WO2005066138A1 - Amides heterocycliques substitues a effet fongicide - Google Patents

Amides heterocycliques substitues a effet fongicide Download PDF

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Publication number
WO2005066138A1
WO2005066138A1 PCT/EP2004/014453 EP2004014453W WO2005066138A1 WO 2005066138 A1 WO2005066138 A1 WO 2005066138A1 EP 2004014453 W EP2004014453 W EP 2004014453W WO 2005066138 A1 WO2005066138 A1 WO 2005066138A1
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Prior art keywords
formula
methyl
ethyl
butyl
propyl
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PCT/EP2004/014453
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Joachim Kluth
Thomas Seitz
Heiko Rieck
Ulrike Wachendorff-Neumann
Karl-Heinz Kuck
Adeline Mousques
Nathalie Huser-Schwarz
Hélène LACHAISE
Gilbert Spica
Pierre Genix
Jean-Pierre Vors
Jean-Luc Zundel
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Bayer Cropscience Ag
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Priority to EP04804054A priority Critical patent/EP1706387A1/fr
Priority to JP2006546013A priority patent/JP2007515444A/ja
Publication of WO2005066138A1 publication Critical patent/WO2005066138A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

Definitions

  • the invention relates to amides, several processes for their preparation and their use for controlling harmful organisms.
  • Rl, R 2 , and R 3 are the same or different and are independently hydrogen, halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio.
  • Alkylsulfonyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfmyl 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; each straight-chain
  • Rl, R 2 , and R 3 are not simultaneously hydrogen, or
  • R and R 2 together with the carbon atoms to which they are attached form a carbocyclic ring
  • Het represents an unsubstituted or substituted five-membered aromatic heterocyclic ring
  • R ⁇ represents hydrogen, halogen, cyano, alkyl having 1 to 8 carbon atoms, alkenyl or alkynyl having 2 to 8 carbon atoms or haloalkyl having 1 to 8 carbon atoms and 1 to 9 halogen atoms,
  • R 5 and R ⁇ are the same or different and are independently of one another unsubstituted or halogen or cyano-substituted alkyl, alkoxyalkyl each having 1-8 carbon atoms in the respective alkyl chains or alkenyl or alkynyl each having 2-8 carbon atoms or cycloalkyl having 3-8 Carbon atoms or. Represents unsubstituted or substituted arylalkyl having 1 to 8 carbon atoms in the alkyl chain,
  • A represents alkanediyl or cycloalkanediyl
  • Y stands for oxygen or sulfur.
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as.
  • Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings.
  • Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused-on ⁇ i or bridged rings.
  • the new amides of the general formula (I) have a very good activity against harmful organisms, in particular a strong fungicidal activity.
  • the compounds according to the invention are optionally in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as, for. B. E and Z, eis or trans, threo and erythro, and optical isomers before. Both the E and the Z isomers, as well as the threo- and erythro, the optical isomers, and any mixtures of these isomers, tautomers are described and claimed.
  • the invention preferably relates to compounds of the formula (Ia)
  • R ⁇ R 2, and R 3 are identical or different and independently hydrogen ", fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, ⁇ -pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy , Trifluoromethoxy, difluorochloro ethoxy, Trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluor
  • Rl and R 2 together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members, where Rl, R 2 and R 3 are not simultaneously hydrogen,
  • R ⁇ a represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl,
  • R ⁇ and R ⁇ are the same or different and are independently methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl,
  • Y stands for oxygen or sulfur
  • G represents oxygen, sulfur or -R ⁇ a , where R 7a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R 7a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention also preferably relates to compounds of the formula (Ib)
  • A, R1, R 2 , R 3 , R ⁇ , R ⁇ and Y have the same meaning as preferably given for A, R% R 2 , R 3 , R 5 , R ⁇ and Y in formula (Ia) is
  • R ⁇ b represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl,
  • G 2 represents oxygen, sulfur or NR 71D , where
  • R ⁇ b represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention further preferably relates to compounds of the formula (Ic)
  • R 1 , R 2 , R 3 , R 5 , R 6 and Y have the same meaning as has preferably been given for AR *, R 2 , R 3 , R 5 , R ⁇ and Y in formula (la) .
  • R ⁇ 0 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Is allyl, propargyl or trifluoromethyl
  • G 3 represents oxygen, sulfur or NR 7c , where
  • R 7c represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention further preferably relates to compounds of the formula (Id)
  • A, Rl, R 2 , R 3 , R 5 , R 6 and Y have the same meaning as preferably given for A, R *, R 2 , R 3 , R 5 , R ⁇ and Y in formula (la) is TM represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • G ⁇ stands for oxygen, sulfur or N-R,
  • R 7 ( ⁇ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention further preferably relates to compounds of the formula (Ie)
  • R 1 , R 2 , R 3 , R 5 , R 6 and Y have the same meaning as preferably given for AR 1 , R 2 , R 3 , R 5 , R 6 and Y in formula (1 a) is
  • G 5 represents oxygen, sulfur or NR 7e , where R 7e represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention further preferably relates to compounds of the formula (If)
  • A, R, R 2 , R 3 , R 5 , R ⁇ and Y have the same meaning as has preferably been given for A, R, R 2 , R 3 , R ⁇ , R ⁇ and Y in formula (la) .
