EP0786937A2 - Compositions herbicides - Google Patents

Compositions herbicides

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Publication number
EP0786937A2
EP0786937A2 EP95934134A EP95934134A EP0786937A2 EP 0786937 A2 EP0786937 A2 EP 0786937A2 EP 95934134 A EP95934134 A EP 95934134A EP 95934134 A EP95934134 A EP 95934134A EP 0786937 A2 EP0786937 A2 EP 0786937A2
Authority
EP
European Patent Office
Prior art keywords
substituted
unsubstituted
formula
alkyl
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP95934134A
Other languages
German (de)
English (en)
Inventor
Jutta Glock
Manfred Hudetz
Elmar Kerber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG, Novartis AG filed Critical Ciba Geigy AG
Publication of EP0786937A2 publication Critical patent/EP0786937A2/fr
Ceased legal-status Critical Current

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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
    • A01N43/48—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
    • A01N43/90—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

  • the present invention relates to a selective herbicidal composition for controlling grasses and weeds in crops of cultivated plants, especially in crops of maize and cereals, which composition comprises a herbicide and a safener (antidote) and protects the cultivated plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of said composition for controlling weeds in crops of cultivated plants.
  • the cultivated plants may also suffer severe damage owing to factors that include the concentration of the herbicide and the mode of application, the cultivated plant itself, the nature of the soil, and the climatic conditions such as exposure to light, temperature and rainfall.
  • EP-A-0 094 349 discloses quinoline derivatives that protect cultivated plants from the phytotoxic action of herbicides of specific substance classes including chloroacetanilides, phenoxypropioniate herbicides, ureas, triazines, carbamates or diphenyl ethers.
  • EP-A-0558 448 discloses l,5-diphenylpyrazole-3-carboxylic acid derivatives for protecting cultivated plants from the phytotoxic action of sulfonyl ureas.
  • the safeners selected from the two compound classes of the quinoline derivatives and 1 -pheny lazole-3-carboxylic acid derivatives are suitable for protecting cultivated plants from the phytotoxic action of 3-hydroxy-4-aryl-5- oxopyrazoline derivatives.
  • the invention provides a selective herbicidal composition
  • a selective herbicidal composition comprising, in addition to customary inert formulation assistants such as carriers, solvents and wetting agents, a mixture of a) a herbicidally effective amount of a herbicide of formula I
  • Rj is the ⁇ T T " , (R 4 ) n group; the substituents R 4 are each independently of one another halogen, nitro, cyano, C r C 4 alkyl, C ⁇ haloalkyl, C r C 10 alkoxy, C r C 4 haloalkoxy, C 3 -C 6 alkenyloxy, C 1 -C 4 alkoxy-C 2 -C 4 alkoxy, C 3 -C 6 alkynyloxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C alkylsulfinyl, ⁇ alkylsulfonyl, amino, C 1 -C 4 alkylamino or di-C 1 -C 4 alkylamino;
  • R 5 is the group; n is O, 1, 2, 3 or 4; m is 0 or 1, the sum of m and n being 0, 1, 2, 3 or 4; q is O, 1, 2 or 3;
  • X ! is oxygen, sulfur, -CH 2 - or -NCR )- ; the substituents Rg are each independently of one another C 1 -C 4 alkyl, halogen,
  • R 7 is hydrogen, C 1 -C 4 alkyl, formyl or C 1 -C 4 alkylcarbonyl;
  • a and B are each independently of the other hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or cycloalkyl, or substituted or unsubstituted aryl; or
  • a and B taken together, form the divalent radical of a saturated or unsaturated and unsubstituted or substituted mono-, bi-, tri- or polycyclic system;
  • G is hydrogen or a group -CO-R 18 (a), 22 (d), R 2 ⁇
  • L and M are each independently of the other oxygen or sulfur
  • R 18 is halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl, which may contain hetero atoms; unsubstituted or substituted phenyl, unsubstituted or substituted phenylalkyl, substituted heteroaryl, substituted phenoxyalkyl, or substituted heteroaryloxyalkyl;
