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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• • 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
  • A01N43/48—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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

• the invention relates to the technical field of the crop protection products, in particular the herbicide/antidote combinations (herbicide/safener combinations) which are outstandingly suitable for the use against competing harmful plants in crops of useful plants.
• HPPDO p-hydroxyphenylpyruvate dioxygenase
• U.S. Pat. No. 5,627,131, EP 551650 and EP 298680 disclose specific mixtures of herbicides with safeners, particularly pre-emergence safeners.
• a safener is, for the purposes of the invention, a compound or a mixture of compounds which compensates for, or reduces, the phytotoxic properties of a herbicide toward useful plants without essentially reducing the herbicidal action against harmful plants.
• the invention therefore relates to a herbicidally active composition
• a herbicidally active composition comprising a mixture of
• a herbicidally active amount is, for the purposes of the invention, such an amount of one or more herbicides which is capable of adversely affecting plant growth.
• An antidotically effective amount is, for the purposes of the invention, such an amount of one or more safeners which is capable of at least partially countering the phytotoxic effect of a herbicide or herbicide mixture on a useful plant.
• alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can be in each case straight-chain or branched in the carbon skeleton.
• Alkyl radicals also the composite meanings such as alkoxy, haloalkyl and the like, preferably have 1 to 4 carbon atoms and are, for example, methyl, ethyl, n- or i-propyl or n-, i-, t- or 2-butyl.
• Alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl.
• Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.
• (C 1 -C 4 )-Alkyl is the abbreviation for alkyl having 1 to 4 carbon atoms; the same applies analogously to other general definitions of radicals, where the range of the possible number of carbon atoms is indicated in brackets.
• Cycloalkyl is, preferably, a cyclic alkyl radical having 3 to 8, preferably 3 to 7, especially preferably 3 to 6, carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
• Cycloalkenyl and cycloalkinyl denote corresponding unsaturated compounds.
• Halogen is fluorine, chlorine, bromine or iodine.
• Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl or alkynyl which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCl 3 , CHCl 2 , CH 2 CH 2 Cl.
• Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl. This also applies analogously to other halogen-substituted radicals.
• a hydrocarbon radical can be an aromatic or an aliphatic hydrocarbon radical, where an aliphatic hydrocarbon radical is generally a straight-chain or branched saturated or unsaturated hydrocarbon radical, preferably having 1 to 18, especially preferably 1 to 12, carbon atoms, for example alkyl, alkenyl or alkynyl.
• Aliphatic hydrocarbon radical preferably means alkyl, alkenyl or alkynyl having up to 12 carbon atoms; the same applies analogously to an aliphatic hydrocarbon radical in a hydrocarbon-oxy radical.
• Aryl is generally a mono-, bi- or polycyclic aromatic system having by preference 6-20 carbon atoms, preferably 6 to 14 carbon atoms, especially preferably 6 to 10 carbon atoms, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, especially preferably phenyl.
• Heterocyclic ring, heterocyclic radical or heterocyclyl is a mono-, bi- or polycyclic ring system which is saturated, unsaturated and/or aromatic and contains one or more, preferably 1 to 4, hetero atoms, preferably selected from the group consisting of N, S and O.
• saturated heterocycles having 3 to 7 ring atoms and one or two hetero atoms selected from the group consisting of N, O and S, their chalcogens not being adjacent.
• monocyclic rings having 3 to 7 ring atoms and a hetero atom selected from the group consisting of N, O and S, and also morpholine, dioxolane, piperazine, imidazoline and oxazolidine.
• Very especially preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.
• partially unsaturated heterocycles having 5 to 7 ring atoms and one or two hetero atoms selected from the group consisting of N, O and S.
• partially unsaturated heterocycles having 5 to 6 ring atoms and one hetero atom selected from the group consisting of N. O and S.
• Very especially preferred partially unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.
• heteroaryl for example mono- or bicyclic aromatic heterocycles having 5 to 6 ring atoms which contain one to four hetero atoms selected from the group consisting of N. O, S, the chalcogens not being adjacent.
• monocyclic aromatic heterocycles having 5 to 6 ring atoms which contains a hetero atom selected from the group consisting of N, O and S, and also pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole and isoxazole.
• pyrazole, thiazole, triazole and furan are especially preferred.
• Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl such as phenyl and arylalkyl such as benzyl, or substituted heterocyclyl, are a substituted radical which is derived from an unsubstituted skeleton, the substituents being, by preference, one or more, by preference 1, 2 or 3, in the case of Cl and F also up to the maximum possible number of, substituents selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino and alkylsulfynyl, haloalkylsulfyny
• radicals having carbon atoms those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
• preferred substituents are those seelected from the group consisting of halogen, for example fluorine or chlorine, (C 1 -C 4 )-alkyl, preferably methyl or ethyl, (C 1 -C 4 )-haloalkyl, preferably trifluoromethyl, (C 1 -C 4 )-alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 )-haloalkoxy, nitro and cyano.