  • G ⁇ stands for oxygen, sulfur or -R 7 ⁇ , wherein
  • R 7 ⁇ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • the invention further preferably relates to compounds of the formula (Ig)
  • A, R, R 2 , R 3 , R 5 , R6 and Y have the same meaning as preferably given for A, Rl, R 2 , R 3 , R 5 , R ° and Y in formula (Ia),
  • G 7 represents oxygen, sulfur or NR 7 S, where
  • R 7 ⁇ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • Rl, R 2 and R 3 are the same or different and, independently of one another, are also particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl
  • R and R 2 together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members:
  • R, R 2 , and R 3 do not simultaneously represent hydrogen.
  • Y particularly preferably represents oxygen.
  • R5 and R6 are identical or different and, independently of one another, are particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl.
  • R ⁇ a is particularly preferred for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and
  • G particularly preferably represents oxygen, sulfur or NR 7a , where R 7a particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R ⁇ b particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano and G 2 particularly preferably represents oxygen, sulfur or NR 71 :) , where
  • R 71D particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R ⁇ 0 particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano and
  • G 3 particularly preferably for oxygen, sulfur or NR 7c , wherein
  • R 7c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R ⁇ d particularly preferably for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and
  • G ⁇ particularly preferred for oxygen, sulfur or NR 7c *, wherein
  • R 7 d particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • G ⁇ particularly preferably represents oxygen, sulfur or NR e , where
  • R 7e particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • G ⁇ particularly preferably represents oxygen, sulfur or NR 7 ⁇ , wherein
  • R 7f particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • G 7 particularly preferably represents oxygen, sulfur or NR 7 S, where R 7 S particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • radical definitions given for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.
  • R, R 2 , R 3 and R ⁇ have the meanings given above and represent hydroxyl, halogen or alkoxy,
  • Formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process a) according to the invention.
  • R *, R 2 , R 3 and R ⁇ preferably, or in particular, have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R1 , R 2 , R 3 and R ⁇ were specified;
  • T preferably represents alkoxy having 1 to 4 carbon atoms, in particular methoxy or ethoxy, hydroxyl or chlorine.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (see, for example, J. Org. Chem. 27 (1962) 4305; J. Chem. Soc. (1963) 5838, 'J. Chem Soc. (1963) 5845; Chem. Ber. 106, 3275 (1973); US 3,479,365; US 3,551,440; J. Org. Chem. (1967) 32 (10) 3132; Tetrahedron 25, (1969), 389; Synthetic Com. (1987), 17 (2), 165; EP 352581; EP 352581; EP 1186598; Bioor. & Medicinal Chem.
  • the amines required for starting materials are generally defined by the formula (HI).
  • A, R 5 and R ⁇ preferably, or in particular, have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R ⁇ and R ° were specified.
  • Some of the amines of the formula (IH) are known organic synthetic chemicals and / or can be prepared by processes known per se.
  • a and R 5 have the meanings given above and
  • R 8 represents allyl, propargyl, 2-butynyl or cyanoethyl
  • R9 represents allyl, propargyl, 2-butinyl or cyanomethyl.
  • a and R 5 have the meanings given above,
  • the amino group of the compounds of the formulas (IV-a) and (IV-b) is optionally provided with a protective group which is customary for amines, such as, for example, t-butoxycarbonyl, by customary methods. This gives rise to compounds of the formula (IV-a *) or (IV-b *)
  • PG stands for the protective group.
  • R °, R ", PG, and R ⁇ and R ° have the meanings given above,
  • Hydroxy compounds are generally defined by the formula (TV-a).
  • this formula (IV-a) preferably, or in particular, has the meaning which has already been stated in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for R ⁇ .
  • hydroxy compounds of the formula (IV-a) are commercially available synthetic chemicals or can be obtained by known methods (compare, for example, J. Chem. Soc. 127 (1925), 560 and J. Amer. Chem. Soc. 72 (1950), 2781; JP 11130739 or DE 19958165).
  • Formula (IV-b) provides a general definition of the hydroxy compounds required alternatively as starting materials for carrying out process c) according to the invention.
  • R ° preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for RP in connection with the description of the compounds of the formula (I) according to the invention.
  • the hydroxy compounds of the formula (IV-b) are commercially available synthetic chemicals or can be obtained by known methods (compare, for example, Ger. Offen, 4322065; J. Org. Chem., 53 (5), 1064-71 (1988); Synth. Comm., 7 (1), 71-8 (1977)).
  • the compounds allyl, propargyl, 2-butynyl chloride, bromide or iodide or chlorine, bromine or iodoacetonitrile which are furthermore required as starting materials for carrying out process c) according to the invention are generally customary synthetic chemicals.
  • Amides required as starting materials for carrying out process b) according to the invention are compounds according to the invention and can be obtained by process a) according to the invention.
  • All reagents that are capable of exchanging carbon-bound oxygen atoms for sulfur atoms such as e.g. Hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent.
  • Hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent are commercially available
