EP2225234A1 - Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées - Google Patents

Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées

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Publication number
EP2225234A1
EP2225234A1 EP08864548A EP08864548A EP2225234A1 EP 2225234 A1 EP2225234 A1 EP 2225234A1 EP 08864548 A EP08864548 A EP 08864548A EP 08864548 A EP08864548 A EP 08864548A EP 2225234 A1 EP2225234 A1 EP 2225234A1
Authority
EP
European Patent Office
Prior art keywords
halogen
general formula
optionally substituted
substituted
optionally
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Withdrawn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
EP08864548A
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German (de)
English (en)
Inventor
Klaus-Helmut Müller
Ernst Rudolf Gesing
Christian Waldraff
Heinz Kehne
Dieter Feucht
Martin Jeffrey Hills
Christopher Hugh Rosinger
Jan Dittgen
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Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Priority claimed from EP07024727A external-priority patent/EP2072512A1/fr
Priority claimed from DE102008006005A external-priority patent/DE102008006005A1/de
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP08864548A priority Critical patent/EP2225234A1/fr
Publication of EP2225234A1 publication Critical patent/EP2225234A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Definitions

  • the present invention relates to N-azinyl-N'-pyridylsulfonylureas.
  • the present invention relates to mixtures of the aforementioned urea derivatives with other herbicides and / or safeners. Moreover, the present invention relates to processes for the preparation of the aforementioned urea derivatives and the use of these compounds as herbicides and plant growth regulators alone and in admixture with safeners and / or in admixture with other herbicides, in particular their use for plant control in specific crops or as crop protection regulators ,
  • N-azinyl-N'-arylsulphonylureas are linked to simple open-chain hydroxamic acid ester groups in the aryl part, e.g. N- (4,6-dimethylpyrimidin-2-yl) -N '- (2-methoxyaminocarbonyl-phenylsulfonyl) -urea and the corresponding N42-n-octyloxyaminocycloconphenylsulfonyl) -urea have herbicidal properties (compare DE 3 516 435 A, EP 0173958 A, US 4,704,158).
  • N-azinyl-N'-hetarylsulfonylureas which are substituted in the hetaryl by O.N-dialkylated, also open-chain hydroxamic acid groups (see, EP 0 301 784 A); corresponding cyclic hydroxamic acid derivatives, however, have not previously been described.
  • urea derivatives which are used as herbicides or plant growth regulators, in particular with a satisfactory herbicidal activity against harmful plants, with a broad spectrum against harmful plants and / or with a high selectivity in crops can be.
  • These urea derivatives should preferably have a better property profile, in particular a better herbicidal action against harmful plants, a broader spectrum of harmful plants and / or a higher selectivity in crops than the urea derivatives known from the prior art.
  • V, W, X and Y are chosen such that one of these indices is nitrogen and the remaining indices are carbon atoms which unsubstituted or may be substituted with the illustrated R 8 ;
  • A is selected from the group consisting of nitrogen and CR 9 ; in which
  • R 9 is selected from the group consisting of hydrogen, alkyl, halo and haloalkyl
  • R 1 is selected from the group consisting of hydrogen and an optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl,
  • R 2 is selected from the group consisting of hydrogen, halogen, optionally substituted by halogen alkyl, optionally substituted by halogen alkoxy, optionally substituted by halogen
  • Alkylthio optionally substituted by halogen alkylamino or optionally substituted by halogen dialkylamino;
  • R 3 is selected from the group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally
  • Halogen-substituted alkoxy optionally halogen-substituted alkylthio, optionally halogen-substituted alkylamino or optionally halogen-substituted dialkylamino,
  • R 4 to R 7 are selected from the group consisting of hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, the radicals being unsubstituted or one or more radicals selected from the group consisting of halogen, cyano, alkoxy and
  • Alkylthio, or R 4 and R 6 or R 5 and R 7 is an optionally interrupted by oxygen or sulfur alkylidene Represent group
  • R 8 is selected from the group consisting of hydrogen, halogen,
  • Q is selected from the group consisting of oxygen or sulfur, in particular oxygen,
  • a first embodiment of the present invention comprises compounds of the general formula (I) in which
  • A is preferably selected from the group consisting of nitrogen and CH.0
  • a second embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 1 is preferably selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxyalkyl, alkenyl and alkynyl, where the radicals may be unsubstituted or may carry one or more halogen atoms,
  • R 1 is particularly preferably selected from the group consisting of
  • R 1 is particularly preferably selected from the group consisting of hydrogen and methyl
  • R 1 is particularly preferably hydrogen.