• halogen for example fluorine or chlorine
• (C 1 -C 4 )-alkyl preferably methyl or ethyl
• C 1 -C 4 )-haloalkyl preferably trifluoromethyl
• C 1 -C 4 )-alkoxy preferably methoxy or ethoxy
• Mono- or disubstituted amino is a chemically stable radical selected from the group of the substituted amino radicals which are N-substituted by, for example, one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-Arylamino and N-heterocycles.
• aryl is phenyl.
• substituted aryl is substituted phenyl.
• acyl preferably (C 1 -C 4 )-alkanoyl. This also applies analogously to substituted hydroxylamino or hydrazino.
• optionally substituted phenyl is phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, in the case of halogen such as Cl and F also up to pentasubstituted, by identical or different radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chloro-phenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
• halogen such as Cl and
• An acyl radical is the radical of an organic acid having by preference up to 6 carbon atoms, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radical of carbonic monoesters, optionally N-substituted carbamic acids, sulfonic acid, sulfinic acids, phoshonic acids, phosphinic acids.
• Acyl is, for example, formyl, alkylcarbonyl such as (C 1 -C 4 -alkyl)-carbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxy-carbonyl, alkylsulfonyl, alkylsulfynyl or N-alkyl-1-iminoalkyl.
• stereoisomers which show the same topological linkage of the atoms, and their mixtures, also fall under the formulae (I) to (VIII). Such compounds contain one or more asymmetric carbon atoms or else double bonds which are not indicated specifically in the general formulae.
• the stereoisomers which are possible which are defined by their specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, can be obtained form mixtures of the stereoisomers by customnary methods or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
• Herbicidally active substances which are suitable in accordance with the invention are those compounds of the formula (I) which, on their own, cannot be used, or not optimally used, in cereal crops, rice and/or maize because they are too harmful to the crop plants.
• Herbicides of the formula (I) are known, for example, from EP-A 0 137 963, EP-A 0 352 543, EP-A 0 418 175, EP-A 0 496 631 and AU-A 672 058.
• the compounds of the formula (II) are known, for example, from EP-A-0 333 131 (ZA-89/1960), EP-A-0 269 806 (U.S. Pat. No.
• EP-A-0 346 620 (AU-A-89/34951), EP-A-0 174 562, EP-A-0 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 9417120) and the literature cited therein or can be prepared by or analogously to the processes described therein.
• the compounds of the formula. (III) are known from EP-A-0 086 750, EP-A-0 94349 (U.S. Pat. No. A-902,340), EP-A-0 191736 (U.S. Pat. No.
• Preferred herbicide/safener combinations are those which comprise safeners of the formula (II) and/or (III) where the symbols and indices have the following meanngs:
• R 24 is hydrogen, (C 1 -C 18 )-alkyl, (C 3 -C 12 )-cycloalkyl, (C 2 -C 8 )-alkenyl and (C 2 -C 18 )-alkynyl, where the carbon-containing groups can be substituted by one or more preferably up to three, radicals R 50 ;
• R 50 is identical or different halogen, hydroxyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkylthio, (C 2 -C 8 )-alkenylthio, (C 2 -C 8 )-alkynylthio, (C 2 -C 8 )-alkenyloxy, (C 2 -C 8 )-alkynyloxy, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkoxy, cyano, mono- and di-(C 1 -C 4 )-alkyl)amino, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2 -C 8 )-alkynyloxycarbonyl, (C 1
• herbicide/safener combinations which comprise safeners of the formula (II) and/or (III) where the symbols and indices have the following meanings:
• herbicidal compositions comprising a safener of the formula (II) where the symbols and indices have the following meanings:
• safeners are compounds of the formula (V) or salts thereof in which
• This allows the field of application of conventional crop protection products to be widened quite considerably and to be extended to, for example, crops such as wheat, barley, maize, rice and other crops in which a use of the herbicides was hitherto impossible, or only limited, that is to say at low rates and with a restricted spectrum.
• the herbicidally active substances and the abovementioned safeners can be applied together (as a readymix or by the tank mix method) or in succession in any desired sequence.
• the weight ratio of safener: herbicidally active substance may vary within wide limits and is preferably within the range from 1:100 to 100:1, in particular from 1:10 to 10:1.
• the optimum amounts of herbicidally active substance and safener in each case depend on the type of the herbicidally active substance used or on the safener used and on the species of the crop stand to be treated and can be determined in each individual case by simple, routine preliminary experiments.
• the main fields of application for the combinations according to the invention are, in particular, maize and cereal crops (for example wheat, rye, barley, oats), rice, sorghum, but also cotton and soybeans, preferably cereals, rice and maize.
• maize and cereal crops for example wheat, rye, barley, oats
• rice, sorghum but also cotton and soybeans, preferably cereals, rice and maize.
• the safeners employed in accordance with the invention can be used for pretreating the seeds of a crop plant (seed dressing), or be incorporated into the seed furrows prior to sowing or applied together with the herbicide before or after plant emergence.
• the preemergence treatment includes not only the treatment of the area under cultivation prior to sowing and the treatment of the areas under cultivation where the seeds have been planted but the plants have not yet emerged.
