Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
  • C07D498/04—Ortho-condensed systems
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/04—Ortho-condensed systems
• • 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

Definitions

• the present invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and weeds in crops and ornamental garden and general control of weeds and weeds in environmental areas where plant growth is disturbing.
• the present invention relates to the provision of new sieve ring-fused 3-phenyltetramic acid derivatives of the general formula (I) or an agrochemically acceptable salt thereof,
• fused 4-phenylpyrazolines are also described, for example, in WO 99/47525 (Pinoxaden).
• the compounds described in the prior art often have insufficient herbicidal activity and / or insufficient selectivity in crops.
• the object of the present invention is therefore to provide novel compounds which do not have the disadvantages mentioned.
• X is hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, Ci- C 3 -
• Y is hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C6 alkoxy, C1-C3
• W is hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C6 alkoxy, C1-C3
• Z is an oxygen atom, a group -S (O) n - or a group -IM ⁇ OR 1 ) - and n is 0, 1 or 2;
• R 1 is hydrogen, C 1 -C 1 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkanoyl;
• G is hydrogen, a leaving group L or a cation E, where L is one of the following
• R 2 is C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl;
• R 3 is C 1 -C 4 -alkyl
• R 4 is C 1 -C 4 -alkyl or phenyl which is unsubstituted or optionally with one or more substituents independently selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy , Nitro or cyano may be substituted;
• R 5 and R 5 ' are each independently methoxy or ethoxy
• R 6 and R 7 are each independently methyl, ethyl or phenyl, or together they are
• E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
• Sulfur atoms can be interrupted, or
• a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion for example, morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undec- 7-en (DBU), or
• a heterocyclic ammonium cation is, for example, in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, Pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate, or a sulfonium ion.
• the compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below. The remaining substituents of the general formula (I), which are not mentioned below, have the abovementioned meaning.
• a first embodiment of the present invention comprises compounds of the general formula (I) in which
• X is preferably hydrogen, C 1 -C -alkyl, C 1 -C -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy
• Ci-C i-alkyl Ci-C3-haloalkoxy or halogen
• X is particularly preferably hydrogen, C 1 -C 18 -alkyl, methoxy, ethoxy or halogen.
• a second embodiment of the present invention comprises compounds of the general formula (I) in which
• Y is preferably Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-Ce-alkoxy, Ci-C 3 alkoxy-Ci-C 4 alkyl,
• Ci-C3-haloalkoxy or halogen in which
• Y is particularly preferably C 1 -C 4 -alkyl, methoxy, ethoxy, or halogen.
• a third embodiment of the present invention comprises compounds of the general formula (I) in which
• W is preferably hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 6 -
• W particularly preferably hydrogen, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C3-alkoxy,
• a fourth embodiment of the present invention comprises compounds of the general formula (I) in which U and V preferably together form a seven-membered ring of the type T'-T 4 ,
• Z is an oxygen atom, a group -S (0) n - or a group -IM ⁇ OR 1 ) -, n is 0, 1 or 2, and
• R 1 is Ci-C i-alkyl, Ci-C i-haloalkyl or Ci-C i-alkanoyl; and in which
• U and V particularly preferably together form a seven-membered ring of the type T 1 or T,
• Z is an oxygen atom, a group -S (0) n - or a group -N (OCH3) and n is 0, 1 or 2.
• a fifth embodiment of the present invention comprises compounds of the general formula (I) in which
• G preferably denotes hydrogen, a leaving group L or a cation E, where L is one of the following radicals
• R 2 is C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl
• R 3 is C 1 -C 4 -alkyl
• C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from halogen or C 1 -C 1 -alkyl, Methoxy or ethoxy, each independently is methyl, ethyl or phenyl, and
• E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
• a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion for example, morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] undec- 7-ene (DBU) or choline; and in which
• G particularly preferably hydrogen, a leaving group L or a cation E, wherein L is one of the following radicals
• R Ci-C 4 alkyl or Ci-C 3 alkoxy-Ci-C 4 alkyl
• E is an alkali metal ion, an alkaline earth metal ion equivalent, an ion equivalent
• G is most preferably hydrogen, a leaving group L or a cation E, where L is one of the following radicals R is C 1 -C 4 -alkyl, Methyl or ethyl, and
• E is sodium, potassium, an ion equivalent of calcium, magnesium or aluminum.
