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EP2048945A2 - New microemulsifiable concentrates - Google Patents

New microemulsifiable concentrates

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Publication number
EP2048945A2
EP2048945A2 EP07801442A EP07801442A EP2048945A2 EP 2048945 A2 EP2048945 A2 EP 2048945A2 EP 07801442 A EP07801442 A EP 07801442A EP 07801442 A EP07801442 A EP 07801442A EP 2048945 A2 EP2048945 A2 EP 2048945A2
Authority
EP
European Patent Office
Prior art keywords
methyl
alkyl
ethyl
group
acid
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.)
Withdrawn
Application number
EP07801442A
Other languages
German (de)
French (fr)
Inventor
Thomas Maier
Detlev Haase
Gerhard Schnabel
Gerhard Frisch
Dorel-Gheorghe Merk
Gerd Schweinitzer
Ralph Grohs
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP07801442A priority Critical patent/EP2048945A2/en
Publication of EP2048945A2 publication Critical patent/EP2048945A2/en
Withdrawn legal-status Critical Current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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels

Definitions

  • the present invention relates to the field of crop protection formulations.
  • the invention relates to liquid agrochemical formulations in the form of microemulsion concentrates and microemulsions.
  • Active ingredients for crop protection are generally not used in their pure form. Depending on the field of application and the type of application, as well as on physical, chemical and biological parameters, the active ingredient is used in admixture with customary auxiliaries and additives as a solid or liquid active substance formulation. But the drug formulation of combinations (mixtures) with other agents to extend the spectrum of activity and / or protection of crops, such as safeners (antidotes), is an important field of formulation technology, since here are active substances with sometimes quite different physical, chemical and biological parameters must be adequately formulated together.
  • formulations of combinations of several active ingredients for plant protection should generally have a high chemical and physical stability, good applicability and user-friendliness and a broad biological activity with high selectivity with regard to the active ingredients used, in addition to a technically good formability in the manufacturing process.
  • Liquid formulations are described, for example, in EP 0 261 492, EP 0 394 847, WO 95/17822, WO 98/31223, WO 89/03176, EP 0 357 149, WO 02/45507, GB 2 267 825 A, WO 94 / 23578, EP 0 330 904, EP 0 533 057, EP 0 533 057, DE 36 24 910, WO 01/74785, EP 0 400 585, EP 0 118 579, XP 002 177 928, EP 0 648 414 A1, US 5 300 529, US Pat. No.
  • EP 0257286 A1 the preparation of a microemulsion (ME) for the insecticide Endosulfan is described which comprises a solvent mixture used in the isobutanol in a C, is 4 alcohol.
  • the object of the present invention was to provide an improved crop protection formulation which is also advantageous with regard to the active ingredients used and / or combinations thereof, e.g. has improved effectiveness.
  • the present invention thus relates to a microemulsion concentrate comprising (a) one or more agrochemical active compounds, in particular from the group of fungicides, insecticides, plant growth regulators, herbicides and safeners, (b) one or more alcoholic solvents having at least 5 carbon atoms,
  • microemulsion concentrate according to the invention may optionally still contain as further components (f) customary auxiliaries and additives.
  • microemulsion concentrate a composition which, when diluted with water, forms microemulsions (ME), e.g. Oil-in-water microemulsions or water-in-oil microemulsions.
  • ME microemulsions
  • Microemulsion is understood to be an emulsion which is thermodynamically stable and has a small droplet size of the emulsified phase, which is generally in the range of 10 - 400 nm, preferably 20 - 350 nm.
  • microemulsion concentrates i.a. in that no water is used as a formulation adjuvant. Nevertheless, impurities in water can be introduced via the individual components. This water content to a maximum of ⁇ 2 wt .-%, usually 0 to ⁇ 1 wt .-%, but is irrelevant to the quality of the microemulsion concentrate.
  • microemulsion concentrates according to the invention generally contain the following amounts of components (a), (b), (c), (d), (e) and (f), in which case
  • Component (a) 0.001-50% by weight, preferably 0.1-45% by weight, particularly preferably 1-40% by weight.
  • Component (d) 0.1-30% by weight, preferably 0.5-25% by weight, particularly preferably 1-40% by weight.
  • Suitable active ingredients (component a) in the microemulsion concentrate according to the invention are all active substances which can be used in the agrochemical field.
  • fungicides fungicides, bactericides, insecticides, acaricides, nematicides, molluscicides, rodenticides, repellents, plant growth regulators, herbicides and safeners and plant nutrients.
  • insecticides both insecticides and bactericides and viricides
  • insecticides both insecticides and acaricides, nematicides, molluscicides, rodenticides and repellents
  • herbicides herbicides as well as plant growth regulators - unless the context otherwise indicates.
  • the agrochemically active compounds may be fungicides, for example inhibitors of nucleic acid synthesis, in particular
  • Azoxystrobin cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximmethyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin; Decouplers, especially dinocap, fluazinam;
  • Fentin acetate Fentin chloride, fentin hydroxide, silthiofam; Inhibitors of amino acid and protein biosynthesis, in particular
  • blasticidin-S blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
  • Signal transduction inhibitors in particular fenpiclonil, fludioxonil, quinoxyfen; Inhibitors of fat and membrane synthesis, in particular
  • Fenbuconazole fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis,
  • Paclobutrazole penconazole, propiconazole, prothioconazole, simeconazole,
  • Iminoctadinalesilate iminoctadine triacetate, mancopper, mancozeb, maneb, Metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram; Fungicides with unknown mechanism, in particular
  • the agrochemically active compounds may also be bactericides, for example bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • bactericides for example bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • fungicides are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
  • the agrochemically active compounds may also be insecticides / acaricides and / or nematicides, for example acetylcholinesterase (AChE) inhibitors carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendabarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb,
  • AChE acetylcholinesterase
  • Organophosphates for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophosphethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl ), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos,
  • Oxadiazines for example indoxacarb
  • Semicarbazone for example metaflumizone (BAS3201); Acetylcholine receptor agonists / antagonists
  • Chloronicotinyls for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam
  • Organochlorines for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH,
  • Fiproles for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole,
  • Mectins for example Abamectin, Emamectin, Emamectin benzoate, Ivermectin,
  • Lepimectin Lepimectin, milbemycin; Juvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprene,
  • Benzoylureas for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron; buprofezin;
  • Pyrroles for example chlorfenapyr
  • Dinitrophenols for example binapacyrl, dinobutone, dinocap, DNOC
  • Site I Electron Transport Inhibitors METI's for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad,
  • Tetronic acids for example spirodiclofen, spiromesifen
  • Tetramic acids for example spirotetramat
  • Carboxamides for example flonicamid octopaminergic agonists, for example amitraz; Inhibitors of magnesium-stimulated ATPase,
  • Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium;
  • Benzoic acid dicarboxamides for example flubendiamide
  • Anthranilamides for example DPX E2Y45 (3-bromo-N- ⁇ 4-chloro-2-methyl-6-)
  • Feed inhibitors for example cryolites, flonicamide, pymetrozines;
  • Mite growth inhibitors for example clofentezine, etoxazole, hexythiazox;
  • insecticides listed above are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
  • the agrochemically active compounds may also be herbicides and / or plant growth regulators;
  • ALS inhibitors acetolactate synthetase inhibitors
  • herbicides other than ALS inhibitors such as herbicides from the group of carbamates, thiocarbamates, haloacetanilides, substituted phenoxy, naphthoxy and Phenoxyphenoxycarbonklare derivatives and heteroaryloxy-phenoxyalkanecarboxylic acid derivatives such as quinolyloxy -, Chinoxalyl-oxy-, pyridyloxy, Benzoxazolyloxy- and Benzthiazolyloxyphenoxyalkan- carboxylic acid esters, cyclo-hexanedione derivatives, phosphorus-containing herbicides, eg glufosinate-type or glyphosate-type, S- (N-aryl-N-alkylcarbamoylmethyl) -dithiophosphoric acid esters,
  • the ALS inhibitors are in particular imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, triazolo-pyrimidine-sulfonamide derivatives and sulfonamides, preferably from the group of sulfonylureas.
  • the active compounds from the group of ALS inhibitors such as sulfonylureas, which are contained as component in the microemulsion concentrates according to the invention are always to be understood as meaning their salts with inorganic and / or organic counterions.
  • sulfonylureas can form, for example, salts in which the hydrogen of the -SO 2 -NH group is protected by a cation suitable for agriculture is replaced.
  • These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts or salts with organic amines.
  • salt formation can take place by addition of an acid to basic groups, such as, for example, amino and alkylamino.
  • Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H 2 SO 4 or HNO 3 .
  • Preferred ALS inhibitors are derived from the series of sulfonylureas, e.g.
  • Pyrimidine or triazinylaminocarbonyl [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides.
  • Preferred substituents on the pyrimidine or triazine ring are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or
  • Alkylsulfonyl alkylamino moiety are alkyl, alkoxy, halogen such as F, Cl, Br or J, amino, alkylamino, dialkylamino, acylamino such as formylamino, nitro,
  • Alkylsulfonylaminoalkyl (alkanesulfonyl) alkylamino.
  • Sulfonylureas are for example
  • N N-dimethyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-formylaminobenzamide (foramsulfuron and its salts, such as the sodium salt, WO 95/01344);
  • sulfone diamide derivatives e.g. 3- (4,6-dimethoxypyrimidin-2-yl) -1- (N-methyl-N-methylsulfonylaminosulfonyl) urea (amidosulfuron) and its structural analogs (EP-A-0 131 258 and Z. Pfi. Ill. PfI Special Edition XII, 489-497 (1990));
  • pyridylsulfonylureas e.g. I ⁇ S-N, N-dimethylaminocarbonylpyridine, -sylsulfonyo-S, N- ⁇ -dimethoxypyrimidin-yl) urea (nicosulfuron),
  • Alkoxyphenoxysulfonylureas as described e.g. in EP-A 0 342 569, preferably 3- (4,6-dimethoxypyrimidin-2-yl) -1- (2-ethoxyphenoxy) sulfonylurea (ethoxysulfuron) or its salts, such as the sodium salt;
  • MON 37500 sulfosulfuron (see Brighton Crop Prot. Conf., "Weeds 1 ,” 1995, p. 57), and other related sulfonylurea derivatives and mixtures thereof.
  • Typical representatives of these active substances are, inter alia, the compounds listed below and their salts, such as the sodium salts: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
  • Suitable ALS inhibitors are e.g.
  • Triazolopyrimidine sulfonamide derivatives e.g. N- (2,6-Difluorophenyl) -7-methyl-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide (flumetsulam), N- (2,6-dichloro-3-methylphenyl) 5,7-dimethoxy-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide,
  • Suitable herbicidally active compounds which differ from ALS inhibitors and can be contained as component in the microemulsion concentrates according to the invention are, for example:
  • Chloroacetanilides e.g. N-methoxymethyl-2,6-diethyl-chloroacetanilide (alachlor), N- (3-methoxyprop-2-yl) -2-methyl-6-ethyl-chloroacetanilide (metolachlor),
  • G) thiocarbamates eg S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates);
  • H) cyclohexanedione oximes eg
  • L) phosphorus-containing herbicides for example one or more compounds of the formula (IV) or derivatives thereof, such as salts,
  • R 2 , R 3 are each independently H, alkyl, C ⁇ -Cio-aryl, which is unsubstituted or substituted and is preferably unsubstituted or substituted by one or more radicals from the group alkyl, alkoxy, halogen, CF 3 , NO 2 and CN , or
  • active compounds of the formulas (IV) and (V) are as follows: glufosinates and their ammonium salt in racemic form, i. 2-Amino-4-
  • auxins and auxin analogs e.g. 4-indole-3-butyric acid, indole-3-acetic acid, 1-naphthylacetic acid, 2- (1-naphthyl) acetamide and 2-naphthyloxyacetic acid;
  • cytokinins e.g. Cythokinin, Kinetin and 6-Benzylaminopurine;
  • gibberellins e.g. Gibberillic Acid, Gibberillin A4 and A7;
  • T) ethylene precursors e.g. ethephon
  • V) ureas e.g. Chlorotoluron, dimefuron, diuron, fluometuron, isoproturon, isourone, carbutilate, linuron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron and tebuthiuron and
  • Hydroxybenzonitriles for example, such as bromoxynil and loxynil and their salts and esters, such as Bromoxyniloctanoat and loxyniloctanoat.
  • the agrochemical active substances can also be growth regulators. Examples are tribufos, cyclanilides and thidiazuron.
  • Fungicides bactericides
  • insecticides acaricides, nematicides
  • herbicides plant growth regulators
  • Atrazine acetochlor, aclonifen, alachlor, amidochlor, amidosulfuron, azimsulfuron, alloxydim, amitraz, anilofos, asulam, acetamiprid, acrinathrin, aldicarb, azinophosmethyl, amicarbazones, bentazone, bensulfuron (-methyl), bromoxynil (-octanoate / - heptanoate) , Butachlor, Bispyribac (-sodium), Benzobicyclone, Benzofenap, Butroxydim, Bitertanol, Bromuconazole, Benfuresate, Beta-Cyfluthrin, Chlorsulfuron, Chlorimuron, Clomazone, Clopyralid, Cinosulfuron, Cyclosulfamuron, Clethodim, Clodinafop-propargyl, Cycloxyd
  • the agrochemical active ingredients listed above are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
  • the agrochemical active substances can also be safeners. Examples include: a) compounds of the formulas (S-II) to (S-IV),
  • n ' is a natural number from 0 to 5, preferably 0 to 3;
  • T is a (Ci or C 2 ) alkanediyl chain, which is unsubstituted or substituted by one or two (C-rC-OAlkylresten or with [(C- ⁇ -C 3 ) alkoxy] carbonyl;
  • W is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N or O atoms, at least one N atom and at most one O atom in the ring, preferably a radical from the group (W 1) to (W4),
  • R 17 , R 19 are the same or different halogen
  • R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S.
  • R 21 is (C r C 4 ) Alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl,
  • R 22 , R 23 is identical or different hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl,
  • compounds such as 1- (2,4-dichloro-phenyl) - Ethyl 5-methyl-pyrazole-3-carboxylate (II-2), 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylate (II-3), 1- (2,4-dichlorophenyl) - Ethyl 5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylate (II-4),
  • EP-A-0492366 Compounds of the (5-chloro-8-quinolinoxy) -malonic acid type, i. the formula
  • R 30 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbylthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more identical or different radicals from the group halogen, cyano, nitro , Amino, hydroxy, carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Z a -R a is substituted, wherein each hydrocarbon moiety preferably 1 to 20 carbon atoms and a C-containing radical R 30 including substituents preferably 1 to 30 Having C atoms;
  • R 31 is hydrogen or (dC 4) -alkyl, preferably hydrogen, or
  • R 30 and R 31 together with the group of the formula -CO-N- denote the radical of a 3- to 8-membered saturated or unsaturated ring;
  • R 32 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula -Z b -R b ;
  • R 33 is hydrogen or (C 1 -C 4 ) -alkyl, preferably H;
  • R 34 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula -Z c -R c ;
  • R a is a hydrocarbon radical or a heterocyclyl radical, where each of the latter two radicals is unsubstituted or substituted by one or more identical or different radicals from the group of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(C 1 -C 4 ) -alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom;
  • R b , R c identically or differently, are a hydrocarbon radical or a
  • Heterocyclylrest wherein each of the last two radicals unsubstituted or by one or more identical or different radicals selected from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halogeno (C 1 -C 4 ) alkoxy, mono- and di- [(CrC 4 ) -alkyl] -amino, or a
  • Alkyl radical in which a plurality, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom;
  • Z a is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-,
  • R a is the bond to the radical R a and the R * in the 5 last-mentioned radicals independently of one another are each H, (dC 4) -alkyl or halo- (CrC 4) - alkyl;
  • Z b , Z c independently of one another a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-,
  • R 30 cyclopropyl
  • R 34 2-OMe is (V-3)
  • X 3 is CH or N
  • R 35 is hydrogen, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 and Z a -R are a substituted;
  • R 36 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (CrC 6) - alkoxy, (C 2 -C 6) - alkenyloxy, wherein the five last-mentioned radicals are optionally substituted by one or more identical or different radicals from the group halogen, hydroxy, (CICO-alkyl, (Ci-C 4) -alkoxy and (C 1 -C 4) - substituted alkylthio, or R 35 and R 36 together with the nitrogen atom carrying them
  • R 37 is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 or Z b -R b ;
  • R 38 is hydrogen, (C r C4) alkyl, (C 2 -C 4) -alkenyl or (C 2 -C 4) alkynyl;
  • R 39 is halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z c -R c ;
  • R a is a (C 2 -C 20 ) -alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group
  • R b , R c are a (C 2 -C 20 ) -alkyl radical whose carbon chain interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, phosphoryl, (C 1 -C 4 substituted [(Ci-C 4) alkyl] -amino) - - haloalkoxy, mono- and di;
  • Z a is a divalent unit from the group O 1 S, CO, CS, C (O) O, C (O) S 1 SO, SO 2 , NR d , C (O) NR d or SO 2 NR d ;
  • Z b , Z c identically or differently, denote a direct bond or a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 , NR d , SO 2 NR d or C (O) NR d ;
  • R d is hydrogen, (C r C 4 ) alkyl or (C r C 4 ) haloalkyl; n is an integer from 0 to 4, and m in the case that X is CH, an integer from 0 to 5, and for the
  • R 35 is hydrogen, (C r C6) alkyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (C 5 -C 6) - cycloalkenyl, phenyl or 3- to 6 hetero-cyclic heterocyclyl having up to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur, wherein the six last-mentioned radicals are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C 1 -C 6 ) -alkoxy, (C r C 6) haloalkoxy, (Ci-C2) alkylsulfinyl, (CrC 2) alkylsulfonyl, (C 3 -C 6) -cycloalkyl, (CrC 4) alkoxycarbonyl, (C r C 4) -alkylcarbonyl and phenyl and, in (C r C4) al
  • R 36 is hydrogen, (C r C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where the last three radicals mentioned are optionally substituted by one or more, identical or different substituents from the group halogen, hydroxy, (C 1 -C 4) - alkyl, (CrC 4) -alkoxy and (CrC 4) -alkylthio; R 37 is halogen, (CrC 4) -haloalkyl, (CrC 4) -haloalkoxy, nitro, (CrC 4) alkyl, (C 1 -C 4) - alkoxy, (CrC 4) alkylsulfonyl, (CrC 4) alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl; R 38 is hydrogen; R 39 is halogen, nitro, (CrC
  • R ⁇ and R ß independently hydrogen, Ci-C ⁇ alkyl, C 3 -C 8 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl,
  • R ⁇ and R ß together are a C 4 -C 6 alkylene or by oxygen, sulfur, SO, SO 2, NH or -N (C r C 4 alkyl) - interrupted C 4 -C 6 - alkylene bridge,
  • R ⁇ is hydrogen or C 1 -C 4 -alkyl
  • R a and R b independently of one another represent hydrogen, halogen, cyano, nitro,
  • R 9 and R h independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl, trifluoromethyl, methoxy, methylthio or -COOR j , where R c is hydrogen, halogen, C r C 4 alkyl or methoxy,
  • R d is hydrogen, halogen, nitro, -C 4 alkyl, Ci-C 4 alkoxy, dC 4 alkylthio, dC 4 -
  • R e is hydrogen, halogen, -C 4 alkyl, -COOR j, trifluoromethyl or methoxy, or R d and R e together represent a C 3 -C 4 alkylene bridge,
  • R f is hydrogen, halogen or C r C 4 alkyl
  • R x and R ⁇ independently represent hydrogen, halogen, -C 4 alkyl, -C 4 -
  • R j, R k and R m are independently hydrogen or C- ⁇ -C 4 alkyl, R k and R m together form a C 4 - C 6 -alkylene bridge or a C 4 -C 6 -alkylene bridge interrupted by oxygen, NH or -N (C 1 -C 4 -alkyl), and R n is C r C 4 -alkyl, phenyl or by halogen, C 1 -C 4 -alkyl, methoxy , Nitro or
  • Trifluoromethyl substituted phenyl preferably safeners of the formula (S-VIII) are 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
  • Alkyl radicals, even in the composite meanings such as alkoxy, haloalkyl, etc., preferably have 1 to 4 carbon atoms and, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
  • Alkenyl is for example AlII, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl , 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl.
  • Alkynyl means, for example Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • (C 1 -C 4 ) -alkyl is the short notation for alkyl having 1 to 4 carbon atoms; the same applies to other general remainder definitions with bracketed ranges for the possible number of C atoms.
  • Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8, preferably 3 to 7, particularly preferably 3 to 6, C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Cycloalkenyl and cycloalkynyl refer to corresponding unsaturated compounds.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl, haloalkenyl and haloalkynyl by halogen preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or fully substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 2 CF 3 , CH 2 CHFCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl.
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl.
  • a hydrocarbon radical can be an aromatic or an aliphatic radical
  • Hydrocarbon radical wherein an aliphatic hydrocarbon radical is generally a straight-chain or branched saturated or unsaturated hydrocarbon radical, preferably having 1 to 18, particularly preferably 1 to 12 C-atoms, e.g. Alkyl, alkenyl or alkynyl.
  • aliphatic hydrocarbon radical alkyl, alkenyl or alkynyl having up to 12 carbon atoms; the same applies to an aliphatic hydrocarbon radical in a Kohlenwasserstoffoxyrest.
  • Aryl is generally a mono-, bi- or polycyclic aromatic system having preferably 6-20 C atoms, preferably 6 to 14 C atoms, more preferably 6 to 10 C atoms, e.g. Phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, more preferably phenyl.
  • Heterocyclic ring, heterocyclic radical or heterocyclyl means a mono-, bi- or polycyclic ring system which is saturated, unsaturated and / or aromatic and contains one or more, preferably 1 to 4, heteroatoms, preferably from the group N, S and O. ,
  • saturated heterocycles having 3 to 7 ring atoms and one or two heteroatoms from the group N, O and S, wherein the chalcogens are not adjacent are.
  • Particularly preferred are monocyclic rings having 3 to 7 ring atoms and a heteroatom from the group N, O and S, and morpholine, dioxolane, piperazine, imidazoline and oxazolidine.
  • Very particularly preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.
  • partially unsaturated heterocycles having 5 to 7 ring atoms and one or two heteroatoms from the group N, O and S.
  • partially unsaturated heterocycles having 5 to 6 ring atoms and one heteroatom from the group N, O and S.
  • Very particular preferred partially unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.
  • heteroaryl for example mono- or bicyclic aromatic
  • Heterocycles having 5 to 6 ring atoms containing one to four heteroatoms from the group N, O, S, wherein the chalcogens are not adjacent.
  • Particularly preferred are monocyclic aromatic heterocycles having 5 to 6 ring atoms which contain a heteroatom from the group, N, O and S, and pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole and isoxazole.
  • pyrazole, thiazole, triazole and furan Very particular preference is given to pyrazole, thiazole, triazole and furan.
  • Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, such as phenyl and arylalkyl, such as benzyl, or substituted heterocyclyl, represent a substituted radical derived from the unsubstituted radical, where the substituents are preferably one or more, preferably 1, 2 or 3 , in the case of Cl and F also up to the maximum possible number, substituents from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl , substituted amino such as acylamino, mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfon
  • substituents are selected from the group halogen, for example fluorine or chlorine, (dC 4) alkyl, preferably methyl or ethyl, (C r C4) haloalkyl, preferably trifluoromethyl, (C 1 -C 10 -alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 ) halogenoalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy and chlorine.
  • halogen for example fluorine or chlorine
  • substituents methyl, methoxy and chlorine.
  • Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are N-substituted by, for example, one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles.
  • alkyl radicals having 1 to 4 carbon atoms are preferred.
  • Aryl is preferably phenyl.
  • Substituted aryl is preferably substituted phenyl. This is true for acyl the definition mentioned further below applies, preferably (CrC 4) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times, in halogens such as Cl and F also up to five times, by identical or different radicals from the group
  • Halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C- ⁇ -C 4 ) haloalkyl, (C r C 4 ) haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl , Dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluorophenyl and 2-, 3- and 4-trichlorophenyl, 2,4-, 3,5-, 2,5- and 2, 3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • An acyl radical is the radical of an organic acid having preferably up to 6 C atoms, for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radical of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids , Sulfinic acids, phosphonic acids, phosphinic acids.
  • Acyl is for example formyl, alkylcarbonyl such as (C r C 4 alkyl) -carbonyl, phenylcarbonyl, where the phenyl ring may be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl or N-alkyl 1-iminoalkyl. Also encompassed by the formulas (S-II) to (S-VIII) are all stereoisomers which have the same topological linkage of the atoms, and mixtures thereof.
  • Such compounds contain one or more asymmetric C atoms or double bonds, which are not specified separately in the general formulas are.
  • the possible defined by their specific spatial form possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers can be obtained by conventional methods from mixtures of stereoisomers or prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
  • the compounds of formula (S-II) are e.g. from EP-A-0333131 (ZA-89/1960), EP-A-0269806 (US 4,891,057), EP-A-0346620 (AU-A-89/34951), EP-A-0174562, EP-A No.
  • the compounds of formula (S-IV) are known from numerous patent applications, for example US 4,021,224 and US 4,021,229.
  • Compounds of subgroup b) are further from CN-A-87/102789, EP-A-365484 and from "The Pesticide Manual", 11th to 13th edition, British Crop Protection Council and the Royal Society of Chemistry (1997), known.
  • the compounds of subgroup c) are described in WO-A-97/45016, those of subgroup d) in WO-A-99/16744 (in particular in EP-A-365484).
  • the cited documents contain detailed information on preparation processes and starting materials and name preferred compounds. These documents are expressly referred to, they are by quotation as part of this description.
  • the safeners of the above groups a) to e) reduce or prevent the phytotoxic effects which can occur when using the herbicidal compositions according to the invention in crops without impairing the effectiveness of the herbicides against harmful plants.
  • the field of application of herbicides can be significantly extended and in particular by the use of safeners, the use of herbicides, which have so far only limited or not could be used, that is, of combinations that led to insufficient control of the harmful plants without safeners in low dosages with little broader effect.
  • Formulations include: 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] -pyrimidine -6 (2H) -one (dicyclonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor), cloquintocet, 5-chloro-quinolin-8- oxy-acetic acid (1-methyl-hexyl ester) (cloquintocet-mexyl), ⁇ - (cyanomethoxyimino) -phenylacetonitrile (cyometrinil), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl ) -N- (2-propenyl) -
  • a particular embodiment of the microemulsion concentrates according to the invention is the joint formulation of herbicides and safeners as agrochemical active ingredients.
  • ACCase inhibitors such as alloxydim, butroxydim, clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofopmethyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop , Fluazifop-P-butyl, Fluazifop-butyl, Haloxyfop, Haloxyfop-P, Haloxyfopetotyl, Haloxyfop-P-methyl, Metamifop, Profoxydim, Propaquizafop, Quizalofop-P-tefuryl, Quizalofop-P-ethyl, Sethoxydim, Tepraloxydim, Tralkoxydim and isoxapyr
  • HPPD p-hydroxyphenyl pyruvate dioxygenase
  • d) compounds which act as safeners such as AD 67 (4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane), benoxacor, CL 304,415 (4-carboxymethylchroman-4-carboxylic acid), cloquintocet, Cloquintocet-mexyl, cyprosulfamides, dichloromide, dicyclonon, DKA-24 (N1, N2-diallyl-N2-dichloroacetylglycine amides), fenchlorazoles, fenchlorazoles-ethyl, fenclorim, flurazoles, fluxofenim, furilazoles, isoxadifen-ethyl, mefenpyr-diethyl, MW 191 ( 2-dichloromethyl-2-methyl-1,3-dioxolane), naphthalic anhydride (naphthalene-1,8-dicarboxylic
  • herbicides are combined, e.g. Fenoxaprop-p-ethyl + loxyniloctanoate, diclofopmethyl + bromoxyniloctanoate, CMPP + bromoxyniloctanoate, MCPA + loxyniloctanoate, bromoxyniloctanoate + bromoxynil heptanoate, bromoxyniloctanoate + bromoxynilheptanoate + MCPA, bromoxynil octanoate + bromoxynil-heptanoate + 2,4-D, phenmedipham + desmedipham, phenmedipham + desmedipham + ethofumesate, metamitron + ethofumesate, phenmedipham + ethofumesate + metamitron, fenoxaprop-p-ethyl + iodo
  • the weight ratio safener: herbicide 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, very particularly preferably from 1:10 to 10: 1
  • Herbicide (s) and safener (s) are usually dependent on the type of herbicide and / or the safener used and on the nature of the plant stock to be treated.
  • Alcoholic solvents having at least 5 carbon atoms are in particular aromatic and non-aromatic alcohols.
  • Aromatic alcohols contain at least one aromatic and / or non-heteroaromatic group and at least one OH function.
  • Preferred aromatic alcohols are those derived from benzene, especially monofunctional benzene-derived alcohols, e.g. those of the general formula (I)
  • R is a C 1 -C 6 alkyl radical, e.g. Is methyl, ethyl, propyl or butyl, or H, n is an integer from 0 to 5, preferably 0, 1 or 2, more preferably 0, m is an integer from 0 to 10, preferably from 0 to 5, in particular from 1 to 5, especially 1 or 2.
  • Non-aromatic alcohols are cyclic, aliphatic, saturated or unsaturated or branched or unbranched alcohols.
  • Examples of monohydric alcohols having 5 to 25 carbon atoms are n-, i- or neo-pentanol, n-, i-, s-hexanol, n-, i-, s-heptanol, n-, i-, s- Octanol, n-, i-, s-decanol, n-, i-, s-undecanol, n-, i-, s-dodecanol, n-, i-, s-tridecyl alcohol, eg Cyclohexanol.
  • polyhydric alcohols examples include neopentyl glycol.
  • polyglycols commercially available e.g. available as Exxal® series (ExxonMobil), Agrisynth® PA (ISP), Arcosolv® series (Lyondell Chemical) or Nacol® 6-98 (DEA).
  • Alcohols having at least 5 carbon atoms particularly preferably alcohols having 5 to 25 carbon atoms, very particularly preferably alcohols having 6 to 20 carbon atoms, are preferred.
  • the alcohols may be primary, secondary or tertiary alcohols.
  • Particularly preferred alcoholic solvents (component b) are benzyl alcohol, n-, i-, s-hexanol, n-, i-, s-heptanol and n-, i-, s-octanol.
  • Suitable non-alcoholic solvents are, for example, hydrocarbons or polar solvents such as carboxylic acid derivatives, phosphoric esters, ethers, ketones or sulfoxides such as dimethyl sulfoxide, where water is at most impurity in an inert content of ⁇ 2 wt .-%, in particular ⁇ 1 Wt .-%, can occur.
  • hydrocarbons see, for example, Römpp Lexikon Chemie, 10th Edition, Volume 3, page 2202 (1997), Georg Thieme Verlag Stuttgart / New York
  • the hydrocarbons may be acyclic (aliphatic) hydrocarbons, or cyclic hydrocarbons, eg aromatic, alicyclic (cycloaliphatic) or heterocyclic hydrocarbons.
  • hydrocarbons as component (c) are:
  • aromatic hydrocarbons e.g. mono- or poly-alkyl-substituted (for example mono-, di- or trisubstituted (d-
  • Cio alkyl-substituted) aromatics, e.g. Benzenes such as toluene, xylene, mesitylene,
  • Ethylbenzene, or - hydrocarbons with fused aromatic ring systems such as
  • Naphthalenes e.g. 1-methylnaphthalene, 2-methylnaphthalene or dimethylnaphthalene, or other condensed aromatic hydrocarbons such as indane or tetralin,
  • cycloaliphatic hydrocarbons e.g. saturated or unsaturated, optionally mono- or poly-alkyl-substituted (for example mono-, di- or tri (C 1-10 -alkyl-substituted) cycloaliphatics, such as cycloalkanes, cycloalkenes or cycloalkynes, for example cyclohexane or methylcyclopentane,
  • heterocyclic hydrocarbons e.g. Dioxane, furan,
  • aliphatic hydrocarbons for example, linear or branched, saturated or unsaturated aliphatic, C 5 preferably - C 6 aliphatics, such as alkanes, alkenes or alkynes, such as pentane, hexane, octane, 2-
  • Methylbutane or 2,2,4-trimethylpentane Methylbutane or 2,2,4-trimethylpentane.
  • polar solvents are aprotic, polar solvents such as carboxylic acid derivatives, for example the full ethers and full esters of CrCg-alkanoic acids, which may be mono-, di- or polyfunctional, for example the ethers and esters with C 1 -C 20 -alkyl alcohols, such as Ketones, phosphoric esters such as tri (butoxyethyl) phosphate, triethyl phosphate, amides, nitriles or sulphones, eg diisobutyl adipate, Rhodiasolv® RPDE (Rhodia), cyclohexanone, Jeffsol® PC (Huntsman), ⁇ -butyrolactone, N-methylpyrrolidone, N-octylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetonitrile, tributyl phosphate or Hostarex® PO series (Clariant), or pro
  • the alcohols, amines or carboxylic acids preferably have 1 to 18 C atoms and can be linear, branched or cyclic, saturated or unsaturated, optionally contain heteroatoms and be mono- or polyfunctionalized.
  • amines are diethylamine, hexylamine or aniline.
  • carboxylic acids are monocarboxylic acids or partially esterified di- or polycarboxylic acids, for example adipic acid and adipic acid monoester.
  • carboxylic acid derivatives are e.g. the fullest or amides of carboxylic acids.
  • carboxylic acid derivatives are e.g. the esters and amides of monocarboxylic acids, dicarboxylic acids or polycarboxylic acids such as tri-, tetra- or even higher-functional carboxylic acids, preferably having 2-26 C atoms in question.
  • esters with Carbon Textreester -C 2 o-alcohols for example methanol, ethanol, propanol or butanol
  • esters with carboxylic acid esters for example methanol, ethanol, propanol or butanol
  • carboxylic acid esters internal esters such as lactones are also suitable.
  • monocarboxylic esters are the esters of aliphatic and aromatic monocarboxylic acids, for example aliphatic C 1 -C 4 -monocarboxylic acid esters, such as formic acid esters, acetic acid esters and propionic acid esters, or aliphatic fatty acid esters, such as C 10 -C 2 -fatty acid esters, for example of natural origin as contained in natural oils or vegetable oils, or synthetic ones Origin, or aromatic C 7 -C 22 monocarboxylic acid esters such as benzoic acid ester or phenylacetic acid ester.
  • monocarboxylic esters are the esters of aliphatic and aromatic monocarboxylic acids, for example aliphatic C 1 -C 4 -monocarboxylic acid esters, such as formic acid esters, acetic acid esters and propionic acid esters, or aliphatic fatty acid esters, such as C 10 -C 2 -fatty acid esters, for example of natural origin
  • fatty acid esters are, for example, those of natural origin, for example natural oils such as animal oils or vegetable oils, or of synthetic origin, eg Edenor® MESU or Agnique® ME series (Cognis), the Salim® ME series (Salim), the Stepan® C-series (Stepan) or the Witconol® 23-series (Witco).
  • a fatty acid ester are preferably esters of C10-C22, preferably C 2 -C 2 o-fatty acids.
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 fatty acids, in particular having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and, in particular, fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • fatty acid esters such as Cio-C 22 fatty acid esters are glycerol and glycol esters of fatty acids such as C- ⁇ o-C- 22 fatty acids or their
  • Transesterification products for example alkyl-fatty acid ester such as Ci-C2o-alkyl-Cio-C 22 -Fettklare- esters, such as for example, by transesterification of the abovementioned glycerol or glycol fatty acid ester such as C10-C22 -Fett.saure-Est.er with C r C 2 o alcohols (eg, methanol, ethanol, propanol or butanol) can be obtained.
  • the transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • Preferred fatty acid esters are, for example, oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, walnut oil, peanut oil, olive oil or castor oil, in particular rapeseed oil, where the vegetable oils are also understood to be transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, walnut oil, peanut oil, olive oil or castor oil, in particular rapeseed oil, where the vegetable oils are also understood to be transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • dicarboxylic esters and polycarboxylic esters are the full esters of oxalic, malonic, succinic, glutaric, adipic, pimelic, sebacic, azelaic, suberic, maleic, phthalic, terephthalic, mellitic, trimellitic and polymaleic acid, in particular the C 1 -C 10 -alkyl esters, such as the methyl esters, ethyl esters, propyl esters, such as n-propyl or isopropyl esters, butyl esters, such as n-butyl ester, isobutyl ester, sec-butyl ester or tert-butyl ester.
  • carboxamides are also -C 26 -carboxylic acid-N, N-di (2 CrC o- alkyl) amides such as Ci-C 26 -carboxylic acid-N, N-dimethylamide, such as N, N-dimethylformamide or N, N-dimethylacetamide in question , or internal amides such as lactams, eg
  • Pyrrolidones such as N-substituted CrCi 2 alkyl-pyrrolidone such as N-methyl-pyrrolidone, N-butyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone and N-cyclohexyl-pyrrolidone.
  • Suitable phosphoric esters are triesters of phosphoric acid with alcohols, the alcohols preferably being selected from the group consisting of
  • monohydric alkanols having 1 to 22 C atoms e.g. n-, i- or neo-pentanol, n-hexanol, n-octanol, 2-ethylhexanol, 2) diols or polyols, such as ethylene glycol, propylene glycol or glycerol,
  • aryl, alkylaryl, poly (alkyl) aryl and poly (arylalkyl) aryl alcohols for example phenol and / or cresol, octylphenol, nonylphenol, triisobutylphenol, tristyrylphenol,
  • alkoxylated alcohols which are obtained by reacting the alcohols mentioned above under 1), 2) or 3) with alkylene oxides, preferably (C 1 -C 4 ) alkylene oxides.
  • Preferred phosphoric esters are triesters of orthophosphoric acid, in particular alkoxylated triesters of orthophosphoric acid, such as tri (butyoxyethyl) phosphate.
  • Suitable ketones are, for example, aromatic, cycloaliphatic or aliphatic ketones, such as acetophenone, benzophenone, isophorone, cyclohexanone and methyl ethyl ketone, ethyl butyl ketone, diethyl ketone, dibutyl ketone.
  • Suitable ethers are aromatic, cycloaliphatic or aliphatic ethers, such as anisole, tetrahydrofuron, oxirane, dibutyl ether, dipentyl ether, butylhexyl ether, methyl tert-butyl ether.
  • Preferred non-alcoholic solvent (component c) are aromatic hydrocarbons, such as, -C 6 alkyl-benzenes such as toluene or xylene, CrC 6 - alkylnaphthalenes and mixtures of aromatic compounds such as the Solvesso series from Exxon, ketones such as acetophenone, isophorone, cyclohexanone and methyl ethyl ketone, N-substituted CrCl 2 -alkyl-pyrrolidones such as N-methyl-pyrrolidone, N-butyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone and N-cyclohexyl-pyrrolidone, cyclic aliphatic hydrocarbons such as decalin and cyclohexane, acid amides such as dimethylformamide , Dimethyl sulfoxide, lactones such as
  • Component c are aromatic solvents, such as Solvesso® 100, Solvesso® 150, Solvesso® 200 or Solvesso® 200 ND, xylene, triethyl phosphate, rapeseed oil methyl ester (eg Edenor® MESU or Agnique® ME series) or rapeseed oil ethyl ester, N-octylpyrrolidone and N-methylpyrrolidone.
  • aromatic solvents such as Solvesso® 100, Solvesso® 150, Solvesso® 200 or Solvesso® 200 ND, xylene, triethyl phosphate, rapeseed oil methyl ester (eg Edenor® MESU or Agnique® ME series) or rapeseed oil ethyl ester, N-octylpyrrolidone and N-methylpyrrolidone.
  • Suitable anionic surfactants are, for example, sulfates, sulfonates, sulfosuccinates, phosphates and phosphonates of hydrocarbons, which may optionally contain alkylene oxide units.
  • the sulfates, sulfonates, phosphates and phosphonates may be in the form of the acids or as salts.
  • Anionic surfactants (d) of the following formula (II) are preferred:
  • R - Q (II) where Q - O - SO 3 M 1 --SO 3 M, - O - PO 3 HM or PO 3 HM, in which M is H or a cation, in particular a metal cation such as an alkali metal ion or alkaline earth metal ion, or an ammonium ion,
  • R is an unsubstituted or substituted CrC 30 -hydrocarbon radical such as a -C 2 -alkyl radical or C 6 -C 24 -aryl radical which optionally via
  • Alkylene oxide units may be bonded, or R is an alkylene oxide unit.
  • alkylene oxide units is understood to mean, in particular, units of C 2 -C 10 -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, where the units within the surfactant may be the same or different and may be randomly mixed or blockwise arranged.
