Classifications

• • 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
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
  • A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
  • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
  • C07D241/52—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • 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
  • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • 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
  • C07D417/14—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 three or more hetero rings

Definitions

• the present invention relates to crop protection agents which contain quinoxalinone derivatives, especially 1,2-dihydroquinoxalin-2-one derivatives, as safeners and, if appropriate, pesticides, and to certain quinoxalinone derivatives and processes for their preparation.
• WO-A-99/00020 describes 3- (5-tetrazolylcarbonyl) -2-quinolinones and their use as safeners.
• DE 19621522.6 (WO-A-97/45016)
• DE 19742951.3 (WO-A-99/16744) describe N-acylsulfonamides as safeners, preferably for protecting maize plants.
• WO 2002/002550 relates to the use of aryl-condensed pyrazinones as kinase inhibitors.
• 1-carboethoxymethyl and 1-carboxymethyl-3-aminophenyl-1, 2-dihydroquinoxalinone derivatives are said to have antiamoebetic and diuretic activity (Indian J. of Chem. (1974) 124).
• the use of such compounds as safeners is not yet known.
• the known safeners can have disadvantages in many cases. These include: the safener reduces the action of the pesticides, in particular those of herbicides, against the harmful plants, the crop protection properties are inadequate; in combination with a particular herbicide, the spectrum of useful plants in which the safener / herbicide use is to be carried out is not sufficiently large , a certain safener can only be combined with a few herbicides. The use of safeners increases the application rate and amount of formulation to be applied and can therefore cause application problems.
• the invention relates to the use of compounds of the general formula (I) or their salts (1, 2-dihydro-quinoxalin-2-one-dehvate),
• X is oxygen or sulfur, (Y) n n substituents Y, where each Y independently of one another is a radical halogen, cyano, nitro, (CrC 6 ) AlkVl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) AlkOXy, (dC 6 ) alkylthio, (CrCe) alkylsulfinyl, (CrC 6 ) alkylsulfonyl, (Ci-C 6 ) alkoxycarbonyl, (Cr
• Cyano, nitro, (Ci-C 4 ) alkyl, (CrC 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C r C 4 ) haloalkoxy and (CrC 4 ) alkylthio is substituted
• n denotes 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, in particular 0, 1 or 2
• R 1 is hydrogen, hydroxy, amino, (CrC 4 ) alkylamino, di - [(CrC 4 ) alkyl] amino, ( C 1 -C 10 ) alkyl, (C 3 -C 10 ) alkenyl, (C 3 -C 10 ) alkynyl or (C 1 -C 10 ) alkoxy, each of the latter 4 residues being unsubstituted or by one or more identical or different R a is substituted and has substituents including 1 to 30 C atoms, preferably 1 to 24 C atoms, or (C
• R a in each case independently of other radicals R a for an inorganic or organic radical, preferably a radical from the group
• R c is an inorganic or organic radical, preferably a radical from the group
• R d each independently of other radicals
• R d is an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formula -Z d -R d * and R d ** , where in the radicals R a , R b , R c and R d Z a , Z b , Z c and Z d each independently have a divalent functional monatomic or polyatomic group with at least one
• Heteroatom and R cyc - a unc jp cyc - c each represent an optionally substituted cyclic
• R a *, R b *, R c *, R d *, R b ** and R 0 ** each independently of one another are an optionally substituted hydrocarbon radical with a total of 1 to 24 carbon atoms or optionally substituted heterocyclic
• the compounds of the general formula (I) can be present as stereoisomers.
• the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I).
• stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. Likewise, stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances. 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 to their mixtures.
• 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 structure of chemical compounds are to be observed, ie the formula (I) does not include compounds which the person skilled in the art knows that they are not chemically possible ,
• the compounds of formula (I) can form salts. Salt formation can take place by the action of a base on those compounds of formula (I) which carry an acidic hydrogen atom, for example in the case where R 1 contains a COOH group or a sulfonamide group -NHSO 2 -.
• Suitable bases are, for example, organic amines and ammonium, alkali or alkaline earth metal hydroxides,
• carbonates and bicarbonates in particular sodium and potassium hydroxide, carbonate and bicarbonate.
• These salts 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 also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
• the compounds of the formula (I) can be added by addition of a suitable inorganic or organic acid, such as, for example, mineral acids, such as, for example, HCl, HBr, H 2 SO 4 or HNO3, or organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid or sulfonic acids 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.
• a suitable inorganic or organic acid such as, for example, mineral acids, such as, for example, HCl, HBr, H 2 SO 4 or HNO3, or organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid or sulfonic acids form a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or
• Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids are present, can form inner salts with groups that can be protonated, such as amino groups.
• An inorganic radical is a radical without carbon atoms, preferably halogen, OH and its inorganic salts, in which the H is replaced by a cation, for example alkali metal and alkaline earth metal salts, NH 2 and its ammonium salts with (inorganic) acids, for example mineral acids, N 3 (Azide), N 2 + A " (diazonium radical, where A " represents an anion), NO, NHOH, NHNH 2 , NO 2 , S (O) OH (sulfinic acid residue), S (O) 2 OH (or also short SO 3 H, sulfonic acid residue), -0-SO 2 H (sulfite), -0-SO 3 H (sulfate), -P (O) (OH) 2 (phosphonic acid residue), -0-P (OH) 3 , (Phosphate residue) and the hydrated or dehydrated forms of
• organic radical here preferably does not include pseudohalogen groups such as CN, SCN, organic metal complexes, carbonate or COOH, which are better assigned to the organic radicals on account of the content of carbon atoms.
• An organic radical is a radical with carbon atoms, which radical can also be bound via heteroatoms. It is preferably an optionally substituted hydrocarbon radical or an optionally substituted heterocyclic radical. However, it also preferably comprises acyl radicals, ie. H. Remains of organic acids, which arise from the removal of an OH group.
• Acyclic residues also include sulfonic acid ester, phosphonic acid ester, phosphinic acid ester groups, each with organic alcohol components (and are then derived from polybasic acids), or alkylsulfonyl or alkylsulfinyl, which are derived from sulfonic acids or sulfinic acids.
• a hydrocarbon residue is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted one
• Hydrocarbon radical also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, for example comprising the Residues alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, naphthyl, indanyl, indenyl, etc .;
• the hydrocarbon or hydrocarbonoxy radicals in the above definitions preferably have 1 to 20 C atoms, more preferably 1 to 16 C atoms, in particular 1 to 12 C atoms.
• hydrocarbon radicals and the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
• (CrC 4 ) alkyl means a shorthand notation for open-chain alkyl with one to 4 carbon atoms corresponding to the range for C atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2- Butyl, 2-methylpropyl or tert-butyl.
• General alkyl radicals with a larger specified range of carbon atoms e.g. B.
• "(Ci-C 6 ) alkyl” accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
• the lower carbon skeletons for example those having 1 to 6 carbon atoms or unsaturated groups having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
• Alkyl radicals also 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
• Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
• Alkenyl means, for example, vinyl, AIIyI, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably 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 or 1- methyl-but-2-en-1-yl.
• (C 2 -C 6 ) -alkynyl means, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-in-1-yl, but-3-in-1-yl or 1-methyl-but-3-in-1-yl.
• Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
• substituents also having a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included.
• multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
• Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl.
• substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
• halogen means, for example, fluorine, chlorine, bromine or iodine.
• Aryl means a mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 12 carbon atoms, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl, biphenylyl and the like, preferably phenyl.
• a heterocyclic radical or ring contains at least one heterocyclic ring which is saturated, unsaturated or heteroaromatic and which, in the generally substituted case, can be fused with other carbocyclic or heterocyclic rings; unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, although two oxygen atoms should not be directly adjacent and at least one carbon atom must be present in the ring, for example a residue of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1, 3,4-oxadiazole, 1, 3,4-thiadiazole, 1, 3,4-triazole, 1, 2,4 -Oxadiazole, 1, 2,
• Heteroaryl means from the groups mentioned above under “Heterocyclyl” in each case the completely unsaturated aromatic heterocyclic compounds, for. B. pyridine, pyrimidine, (1, 2,4) -oxadiazole, (1, 3,4) -oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1, 2,4-triazole, Tetrazole, pyrazine or pyridazine.
• Heterocyclyl is preferably an aliphatic, saturated or unsaturated, in particular saturated, heterocyclyl radical with 3 to 7, in particular 3 to 6 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
• Heterocyclyl preferably contains hetero ring atoms from the group N, O and S,
• heterocyclyl are a heterocyclic radical with 3 to 6
• Ring atoms from the group pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl ( tetrahydrofuryl), pyrrolidinyl, piperidinyl, in particular oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical with two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, dioxanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, o
• Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo.
• the oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams.
• the oxo group can also occur on the hetero atoms which can exist in various oxidation states, for example in the case of N and S, and then form, for example, the divalent groups -N (O) -, -S (O) - (also SO for short) and -S (O) 2 - (also SO 2 for short) in the heterocyclic ring.
• Substituents other than the oxo group can also be bonded to a hetero atom on a heterocyclic ring, for example to a nitrogen atom, if a hydrogen atom on the nitrogen atom of the main body is replaced.
• a heteroatom on the nitrogen atom of the main body is replaced.
• the nitrogen atom and also other heteroatoms such as e.g. B. the sulfur atom
• a further substitution with the formation of quaternary ammonium compounds or sulfonium compounds is also possible.
• Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents for example one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, Mono- and dialkylamino, thalkylsilyl and optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, each of the latter cyclic groups also via heteroatoms or divalent functional
• cyclic systems are also included with those substituents which are bonded to the ring with a double bond, for. B. are substituted with an alkylidene group such as methylidene or ethylidene or an oxo group, imino group or substituted imino group.
• first substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
• second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
• substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
• second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
• substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined
• Preferred substituents for the substituent levels are, for example
• radicals with carbon atoms those with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
• Substituents from the group halogen for example fluorine and chlorine, (Ci-C 4 ) alkyl, preferably methyl or ethyl, (Ci-C 4 ) haloalkyl, preferably trifluoromethyl, (Ci-C 4 ) alkoxy, preferably methoxy, are generally preferred or ethoxy, (CrC 4 ) haloalkoxy, nitro and cyano.
• the substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
• Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and saturated N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (CrC 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino. Substituted amino also includes quaternary ammonium compounds (salts) with four organic substituents on the nitrogen atom.
• Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy,
• (CrC ⁇ haloalkyl, (C- ⁇ -C 4 ) haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4- Fluorophenyl, 2-, 3- and 4-trifluoromethyl and trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
• Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or one or more times, preferably up to three times, the same or different radicals from the group halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci-C 4) substituted haloalkyl, and (CrC 4) haloalkoxy, in particular by one or two (Ci-C 4 ) Alkyl radicals is substituted,
• Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (Ci-C 4 ) alkyl, (CrC 4 ) alkoxy, (Ci-C 4 ) haloalkyl , (CrC 4 ) Haiogenalkoxy, nitro and oxo is substituted, in particular one or more times by radicals from the group halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (CrC 4 ) haloalkyl and oxo, quite is especially substituted by one or two (C 1 -C 4 ) alkyl radicals,
• Acyl means a residue of an organic acid which is formally formed by removing a hydroxyl group on the acid function, the organic residue in the acid also being able to be linked to the acid function via a hetero atom.
• Examples of acyl are the residue -CO-R of a carboxylic acid HO-CO-R and residues of acids derived therefrom such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids , Phosphonic acids, phosphinic acids.
• Acyl means, for example, formyl, alkylcarbonyl such as [(Ci-C 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl, N-alkyl- and N, N-dialkylcarbamoyl and other residues of organic acids.
• alkylcarbonyl such as [(Ci-C 4 ) alkyl] carbonyl
• phenylcarbonyl alkyloxycarbonyl
• phenyloxycarbonyl benzyloxycarbonyl
• alkylsulfonyl alkylsulfinyl
• N-alkyl-1-iminoalkyl N-alkyl- and N, N-dialkylcarbamoyl and other residues of organic
• radicals in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy;
• substituents in the phenyl part are the substituents mentioned generally above for substituted phenyl.
• Acyl preferably means an acyl radical in the narrower sense, ie a radical of an organic acid in which the acid group is directly linked to the carbon atom organic radical, for example alkanoyl such as formyl and acetyl, aroyl such as phenylcarbonyl, and other radicals of saturated or unsaturated organic acids.
• Aroyl means an aryl radical as defined above which is attached via a carbonyl group, e.g. the benzoyl group.
• (C 1 -C 6 ) alkyl methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl;
• (CrCio) alkyl accordingly comprises the aforementioned alkyl radicals and isomers
• Pentyl radicals such as n-pentyl, 1, 1-dimethylpropyl or 2-methylbutyl, isomeric hexyl,
• (C 2 -C 4 ) alkenyr accordingly represents, for example, the vinyl, allyl, 2-methyl-2-propen-1-yl, 2- or 3-buten-1-yl,
• (C 3 -Ci 0 ) alkenyr 'thus represents, for example, the AIIyI-, 2-methyl-2-propen-1-yl-, 2- or
• (C 2 -C 4 ) alkynyl stands for example for the ethynyl, propargyl or 2-butyn-1-yl group
• (C 3 -Ci 0 ) alkynyl stands for for example the propargyl, 2- butyn-1-yl
• (C 3 -C 6 ) cycloalkyl stands for the cyclopropyl, cyclobutyl, cyclopentyl or
• (C 3 -Ci 0 ) cycloalkyl stands for monocyclic alkyl radicals, such as the cyclopropyl
• (C 4 -Cio) cycloalkenyl stands for monocyclic cycloalkylene radicals, such as the
• Cyclodecenyl radical for bicyclic alkyl radicals, such as the norbornenyl or bicyclo [2,2,2] octenyl radical, or for condensed systems, such as the tetra, hexa- or octahydronaphthyl radical.