  • a third embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 2 is preferably selected from the group consisting of hydrogen, halogen,
  • R 2 is particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoroethoxy, difluoromethoxy, methylthio, methylamino and dimethylamino,
  • R 2 is particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, methoxy, methylthio and dimethylamino.
  • a fourth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 3 is preferably selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, alkylamino and dialkylamino, where the radicals may be unsubstituted or may carry one or more halogen atoms,
  • R 3 is particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoroethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
  • R 3 is particularly preferably selected from the group consisting of methyl, methoxy and trifluoroethoxy.
  • a fifth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 4 to R 7 are preferably selected from the group consisting of hydrogen, halogen, cyano,, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino,
  • R 4 to R 7 are particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, cyclopropyl, n-, i- s- or tertertert.
  • R 4 and R 6 or R 5 and R 7 is a CH 2 -CH 2 -CH 2 group, a CH 2 -CH 2 -CH 2 -CH 2 -GrUpPe, a CH 2 -O-CH 2 -group, CH 2 -S-CH 2 -group, a CH 2 -O-CH 2 -CH 2 -group, represents a CH 2 -CH 2 -O-CH 2 group or CH 2 -CH 2 -O-CH 2 -CH 2 group,
  • R 4 to R 7 are particularly preferably selected from the group consisting of hydrogen, methyl, ethyl, propyl and isopropyl, or R 4 and R 6 or R 5 and R 7 is a CH 2 -CH 2 - CH 2 -group, a CH 2 -CH 2 -CH 2 -CH 2 -group, a CH 2 -O-CH 2 -group, CH 2 -S-CH 2 - group, a CH 2 -O-CH 2 -CH 2 group, a CH 2 -CH 2 -O-CH 2 group or CH 2 is -CH 2 -O-CH 2 -CH 2 -GrUpPe.
  • a sixth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 8 is preferably selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl, where the radicals may be unsubstituted or can carry one or more halogen atoms,
  • R 8 is particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino and dimethylamino, where the radicals are unsubstituted may be or may carry one or more halogen atoms,
  • R 8 is particularly preferably hydrogen.
  • a nitrogen atom ie, a group selected from the group consisting of V, W, X and Y, corresponds to a nitrogen atom.
  • the remaining three radicals have the meaning of a carbon atom, wherein the carbon atoms may optionally be substituted by the radical R 8 .
  • the compound of the general formula (I) therefore has the following structure (Ia) in which V has the meaning of a nitrogen atom:
  • the compound of the general formula (I) therefore has the following structure (Ib), in which W has the meaning of a nitrogen atom:
  • the compound of the general formula (I) therefore has the following structure (Ic) in which X has the meaning of a nitrogen atom:
  • the compound of the general formula (I) therefore has the following structure (Id), in which Y has the meaning of a nitrogen atom:
  • the individual radicals R 1 to R 8 , A and Q may be the general, preferred and particularly preferred ones defined above Have meanings.
  • the present invention preferably also provides the lithium, sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkyl ammonium, di- (C 1 -C 4 -alkyl) -ammonium, tri- (C 1 -C 4 -alkyl) ammonium Ci-C 4 -alkyl) -ammonium, tetra- (-C 4 alkyl) - ammonium-, tri (Ci-C4-alkyl) sulfonium, C 5 - or C ⁇ cycloalkyl-ammonium, di- ( -C 2 - alkyl) -benzyl-ammonium, and tri (Ci-C 2 alkyl) -benzyl-ammonium salts of compounds of formula (I) in which R 1 to R 8, A and Q have the general above preferred , Particularly preferred and particularly preferred meanings and which can be prepared by generally conventional methods.
  • the compounds of the general formula (I) can furthermore, if appropriate, be prepared by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, such as, for example, As amino or alkylamino, salts.
  • a suitable inorganic or organic acid such as, for example, HCl, HBr, H 2 SO 4 or HNO 3
  • oxalic acid or sulfonic acids to a basic group, such as, for example, As amino or alkylamino, salts.
  • Suitable substituents which are present in deprotonated form such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can themselves be protonated, such as amino groups. Salts can also be formed by having suitable substituents, such as.
  • salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts with cations of the formula [NRR 1 R 11 R 111 J + , where R to R 1 each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl means e.g. Vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methyl-but-2-en-1-yl;
  • Alkynyl means e.g. Ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.
  • Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
  • Cycloheptyl and cyclooctyl can occur in bi- or tri-cyclic form.
  • haloalkyl groups and haloalkyl radicals of haloalkoxy, haloalkylthio, haloalkenyl, haloalkynyl, etc. are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl, 1-chloroprop-1-yl-3-yl.
  • halo is used according to the invention synonymously with "halogen”.
  • Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 C-atoms, in particular 1 to 6 C-atoms or preferably 2 to 4 C-atoms (unless otherwise defined), and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which are each straight-chain or branched can.
  • Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene.
  • Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples of these are 1, 2-dihydroxyethyl and 3-hydroxypropyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl. Unless defined otherwise, the definition "substituted by one or more radicals" means one or more identical or different radicals.
  • first substituent level if they contain hydrocarbon-containing moieties, may optionally be further substituted there (“second substituent plane"), for example by one of the substituents as defined for the first substituent level.
  • second substituent plane corresponds further substituent levels.
  • substituted radical includes only one or two substituent levels.
  • radicals with C atoms those having 1 to 6 C atoms, preferably 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred.
  • substituents from the group halogen for example fluorine and chlorine, (C 1 -C 4 ) -alkyl, preferably methyl or ethyl, (C 1 -C 4 ) -haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) -alkoxy, preferably methoxy or ethoxy, (CrC 4 ) haloalkoxy, nitro and cyano.
  • an aryl radical may preferably be phenyl which is one or more times, preferably up to three times, by identical or different radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4) - haloalkyl, (CrC 4) -haloalkoxy, cyano and nitro, for example o-, m- and p-tolyl, di-methylphenyle, 2-, 3- and 4-chlorophenyl , 2-, 3- and 4-trifluoromethyl and 2-, 3- and 4-trichloromethyl-phenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I).
  • stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods.
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • Another object of the present invention are methods for preparing corresponding compounds of general formula (I) and / or salts thereof.
  • the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of the general formula (II)
  • R 12 is a substituted or unsubstituted (C 1 -C 20 ) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C 1 -C 4 ) -alkyl, and wherein V, W, X, Y, R 1 to R 8 , Q and A are as defined above.
  • the compounds of general formula (II) can be obtained by reacting the compounds of general formula (X) with a chlorinating agent such as chlorine gas and ammonia solution according to the following reaction scheme:
  • the compounds of the general formula (X) can in turn be obtained by reacting compounds of the general formula (XI) with benzylmercaptan according to the following reaction scheme starting from the compounds of the general formula (XI):
  • 2-chloronicotinaldehyde oxime and substituted 2-chloronicotinaldehyde oximes are known, for example, from the prior art and can be prepared by methods known to the person skilled in the art (cf., WO 2003/090539, Helvetica Chimica Acta 59, 211-21 (1976), EP 0 012 158).
  • V, W, X, Y, R 1 to R 8 , Q and A are as defined above.
  • the compounds of general formula (I) are prepared by reacting sulfonyl (thio) carbamates of general formula (VI)
  • R 12 is a substituted or unsubstituted (CrC 2 O) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (DCO-alkyl, with an amino heterocycle of the general formula (V)
  • V, W, X, Y, R 1 to R 8 , Q and A are as defined above.
  • the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of the general formula (II)
  • reaction auxiliary wherein R 1 is hydrogen and R 2 to R 8 , V, W, X, Y, Q and A have the above significance.
  • the production takes place the compounds of the general formula (I) in that an aminoheterocycle of the general formula (V)
  • Hal is a halogen atom, preferably chlorine, with a (thio) cyanate, for example a metal (thio) cyanate, in particular an alkali metal (thio) cyanate, such as sodium (thio) cyanate, to a iso (thio) cyanate of Formula (IV)
  • V, W, X, Y, R 1 to R 8 , Q and A are as defined above.
  • R 12 is a substituted or unsubstituted (C 1 -C 2 0) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (dCO-alkyl, in the presence of a basic reaction auxiliary, wherein V, W, X, Y, R 1 to R 8 and A have the above significance.
  • the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid amides of the general formula (II)
  • V, W, X, Y, R 1 to R 8 , Q and A are as defined above.
  • inert solvents are used in each case.
  • inert solvents are used in the sense of the present This invention means solvents which are inert under the respective reaction conditions, ie in particular do not react with the educts, but need not be inert under any reaction conditions.
