WO2000003592A2 - Herbizide mittel mit substituierten phenoxysulfonylharnstoffen - Google Patents

Herbizide mittel mit substituierten phenoxysulfonylharnstoffen Download PDF

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Publication number
WO2000003592A2
WO2000003592A2 PCT/EP1999/004957 EP9904957W WO0003592A2 WO 2000003592 A2 WO2000003592 A2 WO 2000003592A2 EP 9904957 W EP9904957 W EP 9904957W WO 0003592 A2 WO0003592 A2 WO 0003592A2
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Prior art keywords
compounds
rice
group
active
herbicides
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PCT/EP1999/004957
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German (de)
English (en)
French (fr)
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WO2000003592A3 (de
Inventor
Erwin Hacker
Hermann Bieringer
Thomas Auler
Alvaro Melendez
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Aventis Cropscience Gnbh
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Priority claimed from DE19832017A external-priority patent/DE19832017A1/de
Priority claimed from DE1999128453 external-priority patent/DE19928453A1/de
Application filed by Aventis Cropscience Gnbh filed Critical Aventis Cropscience Gnbh
Priority to EP99936162A priority Critical patent/EP1096854A2/de
Priority to JP2000559736A priority patent/JP2002520341A/ja
Priority to AU52812/99A priority patent/AU5281299A/en
Priority to BRPI9912823A priority patent/BRPI9912823B1/pt
Publication of WO2000003592A2 publication Critical patent/WO2000003592A2/de
Publication of WO2000003592A3 publication Critical patent/WO2000003592A3/de

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the technical field of plant protection products, in particular the invention relates to herbicidal compositions containing certain phenoxysulfonylureas and / or their salts which are outstanding for combating weeds in rice, in particular grassy, dicotyledon, which have hitherto been difficult to control with individual herbicides and / or cyperaceae-like weeds in rice or transgenic rice cultures.
  • Herbicidal compositions are known from IT 1270985, characterized by an effective content of substituted phenoxysulfonylureas in combination with herbicidal active ingredients.
  • herbicidal compositions having the features of claim 1.
  • the present invention thus relates to herbicidal compositions comprising
  • Fentrazamide (NBA 061), haloxyfop, sethoxydim, dithiopyr, etobenzanide., Clefoxidim, KIH 6127, and clethodim,
  • Bb selectively in rice herbicides active mainly against dicotyledonous harmful plants and cyperaceae, selected from the group consisting of 2,4-D, MCPA, mecoprop, mecoprop-P, tritosulfuron, halosulfuron-methyl, dicamba, acifluorfen, carfentrazone, bentazo ⁇ and triclopyr ,
  • Bc selectively in rice, predominantly herbicides active against grass and dicotyledonous harmful plants and cyperaceae, selected from the group consisting of pendimethalin, clomazone, KIH 2023, oxadiargyl, cyclos ulfamuro ⁇ (AC 322, 140), azimsulfuron (DPX-A-8947) , Nicosulfuron, cinmethylin, indanofan, pentoxazone,
  • the combinations of herbicidal active ingredients of types A and B according to the invention make it particularly advantageous to achieve the control of the weed spectrum required by the practitioner, individual species which are difficult to control also being recorded.
  • the combinations of active ingredients in the individual combination partners contained in the combination can be significantly reduced with the combinations according to the invention, which allows more economical solutions on the part of the users.
  • the compounds of formula I can form salts in which the hydrogen of the -S0 2 -NH group is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal, in particular alkali salts (for example Na or K salts) or alkaline earth metal salts, or also ammonium salts or salts with organic amines. Salt formation can also take place by the addition of a strong acid to the heterocyclic part of the compounds of the formula I. Suitable for this are, for. B. HCl, HN0 3 , trichloroacetic acid, acetic acid or palmitic acid.
