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EP1198172A1 - Heterocyclylalkylamines substitues par un azote utilises comme herbicides et nouveaux thienylalkylamines substitues par un azote - Google Patents

Heterocyclylalkylamines substitues par un azote utilises comme herbicides et nouveaux thienylalkylamines substitues par un azote

Info

Publication number
EP1198172A1
EP1198172A1 EP00929377A EP00929377A EP1198172A1 EP 1198172 A1 EP1198172 A1 EP 1198172A1 EP 00929377 A EP00929377 A EP 00929377A EP 00929377 A EP00929377 A EP 00929377A EP 1198172 A1 EP1198172 A1 EP 1198172A1
Authority
EP
European Patent Office
Prior art keywords
cyano
alkyl
alkoxy
thienyl
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00929377A
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Ernst Rudolf F. Gesing
Kristian Kather
Stefan Lehr
Lothar Rohe
Katharina Voigt
Mark Wilhelm Drewes
Dieter Feucht
Rolf Pontzen
Ingo Wetcholowsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1198172A1 publication Critical patent/EP1198172A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N25/02—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 containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/58—Radicals substituted by nitrogen atoms

Definitions

  • N-substituted heterocyclylalkylamines as herbicides and new N-substituted thienylalkylamines
  • the invention relates to the use of N-substituted heterocyclylalkylamines as herbicides and to new N-substituted thienylalkylamines and processes for their preparation.
  • A represents a single bond or alkanediyl
  • R 1 represents optionally substituted alkyl
  • R 2 for hydrogen, amino or for each optionally substituted alkyl alkoxy, alkylthio.
  • Y stands for cyano or nitro and
  • Z represents optionally substituted heterocyclyl
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • alkyl or alkenyl are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as in alkoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, with multiple substitution the substituents can be the same or different.
  • the compounds of the general formula (I) according to the invention contain at least one carbon-nitrogen double bond and can therefore be present in various E- and Z-configured isomeric forms.
  • the invention relates both to the use of the individual E- and Z-configured isomeric forms of the compounds of the general formula (I) and to the mixtures of these isomeric compounds.
  • the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be in various enantiomeric (R- and S-configured forms) or diastereoisomers
  • Shapes are available.
  • the invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these isomeric compounds.
  • A preferably represents a single bond or alkanediyl having 1 to 4 carbon atoms.
  • R 1 preferably represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy.
  • R 2 preferably represents hydrogen, amino or, if appropriate, in each case
  • Z preferably represents an optionally substituted, monocyclic or bicyclic heterocyclic group from the series furyl, tetrahydrofuryl,
  • R ' particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
  • R 2 particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, n each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t
  • Z particularly preferably represents an optionally substituted, monocyclic or bicyclic heterocyclic grouping from the furyl series.
  • R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl.
  • R 2 very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
  • Z very particularly preferably represents in each case optionally substituted
  • substituents from the series nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl. Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy.
  • n- or i-propoxy di fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl.
  • Methylsulfonyl Methylsulfonyl.
  • Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxy-carbonyl are selected.
  • radicals listed above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the herbicidal use of compounds of the formula (I) in which a combination of the meanings listed above as very particularly preferred is present is very particularly preferred.
  • A represents a single bond or alkanediyl having 1 to 4 carbon atoms
  • R 1 represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,
  • R 2 represents hydrogen, amino or, in each case optionally by cyano
  • Halogen C, -C 4 alkoxy, C, -C 4 alkylthio, C, -C 4 alkylsulfinyl or C, -C 4 - alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups,
  • Y represents cyano or nitro
  • Z represents in each case optionally substituted thienyl or benzothienyl
  • Haloalkyl C, -C 4 alkoxy, C, -C 4 haloalkoxy, C, -C 4 alkylthio, C, -C 4 - haloalkylthio.
  • Phenyl are selected where the compounds N'-cyano-N- [l-methyl-3- (3-thienyl) propyl] ethanimide amide, N'-cyano-N- [l-ethyl-3- (3-thienyl) - propyl] ethanimidamide, N'-cyano-N- [1- methyl-3- (2-thienyl) propyl] -ethanimidamide, N'-cyano-N- [1- (2-thienyl) ethyl] ethanimidamide and N'-cyano-N- [l- (3-thienyl) ethyl] ethanimidamide (cf. DE-A-
  • R 1 , R 2 and the substituents listed for Z preferably have the preferred meanings indicated above.
  • R 1 , R 2 and Y have, for example, the meanings listed in the table below.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 . R 2 and Y have, for example, the meanings listed above in the table for group 1.
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R ', R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R ', R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R ', R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R 1 , R 2 and Y have, for example, the meanings listed above in Table 1 for group 1.
  • Group 24
