WO2010066679A2 - Mélanges herbicides - Google Patents

Mélanges herbicides Download PDF

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Publication number
WO2010066679A2
WO2010066679A2 PCT/EP2009/066528 EP2009066528W WO2010066679A2 WO 2010066679 A2 WO2010066679 A2 WO 2010066679A2 EP 2009066528 W EP2009066528 W EP 2009066528W WO 2010066679 A2 WO2010066679 A2 WO 2010066679A2
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WIPO (PCT)
Prior art keywords
inhibitors
active ingredient
contain
methyl
active
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PCT/EP2009/066528
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German (de)
English (en)
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WO2010066679A3 (fr
Inventor
Liliana Parra Rapado
William Karl Moberg
Matthias Witschel
Thomas Seitz
Anja Simon
Trevor William Newton
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Basf Se
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Publication of WO2010066679A3 publication Critical patent/WO2010066679A3/fr

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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
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • 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 present invention relates to herbicidal mixtures containing
  • Inhibitors selected from chlorothiamide, dichlobenil, flupoxam, isoxaben, triacidlam, indaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-1 ⁇ 4 - [1, 2,4,6] thiatriazine-3-ylamine and thaxtomin derivatives of the formula I.
  • R a is CN, CF 3 or NO 2 ;
  • R 1 is H or OH;
  • A is phenyl or a five- or six-membered fully unsaturated ring which, in addition to carbon, may contain 1, 2 or 3 heteroatoms selected from O, N and S; and
  • R 1, R 2 H, OH, halogen, C -C alkyl or C 4 -alkyl mean 4 haloalkyl,
  • Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R; R is halogen, Ci -C4 -alkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkyl, or -C 4 -
  • R 21 , R 22 , R 23 , R 24 are H, halogen or C 1 -C 4 -alkyl; X is O or NH; n is 0 or 1.
  • the problem is that their compatibility with crops, especially dicotyledonous crops such as cotton, rape and grass plants such as barley, millet, corn, rice, wheat and sugar cane is not always satisfactory, ie in addition to the harmful plants and the crops in one not tolerable dimensions damaged. By reducing the application rates while the crops are spared, but at the same time naturally decreases the extent of harmful plant control.
  • the herbicides can be used only in a narrow time window in order to achieve the desired herbicidal action, wherein the time window can be influenced in an unpredictable manner by weather conditions.
  • the z.T. themselves have herbicidal activity, better crop compatibility can be achieved.
  • the active ingredients act as antidotes or antagonists in these cases and are also referred to as safeners, as they reduce the damage to the crop or even prevent it.
  • the object of the invention is to provide herbicidal compositions which have a high activity against unwanted harmful plants.
  • the compositions should at the same time have good crop compatibility. sen.
  • the compositions of the invention should show a broad spectrum of activity.
  • the invention relates to compositions in the form of herbicidally active crop protection compositions containing a herbicidally effective amount of a drug combination comprising at least one CBI and at least one VLCFA inhibitor, and at least one liquid and / or solid carrier and / or one or more surfactants and, if desired one or more further auxiliaries customary for pesticides.
  • the invention also relates to compositions in the form of a plant protection composition formulated as a 1-component composition, comprising a combination of active substances comprising at least one active substance A and at least one further active ingredient B, and at least one solid or liquid carrier and / or one or more surface-active substances if desired, one or more further auxiliaries customary for pesticides.
  • the invention also relates to compositions in the form of a plant protection composition formulated as a 2-component composition comprising a first component comprising at least one active substance A, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient, selected from the active compounds B, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.
  • compositions of the invention containing at least one active ingredient A and at least one active ingredient B exhibit better herbicidal efficacy, i. H. a better action against harmful plants than would have been expected due to the herbicidal activity observed for the individual compounds (synergistic effect), or a broader spectrum of activity.
  • compositions according to the invention which contain both at least one active ingredient A and one active ingredient B, the time window within which the desired herbicidal action can be achieved is increased. This allows a more flexible temporal use of the compositions of the invention compared to the individual compounds.