• Hydrocarbon radicals which are expressed under the terms "(Ci-C 4 ) -alkyl" and "(Ci-Ci 0 ) -
• Alkyl "have the meanings given.” (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkoxy "means an alkoxy as defined above.
• a group which is substituted by a further alkoxy group such as the ethoxy methoxy, methoxymethoxy, 1 methoxyethoxy, 1 ethoxyethoxy or the 1-
• (C 3 -Ci 0 ) cycloalkyl- (C 3 -C 4 ) alkenyloxy stands for.
• (C 4 -Ci 0 ) cycloalkenyl- (C 3 -C 4 ) alkenyloxy stands for. B. for the cyclobutenylallyloxy or the cyclopentenylallyloxy group.
• (C r C 4 ) alkyl (C 3 -Cio) cycloalkoxy stands for. B. for the methylclopentyloxy, ethylcyclopentyloxy, methylcyclohexyloxy or the ethylcyclohexyloxy group.
• (C 2 -C 4 ) alkenyl (C 3 -Ci 0 ) cycloalkoxy stands for. B.
• (Ci-C 4 ) alkyl- (C 4 -Cio) cycloalkenyloxy stands for. B. for the methylcyclopentenyloxy, ethylcyclopentenyloxy, methylcyclohexenyloxy or the ethylcyclohexenyloxy group.
• (C 2 -C 4 ) Alkenyl- (C 3 -C- ⁇ o) cycloalkenyloxy stands for. B. for the Vinylyclopentenyloxy-, Allylcyclopentenyloxy-, Vinylcyclohexenyloxy- or the Allylcyclohexenyloxy group.
• (Ci-C 4 ) alkoxy- (C 3 -C 4 ) alkenyloxy means e.g. B. the methoxyallyloxy or the ethoxyallyloxy group.
• (Ci-Cio) alkanoyl stands for example for the formyl, acetyl, propionyl, butyryl, 2-methylbutyryl, pivaloyl, octanoyl or decanoyl group.
• (C 4 -Cio) cycloalkanoyl stands for example for the cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl or the cyclononylcarbonyl group
• (C 3 -Cio) alkenoyl stands for example for the acrylic, methacrylic, crotonoyl, dimethylacryl- or octenoyl group.
• (C 3 -Cio) Alkinoyl stands for example for the propinoyl, butinoyl, hexinoyl or octinoyl
• "Mono- or di- (C 3 -Cio) cycloalkylcarbamoyl”
• (CrCio) alkoxycarbonyl means e.g. B. the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec
• (C 3 -Cio) cycloalkoxycarbonyl means e.g. B. the cyclopropoxycarbonyl
• (Ci-Cio) alkanoyloxy means e.g. B. the acetoxy, propionyloxy, butanoyloxy or the pivaloyloxy group.
• (C 4 -C 10 ) Cycloalkanoyloxy means e.g. B. the cyclopropylcarbonyloxy
• (Ci-CioJalkoxycarbonyloxy) means a carbonate group, such as the methoxy
• (CrC 10 ) alkylamine carbonyloxy means a carbamate group, such as. B.
• Group S (O), S (O) 2 or NR 3 can be replaced and R 3 (C r C 4 ) alkyl, (CrC 4 ) -
• Alkanoyl, (CrC 4 ) -alkoxycarbonyl, di- (CrC 4 ) -alkylcarbamoyl or optionally substituted aryl means "means a carbamate group, such as, for example, the dimethyl, diethyl, methyl-ethyl, dibutyl-pyrrolidino- , Piperidino, morpholino,
• (CrCio) alkylsulfonylamino means e.g. B. a methyl, ethyl, propyl, isopropyl,
• (Ci-C 10 ) alkanoylamino means e.g. B. the formylamino, acetylamino, propionylamino, isopropionylamino, butanoylamino or the pivaloylamino
• (C 3 -Cio) alkenoylamino means e.g. B. the acrylamino, methacrylamino,
• (C 4 -Cio) cycloalkanoylamino means e.g. B. the cyclopropanoylamino
• Cyclobutanoylamino Cyclopentanoylamino or the Cyclohexanoylamino group.
• (C 3 -Cio) cycloalkyl (Ci-C 4 ) alkanoylamino means e.g. B. the
• Alkyl groups can also be linked cyclically to form a three- to eight-membered ring in which a carbon unit can optionally be replaced by oxygen, sulfur or a group S (O), S (O) 2 or NR 3 and R 3 (Ci-C 4 ) alkyl, (Cr
• C 4 ) -alkanoyl, (Ci-C 4 ) -alkoxycarbonyl, di- (Ci-C 4 ) -alkylcarbamoyl or optionally substituted aryl means "means a urea group, such as.
• (Ci-Cio) -alkylthio stands for an alkylthio group whose hydrocarbon radical has the meaning given under the expression "(Ci-Cio) -alkyl”.
• (C 3 -Cio) alkenylthio stands for an alkenylthio group whose hydrocarbon radical has the meaning given under the expression "(C 3 -Cio) alkenyl”.
• (C 3 -Cio) alkynylthio represents an alkynylthio group whose hydrocarbon radical has the meaning given under the expression "(C 3 -Ci 0 ) alkynyl”.
• (C 3 -Cio) cycloalkylthio stands for a cycloalkylthio group, the hydrocarbon radical of which is given under the expression “(C 3 -Cio) cycloalkyl”
• (C 4 -Cio) cycloalkenylthio stands for a cycloalkenylthio group
• (C 3 -C 10 ) cycloalkyl (Ci-C 4 ) alkylthio stands for example for the cyclopropylmethylthio
• Cyclopropylethylthio, Cyclopentylmethylthio or the Cyclohexylmethylthio group represents, for example, the Cyclopentenylmethylthio- or Cyclohexenylmethylthio group.
• (C 3 -C 10 ) cycloalkyl- (C 3 -C 4 ) alkenylthio stands for example for the cyclopropylallylthio-
• Cyclopentylallylthio or the Cyclohexylallylthio group (C 4 -Cio) cycloalkenyl (C 3 -C 4 ) alkenylthio" stands for example for the cyclopentenylallylthio or the cyclohexenylallylthio group.
• (CrC 4 ) -alkyl- (C 3 -Cio) -cycloalkylthio stands for example for the methycyclopentyllthio or the methyclohexylthio group.
• (Ci-C 4 ) -alkyl- (C 4 -C 10 ) -cycloalkenylthio stands for example for the methylcyclopentenylthio or the methylcyclohexenylthio group.
• (C 2 -C 4 ) alkenyl (C 3 -Cio) cycloalkylthio stands for example for the vinylcyclopentylthio
• (CrC 4 ) -alkyl- (C4-Ci 0 ) -cycloalkenylthio stands for example for the methylcyclopentenylthio or the methylcyclohexenylthio group.
• (C 2 -C 4 ) alkenyl (C 4 -C 8 ) cycloalkenylthio stands for example for the allylcyclopentenylthio or the allylcyclohexenylthio group.
• (Ci-C 10 ) alkylsulfinyl stands for example for the methyl, ethyl, propyl, isopropyl, butyl,
• (C 3 -C 10 ) alkenylsulfinyl stands for example for the AIIyI, methylallyl, butenyl or
• (C 3 -Cio) alkynylsulfinyl stands for example for the propargyl, butynyl or octynylsulfinyl group.
• (C 3 -Cio) cycloalkylsulfinyl represents a cycloalkylsulfinyl group whose
• (C 3 -Cio) cycloalkyl- (Ci-C 4 ) alkylsulfinyl stands for example for the cyclopropylmethylsulfinyl
• (C 4 -Cio) cycloalkenyl (Ci-C 4 ) alkylsulfinyl stands for example for the cyclopentenylmethylsulfinyl or the cyclohexenylmethylsulfinyl group.
• (C 3 -C 10 ) -cycloalkyl- (C 3 -C 4 ) alkenylsulfinyr stands for example for the cyclopropylallylsulfinyl-
• Cyclopentenylallylsulfinyl or the Cyclohexenylallylsulfinyl group is a Cyclopentenylallylsulfinyl or the Cyclohexenylallylsulfinyl group.
• (Ci-C 4 ) alkyl- (C 3 -Ci 0 ) -cycloalkylsulfinyl stands for example for the methylcyclopentylsulfinyl or the methylcyclohexylsulfinyl group.
• Methylcyclopentenylsulfinyl or the methylcyclohexenylsulfinyl group isobutylcyclopentenylsulfinyl or the methylcyclohexenylsulfinyl group.
• (C 2 -C 4 ) alkenyl (C 3 -Ci 0 ) cycloalkylsulfinyl stands for example for vinylcyclopentylsulfinyl, allylcyclopentylsulfinyl, vinylcyclohexylsulfinyl or allylcyclohexylsulfinyl
• (C 2 -C 4 ) alkynyl (C 3 -Cio) cycloalkylsulfinyl represents, for example
• Ethynylcyclopentenylsulfinyl propargylcyclopentenylsulfinyl, ethynylcyclohexenylsulfinyl or the propargylcyclohexenylsulfinyl group.
• (CrdoJ-alkylsulfonyl) stands for example for the methyl, ethyl, propyl, isopropyl, butyl,
• (C 3 -Cio) alkenylsulfonyl stands for example for the AIIyI, methylallyl, butenyl or
• (C 3 -Ci 0 ) cycloalkylsulfonyl represents a cycloalkylsulfonyl group
• (C 4 -Cio) cycloalkenylsulfonyl stands for a cycloalkenylsulfonyl group, the hydrocarbon radical of which is given under the expression “(C 4 -Cio) cycloalkenyl”
• I l (C 4 -C 10 ) cycloalkenyl (C 1 -C 4 ) alkylsulfonyl "represents, for example
• (Ci-C 4 ) alkyl (C 3 -Cio) cycloalkylsulfonyl stands for example for the methylcyclopentylsulfonyl or the methylcyclohexylsulfonyl group.
• (CrC 4 ) alkyl (C 4 -C 10 ) cycloalkenylsulfonyl represents, for example, the methylcyclopentenylsulfonyl or methylcyclohexenylsulfonyl group.
• (C 2 -C 4 ) alkenyl (C 3 -Ci 0 ) cycloalkylsulfonyl represents, for example
• (C 2 -C 4 ) alkynyl (C 3 -Cio) cycloalkylsulfonyl represents, for example, the ethynylcyclopentylsulfonyl, propargylcyclopentylsulfonyl, ethynylcyclohexylsulfonyl or the propargylcyclohexylsulfonyl group.
• (C 2 -C 4 ) alkenyl (C 4 -Cio) cycloalkenylsulfonyl represents, for example
• Alkyl groups can also be linked cyclically to form a three- to eight-membered ring, in which a carbon unit is optionally formed by oxygen or sulfur or a group S (O) 1 S (O) 2 or NR 3 can be replaced and R 3 (Ci-C 4 ) alkyl,
• (Ci-C 4 ) -alkanoyl, (CrC 4 ) -alkoxycarbonyl, di- (C 1 -C 4 ) -alkylcarbamoyl or optionally substituted aryl means "represents, for example, the methyl, ethyl,
• (Ci-C- ⁇ o) alkylamino stands for an amino group whose hydrocarbon radical has the meaning given under the expression "(CiC 10 ) alkyl”.
• (C 3 -Cio) alkenylamino stands for an amino group whose hydrocarbon radical has the meaning given under the expression "(Ci-Cio) alkenyl”.
• (C 3 -Cio) -alkynylamino represents an amino group whose hydrocarbon radical is as defined under the term “(C 3 -C O) alkynyl” has the meaning given.
• (C 3 -Cio) cycloalkylamino stands for an amino group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) cycloalkyl”.
• (C 3 -Cio) cycloalkenylamino represents an amino group whose
• (C 3 -Cio) cycloalkyl- (CrC 4 ) alkylamino stands for example for the cyclopropylmethylamino- cyclopropylethylamino-, cyclopentylmethylamino- or the cyclohexylmethyamino-
• (C 4 -Cio) cycloalkyl (C 3 -C 4 ) alkenylamino stands for example for the cyclopropylallylamino-cyclopentylallylamino or the cyclohexylallylamino group.
• (Ci-C 4 ) alkyl (C 3 -C 10 ) cycloalkylamino stands for example for the methylcyclopentylamino or the methylcyclohexylamino group.
• (CrC 4 ) alkyl (C 4 -C 10 ) cycloalkenylamino stands for example for the
• Methylcyclopentenylamino or the methylcyclohexenylamino group Methylcyclopentenylamino or the methylcyclohexenylamino group.
• (C 2 -C 4 ) alkenyl (C 3 -Cio) cycloalkylamino stands for example for the vinylcyclopentylamino, allylcyclopentylamino, vinylcyclohexylamino or the allylcyclohexylamino group.
• (C 2 -C 4 ) alkynyl (C 3 -Cio) cycloalkylamino stands for example for the ethynylcyclopentylamino, propargylcyclopentyamino, ethynylcyclohexylamino or the propargylcyclohexylamino group.
• (C 2 -C 4 ) alkenyl (C 4 -Cio) cycloalkenylamino stands for example for the vinylcyclopentenylamino, allylcyclopentenylamino, vinylcyclohexenylamino or the allylcyclohexenylamino group.