  • R 1 , R 2 and Y have, for example, the meanings given above in Table 1 for group 1.
  • R 2 and Y have the meaning given above and
  • X represents alkoxy or alkylthio, if appropriate in the presence of a diluent.
  • Formula (II) provides a general definition of the heterocyclylalkylamines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • A, R 1 and Z preferably have those meanings which are preferred, particularly preferred or very particularly preferred for A, R 1 and Z already in connection with the description of the compounds of the general formula (I) have been specified.
  • heterocyclylalkylamines of the general formula (II) are known and / or can be prepared by processes known per se (cf. DE-A-19744232 / LeA 32589, DE-A-19816055).
  • Formula (III) provides a general definition of the imino compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • R 2 and Y preferably have those meanings which are preferred, particularly preferred or very particularly preferred for R 2 and Y, in connection with the description of the compounds of the general formula (I) according to the invention have been specified;
  • X stands in particular for C, -C 4 -alkoxy or C, -C 4 -alkylthio, in particular for methoxy, ethoxy, methylthio or ethylthio.
  • the imino compounds of the general formula (III) are known and / or can be prepared by processes known per se (cf. Chem. Ber. 100 (1967),
  • Formula (I) is preferably carried out using a diluent.
  • suitable diluents for carrying out the process according to the invention are, above all, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene,
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Galinsoga Chenopodium, Urtica, Senecio, Amaranthus, Portulaca.
  • Ambrosia cirsium. Carduus, Sonchus. Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex. Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention can also be used to control weeds in permanent crops. e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process. To a certain extent, the compounds of the general formula (I) according to the invention also have strong activity against animal pests, in particular against nematodes.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers. Rhizomes, cuttings and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and. in the case of propagation material, in particular in the case of seeds, also by means of single or multi-layer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts. Pastes, soluble powders. Granules, suspension emulsion concentrates, active ingredient in impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • Possible solid carriers are: e.g. Ammonium salts and natural
  • Rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: eg broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • Suitable emulsifying and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates. Arylsulfonates as well as protein hydrolyzates; Possible dispersants
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron. Copper. Cobalt, molybdenum and zinc can be used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron. Copper. Cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0J and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations as a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos. Asulam, Atrazine.
  • Benzobicyclone benzofenap, benzoylprop (-ethyl). Bialaphos, Bifenox.
  • Bispyribac (- odium), bromobutide, bromofenoxime. Bromoxynil. Butachlor. Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Coxulfydin, Cloxulfodon, Cloxulfodon, -propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-me hyl), Cumyluron, Cyanazine,
  • Cybutryne Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethyl ( -ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron. Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb.
  • Ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron.
  • Etobenzanid fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl), flamprop (- isopropyl-L), flamprop (-methyl), flazasulfuron.
  • Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox. Imazapic, Imazapyr, Imazaquin,
  • Imazethapyr imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, motrionezloron , Metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron.
  • P razosulfuron (-ethyl). Pyrazoxylene, P ⁇ rib ⁇ n / - oxime, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-p-ethyl), quizalofop (-p-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, Sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulf ron (-methyl),
  • Insecticides Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. from. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the Retention times by linear interpolation between two consecutive alkanones).
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Methyl methoxyacetate 15 g of Novenzym-435 and 1 liter of methyl t-butyl ether are stirred at 60 ° C. for 24 hours and after addition of a further 5 g of Novenzym-435.
  • the mixture is then filtered, the filtrate is concentrated in a water jet vacuum, the residue is taken up in 500 ml of dichloromethane and shaken with 1 liter of 10% aqueous hydrochloric acid.
  • the organic phase is separated off and worked up as described below.
  • the aqueous phase is by adding conc. Sodium hydroxide solution made alkaline and extracted with dichloromethane.
  • the organic extraction solution is dried with sodium sulfate and filtered.
  • the desired product is isolated from the filtrate by distillation under reduced pressure.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation Examples 5 and 44 show, in some cases, good tolerance to crop plants, such as Barley. Corn and wheat, strong weed control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Toxicology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

