EP1956902A2 - Melanges herbicides - Google Patents

Melanges herbicides

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Publication number
EP1956902A2
EP1956902A2 EP06819608A EP06819608A EP1956902A2 EP 1956902 A2 EP1956902 A2 EP 1956902A2 EP 06819608 A EP06819608 A EP 06819608A EP 06819608 A EP06819608 A EP 06819608A EP 1956902 A2 EP1956902 A2 EP 1956902A2
Authority
EP
European Patent Office
Prior art keywords
methyl
components
mixture
component
mixtures
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP06819608A
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German (de)
English (en)
Inventor
Herve R. Vantieghem
Bernd Sievernich
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1956902A2 publication Critical patent/EP1956902A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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 mixtures which
  • R is chlorine or methyl, or one of its environmentally compatible salts, esters or amides; and b) esters of C6-C22 fatty acids of vegetable origin.
  • the present invention also relates to herbicidally active mixtures.
  • the mixture may contain, in addition to the components a) and b) further components. Examples include c) nitrogen-containing fertilizers, d) other herbicides or e) safeners.
  • the invention furthermore relates to compositions such as, for example, the ready-to-use spray mixture containing the mixtures and at least one solid or liquid carrier and optionally at least one surface-active agent. Methods for the preparation of these agents and their use as well as methods for controlling undesired plant growth are also the subject of this invention.
  • 3-Heterocyclyl-substituted benzoyl derivatives are suitable as herbicides. It was also known to use them in herbicidal mixtures.
  • WO 99/63823 discloses herbicidal mixtures of 3-heterocyclyl-substituted benzoyl derivatives, nitrogen fertilizers and an adjuvant.
  • WO 00/53014 discloses a synergistic mixture of 3-heterocyclyl-substituted benzoyl derivatives and an adjuvant containing a C 1 -C 5 -alkyl-C 5 -C 22 -alkanoate, a C 10 -C 20 -carboxylic acid, a partial phosphoric acid ester or a partial sulfuric acid ester of a monohydroxy-functional one Polyalkyl ether and optionally an alkylpolyoxyalkylene polyether.
  • An object of the present invention was to develop mixtures based on 4,5-dihydroisoxazol-3-yl-substituted benzoyl derivatives, which have a broad applicability.
  • the object of the present invention was, in particular, to develop a herbicidally active mixture based on this class of active ingredient, which assists the specific activity of the active ingredient used and at the same time ensures reliable use.
  • Component a) of the mixtures according to the invention is 4- [2-methyl-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulphonylbenzoyl] -1-methyl-5-hydroxy-1H-pyrazole or 4- [2 Chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulphonylbenzoyl] -1-methyl-5-hydroxy-1H-pyrazole, preferably 4- [2-methyl-3- (4,5-) dihydroisoxazol-3-yl) -4-methylsulfonylbenzoyl] -1-methyl-5-hydroxy-1H-pyrazole.
  • esters of C6-C22 fatty acids of plant origin used as component b) are known per se to the person skilled in the art as "methylated seed oil” or MSO.
  • methylated seed oil For their production, for example, native vegetable oil is split into glycerol and fatty acids; the fatty acids are separated and esterified, e.g. methylated or ethylated.
  • Suitable plants or their seeds for obtaining the native oil are, for example, soybean, maize, sunflower, oilseed rape, cotton, linseed, coconut, palm, thistle, walnut, peanut, olive or castor, in particular oilseed rape.
  • the fatty acids have 6 to 22 carbon atoms, with the majority being C14 to C18.
  • the fatty acids can be both saturated and unsaturated.
  • the MSOs contain methyl capronate, methyl caprylate, methyl caprinate, Methyl laurate, methyl myristate, methyl stearate, methyl palmitate, methyl oleate, methyl linoleate, methyl linolenate and the ethyl esters in different distribution patterns depending on the type of oil or treatment. MSOs of various origins can also be mixed.
  • MSO is commercially available. Examples are DESTINY from Cenex, MSO Concentrate OiI 'from Loveland,' MSO 'from Helena Chemical and SCOIL from Agsco.
  • commercial products besides MSO may contain either UAN (ijrea ammonium riitrate ⁇ urea ammonium nitrate) or AMS (ammonium sulfate ⁇ ammonium sulfate), such as PERSIST PLUS and PERSIST EXTRA from Prescision (MSO plus UAN) and DYNE-A-PAK from Helena Chemical (MSO plus UAN).
  • the user for example the farmer, uses the inventive herbicidal mixture or the herbicidal agent, usually for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane.
  • the herbicidal mixture with water and / or buffer is brought to the desired application concentration, optionally further auxiliaries and additives are added, and thus the ready-spray mixture or the herbicidal composition according to the invention is obtained.
  • 50 to 500 liters of ready-spray mixture per hectare of agricultural land preferably 100 to 400 liters.
