EP0775136A1 - Derives de saccharine substitues par 5-hydroxypyrazol-4-yl-carbonyle presentant des proprietes herbicides - Google Patents

Derives de saccharine substitues par 5-hydroxypyrazol-4-yl-carbonyle presentant des proprietes herbicides

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Publication number
EP0775136A1
EP0775136A1 EP95927734A EP95927734A EP0775136A1 EP 0775136 A1 EP0775136 A1 EP 0775136A1 EP 95927734 A EP95927734 A EP 95927734A EP 95927734 A EP95927734 A EP 95927734A EP 0775136 A1 EP0775136 A1 EP 0775136A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
methyl
hydrogen
saccharin
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Withdrawn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
EP95927734A
Other languages
German (de)
English (en)
Inventor
Peter Plath
Wolfgang Von Deyn
Stefan Engel
Uwe Kardorff
Hartmann König
Harald Rang
Matthias Gerber
Helmut Walter
Karl-Otto Westphalen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0775136A1 publication Critical patent/EP0775136A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present application relates to 5-hydroxypyrazol-4-ylcarbonyl-substituted saccharin derivatives of the formula I.
  • L, M is hydrogen, -CC 4 alkyl, -C-C 4 alkoxy, -C-C 4 alkylthio, chlorine, cyano, methylsulfonyl, itro or trifluoromethyl;
  • Z is hydrogen, -CC 4 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, 20 C 3 -C 5 -alkynyl, -C-C 4 -acyl, optionally by halogen or C ⁇ -C 4th -Alkyl substituted benzyl or phenyl;
  • 25 J is a 5-hydroxypyrazole ring of the formula II linked in position 4
  • R2 is hydrogen or methyl
  • the invention further relates to herbicidal compositions comprising the compounds I and processes for controlling unwanted vegetation with the saccharin derivatives I.
  • saccharin derivatives with herbicidal activity cannot be found in the prior art.
  • 4-Hydroxy-saccharin (DE-OS 36 07 343) is also known as a sweetener.
  • saccharin derivatives in pest control, for example JP publication 72/00419, 73/35457 (fungicides) and in pharmacy, for example EP-A-594 257 and patents mentioned therein.
  • Heterocyclic compounds with a ring containing a sulfonamide group have become known as herbicides, and bentazone is a typical representative here
  • the object of the invention was to provide new herbicides with a basic structure hitherto unknown for this indication. Accordingly, the compounds I defined at the outset were found.
  • the first step of the reaction sequence, the acylation is carried out in a generally known manner, e.g. B. by adding an acid chloride of formula IV to the solution or suspension of a 5-hydroxypyrazole II in the presence of an auxiliary base.
  • the reactants and the auxiliary base are expediently used in approximately equimolar amounts. A slight excess of the auxiliary base, for example 1.2 to 1.5 molar equivalents, based on II, may be advantageous.
  • Suitable auxiliary bases are e.g. tertiary alkyl amines, pyridine or alkali carbonates, while methylene chloride, diethyl ether, toluene or ethyl acetate can be used as the solvent.
  • the reaction mixture is advantageously cooled to 0-10 ° C, then at a higher temperature, e.g. stirred at a temperature of 25-50 ° C until the reaction is complete.
  • the processing takes place in the usual way, e.g. the reaction mixture is poured into water and extracted with methylene chloride. After drying the organic phase and removing the solvent, the crude 5-hydroxypyrazole ester can be used for rearrangement without further purification.
  • Preparation examples for benzoic acid esters of 5-hydroxy-pyrazoles can be found, for. B. in EP-A-282 944 or US 4,643,757.
  • the rearrangement of the 5-hydroxypyrazole esters to the compounds of the formula 1.1 is advantageously carried out at from 20 ° C. to 40 ° C. in a solvent and in the presence of an auxiliary base and with the aid of a cyano compound as catalyst.
  • a solvent e.g. Acetonitrile, methylene chloride, 1,2-dichloroethane, ethyl acetate or toluene can be used.
  • the preferred solvent is acetonitrile.
  • Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali carbonates, which are used in equimolar amounts or up to four times the excess.
  • Preferred auxiliary base is tri-ethylamine in double
  • Suitable catalysts are cyanide compounds such as potassium cyanide or acetone cyanohydrin, e.g. in an amount of 1 to 50, especially 5-20 mole percent, based on the 5-hydroxy-pyrazole ester.
