EP3720853A1 - 3-amino-[1,2,4]-triazole derivatives and their use for controlling undesired plant growth - Google Patents

3-amino-[1,2,4]-triazole derivatives and their use for controlling undesired plant growth

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Publication number
EP3720853A1
EP3720853A1 EP18807364.7A EP18807364A EP3720853A1 EP 3720853 A1 EP3720853 A1 EP 3720853A1 EP 18807364 A EP18807364 A EP 18807364A EP 3720853 A1 EP3720853 A1 EP 3720853A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
haloalkyl
amino
cycloalkyl
alkoxy
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Withdrawn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
EP18807364.7A
Other languages
German (de)
French (fr)
Inventor
Estella Buscato Arsequell
Klemens Minn
Harald Jakobi
Hansjörg Dietrich
Anu Bheemaiah MACHETTIRA
Elmar Gatzweiler
Dirk Schmutzler
Christopher Hugh Rosinger
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.)
Bayer AG
Bayer CropScience AG
Original Assignee
Bayer AG
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer AG, Bayer CropScience AG filed Critical Bayer AG
Publication of EP3720853A1 publication Critical patent/EP3720853A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants and in the
  • the invention relates to substituted 3-amino [1,2,4] triazole derivatives, processes for their preparation and their use for controlling harmful plants.
  • the herbicidal action of such 3-amino [1,2,4] triazole derivatives is not known from the prior art.
  • the object of the present invention is to provide alternative active substances which can be used as herbicides or plant growth regulators, with a satisfactory herbicidal action and a broad spectrum of activity against harmful plants and / or with a high selectivity in crops of useful plants.
  • the object is achieved by specifically substituted 3-amino [1,2,4] triazole derivatives of the formula (I) according to claim 1, which can be used advantageously as herbicides and also as plant growth regulators.
  • the present invention therefore relates to compounds of formula (I) and their agrochemical-ve Nursingen salts
  • R1 is selected from the group consisting of
  • C 3 -C 8 ) -cycloalkyl which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -
  • C 3 -C 8 ) -cycloalkyl which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -
  • R6 and R7 are each independently hydrogen, (C1-C6) -alkyl, (C1-C6) -haloalkyl, (C1-C6) -alkoxy, (C1-C6) -haloalkoxy, (C6-C14) -aryl, (C6 -C14) -aryloxy, (C6-C14) -arylcarbonyl or (C6-C14) -aryloxycarbonyl; or R6 and R7 together with the carbon to which they are attached form a (C3-C7) -alkylene group which may contain one or more oxygen and / or sulfur atoms, the (C3-C3)
  • the compounds of the formula (I) are distinguished, in addition to a good activity profile and good crop plant compatibility, by their cost-effective production, since the substances according to the invention can be prepared from inexpensive and easily accessible precursors by inexpensive processes.
  • a first embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is preferably hydrogen, halogen, cyano, C (OO) NH 2, NO 2, (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, (C1-C6) -haloalkyl, (C3-C6) -cyclopropyl, (C1-C6) -alkoxy, (C1-C6) -thioalkyl, (C1-C6) -alkylthio, (C2-C6) -alkynyl, mono- (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamio or tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl; R1 particularly preferably hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, trimethylsilylethynyl,
  • a second embodiment of the present invention comprises compounds of the general formula (I) in which R 2 is preferably hydrogen, halogen, (C 1 -C 6 ) -alkylphenyl, (C 6 -C 14 ) -aryl which is bonded to the aryl radical by (C 1 -C 6 ) -alkyl, (C 6 -C 14 ) -haloalkyl and / or halogen; C 6 aryl (C 1 - C 6) -haloalkyl, (C 1 -C 6) alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C
  • a third embodiment of the present invention comprises compounds of the general formula (I) in which R1 and R2 together with the carbon atom or nitrogen atom to which they are attached form a saturated six- or seven-membered ring, as shown below
  • saturated six- or seven-membered ring is represented by m substituents selected from halo, acetyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, trifluoromethyl, (C 1 -C 6) alkylsulfonyl, (C 3 -C 6) cycloalkylsulfonyl or phenylsulfonyl may be substituted, and wherein R 1a is preferably selected from hydrogen, acetyl, trifluoroacetyl, (C 1 -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) cycloalkylcarbonyl, ( C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl, phenyl,
  • saturated six- or seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, trifluoromethyl, (C 1 -C 6 ) -alkylsulfonyl, ( C 3 -C 6 ) -cycloalkylsulfonyl or phenylsulfonyl, and wherein R 1a is preferably selected from hydrogen, acetyl, trifluoroacetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkylcarbonyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkylsulf
  • a fourth embodiment of the present invention comprises compounds of the general formula (I) in which R3 is preferably hydrogen.
  • a fifth embodiment of the present invention comprises compounds of the general formula (I) in which R 4 and R 5 are each independently of one another, preferably hydrogen, (C 1 -C 6 ) -alkyl, hydroxy,
  • R4 and R5 are each independently of one another, more preferably hydrogen, methyl, ethyl,
  • R4 and R5 are each independently, most preferably hydrogen, methyl or
  • R4 and R5 are ethyl.
  • R4 and R5 is hydrogen.
  • at least one of the radicals R4 or R5 is hydrogen and the other radical R4 or R5 is different from hydrogen and in particular (C1-C6) -alkyl.
  • one of the radicals R4 or R5 is hydrogen and the other radical R4 or R5 is methyl.
  • a sixth embodiment of the present invention comprises compounds of the general formula (I) in which R4 and R5 preferably together form a (C 2 -C 7) -alkylene group which is one or more
  • (C2-C7) - alkylene group may be monosubstituted or polysubstituted by halogen and the respective halogen substituents may be the same or different; R4 and R5 particularly preferably together with the carbon atom to which they are attached form a three- or four-membered ring; and R4 and R5 most preferably together form a non-substituted (C2-C3) alkylene group.
  • a seventh embodiment of the present invention comprises compounds of the general formula (I) in which R6 and R7 are independently hydrogen, (C1-C6) -alkyl or (C6-C14) -aryl; R6 and R7 are independently of each other, more preferably hydrogen, methyl or phenyl;
  • An eighth embodiment of the present invention comprises compounds of the general formula (I) in which R 8 is preferably hydrogen, (C 1 -C 6 ) -alkyl or halogen; R 8 is particularly preferably hydrogen, methyl or fluorine; and R8 is very particularly preferably hydrogen.
  • a ninth embodiment of the present invention comprises compounds of the general formula (I) in which R 9 is preferably hydrogen or (C 1 -C 6) -alkyl; R 9 is particularly preferably hydrogen or methyl; and R9 is very particularly preferably hydrogen.
  • a tenth embodiment of the present invention comprises compounds of the general formula (I) in which R 10 is preferably hydrogen, (C 1 -C 6) -alkyl, di (C 1 -C 6) -alkylamino, halogen, (C 2 -C 6) -alkenyl, ( C 2 -C 6) alkynyl, (C 1 -C 6) -alkyl- (C 2 -C 6) -alkynyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl- (C 2 -C 6) -alkynyl, cyano, ( C1-C6) alkoxycarbonyl or aminocarbonyl;
  • R 10 is particularly preferably hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluorine, chlorine, bromine, iodine, ethenyl, ethy
  • An eleventh embodiment of the present invention comprises compounds of the general formula (I) in which R 11 is preferably hydrogen or (C 1 -C 6) alkyl; R11 is more preferably hydrogen or methyl; and R11 is very particularly preferably hydrogen.
  • X is very particularly preferably a bond, where n is 1 or 2.
  • a thirteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 12 is preferably hydrogen.
  • a fourteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 13 is preferably hydrogen.
  • a fifteenth embodiment of the present invention comprises compounds of the general formula (I) in which the number of run m is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2, or 3 and most preferably 0, 1 or 2.
  • a sixteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 and R 2 together with the carbon atom or nitrogen atom to which they are attached
  • saturated six- or seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, trifluoromethyl, (C 1 -C 6 ) -alkylsulfonyl, ( C 3 -C 6 ) -cycloalkylsulfonyl or phenylsulfonyl, and wherein R 1a is hydrogen, acetyl, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl or phenylcarbonyl, wherein the
  • Phenyl may be substituted with a halogen
  • R3 is hydrogen
  • R4 and R5 are each independently hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy or methoxy
  • R6 and R7 are independently hydrogen, methyl or phenyl
  • R8 is hydrogen, methyl or fluorine
  • R9 is hydrogen or methyl
  • R 10 is hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluoro, chloro, bromo, iodo, ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH 2 C 1 -C-, cyano, COOMe or CONH 2
  • R11 is hydrogen or methyl
  • X is a bond, where n is 1 or 2.
  • a seventeenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 and R 2 together with the carbon atom or nitrogen atom to which they are attached
  • saturated six- or seven-membered ring is represented by m substituents selected from halo, acetyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, trifluoromethyl, (C 1 -C 6) alkylsulfonyl, (C 3 -C 6) cycloalkylsulfonyl or phenylsulfonyl may be substituted,
  • R 1a is hydrogen, acetyl or (C 1 -C 4) -alkyl
  • R3 is hydrogen
  • R4 and R5 are each independently methyl, ethyl or hydrogen
  • R6, R7, R8, R9 and R11 are hydrogen
  • R 10 is hydrogen, methyl or fluorine
  • X is a bond, where n is 1 or 2.
  • An eighteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, trimethylsilylethynyl, methyl, ethyl,
  • R2 is hydrogen, chloro, phenyl , 2-methylphenyl, 3-trifluoromethylphenyl, methyl, ethyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl,
  • R3 is hydrogen;
  • R4 and R5 are each independently hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy or methoxy;
  • R6 and R7 are independently hydrogen, methyl or phenyl;
  • R8 is hydrogen, methyl or fluorine;
  • R9 is hydrogen or methyl;
  • R 10 is hydrogen, methyl, propy
  • a nineteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is methyl, ethyl, propyl, dimethylamino, diethylamio, 1-pyrrolidino, 1-piperidino, 4-morpholino, acetyl or trifluoromethyl; R 2 is methyl or ethyl; R3 is hydrogen; R4 and R5 are each independently hydrogen, methyl or ethyl; R6 and R7 are hydrogen; R8 is hydrogen; R9 is hydrogen; R 10 is hydrogen, methyl or fluorine; R11 is hydrogen; and X is a bond, where n is 1 or 2.
  • the compound of the general formula (I) also includes compounds which are characterized by a) protonation, b) alkylation or c) oxidation on a
  • Nitrogen atom are quaternized. In particular, these include the corresponding N-oxides.
  • the compounds of formula (I) can form salts. Salt formation can be caused by the action of a base to those compounds of the formula (I) take place, which carry an acidic hydrogen atom.
  • suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
  • Potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, 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, for example with cations of the formula [NRR'R''R''] +, where R to R'''Each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents which are present in deprotonated form can form internal salts with groups which can themselves be protonated, such as amino groups.
  • the compounds of the formula (I) and their salts are also referred to briefly as "compounds (I)" used according to the invention or according to the invention.
  • the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched. Unless specifically stated, these residues are the lower ones
  • Carbon skeletons e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred.
  • Alkyl radicals including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexy and 1,4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; wherein at least one double bond or triple bond, preferably a double
  • Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2- Methyl-prop-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-ene-1-yl;
  • Alkynyl includes, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl. Cycloalkyl groups are, for.
  • cycloalkyl groups 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 C-atoms or 2 to 6, in particular 1 to 4 C-atoms or preferably 2 to 4 C-atoms, as well as the
  • 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.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl, alkenyl and alkynyl are alkyl, alkenyl or alkynyl, for example, partially or completely substituted by halogen, preferably by fluorine, chlorine or bromine, in particular by fluorine and / or chlorine.
  • Monohaloalkyl (
  • 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;
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.
  • compounds of the general formula (II) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.
  • this carbon atom can have both an (R) and an (S) configuration.
  • the present invention covers compounds of the general formula (I) having both (S) and (R) configurations, that is to say that the present invention covers the compounds of the general formula (I) in which the relevant carbon atom ( 1) an (R) configuration; or (2) has an (S) configuration.
  • the respective (R) compound having an enantioselectivity of more than 50% ee, preferably 60 to 100% ee, in particular 80 to 100% ee, very particular 90 to 100% ee, most preferably 95 to 100% ee, based on the total content of the relevant (R) compound is present.
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R, or analog-R), preferably 80 to 100 % (R, or analog-R), in particular 90 to 100% (R, or analog-R), very particularly 95 to 100% (R, or analog-R), is present.
  • the compounds of the general formula (I) according to the invention may have further chiral centers on the carbon atoms marked (**) and (***)
  • Enantiomers and diastereomers occur.
  • Corresponding stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic 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 are encompassed by the general formula (I) but are not specified with their specific stereoform and their mixtures. Particular preference is given to compounds of the general formula (I)
  • Another object of the present invention are methods for preparing corresponding compounds of general formula (I) and / or salts thereof and / or their agrochemically compatible quaternized nitrogen derivatives
  • R 1, R 2 have the abovementioned meaning and Z 1 is an exchangeable radical or a leaving group, with an amine of the general formula (III)
  • the exchangeable radical Z1 or the leaving group Z1 is fluorine, chlorine, bromine, iodine, a (C1-4) -alkylsulfanyl or a (C1-4) -alkylsulfinyl or a (C1-4) -alkylsulfonyl, an unsubstituted or a phenyl (C1-4) -alkylsulfonyl which is monosubstituted or polysubstituted by fluorine, chlorine, bromine or (C1-4) -alkyl or (C1-4) -alkoxy or a (C1-4) -alkylphenyl-sulfonyl.
  • a radical Z1 can be converted into another, more easily exchangeable group.
  • a radical Z1 can be converted into another, more easily exchangeable group.
  • Oxidizing agents such as m-chloroperbenzoic acid or Oxone® in a (C 1-4 ) alkylsulfinyl or a (C 1-4 ) alkylsulfonyl or mixtures thereof are converted and then with an amine of general formula (III) or an acid addition salt using a Auxiliary base such as triethylamine or potassium carbonate are reacted.
  • the reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
  • Transition metal catalyst systems and bases are e.g. [(2-Dicyclohexylphosphino-3,6-dimethoxy-2 ', 4', 6'-triisopropyl-1,1'-biphenyl) -2- (2'-amino-1,1'-biphenyl)] palladium (II) Methanesulfonate methanesulfonates (G3 Brettphos Pd®) and 2- (dicyclohexylphosphino) -3,6-dimethoxy-2 ', 4', 6'-triisopropyl-1,1'-biphenyl (Brettphos®) with t-butoxide or chloro [2- (dicyclohexylphosphino) -3,6-dimethoxy-2 ', 4', 6'-triisopropylbiphenyl] [2- (2-aminoethyl) phenyl] Pd
  • Z1 is an exchangeable group or a leaving group
  • the sulfur can be successfully oxidized with an oxidizing agent such as m-chloroperbenzoic acid or potassium peroxymonosulfate (Oxone®) (Scheme 2).
  • the substituted cyclic 1,2,4-triazoles of the general formula (II) according to the invention can be prepared as follows (Scheme 3).
  • Acid addition salt of the amine of the general formula (III) are reacted with dimethyl-N-cyanodithioiminocarbonate, for example, by the methods described in J. Med. Chem. 56, 9071-9088 (2013). and cyclized with hydrazine hydrate to aminotriazole (IX).
  • the aminotriazole can be converted to the 6,7-dihydro-4H- [1,2,4] triazolo [1,5-a] pyrimidin-5-one by a Michael addition with methyl acrylate.
  • the starting compounds used in the above Scheme 4 are either commercially available or can be prepared by known methods.
  • the substituted cyclic 1,2,4-triazoles according to the invention can be prepared with the general formula (II).
  • 1H-1,2,4-triazole-3,5-diamine is converted into a 2-amino group by a Michael addition with methyl acrylate -6,7-dihydro-4H- [1,2,4] triazolo [1,5-a] pyrimidin-5-one (XI).
  • the amino group can be converted into a leaving group Z1 in a Sandmeyer reaction, for example by the methods described in MedChemComm, 4, 422-431 (2013), where Xa is as defined above.
  • the exchangeable radical Z1, and the leaving group Z1 represents fluorine, chlorine, bromine, iodine, a (C 1-4) - alkylsulphanyl or a (C 1-4) alkylsulfinyl or a (C 1-4) alkylsulfonyl, an unsubstituted or mono- or polysubstituted with fluorine, chlorine, bromine or (C 1-4 ) -alkyl or (C 1-4 ) -alkoxy-substituted phenyl- (C 1-4 ) -alkylsulfonyl or a (C 1-4 ) alkylphenyl-sulfonyl.
  • reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
  • Transition metal catalyst systems The last reaction is by alkylation under basic conditions.
  • the exchangeable radical Z1 or the leaving group Z1 is fluorine, chlorine, bromine, iodine, a (C1-4) -alkylsulfanyl or a (C1-4) -alkylsulfinyl or a (C1-4) -alkylsulfonyl, an unsubstituted or a phenyl (C1-4) -alkylsulfonyl which is monosubstituted or polysubstituted by fluorine, chlorine, bromine or (C1-4) -alkyl or (C1-4) -alkoxy or a (C1-4) -alkylphenyl-sulfonyl.
  • reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
  • amines of the general formula (III) or the acid addition salt thereof are commercially available or their synthesis is described in WO 2004/069814 A1.
  • Compounds of the general formula (I) can also be prepared by first preparing a compound of the general formula (I), which are then converted into other target molecules in further reaction steps.
  • sulfur atoms in R1 can be converted by oxidation into SO or SO2, or NH can be converted to the corresponding amides by reaction with acid chlorides or anhydrides or by reaction with sulfonyl chlorides
  • Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may 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, pages 1 to 34.
  • reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451 , UNITED STATES.
  • chromatographic apparatuses are available, inter alia, for example Teledyne ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. 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.
  • Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically. Both solid and liquid phases may require the performance of one or more
  • Pre-emergence herbicides breaks through (pre-emergence herbicides). Postemergence herbicides are finally used when either the cotyledons or leaves are already formed from the crop.
  • the compounds of the invention can be used both in the forerun and in the wake, wherein a use of the compounds of the invention in the flow is preferred.
  • Pre-emergence treatment includes pre-sowing (ppi) pre-sowing treatment as well as treatment of sown, but not overgrown crop areas. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of general formula (I) and / or their salts.
  • Application rate can vary within wide limits.
  • the total amount of compounds of general formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in Range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications.
  • the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / Ha. This applies to both the application in the
  • 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. In the individual examples may be mentioned some representatives of the monocotyledonous and dicotyledonous weed flora, which can be controlled by the compounds of the general formula (I) according to the invention, without the intention of limiting them to certain species.
  • Fimbristylis ischaemum, lolium, monochoria, panicum, paspalum, phalaris, phleum, poa, sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperusart mainly from the Terryle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusart well grasped. 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, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium are observed.
  • 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 influence the metabolism
  • Plant ingredients and harvest relief such. 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 storage can be reduced or completely prevented. Due to their herbicidal and plant growth regulatory properties, 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. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Other special properties may be in a tolerance or resistance to abiotic stressors z.
  • heat, cold, drought, salt and ultraviolet radiation Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful and ornamental plants, eg. As 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.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
  • EP 0131624 genetic engineering alterations of crop plants for the purpose of modifying the starch synthesized in plants (eg WO 92/011376, WO 92/014827, WO 91/019806) have been described in several cases, - transgenic crop plants which are resistant to certain herbicides of the type Glufosinate (cf., for example,
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins
  • 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. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat.
  • the production of plant cells with 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 for the purpose of achieving a cosuppression effect or expression at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA Sequences that 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.
  • transgenic plants can in principle be plants of any one
  • 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.
  • acetolactate synthases As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (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 synthases
  • HPPD Hydoxyphenylpyruvat dioxygenases
  • the active compounds of the general formula (I) according to the invention in addition to the effects observed in other crops against harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum, that can be combated, changed application rates, which can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the 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 according to which biological and / or chemical-physical parameters are given.
  • 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
  • EW emulsions
  • SC Suspension concentrates
  • SC oil or water based dispersions
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersant e.g. Example, polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine.
  • 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 made by dissolving the active ingredient in an organic solvent z.
  • organic solvent z As butanol, cyclohexanone, dimethylformamide, xylene or 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).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as. B. sorbitan fatty acid esters or
  • 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.
  • Emulsions eg. As oil-in-water emulsions (EW), for example, by stirring,
  • Colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as. B. are listed above in the other types of formulation produced.
  • 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, 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 mixed with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying for the preparation of plate, fluidized bed, extruder and spray granules see, for. B. Methods in "Spray-Drying Handbook” 3rd ed.1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff .; “Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
  • pesticide formulation see, e.g.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound 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 .-%.
  • 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.
  • Growth regulators are used in combination, z. B. as a ready-made formulation or as
  • Tank mixes examples of combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase,
  • Photosystem I, photosystem II or protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 17th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2015 (see https://www.bcpc.org/product/the-pesticide- manual- 17th-edition) or online https://www.bcpc.org/product/bcpc-online-pesticide- manual-latest version and literature cited therein.
  • herbicidal mixture partners are: acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro) 2-fluoro-3-methylphenyl) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorotassium, aminocyclopyrachloromethyl, aminopyralid, amitrole, ammonium sulfamates, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazol
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, - dimethylammonium and methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate , glufosinate-ammonium, glufosinate-P-s
  • methabenzothiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (Pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, ox
  • plant growth regulators as possible mixing partners are: acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
  • n A is a natural number from 0 to 5, preferably 0 to 3; R 1
  • W A is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N and O groups, wherein at least one N atom and at most one O atom is contained in the ring, preferably a residue from the group (W 1
  • mA is 0 or 1; R 2
  • A is OR 3 3
  • 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 with the carbonyl group in (S1) and unsubstituted or by radicals from the group (C 1 -C 4 ) Alkyl, (C 1 -C 4 ) alkoxy or
  • phenyl is substituted, preferably a radical of the formula OR 3
  • A is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;
  • A is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl; R 5
  • A is H, (C 1 -C 8) alkyl, (C 1 -C 8) haloalkyl, (C 1 -C 4) alkoxy (C 1 -C 8) alkyl, cyano or COOR 9
  • A is hydrogen, (C 1 -C 8) alkyl, (C 1 -C 8) haloalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl,
  • A are the same or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1a), preferably
  • B is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl;
  • nB is a natural number from 0 to 5, preferably 0 to 3;
  • B is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;
  • B is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (C1 or C2) alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4) alkyl radicals or by [(C1-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid (S2a) type, preferably
  • C is (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) cycloalkyl, preferably dichloromethyl; R 2
  • C are identical or different hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (C 1 -C 4) haloalkyl, (C 2 -C 4) haloalkenyl, (C 1 -C 4) alkylcarbamoyl ( C1-C4) alkyl, (C2-C4) alkenylcarbamoyl- (C1-C4) alkyl, (C1-C4) alkoxy- (C1-C4) alkyl, dioxolanyl- (C1-C4) alkyl, thiazolyl, furyl, furylalkyl, thienyl , Piperidyl, substituted or unsubstituted phenyl, or R 2
  • C together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-active safeners), such as. B.
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2)
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3)
  • 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
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • a D is SO 2 -NR 3
  • D is -CO or CO-NR 3
  • D is halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (Cl -C 4) alkylcarbonyl; R 3
  • D is hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl or (C 2 -C 4) alkynyl; R 4
  • D is halogen, nitro, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 3 -C 6) cycloalkyl, phenyl, (C 1 -C 4) alkoxy, cyano, (C 1 -C 4) Alkylthio, (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (C 1 -C 4) alkylcarbonyl; R 5
  • D is hydrogen, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 5 -C 6) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing vD Heteroatoms from the group of nitrogen, oxygen and sulfur, where the seven latter radicals by vD substituents selected from the group consisting of halogen, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 1 - C 2 ) alkylsulfinyl, (C 1 -C 2) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxycarbonyl, (C 1 - C 4) alkylcarbonyl and phenyl and, in the case of
  • D is hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, wherein the three
  • D is hydrogen, (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, where the latter two radicals are represented by v D substituents from the group halogen, (C 1 - C4) alkoxy, (C1-C6) haloalkoxy and (C1-C4) alkylthio and in case of cyclic radicals, also (C1-C4) alkyl and (C 1 -C 4) haloalkyl substituted are; n D is 0, 1 or 2; m D is 1 or 2; v D is 0, 1, 2 or 3; of these preferred are compounds of the type of N-acylsulfonamides, for example of the following formula (S4a), the z. B. are known from WO-A-97/45016
  • D is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, CF 3; mD 1 or 2; vD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4b), e.g. are known from WO-A-99/16744,
  • D are independently hydrogen, (C 1 -C 8) alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 6) alkenyl, (C 3 -C 6) alkynyl, R 4
  • D is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, CF 3 mD is 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • D is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; m D 1 or 2; R 5
  • D is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • E are independently halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl,
  • E are each independently hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,
  • E is 0 or 1 n 2
  • E are independently 0, 1 or 2, preferably:
  • F is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl, (Cl -C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy, R 2
  • F is hydrogen or (C 1 -C 4 ) alkyl
  • F is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the
  • said C-containing radicals unsubstituted or substituted by one or more, preferably up to three identical or different radicals selected from the group consisting of halogen and alkoxy; or their salts, preferably compounds wherein X is F , F n is an integer from 0 to 2, R 1
  • F is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, R 2
  • F is hydrogen or (C 1 -C 4 ) alkyl
  • F is hydrogen, (C 1 -C 8) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, wherein each of the
  • S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • G is halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y G , Z G independently of one another O or S, n G is an integer from 0 to 4, R 2
  • G is hydrogen or (C 1 -C 6 ) alkyl.
  • Oxabetrinil ((Z) -1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as millet safener for millet against damage by metolachlor, "Fluxofenim” (1- (4 -Chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S11-2), which has been known as seed-etch safener for millet against damage by metolachlor and "Cyometrinil” or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as millet safener for millet against damage by metolachlor.
  • S12 active substances from the class of isothiochromanones (S12), such as, for example, methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg.No.205121-04-6 ) (S12-1) and related compounds of WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): “naphthalene anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides, "Fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as safener for pretilachlor in seeded rice, "flurazole” (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole -5-carboxylate) (S13-3) known as millet safener for millet against damages of alachlor and metolachlor, "CL 304415” (CAS Reg. No. 31541-57-8)
  • Cyanamide known as safener for maize against damage of imidazolinones "MG 191” (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5 ) of Nitrokemia Company, known as safener for corn, "MG 838” (CAS Reg. No. 33993-74-5)
  • H is a (C 1 -C 6 ) haloalkyl radical and R 2
  • H is hydrogen or halogen and R 3
  • H is independently hydrogen, (C 1 -C 16 ) alkyl, (C 2 -C 16 ) alkenyl or (C 2 -C 16 ) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, Hydroxy, cyano, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylamino, di [(C 1 -C 4 ) alkyl ] -amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or is
  • H is hydrogen or (C 1 -C 4) -alkyl or R 3 4
  • heterocyclic ring which, in addition to the nitrogen atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-4) C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy and (C1-C4) alkylthio substituted.
  • S16) active substances which are used primarily as herbicides, but also have safener action on crop plants, e.g. (2,4-dichlorophenoxy) acetic acid (2,4-D),
  • Preferred safeners are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, particular preference is given to:
  • Cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl are optionally diluted in a customary manner, for.
  • wettable powders emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
  • Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the external conditions such as temperature, humidity, the nature of the herbicide used, inter alia, the required application rate of the compounds of the general formula (I) varies. 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.
  • the present invention will be explained in more detail with reference to the following examples which the However, in no way limit the invention.
  • the resulting reaction mixture was then stirred in a microwave oven for 1.5 hours at a temperature of 120 ° C and concentrated after cooling to room temperature under reduced pressure.
  • the resulting residue was taken up with dichloromethane, water added, and the water phase was extracted several times thoroughly with dichloromethane.
  • the combined organic phases were washed with sat. Sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure.
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
  • a dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as inert material and comminuting in a hammer mill.
  • a water-dispersible, wettable powder is obtained by 25
  • Alkylphenolpolyglykolether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 ° C) mixed and in a ball mill to a fineness of less than 5 microns married.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight
  • a water-dispersible granules are obtained by reacting 75 parts by weight of a compound of formula (I) and / or salts thereof, 10 parts by weight calcium lignosulfonate, 5 parts by weight sodium lauryl sulfate, 3 parts by weight polyvinyl alcohol and 7 parts by weight of kaolin mixed, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as granulating.
  • a water-dispersible granule is also obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium 2 parts by weight of oleoylmethyltaurine acid, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water on a colloid mill homogenized and pre-crushed, then ground on a bead mill and the suspension thus obtained in a spray tower by means of a single-fluid nozzle atomized and dried.
  • Seeds of monocotyledonous or dicotyledonous weeds and crops are laid out in plastic or organic plant pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a water application rate of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • the pots are placed in the greenhouse and kept under good growth conditions for the test plants.
  • AMARE Amaranthus retroflexus AVEFA: Avena fatua
  • ECHCG Echinochloa crus-galli
  • PHBPU Ipomoea purpurea
  • POLCO Polygonum convolvulus
  • VERPE Veronica persica VIOTR: Viola tricolor Table B1: Pre-emergence herbicidal activity
  • Compounds Nos. I-248, I-353 and I-231 and other compounds from Table B5 have a good herbicidal activity against harmful plants during postemergence treatment.
