WO1997027184A1 - Heterocycles a substitution sulfoxyde et sulfone, leur procede de production et leur utilisation en tant qu'herbicides - Google Patents

Heterocycles a substitution sulfoxyde et sulfone, leur procede de production et leur utilisation en tant qu'herbicides Download PDF

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Publication number
WO1997027184A1
WO1997027184A1 PCT/EP1997/000173 EP9700173W WO9727184A1 WO 1997027184 A1 WO1997027184 A1 WO 1997027184A1 EP 9700173 W EP9700173 W EP 9700173W WO 9727184 A1 WO9727184 A1 WO 9727184A1
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Prior art keywords
alkyl
alkoxy
group
formula
hydrogen
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PCT/EP1997/000173
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German (de)
English (en)
Inventor
Aktiengesellschaft Basf
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Vogelbacher, Uwe, Josef
Rheinheimer, Joachim
Baumann, Ernst
Misslitz, Ulf
Walter, Helmut
Westphalen, Karl-Otto
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.)
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Application filed by Vogelbacher, Uwe, Josef, Rheinheimer, Joachim, Baumann, Ernst, Misslitz, Ulf, Walter, Helmut, Westphalen, Karl-Otto filed Critical Vogelbacher, Uwe, Josef
Publication of WO1997027184A1 publication Critical patent/WO1997027184A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to aromatic 5-sulfoxides and sulfones of the formula I.
  • X is nitrogen or a methine group C-H
  • Z nitrogen or a grouping CR 5 ; n 1 or 2; R is hydrogen, halogen, alkyl, alkoxy, nitro, under which
  • R 1 halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,
  • R 2 alkyl, haloalkyl, alkoxy, haloalkoxy
  • R 3 is hydrogen; a residue OR 6 ; a rest
  • R 7 and R 8 can be the same or different and in which m can assume the values 0 or 1;
  • R 4 is alkyl, haloalkyl, benzyl
  • R 5 is hydrogen, halogen, alkyl or together with R 1
  • R 6 is hydrogen, an alkali metal cation, the equivalent of one
  • R 7 , R 8 are hydrogen
  • R 9 , R 10 alkyl which can carry a phenyl radical, an alkoxy and / or an alkylthio group, cycloalkyl, phenyl, together an alkylene chain, which can carry one to five alkyl groups and which can be bridged by an alkylene chain; where substituted phenyl means that the phenyl ring can carry one to five halogen atoms, one to three alkyl or alkoxy groups and / or one to three of the following radicals: nitro, cyano, haloalkyl, haloalkoxy, alkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, Phenyl, phenyl substituted with one to three halogen atoms or one to three methyl groups.
  • Patent applications WO 91/13065 and DE-A 3919435 describe salicylic acid derivatives with a heterocyclic substituent in the 6-position which can carry an alkylthio substituent and which have a herbicidal action.
  • the action of the compounds described there is not always satisfactory in terms of herbicidal action or crop selectivity. Therefore, the task was to provide salicylic acid derivatives with an improved biological effect.
  • Benzo [1,3] dioxinones IV which can be prepared from the heteroeyclic tin compounds Ha and the benzodioxinones III under palladium catalysis analogously to EP657441 and which may initially be in the presence of a base with a nucleophile R 3 -H to form the salicylic acid derivatives V opened, which are then reacted with heterocycles of type VI, if appropriate in the presence of a base:
  • R 11 stands for C 1 -C 6 alkyl and C 1 -C 6 cycloalkyl
  • R 12 stands for a halogen atom, preferably bromine or iodine, or a trifluoromethylsulfonyloxy group
  • R 13 is a nucleofugic leaving group such as halogen, alkyl or arylsulfonyl.
  • a sulfur compound IIb can be reacted with a tin-substituted benzoic acid of the formula VII, in which R 14 denotes optionally substituted benzyl, C 1 -C 4 alkyl, dihydropyranyl, trialkylsilyl, alkoxyalkyl and dialkoxyalkyl, and the resultant
  • a catalytically active palladium compound is used in each of the two processes listed above. Any palladium salts or complexes which are at least partially soluble in the reaction mixture are suitable.
  • the oxidation state of the palladium can be 0 or 2.