  • compositions of the invention also show a good herbicidal activity against harmful plants and a better crop compatibility.
  • the compositions according to the invention have a better herbicidal activity, ie a better action against harmful plants than would have been expected on account of the herbicidal activity observed for the individual compounds.
  • the invention relates to a method for controlling undesired plant growth, in particular in cultivated areas of crop plants, for example in crops of the following crop plants: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var.
  • Theobroma cacao Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays, especially cereal, maize, soybean, rice, rapeseed, cotton, potato, peanut or permanent crops, as well as in crops that are resistant to one or more herbicides or to insect infestation through genetic engineering or breeding measures.
  • the invention also relates to a method for desiccation or defoliation of plants. In the latter method, it is irrelevant whether the herbicidally active compounds of components A) and B) are formulated and applied together or separately and in which order the application is carried out with separate application.
  • a preferred embodiment of the combinations according to the invention contains as active ingredient A chlorothiamide.
  • a further preferred embodiment contains dichlobenil as active ingredient A.
  • a further preferred embodiment contains as active ingredient A flupoxam.
  • a further preferred embodiment contains as active ingredient A isoxaben.
  • a further preferred embodiment contains as active ingredient A triaziflam.
  • a further preferred embodiment contains as active ingredient A 1 -cyclohexyl-5-pentafluorophenyloxy-1 ⁇ 4 - [1, 2,4,6] thiatriazin-3-ylamine (compound A-6).
  • a further preferred embodiment contains Indaziflam as active ingredient A.
  • a further preferred embodiment contains, as active ingredient A, a thaxtomin derivative of the formula I, in particular one in which A is phenyl or thiophene.
  • active ingredients come into question:
  • An embodiment of the invention contains as active ingredient B a chloroacetamide.
  • Another embodiment contains as active ingredient B an oxyacetanilide.
  • Another embodiment contains as active ingredient B an acetanilide.
  • Another embodiment contains as active ingredient B a tetrazolinone.
  • Another embodiment contains as active ingredient B one of the other VLCFA inhibitors, as defined above.
  • Preferred embodiments of the invention relate to combinations of an active substance A with an active ingredient B which is selected from dimethachlor, metolachlor, metolachlor-S, flufenacet, napropamide, fentrazamide and pyroxasulfone.
  • a further preferred embodiment relates to the combination of an active compound A with an isoxazoline compounds of the formula 2.
  • # is the bond to the molecular skeleton
  • R 25 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
  • R 26 is C 1 -C 4 -alkyl;
  • R 27 is halogen, C 1 -C 4 - alkoxy or Ci-C4-haloalkoxy;
  • R 28 is H, halogen, CrC 4 - alkyl, Ci-C 4 haloalkyl or Ci-C4-haloalkoxy;
  • m is 0, 1, 2 or 3;
  • X is oxygen;
  • n is 0 or 1
  • Particularly preferred compounds of the formula 2 have the following meanings:
  • Particularly preferred compounds of the formula 2 are:
  • the binary combinations according to the invention may optionally contain a further active component C.
  • Such ternary combinations may comprise as active component C at least one and preferably one herbicide C and / or at least one and preferably one safener D.
  • compositions according to the invention comprise as third component c) at least one, and preferably a herbicide selected from groups d) to c13) as defined below.
  • at least one, and preferably a safener D is present as the third component C).
  • the third component C) is a herbicide selected from groups d) to c13) and the fourth component at least one, and preferably a safener D before.
  • compositions of the invention those containing at least one herbicide C are preferred.
  • herbicides C that can be used in combination with the active compounds A according to the present invention are: d) from the group of lipid biosynthesis inhibitors:
  • Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; c8) from the group of DHP synthase inhibitors: asulam; c9) from the group of mitosis inhibitors: amiprophos, amiprophos-methyl, benfluralin, butamiphos, butraline, carbetamide,
  • Chlorpropham chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, flulcholine, oryzalin, pendimethalin, prodiamine, prophy, propyzamide, tebutam, thiazopyr and trifluralin; c10) from the group of decoupling herbicides: dinoseb, dinoterb and DNOC and its salts; d 1) from the group of auxin herbicides:
  • MSMA oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamin, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinoline (CAS 499223-49-3) and its salts and esters.