  • the compounds No. I-377 and I-214 postemergence have a very good herbicidal action (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Setaria viridis, and Veronica persica at an application rate of 0.32 kg of active substance or less per hectare.
  • some of the compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize, rice or sugarcane practically unimpaired postemergence even at high doses of active ingredient.
  • some substances also protect dicotyledonous crops such as soybeans, cotton, oilseed rape, or sugarbeet.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable postemergence for combating undesired plant growth in agricultural crops.

Abstract

The invention relates to 3-amino-[1,2,4]-triazole derivatives of general formula (I) and the agrochemically compatible salts (I) thereof, and to the use thereof for controlling undesired plant growth.

Description

Bayer CropScience AG/Bayer AG  Bayer CropScience AG / Bayer AG
3-Amino-[1,2,4]-triazolderivate und deren Verwendung zur Bekämpfung unerwünschten 3-amino- [1,2,4] triazole derivatives and their use in combating undesirable
Pflanzenwachstums Beschreibung Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in Nutzpflanzenkulturen sowie im The invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants and in the
Ziergartenbereich und zur generellen Bekämpfung von Unkräutern und Ungräsern in Umweltbreichen, in denen Pflanzenwuchs störend ist. Insbesondere betrifft die Erfindung substituierte 3-Amino-[1,2,4]-triazolderivate, Verfahren zu deren Herstellung sowie deren Verwendung zur Bekämpfung von Schadpflanzen. Aus dem Stand der Technik ist die herbizide Wirkung derartiger 3-Amino-[1,2,4]-triazolderivate nicht bekannt. Die Anwendung der bekannten selektiven Herbizide zur Schadpflanzenbekämpfung oder als Ornamental garden area and for general control of weeds and weeds in Umweltbreichen in which plant growth is disturbing. In particular, the invention relates to substituted 3-amino [1,2,4] triazole derivatives, processes for their preparation and their use for controlling harmful plants. The herbicidal action of such 3-amino [1,2,4] triazole derivatives is not known from the prior art. The application of the known selective herbicides for controlling harmful plants or as
Pflanzenwachstumsregulatoren in verschiedenen Nutzpflanzenkulturen erfordert häufig eine hohe Kosten verursachende Aufwandmenge oder führt zu unerwünschten Schädigungen der Nutzpflanzen. Zudem ist die Anwendung der Wirkstoffe in vielen Fällen wegen verhältnismäßig hoher Herstellkosten unwirtschaftlich. Es ist deshalb erstrebenswert, alternative chemische Wirkstoffe bereitzustellen, die als Herbizide oder Pflanzenwachstumsregulatoren eingesetzt werden können und mit welchen bestimmte Vorteile im Vergleich zu aus dem Stand der Technik bekannten Systemen verbunden sind. Die Aufgabe der vorliegenden Erfindung besteht in der Bereitstellung alternativer Wirkstoffe, welche als Herbizide oder Pflanzenwachstumsregulatoren, mit einer zufriedenstellenden herbiziden Wirkung und einem breiten Wirkspektrum gegenüber Schadpflanzen und/oder mit einer hohen Selektivität in Nutzpflanzenkulturen, eingesetzt werden können. Gelöst wird die Aufgabe durch speziell substituierte 3-Amino-[1,2,4]-triazolderivate der Formel (I) gemäß Anspruch 1, welche vorteilhaft als Herbizide und auch als Pflanzenwachstumsregulatoren eingesetzt werden können. Gegenstand der vorliegenden Erfindung sind daher Verbindungen der Formel (I) und deren agrochemisch-veträglichen Salze Plant growth regulators in various crops often require a high cost-causing application rate or leads to undesirable damage to crops. In addition, the use of the active ingredients is uneconomical in many cases because of relatively high production costs. It is therefore desirable to provide alternative chemical agents which can be used as herbicides or plant growth regulators and which have certain advantages over prior art systems. The object of the present invention is to provide alternative active substances which can be used as herbicides or plant growth regulators, with a satisfactory herbicidal action and a broad spectrum of activity against harmful plants and / or with a high selectivity in crops of useful plants. The object is achieved by specifically substituted 3-amino [1,2,4] triazole derivatives of the formula (I) according to claim 1, which can be used advantageously as herbicides and also as plant growth regulators. The present invention therefore relates to compounds of formula (I) and their agrochemical-veträglichen salts
worin wherein
R1 ausgewählt ist aus der Gruppe, bestehend aus R1 is selected from the group consisting of
- Wasserstoff, Halogen, Hydroxy, Cyano, Nitro, Amino, C(O)OH, C(O)NH2; - hydrogen, halogen, hydroxy, cyano, nitro, amino, C (O) OH, C (O) NH 2 ;
- (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Haloalkylcar- bonyl, (C1-C6)-Alkylcarbonyloxy, (C1-C6)-Halogenalkylcarbonyloxy, (C1-C6)- Alkylcarbonyl-(C1-C4)-alkyl; (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -haloalkylcarbonyl, (C 1 -C 6 ) -Alkylcarbonyloxy, (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 4 ) -alkyl;
- (C1-C6)-Alkoxy, (C1-C4)-Alkoxyalkyl, (C1-C6)-Halogenalkoxy, (C1-C6)- Alkoxycarbonyl, (C1-C6)-Haloalkoxycarbonyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)- halogenalkyl, (C1-C6)-Halogenalkoxycarbonyl-(C1-C6)-halogenalkyl; - (C 1 -C 6 ) -alkoxy, (C 1 -C 4 ) -alkoxyalkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -haloalkoxycarbonyl , (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl - (C 1 -C 6 ) - haloalkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -haloalkyl;
- (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkenylcarbonyl, (C2-C6)-Haloalke- nylcarbonyl, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alke- nyloxycarbonyl, (C2-C6)-Haloalkenyloxycarbonyl;  (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6) alkenylcarbonyl, (C2-C6) haloalkenylcarbonyl, (C2-C6) alkenyloxy, (C2-C6) haloalkenyloxy , (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -haloalkenyloxycarbonyl;
- (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyloxy- carbonyl, (C2-C6)-Halogenalkinyloxycarbonyl;  - (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 2 -C 6) -alkynylcarbonyl, (C 2 -C 6) -haloalkynylcarbonyl, (C 2 -C 6) -alkynyloxy, (C 2 -C 6) -haloalkynyloxy , (C 2 -C 6) -alkynyloxycarbonyl, (C 2 -C 6) -haloalkynyloxycarbonyl;
- Tri-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Di-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Mono-(C1- C6)-alkylsilyl-(C2-C6)-alkinyl, Phenylsilyl-(C2-C6)-alkinyl;  Tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, di (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, mono (C 1 -C 6) alkylsilyl (C 2 -C 4) alkyl) C6) alkynyl, phenylsilyl (C2-C6) alkynyl;
- (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)-Arylcarbonyl und (C6-C14)-Aryloxycarbonyl, welche jeweils am Arylteil mit Halogen, (C1-C6)-Alkyl und/oder (C1-C6)-Haloalkyl substituiert sein können;  - (C6-C14) -aryl, (C6-C14) -aryloxy, (C6-C14) -arylcarbonyl and (C6-C14) -aryloxycarbonyl, which are each attached to the aryl portion by halogen, (C1-C6) -alkyl and / or (C1-C6) -haloalkyl may be substituted;
- (C6-C14)-Aryl-(C1-C6)-alkyl, (C6-C14)-Aryl-(C1-C6)-alkoxy, (C6-C14)-Aryl-(C1-C6)-alkyl- carbonyl, (C6-C14)-Aryl-(C1-C6)-alkyl-carbonyloxy, (C6-C14)-Aryl-(C1-C6)-alkoxycarbo- nyl, (C6-C14)-Aryl-(C1-C6)-alkoxycarbonyloxy;  - (C6-C14) -aryl (C1-C6) -alkyl, (C6-C14) -aryl (C1-C6) -alkoxy, (C6-C14) -aryl (C1-C6) -alkylcarbonyl , (C6-C14) -aryl (C1-C6) -alkyl-carbonyloxy, (C6-C14) -aryl (C1-C6) -alkoxycarbonyl, (C6-C14) -aryl- (C1-C6) alkoxycarbonyloxy;
- Mono-((C1-C6)-alkyl)-amino, Mono-((C1-C6)-haloalkyl)-amino, Di-((C1-C6)-alkyl)- amino, Di-((C1-C6)-haloalkyl)-amino, ((C1-C6)-Alkyl-(C1-C6)-haloalkyl)-amino, N-((C1- C6)-Alkanoyl)-amino, N-((C1-C6)-Haloalkanoyl)-amino, Aminocarbonyl-(C1-C6)-alkyl, Di-(C1-C6)-Alkylaminocarbonyl-(C1-C6)-alkyl; - Mono-((C1-C6)-alkyl)-amino-carbonyl, Mono-((C1-C6)-haloalkyl)-amino-carbonyl, Di- ((C1-C6)-alkyl)-amino-carbonyl, Di-((C1-C6)-haloalkyl)-amino-carbonyl, ((C1-C6)- Alkyl-(C1-C6)-haloalkyl)-amino-carbonyl, N-((C1-C6)-Alkanoyl)-amino-carbonyl, N- ((C1-C6)-Haloalkanoyl)-amino-carbonyl, Mono-((C6-C14)-aryl)-amino-carbonyl, Di- ((C6-C14)-aryl)-amino-carbonyl, Mono (- C 1 -C 6) alkyl) amino, mono (C 1 -C 6) haloalkyl) amino, di (C 1 -C 6) alkyl) amino, di (C 1 -C 6 ) -haloalkyl) -amino, ((C 1 -C 6) -alkyl- (C 1 -C 6) -haloalkyl) -amino, N - ((C 1 -C 6) -alkanoyl) -amino, N - ((C 1 -C 6) - Haloalkanoyl) amino, aminocarbonyl (C 1 -C 6) alkyl, di (C 1 -C 6) alkylaminocarbonyl (C 1 -C 6) alkyl; Mono (- (C 1 -C 6) alkyl) amino carbonyl, mono - ((C 1 -C 6) haloalkyl) amino carbonyl, di ((C 1 -C 6) alkyl) amino carbonyl, di - ((C 1 -C 6) haloalkyl) amino carbonyl, ((C 1 -C 6) alkyl- (C 1 -C 6) haloalkyl) amino carbonyl, N - ((C 1 -C 6) alkanoyl) amino carbonyl, N- ((C 1 -C 6) -haloalkanoyl) -amino-carbonyl, mono - ((C 6 -C 14) -aryl) -amino-carbonyl, di- ((C 6 -C 14) -aryl) -amino-carbonyl .
- Di-((C1-C6)-alkyl)-amino, mit der Maßgabe, dass die beiden (C1-C6)-alkyl-Reste einen Cyclus bilden, welcher gegebenenfalls durch NH, O oder S unterbrochen sein kann; - (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkoxy, (C1-C6)-Alkoxycar- bonyl-(C1-C6)-alkoxy; - di - ((C 1 -C 6) -alkyl) -amino, provided that the two (C 1 -C 6) -alkyl radicals form a cycle which may optionally be interrupted by NH, O or S; - (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxycar - carbonyl (C 1 -C 6 ) alkoxy;
- (C3-C8)-Cycloalkyl, welches gegebenenfalls am Cycloalkylrest durch (C1-C6)-Alkyl und/oder Halogen substituiert sein kann; (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl-(C1- C6)-alkyl, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxy, (C3-C8)-Cycloalkylcarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyl, (C3-C8)-Cycloalkyl- (C1-C6)-haloalkylcarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxycarbonyl, (C3-C8)- Cycloalkyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-Cycloalkylcarbonyloxy, (C3-C8)- Cycloalkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)- Cycloalkyl-(C1-C6)-halogenalkylcarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy; (C5-C6)- Cycloheteroalkyl, welches gegenbenfalls einfach oder zweifach unabhängig voneinander durch NH, O oder S unterbrochen sein kann; - (C 3 -C 8 ) -cycloalkyl, which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy, (C 3 -C 8) - cycloalkoxycarbonyloxyC, (C 3 -C 8) -cycloalkyl- (C 1 -C 6) alkylcarbonyloxy, (C 3 -C 8) - cycloalkyl (C1-C6) haloalkylcarbonyloxy, (C3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyloxy; (C 5 -C 6 ) -cycloheteroalkyl, which may be interrupted by NH, O or S independently of one another, once or twice;
- (C3-C8)-Cycloalkenyl, (C3-C8)-Cycloalkenyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-alkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkoxy, (C3- C8)-Cycloalkenyl-(C1-C6)-halogenalkoxy, (C3-C8)-Cycloalkenylcarbonyl, (C3-C8)-Cy- cloalkenyloxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkylcarbonyl, (C3-C8)- Cycloalkenyl-(C1-C6)-halogenalkylcarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)- alkoxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)- Cycloalkenylcarbonyloxy, (C3-C8)-Cycloalkenyloxycarbonyloxy, (C3-C8)-Cycloalkenyl- (C1-C6)-alkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkylcarbonyloxy, (C3- C8)-Cycloalkenyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)- haloalkoxycarbonyloxy; - (C 3 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -cycloalkenyloxy, (C 3 -C 8 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkenyl - (C 1 -C 6) -haloalkyl, (C 3 -C 8) cycloalkenyl (C 1 -C 6) alkoxy, (C 3 - C 8) cycloalkenyl (C1-C6) -haloalkoxy, (C3 -C8) -cycloalkenylcarbonyl, (C3-C8) -cycloalkenyloxycarbonyl, (C3-C8) -cycloalkenyl- (C1-C6) -alkylcarbonyl, (C3-C8) -cycloalkenyl- (C1-C6) -haloalkylcarbonyl, (C3 -C8) cycloalkenyl (C 1 -C 6) alkoxycarbonyl, (C 3 -C 8) cycloalkenyl (C 1 -C 6) haloalkoxycarbonyl, (C 3 -C 8) cycloalkenylcarbonyloxy, (C 3 -C 8) cycloalkenyloxycarbonyloxy, (C3-C8 ) -Cycloalkenyl- (C 1 -C 6) -alkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkoxycarbonyloxy, (C 3 -C 8) - Cycloalkenyl (C 1 -C 6) haloalkoxycarbonyloxy;
- Hydroxy-(C1-C6)-alkyl, Hydroxy-(C1-C6)-alkoxy Cyano-(C1-C6)-alkoxy, Cyano-(C1- C6)-alkyl; Hydroxy (C 1 -C 6) alkyl, hydroxy (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkyl;
- (C1-C6)-Alkylsulfonyl, (C1-C6)-Alkylthio, (C1-C6)-Alkylsulfinyl, (C1-C6)-Halo- alkylsulfonyl, (C1-C6)-Halogenalkylthio, (C1-C6)-Halogenalkylsulfinyl, (C1-C6)- Alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-Alkylsulfinyl- (C1-C6)-alkyl, (C1-C6)-Haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkylthio-(C1-C6)- alkyl, (C1-C6)-Haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-Alkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylthio-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Haloalkylthio-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfonyloxy, (C1-C6)- Halogenalkylsulfonyloxy, (C1-C6)-Alkylthiocarbonyl, (C1-C6)-Haloalkylthiocarbonyl, (C1-C6)-Alkylthiocarbonyloxy, (C1-C6)-Haloalkylthiocarbonyloxy, (C1-C6)-Alkylthio- (C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkoxy, (C1-C6)-Alkylthio-(C1-C6)- alkylcarbonyl, (C1-C6)-Alkylthio-(C1-C6)-alkylcarbonyloxy, (C4-C14)-Arylsulfonyl, (C6- C14)-Arylthio, (C6-C14)-Arylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Alkenylthio, (C3- C8)-Cycloalkenylthio, (C3-C6)-Alkinylthio; R2 ausgewählt ist aus der Gruppe, bestehend aus - (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Haloalkylcar- bonyl, (C1-C6)-Alkylcarbonyloxy, (C1-C6)-Halogenalkylcarbonyloxy, (C1-C6)- Alkylcarbonyl-(C1-C4)-alkyl; - (C 1 -C 6) -alkylsulfonyl, (C 1 -C 6) -alkylthio, (C 1 -C 6) -alkylsulfinyl, (C 1 -C 6) -haloalkylsulfonyl, (C 1 -C 6) -haloalkylthio, (C 1 -C 6) -haloalkylsulfinyl , (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylthio (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfinyl- (C 1 -C 6) -alkyl, ( C1-C6) -haloalkylsulfonyl- (C1-C6) -alkyl, (C1-C6) -haloalkylthio (C1-C6) - alkyl, (C 1 -C 6) -haloalkylsulfinyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -haloalkyl, (C 1 -C 6) -alkylthio (C 1 -C 6) -haloalkyl, (C1-C6) -alkylsulfinyl- (C1-C6) -haloalkyl, (C1-C6) -haloalkylsulfonyl- (C1-C6) -haloalkyl, (C1-C6) -haloalkylthio (C1-C6) -haloalkyl, (C1 -C 6) - haloalkylsulfinyl- (C 1 -C 6) -haloalkyl, (C 1 -C 6) -alkylsulfonyloxy, (C 1 -C 6) -halogenoalkylsulfonyloxy, (C 1 -C 6) -alkylthiocarbonyl, (C 1 -C 6) -haloalkylthiocarbonyl, (C 1 -C 6 ) -Alkylthiocarbonyloxy, (C 1 -C 6 ) -haloalkylthiocarbonyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkylcarbonyloxy, (C 4 -C 14 ) -arylsulfonyl, (C 6 -C 14 ) arylthio, (C 6 -C 14 ) arylsulfinyl, (C 3 -C 8 ) -cycloalkylthio, (C 3 -C 8 ) -alkenylthio, (C 3 -C 8 ) -cycloalkenylthio, (C 3 -C 6 ) alkynylthio; R 2 is selected from the group consisting of - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -haloalkylcarboxylic bonyl, (C 1 -C 6 ) -alkylcarbonyloxy, (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 1 -C 6 ) -alkylcarbonyl (C 1 -C 4 ) -alkyl;
- (C1-C6)-Alkoxy, (C1-C6)-Halogenalkoxy, (C1-C6)-Alkoxycarbonyl, (C1-C6)-Haloalkoxy- carbonyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkoxycarbonyl-(C1-C6)- alkyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-halogenalkyl, (C1-C6)-Halogenalkoxycarbonyl- (C1-C6)-halogenalkyl; - (C 1 -C 6) alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) haloalkoxy carbonyl, (C1-C6) -alkoxycarbonyl - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) haloalkoxycarbonyl (C 1 -C 6 ) haloalkyl;
- (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkenylcarbonyl, (C2-C6)-Haloalke- nylcarbonyl, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alke- nyloxycarbonyl, (C2-C6)-Haloalkenyloxycarbonyl; (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -alkenylcarbonyl, (C 2 -C 6 ) -haloalkenylcarbonyl, (C 2 -C 6 ) Alkenyloxy, (C 2 -C 6 ) haloalkenyloxy, (C 2 -C 6 ) alkenyloxycarbonyl, (C 2 -C 6 ) haloalkenyloxycarbonyl;
- (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyloxy- carbonyl, (C2-C6)-Halogenalkinyloxycarbonyl;  - (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 2 -C 6) -alkynylcarbonyl, (C 2 -C 6) -haloalkynylcarbonyl, (C 2 -C 6) -alkynyloxy, (C 2 -C 6) -haloalkynyloxy , (C 2 -C 6) -alkynyloxycarbonyl, (C 2 -C 6) -haloalkynyloxycarbonyl;
- Tri-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Di-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Mono-(C1- C6)-alkylsilyl-(C2-C6)-alkinyl, Phenylsilyl-(C2-C6)-alkinyl;  Tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, di (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, mono (C 1 -C 6) alkylsilyl (C 2 -C 4) alkyl) C6) alkynyl, phenylsilyl (C2-C6) alkynyl;
- (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)-Arylcarbonyl und (C6-C14)-Aryloxycarbonyl, welche jeweils am Arylteil mit Halogen, (C1-C6)-Alkyl und/oder (C1-C6)-Haloalkyl substituiert sein können;  - (C6-C14) -aryl, (C6-C14) -aryloxy, (C6-C14) -arylcarbonyl and (C6-C14) -aryloxycarbonyl, which are each attached to the aryl portion by halogen, (C1-C6) -alkyl and / or (C1-C6) -haloalkyl may be substituted;
- (C6-C14)-Aryl-(C1-C6)-alkyl, (C6-C14)-Aryl-(C1-C6)-alkoxy, (C6-C14)-Aryl-(C1-C6)-alkyl- carbonyl, (C6-C14)-Aryl-(C1-C6)-alkyl-carbonyloxy, (C6-C14)-Aryl-(C1-C6)-alkoxycarbo- nyl, (C6-C14)-Aryl-(C1-C6)-alkoxycarbonyloxy;  - (C6-C14) -aryl (C1-C6) -alkyl, (C6-C14) -aryl (C1-C6) -alkoxy, (C6-C14) -aryl (C1-C6) -alkylcarbonyl , (C6-C14) -aryl (C1-C6) -alkyl-carbonyloxy, (C6-C14) -aryl (C1-C6) -alkoxycarbonyl, (C6-C14) -aryl- (C1-C6) alkoxycarbonyloxy;
- Mono-((C1-C6)-alkyl)-amino, Mono-((C1-C6)-haloalkyl)-amino, Di-((C1-C6)-alkyl)- amino, Di-((C1-C6)-haloalkyl)-amino, ((C1-C6)-Alkyl-(C1-C6)-haloalkyl)-amino, N-((C1- C6)-Alkanoyl)-amino, N-((C1-C6)-Haloalkanoyl)-amino, Aminocarbonyl-(C1-C6)-alkyl, Di-(C1-C6)-Alkylaminocarbonyl-(C1-C6)-alkyl; Mono (- C 1 -C 6) alkyl) amino, mono (C 1 -C 6) haloalkyl) amino, di (C 1 -C 6) alkyl) amino, di (C 1 -C 6 ) -haloalkyl) -amino, ((C 1 -C 6) -alkyl- (C 1 -C 6) -haloalkyl) -amino, N - ((C 1 -C 4) -alkyl) C 6) alkanoyl) amino, N - ((C 1 -C 6) -haloalkanoyl) -amino, aminocarbonyl- (C 1 -C 6) -alkyl, di- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl;
- Mono-((C1-C6)-alkyl)-amino-carbonyl, Mono-((C1-C6)-haloalkyl)-amino-carbonyl, Di- ((C1-C6)-alkyl)-amino-carbonyl, Di-((C1-C6)-haloalkyl)-amino-carbonyl, ((C1-C6)- Alkyl-(C1-C6)-haloalkyl)-amino-carbonyl, N-((C1-C6)-Alkanoyl)-amino-carbonyl, N- ((C1-C6)-Haloalkanoyl)-amino-carbonyl, Mono-((C6-C14)-aryl)-amino-carbonyl, Di- ((C6-C14)-aryl)-amino-carbonyl, Mono (- (C 1 -C 6) alkyl) amino carbonyl, mono - ((C 1 -C 6) haloalkyl) amino carbonyl, di ((C 1 -C 6) alkyl) amino carbonyl, di - ((C 1 -C 6) haloalkyl) amino carbonyl, ((C 1 -C 6) alkyl- (C 1 -C 6) haloalkyl) amino carbonyl, N - ((C 1 -C 6) alkanoyl) amino carbonyl, N- ((C 1 -C 6 ) -haloalkanoyl) -amino-carbonyl, mono - ((C 6 -C 14 ) -aryl) -amino-carbonyl, di- ((C 6 -C 14 ) -aryl) -amino carbonyl,
- (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkoxy, (C1-C6)-Alkoxycar- bonyl-(C1-C6)-alkoxy; - (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxycar - carbonyl (C 1 -C 6 ) alkoxy;
- (C3-C8)-Cycloalkyl, welches gegebenenfalls am Cycloalkylrest durch (C1-C6)-Alkyl und/oder Halogen substituiert sein kann; (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl-(C1- C6)-alkyl, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxy, (C3-C8)-Cycloalkylcarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyl, (C3-C8)-Cycloalkyl- (C1-C6)-haloalkylcarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxycarbonyl, (C3-C8)- Cycloalkyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-Cycloalkylcarbonyloxy, (C3-C8)- Cycloalkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)- Cycloalkyl-(C1-C6)-halogenalkylcarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy; - (C 3 -C 8 ) -cycloalkyl, which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy, (C 3 -C 8) - cycloalkoxycarbonyloxyC, (C 3 -C 8) -cycloalkyl- (C 1 -C 6) alkylcarbonyloxy, (C 3 -C 8) - cycloalkyl (C1-C6) haloalkylcarbonyloxy, (C3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyloxy;
- (C3-C8)-Cycloalkenyl, (C3-C8)-Cycloalkenyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-alkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkoxy, (C3- C8)-Cycloalkenyl-(C1-C6)-halogenalkoxy, (C3-C8)-Cycloalkenylcarbonyl, (C3-C8)-Cy- cloalkenyloxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkylcarbonyl, (C3-C8)- Cycloalkenyl-(C1-C6)-halogenalkylcarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)- alkoxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)- Cycloalkenylcarbonyloxy, (C3-C8)-Cycloalkenyloxycarbonyloxy, (C3-C8)-Cycloalkenyl- (C1-C6)-alkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkylcarbonyloxy, (C3- C8)-Cycloalkenyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)- haloalkoxycarbonyloxy; - (C 3 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -cycloalkenyloxy, (C 3 -C 8 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkenyl - (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkenyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkenyl- (C 1 -C 6 ) -haloalkoxy , (C 3 -C 8 ) -cycloalkenylcarbonyl, (C 3 -C 8 ) -cycloalkenyloxycarbonyl, (C 3 -C 8 ) -cycloalkenyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) - Cycloalkenyl- (C 1 -C 6) -haloalkylcarbonyl, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkoxycarbonyl, (C 3 -C 8) -cycloalkenylcarbonyloxy , (C 3 -C 8) -cycloalkenyloxycarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- C1-C6) -alkoxycarbonyloxy, (C3-C8) -cycloalkenyl- (C1-C6) -haloalkoxycarbonyloxy;
- Hydroxy-(C1-C6)-alkyl, Hydroxy-(C1-C6)-alkoxy Cyano-(C1-C6)-alkoxy, Cyano-(C1- C6)-alkyl; Hydroxy (C 1 -C 6) alkyl, hydroxy (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkyl;
- (C1-C6)-Alkylsulfonyl, (C1-C6)-Alkylthio, (C1-C6)-Alkylsulfinyl, (C1-C6)-Halo- alkylsulfonyl, (C1-C6)-Halogenalkylthio, (C1-C6)-Halogenalkylsulfinyl, (C1-C6)- Alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-Alkylsulfinyl- (C1-C6)-alkyl, (C1-C6)-Haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkylthio-(C1-C6)- alkyl, (C1-C6)-Haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-Alkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylthio-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Haloalkylthio-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfonyloxy, (C1-C6)- Halogenalkylsulfonyloxy, (C1-C6)-Alkylthiocarbonyl, (C1-C6)-Haloalkylthiocarbonyl, (C1-C6)-Alkylthiocarbonyloxy, (C1-C6)-Haloalkylthiocarbonyloxy, (C1-C6)-Alkylthio- (C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkoxy, (C1-C6)-Alkylthio-(C1-C6)- alkylcarbonyl, (C1-C6)-Alkylthio-(C1-C6)-alkylcarbonyloxy, (C4-C14)-Arylsulfonyl, (C6- C14)-Arylthio, (C6-C14)-Arylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Alkenylthio, (C3- C8)-Cycloalkenylthio, (C3-C6)-Alkinylthio; oder R1 und R2 zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie gebunden sind, einen gesättigten fünf - bis siebengliedriegen Ring bilden, der durch die Gruppe Y unterbrochen sein kann, wobei Y ausgewählt ist aus C(O), O, S, S(O), S(O)2, NR1a, C(O)- NR1a, wobei der gesättigte fünf- bis siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, COOMe, COOEt, CONH2, Nitril, (C1-C6)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Phenylsulfonyl oder Phenyl-(C1-C6)-alkylsulfonyl substituiert sein kann, und wobei R1a ausgewählt ist aus Wasserstoff, Acetyl, Trifluoracetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkylcarbonyl, (C3-C6)-Cycloalkyl-(C1-C6)-Alkyl, (C1-C4)-Alkylsulfonyl, Phenyl, Phenyl-(C1-C6)-alkyl, Phenylcarbonyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 2- Pyridinylcarbonyl, 3-Pyridinylcarbonyl, 4-Pyridinylcarbonyl, wobei die 14 zuletzt genannten Reste mit Halogen, (C1-C6)-Alkyl, (C1-C6)-Alkyloxy, Nitril oder Trifluormethyl substiuiert sein können; R3 Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)- Haloalkylcarbonyl oder (C1-C6)-Alkylcarbonyloxy ist; R4 und R5 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Haloalkyl, Hydroxy, - (C 1 -C 6) -alkylsulfonyl, (C 1 -C 6) -alkylthio, (C 1 -C 6) -alkylsulfinyl, (C 1 -C 6) -haloalkylsulfonyl, (C 1 -C 6) -haloalkylthio, (C 1 -C 6) -haloalkylsulfinyl , (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylthio (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfinyl- (C 1 -C 6) -alkyl, ( C1-C6) -haloalkylsulfonyl- (C1-C6) -alkyl, (C1-C6) -haloalkylthio (C1-C6) -alkyl, (C1-C6) -haloalkylsulfinyl- (C1-C6) -alkyl, (C1- C6) -alkylsulfonyl- (C1-C6) -haloalkyl, (C1-C6) -alkylthio (C1-C6) -haloalkyl, (C1-C6) -alkylsulfinyl- (C1-C6) -haloalkyl, (C1-C6) - Haloalkylsulfonyl- (C 1 -C 6) -haloalkyl, (C 1 -C 6) -haloalkylthio (C 1 -C 6) -haloalkyl, (C 1 -C 6) -haloalkylsulfinyl- (C 1 -C 6) -haloalkyl, (C 1 -C 6) -alkylsulfonyloxy, (C1-C6) - haloalkylsulfonyloxy, (C1-C6) -alkylthiocarbonyl, (C1-C6) -haloalkylthiocarbonyl, (C1-C6) -alkylthiocarbonyloxy, (C1-C6) -haloalkylthiocarbonyloxy, (C1-C6) -alkylthio (C1 -C 6) alkyl, (C 1 -C 6) alkylthio (C 1 -C 6) alkoxy, (C 1 -C 6) alkylthio (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) alkylthio (C 1 -C 6 ) alkylcarbonyloxy, (C4-C14) arylsulfonyl, (C6-C14) arylthio, (C 6 -C 14) arylsulfinyl, (C 3 -C 8) -cycloalkylthio, (C 3 -C 8) -alkenylthio , (C 3 -C 8 ) -cycloalkenylthio, (C 3 -C 6 ) -alkynylthio; or R1 and R2 together with the carbon or nitrogen atom to which they are attached form a saturated five to seven membered ring which may be interrupted by the group Y, wherein Y is selected from C (O), O, S, S (O), S (O) 2 , NR 1a, C (O) - NR 1a, wherein the saturated five- to seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -) C 6 ) -cycloalkyl, trifluoromethyl, COOMe, COOEt, CONH 2 , nitrile, (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, phenylsulfonyl or phenyl- (C 1 -C 6 ) -alkylsulfonyl can, and wherein R1a is selected from hydrogen, acetyl, trifluoroacetyl, (C 1 -C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkylcarbonyl, (C 3 -C 6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl, phenylcarbonyl, 2-pyridinyl, 3-pyridinyl, 4- Pyridinyl, 2-pyridinylcarbonyl, 3-pyridinylcarbonyl, 4-pyridinylcarbonyl, wherein the 14 the last-mentioned radicals can be substituted by halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyloxy, nitrile or trifluoromethyl; R 3 is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) haloalkylcarbonyl or (C 1 -C 6) alkylcarbonyloxy; R 4 and R 5 are each independently hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, hydroxy,
(C1-C6)-Alkoxy oder (C1-C6)-Halogenalkoxy sind; oder R4 und R5 zusammen mit dem Kohlenstoffatom, an welchem sie gebunden sind, einen gesättigten drei- bis siebengliedrigen Ring bilden, der ein oder mehrere Heteroatome ausgewählt aus Sauerstoff oder Schwefel oder NH oder NR1a enthalten kann; R6 und R7 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Haloalkyl, (C1-C6)- Alkoxy, (C1-C6)-Halogenalkoxy, (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)-Arylcarbonyl oder (C6-C14)-Aryloxycarbonyl ist ; oder R6 und R7 zusammen mit dem Kohlenstoff, an welchen sie gebunden sind, eine (C3-C7)- Alkylengruppe bilden, die ein oder mehrere Sauerstoff- und/oder Schwefelatome enthalten können, wobei die (C3-C7)-Alkylengruppe durch Halogen einfach oder mehrfach substituiert sein kann und die jeweilgen Halogensubstituenten gleich oder verschieden sein können; R8, R9, R10 und R11 jeweils unabhängig voneinander Wasserstoff, Halogen, Cyano, C(O)OH, (C 1 -C 6) -alkoxy or (C 1 -C 6) -haloalkoxy; or R4 and R5 together with the carbon atom to which they are attached form a saturated three- to seven-membered ring which may contain one or more heteroatoms selected from oxygen or sulfur or NH or NR1a; R6 and R7 are each independently hydrogen, (C1-C6) -alkyl, (C1-C6) -haloalkyl, (C1-C6) -alkoxy, (C1-C6) -haloalkoxy, (C6-C14) -aryl, (C6 -C14) -aryloxy, (C6-C14) -arylcarbonyl or (C6-C14) -aryloxycarbonyl; or R6 and R7 together with the carbon to which they are attached form a (C3-C7) -alkylene group which may contain one or more oxygen and / or sulfur atoms, the (C3-C7) -alkylene group being simple by halogen or may be substituted several times and the respective halogen substituents may be identical or different; R8, R9, R10 and R11 are each independently of one another hydrogen, halogen, cyano, C (O) OH,
C(O)NH2, (C1-C6)-Alkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Alkyloxycarbonyl, (C1-C6)-Alkylaminocarbonyl, (C1-C6)-di-Alkylaminocarbonyl, (C1-C6)- Haloalkyl, (C1-C6)-Alkoxy, (C1-C6)-Halogenalkoxy, (C2-C6)-Alkenyl, (C2-C6)- Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyl- oxycarbonyl, (C2-C6)-Halogenalkinyloxycarbonyl oder Nitro sind, wobei die Reste R9 und R10ringbildend durch eine -O-CH2-O- Gruppe verbunden sein können; X für eine Bindung, CH2, O, S, Carbonyl, NH, CR12R13,NR14,CH2O oder CH2S steht, wobei bei den beiden letztgenannten Gruppen das Kohlenstoffatom an den aromatischen Teil und das C (O) NH 2 , (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkyloxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (C 1 -C 6 ) -di-alkylaminocarbonyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 2 -C 6 ) -alkenyl, ( C 2 -C 6 ) alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 2 -C 6 ) -alkynylcarbonyl, (C 2 -C 6 ) -haloalkinylcarbonyl, (C 2 -C 6 ) -alkynyloxy , (C 2 -C 6 ) -haloalkynyloxy, (C 2 -C 6 ) -alkynyloxycarbonyl, (C 2 -C 6 ) -haloalkynyloxycarbonyl or nitro, where the radicals R 9 and R 10 are ring-forming by an -O-CH 2 - O group can be connected; X is a bond, CH 2 , O, S, carbonyl, NH, CR 12 R 13, NR 14, CH 2 O or CH 2 S, where in the latter two groups the carbon atom to the aromatic part and the
Heteroatom O oder S an den teilhydrierten Teil des Amins gebunden ist; wobei, wenn n = 0, X keine Bindung sein kann; R12 und R13 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl oder (C1-C6)-Haloalkyl sind; R14 Wasserstoff, (C1-C6)-Alkyl oder (C1-C6)-Haloalkyl ist; n die Laufzahl 0, 1 oder 2 ist; und m die Laufzahl 0, 1, 2, 3, 4, oder 5 ist. Die Verbindungen der Formel (I) zeichnen sich, neben einem guten Wirksamkeitsprofil und einer guten Kulturpflanzenverträglichkeit, durch ihre kostengünstige Herstellung aus, da die erfindungsgemäßen Substanzen aus preiswerten und gut zugänglichen Vorstufen durch kostengünstige Prozesse hergestellt werden können. Daher kann auf die Verwendung teurer und schwer zugänglicher Zwischenprodukte verzichtet werden. Im Folgenden werden jeweils für die einzelnen Substituenten bevorzugte, besonders bevorzugte und ganz besonders bevorzugte Bedeutungen beschrieben. Die übrigen Substituenten der allgemeinen Formel (I), welche nachfolgend nicht genannt werden, weisen die oben genannte Bedeutung auf. Das gilt auch für die Laufzahl n, d.h. die Laufzahl n ist in den nachfolgenden Ausführungsformen 0, 1 oder 2. Heteroatom O or S is attached to the partially hydrogenated portion of the amine; where, when n = 0, X can not be a bond; R12 and R13 are each independently hydrogen, (C 1 -C 6 ) alkyl or (C 1 -C 6 ) haloalkyl; R 14 is hydrogen, (C 1 -C 6 ) alkyl or (C 1 -C 6 ) haloalkyl; n is the run number 0, 1 or 2; and m is the run number 0, 1, 2, 3, 4, or 5. The compounds of the formula (I) are distinguished, in addition to a good activity profile and good crop plant compatibility, by their cost-effective production, since the substances according to the invention can be prepared from inexpensive and easily accessible precursors by inexpensive processes. Therefore, the use of expensive and difficult to access intermediates can be dispensed with. In the following, preferred, particularly preferred and very particularly preferred meanings are described in each case for the individual substituents. The remaining substituents of the general formula (I), which are not mentioned below, have the abovementioned meaning. The also applies to the running number n, ie the running number n is 0, 1 or 2 in the following embodiments.
