suitable salts thereof as well as agricultural compositions containing them and their use for controlling undesirable vegetation:
  • T O or S
  • X is a single bond, O, S, or ⁇ R 5 ;
  • Z is CH or N
  • W is CH or N
  • V is CH, CCH 3 or N, provided that V is CH or CCH 3 when W is CH;
  • R 1 is C 1 -C 5 alkyl optionally substituted with C 1 -C 2 alkoxy, OH, 1-7 halogen, or C 1 -C 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); C 3 -C 6 cycloalkyl optionally substituted with 1-3 halogen or 1-4 methyl groups; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; or phenyl optionally substituted with C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, 1-2 halogen, nitro, or cyano; provided that when X is O, S, or NR 5 , then R 1 is other than C 2 alkenyl and C 2 haloalkenyl;
  • R 2 is H, halogen, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 alkylthio, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, cyano, nitro, NH(C 1 -C 2 alkyl), or N(C 1 -C 2 alkyl) 2 ;
  • R 3 is H, halogen, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 alkylthio, C 2 -C 3 alkoxyalkyl,
  • R 4 is C 1 -C 4 haloalkyl, C 1 -C 2 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 2 haloalkylsulfonyl, halogen, cyano, or nitro;
  • R 5 is H, CH 3 , or OCH 3 ;
  • R 6 is H or CH 3 ;
  • n 0 or 1.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl or pentyl isomers.
  • 1-4 methyl groups indicates that one to four of the available positions for that substituent may be methyl.
  • Alkenyl includes straight-chain or branched alkenes such as vinyl, 1 -propenyl, 2-propenyl, and the different butenyl isomers.
  • Alkenyl also includes polyenes such as 1,2-propadienyl.
  • Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 ,
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio and butylthio isomers.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of
  • alkylthioalkyl include CH 3 SCH 2 , CH 3 SCH 2 CH 2 and CH 3 CH 2 SCH 2 .
  • 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 isomers.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • 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.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • 1-7 halogen indicates that one to seven of the available positions for that substituent may be halogen which are independently selected; the terms “1-3 halogen” and “1-2 halogen” are defined
  • haloalkyl 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.
  • haloalkyl include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
  • haloalkenyl “haloalkoxy”, and the like, are defined analogously to the term
  • Examples of "haloalkoxy” include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • Examples of "haloalkylthio” include CCl 3 S, CF 3 S, CCl 3 CH 2 S and ClCH 2 CH 2 CH 2 S.
  • 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 .
  • C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 5.
  • C 1 -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 .
  • 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.
  • 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.
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
  • R 1 is C 1 -C 4 alkyl optionally substituted with methoxy or 1-3 halogen; C 3 -C 4 cycloalkyl optionally substituted with one methyl group; C 2 -C 4 alkenyl; or C 2 -C 4 haloalkenyl;
  • R 2 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, cyano, nitro,
  • R 3 is H.
  • Preferred 2 Compounds of Preferred 1 wherein:
  • X is a single bond
  • R 4 is C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, C 1 -C 2 haloalkylthio, chlorine, or bromine.
  • 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.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-34.
  • the definitions of Q, T, X, Y, Z, W, V, R 1 -R 6 and n in the compounds of Formulae 1-48 below are as defined above in the Summary of the Invention.
  • Compounds of Formulae la-Ic are various subsets of the compounds of Formula I, and all substituents for Formulae la-Ic are as defined above for Formula I.
  • the coupling is carried out by methods known in the art: for example, see Tsuji, J., Organic Synthesis with Palladium Compounds,
  • the coupling of la and 2a is carried out by heating the mixture in the presence of a transition metal catalyst such as tetrakis(triphenylphosphine) palladium(0) or bis(triphenylphosphine)- palladium (II) dichloride in a solvent such as toluene, acetonitrile, glyme, or tetrahydrofuran optionally in the presence of an aqueous inorganic base such as sodium hydrogen carbonate or an organic base such as triethylamine.
  • a transition metal catalyst such as tetrakis(triphenylphosphine) palladium(0) or bis(triphenylphosphine)- palladium (II) dichloride
  • a solvent such as toluene, acetonitrile, glyme, or tetrahydrofuran
  • an aqueous inorganic base such as sodium hydrogen carbonate or an organic base such as triethylamine.