  • R is a 2 CiC o-alkyl (eg methyl, ethyl, propyl, butyl) or a C 6 - C 2 4-aryl (eg, phenyl, biphenyl, naphthyl) which optionally one or more radicals such as 2 CiC o Hydrocarbon radicals may bear, for example, from the group C1-C 20 - alkyl (eg linear or branched Ci-C 2 o-alkyl such as sec-butyl or dodecyl), which one or more radicals such as C 6 -C 2O -AIyI radicals can carry, for example, phenyl, biphenyl, naphthyl), and C 6 -C 2O -AIyI (eg, phenyl, biphenyl or naphthyl) which may carry one or more radicals optionally as CiC-io alkyl (eg methyl, ethyl, propyl, butyl) or a
  • R is a radical R 2 O- (AO) w, wherein w is an integer from 1 to 100, preferably 2 to 50, in particular 2 to 10, and AO is an alkylene oxide unit, for example (EO) x (PO) ⁇ (BO) z, where EO is an ethylene oxide unit, PO is a propylene oxide unit, BO is a butylene oxide unit, x is an integer from 0 to 100, y is an integer from 0 to 100, z is an integer from 0 to 100 and the sum x + y + z is at least 1, and the alkylene oxide unit, for example (EO) ⁇ (PO) ⁇ (BO) z, can be randomly mixed or block-structured, and
  • R 2 is H, a C 1 -C 2 o-alkyl radical (eg, methyl, ethyl, propyl, butyl) or a C 6 -C 24 aryl radical (eg, phenyl, biphenyl, naphthyl) which optionally has one or more radicals, such as CrC can carry 2 o-hydrocarbon radicals, for example from the group dC 2 o-alkyl (for example, linear or branched CrC 2 O-alkyl such as sec.
  • a C 1 -C 2 o-alkyl radical eg, methyl, ethyl, propyl, butyl
  • a C 6 -C 24 aryl radical eg, phenyl, biphenyl, naphthyl
  • CrC can carry 2 o-hydrocarbon radicals, for example from the group dC 2 o-alkyl (for example, linear or branched CrC 2 O-alkyl
  • butyl or dodecyl which comprises one or more radicals such as -C 2 o-hydrocarbon groups such as C 6 -C 2 o-aryl radicals (For example, phenyl, biphenyl, naphthyl), and C 6 -C 2 o-aryl (eg, phenyl, biphenyl, naphthyl), which may optionally carry one or more radicals such as C r do-alkyl (eg, methyl, ethyl, propyl , Butyl), or R 2 is - O - SO 3 M, - SO 3 M 1 - O - PO 3 HM, H or PO 3 HM 1, preferably PO 3 HM, where M is H or a cation, in particular a metal cation, such as an alkali metal ion or alkaline earth metal ion, or an ammonium ion.
  • R 2 is - O - SO 3 M, - SO 3 M 1 - O
  • Particularly preferred anionic surfactants (d) are dialkyl sulfosuccinates, e.g. Di (2-ethylhexyl) sulfosuccinate sodium (e.g., Triton® GR 7 ME from Union Carbide), alkylaryl sulfonates such as dodecyl benzene sulfonates, e.g.
  • Erdalkalidodecylbenzolsulfonate such as calcium dodecylbenzenesulfonates (eg, for example Phenylsulfonat® Ca 100, synonymous Calsogen® AR 100 ND, Phenylsulfonat® Ca 70 from Clariant), Alkylarylpolyglykolethersulfate and sulfonates, in particular Arylalkylarylpolyglykolethersulfate as Tristyrylphenolpolyglykolethersulfate, especially the alkali or ammonium or triethanolamine (eg Soprophor® Rhodia series), alkyl ether sulfates and their salts (eg, such as Genapol® LRO from Clariant), alkyl sulfates and alkyl sulfonates (eg, like Clariant's Hostapur® series), alkyl polyglycol ether phosphates, especially the alkali salts (eg Rhoda
  • Suitable nonionic surfactants are, for example, alkoxylates, for example ethoxylates, propoxylates or butoxylates and combinations thereof.
  • alkoxylates is understood as meaning compounds which contain alkylene oxide units, in particular units of C 2 -C 10 -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, wherein the units within the surfactant may be the same or different and may be randomly mixed or blockwise arranged.
  • alkoxylates as component (e) are compounds of the following formula (III): R 1 - (AO) w R 2 (III) wherein
  • R 1 is selected from the group consisting of H, HO, C 1 -C 3 o-alkyl, which may be linear or branched, (for example methyl, ethyl, propyl, butyl, pentyl, hexyl), C 1 -C 30 -alkoxy, preferably C 10 alkoxy, which may be linear or branched (eg methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy), (For example, phenyl), which may optionally carry one or more radicals such as CrC 3 o-arylalkyl (eg styrylphenyl) or Ci-C 30 alkyl, wherein the alkyl groups may be linear or branched (eg butyl or dodecyl), C 6 -C 2 4- aryloxy (eg phenoxy) which may optionally carry one or more radicals, such as C 1 -C 30 -arylalkyl (eg sty
  • R 1 is a Sorbitanesterrest, a Glycerinesterrest, or C- ⁇ -C 3 o-alkyl-NR 4, preferably Cio-C 2 o-alkyl-NR 4, wherein the C- ⁇ -C2o-alkyl group may be linear or branched ( eg dodecyl, hexadecyl, octadecyl) and wherein R 4 is H or C 1 -C 10 alkyl (eg methyl, ethyl, propyl, butyl),
  • R 2 is H or C 1 -C 6 -alkyl, which may be linear or branched (for example methyl, ethyl, propyl, butyl, pentyl or hexyl), and w is an integer from 1 to 100, preferably 4 to 80, in particular 6 to 50, AO is an alkylene oxide unit, eg (EO) x (PO) ⁇ (BO) 2 , where EO is a
  • Ethylene oxide unit PO is a propylene oxide unit
  • BO is a butylene oxide unit
  • x is an integer of 0-100
  • y is an integer of 0-100
  • z is an integer of 0-100 and the sum of x + y + z is at least 1, and Alkylene oxide unit, for example (EO) ⁇ (PO) ⁇ (BO) z , randomly mixed or constructed in blocks.
  • Nonionic surfactants are Alkylarylpolyalkoxylate, for example the ethoxylates, propoxylates and / or butoxylates, Arylalkylarylpolyalkoxylate as Tristyrylphenylpolyalkoxylate (eg Soprophor® series by Rhodia) and Alkylphenylpolyalkoxylate as Tributylphenylpolyalkoxlate (for example Sapogenat ® series by Clariant), alkylene oxide block copolymers such as ethylene oxide ( EO) propylene oxide (PO) block copolymers (eg Emulsogen® 3510, Emulsogen® V 1816, Genapol® PF 10, Genapol® PF 20, Genapol® PF 40 from Clariant, Berol® 992 from Akzo Nobel) or Ethylene oxide (EO) -butylene oxide (BO) block copolymers (eg Pluronic® series from BASF), polyalkylene oxide
  • radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding unsaturated and / or substituted radicals, they may each be straight-chain or branched in the carbon skeleton. Unless specifically stated, these radicals generally have from 1 to 30 carbon atoms, with the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, are preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • alkenyl preferably denotes an alkenyl radical having 3 to 4, 3 to 5, 3 to 6, 3 to 8 or 3 to 12 C atoms, in which the double bond does not exist on the C atom, which is connected to the remaining part of the molecule of the compound ("y ⁇ " position).
  • alkenyl preferably denotes an alkenyl radical having 3 to 4, 3 to 5, 3 to 6, 3 to 8 or 3 to 12 C atoms, in which the
  • a hydrocarbon radical means a straight, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, e.g. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl.
  • a hydrocarbon radical preferably has 1 to 40 C atoms, preferably 1 to 30 C atoms; particularly preferably a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 C atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring may be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3 heteroatoms.
  • the heterocyclic radical may be e.g. a heteroaromatic radical or ring (heteroaryl), e.g.
  • a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below in question, in addition also oxo.
  • the oxo group may also occur on the hetero ring atoms, which may exist in different oxidation states, eg at N and S.
  • Halogen is, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl by halogen preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl;
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Hydrocarbon radicals for example alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or heterocyclyl or heteroaryl, may be substituted, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, Hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals , Alkyl and haloalkyl and said saturated hydrocarbon-containing radicals corresponding unsatur
  • substituents are selected from the group halogen, for example fluorine and chlorine, (C- ⁇ -C 4) alkyl, preferably methyl or ethyl, (Ci-C4) haloalkyl, preferably trifluoromethyl, (CrC 4) alkoxy, preferably methoxy or Ethoxy, (C 1 -C 4 ) haloalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy and chlorine.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C r C4) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluorophenyl and 2-, 3- and 4-trichlorophenyl , 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • An acyl radical is the radical of an organic acid which is formally formed by cleavage of an OH group from the organic acid, for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radicals of carbonic acid monoesters, optionally N -substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
  • acyl radical is preferably formyl or aliphatic acyl from the group CO-R X ,
  • R x and R ⁇ each represent a C 1 -C 30 -hydrocarbon radical which is unsubstituted or substituted, or aminocarbonyl or aminosulfonyl, where the latter two radicals are unsubstituted, N-monosubstituted or N, N-disubstituted.
  • Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl as
  • Formula (I), (II), (III) and the other compounds mentioned in this description also include all stereoisomers and mixtures thereof.
  • the possible defined by their specific spatial form possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers are all encompassed by the respective formulas and can be obtained by conventional methods from mixtures of stereoisomers or by stereoselective reactions in combination with the use of stereochemically pure Starting materials are produced.
  • the preparation of the microemulsion concentrates according to the invention can be carried out by customary processes, for example mixing by dissolving or emulsifying the individual components, preferably at room temperature. If other auxiliaries and additives are included, they are also preferred at room temperature entered. The order of addition of the individual components is generally arbitrary.
  • agrochemical active substances other than components (a) and (b), such as fungicides, insecticides and / or growth regulators, e.g. in the form of a ready-to-use formulation or as a tank mix.
  • microemulsion concentrates according to the invention can be diluted with water to microemulsions, which are likewise the subject of the present invention.
  • the weight ratio of microemulsion concentrate: water may be, for example, 1: 0.00001 to 0.1: 1000, preferably 1: 0.0001 to 0.1: 100, resulting in concentrated microemulsions which are storage stable as such.
  • these can be further diluted with water to spray liquors, which are generally in the form of emulsions such as microemulsions, aqueous solutions, suspensions or suspoemulsions.
  • microemulsion concentrates and microemulsions according to the invention may be contained together in a ready-to-use formulation which is then in the customary manner, for example in the form of a spray mixture can be applied.
  • microemulsion concentrates according to the invention may contain, in addition to the components (a), (b), (c), (d) and (e) as a further component, various formulation auxiliaries (component f) , eg customary auxiliaries and additives, such as anti-drift agents, humectants, fertilizers, such as ammonium sulfate, urea or multi-component fertilizer, for example.
  • various formulation auxiliaries component eg customary auxiliaries and additives, such as anti-drift agents, humectants, fertilizers, such as ammonium sulfate, urea or multi-component fertilizer, for example.
  • agrochemical agents as well as their preparation and use are also novel and subject of this invention.
  • customary auxiliaries and additives are wetting agents such as Genapol® LRO (0-35% by weight), dispersants such as Tamol® (0-15% by weight) or further surfactants (for example cationic or polymeric surfactants ) (0-30% by weight);
  • Inorganic salts such as NaCl, Na 2 SO 4 , MgCl 2 (0-50% by weight), (oligo-, poly-) phosphates; Carbonates such as potassium carbonate; - Fertilizers such as ammonium sulfate, ammonium nitrate, urea, phosphorus and potassium-containing components, optionally further trace elements (0-60 wt .-%);
  • Defoamers such as Fluowet® PP (0-2% by weight) or from the Rhodorsil® series (for example Rhodorsil® 481);
  • Binders such as suitable natural or synthetic substances such as polyamino acids, polyvinyl alcohols, polyvinylpyrrolidone, polyacrylic acid derivatives
  • the use of the agrochemical compositions according to the invention can be done for example by application to the harmful organisms or the places where they occur, eg by spraying.
  • the agrochemical compositions according to the invention are generally applied in the form of a spray mixture containing the components (a), (b), (c), (d) and (e) in effective amounts and optionally conventional auxiliaries and additives (T), eg for the formulation or application.
  • the spray mixture is generally prepared on the basis of water, it being possible to add customary auxiliaries and additives (f), for example oils, such as vegetable oils or high-boiling hydrocarbons, such as kerosene or paraffin.
  • the concentration of active ingredient (component a) is generally from 10 "6 to 10 wt .-%, preferably at 10 " 5 to 4 wt .-% in the applied agent, eg the spray mixture, at a rate of 1 to 5000 l / ha, preferably 50 to 1000 l / ha.
  • concentrated formulations present in commercial form are optionally diluted in customary manner, e.g. by means of water. It may be advantageous to add to the spray mixtures further amounts of components (c), (d) and (e) and / or other auxiliary agents and additives (f) customary for use, in particular self-emulsifying oils or paraffin oils. Also, additional components (a) may be added or other agrochemical agents other than components (a).
  • Preferred mixtures are compounds which are effective as ACCase inhibitors or as p-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors, with compounds which act as safeners, as stated above, which are then used as ready-to-use formulation or as tank mix for the production of spray liquors can be used.
  • HPPD p-hydroxyphenyl pyruvate dioxygenase
  • Component a agrochemical active ingredients
  • It can vary within wide limits, for example between 0.001 and 10 kg / ha or more active substance, preferably between 0.005 and 5 kg / ha.
  • the agrochemical compositions according to the invention are preferably herbicidal agents, they have an excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even hard-to-control perennial weeds that sprout from rhizomes, rhizomes or other permanent organs are well recorded.
  • the means may e.g. be applied in pre-sowing, pre-emergence or post-emergence.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the herbicidal compositions according to the invention, without the intention of being restricted to certain species.
  • the spectrum of activity extends to species such as, for example, Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp.
  • herbicidal compositions according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die completely after three to four weeks.
  • the herbicidal compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • the rainfastness of the active ingredients in the combinations according to the invention is generally favorable.
  • a particular advantage is the fact that the effective and used in the herbicidal compositions dosages of herbicidal compounds can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contaminations are virtually avoided.
  • the combination of active substances according to the invention enables a considerable reduction in the required application rate of the active substances.
  • herbicidal compositions of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds
  • Crops of economically important crops e.g. dicotyledonous crops such as soybean, cotton, oilseed rape, sugarbeet, or graminaceous crops such as wheat, barley, rye, oats, millet, rice or maize, only marginally or not at all damaged.
  • dicotyledonous crops such as soybean, cotton, oilseed rape, sugarbeet, or graminaceous crops
  • graminaceous crops such as wheat, barley, rye, oats, millet, rice or maize
  • the herbicidal compositions according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
  • the herbicidal compositions according to the invention can also be employed for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z.
  • the application of the herbicidal compositions according to the invention can also be carried out in economically important transgenic crops of useful and ornamental plants, for.
  • B. Graminaceous crops such as wheat, barley, rye, oats, millet, rice and corn or even cultures of sugar beet, cotton, soybeans, rape, potato, tomato, pea and other vegetables.
  • the agents according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the present invention further provides a method for controlling undesired plant growth, preferably in crops such as cereals (eg wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, more preferably in monocotyledonous crops such as cereals, for example wheat, barley, rye, oats, crossings thereof such as triticale, rice, maize and millet, where the herbicidal composition according to the invention is grown on the harmful plants, plant parts, plant seeds or the area on which the plants grow, for example the cultivated area applied, for example in pre-emergence, post-emergence or pre-emergence and post-emergence, preferably in pre-emergence.
  • the plant cultures may also be genetically engineered or obtained by mutation selection and are preferably tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS acetolactate synthase
  • the invention also provides the use of the herbicidal compositions according to the invention for controlling harmful plants, preferably in plant crops.
  • a preferred use relates to the use of herbicidal compositions containing synergistic amounts of components (a), (b), (c), (d), (e) and optionally (f).
  • herbicidal compositions of the invention may also be used non-selectively to control undesired plant growth, e.g. in plantation crops, on roadsides, squares, industrial plants or railway facilities.
  • agrochemical compositions according to the invention may optionally be present as mixed formulations with other agrochemical active compounds (eg further herbicides and safeners, insecticides, fungicides, growth regulators) and customary auxiliaries and additives (f), which are then diluted with water in the customary manner Be made use of, or prepared as so-called tank mixes by co-diluting the separately formulated or partially separately formulated components with water.
  • agrochemical active compounds eg further herbicides and safeners, insecticides, fungicides, growth regulators
  • customary auxiliaries and additives f
  • the invention therefore also relates to a method for selective
  • Control of harmful plants in crops characterized in that a herbicidally effective amount of herbicides (a), alone or together with Safenern, in combination with the components (c), (d) and (e) applied, optionally in combination with component (T), eg in the pre-emergence, post-emergence or pre-emergence and post-emergence, preferably in pre-emergence, the plants, plant parts , Plant seeds or the place or area on which the plants grow, eg the acreage.
  • the required application rates of the safeners (a) in the field may vary within wide limits depending on the indication and the herbicide used and are generally in the range of 0.001 to 1 kg, preferably 0.005 to 0.2 kg of active substance / ha.
  • herbicidal compositions with the active compound combinations according to the invention are therefore used for the selective control of undesired plants.
  • the application of the herbicidal compositions according to the invention can be carried out in a customary manner, for example with water as carrier in Spritzbrühmengen of about 5 to 4000 liters / ha.
  • Low-volume and ultra-low-volume method (ULV) is also possible.
  • compositions usually in subordinate quantities, in addition one, two or more of components (a) different agrochemical active ingredients from other areas (eg insecticides, fungicides, growth regulators) may be included.
  • agrochemical active ingredients from other areas (eg insecticides, fungicides, growth regulators) may be included.
  • Harmful organisms such as to use harmful plants in crops, without departing from the spirit of the invention.
  • microemulsion concentrates and microemulsions according to the invention exhibit improved chemical and physical stability as well as advantageous physical application behavior.
  • the agrochemical active ingredients of components (a), and optionally further added agrochemical active ingredients remain evenly distributed during application in the spray tank, whereby a uniform application to the crop or acreage is made possible.
  • Also formed in the spray tank mixtures (tank mixtures) such as aqueous solutions, suspensions, emulsions or suspoemulsions are stable.
  • the agrochemical compositions according to the invention have an excellent biological activity and are preferably synergistic. These effects allow, inter alia, a reduction of the application rate, the control of a wider range of harmful organisms, the closure of gaps, a faster and safer effect, a longer lasting effect, a complete control of the harmful organisms with only one or a few applications, and an extension of the period of application ,
  • the solvents were initially charged and the agrochemical active substances and then the surfactants and customary auxiliaries and additives were added with stirring.
  • the microemulsion concentrates so obtained were allowed to u.a. over a period of 3 months. stored at -10, 0, 25, 40 and 50 degrees Celsius and were chemically and physically stable throughout the period.
  • Phenmedipham (Bayer CropScience): herbicide Desmedipham (Bayer CropScience): herbicide ethofumesate (Bayer CropScience): herbicide Metamitron (Bayer CropScience): Lactofen herbicide (Bayer CropScience): Fenoxaprop-p-ethyl herbicide (Bayer CropScience): Mefenpyr-diethyl herbicide (Bayer CropScience): Safener Benzyl alcohol (Merck): Aromatic alcohol with at least 5 C atoms
  • Berol® 992 Alcohol ethoxylate propoxylate
  • Emulsogen® 3510 (Clariant): EO-PO-B lock copolymer
  • Emulsogen® V 1816 (Clariant): EO-PO block copolymer
  • Genapol® X-060 (Clariant): isotridecyl alcohol with
  • Genapol® X-080 (Clariant): isotridecyl alcohol with
  • Genapol® PF 10 (Clariant): EO-PO-EO block copolymer
  • Genapol® PF 20 (Clariant): EO-PO-EO block copolymer
  • Genapol® PF 40 (Clariant): EO-PO-EO block copolymer
  • Phenylsulfonate® Ca 70 (Clariant): calcium dodecylbenzenesulfonate
  • Solvesso® 200 ND (Exxon): Aromatic mixture
  • Triton® GR 7 ME (Union Carbide): di (2-ethylhexyl) sulfosuccinate
  • microemulsion concentrates according to the invention listed in Table I have the desired properties.
  • Table II shows the effect of the microemulsion concentrates according to the invention on weeds in comparison with a standard formulation at the same application concentration.
  • microemulsion concentrates according to the invention produce a significantly improved biological effect at the same application dosage as the standard formulation of the prior art.

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Abstract

The present invention relates to a microemulsion concentrate comprising a) one or more agrochemical actives, more particularly from the group of fungicides, insecticides, plant growth regulators, herbicides and safeners, b) one or more alcoholic solvents having at least 5 C atoms, c) one or more non-alcoholic solvents, d) one or more anionic surfactants, and e) one or more nonionic surfactants. The microemulsion concentrate is suitable for the field of crop protection.

Description

Beschreibung description
Neue MikroemulsionskonzentrateNew microemulsion concentrates
Die vorliegende Erfindung betrifft das Gebiet der Pflanzenschutzmittelformulierungen. Insbesondere betrifft die Erfindung flüssige agrochemische Formulierungen in Form von Mikroemulsionskonzentraten und Mikroemulsionen.The present invention relates to the field of crop protection formulations. In particular, the invention relates to liquid agrochemical formulations in the form of microemulsion concentrates and microemulsions.
Wirkstoffe für den Pflanzenschutz werden im allgemeinen nicht in ihrer reinen Form eingesetzt. In Abhängigkeit von dem Anwendungsgebiet und der Anwendungsart, sowie von physikalischen, chemischen und biologischen Parametern wird der Wirkstoff in Mischung mit üblichen Hilfs- und Zusatzstoffen als feste oder flüssige Wirkstoffformulierung eingesetzt. Aber auch die Wirkstoffformulierung von Kombinationen (Mischungen) mit weiteren Wirkstoffen zur Erweiterung des Wirkungsspektrums und/oder zum Schutz der Kulturpflanzen, wie mit Safenern (Antidote), ist ein wichtiges Arbeitsgebiet der Formulierungstechnologie, da hier Wirkstoffe mit zum Teil recht unterschiedlichen physikalischen, chemischen und biologischen Parametern adäquat gemeinsam formuliert werden müssen.Active ingredients for crop protection are generally not used in their pure form. Depending on the field of application and the type of application, as well as on physical, chemical and biological parameters, the active ingredient is used in admixture with customary auxiliaries and additives as a solid or liquid active substance formulation. But the drug formulation of combinations (mixtures) with other agents to extend the spectrum of activity and / or protection of crops, such as safeners (antidotes), is an important field of formulation technology, since here are active substances with sometimes quite different physical, chemical and biological parameters must be adequately formulated together.
So sollten Formulierungen von Kombinationen mehrerer Wirkstoffe, für den Pflanzenschutz im allgemeinen eine hohe chemische und physikalische Stabilität, eine gute Applizierbarkeit und Anwenderfreundlichkeit und eine breite biologische Wirkung mit hoher Selektivität im Hinblick auf die verwendeten Wirkstoffe aufweisen, neben einer technisch guten Formulierbarkeit im Herstellungsprozess.Thus, formulations of combinations of several active ingredients for plant protection should generally have a high chemical and physical stability, good applicability and user-friendliness and a broad biological activity with high selectivity with regard to the active ingredients used, in addition to a technically good formability in the manufacturing process.
Flüssige Formulierungen sind z.B. beschrieben in EP 0 261 492, EP 0 394 847, WO 95/17822, WO 98/31223, WO 89/03176, EP 0 357 149, WO 02/45507, GB 2 267 825 A, WO 94/23578, EP 0 330 904, EP 0 533 057, EP 0 533 057, DE 36 24 910, WO 01/74785, EP 0 400 585, EP 0 118 579, XP 002 177 928, EP 0 648 414 A1 , US 5 300 529, US 0 533 057, EP 0 330 904 A1 , DE 2 328 192 A1 , EP 0 432 062 A1 , EP 0 297 207 A1 , DE 81 162 B1 , EP 0 244 754 A1 , WO 99/45780, WO 99/40784, WO 87/04047, DE 3 618 535 A1 , WO 04/054360 und WO 98/16102.Liquid formulations are described, for example, in EP 0 261 492, EP 0 394 847, WO 95/17822, WO 98/31223, WO 89/03176, EP 0 357 149, WO 02/45507, GB 2 267 825 A, WO 94 / 23578, EP 0 330 904, EP 0 533 057, EP 0 533 057, DE 36 24 910, WO 01/74785, EP 0 400 585, EP 0 118 579, XP 002 177 928, EP 0 648 414 A1, US 5 300 529, US Pat. No. 5,333,057, EP 0 330 904 A1, DE 2 328 192 A1, EP 0 432 062 A1, EP 0 297 207 A1, DE 81 162 B1, EP 0 244 754 A1, WO 99/45780, WO 99/40784, WO 87/04047, DE 3 618 535 A1, WO 04/054360 and WO 98/16102.
In EP 0 257 286 A1 wird die Herstellung einer Mikroemulsion (ME) für das Insektizid Endosulfan beschrieben, welche ein Lösungsmittelgemisch verwendet in dem Isobutanol, ein C-4-Alkohol, enthalten ist.In EP 0257286 A1 the preparation of a microemulsion (ME) for the insecticide Endosulfan is described which comprises a solvent mixture used in the isobutanol in a C, is 4 alcohol.
Die Aufgabe der vorliegenden Erfindung bestand darin, eine verbesserte Pflanzenschutzmittelformulierung zur Verfügung zu stellen, die auch im Hinblick auf die verwendeten Wirkstoffe und/oder Kombinationen daraus vorteilhaft ist, wie z.B. eine verbesserte Wirksamkeit aufweist.The object of the present invention was to provide an improved crop protection formulation which is also advantageous with regard to the active ingredients used and / or combinations thereof, e.g. has improved effectiveness.
Überraschenderweise wurde nun gefunden, dass diese Aufgabe durch das spezielle Mikroemulsionskonzentrat (MC) der vorliegenden Erfindung gelöst wird.Surprisingly, it has now been found that this object is achieved by the special microemulsion concentrate (MC) of the present invention.
Die vorliegende Erfindung betrifft somit ein Mikroemulsionskonzentrat, enthaltend (a) ein oder mehrere agrochemische Wirkstoffe, insbesondere aus der Gruppe der Fungizide, Insektizide, Pflanzenwachstumsregulatoren, Herbizide und Safener, (b) ein oder mehrere alkoholische Lösungsmittel mit mindestens 5 C-Atomen,The present invention thus relates to a microemulsion concentrate comprising (a) one or more agrochemical active compounds, in particular from the group of fungicides, insecticides, plant growth regulators, herbicides and safeners, (b) one or more alcoholic solvents having at least 5 carbon atoms,
(c) ein oder mehrere nicht-alkoholische Lösungsmittel,(c) one or more non-alcoholic solvents,
(d) ein oder mehrere anionische Tenside, und(d) one or more anionic surfactants, and
(e) ein oder mehrere nichtionische Tenside.(e) one or more nonionic surfactants.
Darüber hinaus kann das erfindungsgemäße Mikroemulsionskonzentrat als weitere Komponenten gegebenenfalls noch enthalten (f) übliche Hilfs- und Zusatzstoffe.In addition, the microemulsion concentrate according to the invention may optionally still contain as further components (f) customary auxiliaries and additives.
Unter dem Begriff Mikroemulsionskonzentrat (MC) wird eine Komposition verstanden, die bei Verdünnung mit Wasser Mikroemulsionen (ME) bildet, z.B. Öl-in- Wasser-Mikroemulsionen oder Wasser-in-ÖI-Mikroemulsionen. Unter einerBy the term microemulsion concentrate (MC) is meant a composition which, when diluted with water, forms microemulsions (ME), e.g. Oil-in-water microemulsions or water-in-oil microemulsions. Under one
Mikroemulsion wird eine Emulsion verstanden, die thermodynamisch stabil ist und eine geringe Tröpfchengröße der emulgierten Phase aufweist, die im allgemeinen im Bereich von 10 - 400 nm, vorzugsweise 20 - 350 nm liegt.Microemulsion is understood to be an emulsion which is thermodynamically stable and has a small droplet size of the emulsified phase, which is generally in the range of 10 - 400 nm, preferably 20 - 350 nm.
Somit zeichnen sich Mikroemulsionskonzentrate u.a. dadurch aus, dass kein Wasser als Formulierungshilfsstoff benutzt wird. Dennoch können Verunreinigungen an Wasser über die einzelnen Komponenten eingeschleust werden. Dieser Wassergehalt bis maximal < 2 Gew.-%, in der Regel 0 bis < 1 Gew.-%, ist für die Qualität des Mikroemulsionskonzentrates jedoch unerheblich.Thus, microemulsion concentrates i.a. in that no water is used as a formulation adjuvant. Nevertheless, impurities in water can be introduced via the individual components. This water content to a maximum of <2 wt .-%, usually 0 to <1 wt .-%, but is irrelevant to the quality of the microemulsion concentrate.
Die erfindungsgemäßen Mikroemulsionskonzentrate enthalten im allgemeinen folgende Mengen an Komponenten (a), (b), (c), (d), (e) und (f), dabei bezieht sich dieThe microemulsion concentrates according to the invention generally contain the following amounts of components (a), (b), (c), (d), (e) and (f), in which case
Angabe „Gew.-%" hier und in der gesamten Beschreibung, wenn nicht anders definiert, auf das relative Gewicht der jeweiligen Komponente bezogen auf das"% By weight" herein and throughout the specification, unless otherwise defined, refers to the relative weight of the particular component with respect to the
Gesamtgewicht der Formulierung: Komponente (a): 0,001 - 50 Gew.-%, bevorzugt 0,1 - 45 Gew.-%, besonders bevorzugt 1 - 40 Gew.-%.Total weight of the formulation: Component (a): 0.001-50% by weight, preferably 0.1-45% by weight, particularly preferably 1-40% by weight.
Komponente (b): 1 - 60 Gew.-%, bevorzugt 2 - 50 Gew.-%, besonders bevorzugt 3 -Component (b): 1 - 60% by weight, preferably 2 - 50% by weight, more preferably 3 -
40 Gew.-%.40% by weight.
Komponente (c): 5 - 90 Gew.-%, bevorzugt 8 - 85 Gew.-%, besonders bevorzugt 12 - 70 Gew.-%.Component (c): 5 - 90 wt .-%, preferably 8 - 85 wt .-%, particularly preferably 12 - 70 wt .-%.
Komponente (d): 0,1 - 30 Gew.-%, bevorzugt 0,5 - 25 Gew.-%, besonders bevorzugt 1 - 40 Gew.-%.Component (d): 0.1-30% by weight, preferably 0.5-25% by weight, particularly preferably 1-40% by weight.
Komponente (e): 0,1 - 70 Gew.-%, bevorzugt 1 - 60 Gew.-%, besonders bevorzugtComponent (s): 0.1-70% by weight, preferably 1-60% by weight, more preferably
2 - 50 Gew.-%. Komponente (f): 0 - 40 Gew.-%, bevorzugt 0 - 35 Gew.-%, besonders bevorzugt 0 -2 - 50 wt .-%. Component (f): 0-40% by weight, preferably 0-35% by weight, particularly preferably 0-
30 Gew.-%.30% by weight.
Als Wirkstoffe (Komponente a) im erfindungsgemäßen Mikroemulsionskonzentrat kommen sämtliche im agrochemischen Bereich einsetzbare Wirkstoffe in Betracht. Vorzugsweise genannt seien Fungizide, Bakterizide, Insektizide, Akarizide, Nematizide, Molluskizide, Rodentizide, Repellents, Pflanzenwuchsregulatoren, Herbizide und Safener sowie Pflanzennährstoffe. Im folgenden beinhaltet der Begriff Fungizide sowohl Fungizide wie auch Bakterizide und Virizide, der Begriff Insektizide sowohl Insektizide wie auch Akarizide, Nematizide, Molluskizide, Rodentizide und Repellents und der Begriff Herbizide sowohl Herbizide wie auch Pflanzenwuchsregulatoren - soweit aus dem Zusammenhang nichts anderes hervorgeht.Suitable active ingredients (component a) in the microemulsion concentrate according to the invention are all active substances which can be used in the agrochemical field. Preferably mentioned are fungicides, bactericides, insecticides, acaricides, nematicides, molluscicides, rodenticides, repellents, plant growth regulators, herbicides and safeners and plant nutrients. In the following the term includes Fungicides both fungicides and bactericides and viricides, the term insecticides both insecticides and acaricides, nematicides, molluscicides, rodenticides and repellents and the term herbicides herbicides as well as plant growth regulators - unless the context otherwise indicates.
Die agrochemischen Wirkstoffe können Fungizide sein, beispielsweise Inhibitoren der Nucleinsäure Synthese, insbesondereThe agrochemically active compounds may be fungicides, for example inhibitors of nucleic acid synthesis, in particular
Benalaxyl, Benalaxyl-M, Bupirimat, Chiralaxyl, Clozylacon, Dimethirimol, Ethirimol, Furalaxyl, Hymexazol, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl,Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl,
Oxolinsäure; Inhibitoren der Mitose und Zellteilung, insbesondereoxolinic; Inhibitors of mitosis and cell division, in particular
Benomyl, Carbendazim, Diethofencarb, Fuberidazole, Pencycuron, Thiabendazol, Thiophanat-methyl, Zoxamid; Inhibitoren der Atmungskette Komplex I, insbesondereBenomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide; Inhibitors of the respiratory chain complex I, in particular
Diflumetorim; Inhibitoren der Atmungskette Komplex II, insbesonderediflumetorim; Inhibitors of the respiratory chain complex II, in particular
Boscalid, Carboxin, Fenfuram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamid; Inhibitoren der Atmungskette Komplex III, insbesondereBoscalid, Carboxin, Fenfuram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide; Inhibitors of the respiratory chain complex III, in particular
Azoxystrobin, Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadon, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Picoxystrobin, Trifloxystrobin; Entkoppler, insbesondere Dinocap, Fluazinam;Azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximmethyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin; Decouplers, especially dinocap, fluazinam;
Inhibitoren der ATP Produktion, insbesondereInhibitors of ATP production, in particular
Fentinacetat, Fentinchlorid, Fentinhydroxid, Silthiofam; Inhibitoren der Aminosäure- und Proteinbiosynthese, insbesondereFentin acetate, fentin chloride, fentin hydroxide, silthiofam; Inhibitors of amino acid and protein biosynthesis, in particular
Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycinhydrochlorid Hydrat, Mepanipyrim, Pyrimethanil;Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
Inhibitoren der Signal-Transduktion, insbesondere Fenpiclonil, Fludioxonil, Quinoxyfen; Inhibitoren der Fett- und Membran Synthese, insbesondereSignal transduction inhibitors, in particular fenpiclonil, fludioxonil, quinoxyfen; Inhibitors of fat and membrane synthesis, in particular
Chlozolinat, Iprodion, Procymidon, Vinclozolin,Chlozolinate, iprodione, procymidone, vinclozolin,
Ampropylfos, Kalium-Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolan,Ampropylfos, Potassium Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolane,
Pyrazophos, Tolclofos-methyl, Biphenyl, lodocarb, Propamocarb, Propamocarb hydrochlorid; Inhibitoren der Ergosterol Biosynthese, insbesonderePyrazophos, tolclofos-methyl, biphenyl, iodocarb, propamocarb, propamocarb hydrochloride; Inhibitors of ergosterol biosynthesis, in particular
Fenhexamid,fenhexamid,
Azaconazol, Bitertanol, Bromuconazol, Cyproconazol, Diclobutrazol, Difenoconazol, Diniconazol, Diniconazol-M, Epoxiconazol, Etaconazol,Azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole,
Fenbuconazol, Fluquinconazol, Flusilazol, Flutriafol, Furconazol, Furconazol-cis,Fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis,
Hexaconazol, Imibenconazol, Ipconazol, Metconazol, Myclobutanil,Hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,
Paclobutrazol, Penconazol, Propiconazol, Prothioconazol, Simeconazol,Paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole,
Tebuconazol, Tetraconazol, Triadimefon, Triadimenol, Triticonazol, Uniconazol, Voriconazol, Imazalil, Imazalilsulfat, Oxpoconazol, Fenarimol, Fluφrimidol,Tebuconazole, tetraconazole, triadimefon, triadimol, triticonazole, uniconazole, voriconazole, imazalil, imazalil sulfate, oxpoconazole, fenarimol, fluφrimidol,
Nuarimol, Pyrifenox, Triforin, Pefurazoat, Prochloraz, Triflumizol, Viniconazol,Nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole,
Aldimoφh, Dodemoφh, Dodemoφhacetat, Fenpropimoφh, Tridemoφh,Aldimoφh, Dodemoφh, Dodemoφhacetat, Fenpropimoφh, Tridemoφh,
Fenpropidin, Spiroxamin,Fenpropidin, spiroxamine,
Naftifin, Pyributicarb, Terbinafin; Inhibitoren der Zellwand Synthese, insbesondereNaftifine, pyributicarb, terbinafine; Inhibitors of cell wall synthesis, in particular
Benthiavalicarb, Bialaphos, Dimethomoφh, Flumoφh, Iprovalicarb, Polyoxins,Benthiavalicarb, Bialaphos, Dimethomoφh, Flumoφh, Iprovalicarb, Polyoxins,
Polyoxorim, Validamycin A; Inhibitoren der Melanin Biosynthese, insbesonderePolyoxorim, validamycin A; Inhibitors of melanin biosynthesis, in particular
Capropamid, Diclocymet, Fenoxanil, Phtalid, Pyroquilon, Tricyclazol; Resistenzinduktoren, insbesondereCapropamide, diclocymet, fenoxanil, phtalid, pyroquilon, tricyclazole; Resistance Inductors, in particular
Acibenzolar-S-methyl, Probenazol, Tiadinil; Multisite, insbesondereAcibenzolar-S-methyl, Probenazole, Tiadinil; Multisite, in particular
Captafol, Captan, Chlorothalonil, Kupfersalze wie: Kupferhydroxid,Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide,
Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux Mischung, Dichlofluanid, Dithianon, Dodin, Dodin freie Base, Ferbam,Copper Naphthenate, Copper Oxychloride, Copper Sulphate, Copper Oxide, Oxine Copper and Bordeaux Blend, Dichlofluanid, Dithianone, Dodin, Dodine Free Base, Ferbam,
Folpet, Fluorofolpet, Guazatin, Guazatinacetat, Iminoctadin,Folpet, fluorofolpet, guazatine, guazatine acetate, iminoctadine,
Iminoctadinalbesilat, Iminoctadintriacetat, Mankupfer, Mancozeb, Maneb, Metiram, Metiram Zink, Propineb, Schwefel und Schwefelpräparate enthaltend Calciumpolysulphid, Thiram, Tolylfluanid, Zineb, Ziram; Fungizide mit unbekannten Mechanismus, insbesondereIminoctadinalesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, Metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram; Fungicides with unknown mechanism, in particular
Amibromdol, Benthiazol, Bethoxazin, Capsimycin, Carvon, Chinomethionat, Chloropicrin, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb,Amibromdole, benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb,
Diclomezine, Dichlorophen, Dicloran, Difenzoquat, Difenzoquat Methylsulphat, Diphenylamin, Ethaboxam, Ferimzon, flumetover, Flusulfamid, Fluopicolid, Fluoroimid, Hexachlorobenzol, 8-Hydroxychinolinsulfat, Irumamycin, Methasulphocarb, Metrafenon, Methyl Isothiocyanat, Mildiomycin, Natamycin, Nickel dimethyldithiocarbamat, Nitrothal-isopropyl, Octhilinon, Oxamocarb,Diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimido, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl , Octhilinone, oxamocarb,
Oxyfenthiin, Pentachlorophenol und Salze, 2-Phenylphenol und Salze, Piperalin, Propanosin -Natrium, Proquinazid, Pyrrolnitrin, Quintozen, Tecloftalam, Tecnazen, Triazoxid, Trichlamid, Zarilamid und 2,3,5,6-Tetrachlor-4- (methylsulfonyl)-pyridin, N-(4-Chlor-2-nitrophenyl)-N-ethyl-4-methyl- benzenesulfonamid, 2-Amino-4-methyl-N-phenyl-5-thiazolecarboxamid, 2-Chlor-Oxyfenthiine, pentachlorophenol and salts, 2-phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) - pyridine, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro
N-(2,3-dihydro-1 ,1 ,3-trimethyl-1H-inden-4-yl)-3-pyridincarboxamid, 3-[5-(4- Chloφhenyl)-2,3-dimethylisoxazolidin-3-yl]pyridin, cis-1 -(4-Chlorphenyl)-2-(1 H- 1 ,2,4-triazol-1 -yl)-cycloheptanol, 2,4-Dihydro-5-methoxy-2-methyl-4-[[[[[1 -[3- (trifluorOmethyl)-phenyl]-ethyliden]-amino]-oxy]-methyl]-phenyl]-3H-1 ,2,3-triazol- 3-on (185336-79-2), Methyl 1 -(2,3-dihydro-2,2-dimethyl-1 H-inden-1 -yl)-1 H- imidazole-5-carboxylat, 3,4,5-Trichlor-2,6-pyridindicarbonitril, Methyl 2- [[[cyclopropyl[(4-methoxyphenyl) imino]methyl]thio]methyl]-.alpha.- (methoxymethylen)- benzacetat, 4-Chlor-alpha-propinyloxy-N-[2-[3-methoxy-4- (2-propinyloxy)phenyl]ethyl]-benzacetamide, (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2- propinyl]oxy]-3-methoxyphenyl]ethyl]- 3-methyl-2-[(methylsulfonyl)amino]- butanamid, 5-Chlor-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidin, 5-Chlor-6-(2,4,6-trifluorophenyl)-N- [(1 R)-1 ,2,2-trimethylpropyl][1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amin, 5-Chlor-N- [(1 R)-1 )2-dimethylpropyl]-6-(2,4,6-trifluorophenyl) [1 ,2,4]triazolo[1 ,5-a]pyrimidin- 7-amine, N-[1-(5-BiOm-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamid, N-(5-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl ] pyridine, cis-1 - (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4- [[[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1,2,3-triazol-3-one (185336-79) 2), methyl 1 - (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6- pyridinedicarbonitrile, methyl 2- [[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] -. alpha.- (methoxymethylene) benzoacetate, 4-chloro-alpha-propynyloxy-N- [2- [3- methoxy-4- (2-propynyloxy) phenyl] ethyl] benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl ] - 3-methyl-2 - [(methylsulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1, 2,4 ] triazolo [1,5-a] pyrimidine, 5-chloro-6- (2,4,6-trifluorophenyl) -N- [(1 R) -1, 2,2-trimethylpropyl] [1, 2,4] triazolo [1,5-a] pyrimidin-7-amine, 5-Chl or-N- [(1 R) -1 ) 2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine-7-amine, N - [1- (5-BiOm-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-
Brom-3-chloφyridin-2-yl)methyl-2,4-dichlornicotinamid, 2-Butoxy-6-iod-3-propyl- benzopyranon-4-on, N-{(Z)-[(cyclopropylmethoxy) imino][6-(difluoιmethoxy)-2,3- difluorphenyflmethyl^-benzacetamid, N-(3-Ethyl-3,5,5-trimethyl-cyclohexyl)-3- formylamino-2-hydroxy-benzamid, 2-[[[[1-[3(1 Fluor-2-phenylethyl)oxy] phenyl] ethyliden]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alphaE- benzacetamid, N-{2-[3-Chlor-5-(trifluormethyl)pyridin-2-yl]ethyl}-2- (trifluoromethyl)benzamid, N-(3',4'-dichlor-5-fluorbiphenyl-2-yl)-3-(difluormethyl)-Bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinotin, 2-butoxy-6-iodo-3-propyl-benzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [ 6- (difluoιmethoxy) -2,3 difluorophenylmethyl ^ -benzacetamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2 - [[[[1- [3 (1-fluoro-2-phenylethyl ) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha (methoxyimino) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -ethyl } -2- (trifluoromethyl) benzamide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -
1 -methyl-1 H-pyrazol-4-carboxamid, N-(6-Methoxy-3-pyridinyl)-cyclopropan carboxamid, 1 -[(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl-1 H-imidazol-1 - carbonsäure, O-[1 -[(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1 H- imidazol- 1- carbothioic acid, 2-(2-{[6-(3-Chlor-2-methylphenoxy)-5- fluoφyrimidin-4-yl]oxy}phenyl)-2-(methoxyirnino)-N-methylacetamid.1-methyl-1H-pyrazole-4-carboxamide, N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide, 1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole 1-carboxylic acid, O- [1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazole-1-carbothioic acid, 2- (2 - {[6- (3-chloro-2 -methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxy-imino) -N-methylacetamide.
