EP0333791A1 - Heterocyclische verbindungen - Google Patents

Heterocyclische verbindungen

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Publication number
EP0333791A1
EP0333791A1 EP88907596A EP88907596A EP0333791A1 EP 0333791 A1 EP0333791 A1 EP 0333791A1 EP 88907596 A EP88907596 A EP 88907596A EP 88907596 A EP88907596 A EP 88907596A EP 0333791 A1 EP0333791 A1 EP 0333791A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
chloro
dioxo
dihydro
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Withdrawn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
EP88907596A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jean Wenger
Paul Winternitz
Martin Zeller
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
F Hoffmann La Roche AG
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 Ciba Geigy AG, F Hoffmann La Roche AG filed Critical Ciba Geigy AG
Publication of EP0333791A1 publication Critical patent/EP0333791A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings

Definitions

  • the present invention relates to heterocyclic compounds, namely 3-aryluracils of the general formula
  • R 1 is hydrogen, C 1-4 alkyl. C 1-4 haloalkyl,
  • Haloalkyl C 1-8 hydroxyalkyl.
  • R 2 and R 3 together with the nitrogen atom to which they are linked, a four- to seven-membered heterocyclic ring which is mono- or polysubstituted or substituted by C 1-6 -alkyl and which besides the nitrogen atom also contains an oxygen atom, a sulfur atom and / or can have a second nitrogen atom in the ring,
  • R 4 halogen or cyano.
  • R 5 is hydrogen or halogen
  • R 6 is hydrogen, halogen or C 1-4 alkyl
  • R 7 is C 1-4 alkyl or, if R 1 is different from C 1-4 haloalkyl, also C 1-4 -Haloalkyl, or
  • R 6 and R 7 together mean tri- or tetramethylene, and the corresponding enol ethers of those compounds of
  • R 1 is C 1-4 alkyl, C 3 or 4 alkenyl or C 3 or 4 alkynyl
  • R 6 is hydrogen, halogen or C 1-4 alkyl and R 7 is C 1-4 haloalkyl
  • the compounds according to the invention are herbicidally active and are suitable as active compounds of weed control agents.
  • the invention thus also comprises weed control compositions which comprise compounds according to the invention as active compounds, processes for the preparation of these compounds and the use of the compounds or compositions for controlling weeds.
  • halogen includes fluorine, chlorine, bromine and iodine.
  • the alkyl, alkenyl and alkynyl radicals can be straight-chain or branched, this also being the case for the alkyl part or parts of the haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, cyanoalkyl, nitroalkyl, carboxyalkyl, alkoxycarbonyl , Alkylsulfonylalkyl-, Dialkylphosphonoalkyl-, Alkoxy-, Haloalkoxy- and Phenylalkyl negligence applies.
  • a haloalkyl or haloalkoxy group can have one or more (identical or different) halogen atoms.
  • a substituted phenyl or phenylalkyl group may also have one or more of the substituents mentioned, which may be the same or different.
  • Under the "lower alkyl” mentioned below is to be understood in particular as C 1-6 alkyl.
  • Examples of the bicyclic groups which R 2 and R 3 can denote are 1,3-benzodioxol-5-yl and 1,3-benzodioxan-6-yl.
  • Examples of the four- to seven-membered heterocyclic rings that NR 2 R 3 can form are pyrrolidino,
  • Piperidino Hexahydroazepino, Morpholino. Thiomorpholino. Piperazino and 4-methylpiperazino.
  • the salts of the compounds of formula I and their enol ethers are in particular alkali metal salts, e.g. Sodium and potassium salts; Alkaline earth metal salts, e.g. Calcium and magnesium salts; Ammonium salts, i.e. unsubstituted ammonium salts and mono- or poly-substituted ammonium salts. e.g. Triethylaramonium and methylammonium salts, as well as salts with other organic bases, e.g. with pyridine.
  • R 1 is alkenyl or alkynyl. This radical is preferably allyl or propargyl. In general, any halogen atom that is present is preferably fluorine, chlorine or bromine. A possibly present haloalkyl group is preferably difluoromethyl, trifluoromethyl or pentafluoroethyl.
