EP0775137A1 - Derives saccharine a effet herbicide - Google Patents

Derives saccharine a effet herbicide

Info

Publication number
EP0775137A1
EP0775137A1 EP95927735A EP95927735A EP0775137A1 EP 0775137 A1 EP0775137 A1 EP 0775137A1 EP 95927735 A EP95927735 A EP 95927735A EP 95927735 A EP95927735 A EP 95927735A EP 0775137 A1 EP0775137 A1 EP 0775137A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
hydrogen
saccharin
methyl
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Withdrawn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
EP95927735A
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 EP0775137A1 publication Critical patent/EP0775137A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • 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
    • 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

Definitions

  • the present application relates to saccharin derivatives of the formula I.
  • L, M is hydrogen, -CC alkyl, -CC alkoxy, -C 4 alkylthio, chlorine, cyano, methylsulfonyl, nitro or trifluoromethyl;
  • Z is hydrogen, -CC 4 alkyl, C -C 8 cycloal] ⁇ yl, C 3 -C 6 alkenyl, C 3 -C 5 alkynyl, C ⁇ C 4 -acyl, benzyl or phenyl, the phenyl rings are each optionally substituted by halogen or -CC 4 alkyl;
  • T stands for a carbonyl radical CO or for the radical -CHY, where
  • J is an isoxazole ring of the formula II linked in the 4-position
  • R 1 for hydrogen or -CC 4 alkyl
  • R 2 represents -C-alkyl, cyclopropyl, 1-methylcyclopropyl or 1-methylthiocyclopropyl;
  • Y represents an OH group, a hydroxyl group optionally acylated with C 2 -C 4 -acyl or a chlorine atom;
  • the invention furthermore relates to herbicidal compositions comprising the compounds I and processes for controlling unwanted vegetation with the saccharin derivatives I.
  • the present invention also comprises intermediates for the preparation of the end products I according to the invention and production processes for the products I under Use of the new intermediate products of formulas B2 and IV
  • Saccharin derivatives with herbicidal activity cannot be found in the prior art.
  • 4-Hydroxy-saccharin DE-OS 3 607 343
  • 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 and the intermediates B2 were found.
  • the ß-keto esters of the formula AI used as starting material are known and can, for. B. by reaction of Meldrum's acid with acid chlorides of the formula R 2 -C0C1 and subsequent reaction with tert. Butanol can be obtained.
  • R 1 is C 1 -C 4 -alkyl
  • the compounds of the formula I are obtained by reacting saccharin carboxylic acid chlorides of the formula IV with alkynylstannanes of the formula A2 to give benzoylalkynes of the formula B2 and then using nitrile oxides of the Formula C2 subjects a cycloaddition to the isoxazoles of formula 1.2:
  • M has the meaning given above and Z represents hydrogen, C 1 -C 4 -alkyl,
  • C 3 -C 8 cycloalkyl C 3 -C 6 alkenyl, C 3 -Cs alkynyl, C 1 -C 8 -acyl or for benzyl or phenyl which is optionally substituted by halogen or C 1 -C 4 alkyl.
  • Alkynylstannanes of the formula A2 can be obtained in a known manner from trialkyltin chloride and lithium acetylidene.
  • Aroylalkynes are prepared in a manner known per se from alkynylstannanes and benzoic acid chlorides in the presence of palladium catalysts such as bis (triphenylphosphine) palladium (II) chloride, such as e.g. by Crisp in Synth. Comm. 1_, 1745 (1989).
  • Nitrile oxides of the formula C2 are obtained in a known manner from hydroxamic acid chlorides and tertiary amines such as triethylamine.
  • the cycloaddition of aroylalkynes with nitrile oxides to isoxazoles is e.g. known from EP-A 487 357.
  • the starting materials of the formula IV are prepared in a manner known per se by reacting the saccharin carboxylic acid derivatives III
  • Saccharin carboxylic acids can also be obtained by corresponding bromo or iodo substituted saccharin derivatives of formula II
  • 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 PdCl 2 , RhCl • H 2 O, acetates, for example Pd (0AC) 2 , cyanides etc. in the known valence levels .
  • halogen compounds for example PdCl 2 , RhCl • H 2 O, acetates, for example Pd (0AC) 2 , cyanides etc. in the known valence levels .
  • metal complexes with tertiary phosphines metal alkylcarbonyls, metal carbonyls, for example Co 2 (CO) 8 , Ni (C0) 4 , metal carbonyl complexes with ter-phosphines, for example (PPh 3 ) 2 Ni (CO) 2 or complexed with tertiary phosphines Transition metal salts 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:
  • 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 ⁇ -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 bonded via oxygen, such as -CC 6 alkoxy radicals.
  • Ci-C ⁇ -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 bonded via oxygen such as -CC 6 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 (0C0CH 3 ) 2 and adds the phosphine, for example P (C 6 H 5 ) 3 , P (nC 4 H 9 ) 3 , PCH (C 6 H 5 ) 2 , 1,2-bis (diphenylphosphino) ethane.
  • PdCl 2 or Pd (0C0CH 3 ) 2 adds the phosphine, for example P (C 6 H 5 ) 3 , P (nC 4 H 9 ) 3 , PCH (C 6 H 5 ) 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, rather a small amount, for example from 0.1 to 10 mol%, in particular 1 to 5 mol%, based on the starting material II or III will be used. ⁇
  • the reaction is carried out with carbon onoxide and at least equimolar amounts of water, based on the starting materials A2 and A4.