Die agrochemischen Wirkstoffe können auch Bakterizide sein, beispielsweise Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Teclofta- lam, Kupfersulfat und andere Kupfer-Zubereitungen.The agrochemically active compounds may also be bactericides, for example bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Die vorstehend aufgeführten Fungizide (Bakterizide) sind z.B. bekannt aus „The Pesticide Manual", 12. Auflage (2000) und 13. Auflage (2003), The British Crop Protection Council oder den nach den einzelnen Wirkstoffen aufgeführten Literaturstellen.The above-mentioned fungicides (bactericides) are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
Die agrochemischen Wirkstoffe können auch Insektizide / Akarizide und/oder Nematizide sein, beispielsweise Acetylcholinesterase (AChE) Inhibitoren Carbamate, zum Beispiel Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Bendio- carb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam- sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb,The agrochemically active compounds may also be insecticides / acaricides and / or nematicides, for example acetylcholinesterase (AChE) inhibitors carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendabarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb,
Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, Triazamate; Organophosphate, zum Beispiel Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromo- phos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbopheno- thion, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos,Propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamates; Organophosphates, for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophosphethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl ), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos,
Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofen- thion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxa- benzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fen- amiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, lodofenphos, Iproben- fos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Me- carbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocroto- phos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl/ -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phospho- carb, Phoxim, Pirimiphos (-methyl/-ethyl), Profenofos, Propaphos, Propetam- phos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinal- phos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion; Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker Pyrethroide, zum Beispiel Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifen- thrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-isomer, Bioethanomethrin, Bio- permethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Res- methrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cy- permethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, Deltamethrin, Em- penthrin (1 R-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, FIu- methrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (1R- trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Res- methrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (-1 R- isomer), Tralomethrin, Transfluthrin, ZXI 8901 , PyrethrinsDemeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlorodithione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfonot, EPN, ethion, ethoprophos, etrimfos, famphur, fenambiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocroto - phos, naled, omethoate, oxydemeton-methyl, parathion (-methyl / -ethyl), phenthoates, phorates, phosalones, phosmet, phosphamidone, phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propaphos, propetam - Phos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion; Sodium Channel Modulators / Voltage-Dependent Sodium Channel Blockers Pyrethroids, for example, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifeneprin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioethanomethrin , Biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrine, cycloprothrin, cyfluthrin, cyhalothrin, cyperethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, Deltamethrin, pententhrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, fluethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, Metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, Tetramethrin (-1 R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins
(pyrethrum);(Pyrethrum);
DDT;DDT;
Oxadiazine, zum Beispiel Indoxacarb;Oxadiazines, for example indoxacarb;
Semicarbazon, zum Beispiel Metaflumizon (BAS3201 ); Acetylcholin-Rezeptor-Agonisten/-AntagonistenSemicarbazone, for example metaflumizone (BAS3201); Acetylcholine receptor agonists / antagonists
Chloronicotinyle, zum Beispiel Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Niten- pyram, Nithiazine, Thiacloprid, ThiamethoxamChloronicotinyls, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam
Nicotine, Bensultap, Cartap; Acetylcholin-Rezeptor-ModulatorenNicotine, Bensultap, Cartap; Acetylcholine receptor modulators
Spinosyne, zum Beispiel Spinosad;Spinosyn, for example spinosad;
GABA-gesteuerte Chlorid-Kanal-AntagonistenGABA-driven chloride channel antagonists
Organochlorine, zum Beispiel Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH,Organochlorines, for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH,
Heptachlor, Lindane, Methoxychlor; Fiprole, zum Beispiel Acetoprole, Ethiprole, Fipronil, Pyrafluprole, Pyriprole,Heptachlor, lindane, methoxychlor; Fiproles, for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole,
Vaniliprole; Chlorid-Kanal-Aktivatorenvaniliprole; Chloride channel activators
Mectine, zum Beispiel Abamectin, Emamectin, Emamectin-benzoate, Ivermectin,Mectins, for example Abamectin, Emamectin, Emamectin benzoate, Ivermectin,
Lepimectin, Milbemycin; Juvenilhormon-Mimetika, zum Beispiel Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene,Lepimectin, milbemycin; Juvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprene,
Methoprene, Pyriproxifen, Triprene; Ecdysonagonisten/disruptoren Diacylhydrazine, zum Beispiel Chromafenozide, Halofenozide, Methoxyfenozide, Tebu- fenozide; Inhibitoren der Chitinbiosynthese Benzoylhamstoffe, zum Beispiel Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, FIu- cycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflum- uron, Penfluron, Teflubenzuron, Triflumuron; Buprofezin;Methoprene, pyriproxifen, triprene; Ecdysone agonists / disrupters diacylhydrazines, for example chroma- zozides, halofenozides, methoxyfenozides, tebneumozides; Inhibitors of chitin biosynthesis Benzoylureas, for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron; buprofezin;
Cyromazine;cyromazine;
Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren Diafenthiuron, Organozinnverbindungen, zum Beispiel Azocyclotin, Cyhexatin, Fenbutatin-oxide;Inhibitors of oxidative phosphorylation, ATP disruptors diafenthiuron, organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxides;
Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Proton- gradientenDecoupling of oxidative phosphorylation by interruption of the H proton gradient
Pyrrole, zum Beispiel Chlorfenapyr; Dinitrophenole, zum Beispiel Binapacyrl, Dinobuton, Dinocap, DNOC; Site-I-Elektronentransportinhibitoren METI's, zum Beispiel Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufen- pyrad, Tolfenpyrad,Pyrroles, for example chlorfenapyr; Dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC; Site I Electron Transport Inhibitors METI's, for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad,
Hydramethylnon, Dicofol; Site-Il-ElektronentransportinhibitorenHydramethylnone, dicofol; Site II electron transport inhibitors
Rotenone; Site-Ill-Elektronentransportinhibitoren Acequinocyl, Fluacrypyrim; Mikrowelle Disruptoren der InsektendarmmembranRotenone; Site III Electron Transport Inhibitors Acequinocyl, Fluacrypyrim; Microwave disruptors of insect intestinal membrane
Bacillus thuringiensis-Stämme; Inhibitoren der FettsyntheseBacillus thuringiensis strains; Inhibitors of fat synthesis
Tetronsäuren, zum Beispiel Spirodiclofen, SpiromesifenTetronic acids, for example spirodiclofen, spiromesifen
Tetramsäuren, zum Beispiel SpirotetramatTetramic acids, for example spirotetramat
Carboxamide, zum Beispiel Flonicamid Oktopaminerge Agonisten, zum Beispiel Amitraz; Inhibitoren der Magnesium-stimulierten ATPase,Carboxamides, for example flonicamid octopaminergic agonists, for example amitraz; Inhibitors of magnesium-stimulated ATPase,
Propargitepropargite
Nereistoxin-Analoge, zum Beispiel Thiocyclam hydrogen Oxalate, Thiosultap-sodium;Nereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultap-sodium;
Agonisten des Ryanodin-Rezeptors,Agonists of the ryanodine receptor,
Benzoesäuredicarboxamide, zum Beispiel FlubendiamidBenzoic acid dicarboxamides, for example flubendiamide
Anthranilamide, zum Beispiel DPX E2Y45 (3-bromo-N-{4-chloro-2-methyl-6-Anthranilamides, for example DPX E2Y45 (3-bromo-N- {4-chloro-2-methyl-6-)
[(methylaminoJcarbonyllphenyQ-I^S-chloropyridin^-yO-I H-pyrazole-δ- carboxamide); Biologika, Hormone oder Pheromone[(methylamino) carbonylphenyQ-1-chloropyridine (-YO-1H-pyrazole-d-carboxamides); Biologics, hormones or pheromones
Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec;Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhicon spec, Paecilomyces spec, Thuringiensin, Verticillium spec;
Wirkstoffe mit unbekannten oder nicht spezifischen WirkmechanismenActive substances with unknown or non-specific mechanisms of action
Fraßhemmer, zum Beispiel Cryolite, Flonicamid, Pymetrozine;Feed inhibitors, for example cryolites, flonicamide, pymetrozines;
Milbenwachstumsinhibitoren, zum Beispiel Clofentezine, Etoxazole, Hexythiazox;Mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox;
Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Bupro- fezin, Chinomethionat, Chlordimeform, Chlorobenzilate, Chloropicrin, CIo- thiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, FIu- benzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyridalyl, Sulfluramid, Tetradifon, Tetrasul, Triarathene.Verbutin.Amidoflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezine, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, CIo- thiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flumbenimine, flufenerim, flutenzine, gossyplasty, hydramethylnone, japonilurane, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyrilyl, sulfluramide, tetradifon, tetrasul, triarathene, buterbutin.
Die vorstehend aufgeführten Insektizide (Akarizide, Nematizide) sind z.B. bekannt aus „The Pesticide Manual", 12. Auflage (2000) und 13. Auflage (2003), The British Crop Protection Council oder den nach den einzelnen Wirkstoffen aufgeführten Literaturstellen.The insecticides listed above (acaricides, nematicides) are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
Die agrochemischen Wirkstoffe können auch Herbizide und/oder Pflanzenwachstumsregulatoren sein; beispielsweise ALS-Inhibitoren (Acetolactat- Synthetase-Inhibitoren) oder von ALS-Inhibitoren verschiedene Herbizide, wie Herbizide aus der Gruppe der Carbamate, Thiocarbamate, Halogenacetanilide, substituierte Phenoxy-, Naphthoxy- und Phenoxyphenoxycarbonsäure-Derivate sowie Heteroaryloxy-phenoxyalkancarbonsäure-Derivate, wie Chinolyloxy-, Chinoxalyl-oxy-, Pyridyloxy-, Benzoxazolyloxy- und Benzthiazolyloxyphenoxyalkan- carbonsäureester, Cyclo-hexandionabkömmlinge, Phosphor-haltige Herbizide, z.B. vom Glufosinate-Typ oder vom Glyphosate-Typ, S-(N-Aryl-N-alkylcarbamoylmethyl)- dithiophosphorsäureester, Harnstoffe sowie Hydroxybenzonitrile.The agrochemically active compounds may also be herbicides and / or plant growth regulators; For example, ALS inhibitors (acetolactate synthetase inhibitors) or herbicides other than ALS inhibitors, such as herbicides from the group of carbamates, thiocarbamates, haloacetanilides, substituted phenoxy, naphthoxy and Phenoxyphenoxycarbonsäure derivatives and heteroaryloxy-phenoxyalkanecarboxylic acid derivatives such as quinolyloxy -, Chinoxalyl-oxy-, pyridyloxy, Benzoxazolyloxy- and Benzthiazolyloxyphenoxyalkan- carboxylic acid esters, cyclo-hexanedione derivatives, phosphorus-containing herbicides, eg glufosinate-type or glyphosate-type, S- (N-aryl-N-alkylcarbamoylmethyl) -dithiophosphoric acid esters, ureas and hydroxybenzonitriles.
Bei den ALS-Inhibitoren handelt es sich insbesondere um Imidazolinone, Pyrimidinyloxy-pyridincarbonsäure-Derivate, Pyrimidyloxy-benzoesäure-Derivate, Triazolo-pyrimidin-sulfonamid-Derivate und um Sulfonamide, vorzugsweise aus der Gruppe der Sulfonylharnstoffe.The ALS inhibitors are in particular imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, triazolo-pyrimidine-sulfonamide derivatives and sulfonamides, preferably from the group of sulfonylureas.
Unter den in den erfindungsgemäßen Mikroemulsionskonzentraten als Komponente enthaltenen Wirkstoffen aus der Gruppe der ALS-Inhibitoren wie Sulfonylharnstoffe sind im Sinne der vorliegenden Erfindung neben den neutralen Verbindungen stets auch deren Salze mit anorganischen und/oder organischen Gegenionen zu verstehen. So können z.B. Sulfonylharnstoffe z.B. Salze bilden, bei denen der Wasserstoff der -SO2-NH-Gruppe durch ein für die Landwirtschaft geeignetes Kation ersetzt ist. Diese Salze sind beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze oder Salze mit organischen Aminen. Ebenso kann Salzbildung durch Anlagerung einer Säure an basischen Gruppen, wie z.B. Amino und Alkylamino, erfolgen. Geeignete Säuren hierfür sind starke anorganische und organische Säuren, beispielsweise HCl, HBr, H2SO4 oder HNO3.For the purposes of the present invention, the active compounds from the group of ALS inhibitors, such as sulfonylureas, which are contained as component in the microemulsion concentrates according to the invention are always to be understood as meaning their salts with inorganic and / or organic counterions. Thus, for example, sulfonylureas can form, for example, salts in which the hydrogen of the -SO 2 -NH group is protected by a cation suitable for agriculture is replaced. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts or salts with organic amines. Likewise, salt formation can take place by addition of an acid to basic groups, such as, for example, amino and alkylamino. Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H 2 SO 4 or HNO 3 .
Bevorzugte ALS-Inhibitoren entstammen aus der Reihe der Sulfonylharnstoffe, z.B.Preferred ALS inhibitors are derived from the series of sulfonylureas, e.g.
Pyrimidin- oder Triazinylaminocarbonyl-[benzol-, pyridin-, pyrazol-, thiophen- und (alkylsulfonyl)-alkylamino-]-sulfamide. Bevorzugt als Substituenten am Pyrimidinring oder Triazinring sind Alkoxy, Alkyl, Haloalkoxy, Haloalkyl, Halogen oderPyrimidine or triazinylaminocarbonyl [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides. Preferred substituents on the pyrimidine or triazine ring are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or
Dimethylamino, wobei alle Substituenten unabhängig voneinander kombinierbar sind. Bevorzugte Substituenten im Benzol-, Pyridin-, Pyrazol-, Thiophen- oderDimethylamino, where all substituents are independently combinable. Preferred substituents in the benzene, pyridine, pyrazole, thiophene or
(Alkylsulfonyl)-alkylamino-Teil sind Alkyl, Alkoxy, Halogen wie F, Cl, Br oder J, Amino, Alkylamino, Dialkylamino, Acylamino wie Formylamino, Nitro,(Alkylsulfonyl) -alkylamino moiety are alkyl, alkoxy, halogen such as F, Cl, Br or J, amino, alkylamino, dialkylamino, acylamino such as formylamino, nitro,
Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl,Alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,
Alkoxyaminocarbonyl, Halogenalkoxy, Halogenalkyl, Alkylcarbonyl, Alkoxyalkyl,Alkoxyaminocarbonyl, haloalkoxy, haloalkyl, alkylcarbonyl, alkoxyalkyl,
Alkylsulfonylaminoalkyl, (Alkansulfonyl)alkylamino. Solche geeignetenAlkylsulfonylaminoalkyl, (alkanesulfonyl) alkylamino. Such suitable
Sulfonylharnstoffe sind beispielsweiseSulfonylureas are for example
A1) Phenyl- und Benzylsulfonylharnstoffe und verwandte Verbindungen, z.B.A1) phenyl and benzylsulfonylureas and related compounds, e.g.
1-(2-Chlorphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3>5-triazin-2-yl)hamstoff1- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3> 5-triazin-2-yl) urea
(Chlorsulfuron),(Chlorsulfuron),
1-(2-Ethoxycarbonylphenylsulfonyl)-3-(4-chlor-6-methoxypyrimidin-2-yl)harnstoff (Chlorimuron-ethyl),1- (2-ethoxycarbonylphenylsulfonyl) -3- (4-chloro-6-methoxypyrimidin-2-yl) urea (chlorimuron-ethyl),
1-(2-Methoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)harnstoff1- (2-Methoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea
(Metsulfuron-methyl),(Metsulfuron-methyl),
1-(2-Chlorethoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)harnstoff1- (2-Chloroethoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea
(Triasulfuron), 1-(2-Methoxycarbonylphenylsulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)hamstoff(Triasulfuron), 1- (2-methoxycarbonylphenylsulfonyl) -3- (4,6-dimethylpyrimidin-2-yl) urea
(Sulfumeturon-methyl),(Sulfumeturon-methyl),
1-(2-Methoxycarbonylphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)-3- methylharnstoff (Tribenuron-methyl),1- (2-Methoxycarbonylphenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -3- methylurea (tribenuron-methyl),
1-(2-Methoxycarbonylbenzylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)harnstoff1- (2-Methoxycarbonylbenzylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea
(Bensulfuron-methyl), i^-MethoxycarbonylphenylsulfonyO-S^.β-bis-CdifluormethoxyJpyrimidin^-yl)- harnstoff, (Primisulfuron-methyl),(Bensulfuron-methyl), i ^ -methoxycarbonylphenylsulfonyO-S ^ .β-bis-Cdifluoromethoxy-pyrimidin-1-yl) -urea, (Primisulfuron-methyl),
3-(4-Ethyl-6-methoxy-1 ,3,5-triazin-2-yl)-1 -(2,3-dihydro-i ,1 -dioxo-2-methylbenzo-3- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) -1- (2,3-dihydro-i, 1-dioxo-2-methylbenzoyl)
[b]thiophen-7-sulfonyl)harnstoff (EP-A 0 796 83),[b] thiophene-7-sulfonyl) urea (EP-A 0 796 83),
3-(4-Ethoxy-6-ethyl-1 ,3,5-triazin-2-yl)-1 -(2,3-dihydro-1 ,1 -dioxo-2-methylbenzo[b]- thiophen-7-sulfonyl)harnstoff (EP-A 0 079 683), 3-(4-Methoxy-6-methyl-1 ,3,5-triazin-2-yl)-1 -(2-methoxycarbonyl-5-jod-phenyl- sulfonyl)-harnstoff (lodosulfuron-methyl und dessen Salze wie das Natriumsalz, WO3- (4-Ethoxy-6-ethyl-1,3,5-triazin-2-yl) -1- (2,3-dihydro-1,1-dioxo-2-methylbenzo [b] -thiophene-7 sulfonyl) urea (EP-A 0 079 683), 3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -1- (2-methoxycarbonyl-5-iodophenylsulfonyl ) urea (iodosulfuron-methyl and its salts, such as the sodium salt, WO
92/13845),92/13845)
DPX-66037, Triflusulfuron-methyl (s. Brighton Crop Prot. Conf. - Weeds - 1995, S.DPX-66037, triflusulfuron-methyl (see Brighton Crop Prot. Conf. - Weeds - 1995, p.
853), CGA-277476, (s. Brighton Crop Prot. Conf. - Weeds - 1995, S. 79),853), CGA-277476, (see Brighton Crop Prot. Conf. - Weeds - 1995, p.
Methyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methansulfon-amido- methyl-benzoat (Mesosulfuron-methyl und dessen Salze wie das Natriumsalz, WOMethyl 2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-methanesulfonamido-methyl-benzoate (mesosulfuron-methyl and its salts such as the sodium salt, WO
95/10507),95/10507)
N)N-Dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylamino- benzamid (Foramsulfuron und dessen Salze wie das Natriumsalz, WO 95/01344);N ) N-dimethyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-formylaminobenzamide (foramsulfuron and its salts, such as the sodium salt, WO 95/01344);
A2) Thienylsulfonylharnstoffe, z.B.A2) Thienylsulfonylureas, e.g.
1-(2-Methoxycarbonylthiophen-3-sulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2- yl)harnstoff (Thifensulfuron-methyl);1- (2-Methoxycarbonylthiophene-3-sulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea (thifensulfuron-methyl);
A3) Pyrazolylsulfonylharnstoffe, z.B.A3) pyrazolylsulfonylureas, e.g.
1-(4-Ethoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)harnstoff (Pyrazosulfuron-methyl);1- (4-ethoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (pyrazosulfuron-methyl);
Methyl-3-chlor-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methyl-pyrazol- 4-carboxylat (EP-A 0 282 613);Methyl 3-chloro-5- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -1-methyl-pyrazole-4-carboxylate (EP-A 0 282 613);
5-(4,6-Dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)-pyrazol-4-car- bonsäuremethylester (NC-330, s. Brighton Crop Prot. Conference 'Weeds1 1991 , Vol. 1 , S. 45 ff.),Methyl 5- (4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl) -1- (2-pyridyl) pyrazole-4-carboxylic acid (NC-330, see Brighton Crop Prot. Conference 'Weeds 1 1991, Vol. 1, p. 45 ff.),
DPX-A8947, Azimsulfuron, (s. Brighton Crop Prot. Conf. 'Weeds1 1995, S. 65);DPX-A8947, azimsulfuron, (see Brighton Crop Prot. Conf. 'Weeds 1 1995, p.
A4) Sulfondiamid-Derivate, z.B. 3-(4,6-Dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonylaminosulfonyl)- harnstoff (Amidosulfuron) und dessen Strukturanaloge (EP-A 0 131 258 und Z. PfI. Krankh. PfI. Schutz, Sonderheft XII, 489-497 (1990));A4) sulfone diamide derivatives, e.g. 3- (4,6-dimethoxypyrimidin-2-yl) -1- (N-methyl-N-methylsulfonylaminosulfonyl) urea (amidosulfuron) and its structural analogs (EP-A-0 131 258 and Z. Pfi. Ill. PfI Special Edition XII, 489-497 (1990));
A5) Pyridylsulfonylharnstoffe, z.B. I^S-N.N-Dimethylaminocarbonylpyridin^-ylsulfonyO-S^.β-dimethoxypyrimidin^- yl)hamstoff (Nicosulfuron),A5) pyridylsulfonylureas, e.g. I ^ S-N, N-dimethylaminocarbonylpyridine, -sylsulfonyo-S, N-β-dimethoxypyrimidin-yl) urea (nicosulfuron),
1-(3-Ethylsulfonylpyridin-2-ylsulfonyl)-3-(-(4,6-dimethoxypyrimidin-2-yl)hamstoff1- (3-Ethylsulfonylpyridin-2-ylsulfonyl) -3 - (- (4,6-dimethoxypyrimidin-2-yl) urea
(Rimsulfuron),(Rimsulfuron),
2-[3-(4,6-Dimethoxypyrimidin-2-yl)ureidosulfonyl]-6-trifluormethyl-3-pyridin- carbonsäuremethylester, Natriumsalz (DPX-KE 459, Flupyrsulfuron, s. Brighton CropMethyl 2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -6-trifluoromethyl-3-pyridinecarboxylate, sodium salt (DPX-KE 459, flupyrsulfuron, see Brighton Crop
Prot. Conf. Weeds, 1995, S. 49), Trifloxysulfuron und dessen Natriumsalz;Prot. Conf. Weeds, 1995, p. 49), trifloxysulfuron and its sodium salt;
A6) Alkoxyphenoxysulfonylharnstoffe, wie sie z.B. in EP-A 0 342 569 beschrieben sind, vorzugsweise 3-(4,6-Dimethoxypyrimidin-2-yl)-1-(2- ethoxyphenoxy)-sulfonylharnstoff (Ethoxysulfuron) oder dessen Salze wie das Natriumsalz;A6) Alkoxyphenoxysulfonylureas, as described e.g. in EP-A 0 342 569, preferably 3- (4,6-dimethoxypyrimidin-2-yl) -1- (2-ethoxyphenoxy) sulfonylurea (ethoxysulfuron) or its salts, such as the sodium salt;
A7) Imidazolylsulfonylharnstoffe, z.B.A7) imidazolylsulfonylureas, e.g.
MON 37500, Sulfosulfuron (s. Brighton Crop Prot. Conf. "Weeds1, 1995, S: 57), und andere verwandte Sulfonylharnstoff-Derivate und Mischungen daraus.MON 37500, sulfosulfuron (see Brighton Crop Prot. Conf., "Weeds 1 ," 1995, p. 57), and other related sulfonylurea derivatives and mixtures thereof.
Typische Vertreter dieser Wirkstoffe sind unter anderem die nachfolgend aufgeführten Verbindungen und deren Salze wie die Natriumsalze: Amidosulfuron, Azimsulfuron, Bensulf uron-methyl, Chlorimuron-Ethyl, Chlorsulfuron, Cinosulfuron, Cyclosulfamuron, Ethametsulf uron-methyl, Ethoxysulfuron, Flazasulfuron,Typical representatives of these active substances are, inter alia, the compounds listed below and their salts, such as the sodium salts: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
Flupyrsulfuron-Methyl-Natrium, Halosulfuron-Methyl, Imazosulfuron, Metsulfuron- Methyl, Nicosulfuron, Oxasulfuron, Primisulfuron-Methyl, Prosulfuron, Pyrazosulfuron-Ethyl, Rimsulfuron, Sulfometuron-Methyl, Sulfosulfuron, Thifensulfuron-Methyl, Triasulfuron, Tribenuron-Methyl, Trifloxysulfuron und dessen Natriumsalz, Triflusulfuron-Methyl, lodosulfuron-Methyl und dessen Natriumsalz (WO 92/13845), Mesosulfuron-Methyl und dessen Natriumsalz (Agrow Nr. 347, 3. März 2000, Seite 22 (PJB Publications Ltd. 2000)) und Foramsulfuron und dessen Natriumsalz (Agrow Nr. 338, 15. Oktober 1999, Seite 26 (PJB Publications Ltd. 1999)).Flupyrsulfuron-methyl-sodium, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, Pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron and its sodium salt, triflusulfuron-methyl, iodosulfuron-methyl and its sodium salt (WO 92/13845), mesosulfuron-methyl and its sodium salt (Agrow No. 347, March 3, 2000, page 22 (PJB Publications Ltd. 2000)) and foramsulfuron and its sodium salt (Agrow No. 338, Oct. 15, 1999, page 26 (PJB Publications Ltd. 1999)).
Weitere geeignete ALS-Inhibitoren sind z.B.Other suitable ALS inhibitors are e.g.
B) Imidazolinone, z.B.B) imidazolinones, e.g.
2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylbenzoesäure-methylester und 2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-4-methylbenzoesäure (Imazamethabenz), 5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-pyridin-3-carbonsäure (Imazethapyr),Methyl 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -5-methylbenzoate and 2- (4-isopropyl-4-methyl-5-oxo-2-imidazoline-2 -yl) -4-methylbenzoic acid (imazamethabenz), 5-ethyl-2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -pyridine-3-carboxylic acid (imazethapyr),
2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4-lsopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-pyridin-3-carbonsäure (Imazapyr), 5-Methyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-pyridin-3-carbonsäure (Imazethamethapyr);2- (4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -quinoline-3-carboxylic acid (imazaquin), 2- (4-isopropyl-4-methyl-5-oxo-2-ol imidazolin-2-yl) -pyridine-3-carboxylic acid (imazapyr), 5-methyl-2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -pyridine-3-carboxylic acid ( imazethamethapyr);
C) Triazolopyrimidinsulfonamid-Derivate, z.B. N-(2,6-Difluorphenyl)-7-methyl-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2-sulfonamid (Flumetsulam), N-(2,6-Dichlor-3-methylphenyl)-5,7-dimethoxy-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2- sulfonamid,C) Triazolopyrimidine sulfonamide derivatives, e.g. N- (2,6-Difluorophenyl) -7-methyl-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide (flumetsulam), N- (2,6-dichloro-3-methylphenyl) 5,7-dimethoxy-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide,
N-(2>6-Difluorphenyl)-7-fluor-5-methoxy-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2-sulfonamid,N- (2- > 6-difluorophenyl) -7-fluoro-5-methoxy-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide,
N^.e-Dichlor-S-methylphenyl^-chlor-δ-methoxy-i ^^-triazoloti .δ-clpyrimidin^- sulfonamid, N-(2-Chlor-6-methoxycarbonyl)-5,7-dimethyl-1 ,2,4-triazolo[1 ,5-c]pyrimidin-2- sulfonamid (EP-A 0 343 752, US-A 4,988,812); D) Pyrimidinyloxy-pyridincarbonsäure- bzw. Pyrimidinyloxybenzoesäure- Derivate, z.B.N,... Dichloro-S-methylphenyl-chloro-δ-methoxy-1'-triazoloti-.delta.-c-pyrimidine-sulfonamide, N- (2-chloro-6-methoxycarbonyl) -5,7-dimethyl-1 2,4-triazolo [1,5-c] pyrimidine-2-sulfonamide (EP-A 0 343 752, US-A 4,988,812); D) Pyrimidinyloxy-pyridinecarboxylic or pyrimidinyloxybenzoic acid derivatives, eg
3-(4,6-Dimethoxypyrimidin-2-yl)-oxy-pyridin-2-carbonsäurebenzyl-ester (EP-A 0 249 707), 3-(4,6-Dimethoxypyrimidin-2-yl)-oxy-pyridin-2-carbonsäuremethylester (EP-A 0 249 707),Benzyl 3- (4,6-dimethoxypyrimidin-2-yl) oxy-pyridine-2-carboxylate (EP-A 0 249 707), 3- (4,6-dimethoxypyrimidin-2-yl) -oxy-pyridine 2-carboxylic acid methyl ester (EP-A 0 249 707),
2)6-Bis[(4,6-dimethoxypyrimidin-2-yl)-oxy]-benzoesäure (EP-A 0 321 846), 2,6-Bis[(4,6-dimethoxypyrimidin-2-yl)-oxy]-benzoesäure-1-(ethoxycarbonyl-oxyethyl)- ester (EP-A 0 472 113).2 ) 6-bis [(4,6-dimethoxypyrimidin-2-yl) oxy] benzoic acid (EP-A 0 321 846), 2,6-bis [(4,6-dimethoxypyrimidin-2-yl) oxy] ] -benzoic acid-1- (ethoxycarbonyl-oxyethyl) - ester (EP-A 0 472 113).
Geeignete von ALS-Inhibitoren verschiedene herbizide Wirkstoffe, die in den erfindungsgemäßen Mikroemulsionskonzentraten als Komponente enthalten sein können, sind beispielsweise:Suitable herbicidally active compounds which differ from ALS inhibitors and can be contained as component in the microemulsion concentrates according to the invention are, for example:
E) Herbizide vom Typ der Phenoxyphenoxy- undE) phenoxyphenoxy- and herbicides of the type
Heteroaryloxyphenoxycarbonsäure-Derivate, wieHeteroaryloxyphenoxycarboxylic acid derivatives, such as
E1 ) Phenoxyphenoxy- und Benzyloxyphenoxy-carbonsäure-Derivate, z.B. 2-(4-E1) phenoxyphenoxy- and benzyloxyphenoxy-carboxylic acid derivatives, e.g. 2- (4-
(2,4-Dichlorphenoxy)-phenoxy)-propionsäuremethylester (Diclofop-methyl),(2,4-dichlorophenoxy) -phenoxy) -propionic acid methyl ester (diclofop-methyl),
2-(4-(4-Brom-2-chloφhenoxy)phenoxy)propionsäuremethylester (DE-A 26 01 548), 2-(4-(4-Brom-2-fluorphenoxy)phenoxy)propionsäuremethylester (US-A 4,808,750),Methyl 2- (4- (4-bromo-2-chlorophenoxy) phenoxy) propionate (DE-A 26 01 548), 2- (4- (4-bromo-2-fluorophenoxy) phenoxy) propionic acid methyl ester (US Pat. No. 4,808,750),
2-(4-(2-Chlor-4-trifluormethylphenoxy)phenoxy)propionsäuremethylester (DE-A2- (4- (2-chloro-4-trifluoromethylphenoxy) phenoxy) propionic acid methyl ester (DE-A
24 33 067),24 33 067),
2-(4-(2-Fluor-4-trifluoιτnethylphenoxy)phenoxy)propionsäuremethylester (US-AMethyl 2- (4- (2-fluoro-4-trifluoro-ethylphenoxy) phenoxy) propionate (US Pat
4,808,750), 2-(4-(2,4-Dichlorbenzyl)phenoxy)propionsäuremethylester (DE-A 24 17 487),4,808,750), 2- (4- (2,4-dichlorobenzyl) phenoxy) propionic acid methyl ester (DE-A 24 17 487),
4-(4-(4-Trifluormethylphenoxy)phenoxy)pent-2-en-säureethylester,4- (4- (4-trifluoromethylphenoxy) phenoxy) pent-2-en-oate,
2-(4-(4-Trifluormethylphenoxy)phenoxy)propionsäuremethylester (DE-A 24 33 067);2- (4- (4-trifluoromethylphenoxy) phenoxy) propionic acid methyl ester (DE-A 24 33 067);
E2) "Einkernige" Heteroaryloxyphenoxy-alkancarbonsäure-Derivate, z.B. 2-(4-(3,5-Dichlorpyridyl-2-oxy)phenoxy)propionsäureethylester (EP-A 0 002 925), 2-(4-(3,5-Dichlorpyridyl-2-oxy)phenoxy)propionsäurepropargylester (EP-A 0 003 114), 2-(4-(3-Chlor-5-trifluormethyl-2-pyridyloxy)phenoxy)propionsäure-methylester (EP-A 0 003 890),E2) "mononuclear" heteroaryloxyphenoxyalkanecarboxylic acid derivatives, eg ethyl 2- (4- (3,5-dichloropyridyl-2-oxy) phenoxy) propionate (EP-A 0 002 925), 2- (4- (3,5-) Dichloropyridyl-2-oxy) phenoxy) propionic acid propargyl ester (EP-A 0 003 114), 2- (4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid methyl ester (EP-A 0 003 890),
2-(4-(3-Chlor-5-trifluormethyl-2-pyridyloxy)phenoxy)propionsäureethylester (EP-A 0 003 890), 2-(4-(5-Chlor-3-fluor-2-pyridyloxy)phenoxy)propionsäurepropargylester (EP-A 0 191 736),Ethyl 2- (4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionate (EP-A 0 003 890), 2- (4- (5-chloro-3-fluoro-2-pyridyloxy) phenoxy) propionic acid propargyl ester (EP-A 0 191 736),
2-(4-(5-Trifluormethyl-2-pyridyloxy)phenoxy)propionsäurebutylester (Fluazifop-butyl);Butyl 2- (4- (5-trifluoromethyl-2-pyridyloxy) phenoxy) propionate (fluazifop-butyl);
E3) "Zweikernige" Heteroaryloxyphenoxy-alkancarbonsäure-Derivate, z.B.E3) "binuclear" heteroaryloxyphenoxy-alkanecarboxylic acid derivatives, e.g.
2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäuremethylester und -ethylesterMethyl 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionate and ethyl ester
(Quizalofopmethyl und Quizalofopethyl),(Quizalofopmethyl and quizalofopethyl),
2-(4-(6-Fluor-2-chinoxalyloxy)phenoxy)propionsäuremethylester (s. J. Pest. Sei. Vol.Methyl 2- (4- (6-fluoro-2-quinoxalyloxy) phenoxy) propionate (see J. Pest, Vol.
10, 61 (1985)), 2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäure-2-isopropylidenaminooxy- ethylester (Propaquizafop),10, 61 (1985)), 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid 2-isopropylideneaminooxyethyl ester (propaquizafop),
2-(4-(6-Chlorbenzoxazol-2-yl-oxy)phenoxy)propionsäureethylester (Fenoxaprop- ethyl), dessen D(+) Isomer (Fenoxaprop-P-ethyl) und 2-(4-(6-Chlorbenzthiazol-2- yloxy)phenoxy)propionsäureethylester (DE-A 26 40 730), 2-(4-(6-Chlorchinoxalyloxy)phenoxy)propionsäure-tetrahydro-2-furylmethylester (EP-2- (4- (6-chlorobenzoxazol-2-yl-oxy) phenoxy) propionic acid ethyl ester (fenoxapropethyl), its D (+) isomer (fenoxaprop-P-ethyl) and 2- (4- (6-chlorobenzthiazole-2 ethyl yloxy) phenoxy) propionate (DE-A 26 40 730), 2- (4- (6-chloroquinoxalyloxy) phenoxy) propionic acid tetrahydro-2-furylmethyl ester (EP-
A 0 323 727);A 0 323 727);
F) Chloracetanilide, z.B. N-Methoxymethyl-2,6-diethyl-chloracetanilid (Alachlor), N-(3-Methoxyprop-2-yl)-2-methyl-6-ethyl-chloracetanilid (Metolachlor),F) Chloroacetanilides, e.g. N-methoxymethyl-2,6-diethyl-chloroacetanilide (alachlor), N- (3-methoxyprop-2-yl) -2-methyl-6-ethyl-chloroacetanilide (metolachlor),
N-(3-Methyl-1 ,2,4-oxadiazol-5-yl-methyl)-chloressigsäure-2,6-dimethylanilid, N-(2,6-Dimethylphenyl)-N-(1-pyrazolylmethyl)-chloressigsäureamid (Metazachlor);N- (3-Methyl-1,2,4-oxadiazol-5-ylmethyl) -chloroacetic acid-2,6-dimethylanilide, N- (2,6-dimethylphenyl) -N- (1-pyrazolylmethyl) -chloroacetic acid amide ( metazachlor);
G) Thiocarbamate, z.B. S-Ethyl-N,N-dipropylthiocarbamat (EPTC), S-Ethyl-N,N-diisobutylthiocarbamat (Butylate); H) Cyclohexandionoxime, z.B.G) thiocarbamates, eg S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates); H) cyclohexanedione oximes, eg
3-(1-Allyloxyiminobutyl)-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-encarbon- säuremethylester, (Alloxyd im),3- (1-Allyloxyiminobutyl) -4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-ene-carboxylic acid methyl ester, (alloxide im),
2-(1-Ethoxyiminobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-cyclohex-2-en-1-on (Sethoxydim),2- (1-ethoxyiminobutyl) -5- (2-ethylthiopropyl) -3-hydroxycyclohex-2-en-1-one (sethoxydim),
2-(1-Ethoxyiminobutyl)-5-(2-phenylthiopropyl)-3-hydroxy-cyclohex-2-en-1-on (Cloproxydim),2- (1-ethoxyiminobutyl) -5- (2-phenylthiopropyl) -3-hydroxycyclohex-2-en-1-one (cloproxydime),
2-(1-(3-Chlorallyloxy)iminobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-cyclohex-2-en-1-on, 2-(1-(3-Chlorallyloxy)iminopropyl)-5-(2-ethylthiopropyl)-3-hydroxy-cyclohex-2-en-1- on (Clethodim),2- (1- (3-chloroallyloxy) iminobutyl) -5- (2-ethylthiopropyl) -3-hydroxycyclohex-2-en-1-one, 2- (1- (3-chloroallyloxy) iminopropyl) -5- (2-ethylthiopropyl) -3-hydroxycyclohex-2-en-1-one (clethodim),
2-(1-Ethoxyiminobutyl)-3-hydroxy-5-(thian-3-yl)-cyclohex-2-enon (Cycloxydim),2- (1-ethoxyiminobutyl) -3-hydroxy-5- (thian-3-yl) -cyclohex-2-enone (cycloxydim),
2-(1-Ethoxyiminopropyl)-5-(2,4,6-trimethylphenyl)-3-hydroxy-cyclohex-2-en-1-on2- (1-Ethoxyiminopropyl) -5- (2,4,6-trimethylphenyl) -3-hydroxy-cyclohex-2-en-1-one
(Tralkoxydim);(Tralkoxydim);
I) Benzoylcyclohexandione, z.B.I) benzoylcyclohexanediones, e.g.