• a sixth embodiment of the present invention comprises compounds of the general formula (I) in which
• X is hydrogen, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C 6 alkoxy, Ci. C 3 -alkoxy-C 1 -C 4 -alkyl,
• Ci-C4 alkyl Ci-C4-haloalkyl, Ci-C 3 alkoxy-Ci-C4-alkyl, Ci-C3 haloalkoxy or
• W is hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C6 alkoxy, C1-C3
• G is hydrogen, a leaving group L or a cation E, where L is one of the following radicals:
• R 2 is C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl
• R 3 is C 1 -C 4 -alkyl
• R 4 is C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from halogen or C 1 -C 4 -alkyl,
• R 5 and R 5 ' is methoxy or ethoxy
• R 6 and R 7 each independently represent methyl, ethyl or phenyl, E an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
• Aluminum an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups Ci-Cs-alkyl, Ci-C6-alkoxy or C3-C7 cycloalkyl or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example
• a seventh embodiment of the present invention comprises compounds of the general formula (I) in which
• X is hydrogen, C 1 -C 4 -alkyl, methoxy, ethoxy or halogen,
• Y is C 1 -C 4 -alkyl, methoxy, ethoxy, or halogen
• W is hydrogen, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C3 alkoxy, methoxy-C 2 alkyl, Ci-
• C 4 is haloalkoxy, C 2 -C 3 alkenyl, C 2 -C 6 alkynyl, halogen or phenyl; is unsubstituted or may optionally be substituted by one or more substituents independently selected from methyl, trifluoromethyl, methoxy, ethoxy, trifluoromethyl and fluorine, chlorine or bromine,
• U and V together form a seven-membered ring of the type T 1 or T 3 ,
• Z is an oxygen atom, a group -S (0) n - or a group -N (OCH3) and n is 0, 1 or 2.
• G is hydrogen, a leaving group L or a cation E, where L is one of the following
• R 2 is C 1 -C 4 -alkyl
• R 3 is methyl or ethyl
• E is sodium, potassium, an ion equivalent of calcium, magnesium or aluminum.
• radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched.
• these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred.
• Alkyl radicals including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; where at least one double bond or triple bond, preferably one double bond or triple bond, respectively, is formed.
• Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1 -yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl;
• Alkynyl includes, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.
• Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
• the cycloalkyl groups can occur in bi- or tri-cyc lischer form.
• haloalkyl groups and haloalkyl groups of haloalkoxy, haloalkenyl, haloalkynyl and the like are mentioned. are indicated in these residues, the lower carbon skeletons, z. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl, 1-chloroprop-1-yl-3-yl.
• Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene. Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B.
• Halogen is fluorine, chlorine, bromine or iodine.
• Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
• Aryl means a mono-, bi- or polycyclic aromatic system, for example
• the compounds of formula (I) can form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom.
• Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
• 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, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , wherein R to R'"are each independently one another may represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl, and also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.
• metal salts in particular Alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines
• the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. 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 HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, prop
• Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
• compounds of the general formula (I) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.
• the compounds of the formula (I) can be present as geometrical and / or optical isomers or mixtures of isomers in different compositions, which can optionally be separated in a customary manner. Both the pure isomers and the tautomeric, isomeric or enantiomeric mixtures, their preparation and use and compositions containing them are the subject of the present invention. However, in the following, for the sake of simplicity, reference will always be made to compounds of the formula (I), although both the pure compounds and optionally mixtures with different proportions of isomeric and tautomeric compounds are meant. Including the meanings described above for the groups T'-T 4 , the present invention thus has the following structural types:
• the compounds of the general formula (I) according to the invention are prepared on the basis of processes known from the literature, for example by a) if G is a hydrogen atom, precursors of the general formulas (II-1 to II-4)
• IM Ci-C i-alkyl, preferably methyl or ethyl or for an amino, Ci-C4-alkylamino or C1-C4-dialkylamino group, optionally in the presence of a suitable solvent or
• L has the abovementioned meaning and Hai can be a halogen atom, preferably chlorine or bromine or a sulfonic acid group, if appropriate in the presence of a suitable solvent or diluent and a suitable base, brings to reaction.
• a heterocyclic caprolactam of the general formula (IV) is acylated with a phenylacetic acid chloride of the general formula (V) optionally in the presence of a suitable base to give a compound of the general formula (VI), where in each case Z, X, Y and W are those indicated above Have meaning.
