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WO1998034480A1 - Agent herbicide - Google Patents

Agent herbicide Download PDF

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Publication number
WO1998034480A1
WO1998034480A1 PCT/EP1998/000621 EP9800621W WO9834480A1 WO 1998034480 A1 WO1998034480 A1 WO 1998034480A1 EP 9800621 W EP9800621 W EP 9800621W WO 9834480 A1 WO9834480 A1 WO 9834480A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
alkyl
herbicide
crops
Prior art date
Application number
PCT/EP1998/000621
Other languages
German (de)
English (en)
Inventor
Jutta Glock
Elmar Kerber
Willy Rüegg
Original Assignee
Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft Mbh
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, Novartis-Erfindungen Verwaltungsgesellschaft Mbh filed Critical Novartis Ag
Priority to AU66204/98A priority Critical patent/AU6620498A/en
Publication of WO1998034480A1 publication Critical patent/WO1998034480A1/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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

Definitions

  • the present invention relates to new selective herbicidal compositions for controlling grasses and weeds in crops of useful plants, in particular in crops of cereals, which contain a herbicide and a safener (antidote, antidote) and which contain the useful plants but not the weeds before the phytotoxic Preserve the effect of the herbicide, and the use of this agent for weed control in crops.
  • the cultivated plants are also damaged to a considerable extent.
  • the invention thus proposes a selective herbicidal composition which is characterized in that, in addition to customary inert formulation auxiliaries such as carriers, solvents and wetting agents, it is a mixture of active ingredients a) a herbicidally effective amount of a herbicide of the formula
  • X is halogen and Y is -S (O) mR or a radical of the formula in which RCC -
  • Alkyl or C 2 -C 4 alkenyl, Z is a direct chemical bond or CH 2 and m is 0, 1 or 2, where m is 0 when RC 2 -C 4 alkenyl, or a salt of the compound of the formula I , and b) a herbicide-antagonistically effective amount of a compound of the formula Ila
  • X 2 is hydrogen or chlorine, a compound of formula IIbi wherein
  • Ru is -CCI 3 or phenyl which is optionally substituted by halogen
  • R 12 and R 13 are independently hydrogen or halogen
  • R 14 is dC-alkyl, or a compound of the formula IIb 2
  • R 12 and R 13 have the meanings given above, and
  • Ree, ⁇ 7 and Re ⁇ are independently of one another C 1 -C 4 alkyl, contains.
  • the invention also includes the agronomically acceptable salts which the compounds of the formula I can form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • alkali and alkaline earth metal hydroxides as salt formers, the hydroxides of lithium, sodium, potassium, magnesium or calcium should be emphasized, but especially those of sodium or potassium.
  • Suitable amines for the formation of ammonium salt include both ammonia and also primary, secondary and tertiary C 1 -C 8 -alkylamines, CrC -hydroxyalkylamines and C 2 -C -alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methyl nonylamine, methyl -pentadecylamine, methyl-octadecyl
  • alkyl groups occurring in the substituent definitions of the compounds of the formulas I and IIa to IIb 2 can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and pentyl, hexyl, heptyl, octyl and branched isomers thereof.
  • These alkyl groups can carry further substituents such as. B. alkoxy or alkenyloxy.
  • Examples of unsaturated substituent groups are ethenyloxy, propenyloxy, butenyloxy, pentenyloxy, hexenyloxy, heptenyloxy and octenyloxy as well as isomers which differ in the different position of the unsaturated bond or bonds in the molecule, isomers which contain branches, and cis and trans isomers . If Z in the substituent Y is a direct chemical bond, the result is for
  • Y is a residue of the formula
  • substituted indicates, where possible in the corresponding group, not only single substitution but also multiple substitution.
  • compositions according to the present invention contain, as herbicide, a compound of the formula I in which X is bromine and Y is -SCH 3 .
  • Preferred agents according to the present invention contain, as safeners, a compound of the formula IIIa and in particular such a compound of the formula IIIa, in which X 2 is chlorine and roio -CH (CH3) C 5 H ⁇ n.
  • herbicidal compositions according to the invention which contain one of the active ingredient combinations 1.02 + 2.01; 1.15 + 2.01 or 1.16 + 2.01 contain:
  • the invention also relates to a process for the selective control of weeds in crops, which consists in that the crops, their seeds or cuttings or their cultivated area are treated simultaneously or separately with a herbicidally active amount of the herbicide of the formula I and a herbicidally antagonistically effective amount of the safener of the formula Ila to llb 2 treated.
  • Cereals preferably wheat, are particularly suitable as cultivated plants which can be protected by the safeners against the damaging action of the herbicides mentioned above. Cultures are also to be understood as 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 both monocot and dicot weeds, such as Brachiaria, Polygonum, Kochia, Stellaria, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Sci ⁇ us, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • monocot and dicot weeds such as Brachiaria, Polygonum, Kochia, Stellaria, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Sci ⁇ us, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rott
  • the cultivated areas are the soil areas already overgrown with the cultivated plants or supplied with the seeds of these cultivated plants, as well as the soils intended for cultivation with these cultivated plants.
  • a safener of the formula IIa to IIb 2 can be used for the pretreatment of the seed of the crop (dressing the seed or the cuttings) or added to the soil before or after the seed.
  • it can also be applied on its own or together with the herbicide after the plants have emerged.
  • the treatment of the plants or the seed with the safener can therefore in principle be carried out independently of the time of application of the herbicide.
  • the treatment of the plant can also be carried out by simultaneous application of herbicide and safener (for example as a tank mix).
  • the application rate of safener to herbicide largely depends on the type of application. In the case of field treatment, which is carried out either using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide, there is usually a ratio of heicide to safener of 1:10 to 10: 1 or 10: 1 to 2: 1 before.
  • 0.010 to 0.5 kg of safener / ha preferably 0.010 to 0.1 kg of safener / ha, are applied in the field treatment.
  • the application rates of herbicide are generally between 0.010 to 1 kg / ha, but preferably between 0.010 to 0.5 kg / ha.
  • the compositions according to the invention are suitable for all application methods customary in agriculture, such as, for example, pre-emergence application, post-emergence application and seed dressing. Post-emergence application (eg as a tank mix) is of particular importance.
  • safener solutions which contain the active compound in a concentration of 1 to 10,000, preferably 100 to 1000 ppm.
  • the safeners or combinations of these safeners with the herbicides of the formula are expediently processed into formulations together with the auxiliaries customary in formulation technology, e.g. to emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • the formulations are prepared in a known manner, e.g. by intimately mixing and / or grinding the active ingredients with liquid or solid formulation auxiliaries, e.g. Solvents or solid carriers.