  • Particularly advantageous compounds are those in which the salt of the herbicide of the formula (I) is formed by replacing the hydrogen of the —SO 2 —NH groups with a cation from the group of the alkali metals, alkaline earth metals and ammonium, preferably sodium.
  • the compounds of the formula I contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formula, these nevertheless belong to the type A compounds.
  • the through their Specific spatial forms of possible stereoisomers defined, such as enantiomeric diastereoisomers, Z and E isomers are all encompassed by the formula I and can be obtained from mixtures of the stereoisomers by customary methods or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
  • the stereoisomers mentioned in pure form and their mixtures can thus be used according to the invention.
  • Phenoxysulfonylureas of the formula I are in principle, for. B. from general formula 1 from IT 127 09 85 and their suitability as a synergistic partner for herbicides to be used in crop plants is described there. The outstanding suitability of the special
  • group A phenoxysulfonylureas as combination partners in synergistic mixtures with other herbicides which can be used in rice cannot be found in the prior art.
  • combinations of compounds of group A) with the rice herbicides of group B have such an exceptional position in the control of the most important harmful plants in rice crops.
  • the compounds of group A) are only suitable for controlling harmful plants in rice, it cannot be predicted with a predominant or even some prospect of success whether combinations with other rice herbicides allow increases in effectiveness in combating harmful plants beyond the additive effect.
  • the compound is a preferred combination partner from group A)
  • A1 (ethoxysulfuron): 1 - [2-ethoxy phenoxy . sulfonyl] -3- (4,6-dimethoxy-2-pyhmidyl) urea
  • Pesticide Manual Publ. British Crop Protection Council
  • This compound is preferably used as the sole active ingredient of group A) and can be combined with one or more herbicidally active compounds of group B.
  • the special group A sulfonylurines, in particular the compound A1), in combination with other type B herbicides, are excellently suited to effectively control weed species which are difficult to control in rice crops. In particular, there are unexpected special effects against resistant harmful grasses.
  • the combination partners of type B are generally standard herbicides, but are selected based on certain criteria. Without exception, they are herbicides which are selective in rice against undesirable plants.
  • the harmful plants to be controlled include above all grasses and dicotyledons / cyperaceae.
  • the spelling “dicotyledons / cyperaceae” should express that the activity against dicotyledon and cyperaceae is given, but the effectiveness against dicotyledon is in the foreground.
  • a gradation can be made with regard to the focus of the plants being controlled.
  • Part of the type B herbicides is predominantly, or almost exclusively, active against grasses (subgroup Ba)), another part is predominantly active against dicotyledons and cyperaceae (subgroup Bb)), while another group is active against both grasses and dicotyledons / cyperaceae (Subgroup Bc)) effectiveness developed.
  • the herbicidally active mixture of the invention is characterized in that it contains, as herbicides of type B, one or more herbicides from the group Ba) which are active selectively in rice against grasses and which consists of
  • Pesticide Mannual 1 1st edition, 1997, p. 1 101 -1 103
  • Methyl 2- (4,6-dimethoxy-2-pyrimidinyloxy) -6- (1-methoxyiminooethyl) benzoate also as an acid or sodium salt
  • herbicidal compositions which, as a type B compound, contain one or more compounds which are selective in rice against dicotyledons and in some cases also cyperaceae (subgroup Bb)), which are selected from the group consisting of the herbicides
  • (2,4-dichlorophe ⁇ oxy) acetic acid frequently used forms: 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D- iso-octyl, 2,4-D-isopropyl, 2,4-D-trolamine,
  • 3,6-dichloro-o-aisic acid used i.a. as dicamba-dimethylammonium, dicamba potassium, dicamba
  • Pesticide Manual 10th ed. 1994, p.1015-1017.
  • the herbicidally active combinations contain, as herbicides of type B, one or more herbicides which are selectively active in rice, predominantly against grasses and dicotyledon / cyperaceae (subgroup Bc)) from the group consisting of
  • Compounds B1) to B32) are, for example, herbicides which are known from the source indicated for the particular compound and are used specifically in combination with the compounds of group A) of the invention and are selective in rice and in transgenic rice.