• suitable bases are, for example, organometallic reagents such as n-butyllithium, s-butyllithium or lithium diisopropylamide.
• Compounds of type (IV) are known or can be prepared according to known methods.
• Phenylacetic acids or their chlorides having the general formula (V), in which X, Y and W have the abovementioned meaning, are likewise known from the literature. For relevant methods, see, inter alia, Kobunshi Kagaku 1970, 27 (297), 1-20 or US 2771468 and the patent publications cited at the outset.
• the precursor of general formula ( ⁇ -3) required for process a) is obtained by alkoxycarbonylation of the intermediates of general formula (VII).
• reaction techniques are well known and can be carried out according to methods known in the literature, see, for example, Eur. J. Org. Chem., (7), 1306-1317; 2013 or Synlett, (6), 913-916; In 2009.
• precursors of the general formula ( ⁇ -3) for the reduction of precursors of the general formula ( ⁇ -3) to the optionally desired precursors having the general formula (II-1) are also a variety of methods known from the literature or reducing agents available.
• the catalytic hydrogenation with common transition metal catalysts such as palladium or nickel in suitable standard solvents such as methanol, ethanol or ethyl acetate is also obvious.
• Rearrangement of the double bond is accomplished by treatment with bases, e.g. Potassium tert-butoxide, Kaliumhexamethyltdisilazid or lithium diisopropylamide, in an inert solvent, preferably at low temperatures by literature methods.
• bases e.g. Potassium tert-butoxide, Kaliumhexamethyltdisilazid or lithium diisopropylamide
• bases e.g. Potassium tert-butoxide, Kaliumhexamethyltdisilazid or lithium diisopropylamide
• precursors (II-1) to ( ⁇ -4) can also be carried out on the route outlined in Scheme 2 for the case of compounds (II-2) or ( ⁇ -4).
• starting materials of the general formula (IX), in which Z has the meaning given above are first converted into compounds of the general formula (X), PG being a suitable NH protective group such as benzyl, benzyloxycarbonyl, phenylcarbamoyl or formyl.
• PG being a suitable NH protective group such as benzyl, benzyloxycarbonyl, phenylcarbamoyl or formyl.
• the present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied.
• the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinene.
• some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without it being intended to restrict them to certain species.
• the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
• the compounds of the present invention have excellent herbicidal activity against mono and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus , Avena, Hordeum, Oryza, Panicum, Saccharum, Seeal, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged.
• the present compounds are very well suited for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants.
• the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, such as through Triggering of desiccation and stunting are used. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, for example, as a result of which storage formation can be reduced or completely prevented.
• the active compounds can also be used for controlling harmful plants in crops by genetic engineering or by conventional mutagenesis of modified plants.
• the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
• Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
• transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
• transgenic crops Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
• the compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
• new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
• new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
• genetic modifications of crop plants have been described in several cases in order to modify the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806),
• transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosates
• Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
• transgenic crops which are characterized by higher yields or better quality transgenic crops characterized by a combination of z.
• Numerous molecular biological techniques with which new transgenic plants with altered properties can be produced are known in principle, see, for example, BI Potrykus and G.
• nucleic acid molecules can be introduced into plasmids that have a mutagenesis or a sequence change by recombination of DNA
• base substitutions for example, to carry out base substitutions, to remove partial sequences or to add natural or synthetic sequences
• connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbo Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
• the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
• DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
• the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
• the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106).
• the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
• the transgenic plant cells can be regenerated to whole plants by known techniques.
• the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
• the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
• the essential plant enzymes eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
• the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
• the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
• the compounds of the general formula (I) may also contain such harmful plants, for example from the group Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Digitaria, Echinochloa, Eleusine, Eriochloa, Leptochloa, Lolium , Ottochloa, Panicum, Pennisetum, Phalaris, Poa, Rottboellia, Setaria and / or Sorghum weeds;
• Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Lolium, Panicum, Phalaris, Poa, Setaria and / or Sorghum weeds which are one or more inhibiting the enzyme acetyl-CoA carboxylase (ACCase) Herbicides are resistant.