  • a special group of compounds of the formula I consists of those compounds I in which R 1
  • R 3 is hydrogen
  • C 1-8 alkyl C 2-8 alkenyl, C 3-8 alkynyl,
  • C 1-8 haloalkyl C 1-8 hydroxyalkyl, C 2-8 cyanoalkyl, C 2-5 alkoxycarbonylC 1-8 alkyl, C 3-8 cycloalkyl, C 1-8 alkoxy, if appropriate phenyl substituted with halogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 haloalkoxy and / or C 2 - 5 alkoxycarbonyl, this optionally substituted phenyl being a condensed, saturated. May have 2 heterocyclic five- or six-membered ring containing oxygen atoms, or optionally substituted with nitro
  • R 1 is preferably C 1-4 alkyl, in particular methyl, or C 1-4 fluoroalkyl, in particular difluoromethyl;
  • R 2 is preferably hydrogen or C 1-8 alkyl;
  • R 3 is preferably C 1-8 alkyl,
  • R 4 is preferably halogen, especially chlorine or bromine
  • R 5 is preferably hydrogen or fluorine
  • R 6 is preferably hydrogen, fluorine or methyl
  • R 7 is preferably C 1-4 alkyl.
  • Particularly preferred individual compounds according to the invention are ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, allyl, 2-methyl-2-propenyl, propargyl, 1,1-dimethyl-2 -propinyl-, 1-cyano-1-methylethyl-, 1-cyano-1,2-dimethylpropyl-, cyclopropyl-, cyclohexyl-, benzyl- and 1-phenylethylamide of 2-chloro-5- [3,6-dihydro-2,6- dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidinyl] -4-fluorobenzoic acid, the N, N-diethyl-2-chloro-5- [3.6-dihydro-2,6-dioxo-3-methyl - 4-trifluoromethyl-1 (2H) -pyrimidinyl] -4-fluorobenzamide, the ally
  • R 2 , R 3 , R 4 and R 5 are the above
  • R 8 is lower alkyl, preferably C 1-4 alkyl, with the deprotonated form of a compound of the general formula
  • R 6 and R 7 have the meanings given above and R 9 is lower alkyl, preferably C 1-8 alkyl. means, implements,
  • R 2 , R 3 , R 4 and R 5 are the above
  • R 6 , R 7 and R 9 have the meanings given above and R 10 is lower alkyl, preferably
  • C 3 or 4 alkenyl means C 3 or 4 alkynyl
  • R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above, correspondingly alkylated.
  • R 4 , R 5 , R 6 ' and R 7' are those given above
  • R 2 ' and R 3' have the meanings given above of R 2 and R 3 with the exception of
  • Has hydrogen and shark means chlorine or bromine, with the deprotonated form of an alkanol, alkenol or
  • R 1 is C 1-4 alkyl.
  • C 1-4 alkyl C 3 or 4 alkenyl or C 3 or 4 alkynyl,
  • R is hydrogen, halogen or C 1 _ 4 -alkyl and R 7
  • C 1-4 haloalkyl mean a benzoic acid of the general formula
  • R 4 , R 5 , R 6 and R 7 have the meanings given above and R 1 " C 1-4 alkyl. C 1-4 ⁇
  • -Alkynyl means or the relevant enol ether, i.e. the formula
  • R 1 ' , R 4 , R 5 , R 6' and R 7 ' have the meanings given above, where the benzoic acid or its enol ether may be in the form of a reactive derivative, with an amine of the general formula
  • the product of treating this compound IV with a base such as an alkali metal or alkaline earth metal alcoholate, for example sodium ethanolate, potassium isopropylate, potassium isobutylate or potassium sec-butoxide, is under deprotonated form of the compound of the formula IV. or an alkali metal hydride, for example sodium hydride; with an alkali metal amide. eg lithium amide or sodium amide; with an alkali metal, for example lithium or sodium; or with an organometallic compound such as one Alkyl lithium, for example methyl or butyllithium. or phenyllithium. to understand.