  • Acetone cyanohydrin is preferably used e.g. in amounts of 10 mole percent.
  • the processing takes place in the usual way, e.g. the reaction mixture is acidified with dilute mineral acids such as 5% hydrochloric acid or sulfuric acid and extracted e.g. with methylene chloride or ethyl acetate.
  • dilute mineral acids such as 5% hydrochloric acid or sulfuric acid
  • the extract is extracted with cold 5 - 10% alkali carbonate solution, the end product passing into the aqueous phase.
  • the product of the formula I is precipitated by acidifying the aqueous solution, or extracted again with methylene chloride, dried and then freed from the solvent.
  • 5-hydroxypyrazoles of the formula II used as starting material are known and can be prepared by processes known per se (cf. EP-A 240 001 and J. Prakt. Chem. 3J L, 382 (1973)). 1,3-Dimethyl-5-hydroxypyrazole is a commercially available compound.
  • the starting materials of formula IV are known in a conventional manner by reacting saccharin carboxylic acid III
  • Saccharin carboxylic acids can also be obtained by appropriate bro - or iodine - substituted saccharin derivatives of the formula AI
  • Iodosaccharins are already known from the literature: 6-iodosaccharin: De Roode, Amer. Chem. Journal H, 231 (1891). They are obtained either by permanganate oxidation of iodine-substituted 2-methylbenzenesulfonamides or by a Sandmeyer reaction from amino saccharins. Aminosaccharins are obtained by known methods by reduction of nitrosaccharins, which are either known (Kastle, Amer. Chem. Journal H, 184 (1889) or DRP 551423 (1930) or in a manner known from the literature from suitable nitrobenzene derivatives (Liebigs Ann 669.85 (1963) or nitrobenzenesulfonamides.
  • reaction sequence can be represented as follows:
  • the catalysts nickel, cobalt, rhodium and in particular palladium can be metallic or in the form of conventional salts such as in the form of halogen compounds, for example P Cl 2 , RhCl 3 -H 2 0, acetates, for example Pd (OAc) 2 cyanides etc. in the known valence levels available.
  • Phosphines for example (PPh 3 ) 2 Ni (CO) 2 or transition metal salts complexed with tertiary phosphines are present.
  • the latter embodiment is particularly preferred in the case of palladium as a catalyst.
  • the type of phosphine ligand is widely variable. For example, they can be represented by the following formulas: R 3 R3 ⁇ ⁇ R5
  • n is the numbers 1, 2, 3 or 4 and the radicals R 3 to R 6 for low molecular weight alkyl, for example Ci-C ⁇ -alkyl, aryl, C 1 -C 4 -alkyl aryl, for example benzyl, or phenethyl, or Aryloxy stand.
  • Aryl is, for example, naphthyl, anthryl and preferably optionally substituted phenyl, the substituents only having to be considered for their inertness to the carboxylation reaction, otherwise they can be varied widely and include all inert C-organic radicals such as Ci-C ß -Alkyl radicals, for example methyl, carboxyl radicals such as COOH, COOM (M is, for example, an alkali metal, alkaline earth metal or ammonium salt), or C-organic radicals bound via oxygen, such as Ci-C ⁇ alkoxy radicals.
  • Ci-C ß -Alkyl radicals for example methyl
  • carboxyl radicals such as COOH, COOM (M is, for example, an alkali metal, alkaline earth metal or ammonium salt)
  • C-organic radicals bound via oxygen such as Ci-C ⁇ alkoxy radicals.
  • the phosphine complexes can be prepared in a manner known per se, for example as described in the documents mentioned at the outset. For example, one starts from customary commercially available metal salts such as PdCl 2 or Pd (OCOCH 3 ) 2 and adds the phosphine ZB P (C 6 H 5 ) 3 , P (nC 4 Hg) 3 , PCH 3 (C 6 H 5 ) Add 2 »1,2-bis (diphenylphosphino) ethane.
  • the amount of phosphine, based on the transition metal is usually 0 to 20, in particular 0.1 to 10 mol equivalents, particularly preferably 1 to 5 mol equivalents.
  • the amount of transition metal is not critical. Of course, for reasons of cost, you will rather get a small amount, e.g. from 0.1 to 30 10 mol%, in particular 1 to 5 mol%, based on the starting material AI or A2.
  • reaction is carried out with carbon onoxide and at least equimolar amounts of water, based on the starting materials A1 and A2.
  • the reaction partner water can also serve as a solvent, i.e. the maximum amount is not critical.