• ACCase-inhibiting herbicides include pinoxaden, clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl, fluazifop-p-butyl, haloxyfop-P-methyl, quizalofop-P-ethyl, propaquizafop, cyhalofop-butyl, clethodim, sethoxydim, Cycloxydim, tralkoxydim or butroxydim are resistant;
• acetolactate synthase (ALS) -inhibiting herbicides such as, for example, one or more sulfonylurea herbicides (eg iodosulfuron-methyl, mesosulfuron-methyl, tribenuron-methyl, triasulfuron, prosulfuron, sulfosulfuron, pyrazosulfuronethyl, bensulfuron-methyl, Nicosulfuron, flazasulfuron, iofensulfuron, metsulfuron-methyl, or any other sulfonylurea disclosed in the "The Pesticide Manual", 15th edition (2009) or 16th edition (2012), CDS Tomlin, British Crop Protection Council and / or one or more triazolopyrimidine herbicides (eg florasulam, pyroxsulam or penoxsulam) and / or one or more pyrimidinyl (thio or
• the compounds of the general formula (I) according to the invention can be used against harmful plants which are resistant to one or more ACCase inhibiting herbicides (eg selected from the list above), at least partially due to mutations (eg Substitution) of one or more amino acids in the ACCase target site of the harmful plant (cf., for example, SB Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu. Rev. Plant Biol., 2010, 61, pp. 317-347); and or
• ALS-inhibiting herbicides eg selected from the above list of ALS-inhibiting herbicides
• mutations eg substitution
• mutations eg substitution
• a metabolite conditional herbicide resistance e.g. At least in part by a cytochrome P450-mediated metabolism (see, for example, SB Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu., Rev. Plant Biol., 2010, 61, pp. 317-347).
• the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
• the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
• the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil in water and water in oil emulsions, sprayable solutions, suspension concentrates (SC), Oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water dispersible granules (WG), water soluble Granules (SG), ULV formulations, microcapsules and waxes.
• WP wettable powder
• SP water-soluble powders
• EC emulsifiable concentrates
• EW emulsions
• SC suspension concentrate
• Suitable safeners are e.g. Mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromid.
• Injectable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent, dispersant) in addition to a diluent or inert substance, e.g.
• the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
• Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
• organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
• emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
• Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Suspension concentrates may be water or oil based. They can be prepared, for example, by wet milling using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
• Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.
• EW Oil-in-water emulsions
• Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired when mixed with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray-drying, fluidized-bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical preparations contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
• the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation constituents.
• the active substance concentration may be about 1 to 90, preferably 5 to 80,% by weight.
• Sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt.% Active ingredient.
• the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
• the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
• the active ingredient formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and viscosity-influencing agents.
• the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• the required application rate of the compounds of the formula (I) varies. It can vary within wide limits, for example between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
• the following examples illustrate the preparation of the compounds according to the invention:
• reaction solution is poured onto ice-water and the aqueous phase extracted three times with 300 ml of diethyl ether, with 100 ml of sat. Sodium chloride solution, dried over sodium sulfate and concentrated. After chromatography on silica gel, 6.0 g of the target compound are obtained in the form of a yellow oil.
• Triethylamine in 20 mL dichloromethane at 0 ° C added dropwise. After 3 h at RT, water is added, the phases are separated and the organic phase is concentrated. After chromatography on silica gel, 1.05 g of the target compound are obtained as a colorless oil.
• a dispersion concentrate which is readily dispersible in water is obtained by dissolving 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight
• Alkylphenolpolyglykolether (®Triton X 207), 3 parts by weight of isotopecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and milled in a ball mill 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) and / or its salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight
• a water-dispersible granules are also obtained by
• Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
• the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied.
• ECHCG Echinochloa crus-galli
• Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam soil in wood fiber pots, covered with soil and in the greenhouse under good conditions
• test plants are treated in the single leaf stage.
• WP wettable powders
• compounds of the invention have good post-emergence herbicidal activity against a broad spectrum of grass weeds and weeds.
• the compounds according to the invention are therefore suitable postemergence for controlling unwanted plant growth.

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• 2017
  • 2017-04-06 BR BR112018071025A patent/BR112018071025A2/pt active Search and Examination
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  • 2017-04-06 AU AU2017249659A patent/AU2017249659A1/en not_active Abandoned
  • 2017-04-06 EP EP17716194.0A patent/EP3442978A1/de not_active Withdrawn
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  • 2017-04-06 US US16/093,018 patent/US20190119298A1/en not_active Abandoned
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