2-(2-Chlor-4-methylsulfonylbenzoyl)-cyclohexan-1 ,3-dion (SC-0051 , EP-A2- (2-chloro-4-methylsulfonylbenzoyl) -cyclohexane-1,3-dione (SC-0051, EP-A
0 137 963), 2-(2-Nitrobenzoyl)-4,4-dimethyl-cyclohexan-1 ,3-dion (EP-A 0 274 634),0 137 963), 2- (2-nitrobenzoyl) -4,4-dimethylcyclohexane-1,3-dione (EP-A 0 274 634),
2-(2-Nitro-4-methylsulfonylbenzoyl)-4,4-dimethylcyclohexan-1 ,3-dion (WO 91/13548,2- (2-nitro-4-methylsulfonylbenzoyl) -4,4-dimethylcyclohexane-1,3-dione (WO 91/13548,
Mesotrione);Mesotrione);
J) S-(N-Aιyl-N-alkyl-carbamoylmethyl)-dithiophosphorsäureester, wie S-[N-(4-J) S- (N-Ayl-N-alkyl-carbamoylmethyl) -dithiophosphoric acid esters such as S- [N- (4-
Chlorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-dimethyl-dithiophosphatChlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-dimethyl dithiophosphate
(Anilophos).(Anilophos).
K) Alkylazine, z.B. wie beschrieben in WO-A 97/08156, WO-A-97/31904, DE-A- 19826670, WO-A-98/15536, WO-A-8/15537, WO-A-98/15538, WO-A-98/15539 sowie auch DE-A-19828519, WO-A-98/34925, WO-A-98/42684, WO-A-99/18100, WO-A-99/19309, WO-A-99/37627 und WO-A-99/65882, vorzugsweise solche der Formel (K) worin Rx (CrC4)-Alkyl oder (C1-C4)-Haloalkyl; Rγ (CrC4)-Alkyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C4)-Alkyl und A -CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -O-, -CH2-CH2-O-, -CH2-CH2-CH2-O- bedeuten, besonders bevorzugt solche der Formel K1-K7K) Alkylazines, for example as described in WO-A 97/08156, WO-A-97/31904, DE-A-19826670, WO-A-98/15536, WO-A-8/15537, WO-A-98 / 15538, WO-A-98/15539 and also DE-A-19828519, WO-A-98/34925, WO-A-98/42684, WO-A-99/18100, WO-A-99/19309, WO-A-99/37627 and WO-A-99/65882, preferably those of the formula (K) wherein R x is (C r C 4 ) alkyl or (C 1 -C 4 ) haloalkyl; R γ (C r C4) alkyl, (C 3 -C 6) -cycloalkyl or (C3-C6) cycloalkyl (Ci-C 4) -alkyl and A is -CH 2 -, -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -O-, -CH 2 CH 2 -O-, -CH 2 -CH 2 -CH 2 -O-, particularly preferably those of the formula K1-K7
(K3) (K3)
L) phosphorhaltige Herbizide, z.B. eine oder mehrere Verbindungen der Formel (IV) oder deren Derivate wie Salze, L) phosphorus-containing herbicides, for example one or more compounds of the formula (IV) or derivatives thereof, such as salts,
O OO O
H3C-P-CH-CH2-CH-C-Z1 (IV)H 3 CP-CH-CH 2 -CH-CZ 1 (IV)
OH NH2 worinOH NH 2 wherein
Z1 einen Rest der Formel -OM, -NHCH(CH3)CONHCH(CH3)CO2M oder -NHCH(CH3)CONHCH[CH2CH(CH3)2]CO2M und M = H oder ein Salz bildendes Kation bedeuten, und/oder eine oder mehrere Verbindungen der Formel (V) oder deren Derivate wie Salze,Z 1 is a radical of the formula -OM, -NHCH (CH 3 ) CONHCH (CH 3 ) CO 2 M or -NHCH (CH 3 ) CONHCH [CH 2 CH (CH 3 ) 2 ] CO 2 M and M = H or Salt-forming cation, and / or one or more compounds of the formula (V) or derivatives thereof, such as salts,
(V) worin(V) wherein
Z2 einen Rest der Formel CN oder CO2R1 bedeutet, in dem R1 = Q oder ein Salz bildendes Kation ist und dabei Q = H, Alkyl, Alkenyl, Alkoxyalkyl oder C6-Ci0-Aryl, das unsubstituiert oder substituiert ist und vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Alkyl, Alkoxy, Halogen, CF3, NO2 und CN substituiert ist, undZ 2 is a radical of the formula CN or CO 2 R 1 in which R 1 = Q or a salt-forming cation, while Q = H, alkyl, alkenyl, alkoxyalkyl or C 6 -C 0 aryl which is unsubstituted or substituted is and is preferably unsubstituted or substituted by one or more radicals from the group alkyl, alkoxy, halogen, CF 3 , NO 2 and CN, and
R2, R3 jeweils unabhängig voneinander H, Alkyl, Cβ-Cio-Aryl, das unsubstituiert oder substituiert ist und vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Alkyl, Alkoxy, Halogen, CF3, NO2 und CN substituiert ist, oderR 2 , R 3 are each independently H, alkyl, Cβ-Cio-aryl, which is unsubstituted or substituted and is preferably unsubstituted or substituted by one or more radicals from the group alkyl, alkoxy, halogen, CF 3 , NO 2 and CN , or
Biphenyl oder ein Salz bildendes Kation bedeuten.Mean biphenyl or a salt-forming cation.
Beispiele für Wirkstoffe der Formel (IV) und (V) sind folgende: - Glufosinate und dessen Ammoniumsalz in racemischer Form, d.h. 2-Amino-4-Examples of active compounds of the formulas (IV) and (V) are as follows: glufosinates and their ammonium salt in racemic form, i. 2-Amino-4-
[hydroxy(methyl)phosphinoyl]-butansäure bzw. dessen Ammoniumsalz, - das L-Enantiomer von Glufosinate und dessen Ammoniumsalz, - Bilanafos/Bialaphos, d.h. L-2-Amino-4-[hydroxy(methyl)phosphinoyl]-butanoyl-L- alaninyl-L-alanin und dessen Natriumsalz[hydroxy (methyl) phosphinoyl] -butanoic acid or its ammonium salt, - the L-enantiomer of glufosinate and its ammonium salt, Bilanafos / bialaphos, ie L-2-amino-4- [hydroxy (methyl) phosphinoyl] butanoyl-L-alaninyl-L-alanine and its sodium salt
- Glyphosate.- glyphosate.
M) Carbamate, z.B. Asulam, Carbetamide, Chloropham und Propham;M) carbamates, e.g. Asulam, Carbetamide, Chloropham and Propham;
N) Benzofurane, z.B. Benfuresate und Ethofumesate;N) benzofurans, e.g. Benfuresate and Ethofumesate;
O) Phytohormone;O) phytohormones;
P) Auxine und Auxinanaloga, z.B. 4-lndol-3-buttersäure, lndol-3-essigsäure, 1- Naphthylessigsäure, 2-(1-Naphthyl)acetamid und 2-Naphthyloxyessigsäure;P) Auxins and auxin analogs, e.g. 4-indole-3-butyric acid, indole-3-acetic acid, 1-naphthylacetic acid, 2- (1-naphthyl) acetamide and 2-naphthyloxyacetic acid;
Q) Zytokinine, z.B. Cythokinin, Kinetin und 6-Benzylaminopurin;Q) cytokinins, e.g. Cythokinin, Kinetin and 6-Benzylaminopurine;
R) Gibberelline, z.B. Gibberillinsäure, Gibberillin A4 und A7;R) gibberellins, e.g. Gibberillic Acid, Gibberillin A4 and A7;
S) Absissinsäure- und deren Derivate;S) absissinic acid and its derivatives;
T) Ethylenvorläufer, z.B. Ethephon;T) ethylene precursors, e.g. ethephon;
U) Herbizide aus der Gruppe der Fettsäuresynthetase-Inhibitoren;U) herbicides from the group of fatty acid synthetase inhibitors;
V) Harnstoffe, z.B. Chlorotoluron, Dimefuron, Diuron, Fluometuron, Isoproturon, Isouron, Karbutilate, Linuron, Methabenzthiazuron, Metobenzuron, Metoxuron, Monolinuron, Neburon, Siduron und Tebuthiuron undV) ureas, e.g. Chlorotoluron, dimefuron, diuron, fluometuron, isoproturon, isourone, carbutilate, linuron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron and tebuthiuron and
W) Metamitron;W) metamitron;
X) Hydroxybenzonitrile, z.B. wie Bromoxynil und loxynil und deren Salze und Ester, wie Bromoxyniloctanoat und loxyniloctanoat. Die agrochemischen Wirkstoffe können auch Wachstumsregulatoren sein. Beispiele hierfür sind Tribufos, Cyclanilide und Thidiazuron.X) Hydroxybenzonitriles, for example, such as bromoxynil and loxynil and their salts and esters, such as Bromoxyniloctanoat and loxyniloctanoat. The agrochemical active substances can also be growth regulators. Examples are tribufos, cyclanilides and thidiazuron.
Die Herbizide (Pflanzenwuchsregulatoren) der Gruppen A bis X sind beispielsweise aus den oben jeweils genannten Schriften und/oder aus "The Pesticide Manual", 12. Auflage (2000) und 13. Auflage (2003), The British Crop Protection Council, "Agricultural Chemicals Book Il - Herbicides -", by WT. Thompson, Thompson Publications, Fresno CA1 USA 1990 und "Farm Chemicals Handbook '90", Meister Publishing Company, Willoughby OH, USA.1990, bekannt.The herbicides (plant growth regulators) of groups A to X, for example, from the above-mentioned writings and / or from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council, "Agricultural Chemicals Book II - Herbicides - ", by WT. Thompson, Thompson Publications, Fresno CA 1 USA 1990 and "Farm Chemicals Handbook '90", Meister Publishing Company, Willoughby OH, USA.
Bevorzugt sind für Fungizide (Bakterizide), Insektizide (Akarizide, Nematizide) und Herbizide (Pflanzenwuchsregulatoren):Fungicides (bactericides), insecticides (acaricides, nematicides) and herbicides (plant growth regulators) are preferred:
Atrazin, Acetochlor, Aclonifen, Alachlor, Amidochlor, Amidosulfuron, Azimsulfuron, Alloxydim, Amitraz, Anilofos, Asulam, Acetamiprid, Acrinathrin, Aldicarb, Azinphos- methyl, Amicarbazone, Bentazon, Bensulfuron(-methyl), Bromoxynil(-octanoat/- heptanoat), Butachlor, Bispyribac(-sodium), Benzobicyclon, Benzofenap, Butroxydim, Bitertanol, Bromuconazole, Benfuresate, Beta-Cyfluthrin, Chlorsulfuron, Chlorimuron, Clomazone, Clopyralid, Cinosulfuron, Cyclosulfamuron, Clethodim, Clodinafop-propargyl, Cycloxydim, Cyhalofop-butyl, Cypermethrin, Carbaryl, Cyfluthrin, Cyanazine, 2,4-D-Ester, 2,4-DB-Ester, 2,4-DP-Ester, CMPP-Ester, Cyclanilide, Carbendazim, Carpropamid, Cyproconazole, Chlortoluron, Diclofop- methyl, Desmedipham, Diflufenican, Dicamba, Deltamethrin, Diuron, EPTC, Ethoxysulfuron, Ethofumesate, Ethephon, Edifenphos, Endosulfan, Ethoprophos, Flazasulfuron, Florasulam, Flucarbazone(-sodium), Flumetsulam, Flufenacet, Fluoroglykofen, Fluroxypyr, Flupyrsulfuron, Foramsulfuron, Flumioxazin, Flumiclorac, Fomesafen, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop-P-butyl, Fluazifop-butyl, Fipronil, Fenamidone, Fenhexamid, Fentins, Fluquinconazole, Fosetyl Aluminium, Fentrazamide, Flurtamone, Fenamiphos, Fenthion, Glufosinate(-ammonium), Glyphosate, Halosulfuron, Haloxyfop, Haloxyfop-P, Haloxyfop-etotyl, Haloxyfop-P-methyl, Imazamox, Imazapic, Imazethapyr, Imazaquin, Imazapyr, Imazosulfuron, lodosulfuron, lodosulfuron(- methyl), loxynil(-octanoat), Isoxaflutole und dessen Diketonitrile, Isoxachlortole, Imidacloprid, Isoxadifen-ethyl, Iprodione, Iprovalincarb, Isoproturon, MCPA-Ester, MCPB, Mesotrione, Metamifop, Metosulam, Mesosulfuron(-methyl), (S-)Metolachlor, Metsulfuron-methyl, Metamitron, Metribuzin, Mefenpyr-diethyl, Mefenacet, Methamidophos, Methiocarb, Nicosulfuron, Niclosamide, Lactofen, Linuron, Oxyfluorfen, Oxazinon, Oxadiargyl, Oxadiazon, Oxydemeton-methyl, Pendimethalin, Phenmedipham, Picloram, Pinoxaden, Primisulfuron-methyl, Prosulfuron, Propanil, Propoxycarbazone(-sodium), Pyrazosulfuron(-methyl), Profoxydim, Propaquizafop, Pyrazolynate, Pyrazoxyfen, Prochloraz, Pencycuron, Prochloraz, Propamocarb HCl, Propineb, Pyrimethalin, Phosalone, Prothiofos, Quizalofop-P-tefuryl, Quizalofop-P- ethyl, Rimsulfuron, Sulfentrazone, Sulfosulfuron, Sulfometuron, Sethoxydim,Atrazine, acetochlor, aclonifen, alachlor, amidochlor, amidosulfuron, azimsulfuron, alloxydim, amitraz, anilofos, asulam, acetamiprid, acrinathrin, aldicarb, azinophosmethyl, amicarbazones, bentazone, bensulfuron (-methyl), bromoxynil (-octanoate / - heptanoate) , Butachlor, Bispyribac (-sodium), Benzobicyclone, Benzofenap, Butroxydim, Bitertanol, Bromuconazole, Benfuresate, Beta-Cyfluthrin, Chlorsulfuron, Chlorimuron, Clomazone, Clopyralid, Cinosulfuron, Cyclosulfamuron, Clethodim, Clodinafop-propargyl, Cycloxydim, Cyhalofop-butyl, Cypermethrin , Carbaryl, cyfluthrin, cyanazines, 2,4-D-esters, 2,4-DB-esters, 2,4-DP-esters, CMPP-esters, cyclanilides, carbendazim, carpropamide, cyproconazole, chlortoluron, diclofopmethyl, desmedipham , Diflufenican, Dicamba, Deltamethrin, Diuron, EPTC, Ethoxysulfuron, Ethofumesate, Ethephon, Edifenphos, Endosulfan, Ethoprophos, Flazasulfuron, Florasulam, Flucarbazone (-sodium), Flumetsulam, Flufenacet, Fluoroglycofen, Fluroxypyr, Flupyrsulfuron, Foramsulfuron, Flumioxazin , Flumiclorac, fomesafen, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-p-butyl, fluazifop-butyl, fipronil, fenamidone, fenhexamide, fentins, fluquinconazole, fosetyl aluminum, fentrazamide, flurtamone, Fenamiphos, fenthione, glufosinate (-ammonium), glyphosate, halosulfuron, haloxyfop, haloxyfop-P, haloxyfopetotyl, haloxyfop-P-methyl, imazamox, imazapic, imazethapyr, imazaquin, imazapyr, imazosulfuron, lodosulfuron, lodosulfuron (- methyl), loxynil (octanoate), isoxaflutole and its diketonitrile, isoxachlorotole, Imidacloprid, isoxadifen-ethyl, iprodione, iprovalinecarb, isoproturon, MCPA-esters, MCPB, mesotrione, metamifop, metosulam, mesosulfuron (-methyl), (S-) metolachlor, metsulfuron-methyl, metamitron, metribuzin, mefenpyr-diethyl, mefenacet, Methamidophos, methiocarb, nicosulfuron, niclosamide, lactofen, linuron, oxyfluorfen, oxazinone, oxadiargyl, oxadiazone, oxydemeton-methyl, pendimethalin, phenmedipham, picloram, pinoxaden, primisulfuron-methyl, prosulfuron, propanil, propoxycarbazone (-sodium), pyrazosulfuron (-methyl ), Profoxydim, propaquizafop, pyrazolynates, pyrazoxyfen, prochloraz, pencycuron, prochloraz, propamocarb HCl, propineb, pyrimethalin, phosalones, prothiofos, quizalofop-p-tefuryl, quizalofop-p-ethyl, rimsulfuron, sulfentrazone, sulfosulfuron, sulfometuron, sethoxydim,
Sulcotrione, Spiroxamine, Silafluofen, Terbuthylazin, Thifensulfuron, Triasulfuron, Tribenuron, Triclopyr, Triflusulfuron-methyl, Trifluralin, Tritosulfuron, Topramezone, Tepraloxydim, Tralkoxydim, Terbufos, Thidiazuron, Tebuconazole, Tolylfluanid- Dichlofluanid, Tradimefon, Tradimenol, Trifloxystrobin, Thiacloprid, Thiodicarb, Tralomethrin, Trazophos, Tϊichlorfon, Triflumuron, Triticonazole und Isoxapyrifop, und gegebenenfalls deren Ester und Salze.Sulcotrione, spiroxamine, silafluofen, terbuthylazine, thifensulfuron, triasulfuron, tribenuron, triclopyr, triflusulfuron-methyl, trifluralin, tritosulfuron, toramezone, tepraloxydim, tralkoxydim, terbufos, thidiazuron, tebuconazole, tolylfluanidichlofluanid, tradimefon, tradimenol, trifloxystrobin, thiacloprid, thiodicarb, Tralomethrin, Trazophos, Tϊichlorfon, triflumuron, triticonazole and isoxapyrifop, and optionally their esters and salts.
Die vorstehend aufgeführten agrochemischen Wirkstoffe sind z.B. bekannt aus „The Pesticide Manual", 12. Auflage (2000) und 13. Auflage (2003), The British Crop Protection Council oder den nach den einzelnen Wirkstoffen aufgeführten Literaturstellen.The agrochemical active ingredients listed above are e.g. known from "The Pesticide Manual", 12th edition (2000) and 13th edition (2003), The British Crop Protection Council or the references listed after the individual active ingredients.
Die agrochemischen Wirkstoffe können auch Safener sein. Beispiele hierfür sind unter anderem: a) Verbindungen der Formeln (S-Il) bis (S-IV),The agrochemical active substances can also be safeners. Examples include: a) compounds of the formulas (S-II) to (S-IV),
(S-Il) (S-III) (S-IV) wobei die Symbole und Indizes folgende Bedeutungen haben: n' ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3;(S-II) (S-III) (S-IV) where the symbols and indices have the following meanings: n 'is a natural number from 0 to 5, preferably 0 to 3;
T ist eine (Ci oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (C-rC-OAlkylresten oder mit [(C-ι-C3)-Alkoxy]-carbonyl substituiert ist;T is a (Ci or C 2 ) alkanediyl chain, which is unsubstituted or substituted by one or two (C-rC-OAlkylresten or with [(C-ι-C 3 ) alkoxy] carbonyl;
W ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen des Typs N oder O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (W 1 ) bis (W4),W is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N or O atoms, at least one N atom and at most one O atom in the ring, preferably a radical from the group (W 1) to (W4),
(W1) (W2) (W3) (W4)(W1) (W2) (W3) (W4)
m' ist 0 oder 1 ; R17, R19 sind gleich oder verschieden Halogen,m 'is 0 or 1; R 17 , R 19 are the same or different halogen,
(d-C4)Alkyl, (C1-C4)AIkOXy, Nitro oder (CrC4)Haloalkyl;(C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C r C 4 ) haloalkyl;
R18, R20 sind gleich oder verschieden OR24, SR24 oder NR24R25 oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S-Il) bzw. (S-III) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C-i -C4)AI kyl, (CrC4)AIkOXy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel OR24, NHR25 oder N(CH3)2, insbesondere der Formel OR24; R24 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; R25 ist Wasserstoff, (Ci-C6)Alkyl, (C-ι-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; Rx ist H, (Ci-C8)Alkyl, Ci-C8(Haloalkyl), (CrC4)AIkOXy(C1-C8)AIRyI, Cyano oder COOR26, worin R26 Wasserstoff, (Ci-C8)Alkyl, (CrC8)Haloalkyl, (C1-C4)AIkOXy- (CrC4)alkyl, (CrC6)Hydroxyalkyl, (C3-C12)Cycloalkyl oder Tri-(C1-C4)-alkyl- silyl ist; R27, R28, R29 sind gleich oder verschieden Wasserstoff, (CrC8)Alkyl,R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S. , which is connected via the N-atom with the carbonyl group in (S-II) or (S-III) and unsubstituted or by radicals from the group (Ci-C 4 ) AI kyl, (CrC 4 ) AIkOXy or optionally substituted is phenyl substituted, preferably a radical of the formula oR 24, NHR 25 or N (CH 3) 2, in particular of the formula oR 24; R 24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms; R 25 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl; R x is H, (Ci-C 8 ) alkyl, Ci-C 8 (haloalkyl), (CrC 4 ) AIkOXy (C 1 -C 8 ) AIRyI, cyano or COOR 26 , wherein R 26 is hydrogen, (Ci-C 8 ) Alkyl, (C r C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C r C 4 ) alkyl, (CrC 6 ) hydroxyalkyl, (C 3 -C 12 ) cycloalkyl or tri (C 1 -C 4 ) alkylsilyl; R 27 , R 28 , R 29 are identical or different hydrogen, (C 1 -C 8 ) alkyl,
(C-ι-Cs)Haloalkyl, (C-3-C12)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; R21 ist (CrC4)AIkYl, (CrC4)Haloalkyl, (C2-C4)Alkenyl, (C2-C4)Haloalkenyl,(C 1 -C 5) haloalkyl, (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl; R 21 is (C r C 4 ) Alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl,
(C3-C7)Cycloalkyl, vorzugsweise Dichlormethyl; R22, R23 ist gleich oder verschieden Wasserstoff, (CrC4)Alkyl, (C2-C4)Alkenyl,(C 3 -C 7 ) cycloalkyl, preferably dichloromethyl; R 22 , R 23 is identical or different hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl,
(C2-C4)Alkinyl, (CrC4)Haloalkyl, (C2-C4)Haloalkenyl, (CrC^Alkylcarbamoyl- (CrC4)alkyl, (C2-C4)Alkenylcarbamoyl-(CrC4)alkyl, (C1-C4)AIkOXy-(C1- C4)alkyl, Dioxolanyl-(CrC4)alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder R22 und R23 bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring; vorzugsweise Safener folgender Untergruppen von Verbindungen der Formeln (S-Il) bis (S-IV): - Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (d.h. der(C 2 -C 4) alkynyl, (C r C4) haloalkyl, (C 2 -C 4) haloalkenyl, (CrC ^ alkylcarbamoyl (CrC 4) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (CrC 4) alkyl, (C 1 -C 4) AIkOXy- (C 1 - C 4) alkyl, dioxolanyl (C r C4) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R 22 and R 23 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring, preferably safeners of the following subgroups of compounds of the formulas (S-II) to (S-IV): Dichlorophenylpyrazoline-3-carboxylic acid type compounds (ie, the
Formel (S-Il), worin W = (W1 ) und (R17Jn 1 = 2,4-Cl2), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3- carbonsäureethylester (ll-1 , Mefenpyr-diethyl), Mefenpyr-dimethyl und Mefenpyr (H-O), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind;Formula (S-II) in which W = (W 1 ) and (R 17 J n 1 = 2,4-Cl 2 ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5- methyl-2-pyrazoline-3-carboxylic acid ethyl ester (II-1, mefenpyr-diethyl), mefenpyr-dimethyl and mefenpyr (HO), and related compounds as described in WO-A-91/07874;
- Derivate der Dichlorphenylpyrazolcarbonsäure (d.h. der Formel (S-Il), worin W = (W2) und (R17)n- = 2,4-Cl2 ist ), vorzugsweise Verbindungen wie 1-(2,4- Dichloφhenyl)-5-methyl-pyrazol-3-carbonsäureethylester (II-2), 1-(2,4- Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (II-3), 1 -(2,4- Dichlorphenyl)-5-(1 ,1-dimethyl-ethyl)pyrazol-3-carbonsäureethylester (II-4),Derivatives of dichlorophenylpyrazolecarboxylic acid (ie of formula (S-II) wherein W = (W 2 ) and (R 17 ) n - = 2,4-Cl 2 ), preferably compounds such as 1- (2,4-dichloro-phenyl) - Ethyl 5-methyl-pyrazole-3-carboxylate (II-2), 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylate (II-3), 1- (2,4-dichlorophenyl) - Ethyl 5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylate (II-4),
1-(2,4-Dichloφhenyl)-5-phenyl-pyrazol-3-carbonsäureethylester (ll-5) und verwandte Verbindungen, wie sie in EP-A-0333131 und EP-A-0269806 beschrieben sind;1- (2,4-Dichloro-phenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (II-5) and related compounds as described in EP-A-0333131 and EP-A-0269806;
- Verbindungen vom Typ der Triazolcarbonsäuren (d.h. der Formel (S-Il), worin W = (W3) und (R17V = 2,4-Cl2 ist), vorzugsweise Verbindungen wie Fenchlorazol- ethyl, d.h. 1 -(2,4-Dichlorphenyl)-5-trichlormethyl-(1 H)-1 ,2,4-triazol-3- carbonsäureethylester (II-6), und verwandte Verbindungen (siehe EP-A-0174562 und EP-A-0346620);Compounds of the type of the triazolecarboxylic acids (ie of the formula (S-II) in which W = (W3) and (R 17 V = 2,4-Cl 2 ), preferably compounds such as fenchloroazolethyl, ie 1 - (2, 4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (II-6), and related compounds (see EP-A-0174562 and EP-A-0346620);
- Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3-carbonsäure oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure wie Isoxadifen (11-12), (worin W = (W4) ist), vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3- carbonsäureethylester (II-7) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (II-8) und verwandte Verbindungen, wie sie in WO-A- 91/08202 beschrieben sind, oder der 5,5-Diphenyl-2-isoxazolin-carbonsäureethylester (II-9, Isoxadifen-ethyl) oder -n-propylester (11-10) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3- carbonsäureethylester (11-11 ), wie sie in der WO-A-95/07897 beschrieben sind.Compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, such as isoxadifen (11-12), (wherein W = (W4 ), preferably compounds such as ethyl 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (II-7) or 5-phenyl-2-isoxazoline-3-carboxylate (II-8) and related compounds, as described in WO-A-91/08202, or the ethyl 5,5-diphenyl-2-isoxazoline-carboxylate (II-9, isoxadifen-ethyl) or n-propyl ester (11-10) or the 5- (5-10) 4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (11-11), as described in WO-A-95/07897.
- Verbindungen vom Typ der 8-Chinolinoxyessigsäure, z.B. solche der Formel (S- III), worin (R19)n< = 5-CI, R20 = OR24 und T = CH2 ist, vorzugsweise die- Compounds of the type of 8-quinolinoxyacetic acid, for example those of the formula (S-III), wherein (R 19 ) n <= 5-CI, R 20 = OR 24 and T = CH 2 , preferably the
Verbindungen (5-Chlor-8-chinolinoxy)essigsäure-(1-methylhexyl)-ester (111-1 ,Compounds (5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester (111-1,
Cloquintocet-mexyl), (5-Chlor-8-chinolinoxy)essigsäure-(1 ,3-dimethyl-but-1 -yl)- ester (III-2), (5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (lll-3), (5-Cloquintocet-mexyl), (5-chloro-8-quinolinoxy) acetic acid (1, 3-dimethylbut-1-yl) -ester (III-2), (5-chloro-8-quinolinoxy) acetic acid 4- allyl oxy-butyl ester (III-3), (5-
Chlor-8-chinolinoxy)essigsäure-1 -allyloxy-prop-2-ylester (III-4), (5-Chlor-8- chinolinoxy)essigsäureethylester (III-5), (5-Chlor-8- chinolinoxy)essigsäuremethylester (III-6), (5-Chlor-8- chinolinoxy)essigsäureallylester (lll-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2- propyliden-iminoxy)-1-ethylester (III-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo- prop-1-ylester (III-9), (5-Chlor-8-chinolinoxy)essigsäure (111-10) und dessen Salze wie sie z.B. in der WO-A-02/34048 beschrieben sind, und verwandteChloro-8-quinolinoxy) -acetic acid 1-allyloxy-prop-2-yl ester (III-4), (5-chloro-8-quinolinoxy) -acetic acid ethyl ester (III-5), (5-chloro-8-quinolinoxy) -acetic acid methyl ester ( III-6), (5-chloro-8-quinolinoxy) allyl acetate (III-7), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (III-8) , (5-chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl-ester (III-9), (5-chloro-8-quinolinoxy) acetic acid (III-10) and its salts as described, for example in WO-A-02/34048 and related
Verbindungen, wie sie in EP-A-0860750, EP-A-0094349 und EP-A-0191736 oderCompounds as described in EP-A-0860750, EP-A-0094349 and EP-A-0191736 or
EP-A-0492366 beschrieben sind. - Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)-malonsäure, d.h. der FormelEP-A-0492366. Compounds of the (5-chloro-8-quinolinoxy) -malonic acid type, i. the formula
(S-III), worin (R1V = 5-CI, R20= OR24, T = -CH(COO-Alkyl)- ist, vorzugsweise die(S-III) wherein (R 1 is V = 5-Cl, R 20 = OR 24 , T = -CH (COO-alkyl) -, preferably the
Verbindungen (5-Chlor-8-chinolinoxy)-malonsäure-diethylester (111-11 ), (5-Chlor- 8-chinolinoxy)-malonsäurediallylester, (5-Chlor-8-chinolinoxy)-malonsäure- methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0582198 beschrieben sind.Compounds (5-chloro-8-quinolinoxy) -malonic acid diethyl ester (111-11), (5-chloro) 8-quinolinoxy) -malonic acid diallyl ester, (5-chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds, as described in EP-A-0582198.