  • Suitable inert solvents for carboxylation reactions are conventional solvents such as hydrocarbons, for example toluene, xylene, hexane, pentane, cyclohexane, ethers, for example methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, substituted amides such as Dimethylformamide, per-substituted ureas such as tetra-C 4 -alkylureas or nitriles such as benzonitrile or acetonitrile.
  • hydrocarbons for example toluene, xylene, hexane, pentane, cyclohexane, ethers, for example methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, substituted amides such as Dimethylformamide, per-substituted
  • one of the reactants, in particular the base is used in excess, so that no additional solvent is required.
  • Bases suitable for the process are all inert bases which are able to bind the hydrogen iodide or hydrogen bromide released during the reaction.
  • tertiary amines such as triethylamine, cyclic amines such as N-methylpiperidine or N, N-dimethylpiperazine, pyridine, alkali metal or alkaline earth metal hydroxides, carbonates, or hydrogen carbonates or tetra-alkyl-substituted urea derivatives such as tetra-C 1 -C 4 alkyl urea, for example tetramethyl urea.
  • the amount of base is not critical, usually 1 to 10, in particular 1 to 5, moles were used.
  • the amount is generally measured so that the reactants are dissolved, unnecessarily high excesses being avoided for reasons of practicality in order to save costs, to be able to use small reaction vessels and to give the reactants maximum contact guarantee.
  • the carbon monoxide pressure is adjusted so that there is always an excess of CO, based on AI or A2.
  • the carbon monoxide pressure at room temperature is preferably 1 to 250 bar, in particular 5 to 150 bar CO.
  • the carbonylation is generally carried out continuously or batchwise at temperatures from 20 to 250 ° C., in particular at 30 to 150 ° C.
  • carbon monoxide is expediently pressed continuously onto the reaction mixture in order to maintain a constant pressure.
  • the products can be prepared in the usual way, e.g. be isolated by distillation.
  • the starting materials AI or A2 required for the reaction are known or can be prepared in a manner known per se, for example as described in the prior art cited. In addition, they can be obtained analogously to the preparation instructions from Examples 1 to 12.
  • saccharin derivatives of the formula I are preferred in which the radicals L and M are hydrogen, methyl, methoxy, methylthio, chlorine, cyano, methylsulfonyl, nitro or trifluoromethyl.
  • L and M are preferably hydrogen, -CC 4 -alkyl and chlorine.
  • R 1 in formula I preferably represents methyl and R 2 preferably represents hydrogen or methyl.
  • the radical Z particularly preferably represents one of the organic radicals mentioned, in particular methyl, ethyl, propargyl, acetyl or phenyl.
  • the compounds I can be in the form of their agriculturally useful salts, the type of salt generally not being important. Usually the salts of such bases will be considered which do not adversely affect the herbicidal activity of I.
  • Particularly suitable basic salts are those of the alkali metals, preferably the sodium and potassium salts, those of the earth alkali metals, preferably calcium, magnesium and barium salts and those of the transition metals, preferably manganese, copper, zinc and iron salts and the ammonium salts which can carry one to three C 1 -C 4 alkyl, hydroxy C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl - (2-Hydroxyethyl) ammonium salts, the phosphonium salts, the sulfonium salts, preferably tri- (C 1 -C 4 -) alkylsulfonium salts, and the sulfoxonium salts, preferably tri- (C ⁇ -C 4 -) alkyl
  • the compounds or the herbicidal compositions comprising them and their environmentally compatible salts of, for example, alkali metals, alkaline earth metals or ammonia and amines or the herbicidal compositions comprising them can be very weeds and harmful grasses in crops such as wheat, rice, corn, soybeans and cotton Good fight without significantly damaging the crops. This effect occurs especially at low application rates.
  • the compounds or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants, for example the following crops are suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis , Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • the compounds can also be used in crops which have been made largely resistant to the action of I or other herbicides by breeding and / or by means of genetic engineering methods.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active substances are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active compounds grow more rapidly on the leaves underneath plant undesirable or reach the uncovered floor area (post-directed, lay-by).