Eine erste Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 bevorzugt Wasserstoff, Halogen, Cyano, C(=O)NH2, NO2, (C1-C6)-Alkyl, (C1-C6)- Alkylcarbonyl, (C1-C6)-Haloalkyl, (C3-C6)-Cyclopropyl, (C1-C6)-Alkoxy, (C1-C6)-Thioalkyl, (C1-C6)-Alkylthio, (C2-C6)-Alkinyl, Mono-(C1-C6)-alkylamino, Di-(C1-C6)-alkylamio oder Tri- (C1-C6)-alkylsilyl-(C2-C6)-alkinyl ist; R1 besonders bevorzugt Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Nitro, Trimethylsilylethinyl, Methyl, Ethyl, Propyl, Isopropyl, Butyl, tert.-Butyl, n-Pentyl, n-Heptyl, Cyclopropyl, A first embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is preferably hydrogen, halogen, cyano, C (OO) NH 2, NO 2, (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, (C1-C6) -haloalkyl, (C3-C6) -cyclopropyl, (C1-C6) -alkoxy, (C1-C6) -thioalkyl, (C1-C6) -alkylthio, (C2-C6) -alkynyl, mono- (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamio or tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl; R1 particularly preferably hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, trimethylsilylethynyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl, cyclopropyl,
Cyclobutyl, Acetyl, Ethinyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl,  Cyclobutyl, acetyl, ethynyl, amino, dimethylamino, trifluoromethyl, difluoromethyl,
Monofluormethyl, Methoxy, Ethoxy oder Methoxymethyl ist; und R1 ganz besonders bevorzugt Methyl, Ethyl, Propyl, Acetyl oder Trifluormethyl ist. Eine zweite Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R2 bevorzugt Wasserstoff, Halogen, (C1-C6)-Alkylphenyl, (C6-C14)-Aryl, welches am Arylrest durch (C1-C6)-Alkyl, (C6-C14)-Haloalkyl und/oder Halogen substituiert sein kann; C6-Aryl-(C1- C6)-haloalkyl, (C1-C6)-Alkyl, (C1-C6)-Haloalkyl,(C1-C6)-Alkoxy, (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C3-C6)-Cycloalkyl, welches am Cycloalkylrest durch (C1-C6)-Alkyl, (C6-C14)-Haloaryl und/oder Halogen substituiert sein kann; 1-(C1-C6)-Alkylcyclopropyl, 1-((C1-C6)-Alkyl-C6-aryl)- cyclopropyl, 1-(Monohalogenphenyl)-cyclopropyl, 1-(Dihalogenphenyl)-cyclopropyl, Mono- (C1-C6)-alkylamino, Di-(C1-C6)-alkylamino, (C1-C6)-Thioalkyl, (C1-C6)-Alkylthio, (C1-C6)- Alkoxy, (C1-C4)-Alkoxy-(C1-C6)-alkyl oder Amino ist; R2 besonders bevorzugt Wasserstoff, Chlor, Phenyl, 2-Methylphenyl, 3-Trifluormethylphenyl, Methyl, Ethyl, Isopropy, Butyl, tert.-Butyl, n-Pentyl, n-Heptyl, Trifluormethyl, 1- Methylcyclopropyl, 1-(p-Xylyl)-cyclopropyl, 1-(2,4-Dichlorphenyl)-cyclopropyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl, Monofluormethyl, CHFCH3, CF(CH3)2, CHF(CH2CH3), 1-Fluorcyclopropyl, Cyclopentyl, Methoxy, Ethoxy, Methoxymethyl, Monofluoromethyl, methoxy, ethoxy or methoxymethyl; and R1 is most preferably methyl, ethyl, propyl, acetyl or trifluoromethyl. A second embodiment of the present invention comprises compounds of the general formula (I) in which R 2 is preferably hydrogen, halogen, (C 1 -C 6 ) -alkylphenyl, (C 6 -C 14 ) -aryl which is bonded to the aryl radical by (C 1 -C 6 ) -alkyl, (C 6 -C 14 ) -haloalkyl and / or halogen; C 6 aryl (C 1 - C 6) -haloalkyl, (C 1 -C 6) alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, which on the cycloalkyl radical is substituted by (C 1 -C 6 ) -alkyl, (C 6 -C 14 ) -haloaryl and / or or halogen may be substituted; 1- (C 1 -C 6 ) -alkyl cyclopropyl, 1 - ((C 1 -C 6 ) -alkyl-C 6 -aryl) -cyclopropyl, 1- (monohalophenyl) -cyclopropyl, 1- (dihalophenyl) -cyclopropyl, mono (C 1 -C 6 ) -alkylamino, di- (C 1 -C 6 ) -alkylamino, (C 1 -C 6 ) -thioalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) Alkoxy, (C 1 -C 4 ) alkoxy (C 1 -C 6 ) alkyl or amino; R 2 particularly preferably hydrogen, chlorine, phenyl, 2-methylphenyl, 3-trifluoromethylphenyl, methyl, ethyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl, trifluoromethyl, 1-methylcyclopropyl, 1- (p-xylyl ) -cyclopropyl, 1- (2,4-dichlorophenyl) -cyclopropyl, amino, dimethylamino, trifluoromethyl, difluoromethyl, monofluoromethyl, CHFCH3, CF (CH3) 2, CHF (CH2CH3), 1-fluorocyclopropyl, cyclopentyl, methoxy, ethoxy, methoxymethyl .
Ethoxymethyl, Thiomethyl, Methylthio oder Methoxy ist; und R2 ganz besonders bevorzugt Wasserstoff, Methyl oder Ethyl ist. Eine dritte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 und R2 bilden bevorzugt zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie gebunden sind, einen gesättigten sechs- oder siebengliedrigen Ring, wie im folgenden dargestellt Ethoxymethyl, thiomethyl, methylthio or methoxy; and R 2 is very particularly preferably hydrogen, methyl or ethyl. A third embodiment of the present invention comprises compounds of the general formula (I) in which R1 and R2 together with the carbon atom or nitrogen atom to which they are attached form a saturated six- or seven-membered ring, as shown below
wobei der gesättigte sechs- oder siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, (C1-C6)- Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl oder Phenylsulfonyl substituiert sein kann, und wobei R1a bevorzugt ausgewählt ist aus Wasserstoff, Acetyl, Trifluoracetyl, (C1-C6)-Alkyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkylcarbonyl, (C3-C6)-Cycloalkyl-(C1-C6)-Alkyl, (C1-C4)- Alkylsulfonyl, Phenyl, Phenyl-(C1-C6)-alkyl, Phenylcarbonyl, 2-Pyridinyl, 3-Pyridinyl, 4- Pyridinyl, wobei die 11 zuletzt genannten Reste mit Halogen, (C1-C6)-Alkyl, (C1-C6)-Alkyloxy, Nitril oder Trifluormethyl substiuiert sein können, weiter bevorzugt ausgewählt ist aus Wasserstoff, Acetyl, (C1-C4)-Alkyl, (C1-C4)-Alkylsulfonyl oder Phenylcarbonyl, wobei das Phenyl mit einem Halogen substituiert sein kann, noch weiter bevorzugt bevorzugt Wasserstoff, (C1-C4)-Alkyl oder Acetyl ist, und am meisten bevorzugt Wasserstoff ist. Am meisten bevorzugt bilden R1 und R2zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie gebunden sind, einen gesättigten sechs- oder siebengliedrigen Ring, wie im folgenden dargestellt, wherein the saturated six- or seven-membered ring is represented by m substituents selected from halo, acetyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, trifluoromethyl, (C 1 -C 6) alkylsulfonyl, (C 3 -C 6) cycloalkylsulfonyl or phenylsulfonyl may be substituted, and wherein R 1a is preferably selected from hydrogen, acetyl, trifluoroacetyl, (C 1 -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) cycloalkylcarbonyl, ( C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl, phenylcarbonyl, 2-pyridinyl, 3 Pyridinyl, 4-pyridinyl, where the last-mentioned radicals can be substituted by halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyloxy, nitrile or trifluoromethyl, more preferably selected from hydrogen, acetyl, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkylsulfonyl or phenylcarbonyl, where the phenyl may be substituted by a halogen, even more preferably hydrogen, (C 1 -C 4) -alkyl or acetyl, and most preferably is hydrogen. Most preferably, R1 and R2 together with the carbon or nitrogen atom to which they are attached form a saturated six- or seven-membered ring, as shown below.
wobei der gesättigte sechs- oder siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, (C1-C6)-Alkylsulfonyl, (C3- C6)-Cycloalkylsulfonyl oder Phenylsulfonyl substituiert sein kann, und wobei R1a bevorzugt ausgewählt ist aus Wasserstoff, Acetyl, Trifluoracetyl, (C1-C6)-Alkyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkylcarbonyl, (C3-C6)-Cycloalkyl-(C1-C6)-Alkyl, (C1-C4)- Alkylsulfonyl, Phenyl, Phenyl-(C1-C6)-alkyl, Phenylcarbonyl, 2-Pyridinyl, 3-Pyridinyl, 4- Pyridinyl, wobei die 11 zuletzt genannten Reste mit Halogen, (C1-C6)-Alkyl, (C1-C6)-Alkyloxy, Nitril oder Trifluormethyl substiuiert sein können, weiter bevorzugt ausgewählt ist aus Wasserstoff, (C1-C4)-Alkyl, Acetyl, (C1-C4)-Alkylsulfonyl oder Phenylcarbonyl, wobei das Phenyl mit einem Halogen substituiert sein kann, noch weiter bevorzugt Wasserstoff, (C1-C4)-Alkyl oder Acetyl ist, und am meisten bevorzugt Wasserstoff ist. Eine vierte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welcher R3 bevorzugt Wasserstoff ist. Eine fünfte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R4 und R5 jeweils unabhängig voneinander, bevorzugt Wasserstoff, (C1-C6)-Alkyl, Hydroxy, where the saturated six- or seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, trifluoromethyl, (C 1 -C 6 ) -alkylsulfonyl, ( C 3 -C 6 ) -cycloalkylsulfonyl or phenylsulfonyl, and wherein R 1a is preferably selected from hydrogen, acetyl, trifluoroacetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkylcarbonyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl, phenyl, phenyl (C 1 -C 6 ) -alkyl , Phenylcarbonyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, wherein the last-mentioned radicals may be substituted by halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyloxy, nitrile or trifluoromethyl , more preferably selected from hydrogen, (C 1 -C 4 ) -alkyl, acetyl, (C 1 -C 4 ) -alkylsulfonyl or phenylcarbonyl, where the phenyl may be substituted by a halogen, even more preferably, is hydrogen, (C 1 -C 4) alkyl or acetyl, and most preferably is hydrogen. A fourth embodiment of the present invention comprises compounds of the general formula (I) in which R3 is preferably hydrogen. A fifth embodiment of the present invention comprises compounds of the general formula (I) in which R 4 and R 5 are each independently of one another, preferably hydrogen, (C 1 -C 6 ) -alkyl, hydroxy,
Cyclopropyl oder (C1-C6)-Alkoxy sind; R4 und R5 jeweils unabhängig voneinander, besonders bevorzugt Wasserstoff, Methyl, Ethyl, Cyclopropyl or (C 1 -C 6 ) alkoxy; R4 and R5 are each independently of one another, more preferably hydrogen, methyl, ethyl,
Propyl, Cyclopropyl, Hydroxy oder Methoxy sind; und R4 und R5 jeweils unabhängig voneinander, ganz besonders bevorzugt Wasserstoff, Methyl oder  Propyl, cyclopropyl, hydroxy or methoxy; and R4 and R5 are each independently, most preferably hydrogen, methyl or
Ethyl sind. In dieser fünften Ausführungsform ist speziell bevorzugt, wenn mindestens einer der Reste R4 bzw. R5 Wasserstoff ist. Weiter bevorzugt ist, wenn mindestens einer der Reste R4 bzw. R5 Wasserstoff und der andere Rest R4 bzw. R5 ungleich Wasserstoff und insbesondere (C1-C6)-Alkyl ist. Ganz speziell bevorzugt ist, wenn einer der Reste R4 bzw. R5 Wasserstoff und der andere Rest R4 bzw. R5 Methyl ist. Eine sechste Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R4 und R5 bevorzugt zusammen eine (C2-C7)-Alkylengruppe bilden, die ein oder mehrere  Are ethyl. In this fifth embodiment, it is particularly preferred if at least one of R4 and R5 is hydrogen. It is further preferred if at least one of the radicals R4 or R5 is hydrogen and the other radical R4 or R5 is different from hydrogen and in particular (C1-C6) -alkyl. Especially preferred is when one of the radicals R4 or R5 is hydrogen and the other radical R4 or R5 is methyl. A sixth embodiment of the present invention comprises compounds of the general formula (I) in which R4 and R5 preferably together form a (C 2 -C 7) -alkylene group which is one or more
Sauerstoff- und/oder Schwefelatome enthalten können, wobei die (C2-C7)- Alkylengruppe durch Halogen einfach oder mehrfach substituiert sein kann und die jeweilgen Halogensubstituenten gleich oder verschieden sein können; R4 und R5 besonders bevorzugt zusammen mit dem Kohlenstoffatom, an welchem sie gebunden sind, einen drei- oder viergliedrigen Ring bilden; und R4 und R5 am meisten bevorzugt zusammen eine nicht-substituierte (C2-C3)-Alkylengruppe bilden. Eine siebte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R6 und R7 unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl oder (C6-C14)-Aryl sind; R6 und R7 unabhängig voneinander, besonders bevorzugt Wasserstoff, Methyl oder Phenyl sind; May contain oxygen and / or sulfur atoms, wherein the (C2-C7) - alkylene group may be monosubstituted or polysubstituted by halogen and the respective halogen substituents may be the same or different; R4 and R5 particularly preferably together with the carbon atom to which they are attached form a three- or four-membered ring; and R4 and R5 most preferably together form a non-substituted (C2-C3) alkylene group. A seventh embodiment of the present invention comprises compounds of the general formula (I) in which R6 and R7 are independently hydrogen, (C1-C6) -alkyl or (C6-C14) -aryl; R6 and R7 are independently of each other, more preferably hydrogen, methyl or phenyl;
und R6 und R7 ganz besonders bevorzugt Wasserstoff sind. Eine achte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R8 bevorzugt Wasserstoff, (C1-C6)-Alkyl oder Halogen ist; R8 besonders bevorzugt Wasserstoff, Methyl oder Fluor ist; und R8 ganz besonders bevorzugt Wasserstoff ist. Eine neunte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R9 bevorzugt Wasserstoff oder (C1-C6)-Alkyl; R9 besonders bevorzugt Wasserstoff oder Methyl ist; und R9 ganz besonders bevorzugt Wasserstoff ist. Eine zehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R10 bevorzugt Wasserstoff, (C1-C6)-Alkyl, Di-(C1-C6)-alkylamino, Halogen, (C2-C6)-Alkenyl, (C2- C6)-Alkinyl, (C1-C6)-Alkyl-(C2-C6)-alkinyl, (C1-C6)-Alkoxy-(C1-C6)-alkyl-(C2-C6)-alkinyl, Cyano, (C1-C6)-Alkoxycarbonyl oder Aminocarbonyl ist; R10 besonders bevorzugt Wasserstoff, Methyl, Propyl, Isopropyl, Butyl, tert.-Butyl, Dimethylamino, Fluor, Chlor, Brom, Iod, Ethenyl, Ethinyl, Methylethinyl, Ethylethinyl, MeOCH2C ^C-, Cyano, COOMe oder CONH2 ist; und R10 ganz besonders bevorzugt Wasserstoff, Methyl oder Fluor ist. Eine elfte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R11 bevorzugt Wasserstoff oder (C1-C6)-Alkyl ist; R11 besonders bevorzugt Wasserstoff oder Methyl ist; und R11 ganz besonders bevorzugt Wasserstoff ist. Eine zwölfte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen X bevorzugt für CH2, O oder einer Bindung steht, wobei, wenn n = 0, X keine Bindung sein kann; und and R6 and R7 are most preferably hydrogen. An eighth embodiment of the present invention comprises compounds of the general formula (I) in which R 8 is preferably hydrogen, (C 1 -C 6 ) -alkyl or halogen; R 8 is particularly preferably hydrogen, methyl or fluorine; and R8 is very particularly preferably hydrogen. A ninth embodiment of the present invention comprises compounds of the general formula (I) in which R 9 is preferably hydrogen or (C 1 -C 6) -alkyl; R 9 is particularly preferably hydrogen or methyl; and R9 is very particularly preferably hydrogen. A tenth embodiment of the present invention comprises compounds of the general formula (I) in which R 10 is preferably hydrogen, (C 1 -C 6) -alkyl, di (C 1 -C 6) -alkylamino, halogen, (C 2 -C 6) -alkenyl, ( C 2 -C 6) alkynyl, (C 1 -C 6) -alkyl- (C 2 -C 6) -alkynyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl- (C 2 -C 6) -alkynyl, cyano, ( C1-C6) alkoxycarbonyl or aminocarbonyl; R 10 is particularly preferably hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluorine, chlorine, bromine, iodine, ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH 2 C 1 -C-, cyano, COOMe or CONH 2; and R10 is very particularly preferably hydrogen, methyl or fluorine. An eleventh embodiment of the present invention comprises compounds of the general formula (I) in which R 11 is preferably hydrogen or (C 1 -C 6) alkyl; R11 is more preferably hydrogen or methyl; and R11 is very particularly preferably hydrogen. A twelfth embodiment of the present invention comprises compounds of the general formula (I) in which X is preferably CH 2 , O or a bond, where when n = 0, X can not be a bond; and
X ganz besonders bevorzugt für eine Bindung steht, wobei n 1 oder 2 beträgt. X is very particularly preferably a bond, where n is 1 or 2.
Eine dreizehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R12 bevorzugt Wasserstoff ist. Eine vierzehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R13 bevorzugt Wasserstoff ist. Eine fünfzehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen die Laufzahl m bevorzugt 0, 1, 2, 3 oder 4, mehr bevorzugt 0, 1, 2, oder 3 und am meisten bevorzugt 0, 1 oder 2 beträgt. A thirteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 12 is preferably hydrogen. A fourteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 13 is preferably hydrogen. A fifteenth embodiment of the present invention comprises compounds of the general formula (I) in which the number of run m is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2, or 3 and most preferably 0, 1 or 2.
