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WO1993016079A1 - Triazolopyrimidinesulfonamides en tant qu'herbicides - Google Patents

Triazolopyrimidinesulfonamides en tant qu'herbicides Download PDF

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Publication number
WO1993016079A1
WO1993016079A1 PCT/EP1993/000171 EP9300171W WO9316079A1 WO 1993016079 A1 WO1993016079 A1 WO 1993016079A1 EP 9300171 W EP9300171 W EP 9300171W WO 9316079 A1 WO9316079 A1 WO 9316079A1
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Prior art keywords
formula
hydrogen
methyl
independently
active ingredient
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PCT/EP1993/000171
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English (en)
Inventor
Hans Tobler
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Ciba-Geigy Ag
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Publication date
Application filed by Ciba-Geigy Ag filed Critical Ciba-Geigy Ag
Priority to EP93917370A priority Critical patent/EP0630377A1/fr
Publication of WO1993016079A1 publication Critical patent/WO1993016079A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms

Definitions

  • the present invention relates to novel herbicidally active and plant-growth-inhibiting triazolo[l,5-a]pyrimidine-2-sulfonamides, to processes for their preparation, compositions containing these triazolopyrimidinesulfonamides as active ingredients, and to their use for controlling weeds, especially selectively in crops of useful plants, and for inhibiting the growth of plants.
  • Novel herbicidally active triazolo[l,5-a]pyrimidine-2-sulfonamides have now been which are distinguished from the l-2,4-triazolo[l,5-a]pyrimidine-2-sulfonamides which have already been disclosed by the fact that they are more readily degradable.
  • R 3 is C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, benzyl or optionally substituted phenyl;
  • n is the number 0, 1 or 2;
  • R 4 , R 5 , R 6 , R and R 8 independently of one another are hydrogen or C r C 4 alkyl; and
  • X and Y independently of one another are hydrogen, ⁇ alkyl or C 3 ⁇ C 6 cycloalkyl; and the agrochemically acceptable salts of these compounds, with the proviso that the radicals X and Y are not simultaneously hydrogen.
  • Halogen in the above definitions is to be understood as meaning fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine and bromine.
  • Suitable alkyl groups for Rj to Rg, X and Y can be straight-chain or branched alkyl groups, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl; preferably alkyl groups having 1 to 2 carbon atoms.
  • Haloalkyl groups which are suitable for R l5 R 2 and R 3 are alkyl groups which are mono- or polysubstituted by halogen, halogen specifically being fluorine, chlorine, bromine or iodine.
  • alkyl groups which are mono- or polysubstituted by halogen are alkyl groups which are mono- to trisubstituted by halogen, in particular fluorine or chlorine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl; preferably difluoromethyl and trifluoromethyl.
  • Alkoxy radicals which are suitable for R-- and R 2 are, for example, methoxy, ethoxy, propyloxy, iso-propyloxy, n-butyloxy, iso-butyloxy, sec-butyloxy and tert-butyloxy; preferably methoxy and ethoxy.
  • Haloalkoxy radicals which are suitable for Rj and R 2 are, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2-difluoroethoxy; preferably difluoromethoxy and trifluoromethoxy.
  • and R 2 are, for example, methoxymethyl, methoxyethyl, ethoxy ethyl, ethoxyethyl and propyloxymethyl.
  • alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-l-yl; preferably alkenyl radicals having a chain length of 2 to 3 carbon atoms.
  • alkynyl is to be understood as straight-chain or branched alkynyl, for example ethynyl, propargyl, 1-methylpropargyl, but-2-yn-l-yl or but-3-yn-l-yl.
  • Substituted or unsubstituted phenyl in the radical R 3 is a phenyl ring which is substituted by 1 to 3 substituents, in particular halogen atoms, C r C 3 alkyl, C r C 3 haloalkyl, C C 3 alkoxy, ⁇ haloalkoxy, C 1 -C 3 alkanoyl, C r C 3 alkoxycarbonyl or cyano, or may be 1 to 2 nitro groups.
  • cycloalkyl radicals X and Y which are suitable as substituents are cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl.
  • the invention also embraces the salts of the compounds of the formula I, being sulfonamides with an acidic proton, can form with amines, alkali metal bases and alkaline earth metal bases or quaternary ammonium bases.
  • alkali metal hydroxides and alkaline earth metal hydroxides used in salt formation the hydroxides of lithium, sodium, potassium, magnesium or calcium are preferred and particularly preferred are those of sodium or potassium.
  • amines which are suitable for salt formation are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylehexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptyl
  • Examples of quaternary ammonium bases are generally the cations of haloammonium salts, for example the tetramethylammonium cation, the trimethylbenzylammonium cation, the triethylbenzylammonium cation, the tetraethylammonium cation, the trimethylethylammomum cation, but also the ammonium cation.