  • surface-active compounds surfactants
  • surfactants can also be used in the preparation of the formulations.
  • Aromatic hydrocarbons preferably the fractions C ⁇ to C ⁇ 2 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, and their ethers and esters such as Ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N, N-dimethylformamide, and optionally epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.
  • Aromatic hydrocarbons preferably the fractions C ⁇ to C ⁇ 2 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioc
  • Natural rock flours such as calcite, talc, kaolin, montmorillonite or attapulgite, are generally used as solid carriers, for example for dusts and dispersible powders.
  • highly disperse silica or highly disperse absorbent polymers become.
  • Porous types such as pumice, broken bricks, sepiolite or bentonite can be used as granular, adsorbent granulate carriers, and non-so ⁇ tive carrier materials, such as calcite or sand.
  • a large number of pregranulated materials of inorganic or organic nature such as in particular dolomite or comminuted plant residues, can be used.
  • nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties are suitable as surface-active compounds.
  • Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.
  • Soaps which may be mentioned are the alkali metal, alkaline earth metal or optionally substituted ammonium salts of higher fatty acids (C10-C 22 ), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures which, for example, from coconut or Tallow oil can be extracted.
  • the fatty acid methyl taurine salts should also be mentioned.
  • the fatty alcohol sulfates or sulfates are usually present as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical having 8 to 22 carbon atoms, alkyl also including the alkyl part of acyl radicals, e.g. the Na or Ca salt of lignin sulfonic acid, dodecylsulfuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids.
  • This subheading also includes the salts of sulfuric acid esters and sulphonic acids from fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid residue with 8-22 carbon atoms.
  • Alkylarylsulfonates are e.g. the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a naphthalenesulfonic acid-formaldehyde condensation product.
  • Corresponding phosphates such as, for example, salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct or phospholipids, are also suitable.
  • Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • nonionic surfactants are the water-soluble polyethylene oxide adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol with 1 to 10 carbon atoms in the alkyl chain.
  • the compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate, are also suitable.
  • the cationic surfactants are primarily quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and have low, optionally halogenated alkyl, benzyl or low hydroxyalkyl radicals as further substituents.
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. the stearyl trimethyl ammonium chloride or the benzyl di (2-chloroethyl) ethyl ammonium bromide.
  • the herbicidal formulations usually contain 0.1 to 99% by weight, in particular 0.1 to 95 wt .-% of active ingredient mixture of the compound of formula I with the compounds of the formulas IIa to IIb 2, 1 to 99.9 wt.% a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant.
  • the agents can also contain other additives such as stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
  • stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
  • Seed dressing a) Dressing the seeds with an active ingredient formulated as a wettable powder by shaking in a vessel until uniform distribution on the seed surface (dry dressing). About 1 to 500 g of active ingredient (4 g to 2 kg of wettable powder) per 100 kg of seed are used.
  • the dressing of the seeds or the treatment of the germinated seedlings are naturally the preferred methods of application because the treatment of the active ingredient is completely aimed at the target culture.
  • 1 to 1000 g of antidote are used, preferably 5 to 250 g of antidote, per 100 kg of seed, whereby depending on the method, which also allows the addition of other active ingredients or micronutrients, it can deviate upwards or downwards from the specified limit concentrations (repeat stain).
  • a liquid processing of a mixture of antidote and herbicide (mutual ratio between 10: 1 and 1: 100) is used, the amount of herbicide applied 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 furrow as an emulsion concentrate, wettable powder or as granules. After covering the furrow, the herbicide is applied in the pre-emergence process in the usual way.
  • the active ingredient is applied in solution to mineral granulate carriers or polymerized granules (urea / formaldehyde) and dried. If necessary, a coating can be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
  • mineral granulate carriers or polymerized granules urea / formaldehyde
  • a coating can be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
  • Emulsifiable concentrates are:
  • Active ingredient mixture 1 to 90%, preferably 5 to 20% surface-active agent: 1 to 30%, preferably 10 to 20% liquid carrier: 5 to 94%, preferably 70 to 85%
  • Active ingredient mixture 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension concentrates:
  • Active ingredient mixture 5 to 75%, preferably 10 to 50%
  • Active ingredient mixture 0.5 to 90%, preferably 1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90%
  • Active ingredient mixture 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
  • Emulsion concentrates a) b) c) d)
  • Active ingredient mixture 5% 10% 25% 50 ° /
  • Active ingredient mixture 5% 10% 50% 90%
  • the solutions are suitable for use in the form of tiny drops.
  • Active ingredient mixture 5% 25% 50% 80%
  • the active ingredient is mixed well with the additives and ground well in a suitable grinder.
  • Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.
  • Active ingredient mixture 0.1% 5% 15%
  • the active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated off in vacuo.
  • Active ingredient mixture 0.1% 5% 15%
  • Polyethylene glycol MG 200 1.0% 2% 3%
  • Inorg. Backing material 98.0% 92% 80% (00.1 - 1 mm) such as CaCO 3 or SiO 2
  • the finely ground active ingredient is evenly applied in a mixer to the carrier material moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.
  • Active ingredient mixture 0.1% 3% 5% 15%
  • the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.
  • Active ingredient mixture 0.1% 1% 5%
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carrier substances and grinding them in a suitable mill.
  • Active ingredient mixture 3% 10% 25% 50%
  • the finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
  • Example B1 Post-emergent applications of mixtures of a herbicide of the formula I with a safener of the formulas 11a to 11b 2 in cereals Wheat is grown in plastic pots up to the 2-4 leaf stage under greenhouse conditions. At this stage, on the one hand the heicides of the formula I alone and also the mixture of the herbicides with a safener of the formulas 11a to 11b 2 are applied to the test plants. The application takes place as an aqueous suspension of the test substances with 500 I water / ha. The application rates for the heicides are 250, 125 and 60, g / ha. 17 days after the application is evaluated with a percentage scale. 100% means that the test plant has died; 0% means that no phytotoxic effect can be seen.
  • Alopecurus 100 100 70 100 100 70
  • Polygonum 100 100 85 100 100 85