Im Rahmen der vorliegenden Erfindung ist es möglich, die einzelnen bevorzugten, besonders bevorzugten, ganz besonders bevorzugten und am meisten bevorzugten Bedeutungen für die In the context of the present invention, it is possible to use the individual preferred, particularly preferred, very particularly preferred and most preferred meanings for the
Substituenten R1 bis R14 und X beliebig miteinander zu kombinieren, wobei die Laufzahl n 0, 1 oder 2 ist. Das heißt, dass Verbindungen der allgemeinen Formel (I) von der vorliegenden Erfindung umfasst sind, in welchen beispielsweise der Substituent R1 eine bevorzugte Bedeutung aufweist und die Substituenten R2 bis R14 die allgemeine Bedeutung aufweisen oder aber der Substituent R2 eine bevorzugte Bedeutung aufweist, der Substituent R3 eine besonders bevorzugte, bzw. eine ganz besonders bevorzugte, Substituents R1 to R14 and X to combine with each other, where the run number n is 0, 1 or 2. That is, compounds of the general formula (I) are encompassed by the present invention, in which, for example, the substituent R 1 has a preferred meaning and the substituents R 2 to R 14 have the general meaning or the substituent R 2 has a preferred meaning, the substituent R3 is a particularly preferred, or a very particularly preferred,
Bedeutung aufweist und die übrigen Substituenten eine allgemeine Bedeutung aufweisen. Vier dieser Kombinationen der oben für die Substituenten R1 bis R11und X gegebenen Definitionen werden nachfolgend beispielhaft erläutert und jeweils als weitere Ausführungsformen offenbart: Kombination der oben für die Substituenten R1 bis R11 und X jeweils als besonders bevorzugt bezeichneten Definitionen (zwölfte Ausführungsform), Kombination der oben für die Substituenten R1 bis R14und X jeweils als ganz besonders bevorzugt bezeichneten Definitionen (dreizehnten Has meaning and the other substituents have a general meaning. Four of these combinations of the definitions given above for the substituents R1 to R11 and X are exemplified below and each disclosed as further embodiments: Combination of the above for the substituents R1 to R11 and X respectively as particularly preferred definitions (twelfth embodiment), combination of the above for the substituents R1 to R14 and X are each defined as very particularly preferred definitions (thirteenth
Ausführungsform), und Kombination der oben für den Substituenten R1 als ganz besonders bevorzugt bezeichneten Definition mit den oben für die Substituenten R1 bis R14 und X jeweils als besonders bevorzugt bezeichneten Definitionen (vierzehnte Ausführungsform). Die vorgenannten auf den Kombinationen der Substituenten basierenden weiteren Ausführungsformen werden nachfolgend aus Gründen der Klarheit explizit offenbart: Eine sechszehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 und R2 zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie Embodiment), and combination of the above for the substituent R1 as very particularly preferred definition with the above for the substituents R1 to R14 and X are each designated as particularly preferred definitions (fourteenth embodiment). The aforesaid further embodiments based on the combinations of the substituents are explicitly disclosed below for the sake of clarity: A sixteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 and R 2 together with the carbon atom or nitrogen atom to which they are attached
gebunden sind, einen gesättigten sechs- oder siebengliedrigen Ring, wie im folgenden dargestellt bonded, a saturated six- or seven-membered ring, as shown below
wobei der gesättigte sechs- oder siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, (C1-C6)- Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl oder Phenylsulfonyl substituiert sein kann, und wobei R1a Wasserstoff, Acetyl, (C1-C4)-Alkyl, (C1-C4)-Alkylsulfonyl oder Phenylcarbonyl, wobei das wherein the saturated six- or seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, trifluoromethyl, (C 1 -C 6 ) -alkylsulfonyl, ( C 3 -C 6 ) -cycloalkylsulfonyl or phenylsulfonyl, and wherein R 1a is hydrogen, acetyl, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl or phenylcarbonyl, wherein the
Phenyl mit einem Halogen substituiert sein kann; R3 Wasserstoff ist; R4 und R5 jeweils unabhängig voneinander Wasserstoff, Methyl, Ethyl, Propyl, Cyclopropyl, Hydroxy oder Methoxy sind; R6 und R7 unabhängig voneinander Wasserstoff, Methyl oder Phenyl sind; R8 Wasserstoff, Methyl oder Fluor ist; R9 Wasserstoff oder Methyl ist; R10 Wasserstoff, Methyl, Propyl, Isopropyl, Butyl, tert.-Butyl, Dimethylamino, Fluor, Chlor, Brom, Iod, Ethenyl, Ethinyl, Methylethinyl, Ethylethinyl, MeOCH2C ^C-, Cyano, COOMe oder CONH2 ist; R11 Wasserstoff oder Methyl ist; und X eine Bindung ist, wobei n 1 oder 2 beträgt. Phenyl may be substituted with a halogen; R3 is hydrogen; R4 and R5 are each independently hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy or methoxy; R6 and R7 are independently hydrogen, methyl or phenyl; R8 is hydrogen, methyl or fluorine; R9 is hydrogen or methyl; R 10 is hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluoro, chloro, bromo, iodo, ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH 2 C 1 -C-, cyano, COOMe or CONH 2 ; R11 is hydrogen or methyl; and X is a bond, where n is 1 or 2.
Eine siebzehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 und R2 zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie A seventeenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 and R 2 together with the carbon atom or nitrogen atom to which they are attached
gebunden sind, einen gesättigten sechs- oder siebengliedrigen Ring bilden, wie im folgenden dargestellt  are bound to form a saturated six- or seven-membered ring, as shown below
wobei der gesättigte sechs- oder siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, (C1-C6)- Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl oder Phenylsulfonyl substituiert sein kann, wherein the saturated six- or seven-membered ring is represented by m substituents selected from halo, acetyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, trifluoromethyl, (C 1 -C 6) alkylsulfonyl, (C 3 -C 6) cycloalkylsulfonyl or phenylsulfonyl may be substituted,
und wobei R1a Wasserstoff, Acetyl oder (C1-C4)-Alkyl ist; R3 Wasserstoff ist; R4 und R5 jeweils unabhängig voneinander Methyl, Ethyl oder Wasserstoff sind; R6, R7, R8, R9 und R11 Wasserstoff sind; R10 Wasserstoff, Methyl oder Fluor ist; und X für eine Bindung steht, wobei n 1 oder 2 ist. and wherein R 1a is hydrogen, acetyl or (C 1 -C 4) -alkyl; R3 is hydrogen; R4 and R5 are each independently methyl, ethyl or hydrogen; R6, R7, R8, R9 and R11 are hydrogen; R 10 is hydrogen, methyl or fluorine; and X is a bond, where n is 1 or 2.
Eine achzehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Nitro, Trimethylsilylethinyl, Methyl, Ethyl, An eighteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, trimethylsilylethynyl, methyl, ethyl,
Propyl, Isopropyl, Butyl, tert.-Butyl, n-Pentyl, n-Heptyl, Cyclopropyl, Cyclobutyl, Acetyl, Ethinyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl, Monofluormethyl, Methoxy, Ethoxy oder Methoxymethyl ist;R2 Wasserstoff, Chlor, Phenyl, 2-Methylphenyl, 3- Trifluormethylphenyl, Methyl, Ethyl, Isopropy, Butyl, tert.-Butyl, n-Pentyl, n-Heptyl,  Propyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl, cyclopropyl, cyclobutyl, acetyl, ethynyl, amino, dimethylamino, trifluoromethyl, difluoromethyl, monofluoromethyl, methoxy, ethoxy or methoxymethyl; R2 is hydrogen, chloro, phenyl , 2-methylphenyl, 3-trifluoromethylphenyl, methyl, ethyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl,
Trifluormethyl, 1-Methylcyclopropyl, 1-(p-Xylyl)-cyclopropyl, 1-(2,4-Dichlorphenyl)- cyclopropyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl, Monofluormethyl, CHFCH3, CF(CH3)2, CHF(CH2CH3), 1-Fluorcyclopropyl, Cyclopentyl, Methoxy, Ethoxy, Methoxymethyl, Ethoxymethyl, Thiomethyl, Methylthio oder Methoxy ist; R3 Wasserstoff ist; R4 und R5 jeweils unabhängig voneinander Wasserstoff, Methyl, Ethyl, Propyl, Cyclopropyl, Hydroxy oder Methoxy sind; R6 und R7 unabhängig voneinander Wasserstoff, Methyl oder Phenyl sind; R8 Wasserstoff, Methyl oder Fluor ist; R9 Wasserstoff oder Methyl ist; R10 Wasserstoff, Methyl, Propyl, Isopropyl, Butyl, tert.-Butyl, Dimethylamino, Fluor, Chlor, Brom, Iod, Ethenyl, Ethinyl, Methylethinyl, Ethylethinyl, MeOCH2C ^C-, Cyano, COOMe oder CONH2 ist; R11 Wasserstoff oder Methyl ist; und X eine Bindung ist, wobei n 1 oder 2 beträgt. Trifluoromethyl, 1-methylcyclopropyl, 1- (p-xylyl) -cyclopropyl, 1- (2,4-dichlorophenyl) -cyclopropyl, amino, dimethylamino, trifluoromethyl, difluoromethyl, monofluoromethyl, CHFCH 3 , CF (CH 3 ) 2 , CHF ( CH 2 CH 3 ), 1-fluorocyclopropyl, cyclopentyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, thiomethyl, methylthio or methoxy; R3 is hydrogen; R4 and R5 are each independently hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy or methoxy; R6 and R7 are independently hydrogen, methyl or phenyl; R8 is hydrogen, methyl or fluorine; R9 is hydrogen or methyl; R 10 is hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluoro, chloro, bromo, iodo, ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH 2 C 1 -C-, cyano, COOMe or CONH 2 ; R11 is hydrogen or methyl; and X is a bond, where n is 1 or 2.
Eine neunzehnte Ausführungsform der vorliegenden Erfindung umfasst Verbindungen der allgemeinen Formel (I), in welchen R1 Methyl, Ethyl, Propyl, Dimethylamino, Diethylamio, 1-pyrrolidino-, 1-piperidino, 4- morpholino, Acetyl oder Trifluormethyl ist; R2 Methyl oder Ethyl ist; R3 Wasserstoff ist; R4 und R5 jeweils unabhängig voneinander Wasserstoff, Methyl oder Ethyl sind; R6 und R7 Wasserstoff sind; R8 Wasserstoff ist; R9 Wasserstoff ist; R10 Wasserstoff, Methyl oder Fluor ist; R11 Wasserstoff ist; und X eine Bindung ist, wobei n 1 oder 2 beträgt. A nineteenth embodiment of the present invention comprises compounds of the general formula (I) in which R 1 is methyl, ethyl, propyl, dimethylamino, diethylamio, 1-pyrrolidino, 1-piperidino, 4-morpholino, acetyl or trifluoromethyl; R 2 is methyl or ethyl; R3 is hydrogen; R4 and R5 are each independently hydrogen, methyl or ethyl; R6 and R7 are hydrogen; R8 is hydrogen; R9 is hydrogen; R 10 is hydrogen, methyl or fluorine; R11 is hydrogen; and X is a bond, where n is 1 or 2.
Im Rahmen der vorliegenden Erfindung sind von der Verbindung der allgemeinen Formel (I) auch Verbindungen umfasst, die durch a) Protonierung, b) Alkylierung oder c) Oxidation an einem In the context of the present invention, the compound of the general formula (I) also includes compounds which are characterized by a) protonation, b) alkylation or c) oxidation on a
Stickstoffatom quaterniert sind. Insbesondere sind diesebzüglich die entsprechenden N-Oxide zu nennnen. Die Verbindungen der Formel (I) können Salze bilden. Salzbildung kann durch Einwirkung einer Base auf solche Verbindungen der Formel (I) erfolgen, die ein acides Wasserstoffatom tragen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Nitrogen atom are quaternized. In particular, these include the corresponding N-oxides. The compounds of formula (I) can form salts. Salt formation can be caused by the action of a base to those compounds of the formula (I) take place, which carry an acidic hydrogen atom. Examples of suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular
Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR´R´´R´´´]+, worin R bis R´´´ jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (C1-C4)-Trialkylsulfonium- und (C1-C4)- Trialkylsulfoxoniumsalze. Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p-Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Im Folgenden werden die Verbindungen der Formel (I) und ihre Salze auch kurz als erfindungsgemäß verwendete oder erfindungsgemäße "Verbindungen (I)" bezeichnet. In der allgemeinen Formel (I) und allen übrigen Formeln in der vorliegenden Erfindung können die Reste Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino, Alkylthio, Haloalkylthio, sowie die entsprechenden ungesättigten und/oder substituierten Reste im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein. Wenn nicht speziell angegeben, sind bei diesen Resten die niederen 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, for example with cations of the formula [NRR'R''R'''] +, where R to R'''Each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts. The compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. 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. In the following, the compounds of the formula (I) and their salts are also referred to briefly as "compounds (I)" used according to the invention or according to the invention. In the general formula (I) and all other formulas in the present invention, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched. Unless specifically stated, these residues are the lower ones
Kohlenstoffgerüste, z. B. mit 1 bis 6 Kohlenstoffatomen, insbesondere 1 bis 4 Kohlenstoffatomen, bzw. bei ungesättigten Gruppen mit 2 bis 6 Kohlenstoffatomen, insbesondere 2 bis 4 Kohlenstoffatomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Bedeutungen wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i- Hexyl und 1,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexy und 1,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste; wobei mindestens eine Doppelbindung bzw. Dreifachbindung, vorzugsweise eine Doppelbindung bzw. Dreifachbindung enthalten ist. Alkenyl bedeutet z.B. Vinyl, AIIyI, 1-Methylprop-2-en-1-yl, 2- Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1- yl; Alkinyl bedeutet z.B. Ethinyl, Propargyl, But-2-in-1-yl, But-3-in-1-yl und 1-Methyl-but-3-in-1-yl. Cycloalkyl-Gruppen sind z. B. Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl. Die Cycloalkyl Gruppen können in bi- oder tri-cyclischer Form vorkommen. Wenn Haloalkylgruppen und Haloalkylreste von Haloalkoxy, Haloalkylthio, Haloalkenyl, Haloalkinyl u.a. angegeben sind, sind bei diesen Resten die niederen Kohlenstoffgerüste, z. B. mit 1 bis 6 C-Atomen oder 2 bis 6, insbesondere 1 bis 4 C-Atomen oder bevorzugt 2 bis 4 C-Atomen, sowie die Carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred. Alkyl radicals, including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexy and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; wherein at least one double bond or triple bond, preferably a double bond or triple bond is included. Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2- Methyl-prop-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-ene-1-yl; Alkynyl includes, for example, 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. The cycloalkyl groups can occur in bi- or tri-cyclic form. When haloalkyl groups and haloalkyl radicals of haloalkoxy, haloalkylthio, haloalkenyl, haloalkynyl, etc. are indicated, these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 C-atoms or 2 to 6, in particular 1 to 4 C-atoms or preferably 2 to 4 C-atoms, as well as the
entsprechenden ungesättigten und/oder substituierten Reste im Kohlenstoffgerüst jeweils geradkettig oder verzweigt. Beispiele sind Difluormethyl, 2,2,2-Trifluorethyl, Trifluorallyl, 1-Chlorprop-1-yl-3-yl. Alkylen-Gruppen sind bei diesen Resten die niederen Kohlenstoffgerüste, z. B. mit 1 bis 10 C-Atomen, insbesondere 1 bis 6 C-Atomen oder bevorzugt 2 bis 4 C-Atomen, sowie die entsprechenden ungesättigten und/oder substituierten Reste im Kohlenstoffgerüst, die jeweils geradkettig oder verzweigt sein können. Beispiele sind Methylen, Ethylen, n- und i- Propylen und n-, s-, i-, t-Butylen. Hydroxyalkylgruppen sind bei diesen Resten die niederen Kohlenstoffgerüste, z. B. mit 1 bis 6 C- Atomen, insbesondere 1 bis 4 C-Atomen, sowie die entsprechenden ungesättigten und/oder 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. Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 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 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
substituierten Resten im Kohlenstoffgerüst, die jeweils geradkettig oder verzweigt sein können. substituted radicals in the carbon skeleton, which may each be straight-chain or branched.
Beispiele hierzu sind 1,2-Dihydroxyethyl und 3-Hydroxypropyl. Halogen bedeutet Fluor, Chlor, Brom oder lod. Haloalkyl, -alkenyl und -alkinyl bedeuten durch Halogen, vorzugsweise durch Fluor, Chlor oder Brom, insbesondere durch Fluor und/oder Chlor, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Examples of these are 1,2-dihydroxyethyl and 3-hydroxypropyl. Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, alkenyl and alkynyl are alkyl, alkenyl or alkynyl, for example, partially or completely substituted by halogen, preferably by fluorine, chlorine or bromine, in particular by fluorine and / or chlorine. Monohaloalkyl (=
Monohalogenalkyl), Perhaloalkyl, CF3, CF2Cl, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 und OCH2CH2CI; Monohaloalkyl), perhaloalkyl, CF 3 , CF 2 Cl, CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl; 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;
entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierte Reste. Aryl bedeutet ein mono-, bi- oder polycyclisches aromatisches System, beispielsweise Phenyl oder Naphthyl, vorzugsweise Phenyl. Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der allgemeinen Formel (II) oder deren agrochemischen Salze oder quartären N-Derivate von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. Die oben angeführten allgemeinen oder in Vorzugsbereichen angeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (II) als auch entsprechend für die die jeweils zur Herstellung benötigten Ausgangs- und Zwischenprodukte. Diese Restedefinitionen können untereinander, als auch zwischen den angegebenen bevorzugten Bereichen vertauscht werden. Die vorliegenden Verbindungen der allgemeinen Formel (I) weisen an der Bindestelle zum Amino- [1,2,4]-triazolderivate ein chirales Kohlenstoffatom auf, welches in der unten dargestellten Struktur durch die Kennzeichnung (*) verdeutlicht ist: 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. Above all, for reasons of higher herbicidal activity, better selectivity and / or better manufacturability, compounds of the general formula (II) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination. The general or preferred radical definitions given above apply both for the end products of the general formula (II) and, correspondingly, for the starting materials and intermediates required in each case for the preparation. These residue definitions can be interchanged with each other as well as between the specified preferred ranges. The present compounds of the general formula (I) have, at the binding site to the amino [1,2,4] triazole derivatives, a chiral carbon atom which is illustrated in the structure shown below by the labeling (*):
Gemäß den Regeln nach Cahn, Ingold und Prelog (CIP-Regeln) kann dieses Kohlenstoffatom sowohl eine (R)- als auch eine (S)-Konfiguration aufweisen. Von der vorliegenden Erfindung werden Verbindungen der allgemeinen Formel (I) sowohl mit (S)- als auch mit (R)-Konfiguration erfasst, d.h., dass die vorliegende Erfindung die Verbindungen der allgemeinen Formel (I) erfasst, in welchen das betreffende Kohlenstoffatom (1) eine (R)-Konfiguration; oder (2) eine (S)-Konfiguration aufweist. Darüber hinaus werden im Rahmen der vorliegenden Erfindung auch (3) beliebige Mischungen von Verbindungen der allgemeinen Formel (I), welche eine (R)- Konfiguration (Verbindungen der allgemeinen Formel (I-(R)) aufweisen, mit Verbindungen der allgemeinen Formel (I), welche eine (S)-Konfiguration (Verbindungen der allgemeinen Formel (I-S)) aufweisen, erfasst, wobei eine racemische Mischung der Verbindungen der allgemeinen Formel (I) mit (R)- und (S)-Konfiguration von der vorliegenden Erfindung ebenfalls umfasst ist. Allerdings sind im Rahmen der vorliegenden Erfindung insbesondere Verbindungen der allgemeinen Formel (I) mit (R)-Konfiguration mit einer Selektivität von 60 bis 100%, vorzugsweise 80 bis 100%, insbesondere 90 bis 100%, ganz besonders 95 bis 100%, bevorzugt, wobei die jeweilige (R)-Verbindung mit einer Enantioselektivität von jeweils mehr als 50% ee, vorzugsweise 60 bis 100% ee, insbesondere 80 bis 100% ee, ganz besonders 90 bis 100% ee, meist bevorzugt 95 bis 100% ee, bezogen auf den Gesamtgehalt an betreffender (R)-Verbindung vorliegt. Unter Berücksichtigung der Regel nach Cahn, Ingold und Prelog kann es an dem mit (*) According to the rules of Cahn, Ingold and Prelog (CIP rules), this carbon atom can have both an (R) and an (S) configuration. The present invention covers compounds of the general formula (I) having both (S) and (R) configurations, that is to say that the present invention covers the compounds of the general formula (I) in which the relevant carbon atom ( 1) an (R) configuration; or (2) has an (S) configuration. In addition, in the context of the present invention, (3) any mixtures of compounds of the general formula (I) which have an (R) -configuration (compounds of the general formula (I- (R)) with compounds of the general formula ( I) having an (S) configuration (compounds of general formula (IS)), wherein a racemic mixture of the compounds of general formula (I) having (R) and (S) configuration of the present invention However, in the context of the present invention, in particular compounds of the general formula (I) having (R) -configuration with a selectivity of 60 to 100%, preferably 80 to 100%, in particular from 90 to 100%, very particularly preferably from 95 to 100%, the respective (R) compound having an enantioselectivity of more than 50% ee, preferably 60 to 100% ee, in particular 80 to 100% ee, very particular 90 to 100% ee, most preferably 95 to 100% ee, based on the total content of the relevant (R) compound is present. Taking into account the rule according to Cahn, Ingold and Prelog, it can at the (*)
gekennzeichneten Kohlenstoffatom auch zu einer Situation kommen, in welcher aufgrund der Priorität der jeweiligen Substituenten die (S)-Konfiguration am mit (*) gekennzeichneten Kohlenstoffatom bevorzugt ist. Dieses ist beispielweise dann der Fall, wenn die Reste R4 und/oder R5 einem C1-C6- Alkoxyrest entsprechen. Daher sind im Rahmen der vorliegenden Erfindung insbesondere Verbindungen der allgemeinen Formel (I) bevorzugt, die in ihrer räumlichen Anordnung den jenigen Verbindungen der allgemeinen Formel (I) mit R4 und R5 =Wasserstoff mit (R)-Konfiguration entsprechen, mit einer Selektivität von 60 bis 100 %, vorzugsweise 80 bis 100 %, insbesondere 90 bis 100 %, ganz besonders 95 bis 100 %, bevorzugt, wobei die jeweilige (R)-analoge-Verbindung mit einer Enantioselektivität von jeweils mehr als 50 % ee, vorzugsweise 60 bis 100 % ee, insbesondere 80 bis 100 % ee, ganz besonders 90 bis 100 % ee, meist bevorzugt 95 bis 100 % ee, bezogen auf den Gesamtgehalt an betreffender (R)-analogen-Verbindung, vorliegt. Daher betrifft die vorliegende Erfindung insbesondere Verbindungen der allgemeinen Formel (I), in welchen die stereochemische Konfiguration an dem mit (*) gekennzeichnet Kohlenstoffatom mit einer stereochemischen Reinheit von 60 bis 100 % (R, bzw. analog-R), vorzugsweise 80 bis 100 % (R, bzw. analog-R), insbesondere 90 bis 100 % (R, bzw. analog-R), ganz besonders 95 bis 100 % (R, bzw. analog-R), vorliegt. Insbesondere können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) noch weitere Chiralitätszentren an den mit (**) und (***) gekennzeichneten Kohlenstoffatomen aufweisen also show a situation in which, due to the priority of the respective substituents, the (S) -configuration at the carbon atom marked with (*) is preferred. This is the case, for example, when the radicals R4 and / or R5 correspond to a C 1 -C 6 -alkoxy radical. Therefore, in the context of the present invention, preference is given in particular to compounds of the general formula (I) whose spatial arrangement corresponds to those compounds of the general formula (I) where R 4 and R 5 = hydrogen of (R) -configuration, with a selectivity of 60 to 100%, preferably 80 to 100%, in particular 90 to 100%, very particularly 95 to 100%, preferably, where the respective (R) analogue compound having an enantioselectivity of more than 50% ee, preferably 60 to 100 % ee, in particular 80 to 100% ee, very particularly 90 to 100% ee, most preferably 95 to 100% ee, based on the total content of relevant (R) -analogen compound, is present. Therefore, the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R, or analog-R), preferably 80 to 100 % (R, or analog-R), in particular 90 to 100% (R, or analog-R), very particularly 95 to 100% (R, or analog-R), is present. In particular, the compounds of the general formula (I) according to the invention may have further chiral centers on the carbon atoms marked (**) and (***)
Im Rahmen der vorliegenden Erfindung sind beliebige stereochemische Konfigurationen an den mit (*), (**) und (***) gekennzeichneten Kohlenstoffatomen möglich: Darüber hinaus können, je nach Wahl der jeweiligen Reste, weitere Stereoelemente in den In the context of the present invention, any stereochemical configurations are possible on the carbon atoms labeled with (*), (**) and (3): In addition, depending on the choice of the respective radicals, further stereo elements in the
erfindungsgemäßen Verbindungen der allgemeinen Formel (I) vorliegen. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Compounds of the general formula (I) according to the invention are present. If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, then
Enantiomere und Diastereomere auftreten. Entsprechende Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfaßt werden, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind und deren Gemische. Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I) Enantiomers and diastereomers occur. Corresponding stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, 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 are encompassed by the general formula (I) but are not specified with their specific stereoform and their mixtures. Particular preference is given to compounds of the general formula (I)
in denen das chirale Kohlenstoffatom mit der Kennzeichnung (*) eine (R)-Konfiguration und das chirale Kohlenstoffatom mit der Kennzeichnung (**) eine (S)-Konfiguration aufweist. Die Kombinationsmöglichkeiten der verschiedenen Substituenten der allgemeinen Formel (I) sind so zu verstehen, dass die allgemeinen Grundsätze des Aufbaus chemischer Verbindungen zu beachten sind, d.h. die Formel (I) nicht Verbindungen umfasst, von denen der Fachmann weiß, dass sie chemisch nicht möglich sind. Die im folgenden dargestellten Verbindungen der Formeln (I-a), (I-b), (I-c), (I-d), (I-e), (I-f), (I-g), (I-h) (I-i), (I-j) und (I-k) sind bevorzugte Verbindungen gemäß der Formel (I) der vorliegende Erfindung. in which the chiral carbon atom labeled (*) has an (R) -configuration and the chiral Carbon atom marked (**) has an (S) configuration. The possible combinations of the various substituents of the general formula (I) are to be understood in such a way that the general principles of the construction of chemical compounds are observed, ie the formula (I) does not include compounds which the person skilled in the art knows are not chemically possible , The compounds represented by the formulas (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih) (Ii), (Ij) and (Ik) shown below are preferred compounds according to formula (I) of the present invention.
CC
(I-j) (I-k) In den folgenden Tabellen 1 bis 11 steht Y für (Ij) (Ik) In the following Tables 1 to 11, Y stands for
elle 1: Beispiele der Verbindungen der allgemeinen Formel (I-a): BExample 1: Examples of the compounds of general formula (I-a): B
C C
S S
71 01 4 Rla 1 * * -A 71 01 4 Rla 1 * * - A
NN----1\1 u las dn NN ---- 1 \ 1 ul a s dn
yl yl
- 72 - - 72 -
ispiel-Nr. Y R1a ispiel no. Y R1a
B B
C C
1S 17 40 1 -A u las dn 1S 17 40 1 - A ul a s dn
- 82 - - 82 -
B B
C C
rbonyl S1 rbonyl 17 rbonyl S1 rbonyl 17
40 1 -A u las dn rbonyl 40 1 - A ul a s dn rbonyl
- 92 - - 92 -
rbonyl rbonyl
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 03 - - 03 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 13 - - 13 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 23 - - 23 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 33 - - 33 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 43 - - 43 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 53 - - 53 -
B B
C C
S S
71 01 14 -A u las dn 71 01 14 - A ul a s dn
- 63 - - 63 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 73 - - 73 -
B B
C C
S S
71 1 40 1 -A u las dn d) 71 1 40 1 - A ul a s dn d)
- 83 - - 83 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 93 - - 93 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 04 - - 04 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 14 - - 14 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 24 - - 24 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 34 - - 34 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 44 - - 44 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 54 - - 54 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 64 - - 64 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 74 - - 74 -
B B
C C
S S
71 1 40 1 -A u las dn 71 1 40 1 - A ul a s dn
- 84 - - 84 -
B B
C C
S S
71 01 14 -A su nl a d 71 01 14 - A su n l a d
- 94 - - 94 -
Weiterer Gegenstand der vorliegenden Erfindung sind Verfahren zur Herstellung entsprechender Verbindungen der allgemeinen Formel (I) und/oder deren Salze und/oder deren agrochemisch verträglichen quarternierten Stickstoff-Derivate Another object of the present invention are methods for preparing corresponding compounds of general formula (I) and / or salts thereof and / or their agrochemically compatible quaternized nitrogen derivatives
in welchen die Reste R1 bis R11 sowie X und die Laufzahl n die vorstehenden Bedeutungen aufweisen, und wobei nach einem ersten Verfahren eine Verbindung der allgemeinen Formel (II) in which the radicals R 1 to R 11 and X and the sequence number n have the abovementioned meanings, and where, according to a first process, a compound of the general formula (II)
wobei R1, R2 die vorstehende Bedeutung aufweisen und Z1für einen austauschfähigen Rest oder eine Abgangsgruppe steht, mit einem Amin der allgemeinen Formel (III) where R 1, R 2 have the abovementioned meaning and Z 1 is an exchangeable radical or a leaving group, with an amine of the general formula (III)
wobei die Reste R3 bis R11 sowie X und n die vorstehende Bedeutung aufweisen, oder mit einem Säureadditionssalz des Amins der allgemeinen Formel (III) umgesetzt wird. Der austauschfähige Rest Z1, bzw. die Abgangsgruppe Z1 steht für Fluor, Chlor, Brom, Iod, ein (C1-4)- Alkylsulfanyl oder ein (C1-4)-Alkylsulfinyl oder ein (C1-4)-Alkylsulfonyl, ein unsubstituiertes oder ein einfach oder mehrfach mit Fluor, Chlor, Brom oder (C1-4)-Alkyl oder (C1-4)-Alkoxy substituiertes Phenyl-(C1-4)-alkylsulfonyl oder ein (C1-4)-Alkylphenyl-sulfonyl. Gegebenenfalls kann ein Rest Z1 in eine andere, besser austauschbare Gruppe überführt werden. So kann beispielsweise im Sinne eines Zweistufen-Eintopfverfahren ein (C1-4)-Alkylsulfanyl mit einem wherein the radicals R3 to R11 and X and n have the above significance, or is reacted with an acid addition salt of the amine of the general formula (III). The exchangeable radical Z1 or the leaving group Z1 is fluorine, chlorine, bromine, iodine, a (C1-4) -alkylsulfanyl or a (C1-4) -alkylsulfinyl or a (C1-4) -alkylsulfonyl, an unsubstituted or a phenyl (C1-4) -alkylsulfonyl which is monosubstituted or polysubstituted by fluorine, chlorine, bromine or (C1-4) -alkyl or (C1-4) -alkoxy or a (C1-4) -alkylphenyl-sulfonyl. Optionally, a radical Z1 can be converted into another, more easily exchangeable group. Thus, for example, in the context of a two-stage one-pot process, a (C 1-4) alkylsulfanyl with a
Oxidationsmittel wie m-Chlorperbenzoesäure oder Oxone® in ein (C1-4)-Alkylsulfinyl oder ein (C1-4)- Alkylsulfonyl oder Mischungen davon überführt werden und anschließend mit einem Amin der allgemeinen Formel (III) oder einem Säureadditionssalz unter Verwendung einer Hilfsbase wie z.B. Triethylamin oder Kaliumcarbonat zur Reaktion gebracht werden. Gegebenenfalls kann die Umsetzung auch durch unterschiedliche Hilfsstoffe katalysiert werden, wie beispielswiese durch die Reagenzien Kaliumphosphat, Kupfer(I)iodid und N,N-Diethyl-2- hydroxybenzamid oder im Sinne der Buchwald-Hartwig-Kupplung durch spezielle Oxidizing agents such as m-chloroperbenzoic acid or Oxone® in a (C 1-4 ) alkylsulfinyl or a (C 1-4 ) alkylsulfonyl or mixtures thereof are converted and then with an amine of general formula (III) or an acid addition salt using a Auxiliary base such as triethylamine or potassium carbonate are reacted. Optionally, the reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
Übergangsmetallkatalysatorsysteme und Basen. Geeignete Katalysatorsysteme sind z.B. [(2-Di- cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′ - biphenyl)]palladium(II) methanesulfonate methanesulfonate (G3 Brettphos Pd®) und 2- (Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl (Brettphos®) mit t-Butanolat oder chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropylbiphenyl][2-(2- aminoethyl)phenyl]Pd(II) mit Natriumcarbonat oder tris(dibenzylideneacetone)dipalladium(0) chloroform complex und (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane mit Natriumphenolat oder 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) und tris- (dibenzylideneacetone)dipalladium(0) mit Ceasiumcarbonat. Schema 1 Transition metal catalyst systems and bases. Suitable catalyst systems are e.g. [(2-Dicyclohexylphosphino-3,6-dimethoxy-2 ', 4', 6'-triisopropyl-1,1'-biphenyl) -2- (2'-amino-1,1'-biphenyl)] palladium (II) Methanesulfonate methanesulfonates (G3 Brettphos Pd®) and 2- (dicyclohexylphosphino) -3,6-dimethoxy-2 ', 4', 6'-triisopropyl-1,1'-biphenyl (Brettphos®) with t-butoxide or chloro [2- (dicyclohexylphosphino) -3,6-dimethoxy-2 ', 4', 6'-triisopropylbiphenyl] [2- (2-aminoethyl) phenyl] Pd (II) with sodium carbonate or tris (dibenzylideneacetone) dipalladium (0) chloroform Complex and (5-diphenylphosphino-9,9-dimethyl-xanthen-4-yl) -diphenyl-phosphanes with sodium phenolate or 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (XPhos) and tris (dibenzylideneacetone) dipalladium (0) with ceasium carbonate. Scheme 1
(IV) (V) (VI) (VII) Die in obigen Schemata verwendeten Ausgangsverbindungen sind entweder käuflich oder nach an sich bekannten Methoden herstellbar. So können die substituierten cyklischen 1,2,4-Triazole der allgemeinen Formel (I) beispielsweise nach den in J. Het. Chem.40, 821- 826 (2003) beschriebenen Methoden hergestellt werden. Schema 2 ( IV) (V) (VI) (VII) The starting compounds used in the above schemes are either commercially available or can be prepared by methods known per se. Thus, the substituted cyclic 1,2,4-triazoles of the general formula (I), for example, according to the in J. Het. Chem. 40, 821-826 (2003). Scheme 2
(I-e, I-f, I-g, I-h)  (I-e, I-f, I-g, I-h)
wobei Z1für einen austauschfähigen Rest oder eine Abgangsgruppe steht, mit einem Amin der allgemeinen Formel (III) oder einem Säureadditionssalz des Amins der allgemeinen Formel (III) reagieren kann und die Laufzahl p = 2, 3 oder 4 sowie die Laufzahl q = 1 oder 2 beträgt. Nach der Substitution kann der Schwefel mit einem Oxidationsmittel wie m-Chlorperbenzoesäure oder Kaliumperoxymonosulfat (Oxone®) erfolgreich oxidiert werden (Schema 2). wherein Z1 is an exchangeable group or a leaving group, can react with an amine of general formula (III) or an acid addition salt of the amine of general formula (III) and the run number p = 2, 3 or 4 and the run number q = 1 or 2 is. After substitution, the sulfur can be successfully oxidized with an oxidizing agent such as m-chloroperbenzoic acid or potassium peroxymonosulfate (Oxone®) (Scheme 2).
