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WO1995023509A1 - Hydantoïnes bicycliques herbicides - Google Patents

Hydantoïnes bicycliques herbicides Download PDF

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Publication number
WO1995023509A1
WO1995023509A1 PCT/US1995/002665 US9502665W WO9523509A1 WO 1995023509 A1 WO1995023509 A1 WO 1995023509A1 US 9502665 W US9502665 W US 9502665W WO 9523509 A1 WO9523509 A1 WO 9523509A1
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Prior art keywords
alkyl
halogen
haloalkyl
chr
fluoro
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Application number
PCT/US1995/002665
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English (en)
Inventor
Mathias Schäfer
Original Assignee
E.I. Du Pont De Nemours And Company
Degussa Aktiengesellschaft
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 E.I. Du Pont De Nemours And Company, Degussa Aktiengesellschaft filed Critical E.I. Du Pont De Nemours And Company
Priority to AU21155/95A priority Critical patent/AU2115595A/en
Publication of WO1995023509A1 publication Critical patent/WO1995023509A1/fr

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Classifications

    • 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

Definitions

  • This invention comprises bicyclic hydantoins and their agriculturally suitable salts wherein the piperidine ring which is incorporated into ring system bears a non-hydrogen substituent, for weed control in plantation crops.
  • the yields of selected plantation crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, and fruit trees tend to be lessened by undesired plants such as crabgrass, guineagrass, itchgrass and the like.
  • the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling undesired plants to improve the yields of plantation crops such as those mentioned above.
  • the dashed line indicates that the left-hand ring contains only single bonds or one bond in the ring is a double bond
  • G is O; S or NH;
  • R 1 is halogen; hydroxy; cyano; C 1 -C 3 alkoxy; C 1 -C 3 haloalkoxy; C 2 -C 4
  • alkylcarbonyloxy or C 2 -C 4 haloalkylcarbonyloxy
  • R 2 is H; hydroxy; or halogen; or
  • W is O or S
  • R 3 is halogen
  • R 4 is H; C 1 -C 8 alkyl; C 1 -C 8 haloalkyl; halogen; OH; OR 9 ; SH; S(O) n R 9 ; COR 9 ;
  • n 0; 1 or 2;
  • R 5 is C 1 -C 2 alkyl; C 1 -C 2 haloalkyl; OCH 3 ; SCH 3 ; OCHF 2 ; halogen; CN or NO 2 ; R 6 is H; C 1 -C 3 alkyl or halogen;
  • R 7 is H; C 1 -C 3 alkyl; halogen; C 1 -C 3 haloalkyl; cyclopropyl; vinyl; C 2 alkynyl; CN;
  • R 8 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkoxyalkyl; C 3 -C 6 alkenyl; C 3 -C 6 alkynyl; or
  • R 9 is C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8
  • haloalkyl C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfmylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 alkoxyalkoxyalkyl; C 4 -C 8 cycloalkylalkyl;
  • C 4 -C 8 alkynylthioalkyl C 1 -C 4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with at least one member independently selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; C 4 -C 8 trialkylsilylalkyl; C 3 -C 8 cyanoalkyl; C 3 -C 8 halocycloalkyl; C 3 -C 8 haloalkenyl;
  • R 10 is C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
  • R 11 and R 13 are independently H or C1-C4 alkyl
  • R 12 and R 14 are independently C 1 -C 4 alkyl or phenyl optionally substituted with at least one member independently selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; or
  • R 1 1 and R 12 are taken together with the nitrogen to which they are attached to form a piperidinyl, pyrrolidinyl or morpholinyl ring, each ring optionally substituted with at least one member independently selected from the group C 1 -C 3 alkyl, phenyl and benzyl; or
  • R 13 and R 14 are taken together with the carbon to which they are attached to form C 3 -C 3 cycloalkyl
  • R 15 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 16 and R 17 are independently H or C 1 -C 4 alkyl
  • R 18 is H; C 1 -C 6 alkyl; C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; R 19 is H; C 1 -C 4 alkyl or halogen;
  • R 20 is H or C 1 -C 4 alkyl
  • R 21 is C 1 -C 2 alkyl; C 1 -C 2 haloalkyl; OCH 3 ; SCH 3 ; OCHF 2 ; halogen; CN or NO 2 ; and their corresponding N-oxides and agriculturally suitable salts.
  • Examples of structures of Formula I are:
  • R 1 is halogen
  • R 2 is H or halogen
  • Q is selected from the group consisting of Q-1, Q-2 and Q-5;
  • R 5 is C 1 -C 2 haloalkyl, OCH 3 , OCHF 2 , C ⁇ , ⁇ O 2 , or halogen;
  • R 7 is H or methyl
  • W is O.
  • Preferred 2 Compounds of Preferred 1 wherein:
  • R 5 is halogen
  • R 6 is H or C 1 -C 3 alkyl
  • R 9 is C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8
  • haloalkyl C 2 -C 8 alkoxyalkyl; C 1 -C 4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with at least one member independently selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 haloalkynyl; C 2 -C 8 alkylcarbonyl; benzyl optionally substituted with at least one member independently selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; CHR 16 COR 10 ;
  • Preferred methods-of-use employ compounds selected from the group:
  • Compounds of Formula I may exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers 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 and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkenyl includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene. "Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,7-octadiyne and 2,5,8-decatriyne.
  • Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl.
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • alkoxyalkyl examples include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • 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.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyloxy includes the same groups linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy.
  • Cycloalkenyl includes groups such as
  • cyclopentenyl and cyclohexenyl examples include
  • Alkylcycloalkyl denotes alkyl substitution on a cycloalkyl moiety. Examples include 4-methylcyclohexyl and 3-isopropylcyclopentyl.
  • CF 3 CH 2 CH CHCH 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CCl 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, CF 2 HCH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CCl 3 S, CF 3 S, CCl 3 CH 2 S and CH 2 ClCH 2 CH 2 S.
  • haloalkylsulfonyl examples include CF 3 SO 2 , CCl 3 SO 2 , CF 3 CH 2 SO 2 and CF 3 CF 2 SO2.
  • 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 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 8.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkoxy designates
  • CH 3 OCH 2 O; C 3 alkoxyalkoxy designates, for example, CH 3 OCH 2 CH 2 O or
  • CH 3 CH 2 OCH 2 O; and C4 alkoxyalkoxy designates the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 O, and CH 3 CH 2 OCH 2 CH 2 O.
  • the compounds represented by Formula I can be prepared according to the methods described in EP-A-493,323 and illustrated below in Schemes 1-7, or by other procedures known in the art.
  • the definitions of W, and R 1 through R 21 in the compounds of Formulae 1-10 below are as defined above in the Summary of the Invention.
  • Compounds of Formula la - If are within the definition of compounds of Formula I.
  • the reaction can take place in an inert organic solvent, such as toluene, chlorobenzene, chloroform, methylene chloride, diisopropyl ether, acetonitrile, dimethylformamide and the like, optionally with base catalysis at a preferred temperature of 20-120°C.
  • Preferred bases are organic bases, for example; organic amines such as triethylamine or pyridine (see EP-A-272,594).
  • the reaction can take place in water as the solvent or, preferably, in a two-phase system containing water and an organic solvent.
  • an inorganic base for example, an alkali or alkaline-earth metal hydroxide, carbonate or hydrogen carbonate, such as sodium hydroxide or potassium carbonate, or an organic base, for example, an organic amine such as triethylamine, to water, and then the iso- or isothio-cyanate of Formula 1 (dissolved in an inert solvent such as toluene,
  • chlorobenzene or chloroform is added.
  • the reaction mixture is then held at a temperature between about -40°C and 120°C, preferably -10-40°C, for up to several days, preferably between 3 and 50 hours.
  • the aqueous phase is then adjusted to a pH between 1 and 3 with acid, preferably with an inorganic acid such as aqueous hydrochloric acid or aqueous sulfuric acid.
  • the intermediate ureas of Formula 4 thus formed are then cyclized by (1) heating at a temperature between about 50°C and 100°C or, (2) by heating in the presence of an acid such as aqueous hydrochloric acid and/or hydroformic acid or, (3) by conversion to the alkyl ester by known methods (see Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Vol. XV (1974)).
  • the iso- and isothio-cyanates of Formula 1 are known or can be prepared by known methods.
  • Another method for preparing of compounds of Formula la which is outlined in Scheme 3 involves contacting an iso- or isothio-cyanate of Formula 1 with a piperidine nitrile of Formula 5, optionally in the presence of an acid acceptor and optionally in the presence of a solvent, to form a urea of Formula 6.
  • the urea of Formula 6 so obtained is then hydrolyzed with aqueous acid or base to give the acid of Formula 7, and then cyclized by dehydration to form the bicyclic hydantoin of Formula la.
  • treatment of nitriles of Formula 6 with aqueous acid provides the bicyclic hydantoins of Formula la directly.
  • R 1 and/or R 2 are more conveniently accomplished after cyclization to form the bicyclic hydantoin.
  • an alcohol of Formula lb can be fluorinated with DAST (diethylaminosulfur trifluoride) to give a fluoride of Formula Ic. Fluorination of the alcohol with DAST at a temperature between about -78°C and 100°C in an inert solvent such as dichloromethane affords the fluoride of Formula Ic.
  • DAST diethylaminosulfur trifluoride
  • bicyclic hydantoins of Formula 8 can be prepared using the methods described above wherein the R 4 group on Q is protected with a suitable group T (Scheme 5, for suitable protecting groups see T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley and Sons, Inc., New York, (1991)).
  • T suitable protecting groups see T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley and Sons, Inc., New York, (1991)).