  • Substituted phenyl compounds of Formula 1b wherein X 2 is chlorine, bromine, iodine or trifluoromethylsulfonyloxy (OTf) can be coupled with heteroaromatic compounds of Formula 2b wherein X 1 is trialkyltin (e.g., Me 3 Sn), trialkylsilyl (e.g., Me 3 Si), or a boronic acid derivative (e.g., B(OH) 2 ).
  • the procedure for conducting the coupling is the same as those described and referenced above.
  • compounds of Formula la and 2b are prepared by treating the corresponding halide (i.e., wherein X 1 and X 2 is bromine or iodine) with a metalating agent such as n-butyllithium followed by quenching with a trialkyltin halide, trialkylsilyl halide, boron trichloride, or trialkyl borate.
  • a metalating agent such as n-butyllithium
  • Some compounds of Formula la can also be prepared from the corresponding ort ho-unsubstituted compound (i.e., wherein X 2 is hydrogen) by treatment with a base such as n-butyllithium followed by quenching with a trialkyltin halide, trialkylsilyl halide, or trialkyl borate as reported in the same literature references.
  • a base such as n-butyllithium
  • Anilides and heteroaromatics of Formulae 1 and 2 wherein X 1 and X 2 are chlorine, bromine, iodine, OTf, and hydrogen are either known or readily prepared by procedures and techniques well known in the art, for example: D. E. Pereira, et al., Tetrahedron (1987), 43, 4931-4936; K. Senga, et al., J. Med. Chem. (1981), 24, 610-613;
  • anilines of Formula 3 can be converted into the corresponding isocyanate by treatment with phosgene or known phosgene equivalents
  • the palladium coupling reaction on an N-protected form of the aniline, for example the 2,2-dimethylpropanamide.
  • the N-protecting group can be removed, for example by treatment of the 2,2-dimethylpropanamide with acid, to liberate the amino group.
  • Anilines of Formula 3 are readily prepared by palladium catalyzed coupling of an ⁇ rt/t ⁇ -substituted nitrophenyl compound of Formula 5a, wherein X 2 is as defined above, with a heteroaromatic compound of Formula 2a, wherein X 1 is as defined above, followed by catalytic or chemical reduction of the nitro group (Scheme 4).
  • Scheme 1 the reactivity of the substrates can be reversed, i.e., the coupling is carried out using an ortho-substituted nitrophenyl compound of Formula 5b and a
  • X 3 can be any of a number of heterocycle building blocks, including, but not
  • X 3 COCH 2 NH 2 , COCH 2 -halogen
  • X 3 is as previously defined in Scheme 5.
  • Formula la may be achieved by one of three ways. First, one skilled in the art may simply select the appropriate heteroaromatic compound of Formula 2a,b for the palladium coupling in Schemes 1 and 4 to give examples with a variety of values for R 4 . Alternatively, it may at times be convenient to vary R 4 by performing various functional group transformations on compounds of Formula 9, which can be prepared by the same methods for the preparation of the aryl-substituted heterocycles of Formula la, as shown in Scheme 8.
  • R 4 it may at times be convenient to vary R 4 by performing various functional group transformations on compounds of Formula 10, which can be prepared by the same methods for the preparation of the ⁇ rt ⁇ o-substituted nitrophenyl compounds of Formula 7, and then converting the product to compounds of Formula la (using methods discussed previously) as shown in Scheme 9.
  • Methods to perform these transformations are well known in the literature. Some examples include conversion of chloro to bromo (L. J. Street, et al., J. Med. Chem. (1992), 35, 295-304), bromo to trifluoromethyl (J. Wrobel, et al., J. Med. Chem. (1989), 32(11), 2493-2500), cyano (Ellis, G. P., T.
  • thiophosgene or known thiophosgene equivalents e.g., 1, 1'-thiocarbonyldiimidazole
  • anilines of Formula 11 can be converted into die corresponding isocyanate and then condensed with an appropriate alcohol or amine to afford anilides of Formula lb (Scheme 13). These techniques were described for Scheme 3.
  • Anilines of Formula 11 can be prepared by the reduction of compounds of
  • X 6 can be any number of substituents useful in the synthesis of nitrogen heterocycles, including, but not limited to those shown below:
  • X 3 NO 2 , NH 2 , NHNH 2 , X 5 , CH 2 X 5 , CHO, CO 2 H, COCl, CN;
  • X 5 Cl, Br, I, OTf.
