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WO2004024692A1 - Derives d'acide carboxylite heterocyclyle carbonyle aminocyclopropane - Google Patents

Derives d'acide carboxylite heterocyclyle carbonyle aminocyclopropane Download PDF

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Publication number
WO2004024692A1
WO2004024692A1 PCT/EP2003/009124 EP0309124W WO2004024692A1 WO 2004024692 A1 WO2004024692 A1 WO 2004024692A1 EP 0309124 W EP0309124 W EP 0309124W WO 2004024692 A1 WO2004024692 A1 WO 2004024692A1
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Prior art keywords
optionally substituted
formula
carbon atoms
heterocyclylcarbonyl
acid derivatives
Prior art date
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PCT/EP2003/009124
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German (de)
English (en)
Inventor
Bernd-Wieland Krüger
Lutz Assmann
Astrid Mauler-Machnik
Karl-Heinz Kuck
Yoshinori Kitagawa
Original Assignee
Bayer Cropscience Aktiengesellschaft
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Priority to AU2003255454A priority Critical patent/AU2003255454A1/en
Publication of WO2004024692A1 publication Critical patent/WO2004024692A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to new heterocyclylcarbonylaminocyclopropanecarboxylic acid derivatives, several processes for their production and their use for combating undesirable microorganisms.
  • G represents five- or six-membered heterocyclyl which is substituted by halogen and / or alkyl having 1 to 4 carbon atoms and may also contain a fused cyclohexane radical, and R stands for a group -OR 1 , -NH-R 2 or or for one optionally substituted, saturated N-heterocyclyl radical which is connected to the carbonyl group via nitrogen, where
  • R 1 , R 2 , R 3 and R 4 independently of one another represent optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted aralkyl,
  • R 1 has the meaning given above
  • X represents halogen
  • Substances can not only be used for the direct control of undesired microorganisms, but also have a resistance-inducing effect on plants.
  • heterocyclylcarbonylarino-cyclopropanecarboxylic acid derivatives of the formula (I) according to the invention show a substantially better fungicidal activity than the constitutionally most similar, known active ingredients of the same activity.
  • heterocyclylcarbonylaminocyclopropanecarboxylic acid derivatives according to the invention are generally defined by the formula (I).
  • Preferred substances of the formula (I) are those in which
  • G represents pyridyl which is mono- to trisubstituted by chlorine, bromine and / or methyl,
  • R represents a five- to seven-membered, saturated N-heterocyclyl radical which is optionally substituted by alkyl having 1 to 4 carbon atoms and is linked to the carbonyl group via nitrogen and 1 to 3
  • Sulfur atom can be replaced, or
  • y R 3 R represents a group -OR 1 , -NH-R 2 or ⁇ , wherein
  • cycloalkyl having 3 to 8 carbon atoms optionally substituted by alkyl having 1 to 4 carbon atoms, or
  • radicals in the aryl part can be substituted once to three times, in the same way or differently, by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
  • Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts or
  • aryl radicals can be monosubstituted by alkylene having 3 to 4 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, these radicals being linked in the ortho position can be monosubstituted to tetrasubstituted, identical or different, by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
  • alkyl with 1 to 8 carbon atoms optionally substituted by alkoxy with 1 to 4 carbon atoms
  • alkenyl with 2 to 8 carbon atoms optionally substituted with alkoxy with 1 to 4 carbon atoms for alkynyl with 2 to 8 carbon atoms optionally substituted with alkoxy with 1 to 4 carbon atoms stands, or
  • cycloalkyl having 3 to 8 carbon atoms optionally substituted by alkyl having 1 to 4 carbon atoms, or
  • aryl represents aryl with 6 or 10 carbon atoms or for aralkyl with 6 or 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where these radicals in the aryl part can each be monosubstituted to triple, identical or differently substituted by halogen, cyano, Ni ro, Amino, hydroxy, formyl, carboxy,
  • Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts or
  • aryl radicals can be monosubstituted by double-linked alkylene having 3 or 4 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, these radicals being monosubstituted to quadruple, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
  • R 3 and R 4 independently of one another, optionally by alkoxy
  • 1 to 4 carbon atoms substituted alkyl having 1 to 8 carbon atoms represent alkenyl having 2 to 8 carbon atoms optionally substituted by alkoxy having 1 to 4 carbon atoms, representing alkynyl having 2 to 8 carbon atoms optionally substituted by alkoxy having 1 to 4 carbon atoms, or represent cycloalkyl of 3 to 8 carbon atoms optionally substituted by alkyl having 1 to 4 carbon atoms, or
  • Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts or Cycloalkyl with 3 to 6 carbon atoms,
  • aryl radicals can be monosubstituted by alkylene with 3 or 4 carbon atoms linked in the ortho position or dioxyalkylene with 1 or 2 carbon atoms, where these radicals can be monosubstituted to quadrupled, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.