  • R 19 is halogen-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or unsubstituted or substituted phenyl or benzyl;
  • R 0 , R 2 ⁇ and R 22 are each independently of one another unsubstituted or halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, alkynylthio or cycloalkylthio, or unsubstituted or substituted phenyl, phenoxy or phenylthio;
  • R- 23 and R 24 are each independently of the other hydrogen, unsubstituted or halogen-substituted alkyl, alkenyl, alkoxy or alkoxyalkyl, unsubstituted or substituted phenyl or benzyl; or
  • R 23 and R 24 taken together, form an alkenyl radical, which may contain oxygen as hetero atom;
  • X is a metal ion equivalent or an ammonium ion; as well as salts and diastereoisomers of the compounds of formula I;
  • R 10 is hydrogen, C r C 8 alkyl, or C r C 8 alkyl which is substituted by -Csalkoxy or
  • X is hydrogen or chloro; of a l-phenylazole-3-carboxylic acid derivative of formula ub
  • E is nitrogen or methine
  • R n is -CCI 3 or unsubstituted or halogen-substituted phenyl
  • R 12 and R 13 are each independently of the other hydrogen or halogen
  • R M is C 1 -C 4 alkyl; or of a compound of formula ⁇ bi
  • R 1 and R 13 have the meanings given above, and R ⁇ , R 67 and R ⁇ are each independently of one another C-i-C ⁇ alkyl.
  • alkyl, alkenyl and alkynyl groups contain, unless specifically mentioned, preferably 1 or 2 to 8 carbon atoms and may be straight-chain or branched, as also applies to the alkyl, alkenyl and alkynyl moiety of the haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, alkenyloxy, alkynyloxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkenylthio, alkynylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfonyl, alkylamino and dialkylamino groups.
  • alkyl groups occurring in the substituent definitions are typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, as well as the isomeric pentyls, hexyls, heptyls and octyls.
  • the alkyl groups by themselves or as moieties of other substituents preferably contain 1 to 8 carbon atoms.
  • halogen will be taken to mean fluoro, chloro, bromo and iodo, preferably fluoro, chloro and bromo.
  • Alkenyl will be typically vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-l-yl. Alkenyl radicals containing 2 to 8 carbon atoms in the chain are preferred. The alkenyl radicals are preferably linked via a saturated carbon atom to a hetero atom.
  • Alkynyl will typically be propargyl, but-2-yn-l-yl, 2-methylbutyn-2-yl, but-3-yn-2-yl and pent-4-yn-l-yl.
  • Alkynyl radicals containing 2 to 8 carbon atoms in the chain are preferred.
  • the alkynyl radicals are preferably linked via a saturated carbon atom to a hetero atom.
  • Haloalkyl radicals preferably contain 1 to 8 carbon atoms in the chain.
  • Haloalkyl is typically fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl. Trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl are preferred.
  • Alkoxy radicals preferably contain 1 to 6 carbon atoms in the chain.
  • Alkoxy is typically methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy as well as the pentoxy and hexyloxy isomers. Methoxy and ethoxy are preferred.
  • Alkylcarbonyl is preferably acetyl and propionyl.
  • Alkoxycarbonyl is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl. Methoxycarbonyl and ethoxycarbonyl are preferred.
  • Haloalkoxy radicals preferably contain 1 to 8 carbon atoms in the chain.
  • Haloalkoxy is typically fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy. Difluoromethoxy, 2-chloroethoxy and trifluoromethoxy are preferred.
  • Alkylthio radicals preferably contain 1 to 8 carbon atoms in the chain.
  • Alkylthio is typically methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio. Mmethylthio and ethylthio are preferred.
  • Alkylsulfinyl is methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulf ⁇ nyl, sec-butylsulfinyl, tert-butylsulfinyl. Methylsulfinyl and ethylsulfinyl are preferred.
  • Alkylsulfonyl is methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl. Methylsulfonyl and ethylsulfonyl are preferred.
  • Alkoxyalkoxy radicals preferably contain 1 to 8 carbon atoms in the chain.