- Verbindungen vom Typ der Dichloracetamide, d.h. der Formel (S-IV), vorzugsweise: N,N-Diallyl-2,2-dichloracetamid (Dichlormid (IV-1), aus US- Dichloroacetamide type compounds, i. of the formula (S-IV), preferably: N, N-diallyl-2,2-dichloroacetamide (dichloromide (IV-1), from US
4,137,070), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1 ,4-benzoxazin (IV-2, Benoxacor, aus EP 0149974), N1 ,N2-Diallyl-N2-dichloracetylglycinamid (DKA-24 (IV-3), aus HU 2143821 ), 4-Dichloracetyl-1-oxa-4-aza-spiro[4,5]decan (AD-67), 2,2-Dichlor-N-(1 ,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamid (PPG-1292), 3- Dichloracetyl-2,2,5-trimethyloxazolidin (R-29148, IV-4), 3-Dichloracetyl-2,2- dimethyl-5-phenyloxazolidin, 3-Dichloracetyl-2,2-dimethyl-5-(2-thienyl)oxazolidin, 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyloxazolidin (Furiiazole (IV-5), MON 13900), 1-Dichloracetyl-hexahydro-3,3,8a-trimethylpyrrolo[1 ,2-a]pyrimidin-6(2H)- on (Dicyclonon, BAS 145138), b) eine oder mehreren Verbindungen aus Gruppe:4,137,070), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (IV-2, Benoxacor, from EP 0149974), N1, N2-diallyl-N2-dichloroacetylglycine amide (DKA-24 ( IV-3), from HU 2143821), 4-dichloroacetyl-1-oxa-4-aza-spiro [4,5] decane (AD-67), 2,2-dichloro-N- (1,3-dioxolane) 2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148, IV-4), 3-dichloroacetyl-2,2-dimethyl 5-phenyloxazolidine, 3-dichloroacetyl-2,2-dimethyl-5- (2-thienyl) oxazolidine, 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyloxazolidine (Furiiazole (IV-5), MON 13900 ), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (dicyclonone, BAS 145138), b) one or more compounds from group:
1 ,8-Naphthalsäureanhydrid, Methyl-diphenylmethoxyacetat, 1-(2-Chlorbenzyl)-3-(1- methyl-1-phenylethyl)hamstoff (Cumyluron), O,O-Diethyl S-2-ethylthioethyl phosphordithioat (Disulfoton), 4-Chlorphenyl-methylcarbamat (Mephenate), O, O- Diethyl-O-phenylphosphorotioat (Dietholate), 4-Carboxy-3,4-dihydro-2H-1 - benzopyran-4-essigsäure (CL-304415, CAS-Regno: 31541-57-8), Cyanomethoxyimino(phenyl)acetonitril (Cyometrinil), 1 ,3-Dioxolan-2- ylmethoxyimino(phenyl)acetonitril (Oxabetrinil), 4'-Chlor-2,2,2-trifluoracetophenon-O- 1 ,3-dioxolan-2-ylmethyloxim (Fluxofenim), 4,6-Dichlor-2-phenylpyrimidin (Fenclorim), Benzyl-2-chlor-4-trifluormethyl-1 ,3-thiazol-5-carboxylat (Flurazole), 2-Dichlormethyl- 2-methyl-1 ,3-dioxolan (MG-191 ), N-(4-Methylphenyl)-N'-(1 -methyl-1 - phenylethyl)harnstoff (Dymron), (2,4-Dichlorphenoxy)essigsäure (2,4-D), (4- Chlorphenoxy)essigsäure, (R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop), 4- (2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4-Chlor-o-tolyloxy)essigsäure (MCPA), 4- (4-Chlor-o-tolyloxy)buttersäure, 4-(4-Chloφhenoxy)buttersäure, 3,6-Dichlor-2- methoxybenzoesäure (Dicamba), 1-(Ethoxycarbonyl)ethyl 3,6-dichlor-2- methoxybenzoat (Lactidichlor) sowie deren Salze und Ester, vorzugsweise (CrCe); c) N-Acylsulfonamide der Formel (S-V) und ihre Salze, 1,8-naphthalic anhydride, methyl-diphenylmethoxyacetate, 1- (2-chlorobenzyl) -3- (1-methyl-1-phenylethyl) -urea (cumyluron), O, O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfonyl), 4 -Chlorophenyl-methylcarbamate (mephenate), O, O-diethyl-O-phenylphosphorotioate (dietholate), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Regno: 31541 -57-8), cyanomethoxyimino (phenyl) acetonitrile (Cyometrinil), 1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinil), 4'-chloro-2,2,2-trifluoroacetophenone O-1, 3 dioxolan-2-ylmethyloxime (Fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl- 2-methyl-1,3-dioxolane (MG-191), N- (4-methylphenyl) -N '- (1-methyl-1-phenylethyl) urea (Dymron), (2,4-dichlorophenoxy) acetic acid (2 , 4-D), (4-chlorophenoxy) acetic acid, (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4- DB), (4-chloro-o-tolyloxy) vinegar acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl 3,6- dichloro-2-methoxybenzoate (lactidichloro) and their salts and esters, preferably (CrCe); c) N-acylsulfonamides of the formula (SV) and their salts,
worinwherein
R30 Wasserstoff, einen Kohlenwasserstoffrest, einen Kohlenwasserstoffoxyrest, einen Kohlenwasserstoffthiorest oder einen Heterocyclylrest, der vorzugsweise über ein C-Atom gebunden ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, Formyl, Carbonamid, Sulfonamid und Reste der Formel -Za-Ra substituiert ist, wobei jeder Kohlenwasserstoffteil vorzugsweise 1 bis 20 C-Atome aufweist und ein C-haltiger Rest R30 inklusive Substituenten vorzugsweise 1 bis 30 C-Atome aufweist;R 30 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbylthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more identical or different radicals from the group halogen, cyano, nitro , Amino, hydroxy, carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Z a -R a is substituted, wherein each hydrocarbon moiety preferably 1 to 20 carbon atoms and a C-containing radical R 30 including substituents preferably 1 to 30 Having C atoms;
R31 Wasserstoff oder (d-C4)-Alkyl, vorzugsweise Wasserstoff, oderR 31 is hydrogen or (dC 4) -alkyl, preferably hydrogen, or
R30 und R31 zusammen mit der Gruppe der Formel -CO-N- den Rest eines 3- bis 8-gliedrigen gesättigten oder ungesättigten Rings;R 30 and R 31 together with the group of the formula -CO-N- denote the radical of a 3- to 8-membered saturated or unsaturated ring;
R32 gleich oder verschieden Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, Formyl, CONH2, SO2NH2 oder einen Rest der Formel -Zb-Rb ;R 32 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula -Z b -R b ;
R33 Wasserstoff oder (CrC4)-Alkyl, vorzugsweise H; R34 gleich oder verschieden Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, CHO, CONH2, SO2NH2 oder einen Rest der Formel -Zc-Rc ;R 33 is hydrogen or (C 1 -C 4 ) -alkyl, preferably H; R 34 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula -Z c -R c ;
Ra einen Kohlenwasserstoffrest oder einen Heterocyclylrest, wobei jeder der beiden letztgenannten Reste unsubstituiert oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Nitro, Amino, Hydroxy, Mono- und Di-[(CrC4)-alkyl]-amino substituiert ist, oder einen Alkylrest, in dem mehrere, vorzugsweise 2 oder 3, nicht benachbarte CH2-Gruppen jeweils durch ein Sauerstoffatom ersetzt sind; Rb,Rc gleich oder verschieden einen Kohlenwasserstoffrest oder einenR a is a hydrocarbon radical or a heterocyclyl radical, where each of the latter two radicals is unsubstituted or substituted by one or more identical or different radicals from the group of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(C 1 -C 4 ) -alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom; R b , R c, identically or differently, are a hydrocarbon radical or a
Heterocyclylrest, wobei jeder der beiden letztgenannten Reste unsubstituiert oder durch einen oder mehrere gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Nitro, Amino, Hydroxy, Phosphoryl, Halogen- (CrC4)-alkoxy, Mono- und Di-[(CrC4)-alkyl]-amino substituiert ist, oder einenHeterocyclylrest, wherein each of the last two radicals unsubstituted or by one or more identical or different radicals selected from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halogeno (C 1 -C 4 ) alkoxy, mono- and di- [(CrC 4 ) -alkyl] -amino, or a
Alkylrest, in dem mehrere, vorzugsweise 2 oder 3, nicht benachbarte CH2-Gruppen jeweils durch ein Sauerstoffatom ersetzt sind;Alkyl radical in which a plurality, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom;
Za eine divalente Gruppe der Formel -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-,Z a is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-,
-O-CO-, -S-CO-, -SO-, -SO2-, -NR*-, -CO-NR*-, -NR*-CO-, -SO2-NR*- oder -NR*-SO2-, wobei die rechts angegebene Bindung der jeweiligen divalenten-O-CO-, -S-CO-, -SO-, -SO 2 -, -NR * -, -CO-NR * -, -NR * -CO-, -SO 2 -NR * - or -NR * -SO 2 -, where the binding on the right is the respective divalent one
Gruppe die Bindung zum Rest Ra ist und wobei die R* in den letztgenannten 5 Resten unabhängig voneinander jeweils H, (d-C4)-Alkyl oder HaIo-(CrC4)- alkyl bedeuten;Group is the bond to the radical R a and the R * in the 5 last-mentioned radicals independently of one another are each H, (dC 4) -alkyl or halo- (CrC 4) - alkyl;
Zb, Zc unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formel -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-,Z b , Z c independently of one another a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-,
-S-CO-, -SO-, -SO2-, -NR*-, -SO2-NR*-, -NR*-SO2-, -CO-NR*- oder -NR*-CO-, wobei die rechts angegebene Bindung der jeweiligen divalenten Gruppe die Bindung zum Rest Rb bzw. Rc ist und wobei die R* in den letztgenannten 5 Resten unabhängig voneinander jeweils H, (d-C4)-Alkyl oder Halo-(CrC4)-alkyl bedeuten; n eine ganze Zahl von O bis 4, vorzugsweise O, 1 oder 2, insbesondere O oder 1 , und m eine ganze Zahl von O bis 5, vorzugsweise 0, 1 , 2 oder 3, insbesondere O, 1 oder 2; bedeuten; vorzugsweise Safener von Verbindungen der Formel (S-V), worin-S-CO-, -SO-, -SO 2 -, -NR * -, -SO 2 -NR * -, -NR * -SO 2 -, -CO-NR * - or -NR * -CO-, wherein the bond of the respective divalent group indicated on the right is the bond to the radical R b or R c and wherein the R * in the last-mentioned 5 radicals independently of one another are H, (C 1 -C 4 ) -alkyl or halo- (C 1 -C 4 ) -alkyl mean; n is an integer from 0 to 4, preferably 0, 1 or 2, in particular O or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2; mean; preferably safeners of compounds of formula (SV) wherein
- R30 = H3C-O-CH2-, R31 = R33 = H, R34 = 2-OMe ist (V-1 ),R 30 = H 3 CO-CH 2 -, R 31 = R 33 = H, R 34 = 2-OMe is (V-1),
- R30 = H3C-O-CH2-, R31 = R33 = H, R34 = 2-OMe-5-CI ist (V-2),R 30 = H 3 CO-CH 2 -, R 31 = R 33 = H, R 34 = 2-OMe-5-CI is (V-2),
- R30 = Cyclopropyl, R31 = R33 = H, R34 = 2-OMe ist (V-3),R 30 = cyclopropyl, R 31 = R 33 = H, R 34 = 2-OMe is (V-3),
- R30 = Cyclopropyl, R31 = R33 = H, R34 = 2-OMe-5-CI ist (V-4), - R30 = Cyclopropyl, R31 = R33 = H, R34 = 2-Me ist (V-5),R 30 = cyclopropyl, R 31 = R 33 = H, R 34 = 2-OMe-5-CI is (V-4), R 30 = cyclopropyl, R 31 = R 33 = H, R 34 = 2- Me is (V-5),
- R30 = tert. Butyl, R31 = R33 = H, R34 = 2-OMe ist (V-6). d) Acylsulfamoylbenzoesäureamide der allgemeinen Formel (S-Vl)1 gegebenenfalls auch in Salzform,R 30 = tert. Butyl, R31 = R33 = H, R34 = 2-OMe is (V-6). d) Acylsulfamoylbenzoesäureamide of the general formula (S-Vl) 1 optionally in salt form,
worin X3 CH oder N; wherein X 3 is CH or N;
R35 Wasserstoff, Heterocyclyl oder einen Kohlenwasserstoffrest, wobei die beiden letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, CHO, CONH2, SO2NH2 und Za-Ra substituiert sind; R36 Wasserstoff, Hydroxy, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (CrC6)- Alkoxy, (C2-C6)-Alkenyloxy, wobei die fünf letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Reste aus der Gruppe Halogen, Hydroxy, (C-i-C-O-Alkyl, (Ci-C4)-Alkoxy und (C1-C4)- Alkylthio substituiert sind, oder R35 und R36 zusammen mit dem sie tragenden Stickstoffatom einen 3- bis 8- gliedrigen gesättigten oder ungesättigten Ring;R 35 is hydrogen, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 and Z a -R are a substituted; R 36 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (CrC 6) - alkoxy, (C 2 -C 6) - alkenyloxy, wherein the five last-mentioned radicals are optionally substituted by one or more identical or different radicals from the group halogen, hydroxy, (CICO-alkyl, (Ci-C 4) -alkoxy and (C 1 -C 4) - substituted alkylthio, or R 35 and R 36 together with the nitrogen atom carrying them form a 3- to 8-membered saturated or unsaturated ring;
R37 Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, CHO, CONH2, SO2NH2 oder Zb-Rb;R 37 is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 or Z b -R b ;
R38 Wasserstoff, (CrC4)-Alkyl, (C2-C4)-Alkenyl oder (C2-C4)-Alkinyl; R39 Halogen, Cyano, Nitro, Amino, Hydroxy, Carboxy, Phosphoryl, CHO, CONH2, SO2NH2 oder Zc-Rc;R 38 is hydrogen, (C r C4) alkyl, (C 2 -C 4) -alkenyl or (C 2 -C 4) alkynyl; R 39 is halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z c -R c ;
Ra einen (C2-C20)-Alkylrest, dessen Kohlenstoffkette ein- oder mehrfach durch Sauerstoffatome unterbrochen ist, Heterocyclyl oder einen Kohlenwasserstoffrest, wobei die zwei letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Reste aus der GruppeR a is a (C 2 -C 20 ) -alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group
Halogen, Cyano, Nitro, Amino, Hydroxy, Mono- und Di-[(Ci-C4)-alkyl]-amino substituiert sind;Halogen, cyano, nitro, amino, hydroxyl, mono- and di - [(Ci-C 4) -alkyl] amino groups;
Rb, Rc gleich oder verschieden einen (C2-C20)-Alkylrest, dessen Kohlenstoffkette ein- oder mehrfach durch Sauerstoffatome unterbrochen ist, Heterocyclyl oder einen Kohlenwasserstoffrest, wobei die zwei letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Nitro, Amino, Hydroxy, Phosphoryl, (C1-C4)- Haloalkoxy, Mono- und Di-[(Ci-C4)-alkyl]-amino substituiert sind;R b , R c, identically or differently, are a (C 2 -C 20 ) -alkyl radical whose carbon chain interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, phosphoryl, (C 1 -C 4 substituted [(Ci-C 4) alkyl] -amino) - - haloalkoxy, mono- and di;
Za eine divalente Einheit aus der Gruppe O1 S, CO, CS, C(O)O, C(O)S1 SO, SO2, NRd, C(O)NRd oder SO2NRd;Z a is a divalent unit from the group O 1 S, CO, CS, C (O) O, C (O) S 1 SO, SO 2 , NR d , C (O) NR d or SO 2 NR d ;
Zb, Zc gleich oder verschieden eine direkte Bindung oder eine divalente Einheit aus der Gruppe O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NRd, SO2NRd oder C(O)NRd;Z b , Z c, identically or differently, denote a direct bond or a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 , NR d , SO 2 NR d or C (O) NR d ;
Rd Wasserstoff, (CrC4)-Alkyl oder (CrC4)-Haloa!kyl; n eine ganze Zahl von O bis 4, und m für den Fall, dass X für CH steht, eine ganze Zahl von O bis 5, und für denR d is hydrogen, (C r C 4 ) alkyl or (C r C 4 ) haloalkyl; n is an integer from 0 to 4, and m in the case that X is CH, an integer from 0 to 5, and for the
Fall, dass X für N steht, eine ganze Zahl von O bis 4 bedeuten; vorzugsweise Safener von Verbindungen der Formel (S-Vl), in derCase that X is N, an integer from 0 to 4; preferably safeners of compounds of the formula (S-VI), in which
X3 CH;X 3 CH;
R35 Wasserstoff, (CrC6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C5-C6)- Cycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl mit bis zu drei Heteroatomen aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sechs letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Substituenten aus der Gruppe Halogen, (C1-C6)- Alkoxy, (CrC6)-Haloalkoxy, (Ci-C2)-Alkylsulfinyl, (CrC2)-Alkylsulfonyl, (C3-C6)-Cycloalkyl, (CrC4)-Alkoxycarbonyl, (CrC4)-Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (CrC4)-Alkyl und (CrC4)-Haloalkyl substituiert sind;R 35 is hydrogen, (C r C6) alkyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (C 5 -C 6) - cycloalkenyl, phenyl or 3- to 6 hetero-cyclic heterocyclyl having up to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur, wherein the six last-mentioned radicals are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C 1 -C 6 ) -alkoxy, (C r C 6) haloalkoxy, (Ci-C2) alkylsulfinyl, (CrC 2) alkylsulfonyl, (C 3 -C 6) -cycloalkyl, (CrC 4) alkoxycarbonyl, (C r C 4) -alkylcarbonyl and phenyl and, in (C r C4) alkyl and substituted (C r C 4) -haloalkyl case of cyclic radicals, also;
R36 Wasserstoff, (CrC6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, wobei die drei letztgenannten Reste gegebenenfalls durch einen oder mehrere, gleiche oder verschiedene Substituenten aus der Gruppe Halogen, Hydroxy, (C1-C4)- Alkyl, (CrC4)-Alkoxy und (CrC4)-Alkylthio substituiert sind; R37 Halogen, (CrC4)-Haloalkyl, (CrC4)-Haloalkoxy, Nitro, (CrC4)-Alkyl, (C1-C4)- Alkoxy, (CrC4)-Alkylsulfonyl, (CrC4)-Alkoxycarbonyl oder (C1-C4)- Alkylcarbonyl; R38 Wasserstoff; R39 Halogen, Nitro, (CrC4)-Alkyl, (C-i-C^-Haloalkyl, (Ci-C4)-Haloalkoxy, (C3-C6)-R 36 is hydrogen, (C r C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where the last three radicals mentioned are optionally substituted by one or more, identical or different substituents from the group halogen, hydroxy, (C 1 -C 4) - alkyl, (CrC 4) -alkoxy and (CrC 4) -alkylthio; R 37 is halogen, (CrC 4) -haloalkyl, (CrC 4) -haloalkoxy, nitro, (CrC 4) alkyl, (C 1 -C 4) - alkoxy, (CrC 4) alkylsulfonyl, (CrC 4) alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl; R 38 is hydrogen; R 39 is halogen, nitro, (CrC 4) alkyl, (CiC ^ haloalkyl, (CiC 4) -haloalkoxy, (C 3 -C 6) -
Cycloalkyl, Phenyl, (CrC4)-Alkoxy, Cyano, (CrC4)-Alkylthio, (CrC4)- Alkylsulfinyl, (CrC4)-Alkylsulfonyl, (CrC4)-Alkoxycarbonyl oder (CrC4)- Alkylcarbonyl; n 0, 1 oder 2 und m 1 oder 2 bedeuten.Cycloalkyl, phenyl, (C r C4) alkoxy, cyano, (CrC 4) alkylthio, (C r C 4) - alkylsulfinyl, (C r C 4) alkylsulfonyl, (C r C4) -alkoxycarbonyl or ( CrC 4 ) - alkylcarbonyl; n is 0, 1 or 2 and m is 1 or 2.
Insbesondere Verbindungen vom Typ der Acylsulfamoylbenzoesäureamide der nachfolgenden Formel (S-VII), die z.B. bekannt sind aus WO-A-99/16744,In particular, compounds of the acylsulfamoylbenzoic acid amide type represented by the following formula (S-VII), e.g. are known from WO-A-99/16744,
worin wherein
R21 = Cyclo-Propyl und R22 = H ist (S3-1 =R 21 = cyclopropyl and R 22 = H is (S3-1 =
4-Cyclopropylaminocarbonyl-N-(2-methoxybenzoyl)benzolsulfonamid;4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide;
Cyprosulfamide);Cyprosulfamide);
R21 = Cyclo-Propyl und R22 = 5-CI ist (S3-2), R21 = Ethyl und R22 = H ist (S3-3), R21 = iso-Propyl und R22 = 5-CI ist (S3-4) und R21 = iso-Propyl und R22 = H ist (S3-5 =R 21 = cyclopropyl and R 22 = 5-CI is (S3-2), R 21 = ethyl and R 22 = H is (S3-3), R 21 = iso-propyl and R 22 = 5-CI (S3-4) and R 21 = isopropyl and R 22 = H (S3-5 =
4-iso-propylaminocarbonyl-N-(2-methoxybenzoyl)benzolsulfonamid);4-iso-propylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide);
e) Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S-VIII), die z.B. bekannt sind aus der EP-A-365484,e) N-acylsulfamoylphenylureas of the formula (S-VIII), e.g. are known from EP-A-365484,
worin für einen Rest aus der Gruppe wherein for a rest of the group
Rα und Rß unabhängig voneinander für Wasserstoff, Ci-Cβ-Alkyl, C3-C8-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Alkinyl,R α and R ß independently hydrogen, Ci-Cβ alkyl, C 3 -C 8 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl,
oder durch C1-C4-AIkOXy oder or by C 1 -C 4 -alkoxy or
substituiertes C1-C4-AIkOXy, oder substituted C 1 -C 4 -alkoxy, or
Rα und Rß gemeinsam für eine C4-C6-Alkylenbrücke oder eine durch Sauerstoff, Schwefel, SO, SO2, NH oder -N(CrC4-Alkyl)- unterbrochene C4-C6- Alkylenbrücke,R α and R ß together are a C 4 -C 6 alkylene or by oxygen, sulfur, SO, SO 2, NH or -N (C r C 4 alkyl) - interrupted C 4 -C 6 - alkylene bridge,
Rγ für Wasserstoff oder Ci-C4-Alkyl,R γ is hydrogen or C 1 -C 4 -alkyl,
Ra und Rb unabhängig voneinander für Wasserstoff, Halogen, Cyan, Nitro,R a and R b independently of one another represent hydrogen, halogen, cyano, nitro,
Trifluormethyl, CrC4-Alkyl, CrC4-Alkoxy, d-C4-Alkylthio, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, -COORj, -CONRkRm, -COR", -SO2NRkRm oder -OSO2-C1- C4-Alkyl, oder Ra und Rb gemeinsam für eine C3-C4-Alkylenbrücke, die durch Halogen oder CrC4-Alkyl substituiert sein kann, oder eine C3-C4- Alkenylenbrücke, die durch Halogen oder d-C4-Alkyl substituiert sein kann, oder eine C4-Alkadienylenbrücke, die durch Halogen oder CrC4-Alkyl substituiert sein kann, undTrifluoromethyl, C r C 4 alkyl, C r C 4 alkoxy, dC 4 alkylthio, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, -COOR j, -CONR k R m, -COR ", - SO 2 NR k R m or -OSO 2 -C 1 - C 4 alkyl, or R a and R b together represent a C 3 -C 4 alkylene bridge which may be substituted by halogen or -C 4 alkyl, or C 3 -C 4 - alkenylene, which may be substituted by halogen or C 4 -alkyl, or a C 4 -alkadienylene bridge, which may be substituted by halogen or -C 4 alkyl, and
R9 und Rh unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl, Trifluormethyl, Methoxy, Methylthio oder -COORj stehen, wobei Rc Wasserstoff, Halogen, CrC4-Alkyl oder Methoxy,R 9 and R h independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl, trifluoromethyl, methoxy, methylthio or -COOR j , where R c is hydrogen, halogen, C r C 4 alkyl or methoxy,
Rd Wasserstoff, Halogen, Nitro, CrC4-Alkyl, Ci-C4-Alkoxy, d-C4-Alkylthio, d-C4-R d is hydrogen, halogen, nitro, -C 4 alkyl, Ci-C 4 alkoxy, dC 4 alkylthio, dC 4 -
Alkylsulfinyl, Ci-C4-Alkylsulfonyl, -COORj oder -CON RkRm,Alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, -COOR j or -CON R k R m ,
Re Wasserstoff, Halogen, CrC4-Alkyl, -COORj, Trifluormethyl oder Methoxy, oder Rd und Re gemeinsam für eine C3-C4-Alkylenbrücke,R e is hydrogen, halogen, -C 4 alkyl, -COOR j, trifluoromethyl or methoxy, or R d and R e together represent a C 3 -C 4 alkylene bridge,
Rf Wasserstoff, Halogen oder CrC4-Alkyl, Rx und Rγ unabhängig voneinander Wasserstoff, Halogen, CrC4-Alkyl, CrC4-R f is hydrogen, halogen or C r C 4 alkyl, R x and R γ independently represent hydrogen, halogen, -C 4 alkyl, -C 4 -
Alkoxy, CrC4-Alkylthio, -COOR4, Trifluormethyl, Nitro oder Cyan, Rj, Rk und Rm unabhängig voneinander Wasserstoff oder C-ι-C4-Alkyl, Rk und Rm gemeinsam eine C4-C6-Alkylenbrücke oder eine durch Sauerstoff, NH oder -N(CrC4-Alkyl)- unterbrochene C4-C6-Alkylenbrücke, und Rn CrC4-Alkyl, Phenyl oder durch Halogen, CrC4-Alkyl, Methoxy, Nitro oderAlkoxy, C r C 4 alkylthio, -COOR 4, trifluoromethyl, nitro or cyano, R j, R k and R m are independently hydrogen or C-ι-C 4 alkyl, R k and R m together form a C 4 - C 6 -alkylene bridge or a C 4 -C 6 -alkylene bridge interrupted by oxygen, NH or -N (C 1 -C 4 -alkyl), and R n is C r C 4 -alkyl, phenyl or by halogen, C 1 -C 4 -alkyl, methoxy , Nitro or
Trifluormethyl substituiertes Phenyl bedeuten; vorzugsweise Safener der Formel (S-VIII) sind 1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff,Trifluoromethyl substituted phenyl; preferably safeners of the formula (S-VIII) are 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff,1- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
1-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff,1- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methyl-urea,
1-[4-(N-Naphthoylsulfamoyl)phenyl]-3,3-dimethylharnstoff, einschließlich der Stereoisomeren und der in der Landwirtschaft gebräuchlichen Salze.1- [4- (N-Naphthoylsulfamoyl) phenyl] -3,3-dimethylurea, including the stereoisomers and the salts commonly used in agriculture.
Sofern es im Einzelnen nicht anders definiert wird, gelten für die Reste in denUnless otherwise defined in detail, the radicals in the
Formeln zu (S-Il) bis (S-VIII) im Allgemeinen die folgenden Definitionen.Formulas to (S-II) to (S-VIII) generally have the following definitions.
Die Reste Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino und Alkylthio sowie die entsprechenden ungesättigten und/oder substituierten Reste können im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein. Alkylreste, auch in den zusammengesetzten Bedeutungen wie Alkoxy, Haloalkyl usw. haben vorzugsweise 1 bis 4 C-Atome und, bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl. Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste; Alkenyl bedeutet z.B. AIIyI, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1- yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1-yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl. "(Ci-C4)-Alkyl" ist die Kurzschreibweise für Alkyl mit 1 bis 4 C-Atomen; entsprechendes gilt für andere allgemeine Restedefinitionen mit in Klammern angegebenen Bereichen für die mögliche Anzahl von C-Atomen. Cycloalkyl bedeutet bevorzugt einen cyclischen Alkylrest mit 3 bis 8, vorzugsweise 3 bis 7, besonders bevorzugt 3 bis 6 C-Atomen, beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl. Cycloalkenyl und Cycloalkinyl bezeichnen entsprechende ungesättigte Verbindungen. Halogen bedeutet Fluor, Chlor, Brom oder lod. Haloalkyl, Haloalkenyl und Haloalkinyl bedeuten durch Halogen, vorzugsweise durch Fluor, Chlor und/oder Brom, insbesondere durch Fluor oder Chlor, teilweise oder vollständig substituiertes Alkyl, Alkenyl oder Alkinyl, z.B. CF3, CHF2, CH2F, CF2CF3, CH2CHFCI, CCI3, CHCI2, CH2CH2CI. Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI. Entsprechendes gilt für sonstige Halogen substituierte Reste. Ein Kohlenwasserstoffrest kann ein aromatischer oder ein aliphatischerThe radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton. Alkyl radicals, even in the composite meanings such as alkoxy, haloalkyl, etc., preferably have 1 to 4 carbon atoms and, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl. Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl is for example AlII, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl , 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl. Alkynyl means, for example Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. "(C 1 -C 4 ) -alkyl" is the short notation for alkyl having 1 to 4 carbon atoms; the same applies to other general remainder definitions with bracketed ranges for the possible number of C atoms. Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8, preferably 3 to 7, particularly preferably 3 to 6, C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Cycloalkenyl and cycloalkynyl refer to corresponding unsaturated compounds. Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or fully substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 2 CF 3 , CH 2 CHFCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl. Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl. The same applies to other halogen-substituted radicals. A hydrocarbon radical can be an aromatic or an aliphatic
Kohlenwasserstoffrest sein, wobei ein aliphatischer Kohlenwasserstoffrest im allgemeinen ein geradkettiger oder verzweigter gesättigter oder ungesättigter Kohlenwasserstoffrest ist, vorzugsweise mit 1 bis 18, besonders bevorzugt 1 bis 12 C-Atomen, z.B. Alkyl, Alkenyl oder Alkinyl. Vorzugsweise bedeutet aliphatischer Kohlenwasserstoffrest Alkyl, Alkenyl oder Alkinyl mit bis zu 12 C-Atomen; entsprechendes gilt für einen aliphatischen Kohlenwasserstoffrest in einem Kohlenwasserstoffoxyrest.Hydrocarbon radical, wherein an aliphatic hydrocarbon radical is generally a straight-chain or branched saturated or unsaturated hydrocarbon radical, preferably having 1 to 18, particularly preferably 1 to 12 C-atoms, e.g. Alkyl, alkenyl or alkynyl. Preferably, aliphatic hydrocarbon radical alkyl, alkenyl or alkynyl having up to 12 carbon atoms; the same applies to an aliphatic hydrocarbon radical in a Kohlenwasserstoffoxyrest.
Aryl ist im allgemeinen ein mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6-20 C-Atomen, bevorzugt 6 bis 14 C-Atomen, besonders bevorzugt 6 bis 10 C-Atomen, z.B. Phenyl, Naphthyl, Tetrahydronaphthyl, Indenyl, Indanyl, Pentalenyl und Fluorenyl, besonders bevorzugt Phenyl.Aryl is generally a mono-, bi- or polycyclic aromatic system having preferably 6-20 C atoms, preferably 6 to 14 C atoms, more preferably 6 to 10 C atoms, e.g. Phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, more preferably phenyl.
Heterocyclischer Ring, heterocyclischer Rest oder Heterocyclyl bedeutet ein mono-, bi- oder polycyclisches Ringsystem, das gesättigt, ungesättigt und/oder aromatisch ist und eine oder mehrere, vorzugsweise 1 bis 4, Heteroatome, vorzugsweise aus der Gruppe N, S und O, enthält.Heterocyclic ring, heterocyclic radical or heterocyclyl means a mono-, bi- or polycyclic ring system which is saturated, unsaturated and / or aromatic and contains one or more, preferably 1 to 4, heteroatoms, preferably from the group N, S and O. ,
Bevorzugt sind gesättigte Heterocyclen mit 3 bis 7 Ringatomen und einem oder zwei Heteroatomen aus der Gruppe N, O und S, wobei die Chalcogene nicht benachbart sind. Besonders bevorzugt sind monocyclische Ringe mit 3 bis 7 Ringatomen und einem Heteroatom aus der Gruppe N, O und S, sowie Morpholin, Dioxolan, Piperazin, Imidazolin und Oxazolidin. Ganz besonders bevorzugte gesättigte Heterocyclen sind Oxiran, Pyrrolidon, Morpholin und Tetrahydrofuran. Bevorzugt sind auch teilweise ungesättigte Heterocyclen mit 5 bis 7 Ringatomen und einem oder zwei Heteroatomen aus der Gruppe N, O und S. Besonders bevorzugt sind teilweise ungesättigte Heterocyclen mit 5 bis 6 Ringatomen und einem Heteroatom aus der Gruppe N, O und S. Ganz besonders bevorzugte teilweise ungesättigte Heterocyclen sind Pyrazolin, Imidazolin und Isoxazolin. Ebenso bevorzugt ist Heteroaryl, z.B. mono- oder bicyclische aromatischePreferred are saturated heterocycles having 3 to 7 ring atoms and one or two heteroatoms from the group N, O and S, wherein the chalcogens are not adjacent are. Particularly preferred are monocyclic rings having 3 to 7 ring atoms and a heteroatom from the group N, O and S, and morpholine, dioxolane, piperazine, imidazoline and oxazolidine. Very particularly preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran. Also preferred are partially unsaturated heterocycles having 5 to 7 ring atoms and one or two heteroatoms from the group N, O and S. Particularly preferred are partially unsaturated heterocycles having 5 to 6 ring atoms and one heteroatom from the group N, O and S. Very particular preferred partially unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline. Also preferred is heteroaryl, for example mono- or bicyclic aromatic
Heterocyclen mit 5 bis 6 Ringatomen, die ein bis vier Heteroatome aus der Gruppe N, O, S enthalten, wobei die Chalcogene nicht benachbart sind. Besonders bevorzugt sind monocyclische aromatische Heterocyclen mit 5 bis 6 Ringatomen, die ein Heteroatom aus der Gruppe, N, O und S enthalten, sowie Pyrimidin, Pyrazin, Pyridazin, Oxazol, Thiazol, Thiadiazol, Oxadiazol, Pyrazol, Triazol und Isoxazol. Ganz besonders bevorzugt sind Pyrazol, Thiazol, Triazol und Furan. Substituierte Reste, wie substituierte Kohlenwasserstoffreste, z.B. substituiertes Alkyl, Alkenyl, Alkinyl, Aryl wie Phenyl und Arylalkyl wie Benzyl, oder substituiertes Heterocyclyl, bedeuten einen vom unsubstituierten Grundkörper abgeleiteten substituierten Rest, wobei die Substituenten vorzugsweise einen oder mehrere, vorzugsweise 1 , 2 oder 3, im Falle von Cl und F auch bis zur maximal möglichen Anzahl, Substituenten aus der Gruppe Halogen, Alkoxy, Haloalkoxy, Alkylthio, Hydroxy, Amino, Nitro, Carboxy, Cyano, Azido, Alkoxycarbonyl, Alkylcarbonyl, Formyl, Carbamoyl, Mono- und Dialkylaminocarbonyl, substituiertes Amino wie Acylamino, Mono- und Dialkylamino und Alkylsulfinyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl und, im Falle cyclischer Reste, auch Alkyl und Haloalkyl sowie den genannten gesättigten kohlenwasserstoffhaltigen Substituenten entsprechende ungesättigte aliphatische Substituenten, vorzugsweise Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, bedeuten. Bei Resten mit C-Atomen sind solche mit 1 bis 4 C-Atomen, insbesondere 1 oder 2 C-Atomen, bevorzugt. Bevorzugt sind in der Regel Substituenten aus der Gruppe Halogen, z.B. Fluor oder Chlor, (d-C4)Alkyl, vorzugsweise Methyl oder Ethyl, (CrC4)Haloalkyl, vorzugsweise Trifluormethyl, (C1-C-OAIkOXy, vorzugsweise Methoxy oder Ethoxy, (C1-C4)HaIOaIkOXy, Nitro und Cyano. Besonders bevorzugt sind dabei die Substituenten Methyl, Methoxy und Chlor.Heterocycles having 5 to 6 ring atoms containing one to four heteroatoms from the group N, O, S, wherein the chalcogens are not adjacent. Particularly preferred are monocyclic aromatic heterocycles having 5 to 6 ring atoms which contain a heteroatom from the group, N, O and S, and pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole and isoxazole. Very particular preference is given to pyrazole, thiazole, triazole and furan. Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, such as phenyl and arylalkyl, such as benzyl, or substituted heterocyclyl, represent a substituted radical derived from the unsubstituted radical, where the substituents are preferably one or more, preferably 1, 2 or 3 , in the case of Cl and F also up to the maximum possible number, substituents from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl , substituted amino such as acylamino, mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl and said saturated hydrocarbon-containing substituents corresponding unsaturated aliphatic substituents, preferably alkenyl, alkynyl, alkenyloxy, alkynyloxy , For radicals with C atoms, those having 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred. As a rule, preferred substituents are selected from the group halogen, for example fluorine or chlorine, (dC 4) alkyl, preferably methyl or ethyl, (C r C4) haloalkyl, preferably trifluoromethyl, (C 1 -C 10 -alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 ) halogenoalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy and chlorine.
Mono- oder disubstituiertes Amino bedeutet einen chemisch stabilen Rest aus der Gruppe der substituierten Aminoreste, welche beispielsweise durch einen oder zwei gleiche oder verschiedene Reste aus der Gruppe Alkyl, Alkoxy, Acyl und Aryl N-substituiert sind; vorzugsweise Monoalkylamino, Dialkylamino, Acylamino, Arylamino, N-Alkyl-N-Arylamino sowie N-Heterocyclen. Dabei sind Alkylreste mit 1 bis 4 C-Atomen bevorzugt. Aryl ist dabei vorzugsweise Phenyl. Substituiertes Aryl ist dabei vorzugsweise substituiertes Phenyl. Für Acyl gilt dabei die weiter unten genannte Definition, vorzugsweise (CrC4)Alkanoyl. Entsprechendes gilt für substituiertes Hydroxylamino oder Hydrazino.Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are N-substituted by, for example, one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles. In this case, alkyl radicals having 1 to 4 carbon atoms are preferred. Aryl is preferably phenyl. Substituted aryl is preferably substituted phenyl. This is true for acyl the definition mentioned further below applies, preferably (CrC 4) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
Gegebenenfalls substituiertes Phenyl ist vorzugsweise Phenyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach, bei Halogen wie Cl und F auch bis zu fünffach, durch gleiche oder verschiedene Reste aus der GruppeOptionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times, in halogens such as Cl and F also up to five times, by identical or different radicals from the group
Halogen, (CrC4)Alkyl, (CrC4)Alkoxy, (C-ι-C4)Haloalkyl, (CrC4)Haloalkoxy und Nitro substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyl, 2-, 3- und 4-Trifluorphenyl und 2-, 3- und 4-Trichlorphenyl, 2,4-, 3,5-, 2,5- und 2,3- Dichlorphenyl, o-, m- und p-Methoxyphenyl. Ein Acylrest bedeutet den Rest einer organischen Säure mit vorzugsweise bis zu 6 C-Atomen, z.B. den Rest einer Carbonsäure und Reste davon abgeleiteter Säuren wie der Thiocarbonsäure, gegebenenfalls N-substituierter Iminocarbonsäuren, oder der Rest von Kohlensäuremonoestern, gegebenenfalls N-substituierter Carbaminsäuren, Sulfonsäuren, Sulfinsäuren, Phosphonsäuren, Phosphinsäuren. Acyl bedeutet beispielsweise Formyl, Alkylcarbonyl, wie (CrC4-Alkyl)-carbonyl, Phenylcarbonyl, wobei der Phenylring substituiert sein kann, z.B. wie oben für Phenyl angegeben, oder Alkyloxycarbonyl, Phenyloxycarbonyl, Benzyloxycarbonyl, Alkylsulfonyl, Alkylsulfinyl oder N-Alkyl-1-iminoalkyl. Von den Formeln (S-Il) bis (S-VIII) umfasst sind auch alle Stereoisomeren, welche die gleiche topologische Verknüpfung der Atome aufweisen, und deren Gemische. Solche Verbindungen enthalten ein oder mehrere asymmetrische C-Atome oder auch Doppelbindungen, die in den allgemeinen Formeln nicht gesondert angegeben sind. Die durch ihre spezifische Raumform definierten möglichen Stereoisomeren, wie Enantiomere, Diastereomere, Z- und E-Isomere, können nach üblichen Methoden aus Gemischen der Stereoisomeren erhalten oder auch durch stereoselektive Reaktionen in Kombination mit dem Einsatz von stereochemisch reinen Ausgangsstoffen hergestellt werden.Halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C-ι-C 4 ) haloalkyl, (C r C 4 ) haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl , Dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluorophenyl and 2-, 3- and 4-trichlorophenyl, 2,4-, 3,5-, 2,5- and 2, 3-dichlorophenyl, o-, m- and p-methoxyphenyl. An acyl radical is the radical of an organic acid having preferably up to 6 C atoms, for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radical of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids , Sulfinic acids, phosphonic acids, phosphinic acids. Acyl is for example formyl, alkylcarbonyl such as (C r C 4 alkyl) -carbonyl, phenylcarbonyl, where the phenyl ring may be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl or N-alkyl 1-iminoalkyl. Also encompassed by the formulas (S-II) to (S-VIII) are all stereoisomers which have the same topological linkage of the atoms, and mixtures thereof. Such compounds contain one or more asymmetric C atoms or double bonds, which are not specified separately in the general formulas are. The possible defined by their specific spatial form possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers can be obtained by conventional methods from mixtures of stereoisomers or prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
Die Verbindungen der Formel (S-Il) sind z.B. aus EP-A-0333131 (ZA-89/1960), EP-A-0269806 (US 4,891 ,057), EP-A-0346620 (AU-A-89/34951 ), EP-A-0174562, EP-A-0346620 (WO-A-91/08202), WO-A-91/07874 oder WO-A-95/07897 (ZA 94/7120) und der dort zitierten Literatur bekannt oder können nach oder analog den dort beschriebenen Verfahren hergestellt werden. Die Verbindungen der Formel (S- III) sind aus EP-A-0086750, EP-A-094349 (US 4,902,340), EP-A-0191736 (US 4,881 ,966) und EP-A-0492366 und dort zitierter Literatur bekannt oder können nach oder analog den dort beschriebenen Verfahren hergestellt werden. Einige Verbindungen sind ferner in EP-A-0582198 und WO-A-02/34048 beschrieben. Die Verbindungen der Formel (S-IV) sind aus zahlreichen Patentanmeldungen bekannt, beispielsweise US 4,021 ,224 und US 4,021 ,229. Verbindungen der Untergruppe b) sind weiterhin aus CN-A-87/102789, EP-A-365484 sowie aus "The Pesticide Manual", 11. bis 13. Auflage, British Crop Protection Council and the Royal Society of Chemistry (1997), bekannt. Die Verbindungen der Untergruppe c) sind in der WO- A-97/45016, die der Untergruppe d) in der WO-A-99/16744 (insbesondere in EP-A- 365484) beschrieben. Die zitierten Schriften enthalten ausführliche Angaben zu Herstellungsverfahren und Ausgangsmaterialien und nennen bevorzugte Verbindungen. Auf diese Schriften wird ausdrücklich Bezug genommen, sie gelten durch Zitat als Bestandteil dieser Beschreibung.The compounds of formula (S-II) are e.g. from EP-A-0333131 (ZA-89/1960), EP-A-0269806 (US 4,891,057), EP-A-0346620 (AU-A-89/34951), EP-A-0174562, EP-A No. 0346620 (WO-A-91/08202), WO-A-91/07874 or WO-A-95/07897 (ZA 94/7120) and the literature cited therein, or can be prepared by or analogously to the processes described therein , The compounds of the formula (S-III) are known from EP-A-0086750, EP-A-094349 (US 4,902,340), EP-A-0191736 (US 4,881,966) and EP-A-0492366 and literature cited therein or US Pat can be prepared according to or analogously to the methods described therein. Some compounds are further described in EP-A-0582198 and WO-A-02/34048. The compounds of formula (S-IV) are known from numerous patent applications, for example US 4,021,224 and US 4,021,229. Compounds of subgroup b) are further from CN-A-87/102789, EP-A-365484 and from "The Pesticide Manual", 11th to 13th edition, British Crop Protection Council and the Royal Society of Chemistry (1997), known. The compounds of subgroup c) are described in WO-A-97/45016, those of subgroup d) in WO-A-99/16744 (in particular in EP-A-365484). The cited documents contain detailed information on preparation processes and starting materials and name preferred compounds. These documents are expressly referred to, they are by quotation as part of this description.
Die Safener der vorstehenden Gruppen a) bis e) reduzieren oder unterbinden phytotoxische Effekte, die beim Einsatz der herbiziden Mittel gemäß der Erfindung in Nutzpflanzenkulturen auftreten können, ohne die Wirksamkeit der Herbizide gegen Schadpflanzen zu beeinträchtigen. Hierdurch kann das Einsatzgebiet der Herbizide erheblich erweitert werden und insbesondere ist durch die Verwendung von Safenern der Einsatz von Herbiziden, die bislang nur beschränkt oder mit nicht ausreichendem Erfolg eingesetzt werden konnten, d.h. von Kombinationen, die ohne Safener in niedrigen Dosierungen mit wenig Breitenwirkung zu nicht ausreichender Kontrolle der Schadpflanzen führten, möglich.The safeners of the above groups a) to e) reduce or prevent the phytotoxic effects which can occur when using the herbicidal compositions according to the invention in crops without impairing the effectiveness of the herbicides against harmful plants. As a result, the field of application of herbicides can be significantly extended and in particular by the use of safeners, the use of herbicides, which have so far only limited or not could be used, that is, of combinations that led to insufficient control of the harmful plants without safeners in low dosages with little broader effect.
Besonders bevorzugt kommen sind als Safener in den erfindungsgemäßenParticularly preferred are as safeners in the inventive
Formulierungen unter anderem: 4-Dichloracetyl-1-oxa-4-aza-spiro[4.5]-decan (AD- 67), 1-Dichloracetyl-hexahydro-3,3,8a-trimethylpyrrolo[1 ,2-a]-pyrimidin-6(2H)-on (Dicyclonon, BAS-145138), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1 ,4-benzoxazin (Benoxacor), Cloquintocet, 5-Chlor-chinolin-8-oxy-essigsäure-(1-methyl-hexylester) (Cloquintocet-mexyl), α-(Cyanomethoxyimino)-phenylacetonitril (Cyometrinil), 2,2- Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamid (DKA-24), 2,2- Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-(1-methyl- 1-phenyl-ethyl)-harnstoff (Dymron), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), 1- (2,4-Dichlor-phenyl)-5-trichlormethyl-1 H-1 ,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure- phenylmethylester (Flurazole), 4-Chlor-N-(1 ,3-dioxolan-2-yl-methoxy)-α-trifluor- acetophenonoxim (Fluxofenim), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furilazole, MON-13900), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), Diethyl-1 -(2,4-dichlorphenyl)-4,5-dihydro-5-methyl-1 H-pyrazol-3,5- dicarboxylat (Mefenpyr-diethyl), 2-Dichlormethyl-2-methyl-1 ,3-dioxolan (MG-191 ), 1 ,8-Naphthalsäureanhydrid, α-(1 ,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), 2,2-Dichlor-N-(1 ,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamid (PPG-1292), 3-Dichloracetyl-2,2-dimethyl-oxazolidin (R-28725), 3-Dichloracetyl- 2,2,5-trimethyl-oxazolidin (R-29148), 1-(2-Chlor-phenyl)-5-phenyl-1 H-pyrazol-3- carbonsäure-methylester, 4-Cyclopropylaminocarbonyl-N-(2- methoxybenzoyl)benzolsulfonamid (Cyprosulfamide), 4-iso-propylaminocarbonyl-N- (2-methoxybenzoyl)benzolsulfonamid und N-(2-Methoxy-benzoyl)-4-[(methylamino- carbonyl)-amino]-benzolsulfonamid.Formulations include: 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] -pyrimidine -6 (2H) -one (dicyclonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor), cloquintocet, 5-chloro-quinolin-8- oxy-acetic acid (1-methyl-hexyl ester) (cloquintocet-mexyl), α- (cyanomethoxyimino) -phenylacetonitrile (cyometrinil), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl ) -N- (2-propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methyl-phenyl) -N ' - (1-methyl-1-phenyl-ethyl) -urea (Dymron), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 1- (2,4-dichloro-phenyl) -5-trichloromethyl-1 Ethyl H-1, 2,4-triazole-3-carboxylate (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 4-chloro-N- (1, 3 -dioxolan-2-yl-methoxy) -α-trifluoroacetophenone oxime (Fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13 900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalic anhydride, α- (1,3-dioxolane-2-) yl-methoximino) -phenylacetonitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl -2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 1- (2-chloro-phenyl) -5-phenyl-1 H- methyl pyrazole-3-carboxylate, 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide (cyprosulfamide), 4-iso-propylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide and N- (2-methoxy-benzoyl) -4 - [(methylamino-carbonyl) -amino] -benzenesulfonamide.
Bei den in den erfindungsgemäßen Mikroemulsionskonzentraten enthaltenen Safenern sind ganz besonders bevorzugt Mefenpyr-diethyl, Cloquintocet-mexyl, Isoxadifen-ethyl, 4-Cyclopropylaminocarbonyl-N-(2- methoxybenzoyl)benzolsulfonamid (Cyprosulfamide), 4-iso-propylaminocarbonyl-N- (2-methoxybenzoyl)benzolsulfonamid oder Fenchlorazol-ethyl; insbesondere ganz besonders bevorzugt sind Mefenpyr-diethyl, Cloquintocet-mexyl oder Isoxadifen- ethyl.In the safeners present in the microemulsion concentrates according to the invention, very particular preference is given to mefenpyr-diethyl, cloquintocet-mexyl, isoxadifen-ethyl, 4-cyclopropylaminocarbonyl-N- (2- methoxybenzoyl) benzenesulfonamide (cyprosulfamide), 4-iso-propylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide or fenchlorazole-ethyl; Particular preference is given to mefenpyr-diethyl, cloquintocet-mexyl or isoxadifen-ethyl.