  • a base such as an alkali metal or alkaline earth metal alcoholate, for example sodium ethanolate, potassium isopropylate, potassium isobutylate or potassium sec-butoxide
  • a base such as an alkali metal or alkaline earth metal alcoholate, for example sodium ethanolate, potassium isopropylate, potassium isobutylate or potassium sec-butoxid
  • This treatment is expediently carried out in an inert organic diluent, such as an aromatic hydrocarbon, for example benzene, toluene or a xylene; a heterocyclic solvent, for example N-methylpyrrolidone, pyridine or quinoline; Dimethylformamide; or dimethyl sulfoxide.
  • an aromatic hydrocarbon for example benzene, toluene or a xylene
  • a heterocyclic solvent for example N-methylpyrrolidone, pyridine or quinoline
  • Dimethylformamide or dimethyl sulfoxide.
  • the 3-isocyanatobenzoic acid amide of the formula II or the 3-alkoxycarbonylaminobenzoic acid amide of the formula III is then advantageously reacted with the deprotonated form of the compound IV thus produced in the same diluent by carrying out the deprotonation, generally at reaction temperatures in the range of about -100 ° C to 200 ° C.
  • the reaction according to process variant b) expediently takes place in an essentially water-free diluent and in the presence of an acidic catalyst at elevated temperature.
  • Suitable diluents are, in particular, organic solvents which form azeotropes with water, such as cyclic hydrocarbons, for example cyclohexane; Aromatics, for example benzene, toluene and xylenes; halogenated hydrocarbons. eg methylene chloride, chloroform, carbon tetrachloride and chlorobenzene; and aliphatic or cyclic ethers, for example 1,2-dimethoxyethane, tetrahydrofuran and dioxane.
  • strong mineral acids such as sulfuric acid and hydrochloric acid are used as acidic catalysts; organic acids such as p-toluenesulfonic acid; Acids containing phosphorus, such as orthophosphoric acid and polyphosphoric acid; and acidic cation exchangers, such as "Amberlyst 15" (Fluka). It is generally carried out in a temperature range from about 50 ° C. to 130 ° C., preferably at the reflux temperature of the reaction mixture. Under these reaction conditions, the desired rapid removal of the water formed in the reaction is achieved.
  • the expression is in process variant c)
  • Haloalkyl C 3 or 4 alkenyl or C 3 or 4 alkynyl group.
  • Bromide or iodide, or - in the case of an N- C 1-4 alkyl substitution - a di (C 1-4 alkyl) sulfate is used.
  • the alkylation is advantageously carried out in the presence of an inert organic solvent, optionally in a mixture with water, and in the presence of a base.
  • Protic such as lower alkanols, are suitable as inert organic solvents. eg methanol and ethanol; aprotic, such as aliphatic or cyclic ethers, for example diethyl ether. 1,2-dimethoxyethane, tetrahydrofuran and dioxane.
  • aliphatic ketones for example acetone and 2-butanone; or polar, such as dirnethylformamide, dimethyl sulfoxide and acetonitrile.
  • suitable bases are metal hydrides, for example sodium hydride; Alkali metal alcoholates, for example sodium ethanolate; or alkali metal carbonates and bicarbonates, for example sodium carbonate, potassium carbonate. Sodium bicarbonate and potassium bicarbonate.
  • the reaction temperatures are advantageously between 0 ° C and the reflux temperature of the reaction mixture.
  • the deprotonated form of the alkanol, alkenol or alkmol R 1 ' OH used in process variant d) expediently arises either by using the hydroxy compound R 1' OH in the presence of an organic base, in particular an organic tertiary base such as triethylamine or pyridine or the corresponding metal alcoholate, -alkenolate or alkinolate R 1 ' O ⁇ M ⁇ , wherein M ⁇ means one equivalent of a metal ion, such as an alkali metal ion, for example sodium or potassium, or an alkaline earth metal ion, for example calcium or magnesium.
  • the Sodium ion is the preferred metal ion.