  • Scheme 17 shows a direct displacement reaction with an appropriately substituted pyrrole of Formula 14.
  • an appropriately substituted pyrrole of Formula 14 For example, see: Katritzky, A. R. and Rees, C. E., Eds., Comprehensive Heterocyclic Chemistry, Vol. 4, p. 235 ff., Pergamon Press, London (1984); Smith, L. R., Chem. Heterocycl. Compd. (1972), 25-2, 127; Santaniello, E., Farachi, C., Ponti, F., Synthesis (1979), 617; Jones, R. A. and Bean, G. P., The Chemistry of Pyrroles, Academic Press, London, 1977, Chapter 4, pp. 205-11;
  • Scheme 19 shows an alkylation reaction of an imidazole by compounds of Formula 13.
  • Pyrazole compounds of Formula 23 can be prepared by direct displacement reactions as shown in Scheme 21.
  • N-alkylation and N-arylation are taught by Dorr, H. J. M., Elguero, J., Espada, M. and Hassanaly, P., An Quim. (1978), 74, 1137; Khan, M. A. and Lynch, B. M., J.
  • Example 3 A synthesis of an N-aryl pyrazole by a ring construction method is illustrated in Example 3. Numerous other methods are reviewed in Katritzky, A. R. and Rees, C. E., Comprehensive Heterocyclic Chemistry, Vol. 5, p 272 ff.
  • 1,2,4-triazole compounds of Formula 28 can be prepared by ring construction methods well known in the literature. An illustrative example is given in Scheme 23.
  • Formula lb may be achieved by one of two ways. First, one skilled in the art may simply select the appropriate heteroaromatic compound of Formula 14, in Scheme 15 to give examples with a variety of values for R 4 . Alternatively, it may at times be convenient to vary R 4 by performing various functional group transformations on compounds of Formula 37, which can be prepared by the same methods for the preparation of the aryl-substituted heterocycles of Formula lb, as shown in Scheme 25. Methods to perform these transformations are well known in the literature and were described in the discussion for Schemes 8 and 9.
  • Scheme 26 illustrates the preparation of compounds of Formula Ic (Formula I where Q is Q-3) whereby an appropriately substituted pyridazine of Formula 38 is reacted with a suitably substituted condensing agent such as hydrazides, anhydrides, orthoesters, ⁇ -dicarbonyl compounds and others.
  • a suitably substituted condensing agent such as hydrazides, anhydrides, orthoesters, ⁇ -dicarbonyl compounds and others.
  • the substituent R 4 may often be incorporated by selection of the proper condensing agent. However, it may at times be necessary or convenient to introduce the desired substituents after the cyclization has occurred.
  • This strategy is shown in Scheme 27. Numerous methods for such transformations are known to those skilled in the art. For example: Stanovnik, B., Tisler, M., Tetrahedron, (1967), 387-395; Kobe, J., Stanovnik, B., Tisler, M., Tetrahedron, (1968), 239-245, and methods discussed in Schemes 8 and 9.
  • Compounds of Formula 39 can be prepared by the same methods shown in Scheme 26.
  • the arylpyridazines of Formula 38 can be prepared by palladium-catalyzed coupling of an arylboronic acid of Formula 40 with a pyridazine of Formula 41 as shown in Scheme 28.
  • the pyridazines of Formula 41 are commercially available or can be prepared by methods known in the art. One skilled in the art will notice that for
  • X 7 NHNH 2
  • compounds of Formula 38b can be prepared by nucleophilic displacement of chlorine as shown in Scheme 28.
  • the coupling is carried out by methods known in the literature as discussed for Scheme 1.
  • the coupling is carried out by heating the mixture of 40 and 41 in the presence of a transition metal catalyst such as
  • the requisite boronic acid can be prepared according to literature cited for Scheme 1 as shown in Scheme 29. This involves treating a bromide or iodide of Formula 42 with a metallating agent such as butyllithium followed by quenching with a trialkyl borate and, finally, treating with dilute acid to give the desired boronic acids of Formula 40.