• (Ci-Cio) -trialkylsilyl means a silicon atom which carries three identical or different alkyl radicals as defined above.
• Aryloxy means an aryl radical as defined above which has one
• Oxygen atom is bound, e.g. the phenoxy or naphthyloxy group.
• Arylthio means an aryl residue linked via a sulfur atom, e.g. the phenylthio or the 1- or 2-naphthylthio radical.
• Arylamino means an aryl radical linked via a nitrogen atom, e.g. the
• N- (Ci-C 4 ) -alkyl-arylamino means, for example, the N-methyl or N-ethyl-anilino radical.
• Aryl- (Ci-C 4 ) -alkoxy stands for an aryl radical linked via a (CrC 4 ) alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy
• Aryl- (C 3 -C 4 ) alkenyloxy stands for an aryl radical linked via a (C 3 -C 4 ) alkenyloxy group, for example the 1-, 2- or 3-phenylallyloxy radical.
• Aryl- (Ci-C 4 ) -alkylthio stands for an aryl radical which is linked via an alkylthio radical, for example benzylthio, naphthylmethylthio or 1- or 2-phenylethylthio-
• Aryl- (C 3 -C 4 ) -alkenylthio stands for an aryl radical linked via a (C3-C 4 ) -alkenylthio group, for example the 1, 2- or 3-phenylallylthio radical.
• Aryl- (C 1 -C 4 ) alkylamino stands for an aryl radical linked via a (CrC 4 ) alkylamino group, for example the benzylamino, naphthylamino, the 1- or 2-
• N- (Ci-C 4 ) alkyl-N-aryl- (Ci-C4) alkylamino stands for example for the N-methyl-N-benzylamino-, N-methyl-N-naphthylamino-, the N-methyl -N-1 or 2-phenylethylamino or the N-methyl-N-3-phenylpropylamino radical.
• Aryl- (C 3 -C 4 ) -alkenylamino stands for an aryl radical linked via a (C 3 -C 4 ) -alkenylamino group, for example the 1, 2- or 3-phenylallylamino radical.
• N-td-C ⁇ alkyl-N-aryHCs-C ⁇ alkenylamino is e.g. for the N-methyl-N-1, - 2- or 3-phenylallylamino radical.
• Arylcarbamoyl stands for. B. for phenyl or 1- or 2-naphthyl carbamoyl.
• N-Aryl-N- (C 1 -C 4 ) alkyl carbamoyl is e.g. B. for N-methyl-N-phenyl-carbamoyl or N-methyl-N-1- or 2-naphthyl-carbamoyl.
• Aryl- (CrC 8 ) dialkylsilyl is e.g. B. for a phenyl or naphthyldimethylsilyl
• Diaryl- (C 3 -C 4 ) alkylsilyl is e.g. B. for a diphenyl, phenyl-naphthyl, or
• Triarylsilyl stands for. B. for a triphenyl, diphenyl-naphthyl or trinaphthyl-silyl
• X is oxygen
• (Y) n n are preferably substituents Y, where each Y independently of one another is a radical halogen, cyano, nitro, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, ( C 1 -C 4 ) AlkOXy, (CrC 4 ) alkylthio, (C r C 4 ) alkylsulfinyl, (CrC 4 ) alkylsulfonyl, (Ci-C 4 ) alkoxycarbonyl, (C 1 - C 4 ) alkylamino or di - [(Ci-C 4 ) alkyl] amino, each of the latter 10 radicals unsubstituted or substituted by one or more radicals from the group halogen, (Ci-C 4 ) alkoxy, (C 1 -C 4 ) HaIOaIkOXy and (C- ⁇
• Radicals mentioned in parentheses unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (C 1 -C 4 ) AIKyI, (CrC 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) HaIOaIkOXy and (CrC ⁇ alkylthio and in the case of non-aromatic radicals also oxo is substituted, or two adjacent groups Y together with the directly bonded carbon atoms mean a four- to six-membered fused ring which is carbocyclic or heterocyclic with one or more Hetero ring atoms, preferably one to three hetero ring atoms from the group N, O and S and which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (C 1 -C 4 ) AIKyI, (CrC 4 ) haloal
• Radicals from the group halogen, (Ci-C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (CrC 4 ) haloalkoxy (CrC 4 ) alkylthio and oxo is substituted, and n 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, in particular 0, 1 or 2, very particularly 0 or 1.
• each Y is independently a radical of halogen, cyano, nitro, (C 1 - C 4) alkyl, (dC ⁇ haloalkyl, [(C 1 -C 4) alkoxy] - (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) Cycloalkyl, (C 5 - C 6 ) cycloalkenyl, optionally substituted aryl (preferably phenyl which is unsubstituted or by one or more radicals from the group several radicals from the group halogen, (CrC 4 ) alkyl, (C r C 4 ) haloalkyl and (C 1
• (Y) n n denotes Y, where each Y independently of one another is a radical halogen, cyano, nitro, (C 1 -C 4 ) alkyl, (dC 4 ) haloalkyl, preferably (dC 4 ) fluoroalkyl, (Ci-C 4 ) AlKOXy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) AlkOXy, (C 1 -C 4 ) HaIOaIkOXy, (dC 4 ) alkylthio, (dC 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl , (Ci-C 4 ) haloalkylsulfinyl (preferably (dC 4 ) fluoroalksulfinyl), (Ci-C 4 ) alkylsulfonyl, (dC 4 ) haloalkyl,
• (Y) n n denotes Y, where each Y independently of one another is a radical halogen, (Ci-C 4 ) alkyl, (C 1 - C 4 ) haloalkyl (preferably (CrC 4 ) fluoroalkyl), (dC 4 ) alkoxy or (d-C 4 ) haloalkoxy (preferably (Ci-C 4 ) fluoroalkoxy), (Ci-C 4 ) haloalkylthio (preferably (CrC 4 ) fluoroalkylthio) or two adjacent groups Y together represent the divalent group 2,2-difluoromethylene dioxy (-0-CF 2 -O-; 2,2-difluoro-1,3-dioxapropan-1,3-diyl).
• Y very particularly independently of one another means halogen, cyano, (CrC 4 ) alkyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio,
• Trifluoromethylthio or 2,2-difluoromethylene dioxy in particular fluorine, chlorine, methyl, trifluoromethyl or methoxy.
• R 1 is hydrogen, hydroxy, amino, (Ci-C 4 ) alkylamino, di - [(Ci-C 4 ) alkyl] amino, (Ci-C 6 ) alkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl or (C 1 -C 6 ) AI koxy, each of the latter 4 radicals being unsubstituted or substituted by one or more identical or different radicals R a , including substituents 1 to 30 C atoms, preferably 1 to 24 C. -
• R 2 is hydrogen, (C r Cio) alkyl, (C 3 -C 10 ) alkenyl or (C 3 -Ci 0 ) alkynyl, each of the latter 3 radicals unsubstituted or by one or more identical or different radicals R c is substituted and includes substituents 1 to 30 C atoms, preferably 1 to 24 C atoms
• R a each independently represents an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formulas -Z a -R a * and R cyc a
• R b each independently represents an inorganic or organic radical Radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formulas -Z b -R b * and R b * *
• R c each independently represents an inorganic or organic radical, preferably a radical from the group halogen , Cyano, nitro and radicals of the formulas -Z c -R c * and R cyc "c ,
• R d each independently represents an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formula -Z d -R d * and R d ** , where in the radicals R a , R b , R c and R d Z a , Z b , Z c and Z d each independently represent a divalent group of
• Is 0, 1 or 2 and the radicals R 0 independently of one another are each hydrogen, (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, phenyl, phenyl- (dC 6 ) alkyl, (C 3 -C 6 ) cycloalkyl or acyl with preferably 1 to 10 C atoms (preferably acyl from the group [(CrC 6 ) alkyl] carbonyl [(C r C 6 ) alkoxy] carbonyl or [ (Ci-C 6 ) alkylsulfonyl) and R 1 and R "independently of one another are (CrC ⁇ alkyl, (C 2 - C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, phenyl, phenyl- (CrC 6 ) alkyl or (C 3 - C 6 ) cycl
• a hydrocarbon radical with a total of 3 to 24 carbon atoms, preferably 1 to 18 carbon atoms, or an optionally substituted heterocyclic radical with a total of 1 to 24 carbon atoms, preferably 1 to 18 carbon atoms, and R a *, R b * , R 0 *, R d *, R b ** and R 0 * * each independently of one another are an optionally substituted hydrocarbon radical with a total of 1 to 24 C atoms, preferably 1 to 18 C atoms, or optionally substituted heterocyclic radical with a total of 1 up to 24 carbon atoms, preferably 1 to 18 carbon atoms, or R a *, R b *, R 0 *, R d * each independently represent hydrogen
• Z a , Z b , Z c and Z d each independently of one another a divalent group of the formula -O-, -S (O) P -, -S (O) pO-, -OS (O) P -, -NR ° -S (O) p-, -S (O) P NR ° -, -CO-, -O-CO-,
• R a *, R b ⁇ R 0 *, R d * each independently represent hydrogen.
• R 1 is hydrogen, (C r C 6 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl, each of the latter 3 radicals unsubstituted or substituted by one or more identical or different radicals R a , including substituents 1 to 24 carbon atoms, preferably 1 to 18 carbon atoms
• R a represents an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formulas -Z a -R a * and R cyc ⁇ a
• R b represents an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formulas -Z b -R b * and R b ** , where in the radicals R a and R b Z a , Z b , R cyc "a , R a * , R b * and R b ** are as defined above or below, preferably Z a , Z b independently of one another -O-, -S (O) P -, -S (O) P -O-, -OS (O) P -,
• p is the integer O, 1 or 2 and the radicals R ° independently of one another are each hydrogen, (C r C 4 ) alkyl, phenyl , Phenyl- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl (Ci-C 4 ) alkanoyl, [(C r C 4 ) alkoxy] carbonyl or (Ci-C 4 ) alkylsulfonyl, in particular in each case for hydrogen or (C 1 -
• C 4 ) alkyl and R 'and R "independently of one another are (C 1 -C 4 ) alkyl, phenyl, phenyl- (Ci-C 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, in particular for (CrC 4 ) Are alkyl, R cyc'a (C 3 -C 6 ) cycloalkyl, (C 4 -C 6 ) cycloalkenyl, phenyl, saturated heterocyclyl, unsaturated non-aromatic heterocyclyl or
• each of the latter 6 residues being unsubstituted or by one or more residues from the group halogen, cyano, nitro, amino, hydroxy, thio, (Ci-C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 - C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C r C 4 ) alkoxy, (C 1 - C 4 ) haloalkoxy, (C r C 4 ) alkylthio, (C r C 4 ) haloalkylthio, (C 1 -
• R cyc-a (C 3 -C 6 ) cycloalkyl, phenyl, saturated heterocyclyl with 3 to 6
• Ring atoms or heteroaryl with 5 or 6 ring atoms each of the latter 4 residues unsubstituted or by one or more residues from the group halogen, cyano, nitro, (CrC 4 ) alkyl, (Cr C 4 ) haloalkyl, (C 1 -C 4 ) Alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (C 1 -
• R a *, R b * and R b ** each independently
• R a * and R b * are each independently hydrogen.
• R 2 (Ci-Cio) alkyl, (C 3 -Ci 0 ) alkenyl or (C 3 -C 10 ) alkynyl, in particular (C 1 -C 6 ) alkyl,
• Heteroaryl where each of the latter 5 radicals is unsubstituted or substituted by one or more identical or different radicals R d and, including substituents, has 3 to 24 carbon atoms, preferably 3 to 18 carbon atoms, where
• R c represents an inorganic or organic radical, preferably a radical from the group consisting of halogen, cyano, nitro and radicals of the formulas -Z c -R c * and R cyt> c ,
• R d stands for an inorganic or organic radical, preferably a radical from the group halogen, cyano, nitro and radicals of the formula -Z d -R d * and R d ** , wherein in the radicals R c and R d the radicals or Groups Z c , Z d , R cyc "c , R 0 *, R d * and R d ** are as defined above or below, preferably Z ° and Z d each independently of one another -O-, -S (O ) P -, -S (O) P -O-, -OS (O) P -,
• R 0 are each independently Hydrogen, (C r C 4 ) alkyl, phenyl, phenyl- (Ci-C 4 ) alkyl, (C 3 - C 6 ) cycloalkyl (Ci-C 4 ) alkanoyl, [(C 1 -C 4 ) alkoxy] carbonyl or (Ci-C 4 ) alkylsulfonyl, in particular each representing hydrogen or (C 1 - C 4 ) alkyl and R 1 and R "independently of one another are (C 1 - C 4 ) alkyl, phenyl, phenyl (C r C 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, in particular represent (Ci-C 4 ) alkyl, R cyc -
• Ring atoms or heteroaryl with 5 or 6 ring atoms each of the latter 4 residues being unsubstituted or by one or more residues from the group halogen, (dC 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 - C 4 ) alkoxy, (C 1 -C 4 ) HaIOaIkOXy, (CrC 4 ) alkylthio and in the case of saturated heterocyclyl also oxo is substituted, means and
• R c * and R d * each independently represent hydrogen, in particular
• R 0 * , R d * and R d * * each independently
• R 1 is as defined above, optionally, (CrC 4) substituted alkyl, (C 2 - C 4) alkenyl or (C 2 -C 4) alkynyl, and R 2 a of the optionally defined phenyl and heteroaryl radicals defined above.