  • Illustrative examples of alkoxyalkoxy are methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy and butoxybutoxy.
  • Alkylamino is typically methylamino, ethylamino, n-propylamino, isopropylamino and the isomeric butylamines.
  • Dialkylamino is typically dimethylamino, methy lethylamino, diethy lamino, n-propylmethylamino, dibutylamino and di-isopropylamino.
  • Alkylamino radicals containing 1 to 8 carbon atoms in the chain are preferred.
  • Alkoxyalkyl radicals preferably contain 1 to 8 carbon atoms.
  • Alkoxyalkyl is typically methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl and isopropoxyethyl.
  • Alkylthioalkyl radicals preferably contain 1 to 8 carbon atoms.
  • Alkylthioalkyl is typically methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl.
  • Cycloalkyl radicals preferably contain 3 to 8 ring carbon atoms, and are typically cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. These cycloalkyl radicals may be interrupted by hetero atoms such as oxygen atoms and/or sulfur atoms and/or nitrogen atoms.
  • Phenyl also as moiety of a substituent such as phenoxy, phenylthio, phenylalkyl, phenoxyalkyl, can generally be unsubstituted or substituted. The substituents may then be in ortho-, meta- and/or para-position. Preferred substituent positions are the ortho- and para-position to the ring linkage site. Preferred substituents are halogen, nitro, cyano, C r C 4 alkoxy, C 1 -C 4 haloalkoxy, C r C 4 alkylthio, C r C haloalkylthio, C ⁇ -C 4 alkyl and C,-C 4 haloalkyl.
  • a and B defined as aryl are ⁇ -naphthyl or ⁇ -naphthyl, preferably phenyl, and these aromatic rings may carry one or more than one identical or different substituent, typically halogen, nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C alkylthio, C 1 -C haloalkylthio, C r C 4 alkyl and C r C 4 haloalkyl.
  • Heteroaryl in the definition of the radical R 1 is preferably a five- or six-membered aromatic heterocyclic ring, typically 2-, 3- or 4-pyridyl, pyrimidyl, pyrazinyl, furanyl, thienyl, oxazolyl or isoxazolyl.
  • substituents being halogen, unsubstituted or halogen-substituted C r C 16 alkyl, C 2 -C 16 alkenyl, C 1 -C 16 alkoxy-C 2 -C 6 alkyl, Cj- polyalkoxy-G j -C ⁇ alkyl, or phenyl or benzyl which are unsubstituted or substituted by halogen, nitro, -C ⁇ alkyl, C 1 -C 3 alkoxy, Cj-C 3 haloalkyl; and R 9 is halogen, or unsubstituted or halogen-substituted C j alkoxy or C 2 alkoxy.
  • the invention also embraces the salts which the compounds of formula I may form together with acids.
  • Suitable salts for the formation of the acid addition salts are organic as well as inorganic acids. Examples of such acids are, inter alia, hydrochloric acid, hydrobromic acid, nitric acid, various phosphoric acids, sulfuric acid, acetic acid, propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid, fumaric acid, lactic acid, tartaric acid and salicylic acid.
  • substituents Rj to R 7 , R 18 to R ⁇ , A and B singly or in conjunction with each other or in conjunction with the basic structure to which they are linked, may have chirality.
  • the invention embraces the racemate as well as the enriched and optically pure forms of the respective stereoisomers.
  • the asymmetrically substituted compounds of formula I are usually obtained as racemates, unless chiral educts are used.
  • the stereoisomers can then be isolated in accordance with per se known methods, such as fractionated crystallisation after salt formation with optically pure bases, acids or metal complexes, or chromatographic processes based on physicochemical properties.
  • the compounds of formula I, wherein A and B are alkyl, alkenyl or alkynyl radicals, are derivatives of the pyrazolidine-3,5-dione system.