• the application rates of safener required may vary within wide limits depending on the indication and the herbicidally active substance used and are generally in the range of from 0.001 to 5 kg, preferably 0.005 to 0.5 kg, of active substance per hectare.
• the present invention therefore also relates to a method of protecting crop plants from phytotoxic side effects of herbicides of the formula (I), which comprises applying an antidote-effective amount of a compound of the formula (II), (III), (IV), (V), (VI), (VII) and/or (selected from group (b)) to the plants, the seeds of the plants or the area under cultivation, either before, after or simultaneously with the herbicidally active substance A of the formula (I).
• the herbicide/safener combination according to the invention may also be employed for controlling harmful plants in crops of genetically engineered plants which are either known or still to be developed.
• the transgenic plants are distinguished by particular, advantageous properties, for example by resistances to certain crop protection agents, resistances to plant diseases or pathogens causing plant diseases such as particular insects or microorganisms such as fungi, bacteria or viruses.
• Other particular properties relate for example, to the harvested material in terms of quantity, quality, storing properties, composition and specific constituents.
• transgenic plants are known which have an increased starch content or an altered starch quality, or those where the harvested material has a different fatty acid composition.
• effects on harmful plants to be observed in other crops are frequently accompanied by effects which are specific for application in the transgenic crop in question, for example an altered or specifically widened weed spectrum which can be controlled, altered application rates which may be used, preferably good compatibility with the herbicides to which the transgenic crop is resistant, and altered growth and yield of the transgenic crop plants.
• the invention therefore also relates to the use of the combination according to the invention for controlling harmful plants in transgenic crop plants.
• the safeners of the formulae (III)-(VI) and of group (b) and their combinations with one or more of the abovementioned herbicidally active substances of the formula (II) can be formulated in various ways, depending on the biological and/or chemico-physical parameters specified. Examples of suitable-formulations which are possible are:
• WP wettable powders
• EC emulsifiable concentrates
• SP water-soluble powders
• SL water-soluble concentrates
• BW concentrated emulsions
• CS capsule suspensions
• SC oil- or water-based dispersions
• DP dusts
• O oil-miscible solutions
• GR seed treatment products
• water-soluble granules (SG) water-dispersible granules (WG)
• ULV formulations microcapsules and waxes.
• the formulation auxiliaries which may be required, such as inert materials, surfactants, solvents and other additives are also known and described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2 nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2 nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2 nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ.
• Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinaphthalene-sulfonate, or else sodium oleoylmethyltaurinate, in addition to a diluent or inert substance.
• the herbicidally active substances are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and they
• Emulsifiable concentrates are prepared, for example, by dissolving the active substance in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or else higher-boiling saturated or unsaturated aliphatic or aromatic, or mixtures of the organic solvents with the addition of one or more ionic and/or nonionic surfactants (emulsifiers).
• organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or else higher-boiling saturated or unsaturated aliphatic or aromatic, or mixtures of the organic solvents with the addition of one or more ionic and/or nonionic surfactants (emulsifiers).
• substances which can be used as emulsifiers are: calcium (C 6 -C 18 )-alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, (C 2 -C 18 )-alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
• Dusts are generally obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• finely divided solid substances for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet-grinding using commercially available bead mills with or without addition of surfactants, for example those which have already been mentioned above in the case of the other formulation types.
• Emulsions for example oil-in-water emulsions (EW)
• EW oil-in-water emulsions
• Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils.
• Suitable active substances can also be granulated in the manner which is conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
• water-dispersible granules are prepared by the customary processes such as spray-drying, fluidized-bed granulation, disk granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active substances of the formulae (II)-(VII) and/or (b) or of the herbicide/antidote mixture of active substances (I) and (II)-(VII) and/or (b) and 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid additive and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
• the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration is approximately 1 to 80% by weight.
• Formulations in the form of dusts comprise approximately 1 to 20% by weight of active substance, sprayable solutions approximately 0.2 to 20% by weight of active substance.
• the active substance content depends partly on whether the active compound is in liquid or solid form. The active substance content of the water-dispersible granules is, as a rule, between 10 and 90% by weight.
• the abovementioned formulations of active substances may comprise, if appropriate, the adhesives, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.