  • the formula of which is regularly given for clarification, in some cases it is also referred to modifications of the basic substances that are usually used, which can also be used in the context of the present invention.
  • optically active forms of type B compounds are customary, these are also part of the invention, and in some cases reference has also been made to these forms (for example mecoprop and mecoprop-P etc.).
  • Combinations of the active ingredients A + B show superadditive effects, i . H.
  • the herbicidal compositions according to the invention make it possible to reduce the application rate and / or to increase the safety margin in rice crops. Both make economic and ecological sense.
  • the choice of the amounts to be used by components A + B, the ratio of components A: B and the order in which they are applied, as well as the formulation to be chosen, depend on a whole series of factors.
  • herbicidal compositions according to the invention are characterized in that they have a synergistically active content of a combination of the compounds of the formula I or their salts (type A compounds) with compounds from group B.
  • a compounds type A compounds
  • the herbicidal compositions of the invention are generally inherent in a synergistic effect.
  • the weight ratios A: B of the combined herbicides and their application rates can vary within wide limits.
  • a range according to the invention of the application rate ratios (wt / wt) comprises approximately A: B such as 1: 20,000 to approximately 200: 1.
  • Agents which compounds of the formula I or their salts (type A compounds) and compounds are preferred in the context of the invention from group B in a weight ratio of about 1: 8000 to 100: 1.
  • Means are particularly expedient with A: B ratio ratios between 1: 4000 and 50: 1.
  • the following picture results for the various herbicides of group B ie the following application rates and weight ratios (A: B) are preferably used:
  • the active compound combinations according to the invention can be present both as mixed formulations of the two components, which are then diluted with water in the customary manner, or else as So-called tank mixes can be prepared by diluting the separately formulated components together with water.
  • the active ingredients of types A and B can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified.
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SP water-soluble powders
  • SL water-soluble concentrates
  • EW concentrated emulsions
  • CS capsule suspensions
  • SC oil or water-based dispersions
  • SC Suspoemulsio ⁇ e ⁇
  • Suspensionsko ⁇ ze ⁇ trate dusts
  • DP oil-miscible solutions
  • pickling agents granules (GR) in the form of micro, spray, elevator and adsorbent granules, granules for the soil or litter application, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules and waxes.
  • WP water-soluble wettable powders
  • WG water-dispersible granules
  • EC water-emulsifiable granules
  • SE suspoemulsions
  • SC oil suspension concentrates
  • combinations with other pesticidally active substances, herbicides, insecticides, fungicides, and also antidotes, safeners, fertilizers and / or growth regulators can be prepared, for. B. in the form of a finished formulation or as a tank mix.
  • the herbicide combinations of the invention are produced particularly advantageously by combining the compounds of the formula I or their salts (type A compounds) with one or more compounds of the type B analogously to a conventional crop protection formulation from the group comprising water-soluble wettable powders (WP), water-dispersible granules (WDG), water-emulsifiable granules (WEG), suspoemulsions (SE) and oil suspension concentrates (SC).
  • WP water-soluble wettable powders
  • WDG water-dispersible granules
  • WEG water-emulsifiable granules
  • SE suspoemulsions
  • SC oil suspension concentrates
  • Spray powders are preparations which are uniformly dispersible in water and, in addition to the active ingredients, in addition to a diluent or inert substance, are also surfactants of an ionic and / or nonionic type (wetting agents, dispersants), for. B.
