WO1997018712A1 - Composition herbicide - Google Patents

Composition herbicide Download PDF

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Publication number
WO1997018712A1
WO1997018712A1 PCT/EP1996/004914 EP9604914W WO9718712A1 WO 1997018712 A1 WO1997018712 A1 WO 1997018712A1 EP 9604914 W EP9604914 W EP 9604914W WO 9718712 A1 WO9718712 A1 WO 9718712A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
formula
fluorine
halogen
Prior art date
Application number
PCT/EP1996/004914
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English (en)
Inventor
Jutta Glock
Original Assignee
Novartis Ag
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 Novartis Ag filed Critical Novartis Ag
Priority to EA199800469A priority Critical patent/EA001418B1/ru
Priority to CA 2236802 priority patent/CA2236802C/fr
Priority to EP96938166A priority patent/EP0863708A1/fr
Priority to US09/068,877 priority patent/US7071146B1/en
Priority to AU75691/96A priority patent/AU719770B2/en
Publication of WO1997018712A1 publication Critical patent/WO1997018712A1/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
    • 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<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to novel selectively herbicidal compositions for controlling grasses and weeds in crops of useful plants, in particular in cereal and rice crops, which comprise a herbicide and a safener (antidote) and which protect the useful plants, but not the weeds, against the phytotoxic activity of the herbicide, and to the use of this composition for controlling weeds in crops of useful plants.
  • a herbicide and a safener antidote
  • a selectively herbicidal composition which comprises, besides customary inert formulation auxiliaries such as carriers, solvents and wetting agents, as active ingredient a mixture of a) a herbicidally active amount of a herbicide selected from the group consisting of the compounds of the formula la
  • R is hydrogen or fluorine and/or Ic
  • R 0 ⁇ o is hydrogen, CrCealkyl or C ⁇ -C 8 alkyl which is substituted by CrCealkoxy or C 3 -
  • X 2 is hydrogen or chlorine, of a compound of the formula llb ⁇
  • E is nitrogen or methine
  • Ri ⁇ is - CCI 3 or phenyl which is unsubstituted or substituted by halogen
  • R 12 and R 13 independently of one another are hydrogen or halogen
  • R1 is CrC 4 alkyl, of a compound of the formula llb 2
  • R 12 and R 13 have the abovementioned meanings and
  • Ree, Re7 and R ⁇ independently of one another are C 1 -C 4 alkyl
  • R 5 and R 26 independently of one another are hydrogen, C ⁇ -C 8 alkyl, C 3 -C ⁇ cycloalkyl, C 3 -
  • C 4 alkoxy or can be interrupted by oxygen, sulfur, SO, SO 2 , NH or -N(C C 4 alkyl)-,
  • R 27 is hydrogen or d-C alkyl
  • R aa is hydrogen, halogen, cyano, trifluoromethyl, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 alkoxy, d-
  • R g is hydrogen, halogen, cyano, nitro, CrC 4 alkyl, C C 4 haloalkyl, CrC alkylthio,
  • Rbb and R h independently of one another are hydrogen, halogen, d-C 4 alkyl, trifluoromethyl, d-C 6 alkoxy, d-C 6 alkylthio or -COOR,;
  • R c is hydrogen, halogen, nitro, d-C alkyl or methoxy
  • R d is hydrogen, halogen, nitro, d-C 4 alkyl, d-C 4 alkoxy, C C 4 alkylthio, C C 4 alkylsulfinyl, d-C 4 alkylsulfonyl, -COOR, or
  • R e is hydrogen, halogen, C C 4 alkyl, -COOR,, trifluoromethyl or methoxy, or R d and R e together form a C 3 -C 4 alkylene bridge;
  • Rt is hydrogen, halogen or d-C alkyl
  • R x and R y independently of one another are hydrogen, halogen, d-C alkyl, d-dalkoxy,
  • Ri, R k and R m independently of one another are hydrogen or C C 4 alkyl; or R k and R m together form a C 4 -C 6 alkylene bridge which can be interrupted by oxygen, NH or -N(C C 4 alkyl)-;
  • R n is d-C 4 alkyl, phenyl, or phenyl which is substituted by halogen, d-C 4 alkyl, methoxy, nitro or trifluoromethyl;
  • R 28 is hydrogen, C C 10 alkyl, d-C alkoxy-C ⁇ -C alkyl, C ⁇ -C 4 alkylthio-d-C 4 alkyl, di- d-dalkylamino-d-dalkyl, halo-d-C ⁇ alkyl, C 2 -C ⁇ alkenyl, halo-C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dcycloalkyl, halo-d-Crcycloalkyl, d-C 8 alkylcarbonyl, allylcarbonyl, C3-C Cycloalkylcarbonyl, benzovl which is unsubstituted or up to trisubstituted on the phenyl ring by identical or different substituents from the series consisting of halogen, d-C alkyl, halo-C ⁇ -C -alkyl, halo-C ⁇ -C 4 alkoxy or
  • R 33 and R ⁇ independently of one another are d-C 6 alkyl or C 2 -C 6 alkenyl; or R 33 and R34
  • R 3 an R 3 ⁇ independently of one another are hydrogen or d-C 6 alkyl
  • R37 and R 38 independently of one another are C ⁇ -C 4 alkyl, or R 37 and R ⁇ together are -(CH 2 ) 5 -;
  • R 39 is hydrogen, d-C alkyl or
  • R 4 o, R 4 , R 42 , R ⁇ , R44, R 5, R46, R47, R48, 4 9, Roso, R511 R52, R53, 54 and R55 independently of one another are hydrogen or C ⁇ -C 4 alkyl; of a compound of the formula I If
  • Re 3 is hydrogen or chlorine