  • G represents 2,6-dichloropyrid-4-yl, 3,4-dichloroisothiazol-5-yl, 5-bromo-2-thienyl, 5-chloro-2-thienyl or 4,5-dibromo-2-thienyl, or
  • G represents 2-chloro-pyrid-4-yl, 2-chloro-6-methyl-pyrid-4-yl or the rest of the formula
  • R for optionally by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • R represents a group -OR 1 , -NH-R 2 or, wherein for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl or octyl, AUyl, butenyl, pentenyl, propargyl, butinyl or substituted by methoxy or ethoxy Pentinyl stands, or
  • Propionyl acetyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl or
  • phenyl radicals can be monosubstituted by trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) or ethylenedioxy which are linked in the ortho position, each of these radicals being simple to fourfold, similar or differently substituted can be by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n-propyl or isopropyl, or
  • the phenyl radicals may be monosubstituted by methylenedioxy which is linked in the ortho position and which may be monosubstituted or disubstituted, identical or differently substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n-propyl or isopropyl
  • Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or the phenyl radicals can be monosubstituted by trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) or ethylenedioxy which are linked in the ortho position, each of these radicals being simple to fourfold, similar or can be differently substituted by fluorine,
  • Chlorine methyl, trifluoromethyl, ethyl, n-propyl or isopropyl, or
  • the phenyl radicals can be monosubstituted by methylenedioxy linked twice in the ortho position, which can be monosubstituted or disubstituted, identical or differently substituted by fluorine, chlorine, methyl,
  • R 3 and R 4 independently of one another each represent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl or octyl, AUyl, butenyl, optionally substituted by methoxy or ethoxy , Pentenyl, propargyl,
  • phenyl radicals can be monosubstituted by trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-dynyl) or ethylenedioxy which are linked in the ortho position, each of these radicals being simple to fourfold, similar or can be differently substituted by fluorine,
  • Chlorine methyl, trifluoromethyl, ethyl, n-propyl or isopropyl
  • phenyl radicals can be monosubstituted by methylenedioxy which is linked in the ortho position and which can be monosubstituted or disubstituted, identical or differently substituted by fluorine, chlorine
  • a very particularly preferred group of substances according to the invention are those compounds of the formula (I) in which
  • G represents 2,6-dichloropyrid-4-yl, 3,4-dichloroisothiazol-5-yl, 5-bromo-2-thienyl, 5-chloro-2-thienyl or 4,5-dibromo-2-thienyl, or
  • G represents 2-chloro-pyrid-4-yl, 2-chloro-6-methyl-pyrid-4-yl or the rest of the formula
  • R represents a group -OR 1 or -NH-R 2 , wherein R 1 for methyl optionally substituted by methoxy or ethoxy,
  • R 2 for methyl optionally substituted by methoxy or ethoxy
  • Pentinyl stands, or represents in each case optionally substituted by methyl or ethyl cyclopropyl, cyclobutyl,, cyclopentyl or cyclohexyl.