• Components which can be used for the mixtures according to the invention in mixed formualtions or in a tank mix are, for example, known active substances as they are described, for example, in Weed Research 26, 441-445 (1986), or “The Pesticide Manual”, 10 th edition, The British Crop Protection Council, 1994, and in the literature cited therein.
• Herbicides which are known from the literature and which can be combined with the mixtures according to the invention are, for example, the following active substances (note: either the common names in accordance with the International Organization for Standardization (ISO) or the chemical names, if appropriate together with the customary code number, of the compounds are given):
• acetochlor acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]-oxy]-acetic acid and its methyl ester; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, i.e.
• ammonium sulfamate ammonium sulfamate; anilofos; asulam; atrazine; azafenidine (DPX-R6447), azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516H, i.e.
• the formulations which are in commercially available form are, if desired, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules.
• Preparations in the form of dusts, soil granules, granules for broadcasting and sprayable solutions are usually not diluted any further with other inert substances prior to use.
• the necessary application rate of the herbicides of the formula (I) varies with the external conditions such as, inter alia, temperature, humidity, and the nature of the herbicide used. It may be varied within wide limits, for example between 0.001 and 10.0 kg/ha or more of herbicide, but it is preferably between 0.005 and 5 kg/ha.
• a dust is obtained by mixing 10 parts by weight of a compound of the formula (II)-(VII) and/or from amongst group B (b) or of an active substance mixture of a herbicidally active substance of the formula (I) and a safener of the formula (II)-(VII) and/or from amongst group (b) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
• a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (II)-(VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidally active substance of the formula (I) and a safener of the formula (II)-(VII) and/or from amongst group B(b), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter and dispersant, and grinding the mixture in a pinned-disk mill.
• a concentrate which is readily dispersible or suspensible in water is obtained by mixing 20 parts by weight of a compound of the formula (II)-(VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidally active substance of the formula (I) and a safener of the formula (II)-(VII) and/or from amongst group B(b), 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanbl polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, approx. 255 to above 277° C.) and grinding the mixture in a ball mill to a fineness of below 5 microns.
• An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (II)-(VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidally active substance of the formula (I) and a safener of the formula (II)-(VII) and/or from amongst group B(b), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.
• Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and useful plants are placed in sandy loam in pots of 9 to 13 cm diameter and covered with soil.
• rice plants and harmful plants which are undesired in this crop of useful plant, are grown in a waterlogged soil.
• Various doses of the herbicides and safeners formulated as emulsifiable concentrates or dusts were applied to the surface of the soil cover in the form of aqueous dispersions or suspensions or emulsions at a rate of 300 to 800 l of water/ha (converted), or, in the case of the rice test, poured into the irrigation water.
• the pots are then kept in the greenhouse under optimal conditions to grow the plants on. 3-4 weeks after the treatment, the damage to useful plants and harmful plants is scored visually. The damage is expressed in percentages in comparison with untreated controls.
• Safener b-1 1-[4-(2-Methoxybenzoylsulfamoyl)phenyl]-3-methylurea
• Safener c-1 2-Methoxy-N-[4-(2-methoxybenzoylsulfamoyl)phenyl]-acetamide
• Safener c-3 N-[4-(2-Methoxybenzoylsulfamoyl)phenyl]-cyclobutane-carboxamide
• Safener c-7 N-[4-(2-Chlorobenzoylsulfamoyl)phenyl]-cyclopropane-carboxamide
• Safener c-10 N-[4-(2-Trifluoromethoxybenzoylsulfamoyl)phenyl]-cyclo-propanecarboxamide
• ECHCG Echinocloa crus galli
• ABUTH Abutilon theophrasti
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and useful plants are placed in sandy loam in pots of 9 to 13 cm diameter and covered with soil.
• rice plants and harmful plants which are undesired in this crop of useful plants are grown in a waterlogged soil. In the three-leaf stage, i.e.
• Herbicide 3-1 100-300 g a.i./ha; herbicide 3-1; wheat Damage [%] Product Dose Wheat Herbicide/safener [kg a.i./ha] (variety Ralle) Herbicide 3-1 300 40 Herbicide 3-1 200 35 Herbicide 3-1 100 30 Herbicide 3-1/safener II-9 300 + 150 10 Herbicide 3-1/safener II-9 200 + 100 5 Herbicide 3-1/safener II-9 100 + 50 0 Herbicide 3-2 300 45 Herbicide 3-2 200 30 Herbicide 3-2 100 30 Herbicide 3-2/safener II-9 300 + 300 10 Herbicide 3-2/safener II-9 200 + 200 0 Herbicide 3-2/safener II-9 100 + 100 0
• Safener II-9 Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate
• Safener b-1 1-[4-(2-Methoxybenzoylsulfamoyl)phenyl]-3-methylurea
• Safener c-1 2-Methoxy-N-[4-(2-methoxybenzoylsulfamoyl)phenyl]-acetamide 2.
• Herbicide/safener [g a.i./ha] 14 dat 42 dat Herbicide 1-1 50 42 18 Herbicide 2 120 13 7 Herbicide 1-1 + herbicide 50 + 120 + 120 10 5 2 + safener II-9 Safener II-9 120 0 0 Herbicide 1-1: Herbicide Example No.
• Herbicide 2 N,N-Dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureido-sulfonyl]-4-formylaminobenzamide
• Safener II-9 Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate

Landscapes

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

Priority Applications (2)

Applications Claiming Priority (5)

Related Parent Applications (3)

Related Child Applications (1)

Publications (1)

Family

ID=7888611

Family Applications (2)

Family Applications After (1)

Country Status (26)

Cited By (17)

Families Citing this family (33)

Citations (17)

Family Cites Families (27)

• 1998
  • 1998-11-21 DE DE19853827A patent/DE19853827A1/de not_active Withdrawn
• 1999
  • 1999-05-11 UA UA2001064309A patent/UA70977C2/uk unknown
  • 1999-11-05 TR TR2001/01399T patent/TR200101399T2/xx unknown
  • 1999-11-05 CA CA2351374A patent/CA2351374C/en not_active Expired - Lifetime
  • 1999-11-05 CN CNB998134678A patent/CN1195414C/zh not_active Expired - Lifetime
  • 1999-11-05 WO PCT/EP1999/008470 patent/WO2000030447A1/de active IP Right Grant
  • 1999-11-05 KR KR1020017006303A patent/KR100678802B1/ko active IP Right Grant
  • 1999-11-05 AT AT99972493T patent/ATE252832T1/de active
  • 1999-11-05 CZ CZ20011773A patent/CZ303927B6/cs not_active IP Right Cessation
  • 1999-11-05 DK DK99972493.3T patent/DK1130965T4/da active
  • 1999-11-05 ES ES99972493T patent/ES2209561T5/es not_active Expired - Lifetime
  • 1999-11-05 PL PL347825A patent/PL199503B1/pl unknown
  • 1999-11-05 DE DE59907567T patent/DE59907567D1/de not_active Expired - Lifetime
  • 1999-11-05 HU HU0105029A patent/HU229028B1/hu unknown
  • 1999-11-05 ID IDW00200101060A patent/ID29434A/id unknown
  • 1999-11-05 RU RU2001117066/04A patent/RU2235464C2/ru active
  • 1999-11-05 EP EP99972493A patent/EP1130965B2/de not_active Expired - Lifetime
  • 1999-11-05 AU AU13800/00A patent/AU768402B2/en not_active Expired
  • 1999-11-05 JP JP2000583345A patent/JP4291516B2/ja not_active Expired - Lifetime
  • 1999-11-05 BR BRPI9915516-8B1A patent/BR9915516B1/pt active IP Right Grant
  • 1999-11-05 IL IL14320599A patent/IL143205A/xx not_active IP Right Cessation
  • 1999-11-05 SK SK681-2001A patent/SK287344B6/sk not_active IP Right Cessation
  • 1999-11-16 CO CO99071922A patent/CO5221023A1/es not_active Application Discontinuation
  • 1999-11-18 AR ARP990105872A patent/AR021321A1/es active IP Right Grant
• 2001
  • 2001-04-25 BG BG105474A patent/BG64932B1/bg unknown
  • 2001-05-08 ZA ZA200103701A patent/ZA200103701B/en unknown
• 2005
  • 2005-10-07 US US11/246,790 patent/US20060030485A1/en not_active Abandoned
• 2012
  • 2012-08-31 US US13/601,247 patent/US8748343B2/en not_active Expired - Fee Related

Patent Citations (19)

Also Published As

Similar Documents

Legal Events