  • the mixture according to the invention is, in particular, herbicidally active and contains the components a) and b) in synergistically effective amounts. It is selective in its action for those crops for which the individual components themselves are also compatible.
  • the application rate of component a) of the mixture according to the invention is usually from 2.5 to 100 g / ha, preferably from 5 to 75 g / ha. Particularly preferred are application rates of 5 to 25 g / hectare. This corresponds to a concentration of the component a) of 0.00625 g / lsp ⁇ tzbmhe to 1 g / lsp ⁇ tzbmhe with a conventional spray liquor volume of 100 to 400 liters per hectare.
  • the destruction of undesired plant growth before planting the crops 2.5 g to 100 g of component a) in 100 to 400 liters of spray mixture for an area of one hectare contain; In a further embodiment for postemergence, 5 to 75 g, preferably 5 to 25 g of component a) are contained in 100 to 400 liters of spray mixture for an area of one hectare.
  • esters of C6-C22 fatty acids of plant origin usually in an amount contain, so that the spray mixture prepared by the user, such as the farmer, has a final concentration of 0.5 to 2.5 vol% MSO.
  • the ready-spray mixture contains a final concentration of 1, 0 to 1, 5 vol% MSO, more preferably from 1, 25 vol% MSO.
  • the indication% by volume refers to the total volume of the herbicidal composition, for example the ready-to-use spray mixture.
  • the ready-spray mixture contains at a conventional spray volume of 100 to 400 liters per hectare 1, 0 to 1, 5 vol% of component b) and component a) in an amount such that 2.5 to 100 g Active ingredient can be applied per hectare.
  • the mixtures according to the invention or the ready-to-use spray mixture at a spray liquor volume of 50 to 500 liters per hectare contain the components a) and b) usually in a ratio (w / w) of 1: 2.5 to 1: 5000.
  • a mixing ratio (w / w) of components a) and b) of from 1: 5 to 1: 1000 is preferred.
  • components a) and b) are present in the ready-to-use spray mixture in a ratio (w / w) of 1:10 to 1: 500.
  • the mixtures according to the invention may contain components a) and b) alone. You can also include one or more other components.
  • a fertilizer c in particular a nitrogen-containing fertilizer, can be added to the mixture according to the invention.
  • Suitable nitrogen-containing fertilizers are aqueous ammonia solutions, ammonium salts, urea, thiourea and mixtures thereof.
  • Ammonium salts are, for example, organic or inorganic salts such as, ammonium nitrate, ammonium sulfate, ammonium hydrogen sulfate, ammonium chloride,
  • urea ammonium nitrate (UAN) into consideration.
  • the nitrogen-containing fertilizers used are urea, ammonium nitrate, urea ammonium nitrate, ammonium sulfate, ammonium phosphate, ammonium hydrogen diphosphate, ammonium dihydrogen monophosphate or ammonium sodium hydrogen phosphate.
  • urea ammonium nitrate and ureaammonium nitrate.
  • Commercially urea ammonium nitrate for example as a solution having a total nitrogen content of 28 - available 33% (w / w) as Ensol 28 ® from BASF.
  • the mixture according to the invention or the herbicidal composition contains nitrogenous fertilizer (component c)) in an amount such that the spray mixture prepared by the user, for example the farmer, has a final concentration of 0.5 to 5 w / w%, for example of urea Ammonium nitrate has.
  • a 20 to 60 w / w% urea-ammonium nitrate-containing solution can be added to a metering device to produce 100 l of the ready-to-use spray mixture.
  • the ready-spray mixture contains a final concentration of 1, 5 to 3.0 w / w%, more preferably from 2.5 w / w% fertilizer.
  • the ready-spray mixture at a conventional spray liquor volume of 50 to 500 liters per hectare 0.5 to 5 w / w% of component c) and component a) in an amount such that 2.5 to 100 g Active ingredient can be applied per hectare.
  • the mixtures according to the invention or the ready-to-use spray mixture usually contain components a) and c) in a ratio (w / w) of 1: 2.5 to 1: 10,000.
  • a mixing ratio (w / w) of the components a) and c) of 1: 20 to 1: 2400 is preferred.
  • components a) and c) are present in the ready-to-use spray mixture in a ratio (w / w) of 1:33 to 1: 2000.
  • the mixture according to the invention may contain one or more herbicides (component d)), for example from the group of D1: acetyl-CoA carboxylase inhibitors (ACC), D2: acetolactate synthase inhibitors (ALS), D3: amides, D4: auxin Herbicides, D5: auxin transport inhibitors, D6: carotenoid biosynthesis inhibitors, D7: enolpyruvyl-shikimate-3-phosphate synthase inhibitors (EPSPS), D8: glutamine synthetase inhibitors, D9: lipid biosynthesis inhibitors , D10: mitosis inhibitors, D1: protoporphyrinogen IX oxidase inhibitors, D12: photosynthesis inhibitors, D13: synergists, D14: growth factors, D15: cell wall biosynthesis inhibitors, and D16: various other herbicides.