  • a and B are defined as a saturated or partially unsaturated C carbon bridge
  • formula I is based on the ring system of the lH-pyrazolo[l,2-a]pyridazine
  • R 2 and R 3 are defined as a saturated or partially unsaturated C 3 carbon bridge
  • formula I is based on the ring system of the lH,5H-pyrazolo[l,2-a]pyrazole.
  • the individual ring positions are numbered in accordance with Chemical Abstracts:
  • R x is the group.
  • R 4 is C r C 4 alkyl
  • n is 1, 2, 3 or 4
  • m is 0.
  • compositions are those wherein R 4 is C ⁇ -C alkyl, trifluoromethyl, fluoro, chloro, bromo, C r C ⁇ 0 alkoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, methoxyethylenoxy, cyano, nitro, di-Cj alkylamino or di-C ⁇ alkylamino, acetyl, C 1 -C 3 alkoxycarbonyl, methylsulfonyl, methylsulfinyl or methylmercapto; R 5 is the
  • —Xi — j or Xj is oxygen, sulfur, -CH 2 - or -N(CHO)-;
  • R $ is fluoro, chloro or trifluoromethyl;
  • n is 0, 1, 2 or 3;
  • m is 0 or 1; and
  • o is 0, 1 or 2, the sum of m and n being 0, 1, 2 or 3.
  • compositions are particularly preferred, wherein R-j is the
  • compositions are also those, wherein R ⁇ is the
  • R 4 is methyl, methoxy, fluoro, chloro or nitro; and n is 0 or 1.
  • compositions comprising a safener of formula lie
  • compositions comprising a safener of formula ⁇ d
  • compositions are those comprising a safener of formula He
  • the product is precipitated from the resultant solution by addition of concentrated hydrochloric acid at O°C.
  • the crude product is purified by recrystallisation from methanol to give 8.9 g of crystals of the desired title product, m.p. 244 - 246°C
  • 6-CH 3 6-CH 3 6-O-CH 3 5-O-i-C 3 H 7 5-O-CH 3 5-O-CH 3 5-CO-O-CH 3 5-CO-O-C 2 H 5 5-CO-O-CH 3 5-C -O-i-C 3 H 7
  • the compounds of formula I are disclosed in WO 92/16510 and EP-A-0508 126 as insecticides, acaricides and herbicides.
  • the invention also relates to a method of selectively controlling weeds in crops of cultivated plants, which comprises treating said cultivated plants, the seeds or seedlings or the crop area thereof, concurrently or separately, with a herbicidally effective amount of the herbicide of formula I and, to antagomse the herbicide, an antidotally effective amount of the safener of formula Ha, ub or ⁇ b ⁇
  • Suitable cultivated plants which can be protected by the safener of formula Ha, ub and ⁇ b j against the harmful action of the aforementioned herbicides are preferably maize and cereals.
  • the weeds to be controlled can be monocot as well as dicot weeds.
  • Crop areas will be understood as meaning the areas already under cultivation with the cultivated plants or seeds thereof, as well as the areas intended for cropping with said cultivated plants.
  • a safener of formula Ila, Ub and Hbj can be used for pretreating seeds of the crop plants (dressing of seeds of seedlings) or it can be incorporated in the soil before or after sowing. It can, however, also be applied by itself alone or together with the herbicide postemergence. Treatment of the plant or the seeds with the safener can therefore in principle be carried out irrespective of the time of application of the herbicide. Treatment can, however, also be carried out by simultaneous application of the phytotoxic chemical and safener (e.g. as tank mixture).
  • the concentration of safener with respect to the herbicide will depend substantially on the mode of application. Where a field treatment is carried out either by using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide, the ratio of safener to herbicide will usually be from 100:1 to 1:10, preferably from 20:1 to 1:1.
  • the concentration of herbicide is usually in the range from 0.001 to 2 kg/ha, but will preferably be from 0.005 to 1 kg/ha.
  • compositions of this invention are suitable for all methods of application commonly used in agriculture, including preemergence application, postemergence application and seed dressing.