  • the reaction is conveniently in excess of the corresponding hydroxy compound R 1 ' OH as a diluent and at temperatures between 0 ° C. and 50 ° C., preferably at room temperature.
  • Process variant e) is an amidation of benzoic acid IX or enol ether IXa or a reactive derivative of the acid or enol ether.
  • This amidation can be carried out according to methods known per se.
  • an acid halide especially the acid chloride, the benzoic acid IX or the enol ether IXa with the amine X in an inert organic diluent such as an aliphatic or cyclic ether, e.g. Diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane; a chlorinated aliphatic hydrocarbon, e.g.
  • Methylene chloride 1,2-dichloroethane or chloroform; or an aliphatic or aromatic hydrocarbon. e.g. n-hexane. Benzene, toluene or a xylene, at temperatures between -20 ° C and the reflux temperature of the reaction mixture.
  • the reaction can be carried out with or without the addition of a base such as a tertiary amine e.g. Triethylamine, pyridine or quinoline; an alkali metal carbonate, e.g. Sodium or potassium carbonate; or excess amine X, take place.
  • a base such as a tertiary amine e.g. Triethylamine, pyridine or quinoline; an alkali metal carbonate, e.g. Sodium or potassium carbonate; or excess amine X, take place.
  • the desired salts of the compounds I according to the invention and enol ethers in which R 1 and / or R 2 is hydrogen can be prepared from them in a manner known per se be, such as by dissolving the compound I or the enol ether in a solution of an inorganic or organic base. Salt formation usually takes place within a short time at room temperature.
  • the sodium salt is prepared by dissolving the uracil derivative I in aqueous sodium hydroxide solution at room temperature, using equivalent amounts of the uracil derivative and the sodium hydroxide.
  • the solid salt can then be isolated by precipitation with a suitable inert solvent or by evaporation of the solvent.
  • Another embodiment is to introduce an aqueous solution of an alkali metal salt of uracil derivative I into an aqueous solution of a salt that has a metal ion other than an alkali metal ion, thereby producing the second metal salt of the uracil derivative.
  • This embodiment is generally used to prepare uracil metal salts that are insoluble in water.
  • Enol ethers and salts can be isolated and purified by methods known per se.
  • the product can be obtained as a mixture of two or more isomers.
  • the isomers can be separated by methods known per se. If desired, for example, pure optically active isomers can also be prepared by synthesis from corresponding optically active starting materials.
  • R 11 is a leaving group, such as
  • Halogen. as chlorine, imidazolyl, triazolyl, or acyloxy, for example acetoxy, and M ' ⁇ eeiinn alkali metal ion, especially the sodium ion, are:
  • the conversion of the benzoic acid of the formula XI into its reactive derivative of the formula XII is carried out according to methods known per se.
  • Formula XII (R 11 means acyloxy, for example acetoxy) can be prepared, for example, by mixing the benzoic acid XI or an alkali metal or alkaline earth metal salt thereof, for example the sodium or potassium salt, with an acyl chloride, for example acetyl chloride, at temperatures between -20 ° C. and converts 150 ° C.
  • the derivative XII is then reacted with the amine X, for example analogously to the process variant e) described above, to give the benzamide XIII, water also being able to be used as the diluent.
  • the reduction of the 3-nitrobenzamide XIII to the corresponding 3-aminobenzamide of the formula XIV is carried out, for example, using iron, zinc, tin or tin chloride or by catalytic hydrogenation.
  • the 3-nitrobenzamide XIII in an organic solvent such as a lower alkanol, for example methanol or ethanol, a lower alkanoic acid, for example acetic acid, or an aliphatic or cyclic ether, for example tetrahydrofuran or dioxane, in water or in a mixture of an organic solvent and water with a metal.
  • an organic solvent such as a lower alkanol, for example methanol or ethanol, a lower alkanoic acid, for example acetic acid, or an aliphatic or cyclic ether, for example tetrahydrofuran or dioxane
  • iron, zinc or tin, or a metal salt with a low oxidation level for example tin (II)
  • the reaction is conveniently carried out in the presence of an acid, such as hydrochloric acid, sulfuric acid, orthophosphoric acid or acetic acid; in general mine are between 0.01 and 20 mol equivalents of acid based on the amount of 3-nitrobenzamide XIII used.