L'invention concerne des hétérocyclylalkylamines substitutés par un azote de la formule générale (I) où A représente une liaison simple ou alkandiyl, R1 représente alkyle éventuellement substitué, R2 représente de l'hydrogène, amino ou bien alkyle, alcoxy, alkylthio, alkylamino ou dialkylamino respectivement éventuellement substitués, Y représente cyano ou nitro et Z représente hétérocyclyle éventuellement substitué. Ces hétérocyclylalkylamines sont utilisés comme herbicides. L'invention concerne également de nouveaux thiénylalkylamines substitués par un azote et leur procédé de production.
EP00929377A 1999-04-30 2000-04-18 Heterocyclylalkylamines substitues par un azote utilises comme herbicides et nouveaux thienylalkylamines substitues par un azote Withdrawn EP1198172A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19919790A DE19919790A1 (de) 1999-04-30 1999-04-30 Verwendung von N-substituierten Heterocyclyalkylaminen als Herbizide und neue N-substituierte Thienylaklylamine
DE19919790 1999-04-30
PCT/EP2000/003496 WO2000065916A1 (fr) 1999-04-30 2000-04-18 Heterocyclylalkylamines substitues par un azote utilises comme herbicides et nouveaux thienylalkylamines substitues par un azote

Publications (1)

Publication Number Publication Date
EP1198172A1 true EP1198172A1 (fr) 2002-04-24

Family

ID=7906473

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00929377A Withdrawn EP1198172A1 (fr) 1999-04-30 2000-04-18 Heterocyclylalkylamines substitues par un azote utilises comme herbicides et nouveaux thienylalkylamines substitues par un azote

Country Status (12)

Country Link
EP (1) EP1198172A1 (fr)
JP (1) JP2002543099A (fr)
KR (1) KR20020008830A (fr)
CN (1) CN1349382A (fr)
AU (1) AU761304B2 (fr)
BR (1) BR0010686A (fr)
CA (1) CA2372031A1 (fr)
DE (1) DE19919790A1 (fr)
HK (1) HK1043916A1 (fr)
MX (1) MXPA01011007A (fr)
PL (1) PL351589A1 (fr)
WO (1) WO2000065916A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10303883A1 (de) * 2003-01-31 2004-08-12 Bayer Cropscience Ag Substituierte Pyrimidine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639268A (en) * 1985-07-29 1987-01-27 American Cyanamid Company Nitro- and cyanoguanidines as selective preemergence herbicides and plant defoliants
US6638979B1 (en) * 1998-07-18 2003-10-28 Bayer Aktiengesellschaft Imidamide derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0065916A1 *

Also Published As

Publication number Publication date
BR0010686A (pt) 2002-02-05
HK1043916A1 (zh) 2002-10-04
CN1349382A (zh) 2002-05-15
KR20020008830A (ko) 2002-01-31
JP2002543099A (ja) 2002-12-17
CA2372031A1 (fr) 2000-11-09
MXPA01011007A (es) 2002-07-22
PL351589A1 (en) 2003-05-05
DE19919790A1 (de) 2000-11-02
AU761304B2 (en) 2003-06-05
AU4749000A (en) 2000-11-17
WO2000065916A1 (fr) 2000-11-09

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