  • Suitable safeners D are in particular: Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamide, Dichlormid, Dicyclonon,
  • herbicides C which can be used in combination with the active compounds A and B according to the present invention are: d) from the group of lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop- P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate; c2) from the group of ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, lodosulfuron, lodosulfuron-methyl- sodium
  • Examples of preferred safeners D are Benoxacor, Cloquintocet, Cyprosulfamide, Dichlormid, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Isoxadifen, Mefenpyr, Naph- thalian acid anhydride, oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3.
  • oxazolidine R-29148, CAS 52836-31-4.
  • Particularly preferred safeners D are benoxacor, cloquintocet, cyprosulfamide, dichloromide, fenchlorazole, isoxadifen, mefenpyr, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2 , 2,5-Trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine (R-29148, CAS 52836-31-4).
  • the active compounds A, B, C and D are known herbicides and safeners, see, for. B. The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 Volume 86, Meister Publishing Company, 2000; Hock, C. Fedtke, R.R. Schmidt, Herbicides, Georg Thieme Verlag, Stuttgart 1995; W.H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine [CAS-No.
  • both the pure isomers and mixtures thereof can be used in the compositions of the invention. If the herbicides and / or safeners have one or more chiral centers and are therefore present as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof can be used in the compositions according to the invention.
  • the herbicides and / or the safeners can also be used in the form of their agriculturally acceptable salts.
  • the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the action of the active ingredients.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, the alkaline earth metals, preferably of calcium and magnesium, and the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium, in which one to four hydrogen atoms are replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably Ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylam
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably Formate, acetate, propionate and butyrate.
  • Such active compounds which have a carboxyl group can be used in the form of the acid, in the form of an agriculturally suitable salt but also in the form of an agriculturally acceptable derivative in the compositions according to the invention, e.g.
  • amides such as mono- and di-C 1 -C 6 -alkylamides or arylamides
  • esters e.g. as allyl esters, propargyl esters, C 1 -C 10 -alkyl esters, alkoxyalkyl esters and thioesters, e.g. be used as Ci-Cio-alkylthioester.
  • Preferred mono- and di-C 1 -C 6 -alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl) or isooctyl (2-ethylhexyl) esters.
  • Preferred C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl esters are the straight-chain or branched C 1 -C 4 -alkoxyethyl esters, for example the methoxyethyl, ethoxyethyl or butoxyethyl esters.
  • An example of the straight-chain or branched C 1 -C 10 -alkyl thioesters is the ethylthioester.
  • binary compositions includes such compositions comprising one or more agents A (CBI) and one or more agents B (VLCFA inhibitors). Accordingly, the term “ternary compositions” includes those compositions which incorporate a or more CBI, one or more VLFA inhibitors, and one or more herbicides C and / or safener D.
  • the weight ratio of the active substances A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1.
  • Weight ratio of component a): c) usually in the range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1, and the weight ratio of components b): c) usually in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1 : 250 to 250: 1, and more preferably in the range of 1: 75 to 75: 1.
  • compositions which correspond to the binary compositions and which additionally comprise a safener D, in particular selected from benoxacor, cloquintocet, cyprosulfamide, dichloromethane, fenchlorazole, isoxadifen, mefenpyr, 4- (dichloroacetyl) -1-oxa-4- azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836-31-4).
  • a safener D in particular selected from benoxacor, cloquintocet, cyprosulfamide, dichloromethane, fenchlorazole, isoxadifen, mefenpyr, 4- (dichloroacetyl) -1-oxa-4- azaspiro [4.5] decane (MON4660, CAS 7152
  • the combination of the active compounds A and B and their agriculturally useful salts are suitable - both as mixtures of isomers and in the form of pure isomers - as herbicides. They are suitable as such or as appropriately formulated agent.