  • ACC acetyl-CoA carboxylase inhibitors
  • ALS acetolac
  • acetyl-CoA carboxylase inhibitors D1, ACC
  • the acetolactate synthase inhibitors include, among others, imidazolinones, pyrimidyl ethers, triazolopyrimidines or sulfonylureas.
  • auxin herbicides D4 are, inter alia, pyridine carboxylic acids, 2,4-D or benazoline of relevance.
  • lipid biosynthesis inhibitors (D9), among others, anilides, chloroacetanilides, thioureas, benfuresates or perfluidones are used.
  • the mitosis inhibitors (D10) are, inter alia, carbamates, dinitroanilines, pyridines, butamifos, chlorothal-dimethyl (DCPA) or maleic hydrazide into consideration.
  • Examples of protoporphyrinogen IX oxidase inhibitors (D1 1) include diphenyl ethers, oxadiazoles, cyclic imides or pyrazoles.
  • Suitable photosynthesis inhibitors are, inter alia, propanil, pyridazole, pyridafol, benzothiadiazinones, dinitrophenols, dipyridylenes, ureas, phenols, chloridazon, triazine, triazinone, uracils or biscarbamates.
  • the synergists (D13) include oxiranes.
  • Growth substances (D14) are, for example, aryloxyalkanoic acid, benzoic acids or quinolinecarboxylic acids.
  • the group "various other herbicides” include, inter alia, the active ingredient classes dichloro-propionic acids, dihydrobenzofurans, phenylacetic acids and individual herbicides as indicated below whose mechanism of action is not (exactly) known.
  • Herbicides d which can be used in combination with a compound of the formula I (component a)) and MSO (component b)) according to the present invention, are, for example:
  • ACC D1 acetyl CoA carboxylase inhibitors (ACC), e.g.
  • Phenoxyphenoxypropionic acid esters such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthia-propethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, Haloxy-fp-P-methyl, isoxapyrifop, metamifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl or quizalofop-tefuryl;
  • Arylaminopropionic acids such as flamprop-methyl or flamprop-isopropyl
  • keto-enols such as pinoxaden
  • D2 acetolactate synthase inhibitors e.g. Imidazolinones, such as imazapyr, imazaquin, imazamethabenzmethyl (imazam), imazamox, imazapic, imazethapyr or imazamethapyr;
  • Pyrimidyl ethers such as pyrithia-bac acid, pyrithiobac-sodium, bispyribac-sodium, KIH-6127 (pyriminobac-methyl), pyriftalid or pyribenzoxym; Triazolopyrimidines such as florasulam, flumetsulam, metosulam, penoxsulam, diclosulam or cloransulam-methyl;
  • Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorofuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl-
  • Sulfonylaminocarbonyltriazolinones such as thiencarbazone, flucarbazone or propoxycarbazone-Na; or
  • D4 Auxin herbicides e.g. Pyridinecarboxylic acids, such as aminopyralid, fluroxypyr, triclopyr, clopyralid or picloram; or
  • D5 auxin transport inhibitor e.g. • Naptalam or Diflufenzopyr
  • D6 carotenoid biosynthesis inhibitors e.g.
  • EPSPS enolpyruvyl-shikimate-3-phosphate synthase inhibitors
  • D8 glutamine synthetase inhibitors e.g.
  • Bilanafos (bialaphos) or glufosinate-ammonium
  • D9 lipid biosynthesis inhibitors e.g.
  • Anilides such as anilofos or mefenacet
  • Chloroacetanilides such as dimethenamid, S-dimethenamid, acetochlor, alachlor, butachlor, butenachlor, diethyl-ethyl, dimethachlor, metazachlor, metolachlor, Metolachlor, pethoxamide, pretilachlor, propachlor, prynachlor, terbuchlor, the- nylchlor or xylachlor;
  • Acetamides such as diphenamid, napropamide and naproanilide
  • Oxyacetamides such as flufenacet; Thioureas such as butylate, cycloate, dialate, dimepiperate, EPTC, esprocarb, monobutyl, pebulate, prosulfocarb, thiobencarb (benthiocarb), triallate or vernolate; or
  • isoxazolines such as pyroxasulfone (KIH-485) • benfuresate, ethofumesate, cafenstrole or perfluidone;
  • D10 mitosis inhibitors e.g.
  • Pyridines such as dithiopyr or thiazopyr
  • D1 1 protoporphyrinogen IX oxidase inhibitors e.g.
  • Diphenyl ethers such as acifluorfen, acifluorfen sodium, aclonifen, bifenox, chloronitrofen (CNP), ethoxyfen, fluorodifene, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen or oxyfluorfen;
  • Oxadiazoles such as oxadiargyl or oxadiazone
  • Cyclic imides such as azafenidine, butafenacil, carfentrazone-ethyl, cinidone-ethyl, flumiclorac-pentyl, flumioxazine, flumipropyne, flupropacil, fluthiacet-methyl, sulfentrazone or thidiazimine;
  • Pyrazoles such as pyraflufen-ethyl (ET-751), fluazolate (JV 485) or nipyraclofen;
  • Pyridazinones such as flufenpyr-ethyl
  • triazolones such as benzcarbazone
  • D12 photosynthesis inhibitors e.g.