  • R M is cyano or trifluoromethyl, or of a compound of the formula Ilg
  • R 65 is hydrogen or methyl.
  • the invention also embraces the agronomically tolerated salts which the compounds of the formulae la, lb and Ic can form, for example with amines, alkali metal bases and alkaline earth metal bases or quaternary ammonium bases.
  • Preferred salt formers amongst the alkali metal hydroxides and alkaline earth metal hydroxides are the hydroxides of lithium, sodium, potassium, magnesium or calcium, but in particular those of sodium or potassium.
  • Examples of amines which are suitable for ammonium salt formation are not only ammonia, but also primary, secondary and tertiary C C ⁇ ⁇ alkylam ⁇ nes, C 1 -C hydroxyalkylammes and C 2 -C 4 alkoxyalkylamines for example methylamine, ethylamine, n-propylamine, iso- propylamine, the four isomeric butylamine, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecy
  • alkyl groups in the definitions of substituents in the compounds of the formulae Ila to Ilg can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and pentyl, hexyl, heptyl, octyl, nonyl, decyl and their branched isomers.
  • halogen in particular fluorine, chlorine or bromine
  • alkoxy, thioalkyl, cycloalkyl, phenyl, amino, acyl (for example R 8 CO-) or oxo (O ).
  • Suitable alkoxy, thioalkyl, haloalkyl and haloalkoxy groups are derived from the alkyl groups mentioned.
  • Examples of unsaturated groups of substituents are ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl and isomers which differ by the different position of the unsaturated bond, or bonds, in the molecule, isomers which contain branchings, and, in the case of the alkenes, cis and trans isomers.
  • alkenyloxy, alkynyloxy, haloalkenyl and haloalkenyloxy groups can be derived from the alkyl groups mentioned.
  • Cycloalkyl groups embrace, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Corresponding cycloalkenes can be mono- or polyunsaturated
  • composition according to the invention comprises, as herbicide, either the compound of the formula la or Id and, as safener, the compound of the formula Ila in which X 2 is chlorine and R0 1 0 is1-methylhexyl.
  • compositions according to the present invention comprise, as safener, a compound of the formula Ila, llbi, llb 2 or He.
  • compositions which comprise, as safener, a compound of the formula lib ! or llb 2 are preferred.
  • compositions comprises, as safener, a compound of the formula Ila, and in particular such a compound of the formula Ila, in which X 2 is chlorine and R 0 ⁇ o is -CH(CH 3 )C 5 H ⁇ n.
  • Herbicidal compositions according to the invention which are very especially important are those which comprise one of the combinations of active ingredients below: la + 4.01 ; la + 4.02; la + 4.03; la + 4.04; lb, where R is hydrogen, + 4.01 ; lb, where R is hydrogen, + 4.02; lb, where R is hydrogen, + 4.03; lb, where R is hydrogen, + 4.04; lb, where R is fluorine, + 4.01 ; lb, where R is fluorine, + 4.02; lb.
  • R is fluorine, + 4.03; lb, where R is fluorine, + 4.04; la + 5.01 ; la + 5.02; la + 5.03; la + 5.04; la + 5.05; la + 5.06; la + 5.07; la + 5.08; lb, where
  • R is hydrogen, + 5.01 ; lb, where R is hydrogen, + 5.02; lb, where R is hydrogen, + 5.03; lb, where R is hydrogen, + 5.04; lb, where R is hydrogen, + 5.05; lb, where R is hydrogen,
  • the invention also relates to a method for the selective control of weeds in crops of useful plants which consists in treating the useful plants, their seeds or vegetative propagation material or the area on which they are grown either simultaneously or separately with a herbicidally active amount of the herbicide of the formula la and/or lb and a herbicidally antagonistically active amount of the safener of the formula II.
  • Suitable crop plants which can be protected by the safeners of the formula II against the damaging action of the abovementioned herbicides are, in particular, cereals and rice. Crops are also to be understood as meaning those which have been made tolerant to herbicides or classes of herbicides by means of conventional breeding or genetic engineering methods.
  • the weeds to be controlled can be either monocotyledon or dicotyledon weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagitta a, Bro us, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagitta a, Bro us, Alopecurus, Sorghum halepense, Rottboellia, Cyper
  • “Areas on which they grow” are the areas of soil on which the crop plants grow already or which are sown with the seed of these crop plants, but also the soils intended to be planted with these crop plants.
  • a safener of the formula II can be employed for pretreating the seed of the crop plant (seed dressing or treatment of propagation material) or incorporated into the soil before or after sowing.
  • seed dressing or treatment of propagation material can also be applied alone or together with the herbicide once the plants have emerged.