  • R ! is in the 2-position
  • R 2 the 3-, 4- or 5-position
  • the oxetan-3-oxycarbonyl radical in the 6-position of the phenyl- 1-amidosulfonyl ring.
  • R 4 , R 5 , R 6 , R and R 8 independently of one another are hydrogen or methyl, in particular hydrogen.
  • R is in the 2-position
  • R 2 in the 4-, 5- or 6-position
  • the oxetan-3-oxycarbonyl radical is in the 3-position of the phenyl- 1-amidosulfonyl ring.
  • Particularly preferred amongst these compounds of the formula lb are those in which the radical R 2 is in the 6-position, and R 4 , R 5 , Rg, R 7 and are R 8 independently of one another are hydrogen or methyl, in particular hydrogen.
  • Important compounds of the formula I, la or lb are those in which the radicals Rj and R 2 independently of one another are hydrogen, fluorine, chlorine, bromine, Cx-Qalkyl, C j -C ⁇ aloalkyl or nitro. Particularly preferred amongst these compounds of the formula I, la or lb are those in which Rj and R 2 independently of one another are fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or nitro.
  • radicals X are hydrogen, methyl or cyclopropyl; and the radicals Y are methyl or cyclopropyl.
  • Rj is hydrogen, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl
  • R 2 is hydrogen, fluorine, chlorine, methyl or methoxy
  • R 4 , R 5 , Rg, R 7 and R 8 independently of one another are hydrogen or methyl
  • X and Y independently of one another are hydrogen, methyl or cyclopropyl.
  • This process is particularly suitable for oxetan-3-oxycarbonylanilines which have activating substituents, i.e. substituents which are electron donors, for example alkyl and alkoxy groups.
  • this intermediate of the formula IV is converted in the presence of 1-hydroxybenzotriazole and the acidic carbodiimide reagent
  • This second process for the preparation of the compounds of the formula I is preferred in those cases where the oxetan-3-oxycarbonylanilines of the formula II are not accessible or cannot be reacted, or only with difficulty, with the l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonyl chlorides of the formula HI according to the first one-step process due to electron-attracting substituents R j , R 2 , for example nitro, S(0) 2 R 3 or halogen.
  • the reactions which give compounds of the formula I are advantageously carried out in aprotic, inert, organic solvents.
  • solvents are hydrocarbons such as benzene, toluene, xylene, hexane or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, diethylformamide or N-methylpyrrolidone, and esters such as ethyl acetate.
  • the reaction temperatures are preferably between -10°C and +150°C.
  • the reactions are generally not, or only weakly, exothermal and can be carried out between 0°C and room temperature. To shorten the reaction time or else to trigger the reaction, it is expedient to heat the reaction mixture briefly at boiling point.
  • the reaction times can also be shortened by adding either catalytic amounts or up to 2 equivalents of a base as reaction catalyst.
  • Bases which are suitable are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, l,4-diazabicyclo-(2,2,2)-octane, l,5-diazabicyclo(4,3,0)non-5-ene or l,5-diazabicyclo(5,4,0)undec-7-ene or pyridine and 4-(N,N-dimethylamino)-pyridine.
  • tertiary amines such as trimethylamine, triethylamine, quinuclidine, l,4-diazabicyclo-(2,2,2)-octane, l,5-diazabicyclo(4,3,0)non-5-ene or l,5-diazabicyclo(5,4,0)undec-7-ene or pyridine and 4-(N,N-dimethylamino)-pyridine.
  • inorganic bases such as hydrides, for example sodium hydride or calcium hydride, hydroxides, for example sodium hydroxide and potassium hydroxide, carbonates, for example sodium carbonate and potassium carbonate, or hydrogen carbonates, for example potassium hydrogen carbonate and sodium hydrogen carbonate, can also be used as bases.
  • hydrides for example sodium hydride or calcium hydride
  • hydroxides for example sodium hydroxide and potassium hydroxide
  • carbonates for example sodium carbonate and potassium carbonate
  • hydrogen carbonates for example potassium hydrogen carbonate and sodium hydrogen carbonate
  • Heterogeneous catalysis with transition metals for example palladium, platinum or nickel (Raney nickel) in absolute, inert, organic solvents, for example tetrahydrofuran or dioxane, is preferably suitable for catalytic hydrogenation.
  • transition metals for example palladium, platinum or nickel (Raney nickel) in absolute, inert, organic solvents, for example tetrahydrofuran or dioxane
  • the end products of the formula I can be isolated by concentration and/or by evaporation of the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, for example ethers, esters, aromatic hydrocarbons or chlorinated hydrocarbons.
  • solvents in which they are not readily soluble, for example ethers, esters, aromatic hydrocarbons or chlorinated hydrocarbons.
  • isolating and purifying the products of the formula I is by means of (flash) silica gel chromatography with the aid of a suitable solvent or solvent mixture, for example ethyl acetate, hexane or tetrahydrofuran.