  • Benzothiadiazinones such as bentazone
  • Dinitrophenols such as bromofenoxime, dinoseb, dinoseb acetate, dinoterb or DNOC;
  • dipyridylenes such as cyperquat chloride, difenzoquat methyl sulfate, diquat or para-quat dichloride;
  • Ureas such as chlorbromuron, chlortoluron, difenoxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, methazol, metobenzuron, metoxuron, monolinuron, neburon, consequenton or tebuthiuron;
  • Phenols such as bromoxynil or loxynil; • chloridazon;
  • Triazines such as ametryn, atrazine, cyanazine, desmetryn, dimethamethryn, hexazinone, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbutryn, terbutylazine or trietazine; Triazinones, such as metamitron or metribuzin;
  • Uracils such as bromacil, lenacil or terbacil
  • Biscarbamates such as Desmedipham or Phenmedipham
  • Oxiranes such as Tridiphan
  • D14 growth substances e.g.
  • Aryloxyalkanoic acids e.g. 2,4-DB, clomeprop, dichlorprop, dichlorprop-P (2,4-DP-P), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P or triclopyr;
  • Benzoic acids such as chloroamben or dicamba
  • Quinolinecarboxylic acids such as quinclorac or quinmerac
  • D15 cell wall synthesis inhibitors e.g. Isoxaben, flupoxam or dichlobenil;
  • D16 various other herbicides, e.g.
  • Dihydrobenzofurans such as ethofumesate
  • Phenylacetic acids such as Chlorfenac (Fenac); or
  • Herbicides d which are preferably used in combination with a compound of the formula I (component a)) and MSO (component b)) according to the present invention, are, for example:
  • D1 acetyl-CoA carboxylase inhibitors e.g. Cyclohexenone oxime ethers such as alloxydim, clethodim, cloproxydime, cycloxydim, sethoxydim, tralkoxydim, butroxydim, clefoxydim or tepraloxydim;
  • Phenoxyphenoxypropionic acid esters such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthia-propyl, fluorine zifop-butyl, fluazifop-p-butyl, haloxyfopethoxyethyl, haloxyfopmethyl, haloxy-fop-P-methyl, isoxapyrifop, metamifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl or quizalofop-tefuryl;
  • Arylaminopropionic acids such as flamprop-methyl or flamprop-isopropyl; or • keto-enols, such as pinoxaden;
  • ALS D2 acetolactate synthase inhibitors
  • Imidazolinones such as imazapyr, imazaquin, imazamethabenzmethyl (imazam), imazamox, imazapic, imazethapyr or imazamethapyr; Pyrimidyl ethers, such as pyrithiobacic acid, pyrithiobac sodium, bispyribac sodium, KIH-6127 or pyribenzoxym;
  • Triazolopyrimidines such as florasulam, flumetsulam, metosulam or penoxsulam;
  • Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, quinosulfuron, cyclosulfamuron, ethamethsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, primisulfuron methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, tritosulforon, sulfosulfuron or lodosulfuron; Sulfonylaminocarbon
  • Sulfonamides such as pyrimisulfane
  • Pyridinecarboxylic acids such as aminopyralid, clopyralid or picloram; or
  • D5 auxin transport inhibitor e.g.
  • D6 carotenoid biosynthesis inhibitors e.g. Beflubutamide, Benzofenap, Clomazone (Dimethazone), Diflufenican,
  • Fluorochloridone fluridone, pyrasulfutole, pyrazolynate, pyrazoxyfen, isoxaflutole, isoxachlorotol, mesotrione, sulcotrione (chlormesulone), tembotrione, ketospiradox, flurtamone, norflurazon, amitrole or CAS No: 352010-68-5;
  • EPSPS D7 enolpyruvyl-shikimate-3-phosphate synthase inhibitors
  • D8 glutamine synthetase inhibitors eg Bilanafos (bialaphos) or glufosinate-ammonium,
  • D9 lipid biosynthesis inhibitors e.g.
  • Anilides such as anilofos or mefenacet
  • Chloroacetanilides such as dimethenamid, S-dimethenamid, acetochlor, alachlor, butachlor, butenachlor, diethatylethyl, dimetha-chloro, metazachlor, metolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, prynachlor, terbuchlor, or nylchlorine Xylachlor;
  • Thioureas such as butylate, cycloate, dialate, dimepiperate, EPTC, esprocarb, monobutyl, pebulate, prosulfocarb, thiobencarb (benthiocarb), triallate or vernolate; or
  • D10 mitosis inhibitors e.g. Carbamates, such as asulam, carbetamide, chlorpropham, orbencarb, pronamide (proprazamide), propham or tiocarbazil;
  • dinitroanilines such as Benefin, Butraline, Dinitramine, Ethalfluralin, Fluchloralin, Oryzalin, Pendimethalin, Prodiamin or Trifluralin;
  • Pyridines such as dithiopyr or thiazopyr; or butamifos, chlorthal-dimethyl (DCPA) or maleic hydrazide;
  • D1 1 protoporphyrinogen IX oxidase inhibitors e.g.