  • Treatment of the plants or of the seed with the safener can therefore be effected in principle independently of the point in time at which the herbicide is applied.
  • the plant can also be treated by simultaneously applying herbicide and safener (for example as a tank mix).
  • the application of safener to be applied relative to the herbicide depends largely on the type of application.
  • the ratio of herbicide to safener is, as a rule, from 1 :100 to 1 :1 , preferably 1 :50 to 5:1.
  • 0.001 to 5.0 kg of safener/ha preferably 0.001 to 0.5 kg of safener/ha, are applied for field treatment.
  • the rates of application of herbicide are between 0.001 and 2 kg/ha, but preferably between 0.005 to 1 kg/ha.
  • compositions according to the invention are suitable for all application methods conventionally used in agriculture, for example pre-emergence application, post- emergence application and seed dressing.
  • seed dressing 0.001 to 10 g of safener/kg of seed, preferably 0.05 to 2 g of safener/kg of seed, are generally applied.
  • safener solutions which comprise the active ingredient at a concentration of from 1 to 10000, preferably from 100 to 1000, ppm.
  • the safeners of the formula II or combinations of these safeners with the herbicides of the formula la and/or lb and/or Ic are expediently processed together with the auxiliaries conventionally used in the art of formulation to give formulations, for example emulsion concentrates, spreadable pastes, directly sprayable or diiutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • the formulations are prepared in a known manner, for example by intimately mixing and/or grinding the active ingredients with liquid or solid formulation auxiliaries, for example solvents or solid carriers.
  • surface-active compounds (surfactants) can additionally be used in the preparation of the formulations.
  • aromatic hydrocarbons preferably the fractions C 8 to C 1 2, for example xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols or else their ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethylformamide, and epoxidized or unepoxidized vegetable oils such as epoxidized coconut oil or soya oil; or water.
  • aromatic hydrocarbons preferably the fractions C 8 to C 1 2, for example xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl phthal
  • Solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as caleite, talc, kaolin, montmorillonite or attapulgite.
  • ground natural minerals such as caleite, talc, kaolin, montmorillonite or attapulgite.
  • highly-disperse silicic acid or highly- disperse absorptive polymers may also be added.
  • Suitable particulate, adsorptive carriers for granules are porous types, for example pumice, brick grit, sepiolite or bentonite, and examples of non-sorptive carrier materials are caleite or sand.
  • Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, non-ionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties.
  • Suitable anionic surfactants can be so-called water-soluble soaps, as well as water-soluble synthetic surface-active compounds.
  • Soaps which may be mentioned are the alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (C 10 -C 22 ), for example the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained from, for example, coconut oil or tallow oil.
  • the fatty acid methyltauride salts may also be mentioned.
  • the fatty alcohol sulfonates or fatty alcohol sulfates are present in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts and have an alkyl radical of 8 to 22 C atoms, alkyl also embracing the alkyl moiety of acyl radicals, for example the sodium or calcium salts of lignosulfonic acid, of the dodecylsutfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids.
  • This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated and benzimidazole derivatives have preferably two sulfonic acid groups and a fatty acid radical with approximately 8-22 C atoms.
  • Alkylarylsulfonates are, for example, the sodium salts, calcium salts or triethanolamine salts of dodeeylbenzenesulfonic acid, of dibutylnaphthalene sulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate.
  • Suitable phosphates for example salts of the phosphoric ester of a p-nonylphenol/(4-14)- ethyleneoxide adduct, or phospholipids, are furthermore also suitable.
  • Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, and these derivatives can have 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to18 carbon atoms in the alkyl radical of the alkylphenol.
  • non-ionic surfactants are the water-soluble adducts of polyethylene oxide to polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol which have 1 to 10 carbon atoms in the alkyl chain and 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
  • the compounds mentioned normally have 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants examples include nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/ polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.