  • the reaction temperatures are expediently between -20 ° C and 150 ° C.
  • the 3-nitrobenzamide in an organic solvent such as a lower alkanol, for example methanol or ethanol, or a lower alkanoic acid, for example acetic acid, at temperatures between 0 ° C and 100 ° C, under elevated pressure up to 100 atm. and in the presence of a transition metal, for example platinum or palladium, as a catalyst.
  • the 3-aminobenzamide XIV thus prepared can then optionally be converted to the 3-isocyanatobenzamide of the formula II.
  • the 3-aminobenzamide XIV with phosgene or diphosgene is expediently in an inert diluent, such as ethyl acetate, toluene or a xylene, at temperatures from 0 ° C. to 150 ° C. preferably 30 ° C to 80 ° C, implemented.
  • an inert diluent such as ethyl acetate, toluene or a xylene
  • the reaction of the 3-aminobenzamide XIV to the 3-alkoxycarbonylaminobenzamide III is expediently carried out using a lower alkyl chloroformate, in particular the ethyl ester. in an organic solvent, such as an aliphatic or cyclic ether, for example diethyl ether, tetrahydrofuran or dioxane, a chlorinated aliphatic hydrocarbon. eg methylene chloride or chloroform, in water, or in a mixture of an organic solvent and water at temperatures between -20 ° C. and 100 ° C.
  • an inorganic base such as an alkali metal or alkaline earth metal hydroxide, eg sodium hydroxide, or an organic base, eg triethylamine, pyridine or quinoline. If an organic base is used, it can also serve as a solvent.
  • the reaction is carried out in a tertiary amine, for example Pyridine, as a solvent and carried out in a temperature range from 0 ° C to 30 ° C.
  • the 3-aminobenzamide XIV is used with an alkali metal cyanate M ' ⁇ OCN ⁇ , in particular with sodium cyanate. Conveniently in water at temperatures between 0 ° C and 50 ° C and in the presence of an inorganic acid, for example hydrochloric acid or sulfuric acid, or an organic acid. eg acetic acid, to 3-ureidobenzoic acid V um.
  • an inorganic acid for example hydrochloric acid or sulfuric acid, or an organic acid. eg acetic acid
  • the 3-isocyanatobenzamide II can be incorporated into the 3-isocyanatobenzamide II.
  • an inert organic solvent such as an aliphatic or cyclic ether, e.g. Diethyl ether. Tetrahydrofuran or dioxane, an aromatic hydrocarbon, e.g. Toluene, or water and at temperatures between -20 ° C and 50 ° C.
  • R 2 , R 3 , R 4 and R 5 are the above
  • R 12 denotes nitro, amino, isocyanato, a lower alkoxycarbonyl group R 8 OOCNH or ureido and R 8 has the meaning given above, where, if R 12 denotes nitro or amino,.
  • R 5 only represents fluorine, are new and form a further subject of the present invention.
  • Diluent can serve.
  • the chlorination or bromination can be carried out in the presence of an inert diluent, in particular an aprotic organic solvent, such as an aliphatic or aromatic hydrocarbon. e.g. n-hexane, benzene, toluene or a xylene; a halogenated aliphatic hydrocarbon, e.g. Methylene chloride, chloroform or 1,2-dichloroethane; or a halogenated aromatic hydrocarbon, e.g.
  • an inert diluent in particular an aprotic organic solvent, such as an aliphatic or aromatic hydrocarbon. e.g. n-hexane, benzene, toluene or a xylene; a halogenated aliphatic hydrocarbon, e.g. Methylene chloride, chloroform or 1,2-dichloroethane; or a halogenated aromatic hydrocarbon, e
  • the reaction temperatures are generally between 0 ° C and the reflux temperature of the reaction mixture, preferably between 20 ° C and 70 ° C.