  • aromatic or aliphatic solvents such as benzene, toluene, xylene, mesitylene, hexane, heptane, octane, cyclohexane
  • aliphatic and aromatic halogenated hydrocarbons such as methylene chloride, dichloroe
  • Cyclohexanone Particularly preferred are toluene, xylene, dichlorobenzene, chlorobenzene, acetonitrile, acetone, butyronitrile or ethyl acetate.
  • the present invention is not limited to the solvents exemplified above.
  • the reaction temperature at which the reactions according to the above embodiments can be carried out can vary within wide ranges.
  • Normal pressure performed. However, it is also possible to work under elevated pressure or reduced pressure, generally between 0.1 bar and 10 bar.
  • the processes for preparing the N-azinyl-N'-pyridylsulfonylureas of the general formula (I) according to the invention are carried out in the presence of a basic reaction auxiliary.
  • a basic reaction auxiliary As such, all customary inorganic or organic bases are suitable.
  • alkali metal or alkaline earth metal hydrides such as lithium, sodium, potassium or calcium hydride, lithium, sodium or potassium amide, sodium or Potassium methoxide, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate , Sodium or potassium bicarbonate, as well as basic organic
  • Nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, NN-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, 2-methyl, 3-methyl and 4-methylpyridine , 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, N-methylpyridine, 4- (N 1 N-
  • DBU diazabicyclooctane
  • DBN diazabicyclononene
  • DBU diazabicycloundecene
  • Another object of the present invention are also certain intermediates, which are run in accordance with the synthetic routes shown above in the preparation of the compounds of general formula (I) according to the invention.
  • the present invention also relates to compounds of the general formula (II)
  • Another object of the present invention are in a second embodiment of the intermediates and compounds of general formula (IV)
  • Another object of the present invention are in a third
  • Libraries of compounds of formula (I) and / or their salts, which can be synthesized after the above reactions, can also be prepared in a parallelized manner, which can be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
  • Chromatographieapparaturen available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, United States.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods.
  • solid-phase assisted synthesis methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999.
  • Use Solid-phase assisted synthesis methods allow a series of protocols known from the literature, which in turn can be performed manually or automatically.
  • the "teabag method" (Houghten, US 4,631,211; Houghten et al., Proc. Natl. Acad. Sei., 1985, 82, 5131-5135) can be used with products of IRORI, 11149 North Torrey Pines Road, La JoIIa, CA 92037, USA.
  • the automation of solid phase assisted parallel synthesis succeeds, for example, by equipment of the companies Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Wirten, Germany.
  • the reactions can also be carried out, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • Another object of the invention is due to the herbicidal property of the compounds of general formula (I), the use of the compounds of general formula (I) according to the invention as herbicides for controlling harmful plants.
  • Another object of the invention is due to the herbicidal property of the compounds of general formula (I), the use of the compounds of general formula (I) according to the invention as herbicides for controlling harmful plants.
  • the required application rate of the compounds of the formula (I) varies. It can vary within wide limits, for example between 0.001 and 10000 g / ha or more of active substance, but is preferably between 0.5 and 5000 g / ha, preferably between 0.5 and 1000 g / ha and most preferably between 0.5 and 500 g / ha.
  • the compounds of the formula (I) according to the invention and their salts, also referred to below together as compounds of the formula (I), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • dicotyledonous weed species In dicotyledonous weed species, the spectrum of activity extends to species such. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annall side as well as Convolvulus, Cirsium, Rumex and Artemisia in perennial weeds.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga,
  • the compounds of general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton, oilseed rape and soy only insignificant or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • the substances of the general formula (I) according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, such as, for example, B. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures as it reduces or completely eliminates storage can be.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • z. B the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds of general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, EP 0131624).
  • genetic modifications of crop plants have been described in several cases for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376, WO 92/014827, US Pat.
  • transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP 0242236, EP 0242246) or glyphosate (WO 92/000377) or the sulfonylureas (EP 0257993, US Pat. No. 5,013,659)
  • Transgenic crops such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP 0142924, EP 0193259).
  • Transgenic crop plants with modified fatty acid composition (WO 91/013972). genetically modified crops with new content or secondary substances z.
  • Produce proteins ("molecular pharming") transgenic crops that are characterized by higher yields or better quality - transgenic crops which are characterized by a combination of, for example, the above-mentioned new properties (“gene stacking”)
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such.