  • safener/kg of seeds For seed dressing, 0.001 to 10 g of safener/kg of seeds, preferably 0.05 to 2 g of safener/kg of seeds, is usually applied. If the safener is used in liquid form shortly before sowing to effect soaking, then it is preferred to use safener solutions that contain the active ingredient in a concentration of 1 to 10000 ppm, preferably of 100 to 1000 ppm.
  • the safeners of formula Ila, ub or ub ⁇ are processed together with the herbicides tof formula I together with the assistants conventionally employed in formulation technology to emulsif ⁇ able concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules.
  • the formulations are prepared in known manner, conveniently by homogeneously mixing or grinding, or mixing and grinding, the active ingredients with liquid or solid formulation assistants, typically solvents or solid carriers. Surface-active compounds (surfactants) may additionally be used for preparing the formulations.
  • Suitable solvents may typically be: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms such as xylene mixtures or substituted naphthalenes; phthalates such as dibutyl or dioctyl phthalate; aliphatic hydrocarbons such as cyclohexane or paraffins; alcohols and glycols and their ethers and esters such as ethanol, diethylene glycol, 2-methoxyethanol or 2-ethoxyethanol; ketones such as cyclohexanone; strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide; as well as vegetable oils or epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water.
  • aromatic hydrocarbons preferably the fractions containing 8 to 12 carbon atoms such as xylene mixtures or substituted naphthalenes
  • phthalates such as dibutyl or dioctyl phthalate
  • the solid carriers typically used for dusts and dispersible powders are usually natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • highly dispersed silicic acid or highly dispersed absorbent polymers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • Suitable granulated adsorptive carriers are porous types, including pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand.
  • innumerable pregranulated materials of inorganic or organic origin may be used, especially dolomite or pulverised plant residues.
  • suitable surface-active compounds are nonionic, canonic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Suitable anionic surfactants may be water-soluble soaps as well as water-soluble synthetic surface-active compounds.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids ( 0 -C 22 , e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, inter alia from coconut oil or tallow oil. Further suitable soaps are also the fatty acid methyl taurin salts.
  • so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts, and they contain a Cg-C ⁇ alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of ligninsulf onic acid, of dodecylsulf ate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts.
  • the sulfonated benz ⁇ imidazole derivatives preferably contain two sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaph- thalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.
  • Corresponding phosphates typically salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable.
  • Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols or of saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
  • nonionic surfactants are the water-soluble polyadducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which polyadducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit
  • nonionic surfactants are nonylphenol polyethoxylates, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol and octylphenol polyethoxylate.
  • Fatty acid esters of polyoxyethylene sorbitan are also suitable nonionic surfactants, typically polyoxyethylene sorbitan trioleate.
  • Cationic surfactants are preferably quaternary ammonium salts carrying, as N-substituent, at least one Cg-C 2 _ a U c yl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyl trimethylammonium chloride or benzyl bis(2-chloroethyl)ethylammonium bromide.
  • the agrochemical compositions will usually contain from 0.1 to 99 % by weight, preferably from 0.1 to 95 % by weight, of safener or mixture of safener and herbicide, from 1 to 99.9 % by weight, preferably from 5 to 99.8 % by weight, of a solid or liquid formulation assistant, and from 0 to 25 % by weight, preferably from 0.1 to 25 % by weight, of a surfactant
  • compositions may also contain further ingredients such as stabilisers, antifoams, viscosity regulators, binders, tackifiers, as well as fertilisers or other chemical agents.
  • Seed dressing a) Dressing the seeds with a wettable powder formulation of the compound of formula Ha, Ub or Ilb j by shaking in a vessel until the safener is uniformly distributed on the surface of the seeds (dry treatment), using up to c. 1 to 500 g of compound of formula Ua, Ub or Ubi (4 g to 2 g of wettable powder) per 100 kg of seeds.
  • Seed dressing or treatment of the germinated seedlings are naturally the preferred methods of application, as the safener treatment is fully concentrated on the target crop.
  • 1 to 1000 g, preferably 5 to 250 g, of safener is used per 100 kg of seeds.
  • other chemical agents or micronutrients plus or minus deviations from the indicated limiting concentrations are possible (repeat dressing).