• substituents R a and R c with which the alkyl, alkenyl, alkynyl and alkoxy groups listed for the radicals R 1 and R 2 are optionally substituted one or more times, identically or differently, are the following:
• Carboxy (Ci-Ci 0 ) alkoxy-carbonyl, (C 3 -Ci 0 ) cycloalkoxy-carbonyl, (CrCio) alkanoyloxy, (C 4 -C 10 ) cycloalkanoyloxy, (Ci-Cio) alkoxy-carbonyloxy, [(Cr C 10 ) alkyl] aminocarbonyloxy, di - [(Ci-Ci 0 ) alkyl] aminocarbonyloxy, or
• Cio alkylaminosulfonyl, heterocyclylsulfonyl, optionally N-substituted heterocyclylsulfonylamino, aryl-di - [(Ci-C 8 ) alkyl] -silyl, diaryl- (Ci-C 8 ) alkyl-silyl or triarylsilyl, the cyclic part of the latter 40 residues unsubstituted or by one or more radicals from the group halogen, cyano, nitro, amino,
• the optionally N-substituted radicals are preferably unsubstituted on the amino group or by a radical from the group (C r C 4 ) alkyl, (C r C 4 ) alkanoyl, [(C r C 4 ) alkoxy] carbonyl and phenyl substituted, in particular unsubstituted or by a radical from the group (CrC 4 ) alkyl and phenyl, very particularly unsubstituted or substituted by (C 1 -C 4 ) alkyl (the latter for example N-aryl-N- (CrC 4 ) alkyl-carbamoyl).
• the last-mentioned radicals which contain heterocyclyl are preferably those of the formulas NHet N Het-CO NHet-CO-O-NHet-CO-NH-NHet-CO-NR-NHet-S (O) 2 - or
• N Het denotes the residue of a saturated heterocycle having at least one nitrogen atom as ring atom (N-heterocyclyl) with the free bond (yl position) on the N-ring atom, where N Het is another in addition to the N-ring atom
• R and R 'independently of one another each represent (C 1 -C 4 ) alkyl, (CrC 4 ) alkanoyl, [(CrC ⁇ alkoxyj-carbonyl, di - [(C 1 -C 4 ) alkyl] carbamoyl or optionally substituted phenyl R is preferably (Ci-C 4 ) alkyl.
• R ' is (Ci-C 4) alkyl, (Ci-C4) alkanoyl, or [(C 1 -C 4) -alkoxy] - carbonyl.
• R b and R d with which the cycloalkyl, cycloalkenyl, aryl or heterocyclyl groups listed for the radicals R 1 and R 2 are optionally mono- or polysubstituted and substituted identically or differently, are those as for R a and R b are defined, or else those as mentioned below: (C 1 -C O) AIlCyI 1 (Ci-C 4) alkoxy- (C 1 -C 4) alkyl, (C 3 -C 10) alkenyl , (C 3 -C 10 ) alkynyl, (C 3 -
• Ci 0 cycloalkyl- (Ci-C 4 ) alkyl, (C 4 -Ci 0 ) cycloalkenyl- (Ci-C 4 ) alkyl, (C 3 -Ci 0 ) cycloalkyl- (C 3 - C 4 ) alkenyl, (C 4 -Ci 0 ) cycloalkenyl- (C 3 -C 4 ) alkenyl, (Ci-C 4 ) alkoxy- (C 3 -C 4 ) alkenyl, aryl- (Ci-C 4 ) alkyl, heterocyclyl- (CrC 4 ) alkyl or aryl- (C 3 -C 4 ) alkenyl, where the cyclic part of the last 3 radicals mentioned is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, amino,
• Adjacent substituents on aryl, heterocyclyl or cycloalkyl groups can, if chemically reasonable, be linked to form a four- to eight-membered ring.
• R 1 (Ci-C 6 ) alkyl, in particular (Ci-C 4 ) AIlCyI, which is unsubstituted or by one or more radicals from the group
• C 4 alkoxy is substituted, and a five- to eight-membered, preferably five- or six-membered saturated heterocycle, preferably with 1 to 3 hetero ring atoms from the group N, O and S, in particular O and S, which is optionally substituted, preferably unsubstituted or by one or more radicals from the group (C 1 -C 4) AIRyI and (C 1 - C 4) alkoxy, preferably (C 1 -C 4) AIKyI substituted, is substituted means.
• Heterocyclylcarbonyl is preferably a radical of the formula N Het-CO, where N Het- is as defined above or is preferably defined.
• R 1 (C 3 -C 6 ) alkenyl which is unsubstituted or by one or more radicals from the group halogen, preferably fluorine or chlorine, and aryl which is unsubstituted or by one or more radicals from the group halogen, (CrC ⁇ alkyl, (C 1 -C 4 ) haloalkyl and (C 1 -C 4 ) alkoxy is substituted, is substituted.
• R 1 is (C 3 -C 6 ) alkynyl or (C 3 -C 6 ) haloalkynyl is particularly preferred. Also particularly preferred is the use according to the invention with compounds (I) in which R 1 (C 3 -C 6 ) cycloalkyl or a five- to eight-membered saturated heterocycle which is unsubstituted or by one or more radicals from the group (C- ⁇ -C 4 ) Alkyl and (C 1 -C 4 ) AlkOXy, preferably (CrC 4 ) alkyl, is substituted.
• R 2 (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, aryl or heteroaryl, where each of the latter two radicals is unsubstituted or by one or more radicals from the group halogen, (dC 4 ) alkyl, (Ci -C 4 ) Haloalkyl and (Ci-C 4 ) alkoxy is substituted, and here heteroaryl preferably 5 or 6 ring atoms and 1 to 3, in particular 1 or 2 hetero ring atoms from the group N, O and S, very particularly thienyl, furyl , Thiazolyl or pyridyl, for example 2-thienyl, 3-thienyl,
• the invention therefore also relates to new compounds of the formula (I) and their salts, in which X is oxygen or sulfur,
• each Y is independently a radical halogen, cyano, nitro, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 - C 6 ) AlkOXy, (C 1 -C 6 ) alkylthio, (C r C 6 ) alkylsulfinyl, (CrC 6 ) alkylsulfonyl, (C 1 -C 6 ) -
• C atoms is a four- to eight-membered fused ring which is carbocyclic or heterocyclic with one to three hetero ring atoms from the group N, O and S and which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (Ci -C 4) alkyl, (C 1 - C 4) haloalkyl, (C 1 -C 4) -alkoxy, (C r C is substituted 4) haloalkoxy and (C r C 4) alkylthio, mean, n is 0, 1, 2 , 3 or 4, preferably 0, 1, 2 or 3, in particular 0, 1 or 2, and R 1 (C 1 -C 4 ) A ⁇ yI, (C 3 -C 10 ) alkenyl or (C 3 -C 10 ) Alkynyl, where each of the latter two (2) radicals is unsubstituted or each of the latter three (3) radicals is substituted by one or more
• R a each independently represents a radical from the group halogen, cyano, nitro and radicals of the formulas -Z a -R a * and R cyc a ,
• R b each independently for a radical from the group halogen, cyano,
• R d each independently represents a radical from the group halogen, cyano, nitro and radicals of the formula -Z d -R d * and R d ** , wherein in the radicals R a and R b
• Z a and Z b each independently of one another a divalent group of the formula -O-, -S (O) p-, -S (O) pO-, -OS (O) P -, -NR ° -S (O) P -, -S (O) P NR ° -, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S -, -O-CO-O-, -NR 0 -, -O-NR 0 -, -NR ° -O-, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR 0 -, -O-CO-NR ° - or -NR ° -CO-O-, -NR ° -CO-NR ° -, -NR ° -CO-NR °
• [(CrC 6 ) alkoxy] carbonyl or [(CrC ⁇ alkylsulfonyl) and R 1 and R "independently of one another are (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 - C 6 ) Alkynyl, phenyl, phenyl- (C r C 6 ) alkyl or (C 3 -C 6 ) cycloalkyl, and R cy c- a e j nen optionally substituted cyclic hydrocarbon radical with a total of 1 to 24 carbon atoms, preferably 1 to 18 C atoms, or an optionally substituted heterocyclic radical with a total of 1 to 24 C atoms, preferably 1 to 18 C atoms, and R a * , R b * and R b ** each independently of one another optionally substituted hydrocarbon radical a total of 1 to 24 carbon atoms, preferably 1 to 18 carbon
• Z d is a divalent group of the formula -O-, -S (O) P -, -S (O) P -O-, -OS (O) P -, -S (O) P NR ° -, -CO- , -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, - O-CO-O-, -CO-NR 0 -, -O-CO-NR 0 - or -SiR 1 R "-, in which each p is the integer O, 1 or 2 and the radicals R ° independently of one another are each hydrogen, (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -
• R d * and R d * * each independently of one another are an optionally substituted hydrocarbon radical with a total of 1 to 24 C atoms or optionally substituted heterocyclic radical with a total of 1 to 24 C.
• -Atoms mean or
• R d * denotes hydrogen, with the exception of compounds of the formula (I) and their salts, in which
• R 1 (Ci-C 4 ) alkyl which is substituted by a cyclohexylcarbamoyl radical and R 2 is a bicyclic heteroaryl radical
• R 1 (CrC 4 ) alkyl which is substituted by an N-substituted carbamoyl radical and at the same time optionally substituted cycloalkyl, heteroaryl or phenyl, and R 2 is phenyl,
• R 1 (dC 4 ) alkyl which is substituted by 2- (trimethylsilyl) ethoxy and R 2 is optionally substituted phenyl
• R 2 denotes optionally substituted phenyl or heteroaryl, where one substituent contains more than one cyclic group or where two or more substituents are cyclic
• R 1 (CrC 4 ) alkyl which is substituted by an optionally substituted aryl radical and R 2 is an optionally substituted aryl radical,
• R 2 denotes an optionally substituted indolyl residue or an N- (4-bromophenyl) - or N-phenyl-5- (hydroxymethyl) -pyrazol-3-yl residue and the following compounds are also excluded: (h) 1- (2-hydroxyethyl) -3-phenylquinoxaline-2 (1 H) -one, (i) 1- [2- (diethylamino) ethyl] -3-phenylquinoxaline-2 (1 H) -one, (j) 1- [ 3- (diethylamino) propyl] -3-phenylquinoxaline-2 (1 H) -one, (k) 7-ChIoM - [3- (dimethylamino) propyl] -3-phenylquinoxaline-2 (1 H) -one, (I ) 1- ⁇ 3- [2- (pyrrolidinyl-1-carbonyl) pyrrolidinyl-1-carbonyl] propyl ⁇ -3
• Residues in formula (I) as mentioned above for preferred definitions Have meanings, the conditions for the new compounds being taken into account as explained above.
• R 1 is (CrC 4 ) alkylene, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl, each of the latter 2 residues being unsubstituted or each of the latter 3 residues being substituted one or more identical or different radicals
• R a is substituted and includes substituents from 1 to 24 carbon atoms, preferably 1 to 18 carbon atoms, or (C 3 -C 6 ) cycloalkyl or saturated heterocyclyl, each of the latter 2 radicals being unsubstituted or is substituted by one or more identical or different radicals R b and including substituents has 3 to 24 carbon atoms, preferably 3 to 18 carbon atoms, where
• R a each independently for a radical from the group halogen, cyano,
• Nitro and radicals of the formulas -Z a -R a * and R cyc "a , R b each independently represents a radical from the group halogen, cyano,
• Z a and Z b independently of one another -O-, -S (O) P -, -S (O) P -O-, -OS (O) P -, -NR ° -S (O) p-, -S (O) pNR ° -, -CO-, -O-CO-, -CO-O-, -NR 0 -, -NR ° -CO-,
• (Ci-C 4 ) alkylsulfonyl in particular each represent hydrogen or (C 1 - C 4 ) alkyl and R 1 and R "independently of one another are (Cr C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, in particular represent (CrC 4 ) alkyl, R cyc - a (c 3 .c 6 ) cycloalkyl, (C 4 - C 6 ) cycloalkenyl, phenyl, saturated
• C 4 haloalkylsulfonyl, (CrC 4 ) alkylamino, di - [(C 1 -C 4 ) alkyl] amino, trimethylsilyl, (Ci-C 4 ) alkanoyl, [(CrC 4 ) alkoxy] carbonyl, di- [ (C r C 4 ) alkyl] -carbamoyl and in the case of saturated or unsaturated non-aromatic heterocyclyl also oxo is substituted, means and in particular
• Ring atoms or heteroaryl with 5 or 6 ring atoms each of the latter 4 residues unsubstituted or by one or more residues from the group halogen, cyano, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (dC ⁇ alkoxy ⁇ CrC ⁇ alkyl, (C 1 -C 4 ) AI koxy, (C 1 -
• C 4 ) alkyl is substituted, or phenyl or saturated heterocyclyl with 3 to 6 ring atoms or heteroaryl with 5 or 6 ring atoms, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, cyano, nitro, (C 1 -C 4 ) AIKyI, (C r C 4 ) haloalkyl, (C 1 - C 4 ) alkoxy- (C r C 4 ) alkyl, (C 1 -C 4 ) AlkOXy, (C 1 -C 4 ) HaIOaIkOXy, ( C 1 -C 4 ) alkylthio and in the case of saturated heterocyclyl also oxo is substituted.
• Ring atoms or heteroaryl with 5 or 6 ring atoms each of the latter 5 residues unsubstituted or by one or more residues from the group halogen, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (dC 4 ) alkylthio and in the case of cyclic radicals also (C 1 -C 4 ) AIKyI, (CrC 4 ) haloalkyl, (Cr C 4 ) Alkoxy- (C r C 4 ) alkyl and in the case of saturated heterocyclyl also oxo is substituted, or R a * and R b * each independently represent hydrogen.