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Agent herbicide sélectif renfermant, comme matière active, en plus des auxiliaires de formulation habituels, un mélange comprenant a) une quantité à activité herbicide, d'un herbicide de formule (I), dans laquelle X est un halogène et Y désigne -S(O)mR ou un reste de formule (II), où R désigne un alkyle en C1-C4 ou un alkényle en C2-C4, Z est une liaison chimique directe ou CH2 et m est égal à 0, 1 ou 2, m étant égal à 0 lorsque R est un alkényle en C2-C4, ou un sel du composé de formule (I), et b) une quantité à activité antagoniste-herbicide d'un composé de formule (IIa), dans laquelle R010 est l'oxygène, un alkyle en C1-C8 ou un alkyle en C1-C8 substitué par un alkoxy en C1-C6 ou par un alkényloxy en C3-C6, et X2 est l'hydrogène ou le chlore, et d'un composé de formule (IIb1), dans laquelle E désigne l'azote ou une méthine, R11-CCl3 ou un phényle éventuellement substitué par un halogène, R12 et R13 désignent, indépendamment l'un de l'autre, un hydrogène ou un halogène et R14 est un alkyle en C1-C4, ou d'un composé de formule (IIb2) dans laquelle R12 et R13 ont les significations précitées, et R66, R67 et R68 désignent, indépendamment l'un de l'autre, un alkyle en C1-C4.
PCT/EP1998/000621 1997-02-07 1998-02-05 Agent herbicide WO1998034480A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU66204/98A AU6620498A (en) 1997-02-07 1998-02-05 Herbicidal agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH27297 1997-02-07
CH272/97 1997-02-07