  • polyoxyethylated alkylphenols polyoxyethylated fatty alcohols and Fettami ⁇ e
  • fatty alcohol polyglycol ether alkane
  • alkane or Alkylarylsulfo ⁇ ate
  • sodium ligninsulfonate sodium 2,2'-dinaphthylmethane-6,6' -disulfo ⁇ saures sodium dibutylnaphthalenesulfonate or else sodium oleylmethyltaurate.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient or ingredients in an organic solvent, e.g. As butanol, cyclohexanone, dimethylformamide, xylene or even higher aromatics ⁇ or Hydrocarbons with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. As butanol, cyclohexanone, dimethylformamide, xylene or even higher aromatics ⁇ or Hydrocarbons
  • surfactants of ionic and / or nonionic type (emulsifiers) examples of emulators that can be used are: alkylarylsulfonic acid calcium salts such as cadodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products (e.g
  • Dusts are obtained by grinding the active ingredient or ingredients with finely divided substances, e.g. B. talc, natural clays, such as kaolin, bentonite and pyrophyllite, or granules of diatomaceous earth can be prepared either by spraying the active ingredient or the active ingredients onto adsorbable, granulated inert material or by applying active ingredient concentrations by means of adhesives, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material.
  • adhesives e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • the agrochemical preparations according to the invention generally contain 0.1 to 99% by weight, in particular 2 to 95% by weight, very particularly preferably 3 to 92% by weight, of active ingredients of types A and B, in addition to conventional formulation auxiliaries.
  • the concentrations of the active ingredients A + B can vary in the formulations. In Spritzpuivern the active ingredient concentration is z. B. about 10 to 95 wt .-%, the rest of 100 wt .-% consists of conventional Formulation components. In the case of emulsifiable concentrates, the active ingredient concentration can be about 1 to 85% by weight, preferably 5 to 80% by weight. Dust-like formulations contain about 1 to 25% by weight, mostly 5 to 20% by weight of active substances, sprayable solutions about 0.2 to 25% by weight . -% , preferably 2 to 20 wt .-% active ingredients.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating agents and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned contain, if appropriate, the customary adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, anti-freeze agents and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and the pH and viscosity influencing means.
  • the combinations according to the invention achieve a reduction in the absolute application rate compared to the single application of a herbicidal active ingredient.
  • it is advantageous to use them together in a mixture or in succession in succession together with safeners or antidotes. Suitable safeners or antidots for the combinations according to the invention are, for. B.
  • antidots or safeners or groups of compounds which have proven themselves as safeners or antidots for the above-described product combinations of the invention include:
  • dichlorophenylpyrazole carboxylic acid preferably compounds such as 1 - (2,4-dichlorohenyl) -5-methyl-pyrazole-3-carboxylic acid ethyl ester (compound C1 - 2), 1- (2,4-dichlorophenyl) -5-isopropyl- ethyl pyrazole-3-carboxylic acid ester (compound C1-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) ethyl pyrazole-3-carboxylate (compound C1-4), 1- (2, 4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (compound C1-5) and related compounds as described in EP-A-0 333 131 and EP-A-0 269 806;
  • Patent application EP-A-0 582 198 has been described and proposed;
  • active substances of the type of Phe ⁇ oxyessig- or -propio ⁇ klarivate or aromatic carboxylic acids such as.
  • h) Compounds of the 5,5-diphenyl-2-isoxazoiin-3-carboxylic acid type, preferably 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (C3-1).
  • fenclorim 46-dichloro-2-phenyipyrimidine, Pesticide Manual, 11th edition, 1997, pp. 511-512
  • daimuron 1 - (1-methyl-1-phenylethyl) -3-p-tolylurea, pesticide Manual, 11th edition, 1997, p.
  • the safeners (antidotes) from groups a) to j) above reduce or prevent phytotoxic effects which can occur when the product combinations according to the invention are used in crops without impairing the effectiveness of the herbicides against harmful plants.
  • the field of use of the mixtures of herbicides according to the invention can be expanded considerably and, in particular, the use of safeners enables the use of combinations which have hitherto been able to be used only to a limited extent or with insufficient success. H. of combinations which, without Safe ⁇ er in low dosages with little breadth effect, did not lead to adequate control of the harmful plants.