  • the reaction partner water or Ci-C ⁇ -alkyl-OH 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 ⁇ -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-substitute
  • 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, amides such as N-methyl or N, N-dimethylformnamide, alkali or alkaline earth metal hydroxides,
  • the amount of base is not critical, usually 1 to 10, in particular 1 to 5, moles are used. If the base is simultaneously used as solvent, the amount is generally such that the reactants are dissolved, unnecessarily high excesses being avoided for reasons of practicality; to save costs, to be able to use small reaction vessels and to ensure maximum contact for the reaction partners.
  • the carbon monoxide pressure is adjusted so that there is always an excess of CO, based on A3 or A4.
  • 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. In the case of discontinuous operation, 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. isolated by distillation.
  • the starting materials A3 or A4 required for the reaction are known or can be prepared in a manner known per se. They can either be obtained by permanganate oxidation of iodine-substituted 2-methylbenzenesulfonamides or by Sandmeyer reaction from aminosaccharides. Aminosaccharins are obtained by known methods by reduction of nitrosaccharides, which in turn 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 benzene sulfonamides.
  • radicals L and M are hydrogen, methyl, methoxy, methylthio, chlorine, cyano, methylsulfonyl, nitro or trifluoromethyl.
  • one of the radicals L or M is hydrogen and the other radical is one of the radicals mentioned above.
  • Q particularly preferably denotes the radical CO-J.
  • the radical R 1 is preferably hydrogen and R 5 is preferably cyclopropyl or tert. Butyl.
  • the radical Z particularly preferably represents one of the C-organic radicals mentioned, in particular methyl, ethyl, acetyl, phenyl or propargyl.
  • 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 as basic salts are those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium, magnesium and barium salts and those of the transition metals, preferably manganese, copper, zinc and iron salts as well as the ammonium salts, which can carry one to three C 1 -C 4 alkyl, hydroxy C 1 -C 4 alkyls and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimeth 1 - (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 1 -C 4) al
  • the compounds I 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 weeds and harmful grasses very well in crops such as wheat, rice, corn, soybeans and cotton fight without significantly damaging the crops. This effect occurs especially at low application rates.
  • the compounds I 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:
  • the compounds I 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 unwanted plants or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • directly sprayable aqueous solutions, powders, suspensions including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules , 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 point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons , for example 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, for example amines such as N-methylpyrrolidone, or Water.
  • mineral oil fractions from medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons , for example paraffins, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the 5 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 an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as from
  • Powders, materials for broadcasting 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 45 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 I according to the invention can be formulated, for example, as follows:
  • Benzene 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid-N-monoethanol amide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
  • Dissolved mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the additive of 40 moles of ethylene oxide with 1 mole of castor oil.
  • 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 with 1 mole of castor oil.
  • the saccharin carboxylic acid derivatives I 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, cyclohexane-1 come as mixing partners.
  • 3-dione derivatives e.g.
  • the active compound application rates are from 0.01 to 3.0, preferably from 0.01 to 1.0, kg / ha of active substance (a.S.).
  • This substance can be prepared by subsequent methylation of the saccharin obtained under 8. with dimethyl sulfate in the presence of NaOH.
  • 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) 45, with NaHC0 3 solution. extracted and after acidification with HCl again with MTBE extracted. After concentration, 2.8 g of 4-methyl-1-saccharin-5-carboxylic acid (58% of theory) are obtained.
  • MTBE methyl tert-butyl ether
  • Tetramethylurea placed in a 300 ml autoclave, the mixture heated to 100 ° C and stirred for 36 h at a pressure of 100 bar carbon monoxide.
  • the herbicidal activity of the saccharin derivatives of the formula I was demonstrated by greenhouse experiments: 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 evenly, unless this was adversely affected by the active ingredients.
  • test plants For the 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. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept 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.