  • novel intermediates oxetan-3-oxycarbonylanilines of the formula II can be prepared by a range of standard processes known from the literature, for example by the following equation:
  • the compounds of the formula II are obtained by reacting a nitrobenzoic acid derivative of the formula VII in which Rj and R 2 are as defined in formula I with N,N-bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (see Synthesis 1980, 547), or thionyl chloride, oxalyl chloride and 3-oxetanol of the formula IX in which R 4 , R 5 , R 6 , R 7 and R 8 are as defined in formula I, in the presence of a suitable base, for example triethylamine, to give a compound of the formula VI in which R l ⁇ R 2 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in formula I, and subsequently subjecting this intermediate to catalytic hydrogenation in an inert solvent.
  • a suitable base for example triethylamine
  • R 4 , R 5 , R 6 , R 7 and Rg independently of one another are hydrogen or methyl are known from the literature; see J. Org. Chem. 48, 2953 (1983); J. Am. Chem. Soc. 112, 3535 (1990); Tetrahedron Lett. 30, 2505 (1969); Bull. Chem. Soc. Japan 62, 2032 (1989); and J. Am. Chem. Soc. 77, 4430 (1955).
  • R 9 is hydrogen or C r C 4 alkyl are disclosed in US-A-4 818 273 and EP-A-434 624.
  • the active ingredients of the formula I are successfully applied at application rates from 0.001 to 2 kg/ha, in particular 0.005 to 1 kg/ha.
  • the dosage rate required for the desired effect can be determined by experiments. It depends on the type of action, the development stage of the crop plant and of the weed and on the application (location, time, method) and can vary within wide ranges due to these parameters.
  • the compounds of the formula I are distinguished by growth-inhibiting and herbicidal properties which make them outstandingly suitable for use in crops of useful plants, in particular in cereals, cotton, soya beans, oilseed rape, maize and rice, the use in cotton, soya crops and cereals being very particularly preferred. Weeds in cotton and soya crops are preferably controlled pre- and post-emergence.
  • the compounds of the formula I are distinguished in particular by the fact that they are readily degraded.
  • the invention also relates to herbicidal compositions which comprise a novel active ingredient of the formula I and to a method for inhibiting the growth of plants.
  • a method for inhibiting plant growth is understood as meaning controlling the natural development of the plant without altering the life cycle of the plant, which is determined by its genetic make-up, in the sense of a mutation.
  • the method of growth inhibition is applied at a particular point in time of the development of the plant, which is to be determined in the particular case.
  • the active ingredients of the formula I can be applied before or after emergence of the plants, for example even to the seeds or seedlings, to roots, tubers, stalks, leaves, flowers or other parts of the plants. This can be effected, for example, by applying the active ingredient, as pure active ingredient or in the form of a composition, to the plants and/or by treating the nutrient substrate of the plant (soil).
  • Seed treatment a) The seeds are treated with an active ingredient formulated as a wettable powder by shaking in a container until the seed surface is uniformly covered (dry seed treatment). Up to 4 g of active ingredient of the formula I are used per kg of seed in this method (up to 8.0 g of wettable powder in the case of a 50 % formulation).
  • the seeds are treated with an emulsion concentrate of the active ingredient or with an aqueous solution of the active ingredient of the formula I formulated as a wettable powder, using method a) (wet seed treatment).
  • Seed treatment by immersing the seeds in a liquor containing up to 1000 ppm of active ingredient of the formula I for 1 to 72 hours, which, if desired, is followed by drying the seeds (seed soaking).
  • seed treatment or treatment of the germinated seedling are the preferred application methods since the treatment with active ingredient is directed entirely at the target crop.
  • 0.001 g to 4.0 g of active ingredient are used per kg of seed, but it is possible to deviate from the limit concentrations given in both directions, depending on the method chosen which also makes possible the addition of other active ingredients or micronutrients (repeated seed treatment).
  • the dissolved active ingredient is applied to mineral granule carriers or polymerized granules (urea/formaldehyde) and allowed to dry. If desired, a coating can be applied
  • the compounds of the formula I are employed in unaltered form, as obtained from synthesis or preferably together with the auxiliaries conventionally used in the art of formulation, and they are therefore processed in a known manner to give, for example, emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations, for example in polymeric substances.
  • the application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the kind of the compositions are selected to suit the intended aims and the prevailing circumstances.