  • Process a) according to the invention is optionally carried out in the presence of a diluent.
  • a diluent water and organic solvents come into consideration. 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 benzonitrile; Amides such as N, N-dimethylformamide
  • Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, for example, 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, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as.
  • Trimethylamine triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecen (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecen
  • Process a) according to the invention is optionally carried out in the presence of a suitable condensing agent.
  • a suitable condensing agent include acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl 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-l, 2-dihydroquinoline (EEDQ) or triphehyl-
  • Process a) according to the invention is optionally carried out in the presence of a catalyst.
  • a catalyst examples include 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out process a) according to the invention. In general, temperatures between - 50 ° C and + 150 ° C, preferably at temperatures between -20 ° C and 150 ° C.
  • process a) according to the invention 1 to 5 mol, preferably 1.0 to 2.5 mol, of amine are generally employed per mol of carboxylic acid derivative of the formula (11).
  • the process a) according to the invention can also be carried out as a two-stage process.
  • the carboxylic acid derivatives of the general formula (II) are first converted into an activated form and, in a subsequent step, reacted with the amines of the general formula (TU) to give the amides of the general formula (I) according to the invention.
  • all carboxy-activated derivatives can be used, e.g. Acid halides, preferably acid chlorides, acid azides, furthermore symmetrical and mixed anhydrides, such as for example the mixed o-alkyl carbonic anhydrides, further activated esters, such as e.g. p-nitrophenyl ester or N-hydroxisuccinimide ester as well as adducts with condensing agents, e.g. Dicyclohexyl carbodiimide or activated forms of the carboxylic acids generated in situ.
  • Acid halides preferably acid chlorides, acid azides, furthermore symmetrical and mixed anhydrides, such as for example the mixed o-alkyl carbonic anhydrides, further activated esters, such as e.g. p-nitrophenyl ester or N-hydroxisuccinimide ester as well as adducts with condensing agents, e.g. Dicyclohexyl carbodiimide or activate
  • Suitable diluents for carrying out process b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene 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.
  • reaction temperatures can be varied within a substantial range when carrying out process b) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • reaction is carried out, worked up and isolated using known processes (see also the preparation examples).
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the reaction is carried out, worked up and isolated according to known methods.
  • 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 in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, 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 hu uli 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. graminea (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (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, 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 herpotrichoides.
  • 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 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 materials of the invention 'are thus used to protect plants for a certain period of time after treatment against attack by the pathogens mentioned.
  • 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 particularly successfully to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Alternaria, Phytophtora and Plasmopara 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 precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop 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 shoots, leaves, flowers and roots, 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, offshoots and seeds.
  • the treatment of the plants and plant parts according to the invention with the active compounds takes place directly or by influencing their surroundings, living space or storage space according to the usual treatment methods, for example by 'dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • 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 adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production plants for example cooling water circuits, which may be impaired by the multiplication of microorganisms, may also be mentioned.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, 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 molds, wood-coloring 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
  • a ⁇ ireobasidium 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • 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 Glyc ⁇ l 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.
  • 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.
  • Solid carrier materials come into question: 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.
  • Solid carrier materials for granules are considered: for example broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, Corn cobs and tobacco stalks.
  • Suitable emulsifiers and / or foaming 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.
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • 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 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 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 spread the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate;
  • Buthiobate butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin;