Eine besondere Ausführungsform der erfindungsgemäßen Mikroemulsionskonzentrate ist die gemeinsame Formulierung von Herbiziden und Safenern als agrochemischen Wirkstoffen.A particular embodiment of the microemulsion concentrates according to the invention is the joint formulation of herbicides and safeners as agrochemical active ingredients.
Bei den in den erfindungsgemäßen Mikroemulsionskonzentraten enthaltenen Herbiziden-Safener-Mischungen sind bevorzugt Kombinationen der folgenden Verbindungen miteinander:In the herbicidal-safener mixtures contained in the microemulsion concentrates according to the invention, preference is given to combinations of the following compounds with one another:
a) Verbindungen, die als ACCase-lnhibitoren wirksam sind, wie Alloxydim, Butroxydim, Clethodim, Clodinafop-propargyl, Cycloxydim, Cyhalofop-butyl, Diclofop- methyl, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop-P-butyl, Fluazifop-butyl, Haloxyfop, Haloxyfop-P, Haloxyfop- etotyl, Haloxyfop-P-methyl, Metamifop, Profoxydim, Propaquizafop, Quizalofop-P- tefuryl, Quizalofop-P-ethyl, Sethoxydim, Tepraloxydim, Tralkoxydim und Isoxapyrifop,a) compounds which are active as ACCase inhibitors, such as alloxydim, butroxydim, clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofopmethyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop , Fluazifop-P-butyl, Fluazifop-butyl, Haloxyfop, Haloxyfop-P, Haloxyfopetotyl, Haloxyfop-P-methyl, Metamifop, Profoxydim, Propaquizafop, Quizalofop-P-tefuryl, Quizalofop-P-ethyl, Sethoxydim, Tepraloxydim, Tralkoxydim and isoxapyrifop,
b) Verbindungen, die als p-Hydroxyphenyl pyruvate dioxygenase (HPPD)-Inhibitoren wirksam sind, wie Benzobicyclon, Benzofenap, Isoxaflutole und dessen Diketonitrile, Mesotrione, Pyrazolynate, Pyrazoxyfen, Sulcotrione und Isoxachlortole,b) compounds which are effective as p-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors, such as benzobicyclone, benzofenap, isoxaflutole and its diketronitrile, mesotrione, pyrazolynate, pyrazoxyfen, sulcotrione and isoxachlortole,
c) Verbindungen verschiedener Wirkstoffgruppen, wie Atrazin, Acetochlor, Aclonifen, Alachlor, Amidochlor, Amidosulfuron, Azimsulfuron, Bentazon, Bensulfuron(-methyl), Bromoxynil(-octanoat/-heptanoat), Butachlor, Bispyribac, Chlorsulf uron, Chlorimuron, Clomazone, Clopyralid, Cinosulfuron, Cyclosulfamuron, 2,4-D-Ester, 2,4-DB-Ester, 2,4-DP-Ester, CMPP-Ester, MCPA-Ester, MCPB, EPTC, Desmedipham,c) Compounds of various active ingredient groups, such as atrazine, acetochlor, aclonifen, alachlor, amidochlor, amidosulfuron, azimsulfuron, bentazone, bensulfuron (-methyl), bromoxynil (-octanoate / heptanoate), butachlor, bispyribac, chlorosulfuron, chlorimuron, clomazone, clopyralid , Cinosulfuron, cyclosulfamuron, 2,4-D-ester, 2,4-DB-ester, 2,4-DP-ester, CMPP-ester, MCPA-ester, MCPB, EPTC, Desmedipham,
Diflufenican, Dicamba, Ethoxysulfuron, Ethofumesat, Flazasulfuron, Florasulam, Flucarbazone, Flumetsulam, Flufenacet, Fluoroglykofen, Fluroxypyr, Flupyrsulfuron, Foramsulfuron, Flumioxazin, Flumiclorac, Fomesafen, Glufosinate, Glyphosate, Imazapyr, Imazosulfuron, lodosulfuron, lodosulfuron-methyl, loxynil(-octanoat), Lactofen, Halosulfuron, Imazamox, Imazapic, Imazapyr, Imazethapyr, Imazaquin, Metosulam, Mesosulfuron(-methyl), (S-)Metolachlor, Metsulfuron-methyl, Metamitron, Nicosulfuron, Oxyfluorfen, Pendimethalin, Phenmedipham, Picloram, Pinoxaden, Primisulfuron-methyl, Prosulfuron, Propanil, Propoxycarbazone,Diflufenican, dicamba, ethoxysulfuron, ethofumesate, flazasulfuron, florasulam, flucarbazone, flumetsulam, flufenacet, fluoroglycofen, fluroxypyr, flupyrsulfuron, foramsulfuron, flumioxazine, flumiclorac, fomesafen, glufosinate, glyphosate, Imazapyr, imazosulfuron, lodosulfuron, lodosulfuron-methyl, loxynil (-octanoate), lactofen, halosulfuron, imazamox, imazapic, imazapyr, imazethapyr, imazaquin, metosulam, mesosulfuron (-methyl), (S) -metolachlor, metsulfuron-methyl, metamitron, Nicosulfuron, oxyfluorfen, pendimethalin, phenmedipham, picloram, pinoxaden, primisulfuron-methyl, prosulfuron, propanil, propoxycarbazone,
Pyrazosulfuron(-methyl), Rimsulfuron, Sulfentrazone, Sulfosulfuron, Sulfometuron, Terbuthylazin, Thifensulfuron, Triasulfuron, Tribenuron, Triclopyr, Triflusulfuron- methyl, Trifluralin, Tritosulfuron, Topramezone, Oxazinon, Oxadiargyl, Metribuzin, und deren Salze, z.B. die Natriumsalze.Pyrazosulfuron (-methyl), rimsulfuron, sulfentrazone, sulfosulfuron, sulfometuron, terbuthylazine, thifensulfuron, triasulfuron, tribenuron, triclopyr, triflusulfuron-methyl, trifluralin, tritosulfuron, toramezone, oxazinone, oxadiargyl, metribuzin, and their salts, e.g. sodium salts.
d) Verbindungen, die als Safener wirksam sind, wie AD 67 (4-(dichloroacetyl)-1-oxa- 4-azaspiro[4.5]decane), Benoxacor, CL 304,415 (4-carboxymethylchroman-4- carboxylic acid), Cloquintocet, Cloquintocet-mexyl, Cyprosulfamide, Dichlormid, Dicyclonon, DKA-24 (N1 ,N2-diallyl-N2-dichloroacetylglycinamide), Fenchlorazole, Fenchlorazole-ethyl, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen-ethyl, Mefenpyr-diethyl, MG 191 (2-dichloromethyl-2-methyl-1 ,3-dioxolane), Naphthalsäureanhydrid (naphthalene-1 ,8-dicarboxylic anhydride), Oxabetrinil and Tl- 35 (1-dichloroacetylazepane).d) compounds which act as safeners, such as AD 67 (4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane), benoxacor, CL 304,415 (4-carboxymethylchroman-4-carboxylic acid), cloquintocet, Cloquintocet-mexyl, cyprosulfamides, dichloromide, dicyclonon, DKA-24 (N1, N2-diallyl-N2-dichloroacetylglycine amides), fenchlorazoles, fenchlorazoles-ethyl, fenclorim, flurazoles, fluxofenim, furilazoles, isoxadifen-ethyl, mefenpyr-diethyl, MW 191 ( 2-dichloromethyl-2-methyl-1,3-dioxolane), naphthalic anhydride (naphthalene-1,8-dicarboxylic anhydride), oxabetrinil and Tl-35 (1-dichloroacetylazepane).
In einer weiteren Ausfϋhrungsform können z.B. verschiedene Herbizide miteinander kombiniert werden, z.B. Fenoxaprop-p-ethyl + loxynil-octanoat, Diclofop-methyl + Bromoxynil-octanoat, CMPP + Bromoxynil-octanoat, MCPA + loxynil-octanoat, Bromoxynil-octanoat + Bromoxynil-heptanoat, Bromoxynil-octanoat + Bromoxynil- heptanoat + MCPA, Bromoxynil-octanoat + Bromoxynil-heptanoat+ 2,4-D, Phenmedipham + Desmedipham, Phenmedipham + Desmedipham + Ethofumesate, Metamitron + Ethofumesate, Phenmedipham + Ethofumesate + Metamitron, Fenoxaprop-p-ethyl + lodosulfuron-methyl-natrium, Fenoxaprop-p-ethyl + Diclofop- methyl, Fenoxaprop-p-ethyl + lodosulfuron-methyl-natrium + Diclofop-methyl.In a further embodiment, e.g. different herbicides are combined, e.g. Fenoxaprop-p-ethyl + loxyniloctanoate, diclofopmethyl + bromoxyniloctanoate, CMPP + bromoxyniloctanoate, MCPA + loxyniloctanoate, bromoxyniloctanoate + bromoxynil heptanoate, bromoxyniloctanoate + bromoxynilheptanoate + MCPA, bromoxynil octanoate + bromoxynil-heptanoate + 2,4-D, phenmedipham + desmedipham, phenmedipham + desmedipham + ethofumesate, metamitron + ethofumesate, phenmedipham + ethofumesate + metamitron, fenoxaprop-p-ethyl + iodosulfuron-methyl-sodium, fenoxaprop-p-ethyl + diclofop - methyl, fenoxaprop-p-ethyl + iodosulfuron-methyl-sodium + diclofop-methyl.
Als besonders bevorzugt sind die Kombinationen aus: Foramsulfuron + lodosulfuron- methyl-sodium + Isoxadifen-ethyl, lodosulfuron-methyl-sodium + Isoxadifen-ethyl, Foramsulfuron + Isoxadifen-ethyl, Fenoxaprop-P-ethyl + Ethoxysulfuron + Isoxadifen-ethyl, Ethoxysulfuron + Isoxadifen-ethyl, Fenoxaprop-P-ethyl + Isoxadifen-ethyl, lodosulfuron-methyl-sodium + Mesosulfuron-methyl + Mefenpyr- diethyl, Mesosulfuron-methyl + Mefenpyr-diethyl, lodosulfuron-methyl-sodium + Mefenpyr-diethyl, Fenoxaprop-P-ethyl + Mefenpyr-diethyl, Fenoxaprop-P-ethyl + Diclofop-methyl + Mefenpyr-diethyl, Diclofop-methyl + Mefenpyr-diethyl, Diclofop- methyl + Sethoxydim + Mefenpyr-diethyl, Sethoxydim + Mefenpyr-diethyl, Fenoxaprop-P-ethyl + Isoproturon + Mefenpyr-diethyl, Isoproturon + Mefenpyr- diethyl, Clodinafop-propargyl + Cloquintocet-mexyl, Fenoxaprop-ethyl + Fenchlorazole-ethyl, Fenoxaprop-P-ethyl + Fenchlorazole-ethyl, Flucarbazone + Cyprosulfamide, Foramsulfuron + Cyprosulfamide, lodosulfuron(-methyl) + Cyprosulfamide, Metosulam + Cyprosulfamide, Metsulfuron(-methyl) + Cyprosulfamide, Nicosulfuron + Cyprosulfamide, Primisulfuron(.methyl) + Cyprosulfamide, Prosulfuron + Cyprosulfamide + Cyprosulfamide, Thifensulfuron + Cyprosulfamide, Tribenuron + Cyprosulfamide, Cloransulam-methyl + Cyprosulfamide, Chlorimuron + Cyprosulfamide, Ethoxysulfuron + Cyprosulfamide, Flazasulfuron + Cyprosulfamide, Florasulam + Cyprosulfamide, Flumetsulam + Cyprosulfamide, Halosulfuron + Cyprosulfamide, Imazamox + Cyprosulfamide, Imazapic + Cyprosulfamide, Imazapyr + Cyprosulfamide, Imazethapyr + Cyprosulfamide, Mesosulfuron + Cyprosulfamide, Propoxycarbazone + Cyprosulfamide, Sulfosulfuron + Cyprosulfamide, Amidosulfuron + Cyprosulfamide, Chlorsulfuron + Cyprosulfamide, Imazaquin + Cyprosulfamide, Triasulfuron + Cyprosulfamide, Sulfometuron + Cyprosulfamide, Cyclosulfamuron + Cyprosulfamide, Flupyrsulfuron + Cyprosulfamide, Pyrazosulfuron + Cyprosulfamide, Azimsulfuron + Cyprosulfamide, Bensulfuron + Cyprosulfamide, Bispyribac + Cyprosulfamide, Rimsulfuron + Cyprosulfamide, Tritosulfuron + Cyprosulfamide, Sulcotrione + Cyprosulfamide, Clomazone + Cyprosulfamide, Mesotrione + Cyprosulfamide, Topramezone + Cyprosulfamide, Metribuzin + Cyprosulfamide, Bentazon + Cyprosulfamide, Bromoxynil + Cyprosulfamide, Propanil + Cyprosulfamide, Atrazin + Cyprosulfamide, Terbuthylazin + Cyprosulfamide, EPTC + Cyprosulfamide, Tepraloxydim + Cyprosulfamide, Clethodim + Cyprosulfamide, Alloyxdim + Cyprosulfamide, Sethoxydim + Cyprosulfamide, Tralkoxydim + Cyprosulfamide, Clodinafop-propargyl + Cyprosulfamide, Cyhalofop-butyl + Cyprosulfamide, Diclofop-methyl + Cyprosulfamide, Fenoxaprop-P-ethyl + Cyprosulfamide, Fluazifop-P-butyl + Cyprosulfamide, Haloxyfop-methyl + Cyprosulfamide, Haloxyfop-etotyl + Cyprosulfamide, Haloxyfop-R-methyl + Cyprosulfamide, Haloxyfop-ethoxyethyl + Cyprosulfamide, Propaquizafop + Cyprosulfamide, Quizalofop-P-tefuryl + Cyprosulfamide, Quizalofop-P-ethyl + Cyprosulfamide, Acetochlor + Cyprosulfamide, S-Metolachlor + Cyprosulfamide, Flumioxazin + Cyprosulfamide, Flumiclorac + Cyprosulfamide, Fomesafen + Cyprosulfamide, Sulfentrazone + Cyprosulfamide, Dicamba + Cyprosulfamide, MCPA + Cyprosulfamide, MCPB + Cyprosulfamide, 2,4-D + Cyprosulfamide, Clopyralid + Cyprosulfamide, Fluroxypyr + Cyprosulfamide, Picloram +The combinations of foramsulfuron + iodosulfuron-methyl-sodium + isoxadifen-ethyl, iodosulfuron-methyl-sodium + isoxadifen-ethyl, foramsulfuron + isoxadifen-ethyl, fenoxaprop-P-ethyl + ethoxysulfuron + are particularly preferred Isoxadifen-ethyl, ethoxysulfuron + isoxadifen-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, iodosulfuron-methyl-sodium + mesosulfuron-methyl + mefenpyr-diethyl, mesosulfuron-methyl + mefenpyr-diethyl, iodosulfuron-methyl-sodium + mefenpyr- diethyl, fenoxaprop-P-ethyl + mefenpyr-diethyl, fenoxaprop-P-ethyl + diclofop-methyl + mefenpyr-diethyl, diclofop-methyl + mefenpyr-diethyl, diclofopmethyl + sethoxydim + mefenpyr-diethyl, sethoxydim + mefenpyr-diethyl, Fenoxaprop-P-ethyl + isoproturon + mefenpyr-diethyl, isoproturon + mefenpyr-diethyl, clodinafop-propargyl + cloquintocet-mexyl, fenoxaprop-ethyl + fenchlorazole-ethyl, fenoxaprop-P-ethyl + fenchlorazole-ethyl, flucarbazone + cyprosulfamide, foramsulfuron + Cyprosulfamides, iodosulfuron (-methyl) + Cyprosulfamide, Metosulam + Cyprosulfamide, Metsulfuron (-methyl) + Cyprosulfamide, Nicosulfuron + Cyprosulfamide, Primisulfuron (.methyl) + Cyprosulfamide, Prosulfuron + Cyprosulfamide + Cyprosulfamide, Thifensulfuron + Cyprosulfamide, Tribe nuron + Cyprosulfamide, Cloransulam-methyl + Cyprosulfamide, Chlorimuron + Cyprosulfamide, Ethoxysulfuron + Cyprosulfamide, Flazasulfuron + Cyprosulfamide, Florasulam + Cyprosulfamide, Flumetsulam + Cyprosulfamide, Halosulfuron + Cyprosulfamide, Imazamox + Cyprosulfamide, Imazapic + Cyprosulfamide, Imazapyr + Cyprosulfamide, Imazethapyr + Cyprosulfamide, mesosulfuron + cyprosulfamide, propoxycarbazone + cyprosulfamide, sulfosulfuron + cyprosulfamide, amidosulfuron + cyprosulfamide, chlorsulfuron + cyprosulfamide, imazaquin + cyprosulfamide, triasulfuron + cyprosulfamide, sulfometuron + cyprosulfamide, cyclosulfamuron + cyprosulfamide, flupyrsulfuron + cyprosulfamide, pyrazosulfuron + cyprosulfamide, azimsulfuron + cyprosulfamide, bensulfuron + Cyprosulfamide, Bispyribac + Cyprosulfamide, Rimsulfuron + Cyprosulfamide, Tritosulfuron + Cyprosulfamide, Sulcotrione + Cyprosulfamide, Clomazone + Cyprosulfamide, Mesotrione + Cyprosulfamide, Topramezone + Cyprosulfamide, Metribuzin + Cyprosulf amide, Bentazone + Cyprosulfamide, Bromoxynil + Cyprosulfamide, Propanil + Cyprosulfamide, Atrazine + Cyprosulfamide, Terbuthylazine + Cyprosulfamide, EPTC + Cyprosulfamide, Tepraloxydim + Cyprosulfamide, Clethodim + Cyprosulfamide, Alloyxdim + Cyprosulfamide, Sethoxydim + Cyprosulfamide, Tralkoxydim + Cyprosulfamide, Clodinafop-propargyl + Cyprosulfamide, cyhalofop-butyl + Cyprosulfamides, diclofop-methyl + cyprosulfamides, fenoxaprop-P-ethyl + cyprosulfamides, fluazifop-p-butyl + cyprosulfamides, haloxyfop-methyl + cyprosulfamides, haloxyfop-etotyl + cyprosulfamides, haloxyfop-R-methyl + cyprosulfamides, haloxyfop-ethoxyethyl + cyprosulfamides, Propaquizafop + Cyprosulfamide, Quizalofop-P-tefuryl + Cyprosulfamide, Quizalofop-P-ethyl + Cyprosulfamide, Acetochlor + Cyprosulfamide, S-Metolachlor + Cyprosulfamide, Flumioxazin + Cyprosulfamide, Flumiclorac + Cyprosulfamide, Fomesafen + Cyprosulfamide, Sulfentrazone + Cyprosulfamide, Dicamba + Cyprosulfamide, MCPA + Cyprosulfamide, MCPB + Cyprosulfamide, 2,4-D + Cyprosulfamide, Clopyralid + Cyprosulfamide, Fluroxypyr + Cyprosulfamide, Picloram +
Cyprosulfamide, Triclopyr + Cyprosulfamide, Glufosinate + Cyprosulfamide, Glyphosate + Cyprosulfamide und Pendimethalin + Cyprosulfamide.Cyprosulfamide, triclopyr + cyprosulfamide, glufosinate + cyprosulfamide, glyphosate + cyprosulfamide and pendimethalin + cyprosulfamide.
Das Gewichtsverhältnis Safener : Herbizid kann innerhalb weiter Grenzen variieren und liegt vorzugsweise im Bereich von 1 : 100 bis 100 : 1 , insbesondere von 1 : 100 bis 50 : 1 , ganz besonders bevorzugt 1 : 10 bis 10 : 1. Die jeweils optimalen Mengen an Herbizid(en) und Safener(n) sind üblicherweise vom Typ des Herbizids und/oder vom verwendeten Safener sowie von der Art des zu behandelnden Pflanzenbestandes abhängig.The weight ratio safener: herbicide 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, very particularly preferably from 1:10 to 10: 1 Herbicide (s) and safener (s) are usually dependent on the type of herbicide and / or the safener used and on the nature of the plant stock to be treated.
Als alkoholische Lösungsmittel mit mindestens 5 C-Atomen (Komponente b) eignen sich insbesondere aromatische und nichtaromatische Alkohole.Alcoholic solvents having at least 5 carbon atoms (component b) are in particular aromatic and non-aromatic alcohols.
Aromatische Alkohole enthalten mindestens eine aromatische und/oder nicht heteroaromatische Gruppe und mindestens eine OH-Funktion. Bevorzugte aromatische Alkohole sind solche, die vom Benzol abgeleitet sind, insbesondere monofunktionelle vom Benzol abgeleitete Alkohole, z.B. solche der allgemeinen Formel (I)Aromatic alcohols contain at least one aromatic and / or non-heteroaromatic group and at least one OH function. Preferred aromatic alcohols are those derived from benzene, especially monofunctional benzene-derived alcohols, e.g. those of the general formula (I)
worin wherein
R ein Crdo-Alkylrest, z.B. Methyl, Ethyl, Propyl oder Butyl, oder H ist, n eine ganze Zahl von 0 bis 5, vorzugsweise 0, 1 oder 2, besonders bevorzugt 0 ist, m eine ganze Zahl von 0 bis 10, vorzugsweise von 0 bis 5 bedeutet, insbesondere von 1 bis 5, speziell 1 oder 2.R is a C 1 -C 6 alkyl radical, e.g. Is methyl, ethyl, propyl or butyl, or H, n is an integer from 0 to 5, preferably 0, 1 or 2, more preferably 0, m is an integer from 0 to 10, preferably from 0 to 5, in particular from 1 to 5, especially 1 or 2.
Besonders bevorzugt als Komponente (b) sind Verbindungen der Formel (I), worin n = 0 und m eine ganze Zahl von 1 bis 5 ist, ganz besonders bevorzugt hier ist Benzylalkohol.Particularly preferred as component (b) are compounds of the formula (I) in which n = 0 and m is an integer from 1 to 5, very particularly preferred here is benzyl alcohol.
Bei nichtaromatischen Alkoholen handelt es sich um cyclische, aliphatische, gesättigte oder ungesättigte bzw. verzweigte oder unverzweigte Alkohole. Beispiele einwertiger Alkohole mit 5 bis 25 C- Atomen sind n-, i-, oder neo-Pentanol, n-, i-, s- Hexanol, n-, i-, s- Heptanol, n-, i-, s- Octanol, n-, i-, s- Decanol, n-, i-, s- Undecanol, n-, i-, s- Dodecanol, n-, i-, s- Tridecyclalkohol, z.B. Cyclohexanol. Beispiele mehrwertiger Alkohole sind Neopentylglykol. Geeignet sind auch Polygykole, kommerziell z.B. erhältlich als Exxal®-Reihe (ExxonMobil), Agrisynth® PA (ISP), Arcosolv®-Reihe (Lyondell Chemical) oder Nacol® 6-98 (DEA).Non-aromatic alcohols are cyclic, aliphatic, saturated or unsaturated or branched or unbranched alcohols. Examples of monohydric alcohols having 5 to 25 carbon atoms are n-, i- or neo-pentanol, n-, i-, s-hexanol, n-, i-, s-heptanol, n-, i-, s- Octanol, n-, i-, s-decanol, n-, i-, s-undecanol, n-, i-, s-dodecanol, n-, i-, s-tridecyl alcohol, eg Cyclohexanol. Examples of polyhydric alcohols are neopentyl glycol. Also suitable are polyglycols, commercially available e.g. available as Exxal® series (ExxonMobil), Agrisynth® PA (ISP), Arcosolv® series (Lyondell Chemical) or Nacol® 6-98 (DEA).
Bevorzugt sind Alkohole mit mindestens 5 C-Atomen, besonders bevorzugt Alkohole mit 5 bis 25 C-Atomen, ganz besonders bevorzugt Alkohole mit 6 bis 20 C-Atomen. Bei den Alkoholen kann es sich um primäre, sekundäre oder tertiäre Alkohole handeln. Insbesondere bevorzugt als alkoholische Lösungsmittel (Komponente b) sind Benzylalkohol, n-, i-, s- Hexanol, n-, i-, s- Heptanol und n-, i-, s- Octanol.Alcohols having at least 5 carbon atoms, particularly preferably alcohols having 5 to 25 carbon atoms, very particularly preferably alcohols having 6 to 20 carbon atoms, are preferred. The alcohols may be primary, secondary or tertiary alcohols. Particularly preferred alcoholic solvents (component b) are benzyl alcohol, n-, i-, s-hexanol, n-, i-, s-heptanol and n-, i-, s-octanol.
Als nicht-alkoholische Lösungsmittel (Komponente c) eignen sich beispielsweise Kohlenwasserstoffe oder polare Lösungsmittel wie Carbonsäurederivate, Phosphorsäureester, Ether, Ketone oder Sulfoxide wie Dimethylsulfoxid, wobei Wasser höchstens als Verunreinigung eines Inerts in Gehalten von maximal < 2 Gew.-%, insbesondere < 1 Gew.-%, auftreten kann. Beispiele für Kohlenwasserstoffe (siehe z.B. Römpp Lexikon Chemie, 10. Auflage, Band 3, Seite 2202 (1997), Georg Thieme Verlag Stuttgart / New York) sind bevorzugt solche, die bei Normalbedingungen flüssig sind. Die Kohlenwasserstoffe können acyclische (aliphatische) Kohlenwasserstoffe sein, oder cyclische Kohlenwasserstoffe, z.B. aromatische, alicyclische (cycloaliphatische) oder heterocyclische Kohlenwasserstoffe.Suitable non-alcoholic solvents (component c) are, for example, hydrocarbons or polar solvents such as carboxylic acid derivatives, phosphoric esters, ethers, ketones or sulfoxides such as dimethyl sulfoxide, where water is at most impurity in an inert content of <2 wt .-%, in particular <1 Wt .-%, can occur. Examples of hydrocarbons (see, for example, Römpp Lexikon Chemie, 10th Edition, Volume 3, page 2202 (1997), Georg Thieme Verlag Stuttgart / New York) are preferably those which are liquid under normal conditions. The hydrocarbons may be acyclic (aliphatic) hydrocarbons, or cyclic hydrocarbons, eg aromatic, alicyclic (cycloaliphatic) or heterocyclic hydrocarbons.
Beispiele für Kohlenwasserstoffe als Komponente (c) sind:Examples of hydrocarbons as component (c) are:
1 ) aromatische Kohlenwasserstoffe, z.B. - ein- oder mehrfach alkyl-substituierte (z.B. ein-, zwei- oder dreifach (d-1) aromatic hydrocarbons, e.g. mono- or poly-alkyl-substituted (for example mono-, di- or trisubstituted (d-
Cio)alkyl-substituierte) Aromaten, z.B. Benzole wie Toluol, XyIoI, Mesitylen,Cio) alkyl-substituted) aromatics, e.g. Benzenes such as toluene, xylene, mesitylene,
Ethylbenzol, oder - Kohlenwasserstoffe mit kondensierten aromatischen Ringsystemen wieEthylbenzene, or - hydrocarbons with fused aromatic ring systems such as
Naphthaline, z.B. 1 -Methylnaphthalin, 2-Methylnaphthalin oder Dimethylnaphtalin, oder andere kondensierte aromatische Kohlenwasserstoffe wie Indan oder Tetralin,Naphthalenes, e.g. 1-methylnaphthalene, 2-methylnaphthalene or dimethylnaphthalene, or other condensed aromatic hydrocarbons such as indane or tetralin,
2) cycloaliphatische Kohlenwasserstoffe, z.B. gesättigte oder ungesättigte, gegebenenfalls ein oder mehrfach alkyl- substituierte (z.B. ein-, zwei- oder dreifach (C-i-C-ioJalkyl-substituierte) Cycloaliphaten wie Cycloalkane, Cycloalkene oder Cycloalkine, z.B. Cyclohexan oder Methylcyclopentan,2) cycloaliphatic hydrocarbons, e.g. saturated or unsaturated, optionally mono- or poly-alkyl-substituted (for example mono-, di- or tri (C 1-10 -alkyl-substituted) cycloaliphatics, such as cycloalkanes, cycloalkenes or cycloalkynes, for example cyclohexane or methylcyclopentane,
3) heterocyclische Kohlenwasserstoffe, z.B. Dioxan, Furan,3) heterocyclic hydrocarbons, e.g. Dioxane, furan,
4) aliphatische Kohlenwasserstoffe, z.B. lineare oder verzweigte, gesättigte oder ungesättigte Aliphaten, bevorzugt C5- Ci6-Aliphaten, z.B. Alkane, Alkene oder Alkine, wie Pentan, Hexan, Octan, 2-4) aliphatic hydrocarbons, for example, linear or branched, saturated or unsaturated aliphatic, C 5 preferably - C 6 aliphatics, such as alkanes, alkenes or alkynes, such as pentane, hexane, octane, 2-
Methylbutan oder 2,2,4-Trimethylpentan.Methylbutane or 2,2,4-trimethylpentane.
Es können auch Gemische eines oder mehrerer aromatischer Kohlenwasserstoffe und/oder eines oder mehrerer cycloaliphatischer Kohlenwasserstoffe und/oder eines oder mehrerer aliphatischer Kohlenwasserstoffe enthalten sein. Beispiele sindIt is also possible for mixtures of one or more aromatic hydrocarbons and / or one or more cycloaliphatic hydrocarbons and / or one or more aliphatic hydrocarbons to be present. examples are
Gemische mehrerer aliphatischer Kohlenwasserstoffe, z.B. kommerziell erhältliche Lösungsmittel der Exxsol® D-Reihe, Isopar®-Reihe oder Bayol®-Reihe z.B. Bayol® 85 (Exxon Mobil Chemicals) oder der lsane® IP-Reihe oder Hydroseal® G-Reihe (Total Fina Elf), oder Gemische von aromatischen und aliphatischen Kohlenwasserstoffen, z.B. kommerziell erhältliche Lösungsmittel der Solvesso®- Reihe z.B. Solvesso® 100, Solvesso® 150, Solvesso® 200 oder Solvesso® 200 ND (Exxon Mobil Chemicals), der Solvarex®/Solvaro®-Reihe (Total Fina Elf) oder der Caromax®-Reihe z.B. Caromax® 28 (Petrochem Carless).Mixtures of several aliphatic hydrocarbons, for example commercially available solvents of the Exxsol® D series, Isopar® series or Bayol® series eg Bayol® 85 (Exxon Mobil Chemicals) or the lsane® IP series or Hydroseal® G series (Total Fina Elf), or mixtures of aromatic and aliphatic hydrocarbons, for example commercially available Solvesso® series solvents eg Solvesso® 100, Solvesso® 150 , Solvesso® 200 or Solvesso® 200 ND (Exxon Mobil Chemicals), the Solvarex® / Solvaro® range (Total Fina Elf) or the Caromax® range eg Caromax® 28 (Petrochem Carless).
Beispiele für polare Lösungsmittel, sind aprotische, polare Lösungsmittel wie Carbonsäurederivate, z.B. die Vollether und Vollester von CrCg-Alkansäuren, die mono-, di- oder polyfunktional sein können, z.B. die Ether und Ester mit C-1-C20- Alkylalkoholen, wie Ketone, Phophorsäureester wie Tri(butoxyethyl)phosphat, Triethylphosphat, Amide, Nitrile oder Sulfone, z.B. Diisobutyladipat, Rhodiasolv® RPDE (Rhodia), Cyclohexanon, Jeffsol® PC (Huntsman), γ- Butyrolacton, N-Methylpyrrolidon, N-Octylpyrrolidon, Sulfoxide wie Dimethylsulfoxid, Acetonitril, Tributylphosphat oder Hostarex® PO-Reihe (Clariant), oder protische polare Lösungsmittel wie aliphatische und cycloaliphatische Alkohole, Amine oder Carbonsäuren. Die Alkohole, Amine oder Carbonsäuren, weisen bevorzugt 1 bis 18 C-Atome auf und können linear, verzweigt oder cyclisch, gesättigt oder ungesättigt sein, gegebenenfalls Heteroatome enthalten und ein- oder mehrfach funktionalisiert sein. Beispiele für Amine sind Diethylamin, Hexylamin oder Anilin. Beispiele für Carbonsäuren sind Monocarbonsäuren oder teilveresterte Dioder Polycarbonsäuren, z.B. Adipinsäure und Adipinsäuremonoester.Examples of polar solvents are aprotic, polar solvents such as carboxylic acid derivatives, for example the full ethers and full esters of CrCg-alkanoic acids, which may be mono-, di- or polyfunctional, for example the ethers and esters with C 1 -C 20 -alkyl alcohols, such as Ketones, phosphoric esters such as tri (butoxyethyl) phosphate, triethyl phosphate, amides, nitriles or sulphones, eg diisobutyl adipate, Rhodiasolv® RPDE (Rhodia), cyclohexanone, Jeffsol® PC (Huntsman), γ-butyrolactone, N-methylpyrrolidone, N-octylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetonitrile, tributyl phosphate or Hostarex® PO series (Clariant), or protic polar solvents such as aliphatic and cycloaliphatic alcohols, amines or carboxylic acids. The alcohols, amines or carboxylic acids preferably have 1 to 18 C atoms and can be linear, branched or cyclic, saturated or unsaturated, optionally contain heteroatoms and be mono- or polyfunctionalized. Examples of amines are diethylamine, hexylamine or aniline. Examples of carboxylic acids are monocarboxylic acids or partially esterified di- or polycarboxylic acids, for example adipic acid and adipic acid monoester.
Beispiele für Carbonsäurederivate sind z.B. die Vollester oder Amide von Carbonsäuren. Als Carbonsäurederivate kommen z.B. die Ester und Amide von Monocarbonsäuren, Dicarbonsäuren oder Polycarbonsäuren wie Tri-, Tetra- oder auch höherfunktionellen Carbonsäuren, vorzugsweise mit 2-26 C-Atomen in Frage.Examples of carboxylic acid derivatives are e.g. the fullest or amides of carboxylic acids. As carboxylic acid derivatives are e.g. the esters and amides of monocarboxylic acids, dicarboxylic acids or polycarboxylic acids such as tri-, tetra- or even higher-functional carboxylic acids, preferably having 2-26 C atoms in question.
Bevorzugte Carbonsäureester sind die Ester mit CrC2o-Alkoholen (z.B. Methanol, Ethanol, Propanol oder Butanol), insbesondere bei Fettsäureestern sind auch die Glycerin- und Glykolester bevorzugt. Als Carbonsäureester kommen auch innere Ester wie Lactone in Frage. Beispiele für Monocarbonsäureester sind die Ester aliphatischer und aromatischer Monocarbonsäuren z.B. aliphatische C-i-Cg-Monocarbonsäureester wie Ameisensäureester, Essigsäureester und Propionsäureester, oder aliphatische Fettsäureester wie Cio-C22-Fettsäureester, z.B. natürlichen Ursprungs wie sie in natürlichen Ölen oder Pflanzenölen enthalten sind, oder synthetischen Ursprungs, oder aromatische C7-C22-Monocarbonsäureester wie Benzoesäureester oder Phenylessigsäureester.Preferred are the esters with Carbonsäureester -C 2 o-alcohols (for example methanol, ethanol, propanol or butanol), in particular at Fettsäureestern the glycerol and Glykolester are preferred. As carboxylic acid esters, internal esters such as lactones are also suitable. Examples of monocarboxylic esters are the esters of aliphatic and aromatic monocarboxylic acids, for example aliphatic C 1 -C 4 -monocarboxylic acid esters, such as formic acid esters, acetic acid esters and propionic acid esters, or aliphatic fatty acid esters, such as C 10 -C 2 -fatty acid esters, for example of natural origin as contained in natural oils or vegetable oils, or synthetic ones Origin, or aromatic C 7 -C 22 monocarboxylic acid esters such as benzoic acid ester or phenylacetic acid ester.
Beispiele für Fettsäureester sind, z.B. solche natürlichen Ursprungs, z.B. natürliche Öle wie tierische Öle oder Pflanzenöle, oder synthetischen Ursprungs, z.B. Edenor® MESU oder Agnique® ME-Reihe (Cognis), der Salim® ME-Reihe (Salim), der Stepan® C-Reihe (Stepan) oder der Witconol® 23-Reihe (Witco). Als Fettsäureester sind bevorzugt Ester von C10-C22-, vorzugsweise Ci2-C2o-Fettsäuren. Die C10-C22- Fettsäureester sind beispielsweise Ester ungesättigter oder gesättigter C10-C22- Fettsäuren, insbesondere mit gerader Kohlenstoffatomzahl, z.B. Erucasäure, Laurinsäure, Palmitinsäure und insbesondere da-Fettsäuren wie Stearinsäure, Ölsäure, Linolsäure oder Linolensäure.Examples of fatty acid esters are, for example, those of natural origin, for example natural oils such as animal oils or vegetable oils, or of synthetic origin, eg Edenor® MESU or Agnique® ME series (Cognis), the Salim® ME series (Salim), the Stepan® C-series (Stepan) or the Witconol® 23-series (Witco). As a fatty acid ester are preferably esters of C10-C22, preferably C 2 -C 2 o-fatty acids. The C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 fatty acids, in particular having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and, in particular, fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.
Beispiele für Fettsäureester wie Cio-C22-Fettsäure-Ester sind Glycerin- und Glykolester von Fettsäuren wie C-ιo-C-22-Fettsäuren oder derenExamples of fatty acid esters such as Cio-C 22 fatty acid esters are glycerol and glycol esters of fatty acids such as C-ιo-C- 22 fatty acids or their
Umesterungsprodukte, z.B. Alkyl-Fettsäureester wie Ci-C2o-Alkyl-Cio-C22-Fettsäure- Ester, wie sie z.B. durch Umesterung der vorgenannten Glycerin- oder Glykol- Fettsäureester wie C10-C22-Fett.saure-Est.er mit CrC2o-Alkoholen (z.B. Methanol, Ethanol, Propanol oder Butanol) erhalten werden können. Die Umesterung kann nach bekannten Methoden erfolgen, wie sie z.B. beschrieben sind im Römpp Chemie Lexikon, 9. Auflage, Band 2, Seite 1343, Thieme Verlag Stuttgart.Transesterification products, for example alkyl-fatty acid ester such as Ci-C2o-alkyl-Cio-C 22 -Fettsäure- esters, such as for example, by transesterification of the abovementioned glycerol or glycol fatty acid ester such as C10-C22 -Fett.saure-Est.er with C r C 2 o alcohols (eg, methanol, ethanol, propanol or butanol) can be obtained. The transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
Bevorzugte Fettsäureester sind z.B. Öle aus ölliefernden Pflanzenarten wie Sojaöl, Rapsöl, Maiskeimöl, Sonnenblumenöl, Baumwollsaatöl, Leinöl, Kokosöl, Palmöl, Distelöl, Walnussöl, Erdnussöl, Olivenöl oder Rhizinusöl, insbesondere Rapsöl, wobei unter den Pflanzenölen auch deren Umesterungsprodukte verstanden werden, z.B. Alkylester wie Rapsölmethylester oder Rapsölethylester. Beispiele für Dicarbonsäureester und Polycarbonsäureester sind die Vollester von Oxal-, Malon-, Bernstein-, Glutar-, Adipin-, Pimelin-, Sebacin-, Azelain-, Suberin-, Malein-, Phthal-, Terephthal-, Mellit-, Trimellit- und Polymaleinsäure, insbesondere die Ci-C-io-Alkylester wie die Methylester, Ethylester, Propylester wie n-Propylester oder iso-Propylester, Butylester wie n-Butylester, iso-Butylester, sec-Butylester oder tert-Butylester.Preferred fatty acid esters are, for example, oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, walnut oil, peanut oil, olive oil or castor oil, in particular rapeseed oil, where the vegetable oils are also understood to be transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester. Examples of dicarboxylic esters and polycarboxylic esters are the full esters of oxalic, malonic, succinic, glutaric, adipic, pimelic, sebacic, azelaic, suberic, maleic, phthalic, terephthalic, mellitic, trimellitic and polymaleic acid, in particular the C 1 -C 10 -alkyl esters, such as the methyl esters, ethyl esters, propyl esters, such as n-propyl or isopropyl esters, butyl esters, such as n-butyl ester, isobutyl ester, sec-butyl ester or tert-butyl ester.
Als Carbonsäureamide kommen auch CrC26-Carbonsäure-N,N-di(CrC-2o- alkyl)amide z.B. Ci-C26-Carbonsäure-N,N-dimethylamide wie N,N-Dimethylformamid oder N,N-Dimethylacetamid in Frage, oder innere Amide wie Lactame, z.B.As carboxamides are also -C 26 -carboxylic acid-N, N-di (2 CrC o- alkyl) amides such as Ci-C 26 -carboxylic acid-N, N-dimethylamide, such as N, N-dimethylformamide or N, N-dimethylacetamide in question , or internal amides such as lactams, eg
Pyrrolidone wie N-substituierte CrCi2-Alkyl-pyrrolidone wie N-methyl-pyrrolidon, N- butyl-pyrrolidon, N-octyl-pyrrolidon, N-dodecyl-pyrrolidon und N-cyclohexyl- pyrrolidon.Pyrrolidones such as N-substituted CrCi 2 alkyl-pyrrolidone such as N-methyl-pyrrolidone, N-butyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone and N-cyclohexyl-pyrrolidone.