  • Formula (II) provides a general definition of the ammo-cyclopropane-carboxylic acid esters required as starting substances when carrying out process (a) according to the invention.
  • R 1 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • amino-cyclopropane-carboxylic acid esters of the formula (II) are known or can be prepared by known methods (cf. DE-A 28 24 517, WO 86-03 378, EP-A 0 199257 and Plant Growth Regul. 8 (4) , 297-307 (1989)). So they can be made by adding 1-amino-cyclopropane-carboxylic acid with an alcohol
  • Formula (III) provides a general definition of the acid halides required as reaction components for carrying out process (a) according to the invention.
  • G preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • X preferably represents chlorine or bromine.
  • the acid halides of the formula (ILT) are known or can be prepared according to known ones
  • Suitable diluents for carrying out process (a) according to the invention are all customary, inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, can preferably be used; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-
  • Suitable acid binders for carrying out process (a) according to the invention are all customary inorganic and organic bases.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, are preferably usable.
  • DBU diazabicyclonones
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures from 0 ° C to 120 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • Formula (TV) provides a general definition of the acylamino-cyclopropane-carboxylic acids required as starting materials when carrying out process (b) according to the invention.
  • G preferably has the meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • acylamino-cyclopropane-carboxylic acids of the formula (IV) are hitherto unknown.
  • the acylamino-cyclopropane-carboxylic acids of the formula (IV) can also be used very well to combat unwanted microorganisms. In particular, they have fungicidal properties and can be used both directly
  • acylamino-cyclopropane-carboxylic acids of the formula (TV) can be prepared by
  • Formula (Ia) provides a general definition of the heterocyclylcarbonylamino-cyclopropane-carboxylic acid derivatives required as starting substances when carrying out process (c) according to the invention.
  • G and R 1 preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • heterocyclylcarbonylamino-cyclopropane-carboxylic acid derivatives of the formula (Ia) are substances according to the invention which can be prepared by process (a) according to the invention.
  • Suitable bases for carrying out process (c) according to the invention are all customary inorganic bases.
  • Alkaline earth metal or alkali metal hydroxides such as, for example, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, can preferably be used.
  • Suitable diluents for carrying out process (c) according to the invention are all customary, water-miscible, organic solvents.
  • Alcohols such as methanol, ethanol, n- or i-
  • reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. In general, temperatures from 0 ° C to 80 ° C, preferably at temperatures from 0 ° C to 50 ° C.
  • heterocycliccarbonylamino-cyclopropane-carboxylic acid derivatives of the formula (Ia) are reacted with an excess of water in the presence of an equivalent amount or an excess of base.
  • the processing is again carried out according to the usual
  • Formula (V) provides a general definition of the compounds required as reaction components when carrying out process (b) according to the invention.
  • R preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • the compounds of the formula (V) are known or can be prepared by known methods.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl iso
  • Suitable condensing agents for carrying out process (b) according to the invention are all auxiliaries which can usually be used for amidation reactions.
  • Acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphopentachloride, phosphorus oxychloride or thionyl chloride can preferably be used;
  • Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride;
  • Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), bis- (2
  • Acid acceptors such as conventional inorganic or organic bases, are also suitable as auxiliaries for the condensation when carrying out process (b) according to the invention.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, can preferably be used , Sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, furthermore ammonium
  • Suitable catalysts for carrying out process (b) according to the invention are all reaction accelerators customary for such reactions. 4-Dimethylamino-pyridine, 1-hydroxy-benzotriazole or dimethylformamide can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -78 ° C and + 120 ° C, preferably at temperatures between -60 ° C and + 25 ° C.
  • acylamino-cyclopropane-carboxylic acid of the formula (IV) is generally employed between 0.5 and 5 mol, preferably an equimolar amount of the compound of the formula (V).
  • the processing is again carried out using customary methods.