  • the starting materials of formula IX used in process variant e) are largely described in European Patent Publication No. 195,346. Those starting materials IX, the production of which is not described. can be prepared analogously to the known starting materials.
  • the also as a starting Reactive derivatives of benzoic acids IX which can be used in materials can be prepared from these benzoic acids by methods known per se.
  • all enol ethers of benzoic acids IX which can also be used as starting materials in process variant e), ie the compounds of the general formula IXa, and their reactive derivatives are new.
  • the enol ethers can, for example, according to the reaction scheme below, in which R 1 , R 4 , R 5 , R 6 ' , R 7' and shark have the meanings given above and R 13 is lower alkyl. preferably C 1-4 alkyl. means to be manufactured:
  • halogenation of the 3-aryluracil of the formula XVI can be carried out analogously to the halogenation of the 3-aryluracil of the formula I 'described above to give the starting materials of the formula
  • Catalyst in a chlorinated aliphatic hydrocarbon, preferably methylene chloride, as
  • Solvent and at temperatures between -30 ° C and 30 ° C, preferably between 0 ° C and room temperature. Excess sulfuric acid itself can serve as a solvent without an additional solvent.
  • Enol ethers can be produced by methods known per se.
  • the compounds of the formula I, their enol ethers and the salts of the compounds I and enol ether (hereinafter referred to collectively as the compounds according to the invention) have herbicidal properties and are suitable for Control of weeds, including weeds, e.g. Setaria faberii, Digitaria sanguinalis, Poa annua, Chenopodium album, Amaranthus retroflexus, Abutilon theophrasti, Sinapis alba and Datura stramonium in various crops.
  • the compounds are both pre-emergence and post-emergence herbicides.
  • a concentration of 0.001 to 3 kg compound / ha according to the invention preferably 10 to 300 g compound / ha according to the invention, is usually sufficient to achieve the desired herbicidal effect.
  • concentration series of 15 to 200 g of compound according to the invention / ha is particularly preferred.
  • the weed control composition according to the invention is characterized in that it contains an effective amount of at least one compound according to the invention and formulation auxiliaries.
  • the agent expediently contains at least one of the following formulation auxiliaries: solid carriers; Solvents or dispersants; Surfactants (wetting and emulsifying agents); Dispersants (without surfactant action); and stabilizers.
  • these compounds that is to say the herbicidal active ingredients, can be converted into the customary formulations, such as dusts, powders, granules, solutions, emulsions, suspensions, emulsifiable concentrates, pastes and the like.
  • the compounds of the formula I and their enol ethers are generally water-insoluble, the salts, on the other hand, in particular the alkali metal salts and ammonium salts, are generally water-soluble and can be made up according to the methods customary for water-insoluble or water-soluble compounds, using the formulation auxiliaries relating to this.
  • the preparation of the agents can be carried out in a manner known per se, for example by mixing the respective active ingredient with solid Carriers, by dissolving or suspending in suitable solvents or dispersing agents, possibly using surfactants as wetting or emulsifying agents and / or dispersing agents, by diluting previously prepared emulsifiable concentrates with solvents or dispersing agents, etc.
  • the following are essentially suitable as solid carriers: natural minerals, such as chalk, dolomite, limestone.
  • Clays and silica and their salts for example diatomaceous earth, kaolin, bentonite, talc, attapulgite and montmorrillonite); synthetic minerals such as finely divided silica.
  • Alumina and silicates organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers such as phosphates and nitrates, such carriers e.g. can be present as powder or as granules.
  • aromatics such as benzene, toluene.
  • Xylenes and alkylnaphthalenes chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene and methylene chloride
  • aliphatic hydrocarbons such as cyclohexane and paraffins, for example petroleum fractions
  • Alcohols such as butanol and glycol, and their ethers and esters
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone
  • strongly polar solvents or dispersing agents such as dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, such solvents preferably having flash points of at least 30 ° C.
  • liquefied gaseous extenders or carriers which are products which are gaseous at room temperature and under normal pressure.