  • the amino amide of Formula 9 is treated with trimethylsilyl isothiocyanate to afford the N-trimethylsilyl bicyclic hydantoin. Hydrolysis of the trimethylsilyl group with aqueous acid affords the compound of Formula If. Similar methods for preparing guanidines are taught in Barton, D. and Ollis, W. D., in Comprehensive Organic Chemistry, Vol. 4; Sammes, P. G., Ed.; Pergamon, New York, (1979); p 1116.
  • the amides of Formula 9 can be prepared by treating the corresponding carboxylic acid or ester with the aniline Q-NH 2 and a trialkylaluminum reagent (e.g.,
  • a non-coordinating solvent such as an aromatic hydrocarbon (e.g., benzene and toluene) or halogenated hydrocarbon (e.g., methylene chloride, chloroform, carbon tetrachloride, and dichlorobutane)
  • aromatic hydrocarbon e.g., benzene and toluene
  • halogenated hydrocarbon e.g., methylene chloride, chloroform, carbon tetrachloride, and dichlorobutane
  • the amides of Formula 9 are isolated by extraction into an organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Purification can be accomplished by chromatography or recrystallization.
  • Compounds of Formula 2 are either known or can be prepared from known compounds by known procedures.
  • the chloro, bromo, and iodo R 1 -substituted compounds of Formula 2 can be prepared from the alcohol using methods known to those skilled in the art.
  • the hydroxy group in compounds can be acylated by known methods to prepare the alkylcarbonyloxy and haloalkylcarbonyloxy derivatives.
  • the epoxide of Formula 2b can be prepared from the alkene by epoxidation, for example using m-chloroperoxybenzoic acid in methylene chloride.
  • the ketones of Formulae 2a and 2d are known and can be prepared from the epoxide of Formula 2b by reduction to give the alcohols of Formulae 2c and 2e followed by oxidation with, for example, pyridinium chlorochromate.
  • G. J. Hanson and M. A. Russell, Tetrahedron Lett., (1989), 30, 5751-5754 discusses the preparation of compounds of Formulae 2a and 2b.
  • P. D. Bailey and J. S. Bryans, Tetrahedron Lett., (1988), 29, 2231-2234 discusses compounds of Formula 2e and their conversion to other compounds of Formula 2.
  • alcohols of Formula 2c can be prepared as shown in Scheme 8.
  • 4-Hydroxypiperidine (10) is commercially available from Aldrich Chemical Co., Milwaukee, Wisconsin.
  • the piperidine 10 is treated with HOC1 and NaOMe to afford the corresponding imine followed by the addition of HCN to afford the nitrile 5 a.
  • Geminally substituted difluoro compounds of Formula 2 can be prepared by treating the ketones of Formula 2a and 2d with DAST as described above.
  • Compounds of Formula 2 wherein R 1 is F and R 2 is OH and R 1 and R 2 are bound to adjacent carbon atoms can be obtained by treating the epoxide of Formula 2b with DAST.
  • a mixture of isomeric fluorohydrins is obtained, and the isomers can be separated by chromatography.
  • protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products.
  • the use and choice of the protecting group will be apparent to one skilled in chemical synthesis.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and/or a surfactant wherein the formulation is consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and
  • 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.
  • 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, montmorillinite, 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
  • the compounds of Formula I are active herbicides for selective and/or general broadleaf and grass weed control in plantation crops including coffee, cocoa, oil palm, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, rubber, pineapple and loblolly pine. Preferred is the method of using compounds of Formula I in sugarcane, citrus, grapes, and fruit trees.
  • the compounds of Formula I can be applied as a preemergence or postemergence treatment using techniques such as banding, directed sprays, or broadcast applications. By selecting the appropriate rate which would be apparent to one skilled in the art, the compounds of Formula I can be used in areas where control of vegetation is desired, such as around fuel storage tanks, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures and in fence rows.
  • the compounds of Formula I can be used for selective weed control in plantation crops such as citrus, sugarcane, coffee, oil palm, rubber, cocoa, grapes, fruit trees, and pineapple.
  • plantation crops such as citrus, sugarcane, coffee, oil palm, rubber, cocoa, grapes, fruit trees, and pineapple.
  • the compounds of this invention are used at 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha rate.
  • One skilled in the art can select the proper rates for a given situation.
  • Compositions comprising the active compounds of Formula I are generally used alone or in combination with other commercial herbicides, insecticides or fungicides.
  • the compounds of Formula I are particularly useful in combinations with other herbicides for total vegetation control in plantation crops.
  • Examples of other herbicides with which compounds of Formula I can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid,
  • 1,2-dihydropyridazine-3,6-dione molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynach
  • a1 H-NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, ( ⁇ )-pentet, (m)-multiplet, (bs)-broad singlet, (dd)-doublet of doublets, (dm)-doublet of multiplets.
  • Morningglory 6 4 1 1 4 3 2 0