  • B. Dicamba or against herbicides the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, are resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthase
  • HPPD Hydoxyphenylpyruvat dioxygenases
  • the invention therefore also relates to the use of Compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds of the general formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • Pesticide-active substances such as insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators produce, for. B. in the form of a finished formulation or as a tank mix.
  • Injection powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, also contain ionic and / or nonionic surfactants (wetting agent, dispersant) in addition to a diluent or inert substance, eg.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent z.
  • organic solvent z B. butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products
  • alkyl polyethers sorbitan esters
  • sorbitan esters such as e.g. B. sorbitan fatty acid esters or Polyoxethylenensorbitanester such.
  • Dusts are obtained by grinding the active ingredient with finely divided solids, eg. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as. B. are already listed above in the other formulation types, are produced. 5
  • Emulsions eg. As oil-in-water emulsions (EW) can be, for example, by means of stirring, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as. B. are already listed above in the other formulation types, produce.0
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for.
  • adhesives for.
  • polyvinyl alcohol polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, 5 kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are usually by the usual Aid0 such as spray drying, fluidized bed granulation, plate granulation, mixing with
  • the agrochemical preparations usually contain 0.1 to 99 wt .-%, in particular 0.1 to 95 wt .-%, active ingredient of the formula (I).
  • the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers and the like are present. be used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent-based agents, fillers, carriers and colorants, defoamers, evaporation inhibitors and the pH value and Viscosity-influencing agent.
  • the compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such.
  • pesticidal substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators
  • insecticides acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators
  • As a combination partner for the active compounds of the general formula (I) according to the invention in mixed formulations or in the tank mix for example, known active compounds which are based on an inhibition of, for example
  • Acetolactate synthase acetyl coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, 5
  • Enolpyruvylshikimat-3-phosphate synthetase or cellulose biosynthesis are used. Such compounds and other usable compounds with teilwiese unknown or other mechanism of action are z.
  • PM Pesticide Manual
  • 12th edition 2000 The British Crop Protection Council and the Royal Soc. of Chemistry (publisher) and literature cited therein.
  • literature-known herbicides which can be combined with the compounds of formula (I), z.
  • the following compounds are to be mentioned (note: the compounds are denoted either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
  • CDAA ie 2-chloro-N, N-di-2-propenylacetamide
  • CDEC ie diethyldithiocarbamic acid 2-chloroallyl ester
  • chlorofluorol -methyl
  • chlomethoxyfen clethodim
  • clomeprop chloramben; chlorazifop-butyl, chloromesulon; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron (-ethyl); chloroacetic acid; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal (dimethyl); chlorthiamid; chlorotoluron, cinidone (-methyl and -ethyl), cinmethylin; cinosulfuron; cisanilide; clefoxydim, clethodim; clodinafop and
  • 2,4-DEB dalapon; dazomed; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; ortho-dichlorobenzene; para-dichlorobenzene; dichlo ⁇ rop; dichlorprop-
  • diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (-ethyl); difenoxuron; difenzoquat; difenzoquat methylsulphate; diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethenamid-P; dimethazone, dimexyflam, dimethipine; di-methylarsinic acid; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; diquat-dibromide; dithiopyr; diuron; DNOC; 3,4-DP; DSMA; EBEP; eglinazine-ethyl; EL77, i.
  • cereals wheat, barley, rye, corn, rice, millet
  • sugar beet sugar cane
  • rapeseed cotton and soybeans, preferably cereals.