  • a liquid formulation of a mixture of safener and herbicide (reciprocal ratio from 10:1 to 1 : 100) is used, the concentration of herbicide being from 0.005 to 5.0 kg/ha. This tank mixture is applied before or after sowing.
  • the safener formulated as emulsifiable concentrate, wettable powder or granulate is applied to the open furrow in which the seeds have been sown. After covering the furrow, the herbicide is applied pre-emergence in conventional manner.
  • a solution of the compound of formula Ua, Ub or Ubj is applied to mineral granulate substrates or polymerised granulates (urea/formaldehyde) and allowed to dry.
  • a coating may additionally be applied (coated granulates) which permits controlled release of the safener over a specific period of time.
  • Emulsions of any desired concentration can be prepared by diluting such concentrates with water.
  • the solutions are suitable for use as microdrops.
  • the compound mixture is throughly mixed with the adjuvants and this mixture is ground in a suitable mill to give wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • the compound mixture is dissolved in methylene chloride, the solution is sprayed on to the carrier, and the solvent is removed under vacuum.
  • compound mixture polyethylene glycol 200 highly dispersed silica inorganic carrier (00.1 - l mm) e.g. CaCO 3 or SiO 2
  • the compound mixture is mixed with the adjuvants and the mixture is moistened with water. This mixture is extruded and then dried in a stream of air.
  • Ready for use dusts are obtained by mixing the the active ingredient with the carriers on a suitable mill.
  • the finely ground compound mixture is intimately mixed with the adjuvants to give a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
  • the following Examples illustrate the ability of the safeners of formula Ua, ub or Ub ] to protect cultivated plants from the phytotoxic action of herbicides of formula L
  • Examples BI to B6 The test plants are raised under greenhouse conditions in plastic pots to the 2- to 3-leaf stage.
  • the growth substrate is standard soil.
  • To the test plants are applied at this stage on the one hand the herbicidal composition by itself and, on the other hand, the mixtures of the herbicidal composition with the substances to be tested as safeners.
  • Application is made with an aqueous suspension of the test substances, prepared from a 25% wettable powder formulation (Example F3, b)) in 5001 of water/ha, with a standard spray nozzle.
  • Table BI Phtotoxic action of herbicide 1.010 sin l and in admixture with afenr 16.

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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)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Ces compositions herbicides sélectives, destinées à la lutte contre les graminées et les mauvaises herbes dans des cultures de végétaux, comprennent: a) une quantité efficace sur le plan herbicide d'un composé de la formule (I), ainsi que les sels et diastéréoisomères de celui-ci; dans cette formule, R1 représente le groupe (i), (ii) ou (iii); les substituants R4 représentent chacun indépendamment halogène, nitro, cyano, alkyle C1-C4, haloalkyle C1-C4, alcoxy C1-C10, haloalcoxy C1-C4, alcényloxy C3-C6, alcoxy C1-C4-alcoxy C2-C4, alcynyloxy C3-C6, alkylcarbonyle C1-C4, alcoxycarbonyle C1-C4, alkylthio C1-C4, alkylsulfinyle C1-C4, alkylsulfonyle C1-C4, amino, alkylamino C1-C4, ou di-alkylamino C1-C4; R5 représente