  • compositions, preparations or combinations comprising the active ingredient of the formula I and, if desired, one or more solid or liquid additives, are prepared in a known manner, for example by intimately mixing and/or grinding the active ingredients with extenders, for example with solvents, solid carriers and, if desired, surface-active compounds (surfactants).
  • extenders for example with solvents, solid carriers and, if desired, surface-active compounds (surfactants).
  • aromatic hydrocarbons in particular the fractions Cg to C 12 , such as mixtures of alkylbenzenes, for example xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols such as ethanol, propanol or butanol; glycols as well as their ethers and esters, such as propylene glycol or dipropylene glycol ethers, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils as well as esters thereof, such as rapeseed, castor or soya oil; or, if desired, silicone oils.
  • aromatic hydrocarbons in particular the fractions Cg to C 12 , such as mixtures of alkylbenzenes, for
  • Solid carriers which are generally used, for example for dusts and dispersible powders are ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly-disperse silicas or highly-disperse abso ⁇ ptive polymers.
  • Possible paniculate, adsorptive carriers for granules are either porous types, for example pumice, brick grit, sepiolite or bentonite, or non-sorptive carrier materials, such as calcite or sand.
  • a large number of pregranulated materials of inorganic or organic nature can be used, such as, in particular, dolomite or comminuted plant residues.
  • Suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties, depending on the nature of the active ingredient of the formula I to be formulated.
  • Surfactants are also to be understood as meaning mixtures of surfactants.
  • Anionic surfactants which are suitable can be either so-called wa;: -soluble soaps or water-soluble synthetic surface-active compounds.
  • Suitable soaps which may be mentioned are the alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (C ⁇ -C ⁇ such as the sodium salts or potassium salts of oleic or stearic acid, or of natural mixtures of fatty acids which can be obtained, for example, from coconut or tallow oil. Mention must also be made of the fatty acid methyltaurinates.
  • the fatty alcohol sulfonates or fatty alcohol sulfates are as a rule in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts, and have an alkyl radical having 8-22 C atoms, alkyl also including the alkyl moiety of acyl radicals, for example the sodium or calcium salt of ligninsulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids.
  • This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and one fatty acid radical having 8 to 22 C atoms.
  • alkylarylsulfonates are the sodium/calcium or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensation product.
  • Suitable compounds are the corresponding phosphates, such as the salts of the phosphoric ester of a p-nonylphenol/(4-14)-ethylene oxide adduct, or phospholipids.
  • Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • non-ionic surfactants which are suitable are the water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol which have 1 to 10 carbon atoms in the alkyl chain and which contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
  • the abovementioned compounds customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants examples include nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Suitable substances are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylenesorbitan trioleate.
  • the cationic surfactants are mainly quaternary ammonium salts, which contain at least one alkyl radical having 8 to 22 C atoms as N-substituents and which have lower, possibly halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
  • the pesticidal preparations comprise 0.1 to 99 , in particular 0.1 to 95 %, of the active ingredient of the formula 1, 1 to 99 % of a solid or liquid additive and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.
  • compositions are more preferred as commercial products, the end user, as a rule, applies dilute compositions.
  • compositions can also comprise further additives such as stabilisers, for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers as well as fertilisers or other active ingredients for achieving specific effects.
  • stabilisers for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers as well as fertilisers or other active ingredients for achieving specific effects.
  • Emulsifiable concentrates are:
  • Active ingredient 1 to 90 %, preferably 5 to 50 %
  • Surfactant 5 to 30 %, preferably 10 to 20 %
  • Liquid carrier 15 to 94 %, preferably 70 to 85 %
  • Active ingredient 0.1 to 10 %, preferably 0.1 to 1 %
  • Solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • Active ingredient 5 to 75 %, preferably 10 to 50 %
  • Active ingredient 0.5 to 90 %, preferably 1 to 80 %
  • Surfactant 0.5 to 20 %, preferably 1 to 15 %