  • the herbicidal mixtures according to the invention and the safeners mentioned can be used together (as a finished formulation or in the Ta ⁇ k-mix process) or in in any order.
  • the weight ratio of safener: herbicide (group A, ie the compound of the formula I and its salts) can vary within wide limits and is preferably in the range from 1: 100 to 100: 1, in particular from 1: 100 to 50: 1.
  • the optimum in each case Amounts of herbicides (type A and type B compounds) and safeners are usually dependent on the type of herbicide mixture used and / or on the safener used and on the type of crop to be treated.
  • the safeners of type C can be used for pretreating the seed of the crop (dressing the seeds) or introduced into the seed furrows before sowing or used together with the herbicide mixture before or after emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the cultivated area before sowing and the treatment of the sown but not yet overgrown cultivated areas. Common use with the herbicide mixture is preferred. Tank mixes or ready formulations can be used for this.
  • the required amounts of the Safe ⁇ er can vary within wide limits and are generally in the range from 0.001 to 1 kg, preferably 0.005 to 0.2 kg, of active ingredient per hectare.
  • Particularly inexpensive herbicidal compositions which are outstandingly suitable for use in rice result in the context of the invention when herbicides from group A) are used in combination with type B compounds and the Safe ⁇ er C2-1 and / or C3-1.
  • the formulations present in commercial form are optionally diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Dust-like preparations, ground or scatter granules, as well as sprayable Solutions are usually no longer diluted with other inert substances before use.
  • the invention also relates to a process for controlling unwanted plants, which is characterized in that a herbicidally effective amount of a combination of active compounds A + B according to the invention is applied to this or the cultivated area.
  • the active ingredients can be applied to the plants, parts of plants, plant seeds or the area under cultivation.
  • the compounds of the formula (I) or their salts (type A compounds) are applied in amounts of from 1 to 120 g ai / ha, preferably from 5 to 90 g ai / ha, very particularly preferably between 6 and 60 g ai / ha, while the application rates for the compounds of type B are generally 1 to 5000 g ai / ha. It is preferred to apply the active ingredients of types A and B simultaneously or at different times in a weight ratio of 1: 20000 to 200: 1. Also particularly preferred is the joint application of the active ingredients in the form of sachet mixtures, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
  • herbicidal compositions with the active compound combinations according to the invention are therefore used for the selective control of undesired plants.
  • the process for the selective control of harmful plants is particularly favorable when the herbicidal compositions of the invention are used in rice.
  • the combination partners of type A control a limited spectrum of annual and perennial weeds and cyperaceae when used alone in rice.
  • the spectrum of activity of the type A compounds is, however, significantly improved further by the combination with the type B partners mentioned in the invention, individual type groups additionally being recorded.
  • the herbicidal combinations according to the invention can advantageously be used to control unwanted plants in transgenic rice crops.
  • Transgenic crops are those in which the plants are made resistant to herbicides or pesticides through genetic manipulation. Rice crops modified in this way then allow selective use.
  • Bc selectively in rice, predominantly herbicides active against grass and dicotyledonous harmful plants and cyperaceae, selected from the group consisting of pendimethalin, clomazone, KIH 2023, oxadiargyl, cycloslulfamuron (AC 322, 140), azimsulfuron (DPX-A-8947), nicosulfuro , Cinmethylin, Indanofan, Pentoxazone,
  • the weight ratio of compounds of the formula I or their salts (type A compounds) and compounds from group B is generally in the range from 1: 20,000 to 200: 1, preferably 1: 8,000 to 100: 1, particularly preferably 1: 4000 to 50: 1.
  • a preferred use relates to the use of combinations which have contents of A and B compounds in a synergistically effective amount.
  • mixtures with combinations of A) and Ba for the selective control of grasses in rice. It is also preferred to use mixtures with combinations of A) and Bb) for the selective control of dicotyledons and cyperaceae in rice. It is further preferred to use mixtures with combinations of A) and Bc) for the selective control of grasses, dicotyledons and cyperaceae in rice.