  • the palladium salts include a. the following counterions are considered: chloride, bromide, iodide, sulfate, acetate, trifluoroacetate, acetylacetonate or hexafluoro-2,4-pentadionate.
  • Many different palladium complexes can be used. The only requirement is that the ligands on the palladium can be displaced from the substrate under the reaction conditions. Are particularly suitable
  • Phosphine ligands such as B. aryl alkyl phosphines such as u. a. Methyldiphenylphosphine, isopropyldiphenylphosphine, triarylphosphines such as u. a. Triphenylphosphine, tritolylphosphine, trixylylphosphine, trihetarylphosphines such as trifurylphosphine or dimeric phosphines.
  • Olefinic ligands such as u. a. Dibenzylidene acetone or its salts, cycloocta-1,5-diene or amines such as trialkylamines (e.g. triethylamine, tetramethylethylene diamine, N-methylmorpholine) or pyridine.
  • the complex used can be used directly in the reaction. So you can z. B. with tetrakistriphenylphosphine palladium (O), bistriphenylphosphine palladium dichloride, bistriphenylphosphine palladium diacetate, a dibenzylidene acetone-palladium (0) complex, tetrakismethyldiphenylphosphine palladium (O) or bis (1,2-diphenylphosphino dichloride).
  • a palladium salt and, in addition, a suitable ligand can also be used, which then only form the catalytically active complex in situ. This procedure offers z. B. in the above ge called salts and phosphine ligands such as.
  • Palladium complexes such as. B. tris (dibenzylidene acetone) dipalladium, bis (dibenzylidene acetone) palladium or 1,5-cyclooctadiene palladium dichloride by the addition of ligands such as. B. trifurylphosphine or tritolylphosphine can be activated further.
  • the palladium compound (salt or complex), based on the compounds II or VII are used. Higher quantities are possible but rather uneconomical.
  • the amount of II or VII, based on the reactants III or AR 13, is generally from 0.8 to 3, preferably from 0.95 to 1.5, molar equivalents. All solvents which do not themselves react with the substrates used are suitable for the reaction. Polar solvents accelerate the reaction.
  • Ethers such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylpropyleneurea or amines such as triethylamine are particularly suitable. It is often advantageous to use mixtures such.
  • Alkyl alcohols and water can also be considered as mixing partners, especially if the radical B contains a boron atom.
  • the addition of tetraalkylammonium halides or alkali metal halides such as.
  • Lithium chloride is often helpful and particularly advisable if Z is a sulfonyloxy radical.
  • the B radical contains a boron atom, it is often useful to use an organic or inorganic base such as
  • the reaction temperature is between -20 and 200 ° C, preferably between 50 and 160 ° C.
  • the response times are
  • the organic tin compounds of the formula VII are prepared by metalating the underlying benzoic acid with a suitable base at low temperatures and then reacting it with a trialkyltin compound to VII: Cycloalkyl or alkyl-lithium compounds are particularly suitable as bases, the commercially available isomers of butyl and hexyllithium are particularly suitable. It is often advisable to add an auxiliary to promote the metallization. For this come ethers, alcoholates such. B. potassium tert-butoxide or amines such as tetramethylethylenediamine in question.
  • the metalation can take place at temperatures from (-130) ° C to 0 ° C, preferably between (-100) and (-50) ° C. All solvents usually used in metallations are also suitable for this reaction, diethyl ether, methyl tert-butyl ether, tetrahydrofuran and simple hydrocarbons are particularly suitable, it being possible to use mixtures of these substances.
  • the reaction times for the metalation can range from a few minutes to a few hours.
  • the trialkyltin compound is then added, where R 12 is the usual leaving groups, preferably chlorine or bromine. The above applies to the temperature during the addition and the subsequent reaction time.
  • aqueous or non-aqueous workup can then be carried out, in which case it can prove useful in the first case to keep the pH of the aqueous phase constant with a buffer. If necessary, it increases the yield considerably if, before working up, a substance is added at low temperatures that is suitable for destroying excess base. For example, carbon dioxide, water, alkyl or benzyl halides are suitable.
  • organic tin compounds of the formula VII can be further purified, for example by chromatography on silica gel. During processing, they also prove to be stable against water at various pH values and can be stored at room temperature.