  • the combinations of active compounds A and B, in particular the preferred embodiments thereof, or agents containing them can be used in a further number of crop plants for the removal of undesirable plants.
  • the cultures mentioned in the introduction may be considered.
  • crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods.
  • Genetically engineered plants are plants whose genetic material has been altered in a way that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information).
  • one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • the combination of the active compounds A and B is also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration.
  • compositions for the desiccation and / or defoliation of plants, processes for the preparation of these agents and methods for the desiccation and / or defoliation of plants with the compounds of formula I have been found.
  • the compounds of the formula I are particularly suitable for drying out the aerial parts of crop plants such as potatoes, rape, sunflower me and soybean but also cereals. This enables a completely mechanical harvesting of these important crops.
  • harvest facilitation which is made possible by the time-concentrated dropping or reducing the adhesion of the tree to citrus fruit, olives or other types and varieties of pome, stone and peel fruit.
  • the same mechanism i.e. promoting the formation of release webs between fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of crops, especially cotton.
  • shortening the time interval in which each cotton plant ripens leads to increased fiber quality after harvest.
  • the active compounds or the herbicidal compositions containing them can, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, Dusting, scattering, pouring or treatment of the seed or mixing with the seed are applied.
  • the forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions contain a herbicidally effective amount of at least one active substance A and at least one active substance B or an agriculturally useful salt thereof and auxiliaries customary for the formulation of pesticides.
  • auxiliaries are preferred auxiliaries, solid carriers, surface-active substances (such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.
  • surface-active substances such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives
  • organic and inorganic thickeners such as bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.
  • thickeners ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides may be added to stabilize the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS der Fa. Thor Chemie)
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 1 12 and Cl.
  • Solvent Red 1 known dyes, and pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 1, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and
  • Suitable inert additives are, for example: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthal
  • Solid carriers are mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • alkali alkaline earth
  • ammonium salts of aromatic sulfonic acids eg lignosulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types , Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE)
  • fatty acids alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, e.g. Coating, impregnation and homogeneous granules can by
  • Binding of the active ingredients to solid carriers are produced.
  • Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of the formula I or Ia, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
  • concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits.
  • the formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the combinations according to the invention can be formulated, for example, as follows:
  • Dispersible Concentrates 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • active compound 25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • organic solvent for example alkylaromatics
  • calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and a homogeneous emulsion brought. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the application of the active substances or herbicidal compositions containing them can be carried out in the pre-emergence, post-emergence or together with the seed of a crop. It is also possible to apply the herbicidal compositions or active ingredients by pretreating with the herbicidal compositions or active ingredients. seed of a crop plant is applied. If the active ingredients are less compatible with certain crops, application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so as not to hit the leaves of the sensitive crops as far as possible, while the active ingredients on the leaves below grow undesirable plants or the uncovered soil surface (post-directed, lay-by).
  • the application of the active ingredients or of the herbicidal agents can be carried out by treating seed.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, e.g. Grains, seeds, fruits,
  • seed preferably describes grains and seeds here.
  • Seeds of the crops mentioned above, but also the seed of transgenic plants or plants obtained by conventional breeding methods, can be used as seed.
  • the required application rate of pure drug composition i. A and B and optionally C / D without formulation auxiliaries, is dependent on the composition of the plant population, on the developmental stage of the plants, on the climatic conditions at the place of use and on the application technique.
  • the application rate of A and B and optionally C / D is 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha and in particular 0.01 to 2 kg / ha of active substance (a.S.).
  • the required application rates of active substances A are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the required application rates of active substances B are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the required application rates of active substances C are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the required application rates of safeners D are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the funds are fed to the plants primarily by foliar spraying.
  • the application can, for example, with water as a carrier by conventional spraying techniques
  • Spray mixture amounts of about 100 to 1000 l / ha (eg 300 to 400 l / ha) take place.