  • Solid carrier material 5 to 95 %, preferably 15 to 90 %.
  • Granules Active ingredient: 0.5 to 30 %, preferably 3 to 15 %
  • Solid carrier 99.5 to 70 %, preferably 97 to 85 %.
  • Emulsion concentrates a) b) c)
  • Tributylphenol polyethylene glycol ether (30 mol of EO)
  • Emulsions of any desired concentration can be prepared from such concentrates by diluting them with water.
  • Petroleum spirit (boiling range 160-190°C) 94%
  • the solutions are suitable for use in the form of microdrops.
  • the active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, the solvent is subsequently evaporated in vacuo.
  • Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient.
  • Wettable powders a) b) c) Active ingredient as per Tables 1 and 2 Sodium ligninsulfonate Sodium lauryl sulfate Sodium diisobutylnaphthalene- sulfonate - 6% 10%
  • the active ingredient is mixed thoroughly with the additives, and the mixture is ground thoroughly in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • Emulsions of any desired concentration can be prepared from this concentrate by diluting it with water. 7. Dusts a) b) Active ingredient as per
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture on a suitable mill.
  • the active ingredient is mixed with the additives, and the mixture is ground and moistened with water. This mixture is extruded and subsequently dried in a stream of air.
  • the finely ground active ingredient is applied uniformly to the kaolin which has been moistened with polyethylene glycol. Dust-free coated granules are obtained in this manner.
  • the finely ground active ingredient is mixed intimately with the additives.
  • a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water is obtained in this manner.
  • Example B 1 Herbicidal activity, preemergence
  • test plants are sown into seed dishes, and the soil surface is immediately afterwards treated with an aqueous spray mixture prepared with a suspension concentrate
  • Test plants Avena, Setaria, Sinapis and Stellaria.
  • aqueous spray mixture is prepared with an emulsion concentrate (Formulation Examples Nos. 1 and 6), solutions (Formulation Example No. 2), granules (Formulation Example No. 3), dusts (Formulation Examples Nos. 4 and 7), wettable powders (Formulation Example No. 5), extruder granules and coated granules (Formulation Examples Nos. 8 and 9).
  • Table Bl shows examples of the good herbicidal activity of the compounds of the formula I.
  • Test plants Avena, Setaria, Sinapis and Stellaria.
  • aqueous spray mixture is prepared with an emulsion concentrate (Formulation Examples Nos. 1 and 6), solutions (Formulation Example No. 2), granules (Formulation Example No. 3), dusts (Formulation Examples Nos. 4 and 7), wettable powders (Formulation Example No. 5), extruder granules and coated granules (Formulation Examples Nos. 8 and 9).
  • Table B2 shows examples of the good herbicidal activity of the compounds of the formula I.
  • Monochoria vag. are sown in plastic beakers (surface area 60 cm 2 , volume 500 ml). After sowing, the beakers are filled with water to the soil surface. 3 days after sowing, the water level is raised just above the soil surface (3-5 mm). Application is effected 3 days after sowing by spraying the test substances onto the containers. The dosage rate used corresponds to an amount of 8-500 g of active ingredient per hectare.
  • the beakers with the plants are then placed in a greenhouse under optimum growth conditions for the rice weeds, i.e. at 25-30°C and high atmospheric humidity.
  • the compounds of the formula I have a damaging effect on the weeds.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne les triazolo[1,5-a]pyrimidine-2-sulfonamides de la formule (I), dans laquelle R1 et R2 sont indépendamment l'un de l'autre un hydrogène, un halogène, un (C1-C4)alkyle, un (C1-C4)haloalkyle, un (C1-C4)alcoxy, un (C1-C4)haloalcoxy, un (C1-C4)alcoxy-(C1-C4)alkyle, un nitro, un phényle ou un groupe S(On)R3; R3 est un (C1-C4)alkyle, un (C1-C4)haloalkyle, un (C2-C4)alcényle, un (C2-C4)alcynyle, un benzyle ou un phényle, le cas échéant substitué; n est un nombre égal à 0, 1 ou 2; R4, R5 R6, R7 et R8 sont indépendamment l'un de l'autre un hydrogène ou un (C1-C4)alkyle; et X et Y sont indépendamment l'un de l'autre un hydrogène, un (C1-C4)alkyle ou un (C3-C6)cycloalkyle, avec comme condition toutefois que les radicaux X et Y ne peuvent pas être en même temps des hydrogènes. L'invention concerne également les sels de ces composés acceptables en agrochimie. Ces produits ont des propriétés herbicides en traitement avant et après l'émergence. Ils sont facilement dégradables. On décrit la préparation de ces produits et leur utilisation comme ingrédients actifs de compositions herbicides.
PCT/EP1993/000171 1992-02-07 1993-01-26 Triazolopyrimidinesulfonamides en tant qu'herbicides WO1993016079A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP93917370A EP0630377A1 (fr) 1992-02-07 1993-01-26 Triazolopyrimidinesulfonamides en tant qu'herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH37992 1992-02-07
CH379/92-6 1992-02-07