  • the procedure is generally carried out under atmospheric pressure.
  • reduced or elevated pressure for example between 0.1 and 10 bar.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Some pathogens of fungal and bacterial eradication that fall under the generic terms listed above may be mentioned as examples, but not by way of limitation:
  • 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 humuh or
  • 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. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. gra inea (conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helniinthosporium);
  • 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, for example, 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 he ⁇ otrichoides.
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
  • the active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • 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 cult 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 varieties which can or cannot be protected by plant breeders' rights.
  • Parts and organs of plants such as sprout, leaf, flower and root, are understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots 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 according to 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, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired ones
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be used.
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, lubricants and heat transfer fluids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dunethyl sulfoxide, as well as water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: e.g.
  • Suitable emulsifiers 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 and protein hydrolyzates.
  • 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 and protein hydrolyzates.
  • dispersants come in
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecillins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phmalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • inorganic pigments for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phmalocyanine 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 of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the range of trends or to prevent the development of resistance.
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Calcium polysulfide Ca ⁇ ropamid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Quinomethionate (Quinomethionate), Chlobenthiazon, Chlorfenazol,
  • Chloroneb chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemo ⁇ h, Dodine, Drazoxolon,
  • Famoxadone Fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, Fenitropan, fenpiclonil, fenpropidin, Fenpropimo ⁇ h, fentin acetate, Fentinhydroxyd, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, Flmprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl Alminium, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, metiimroxam, metiram, metomeclam, metsulfovax, müdiomycin, myclobutanil, myclozolin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, trifloxystrobin, triflumizole, triforine, triticonazole,
  • Bacillus popiUiae Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, Bistrifluron, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,
  • Chloethocarb Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, CMovaporthrin, Chromafenozide, Cis- Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezyan, Cyclophrine, Cyclophrine, Cyclophrine, Cyclophrinine, Clothianhrinin, Cyclophrinine .
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,
  • Fipronil Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Methoxyfenozide metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat
  • Tefluthrin temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon theta cypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, oxalate hydrogen thiocyclam, thiodicarb, Tbiofanox, thuringiensin, Tralocvthrin, tralomethrin, triarathene, Triazamate, triazophos, triazuron, Trichlophenidine, trichlorfon, triflumuron Trimethacarb Vamidothion, Vaniliprole, Verticillium lecanii
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans,
  • Candida glabrata and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these mushrooms in no way represents a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying,
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g ha.
  • all plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting,
  • transgenic plants Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CryllJA, Cry ⁇ iB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the traits that are particularly emphasized are the increased tolerance of the plants to certain ones herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • herbicidal active ingredients for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” include corn, cotton, soy and potato, which are among the
  • YIELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties, which are sold under the trade names Roundup Ready® (tolerance against
  • Glyphosate e.g. Maize, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, e.g. rapeseed
  • IMI® tolerance to imidazolinones
  • STS® tolerance to sulfonylureas e.g. maize
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or which will come onto the market in the future with these or future-developed genetic properties ("traits").
  • n-butylamine 0.1 g (1.45 mmol) of n-butylamine is added to a mixture of 0.2 g (0.73 mmol) of l - [(2,6-dichloroisonicotinoyl) - arnmo] cycloprocranecarboxylic acid in 5 ml of dichloromethane under argon. 0.19 g diisopropylethylamine and 0.204 g bis- (2-oxo-3- oxazolidinyl) phosphinic acid chloride and stirred for 16 hours at room temperature. The reaction mixture is poured into 50 ml of water and extracted three times with 50 ml of ethyl acetate each time.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)
  • Emulsifier 1 part 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.
  • the plants are treated with spores of Erysiphe grarninis f. sp. hordei pollinated.
  • the plants are then placed in a greenhouse at a temperature of approximately 20 ° C. and a relative atmospheric humidity of approximately 80% in order to promote the development of mildew pustules.
