Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
  • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
  • C07D295/205—Radicals derived from carbonic acid
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
  • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
  • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
  • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
  • C07D295/28—Nitrogen atoms
  • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/54—Radicals substituted by oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
  • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
  • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
• • 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

Definitions

• the invention relates to new substituted alkoxycarbonyl compounds, processes for their preparation and their use as plant treatment agents, in particular as herbicides, fungicides and insecticides.
• n the numbers 0 or 1
• Ar represents an optionally substituted, monocyclic or bicyclic, saturated or - optionally partially - unsaturated, carbocyclic or heterocyclylic group
• R 1 represents alkyl or cycloalkyl
• R 2 represents hydrogen or alkyl
• Y represents NH or N (alkyl)
• Z stands for optionally substituted, monocyclic or bicylic, saturated or partially unsaturated heterocyclyl bonded via N, or - if n stands for 1 or Ar stands for a bicyl group - also stands for optionally substituted cycloalkylamino or arylamino.
• the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in various enantiomeric (R- and S-configured forms) or diasteromeric forms.
• the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these stereoisomeric compounds.
• hydrocarbon chains such as alkyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
• Ar preferably represents an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclic group from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl,
• A is alkanediyl having 1 to 3 carbon atoms which is optionally substituted by halogen, and the substituents which are possible in each case are preferably selected from the following list:
• Q preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (C, -C 4 -
• R 1 preferably represents alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms;
• R 2 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms
• Y is preferably NH or N (C i -C i-alkyl);
• Z preferably represents in each case optionally substituted and bound via N, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S, S-dioxothiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydro - hydroisoindolinyl, tetrahydroquinolinyl, perhydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, or - if n is 1 or Ar is a bicyl group - also optionally substituted cycloalkylamino having 3 to 6 carbon atoms or arylamino having 6 or 10 carbon atoms , where the possible substituents are preferably selected from the following list:
• A stands for methylene or dimethylene (ethane-1,2-diyl) which is optionally substituted by fluorine and / or chlorine, and where the possible substituents are preferably selected from the following list:
• R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, or cyclopropyl;
• R 2 particularly preferably represents hydrogen or methyl
• Y particularly preferably represents NH, N (methyl), N (ethyl) or N (i-propyl);
• Z particularly preferably represents in each case optionally substituted and above
• Q particularly preferably represents oxygen
• R 1 particularly preferably represents methyl, ethyl, n- or i-propyl; Ar particularly preferably represents the grouping below
• R3 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy and
• R4 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl
• Q furthermore very particularly preferably represents CH 2 (methylene);
• Ar still very particularly preferably represents one of the groupings below
• radical definitions listed above 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. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.
• n stands for the numbers 0 or 1
• Y for NH, N (methyl), N (ethyl) or N (i-propyl)
• Z has the meanings listed below:
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• n, Y and Z have the meanings given above in Group 1.
• the new substituted alkoxycarbonyl compounds of the general formula (I) have interesting biological properties; they are characterized in particular by strong and selective herbicidal activity and by fungicidal and insecticidal activity.
• the new substituted alkoxycarbonyl compounds of the general formula (I) are obtained if
• reaction auxiliary optionally in the presence of a reaction auxiliary and optionally in the presence of a reaction auxiliary
• n, Y and Z have the meaning given above,
• Formula (II) provides a general definition of the substituted alkanols to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
• Ar, Q, R 1 and R 2 in formula (II) preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for Ar, Q, R 1 and R 2 were given.
• the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,194,661, US Pat. A-5 399 545, see the production examples).
• Formula (III) provides a general definition of the isocyanates which are further to be used as starting materials in process (a) according to the invention.
• Z preferably has the meaning which has already been given as preferred or particularly preferred for Z in connection with the description of the compounds of the formula (I) according to the invention.
• the starting materials of the general formula (III) are known organic synthetic chemicals.
• Formula (IV) provides a general definition of the chloroformic acid esters to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I).
• Ar, Q, R 1 and R 2 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, as being particularly preferred or very particularly preferred for Ar, Q, R 1 and R 2 were given.
• the starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,194,661, US Pat. A-5 399 545, see the production examples).
• Formula (V) provides a general definition of the nucleophilic compounds to be used further as starting materials in process (b) according to the invention.
• n, Y and Z preferably have those meanings which have already been given above as preferred, particularly preferred or very particularly preferred for n, Y and Z in connection with the description of the compounds of the formula (I) according to the invention were.
• the starting materials of the general formula (V) are known organic synthetic chemicals.
• the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, Potassium or
• Calcium amide sodium, potassium or calcium carbonate, sodium, potassium or Calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine,
• DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
• nucleophilic compounds of the general formula (V) to be used as starting materials if used in a corresponding excess, can also serve as reaction auxiliaries.
• Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene,
• Dichlorobenzene petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide,