  • a metallating agent such as butyllithium
  • X 8 H
  • the anilides of Formula 42 are either known or readily prepared by procedures and techniques well known in the art, for example: Houben-Weyl, Methoden der Organische Chemie, IVth Ed., Eugen Muller, Ed., George Thieme Veriag; I. J. Turchi, The
  • Anilines of Formula 47 are readily prepared by palladium-catalyzed coupling of an ortho-substituted nitrophenyl compound of Formula 48 with a heterocycle of Formula 43 (described previously), followed by catalytic hydrogenation or chemical reduction of the nitro group as shown in Scheme 34. Reduction of nitro groups is well documented in the literature. See for example, Ohme, R., Zubek, A. R. in Preparative Organic Chemistry, 557, Hilgetag, G. and Martini, A., Eds. John Wiley & Sons, New York (1972).
  • 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.
  • Step A Preparation of 1-(2-amino-5-methylphenyl)-2-[[5-(trifluoromethyl)-4H- 1 ,2,4-triazol-3-yl]thio]ethanone
  • Step B Preparation of 4-methyl-2-[2-(trifluoromethyl)thiazolo[3,2- b] [ 1.2.4]triazol-6-yl]benzenamine
  • Step C Preparation of 3-methyl-N-[4-methyl-2-[2-(trifluoromethyl)thiazolo[3,2- b] [ 1 ,2,4]triazol-6-yl]phenyl]butanamide
  • Step B Preparation of 4-methyl-2-[[3-(trifluoromethyl)-1H-pyrazol-1- yl]methyl]benzenamine
  • Step A The title compound of Step A (3.0 g, 18 mmol) in dioxane (30 mL) was heated at reflux with trifluoroacetaldehyde hydrate (3.0 g, 26 mmol) and a catalytic amount of p-toluenesulfonic acid (0.1 g) for 20 h.
  • the product was isolated by evaporation of the solvent and recrystallization from methanol/water to give 3.87 g of the title compound of Step B as a solid melting at 159-160°C.
  • Step C Preparation of 2,2,2-trifluoro-N-(5-methyl-2- nitrophenyl]ethanehydrazonoyl bromide
  • Step D Preparation of 5-butoxy-4,5-dihydro- 1 -(5-methyl-2-nitrophenyl)- 1H- pyrazole
  • Step E the title compound of Step E can be prepared directly from
  • Step F Preparation of 4-methyl-2-[3-(trifluoromethyl)-1H-pyrazol-1- yl]benzenamine
  • Step F To a benzene solution (30 mL) at 25°C was added the title compound of Step F (0.75 g, 3.14 mmol), pyridine (0.5 g, 6.3 mmol), and isobutyryl chloride (2.0 g,
  • Step A Preparation of N-(2-borono-4-methylphenyl)-2,2-dimethylpropanamide
  • a solution of 72.4 g N-(4-methylphenyl)-2,2-dimemylpropanamide in 1000 mL of dry THF was cooled to -70°C under nitrogen and 480 mL of 2.5M H-BuLi in hexanes was added dropwise over 1 h while maintaining the temperature below -60°C. Stirring was continued at -70°C for 1 h, and then the reaction was allowed to warm to room temperature with stirring overnight.
  • reaction mixture was then cooled to - 10°C and 200 mL of trimethyl borate was added dropwise while maintaining the temperature below 0°C. Stirring was continued at 0°C for 2.5 h, 50 mL of water was added dropwise over 0.5 h, and then concentrated HCl was added to acidify the reaction. The solvents were removed in vacuo, 200 mL of water was added to form a slurry which was shaken (or stirred) thoroughly with ether. The white precipitate was collected by filtration, washed well with a 1 : 1 ether/hexane mixture, and then suspended in acetone and stirred for 20 min. While stirring, 600 mL of water was added slowly in portions (more water may be necessary if precipitation is not complete).
  • Step B Preparation of N-[2-(6-chloro-3-pyridazinyl)-4-methylphenyl]-2,2- dimethylpropan amide
  • Step D Preparation of 2,2-dimethyl-N-[4-methyl-2-[3-(trifluoromethyl)-1,2,4- triazolo[4,3-b]pyridazin-6-yl]phenyl]propanamide
  • Example 6 a compound of the invention, as a solid melting at 102-103 °C.