• R 2 is phenyl or heteroaryl, each of the latter 2 radicals being unsubstituted or substituted by one or more identical or different radicals R d and including substituents 3 to 24 carbon atoms, preferably 3 to Has 18 carbon atoms, wherein R d each independently for an inorganic or organic
• Radical preferably a radical from the group consisting of halogen, cyano, nitro and radicals of the formula -Z d -R d * and R d ** , where in the radicals R d the radicals or groups
• Z d , R d * and R d ** are as defined above or below, preferably
• Z d each independently of one another is a divalent group of the formula -O-, -S (O) p-, -S (OJp-O-, -OS (O) P -, -S (O) pNR ° -, -CO- , -O-CO-, -CO-O-,
• each p is the integer O, 1 or 2 and the radicals R ° are each independently of the other hydrogen, (C r C 4 ) alkyl, phenyl, phenyl- (C r C 4 ) alkyl, (C 3 - C 6 ) cycloalkyl (C r C 4 ) alkanoyl, [(C r C 4 ) alkoxy] carbonyl or (CrC 4 ) alkylsulfonyl , especially for hydrogen or (Cr C 4 ) alkyl, phenyl, phenyl- (C r C 4 ) alkyl, (C 3 - C 6 ) cycloalkyl (C r C 4 ) alkanoyl, [(C r C 4 ) alkoxy] carbonyl or (CrC 4 ) alkylsulfonyl , especially for hydrogen or (Cr
• C 4 ) alkyl and R 1 and R "independently of one another are (Cr C 4 ) alkyl, phenyl, phenyl- (CrC 4 ) alkyl or (C 3 -C 6 ) cycloalkyl, in particular stand for (dC 4 ) alkyl, R d * and R d * * each independently of one another (CrCio) alkyl, (C 3 -Cio) alkenyl, (C 3 -Ci 0 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 4 -
• R d each independently represent hydrogen, in particular
• Z d each independently of one another is a divalent group of the formula -O-, -S (O) P -, -CO-, -O-CO-, -CO-O-, -CO -NR 0 - or -O-CO-NR 0 - means, in which p is the integer O, 1 or 2 and the radicals R 0 each independently represent hydrogen or (CrC 4 ) alkyl.
• R 1 mono- or polysubstituted (Ci-C 4 ) -alkyl, where the substituents on the alkyl group can be:
• Cio cycloalkyl] -carbamoyl, N- (CrC 4 ) alkoxy-N- (Ci-C 4 ) alkyl-carbamoyl or
• Cio alkynylsulfonyl, (C 3 -Ci 0 ) cycloalkylsulfonyl, (C 4 -Ci 0 ) cycloalkenylsulfonyl, (C 3 - Ci 0 ) cycloalkyl- (Ci-C 4 ) alkylsulfonyl, (C 4 -C 10 ) cycloalkenyl- (CrC 4 ) alkylsulfonyl, (C 3 -C 10 ) cycloalkyl- (C 3 -C 4 ) alkenylsulfonyl, (C 4 -Ci 0 ) cycloalkenyl- (C 3 -C 4 ) alkenylsulfonyl, (Ci-C 4 ) alkyl- (C 3 -Cio) cycloalkylsulfonyl, (C 2 -C 4) alkenyl (
• Cio cycloalkyl- (C 3 -C 4 ) alkenylamino, (C 4 -Cio) cycloalkenyl- (C 3 -C 4 ) alkenylamino, (Cr C 4 ) alkyl- (C 3 -Cio) cycloalkylamino, (C 2 -C 4 ) alkenyl- (C 3 -Cio) cycloalkylamino, (C 2 - C 4 ) alkynyl- (C 3 -Ci 0 ) cycloalkylamino, (Ci-C 4 ) alkyl- (C 4 -Cio) cycloalkenylamino, (C 2 - C 4 ) alkenyl- (C 4 -Cio) cycloalkenylamino or the N- (CrC 4 ) alkylamino analogs of the fourteen latter groups or
• the optionally N-substituted radicals are preferably unsubstituted on the amino group or substituted by a radical from the group (CrC 4 ) alkyl, (CrC 4 ) alkanoyl, [(Cr C 4 ) alkoxy] carbonyl and phenyl, in particular unsubstituted or by a radical from the Group (Ci-C 4 ) alkyl and phenyl, very particularly unsubstituted or substituted by (CrC 4 ) alkyl (the latter for example N-phenyl-N- (Ci-C 4 ) alkyl-carbamoyl).
• the last-mentioned radicals which contain heterocyclyl are preferably those of the formulas NHet
• N Het denotes the residue of a saturated heterocycle having at least one nitrogen atom as ring atom (N-heterocyclyl) with the free bond (yl position) on the N-ring atom, where N Het is another in addition to the N-ring atom
• R 1 is preferably (Ci-C 4 ) alkyl, (dC 4 ) alkanoyl and [(Ci-C 4 ) alkoxy] carbonyl.
• Preferred compounds (I) are those in which
• R 2 can be used for various purposes or aryl or heteroaryl provided with different substituents, these substituents being (C 1 -C 4 ) -alkyl, (CrC ⁇ -haloalkyl, halogen or alkoxy mean and heteroaryl is preferably thienyl, furyl, thiazolyl or pyridyl, in particular thienyl or pyridyl.
• the compounds of general formula (I) can be prepared by, for example, (a) a compound of general formula (II)
• R 2 is as defined in formula (I) and R 4 is hydrogen, optionally substituted alkyl or optionally substituted aryl, is converted into a compound of the formula (Ia),
• R 1 is as defined in formula (I) and L is a leaving group, such as chlorine, bromine, iodine, optionally substituted alkysulfonyl (preferably (Ci-C 4 )) alkysulfonyl, such as. B. methyl or ethylsulfonyl) or optionally substituted arylsulfonyl (preferably optionally substituted arylsulfonyl, such as, for example, phenylsulfonyl or p-toluenesulfonyl), or in the special case that R 1 is a methyl group, as an alkylating agent with dimethylformamide dimethyl acetal
• R 1 and (Y) n are as defined in formula (I),
• the ring closure reactions to give the quinoxalinones according to variants (a) and (b) can be carried out, for example, in water or an inert organic solvent in a temperature range between 20 ° C. and 150 ° C., preferably 50 ° C. and 100 ° C.
• suitable organic solvents are polar protic or aprotic solvents such as ethers, e.g. B. diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide, or alcohols such as methanol or ethanol.
• the reaction of the compounds (Ia) with the alkylating agent of the formula (IV) to give the products of the formula (I) is preferably carried out in an inert organic solvent in the presence of an acid-binding agent and in a temperature range between 20 ° C. and 150 ° C., preferably 50 0 C and 100 0 C.
• Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, for. B.
• Acid-binding agents are, for example, alkali or alkaline earth metal carbonates such as, for. B.
• alkali or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide, or alkali metal hydrides or amides, such as sodium or potassium hydride or amide, or also organic bases such as triethylamine, pyridine, dimethylaminopyridine, DBU (1, 8- Diazabicyclo [5.4.0] -undec-7-ene), DBN (1, 5-diazabicyclo [4.3.0] non-5-ene) and 1,4-diaza-bicyclo [2.2.2] octane.
• alkali or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide
• alkali metal hydrides or amides such as sodium or potassium hydride or amide
• organic bases such as triethylamine, pyridine, dimethylaminopyridine, DBU (1, 8- Diazabicyclo [5.4.0] -undec-7-ene), DBN (1, 5-diazabicyclo [4.3.
• the product of the formula (I) can be prepared by reacting the reactants in bulk or in an inert organic solvent at elevated temperature, advantageously in a range between 80 ° C. and 150 ° C.
• the derivatization reactions for process (c) come from compounds of the formula (I 1 ) which can be prepared analogously to processes (a) and (b) and which already represent compounds of the formula (I) or the like
• the invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or in particular herbicides, which cause damage to plants, characterized in that compounds of the formula (I) or their salts are used as safeners , preferably an effective amount of the compounds of formula (I) or their salts applied to the plants, parts of the plants or their seeds (or seeds).
• agrochemicals such as pesticides, or in particular herbicides
• the safeners are suitable, together with active ingredients (pesticides) for selective Control of harmful organisms to be used in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, rapeseed, cotton and soy.
• cereals wheat, barley, triticale, rye, rice, corn, millet
• sugar beet sugar cane
• rapeseed cotton and soy.
• monocotyledon crops such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledon vegetable crops, but also in dicotyledon crops such as soybean, rapeseed, cotton, wine, vegetables, Fruit plants and ornamental plants.
• Whole or partially tolerant mutant cultures or fully or partially tolerant transgenic cultures are also of interest for some pesticides, e.g. B. corn crops
• Glyphosate are resistant, or soybean cultures, which are resistant to herbicidal imidazolinones.
• the particular advantage of the new safeners is their effective effect in crops that are normally not sufficiently tolerant of the pesticides mentioned.
• the compounds of the formula (I) according to the invention can be applied together with the pesticides at the same time or in any order with the active compounds and are then able to reduce or completely eliminate harmful side effects of these active compounds in crop plants, without the effectiveness of these active compounds against undesired ones
• these agents are applied after appropriate dilution either directly to the area under cultivation, to the already germinated harmful and / or useful plants or to the already emerged harmful and / or useful plants.
• the advantageous effects of the compounds (I) according to the invention are observed if they are used together with the pesticides in the pre-emergence or in the post-emergence, for example with simultaneous application as a tank mix or as a co-formulation or with a separate application in parallel or in succession (split Application). It is also possible to repeat the application several times. Sometimes it can make sense to combine a pre-emergence application with a post-emergence application. Usually, the application is a post-emergence application to the crop or crop with simultaneous or later application of the pesticide.
• the use of the compounds (I) according to the invention in seed dressing, the (immersion) treatment of seedlings (for example rice) or the treatment of other propagation material (for example potato tubers) is also suitable.
• the agents according to the invention can contain one or more pesticides.
• pesticides are herbicides, insecticides, fungicides, acahidides and nematicides, which, when used alone, cause phytotoxic damage to the Crops would result or where damage would be likely.
• Corresponding pesticidal active substances from the groups of herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides, are of particular interest.
• the weight ratio of safener to pesticide can be varied within wide limits and is generally in the range from 1: 100 to 100: 1, preferably 1:20 to 20: 1, in particular 1:10 to 10: 1.
• the optimal weight ratio of safener to pesticide depends both on the safener used and the particular pesticide as well as on the type of crop or crop to be protected.
• the required amount of safener can be varied within wide limits, depending on the pesticide used and the type of crop to be protected, and is generally in the range from 0.001 to 10 kg, preferably 0.005 to 5 kg, in particular 0.1 to 1 kg, of safener per hectare ,
• the quantities and weight ratios required for successful treatment can be determined by simple preliminary tests.
• seed dressing for example 0.005 to 20 g of safener per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, in particular 0.05 to 5 g of safener per kg of seed, are used.
• the suitable concentration is generally in the range from 1 to 10000 ppm, preferably 100 to 1000 ppm, based on the weight.
• the quantities and weight ratios required for successful treatment can be determined by simple preliminary tests.
• the safeners can be formulated in the customary manner separately or together with the pesticides.
• the subject is therefore also the crop or crop protection agents.
• Preferred is the joint use of safener and pesticide, in particular that of safener and herbicide as a finished formulation or use in the tank mix process.
• Insecticides that can cause plant damage alone or together with herbicides are, for example, the following: organophosphates, for example Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate (Thimet ® ), Chlorpyriphos (Reldan ® ), carbamates, such as Carbofuran (Furadan ® ) , Pyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and tralomethrin (Scout ® ) as well as other insecticidal agents with a different mode of action.
• organophosphates for example Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate (Thimet ® ), Chlorpyriphos (Reldan ® ), carbamates, such as Carbofuran (Furadan ® )
• active substances whose phytotoxic effect on crops and crop plants can be reduced by the compounds (I) according to the invention are: acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] oxy] acetic acid and its methyl ester; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid, amitrol; AMS 1 ie ammonium sulfamate; anilofos
• HC-252 diphenyl ether
• imazamethabenz -methyl
• imazamethapyr imazamox
• imazapic imazapyr
• imazaquin and salts such as the ammonium salts
• imazethamethapyr imazethapyr, imazosulfuron; indanofan; iodosulfuron- (methyl) -
• MCPA thioethyl, MCPB mecoprop (-P); mefenacet; mefluidide; mesosulfuron (- methyl); mesotrione; metam, metamifop, metamitron; metazachlor; methabenzthiazuron; methazole; methoxyphenone; methyldymron; metobenzuron, metobromuron; (S-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MK-616; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, i.e.
• NC 310 ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; othosulfamuron; oryzalin; oxadiargyl (RP-020630); oxadiazone; oxasulfuron; oxaziclomefone; oxyfluorfen; paraquat; pebulate; pelargonic acid; pendimethalin; penoxulam; pentanochlor, pentoxazone; perfluidone; pethoxamide, phenisopham; phenmedipham; picloram; picolinafen; pinoxaden; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primis
• WL 110547 i.e. 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1 H-tetrazole; UBH-509; D-
• Herbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula I are, for example, herbicides from the group of the carbamates, thiocarbamates, halogenoacetanilides, substituted phenoxy, naphthoxy and phenoxyphenoxycarboxylic acid derivatives and heteroaryloxyphenoxyalkane carboxylic acid derivatives, such as quinolyloxy, Quinoxalyloxy, pyridyloxy, Benzoxazolyloxy and benzothiazolyloxyphenoxyalkane carboxylic acid esters, cyclohexanedionoximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylhamidonidyl derivatives, sul
• Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, sulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones and mixtures of the active ingredients mentioned, which are used with one another and / or with the active ingredients, for example, for the purpose of and for enhancing the active ingredients, are used with one another and / or with the active ingredients, for example, for and to enhance the active ingredients, Bentazone, Cyanazine, Atrazine, Bromoxynil, Dicamba and other leaf herbicides.