  • the invention also includes mixtures of one or more combination partners A), preferably only A1 (ethoxysulfuron), and one or several combination partners ⁇ B), optionally in combination with one or more Safe ⁇ em C).
  • the mixtures described above can expediently be used together with one or more safeners.
  • preferred safeners are (5-chloro-8-quinolinooxy) acetic acid (1-methyl-hex-1-yl) ester (C2-1) and 5,5-diphenyl-2-isoxazoline-3-carboxylic acid methyl ester ( C3-1).
  • Safe ⁇ er C2-1 and C3-1 can advantageously be replaced by one or more compounds from the following group of safeners or used together with one or more of the following compounds: 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoli ⁇ -3-carboxylic acid ethyl ester (C1 -1),
  • one or two or more of the following pesticides may additionally be present in the mixtures of the invention in order to round off the properties, usually in minor amounts: abamectin, AC94377, AC263222, AC3-103630, acephate, aclo ⁇ ifen, acrinathrin, acypectas, AKH-7088, alachlor, alanycarb, aldicarb, aldoxycarb, allethrin, alloxydim, alpha-cypermethri ⁇ , ametryn, amidosulfymolate, amidosulfymolate , a ⁇ ilazi ⁇ e, a ⁇ thraquino ⁇ e, asulam, atrazine, azaconazole, azadirachtin, azamethiphos, azinphos-ethyl, azi ⁇ phos-methyl, azocyclotin, BAS480F
  • the herbicidal compositions (combinations) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial weeds that are difficult to control and that sprout from seeds or rhizomes, rhizomes or other permanent organs are also well captured by the active ingredient combinations. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
  • the weeds occurring in rice under specific cultivation conditions such as Sagittaria, Alisma, Rotala, Monochoria, Eleocharis, Scirpus, Cyperus etc., are combated excellently by the active compound combinations according to the invention. If the herbicidal compositions according to the invention are applied before germination, either the emergence of the weed seedlings is prevented completely, or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • compositions according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, the crop is only insignificantly or not at all damaged. For this reason, the agents are particularly suitable, particularly in rice, for the selective control of undesired plant growth.
  • the harmful plants to be controlled include, as already mentioned, grasses, dicotyledons and / or cyperaceae which are otherwise difficult to control.
  • Harmful plants to be controlled preferably with the combinations of type A and type B compounds according to the invention include, among others, Echinochloa colonum, Echinochloa chinese, Echinochloa crus galli, Leptochloa chin./fil., Paspalum dis., Brachiaria platyphylla, Digitaria spp., Ischaemum , Leersia hexandra, Oryza sativa (Red rice), Cenchrus echinatus, Rottboellia exaltata, Leersia and the like on the side of the grasses, Monochoria vag., Potamogeton dis., Rotala indica, Marsilea crenata, Ludwigia ad., Salvi ⁇ a mol., Ipomoea,
  • Cyperus iria Fimbristylis litt, Cyperus ferax, Cyperus esculentes on the side of the annual Cyperaceae as well as Eleocharis spp., Scirpus spp., Scirpus mucronatus and Cyperus rotundus on the side of the perennial Cyperaceae.
  • combinations according to the invention permit the control of otherwise resistant harmful plants in an excellent manner.
  • a dusting agent is obtained by mixing 10 parts by weight of an active compound combination according to the invention and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a water-dispersible, wettable powder is obtained by adding 25 parts by weight of active compounds A + B, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium mixes as a wetting and dispersing agent and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active compounds A + B with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Parts of paraffinic mineral oil (boiling range e.g. approx. 255 to 277 ° C.) and ground in a attritor to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) A water-dispersible granulate is obtained by adding 75 parts by weight of active compounds A + B,
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of active ingredients A + B
  • Extruder granules are obtained by mixing 20 parts by weight of active ingredients A + B, 3 parts by weight of sodium lignosulfonate, 1 part by weight of carboxymethyl cellulose and 76 parts by weight of kaolin, and grinding and moistening them with water. This mixture is extruded and then dried in an air stream.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous herb plants are placed in sandy loam in plastic pots 9 cm in diameter and covered with earth.