le groupe (iv) ou (v); n vaut 0, 1, 2, 3 ou 4; m vaut 0 ou 1, la somme de m et de n valant 0, 1, 2, 3 ou 4; q vaut 0, 1, 2 ou 3; X1 représente oxygène, soufre, -CH2- ou -N(R7)-; les substituants R6 représentent chacun indépendamment alkyle C1-C4, halogène, haloalkyle C1-C4, alcoxy C1-C4, haloalcoxy C1-C4, nitro, cyano, alcoxycarbonyle C1-C4, amino, alkylamino C1-C4 ou di-alkylamino C1-C4; R7 représente hydrogène, alkyle C1-C4, formyle ou alkylcarbonyle C1-C4; A et B représentent chacun indépendamment hydrogène, alkyle, alcényle, alcynyle, alcoxyalkyle, alkylthioalkyle ou cycloalkyle, ou aryle substitué ou non substitué; ou bien A et B pris ensemble forment le radical divalent d'un système mono, bi, tri ou polycyclique, saturé ou non, substitué ou non; G représente hydrogène ou un groupe (a) -CO-R18, (b), (c) -SO2-R20, (d), (e) ou (f) X; L et M représentent chacun indépendamment oxygène ou soufre; R18 représente alkyle, alcényle, alcoxyalkyle, alkylthioalkyle, polyalcoxyalkyle ou cycloalkyle substitués par halogène et pouvant contenir des hétéroatomes; phényle non substitué ou substitué, phénylalkyle non substitué ou substitué, hétéroaryle substitué, phénoxyalkyle substitué, ou hétéroaryloxyalkyle substitué; R19 représente alkyle, alcényle, alcoxyalkyle ou polyalcoxyalkyle substitués par halogène, ou phényle ou benzyle non substitués ou substitués; R20, R21 et R22 représentent chacun indépendamment alkyle, alcoxy, alkylamino, dialkylamino, alkylthio, alcénylthio, alcynylthio ou cycloalkylthio non substitués ou substitués par halogène, ou bien phényle, phénoxy ou phénylthio non substitués ou substitués; R23 et R24 représentent chacun indépendamment hydrogène, alkyle, alcényle, alcoxy ou alcoxyalkyle non substitués ou substitués par halogène, phényle ou benzyle non substitués ou substitués; ou bien R23 et R24, pris ensemble, forment un radical alcényle qui peut contenir oxygène en tant qu'hétéroatome; et X représente un équivalent d'un ion métal ou un ion ammonium; et b) afin d'exercer une action antagoniste à l'égard de cet herbicide, une quantité efficace en tant qu'antidote de: soit un dérivé quinoléine de la formule (IIa) dans laquelle R10 représente hydrogène, alkyle C1-C8 ou alkyle C1-C8 substitué par alcoxy C1-C6 ou alcényloxy C3-C6; et X2 représente hydrogène ou chloro, soit un dérivé de l'acide 1-phénylazole-3-carboxylique de la formule (IIb) dans laquelle E représente azote ou méthine; R11 représente -CCl3 ou phényle non substitué ou substitué par halogène; R12 et R13 représentent chacun indépendamment hydrogène ou halogène; et R14 représente alkyle C1-C4. Ces composés sont particulièrement appropriés à la lutte contre les mauvaises herbes dans des cultures de végétaux, notamment le maïs et les céréales.
EP95934134A 1994-10-17 1995-10-05 Compositions herbicides Ceased EP0786937A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH312094 1994-10-17
CH3120/94 1994-10-17
PCT/EP1995/003935 WO1996011574A1 (fr) 1994-10-17 1995-10-05 Compositions herbicides

Publications (1)

Publication Number Publication Date
EP0786937A2 true EP0786937A2 (fr) 1997-08-06

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP95934134A Ceased EP0786937A2 (fr) 1994-10-17 1995-10-05 Compositions herbicides

Country Status (9)

Country Link
EP (1) EP0786937A2 (fr)
JP (1) JPH10507189A (fr)
AU (1) AU3653695A (fr)
BR (1) BR9509374A (fr)
CA (1) CA2199636A1 (fr)
IL (1) IL115624A0 (fr)
PL (1) PL319092A1 (fr)
WO (1) WO1996011574A1 (fr)