Schema 3 Scheme 3
Die erfindungsgemäßen substituierten cyklischen 1,2,4-Triazole mit der allgemein Formel (II) können wie folgend hergestellt werden (Schema 3). Die Amine der allgemein Formel (III) oder einem The substituted cyclic 1,2,4-triazoles of the general formula (II) according to the invention can be prepared as follows (Scheme 3). The amines of the general formula (III) or a
Säureadditionssalz des Amins der allgemein Formel (III) werden mit Dimethyl-N- cyanodithioiminocarbonat umgesetzt beispielsweise nach den in J. Med. Chem.56, 9071-9088 (2013) beschriebene Methoden. und mit Hydrazinhydrat zum Aminotriazol (IX) cyklisiert. Das Aminotriazol kann durch eine Michael-Addition mit Acrylsäuremethylester zum 6,7-dihydro-4H-[1,2,4]triazolo[1,5- a]pyrimidin-5-one umgewandelt werden. Die letzte Stufe erfolgt mit einer Alkylierung unter basischen Bedingungen, wobei Xa = Chlor, Brom, Jod oder (C1-4)-Alkylsulfonyl oder ein Phenyl-(C1-4)-alkyl- sulfonyl sein kann. Acid addition salt of the amine of the general formula (III) are reacted with dimethyl-N-cyanodithioiminocarbonate, for example, by the methods described in J. Med. Chem. 56, 9071-9088 (2013). and cyclized with hydrazine hydrate to aminotriazole (IX). The aminotriazole can be converted to the 6,7-dihydro-4H- [1,2,4] triazolo [1,5-a] pyrimidin-5-one by a Michael addition with methyl acrylate. The last stage is carried out with an alkylation under basic conditions, where Xa = chlorine, bromine, iodine or (C 1-4 ) alkylsulfonyl or a phenyl (C 1-4 ) alkylsulfonyl.
Schema 4 LiAlH 4 Scheme 4 L iAlH 4
Die im obigen Schema 4 verwendeten Ausgangsverbindungen sind entweder käuflich oder nach bekannten Methoden herstellbar. So können die erfindungsgemäßen substituierten cyklische 1,2,4- triazole mit der allgemein Formel (II) hergestellt werden.1H-1,2,4-triazole-3,5-diamin wird durch eine Michael-Addition mit Acrylsäuremethylester zum 2-Amino-6,7-dihydro-4H-[1,2,4]triazolo[1,5- a]pyrimidin-5-on (XI) umgewandelt. Die Aminogruppe kann in einer Sandmeyer-Reaktion in eine Abgangsgruppe Z1 umgewandelt werden, beispielsweise nach den in MedChemComm, 4, 422-431 (2013) beschriebenen Methoden, wobei Xa wie oben definiert ist. Der austauschfähige Rest Z1, bzw. die Abgangsgruppe Z1 steht für Fluor, Chlor, Brom, Iod, ein (C1-4)- Alkylsulfanyl oder ein (C1-4)-Alkylsulfinyl oder ein (C1-4)-Alkylsulfonyl, ein unsubstituiertes oder ein einfach oder mehrfach mit Fluor, Chlor, Brom oder (C1-4)-Alkyl oder (C1-4)-Alkoxy substituiertes Phenyl-(C1-4)-alkylsulfonyl oder ein (C1-4)-Alkylphenyl-sulfonyl. Gegebenenfalls kann die Umsetzung auch durch unterschiedliche Hilfsstoffe katalysiert werden, wie beispielswiese durch die Reagenzien Kaliumphosphat, Kupfer(I)iodid und N,N-Diethyl-2- hydroxybenzamid oder im Sinne der Buchwald-Hartwig-Kupplung durch spezielle The starting compounds used in the above Scheme 4 are either commercially available or can be prepared by known methods. Thus, the substituted cyclic 1,2,4-triazoles according to the invention can be prepared with the general formula (II). 1H-1,2,4-triazole-3,5-diamine is converted into a 2-amino group by a Michael addition with methyl acrylate -6,7-dihydro-4H- [1,2,4] triazolo [1,5-a] pyrimidin-5-one (XI). The amino group can be converted into a leaving group Z1 in a Sandmeyer reaction, for example by the methods described in MedChemComm, 4, 422-431 (2013), where Xa is as defined above. The exchangeable radical Z1, and the leaving group Z1 represents fluorine, chlorine, bromine, iodine, a (C 1-4) - alkylsulphanyl or a (C 1-4) alkylsulfinyl or a (C 1-4) alkylsulfonyl, an unsubstituted or mono- or polysubstituted with fluorine, chlorine, bromine or (C 1-4 ) -alkyl or (C 1-4 ) -alkoxy-substituted phenyl- (C 1-4 ) -alkylsulfonyl or a (C 1-4 ) alkylphenyl-sulfonyl. Optionally, the reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
Übergangsmetallkatalysatorsysteme. Die letzte Reaktion erfolg mit einer Alkylierung unter basischen Bedingungen. Transition metal catalyst systems. The last reaction is by alkylation under basic conditions.
Schema 5 Die im obigen Schema 5 verwendeten Ausgangsverbindungen sind entweder käuflich oder nach bekannten Methoden herstellbar. So können die erfindungsgemäßen substituierten cyklischen 1,2,4- triazole mit der allgemein Formel (I-a) hergestellt werden. [1,2,4]Triazolo[1,5-a]pyrazin-2-amine wird durch Reaktion zwischen 2-Aminopyrazin, Ethoxycarbonylisothiocyanat und Hydroxylamin Scheme 5 The starting compounds used in Scheme 5 above are either commercially available or can be prepared by known methods. Thus, the substituted cyclic 1,2,4-triazoles according to the invention can be prepared with the general formula (Ia). [1,2,4] Triazolo [1,5-a] pyrazine-2-amine is obtained by reaction between 2-aminopyrazine, ethoxycarbonylisothiocyanate and hydroxylamine
Hydrochlorid unter basischen Bedingungen (analog zu J. Med. Chem., 2014, Vol.57, Seiten 3687-3706) hergestellt. Anschliessend wird die Aminogruppe durch eine Sandmeyer-Reaktion in einen Hydrochloride under basic conditions (analogous to J. Med. Chem., 2014, Vol. 57, pages 3687-3706). Subsequently, the amino group by a Sandmeyer reaction in a
austauschfähigen Rest Z1 umgewandelt. Der austauschfähige Rest Z1, bzw. die Abgangsgruppe Z1 steht für Fluor, Chlor, Brom, Iod, ein (C1-4)- Alkylsulfanyl oder ein (C1-4)-Alkylsulfinyl oder ein (C1-4)-Alkylsulfonyl, ein unsubstituiertes oder ein einfach oder mehrfach mit Fluor, Chlor, Brom oder (C1-4)-Alkyl oder (C1-4)-Alkoxy substituiertes Phenyl-(C1-4)-alkylsulfonyl oder ein (C1-4)-Alkylphenyl-sulfonyl. Gegebenenfalls kann die Umsetzung auch durch unterschiedliche Hilfsstoffe katalysiert werden, wie beispielswiese durch die Reagenzien Kaliumphosphat, Kupfer(I)iodid und N,N-Diethyl-2- hydroxybenzamid oder im Sinne der Buchwald-Hartwig-Kupplung durch spezielle exchangeable remainder Z1 converted. The exchangeable radical Z1 or the leaving group Z1 is fluorine, chlorine, bromine, iodine, a (C1-4) -alkylsulfanyl or a (C1-4) -alkylsulfinyl or a (C1-4) -alkylsulfonyl, an unsubstituted or a phenyl (C1-4) -alkylsulfonyl which is monosubstituted or polysubstituted by fluorine, chlorine, bromine or (C1-4) -alkyl or (C1-4) -alkoxy or a (C1-4) -alkylphenyl-sulfonyl. Optionally, the reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
Übergangsmetallkatalysatorsysteme. Im letzten Schritt wird eine Alkylierung unter basischen Transition metal catalyst systems. In the last step, an alkylation under basic
Bedingungen durchgeführt. Die Amine der allgemeinen Formel (III) oder die Säureadditionssalz davon sind kommerziell verfügbar bzw. deren Synthese ist in WO 2004/069814 A1 beschrieben. Verbindungen der allgemeinen Formel (I) können auch dadurch hergestellt werden, dass zunächst eine Verbindung der allgemeinen Formel (I) hergestellt wird, die dann in weiteren Reaktionsschritten in andere Zielmoleküle überführt werden. Beispielswiese können Schwefelatome in R1 durch Oxidation in SO oder SO2 überführt werden, oder NH kann durch Umsetzung mit Säurechloriden oder Anhydride in die entsprechenden Amide oder duch Umsetzung mit Sulfonylchloriden in die entsprechenden Conditions performed. The amines of the general formula (III) or the acid addition salt thereof are commercially available or their synthesis is described in WO 2004/069814 A1. Compounds of the general formula (I) can also be prepared by first preparing a compound of the general formula (I), which are then converted into other target molecules in further reaction steps. For example, sulfur atoms in R1 can be converted by oxidation into SO or SO2, or NH can be converted to the corresponding amides by reaction with acid chlorides or anhydrides or by reaction with sulfonyl chlorides
Sulfonamide überführt werden, Sulfonamides are transferred,
Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry– Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England oder MultiPROBE Automated Workstations der Firma Perkin Elmer, Waltham, Massachusetts 02451, USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma Teledyne ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer- supported reagents/Scavanger-Harze unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol.4, No.1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich). Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998 und Combinatorial Chemistry– Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may 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, pages 1 to 34. For parallelized reaction performance and work-up, a number of commercially available devices may be used, for example reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451 , UNITED STATES. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, chromatographic apparatuses are available, inter alia, for example Teledyne ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. 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. The implementation of single or several synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. A number of experimental protocols are described in the literature, for example in ChemFiles, Vol.4, No.1, Polymer-Supported Scavengers and Reagents for Solution Phase Synthesis (Sigma-Aldrich). In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin. Solid-phase assisted synthesis methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", published by Academic Press, 1998 and Combinatorial Chemistry Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. Use from
Festphasen- unterstützten Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically. Both solid and liquid phases may require the performance of one or more
Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Synthetic steps are supported by the use of microwave technology. In the
Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und A. Stadler), Verlag Wiley, 2005. Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. Weiterer Gegenstand der Erfindung ist aufgrund der herbiziden Eigenschaft der Verbindungen der allgemeinen Formel (I) auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als Herbizide zur Bekämpfung von Schadpflanzen. Herbizide werden in landwirtschaftlich genutzten Kulturen während verschiedener Anbauphasen eingesetzt. So erfolgt die Applikation einiger Produkte schon vor oder während der Saat. Andere werden ausgebracht, bevor die Kulturpflanze aufläuft, d.h. bevor der Keimling die Erdoberfläche A number of experimental protocols are described in specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (Editor CO Kappe and A. Stadler), published by Wiley, 2005. The preparation according to the processes described here yields compounds of the formula (I) and their salts in the form 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. Herbicides are used in agricultural crops during various stages of cultivation. Thus, the application of some products already before or during the sowing. Others are applied before the crop is run up, i. before the seedling the earth's surface
durchbricht (Vorauflauf-Herbizide). Nachauflauf-Herbizide schließlich werden verwendet, wenn von der Kulturpflanze entweder bereits die Keimblätter oder Laubblätter ausgebildet sind. Die erfindungsgemäßen Verbindungen können dabei sowohl im Vorlauf als auch im Nachlauf angewendet werden, wobei eine Verwendung der erfindungsgemäßen Verbindungen im Vorlauf bevorzugt ist. Die Vorauflauf-Behandlung schließt sowohl die Behandlung der Anbaufläche vor der Aussaat (ppi = pre plant incorporation) als auch die Behandlung der angesäten, aber noch nicht bewachsenen Anbauflächen ein. Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die breaks through (pre-emergence herbicides). Postemergence herbicides are finally used when either the cotyledons or leaves are already formed from the crop. The compounds of the invention can be used both in the forerun and in the wake, wherein a use of the compounds of the invention in the flow is preferred. Pre-emergence treatment includes pre-sowing (ppi) pre-sowing treatment as well as treatment of sown, but not overgrown crop areas. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. Bei der Anwendung von erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt-Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im Application rate can vary within wide limits. For use as a herbicide for controlling harmful plants, the total amount of compounds of general formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in Range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications. In the application of compounds of the general formula (I) according to the invention and / or salts thereof as a plant growth regulator, for example as Halmverkürzer in crops, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn , the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / Ha. This applies to both the application in the
Vorauflauf oder im Nachauflauf. Pre-emergence or postemergence.
Die erfindungsgemäßen Verbindungen der Formel (I) und deren Salze, im folgenden auch synonym zusammen auch als Verbindungen der Formel (I) bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen auf. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Dabei ist es gleichgültig, ob die Substanzen im Vorsaat-, Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnem seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kontrolliert werden können, ohne daß durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Auf der Seite der monokotylen Unkrautarten werden z. B. Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, 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. In the individual examples may be mentioned some representatives of the monocotyledonous and dicotyledonous weed flora, which can be controlled by the compounds of the general formula (I) according to the invention, without the intention of limiting them to certain species. On the side of monocotyledonous weed species, for. Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca,
Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, sowie Cyperusarten vorwiegend aus der annuellen Gruppe und auf Seiten der perennierenden Spezies Agropyron, Cynodon, Imperata sowie Sorghum und auch ausdauernde Cyperusarten gut erfaßt. Bei dikotylen Unkrautarten erstreckt sich das Wirkungsspektrum auf Arten wie z. B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon und Sida auf der annuellen Seite sowie Convolvulus, Cirsium, Rumex und Artemisia bei den perennierenden Unkräutern. Außerdem wird herbizide Wirkung bei dikotylen Unkräutern wie Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica und Xanthium beobachtet. Werden die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. Bei Applikation der Wirkstoffe der allgemeinen Formel (I) auf die grünen Pflanzenteile im Fimbristylis, ischaemum, lolium, monochoria, panicum, paspalum, phalaris, phleum, poa, sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperusarten mainly from the annuelle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusarten well grasped. 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. In addition, herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium are observed. If the compounds of the general formula (I) according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die after the lapse of three to three weeks four weeks completely off. When applying the active compounds of the general formula (I) to the green plant parts in
Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so daß auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Obgleich die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen wie z. B. Weizen, Gerste, Roggen, Reis, Mais, Zuckerrübe, Baumwolle, Raps und Soja nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Nutzpflanzungen. Darüber hinaus weisen die erfindungsgemäßen Substanzen der allgemeinen Formel (I) hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Postemergence also occurs very rapidly after treatment, a drastic halt in growth and the weed plants remain in the existing at the time of application growth stage or die after a period of time completely, so that in this way harmful to the crop weed competition is eliminated very early and sustainable. Although 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. In addition, 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 influence the metabolism
Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z. B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da das Lagern hierdurch verringert oder völlig verhindert werden kann. Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Plant ingredients and harvest relief such. 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 storage can be reduced or completely prevented. Due to their herbicidal and plant growth regulatory properties, 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. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
Fettsäurezusammensetzung des Ernteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z. B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung liegen. Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in Fatty acid composition of the crop known. Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation. Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful and ornamental plants, eg. As 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. Preferably, the compounds of general formula (I) as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant. Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z. B. EP 0221044, Breeding methods and the generation of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, US Pat.
EP 0131624). Beschrieben wurden beispielsweise in mehreren Fällen - gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/011376, WO 92/014827, WO 91/019806), - transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z. B. EP 0131624). For example, genetic engineering alterations of crop plants for the purpose of modifying the starch synthesized in plants (eg WO 92/011376, WO 92/014827, WO 91/019806) have been described in several cases, - transgenic crop plants which are resistant to certain herbicides of the type Glufosinate (cf., for example,
EP 0242236, EP 0242246) oder Glyphosate (WO 92/000377) oder der Sulfonylharnstoffe (EP 0257993, US 5013659) resistent sind, - transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis- Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen (EP 0142924, EP 0193259), - transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/013972), - gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen (EP 0309862, EP 0464461), - gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EP 0305398), - transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming“), - transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualitat auszeichnen - transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking“). Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt; siehe z. B. I. Potrykus und EP 0242236, EP 0242246) or glyphosate (WO 92/000377) or the sulfonylureas (EP 0257993, US 5013659), - transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP 0142924, EP 0193259), - Transgenic crops with modified fatty acid composition (WO 91/013972), - genetically modified crops with new content or secondary substances z. B. new phytoalexins which cause increased disease resistance (EP 0309862, EP 0464461), - genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398), - transgenic crops which produce pharmaceutically or diagnostically important proteins ( "Molecular pharming"), - transgenic crops, which are characterized by higher yields or better quality - transgenic crops characterized by a combination of z. B. the above-mentioned new properties ("gene stacking"). Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; see, for. BI Potrykus and
G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg oder Christou, "Trends in Plant Science" 1 (1996) 423-431). Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA- Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996. Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J.11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J.1 (1991), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, "Trends in Plant Science" 1 (1996) 423-431). For such genetic engineering, 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. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996. The production of plant cells with 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 for the purpose of achieving a cosuppression effect or expression at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, on the one hand DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA Sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such 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 Sci., USA 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 can in principle be plants of any one
Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Bei der Anwendung der erfindungsgemäßen Wirkstoffe der allgemeinen Formel (I) in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen. Die Verbindungen der allgemeinen Formel (I) können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in- Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse. Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl.1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed.1979, G. Goodwin Ltd. London. Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösemittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, Plant species, ie, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences. Preferably, 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 synthases (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, are resistant. In the application of the active compounds of the general formula (I) according to the invention in transgenic crops, in addition to the effects observed in other crops against harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum, that can be combated, changed application rates, which can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crops. The invention therefore also relates to the use of the 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 according to which biological and / or chemical-physical parameters are given. 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. These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed.1979, G. Goodwin Ltd. London. The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen,
"Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y.1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y.1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl.1986. Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z. B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z. B. in Form einer Fertigformulierung oder als Tankmix. Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y.1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y.1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing company, Stuttgart 1976; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986. On the basis of these formulations, combinations with other pesticidal 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. Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
Dispergiermittel), z. B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-Dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösemittel z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösemittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca- dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Dispersant), e.g. Example, polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine. To prepare the wettable powders, 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 made by dissolving the active ingredient in an organic solvent z. As butanol, cyclohexanone, dimethylformamide, xylene or 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). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z. B. Sorbitanfettsäureester oder Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as. B. sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z. B. Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z. B. Polyoxethylenesorbitanester such. B. Polyoxyethylensorbitanfettsäureester. Dusts are obtained by grinding the active ingredient with finely divided solids, eg. B.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß- Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z. B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Emulsionen, z. B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rühren, 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. Emulsions, eg. As oil-in-water emulsions (EW), for example, by stirring,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösemitteln und gegebenenfalls Tensiden, wie sie z. B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z. B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirk- stoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise– gewünschtenfalls in Mischung mit Düngemitteln– granuliert werden. Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z. B. Verfahren in "Spray- Drying Handbook" 3rd ed.1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S.8-57. Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z. B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. Die agrochemischen Zubereitungen enthalten in der Regel 0,1 bis 99 Gew.-%, insbesondere 0,1 bis 95 Gew.-%, Wirkstoff der Formel (I). In Spritzpulvern beträgt die Wirkstoffkonzentration z. B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as. B. are listed above in the other types of formulation produced. 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. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, 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 mixed with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluidized bed, extruder and spray granules see, for. B. Methods in "Spray-Drying Handbook" 3rd ed.1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff .; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For more details on pesticide formulation see, e.g. BGC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I). In wettable powders, the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Powdery
Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe u.a. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösemittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Die Verbindungen der allgemeinen Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z. B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder 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. In the case of water-dispersible granules, 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. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight. In addition, 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. As insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
Wachstumsregulatoren kombiniert eingesetzt werden, z. B. als Fertigformulierung oder als Growth regulators are used in combination, z. B. as a ready-made formulation or as
Tankmischungen. Als Kombinationspartner für die erfindungsgemäßen Verbindungen in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat- Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Tank mixes. Examples of combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase,
Photosystem I, Photosystem II oder Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 17th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2015 (vergl. https://www.bcpc.org/product/the- pesticide-manual-17th-edition) bzw. online https://www.bcpc.org/product/bcpc-online-pesticide- manual-latest-version und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Photosystem I, photosystem II or protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 17th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2015 (see https://www.bcpc.org/product/the-pesticide- manual- 17th-edition) or online https://www.bcpc.org/product/bcpc-online-pesticide- manual-latest version and literature cited therein. The following are examples of known herbicides or plant growth regulators, which can be combined with the compounds of the invention, these agents either with their "common name" in the English version according to International Organization for Standardization (ISO) or with the chemical name or code number. There are always all
Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Beispiele für solche herbiziden Mischungspartner sind: Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F- 7967, i.e.3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6- (trifluormethyl)pyrimidin-2,4(1H,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, Use forms such as acids, salts, esters as well as all isomeric forms such as stereoisomers and optical isomers, even if they are not explicitly mentioned. Examples of such herbicidal mixture partners are: acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro) 2-fluoro-3-methylphenyl) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorotassium, aminocyclopyrachloromethyl, aminopyralid, amitrole, ammonium sulfamates, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil-butyrate, -potassium , -heptanoates and -octanoates, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbr omuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorofluorol, chlorofluorol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlororthal-dimethyl, chlorosulfuron, cinidone, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D butotyl, -butyl, - dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4 -dimethyl-1,2-oxazolidin-3-one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidin-3-one, dichloroprop, dichlor orprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozine, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, ie N- [2-Chloro-4-fluoro-5- [4- (3-fluoro-propyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967, ie3- [7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, fenoxaprop , fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop -P-butyl,
flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e.1-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e.3-({[5-(Difluormethyl)-1- methyl-3-(trifluormethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, - dimethylammonium and methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate , glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201 , ie, O- (2,4-dimethyl-6-nitrophenyl) -O-ethyl-isopropylphosphoramidothioate, halo-cyano, halo-cyano-methyl, halosulfur, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfopethoxyethyl, haloxyfop-P, ethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, HW-02, ie1- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic -ammonium, imazapyr, imazapyr-isopropylammonium, imazaqu in, imaza-quin-ammonium, imazethapyr, imazethapyr-imonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH -043, ie3 - ({[5- (difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1 , 2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, 2-ethylhexyl, - isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzothiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(1-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e.4-(2,4-Dichlorbenzoyl)-1-methyl- 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e.1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl- 5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e.1-[7-Fluor-3-oxo-4-(prop-2-in-1- yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e.3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: methabenzthiazuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (Pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamide, petroleum oils, phenmedipham , picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulf uron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuronethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid , pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil , sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] - 2-nitrobenzoate, SYP-300, ie1- [7-fluoro-3-oxo-4- (prop-2-yn-1-yl) -3,4-dihydro-2H-1,4-benzoxazin-6-yl ] -3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn , thenylchloro, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron -sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, ie3,4-dichloro-N- {2- [(4,6-dimethoxypyrimidin-2-yl ) oxy] benzyl} aniline, and the following compounds:
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Examples of plant growth regulators as possible mixing partners are: acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-1-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Die Safener sind vorzugsweise ausgewählt aus der Gruppe bestehend aus: S1) Verbindungen der Formel (S1), Brassinolide, catechol, chloroformate chloride, cloprop, cyclanilide, 3- (cycloprop-1-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothaldipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-yl-butyric acid, isoprothiolane, probenazole, jasmonic acid, methyl jasmonate , maleic hydrazides, mepiquat chloride, 1-methylcyclopropenes, 2- (1-naphthyl) acetamides, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole , N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. The safeners are preferably selected from the group consisting of: S1) compounds of the formula (S1),