Landscapes

  • 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)

Abstract

L'invention concerne des dérivés saccharine de la formule (I) dans laquelle les substituants ont la notation suivante: L,M désignent hydrogène, alkyle C1-C4, alcoxy C1-C4, alkylthio C1-C4, chlore, cyano, méthylsulfonyle, nitro ou trifluorométhyle; Z désigne hydrogène, alkyle C1-C4, cycloalkyle C3-C8, alcényle C3-C6, alcinyle C3-C5, acyle C1-C4, benzyle ou phényle, les composés cycliques phényle étant éventuellement substitués par halogène ou alkyle C1-C4; Q désigne un reste T-J, T désignant un reste carbonyle CO ou le reste -CHY, J désignant un composé cyclique isoxazole de la formule (II), présentant une liaison en position 4 (II) dans laquelle R1 désigne hydrogène ou alkyle C¿1?-C4 et R?2¿ désigne alkyle C¿1?-C4, cyclopropyle, 1-méthylcyclopropyle ou 1-méthylthiocyclopropyle; Y désigne un groupe OH, un groupe hydroxy éventuellement acylé par acyle C2-C4 ou un atome de chlore. L'invention concerne en outre des sels des composés (I), d'usage courant en agriculture.
EP95927735A 1994-08-08 1995-07-27 Derives saccharine a effet herbicide Withdrawn EP0775137A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4427998A DE4427998A1 (de) 1994-08-08 1994-08-08 Saccharinderivate
DE4427998 1994-08-08
PCT/EP1995/002975 WO1996005198A1 (fr) 1994-08-08 1995-07-27 Derives saccharine a effet herbicide

Publications (1)

Publication Number Publication Date
EP0775137A1 true EP0775137A1 (fr) 1997-05-28

Family

ID=6525162

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95927735A Withdrawn EP0775137A1 (fr) 1994-08-08 1995-07-27 Derives saccharine a effet herbicide

Country Status (9)

Country Link
US (1) US5716906A (fr)
EP (1) EP0775137A1 (fr)
JP (1) JPH10505589A (fr)
AU (1) AU3166795A (fr)
CA (1) CA2197119A1 (fr)
DE (1) DE4427998A1 (fr)
TW (1) TW300891B (fr)
WO (1) WO1996005198A1 (fr)
ZA (1) ZA956578B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19543640A1 (de) * 1995-11-23 1997-05-28 Basf Ag Isoxazol-4-yl-benzoylderivate
DE19614856A1 (de) * 1996-04-16 1997-10-23 Basf Ag Herbizide heterocyclisch anellierte Benzoylisothiazole
GB9724586D0 (en) * 1997-11-20 1998-01-21 Rhone Poulenc Agriculture New herbicides
EP0945449B1 (fr) * 1998-03-25 2001-05-23 Basf Aktiengesellschaft Procédé de préparation d'halogénures d'acides saccharinecarboxyliques
BR112022024428A2 (pt) * 2020-06-04 2023-01-31 Tindall Aaron Composição e método para eliminar ou reduzir o crescimento indesejado de plantas

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Publication number Priority date Publication date Assignee Title
US1937521A (en) * 1929-10-19 1933-12-05 Flintkote Co Process for the manufacture of sulphonic acids or their salts
DE551423C (de) * 1930-05-27 1932-06-02 Chem Fab Von Heyden Akt Ges Verfahren zur Darstellung von 4-Nitro-2-sulfamid-1-benzolcarbonsaeure
US4006007A (en) * 1975-01-02 1977-02-01 Monsanto Company N-(Substituted phenyl) derivatives of saccharin
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
GB9025469D0 (en) * 1990-11-22 1991-01-09 Rhone Poulenc Agriculture New compositions of matter
US5306818A (en) * 1990-11-01 1994-04-26 Sterling Winthrop Inc. Tetrahydro 2-saccharinylmerthyl aryl carboxylates
DE69209576D1 (de) * 1991-05-10 1996-05-09 Takeda Chemical Industries Ltd Pyridinderivate, deren Herstellung und Anwendung
IL102674A (en) * 1991-08-05 1996-11-14 Rhone Poulenc Agriculture History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the same
GB9116834D0 (en) * 1991-08-05 1991-09-18 Rhone Poulenc Agriculture Compositions of new matter
TR27434A (tr) * 1992-03-12 1995-05-23 Rhone Poulenc Agrochimie Yeni 4-benzoilisoksazol türevleri, bunlari ihtiva eden terkipler ve bunlarin herbisidler olarak kullanilmalari.
GB9219779D0 (en) * 1992-09-18 1992-10-28 Rhone Poulenc Agriculture Compositions of new matter
CA2117413C (fr) * 1993-07-30 2006-11-21 Neil Geach Derives herbicides isoxazole-4-yl-methanone

Non-Patent Citations (1)

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Title
See references of WO9605198A1 *

Also Published As

Publication number Publication date
ZA956578B (en) 1997-02-07
CA2197119A1 (fr) 1996-02-22
US5716906A (en) 1998-02-10
JPH10505589A (ja) 1998-06-02
DE4427998A1 (de) 1996-02-15
AU3166795A (en) 1996-03-07
TW300891B (fr) 1997-03-21
WO1996005198A1 (fr) 1996-02-22

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