  • aerosol propellants such as halogenated hydrocarbons, for example dichlorodifluoromethane.
  • the weed control according to the invention is in the form of a compressed gas pack before, a solvent is expediently used in addition to the propellant gas.
  • the surfactants can be nonionic compounds, such as condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide; Fatty acid esters and ethers of sugars or polyhydric alcohols; the products obtained from sugars or polyhydric alcohols by condensation with ethylene oxide; Block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.
  • the surfactants can also be anionic compounds, such as soaps; Fatty sulfate ester. e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate; Alkyl sulfonates, aryl sulfonates and fatty aromatic sulfonates such as alkyl benzene sulfonates. e.g. Calcium dodecylbenzenesulfonate, and butylnaphthalenesulfonates; and more complex fatty sulfonates, e.g. the amide condensation products of oleic acid and N-methyl taurine and the sodium sulfonate of dioctyl succinate.
  • anionic compounds such as soaps
  • Fatty sulfate ester e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate
  • the tenisides can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.
  • lignin sodium and ammonium salts of lignin sulfonic acids, sodium salts of maleic anhydride-diisobutylene copolymers, sodium and ammonium salts of sulfonated polycondensation products made from naphthalene and formaldehyde, and sulfite waste liquors.
  • Dispersants which are particularly suitable as thickeners or anti-settling agents are, for example, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, alginates. Caseinates and blood albumin be set.
  • Suitable stabilizers are acid-binding agents. e.g. Epichlorohydrin. Phenylglycidyl ether and soya epoxides; Antioxidants, e.g. Gallic acid esters and
  • Butylated hydroxytoluene e.g. substituted benzophenones.
  • Diphenylacrylonitrile acid esters and cinnamic acid esters e.g., ethylenediaminotetraacetic acid and polyglycols.
  • the weed control agents according to the invention can contain synergists and other active compounds, e.g. Insecticides, acaricides, fungicides, plant growth regulators and fertilizers. Such combination agents are suitable for increasing the activity or for broadening the spectrum of action.
  • the weed control compositions according to the invention generally contain between 0.001 and 95 percent by weight. preferably between 0.5 and 75 percent by weight of one or more compounds according to the invention as active ingredient (s). You can e.g. be in a form suitable for storage and transportation. In such formulations, e.g. emulsifiable concentrates, the active ingredient concentration is normally in the higher range, preferably between 1 and 50 percent by weight, in particular between 10 and 30 percent by weight. These formulations can then e.g. with the same or different inert substances, to be diluted to active substance concentrations. which are suitable for practical use, that is preferably about 0.001 to 10 percent by weight, in particular about 0.005 to 5 percent by weight. However, the drug concentrations can also be smaller or larger.
  • the weed control compositions according to the invention can be produced in a manner known per se.
  • the active ingredient ie at least one compound according to the invention
  • the active ingredient can be mixed with solid carrier, for example by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then evaporate the solvent or dispersant. Remove heating or suction under reduced pressure.
  • the addition of surfactants or dispersants can make such powdery compositions readily wettable with water, so that they can be converted into aqueous suspensions which are suitable, for example, as spray compositions.
  • the active ingredient can also be mixed with a surfactant and a solid carrier to form a wettable powder which is dispersible in water, or it can be mixed with a solid pre-granulated carrier to form a granular product.
  • the active ingredient can be dissolved in a water-immiscible solvent, such as, for example, a high-boiling hydrocarbon, which advantageously contains dissolved emulsifiers, so that the solution has a self-emulsifying effect when added to water. Otherwise, the active ingredient can be mixed with an emulsifier and the mixture can then be diluted with water to the desired concentration. In addition, the active ingredient can be dissolved in a solvent and then mixed with an emulsifier. Such a mixture can also be diluted with water to the desired concentration. In this way, emulsifiable concentrates or ready-to-use emulsions are obtained.
  • a water-immiscible solvent such as, for example, a high-boiling hydrocarbon, which advantageously contains dissolved emulsifiers
  • the use of the weed control compositions according to the invention, which forms a further object of the present invention, can be carried out by customary application methods, such as spraying. Spraying, dusting, pouring or Scatter, done.