• Suitable herbicides which can be combined with the safeners according to the invention are, for example:
• Phenoxyphenoxy and benzyloxyphenoxy carboxylic acid derivatives e.g. 2- (4-
• Triazinylaminocarbonyl-fbenzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) - alkylamino -] - sulfamides Preferred as a substituent on the pyrimidine ring or
• Triazine rings are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another.
• Substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl) alkylamino part are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl,
• Alkylaminocarbonyl dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy
• Haloalkyl alkylcarbonyl, alkoxyalkyl, (alkanesulfonyl) alkylamino.
• alkanesulfonyl alkylamino.
• sulfone diamide derivatives e.g. 3- (4,6-Dimethoxypyrimidin-2-yl) -1- (N-methyl-N-methylsulfonylaminosulfonyl) urea (amidosulfuron) and its structural analogs (EP-A 0 131 258 and Z. PfI. Krank. PfI. Protection , Special Issue XII, 489-497 (1990));
• pyridylsulfonylureas e.g. 1- (3-N, N-dimethylaminocarbonylpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (nicosulfuron),
• alkoxyphenoxysulfonylureas e.g. B.
• Acetochlor alachlor, butachlor, dimethachlor, dimethenamid, metazachlor, metolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and thenylchlor;
• Imazamethabenz-methyl imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
• G) triazolopyrimidine sulfonamide derivatives e.g. Chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam and penoxulam;
• M phosphinic acids and derivatives, e.g. B. 4- [hydroxy (methyl) phosphinoyl] -L-homoalanyl-L-alanyl-L-alanine (Bilanafos), DL-homoalanin-4-yl (methyl) phosphinic acid ammonium salt (glufosinate ammonium);
• N) glycine derivatives e.g. B. ⁇ / - (phosphonomethyl) glycine and its salts (glyphosate and salts, e.g. the sodium salt or the isopropylammonium salt), ⁇ / - (phosphonomethyl) glycine trimesium salt (sulfosate);
• S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid esters such as S- [N- (4-chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-dimethyl-dithiophosphate (Anilophos);
• T) pyridinecarboxamides e.g. B. Diflufenican and Picolinafen;
• V Plant growth regulators, e.g. B. Forchlorfenuron and thidiazuron.
• ketoenols e.g. B. 8- (2,6-diethyl-p-tolyl) -1, 2,4,5-tetrahydro-7-oxo-7H-pyrazolo [1,2-d] [1,4,5] oxadiazepine-9 -yl 2,2-dimethylpropionate (Pinoxaden).
• the herbicides of groups A to W are known, for example, from the publications mentioned above and from "The Pesticide Manual", The British Crop Protection Council, 13th Edition, 2003, or the e-Pesticide Manual, Version 3.0, British Crop Protection Council 2003 ,
• the compounds of the general formula (I) and their combinations with one or more of the pesticides mentioned can be formulated in various ways depending on the given chemical-physical and biological parameters. Examples of suitable types of formulation are:
• Emulsifiable concentrates which are obtained by dissolving the active ingredients in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, XyIoI or higher-boiling hydrocarbons or mixtures of organic solvent
• organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, XyIoI or higher-boiling hydrocarbons or mixtures of organic solvent
• Solvents with the addition of one or more surfactants of ionic and / or nonionic type are prepared.
• Suitable emulsifiers are for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkyaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters;
• Dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours. suspension concentrates based on water or oil, which can be prepared, for example, by wet grinding using bead mills; - water soluble powder; water soluble concentrates;
• Granules such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
• Wettable powders which, in addition to the active substance, also contain diluents or inert substances and surfactants;
• the crop protection agents can optionally include customary adhesives, wetting agents, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH or the like Contain viscosity-influencing agents.
• the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula (I) or a combination of safener and pesticide , They also contain 1 to 99.9, in particular 4 to 99.5% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant.
• the active substance concentration in emulsifiable concentrates is the concentration of safener and / or pesticide, usually 1 to 90, in particular 5 to 80 wt .-%. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient.
• the active substance concentration in wettable powders is generally 10 to 90% by weight.
• the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
• the formulations present in commercial form are optionally diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Dust-like preparations, granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• the application rate of the safener varies with the external conditions, such as temperature, humidity, the type of herbicide used and others. In the following examples, which illustrate but do not limit the invention, the amounts given relate to the weight, unless otherwise specified.
• a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of the formula (I) and 90 parts by weight of talc as an inert substance and crushed in a hammer mill.
• a pesticide e.g. herbicide
• a safener of the formula (I) 90 parts by weight of talc as an inert substance and crushed in a hammer mill.
• a water-dispersible, wettable powder is obtained by adding 25 parts by weight of a compound of the formula (I) or a mixture of active ingredients from a pesticide (e.g. herbicide) and a safener of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance , 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and ground in a pin mill.
• a pesticide e.g. herbicide
• a safener of the formula (I) 64 parts by weight of kaolin-containing quartz as an inert substance
• 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and ground in a pin mill.
• a water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) or a mixture of active ingredients from a pesticide (e.g. herbicide) and a safener of the formula (I) with 6 parts by weight Alkylphenol polyglycol ether ( ® Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil are mixed and ground in a attritor to a fineness of less than 5 microns.
• a pesticide e.g. herbicide
• a safener of the formula (I) with 6 parts by weight Alkylphenol polyglycol ether ( ® Triton X 207)
• 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil are mixed and ground in a attritor to a fineness of less than 5 microns.
• An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 Parts by weight of oxyethylated nonylphenol as an emulsifier.
• a pesticide e.g. herbicide
• 75 parts by weight of cyclohexanone as solvent
• 10 Parts by weight of oxyethylated nonylphenol as an emulsifier.
• a water-dispersible granulate is obtained by:
• a water-dispersible granulate is also obtained by
• Example No. 405 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.59 (s, 3H, CH 3); 2.68 (q, 4H, CH 2 CH 3); 2.75 (tr, 2H, NCH 2); 4.35 (tr, 2H, CH 2 Het); 7.82 (d, 1H, quinoxaline-H)
• Example No. 408 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 1.31 (d, 6H, iPrCH3); 2.69 (q, 4H, CH 2 CH 3); 2.75 (tr, 2H, NCH 2); 3.62 (sept, 1H, methine-H); 4.35 (tr, 2H, CH 2 Het); 7.83 (d, 1H, quinoxaline-H)
• Example No. 412 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 1, 49 (s, 9H, C (CH 3) 3); 2.65 (q, 4H, CH 2 CH 3); 2.75 (tr, 2H, NCH 2); 4.32 (tr, 2H, CH 2 Het); 7.82 (d, 1H, quinoxalinone-H)
• Example No. 415 (CDCI 3 ) 1, 12 (tr, 6H, CH 2 CH 3 ); 1.88-2.12 (m, 6H, cyclopentyl-H); 2.43 - 2.58 (m, 2H, cyclopentyl-H); 2.71 (q, 4H, CH 2 CH 3 ); 2.81 (tr, 2H, NCH 2); 4.44 (tr, 2H, CH 2 Het); 7.97 (d, 1H, quinoxalinone-H)
• Example No. 431 (CDCI 3 ) 1.08 (tr, 6H, CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 8.50 (m, 2H, phenyl-H)
• Example No. 434 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3 ); 2.48 (s, 3H, CH3); 2.69 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.40 (tr, 2H, CH 2 Het); 7.75 (s, 1H, quinoxalinone-H); 8.30 (m, 2H, phenyl-H)
• Example No. 451 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.66 (q, 4H, CH 2 CH 3); 2.81 (tr, 2H, NCH 2); 4.43 (tr, 2H, CH 2 Het); 8.23 (s, 1H, quinoxalinone-H); 8.34 (m, 2H, phenyl-H)
• Example No. 478 (CDCI 3 ) 1, 07 (tr, 6H 1 CH 3 ); 2.65 (q, 4H, CH 2 CH 3); 2.79 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 8.48 (d, 1H, Th)
• Example No. 481 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.51 (s, 3H, CH 3); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H 1 NCH 2 ); 4.38 (tr, 2H, CH 2 Het); 8.47 (d, 1H, Th)
• Example No. 482 (CDCI 3 ) 1, 50 (tr, 6H 1 CH 2 CH 3 ); 3.29 (m, 6H, 3CH 2); 4.99 (tr, 2H 1 CH 2 Het); 8.42 (2d, 2H, thienyl-H, quinoxaline-H)
• Example No. 486 (CDCI 3 ) 1.05 (tr, 6H, CH 3 ); 2.65 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.38 (tr, 2H, CH 2 Het); 8.48 (d, 1H, Th)
• Example No. 487 (CDCI 3 ) 1, 02 (tr, 6H, CH 3 ); 2.65 (q, 4H, CH 2 CH 3); 2.78 (tr, 2H, NCH 2); 4.38 (tr, 2H, CH 2 Het); 8.48 (d, 1H, Th)
• Example No. 501 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3 ); 2.36, 2.42 (2s, 6H, 2CH 3); 2.69 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 8.42 (d, 1H, Th)
• Example No. 507 (CDCI 3 ) 1, 03 (tr, 6H, CH 2 CH 3 ); 2.62 (q, 4H, CH 2 CH 3); 2.79 (tr, 2H, NCH 2); 4.36 (tr, 2H, CH 2 Het); 7.58, 7.98 (2s, 2H 1 quinoxalinone-H); 8.48 (d, 1H, thiophene-H)
• Example No. 525 (CDCI 3 ) 1, 09 (tr, 6H, CH 3 ); 1.47 (tr, 3H, ester-CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.83 (tr, 2H 1 NCH 2 ); 4.47 (m, 4H 1 OCH 2 , CH 2 Het); 8.44 (d, 1H, Th)
• Example No. 525 (CDCI 3 ) 1, 09 (tr, 6H, CH 3 ); 1.47 (tr, 3H, ester-CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.83 (tr, 2H 1 NCH 2 ); 4.47 (m, 4H 1 OCH 2 , CH 2 Het); 8.44 (d, 1H, Th)
• Example No. 525 (CDCI 3 ) 1, 09 (tr, 6H, CH 3 ); 1.47 (tr, 3H, ester-CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.83 (tr, 2
• Example No. 527 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.42 (s, 3H 1 ToIyI-CH 3 ); 2.69 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.41 (tr, 2H, CH 2 Het); 7.95 (d, 1H, quinoxalinone-H); 8.10 (d, 2H, phenyl-H)
• Example No. 529 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 1.36 (s, 9H, tert -butyl); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 7.94 (d, 1H, quinoxalinone-H); 8.12 (d, 2H, phenyl-H)
• Example No. 529 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 1.36 (s, 9H, tert -butyl); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 7.94 (d, 1H, quinoxalinone-H); 8.12 (d, 2H, phenyl-H)
• Example No. 529 1, 09 (tr, 6H, CH 2 CH 3 ); 1.36
• Example No. 536 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3 ); 2.69 (q, 4H, CH 2 CH 3); 2.81 (tr, 2H, NCH 2); 3.89 (s, 3H, OCH 3 ); 4.42 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 6.99, 8.38 (2d, 4H, phenyl-H)
• Example No. 536 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3 ); 2.69 (q, 4H, CH 2 CH 3); 2.81 (tr, 2H, NCH 2); 3.89 (s, 3H, OCH 3 ); 4.42 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 6.99, 8.38 (2d, 4H, phenyl-H)
• Example No. 536 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3
• Example No. 543 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.35, 2.38 (2s, 6H, dimethylphenyl CH 3 ); 2.69 (q, 4H, CH 2 CH 3); 2.83 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 7.16 (s, 1H, phenyl-H); 7.96 (d, 1H, quinoxalinone-H);
• Example No. 546a (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.34, 2.37 (2s, 6H, dimethylphenyl CH 3 ); 2.67 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 7.94 (d, 1H, quinoxalinone-H); 8.07 (d, 1H, phenyl-H); 8.09 (s, 1H, phenyl-H);
• Example No. 547 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.40 (s, 6H, dimethylphenyl CH 3 ); 2.69 (q, 4H 1 CH 2 CH 3 ); 2.81 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 7.11 (s, 1H, phenyl-H); 7.88 (s, 2H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H);
• Example No. 548 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.07 (s, 6H, trimethylphenyl CH 3 ); 2.33 (s, 3H, trimethylphenyl CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.83 (tr, 2H, NCH 2); 4.42 (tr, 2H 1 CH 2 Het); 6.94 (s, 2H 1 phenyl-H); 7.97 (d, 1H, quinoxalinone-H); Example No.
• Example No. 560 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.69 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.30 (m, 4H, OCH 2 ); 4.41 (tr, 2H, CH 2 Het); 6.96 (d, 1H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H); 7.95 (m, 2H 1 phenyl-H);
• Example No. 561 (CDCI 3 ) 1.08 (tr, 6H 1 CH 2 CH 3 ); 2.67 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, NCH 2); 4.40 (tr, 2H 1 CH 2 Het); 7.55 (d, 1H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H); 7.95 (m, 2H, phenyl-H); Example No.