Als Phosphorsäureester kommen beispielsweise Triester der Phosphorsäure mit Alkoholen in Frage, wobei die Alkohole bevorzugt ausgewählt sind aus der Gruppe bestehend aus,Examples of suitable phosphoric esters are triesters of phosphoric acid with alcohols, the alcohols preferably being selected from the group consisting of
1 ) einwertige Alkanole mit 1 bis 22 C-Atomen, z.B. n-, i- oder neo-Pentanol, n- Hexanol, n-Octanol, 2-Ethylhexanol, 2) Diole oder Polyole, wie Ethylenglykol, Propylenglykol oder Glycerin,1) monohydric alkanols having 1 to 22 C atoms, e.g. n-, i- or neo-pentanol, n-hexanol, n-octanol, 2-ethylhexanol, 2) diols or polyols, such as ethylene glycol, propylene glycol or glycerol,
3) Aryl-, Alkylaryl-, Poly(alkyl)aryl- und Poly(arylalkyl)arylalkohole, beispielsweise Phenol und/oder Kresol, Octylphenol, Nonylphenol, Triisobutylphenol, Tristyrylphenol,3) aryl, alkylaryl, poly (alkyl) aryl and poly (arylalkyl) aryl alcohols, for example phenol and / or cresol, octylphenol, nonylphenol, triisobutylphenol, tristyrylphenol,
4) alkoxylierte Alkohole, die durch Umsetzung der vorstehend unter 1 ), 2) oder 3) genannten Alkohole mit Alkylenoxiden, vorzugsweise (Ci-C4)Alkylenoxiden erhalten werden.4) alkoxylated alcohols which are obtained by reacting the alcohols mentioned above under 1), 2) or 3) with alkylene oxides, preferably (C 1 -C 4 ) alkylene oxides.
Bevorzugte Phosphorsäureester sind Triester der ortho-Phosphorsäure, insbesondere alkoxylierte Triester der ortho-Phosphorsäure wie Tri(butyoxyethyl)phosphat. Als Ketone kommen beispielsweise aromatische, cycloaliphatische oder aliphatische Ketone in Frage wie Acetophenon, Benzophenon, Isophoron, Cyclohexanon und Methylethylketon, Ethylbutylketon, Diethylketon, Dibutylketon.Preferred phosphoric esters are triesters of orthophosphoric acid, in particular alkoxylated triesters of orthophosphoric acid, such as tri (butyoxyethyl) phosphate. Suitable ketones are, for example, aromatic, cycloaliphatic or aliphatic ketones, such as acetophenone, benzophenone, isophorone, cyclohexanone and methyl ethyl ketone, ethyl butyl ketone, diethyl ketone, dibutyl ketone.
Als Ether kommen beispielsweise aromatische, cycloaliphatische oder aliphatische Ether in Frage wie Anisol, Tetrahydrofuron, Oxiran, Dibutylether, Dipentylether, Butylhexylether, Methyl-tert.Butylether.Examples of suitable ethers are aromatic, cycloaliphatic or aliphatic ethers, such as anisole, tetrahydrofuron, oxirane, dibutyl ether, dipentyl ether, butylhexyl ether, methyl tert-butyl ether.
Bevorzugte nicht-alkoholische Lösungsmittel (Komponente c) sind aromatische Kohlenwasserstoffe wie, CrC6-Alkyl-benzole z.B. Toluol oder XyIoI, CrC6- Alkylnaphthaline und Aromatengemische wie die Solvesso®-Reihe von Exxon, Ketone wie Acetophenon, Isophoron, Cyclohexanon und Methylethylketon, N- substituierte CrCi2-Alkyl-pyrrolidone wie N-methyl-pyrrolidon, N-butyl-pyrrolidon, N- octyl-pyrrolidon, N-dodecyl-pyrrolidon und N-cyclohexyl-pyrrolidon, cyclische aliphatische Kohlenwasserstoffe wie Decalin und Cyclohexan, Säureamide wie Dimethylformamid, Dimethylsulfoxid, Lactone wie Gamma-Butyrolacton, Di- oder Polycarbonsäureester wie CrCi2-Alkyl-Phthalsäureester, Adipinsäureester z.B. Diisopropyladipat, Dimethyladipat und Diisobutyladipat, Phosphorsäureester wie Tri- alkenyl-phosphate, z.B. Tri(butoxyethyl)phosphat oder Triethylphosphat, sowie Fettsäureester. Besonders bevorzugte nicht-alkoholische LösungsmittelPreferred non-alcoholic solvent (component c) are aromatic hydrocarbons, such as, -C 6 alkyl-benzenes such as toluene or xylene, CrC 6 - alkylnaphthalenes and mixtures of aromatic compounds such as the Solvesso series from Exxon, ketones such as acetophenone, isophorone, cyclohexanone and methyl ethyl ketone, N-substituted CrCl 2 -alkyl-pyrrolidones such as N-methyl-pyrrolidone, N-butyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone and N-cyclohexyl-pyrrolidone, cyclic aliphatic hydrocarbons such as decalin and cyclohexane, acid amides such as dimethylformamide , Dimethyl sulfoxide, lactones such as gamma-butyrolactone, di- or polycarboxylic acid esters such as CrCl 2 -alkyl phthalic acid esters, adipic acid esters eg diisopropyl adipate, dimethyl adipate and diisobutyl adipate, phosphoric esters such as tri alkenyl phosphate, for example tri (butoxyethyl) phosphate or triethyl phosphate, and fatty acid esters. Particularly preferred non-alcoholic solvents
(Komponente c) sind aromatische Lösemittel, wie Solvesso® 100, Solvesso® 150, Solvesso® 200 oder Solvesso® 200 ND, XyIoI, Triethylphosphat, Rapsölmethylester (z.B. Edenor® MESU oder Agnique® ME-Reihe) oder Rapsölethylester, N- Octylpyrrolidon sowie N-Methylpyrrolidon.(Component c) are aromatic solvents, such as Solvesso® 100, Solvesso® 150, Solvesso® 200 or Solvesso® 200 ND, xylene, triethyl phosphate, rapeseed oil methyl ester (eg Edenor® MESU or Agnique® ME series) or rapeseed oil ethyl ester, N-octylpyrrolidone and N-methylpyrrolidone.
Als anionische Tenside (Komponente d) eignen sich beispielsweise Sulfate, Sulfonate, Sulfosuccinate, Phosphate und Phosphonate von Kohlenwasserstoffen, die optional Alkylenoxideinheiten enthalten können. Die Sulfate, Sulfonate, Phosphate und Phosphonate können in Form der Säuren oder als Salze vorliegen. Bevorzugt sind anionische Tenside (d) der nachfolgenden Formel (II):Suitable anionic surfactants (component d) are, for example, sulfates, sulfonates, sulfosuccinates, phosphates and phosphonates of hydrocarbons, which may optionally contain alkylene oxide units. The sulfates, sulfonates, phosphates and phosphonates may be in the form of the acids or as salts. Anionic surfactants (d) of the following formula (II) are preferred:
R - Q (II) worin Q - O - SO3 M1 - SO3 M, - O - PO3H M oder PO3H M ist, worin M gleich H oder ein Kation ist, insbesondere ein Metallkation wie ein Alkalimetallion oder Erdalkalimetallion, oder ein Ammoniumion,R - Q (II) where Q - O - SO 3 M 1 --SO 3 M, - O - PO 3 HM or PO 3 HM, in which M is H or a cation, in particular a metal cation such as an alkali metal ion or alkaline earth metal ion, or an ammonium ion,
R ein unsubstituierter oder substituierter CrC30-Kohlenwasserstoffrest wie ein CrC2o-Alkylrest oder C6-C24-Arylrest ist, der optional überR is an unsubstituted or substituted CrC 30 -hydrocarbon radical such as a -C 2 -alkyl radical or C 6 -C 24 -aryl radical which optionally via
Alkylenoxideinheiten gebunden sein kann, oder R ist eine Alkylenoxideinheit.Alkylene oxide units may be bonded, or R is an alkylene oxide unit.
Unter dem Begriff Alkylenoxideinheiten werden insbesondere Einheiten von C2-C10- Alkylenoxiden, wie Ethylenoxid, Propylenoxid oder Butylenoxid verstanden, wobei die Einheiten innerhalb des Tensids gleich oder voneinander verschieden und dabei statistisch gemischt oder blockweise angeordnet sein können.The term alkylene oxide units is understood to mean, in particular, units of C 2 -C 10 -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, where the units within the surfactant may be the same or different and may be randomly mixed or blockwise arranged.
Bevorzugt ist R ein C-i-C2o-Alkylrest (z.B. Methyl, Ethyl, Propyl, Butyl) oder ein C6- C24-Arylrest (z.B. Phenyl, Biphenyl, Naphthyl), der optional einen oder mehrere Reste wie Ci-C2o-Kohlenwasserstoffreste tragen kann, z.B. aus der Gruppe C1-C20- Alkyl (z.B. lineares oder verzweigtes Ci-C2o-Alkyl wie sec. Butyl oder Dodecyl), welches einen oder mehrere Reste wie C6-C2O-AIyI reste (z.B. Phenyl, Biphenyl, Naphthyl) tragen kann, und C6-C2O-AIyI (z.B. Phenyl, Biphenyl oder Naphthyl), welches optional einen oder mehrere Reste tragen kann wie C-i-C-io-Alkyl (z.B. Methyl, Ethyl, Propyl, Butyl), oderPreferably, R is a 2 CiC o-alkyl (eg methyl, ethyl, propyl, butyl) or a C 6 - C 2 4-aryl (eg, phenyl, biphenyl, naphthyl) which optionally one or more radicals such as 2 CiC o Hydrocarbon radicals may bear, for example, from the group C1-C 20 - alkyl (eg linear or branched Ci-C 2 o-alkyl such as sec-butyl or dodecyl), which one or more radicals such as C 6 -C 2O -AIyI radicals can carry, for example, phenyl, biphenyl, naphthyl), and C 6 -C 2O -AIyI (eg, phenyl, biphenyl or naphthyl) which may carry one or more radicals optionally as CiC-io alkyl (eg methyl, ethyl, propyl, butyl ), or
R ist ein Rest R2O-(AO)w, worin w eine ganze Zahl von 1 bis 100, vorzugsweise 2 bis 50, insbesondere 2 bis 10, ist, und AO eine Alkylenoxideinheit ist, z.B. (EO)x(PO)γ(BO)z, worin EO eine Ethylenoxideinheit, PO eine Propylenoxideinheit, BO eine Butylenoxideinheit, x eine ganze Zahl von 0 - 100, y eine ganze Zahl von 0 - 100, z eine ganze Zahl von 0 bis 100 und die Summe x + y + z mindestens 1 ist, und die Alkylenoxideinheit, z.B. (EO)χ(PO)γ(BO)z, statistisch gemischt oder blockweise aufgebaut sein kann, undR is a radical R 2 O- (AO) w, wherein w is an integer from 1 to 100, preferably 2 to 50, in particular 2 to 10, and AO is an alkylene oxide unit, for example (EO) x (PO) γ (BO) z, where EO is an ethylene oxide unit, PO is a propylene oxide unit, BO is a butylene oxide unit, x is an integer from 0 to 100, y is an integer from 0 to 100, z is an integer from 0 to 100 and the sum x + y + z is at least 1, and the alkylene oxide unit, for example (EO) χ (PO) γ (BO) z, can be randomly mixed or block-structured, and
R2 ist H, ein C1-C2o-Alkylrest (z.B. Methyl, Ethyl, Propyl, Butyl) oder ein C6-C24- Arylrest (z.B. Phenyl, Biphenyl, Naphthyl), der optional einen oder mehrere Reste wie CrC2o-Kohlenwasserstoffreste tragen kann, z.B. aus der Gruppe d-C2o-Alkyl (z.B. lineares oder verzweigtes CrC2o-Alkyl wie sec. Butyl oder Dodecyl), welches einen oder mehrere Reste wie CrC2o-Kohlenwasserstoffreste wie C6-C2o-Arylreste (z.B. Phenyl, Biphenyl, Naphthyl) tragen kann, und C6-C2o-Aryl (z.B. Phenyl, Biphenyl, Naphthyl), welches optional einen oder mehrere Reste tragen kann wie Cr do-Alkyl (z.B. Methyl, Ethyl, Propyl, Butyl), oder R2 ist - O - SO3 M, - SO3 M1 - O - PO3H M, H oder PO3H M1 vorzugsweise PO3H M, worin M gleich H oder ein Kation, insbesondere ein Metallkation wie ein Alkalimetallion oder Erdalkalimetallion, oder ein Ammoniumion ist.R 2 is H, a C 1 -C 2 o-alkyl radical (eg, methyl, ethyl, propyl, butyl) or a C 6 -C 24 aryl radical (eg, phenyl, biphenyl, naphthyl) which optionally has one or more radicals, such as CrC can carry 2 o-hydrocarbon radicals, for example from the group dC 2 o-alkyl (for example, linear or branched CrC 2 O-alkyl such as sec. butyl or dodecyl) which comprises one or more radicals such as -C 2 o-hydrocarbon groups such as C 6 -C 2 o-aryl radicals (For example, phenyl, biphenyl, naphthyl), and C 6 -C 2 o-aryl (eg, phenyl, biphenyl, naphthyl), which may optionally carry one or more radicals such as C r do-alkyl (eg, methyl, ethyl, propyl , Butyl), or R 2 is - O - SO 3 M, - SO 3 M 1 - O - PO 3 HM, H or PO 3 HM 1, preferably PO 3 HM, where M is H or a cation, in particular a metal cation, such as an alkali metal ion or alkaline earth metal ion, or an ammonium ion.
Besonders bevorzugte anionische Tenside (d) sind Dialkyl-Sulfosuccinate wie z.B. Di-(2-Ethylhexyl)Sulfosuccinat-Natrium (z.B. Triton® GR 7 ME von Union Carbide), Alkylarylsulfonate wie Dodecylbenzolsulfonate, z.B. Erdalkalidodecylbenzolsulfonate wie Calcium-dodecylbenzolsulfonate (z.B. z.B. Phenylsulfonat® Ca 100, synonym Calsogen® AR 100 ND, Phenylsulfonat® Ca 70 von Clariant), Alkylarylpolyglykolethersulfate und -sulfonate, insbesondere Arylalkylarylpolyglykolethersulfate wie Tristyrylphenolpolyglykolethersulfate, insbesondere die Alkali- oder Ammonium- oder Triethanolaminsalze (z.B. Soprophor®-Reihe von Rhodia), Alkylethersulfate und deren Salze (z.B. wie Genapol® LRO von Clariant), Alkylsulfate und Alkylsulfonate (z.B. wie die Hostapur® Reihe von Clariant), Alkylpolyglykoletherphosphate, insbesondere die Alkalisalze (z.B. die Rhodafac®-Reihe Rhodia), Alkylarylpolyglykoletherphosphate und - phosphonate, insbesondere in Form der Alkalimetallsalze. Die Salze sind im allgemeinen bevorzugt Metallsalze wie Alkali- oder Erdalkalimetallsalze oder Ammonium- oder Trialkylaminsalze.Particularly preferred anionic surfactants (d) are dialkyl sulfosuccinates, e.g. Di (2-ethylhexyl) sulfosuccinate sodium (e.g., Triton® GR 7 ME from Union Carbide), alkylaryl sulfonates such as dodecyl benzene sulfonates, e.g. Erdalkalidodecylbenzolsulfonate such as calcium dodecylbenzenesulfonates (eg, for example Phenylsulfonat® Ca 100, synonymous Calsogen® AR 100 ND, Phenylsulfonat® Ca 70 from Clariant), Alkylarylpolyglykolethersulfate and sulfonates, in particular Arylalkylarylpolyglykolethersulfate as Tristyrylphenolpolyglykolethersulfate, especially the alkali or ammonium or triethanolamine (eg Soprophor® Rhodia series), alkyl ether sulfates and their salts (eg, such as Genapol® LRO from Clariant), alkyl sulfates and alkyl sulfonates (eg, like Clariant's Hostapur® series), alkyl polyglycol ether phosphates, especially the alkali salts (eg Rhodafac® Rhodia series), alkylaryl polyglycol ether phosphates and - phosphonates, in particular in the form of the alkali metal salts. The salts are generally preferably metal salts such as alkali or alkaline earth metal salts or ammonium or trialkylamine salts.
Als nichtionische Tenside (Komponente e) eignen sich beispielsweise Alkoxylate, z.B. Ethoxylate, Propoxylate oder Butoxylate und deren Kombinationen. Unter dem Begriff Alkoxylate werden Verbindungen verstanden, die Alkylenoxideinheiten enthalten, insbesondere Einheiten von C2-Cio-Alkylenoxiden, wie Ethylenoxid, Propylenoxid oder Butylenoxid, wobei die Einheiten innerhalb des Tensids gleich oder voneinander verschieden und dabei statistisch gemischt oder blockweise angeordnet sein können. Beispiele für Alkoxylate als Komponente (e) sind Verbindungen der nachfolgenden Formel (III): R1-(AO)w-R2 (III) , worinSuitable nonionic surfactants (component e) are, for example, alkoxylates, for example ethoxylates, propoxylates or butoxylates and combinations thereof. The term alkoxylates is understood as meaning compounds which contain alkylene oxide units, in particular units of C 2 -C 10 -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, wherein the units within the surfactant may be the same or different and may be randomly mixed or blockwise arranged. Examples of alkoxylates as component (e) are compounds of the following formula (III): R 1 - (AO) w R 2 (III) wherein
R1 ausgewählt ist aus der Gruppe H, HO, CrC3o-Alkyl, welches linear oder verzweigt sein kann, (z.B. Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl), C1-C30-AIkOXy, vorzugsweise Ci-Cio-Alkoxy, welches linear oder verzweigt sein kann (z.B. Methoxy, Ethoxy, Propoxy, Butoxy, Pentoxy, Hexoxy), (z.B. Phenyl), welches optional einen oder mehrere Reste tragen kann wie CrC3o-Arylalkyl (z.B. Styrylphenyl) oder Ci-C30-Alkyl, worin die Alkylgruppen linear oder verzweigt sein können (z.B. Butyl oder Dodecyl), C6-C24-Aryloxy (z.B. Phenoxy), welches optional einen oder mehrere Reste tragen kann wie Ci-C3o-Arylalkyl (z.B. Styrylphenyl), oder CrC-30-Alkyl, worin die Alkylgruppen linear oder verzweigt sein können (z.B. Butyl oder Dodecyl), oderR 1 is selected from the group consisting of H, HO, C 1 -C 3 o-alkyl, which may be linear or branched, (for example methyl, ethyl, propyl, butyl, pentyl, hexyl), C 1 -C 30 -alkoxy, preferably C 10 alkoxy, which may be linear or branched (eg methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy), (For example, phenyl), which may optionally carry one or more radicals such as CrC 3 o-arylalkyl (eg styrylphenyl) or Ci-C 30 alkyl, wherein the alkyl groups may be linear or branched (eg butyl or dodecyl), C 6 -C 2 4- aryloxy (eg phenoxy) which may optionally carry one or more radicals, such as C 1 -C 30 -arylalkyl (eg styrylphenyl), or C 1 -C 30 -alkyl, in which the alkyl groups may be linear or branched (eg butyl or dodecyl) , or
R1 ist ein Sorbitanesterrest, ein Glycerinesterrest, oder C-ι-C3o-Alkyl-NR4, vorzugsweise Cio-C2o-Alkyl-NR4, worin die C-ι-C2o-Alkylgruppe linear oder verzweigt sein kann (z.B. Dodecyl, Hexadecyl, Octadecyl) und worin R4 gleich H oder C1-C10- Alkyl ist (z.B. Methyl, Ethyl, Propyl, Butyl),R 1 is a Sorbitanesterrest, a Glycerinesterrest, or C-ι-C 3 o-alkyl-NR 4, preferably Cio-C 2 o-alkyl-NR 4, wherein the C-ι-C2o-alkyl group may be linear or branched ( eg dodecyl, hexadecyl, octadecyl) and wherein R 4 is H or C 1 -C 10 alkyl (eg methyl, ethyl, propyl, butyl),
R2 gleich H oder CrC6-Alkyl, welches linear oder verzweigt sein kann (z.B. Methyl, Ethyl, Propyl, Butyl, Pentyl oder Hexyl) ist, und w ist eine ganze Zahl von 1 bis 100, vorzugsweise 4 bis 80, insbesondere 6 bis 50, AO ist eine Alkylenoxideinheit, z.B. (EO)x(PO)γ(BO)2, worin EO eineR 2 is H or C 1 -C 6 -alkyl, which may be linear or branched (for example methyl, ethyl, propyl, butyl, pentyl or hexyl), and w is an integer from 1 to 100, preferably 4 to 80, in particular 6 to 50, AO is an alkylene oxide unit, eg (EO) x (PO) γ (BO) 2 , where EO is a
Ethylenoxideinheit, PO eine Propylenoxideinheit, BO eine Butylenoxideinheit, x eine ganze Zahl von 0 - 100, y eine ganze Zahl von 0 - 100, z eine ganze Zahl von 0 bis 100 und die Summe x + y + z mindestens 1 ist, und die Alkylenoxideinheit, z.B. (EO)χ(PO)γ(BO)z, statistisch gemischt oder blockweise aufgebaut ist.Ethylene oxide unit, PO is a propylene oxide unit, BO is a butylene oxide unit, x is an integer of 0-100, y is an integer of 0-100, z is an integer of 0-100 and the sum of x + y + z is at least 1, and Alkylene oxide unit, for example (EO) χ (PO) γ (BO) z , randomly mixed or constructed in blocks.
Besonders bevorzugte nichtionische Tenside (e) sind Alkylarylpolyalkoxylate, z.B. die Ethoxylate, Propoxylate und/oder Butoxylate, Arylalkylarylpolyalkoxylate wie Tristyrylphenylpolyalkoxylate (z.B. Soprophor® Reihe von Rhodia) und Alkylphenylpolyalkoxylate wie Tributylphenylpolyalkoxlate (z.B. Sapogenat® Reihe von Clariant), Alkylenoxid-Blockcopolymere wie Ethylenoxid(EO)-Propylenoxid(PO)- Blockcopolymere (z.B. Emulsogen® 3510, Emulsogen® V 1816, Genapol® PF 10, Genapol® PF 20, Genapol® PF 40 von Clariant, Berol® 992 von Akzo Nobel) oder Ethylenoxid(EO)-Butylenoxid(BO)-Blockcopolymere (z.B. Pluronic® Reihe von BASF), Polyalkylenoxide wie Polyethyenoxide, Polypropylenoxide oder Polybutylenoxide, die an einem der beiden endständigen Sauerstoffatome mit Cr C22-Kohlenwasserstoffresten, vorzugsweise Cio-C22-Kohlenwasserstoffresten wie geradkettigen oder verzweigten Cio-C22-Alkylresten (z.B. Decyl, Dodecyl, Tetradecyl, Hexadecyl) substituiert sein können, z.B. Polyglykolether, die isotridecylsubstituiert sein können (z.B. Genapol® X-060, Genapol® X-080, Genapol® X-150 und andere aus den Genapol®-Reihen von Clariant), alkoxylierte wie ethoxylierte Öle wie Pflanzenöle, z.B. alkoxyliertes wie ethoxyliertes Rhizinusöl (Emulsogen® Reihe Clariant), epoxidiertes Sojabohnenöl (z.B. Edenol® D-81 , synonym Agnique® ESO 81 G von Cognis), alkoxylierte wie ethoxylierte (Cio-C-22)-Fettamine (z.B. Genamin®Reihe, z.B. Genamin® S080 von Clariant).Particularly preferred nonionic surfactants (s) are Alkylarylpolyalkoxylate, for example the ethoxylates, propoxylates and / or butoxylates, Arylalkylarylpolyalkoxylate as Tristyrylphenylpolyalkoxylate (eg Soprophor® series by Rhodia) and Alkylphenylpolyalkoxylate as Tributylphenylpolyalkoxlate (for example Sapogenat ® series by Clariant), alkylene oxide block copolymers such as ethylene oxide ( EO) propylene oxide (PO) block copolymers (eg Emulsogen® 3510, Emulsogen® V 1816, Genapol® PF 10, Genapol® PF 20, Genapol® PF 40 from Clariant, Berol® 992 from Akzo Nobel) or Ethylene oxide (EO) -butylene oxide (BO) block copolymers (eg Pluronic® series from BASF), polyalkylene oxides such as polyethylene oxides, polypropylene oxides or polybutylene oxides, which are attached to one of the two terminal oxygen atoms with Cr C 2 2 hydrocarbon radicals, preferably Cio-C 22 hydrocarbon radicals such as straight-chain or branched Cio-C 22 -alkyl radicals (eg decyl, dodecyl, tetradecyl, hexadecyl) may be substituted, for example polyglycol ethers which may be Isotridecylsubstituiert (eg Genapol® X-060, Genapol® X-080, Genapol® X-150 and others from the Genapol® series from Clariant), alkoxylated and ethoxylated oils such as vegetable oils, eg alkoxylated and ethoxylated castor oil (Emulsogen® series Clariant), epoxidized soybean oil (eg Edenol® D-81, synonym Agnique® ESO 81 G from Cognis) , alkoxylated as ethoxylated (Cio-C- 22 ) fatty amines (eg Genamin® series, eg Genamin® S080 from Clariant).
Soweit in dieser Beschreibung kohlenstoffhaltige Reste genannt werden wie Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino und Alkylthio sowie die entsprechenden ungesättigten und/oder substituierten Reste, können diese im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein. Wenn nicht speziell angegeben, weisen diese Reste im allgemeinen 1 bis 30 C-Atome auf, wobei die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt sind. Alkylreste, auch in den zusammengesetzten Bedeutungen wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder sec-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste; Alkenyl bedeutet z.B. AIIyI, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1-yl; Alkinyl bedeutet z.B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl.Insofar as carbon-containing radicals are mentioned in this description, such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding unsaturated and / or substituted radicals, they may each be straight-chain or branched in the carbon skeleton. Unless specifically stated, these radicals generally have from 1 to 30 carbon atoms, with the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, are preferred. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or sec-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl means e.g. Allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1 Methyl-but-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
Alkenyl in der Form (C3-C4)Alkenyl, (C3-C5)AI kenyl, (C3-C6)Alkenyl, (C3-C8)Alkenyl oder (C3-Ci2)-Alkenyl bedeutet vorzugsweise einen Alkenylrest mit 3 bis 4, 3 bis 5, 3 bis 6, 3 bis 8 bzw. 3 bis 12 C-Atomen, bei dem die Doppelbindung nicht an dem C-Atom liegt, das mit dem übrigen Molekülteil der Verbindung verbunden ist ("yϊ"-Position). Entsprechendes gilt für (C3-C4)Alkinyl etc., (C3-C4)Alkenyloxy etc. und (C3-C4)Alkinyloxy etc.Alkenyl in the form (C 3 -C 4) alkenyl, (C 3 -C 5) AI -alkenyl, (C 3 -C 6) alkenyl, (C 3 -C 8) alkenyl or (C 3 -C 2) alkenyl preferably denotes an alkenyl radical having 3 to 4, 3 to 5, 3 to 6, 3 to 8 or 3 to 12 C atoms, in which the double bond does not exist on the C atom, which is connected to the remaining part of the molecule of the compound ("yϊ" position). The same applies to (C 3 -C 4 ) alkynyl, etc., (C 3 -C 4 ) alkenyloxy etc. and (C 3 -C 4 ) alkynyloxy etc.
Ein Kohlenwasserstoffrest bedeutet ein geradkettiger, verzweigter oder cyclischer und gesättigter oder ungesättigter aliphatischer oder aromatischer Kohlenwasserstoffrest, z.B. Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl oder Aryl. Ein Kohlenwasserstoffrest weist bevorzugt 1 bis 40 C-Atome, vorzugsweise 1 bis 30 C-Atome auf; besonders bevorzugt bedeutet ein Kohlenwasserstoffrest Alkyl, Alkenyl oder Alkinyl mit bis zu 12 C-Atomen oder Cycloalkyl mit 3, 4, 5, 6 oder 7 Ringatomen oder Phenyl.A hydrocarbon radical means a straight, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, e.g. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl. A hydrocarbon radical preferably has 1 to 40 C atoms, preferably 1 to 30 C atoms; particularly preferably a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 C atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl.
Aryl bedeutet ein mono-, bi- oder polycyclisches aromatisches System, beispielsweise Phenyl, Naphthyl, Tetrahydronaphthyl, Indenyl, Indanyl, Pentalenyl, Fluorenyl und ähnliches, vorzugsweise Phenyl.Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
Ein heterocyclischer Rest oder Ring (Heterocyclyl) kann gesättigt, ungesättigt oder heteroaromatisch und unsubstituiert oder substituiert sein; er enthält vorzugsweise ein oder mehrere Heteroatome im Ring, vorzugsweise aus der Gruppe N, O und S; vorzugsweise ist er ein aliphatischer Heterocyclyl rest mit 3 bis 7 Ringatomen oder ein heteroaromatischer Rest mit 5 oder 6 Ringatomen und enthält 1 , 2 oder 3 Heteroatome. Der heterocyclische Rest kann z.B. ein heteroaromatischer Rest oder Ring (Heteroaryl) sein, wie z.B. ein mono-, bi- oder polycyclisches aromatisches System, in dem mindestens 1 Ring ein oder mehrere Heteroatome enthält, beispielsweise Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl,A heterocyclic radical or ring (heterocyclyl) may be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3 heteroatoms. The heterocyclic radical may be e.g. a heteroaromatic radical or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,
Thiazolyl, Oxazolyl, Furyl, Pyrrolyl, Pyrazolyl und Imidazolyl, oder ist ein partiell oder vollständig hydrierter Rest wie Oxiranyl, Oxetanyl, Pyrrolidyl, Piperidyl, Piperazinyl, Dioxolanyl, Morpholinyl, Tetrahydrofuryl. Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten. Halogen bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Haloalkyl, -alkenyl und -alkinyl bedeuten durch Halogen, vorzugsweise durch Fluor, Chlor und/oder Brom, insbesondere durch Fluor oder Chlor, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 und OCH2CH2CI; entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierte Reste.Thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below in question, in addition also oxo. The oxo group may also occur on the hetero ring atoms, which may exist in different oxidation states, eg at N and S. Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl; Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
Kohlenwasserstoffreste, z.B. Alkyl, Alkenyl, Alkinyl, Aryl, Phenyl und Benzyl, oder Heterocyclyl oder Heteroaryl, können substituiert sein, wobei die Substituenten beispielsweise einen oder mehrere, vorzugsweise 1 , 2 oder 3 Reste aus der Gruppe Halogen, Alkoxy, Haloalkoxy, Alkylthio, Hydroxy, Amino, Nitro, Carboxy, Cyano, Azido, Alkoxycarbonyl, Alkylcarbonyl, Formyl, Carbamoyl, Mono- und Dialkylaminocarbonyl, substituiertes Amino, wie Acylamino, Mono- und Dialkylamino, und Alkylsulfinyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl und, im Falle cyclischer Reste, auch Alkyl und Haloalkyl sowie den genannten gesättigten kohlenwasserstoffhaltigen Resten entsprechende ungesättigte aliphatische Reste, wie Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy etc. bedeuten. Bei Resten mit C-Atomen sind solche mit 1 bis 4 C-Atomen, insbesondere 1 oder 2 C-Atomen, bevorzugt. Bevorzugt sind in der Regel Substituenten aus der Gruppe Halogen, z.B. Fluor und Chlor, (C-ι-C4)Alkyl, vorzugsweise Methyl oder Ethyl, (Ci-C4)Haloalkyl, vorzugsweise Trifluormethyl, (CrC4)Alkoxy, vorzugsweise Methoxy oder Ethoxy, (Ci-C4)Haloalkoxy, Nitro und Cyano. Besonders bevorzugt sind dabei die Substituenten Methyl, Methoxy und Chlor.Hydrocarbon radicals, for example alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or heterocyclyl or heteroaryl, may be substituted, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, Hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals , Alkyl and haloalkyl and said saturated hydrocarbon-containing radicals corresponding unsaturated aliphatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, etc. mean. For radicals with C atoms, those having 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred. As a rule, preferred substituents are selected from the group halogen, for example fluorine and chlorine, (C-ι-C 4) alkyl, preferably methyl or ethyl, (Ci-C4) haloalkyl, preferably trifluoromethyl, (CrC 4) alkoxy, preferably methoxy or Ethoxy, (C 1 -C 4 ) haloalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy and chlorine.
Gegebenenfalls substituiertes Phenyl ist vorzugsweise Phenyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, (CrC4)Alkyl, (CrC4)Alkoxy, (CrC4)Halogenalkyl, (CrC4)Halogenalkoxy und Nitro substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyl, 2-, 3- und 4-Trifluorphenyl und 2-, 3- und 4-Trichlorphenyl, 2,4-, 3,5-, 2,5- und 2,3-Dichlorphenyl, o-, m- und p-Methoxyphenyl. Ein Acylrest bedeutet den Rest einer organischen Säure, der formal durch Abspaltung einer OH-Gruppe aus der organischen Säure entsteht, z.B. der Rest einer Carbonsäure und Reste davon abgeleiteter Säuren wie der Thiocarbonsäure, gegebenenfalls N-substituierten Iminocarbonsäuren oder die Reste von Kohlensäuremonoestern, gegebenenfalls N-substituierter Carbaminsäuren, Sulfonsäuren, Sulfinsäuren, Phosphonsäuren, Phosphinsäuren.Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C r C4) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluorophenyl and 2-, 3- and 4-trichlorophenyl , 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl. An acyl radical is the radical of an organic acid which is formally formed by cleavage of an OH group from the organic acid, for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radicals of carbonic acid monoesters, optionally N -substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
Ein Acylrest ist bevorzugt Formyl oder aliphatisches Acyl aus der Gruppe CO-RX,An acyl radical is preferably formyl or aliphatic acyl from the group CO-R X ,
CS-RX, CO-ORX, CS-ORX, CS-SRX, SORY oder SO2RY, wobei Rx und Rγ jeweils einen Ci-C30-Kohlenwasserstoffrest bedeutet, der unsubstituiert oder substituiert ist, oder Aminocarbonyl oder Aminosulfonyl, wobei die beiden letztgenannten Reste unsubstituiert, N-monosubstituiert oder N,N-disubstituiert sind.CS-R X , CO-OR X , CS-OR X , CS-SR X , SOR Y or SO 2 R Y , where R x and R γ each represent a C 1 -C 30 -hydrocarbon radical which is unsubstituted or substituted, or aminocarbonyl or aminosulfonyl, where the latter two radicals are unsubstituted, N-monosubstituted or N, N-disubstituted.
Acyl bedeutet beispielsweise Formyl, Halogenalkylcarbonyl, Alkylcarbonyl wieAcyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl as
(C-rC-OAlkylcarbonyl, Phenylcarbonyl, wobei der Phenylring substituiert sein kann, z.B. wie oben für Phenyl angegeben, oder Alkyloxycarbonyl, Phenyloxycarbonyl,(C 1 -C 6 -alkylcarbonyl, phenylcarbonyl, where the phenyl ring may be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl,
Benzyloxycarbonyl, Alkylsulfonyl, Alkylsulfinyl, N-Alkyl-1-iminoalkyl und andereBenzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and others
Reste von organischen Säuren.Residues of organic acids.
Von Formel (I), (II), (III) und den anderen in dieser Beschreibung genannten Verbindungen sind auch alle Stereoisomeren und deren Gemische umfasst. Solche Verbindungen der enthalten ein oder mehrere asymmetrische C-Atome oder auch Doppelbindungen, die in der allgemeinen Formel nicht gesondert angegeben sind. Die durch ihre spezifische Raumform definierten möglichen Stereoisomeren, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von den jeweiligen Formeln umfaßt und können nach üblichen Methoden aus Gemischen der Stereoisomeren erhalten oder auch durch stereoselektive Reaktionen in Kombination mit dem Einsatz von stereochemisch reinen Ausgangsstoffen hergestellt werden.Formula (I), (II), (III) and the other compounds mentioned in this description also include all stereoisomers and mixtures thereof. Such compounds containing one or more asymmetric C atoms or double bonds, which are not specified separately in the general formula. The possible defined by their specific spatial form possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers are all encompassed by the respective formulas and can be obtained by conventional methods from mixtures of stereoisomers or by stereoselective reactions in combination with the use of stereochemically pure Starting materials are produced.
Die Herstellung der erfindungsgemäßen Mikroemulsionskonzentrate kann durch übliche Verfahren erfolgen, z.B. Mischen durch Lösen oder Emulgieren der Einzelkomponenten, bevorzugt bei Raumtemperatur. Sofern weitere Hilfs- und Zusatzstoffe enthalten sind, werden diese ebenfalls bevorzugt bei Raumtemperatur eingetragen. Die Zugabereihenfolge der Einzelkomponenten ist dabei im allgemeinen beliebig.The preparation of the microemulsion concentrates according to the invention can be carried out by customary processes, for example mixing by dissolving or emulsifying the individual components, preferably at room temperature. If other auxiliaries and additives are included, they are also preferred at room temperature entered. The order of addition of the individual components is generally arbitrary.
Die Herstellprozesse sind im Prinzip bekannt und beispielsweise beschrieben in Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3^ Ed. 1979, G. Goodwin Ltd. London; H. Mollet, A. Grubenmann, "Formulierungstechnik", Wiley-VCH, Weinheim 2000.The production processes are known in principle and are described, for example, in Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3 ^ Ed. 1979, G. Goodwin Ltd. London; H. Mollet, A. Grubenmann, "Formulation Technology", Wiley-VCH, Weinheim 2000.
Die Formulierungshilfsstoffe wie Inertmaterialien und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986.The formulation auxiliaries, such as inert materials and other additives, are likewise known and are described, for example, in: "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing company, Stuttgart 1976; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit von Komponenten (a) und (b) verschiedenen agrochemischen Wirkstoffen, wie Fungiziden, Insektiziden und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmischung.On the basis of these formulations, it is also possible to prepare combinations with agrochemical active substances other than components (a) and (b), such as fungicides, insecticides and / or growth regulators, e.g. in the form of a ready-to-use formulation or as a tank mix.
Die erfindungsgemäßen Mikroemulsionskonzentrate lassen sich mit Wasser zu Mikroemulsionen verdünnen, die ebenfalls Gegenstand der vorliegenden Erfindung sind. Dabei kann das Gewichtsverhältnis Mikroemulsionskonzentrat : Wasser beispielsweise 1 :0,00001 bis 0,1 :1000, vorzugsweise 1 :0,0001 bis 0,1 :100 betragen, was zu konzentrierten Mikroemulsionen führt, die als solche lagerstabil sind. Diese können für Applikationszwecke mit Wasser weiter zu Spritzbrühen verdünnt werden, die im allgemeinen in Form von Emulsionen wie Mikroemulsionen, wässrigen Lösungen, Suspensionen oder Suspoemulsionen vorliegen. Die Komponenten (a), (b), (c), (d), (e) und optional (f) der erfindungsgemäßen Mikroemulsionskonzentrate und Mikroemulsionen können zusammen in einer Fertigformulierung enthalten sein, die dann in üblicher weise, z.B. in Form einer Spritzbrühe appliziert werden kann.The microemulsion concentrates according to the invention can be diluted with water to microemulsions, which are likewise the subject of the present invention. The weight ratio of microemulsion concentrate: water may be, for example, 1: 0.00001 to 0.1: 1000, preferably 1: 0.0001 to 0.1: 100, resulting in concentrated microemulsions which are storage stable as such. For application purposes, these can be further diluted with water to spray liquors, which are generally in the form of emulsions such as microemulsions, aqueous solutions, suspensions or suspoemulsions. The components (a), (b), (c), (d), (e) and optionally (f) of the microemulsion concentrates and microemulsions according to the invention may be contained together in a ready-to-use formulation which is then in the customary manner, for example in the form of a spray mixture can be applied.
Die erfindungsgemäßen Mikroemulsionskonzentrate einschließlich der daraus erhältlichen Spritzbrühen (nachstehend gemeinsam als erfindungsgemäße agrochemische Mittel bezeichnet) können neben den Komponenten (a), (b), (c), (d) und (e) als weitere Komponente verschiedene Formulierungshilfsmittel (Komponente f) enthalten, z.B. übliche Hilfs- und Zusatzstoffe, wie Anti-Driftagentien, Stoffe zur Beeinflussung der Feuchtigkeit (Humectants), Dünger wie Ammoniumsulfat, Harnstoff oder Mehrkomponenten-Dünger z.B. auf Phosphor-, Kalium- und Stickstoffbasis wie P,K,N-Dünger, oder handelsübliche von Komponenten (d) und (e) verschiedene Tenside wie betainische oder polymere Tenside, Stabilisatoren wie pH-Stabilisatoren, Bioeide, UV-Stabilisatoren, Entschäumer, synthetische oder natürliche Polymere. Diese agrochemischen Mittel sowie deren Herstellung und Anwendung sind ebenfalls neu und Gegenstand dieser Erfindung.The microemulsion concentrates according to the invention, including the spray liquors obtainable therefrom (hereinafter referred to collectively as agrochemical agents according to the invention), may contain, in addition to the components (a), (b), (c), (d) and (e) as a further component, various formulation auxiliaries (component f) , eg customary auxiliaries and additives, such as anti-drift agents, humectants, fertilizers, such as ammonium sulfate, urea or multi-component fertilizer, for example. based on phosphorus, potassium and nitrogen such as P, K, N fertilizer, or commercially available of components (d) and (e) various surfactants such as Betainic or polymeric surfactants, stabilizers such as pH stabilizers, biocides, UV stabilizers, defoamers, synthetic or natural polymers. These agrochemical agents as well as their preparation and use are also novel and subject of this invention.