  • compositions in the so-called “low-volume” and “ultra-low-volume” method is just as possible as their application in the form of so-called microgranules
  • the administration of the active substances or of the herbicidal compositions containing them can be carried out in the pre-emergence phase It is also possible to apply the compositions by applying seed of a crop plant pretreated with a composition according to the invention: If the active compounds A and B and, if appropriate, C are less compatible for certain crops
  • application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so that the leaves of the sensitive crops are not affected if possible, while the active ingredients on the leaves underneath growing unwanted plants or the uncovered Bodenflä (post-directed, lay-by).
  • the application of the composition may be by treatment of seed.
  • the treatment of seed comprises essentially all techniques familiar to the person skilled in the art (seed dressing, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting) based on the compounds according to the invention
  • seed dressing seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms.
  • seed preferably describes grains and seeds here.
  • Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
  • the application rates of active ingredient are 0.001 to 3.0 kg / ha, preferably 0.01 to 1.0 kg / ha of active substance (a.
  • the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
  • mineral salt solutions which are used for the elimination of nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • the active compounds and the compositions according to the invention may also have a plant-strengthening effect. They are therefore willing to mobilize zenstru defenses against infestation by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.
  • the active ingredients can be used to protect plants against attack by undesirable microorganisms within a certain period of time after the treatment.
  • the period within which protection is induced generally extends to 1 to 28 days, preferably 1 to 14 days after treatment of the plants with the compounds I or after treatment of the seeds, up to 9 months after sowing.
  • the active compounds and the compositions according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the culture vessels used were plastic pots with loamy sand with about 5.8% humus as substrate.
  • the seeds of the test plants were sown separately by species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
  • the test plants were grown depending on the growth form only to a stature height of 1, 5 to 15 cm and then treated with the suspended or emulsified in water agents.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively.
  • the trial period lasted for 1 to 4 weeks.
  • the plants were cared for, and their response to each treatment was evaluated.
  • the rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course.
  • a good herbicidal activity is at Wer- at least 70 and a very good herbicidal activity is given at values of at least 85.
  • the plants used in the greenhouse experiments are composed of the following species:
  • a.S. active substance, based on 100% active ingredient.
  • the Colby values E are given in parentheses () in Application Examples 1 to 9.
  • Agent I-9 was used as a 3S, 6S isomer.
  • Drug I-9 was used as 3S, 6S isomer.
  • Use Example 9 Synergistic herbicidal action of 1-10 with post-emergence 2-10

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  • Pest Control & Pesticides (AREA)
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Abstract

L'invention porte sur des mélanges herbicides contenant a) au moins une matière active A du groupe des inhibiteurs de la biosynthèse de la cellulose choisis parmi le chlorthiamide, le dichlobénil, le flupoxam, l'isoxabène, le triaziflam, l'indaziflam, la 1-cyclohexyl-5-pentafluorophényloxy-1-λ4-[1,2,4,6]thiatriazin-3-ylamine et les dérivés de la thaxtomine de formule (I), où les variables sont définies dans la description, et b) au moins une matière active B du groupe des inhibiteurs du VLCFA choisis parmi les chloracétamides, les oxyacétanilides, les acétanilides, les tétrazolinones, et d'autres inhibiteurs du VLCFA ; l'invention porte également sur des produits contenant ces mélanges herbicides, ainsi que sur des procédés pour lutter contre une croissance indésirable de végétaux.