  • Diphenyl ethers such as acifluorfen, acifluorfen sodium, aclonifen, bifenox, chloronitrofen (CNP), ethoxyfen, fluorodifene, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen or oxyfluorfen;
  • Oxadiazoles such as oxadiargyl or oxadiazone
  • Cyclic imides such as azafenidine, butafenacil, carfentrazone-ethyl, cinidone-ethyl, flumiclorac-pentyl, flumioxazine, flumipropyne, flupropacil, fluthiacet-methyl, sulfentrazone or thidiazimine; • pyrazoles, such as ET-751, JV 485 or nipyraclofen;
  • Pyridazinones such as flufenpyr-ethyl
  • Triazolones such as benzcarbazone
  • D12 photosynthesis inhibitors e.g. Propanil, pyridate or pyridafol
  • Benzothiadiazinones such as bentazone
  • Dinitrophenols such as bromofenoxime, dinoseb, dinoseb acetate, dinoterb or DNOC;
  • dipyridylenes such as cyperquat chloride, difenzoquat methyl sulfate, diquat or para-quat dichloride;
  • Ureas such as chlorbromuron, chlortoluron, difenoxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isourone, linuron, methabenzthiazuron, methazol, metobenzuron, metoxuron, monolinuron, neburon, duron or tebuthiuron;
  • Phenols such as bromoxynil or loxynil
  • Triazines such as ametryn, atrazine, cyanazine, desmetryn, dimethamethryn, hexazinone, prometon, prometryn, propazine, simazine, simetryn, terbumetone, terbutryn,
  • Triazinones such as metamitron or metribuzin
  • Uracils such as bromacil, lenacil or terbacil
  • Biscarbamates such as Desmedipham or Phenmedipham
  • Oxiranes such as Tridiphan
  • D14 growth substances e.g. Aryloxyalkanoic acids, e.g. 2,4-DB, Clomeprop, dichlorprop, dichloroprop-P
  • Benzoic acids such as chloroamben or dicamba
  • Quinolinecarboxylic acids such as quinclorac or quinmerac
  • D15 cell wall synthesis inhibitors e.g.
  • D16 various other herbicides, e.g.
  • dichloropropionic acids such as dalapon
  • Dihydrobenzofurans such as ethofumesate
  • Phenylacetic acids such as chlorfenac (fenac); or
  • components d) from the following classes of active compound or the following compounds are particularly preferred:
  • ALS D2 Acetolactate synthase inhibitors • Sulfonylureas, especially nicosulfuron
  • Chloroacetanilides especially dimethenamid, S-dimethenamid, acetochlor, metolachlor, S-metolachlor; • thioureas, especially benthiocarb;
  • Isoxazolines such as pyroxasulfone (KIH-485);
  • Dipyridylenes especially paraquat dichloride
  • Ureas in particular diuron or isoproturon, in particular diuron;
  • Phenols in particular bromoxynil
  • Triazinones in particular metribuzin
  • components d) from the following classes of active compound or the following compounds are likewise particularly preferred:
  • D9 Lipid biosynthesis inhibitors • Chloroacetanilides, in particular dimethenamid, S-dimethenamid, acetochlor, metolachlor or S-metolachlor;
  • D12 photosynthesis inhibitors • pyridate
  • Dipyridylenes especially paraquat dichloride
  • Ureas in particular diuron or isoproturon, in particular diuron;
  • Phenols in particular bromoxynil; • chloridazon;
  • Triazines in particular atrazine or terbutylazine
  • Triazinones in particular metribuzin; According to another embodiment, as component d) of the mixtures according to the invention, triazines are particularly preferred, in particular atrazine or tert-butylazine.
  • the combination of triazines and chloroacetanilides in particular from atrazine and dimethenamid or S-dimethenamid, is preferred as component d) of the mixtures according to the invention.
  • chloroacetanilides in particular metazachlor, are preferred as component d) of the mixtures according to the invention.
  • quinolinecarboxylic acids in particular quinmerac, are preferred.
  • component d) of the mixtures according to the invention is the combination of triazines and sulfonylureas, in particular of atrazine and nicosulfuron.
  • the weight ratio of component a) and component d) in the herbicidal mixture or in the agent according to the invention is preferably in the range from 1: 0.001 to 1: 500, preferably from 1: 0.01 to 1: 200, particularly preferably from 1: 0 , 01 to 1: 100.