  • the compounds or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous oily or other suspensions or dispersions, emulsions, old dispersions, pastes, dusts, sprays or granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons , e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. Amines such as N-methylpyrrolidone, or water.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons , e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes or their
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols and of fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octylphenylphenylphenylphenylphenylphenylphen
  • Powders, materials for spreading and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urinary
  • the formulations generally contain between 0.01 and 20 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds Ia or Ia 'according to the invention can be formulated, for example, as follows: 25
  • Dissolved mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
  • the saccharin carboxylic acid derivatives can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexan-l come as mixing partners.
  • 3-dione derivatives which carry, for example, a carboxy or carbimino group, quinoline carboxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy, heteroaryloxyphenoxypropionic acids and their salts, esters and amides and others. It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
  • the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • This substance can be prepared by subsequent methylation of the saccharin obtained under 6 with dimethyl sulfate in the presence of NaOH. 0
  • the product is sufficiently pure for subsequent implementation.
  • the mixture is filtered and water and tetramethylurea are removed by distillation in a high vacuum.
  • the residue is taken up in methyl tert-butyl ether (MTBE), with NaHCO 3 solution. extracted and extracted again with MTBE after acidification with HCl. After concentration, 2.8 g of 4-methyl-saccharin-5-carboxylic acid (58% of theory) are obtained.
  • MTBE methyl tert-butyl ether
  • Methylene chloride remains an oil that is used for rearrangement without further purification.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the vessels were sprinkled lightly to promote germination and growth, and then covered with transparent plastic hoods until the plants had grown. This cover causes the test plants to germinate uniformly, provided this was not impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. The test plants were either sown directly and grown in the same containers or they are first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to the individual treatments was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des dérivés de saccharine substitués par 5-hydroxypyrazol-4-yl-carbonyle, de formule (I), où: L,M représentent hydrogène, alkyle comportant un à quatre atomes de carbone, alcoxy comportant un à quatre atomes de carbone, alkylthio comportant un à quatre atomes de carbone, chlore, cyano, méthylsulfonyle, nitro ou trifluorométhyle; Z représente hydrogène, alkyle comportant un à quatre atomes de carbone, cycloalkyle comportant trois à huit atomes de carbone, alcényle comportant trois à six atomes de carbone, alkynyle comportant trois à cinq atomes de carbone, acyle comportant un à quatre atomes de carbone, benzyle ou phényle, les noyaux phényle étant éventuellement substitués chacun par halogène ou alkyle comportant un à quatre atomes de carbone; Q représente un radical CO-J; J représente un noyau 5-hydroxypyrazole lié en position 4, de formule (II), où R1 représente alkyle comportant un à quatre atomes de carbone et R2 représente hydrogène ou méthyle. L'invention concerne également les sels utilisés communément en agriculture des composés de formule (I).
EP95927734A 1994-08-08 1995-07-27 Derives de saccharine substitues par 5-hydroxypyrazol-4-yl-carbonyle presentant des proprietes herbicides Withdrawn EP0775136A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4427997 1994-08-08
DE4427997A DE4427997A1 (de) 1994-08-08 1994-08-08 5-Hydroxypyrazol-4-yl-carbonyl-substituierte Saccharinderivate
PCT/EP1995/002974 WO1996005197A1 (fr) 1994-08-08 1995-07-27 Derives de saccharine substitues par 5-hydroxypyrazol-4-yl-carbonyle presentant des proprietes herbicides