  • Weeds found in rice cultivation are cultivated in soil saturated with water, with enough water being poured into the pots that the water is up to the surface of the soil or a few millimeters above it.
  • the active compound combinations according to the invention formulated in the form of wettable powders or emulsion concentrates and, in parallel experiments, the correspondingly formulated individual active compounds are then applied as aqueous suspensions or as emulsions with a water application rate of the equivalent of 300 to 600 l / ha, in different dosages to the surface of the covering earth or poured into the irrigation water for rice.
  • the herbicidal compositions according to the invention have good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous herb plants are placed in plastic pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions (temperature, air humidity, water supply).
  • Weeds found in rice cultivation are cultivated in pots in which water is up to 2 cm above the surface of the soil. Three weeks after sowing, the test plants are treated at the three-leaf stage.
  • the active compound combinations according to the invention formulated as wettable powder or emulsion concentrates and, in parallel tests, the correspondingly formulated individual active compounds are sprayed onto the green plant parts in various dosages with a water application rate of the equivalent of 300 to 600 l / ha, and after about 3 to 4 weeks of the test plants in the greenhouse under optimal conditions Growth conditions (temperature, humidity, water supply) rated the effect of the preparations visually in comparison to untreated controls.
  • the active ingredients are also added directly to the irrigation water (application in analogy to the so-called granulate application) or sprayed onto plants and the irrigation water.
  • the experiments are repeated several times, up to five times.
  • the herbicidal compositions according to the invention also have good post-emergence properties herbicidal activity against a broad spectrum of economically important grasses and weeds.
  • Field trials are carried out on areas that are cultivated in practice with natural changes. After sowing or emergence of the culture / weeds / grasses, plots with about 20 to 1 Om 2 and 2 to 4 repetitions are applied. Plot sprayers are used for this. The effects of the herbicide / combinations are assessed visually in the period from 1 to 8 weeks after application and the effects are recorded as a percentage (0-100%) compared to untreated control plots. The results represent mean values of the 2 to 4 repetitions for the respective herb / grass species.
  • the effect of the individual components is added and compared with the effectiveness of the mixtures of the same dosage. It was often found that the combinations showed higher efficiencies than the sum of the individual effects.
  • the expected value is calculated using the COLBY formula and compared with the empirically determined result.
  • the calculated, theoretically expected efficiency of a combination is determined using the formula by SR Colby: "Calculation of synergistic and antagonistic responses of herbicide combinations", Weeds 15 (1967), pages 20 to 22.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
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  • Plant Pathology (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP1999/004957 1998-07-16 1999-07-14 Herbizide mittel mit substituierten phenoxysulfonylharnstoffen WO2000003592A2 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP99936162A EP1096854A2 (de) 1998-07-16 1999-07-14 Herbizide mittel mit substituierten phenoxysulfonylharnstoffen