  • Benzoic acid derivatives ie compounds Ia in which R 3 is an OH group
  • Compounds of the formula I can also be synthesized by starting from the free acids, ie substances in which R 3 is OH, and converting them into an activated form, such as a halide or an imidazolide, and then using a nucleophile R 3 -H possibly in the presence of a base.
  • R 3 is OH
  • R 3 -H possibly in the presence of a base.
  • R * here stands for any residue occurring in the described description methods.
  • suitable oxidizing agents are hydrogen peroxide, organic peracids such as meta-chloroperbenzoic acid or peracetic acid, iodates, periodates, potassium permanganate, iodosobenzene, acetyl nitrate or nitric acid.
  • a catalyst such as sodium tungstate or phenylselenic acid can be added.
  • the substituents mentioned preferably have the following meaning:
  • C 1 -C 4 alkyl methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-propyl, 1, 1-dimethyl-ethyl;
  • C 1 -C 6 alkyl C 1 -C 4 alkyl and 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-butyl, 3-methyl-butyl, 2-methyl-2-butyl, 3- Methyl-2-butyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 2,2-dimethyl-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-pentyl, 3- Methyl-pentyl, 4-methyl-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,
  • C 1 -C 4 haloalkyl chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl,
  • C 3 -C 6 cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, particularly preferably cyclopropyl, cyclopentyl and cyclohexyl;
  • C 1 -C 4 alkylcarbonyl acetyl, propionyl, 1-propylcarbonyl,
  • C 1 -C 4 haloalkoxy difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy,
  • C 1 -C 4 alkylcarbonyloxy acetoxy, propionyloxy, 1-propylcarbonyloxy, 2-propylcarbonyloxy, 1-butylcarbonyloxy, 2-butylcarbonyloxy, 2-methyl-propylcarbonyloxy, 1,1-dimethyl-ethylcarbonyloxy;
  • C 1 -C 4 alkylthio methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 2-butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, especially methylthio, ethylthio, 1-methylethylthio;
  • C 1 -C 4 alkylamino methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 2-butylamino, 1-methylpropylamino,
  • Di-C 1 -C 4 alkylamino dimethylamino, N-methyl-N-ethylamino,
  • C 3 -C 6 alkylene chain propylene, butylene, pentylene, hexylene;
  • Het is a five- or six-membered heterocycle from the group thiophene, furan, pyrrole, pyrazole, imidazole, oxazole, thiazole, isoxazole, isothiazole, pyridine, pyridine-N-oxide, pyridazine, pyrimidine, pyrazine, 1,3,5- Triazine, 1,2,4-triazine;
  • R is hydrogen, halogen, alkyl, provided that there is still a free substitution site on the heterocycle;
  • R 1 is alkyl, haloalkyl, alkoxy, haloalkoxy
  • R 3 is hydrogen
  • R 5 is hydrogen or together with R 1 a unit - CH 2 -CH 2 -O-;
  • R 6 is hydrogen, an alkali metal cation, the equivalent of one
  • R 9 , R 10 alkyl which can carry an alkoxy and / or an alkylthio group, together an alkylene chain; where substituted phenyl means that the phenyl ring can carry one to five halogen atoms, one to three alkyl or alkoxy groups and / or one to three nitro groups.
  • R is hydrogen, halogen, C 1 -C 4 alkyl, provided that a free substitution site still exists on the heterocycle;
  • R 1 C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy,
  • R 3 is hydrogen
  • R 5 is hydrogen or together with R 1 a unit - CH 2 -CH 2 -O-;
  • R 6 is hydrogen, an alkali metal cation, the equivalent of one
  • R 9 , R 10 C 1 -C 4 alkyl, which is a C ⁇ -C 4 alkoxy and / or
  • C 1 -C 4 alkylthio group can carry, together a C 3 -C 11 alkylene chain; where substituted phenyl means that the phenyl ring can carry one to five halogen atoms, one to three C 1 -C 4 alkyl or C ⁇ -C 4 alkoxy groups and / or one to three nitro groups. Also preferred are compounds of the formula I in which the substituents and the index have the following meaning:
  • Z is nitrogen or a C-H group
  • R is hydrogen, alkyl, provided that on
  • Heterocycle still has a free substitution site; R 1 alkoxy;
  • Z is nitrogen or a C-H group
  • R is hydrogen, C 1 -C 4 alkyl, provided that on
  • Heterocycle still has a free substitution site
  • R 3 is hydrogen
  • R 4 C 1 -C 4 alkyl
  • R 6 is hydrogen; a C 1 -C 6 alkyl group which can carry one to five halogen atoms, a phenyl ring or a C 1 -C 4 alkoxy group; a C 3 -C 6 alkenyl or a C 3 -C 6 alkynyl group;
  • radical -N CR 9 R 10 , in which R 9 and R 10 may be the same or different; R 9 , R 10 are C 1 -C 4 alkyl, together a C 3 -C 8 alkylene chain;
  • Z is nitrogen or a C-H group
  • R is hydrogen, provided that there is still a free substitution site on the heterocycle
  • Z is nitrogen or a C-H group
  • R is hydrogen, provided that there is still a free substitution site on the heterocycle
  • R 4 C 1 -C 4 alkyl
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. 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.