Publications (1)

Publication Number Publication Date
EP0775136A1 true EP0775136A1 (fr) 1997-05-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP95927734A Withdrawn EP0775136A1 (fr) 1994-08-08 1995-07-27 Derives de saccharine substitues par 5-hydroxypyrazol-4-yl-carbonyle presentant des proprietes herbicides

Country Status (12)

Country Link
US (1) US5723415A (fr)
EP (1) EP0775136A1 (fr)
JP (1) JPH10506618A (fr)
CN (1) CN1157616A (fr)
AU (1) AU3166695A (fr)
BR (1) BR9508553A (fr)
CA (1) CA2197118A1 (fr)
DE (1) DE4427997A1 (fr)
HU (1) HU216284B (fr)
RU (1) RU2159244C2 (fr)
WO (1) WO1996005197A1 (fr)
ZA (1) ZA956577B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0945449B1 (fr) * 1998-03-25 2001-05-23 Basf Aktiengesellschaft Procédé de préparation d'halogénures d'acides saccharinecarboxyliques
AU4562000A (en) * 1999-05-07 2000-11-21 Basf Aktiengesellschaft 4-(3',4'-heterocyclyl benzoyl) pyrazoles as herbicidal agents
AR031786A1 (es) * 2000-12-11 2003-10-01 Basf Ag 5-((pirazol-4-il)carbonil)benzazolonas
CN114133345A (zh) * 2020-12-17 2022-03-04 顺毅宜昌化工有限公司 一种2-氯磺酰基-4-甲磺酰胺甲基苯甲酸甲酯的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4146726A (en) * 1974-03-28 1979-03-27 Sankyo Company Limited Pyrazole sulfonates
US4006007A (en) * 1975-01-02 1977-02-01 Monsanto Company N-(Substituted phenyl) derivatives of saccharin
JPS5716867A (en) * 1980-07-04 1982-01-28 Sankyo Co Ltd Pyrazole derivative and herabicide containing the same as active principle
US4410353A (en) * 1981-07-17 1983-10-18 Rhone-Poulenc Agrochimie Herbicidal N-sulfonyl 5-[substituted phenoxy]-2-substituted benzamides
DE3607343A1 (de) * 1985-03-19 1986-09-25 Dr. Karl Thomae Gmbh, 88400 Biberach Verfahren zur herstellung von 4-hydroxy-1,2-benzisothiazol-3(2h)-on-1,1-dioxid und seinen salzen
EP0323869A1 (fr) * 1988-01-06 1989-07-12 Shell Internationale Researchmaatschappij B.V. Dérivés de saccharine
US5306818A (en) * 1990-11-01 1994-04-26 Sterling Winthrop Inc. Tetrahydro 2-saccharinylmerthyl aryl carboxylates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9605197A1 *

Also Published As

Publication number Publication date
ZA956577B (en) 1997-02-07
HUT77177A (hu) 1998-03-02
HU216284B (hu) 1999-06-28
CN1157616A (zh) 1997-08-20
WO1996005197A1 (fr) 1996-02-22
JPH10506618A (ja) 1998-06-30
BR9508553A (pt) 1997-11-11
AU3166695A (en) 1996-03-07
DE4427997A1 (de) 1996-02-15
RU2159244C2 (ru) 2000-11-20
CA2197118A1 (fr) 1996-02-22
US5723415A (en) 1998-03-03

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