  • the following groups of compounds are suitable, for example, as safeners for the compounds (I), alone or in combinations thereof with other pesticides:
  • the safeners are preferably selected from the group consisting of:
  • ⁇ A is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (dC 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the pentally unsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group consisting of N and O, where at least one
  • N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • ITIA is 0 or 1;
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (CrC 4 ) alkyl, (Ci-C 4 ) AIkOXy or optionally substituted phenyl, preferably a radical of the formula OR A 3 , NHRA 4 or N (CH 3 ) 2 , in particular the formula OR A 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having in total 1 to 18 carbon atoms;
  • RA 4 is hydrogen, (CRCE) -alkyl 1 (CrC ⁇ JAlkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H 1 (Ci-C 8) alkyl, (C r C 8) haloalkyl, (d ⁇ Alkoxytd-CsJAlkyl, cyano or COOR 9, wherein R A 9 is hydrogen, (C r C 8) alkyl, (CrC 8 is) haloalkyl, (CrC 4) alkoxy (CrC 4) alkyl, (CrC 6) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri- (C r C 4) -alkyl-silyl;
  • RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl,
  • RB 1 is halogen, (CrC 4) alkyl, (C r C 4) alkoxy, nitro or (C r C 4) haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is ORB 3 , SR B 3 or NR 6 3 RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N atom to the carbonyl group in (S2) and unsubstituted or by radicals from the group (C 1 -C 4 ) alkyl, (C 1 -C 4 ) Alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR 8 3 , NHR 6 4 or N (CH 3 ) 2 , in particular the formula OR 8 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (CrC 4 ) alkyl radicals or by [(CrC 3 ) alkoxy] carbonyl;
  • Rc 1 is (C r C 4 ) alkyl, (CrC 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) Cycloalkyl, preferably dichloromethyl;
  • Rc 2, rc 3 are identical or different hydrogen, (CrC 4) alkyl, (C 2 -C 4) -alkenyl AI,
  • active agents of the dichloroacetamide type preferably: active agents of the dichloroacetamide type, often as pre-emergence safeners
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "diclonone” (dicyclonone) or “BAS145138” or “LAB145138” (S3-9) (3-dichloroacetyl-2, 5,5-trimethyl-1,3-diazabicyclo [4.3.0] nonane) from BASF, "furilazole” or "MON 13900” ((RS) -3-dichloroacetyl-5- (2-furyl) -2,2 dimethyl oxazolidine) (S3-10); and its (R) isomer (S3-11).
  • X 0 is CH or N
  • R 0 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (C r C 4 ) haloalkyl, (C r C 4 ) haloalkoxy, nitro, (C r C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) alkylsulfonyl, (C r C 4 ) alkoxycarbonyl or
  • R 0 3 is hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl; RD 4 is halogen, nitro, (Ci-C 4) alkyl, (dC 4) haloalkyl, (C r C4) haloalkoxy,
  • R 0 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl,
  • R 0 6 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the three latter radicals by v D radicals from the group halogen, hydroxy, (CrC 4 ) alkyl, (C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, or RD 5 and RD 6 together with the nitrogen atom bearing them form a pyrrolidinyl or piperidinyl radical;
  • R 7 0 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (CrC 6) alkyl,
  • (C 3 -C 6 ) cycloalkyl where the 2 latter radicals by VD substituents selected from the group consisting of halogen, (CrC 4 ) alkoxy, (CrC 6 ) haloalkoxy and (C r C 4 ) alkylthio and in the case of cyclic radicals also (C r C 4 ) alkyl and
  • V 0 is 0, 1, 2 or 3;
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
  • N-acylsulfamoylphenyl urea compounds of formula (S4) e.g. are known from EP-A-365484,
  • R 0 8> u ln DR D ndj 9 are independently hydrogen, (CrC ⁇ ) alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl, RD 4 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 m D 1 or 2;
  • RE 1 are independently halogen, (CrC 4) alkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, nitro;
  • a E is COORE 3 or COSR E 4
  • RE 3 , RE 4 are independently hydrogen, (CrC 4 ) AIKyI,
  • n E 1 is 0 or 1
  • n E 2 , n ⁇ 3 are independently 0, 1 or 2, preferably:
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
  • RF 3 is hydrogen, (C r C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably to to three equal or different residues from the
  • a group consisting of halogen and alkoxy is substituted; mean, or their salts,
  • ⁇ F is an integer from 0 to 2
  • n G is an integer from 0 to 4,
  • RG 2 (C 1 -C 16 ) Al kVl, (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
  • RG 3 is hydrogen or (C 1 -C 6 -alkyl.
  • S11) oxyimino compound type compounds (S11) known as seed dressings such as those described in US Pat. B.
  • Class I) isothiochromanone (S12) actives e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a corn seed safener for corn against damage by thiocarbamate herbicides, "fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2) as a safener for
  • Pretilachlor is known in sown rice
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn, " MG-838 "(CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) of the company
  • NK 049 3,3'-dimethyl-4-methoxybenzophenone known as safener for rice against damage of some herbicides
  • COD (1-bromo-4- (chloromethylsulfonyl) benzene) by Kumiai, (CAS Reg. No. 54091-06-4), which is known as safener against damage of some herbicides in rice.
  • active substances primarily used as herbicides, but also having safener action on crop plants e.g. (2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid,
  • Preferred herbicide-safener combinations comprising (A) a herbicidally effective amount of one or more compounds of formula (I) or their salts, and (B) an antidote effective amount of one or more safeners.
  • herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth.
  • Antidote effective amount in the sense of the invention means an amount of one or more safeners which is suitable for reducing the phytotoxic effect of crop protection active ingredients (eg of herbicides) on crop plants.
  • Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • the formulations present in commercially available form are optionally diluted in a customary manner, for.
  • emulsifiable Concentrates emulsifiable Concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of general formula (I). It can vary within wide limits, eg. B. between 0.001 and 10.0 kg / ha or more active substance, but it is preferably between 0.005 and 5 kg / ha.
  • N-dimethylformamide 2.86 g (0.11 mol) of sodium hydride (95%) are suspended. While stirring, 13.64 g (0.11 mol) of benzylmercaptan are added dropwise, with heating taking place.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a readily dispersible in water, wettable powder is obtained by reacting 25 parts by weight of a compound of formula (I), 64 parts by weight of kaolin ambiencen quartz as inert material, 10 parts by weight of lignosulfonate and 1 part by weight oleoylmethyltaurinsaures sodium as net and
  • Dispersant mixed and ground in a pin mill.
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Isotridecanolpolyglykolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 0 C) mixed and milled in a ball mill to a fineness of less than 5 microns.
  • a water-dispersible granule is obtained by reacting 75 parts by weight of a compound of the formula (I)
  • a water-dispersible granules are also obtained by 25 parts by weight of a compound of formula (I), 5 "2,2'-dinaphthylmethane-6,6 l -disulfonate sodium,
  • Wood fiber pots laid in sandy loam soil and covered with soil are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 l / ha, with the addition of 0.2% wetting agent.
  • WP wettable powders
  • compounds of the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of the invention have for example a very good herbicidal activity against harmful plants such as Alopecurus myosuroides, Matricaria inodora and Stellaria media pre-emergence in a Application rate of 0.08 kg and less active substance per hectare.
  • ALOMY Field Foxtail (gras) (Alopecurus myosuroides)
  • MATIN Odorless Chamomile (Matricaria inodora)
  • STEME Chickweed (Stellaria media)
  • compounds according to the invention have a good herbicidal postemergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of the invention have a very good herbicidal activity against harmful plants such as Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum, Abutilon theophrasti, Amaranthus retroflexus, Pharitis purpurea, Stellaria media and Viola tricolor postemergence at an application rate of 0.08 kg and less active substance per hectare.
  • ECHCG Barnyardgrass (Echinochloa crus-galli)
  • ABUTH Velvet Poplar (Abutilon theophrasti)
  • AMARE Curved Foxtail (Amaranthus retroflexus)
  • PHBPU Purple Glory (Pharbitis / Ipomoea purpurea)
  • STEME Chickweed (Stellaria media)

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne des composés de formule générale (I), dans laquelle les substituants respectifs ont les significations indiquées dans la description. Les composés de formule générale (I) peuvent être utilisés comme herbicides et comme régulateurs de la croissance des plantes.
EP08864548A 2007-12-20 2008-12-04 Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées Withdrawn EP2225234A1 (fr)

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EP08864548A EP2225234A1 (fr) 2007-12-20 2008-12-04 Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées

Applications Claiming Priority (4)

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EP07024727A EP2072512A1 (fr) 2007-12-20 2007-12-20 Composés herbicides à base d'urées N-azinyl-N'-pyridylsulfonyl
DE102008006005A DE102008006005A1 (de) 2008-01-25 2008-01-25 Herbizide Verbindungen auf Basis von N-Azinyl-N'-pyridylsulfonyl-harnstoffen
PCT/EP2008/010265 WO2009080182A1 (fr) 2007-12-20 2008-12-04 Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées
EP08864548A EP2225234A1 (fr) 2007-12-20 2008-12-04 Composés herbicides à base de n-azinyl-n'-pyridylsulfonyl-urées

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EP3159331A1 (fr) 2010-05-05 2017-04-26 Infinity Pharmaceuticals, Inc. Tretrazolones utilisées comme inhibiteurs de synthase d'acide gras
CN102993176A (zh) * 2012-11-02 2013-03-27 安徽丰乐农化有限责任公司 一种烟嘧磺隆的合成新工艺
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AR072040A1 (es) 2010-08-04
CN101903379A (zh) 2010-12-01
CA2710113A1 (fr) 2009-07-02

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