  • the mixture according to the invention as component e) may contain a safener.
  • Suitable safener e are substances such as Benoxacor, Cloquintocet, Cyometrinil, dichloromide, dicyclonone, dietholate, fenchchlorazole, fenclorim, flurazole, Fluxofenim, Furilazol, Isoxadifen, Mefenpyr, Mephenat, Naphtalic anhydride, 2,2,5-trimethyl -3- (dichloroacetyl) -i, 3-oxazolidine (R-29148), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (AD-67, MON 4660), N - [[4- [(Cyclopropylamino) carbonyl] phenyl] sulfonyl] -2-methoxybenzamide II (CAS no. 221667-31-8, cyprosulfamide) and oxabetrinil.
  • the following safeners are particularly preferred: Benoxacor, Cloquintocet, Dichlormid, Fenchchlorazol, Fenclorim, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr, AD-67 and Oxabetrinil used.
  • the following safeners are particularly preferred: Benoxacor, Cloquintocet, Dichlormid, Fenchchlorazol, Fenclorim, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr and Oxabetrinil used.
  • Both the component a) and the herbicides d) from groups D1 to D16 and the components e) can also be present in the form of their environmentally acceptable salts, esters and amides.
  • Suitable salts are in general the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal action of the active ingredients.
  • Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, in which case it is possible, if desired to four hydrogen atoms 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, isopropylammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium,
  • Anions of suitable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably format, acetate, propionate and butyrate.
  • Suitable esters are alkyl, alkoxyalkyl, allyl, propargyl and oxetan-3-yl esters, preferably C 1 -C 10 -esters, for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl , Mexyl- ( ⁇ i-methyl-hexyl) or isooctyl ( ⁇ 2-ethyl-hexyl) esters, Ci-C4-alkoxyethyl esters, for example methoxyethyl, ethoxyethyl or butoxyethyl esters, allyl esters, proparyl esters and oxetane-3-yl ester.
  • C 1 -C 10 -esters for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl , Mexyl- ( ⁇ i
  • Suitable amides are unsubstituted amides, alkyl and dialkyl amides and anilides, preferably C 1 -C 4 -alkyl amides, for example methyl or ethyl amides, di (C 1 -C 4 -alkyl) amides, for example dimethyl or diethyl amides, or anilides, prefers the unsubstituted anilide or 2-chloroanilide.
  • the components a), d) and e) and / or their salts, esters, amides and hydrates can be present in the mixture according to the invention as pure enantiomers, as well as racemates or diastereomer mixtures or as tautomers.
  • the components a) to e) can be used individually or already partially or completely mixed with one another for the preparation of the herbicidal mixture according to the invention. It is also possible that they are packaged and reused as a kit of parts like a kit of parts.
  • component a) can be used as pure active ingredient for the preparation of the herbicidal mixture.
  • component a) is present as, for example, excipients formulated with excipients.
  • the component a) can be used separately or together with the other components or as a constituent of a combination agent according to the invention for the preparation of the mixture according to the invention.
  • the other components of the mixture according to the invention can also be formulated with excipients for their preparation.
  • the mixture according to the invention or the herbicidal composition according to the invention can be used, for example, in the form of directly sprayable aqueous solutions or dispersions, also high-percentage aqueous, oily or other suspensions or emulsions by spraying, atomizing or pouring.
  • the forms of application depend on the intended use; In each case they should ensure the finest possible distribution of the herbicidal mixture according to the invention.
  • Aqueous application forms of the mixture according to the invention can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules.
  • the herbicidal mixture or its components as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be prepared from the herbicidal mixture or its components, wetting agents, adhesives, dispersants or emulsifiers and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • Powders, litter and dusting agents can be prepared, for example, by mixing or jointly grinding component a), if appropriate fertilizer c) if appropriate, further herbicides d) and optionally safener e) with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding component a), if appropriate fertilizer c), if appropriate, further herbicides d) and optionally safener e) to solid carriers.
  • the user for example the farmer, uses the inventive herbicidal mixture or the herbicidal agent, usually for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane.
  • the herbicidal mixture is brought to the desired application concentration with water and / or buffer, optionally further auxiliaries and additives being added.
  • the user can himself mix the individual components of the herbicidal mixture according to the invention in the spray tank and, if appropriate, add further auxiliaries and additives (tank mixing method).
  • the user can mix both individual components of the herbicidal mixture according to the invention and partially premixed components, for example a) and d), in the spray tank and optionally add further auxiliaries and additives (tank mixing method).
  • the components a) and / or optionally d) and / or optionally e) are already formulated in the metering device and diluted to the desired application concentration.
  • component b), MSO is admixed in the tank.
  • auxiliary agents and additives are, for example:
  • Inert adjuncts or carriers such as medium to high boiling point mineral oil fractions 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, e.g. Amines such as N-methylpyrrolidone or water.