  • IR (mineral oil) 3280, 1682 cm -1 ; 1 H ⁇ MR (300 MHz, CDCl 3 ): ⁇ 0.92 (d,6H), 2.1 (m,1H), 2.2 (d,2H), 2.38 (s,3H), 6.8 (s,1H), 7.15 (s,1H), 7.2 (d,1H), 7.8 (s,1H), 8.23 (d,1H), 9.5 (s,1H).
  • 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
  • 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 any suitable ingredient such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
  • Active ingredient can be any suitable ingredient such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
  • Active ingredient can be
  • the entire formulation of active ingredient can be encapsulated (or
  • 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.
  • 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,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and
  • 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,
  • Solutions 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
  • 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 barley, cotton, wheat, rape, sugar beets, corn (maize), soybeans, rice, oats, peanuts, vegetables, tomato, potato, and plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea, forests such as eucalyptus and conifers, e.g., loblolly pine, and turf species, e.g.,
  • 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.
  • 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
  • flumiclorac-pentyl flumioxazin, fluometuron, fluoroglycofen-ethyl, fiupoxam, fluridone, flurochloridone, fluroxypyr, fomesafen, fosamine-ammonium, glufosinate,
  • Preferred for better control of undesired vegetation e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group atrazine, chlorimuron-ethyl, imazaquin,
  • imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, norflurazon, and pyrithiobac are selected from the group: compound 1 and atrazine; compound 1 and chlorimuron-ethyl; compound 1 and imazaquin; compound 1 and imazethapyr; compound 1 and norflurazon; compound 1 and pyrithiobac; compound 4 and atrazine; compound 4 and chlorimuron-ethyl; compound 4 and imazaquin; compound 4 and imazethapyr; compound 4 and norflurazon; compound 4 and pyrithiobac; compound 40 and atrazine; compound 40 and chlorimuron-ethyl; compound 40 and imazaquin;
  • compound 40 and imazethapyr compound 40 and norflurazon; compound 40 and pyrithiobac; compound 41 and atrazine; compound 41 and chlorimuron-ethyl;
  • compound 46 and imazethapyr compound 46 and norflurazon; compound 46 and pyrithiobac; compound 133 and atrazine; compound 133 and chlorimuron-ethyl;
  • compound 133 and imazaquin compound 133 and imazethapyr; compound 133 and norflurazon; and compound 133 and pyrithiobac.
  • 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. 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.
  • 1 1 H NMR data are in ppm downf ⁇ eld from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (m)-multiplet, (br s)-broad singlet.
  • Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.
  • Plants ranged in height from two to eighteen cm (one to four 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 B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • the compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes 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).
  • preemergence application to water that covered the soil surface
  • postemergence application to plants that were in the one-to-four leaf stage
  • a sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.
  • barnyardgrass Echinochloa crus-galli
  • barley Hordeum vulgare
  • bedstraw Galium aparine
  • blackgrass Alopecur ⁇ s myosuroides
  • chickweed Stellaria media
  • cocklebur Xanthium strumarium
  • corn Zea mays
  • cotton Gossypium hirsutum
  • crabgrass Digitaria sanguinalis
  • downy brome Bromus tectorum
  • giant foxtail Setaria faberi ⁇
  • johnsongrass Sorghum halepense
  • lambsquarters Choenopodium album
  • momingglory Ipomoea hederacea
  • pigweed Amaranthus retroflexus
  • rape Brassica napus
  • ryegrass Lolium multiflorum
  • soybean Glycine max
  • speedwell Veronica persica
  • sugar beet Beta vulgaris
  • velvetleaf Abutilon theophrast ⁇
  • wheat Tri
  • Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and late watergrass (Echinochloa oryzicola) grown to the 2 leaf stage for testing.
  • Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were grown for various periods of time before treatment (postemergence application).
  • a sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
  • Test compounds were applied within approximately one day after planting seeds for the preemergence 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 american black nightshade (Solanum americanum), arrowleaf sida (Sida rhombifolia), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common lambsquarters (Chenopodium album), common ragweed (Ambrosia artemisiifoli ⁇ ), corn (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum
  • dichotomiflorum field bindweed (Convolvulus arvensis), Florida beggarweed
  • 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 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.
  • Plastic pots were partially filled with silt loam soil. The soil was then saturated with water.