Bevorzugte Beispiele für übliche Hilfs- und Zusatzstoffe (f) sind - Netzmittel wie Genapol® LRO (0-35 Gew.-%), Dispergiermittel wie Tamol® (0-15 Gew.-%) oder weitere Tenside (z.B. kationische oder polymere Tenside) (0-30 Gew.-%);Preferred examples of customary auxiliaries and additives (f) are wetting agents such as Genapol® LRO (0-35% by weight), dispersants such as Tamol® (0-15% by weight) or further surfactants (for example cationic or polymeric surfactants ) (0-30% by weight);
- Anorganische Salze wie NaCI, Na2SO4, MgCI2 (0-50 Gew.-%), (oligo-; poly-)- Phosphate; Carbonate wie Kaliumcarbonat; - Dünger wie Ammoniumsulfat, Ammoniumnitrat, Harnstoff, Phosphor- und Kalium- haltige Komponenten, gegebenenfalls weitere Spurenelemente (0-60 Gew.-%);Inorganic salts such as NaCl, Na 2 SO 4 , MgCl 2 (0-50% by weight), (oligo-, poly-) phosphates; Carbonates such as potassium carbonate; - Fertilizers such as ammonium sulfate, ammonium nitrate, urea, phosphorus and potassium-containing components, optionally further trace elements (0-60 wt .-%);
- Entschäumer wie Fluowet® PP (0-2 Gew.-%) oder aus der Rhodorsil®-Reihe (z.B. Rhodorsil® 481 );Defoamers such as Fluowet® PP (0-2% by weight) or from the Rhodorsil® series (for example Rhodorsil® 481);
- Bindemittel wie geeignete natürliche oder synthetische Stoffe wie Polyaminosäuren, Polyvinylalkohole, Polyvinylpyrrolidon, Polyacrylsäure-Derivate- Binders such as suitable natural or synthetic substances such as polyamino acids, polyvinyl alcohols, polyvinylpyrrolidone, polyacrylic acid derivatives
(0-15 Gew.-%);(0-15 wt%);
- Kristallisationsinhibitoren (0-8 Gew.-%). Der Einsatz der erfindungsgemäßen agrochemischen Mittel kann z.B. geschehen durch Applikation auf die Schadorganismen oder die Orte, an denen sie auftreten, z.B. durch Spritzung. Die erfindungsgemäßen agrochemischen Mittel werden in der Regel in Form einer Spritzbrühe ausgebracht, welche die Komponenten (a), (b), (c), (d) und (e) in wirksamen Mengen und gegebenenfalls übliche Hilfs- und Zusatzstoffe (T), z.B. für die Formulierung oder Anwendung enthält. Die Spritzbrühe wird im allgemeinen auf Basis von Wasser hergestellt, wobei übliche Hilfs- und Zusatzstoffe (f), z.B. Öle, wie Pflanzenöle oder hochsiedende Kohlenwasserstoffe wie Kerosin oder Paraffin zugesetzt werden können.- Crystallization inhibitors (0-8 wt .-%). The use of the agrochemical compositions according to the invention can be done for example by application to the harmful organisms or the places where they occur, eg by spraying. The agrochemical compositions according to the invention are generally applied in the form of a spray mixture containing the components (a), (b), (c), (d) and (e) in effective amounts and optionally conventional auxiliaries and additives (T), eg for the formulation or application. The spray mixture is generally prepared on the basis of water, it being possible to add customary auxiliaries and additives (f), for example oils, such as vegetable oils or high-boiling hydrocarbons, such as kerosene or paraffin.
Bei der Applikation liegt die Konzentration an Wirkstoff (Komponente a) im allgemeinen bei 10"6 bis 10 Gew.-%, vorzugsweise bei 10"5 bis 4 Gew.-% in dem applizierten Mittel, z.B. der Spritzbrühe, bei einer Aufwandmenge von 1 bis 5000 l/ha, vorzugsweise 50 bis 1000 l/ha.In the application, the concentration of active ingredient (component a) is generally from 10 "6 to 10 wt .-%, preferably at 10 " 5 to 4 wt .-% in the applied agent, eg the spray mixture, at a rate of 1 to 5000 l / ha, preferably 50 to 1000 l / ha.
Zur Anwendung werden in handelsüblicher Form vorliegende konzentrierte Formulierungen gegebenenfalls in üblicherweise verdünnt, z.B. mittels Wasser. Es kann vorteilhaft sein, den Spritzbrühen weitere Mengen an Komponenten (c), (d) und (e) und/oder andere zur Anwendung übliche Hilfs- und Zusatzstoffe (f), insbesondere selbstemulgierende Öle oder Paraffinöle zuzugeben. Auch können zusätzliche Komponenten (a) zugegeben werden oder andere von Komponenten (a) verschiedene agrochemische Wirkstoffe.For use, concentrated formulations present in commercial form are optionally diluted in customary manner, e.g. by means of water. It may be advantageous to add to the spray mixtures further amounts of components (c), (d) and (e) and / or other auxiliary agents and additives (f) customary for use, in particular self-emulsifying oils or paraffin oils. Also, additional components (a) may be added or other agrochemical agents other than components (a).
Bevorzugte Mischungen sind Verbindungen, die als ACCase-lnhibitoren oder als p- Hydroxyphenyl pyruvate dioxygenase (HPPD)-Inhibitoren wirksam sind, mit Verbindungen, die als Safener wirksam sind, wie oben ausgeführt, die dann als Fertigformulierung oder als Tankmischung für die Herstellung von Spritzbrühen eingesetzt werden können.Preferred mixtures are compounds which are effective as ACCase inhibitors or as p-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors, with compounds which act as safeners, as stated above, which are then used as ready-to-use formulation or as tank mix for the production of spray liquors can be used.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, Art des verwendeten Herbizids, kann die erforderliche Aufwandmenge der agrochemischen Wirkstoffe (Komponente a) variieren. Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 10 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie zwischen 0,005 und 5 kg/ha.With the external conditions such as temperature, humidity, type of herbicide used, the required application rate of agrochemical active ingredients (Component a) vary. It can vary within wide limits, for example between 0.001 and 10 kg / ha or more active substance, preferably between 0.005 and 5 kg / ha.
Sind die erfindungsgemäßen agrochemischen Mittel bevorzugt herbizide Mittel, weisen diese eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen auf. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden gut erfasst. Dabei können die Mittel z.B. im Vorsaat-, Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen herbiziden Mittel kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.If the agrochemical compositions according to the invention are preferably herbicidal agents, they have an excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even hard-to-control perennial weeds that sprout from rhizomes, rhizomes or other permanent organs are well recorded. The means may e.g. be applied in pre-sowing, pre-emergence or post-emergence. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the herbicidal compositions according to the invention, without the intention of being restricted to certain species.
Auf der Seite der monokotylen Unkrautarten werden z.B. Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Leptochloa spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. sowie Bromus spp. wie Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum und Bromus japonicus und Cyperusarten aus der annuellen Gruppe und auf seiten der perennierenden Spezies Agropyron, Cynodon, Imperata sowie Sorghum und auch ausdauernde Cyperusarten gut erfaßt.On the side of the monocotyledonous weeds, e.g. Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Leptochloa spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and Bromus spp. such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum and Bromus japonicus and Cyperusarten from the annuelle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusarten well.
Bei dikotylen Unkrautarten erstreckt sich das Wirkungsspektrum auf Arten wie z.B. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. wie Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp.,Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. und Viola spp., Xanthium spp., auf der annuellen Seite sowie Convolvulus, Cirsium, Rumex und Artemisia bei den perennierenden Unkräutern. Unter den spezifischen Kulturbedingungen im Reis vorkommende Schadpflanzen wie z.B. Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus und Cyperus werden von den erfindungsgemäßen Mitteln ebenfalls hervorragend bekämpft.For dicotyledonous weed species, the spectrum of activity extends to species such as, for example, Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds. Harmful plants occurring under the specific culture conditions in rice such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are also excellently controlled by the compositions according to the invention.
Werden die erfindungsgemäßen herbiziden Mittel vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab.If the herbicidal compositions according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die completely after three to four weeks.
Bei Applikation der erfindungsgemäßen herbiziden Mittel auf die grünen Pflanzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird.Upon application of the herbicidal compositions according to the invention to the green plant parts in the postemergence process, a drastic growth arrest also occurs very rapidly after the treatment and the weed plants remain in the growth stage existing at the time of application or die off completely after a certain time, so that in this way one for the crops harmful weed competition is eliminated very early and sustainable.
Die erfindungsgemäßen herbiziden Mittel zeichnen sich durch eine schnell einsetzende und lang andauernde herbizide Wirkung aus. Die Regenfestigkeit der Wirkstoffe in den erfindungsgemäßen Kombinationen ist in der Regel günstig. Als besonderer Vorteil fällt ins Gewicht, dass die in den herbizide Mitteln verwendeten und wirksamen Dosierungen von herbiziden Verbindungen so gering eingestellt werden können, dass ihre Bodenwirkung optimal niedrig ist. Somit wird deren Einsatz nicht nur in empfindlichen Kulturen erst möglich, sondern Grundwasser- Kontaminationen werden praktisch vermieden. Durch die erfindungsgemäße Kombination von Wirkstoffen wird eine erhebliche Reduzierung der nötigen Aufwandmenge der Wirkstoffe ermöglicht.The herbicidal compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action. The rainfastness of the active ingredients in the combinations according to the invention is generally favorable. A particular advantage is the fact that the effective and used in the herbicidal compositions dosages of herbicidal compounds can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contaminations are virtually avoided. The combination of active substances according to the invention enables a considerable reduction in the required application rate of the active substances.
Die genannten Eigenschaften und Vorteile sind in der praktischen Unkrautbekämpfung von Nutzen, um landwirtschaftliche Kulturen von unerwünschten Konkurrenzpflanzen freizuhalten und damit die Erträge qualitativ und quantitativ zu sichern und/oder zu erhöhen. Der technische Standard wird durch diese neuen Mittel hinsichtlich der beschriebenen Eigenschaften deutlich übertroffen.The said properties and advantages are useful in the practical weed control to keep agricultural crops free from undesirable competing crops and thus the yields qualitatively and to secure and / or increase quantitatively. The technical standard is significantly exceeded by these new means in terms of the properties described.
Obgleich die erfindungsgemäßen herbiziden Mittel eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werdenAlthough the herbicidal compositions of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds
Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. zweikeimblättriger Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben, oder Gramineen-Kulturen wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis oder Mais, nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Nutzpflanzungen oder in Zierpflanzungen.Crops of economically important crops e.g. dicotyledonous crops such as soybean, cotton, oilseed rape, sugarbeet, or graminaceous crops such as wheat, barley, rye, oats, millet, rice or maize, only marginally or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops or in ornamental plantings.
Darüber hinaus weisen die erfindungsgemäßen herbiziden Mittel hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da das Lagern hierdurch verringert oder völlig verhindert werden kann.In addition, the herbicidal compositions according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfindungsgemäßen herbiziden Mittel auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt.On account of their herbicidal and plant growth-regulating properties, the herbicidal compositions according to the invention can also be employed for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop.
Die Anwendung der erfindungsgemäßen herbiziden Mittel kann auch in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen erfolgen, z. B. von Gramineen-Kulturen wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die erfindungsgemäßen Mittel als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind.The application of the herbicidal compositions according to the invention can also be carried out in economically important transgenic crops of useful and ornamental plants, for. B. Graminaceous crops such as wheat, barley, rye, oats, millet, rice and corn or even cultures of sugar beet, cotton, soybeans, rape, potato, tomato, pea and other vegetables. Preferably, the agents according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Bei der Anwendung der erfindungsgemäßen herbiziden Mittel in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen.In the application of the herbicidal compositions according to the invention in transgenic crops, in addition to the effects observed in other crops against harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be combated. modified application rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crops.
Gegenstand der vorliegenden Erfindung ist weiterhin auch ein Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, vorzugsweise in Pflanzenkulturen wie Getreide (z.B. Weizen, Gerste, Roggen, Hafer, Reis, Mais, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, besonders bevorzugt in monokotylen Kulturen wie Getreide, z.B. Weizen, Gerste, Roggen, Hafer, Kreuzungen davon wie Triticale, Reis, Mais und Hirse, wobei man das erfindungsgemäße herbizide Mittel auf die Schadpflanzen, Pflanzenteile, Pflanzensamen oder die Fläche auf der die Pflanzen wachsen, z.B. die Anbaufläche appliziert, z.B. im Vorauflauf, Nachauflauf oder im Vor- und Nachauflauf, vorzugsweise im Vorauflauf. Die Pflanzenkulturen können auch gentechnisch verändert oder durch Mutationsselektion erhalten sein und sind bevorzugt tolerant gegenüber Acetolactatsynthase (ALS)-Inhibitoren.The present invention further provides a method for controlling undesired plant growth, preferably in crops such as cereals (eg wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, more preferably in monocotyledonous crops such as cereals, for example wheat, barley, rye, oats, crossings thereof such as triticale, rice, maize and millet, where the herbicidal composition according to the invention is grown on the harmful plants, plant parts, plant seeds or the area on which the plants grow, for example the cultivated area applied, for example in pre-emergence, post-emergence or pre-emergence and post-emergence, preferably in pre-emergence. The plant cultures may also be genetically engineered or obtained by mutation selection and are preferably tolerant to acetolactate synthase (ALS) inhibitors.
Gegenstand der Erfindung ist auch die Verwendung der erfindungsgemäßen herbiziden Mittel zur Bekämpfung von Schadpflanzen, vorzugsweise in Pflanzenkulturen. Eine bevorzugte Verwendung betrifft den Einsatz von herbiziden Mitteln, die synergistische Mengen an Komponenten (a), (b), (c), (d), (e) und gegebenenfalls (f) enthalten.The invention also provides the use of the herbicidal compositions according to the invention for controlling harmful plants, preferably in plant crops. A preferred use relates to the use of herbicidal compositions containing synergistic amounts of components (a), (b), (c), (d), (e) and optionally (f).
Die erfindungsgemäßen herbiziden Mittel können auch nicht-selektiv zur Bekämpfung unerwünschten Pflanzenwuchses eingesetzt werden, z.B. in Plantagenkulturen, an Wegrändern, Plätzen, Industrieanlagen oder Eisenbahnanlagen.The herbicidal compositions of the invention may also be used non-selectively to control undesired plant growth, e.g. in plantation crops, on roadsides, squares, industrial plants or railway facilities.
Die erfindungsgemäßen agrochemischen Mittel, insbesondere herbiziden Mittel, können gegebenenfalls als Mischformulierungen mit weiteren agrochemischen Wirkstoffen (z.B. weitere Herbizide und Safener, Insektizide, Fungizide, Wachstumsregulatoren) und üblichen Hilfs- und Zusatzstoffen (f) vorliegen, die dann in üblicher Weise mit Wasser verdünnt zur Anwendung gebracht werden, oder als so genannte Tankmischungen durch gemeinsame Verdünnung der getrennt formulierten oder partiell getrennt formulierten Komponenten mit Wasser hergestellt werden.The agrochemical compositions according to the invention, in particular herbicidal compositions, may optionally be present as mixed formulations with other agrochemical active compounds (eg further herbicides and safeners, insecticides, fungicides, growth regulators) and customary auxiliaries and additives (f), which are then diluted with water in the customary manner Be made use of, or prepared as so-called tank mixes by co-diluting the separately formulated or partially separately formulated components with water.
Aufgrund der relativ geringen Aufwandmenge der erfindungsgemäßen herbiziden Mittel ist deren Verträglichkeit im allgemeinen sehr gut. Insbesondere wird durch die erfindungsgemäßen Kombinationen eine Senkung der absoluten Aufwandmenge erreicht, verglichen mit der Einzelanwendung eines herbiziden Wirkstoffs.Due to the relatively low application rate of the herbicidal compositions according to the invention their compatibility is generally very good. In particular, a reduction of the absolute application rate is achieved by the combinations according to the invention, compared with the individual application of a herbicidal active ingredient.
Gegenstand der Erfindung ist deshalb auch ein Verfahren zur selektivenThe invention therefore also relates to a method for selective
Bekämpfung von Schadpflanzen in Pflanzenkulturen, dadurch gekennzeichnet, dass man eine herbizid wirksame Menge an Herbiziden (a), allein oder zusammen mit Safenern, in Kombination mit den Komponenten (c), (d) und (e) appliziert, gegebenenfalls in Kombination mit Komponente (T), z.B. im Vorauflauf, Nachauflauf oder im Vor- und Nachauflauf, vorzugsweise im Vorauflauf, auf die Pflanzen, Pflanzenteile, Pflanzensamen oder den Ort bzw. die Fläche auf der die Pflanzen wachsen, z.B. die Anbaufläche.Control of harmful plants in crops, characterized in that a herbicidally effective amount of herbicides (a), alone or together with Safenern, in combination with the components (c), (d) and (e) applied, optionally in combination with component (T), eg in the pre-emergence, post-emergence or pre-emergence and post-emergence, preferably in pre-emergence, the plants, plant parts , Plant seeds or the place or area on which the plants grow, eg the acreage.
In bevorzugter Verfahrensvariante werden die Herbizide (a) in Feld-Aufwandmengen von 0,1 bis 2000 g Aktivsubstanz/ha, bevorzugt von 0,5 bis 1000 g Aktivsubstanz/ha, ausgebracht. Die benötigten Aufwandmengen der Safener (a) im Feld können je nach Indikation und verwendetem Herbizid innerhalb weiter Grenzen schwanken und liegen in der Regel im Bereich von 0,001 bis 1 kg, vorzugsweise 0,005 bis 0,2 kg Aktivsubstanz/ha.In a preferred process variant, the herbicides (a) in field application rates of 0.1 to 2000 g of active ingredient / ha, preferably from 0.5 to 1000 g of active ingredient / ha, applied. The required application rates of the safeners (a) in the field may vary within wide limits depending on the indication and the herbicide used and are generally in the range of 0.001 to 1 kg, preferably 0.005 to 0.2 kg of active substance / ha.
Weiterhin besonders bevorzugt ist die Ausbringung der Wirkstoffe in Form einer Co- Formulierung oder in Form von Tankmischungen, wobei die Einzelkomponenten, z.B. in Form von Formulierungen, gemeinsam im Tank mit Wasser gemischt werden und die erhaltene Spritzbrühe ausgebracht wird.It is furthermore particularly preferred to dispense the active ingredients in the form of a co-formulation or in the form of tank mixes, the individual components, e.g. in the form of formulations, mixed together in the tank with water and the resulting spray mixture is discharged.
Da die Kulturpflanzenverträglichkeit der erfindungsgemäßen Kombinationen bei gleichzeitig sehr hoher Kontrolle der Schadpflanzen ausgesprochen gut ist, können diese als selektiv angesehen werden. In bevorzugter Verfahrensabwandlung werden herbizide Mittel mit den erfindungsgemäßen Wirkstoffkombinationen daher zur selektiven Bekämpfung unerwünschter Pflanzen eingesetzt.Since the crop plant compatibility of the combinations according to the invention is extremely good, with very high control of harmful plants at the same time, these can be regarded as selective. In a preferred process modification, herbicidal compositions with the active compound combinations according to the invention are therefore used for the selective control of undesired plants.
Die Ausbringung der erfindungsgemäßen herbiziden Mittel kann in üblicher Weise erfolgen, zum Beispiel mit Wasser als Träger in Spritzbrühmengen von etwa 5 bis 4000 Liter/ha. Eine Anwendung der Mittel im sog. Low-Volume- und Ultra-Low- Volume-Verfahren (ULV) ist ebenso möglich.The application of the herbicidal compositions according to the invention can be carried out in a customary manner, for example with water as carrier in Spritzbrühmengen of about 5 to 4000 liters / ha. An application of the means in the so-called. Low-volume and ultra-low-volume method (ULV) is also possible.
Daneben können in den herbiziden Mitteln der Erfindung zur Abrundung derIn addition, in the herbicidal compositions of the invention for rounding the
Eigenschaften, meist in untergeordneten Mengen, zusätzlich ein, zwei oder mehrere von Komponenten (a) verschiedene agrochemische Wirkstoffe aus anderen Bereichen (z.B. Insektizide, Fungizide, Wachstumsregulatoren) enthalten sein.Properties, usually in subordinate quantities, in addition one, two or more of components (a) different agrochemical active ingredients from other areas (eg insecticides, fungicides, growth regulators) may be included.
Damit ergeben sich zahlreiche Möglichkeiten mehrere agrochemische Wirkstoffe miteinander zu kombinieren und gemeinsam zur Bekämpfung vonThis results in numerous opportunities to combine several agrochemical active ingredients together and together to combat
Schadorganismen, wie Schadpflanzen in Pflanzenkulturen einzusetzen, ohne vom Gedanken der Erfindung abzuweichen.Harmful organisms, such as to use harmful plants in crops, without departing from the spirit of the invention.
Die erfindungsgemäßen Mikroemulsionskonzentrate und Mikroemulsionen zeigen eine verbesserte chemische und physikalische Stabilität sowie ein vorteilhaftes physikalisches Applikationsverhalten. Die agrochemischen Wirkstoffe der Komponenten (a), sowie gegebenenfalls weitere zugesetzte agrochemische Wirkstoffe, bleiben während der Applikation gleichmäßig im Spritztank verteilt, wodurch eine gleichmäßige Ausbringung auf die Kultur bzw. Anbaufläche ermöglicht wird. Auch im Spritztank gebildete Mischungen (Tank-Mischungen) wie wässrige Lösungen, Suspensionen, Emulsionen oder Suspoemulsionen sind stabil.The microemulsion concentrates and microemulsions according to the invention exhibit improved chemical and physical stability as well as advantageous physical application behavior. The agrochemical active ingredients of components (a), and optionally further added agrochemical active ingredients remain evenly distributed during application in the spray tank, whereby a uniform application to the crop or acreage is made possible. Also formed in the spray tank mixtures (tank mixtures) such as aqueous solutions, suspensions, emulsions or suspoemulsions are stable.
Die erfindungsgemäßen agrochemischen Mittel weisen eine ausgezeichnete biologische Wirkung auf und sind bevorzugt synergistisch. Diese Effekte erlauben unter anderem eine Reduzierung der Aufwandmenge, die Bekämpfung eines breiteren Spektrums von Schadorganismen, die Schließung von Wirkungslücken, eine schnellere und sicherere Wirkung, eine längere Dauerwirkung, eine komplette Kontrolle der Schadorganismen mit nur einer oder wenigen Applikationen, und eine Ausweitung des Anwendungszeitraumes.The agrochemical compositions according to the invention have an excellent biological activity and are preferably synergistic. These effects allow, inter alia, a reduction of the application rate, the control of a wider range of harmful organisms, the closure of gaps, a faster and safer effect, a longer lasting effect, a complete control of the harmful organisms with only one or a few applications, and an extension of the period of application ,
Die nachfolgenden Ausführungsbeispiele erläutern die Erfindung und haben keinerlei limitierenden Charakter. BeispieleThe following embodiments illustrate the invention and have no limiting character. Examples
1. Herstellung und Lagerung der Formulierungen:1. Preparation and storage of the formulations:
Es wurden die Lösungsmittel vorgelegt und unter Rühren zunächst die agrochemischen Wirkstoffe und dann die Tenside und üblichen Hilfs- und Zusatzstoffe zugegeben. Die so erhaltenen Mikroemulsionskonzentrate wurden über einen Zeitraum von 3 Monaten u.a. bei -10, 0, 25, 40 und 50 Grad Celsius gelagert und waren während der gesamten Zeitdauer chemisch und physikalisch stabil.The solvents were initially charged and the agrochemical active substances and then the surfactants and customary auxiliaries and additives were added with stirring. The microemulsion concentrates so obtained were allowed to u.a. over a period of 3 months. stored at -10, 0, 25, 40 and 50 degrees Celsius and were chemically and physically stable throughout the period.
2. Zusammensetzungen:2. Compositions:
Die Mengen der zusammengegebenen Komponenten der einzelnen Formulierungen sind in der nachfolgenden Tabelle I in Gew.-% angegeben.The amounts of the combined components of the individual formulations are given in the following Table I in% by weight.
Alle Angaben in Gew.-%; ***) Beispiele für VergleichsversucheAll data in% by weight; * * *) Examples of comparative experiments
Alle Angaben in Gew.-%All data in% by weight
Tabelle I - Formulierungsbeispiel Nr. 21Table I - Formulation Example No. 21
Alle Angaben in Gew.-%All data in% by weight
Die verwendeten Handelsprodukte sind nachfolgend erläutert:The commercial products used are explained below:
Phenmedipham (Bayer CropScience): Herbizid Desmedipham (Bayer CropScience): Herbizid Ethofumesat (Bayer CropScience): Herbizid Metamitron (Bayer CropScience): Herbizid Lactofen (Bayer CropScience): Herbizid Fenoxaprop-p-ethyl (Bayer CropScience): Herbizid Mefenpyr-diethyl (Bayer CropScience): Safener Benzylalkohol (Merck): Aromatischer Alkohol mit mindestens 5 C-AtomenPhenmedipham (Bayer CropScience): herbicide Desmedipham (Bayer CropScience): herbicide ethofumesate (Bayer CropScience): herbicide Metamitron (Bayer CropScience): Lactofen herbicide (Bayer CropScience): Fenoxaprop-p-ethyl herbicide (Bayer CropScience): Mefenpyr-diethyl herbicide (Bayer CropScience): Safener Benzyl alcohol (Merck): Aromatic alcohol with at least 5 C atoms
Berol® 992 (Akzo Nobel): Alkohol-ethoxylat-propoxylatBerol® 992 (Akzo Nobel): Alcohol ethoxylate propoxylate
Edenol® D 81Edenol® D 81
(synonym Agnique® ESO 81 G; Cognis): Epoxidiertes Sojabohnenöl(synonym Agnique® ESO 81 G; Cognis): Epoxidized soybean oil
Edenor® MESU (Cognis): RapsölmethylesterEdenor® MESU (Cognis): rapeseed oil methyl ester
Emulsogen® 3510 (Clariant): EO-PO-B lockcopolymerEmulsogen® 3510 (Clariant): EO-PO-B lock copolymer
Emulsogen® V 1816 (Clariant): EO-PO-BlockcopolymerEmulsogen® V 1816 (Clariant): EO-PO block copolymer
Genapol® X-060 (Clariant): Isotridecylalkohol mitGenapol® X-060 (Clariant): isotridecyl alcohol with
6 Ethylenoxideinheiten Genapol® X-080 (Clariant): Isotridecylalkohol mit6 ethylene oxide units Genapol® X-080 (Clariant): isotridecyl alcohol with
8 Ethylenoxideinheiten8 ethylene oxide units
Genapol® PF 10 (Clariant): EO-PO-EO-BlockcopolymerGenapol® PF 10 (Clariant): EO-PO-EO block copolymer
Genapol® PF 20 (Clariant): EO-PO-EO-BlockcopolymerGenapol® PF 20 (Clariant): EO-PO-EO block copolymer
Genapol® PF 40 (Clariant): EO-PO-EO-BlockcopolymerGenapol® PF 40 (Clariant): EO-PO-EO block copolymer
Phenylsulfonat® Ca 70 (Clariant): CalciumdodecylbenzolsulfonatPhenylsulfonate® Ca 70 (Clariant): calcium dodecylbenzenesulfonate
Phenylsulfonat® Ca 100Phenylsulfonate® Ca 100
(synonym Calsogen® AR 100 ND, Clariant): Calciumdodecylbenzolsulfonat(synonymous Calsogen® AR 100 ND, Clariant): Calcium dodecylbenzenesulfonate
Solvesso® 200 (Exxon): AromatengemischSolvesso® 200 (Exxon): Aromatic mixture
Solvesso® 200 ND (Exxon) : AromatengemischSolvesso® 200 ND (Exxon): Aromatic mixture
(Naphthalingehalt < 1 Gew.-%)(Naphthalene content <1% by weight)
Triton® GR 7 ME (Union Carbide): Di-(2-Ethylhexyl)Sulfosuccinat-Triton® GR 7 ME (Union Carbide): di (2-ethylhexyl) sulfosuccinate
Natriumsodium
Arkopal® N100 (Clariant): Nonylphenyolpolyglykolether Crillet® 45 (Croda): POE-20 Sorbitantrioleat Etocas® 29 (Croda): Ethoxy(29) Castor oil Triethylphosphat (Merck): Triethylphosphat XyIoI (Exxon): aromatischer Kohlenwasserstoff n-Methylpyrrolidon (BASF): N-Methyl-2-pyrrolidon n-Decanol (Merck): C10-AIkOhOl n-Octanol (Merck): C8-AIkOhOl. n-Heptanol (Merck): C7-AIkOhOl n-Hexanol (Merck): C6-AIkOhOlArkopal® N100 (Clariant): Nonylphenyol polyglycol ether Crillet® 45 (Croda): POE-20 Sorbitan trioleate Etocas® 29 (Croda): ethoxy (29) Castor oil Triethyl phosphate (Merck): Triethyl phosphate XyIoI (Exxon): Aromatic Hydrocarbons n-methylpyrrolidone (BASF): N-methyl-2-pyrrolidone n-decanol (Merck): C 10 -AlkOhOl n-octanol (Merck): C 8 -AlkOhOl. n-Heptanol (Merck): C 7 -AlkOhOl n-Hexanol (Merck): C 6 -AlkOhOl
3. Biologische Vergleichsversuche:3. Biological Comparative Experiments:
Die in der Tabelle I aufgelisteten erfindungsgemäßen Mikroemulsionskonzentrate weisen die gewünschten Eigenschaften auf. In Tabelle Il ist die Wirkung der erfindungsgemäßen Mikroemulsionskonzentrate auf Unkräuter im Vergleich zu einer Standardformulierung bei gleicher Anwendungskonzentration dargestellt.The microemulsion concentrates according to the invention listed in Table I have the desired properties. Table II shows the effect of the microemulsion concentrates according to the invention on weeds in comparison with a standard formulation at the same application concentration.
3.1 Versuchsdurchführung -3.1 Experimental Procedure -
Durchführung als Feldversuch in Nordamerika. Unkräuter und Kulturpflanzen wurden in Parzellen nebeneinander ausgesät und nach Auflauf gleichmäßig im Querstreifenverfahren mit den Versuchsgliedern behandelt. Bonitur erfolgte 4 Wochen nach Behandlung mit den Boniturwerten: O (keine Unkrautkontrolle) - 100 (vollständige Unkrautkontrolle). Execution as a field trial in North America. Weeds and crop plants were sown in plots side by side and treated after emergence evenly in the transverse stripe method with the experimental limbs. Evaluation took place 4 weeks after treatment with the rating values: O (no weed control) - 100 (complete weed control).
3.2 Versuchsergebnisse -3.2 Test results -
Tabelle Il - Wirkung unterschiedlicher FormulierungstypenTable II - Effect of Different Formulation Types
*) Zusammensetzung von "Furore Super EW 69" (Hersteller Bayer CropScience, im Handel erhältlich).*) Composition of "Furore Super EW 69" (manufacturer Bayer CropScience, commercially available).
3.3 Diskussion der Ergebnisse -3.3 Discussion of the results -
Wie aus Tabelle Il hervorgeht, bewirken die erfindungsgemäßen Mikroemulsionskonzentrate eine deutlich verbesserte biologische Wirkung bei gleicher Anwendungsdosierung als die Standardformulierung des Standes der Technik. As can be seen from Table II, the microemulsion concentrates according to the invention produce a significantly improved biological effect at the same application dosage as the standard formulation of the prior art.

Claims

Patentansprüche: claims:
1. Mikroemulsionskonzentrat, enthaltend a) ein oder mehrere agrochemische Wirkstoffe, insbesondere aus der Gruppe der Fungizide, Insektizide, Pflanzenwachstumsregulatoren, Herbizide und Safener, b) ein oder mehrere alkoholische Lösungsmittel mit mindestens 5 C-Atomen, c) ein oder mehrere nicht-alkoholische Lösungsmittel, d) ein oder mehrere anionische Tenside, und e) ein oder mehrere nichtionische Tenside.1. microemulsion concentrate containing a) one or more agrochemical active ingredients, in particular from the group of fungicides, insecticides, plant growth regulators, herbicides and safeners, b) one or more alcoholic solvents having at least 5 carbon atoms, c) one or more non-alcoholic Solvent, d) one or more anionic surfactants, and e) one or more nonionic surfactants.
2. Mikroemulsionskonzentrat gemäß Anspruch 1 , worin als Komponente (a) enthalten sind, ein oder mehrere herbizide Wirkstoffe, allein oder zusammen mit Safenern.2. microemulsion concentrate according to claim 1, wherein as component (a) are contained, one or more herbicidal active compounds, alone or together with safeners.
3. Mikroemulsionskonzentrat gemäß Anspruch 1 oder 2, worin als Komponente (b) enthalten sind, ein oder mehrere Lösungsmittel aus der Gruppe Benzylalkohol, n-, i-, s- Hexanol, n-, i-, s- Heptanol und n-, i-, s- Octanol.3. microemulsion concentrate according to claim 1 or 2, wherein as component (b) are contained, one or more solvents from the group benzyl alcohol, n-, i-, s-hexanol, n-, i-, s-heptanol and n-, i, s octanol.
4. Mikroemulsionskonzentrat gemäß einem oder mehreren der Ansprüche 1 bis 3, worin als Komponente (d) enthalten sind, ein oder mehrere anionische Tenside aus der Gruppe Sulfate, Sulfonate, Phosphate und Phosphonate von Kohlenwasserstoffen, die optional alkoxyliert sein können, vorzugsweise Dialkyl- Sulfosuccinate, Alkylarylsulfonate, Alkylethersulfate, Alkylsulfate, Alkylsulfonate, Alkylpolyglykoletherphosphate, Alkylarylpolyglykoletherphosphate und - phosphonate.4. microemulsion concentrate according to one or more of claims 1 to 3, wherein as component (d), one or more anionic surfactants selected from the group sulfates, sulfonates, phosphates and phosphonates of hydrocarbons, which may optionally be alkoxylated, preferably dialkyl sulfosuccinates , Alkylaryl sulfonates, alkyl ether sulfates, alkyl sulfates, alkyl sulfonates, alkyl polyglycol ether phosphates, alkylaryl polyglycol ether phosphates and phosphonates.
5. Mikroemulsionskonzentrat gemäß einem oder mehreren der Ansprüche 1 bis 4, worin als Komponente (e) enthalten sind, ein oder mehrere nichtionische Tenside aus der Gruppe Alkoxylate, vorzugsweise Alkylarylpolyalkoxylate, Alkylenoxid- Blockcopolymere, Polyalkylenoxide, die mit Cio-C22-Kohlenwasserstoffresten substituiert sein können, alkoxylierte Öle, alkoxylierte Cio-C22-Fettamine.5. microemulsion concentrate according to one or more of claims 1 to 4, wherein contained as component (e), one or more nonionic surfactants from the group alkoxylates, preferably alkylarylpolyalkoxylates, alkylene oxide Block copolymers, polyalkylene oxides, which may be substituted by Cio-C 22 hydrocarbon radicals, alkoxylated oils, alkoxylated Cio-C 22 fatty amines.
6. Mikroemulsionskonzentrat gemäß einem oder mehreren der Ansprüche 1 bis 5, zusätzlich enthaltend übliche Hilfs- und Zusatzstoffe (Komponente f).6. microemulsion concentrate according to one or more of claims 1 to 5, additionally containing customary auxiliaries and additives (component f).
7. Verfahren zur Herstellung eines Mikroemulsionskonzentrats gemäß einem oder mehreren der Ansprüche 1 bis 6, worin die Komponenten gemischt werden.7. A process for the preparation of a microemulsion concentrate according to one or more of claims 1 to 6, wherein the components are mixed.
8. Verwendung eines Mikroemulsionskonzentrats gemäß einem oder mehreren der Ansprüche 1 bis 6, zur Herstellung einer Mikroemulsion.8. Use of a microemulsion concentrate according to one or more of claims 1 to 6, for the preparation of a microemulsion.
9. Agrochemisches Mittel in Form einer Mikroemulsion oder der daraus erhältlichen Spritzbrühe, enthaltend a) ein oder mehrere agrochemische Wirkstoffe, insbesondere aus der Gruppe der Fungizide, Insektizide, Pflanzenwachstumsregulatoren, Herbizide und Safener, b) ein oder mehrere alkoholische Lösungsmittel mit mindestens 5 C-Atomen, c) ein oder mehrere nicht-alkoholische Lösungsmittel, d) ein oder mehrere anionische Tenside, e) ein oder mehrere nichtionische Tenside, und Wasser.9. An agrochemical composition in the form of a microemulsion or the spray mixture obtainable therefrom, comprising a) one or more agrochemical active compounds, in particular from the group of fungicides, insecticides, plant growth regulators, herbicides and safeners, b) one or more alcoholic solvents having at least 5 C C) one or more non-alcoholic solvents, d) one or more anionic surfactants, e) one or more nonionic surfactants, and water.
10. Agrochemisches Mittel gemäß Anspruch 9, zusätzlich enthaltend übliche Hilfs- und Zusatzstoffe (Komponente f).10. Agrochemical composition according to claim 9, additionally containing customary auxiliaries and additives (component f).
11. Agrochemisches Mittel gemäß Anspruch 9 oder 10, enthaltend als Komponente (b) ein oder mehrere Lösungsmittel aus der Gruppe Benzylalkohol, n-, i-, s- Hexanol, n-, i-, s- Heptanol und n-, i-, s- Octanol. 11. Agrochemical composition according to claim 9 or 10, comprising as component (b) one or more solvents from the group of benzyl alcohol, n-, i-, s-hexanol, n-, i-, s-heptanol and n-, i- , s-octanol.
12. Agrochemisches Mittel, erhältlich durch Verdünnen eines Mikroemulsionskonzentrats gemäß einem oder mehreren der Ansprüche 1 bis 6, mit Wasser.12. Agrochemical agent obtainable by diluting a microemulsion concentrate according to one or more of claims 1 to 6, with water.
13. Verfahren zur Herstellung eines agrochemischen Mittels gemäß einem oder mehreren der Ansprüche 9 bis 12, worin die Komponenten gemischt werden.13. A process for the preparation of an agrochemical composition according to one or more of claims 9 to 12, wherein the components are mixed.
14. Verfahren zur Bekämpfung von Schadorganismen, worin eine wirksame Menge eines agrochemischen Mittels gemäß einem oder mehreren der Ansprüche 1 bis 6 oder 9 bis 12 auf die Schadorganismen oder die Orte an denen sie auftreten appliziert wird.14. A method for controlling harmful organisms, wherein an effective amount of an agrochemical composition according to one or more of claims 1 to 6 or 9 to 12 is applied to the harmful organisms or the places where they occur.
15. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, worin eine wirksame Menge eines herbiziden Mittels gemäß einem oder mehreren der15. A method for controlling undesired plant growth, wherein an effective amount of a herbicidal composition according to one or more of
Ansprüche 1 bis 6 oder 9 bis 12 auf die Schadpflanzen, Teile der Pflanzen, Pflanzensamen, Ort oder Fläche auf der Pflanzen wachsen appliziert wird.Claims 1 to 6 or 9 to 12 is applied to the harmful plants, parts of plants, plant seeds, place or area on the plants grow.
16. Verwendung eines agrochemischen Mittels gemäß einem oder mehreren der Ansprüche 1 bis 6 oder 9 bis 12, zur Bekämpfung von Schadorganismen.16. Use of an agrochemical composition according to one or more of claims 1 to 6 or 9 to 12, for controlling harmful organisms.
17. Verwendung gemäß Anspruch 16, worin die Schadorganismen Schadpflanzen sind. 17. Use according to claim 16, wherein the harmful organisms are harmful plants.
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EP1886560A1 (en) 2008-02-13
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CO6150082A2 (en) 2010-04-20
AR062169A1 (en) 2008-10-22
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KR20090038032A (en) 2009-04-17
CA2660023A1 (en) 2008-02-14
AU2007283110A1 (en) 2008-02-14
WO2008017378A3 (en) 2009-02-19
ZA200900778B (en) 2009-12-30
CN101562968A (en) 2009-10-21
UA96771C2 (en) 2011-12-12

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