• Example No. 569 (CDCI 3 ) 1, 10 (tr, 6H, CH 3 ); 2.69 (q, 4H, CH 3 CH 2); 2.80 (tr, 2H, CH 2 NEt 2 ); 4.43 80 (tr, 2H, CH 2 Het); 8.90 (d, 1H, thienyl)
• Example No. 570 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.81 (tr, 2H, NCH 2); 4.42 (tr, 2H, CH 2 Het); 6.62 (dd, 1H, furyl-H); 7.72 (d, 1H, furyl-H); 7.93 (d, 1H, furyl-H); 8.02 (d, 1H, quinoxalinone-H);
• Example No. 575a (CDCI 3 ) 1, 23 (tr, 6H, CH 2 CH 3 ); 3.31 (m, 6H, CH 2 CH 3, NCH 2); 4.82 (tr, 2H, CH 2 Het); 8.09, 8.18 (2 dd, 2H, pyridyl-H, quinoxalinone-H); 8.88 (dd, 1H, pyridyl-H);
• Example No. 575a (CDCI 3 ) 1, 23 (tr, 6H, CH 2 CH 3 ); 3.31 (m, 6H, CH 2 CH 3, NCH 2); 4.82 (tr, 2H, CH 2 Het); 8.09, 8.18 (2 dd, 2H, pyridyl-H, quinoxalinone-H); 8.88 (dd, 1H, pyridyl-H);
• Example No. 575a (CDCI 3 ) 1, 23 (tr, 6H, CH 2 CH 3 ); 3.31 (m, 6H, CH 2 CH 3, N
• Example No. 579 (CDCI 3 ) 1, 10 (tr, 6H, CH 2 CH 3 ); 2.48 (s, 3 H 1 CH 3 Pyr); 2.68 (q, 4H, CH 2 CH 3); 2.82 (tr, 2H, NCH 2); 4.41 (tr, 2H, CH 2 Het); 7.21 (d, 1H, pyridyl-H); 8.09 (d, 1H, quinoxalinone-H); 8.10 (s, 1H, pyridyl-H); 8.71 (d, 1H, pyridyl-H)
• Example No. 581a (CDCI 3 ) 1, 43 (tr, 6H, CH 2 CH 3 ); 2.71 (s, 3 H 1 CH 3 Pyr); 3.31 (m, 6H, CH 2 CH 3, NCH 2); 4.83 (tr, 2H, CH 2 Het); 7.31 (d, 1H, pyridyl-H); 7.90 (d, 1H, pyridyl-H); 8.07 (d, 1H, quinoxalinone-H); Example No.
• 588a (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H 1 CH 2 CH 3 ); 2.78 (s, 3H, CH 3 Th); 2.82 (tr, 2H, NCH 2); 4.43 (tr, 2H, CH 2 Het); 7.02 (d, thienyl-H); 7.92 (d, 1H, quinoxalinone-H);
• Example No. 595 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.45, 2.63 (2s, 6H, 2 CH 3 Th); 2.70 (q, 4H, CH 2 CH 3 ); 2.78 (tr, 2H, NCH 2); 4.43 (tr, 2H, CH 2 Het); 7.29 (s, thienyl-H); 7.89 (d, 1H, quinoxalinone-H);
• Example No. 612 (CDCI 3 ) 1, 32 (d, 6H, 2CH 3 ); 3.61 (sept, 1H, methine-H); 3.78 (s, 3H, OCH 3 ); 2.80 (tr, 2H, NCH 2); 5.05 (s, 2H, CH 2 Het); 7.98 (d, 1H, quinoxaline-H)
• Example No. 638 (CDCI 3 ) 3.80 (s, 3H, OCH 3 ); 5.12 (s, 2H, CH 2 Het); 8.32 (m, 2H, phenyl-H)
• Example No. 688 (CDCI 3 ) 2.76 (s, 3H, CH 3 ); 3.78 (s, 3H, OCH 3 ); 5.14 (s, 2H, CH 2 Het); 8.47 (d, 1H, thienyl-H)
• Example No. 689 (CDCI 3 ) 2.52 (s, 3H, CH 3 ); 3.80 (s, 3H, OCH 3 ); 5.12 (s, 2H, CH 2 Het); 8.47 (d, 1H, thienyl-H)
• Example No. 691 (CDCI 3 ) 2.62 (s, 3H, CH 3 ); 3.80 (s, 3H, OCH 3 ); 5.17 (s, 2H, CH 2 Het); 8.34 (d, 1H, thienyl-H)
• Example No. 708 (CDCI 3 ) 2.35, 2.41 (2s, 6H, 2CH 3 ); 3.78 (s, 3H, OCH 3 ); 5.12 (s, 2H, CH 2 Het); 8.45 (d, 1H, thienyl-H)
• Example No. 856 (CDCI 3 ) 1, 21 (tr, 3H, CH 3 ); 3.71 (q, 2H, CH 2 Et); 5.82 (s, 2H, CH 2 Het); 8.28 (m, 2H, Ph)
• Example No. 857 (CDCI 3 ) 3.37 (s, 3H, CH 3 ); 3.80 (tr, 2H, OCH 2); 4.53 (tr, 2H, CH 2 Het); 8.30 (m, 2H, Ph)
• Example No. 858 (CDCI 3 ) 1, 15 (tr, 3H, CH 3 ); 3.51 (q, 2H, CH 2 Et); 3.82 (s, 2H, OCH 2); 8.30 (m, 2H, Ph)
• Example No. 861 (CDCI 3 ) 1, 09 (s, 9H, C (CH 3 ) 3 ); 3.78 (tr, 3H, CH 2 O); 4.49 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 8.30 (m, 2H, phenyl-H)
• Example No. 862 (CDCI 3 ) 3.32 (s, 3H, OCH 3 ); 3.50, 3.65 (2m, 4H, OCH 2 CH 2 O); 3.90 (tr, 2H, OCH 2); 4.57 (tr, 2H 1 CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 8.30 (m, 2H, phenyl-H)
• Example No. 883 (CDCI 3 ) 3.30 (tr, 2H, SCH 2 ); 4.50 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxaline-H) 8.47 (m, 2H, Ph)
• Example No. 907 (CDCI 3 ) 1, 31 (tr, 6H, 2CH 3 ); 2.29 (sext, 2H, CH2) 3.05-3.30 (m, 6H, 3CH 2 N); ): 4.41 (tr, 2H, CH 2 Het); 7.95 (d, 1H, quinox.-H) 8.38 (m, 2H, Ph)
• Example No. 913 (CDCI 3 ) 2.00 (quintet, 2H, CH 2 CH 2 CH 2 ); 2.50 (m, 6H, 3CH 2 N) 3.71 (tr, 4H, CH 2 O;): 4.42 (tr, 2H, CH 2 Het); 7.95 (d, 1H, quinox.-H) 8.40 (m, 2H, Ph)
• Example No. 1010 (CDCI 3 ) 1, 32, 1, 42 (2s, 6H, 2CH 3 ); 3.91, 4.17 (2dd, 2H, OCH 2 ); 4.34, 4.68 (2dd, 2H, CH 2 Het); 4.56 (m, 1H, methine-H), 8.30 (m, 2H, phenyl-H)
• Example No. 1011 (CDCI 3 ) 1, 32, 1, 42 (2s, 6H, 2CH 3 ); 3.91, 4.17 (2dd, 2H, OCH 2 ); 4.34, 4.68 (2dd, 2H 1 CH 2 Het); 4.56 (m, 1H, methine-H), 8.30 (m, 2H, phenyl-H)
• Example No. 1088 (CDCI 3 ) 3.32 (s, 3H, OCH 3 ); 3.48, 3.65 (2m, 4H, OCH 2 CH 2 O); 3.90 (tr, 2H, OCH 2); 4.58 (tr, 2H, CH 2 Het); 7.88 (d, 1H, quinoxalinone-H); 8.48 (dd, 1H, thienyl-H)
• Example No. 1103 (CDCI 3 ) 3.34, 3.42 (2s 6H, 2CH 3 ); 3.48, 3.68 (2dd, 2H 1 OCH 2 ); 3.88 (m, 1H, methine-H); 4.53 (dd, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1106 (CDCI 3 ) 1, 34 (tr, 3H, CH 3 ); 2.74 (q, 2H, CH 2 CH 3 ); 2.90 (tr, 2H, SCH 2 CH 2 ); 4.52 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1108 (CDCI 3 ) 1.35 (d, 6H, 2CH 3 ); 2.91 (tr, 2H, SCH 2 ); 3.13 (sept, 1H, methine-H); 4.52 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1110 (CDCI 3 ) 3.29 (tr, 2H 1 SCH 2 ); 4.50 (tr, 2H, CH 2 Het); 7.88 (d, 1H, quinoxaline-H); 8.48 (d, 1H, thienyl)
• Example No. 1111 (CDCI 3 ) 3.07 (tr, 2H, SCH 2 ); 3.29 (q, 2H, SCH 2 CF 3 ); 4.58 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1112 (CDCI 3 ) 1, 50-1, 70, 1, 70-1, 80, 2.05-2.15 (3m, 8H, cyclopentyl); 2.91 (tr, 2H, SCH 2 ); 3.31 (quint, 1H, methine-H); 4.53 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1113 (CDCI 3 ) 2.90 (tr, 2H, SCH 2 ); 3.89 (s, 2H, SCH 2 furyl); 4.51 (tr, 2H, CH 2 Het); 6.31 (s, 2H, furyl-H); 8.48 (d, 1H, thienyl)
• Example No. 1129 (CDCI 3 ) 1, 02 (d, 12H, 4CH 3 ) 2.79 (tr, 2H, NCH 2 ); 3.09 (sept, 2H, methine-H); 4.32 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1134 (CDCI 3 ) 1, 48 (m, 2H, CH 2 ) 1, 62 (m, 4H, 2CH 2 ); 2.50-2.95 (m, 6H, 3NCH 2 ); 4.49 (tr, 2H, CH 2 Het); 8.48 (d, 1H, thienyl)
• Example No. 1145 (CDCI 3 ) 2.20 (sext, 2H, CH 2 ) 2.42-2.55 (m, 6H, 3CH 2 N); 3.70 (tr, 4H, OCH 2); 4.44 (tr, 2H, CH 2 Het); 7.92 (d, 1 H, quinox.-H) 8.47 (d, 1 H, thienyl)
• Example No. 1146 (DMSO) 0.87 (d, 3H, CH 3 ) 2.12 (s, 6H, CH 3 N); 2.10-2.40 (m, 3H, methine-H, NCH 2 ); 4.33 (m, 2H, CH 2 Het); 7.92 (d, 2H, quinox.-H) 8.40 (d, 1H, thienyl)
• Example No. 1147 (CDCI 3 ) 2.33 (d, 3H, CH 3 ) 2.92 (s, 6H, CH 3 N); 3.90 (m, 1H, methine-H); 4.68, 4.95 (2dd, 2H, CH 2 Het); 7.92 (d, 2H, quinox.-H) 8.45 (d, 1H, thienyl)
• Example No. 1149 (CDCI 3 ) 1, 65-1, 90 (m, 6H, 3CH 2 ) 2.05-2.20 (m, 2H, CH 2 N); 2.38 (s, 3H, CH 2); 3.12 (tr, 1H, methine-H); 4.32, 4.49 (2m, 2H, CH 2 Het); 7.92 (d, 2H, quinox.-H) 8.48 (d, 1H, thienyl)
• Example No. 1151 (CDCI 3 ) 1, 43 (m, 1 H); 1.85-2.10 (m, 3H,); 2.38 (s, 3H, CH 2); 2.55-2.90 (m, 3H); 3.78 (s, 3H, CH 3); 3.60 (dd, 2H); 4.32 (dd, 2H, CH 2 Het); 7.92 (d, 2H, quinox.-H) 8.42 (d, 1H, thienyl)
• Example No. 1152 (CDCI 3 ) 2.87 (s, 3H, CH 3 ); 3.60 (dd, 2H); 4.32, 4.60 (2m, 2H, CH 2 Het); 7.92 (d, 2H, quinox.-H) 8.45 (d, 1H, thienyl)
• Example No. 1196 (CDCI 3 ) 1.41 (d, 3H, CH 3 ); 4.30-4.40 (m, 2H,); 4.45-4.60 (m, 1H); 7.92 (d, 2H, quinox.-H) 8.47 (d, 1H, thienyl)
• Example No. 1197 (DMSO) 3.51 (m, 2H, OCH 2 ); 3.98 (m, 1H, methine-H); 4.39 (d, 2H, CH 2 Het); 4.80 (tr, 1 H, CH 2 OH), 4.93 (d, 1 H, CHOH) 8.40 (d, 1 H, thienyl)
• Example No. 1243 (CDCI 3 ) 1, 32, 1, 41 (2s, 6H, 2CH 3 ); 3.92, 4.18 (2dd, 2H, OCH 2 ); 4.35, 4.70 (2dd, 2H, CH 2 Het); 4.58 (m, 1H, methine-H), 8.48 (d, 1H, thienyl)
• Example No. 1244 (CDCI 3 ) 1, 32, 1, 41 (2s, 6H, 2CH 3 ); 3.92, 4.18 (2dd, 2H, OCH 2 ); 4.35, 4.70 (2dd, 2H, CH 2 Het); 4.58 (m, 1H 1 methine-H), 8.48 (d, 1H, thienyl)
• Example No. 1268 (CDCI 3 ) 1, 31 (d, 6H, JPrCH 3 ); 1.69 (d, 2H, crotyl-CH 3 ); 3.67 (sept, 1H, methine-H); 4.83 (m, 2H, CH 2 Het); 5.59, 5.82 (2m, 2H, olefin-H); 7.93 (d, 2H, quinox.-H)
• Example No. 1273 (CDCI 3 ) 1, 52 (tr, 6H, CH 2 CH 3 ); 2.52 (s, 3H CH 3); 3.49 (m, 6H, CH 2 CH 3, NCH 2); 5.03 (tr, 2H, CH 2 Het); 6.32, 7.97 (2d, 2H, furyl-H); 8.32 (d, 1H, quinoxalinone-H);
• Example No. 1282 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.10 (m, 2H, 2-indanyl-CH 2 ); 2.48 (s, 3H CH 3); 2.80 (tr, 4H, CH 2 CH 3 ); 2.96 (m, 4H, 1,3-indanyl-CH 2 ); 4.42 (tr, 2H, CH 2 Het); 7.92 (d, 1H 1 quinoxalinone-H); 8.08 (d, 1H, indan-6-yl-H); 8.13 (d, 1H, indan-4-yl-H)
• Example No. 1283 (CDCI 3 ) 1.08 (tr, 6H, CH 2 CH 3 ); 2.10 (m, 2H, 2-indanyl-CH 2 ); 2.68 (q, 4H, CH 2 CH 3 ), 2.80 (tr, 2H, NCH 2 ); 2.96 (m, 4H, 1,3-indanyl-CH 2 ); 4.42 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 8.08 (d, 1H, indan-6-yl-H); 8.13 (d, 1H, indan-4-yl-H)