  • Rice Oryza sativa seed or seedlings at the 2.0 to 3.5 leaf stage; seeds tubers or plant parts selected from barnyardgrass (Echinochloa crus-gall ⁇ ), duck salad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), junglerice
  • Treated plants and controls were maintained in a greenhouse for approximately
  • 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.
  • alexandergrass (Brachiaria plantaginea), alfalfa (Medicago sativa), bermudagrass (Cynodon dactylo ⁇ ), broadleaf signalgrass (Brachiaria platyphylla), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hirsutum), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), johnsongrass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanuts (Arachis hypogaea), pitted momingglory (Ipomoea lacunos ⁇ ), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sour
  • Plant species were grown in separate pots or individual compartments. Test chemicals were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied preemergence and postemergence to the plants. 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).
  • Plant response ratings 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.
  • Test compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to four leaf stage (postemergence application).
  • a sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
  • Test compounds were applied within approximately one day after planting seeds for the preemergence test.
  • Crop and weed species include annual bluegrass (Poa annua), black nightshade (Solanum nigrum), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters
  • Wild oat was treated at two growth stages. The first stage (1) was when the plant had two to three leaves. The second stage (2) was when the plant had approximately four leaves or in the initial stages of tillering.
  • 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 H, 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.
  • Test compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were grown for various periods of time before treatment (postemergence application).
  • a sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
  • Test compounds were applied within approximately one day after planting seeds for the preemergence test, and 13 days after the last postemergence planting.
  • Crop and weed species include alexandergrass (Brachiaria plantaginea), american black nightshade (Solanum americanum), apple-of-Peru).
  • Treated plants and untreated controls were maintained in a greenhouse for approximately 13 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table I, 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.

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Abstract

L'invention décrit des composés de formule (I) et leurs -oxydes et sels pouvant être utilisés dans l'agriculture, lesquels sont utiles pour éliminer les végétaux indésirables; où Q est (Q-1), (Q-2), (Q-3), T est O ou S; X est une liaison simple, O, S ou NR5; Y est O, S, NR6, -CH=CH- ou -CH=N-, où -CH=N- peut être attaché suivant l'une des deux orientations possibles; Z est CH ou N; W est CH ou N; V est CH, CCH¿3? ou N, à condition que V soit CH ou CCH3 quand W est CH; n vaut 0 ou 1; et R?1-R6¿ sont tels que définis dans l'invention. L'invention décrit également des compositions contenant lesdits composés de formule (I) ainsi qu'un procédé pour éliminer les végétaux indésirables qui consiste à mettre en contact lesdits végétaux ou ce qui les environne avec une quantité efficace d'un composé de formule (I).
PCT/US1996/003803 1995-04-04 1996-03-20 Anilides herbicides heteroaryl-substitues Ceased WO1996031517A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1024138A4 (fr) * 1997-10-13 2002-02-06 Yamanouchi Pharma Co Ltd Derives de pyrazole
WO2002102809A1 (fr) * 2001-06-13 2002-12-27 Kaken Pharmaceutical Co., Ltd. Derives thiazolotriazole, leurs intermediaires, et herbicides contenant ces derives comme ingredient actif