  • the method according to the invention for controlling weeds is characterized in that the crop to be protected against weeds and / or the weeds is treated with a compound according to the invention or with a weed control agent according to the invention.
  • the mixture is then poured onto 200 ml of ice water, the aqueous mixture is acidified to pH 3 with 2N hydrochloric acid, and the aqueous phase is extracted three times with 150 ml of ethyl acetate each time. washes the combined organic extracts until neutral, dries the organic phase over anhydrous sodium sulfate and evaporates it.
  • the oily product is treated with activated carbon and then crystallized from diethyl ether.
  • N-isopropyl-2 is obtained starting from ethyl 4,4,4-trifluoro-3-aminocrotonic acid and ethyl 4-chloro-2-fluoro-5- (N-isopropylcarbamoyl) carbanilate -chloro-5- [3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl] -4-fluorobenzamide, mp. 234-239 ° C.
  • the mixture is then mixed with 400 ml of water, extracted twice with 400 ml of ethyl acetate, washes the organic phases twice with 200 ml each in hydrochloric acid, then twice with 200 ml each of saturated sodium chloride solution, dries the combined organic phases over anhydrous sodium sulfate and evaporates them.
  • the residue is purified by chromatography on silica gel with ethyl acetate / n-hexane (1: 2) as the eluent.
  • nitrobenzoic acid amide and the corresponding amine HNR 2 R 3 is the N-monosubstituted or N, N-disubstituted 2-chloro-4-fluoro-5-nitro-benzamide of the formula XIII listed in Table 5 below:
  • Example 65 Analogously to the process described in Example 65, starting from N-isopropyl-5-amino-2-chloro-4-fluorobenzamide and ethyl chloroformate, the 4-chloro-2-fluoro5- (N-isopropylcarbamoyl) used as starting material in Example 2 is obtained. -carbanilic acid -ethyl ester, mp. 127-130 ° C.
  • Example 67 Example 67
  • a mixture of 35 g of 2-chloro-5- [3,6-dihydro-2,6-dioxo-3,4-dimethyl-1 (2H) pyrimidinyl] -4-fluorobenzoic acid isopropyl ester.
  • 165 ml of concentrated sulfuric acid and 165 ml of methylene chloride are stirred well at room temperature for 30 minutes.
  • the reaction mixture is then carefully poured onto 500 g of ice.
  • the aqueous mixture is extracted twice with 250 ml of ethyl acetate and the organic phase is extracted three times with 200 ml of saturated sodium hydrogen carbonate solution.
  • the aqueous sodium bicarbonate solutions are combined and acidified with concentrated sulfuric acid.
  • An emulsifiable concentrate contains the following components:
  • active ingredient 250 g / l polyaryl polyethoxylate (emulsifier) 300 g / l N-methylpyrrolidone (solvent) ad 1000 ml
  • solvent 300 g / l N-methylpyrrolidone (solvent) ad 1000 ml
  • active ingredient and the emulsifier are dissolved in the solvent with stirring, and the solution is made up to 1 liter with additional solvent.
  • the resulting emulsifiable concentrate can be emulsified in water and thus results in a ready-to-use spray mixture with the desired concentration.
  • the mixture is then finely ground using a pin mill or comparable grinding device.
  • the resulting wettable powder gives a fine suspension when stirred into water, which is suitable as a ready-to-use spray liquor.

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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)
EP88907596A 1987-09-23 1988-09-19 Heterocyclische verbindungen Withdrawn EP0333791A1 (de)

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CH3677/87 1987-09-23

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AU2328188A (en) 1989-04-18
JPH02501388A (ja) 1990-05-17
DK247889D0 (da) 1989-05-22
HU203542B (en) 1991-08-28
WO1989002891A1 (fr) 1989-04-06
US5017211A (en) 1991-05-21
DK247889A (da) 1989-05-22
BR8807217A (pt) 1989-10-17
KR890701567A (ko) 1989-12-21

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