JP2000559736A JP2002520341A (ja) 1998-07-16 1999-07-14 置換されたフェノキシスルホニル尿素を含有する除草組成物
AU52812/99A AU5281299A (en) 1998-07-16 1999-07-14 Herbicidal agents with substituted phenoxysulfonylureas
BRPI9912823A BRPI9912823B1 (pt) 1998-07-16 1999-07-14 composições herbicidas compreendendo fenoxissulfoniluréias substituídas, processo para combater plantas daninhas, aplicação e processo para a preparação das mesmas

Applications Claiming Priority (4)

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DE19832017A DE19832017A1 (de) 1998-07-16 1998-07-16 Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis
DE19832017.5 1998-07-16
DE19928453.9 1999-06-24
DE1999128453 DE19928453A1 (de) 1999-06-24 1999-06-24 Herbizide Mittel mit substituierten Phenoxysulfonylharnstoffen

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WO2000003592A3 WO2000003592A3 (de) 2000-11-09

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US7741246B2 (en) * 2002-03-27 2010-06-22 Kumiai Chemical Industry Co., Ltd. Herbicide composition and weed-controlling method using the same
EP1130965B2 (de) † 1998-11-21 2012-04-04 Bayer CropScience AG Kombinationen aus herbiziden und safenern
CN102405924A (zh) * 2011-11-17 2012-04-11 广东中迅农科股份有限公司 一种含有苄嘧磺隆和二甲戊灵的农药组合物
EP2959776A4 (en) * 2013-02-22 2016-07-20 Ishihara Sangyo Kaisha HERBICIDE COMPOSITION
CN105284854B (zh) * 2015-11-30 2017-03-22 山东汤普乐作物科学有限公司 一种靶标为水稻田水葱的除草剂组合物及其制备方法

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TWI510190B (zh) * 2010-11-26 2015-12-01 Ishihara Sangyo Kaisha 除草組成物
JP5927007B2 (ja) * 2011-04-11 2016-05-25 石原産業株式会社 除草組成物
CN102405922A (zh) * 2011-10-25 2012-04-11 陕西美邦农药有限公司 一种含乙氧磺隆与2甲4氯钠的除草组合物
CN102365965B (zh) * 2011-11-04 2014-06-18 陕西美邦农药有限公司 一种含乙氧磺隆的农药组合物
CN102657208B (zh) * 2012-05-30 2015-04-08 广西新晶科技有限公司 含乙氧磺隆的除草剂组合物及其生产方法
CN102894005B (zh) * 2012-11-14 2014-08-13 联保作物科技有限公司 一种除草组合物
CN103271069A (zh) * 2013-06-19 2013-09-04 北京燕化永乐农药有限公司 一种复配除草剂
CN104094954A (zh) * 2014-03-21 2014-10-15 江苏省农业科学院 一种含乙氧磺隆和氯吡嘧磺隆的农药组合物及其应用
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WO2000060944A1 (en) * 1999-04-13 2000-10-19 Aventis Cropscience S.A. Herbicidal compositions for paddy fields
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EA008437B1 (ru) * 2001-12-07 2007-06-29 Байер Кропсайенс Гмбх Синергические гербицидные средства
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EP2140761A3 (de) * 2001-12-07 2010-07-21 Bayer CropScience Aktiengesellschaft Synergische herbizide Mittel
CN101731263B (zh) * 2001-12-07 2013-10-30 拜尔作物科学股份公司 增效除草组合物
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WO2004004459A1 (en) * 2002-07-04 2004-01-15 Syngenta Participations Ag Weed control process comprising the application of mesotrione and a second herbicide
RU2313219C2 (ru) * 2006-01-18 2007-12-27 Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством" (НИТИГ) Гербицидное средство и способ его получения (варианты)
CN102405924A (zh) * 2011-11-17 2012-04-11 广东中迅农科股份有限公司 一种含有苄嘧磺隆和二甲戊灵的农药组合物
EP2959776A4 (en) * 2013-02-22 2016-07-20 Ishihara Sangyo Kaisha HERBICIDE COMPOSITION
JPWO2014129512A1 (ja) * 2013-02-22 2017-02-02 石原産業株式会社 除草組成物
CN105284854B (zh) * 2015-11-30 2017-03-22 山东汤普乐作物科学有限公司 一种靶标为水稻田水葱的除草剂组合物及其制备方法

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KR20010079532A (ko) 2001-08-22
WO2000003592A3 (de) 2000-11-09
CO5090896A1 (es) 2001-10-30
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EP1096854A2 (de) 2001-05-09
AU5281299A (en) 2000-02-07
CN1318978A (zh) 2001-10-24
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