wobei die Symbole und Indizes folgende Bedeutungen haben: nA ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; R 1 where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3; R 1
A ist Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, Nitro oder (C1-C4)Haloalkyl; WA ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (W 1A is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl; W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N and O groups, wherein at least one N atom and at most one O atom is contained in the ring, preferably a residue from the group (W 1
A ) bis (W 4 A) to (W 4
A ),  A),
mA ist 0 oder 1; R 2 mA is 0 or 1; R 2
A ist OR 3 3 A is OR 3 3
A , SR 3 A, SR 3
A oder NRA R 4 A or NRA R 4
A oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger  A or a saturated or unsaturated 3- to 7-membered
Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S1) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C1-C4)Alkyl, (C1-C4)Alkoxy oder 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 with the carbonyl group in (S1) and unsubstituted or by radicals from the group (C 1 -C 4 ) Alkyl, (C 1 -C 4 ) alkoxy or
gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel OR 3 optionally substituted phenyl is substituted, preferably a radical of the formula OR 3
A , NHR 4 A, NHR 4
A oder N(CH3)2, insbesondere der Formel OR 3A or N (CH 3 ) 2 , in particular of the formula OR 3
A ; R 3A; R 3
A ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; R 4 A is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms; R 4
A ist Wasserstoff, (C1-C6)Alkyl, (C1-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; R 5 A is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl; R 5
A ist H, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C1-C4)Alkoxy(C1-C8)Alkyl, Cyano oder COOR 9 A is H, (C 1 -C 8) alkyl, (C 1 -C 8) haloalkyl, (C 1 -C 4) alkoxy (C 1 -C 8) alkyl, cyano or COOR 9
A , worin R 9 A, wherein R 9
A Wasserstoff, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl,  A is hydrogen, (C 1 -C 8) alkyl, (C 1 -C 8) haloalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl,
(C1-C6)Hydroxyalkyl, (C3-C12)Cycloalkyl oder Tri-(C1-C4)-alkyl-silyl ist; R 6 (C 1 -C 6) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri (C 1 -C 4) alkylsilyl; R 6
A , R 7 A, R 7
A , R 8 A, R 8
A sind gleich oder verschieden Wasserstoff, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C3- C12)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; vorzugsweise: a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1a), vorzugsweise A are the same or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1a), preferably
Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbon- säure, 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S1-1) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; b) Derivate der Dichlorphenylpyrazolcarbonsäure (S1b), vorzugsweise Verbindungen wie  Compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5- methyl 2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("mefenpyr-diethyl"), and related compounds as described in WO-A-91/07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1b), preferably compounds such as
1-(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1-2),  1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylic acid ethyl ester (S1-2),
1-(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1-3),  1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (S1-3),
1-(2,4-Dichlorphenyl)-5-(1,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1-4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind; c) Derivate der 1,5-Diphenylpyrazol-3-carbonsäure (S1c), vorzugsweise Verbindungen wie  Ethyl 1- (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) -pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A- 269806; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1c), preferably compounds such as
1-(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S1-5),  Ethyl 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5),
1-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S1-6) und verwandte  1- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related
Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; d) Verbindungen vom Typ der Triazolcarbonsäuren (S1d), vorzugsweise Verbindungen wie  Compounds as described, for example, in EP-A-268554; d) compounds of the type of the triazolecarboxylic acids (S1d), preferably compounds such as
Fenchlorazol(-ethylester), d.h.1-(2,4-Dichlorphenyl)-5-trichlormethyl-(1H)-1,2,4-triazol-3- carbonsäureethylester (S1-7), und verwandte Verbindungen wie sie in EP-A-174562 und EP-A-346620 beschrieben sind; e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure (S1e), vorzugsweise Verbindungen wie  Fenchlorazole (ethyl), ie, ethyl (1-1,4,4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2,4-triazole-3-carboxylate (S1-7), and related compounds as described in EP-A A-174562 and EP-A-346620 are described; e) compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1e), preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1-8) oder  5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or
5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw.5,5-Diphenyl-2-isoxazolin-3-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (S1-11) ("Isoxadifen-ethyl") 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in Or 3,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) (WO-A-91/08202; "isoxadifen-ethyl")
oder -n-propylester (S1-12) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3- carbonsäureethylester (S1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. S2) Chinolinderivate der Formel (S2),  or n-propyl ester (S1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13) as described in the patent application WO-A-95/07897 are. S2) quinoline derivatives of the formula (S2)
wobei die Symbole und Indizes folgende Bedeutungen haben: R 1where the symbols and indices have the following meanings: R 1
B ist Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, Nitro oder (C1-C4)Haloalkyl; nB ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; R 2 B is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl; nB is a natural number from 0 to 5, preferably 0 to 3; R 2
B ist OR 3 3 B is OR3 3
B , SRB oder NR 3 B, SRB or NR 3
B R 4 B R 4
B oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der  B 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, via the N-atom with the
Carbonylgruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C1- C4)Alkyl, (C1-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel OR 3 Carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR 3
B , NHR 4 B, NHR 4
B oder N(CH3)2, insbesondere der Formel OR 3 B or N (CH 3) 2, in particular of the formula OR 3
B ; R 3 B; R 3
B ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; R 4 B is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms; R 4
B ist Wasserstoff, (C1-C6)Alkyl, (C1-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; TB ist eine (C1 oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (C1- C4)Alkylresten oder mit [(C1-C3)-Alkoxy]-carbonyl substituiert ist; vorzugsweise: a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise  B is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl; TB is a (C1 or C2) alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4) alkyl radicals or by [(C1-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid (S2a) type, preferably
(5-Chlor-8-chinolinoxy)essigsäure-(1-methylhexyl)ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8-chinolinoxy)essigsäure-(1,3-dimethyl-but-1-yl)ester (S2-2),  (5-Chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-butoxy) 1-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyloxy-butylester (S2-3), (5-Chlor-8-chinolinoxy)essigsäure-1-allyloxy-prop-2-ylester (S2-4), (5-chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy) acetic acid 1-allyloxy-prop-2-yl ester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5),  (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6),  (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),
(5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7),  Allyl (5-chloro-8-quinolinoxy) acetates (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-1-ethylester (S2-8), (5-Chlor-8- chinolinoxy)essigsäure-2-oxo-prop-1-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0492366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind; b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise  (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366, and (5-chloro-8-quinolinoxy) acetic acid ( S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as described in the A-2002/34048; b) compounds of the (5-chloro-8-quinolinoxy) malonic acid (S2b) type, preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester,  Compounds such as diethyl (5-chloro-8-quinolinoxy) malonate,
(5-Chlor-8-chinolinoxy)malonsäurediallylester, (5-Chlor-8-chinolin- oxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0582198 beschrieben sind. S3) Verbindungen der Formel (S3)  (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5-chloro-8-quinolineoxy) malonic acid methyl ethyl ester and related compounds, as described in EP-A-0582198. S3) compounds of the formula (S3)
wobei die Symbole und Indizes folgende Bedeutungen haben: R 1where the symbols and indices have the following meanings: R 1
C ist (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C2-C4)Alkenyl, (C2-C4)Haloalkenyl, (C3-C7)Cycloalkyl, vorzugsweise Dichlormethyl; R 2 C is (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) cycloalkyl, preferably dichloromethyl; R 2
C , R 3 C, R 3
C sind gleich oder verschieden Wasserstoff, (C1-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C1- C4)Haloalkyl, (C2-C4)Haloalkenyl, (C1-C4)Alkylcarbamoyl-(C1-C4)alkyl, (C2- C4)Alkenylcarbamoyl-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Dioxolanyl-(C1-C4)alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder R 2 C are identical or different hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (C 1 -C 4) haloalkyl, (C 2 -C 4) haloalkenyl, (C 1 -C 4) alkylcarbamoyl ( C1-C4) alkyl, (C2-C4) alkenylcarbamoyl- (C1-C4) alkyl, (C1-C4) alkoxy- (C1-C4) alkyl, dioxolanyl- (C1-C4) alkyl, thiazolyl, furyl, furylalkyl, thienyl , Piperidyl, substituted or unsubstituted phenyl, or R 2
C und R 3 C and R 3
C bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring; vorzugsweise: Wirkstoffe vom Typ der Dichloracetamide, die häufig als Vorauflaufsafener (bodenwirksame Safener) angewendet werden, wie z. B. C together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-active safeners), such as. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1),  "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-1,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-1,3-oxazolidin) der Firma Stauffer (S3-3),  "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin) (S3-4),  "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]-dichloracetamid) der Firma PPG  "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG
Industries (S3-5),  Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),  "DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] -dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan) der Firma  "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7),  Nitrokemia and Monsanto (S3-7),
"TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),  "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9)  "Diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)
((RS)-1-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10); sowie dessen (R)-Isomer (S3-11). S4) N-Acylsulfonamide der Formel (S4) und ihre Salze,  ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "furilazole" or "MON 13900" ((RS) -3-dichloroacetyl) 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11). S4) N-acylsulfonamides of the formula (S4) and their salts,
worin die Symbole und Indizes folgende Bedeutungen haben: AD ist SO2-NR 3 wherein the symbols and indices have the following meanings: A D is SO 2 -NR 3
D -CO oder CO-NR 3 D is -CO or CO-NR 3
D -SO2 XD ist CH oder N; R 1D -SO 2 X D is CH or N; R 1
D ist CO-NR 5 D is CO-NR 5
D R 6 D R 6
D oder NHCO-R 7 D or NHCO-R 7
D ; R 2 D; R 2
D ist Halogen, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy, Nitro, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1- C4)Alkylsulfonyl, (C1-C4)Alkoxycarbonyl oder (C1-C4)Alkylcarbonyl; R 3 D is halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (Cl -C 4) alkylcarbonyl; R 3
D ist Wasserstoff, (C1-C4)Alkyl, (C2-C4)Alkenyl oder (C2-C4)Alkinyl; R 4D is hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl or (C 2 -C 4) alkynyl; R 4
D ist Halogen, Nitro, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy, (C3-C6)Cycloalkyl, Phenyl, (C1-C4)Alkoxy, Cyano, (C1-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (C1-C4)Alkoxycarbonyl oder (C1-C4)Alkylcarbonyl; R 5 D is halogen, nitro, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 3 -C 6) cycloalkyl, phenyl, (C 1 -C 4) alkoxy, cyano, (C 1 -C 4) Alkylthio, (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (C 1 -C 4) alkylcarbonyl; R 5
D ist Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5- C6)Cycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend vD Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1-C6)Alkoxy, (C1-C6)Haloalkoxy, (C1- C2)Alkylsulfinyl, (C1-C2)Alkylsulfonyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxycarbonyl, (C1- C4)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (C1-C4) Alkyl und (C1- C4)Haloalkyl substituiert sind; R 6D is hydrogen, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 5 -C 6) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing vD Heteroatoms from the group of nitrogen, oxygen and sulfur, where the seven latter radicals by vD substituents selected from the group consisting of halogen, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 1 - C 2 ) alkylsulfinyl, (C 1 -C 2) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxycarbonyl, (C 1 - C 4) alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (C 1 -C 4) Alkyl and (C 1 -C 4 ) haloalkyl; R 6
D ist Wasserstoff, (C1-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei die drei D is hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, wherein the three
letztgenannten Reste durch vD Reste aus der Gruppe Halogen, Hydroxy, (C1-C4)Alkyl, latter radicals by v D radicals from the group halogen, hydroxy, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy und (C1-C4)Alkylthio substituiert sind, oder R 5(C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio are substituted, or R 5
D und R 6 D and R 6
D gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden; R 7 D together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical; R 7
D ist Wasserstoff, (C1-C4)Alkylamino, Di-(C1-C4)alkylamino, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1- C4)Alkoxy, (C1-C6)Haloalkoxy und (C1-C4)Alkylthio und im Falle cyclischer Reste auch (C1- C4)Alkyl und (C1-C4)Haloalkyl substituiert sind; nD ist 0, 1 oder 2; mD ist 1 oder 2; vD ist 0, 1, 2 oder 3; davon bevorzugt sind Verbindungen vom Typ der N-Acylsulfonamide, z.B. der nachfolgenden Formel (S4a), die z. B. bekannt sind aus WO-A-97/45016 D is hydrogen, (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, where the latter two radicals are represented by v D substituents from the group halogen, (C 1 - C4) alkoxy, (C1-C6) haloalkoxy and (C1-C4) alkylthio and in case of cyclic radicals, also (C1-C4) alkyl and (C 1 -C 4) haloalkyl substituted are; n D is 0, 1 or 2; m D is 1 or 2; v D is 0, 1, 2 or 3; of these preferred are compounds of the type of N-acylsulfonamides, for example of the following formula (S4a), the z. B. are known from WO-A-97/45016
worin R 7 wherein R 7
D (C1-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1-C4)Alkoxy, (C1-C6)Haloalkoxy und (C1-C4)Alkylthio und im Falle cyclischer Reste auch (C1-C4)Alkyl und (C1-C4)Haloalkyl substituiert sind; R 4 D (C1-C6) alkyl, (C3-C6) cycloalkyl, where the 2 last-mentioned radicals by vD substituents selected from the group consisting of halogen, (C1-C4) alkoxy, (C1-C6) haloalkoxy and (C1-C4) alkylthio and im Cyclic radicals are also substituted by (C 1 -C 4) alkyl and (C 1 -C 4) haloalkyl; R 4
D Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3; mD 1 oder 2; vD ist 0, 1, 2 oder 3 bedeutet; sowie Acylsulfamoylbenzoesäureamide, z.B. der nachfolgenden Formel (S4b), die z.B. bekannt sind aus WO-A-99/16744,  D is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, CF 3; mD 1 or 2; vD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4b), e.g. are known from WO-A-99/16744,
z.B. solche worin R 5 for example, those in which R 5
D = Cyclopropyl und (R 4 D = cyclopropyl and (R 4
D ) = 2-OMe ist ("Cyprosulfamide", S4-1), R 5 D) = 2-OMe ("Cyprosulfamide", S4-1), R5
D = Cyclopropyl und (R 4 D = cyclopropyl and (R 4
D ) = 5-Cl-2-OMe ist (S4-2), R 5 D) = 5-Cl-2-OMe is (S4-2), R5
D = Ethyl und (R 4 D = ethyl and (R 4
D ) = 2-OMe ist (S4-3), R 5 D) = 2-OMe is (S4-3), R5
D = Isopropyl und (R 4 D = isopropyl and (R 4
D ) = 5-Cl-2-OMe ist (S4-4) und R 5 D) = 5-Cl-2-OMe is (S4-4) and R5
D = Isopropyl und (R 4 D = isopropyl and (R 4
D ) = 2-OMe ist (S4-5). sowie Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S4c), die z.B. bekannt sind aus der EP-A-365484,  D) = 2-OMe is (S4-5). and N-acylsulfamoylphenylurea type compounds of formula (S4c), e.g. are known from EP-A-365484,
worin R 8 wherein R 8
D und R 9 D and R 9
D unabhängig voneinander Wasserstoff, (C1-C8)Alkyl, (C3-C8)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl, R 4 D are independently hydrogen, (C 1 -C 8) alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 6) alkenyl, (C 3 -C 6) alkynyl, R 4
D Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3 mD 1 oder 2 bedeutet; beispielsweise 1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff,  D is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, CF 3 mD is 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff, 1- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
1-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff, sowie N-Phenylsulfonylterephthalamide der Formel (S4d), die z.B. bekannt sind aus CN 101838227, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, and N-phenylsulfonylterephthalamides of the formula (S4d), e.g. are known from CN 101838227,
z.B. solche worin R 4 for example, those in which R 4
D Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3; mD 1 oder 2; R 5D is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; m D 1 or 2; R 5
D Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5- C6)Cycloalkenyl bedeutet. S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen D is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl. S5) active ingredients from the class of hydroxyaromatic and aromatic-aliphatic
Carbonsäurederivate (S5), z.B.  Carboxylic acid derivatives (S5), e.g.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001 beschrieben sind. S6) Wirkstoffe aus der Klasse der 1,2-Dihydrochinoxalin-2-one (S6), z.B.  3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A- 2004/084631, WO-A-2005/015994, WO-A-2005/016001. S6) Agents from the class of 1,2-dihydroquinoxaline-2-ones (S6), e.g.
1-Methyl-3-(2-thienyl)-1,2-dihydrochinoxalin-2-on, 1-Methyl-3-(2-thienyl)-1,2-dihydro- chinoxalin-2-thion, 1-(2-Aminoethyl)-3-(2-thienyl)-1,2-dihydro-chinoxalin-2-on-hydrochlorid, 1-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydro-chinoxalin-2-on, wie sie in der WO- A-2005/112630 beschrieben sind. S7) Verbindungen der Formel (S7),wie sie in der WO-A-1998/38856 beschrieben sind 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 aminoethyl) -3- (2-thienyl) -1,2-dihydro-quinoxalin-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydro-quinoxalin-2-one as described in WO-A-2005/112630. S7) Compounds of the formula (S7) as described in WO-A-1998/38856
worin die Symbole und Indizes folgende Bedeutungen haben: R 1 in which the symbols and indices have the following meanings: R 1
E , R 2 E, R 2
E sind unabhängig voneinander Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkyl, E are independently halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl,
(C1-C4)Alkylamino, Di-(C1-C4)Alkylamino, Nitro; AE ist COOR 3(C 1 -C 4 ) alkylamino, di- (C 1 -C 4 ) alkylamino, nitro; A E is COOR 3
E oder COSR 4 E or COSR 4
E R 3 E R 3
E , R 4 E, R 4
E sind unabhängig voneinander Wasserstoff, (C1-C4)Alkyl, (C2-C6)Alkenyl, E are each independently hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,
(C2-C4)Alkinyl, Cyanoalkyl, (C1-C4)Haloalkyl, Phenyl, Nitrophenyl, Benzyl, (C 2 -C 4 ) alkynyl, cyanoalkyl, (C 1 -C 4 ) haloalkyl, phenyl, nitrophenyl, benzyl,
Halobenzyl, Pyridinylalkyl und Alkylammonium, n 1 Halobenzyl, pyridinylalkyl and alkylammonium, n 1
E ist 0 oder 1 n 2 E is 0 or 1 n 2
E , n 3 E, n 3
E sind unabhängig voneinander 0, 1 oder 2, vorzugsweise:  E are independently 0, 1 or 2, preferably:
Diphenylmethoxyessigsäure,  diphenylmethoxy,
Diphenylmethoxyessigsäureethylester,  Diphenylmethoxyessigsäureethylester,
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr.41858-19-9) (S7-1). S8) Verbindungen der Formel (S8),wie sie in der WO-A-98/27049 beschrieben sind  Methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1). S8) compounds of the formula (S8) as described in WO-A-98/27049
worin XF CH oder N, nF für den Fall, dass XF=N ist, eine ganze Zahl von 0 bis 4 und für den Fall, dass XF=CH ist, eine ganze Zahl von 0 bis 5, R 1 wherein XF is CH or N, nF in the case where XF = N, an integer of 0 to 4, and in the case that XF = CH, an integer of 0 to 5, R 1
F Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, Nitro, (C1- C4)Alkylthio, (C1-C4)-Alkylsulfonyl, (C1-C4)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. substituiertes Phenoxy, R 2 F is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl, (Cl -C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy, R 2
F Wasserstoff oder (C1-C4)Alkyl R 3F is hydrogen or (C 1 -C 4 ) alkyl R 3
F Wasserstoff, (C1-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der F is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the
vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; bedeuten, oder deren Salze, vorzugsweise Verbindungen worin XF CH, nF eine ganze Zahl von 0 bis 2 , R 1said C-containing radicals unsubstituted or substituted by one or more, preferably up to three identical or different radicals selected from the group consisting of halogen and alkoxy; or their salts, preferably compounds wherein X is F , F n is an integer from 0 to 2, R 1
F Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, R 2F is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, R 2
F Wasserstoff oder (C1-C4)Alkyl, R 3F is hydrogen or (C 1 -C 4 ) alkyl, R 3
F Wasserstoff, (C1-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der  F is hydrogen, (C 1 -C 8) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, wherein each of the
vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist, bedeuten,  aforementioned C-containing radicals unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy,
oder deren Salze. S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B.  or their salts. S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr.219479-18- 2), 1,2-Dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr.95855- 00-8), wie sie in der WO-A-1999/000020 beschrieben sind. S10) Verbindungen der Formeln (S10a) oder (S10b) wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind 1,2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg. No. 95855-00-8) as described in WO-A-1999/000020. S10) Compounds of the formulas (S10a) or (S10b) as described in WO-A-2007/023719 and WO-A-2007/023764
worin R 1 wherein R 1
G Halogen, (C1-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 YG, ZG unabhängig voneinander O oder S, nG eine ganze Zahl von 0 bis 4, R 2G is halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y G , Z G independently of one another O or S, n G is an integer from 0 to 4, R 2
G (C1-C16)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, R 3G (C 1 -C 16 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, R 3
G Wasserstoff oder (C1-C6)Alkyl bedeutet. S11) Wirkstoffe vom Typ der Oxyimino-Verbindungen (S11), die als Saatbeizmittel bekannt sind, wie z. B. G 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.
"Oxabetrinil" ((Z)-1,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (S11-1), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "Fluxofenim" (1-(4-Chlorphenyl)-2,2,2-trifluor-1-ethanon-O-(1,3-dioxolan-2-ylmethyl)-oxim) (S11-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (S11-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. S12) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3-oxo-1H-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr.205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361. S13) Eine oder mehrere Verbindungen aus Gruppe (S13): "Naphthalic anhydrid" (1,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "Flurazole" (Benzyl-2-chlor-4-trifluormethyl-1,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, "CL 304415" (CAS-Reg.Nr.31541-57-8) "Oxabetrinil" ((Z) -1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as millet safener for millet against damage by metolachlor, "Fluxofenim" (1- (4 -Chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S11-2), which has been known as seed-etch safener for millet against damage by metolachlor and "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as millet safener for millet against damage by metolachlor. S12) active substances from the class of isothiochromanones (S12), such as, for example, methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg.No.205121-04-6 ) (S12-1) and related compounds of WO-A-1998/13361. S13) One or more compounds from group (S13): "naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as safener for pretilachlor in seeded rice, "flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole -5-carboxylate) (S13-3) known as millet safener for millet against damages of alachlor and metolachlor, "CL 304415" (CAS Reg. No. 31541-57-8)
(4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-essigsäure) (S13-4) der Firma American  (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, "MG 191" (CAS-Reg.Nr.96420-72-3) (2-Dichlormethyl-2-methyl-1,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG 838" (CAS-Reg.Nr.133993-74-5)  Cyanamide known as safener for maize against damage of imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5 ) of Nitrokemia Company, known as safener for corn, "MG 838" (CAS Reg. No. 33993-74-5)
(2-propenyl 1-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8), "Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). S14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B.  (2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfone" (O, O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7) , "Dietholate" (O, O-diethyl-O-phenyl phosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9). S14) active substances, in addition to a herbicidal activity against harmful plants and safener action on crop plants such as rice, such as. B.
"Dimepiperate" oder "MY 93" (S-1-Methyl-1-phenylethyl-piperidin-1-carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Daimuron" oder "SK 23" (1-(1-Methyl-1-phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Cumyluron" = "JC 940" (3-(2-Chlorphenylmethyl)-1-(1-methyl-1-phenyl-ethyl)harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (1-Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr.54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. S15) Verbindungen der Formel (S15) oder deren Tautomere wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind worin R 1"Dimepiperate" or "MY 93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide Molinate, "daimuron" or "SK 23" (1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea) known as safener for rice against damage of the herbicide imazosulfuron, "cumyluron" = "JC 940" (3- (2-chlorophenylmethyl) -1 - (1-methyl-1-phenyl-ethyl) urea, see JP-A-60087254) known as safener for rice against damage of some herbicides, "methoxyphenone" or "NK 049"(3,3'-dimethyl) 4-methoxy-benzophenone) known as a safener for rice against damage of some herbicides, "COD" (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 5,409,091-06-4) , which is known as safener against damage of some herbicides in rice. S15) compounds of the formula (S15) or their tautomers as described in WO-A-2008/131861 and WO-A-2008/131860 wherein R 1
H einen (C1-C6)Haloalkylrest bedeutet und R 2H is a (C 1 -C 6 ) haloalkyl radical and R 2
H Wasserstoff oder Halogen bedeutet und R 3 H is hydrogen or halogen and R 3
H , R 4 H, R 4
H unabhängig voneinander Wasserstoff, (C1-C16)Alkyl, (C2-C16)Alkenyl oder (C2-C16)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylamino, Di[(C1-C4)alkyl]-amino, [(C1-C4)Alkoxy]- carbonyl, [(C1-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylamino, Di[(C1- C4)alkyl]-amino, [(C1-C4)Alkoxy]-carbonyl, [(C1-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, bedeutet oder R 3H is independently hydrogen, (C 1 -C 16 ) alkyl, (C 2 -C 16 ) alkenyl or (C 2 -C 16 ) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, Hydroxy, cyano, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylamino, di [(C 1 -C 4 ) alkyl ] -amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or is substituted, and heterocyclyl which is unsubstituted or substituted, or (C 3 -C 6 ) cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl which is on one side of the ring with a 4 to 6 membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 ) cycloalkenyl fused on one side of the ring with a 4 to 6 membered saturated or unsaturated carbocyclic ring, each of the latter n 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, C4) alkylthio, (C1-C4) alkylamino, di [(C1-C4) alkyl] amino, [(C1-C4) alkoxy] carbonyl, [(C1-C4) haloalkoxy] carbonyl, (C3-C6) Cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or R 3
H (C1-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und R 4H (C 1 -C 4) alkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4) haloalkoxy and R 4
H Wasserstoff oder (C1-C4)-Alkyl bedeutet oder R 3 4 H is hydrogen or (C 1 -C 4) -alkyl or R 3 4
H und RH zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen  H and RH, together with the directly attached N atom, form a four- to eight-membered atom
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (C1- C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy und (C1-C4)Alkylthio substituiert ist, bedeutet. S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z.B. (2,4-Dichlorphenoxy)essigsäure (2,4-D),  heterocyclic ring which, in addition to the nitrogen atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-4) C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy and (C1-C4) alkylthio substituted. S16) active substances which are used primarily as herbicides, but also have safener action on crop plants, e.g. (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure,  (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),  (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB),  4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA),  (4-chloro-o-tolyloxy) acetic acid (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure,  4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure,  4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),  3,6-dichloro-2-methoxybenzoic acid (Dicamba),
1-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl).  1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).
Bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen- ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, besonders bevorzugt sind: Preferred safeners are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, particular preference is given to:
Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl. Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z. B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl. For use, the formulations present in commercially available form are optionally diluted in a customary manner, for. As in wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der allgemeinen Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z. B. zwischen 0,001 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 5 kg/ha. Die vorliegende Erfindung wird anhand der nachfolgenden Beispiele näher erläutert, welche die Erfindung jedoch keinesfalls beschränken. Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use. With the external conditions such as temperature, humidity, the nature of the herbicide used, inter alia, the required application rate of the compounds of the general formula (I) varies. 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. The present invention will be explained in more detail with reference to the following examples which the However, in no way limit the invention.