Publications (1)

Publication Number Publication Date
WO1993016079A1 true WO1993016079A1 (fr) 1993-08-19

Family

ID=4185678

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/000171 WO1993016079A1 (fr) 1992-02-07 1993-01-26 Triazolopyrimidinesulfonamides en tant qu'herbicides

Country Status (7)

Country Link
EP (1) EP0630377A1 (fr)
AU (1) AU3451593A (fr)
CA (1) CA2105278A1 (fr)
IL (1) IL104627A0 (fr)
MX (1) MX9300599A (fr)
WO (1) WO1993016079A1 (fr)
ZA (1) ZA93795B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998003508A3 (fr) * 1996-07-19 1998-05-22 Bayer Ag Sulfonamides de triazoloazine substitues

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0434624A1 (fr) * 1989-12-22 1991-06-26 Ciba-Geigy Ag Triazolylsulfonamides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0434624A1 (fr) * 1989-12-22 1991-06-26 Ciba-Geigy Ag Triazolylsulfonamides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998003508A3 (fr) * 1996-07-19 1998-05-22 Bayer Ag Sulfonamides de triazoloazine substitues
US6297195B1 (en) 1996-07-19 2001-10-02 Bayer Aktiengesellschaft Substituted triazoloazine sulphonamides

Also Published As

Publication number Publication date
CA2105278A1 (fr) 1993-08-08
MX9300599A (es) 1993-09-01
AU3451593A (en) 1993-09-03
EP0630377A1 (fr) 1994-12-28
ZA93795B (en) 1993-08-09
IL104627A0 (en) 1993-06-10

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