ZA (1) ZA958712B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0929543B1 (fr) 1996-09-26 2001-10-31 Syngenta Participations AG Composition herbicide
UA66837C2 (uk) * 1998-03-13 2004-06-15 Сінгента Партісіпейшнс Аг Похідні 3-гідроксі-4-арил-5-оксопіразоліну, які проявляють гербіцидну активність
AU3982699A (en) * 1998-05-14 1999-11-29 E.I. Du Pont De Nemours And Company Crop-safened herbicidal mixtures
AU2623399A (en) * 1999-02-11 2000-08-29 Novartis Ag 3-hydroxy-4-aryl-5-pyrazoline derivatives as herbicides
US6555499B1 (en) * 1999-09-07 2003-04-29 Syngenta Crop Protection, Inc. Herbicide agent
CN1198506C (zh) 1999-09-07 2005-04-27 辛根塔参与股份公司 除草组合物
RU2269537C2 (ru) 1999-09-07 2006-02-10 Зингента Партисипейшнс Аг Фенилзамещенные гетероциклические 1,3-кетоенолы, способ их получения, гербицидное средство на их основе и способ борьбы с ростом нежелательной растительности
HU228800B1 (en) 1999-09-07 2013-05-28 Syngenta Participations Ag Synergistic herbicidal composition and use thereof
AR042282A1 (es) 2002-12-05 2005-06-15 Syngenta Participations Ag Proceso para la preparacion de dinitrilos de acido fenilmalonico
DE10301806A1 (de) * 2003-01-20 2004-07-29 Bayer Cropscience Ag Selektive Herbizide auf Basis von substituierten, cyclischen Dicarbonylverbindungen und Safenern
DE10326386A1 (de) 2003-06-12 2004-12-30 Bayer Cropscience Ag N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole
DE10331675A1 (de) * 2003-07-14 2005-02-10 Bayer Cropscience Ag Hetarylsubstituierte Pyrazolidindion-Derivate
DE102004014620A1 (de) 2004-03-25 2005-10-06 Bayer Cropscience Ag 2,4,6-phenylsubstituierte cyclische Ketoenole
DE102004035133A1 (de) 2004-07-20 2006-02-16 Bayer Cropscience Ag Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern
DE102004041529A1 (de) * 2004-08-27 2006-03-02 Bayer Cropscience Gmbh Herbizid-Kombinationen mit speziellen Ketoenolen
DE102004044827A1 (de) 2004-09-16 2006-03-23 Bayer Cropscience Ag Jod-phenylsubstituierte cyclische Ketoenole
DE102005059469A1 (de) 2005-12-13 2007-06-14 Bayer Cropscience Ag Insektizide Zusammensetzungen mit verbesserter Wirkung
DE102006007882A1 (de) 2006-02-21 2007-08-30 Bayer Cropscience Ag Cycloalkyl-phenylsubstituierte cyclische Ketoenole
GB0900641D0 (en) 2009-01-15 2009-02-25 Syngenta Ltd Novel herbicides
GB0901086D0 (en) 2009-01-22 2009-03-11 Syngenta Ltd Novel herbicides
GB0901835D0 (en) 2009-02-04 2009-03-11 Syngenta Ltd Novel herbicides
GB0901834D0 (en) 2009-02-04 2009-03-11 Syngenta Ltd Novel herbicides
CN102348684B (zh) 2009-03-11 2014-11-12 拜尔农作物科学股份公司 被卤代烷基亚甲基氧基苯基取代的酮烯醇
DE102010008644A1 (de) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft, 13353 Zyklische Ketoenole zur Therapie
KR102030337B1 (ko) 2012-01-26 2019-10-10 바이엘 인텔렉쳐 프로퍼티 게엠베하 어류 기생충 방제용의 페닐-치환된 케토에놀

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE103902T1 (de) * 1982-05-07 1994-04-15 Ciba Geigy Ag Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen.
ATE139768T1 (de) * 1991-03-19 1996-07-15 Ciba Geigy Ag Verbindungen mit herbiziden,acarizider und insektizider wirkung
DE4109208A1 (de) * 1991-03-21 1992-09-24 Bayer Ag 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9611574A1 *

Also Published As

Publication number Publication date
PL319092A1 (en) 1997-07-21
BR9509374A (pt) 1997-12-30
IL115624A0 (en) 1996-01-19
WO1996011574A1 (fr) 1996-04-25
JPH10507189A (ja) 1998-07-14
AU3653695A (en) 1996-05-06
CA2199636A1 (fr) 1996-04-25
ZA958712B (en) 1996-07-10

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