  • 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.
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%

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Abstract

L'invention concerne des dérivés d'acide carboxylite hétérocyclyle carbonyle aminocyclopropane de formule (I), dans laquelle G signifie hétérocyclyle à cinq ou six éléments, lequel est substitué par halogène et/ou alkyle comportant 1 à 4 atomes de carbone, et peut également comprendre un groupe cyclohexane annelé, R désigne un groupe -O-R1, -NH-R2 ou (Ia), ou bien un groupe N-hétérocyclyle saturé et éventuellement substitué, lié au groupe carbonyle par de l'azote, R1, R2, R3 et R4 représentent indépendamment l'un de l'autre alkyle éventuellement substitué, alcényle éventuellement substitué, alkinyle éventuellement substitué, cycloalkyle éventuellement substitué, aryle éventuellement substitué ou aralkyle éventuellement substitué. La présente invention porte également sur plusieurs procédés pour produire ces substances actives et sur leur utilisation comme microbicides. L'invention concerne aussi des acides carboxylites acylamino-cyclopropane de formule (IV), dans laquelle G a la signification susmentionnée, ainsi qu'un procédé de production associé.
PCT/EP2003/009124 2002-08-28 2003-08-18 Derives d'acide carboxylite heterocyclyle carbonyle aminocyclopropane WO2004024692A1 (fr)

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WO2009011305A1 (fr) * 2007-07-13 2009-01-22 Sumitomo Chemical Company, Limited Composé amide et procédé de lutte contre des maladies des plantes à l'aide de ce composé
WO2020007904A1 (fr) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
WO2021001331A1 (fr) 2019-07-03 2021-01-07 Bayer Aktiengesellschaft Thiophène carboxamides substitués et leurs dérivés comme microbicides
WO2021123051A1 (fr) 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thiophène carboxamides substitués, acides thiophène carboxyliques et leurs dérivés
WO2021122975A1 (fr) * 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thiophène carboxamides substitués et leurs dérivés comme microbicides
RU2797316C2 (ru) * 2018-07-05 2023-06-02 Байер Акциенгезельшафт Замещенные тиофенкарбоксамиды и аналоги в качестве антибактериальных средств

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CN102391147B (zh) * 2011-09-27 2014-03-26 中国农业大学 芳甲酰氨基环丙酸的制备和活性

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JPH06228101A (ja) * 1993-01-29 1994-08-16 Ube Ind Ltd イソニコチン酸アミド誘導体、その製法及び農園芸用病害防除剤

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WO2009011305A1 (fr) * 2007-07-13 2009-01-22 Sumitomo Chemical Company, Limited Composé amide et procédé de lutte contre des maladies des plantes à l'aide de ce composé
JP2009040775A (ja) * 2007-07-13 2009-02-26 Sumitomo Chemical Co Ltd アミド化合物とその植物病害防除用途
US11884643B2 (en) 2018-07-05 2024-01-30 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
WO2020007904A1 (fr) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
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JP2021530449A (ja) * 2018-07-05 2021-11-11 バイエル・アクチエンゲゼルシヤフト 抗菌剤としての置換チオフェンカルボキサミド類及び類縁体
JP2021530450A (ja) * 2018-07-05 2021-11-11 バイエル・アクチエンゲゼルシヤフト 抗菌剤としての置換チオフェンカルボキサミド類及び類縁体
CN112638894B (zh) * 2018-07-05 2024-03-29 拜耳公司 作为抗菌剂的取代的噻吩甲酰胺及类似物
US11401254B2 (en) 2018-07-05 2022-08-02 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
WO2020007902A1 (fr) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
AU2019297400B2 (en) * 2018-07-05 2024-05-02 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
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RU2797513C2 (ru) * 2018-07-05 2023-06-06 Байер Акциенгезельшафт Замещенные тиофенкарбоксамиды и аналоги в качестве антибактериальных средств
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