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'herbicides de formule (I) ainsi que leurs N-oxydes et leurs sels à usage agricole correspondants, formule dans laquelle R1, R2, Q et G sont tel que définis dans le texte. Des herbicides comprenant des composés de formule (I) constituent des désherbants à large spectre convenant pour les agrumes, la canne à sucre, les caféiers, les bananiers, les palmiers à huile, les pins à encens, les hévéas, les cacoïers, la vigne, le plantain, les ananas, les arbres fruitiers, les arbres à noix, etc.
PCT/US1995/002665 1994-03-01 1995-02-28 Hydantoïnes bicycliques herbicides WO1995023509A1 (fr)

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US20402794A 1994-03-01 1994-03-01
US08/204,027 1994-03-01

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6060432A (en) * 1995-10-25 2000-05-09 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
US6355799B1 (en) 1997-10-27 2002-03-12 Isk Americas Incorporated Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
WO2002008227A3 (fr) * 2000-07-21 2002-08-29 Lion Bioscience Ag Derives d'hydantoine bicycliques et bibliotheques combinatoires de ces derniers
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0211805A2 (fr) * 1985-07-24 1987-02-25 Ciba-Geigy Ag N-(2-fluorophényl)-azolidines
EP0349748A1 (fr) * 1988-06-08 1990-01-10 Bayer Ag N-aryl-hétérocycles substitués contenant de l'azote
EP0493323A1 (fr) * 1990-12-18 1992-07-01 Sandoz Ltd. Composés d'hydantoine
WO1993008689A1 (fr) * 1991-11-05 1993-05-13 Schering Aktiengesellschaft Compositions herbicides a activite synergique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0211805A2 (fr) * 1985-07-24 1987-02-25 Ciba-Geigy Ag N-(2-fluorophényl)-azolidines
EP0349748A1 (fr) * 1988-06-08 1990-01-10 Bayer Ag N-aryl-hétérocycles substitués contenant de l'azote
EP0493323A1 (fr) * 1990-12-18 1992-07-01 Sandoz Ltd. Composés d'hydantoine
WO1993008689A1 (fr) * 1991-11-05 1993-05-13 Schering Aktiengesellschaft Compositions herbicides a activite synergique

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6060432A (en) * 1995-10-25 2000-05-09 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
US6355799B1 (en) 1997-10-27 2002-03-12 Isk Americas Incorporated Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
US6545161B2 (en) 1997-10-27 2003-04-08 Isk Americas Incorporated Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
USRE39590E1 (en) * 1997-10-27 2007-04-24 Isk Americas Incorporated Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
WO2002008227A3 (fr) * 2000-07-21 2002-08-29 Lion Bioscience Ag Derives d'hydantoine bicycliques et bibliotheques combinatoires de ces derniers
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides

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