PCT/EP2009/066528 2008-12-09 2009-12-07 Mélanges herbicides WO2010066679A2 (fr)

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WO2013066894A3 (fr) * 2011-10-31 2013-09-26 Novozymes Biologicals, Inc. Procédés de lutte contre les mauvaises herbes faisant appel à la thaxtomine ou à des compositions de thaxtomine en combinaison avec un herbicide bénéfique
US20140256551A1 (en) * 2013-03-08 2014-09-11 Dow Agrosciences Llc Herbicidal compositions comprising isoxaben and flufenacet
WO2014138561A1 (fr) * 2013-03-08 2014-09-12 Dow Agrosciences Llc Compositions herbicides comprenant de l'isoxabène et de l'aminopyralide
AU2013203762B2 (en) * 2012-07-19 2015-04-09 Marrone Bio Innovations, Inc. Uses of thaxtomin and thaxtomin compositions as herbicides
CN104982443A (zh) * 2015-06-25 2015-10-21 陕西上格之路生物科学有限公司 一种含噁嗪草酮和苯噻酰草胺的除草组合物
AU2015202036B2 (en) * 2012-07-19 2016-07-21 Marrone Bio Innovations, Inc. Uses of thaxtomin and thaxtomin compositions as herbicides
WO2019222552A1 (fr) 2018-05-16 2019-11-21 University Of Florida Research Foundation Procédés et compositions pour des analogues de 2,5-dicétopipérazines substituées

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Cited By (17)

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CN104284583A (zh) * 2011-10-31 2015-01-14 诺维信生物农业公司 用Thaxtomin和组合有益除草剂的Thaxtomin组合物控制杂草的方法
WO2013066894A3 (fr) * 2011-10-31 2013-09-26 Novozymes Biologicals, Inc. Procédés de lutte contre les mauvaises herbes faisant appel à la thaxtomine ou à des compositions de thaxtomine en combinaison avec un herbicide bénéfique
AU2015202036B2 (en) * 2012-07-19 2016-07-21 Marrone Bio Innovations, Inc. Uses of thaxtomin and thaxtomin compositions as herbicides
AU2013203762B2 (en) * 2012-07-19 2015-04-09 Marrone Bio Innovations, Inc. Uses of thaxtomin and thaxtomin compositions as herbicides
EP2964021A1 (fr) * 2013-03-08 2016-01-13 Dow AgroSciences LLC Compositions herbicides contenant de l'isoxabène et du flufénacet
WO2014138561A1 (fr) * 2013-03-08 2014-09-12 Dow Agrosciences Llc Compositions herbicides comprenant de l'isoxabène et de l'aminopyralide
CN105007727A (zh) * 2013-03-08 2015-10-28 美国陶氏益农公司 包含异噁酰草胺和氟噻草胺的除草组合物
WO2014138547A1 (fr) 2013-03-08 2014-09-12 Dow Agrosciences Llc Compositions herbicides contenant de l'isoxabène et du flufénacet
EP2964021A4 (fr) * 2013-03-08 2016-07-20 Dow Agrosciences Llc Compositions herbicides contenant de l'isoxabène et du flufénacet
US20140256551A1 (en) * 2013-03-08 2014-09-11 Dow Agrosciences Llc Herbicidal compositions comprising isoxaben and flufenacet
US9730444B2 (en) 2013-03-08 2017-08-15 Dow Agrosciences Llc Herbicidal compositions comprising isoxaben and aminopyralid
AU2014225487B2 (en) * 2013-03-08 2017-09-14 Corteva Agriscience Llc Herbicidal compositions comprising isoxaben and flufenacet
CN105007726B (zh) * 2013-03-08 2017-09-29 美国陶氏益农公司 包含异噁酰草胺和氯氨基吡啶酸的除草组合物
RU2650555C2 (ru) * 2013-03-08 2018-04-16 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Гербицидные композиции, содержащие изоксабен и аминопиралид
CN104982443A (zh) * 2015-06-25 2015-10-21 陕西上格之路生物科学有限公司 一种含噁嗪草酮和苯噻酰草胺的除草组合物
WO2019222552A1 (fr) 2018-05-16 2019-11-21 University Of Florida Research Foundation Procédés et compositions pour des analogues de 2,5-dicétopipérazines substituées
EP3793360A4 (fr) * 2018-05-16 2022-02-16 University of Florida Research Foundation Procédés et compositions pour des analogues de 2,5-dicétopipérazines substituées

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