• N-methyl-pyrrolidone or hexamethylphosphoric triamide Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
• the reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
• Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes 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 large excess.
• the reaction is generally carried out in a suitable diluent, if appropriate 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:
• Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
• Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
• the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut,
• Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants are used on ornamental and sports turf and pasture land and for selective weed control in annual crops.
• the compounds of the formula (I) according to the invention are particularly 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 method.
• the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
• the active ingredients are suitable for use as fungicides.
• Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes,
• Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
• Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv.
• Lachrymans Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P.
• Erwinia species such as, for example, Erwinia amylovora
• Pythium species such as, for example, Pythium ultimum
• Phytophthora species such as, for example, Phytophthora infestans
• Erysiphe species such as, for example, Erysiphe graminis
• Sphaerotheca species such as, for example, Sphaerotheca fuliginea
• Podosphaera species such as, for example, Podosphaera leucotricha
• Species such as Venturia inaequalis; Pyrenophora species, such as wise Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia-
• Species such as Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
• the active compounds of the general formula (I) according to the invention in particular show good activity against mildew (Erisyphe graminis).
• the active ingredients are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include:
• Isopoda for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• Diplopoda for example, Blaniulus guttulatus.
• Chilopoda for example, Geophilus carpophagus and Scutigera spec.
• Symphyla e.g. Scutigerella immaculata.
• Thysanura for example Lepisma saccharina.
• Collembola for example Onychiurus armatus.
• Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
• Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Pemphigylloxumum.
• Anthenhrenus spp. Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp Monomorium pharaonis, Vespa spp.
• Gastrophilus spp. Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula palosa. From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the order of the Arachnida e.g. Sco ⁇ io maurus, Latrodectus mactans.
• the plant parasitic nematodes include, for example Pratylenchus spp., Radopholus spp.,
• the compounds of the general formula (I) according to the invention are very suitable for controlling plant-damaging insects, such as e.g. Cabbage cockroaches (Plutella spp.) And aphids (Mycus spp.).
• the active ingredients 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 im 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, aryl sulfonates as well as protein hydrolyzates; Possible dis
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
• 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.
• the formulations generally contain between 0.1 and 95 percent by weight
• Active ingredient preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
• herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate , Bensulfuron (-methyl), bentazone,
• Benzofenap Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidaz, Chloronben, Chloramben, Chloramben, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cin- methylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop,
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. 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. 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 lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
• a mixture of 65 g (0.50 mol) of propionylacetic acid methyl ester, 34 g (0.50 mol) of sodium ethylate and 300 ml of 1,4-dioxane is at 30 ° C for 30 minutes
• a solution of 120 g (0.52 mol) is added to a mixture of 800 ml of toluene, 3 ml of N, N-dimethylformamide and 54 g (0.55 mol) of phosgene at room temperature (approx. 20 ° C.) with stirring.
• the reaction mixture is then stirred at 60 ° C. for 8 hours.
• the solvent is then carefully distilled off in a water jet vacuum.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
• Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor.
• the amount of water per unit area is expediently kept constant.
• the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
• Solvent 5 parts by weight of acetone 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.
• Solvent 48.8 parts by weight of N, N-dimethylformarnide emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
• Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• the compounds according to Preparation Examples 8, 10, 11, 12, 13, 14, 15, 16 and 56 show an efficiency of 80% to 95% at a rate of 750 g / ha.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Field bean seedlings (Vicia faba minor), which are infested with the green peach aphid (Myzus persicae), are immersed in the active compound preparation of the desired concentration and placed in a plastic can.
• the kill is determined in percent. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
• the compounds according to Preparation Examples 21, 26, 29 and 40 show a degree of destruction of 90%> to 100% at an active ingredient concentration of 0.1%.
• Solvent 100 parts by weight of acetone emulsifier: 1900 parts by weight of methanol
• a specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, a film can lid with about 100 plutella eggs is placed on each cavity. The newly hatched larvae migrate to the treated synthetic food.
• the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

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• Chemical & Material Sciences (AREA)
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• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
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• Other In-Based Heterocyclic Compounds (AREA)
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• 1999
  • 1999-02-13 WO PCT/EP1999/000951 patent/WO1999042457A2/de not_active Application Discontinuation
  • 1999-02-13 EP EP99907551A patent/EP1056734A2/de not_active Withdrawn
  • 1999-02-13 CN CN 99805262 patent/CN1298399A/zh active Pending
  • 1999-02-13 CA CA002321460A patent/CA2321460A1/en not_active Abandoned
  • 1999-02-13 BR BR9908098-2A patent/BR9908098A/pt not_active Application Discontinuation
  • 1999-02-13 JP JP2000532409A patent/JP2002504482A/ja active Pending
  • 1999-02-13 AU AU27255/99A patent/AU2725599A/en not_active Abandoned

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