  • mineral oil fractions 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
  • Suitable adjuvants for a formulation of component a) and / or optionally d) and / or optionally e) are vegetable oils which may be partially hydrogenated and hydrogenated, modified, eg esterified vegetable oils, mineral oils, alcohol alkoxylates, alcohol ethoxylates, alkylated (ethylene oxide (EO ) / Propylene oxide (PO)) block copolymers, alkylphenol ethoxylates, polyols, EO / PO block copolymers, organosilicon compounds, alkyl glycosides, alkyl polyglycosides, alkyl sulfates, sulfated alcohol alkoxylates, alkylaryl sulfonates, alkyl sulfonates, dialkyl sulfosuccinates, phosphated alcohol alkoxylates, fatty acids.
  • vegetable oils which may be partially hydrogenated and hydrogenated, modified, eg esterified vegetable oils, mineral oils, alcohol alkoxy
  • Preferred adjuvants are alcohol alkoxylates, such as alkyl ethers of (ethylene oxide (EO) / propylene oxide (PO)) - copolymers, including Plurafac ® (BASF AG), SynperionicR LF (ICI), alcohol ethoxylates, where the alcohol is a Cs-Ci s-alcohol of synthetic or natural Origin is that can be both linear and branched. Depending on the alcohol used, the ethoxylate part contains on average from 3 to 20 mol of ethylene oxide.
  • alcohol alkoxylates such as alkyl ethers of (ethylene oxide (EO) / propylene oxide (PO)) - copolymers, including Plurafac ® (BASF AG), SynperionicR LF (ICI), alcohol ethoxylates, where the alcohol is a Cs-Ci s-alcohol of synthetic or natural Origin is that can be both linear and branched.
  • the ethoxylate part contains on average from 3
  • Exemplary products used are Lutensol ® ON, TO, AO and A BASF, alkylamine rylsulfonate as nonylphenol ethoxylates with 5-15 moles EO, polyols such as polyethylene glycol or polypropylene glycol, EO / PO block copolymers such as Pluronic ® PE (BASF) or Synperionic ® PE (ICI), organosilicon compounds, alkyl polyglycosides such as Agrimul ® (Henkel KGA), AG 6202 (Akzo-Nobel) Atplus ® 450 (ICI) or Lutensol ® GD 70 (BASF), fatty amine alkoxylates such as Ethomeen ® and Armobleem ® from Akzo Nobel, esters of natural and synthetic fatty acids such as methyl oleate or methyl cocoate, dialkyl adipates, ethoxylated sorbitan esters of natural fatty acids such as Tween ® from ICI surfact
  • Buffers or buffer solutions are solutions that barely change their pH with the addition of strong acids or bases. Buffer solutions usually consist of a weak acid, for example acetic acid, and one of its salts, for example sodium adenate,
  • auxiliaries and additives can be added.
  • the following components have proven useful: other solvents, defoamers, buffer substances, thickeners, spreading agents, compatibilizers, liquid and solid carriers, surfactants.
  • Solid carriers are, for example, mineral earths 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 nut shell flour, cellulose powder or other solid carriers.
  • mineral earths 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
  • surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and Dibutylnaphtha- linsulfonklare and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl
  • the mixture according to the invention is suitable as a herbicide.
  • the herbicidal mixture combats plant growth on non-cultivated areas very well. In crops such as wheat, rice, maize, soya and cotton, it works against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
  • the herbicidal mixture can still be used in a further number of crop plants for the removal of unwanted plants.
  • the following cultures may be considered:
  • Cynodon dactylon Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgaris, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus sp., Pisum sativum,
  • the herbicidal mixture can also be used in crops which are tolerant to the action of herbicides both by classical breeding and by the use of genetic engineering methods.
  • the application of the herbicidal mixture can be carried out in the pre-plant burn-down or post-emergence process. If the herbicidal mixture is less compatible with certain crops, then application techniques may be employed in which the herbicidal mixture is sprayed by the sprayers so as not to strike the leaves of the sensitive crops while the herbicidal mixture is growing on the leaves below undesirable plants or the uncovered soil surface (post-directed, lay-by).
  • the individual components were added to the metering device, made up with water ad 100 l and stirred. It may be beneficial to provide some of the water you need.
  • the individual components were added to the metering device, made up with water ad 100 l and stirred. It may be beneficial to provide some of the water you need. 3.
  • the following components were used to prepare 100 l of a spray mixture:
  • the individual components were added to the metering device, made up with water ad 100 l and stirred. It may be beneficial to provide some of the water you need.
  • the herbicidal action of the mixture according to the invention or of the herbicidal agents was determined by greenhouse experiments (Tables 1-4) with component a) 4- [2-methyl-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulphonylbenzoyl ] -1-methyl-5-hydroxy-1H-pyrazole post-emergence;
  • the culture vessel used were plastic flower pots which were filled with loamy sand with about 3% humus content as substrate.
  • the seeds of the test plants were sown separately by species.