Publications (1)

Publication Number Publication Date
WO1998034480A1 true WO1998034480A1 (fr) 1998-08-13

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/000621 WO1998034480A1 (fr) 1997-02-07 1998-02-05 Agent herbicide

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AU (1) AU6620498A (fr)
WO (1) WO1998034480A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2350298A (en) * 1999-05-28 2000-11-29 Zeneca Ltd The safening of 2-benzoylcyclohexane-1,3-dione herbicides with 1-phenyl-1,2,4-triazole, 1-phenyl-pyrazolin-3-carboxylate & 8-oxy-quinoline derivatives
WO2002085120A3 (fr) * 2001-04-21 2003-02-20 Bayer Cropscience Gmbh Agents herbicides contenant des benzoylcyclohexanediones et des phytoprotecteurs
WO2003020033A1 (fr) * 2001-08-30 2003-03-13 Bayer Cropscience Ag Melanges herbicides a base d'arylcetones substituees
WO2008031507A3 (fr) * 2006-09-13 2009-04-16 Bayer Cropscience Ag Compositions herbicides à phytotoxicité réduite
WO2013176282A1 (fr) * 2012-05-22 2013-11-28 Ishihara Sangyo Kaisha, Ltd. Composition herbicide

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0551650A2 (fr) * 1991-12-31 1993-07-21 Hoechst Schering AgrEvo GmbH Combinaisons d'herbicides avec des agents protecteurs des plantes
WO1997045404A1 (fr) * 1996-05-30 1997-12-04 Hokko Chemical Industry Co., Ltd. Derives de cyclohexanedione et compositions herbicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0551650A2 (fr) * 1991-12-31 1993-07-21 Hoechst Schering AgrEvo GmbH Combinaisons d'herbicides avec des agents protecteurs des plantes
WO1997045404A1 (fr) * 1996-05-30 1997-12-04 Hokko Chemical Industry Co., Ltd. Derives de cyclohexanedione et compositions herbicides

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2350298A (en) * 1999-05-28 2000-11-29 Zeneca Ltd The safening of 2-benzoylcyclohexane-1,3-dione herbicides with 1-phenyl-1,2,4-triazole, 1-phenyl-pyrazolin-3-carboxylate & 8-oxy-quinoline derivatives
WO2002085120A3 (fr) * 2001-04-21 2003-02-20 Bayer Cropscience Gmbh Agents herbicides contenant des benzoylcyclohexanediones et des phytoprotecteurs
US6884757B2 (en) 2001-04-21 2005-04-26 Aventis Cropscience Gmbh Herbicides comprising benzoylcyclohexanediones and safeners
US7101827B2 (en) 2001-04-21 2006-09-05 Aventis Cropscience Gmbh Herbicides comprising benzoylcyclohexanediones and safeners
RU2311766C2 (ru) * 2001-04-21 2007-12-10 Байер Кропсайенс Гмбх Гербицидное средство, содержащее бензоилциклогександион и защитное средство
RU2311766C9 (ru) * 2001-04-21 2008-10-20 Байер Кропсайенс Гмбх Гербицидное средство, содержащее бензоилциклогександион и защитное средство
WO2003020033A1 (fr) * 2001-08-30 2003-03-13 Bayer Cropscience Ag Melanges herbicides a base d'arylcetones substituees
WO2008031507A3 (fr) * 2006-09-13 2009-04-16 Bayer Cropscience Ag Compositions herbicides à phytotoxicité réduite
KR101432627B1 (ko) 2006-09-13 2014-08-21 바이엘 크롭사이언스 아게 식물 독성이 감소된 제초제 조성물
WO2013176282A1 (fr) * 2012-05-22 2013-11-28 Ishihara Sangyo Kaisha, Ltd. Composition herbicide
JP2014001202A (ja) * 2012-05-22 2014-01-09 Ishihara Sangyo Kaisha Ltd 除草組成物

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