A. Synthesebeispiele N-[(1R)-indan-1-yl]-4-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin (Bspl. I-369) Zu einer Lösung von 0.050 g (0.18 mmol) N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1- b][1,3]thiazepin-2-amin in 5 ml Essigsäure gab man 0.02 ml (0.18 mmol) Wasserstofperoxid und katalytischen Mengen an Natriumwolframat und rührte über Nacht bei Raumtemperatur. Das A. Synthesis Examples N - [(1R) -indan-1-yl] -4-oxo-5,6,7,8-tetrahydro [1,2,4] triazolo [5,1-b] [1,3 ] thiazepin-2-amine (Bspl I-369) To a solution of 0.050 g (0.18 mmol) of N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro- [1, 2,4] triazolo [5,1-b] [1,3] thiazepine-2-amine in 5 ml of acetic acid was added 0.02 ml (0.18 mmol) of hydrogen peroxide and catalytic amounts of sodium tungstate and stirred overnight at room temperature. The
Reaktionsgemisch wurde ohne weitere Aufreinigung unter vermidertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Acetonitril/Wasser) wurde N-[(1R)-indan-1-yl]-4-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin 0.015 g, 28 % der Theorie) als Feststoff isoliert. N-[(1R)-indan-1-yl]-4,4-dioxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin (Bspl. I- 364) Zu einer Lösung von 0.050 g (0.18 mmol) N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1- b][1,3]thiazepin-2-amin in 5 ml Essigsäure gab man 0.04 ml (0.36 mmol) Wasserstofperoxid und katalytischen Mengen an Natriumwolframat und rührte über Nacht bei Raumtemperatur. Das The reaction mixture was concentrated under reduced pressure without further purification. Purification by column chromatography of the obtained crude product (gradient acetonitrile / water) gave N - [(1R) -indan-1-yl] -4-oxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [ 5,1-b] [1,3] thiazepine-2-amine 0.015 g, 28% of theory) as a solid. N - [(1R) -indan-1-yl] -4,4-dioxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepin-2-amine (Comp. I-364) To a solution of 0.050 g (0.18 mmol) of N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro- [1,2 , 4] Triazolo [5,1-b] [1,3] thiazepine-2-amine in 5 ml of acetic acid was added 0.04 ml (0.36 mmol) of hydrogen peroxide and catalytic amounts of sodium tungstate and stirred overnight at room temperature. The
Reaktionsgemisch wurde ohne weitere Aufreinigung unter vermidertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Acetonitril/Wasser) wurde N-[(1R)-indan-1-yl]-4,4-dioxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin 0.026 g, 47 % der Theorie) als Feststoff isoliert. N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin (Bspl. I-352) Zu einer Lösung unter Argon von 0.3 g (1.28 mmol) 2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1- b][1,3]thiazepin und 0.25 g (1.92 mmol) (1R)-indan-1-amine in 5 ml trockenem 1,4-dioxane gab man 0.13 g (0.25 mmol) BrettPhos, 0.16 g (0.12 mmol) 3G BrettPhos precatalyst und 0.30 g (3.2 mmol) Natriumtertbutylat. Das resultierende Reaktionsgemisch wurde danach in einem Mikrowellengerät 1.5 h lang bei einer Temperatur von 120 °C gerührt und nach dem Abkühlen auf Raumtemperatur unter vermindertem Druck eingeengt. Der resultierende Rückstand wurde mit Dichlormethan aufgenommen, mit Wasser versetzt, und die Wasserphase wurde mehrfach gründlich mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden mit ges. Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurde N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro- [1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin 0.19 g (52 % der Theorie) als Feststoff isoliert. 2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin The reaction mixture was concentrated under reduced pressure without further purification. Purification by column chromatography of the obtained crude product (gradient acetonitrile / water) gave N - [(1R) -indan-1-yl] -4,4-dioxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepin-2-amine 0.026 g, 47% of theory) as a solid. N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro [1,2,4] triazolo [5,1-b] [1,3] thiazepine-2-amine ( Bspl. I-352) to a solution under argon of 0.3 g (1.28 mmol) of 2-bromo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1, 3] thiazepine and 0.25 g (1.92 mmol) of (1R) -indan-1-amine in 5 ml of dry 1,4-dioxane were added 0.13 g (0.25 mmol) of BrettPhos, 0.16 g (0.12 mmol) of 3G BrettPhos precatalyst and 0.30 g (3.2 mmol) sodium tert-butylate. The resulting reaction mixture was then stirred in a microwave oven for 1.5 hours at a temperature of 120 ° C and concentrated after cooling to room temperature under reduced pressure. The resulting residue was taken up with dichloromethane, water added, and the water phase was extracted several times thoroughly with dichloromethane. The combined organic phases were washed with sat. Sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. By column chromatography of the obtained crude product (gradient ethyl acetate / heptane) was N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1 , 3] thiazepine-2-amine 0.19 g (52% of theory) as a solid isolated. 2-bromo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepine
8 g (46.9 mmol) 2-amino-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin, 11.5 g 8 g (46.9 mmol) of 2-amino-5,6,7,8-tetrahydro [1,2,4] triazolo [5,1-b] [1,3] thiazepine, 11.5 g
Kupfer(II)bromid (51.6 mmol) und 10.7 g (93.9 mmol) Tert-Butylnitrit wurden in 50 ml Acetonitril 2 h bei 90°C erhitzt. Das Reaktionsgemisch wurde ohne weitere Aufreinigung unter vermidertem Druck eingeengt. Der resultierende Rückstand wurde mit Dichlormethan aufgenommen, mit 150 ml 2N NaOH gewaschen, und die Wasserphase wurde mehrfach gründlich mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden mit ges. Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurde 2-bromo-5,6,7,8-tetrahydro- [1,2,4]triazolo[5,1-b][1,3]thiazepin 1.7 g (15% der Theorie) als Öl isoliert. N-[(1R)-indan-1-yl]-4-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin (Bspl. I-369) Zu einer Lösung von 0.050 g (0.18 mmol) N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1- b][1,3]thiazepin-2-amin in 5 ml Essigsäure gab man 0.02 ml (0.18 mmol) Wasserstofperoxid und katalytischen Mengen an Natriumwolframat und rührte über Nacht bei Raumtemperatur. Das Copper (II) bromide (51.6 mmol) and 10.7 g (93.9 mmol) of tert-butylnitrite were heated in 50 ml of acetonitrile at 90 ° C for 2 h. The reaction mixture was concentrated under reduced pressure without further purification. The resulting residue was taken up in dichloromethane, washed with 150 ml of 2N NaOH, and the water phase was extracted several times thoroughly with dichloromethane. The combined organic phases were washed with sat. Sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) was 2-bromo-5,6,7,8-tetrahydro [1,2,4] triazolo [5,1-b] [1,3] thiazepine 1.7 g (15% of theory) isolated as oil. N - [(1R) -indan-1-yl] -4-oxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepin- 2-amine (Comp. I-369) To a solution of 0.050 g (0.18 mmol) of N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro- [1,2,4 ] triazolo [5,1-b] [1,3] thiazepine-2-amine in 5 ml of acetic acid were added 0.02 ml (0.18 mmol) of hydrogen peroxide and catalytic amounts of sodium tungstate and stirred overnight at room temperature. The
Reaktionsgemisch wurde ohne weitere Aufreinigung unter vermidertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Acetonitril/Wasser) wurde N-[(1R)-indan-1-yl]-4-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin 0.015 g, 28 % der Theorie) als Feststoff isoliert. N-[(1R)-indan-1-yl]-4,4-dioxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin (Bspl. I- 364) The reaction mixture was concentrated under reduced pressure without further purification. Purification by column chromatography of the obtained crude product (gradient acetonitrile / water) gave N - [(1R) -indan-1-yl] -4-oxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [ 5,1-b] [1,3] thiazepine-2-amine 0.015 g, 28% of theory) as a solid. N - [(1R) -indan-1-yl] -4,4-dioxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepine-2-amine (Comp. I-364)
Zu einer Lösung von 0.050 g (0.18 mmol) N-[(1R)-indan-1-yl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1- b][1,3]thiazepin-2-amin in 5 ml Essigsäure gab man 0.04 ml (0.36 mmol) Wasserstofperoxid und katalytischen Mengen an Natriumwolframat und rührte über Nacht bei Raumtemperatur. Das To a solution of 0.050 g (0.18 mmol) of N - [(1R) -indan-1-yl] -5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] 1.3] thiazepine-2-amine in 5 ml of acetic acid was added 0.04 ml (0.36 mmol) of hydrogen peroxide and catalytic amounts of sodium tungstate and stirred overnight at room temperature. The
Reaktionsgemisch wurde ohne weitere Aufreinigung unter vermidertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Acetonitril/Wasser) wurde N-[(1R)-indan-1-yl]-4,4-dioxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b][1,3]thiazepin-2-amin 0.026 g, 47 % der Theorie) als Feststoff isoliert. NMR-Daten ausgewählter Beispiele NMR-Peak-Listenverfahren Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der ^-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die ^-Wert– Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispieles hat daher die Form: ^1 (Intensität )The reaction mixture was concentrated under reduced pressure without further purification. Purification by column chromatography of the obtained crude product (gradient acetonitrile / water) gave N - [(1R) -indan-1-yl] -4,4-dioxo-5,6,7,8-tetrahydro- [1,2,4] triazolo [5,1-b] [1,3] thiazepin-2-amine 0.026 g, 47% of theory) as a solid. NMR data of selected examples NMR peak list method The 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak first the ^ value in ppm and then the signal intensity in parentheses is listed. The ^ value signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form: ^ 1 (intensity)
1 ; ^2 (Intensität2);……..; ^i (Intensität) 1 ; ^ 2 (intensity2); ...... ..; ^ i (intensity)
i ;……; ^n (Intensitätn) Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige  i; ......; The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum. To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, like classical 1H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities. When indicating compound signals in the delta range of solvents and / or water, our lists of 1H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a high intensity. The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%). Such stereoisomers and / or impurities may be typical of each
Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Be manufacturing process. Their peaks can thus help the reproduction of our
Herstellungsverfahrens anhand von“Nebenprodukt-Fingerabdrücken” zu erkennen. Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Detect manufacturing process by "by-product fingerprints". An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation. Further details on 1H NMR peaks can be found in Research Disclosure Database Number 564025.
B. Formulierungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 B. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as inert material and comminuting in a hammer mill. b) A water-dispersible, wettable powder is obtained by 25
Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil Parts by weight of a compound of the formula (I) and / or salts thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight
oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Mix oleoylmethyl tauric acid sodium as wetting and dispersing agent and mill in a pin mill. c) A dispersion concentrate which is readily dispersible in water is obtained by reacting 20
Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight
Alkylphenolpolyglykolether (®Triton X 207), 3 Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca.255 bis über 277° C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen Alkylphenolpolyglykolether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 ° C) mixed and in a ball mill to a fineness of less than 5 microns married. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight
oxethyliertes Nonylphenol als Emulgator. e) Ein in Wasser dispergierbares Granulat wird erhalten indem man 75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 10 Gew.-Teile ligninsulfonsaures Calcium, 5 Gew.-Teile Natriumlaurylsulfat, 3 Gew.-Teile Polyvinylalkohol und 7 Gew.-Teile Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man 25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium 2 Gew.-Teile oleoylmethyltaurinsaures Natrium, 1 Gew.-Teil Polyvinylalkohol, 17 Gew.-Teile Calciumcarbonat und 50 Gew.-Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. ethoxylated nonylphenol as emulsifier. e) A water-dispersible granules are obtained by reacting 75 parts by weight of a compound of formula (I) and / or salts thereof, 10 parts by weight calcium lignosulfonate, 5 parts by weight sodium lauryl sulfate, 3 parts by weight polyvinyl alcohol and 7 parts by weight of kaolin mixed, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as granulating. f) A water-dispersible granule is also obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium 2 parts by weight of oleoylmethyltaurine acid, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water on a colloid mill homogenized and pre-crushed, then ground on a bead mill and the suspension thus obtained in a spray tower by means of a single-fluid nozzle atomized and dried.
C. Biologische Beispiele C.1 Herbizide Wirkung und Kulturverträglichkeit im Vorauflauf C. Biological Examples C.1 Herbicidal action and pre-emergence culture compatibility
Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen werden in Kunststoff- oder organischen Pflanztöpfen ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca.3 Wochen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Seeds of monocotyledonous or dicotyledonous weeds and crops are laid out in plastic or organic plant pots and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a water application rate of 600 l / ha. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. After approx. 3 weeks, the effect of the preparations is scored visually in comparison with untreated controls in percentage values. For example, 100% means action = plants are dead, 0% effect = like control plants.
In den nachfolgenden Tabellen werden folgende Abkürzungen verwendet: Unerwünschte Pflanzen / Weeds: ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides The following abbreviations are used in the following tables: Undesirable plants / Weeds: ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides
AMARE: Amaranthus retroflexus AVEFA: Avena fatua AMARE: Amaranthus retroflexus AVEFA: Avena fatua
CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli
LOLMU: Lolium multiflorum MATIN: Matricaria inodora LOLMU: Lolium multiflorum MATIN: Matricaria inodora
PHBPU: Ipomoea purpurea POLCO: Polygonum convolvulus PHBPU: Ipomoea purpurea POLCO: Polygonum convolvulus
SETVI: Setaria viridis STEME: Stellaria media SETVI: Setaria viridis STEMS: Stellaria media
VERPE: Veronica persica VIOTR: Viola tricolor Tabelle B1: Herbizide Wirksamkeit im Vorauflauf VERPE: Veronica persica VIOTR: Viola tricolor Table B1: Pre-emergence herbicidal activity
Tabelle B2: Herbizide Wirksamkeit im Vorauflauf Table B2: Pre-emergence herbicidal activity
Tabelle B3: Herbizide Wirksamkeit im Vorauflauf Table B3: Pre-emergence herbicidal activity
Wie die Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen, wie beispielsweise die As the results show, compounds of the invention, such as the
Verbindungen Nr. I-231, I-199 und andere Verbindungen aus der Tabelle B1 , bei Behandlung im Vorauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf. Beispielsweise haben dabei die Verbindungen Nr. I-214 und I-196 im Vorauflaufverfahren eine sehr gute Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica und Viola tricolor bei einer Aufwandmenge von 0.32 kg Aktivsubstanz oder weniger pro Hektar. Gleichzeitig lassen einige erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais Reis oder Zuckerrohr im Compounds Nos. I-231, I-199 and other compounds from Table B1, when treated pre-emergence a good herbicidal activity against harmful plants on. For example, the compounds Nos. I-214 and I-196 have a very good effect (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor at a rate of 0.32 kg Active ingredient or less per hectare. At the same time, some of the compounds of the invention leave graminaceous crops such as barley, wheat, rye, millet, corn rice or sugarcane
Vorauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps oder Zuckerrüben. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Vorauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Pre-emergence even with high doses of active ingredient virtually undamaged. In addition, some substances also protect dicotyledonous crops such as soya, cotton, oilseed rape or sugar beets. Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops.
C.2 Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Kunststoff- oder organischen Pflanztöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen.2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die grünen Pflanzenteile gesprüht. Nach ca.3 Wochen Standzeit der C.2 Herbicidal activity and postharvest culture Seeds of monocotyledonous or dicotyledonous weed or crop plants are placed in sandy or loamy soil in plastic or organic planters, covered with soil and grown in the greenhouse under controlled growing conditions.2 to 3 weeks after harvest Sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% of additive at a rate of 600 l / ha. After approx. 3 weeks service life of the
Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Test plants in the greenhouse, under optimal growth conditions, the effect of the preparations is scored visually compared to untreated controls. For example, 100% means action = plants are dead, 0% effect = like control plants.
Tabelle B4: Herbizide Wirksamkeit im Nachauflauf Table B4: Post-emergence herbicidal activity
Tabelle B5: Herbizide Wirksamkeit im Nachauflauf Table B5: Post-emergence herbicidal activity
Tabelle B6: Herbizide Wirksamkeit im Nachauflauf Table B6: Post-emergence herbicidal activity
Tabelle B7: Herbizide Wirksamkeit im Nachauflauf Table B7: Post-emergence herbicidal activity
Wie die Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen, wie beispielsweise die As the results show, compounds of the invention, such as the
Verbindungen Nr. I-248, I-353 und I-231 und andere Verbindungen aus der Tabelle B5 bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf. Beispielsweise haben dabei die Verbindungen Nr. I-377 und I-214 im Nachauflaufverfahren eine sehr gute herbizide Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Abutilon theophrasti, Amaranthus retroflexus, Setaria viridis, und Veronica persica bei einer Aufwandmenge von 0.32 kg Aktivsubstanz oder weniger pro Hektar. Gleichzeitig lassen einige erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais, Reis oder Zuckerrohr im Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps, oder Zuckerrüben. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Nachauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Compounds Nos. I-248, I-353 and I-231 and other compounds from Table B5 have a good herbicidal activity against harmful plants during postemergence treatment. For example, the compounds No. I-377 and I-214 postemergence have a very good herbicidal action (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Setaria viridis, and Veronica persica at an application rate of 0.32 kg of active substance or less per hectare. At the same time, some of the compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize, rice or sugarcane practically unimpaired postemergence even at high doses of active ingredient. In addition, some substances also protect dicotyledonous crops such as soybeans, cotton, oilseed rape, or sugarbeet. Some of the compounds according to the invention show a high selectivity and are therefore suitable postemergence for combating undesired plant growth in agricultural crops.

Claims

Patentansprüche claims
1. Verbindungen der allgemeinen Formel (I) 1. Compounds of the general formula (I)
und deren agrochemisch verträglichen Salze, in welchen R1 ausgewählt ist aus der Gruppe, bestehend aus  and their agrochemically acceptable salts in which R1 is selected from the group consisting of
- Wasserstoff, Halogen, Hydroxy, Cyano, Nitro, Amino, C(O)OH, C(O)NH2; - hydrogen, halogen, hydroxy, cyano, nitro, amino, C (O) OH, C (O) NH 2 ;
- (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Haloalkylcar- bonyl, (C1-C6)-Alkylcarbonyloxy, (C1-C6)-Halogenalkylcarbonyloxy, (C1-C6)- Alkylcarbonyl-(C1-C4)-alkyl; (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -haloalkylcarbonyl, (C 1 -C 6 ) -Alkylcarbonyloxy, (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 4 ) -alkyl;
- (C1-C6)-Alkoxy, (C1-C4)-Alkoxyalkyl, (C1-C6)-Halogenalkoxy, (C1-C6)- Alkoxycarbonyl, (C1-C6)-Haloalkoxycarbonyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)- halogenalkyl, (C1-C6)-Halogenalkoxycarbonyl-(C1-C6)-halogenalkyl; - (C 1 -C 6 ) -alkoxy, (C 1 -C 4 ) -alkoxyalkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -haloalkoxycarbonyl , (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) - haloalkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -haloalkyl;
- (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkenylcarbonyl, (C2-C6)-Haloalke- nylcarbonyl, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alke- nyloxycarbonyl, (C2-C6)-Haloalkenyloxycarbonyl; (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -alkenylcarbonyl, (C 2 -C 6 ) -haloalkenylcarbonyl, (C 2 -C 6 ) Alkenyloxy, (C 2 -C 6 ) haloalkenyloxy, (C 2 -C 6 ) alkenyloxycarbonyl, (C 2 -C 6 ) haloalkenyloxycarbonyl;
- (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyloxy- carbonyl, (C2-C6)-Halogenalkinyloxycarbonyl; - (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 2 -C 6 ) -alkynylcarbonyl, (C 2 -C 6 ) -haloalkinylcarbonyl, (C 2 -C 6 ) -alkynyloxy , (C 2 -C 6) -haloalkynyloxy, (C 2 -C 6) -alkynyloxycarbonyl, (C 2 -C 6) -haloalkynyloxycarbonyl;
- Tri-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Di-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Mono- (C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Phenylsilyl-(C2-C6)-alkinyl;  Tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, di (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, mono (C 1 -C 6) alkylsilyl (C 2 -C 4) alkyl) C6) alkynyl, phenylsilyl (C2-C6) alkynyl;
- (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)-Arylcarbonyl und (C6-C14)-Aryloxycarbonyl, welche jeweils am Arylteil mit Halogen, (C1-C6)-Alkyl und/oder (C1-C6)-Haloalkyl substituiert sein können;  - (C6-C14) -aryl, (C6-C14) -aryloxy, (C6-C14) -arylcarbonyl and (C6-C14) -aryloxycarbonyl, which are each attached to the aryl portion by halogen, (C1-C6) -alkyl and / or (C1-C6) -haloalkyl may be substituted;
- (C6-C14)-Aryl-(C1-C6)-alkyl, (C6-C14)-Aryl-(C1-C6)-alkoxy, (C6-C14)-Aryl-(C1-C6)-alkyl- carbonyl, (C6-C14)-Aryl-(C1-C6)-alkyl-carbonyloxy, (C6-C14)-Aryl-(C1-C6)-alkoxycarbo- nyl, (C6-C14)-Aryl-(C1-C6)-alkoxycarbonyloxy; - Mono-((C1-C6)-alkyl)-amino, Mono-((C1-C6)-haloalkyl)-amino, Di-((C1-C6)-alkyl)- amino, Di-((C1-C6)-haloalkyl)-amino, ((C1-C6)-Alkyl-(C1-C6)-haloalkyl)-amino, N- ((C1-C6)-Alkanoyl)-amino, N-((C1-C6)-Haloalkanoyl)-amino, Aminocarbonyl-(C1-C6)- alkyl, Di-(C1-C6)-Alkylaminocarbonyl-(C1-C6)-alkyl; - (C6-C14) -aryl (C1-C6) -alkyl, (C6-C14) -aryl (C1-C6) -alkoxy, (C6-C14) -aryl (C1-C6) -alkylcarbonyl , (C6-C14) -aryl (C1-C6) -alkyl-carbonyloxy, (C6-C14) -aryl (C1-C6) -alkoxycarbonyl, (C6-C14) -aryl- (C1-C6) alkoxycarbonyloxy; Mono (- C 1 -C 6) alkyl) amino, mono (C 1 -C 6) haloalkyl) amino, di (C 1 -C 6) alkyl) amino, di (C 1 -C 6 ) -haloalkyl) -amino, ((C 1 -C 6) -alkyl- (C 1 -C 6) -haloalkyl) -amino, N- ((C 1 -C 6) -alkanoyl) -amino, N - ((C 1 -C 6) - Haloalkanoyl) amino, aminocarbonyl (C 1 -C 6) alkyl, di (C 1 -C 6) alkylaminocarbonyl (C 1 -C 6) alkyl;
- Mono-((C1-C6)-alkyl)-amino-carbonyl, Mono-((C1-C6)-haloalkyl)-amino-carbonyl, Di- ((C1-C6)-alkyl)-amino-carbonyl, Di-((C1-C6)-haloalkyl)-amino-carbonyl, ((C1-C6)- Alkyl-(C1-C6)-haloalkyl)-amino-carbonyl, N-((C1-C6)-Alkanoyl)-amino-carbonyl, N- ((C1-C6)-Haloalkanoyl)-amino-carbonyl, Mono-((C6-C14)-aryl)-amino-carbonyl, Di- ((C6-C14)-aryl)-amino-carbonyl, Mono (- (C 1 -C 6) alkyl) amino carbonyl, mono - ((C 1 -C 6) haloalkyl) amino carbonyl, di ((C 1 -C 6) alkyl) amino carbonyl, di - ((C 1 -C 6 ) -haloalkyl) -amino-carbonyl, ((C 1 -C 6 ) -alkyl- (C 1 -C 6 ) -haloalkyl) -amino-carbonyl, N - ((C 1 -C 6 ) - Alkanoyl) -amino-carbonyl, N- ((C 1 -C 6 ) -haloalkanoyl) -amino-carbonyl, mono - ((C 6 -C 14 ) -aryl) -amino-carbonyl, di- (C 6 - C 14 ) -aryl) -amino-carbonyl,
- Di-((C1-C6)-alkyl)-amino, mit der Maßgabe, dass die beiden (C1-C6)-alkyl-Reste einen Cyclus bilden, welcher gegebenenfalls durch NH, O oder S unterbrochen sein kann; - (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkoxy, (C1-C6)-Alkoxycar- bonyl-(C1-C6)-alkoxy; - Di - ((C 1 -C 6 ) -alkyl) -amino, with the proviso that the two (C 1 -C 6 ) -alkyl radicals form a cycle which may optionally be interrupted by NH, O or S. ; - (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxycar - carbonyl (C 1 -C 6 ) alkoxy;
- (C3-C8)-Cycloalkyl, welches gegebenenfalls am Cycloalkylrest durch (C1-C6)-Alkyl und/oder Halogen substituiert sein kann; (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl- (C1-C6)-alkyl, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkyl, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxy, (C3-C8)-Cycloalkylcarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyl, (C3-C8)-Cycloalkyl- (C1-C6)-haloalkylcarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxycarbonyl, (C3-C8)- Cycloalkyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-Cycloalkylcarbonyloxy, (C3-C8)- Cycloalkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)- Cycloalkyl-(C1-C6)-halogenalkylcarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy; (C5-C6)- Cycloheteroalkyl, welches gegenbenfalls einfach oder zweifach unabhängig voneinander durch NH, O oder S unterbrochen sein kann; - (C 3 -C 8 ) -cycloalkyl, which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyl, (C 3 -C 8 ) -Cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy, (C 3 -C 8 ) - Cycloalkoxycarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 3 -C 8 ) -Cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyloxy; (C 5 -C 6 ) -cycloheteroalkyl, which may be interrupted by NH, O or S independently of one another, once or twice;
- (C3-C8)-Cycloalkenyl, (C3-C8)-Cycloalkenyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-alkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkoxy, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkoxy, (C3-C8)-Cycloalkenylcarbonyl, (C3-C8)- Cycloalkenyloxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkylcarbonyl, (C3-C8)- Cycloalkenyl-(C1-C6)-halogenalkylcarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)- alkoxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)- Cycloalkenylcarbonyloxy, (C3-C8)-Cycloalkenyloxycarbonyloxy, (C3-C8)-Cycloalkenyl- (C1-C6)-alkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)- haloalkoxycarbonyloxy; (C 3 -C 8) -cycloalkenyl, (C 3 -C 8) -cycloalkenyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkyl, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkyl, ( C3-C8) -cycloalkenyl- (C1-C6) -alkoxy, (C3-C8) -cycloalkenyl- (C1-C6) -haloalkoxy, (C3-C8) -cycloalkenylcarbonyl, (C3-C8) -cycloalkenyloxycarbonyl, (C3-C8) -alkoxy C8) cycloalkenyl (C1-C6) alkylcarbonyl, (C3-C8) cycloalkenyl (C1-C6) haloalkylcarbonyl, (C3-C8) cycloalkenyl (C1-C6) alkoxycarbonyl, (C3-C8) Cycloalkenyl (C 1 -C 6) haloalkoxycarbonyl, (C 3 -C 8) cycloalkenylcarbonyloxy, (C 3 -C 8) cycloalkenyloxycarbonyloxy, (C 3 -C 8) cycloalkenyl (C 1 -C 6) alkylcarbonyloxy, (C 3 -C 8) cycloalkenyl - (C 1 -C 6) -haloalkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkoxycarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkoxycarbonyloxy;