  • test plants were grown depending on the growth form only to a stature height of 3 - 17 cm and only 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 15 ° C to 25 ° C and 20 to 35 ° C. The trial period lasted over 3 weeks. During this time, the plants were maintained and their response to each treatment was evaluated. Was rated according to a scale of 0-100. "100" means complete destruction of at least the above-ground parts of plants and "0" means no damage or normal growth course in comparison to an untreated control.
  • the application in the greenhouse was carried out at an application rate of the spray mixture of 200 l / ha.
  • COC crop oil concentrate
  • AWM application rate
  • d day of the rating.
  • the herbicidal mixture of the invention shows excellent activity against undesirable plants, which was not expected from the efficacy of the individual compounds.
  • mixture according to the invention is distinguished by a substantially higher herbicidal activity than mixtures with customary adjuvants such as COC:
  • Mixtures according to the invention which, in addition to the components a) and b) contain further components, for example a component d), show a substantially higher herbicidal activity than mixtures with customary adjuvants such as COC.
  • a component d for example a component d
  • the component b) MSO or in comparison COC in a concentration of 1.25% by volume was contained in the spray mixture:
  • mixtures according to the invention which, in addition to components a) and b) contain, for example, a component c), exhibit a substantially higher herbicidal activity than mixtures with customary adjuvants such as COC.
  • a component c a component c
  • the component b) MSO or in comparison COC in a concentration of 1.25% by volume was contained in the spray mixture:
  • Mixtures according to the invention which, in addition to components a) and b), contain further components, namely c) and d), exhibit a significantly higher herbicidal activity than mixtures with conventional adjuvants, such as COC.
  • component c), UAN, in a concentration of 2.5% w / w% and component b) MSO or in comparison COC in a concentration of 1.25% by weight were present in the spray mixture.
  • % contain:

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Fertilizers (AREA)

Abstract

L'invention concerne des mélanges contenant: a) un dérivé de benzoyle à substitution 4,5-dihydroisoxazole-3-yle, de formule (I), R signifiant chlore ou méthyle, ou bien un de ses sels, esters ou amides compatibles avec l'environnement, et b) un ester d'acides gras C6-C22 d'origine végétal.
EP06819608A 2005-11-25 2006-11-20 Melanges herbicides Withdrawn EP1956902A2 (fr)

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DE102005056590 2005-11-25
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AR062264A1 (es) 2006-08-04 2008-10-29 Basf Ag Concentrados no acuosos de principios activos con efecto herbicida
WO2008064988A1 (fr) * 2006-11-27 2008-06-05 Basf Se Composition herbicide contenant un sel monovalent de 4-[2-méthyl-3-(4,5-dihydroisoxazol-3-yl)-4-méthylsulfonylbenzoyl]-1-méthyl-5-hydroxy-1h-pyrazole
MX2010005231A (es) * 2007-11-12 2010-05-27 Du Pont Mezcla herbicida.
US20120178626A1 (en) * 2011-01-10 2012-07-12 Dow Agrosciences Llc Synergistic herbicidal composition containing propyzamide and benfluralin
RU2618122C2 (ru) * 2012-03-30 2017-05-02 Исихара Сангио Кайся, Лтд. Гербицидная композиция
JPWO2013180129A1 (ja) * 2012-05-28 2016-01-21 石原産業株式会社 除草組成物
CN111285863B (zh) * 2018-12-07 2022-04-26 青岛清原化合物有限公司 4-(3-杂环基-1-苯甲酰基)吡唑类化合物或其盐、制备方法、除草剂组合物及用途
JP7179645B2 (ja) * 2019-02-25 2022-11-29 日本曹達株式会社 除草方法
CN111978293B (zh) * 2020-08-24 2023-10-27 天津大学 一种烟嘧磺隆-尿素共晶及其制备方法

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AU6207698A (en) * 1997-01-17 1998-08-07 Basf Aktiengesellschaft Process for preparing sulphurous 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-benzoic acids
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PL197922B1 (pl) * 1999-03-05 2008-05-30 Basf Ag Mieszanina chwastobójcza, sposób jej wytwarzania i sposób zwalczania niepożądanej roślinności
EA010978B1 (ru) * 2002-07-24 2008-12-30 Басф Акциенгезельшафт Гербицидные смеси с синергическим действием
UA83031C2 (ru) * 2003-03-13 2008-06-10 Басф Акциенгезелльшафт Гербицидная смесь, содержащая сафенер, гербицидная композиция на ее основе, способ получения композиции и способ борьбы с нежелательной растительностью
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AR057174A1 (es) 2007-11-21
JP2009517365A (ja) 2009-04-30
WO2007060146A2 (fr) 2007-05-31
CA2629086A1 (fr) 2007-05-31
TW200726762A (en) 2007-07-16
US20080293572A1 (en) 2008-11-27
US20070123426A1 (en) 2007-05-31
WO2007060146A3 (fr) 2007-08-02

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