  • the cationic surfactants are mainly quaternary ammonium salts which have, as N substituents, at least one alkyl radical of 8 to 22 C atoms and, as further substituents, lower, halogenated or unhalogenated alkyl, benzyl or lower hydroxyalkyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyl trimethylammonium chloride and benzyl di(2-chloroethyl)ethyl ammonium bromide.
  • the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient mixture of the compound of the formula la and/or lb and/or Ic with the compounds of the formulae II, 1 to 99.9% by weight of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
  • compositions are normally preferred as commercially available goods, the consumer uses, as a rule, dilute compositions.
  • compositions can also comprise other additives such as stabilizers, for example epoxidized or unepoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.
  • stabilizers for example epoxidized or unepoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil)
  • antifoams for example silicone oil
  • preservatives for example silicone oil
  • viscosity regulators binders
  • tackifiers tackifiers
  • fertilizers or other active ingredients.
  • Seed dressing a) Dressing of the seeds with an active ingredient of the formula II, formulated as a wettable powder, by shaking in a container until the active ingredient is distributed uniformly on the seed surface (dry seed treatment). Approximately 1 to 500 g of active ingredient of the formula II (4 g to 2 kg of wettable powder) are used per 100 kg of seed.
  • Seed dressing by immersing the seed in a mixture comprising 100-1000 ppm of active ingredient of the formula II for 1 to 72 hours, if desired followed by drying the seeds (immersion treatment).
  • seed dressing or treatment of the seed kernel which has begun to germinate are the preferred application methods because the treatment with active ingredient is directed entirely at the target crop.
  • 1 to 1000 g of antidote preferably 5 to 250 g of antidote, are used per 100 kg of seed, it being possible to deviate beneath or beyond the limit concentrations given, depending on the methodology, which also allows the addition of other active ingredients or micronutrients (repeated treatment).
  • a liquid formulation of a mixture of antidote and herbicide (mutual weight ratio between 10:1 and 1 :100) is used, the rate of application of herbicide being 0.005 to 5.0 kg per hectare.
  • Such tank mixes are applied before or after sowing.
  • the safener is introduced into the open, seeded seed furrow in the form of an emulsion concentrate, wettable powder or granules. After the seed furrow has been covered, the herbicide is applied pre-emergence in the customary manner.
  • the active ingredient of the formula II is applied, as a solution, to mineral carriers for granules or to polymerized granules (urea/formaldehyde) and dried. If desired, a coating may be applied (coated granules) which allows the active ingredient to be released over a given period at a particular dosage rate.
  • Active ingredient mixture 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Active ingredient mixture 5 to 75 %, preferably 10 to 50 %
  • Surfactant 1 to 40 %, preferably 2 to 30 %
  • Wettable powders Active ingredient mixture: 0.5 to 90 %, preferably 1 to 80 %
  • Surfactant 0.5 to 20 %, preferably 1 to 15 %
  • Solid carrier material 5 to 95 %, preferably 15 to 90 %
  • Active ingredient mixture 0J to 30 %, preferably 0J to 15 %
  • Solid carrier 99.5 to 70 %, preferably 97 to 85 %
  • Active ingredient mixture 5 % 10 % 50 %
  • Aromatic hydrocarbon 75 % 60 % mixture
  • the solutions are suitable for use in the form of microdrops.
  • Active ingredient mixture 5% 25% 50% 80% Sodium lignosulfonate 4% 3% Sodium lauryl sulfate 2% 3% 4% Sodium diisobutylnaphthylene- 6% 5% 6% sulfonate 10 %
  • the active ingredient is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • Active ingredient mixture Highly disperse silica Inorganic carrier material (0 0.1 - 1 mm), for example CaCO 3 or SiO
  • the active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated in vacuo.
  • Active ingredient mixture Polyethylene glycol MW 200 Highly disperse silica Inorganic carrier material (0 0.1 - 1 mm), for example CaC0 3 or SiO 2
  • the finely ground active ingredient is applied uniformly to the carrier material which has been moistened with polyethylene glycol. This gives dust-free coated granules.
  • the active ingredient is mixed with the additives, and the mixture is ground and moistened with water. This mixture is extruded and subsequently dried in a stream of air.
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.
  • Active ingredient mixture 3 % 10 % 25 % 50 %
  • Example B1 Post-emergence applications of mixtures of a herbicide of the formula la and/or lb and/or Ic with a safener of the formulae Ila to Ilg to cereals:

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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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Cette composition à activité herbicide sélective comprend en tant que principe actif, outre les auxiliaires de formulation inertes habituels, un mélange de: a) une dose active d'un herbicide choisi dans le groupe constitué par les composés de la formule (Ia) et/ou (Ib), dans laquelle R représente hydrogène ou fluor, et/ou (Ic), ou d'un sel des composés des formules (Ia) et/ou (Ib) et/ou (Ic), et b) une dose à activité antagoniste par rapport à l'herbicide d'un composé de la formule (IIa), d'un composé de la formule (IIb1), d'un composé de la formule (IIb2), d'un composé de la formule (IIc), d'un composé de la formule (IIe), d'un composé de la formule (IIf), ou d'un composé de la formule (IIg), dans lesquelles les substituants possèdent les notations données dans la revendication 1.
PCT/EP1996/004914 1995-11-23 1996-11-11 Composition herbicide WO1997018712A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EA199800469A EA001418B1 (ru) 1995-11-23 1996-11-11 Гербицидная композиция
CA 2236802 CA2236802C (fr) 1995-11-23 1996-11-11 Composition herbicide
EP96938166A EP0863708A1 (fr) 1995-11-23 1996-11-11 Composition herbicide
US09/068,877 US7071146B1 (en) 1996-11-11 1996-11-11 Herbicidal composition
AU75691/96A AU719770B2 (en) 1995-11-23 1996-11-11 Herbicidal composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH331495 1995-11-23
CH3314/95 1995-11-23