  • the following crops are considered, for example:
  • napobrassica Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients 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 hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • directly sprayable aqueous solutions powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the uses; 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, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsion concentrates suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • Substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • 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.
  • the surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, 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, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicas, 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, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one 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-monoethanolamide, 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.
  • an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • Dissolved mixture consisting of 40 parts by weight of cyclohexanone
  • Dissolved mixture consisting of 25 parts by weight of cyclohexanone
  • V 3 parts by weight of active ingredient No. 1.004 are mixed with 97 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 3% by weight of the active ingredient.
  • VI 20 parts by weight of active ingredient No. 1.004 are mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condesate and 68 parts by weight. Parts of a paraffinic mineral oil are intimately mixed. A stable oily dispersion is obtained. VII 1 part by weight of compound 1.004 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
  • the aromatic sulfoxides and sulfones can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2-aroyl come as mixing partners -1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclo hexane-1,3-dione derivatives, diazines, dichloropropionic acid and their derivatives,
  • Pyridazines pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uraciles.
  • the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also)

Abstract

Sulfoxydes et sulfones aromatiques de formule I, dans laquelle les substituants et les indices ont la signification suivante: Het est un hétérocycle à 5 ou 6 chaînons choisi dans le groupe thiofène, furane, pyrrole, pyrazole, imidazole, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-triazole, (1H)1,2,4-triazole, (4H)1,2,4-triazole, pyridine, pyridin-N-oxyde, pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,3,5-triazine, 1,2,4-triazine; X représente azote ou un groupe méthine C-H; Y représente oxygène ou soufre; Z représente oxygène ou un groupement C-R<5>; n vaut 1 ou 2; et dans laquelle les substituants R, R<1>, R<2>, R<3> et R<4> ont la signification donnée dans la revendication 1. L'invention porte également sur un procédé de production desdits hétérocycles et leur utilisation en tant qu'herbicides.
PCT/EP1997/000173 1996-01-24 1997-01-16 Heterocycles a substitution sulfoxyde et sulfone, leur procede de production et leur utilisation en tant qu'herbicides WO1997027184A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19602404.8960124 1996-01-24
DE1996102404 DE19602404A1 (de) 1996-01-24 1996-01-24 Sulfoxid- und Sulfon-substituierte Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2409753A1 (de) * 1974-03-01 1975-09-11 Basf Ag Substituierte pyrazole
WO1991013065A1 (fr) * 1990-02-20 1991-09-05 Fmc Corporation Herbicides a base d'acide benzoique 6-aryl-2-substitue
DE4337323A1 (de) * 1993-11-02 1995-05-04 Basf Ag Substituierte Pyridylsalicylaldehyd- bzw. salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE4337322A1 (de) * 1993-11-02 1995-05-04 Basf Ag Pyrid-N-oxid substituierte Salicylaldehyd- bzw. Salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2409753A1 (de) * 1974-03-01 1975-09-11 Basf Ag Substituierte pyrazole
WO1991013065A1 (fr) * 1990-02-20 1991-09-05 Fmc Corporation Herbicides a base d'acide benzoique 6-aryl-2-substitue
DE4337323A1 (de) * 1993-11-02 1995-05-04 Basf Ag Substituierte Pyridylsalicylaldehyd- bzw. salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE4337322A1 (de) * 1993-11-02 1995-05-04 Basf Ag Pyrid-N-oxid substituierte Salicylaldehyd- bzw. Salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

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