JP2010501633A (ja) * 2006-08-30 2010-01-21 セルゾーム リミテッド キナーゼ阻害剤としてのトリアゾール誘導体
US7994203B2 (en) * 2008-08-06 2011-08-09 Novartis Ag Organic compounds
WO2013161928A1 (fr) * 2012-04-26 2013-10-31 塩野義製薬株式会社 Dérivé oxazolotriazole et composition médicamenteuse contenant celui-ci
US8865699B2 (en) 2007-11-27 2014-10-21 Cellzome Ltd. Amino triazoles as PI3K inhibitors
WO2022053838A1 (fr) * 2020-09-14 2022-03-17 The University Of Sussex Inhibiteurs à petites molécules de la lémur tyrosine kinase 3
CN115484825A (zh) * 2020-04-22 2022-12-16 住友化学株式会社 苯基化合物及植物病害防除方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4236015A (en) * 1977-01-07 1980-11-25 Westwood Pharmaceuticals, Inc. 1-(2-Acylaminophenyl)imidazoles
EP0244098A2 (fr) * 1986-04-30 1987-11-04 Schering Agrochemicals Limited Herbicides de thiazolotriazole
US4810282A (en) * 1982-01-07 1989-03-07 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
EP0353902A1 (fr) * 1988-07-19 1990-02-07 E.I. Du Pont De Nemours And Company Phényltriazolopyrimidines substitués comme herbicides
JPH0291062A (ja) * 1988-09-27 1990-03-30 Kumiai Chem Ind Co Ltd トリアゾール誘導体及び殺虫剤
WO1993011097A1 (fr) * 1991-11-27 1993-06-10 E.I. Du Pont De Nemours And Company Derives herbicides a base d'amino-(phenyle- ou pyridinyle- ou thienyle-)-phenyle acyles
WO1995009846A1 (fr) * 1993-10-06 1995-04-13 E.I. Du Pont De Nemours And Company Anilides herbicides a substitution heteroaryle

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4236015A (en) * 1977-01-07 1980-11-25 Westwood Pharmaceuticals, Inc. 1-(2-Acylaminophenyl)imidazoles
US4810282A (en) * 1982-01-07 1989-03-07 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
EP0244098A2 (fr) * 1986-04-30 1987-11-04 Schering Agrochemicals Limited Herbicides de thiazolotriazole
EP0353902A1 (fr) * 1988-07-19 1990-02-07 E.I. Du Pont De Nemours And Company Phényltriazolopyrimidines substitués comme herbicides
JPH0291062A (ja) * 1988-09-27 1990-03-30 Kumiai Chem Ind Co Ltd トリアゾール誘導体及び殺虫剤
WO1993011097A1 (fr) * 1991-11-27 1993-06-10 E.I. Du Pont De Nemours And Company Derives herbicides a base d'amino-(phenyle- ou pyridinyle- ou thienyle-)-phenyle acyles
WO1995009846A1 (fr) * 1993-10-06 1995-04-13 E.I. Du Pont De Nemours And Company Anilides herbicides a substitution heteroaryle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9019, Derwent World Patents Index; Class C02, AN 90-144329, XP002009476 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1024138A4 (fr) * 1997-10-13 2002-02-06 Yamanouchi Pharma Co Ltd Derives de pyrazole
US6958339B2 (en) 1997-10-13 2005-10-25 Astellas Pharma Inc. Pyrazole derivative
US7247635B2 (en) 1997-10-13 2007-07-24 Astellas Pharma Inc. Pyrazole derivative
US7285554B2 (en) 1997-10-13 2007-10-23 Astellas Pharma Inc. Pyrazole derivative
WO2002102809A1 (fr) * 2001-06-13 2002-12-27 Kaken Pharmaceutical Co., Ltd. Derives thiazolotriazole, leurs intermediaires, et herbicides contenant ces derives comme ingredient actif
JP2010501633A (ja) * 2006-08-30 2010-01-21 セルゾーム リミテッド キナーゼ阻害剤としてのトリアゾール誘導体
EP2057158B1 (fr) * 2006-08-30 2015-08-12 Cellzome Limited Dérivés de triazole en tant qu'inhibiteurs de kinase
US8883820B2 (en) 2006-08-30 2014-11-11 Cellzome Ltd. Triazole derivatives as kinase inhibitors
CN103641829A (zh) * 2006-08-30 2014-03-19 塞尔佐姆有限公司 作为激酶抑制剂的三唑衍生物
US8865699B2 (en) 2007-11-27 2014-10-21 Cellzome Ltd. Amino triazoles as PI3K inhibitors
US7994203B2 (en) * 2008-08-06 2011-08-09 Novartis Ag Organic compounds
WO2013161928A1 (fr) * 2012-04-26 2013-10-31 塩野義製薬株式会社 Dérivé oxazolotriazole et composition médicamenteuse contenant celui-ci
CN115484825A (zh) * 2020-04-22 2022-12-16 住友化学株式会社 苯基化合物及植物病害防除方法
EP4140303A4 (fr) * 2020-04-22 2024-04-24 Sumitomo Chemical Company, Limited Composé phényle et procédé de lutte contre des maladies de plante
WO2022053838A1 (fr) * 2020-09-14 2022-03-17 The University Of Sussex Inhibiteurs à petites molécules de la lémur tyrosine kinase 3

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