• Example No. 1296 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.91, 4.18, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet, 1H, methine-H); 7.95 (d, 1H, quinoxalinone-H); 8.30 (m, 2H, phenyl-H)
• Example No. 1297 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.91, 4.18, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet, 1H, methine-H); 7.90 (d, 1H, quinoxalinone-H); 8.48 (d, 1H, thienyl-H)
• Example No. 1297 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.91, 4.18, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet, 1H, methine-H); 7.90 (d, 1H, quinoxalinone-H); 8.48 (d, 1H, thienyl-H)
• Example No. 1297 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.91, 4.18, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet,
• Example No. 1300 (CDCI 3 ) 2.2, 2.43-2.70 (2m, 1H, 3H CH 2 CH 2 CO); 4.43, 4.78 (2dd, 2H, CH 2 N); 4.97 (m, 1H, methine-H); 7.96 (d, 1H, quinoxalinone-H); 8.30 (m, 2H, phenyl-H)
• Example No. 1290 (CDCI 3 ) 1, 52 (tr, 6H, CH 2 CH 3 ); 2.34, 2.38 (2s, 6H, 2CH 3 ) 3.29 (m, 6H, CH 2 CH 3 , NCH 2 ); 5.00 (tr, 2H, CH 2 Het); 8.0-8.2 (m, 5H, phenyl-H, quinoxalinone-H);
• Example No. 1301 (CDCI 3 ) 2.2, 2.43-2.70 (2m, 1H, 3H CH 2 CH 2 CO); 4.43, 4.78 (2dd, 2H, CH 2 N); 4.97 (m, 1H, methine-H); 7.90 (d, 1H, quinoxalinone-H); 8.45 (d, 1H, quinoxalinone-H)
• Example No. 1301 (CDCI 3 ) 2.2, 2.43-2.70 (2m, 1H, 3H CH 2 CH 2 CO); 4.43, 4.78 (2dd, 2H, CH 2 N); 4.97 (m, 1H, methine-H); 7.90 (d, 1H, quinoxalinone-H); 8.45 (d, 1H, quinoxalinone-H)
• Example No. 1301 (CDCI 3 ) 2.2, 2.43-2.70 (2m, 1H, 3H CH 2 CH 2 CO); 4.43, 4.78 (2dd, 2H, CH 2 N); 4.97 (m, 1H, methine
• Example No. 1309 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.65 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, CH 2 N); 4.40 (tr, 2H, CH 2 Het); 7.40, 7.57 (2d 2H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1310 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H 1 CH 2 CH 3 ); 2.81 (tr, 2H, CH 2 N); 4.42 (tr, 2H, CH 2 Het); 7.40, 7.57 (2d 2H, phenyl-H); 7.92 (d, 1H, quinoxalinone-H); 8.36 (d 2H, phenyl-H)
• Example No. 1310 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H 1 CH 2 CH 3 ); 2.81 (tr, 2H, CH 2 N); 4.42 (tr, 2H, CH 2 Het); 7.40, 7.57 (2d 2H, phenyl-H); 7.92 (d, 1H, quinoxalinone-H); 8.36 (d 2H, phenyl-H)
• Example No. 1310 (CDCI 3 ) 1, 09 (tr, 6H, CH 2
• Example No. 1315 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.82 (tr, 2H, CH 2 N); 4.41 (tr, 2H, CH 2 Het); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1315 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.82 (tr, 2H, CH 2 N); 4.41 (tr, 2H, CH 2 Het); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1315 (CDCI 3 ) 1, 07 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.82 (tr, 2H, CH 2 N); 4.41 (tr, 2H, CH 2 Het); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1326 (CDCI 3 ) 1, 38, 1, 50 (2s, 6H, CH 3 ); 1, from 9 to 2.2 (m, 2H, CH 2); 3.63, 4.11 (2dd, 2H, CH 2 O); 4.27 (m, 1H, methine-H); 4.49 (tr, 2H, CH 2 Het); 7.95 (d, 1H, quinoxalinone-H); 8.29 (d, 2H, phenyl-H)
• Example No. 1328 (CDCI 3 ) 1, 38, 1, 50 (2s, 6H, CH 3 ); 1, from 9 to 2.2 (m, 2H, CH 2); 3.63, 4.11 (2dd, 2H, CH 2 O); 4.27 (m, 1H, methine-H); 4.49 (tr, 2H, CH 2 Het); 7.95 (d, 1H, quinoxalinone-H); 8.29 (d, 2H, phenyl-H)
• Example No. 1330 (CDCI 3 ) 1.04 (d, 3H, CH (CH 3 )); 1, 29 (tr, 3H, CH 2 CH 3); 2.42 (m, 1H, methine-H), 3.38 (d, 2H, CHCH 2 O); 3.43 (q, 2H, OCH 2 CH 3 ), 4.37 (d, 2H, CH 2 Het); 7.93 (d, 1H, quinoxalinone-H); 8.29 (d, 2H, phenyl-H)
• Example No. 1331 (CDCI 3 ) 1.05 (d, 3H, CH (CH 3 )); 1, 28 (tr, 3H, CH 2 CH 3 ); 2.42 (m, 1H, methine-H), 3.37 (d, 2H, CHCH 2 O); 3.43 (q, 2H, OCH 2 CH 3 ), 4.38 (d, 2H, CH 2 Het); 7.90 (d, 1H, quinoxalinone-H); 8.48 (d, 1H, thienyl-H)
• Example No. 1331 (CDCI 3 ) 1.05 (d, 3H, CH (CH 3 )); 1, 28 (tr, 3H, CH 2 CH 3 ); 2.42 (m, 1H, methine-H), 3.37 (d, 2H, CHCH 2 O); 3.43 (q, 2H, OCH 2 CH 3 ), 4.38 (d, 2H, CH 2 Het); 7.90 (d, 1H, quinoxalinone-H); 8.48 (d, 1H, thieny
• Example No. 1333 (CDCI 3 ) 1, 03 (s, 6H, C (CH 3 ) 2 ); 3.10 (3, 2H, OCH 2 ); 3.35 (s, 3H, OCH 3 ); 4.39 (tr, 2H, CH 2 Het); 7.92 (d, 1H, quinoxalinone-H); 8.28 (d, 2H, phenyl-H)
• Example No. 1335 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, CH 2 N); 4.42 (tr, 2H, CH 2 Het); 5.15 (s, 2H, benzyl CH 2 ); 7.08, 8.38 (2d, 4H 1 C 6 H 4 ); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1342 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.89 (s, 3H OCH 3); 3.91, 4.16, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet, 1H, methine-H); 7.00, 8.38 (2d, 4H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H)
• Example No. 1343 (CDCI 3 ) 1, 32, 1, 42 (2d, 6H, CH 3 ); 3.42 (s, 3H tolyl-CH 3); 3.91, 4.16, 4.33, 4.69 (4dd, 4H, 2CH 2 ); 4.57 (quintet, 1H, methine-H); 7.28, 8.22 (2d, 4H 1 phenyl-H); 7.93 (d, 1H, quinoxalinone-H);
• Example No. 1355 (CDCI 3 ) 3.68 (2tr, 4H, 2CH 2 N); 4.29 (tr, 2H, CH 2 Het); 4.58 (tr, 2H CH 2 O); 7.93 (d, 1H, quinoxalinone-H); 8.45 (i.e. 1 H, thienyl-H)
• Example No. 1358 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.36 (s, 3H, CH 3 aryl); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, CH 2 N); 4.42 (tr, 2H, CH 2 Het); 5.15 (s, 2H, benzyl CH 2 ); 7.93 (d, 1H, quinoxalinone-H); 8.20 (m, 2H, phenyl-H)
• Example No. 1358 (CDCI 3 ) 1, 09 (tr, 6H, CH 2 CH 3 ); 2.36 (s, 3H, CH 3 aryl); 2.68 (q, 4H, CH 2 CH 3); 2.80 (tr, 2H, CH 2 N); 4.42 (tr, 2H, CH 2 Het); 5.15 (s, 2H, benzyl CH 2 ); 7.93 (d, 1H, quinoxalinone-H); 8.20 (m, 2H, phenyl-
• Example No. 1381 (CDCI 3 ) 2.25 (s, 3H, ToIyI-CH 3 ); 2.92 (s, 3H 1 NCH 3 ); 3.73 (tr, 2H, CH 2 N); 4.52 (tr, 2H, CH 2 Het); 6.75, 7.09 (2d, 4H 1 phenyl-H); 7.91 (d, 1H, quinoxalinone-H); 8.49 (d, 1H, thienyl-H)
• Example No. 1382 (CDCI 3 ) 2.27 (s, 3H, ToIyI-CH 3 ); 2.97 (s, 3H, NCH 3); 3.75 (tr, 2H, CH 2 N); 4.50 (tr, 2H, CH 2 Het); 6.75, 7.09 (2d, 4H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H); 8.29 (m, 2H, phenyl-H)
• Example No. 1382 (CDCI 3 ) 2.27 (s, 3H, ToIyI-CH 3 ); 2.97 (s, 3H, NCH 3); 3.75 (tr, 2H, CH 2 N); 4.50 (tr, 2H, CH 2 Het); 6.75, 7.09 (2d, 4H, phenyl-H); 7.93 (d, 1H, quinoxalinone-H); 8.29 (m, 2H, phenyl-H)
• Example No. 1386 (CDCI 3 ) 2.98 (s, 3H 1 NCH 3 ); 3.80 (tr, 2H, CH 2 N); 4.57 (tr, 2H, CH 2 Het); 7.91 (d, 1H, quinoxalinone-H); 8.49 (d, 1H, thienyl-H)
• Example No. 1395 (CDCI 3 ) 1, 28 (tr, 3H, CH 2 CH 3 ); 2.36, 2.40 (2s, 6H, 6,7-Me 2); 4.25 (q, 2H, CH 2 CH 3); 5.10 (s, 2H, CH 2 N); 6.88, 7.69 (2s, 2H, quinoxalinone-H); 7.28, 7.55, 8.45 (tr, d, d, 3H, thienyl-H)
• Example No. 1410 (CDCI 3 ) 1, 69, 1, 87 (2s, 6H, 2CH 3 ); 4.43, 4.63 (2tr, 4H, 2CH 2 ); 7.93 (d, 1H, quinoxalinone-H); 8.33 (m, 2H, phenyl-H)
• Example No. 1411 (CDCI 3 ) 1, 65, 1, 85 (2s, 6H, 2CH 3 ); 4.44, 4.65 (2tr, 4H, 2CH 2 ); 7.89 (d, 1H, quinoxalinone-H); 8.49 (m, 2H, phenyl-H)
• Example No. 1413 (CDCI 3 ) 1, 09 (tr, 6H, 2CH 3 ); 2.70 (tr, 4H, 2CH 2 CH 3 ); 2.83 (2H, tr, CH 2 N); 4.49 (tr, 2H, CH 2 Het); 7.91 (d, 1H, quinoxalinone-H); 8.03, 9.09, 9.22 (2d, s, 3H, benzothiophene-H)
• Plant 100% treated plant dies.
• the herbicide / safener / active substance combinations according to the invention formulated as emulsion concentrates and, in parallel tests, the correspondingly formulated individual active compounds are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 300 l / ha and after 2-3 weeks of standing of the test plants in the greenhouse under optimal growth conditions the effect of the preparations was rated visually in comparison to untreated controls.
• the active ingredients are also added directly to the irrigation water (application in analogy to the so-called
• Granulate application or sprayed on plants and in irrigation water.

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• 2004
  • 2004-05-12 DE DE102004023332A patent/DE102004023332A1/de not_active Withdrawn
• 2005
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  • 2005-04-26 CA CA002566460A patent/CA2566460A1/en not_active Abandoned
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  • 2005-04-26 JP JP2007511945A patent/JP2007537172A/ja active Pending
  • 2005-04-26 AU AU2005245259A patent/AU2005245259A1/en not_active Abandoned
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