- Hydroxy-(C1-C6)-alkyl, Hydroxy-(C1-C6)-alkoxy Cyano-(C1-C6)-alkoxy, Cyano- (C1-C6)-alkyl; - (C1-C6)-Alkylsulfonyl, (C1-C6)-Alkylthio, (C1-C6)-Alkylsulfinyl, (C1-C6)-Halo- alkylsulfonyl, (C1-C6)-Halogenalkylthio, (C1-C6)-Halogenalkylsulfinyl, (C1-C6)- Alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-Alkylsulfinyl- (C1-C6)-alkyl, (C1-C6)-Haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkylthio-(C1-C6)- alkyl, (C1-C6)-Haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-Alkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylthio-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-Haloalkylthio-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfonyloxy, (C1-C6)- Halogenalkylsulfonyloxy, (C1-C6)-Alkylthiocarbonyl, (C1-C6)-Haloalkylthiocarbonyl, (C1-C6)-Alkylthiocarbonyloxy, (C1-C6)-Haloalkylthiocarbonyloxy, (C1-C6)-Alkylthio- (C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkoxy, (C1-C6)-Alkylthio-(C1-C6)- alkylcarbonyl, (C1-C6)-Alkylthio-(C1-C6)-alkylcarbonyloxy, (C4-C14)-Arylsulfonyl, (C6-C14)-Arylthio, (C6-C14)-Arylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Alkenylthio, (C3-C8)-Cycloalkenylthio, (C3-C6)-Alkinylthio; R2 ausgewählt ist aus der Gruppe, bestehend aus - (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Haloalkylcar- bonyl, (C1-C6)-Alkylcarbonyloxy, (C1-C6)-Halogenalkylcarbonyloxy, (C1-C6)- Alkylcarbonyl-(C1-C4)-alkyl; Hydroxy (C 1 -C 6) alkyl, hydroxy (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkyl; - (C 1 -C 6) -alkylsulfonyl, (C 1 -C 6) -alkylthio, (C 1 -C 6) -alkylsulfinyl, (C 1 -C 6) -haloalkylsulfonyl, (C 1 -C 6) -haloalkylthio, (C 1 -C 6) -haloalkylsulfinyl , (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylthio (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfinyl- (C 1 -C 6) -alkyl, ( C1-C6) -haloalkylsulfonyl- (C1-C6) -alkyl, (C1-C6) -haloalkylthio (C1-C6) -alkyl, (C1-C6) -haloalkylsulfinyl- (C1-C6) -alkyl, (C1- C6) -alkylsulfonyl- (C1-C6) -haloalkyl, (C1-C6) -alkylthio (C1-C6) -haloalkyl, (C1-C6) -alkylsulfinyl- (C1-C6) -haloalkyl, (C1-C6) Haloalkylsulfonyl- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkylsulfinyl- (C 1 -C 6 ) haloalkyl, (C 1 -C 6) alkylsulfonyloxy, (C 1 -C 6) - haloalkylsulfonyloxy, (C 1 -C 6) -alkylthiocarbonyl, (C 1 -C 6) -Haloalkylthiocarbonyl, (C 1 -C 6) Alkylthiocarbonyloxy, (C 1 -C 6 ) -haloalkylthiocarbonyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkylcarbonyloxy, (C 4 -C 14 ) arylsulfonyl, (C 6 -C 14 ) arylthio, (C 6 -C 14 ) arylsulfinyl, (C 3 -C 8 ) -cycloalkylthio, (C 3 -C 8 ) -alkenylthio, (C 3 -C 8 ) -cycloalkenylthio, (C 3 -C 6 ) -alkynylthio; R 2 is selected from the group consisting of - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -haloalkylcarbonyl, (C 1 -C 6 ) -Alkylcarbonyloxy, (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 1 -C 6 ) -alkylcarbonyl (C 1 -C 4 ) -alkyl;
- (C1-C6)-Alkoxy, (C1-C6)-Halogenalkoxy, (C1-C6)-Alkoxycarbonyl, (C1-C6)-Haloalk- oxycarbonyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkoxycarbonyl- (C1-C6)-alkyl, (C1-C6)-Alkoxycarbonyl-(C1-C6)-halogenalkyl, (C1-C6)-Ha- logenalkoxycarbonyl-(C1-C6)-halogenalkyl; - (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -haloalkoxycarbonyl, (C 1 -C 6 ) Alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxycarbonyl- (C 1 -C 6 ) -haloalkyl;
- (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkenylcarbonyl, (C2-C6)-Haloal- kenylcarbonyl, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alke- nyloxycarbonyl, (C2-C6)-Haloalkenyloxycarbonyl;  - (C 2 -C 6) alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -alkenylcarbonyl, (C 2 -C 6) -haloalkenylcarbonyl, (C 2 -C 6) -alkenyloxy, (C 2 -C 6) -haloalkenyloxy , (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -haloalkenyloxycarbonyl;
- (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyloxy- carbonyl, (C2-C6)-Halogenalkinyloxycarbonyl;  - (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 2 -C 6) -alkynylcarbonyl, (C 2 -C 6) -haloalkynylcarbonyl, (C 2 -C 6) -alkynyloxy, (C 2 -C 6) -haloalkynyloxy , (C 2 -C 6) -alkynyloxycarbonyl, (C 2 -C 6) -haloalkynyloxycarbonyl;
- Tri-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Di-(C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Mono- (C1-C6)-alkylsilyl-(C2-C6)-alkinyl, Phenylsilyl-(C2-C6)-alkinyl;  Tri (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, di (C 1 -C 6) alkylsilyl (C 2 -C 6) alkynyl, mono (C 1 -C 6) alkylsilyl (C 2 -C 4) alkyl) C6) alkynyl, phenylsilyl (C2-C6) alkynyl;
- (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)-Arylcarbonyl und (C6-C14)-Aryloxycarbo- nyl, welche jeweils am Arylteil mit Halogen, (C1-C6)-Alkyl und/oder (C1-C6)- Haloalkyl substituiert sein können; - (C6-C14)-Aryl-(C1-C6)-alkyl, (C6-C14)-Aryl-(C1-C6)-alkoxy, (C6-C14)-Aryl-(C1-C6)- alkyl-carbonyl, (C6-C14)-Aryl-(C1-C6)-alkyl-carbonyloxy, (C6-C14)-Aryl-(C1-C6)- alkoxycarbonyl, (C6-C14)-Aryl-(C1-C6)-alkoxycarbonyloxy; - (C6-C14) -aryl, (C6-C14) -aryloxy, (C6-C14) -arylcarbonyl and (C6-C14) -aryloxycarbonyl, which are each attached to the aryl moiety with halogen, (C1-C6) -alkyl and / or (C1-C6) - haloalkyl may be substituted; - (C6-C14) -aryl (C1-C6) -alkyl, (C6-C14) -aryl (C1-C6) -alkoxy, (C6-C14) -aryl (C1-C6) -alkyl-carbonyl , (C6-C14) aryl- (C1-C6) -alkyl-carbonyloxy, (C6-C14) -aryl (C1-C6) -alkoxycarbonyl, (C6-C14) -aryl (C1-C6) -alkoxycarbonyloxy ;
- Mono-((C1-C6)-alkyl)-amino, Mono-((C1-C6)-haloalkyl)-amino, Di-((C1-C6)-alkyl)- amino, Di-((C1-C6)-haloalkyl)-amino, ((C1-C6)-Alkyl-(C1-C6)-haloalkyl)-amino, N- ((C1-C6)-Alkanoyl)-amino, N-((C1-C6)-Haloalkanoyl)-amino, Aminocarbonyl- (C1-C6)-alkyl, Di-(C1-C6)-Alkylaminocarbonyl-(C1-C6)-alkyl; Mono (- C 1 -C 6) alkyl) amino, mono (C 1 -C 6) haloalkyl) amino, di (C 1 -C 6) alkyl) amino, di (C 1 -C 6 ) -haloalkyl) -amino, ((C 1 -C 6) -alkyl- (C 1 -C 6) -haloalkyl) -amino, N- ((C 1 -C 6) -alkanoyl) -amino, N - ((C 1 -C 6) - Haloalkanoyl) amino, aminocarbonyl (C 1 -C 6 ) alkyl, di (C 1 -C 6 ) alkylaminocarbonyl (C 1 -C 6 ) alkyl;
- Mono-((C1-C6)-alkyl)-amino-carbonyl, Mono-((C1-C6)-haloalkyl)-amino-carbonyl, Di-((C1-C6)-alkyl)-amino-carbonyl, Di-((C1-C6)-haloalkyl)-amino-carbonyl, ((C1-C6)-Alkyl-(C1-C6)-haloalkyl)-amino-carbonyl, N-((C1-C6)-Alkanoyl)-amino- carbonyl, N-((C1-C6)-Haloalkanoyl)-amino-carbonyl, Mono-((C6-C14)-aryl)-amino- carbonyl, Di-((C6-C14)-aryl)-amino-carbonyl, Mono (C 1 -C 6 ) alkyl) amino carbonyl, mono (C 1 -C 6 ) haloalkyl) amino carbonyl, di (C 1 -C 6 ) alkyl) -amino-carbonyl, di - ((C 1 -C 6 ) -haloalkyl) -amino-carbonyl, ((C 1 -C 6 ) -alkyl- (C 1 -C 6 ) -haloalkyl) -amino-carbonyl, N - ((C 1 -C 6 ) alkanoyl) -aminocarbonyl, N - ((C 1 -C 6 ) -haloalkanoyl) -amino-carbonyl, mono - ((C 6 -C 14 ) -aryl) -amino carbonyl, di (C 6 -C 14 ) aryl) amino carbonyl,
- (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkoxy, (C1-C6)-Alkoxycar- bonyl-(C1-C6)-alkoxy; - (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxycar - carbonyl (C 1 -C 6 ) alkoxy;
- (C3-C8)-Cycloalkyl, welches gegebenenfalls am Cycloalkylrest durch (C1-C6)-Alkyl und/oder Halogen substituiert sein kann; (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl- (C1-C6)-alkyl, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkyl, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxy, (C3-C8)-Cycloalkylcarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyl, (C3-C8)- Cycloalkyl-(C1-C6)-haloalkylcarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-alkoxycarbonyl, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-Cycloalkylcarbonyloxy, (C3-C8)-Cycloalkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-halogenalkylcarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)- alkoxycarbonyloxy, (C3-C8)-Cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy; - (C 3 -C 8 ) -cycloalkyl, which may optionally be substituted on the cycloalkyl radical by (C 1 -C 6 ) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8) ) -Cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyl, (C 3 -C 8 ) -Cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyloxy, (C 3 -C 8 ) -Cycloalkoxycarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkylcarbonyloxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkylcarbonyloxy, (C 3 -C 8 ) -Cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyloxy, (C 3 -C 8) -cycloalkyl- (C 1 -C 6 ) -haloalkoxycarbonyloxy;
- (C3-C8)-Cycloalkenyl, (C3-C8)-Cycloalkenyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)- alkyl, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkyl, (C3-C8)-Cycloalkenyl-(C1-C6)- alkoxy, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkoxy, (C3-C8)-Cycloalkenylcarbonyl, (C3-C8)-Cycloalkenyloxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-alkylcarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-halogenalkylcarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)- alkoxycarbonyl, (C3-C8)-Cycloalkenyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)- Cycloalkenylcarbonyloxy, (C3-C8)-Cycloalkenyloxycarbonyloxy, (C3-C8)- Cycloalkenyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)- halogenalkylcarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-Cycloalkenyl-(C1-C6)-haloalkoxycarbonyloxy; (C 3 -C 8) -cycloalkenyl, (C 3 -C 8) -cycloalkenyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkyl, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkyl, ( C3-C8) -cycloalkenyl- (C1-C6) -alkoxy, (C3-C8) -cycloalkenyl- (C1-C6) -haloalkoxy, (C3-C8) -cycloalkenylcarbonyl, (C3-C8) -cycloalkenyloxycarbonyl, (C3-C8) -cycloalkenylcarbonyl C8) cycloalkenyl (C1-C6) alkylcarbonyl, (C3-C8) cycloalkenyl (C1-C6) haloalkylcarbonyl, (C3-C8) cycloalkenyl (C1-C6) alkoxycarbonyl, (C3-C8) Cycloalkenyl (C 1 -C 6) haloalkoxycarbonyl, (C 3 -C 8) cycloalkenylcarbonyloxy, (C 3 -C 8) cycloalkenyloxycarbonyloxy, (C 3 -C 8) cycloalkenyl (C 1 -C 6) alkylcarbonyloxy, (C 3 -C 8) cycloalkenyl - (C 1 -C 6) - haloalkylcarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -alkoxycarbonyloxy, (C 3 -C 8) -cycloalkenyl- (C 1 -C 6) -haloalkoxycarbonyloxy;
- Hydroxy-(C1-C6)-alkyl, Hydroxy-(C1-C6)-alkoxy Cyano-(C1-C6)-alkoxy, Cyano- (C1-C6)-alkyl; Hydroxy (C 1 -C 6) alkyl, hydroxy (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkoxy, cyano (C 1 -C 6) alkyl;
- (C1-C6)-Alkylsulfonyl, (C1-C6)-Alkylthio, (C1-C6)-Alkylsulfinyl, (C1-C6)-Halo- alkylsulfonyl, (C1-C6)-Halogenalkylthio, (C1-C6)-Halogenalkylsulfinyl, (C1-C6)- Alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-Alkylsulfinyl- (C1-C6)-alkyl, (C1-C6)-Haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-Haloalkylthio- (C1-C6)-alkyl, (C1-C6)-Haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-Alkylsulfonyl- (C1-C6)-haloalkyl, (C1-C6)-Alkylthio-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfinyl- (C1-C6)-haloalkyl, (C1-C6)-Haloalkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)- Haloalkylthio-(C1-C6)-haloalkyl, (C1-C6)-Haloalkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-Alkylsulfonyloxy, (C1-C6)-Halogenalkylsulfonyloxy, (C1-C6)- Alkylthiocarbonyl, (C1-C6)-Haloalkylthiocarbonyl, (C1-C6)-Alkylthiocarbonyloxy, (C1-C6)-Haloalkylthiocarbonyloxy, (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)- Alkylthio-(C1-C6)-alkoxy, (C1-C6)-Alkylthio-(C1-C6)-alkylcarbonyl, (C1-C6)- Alkylthio-(C1-C6)-alkylcarbonyloxy, (C4-C14)-Arylsulfonyl, (C6-C14)-Arylthio, (C6-C14)-Arylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Alkenylthio, (C3-C8)- Cycloalkenylthio, (C3-C6)-Alkinylthio; oder R1 und R2 zusammen mit dem Kohlenstoffatom beziehungsweise Stickstoffatom, an das sie gebunden sind, einen gesättigten fünf - bis siebengliedriegen Ring bilden, der durch die Gruppe Y unterbrochen sein kann, wobei Y ausgewählt ist aus C(O), O, S, S(O), S(O)2, NR1a, C(O)- NR1a, wobei der gesättigte fünf- bis siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, COOMe, COOEt, CONH2, Nitril, (C1-C6)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Phenylsulfonyl oder Phenyl-(C1-C6)-alkylsulfonyl substituiert sein kann, und wobei R1a ausgewählt ist aus Wasserstoff, Acetyl, Trifluoracetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkylcarbonyl, (C3-C6)-Cycloalkyl-(C1-C6)-Alkyl, (C1-C4)-Alkylsulfonyl, Phenyl, Phenyl-(C1-C6)-alkyl, Phenylcarbonyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 2- Pyridinylcarbonyl, 3-Pyridinylcarbonyl, 4-Pyridinylcarbonyl, wobei die 14 zuletzt genannten Reste mit Halogen, (C1-C6)-Alkyl, (C1-C6)-Alkyloxy, Nitril oder Trifluormethyl substiuiert sein können;, R3 Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Halogenalkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)- Haloalkylcarbonyl oder (C1-C6)-Alkylcarbonyloxy ist; R4 und R5 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Haloalkyl, (C1-C6) -alkylsulfonyl, (C1-C6) -alkylthio, (C1-C6) -alkylsulfinyl, (C1-C6) -halo alkylsulfonyl, (C 1 -C 6) -haloalkylthio, (C 1 -C 6) -haloalkylsulfinyl, (C 1 -C 6) -alkylsulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylthio (C 1 -C 6) -alkyl, (C1-C6) -alkylsulfinyl- (C1-C6) -alkyl, (C1-C6) -haloalkylsulfonyl- (C1-C6) -alkyl, (C1-C6) -haloalkylthio (C1-C6) -alkyl, (C1 -C6) -haloalkylsulfinyl- (C1-C6) -alkyl, (C1-C6) -alkylsulfonyl- (C1-C6) -haloalkyl, (C1-C6) -alkylthio (C1-C6) -haloalkyl, (C1-C6 ) -Alkylsulfinyl- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkylsulfonyl- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -haloalkyl, (C 1 -) C 6) -Haloalkylsulfinyl- (C 1 -C 6) -haloalkyl, (C 1 -C 6) alkylsulfonyloxy, (C 1 -C 6) -Halogenalkylsulfonyloxy, (C 1 -C 6) - alkylthiocarbonyl, (C 1 - C 6 ) -haloalkylthiocarbonyl, (C 1 -C 6 ) -alkylthiocarbonyloxy, (C 1 -C 6 ) -haloalkylthiocarbonyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -) C 6 ) - alkylthio (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkylthio (C 1 -) C 6 ) -alkylcarbonyloxy, (C 4 -C 14 ) -arylsulfonyl, (C 6 -C 14 ) -Ary thio, (C 6 -C 14 ) arylsulfinyl, (C 3 -C 8 ) cycloalkylthio, (C 3 -C 8 ) alkenylthio, (C 3 -C 8 ) cycloalkenylthio, (C 3 -C 6 ) - alkynylthio; or R1 and R2 together with the carbon or nitrogen atom to which they are attached form a saturated five to seven membered ring which may be interrupted by the group Y, wherein Y is selected from C (O), O, S, S (O), S (O) 2 , NR 1a, C (O) - NR 1a, wherein the saturated five- to seven-membered ring is represented by m substituents selected from halogen, acetyl, (C 1 -C 6 ) -alkyl, (C 3 -) C 6 ) -cycloalkyl, trifluoromethyl, COOMe, COOEt, CONH 2 , nitrile, (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, phenylsulfonyl or phenyl- (C 1 -C 6 ) -alkylsulfonyl R1a is selected from hydrogen, acetyl, trifluoroacetyl, (C1-C6) alkyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkylcarbonyl, (C3-C6) -cycloalkyl- (C1-C6 ) -Alkyl, (C 1 -C 4) -alkylsulfonyl, phenyl, phenyl- (C 1 -C 6) -alkyl, phenylcarbonyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyridinylcarbonyl, 3-pyridinylcarbonyl, 4-pyridinylcarbonyl, where the 14 last mentioned radicals with Halogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -alkyloxy, nitrile or trifluoromethyl; R 3 is hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) Alkylcarbonyl, (C 1 -C 6) haloalkylcarbonyl or (C 1 -C 6) alkylcarbonyloxy; R 4 and R 5 are each independently hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl,
Hydroxy, (C1-C6)-Alkoxy oder (C1-C6)-Halogenalkoxy sind; oder R4 und R5 zusammen mit dem Kohlenstoffatom, an welchem sie gebunden sind, einen Hydroxy, (C 1 -C 6) alkoxy or (C 1 -C 6) haloalkoxy; or R4 and R5 together with the carbon atom to which they are attached, a
gesättigten drei- bis siebengliedrigen Ring bilden, der ein oder mehrere Heteroatome ausgewählt aus Sauerstoff oder Schwefel oder NH oder NR1a enthalten kann; R6 und R7 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl, (C1-C6)-Haloalkyl,  form a saturated three- to seven-membered ring which may contain one or more heteroatoms selected from oxygen or sulfur or NH or NR1a; R 6 and R 7 are each independently hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl,
(C1-C6)-Alkoxy, (C1-C6)-Halogenalkoxy, (C6-C14)-Aryl, (C6-C14)-Aryloxy, (C6-C14)- Arylcarbonyl oder (C6-C14)-Aryloxycarbonyl ist ; oder R6 und R7 zusammen mit dem Kohlenstoff, an welchen sie gebunden sind, eine (C3-C7)- Alkylengruppe bilden, die ein oder mehrere Sauerstoff- und/oder Schwefelatome enthalten können, wobei die (C3-C7)-Alkylengruppe durch Halogen einfach oder mehrfach substituiert sein kann und die jeweilgen Halogensubstituenten gleich oder verschieden sein können; R8, R9, R10 und R11 jeweils unabhängig voneinander Wasserstoff, Halogen, Cyano, C(O)OH, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 6 -C 14) -aryl, (C 6 -C 14) -aryloxy, (C 6 -C 14) -arylcarbonyl or (C 6 -C 14) -aryloxycarbonyl; or R 6 and R 7 together with the carbon to which they are attached form a (C 3 -C 7 ) -alkylene group which may contain one or more oxygen and / or sulfur atoms, where the (C 3 -C 7 ) - Alkylene group may be monosubstituted or polysubstituted by halogen and the respective halogen substituents may be the same or different; R8, R9, R10 and R11 are each independently of one another hydrogen, halogen, cyano, C (O) OH,
C(O)NH2, (C1-C6)-Alkyl, (C1-C6)-Alkylcarbonyl, (C1-C6)-Alkyloxycarbonyl, (C1-C6)-Alkylaminocarbonyl, (C1-C6)-di-Alkylaminocarbonyl, (C1-C6)- Haloalkyl, (C1-C6)-Alkoxy, (C1-C6)-Halogenalkoxy, (C2-C6)-Alkenyl, (C2-C6)- Alkinyl, (C2-C6)-Halogenalkinyl, (C2-C6)-Alkinylcarbonyl, (C2-C6)-Haloal- kinylcarbonyl, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (C2-C6)-Alkinyl- oxycarbonyl, (C2-C6)-Halogenalkinyloxycarbonyl oder Nitro sind, wobei die Reste R9 und R10ringbildend durch eine -O-CH2-O- Gruppe verbunden sein können; X für eine Bindung, CH2, O, S, Carbonyl, NH, CR12R13,NR14,CH2O oder CH2S steht, wobei bei den beiden letztgenannten Gruppen das Kohlenstoffatom an den aromatischen Teil und das Heteroatom O oder S an den teilhydrierten Teil des Amins gebunden ist; wobei, wenn n = 0, X keine Bindung sein kann; R12 und R13 jeweils unabhängig voneinander Wasserstoff, (C1-C6)-Alkyl oder (C1-C6)-Haloalkyl sind; R14 Wasserstoff, (C1-C6)-Alkyl oder (C1-C6)-Haloalkyl ist; n die Laufzahl 0, 1 oder 2 ist; und m die Laufzahl 0, 1, 2, 3, 4, oder 5 ist. 2. Verbindungen der allgemeinen Formel (I) nach Anspruch 1, wobei R1Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Nitro, Trimethylsilylethinyl, Methyl, Ethyl, Propyl, Isopropyl, Butyl, tert.- Butyl, n-Pentyl, n-Heptyl, Cyclopropyl, Cyclobutyl, Acetyl, Ethinyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl, Monofluormethyl, Methoxy, Ethoxy oder Methoxymethyl ist. 3. Verbindungen der allgemeinen Formel (I) nach Anspruch 1 oder 2, wobei R1 Wasserstoff, Chlor, Phenyl, C (O) NH 2 , (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkyloxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (C 1 -C 6 ) -di-alkylaminocarbonyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 2 -C 6 ) -alkenyl, ( C 2 -C 6 ) alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 2 -C 6 ) -alkynylcarbonyl, (C 2 -C 6 ) -haloalkynylcarbonyl, (C 2 -C 6 ) -alkynyloxy, ( C 2 -C 6 ) -haloalkynyloxy, (C 2 -C 6 ) -alkynyloxycarbonyl, (C 2 -C 6 ) -haloalkynyloxycarbonyl or nitro, where the radicals R 9 and R 10 may be ring-linked by an -O-CH 2 -O- group ; X is a bond, CH 2 , O, S, carbonyl, NH, CR 12 R 13, NR 14, CH 2 O or CH 2 S, where in the latter two groups the carbon atom to the aromatic part and the heteroatom O or S to the partially hydrogenated Part of the amine is bound; where, when n = 0, X can not be a bond; Each of R 12 and R 13 is independently hydrogen, (C 1 -C 6) alkyl or (C 1 -C 6) haloalkyl; R 14 is hydrogen, (C 1 -C 6) alkyl or (C 1 -C 6) haloalkyl; n is the run number 0, 1 or 2; and m is the run number 0, 1, 2, 3, 4, or 5. 2. Compounds of general formula (I) according to claim 1, wherein R 1 is hydrogen, cyano, fluorine, Chlorine, bromine, iodine, nitro, trimethylsilylethynyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl, cyclopropyl, cyclobutyl, acetyl, ethynyl, amino, dimethylamino, trifluoromethyl, difluoromethyl, monofluoromethyl , Methoxy, ethoxy or methoxymethyl. 3. Compounds of general formula (I) according to claim 1 or 2, wherein R 1 is hydrogen, chlorine, phenyl,
2-Methylphenyl, 2-methylphenyl,
3-Trifluormethylphenyl, Methyl, Ethyl, Isopropy, Butyl, tert.-Butyl, n- Pentyl, n-Heptyl, Trifluormethyl, 1-Methylcyclopropyl, 1-(p-Xylyl)-cyclopropyl, 1-(2,4- Dichlorphenyl)-cyclopropyl, Amino, Dimethylamino, Trifluormethyl, Difluormethyl, 3-trifluoromethylphenyl, methyl, ethyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl, trifluoromethyl, 1-methylcyclopropyl, 1- (p-xylyl) -cyclopropyl, 1- (2,4-dichlorophenyl) cyclopropyl, amino, dimethylamino, trifluoromethyl, difluoromethyl,
Monofluormethyl, CHFCH3, CF(CH3)2, CHF(CH2CH3), 1-Fluorcyclopropyl, Cyclopentyl, Methoxy, Ethoxy, Methoxymethyl, Ethoxymethyl, Thiomethyl, Methylthio oder Methoxy ist. Monofluoromethyl, CHFCH 3 , CF (CH 3 ) 2 , CHF (CH 2 CH 3 ), 1-fluorocyclopropyl, cyclopentyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, thiomethyl, methylthio or methoxy.
4. Verbindungen der allgemeinen Formel (i) nach Anspruch 1 bis 3, wobei R1 und R2 zusammen mit dem Kohlenstoff beziehungsweise Stickstoffatom, an das sie gebunden sind, einen gesättigten sechs- oder siebengliedriegen Ring bilden, ausgewählt aus den folgenden Ringen (a) bis (k): 4. Compounds of the general formula (i) according to claim 1 to 3, wherein R1 and R2 together with the carbon or nitrogen atom to which they are attached form a saturated six or seven membered ring selected from the following rings (a) to (k):
(j) (k) wobei der gesättigte sechs- oder siebengliedrige Ring durch m Substituenten ausgewählt aus Halogen, Acetyl, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, Trifluormethyl, (C1-C6)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl oder Phenylsulfonyl substituiert sein kann, und wobei R1a Wasserstoff, Acetyl, (C1-C4)-Alkyl, (C1-C4)-Alkylsulfonyl oder Phenylcarbonyl, ist, und wobei das Phenyl mit einem Halogen substituiert sein kann. (j) (k) wherein the saturated six- or seven-membered ring is substituted by m substituents selected from halo, acetyl, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, trifluoromethyl, (C 1 -C 6) alkylsulfonyl, ( C3-C6) -cycloalkylsulfonyl or phenylsulfonyl, and wherein R1a is hydrogen, acetyl, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl or phenylcarbonyl, and wherein the phenyl is substituted by a halogen may be substituted.
5. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 4, wobei R3 5. Compounds of general formula (I) according to one of claims 1 to 4, wherein R3
Wasserstoff ist.  Is hydrogen.
6. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 5, wobei R4 und R5 jeweils unabhängig voneinander Wasserstoff, Methyl, Ethyl, Propyl, Cyclopropyl, Hydroxy oder Methoxy sind. 6. Compounds of general formula (I) according to any one of claims 1 to 5, wherein R4 and R5 are each independently hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy or methoxy.
7. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 6, wobei R6 und R7 unabhängig voneinander Wasserstoff, Methyl oder Phenyl sind. 7. Compounds of general formula (I) according to any one of claims 1 to 6, wherein R6 and R7 are independently hydrogen, methyl or phenyl.
8. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 7, wobei R8 8. Compounds of general formula (I) according to one of claims 1 to 7, wherein R8
Wasserstoff, Methyl oder Fluor ist.  Is hydrogen, methyl or fluorine.
9. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 8, wobei R9 9. Compounds of general formula (I) according to any one of claims 1 to 8, wherein R9
Wasserstoff oder Methyl ist.  Is hydrogen or methyl.
10. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 9, wobei R10 10. Compounds of general formula (I) according to any one of claims 1 to 9, wherein R10
Wasserstoff, Methyl, Propyl, Isopropyl, Butyl, tert.-Butyl, Dimethylamino, Fluor, Chlor, Brom, Iod, Ethenyl, Ethinyl, Methylethinyl, Ethylethinyl, MeOCH2C ^C-, Cyano, COOMe oder CONH2 ist.  Is hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluorine, chlorine, bromine, iodine, ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH2C ^ C, cyano, COOMe or CONH2.
11. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 10, wobei R11 11. Compounds of general formula (I) according to any one of claims 1 to 10, wherein R11
Wasserstoff oder Methyl ist.  Is hydrogen or methyl.
12. Verbindungen der allgemeinen Formel (I) nach einem der Ansprüche 1 bis 11, wobei X für CH2, O oder einer Bindung steht, wobei, wenn n = 0, X keine Bindung sein kann. 12. Compounds of general formula (I) according to any one of claims 1 to 11, wherein X is CH 2 , O or a bond, where, when n = 0, X can not be a bond.
13. Verbindungen der allgemeinen Formel (I) 13. Compounds of the general formula (I)
nach einem der Ansprüche 1 bis 12, wobei das chirale Kohlenstoffatom mit der Kennzeichnung (*) eine (R)-Konfiguration aufweist. according to any one of claims 1 to 12, wherein the chiral carbon atom marked (*) has an (R) -configuration.
14. Verbindungen der allgemeinen Formel (I) 14. Compounds of the general formula (I)
nach einem der Ansprüche 1 bis 12, wobei das chirale Kohlenstoffatom mit der Kennzeichnung (*) eine (R)-Konfiguration und das chirale Kohlenstoffatom mit der Kennzeichnung (**) eine (S)- Konfiguration aufweist. according to any one of claims 1 to 12, wherein the chiral carbon atom marked (*) has an (R) configuration and the chiral carbon atom labeled (**) has an (S) configuration.
15. Verfahren zur Herstellung von Verbindungen der allgemeinen Formel (I) oder deren 15. A process for the preparation of compounds of general formula (I) or their
agrochemisch verträgliche Salze: Agrochemically acceptable salts:
in welchen die Reste R1 bis R11 sowie X und die Laufzahl n gemäß Anspruch 1 definiert sind, in welchem eine Verbindung der allgemeinen Formel (II) in which the radicals R 1 to R 11 and X and the sequence number n are defined according to claim 1, in which a compound of the general formula (II)
wobei R1 und R2 gemäß Anspruch 1 definiert sind, und Z1 für einen austauschfähigen Rest oder eine Abgangsgruppe steht, mit einem Amin der allgemeinen Formel (III) wherein R1 and R2 are defined according to claim 1, and Z1 represents an exchangeable radical or a leaving group, with an amine of general formula (III)
wobei die Reste R3 bis R11 sowie X und n gemäß Anspruch 1 definiert sind, oder mit einem Säureadditionssalz des Amins der allgemeinen Formel (III) umgesetzt wird. wherein the radicals R3 to R11 and X and n are defined according to claim 1, or is reacted with an acid addition salt of the amine of the general formula (III).
16. Verfahren nach Anspruch 15, wobei Z1 Fluor, Chlor, Brom, Iod, (C1-4)-Alkylsulfanyl, (C1-4)- Alkylsulfinyl, (C1-4)-Alkylsulfonyl, ein unsubstituiertes oder ein einfach oder mehrfach mit Fluor, Chlor, Brom oder (C1-4)-Alkyl oder (C1-4)-Alkoxy substituiertes Phenyl-(C1-4)-alkylsulfonyl oder (C1-4)-Alkylphenyl-sulfonyl ist. 16. The method of claim 15, wherein Z1 is fluoro, chloro, bromo, iodo, (C 1-4 ) alkylsulfanyl, (C 1-4 ) alkylsulfinyl, (C 1-4 ) alkylsulfonyl, an unsubstituted or a mono- or phenyl (C 1-4 ) alkylsulfonyl or (C 1-4 ) alkylphenyl-sulfonyl which is multiple-membered with fluoro, chloro, bromo or (C 1-4 ) alkyl or (C 1-4 ) alkoxy.
17. Verfahren nach einem der Ansprüche 15 oder 16, wobei eine Verbindung der allgemeinen Formel (II) mit einem Amin der allgemeinen Formel (III) umgesetzt wird, wobei die Rekation durch die Reagenzien Kaliumphosphat, Kupfer(I)iodid oder N,N-Diethyl-2-hydroxybenzamid, oder im Sinne der Buchwald-Hartwig-Kupplung durch Übergangsmetallkatalysatorsysteme und Basen katalysiert wird. 17. The method according to any one of claims 15 or 16, wherein a compound of general formula (II) is reacted with an amine of general formula (III), wherein the reaction by the reagents potassium phosphate, copper (I) iodide or N, N- Diethyl 2-hydroxybenzamide, or in the sense of the Buchwald-Hartwig coupling is catalyzed by transition metal catalyst systems and bases.
18. Herbizides Mittel oder pflanzenwachstumsregulierendes Mittel, wobei es eine oder mehrere Verbindungen der allgemeinen Formel (I) oder deren Salze nach einem der Ansprüche 1 bis 14 enthält. 18. An herbicidal or plant growth-regulating agent, wherein it contains one or more compounds of the general formula (I) or salts thereof according to one of claims 1 to 14.
19. Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, wobei eine wirksame Menge von einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen nach einem der Ansprüche 1 bis 14 auf Pflanzen, Pflanzenteile, Pflanzensamen oder auf eine Anbaufläche appliziert. 19. A method for controlling harmful plants or for regulating the growth of plants, wherein an effective amount of one or more compounds of the general formula (I) or salts thereof according to any one of claims 1 to 14 applied to plants, plant parts, plant seeds or on a cultivated area.
20. Verwendung von Verbindungen der allgemeinen Formel (I) oder deren Salzen nach einem der Ansprüche 1 bis 14 als Herbizide oder als Pflanzenwachstumsregulatoren. 20. Use of compounds of general formula (I) or salts thereof according to any one of claims 1 to 14 as herbicides or as plant growth regulators.
21. Verwendung nach Anspruch 20, wobei die Verbindungen der allgemeinen Formel (I) oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen in Kulturen von Nutz- oder Zierpflanzen eingesetzt werden. 21. Use according to claim 20, wherein the compounds of the general formula (I) or salts thereof are used for controlling harmful plants or for regulating the growth of plants in crops of useful or ornamental plants.
22. Verwendung nach den Ansprüchen 20 oder 21, wobei die Kulturpflanzen transgene 22. Use according to claims 20 or 21, wherein the crop transgenic
Kulturpflanzen sind.  Are crops.
EP18807364.7A 2017-12-04 2018-11-29 3-amino-[1,2,4]-triazole derivatives and their use for controlling undesired plant growth Withdrawn EP3720853A1 (en)

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