Publications (1)

Publication Number Publication Date
WO1997018712A1 true WO1997018712A1 (fr) 1997-05-29

Family

ID=4253318

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/004914 WO1997018712A1 (fr) 1995-11-23 1996-11-11 Composition herbicide

Country Status (7)

Country Link
EP (1) EP0863708A1 (fr)
CN (1) CN1202800A (fr)
AR (1) AR004736A1 (fr)
AU (1) AU719770B2 (fr)
EA (1) EA001418B1 (fr)
WO (1) WO1997018712A1 (fr)
ZA (1) ZA969798B (fr)

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WO1998011781A1 (fr) * 1996-09-19 1998-03-26 Hoechst Schering Agrevo Gmbh Associations d'herbicides sulfonylures et de phytoprotecteurs
US6376424B1 (en) 1998-01-21 2002-04-23 Syngenta Crop Protection, Inc. Herbicidal composition
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CN103392721B (zh) * 2013-06-30 2016-12-28 广东中迅农科股份有限公司 含有环丙嘧磺隆和嘧草醚的除草组合物

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EP1468609A1 (fr) * 1996-09-19 2004-10-20 Bayer CropScience GmbH Associations d'herbicides sulfonylures et de phytoprotecteurs
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US6376424B1 (en) 1998-01-21 2002-04-23 Syngenta Crop Protection, Inc. Herbicidal composition
US9782408B2 (en) 2014-10-06 2017-10-10 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US10258624B2 (en) 2014-10-06 2019-04-16 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US11426407B2 (en) 2014-10-06 2022-08-30 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US10758534B2 (en) 2014-10-06 2020-09-01 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US10738030B2 (en) 2016-03-31 2020-08-11 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US11186566B2 (en) 2016-09-30 2021-11-30 Vertex Pharmaceuticals Incorporated Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US10570115B2 (en) 2016-09-30 2020-02-25 Vertex Pharmaceuticals Incorporated Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US10793547B2 (en) 2016-12-09 2020-10-06 Vertex Pharmaceuticals Incorporated Modulator of the cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US11453655B2 (en) 2016-12-09 2022-09-27 Vertex Pharmaceuticals Incorporated Modulator of the cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US11253509B2 (en) 2017-06-08 2022-02-22 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
US11517564B2 (en) 2017-07-17 2022-12-06 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
US11434201B2 (en) 2017-08-02 2022-09-06 Vertex Pharmaceuticals Incorporated Processes for preparing pyrrolidine compounds
US11155533B2 (en) 2017-10-19 2021-10-26 Vertex Pharmaceuticals Incorporated Crystalline forms and compositions of CFTR modulators
US10654829B2 (en) 2017-10-19 2020-05-19 Vertex Pharmaceuticals Incorporated Crystalline forms and compositions of CFTR modulators
US11465985B2 (en) 2017-12-08 2022-10-11 Vertex Pharmaceuticals Incorporated Processes for making modulators of cystic fibrosis transmembrane conductance regulator
US11179367B2 (en) 2018-02-05 2021-11-23 Vertex Pharmaceuticals Incorporated Pharmaceutical compositions for treating cystic fibrosis
US11414439B2 (en) 2018-04-13 2022-08-16 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator

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EA199800469A1 (ru) 1998-12-24
AR004736A1 (es) 1999-03-10
ZA969798B (en) 1997-07-21
AU7569196A (en) 1997-06-11
EA001418B1 (ru) 2001-02-26
AU719770B2 (en) 2000-05-18
EP0863708A1 (fr) 1998-09-16
CN1202800A (zh) 1998-12-23

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