  • fenamidone Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil;
  • fenpiclonil fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover;
  • flumorph fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; Flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
  • iprovalicarb frumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb;
  • Organophosphates e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorophyros (-methyl / -ethyl) Coumaphos, Cyanofenphos, 'Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Ethulophone, EthN.
  • Organophosphates e.g. acephate, azamethiphos, azin
  • EPN Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobefos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathec, Methathionos, Methathionos, Malathion Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl ⁇ ethyl), Profenofos, Propaphos, Pro petamphos, prothiofos, prothoate, pyraclofo
  • Pyrethroids e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-chlorothrinet -Resmethrin, Cis-Perrnethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Delta-methrin, Empenthrin (lR-isomer), Esfenxerate, Fenofen, Etofen , Fenpropathrin, fenpyrithrin, f
  • Chloronicotinyls / neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
  • Fiprole e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
  • Mectins e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin
  • Diacylhydrazine e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • Benzoyl ureas e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • Cyromazines 10. Inhibitors of oxidative phosphorylation, ATP disruptors
  • organotins e.g. azocyclotin, cyhexatin, fenbutatin-oxide
  • METI's e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • tetronic acids e.g. spirodiclofen, spiromesifen
  • 16.2 tetramic acids [e.g. 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] - dec-3-en-4-yl ethyl ester, CAS Reg.No .: 382608-10-8) and carbonic acid, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.-No .: 203313- 25-1)] 17.
  • Carboxamides e.g. 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5
  • fumigants e.g. aluminum phosphide, methyl bromide, sulfuryl fluoride
  • mite growth inhibitors e.g. clofentezine, etoxazole, hexythiazox
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, molds and diphasic fungi (for example 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.
  • Candida species such as Candida albicans, Candida glabrata
  • 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.
  • the list of these fungi is in no way
  • 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, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • 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.
  • plant plants which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are species and plant cultivars and their parts are treated; in a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” 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 cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also result in superadditive (“synergistic”) effects Strengthening the effect 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 crop 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.
  • superadditive superadditive
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”).
  • traits are better plant wax. 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 ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and or workability
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or vir and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, corn, soybeans, potatoes, cotton, tobacco and rapeseed are particularly emphasized.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants").
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • traits are also used Particularly emphasized is the increased, defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazoline, ⁇ sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the desired properties (“traits”) ) conferring genes can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • 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 corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready ⁇ (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • rapeseed rapeseed
  • LMI® tolerance to Imidazolinone
  • STS® tolerance to sulfonylureas such as maize
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or to be marketed in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A 0, by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)
  • logP values were determined in accordance with EEC Directive 79/831 Annex V.
  • a 8 by HPLC gradient method, acetonitrile / 0.1% aqueous phosphoric acid
  • Solvent 24.5 parts by weight of acetone, 24.5 parts by weight of dimethylacetamide
  • Emulsifier . • 1 part by weight of alkyl aryl 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 3 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.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl 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.

Abstract

L'invention concerne des amides de formule (I) dans laquelle les symboles ont les significations indiquées dans la description. L'invention concerne également un procédé pour produire ces substances et leur utilisation pour lutter contre des micro-organismes indésirables. L'invention concerne en outre des produits intermédiaires de formules (IIIa) et (IIIb) dans lesquelles les symboles ont les significations indiquées dans la description.
PCT/EP2004/014453 2003-12-22 2004-12-18 Amides heterocycliques substitues a effet fongicide WO2005066138A1 (fr)

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EP1794167A4 (fr) * 2004-09-10 2009-10-21 Syngenta Ltd Isoxazoles substitues en tant que fongicides
EP1794167A1 (fr) * 2004-09-10 2007-06-13 Syngenta Limited Isoxazoles substitues en tant que fongicides
US8283349B2 (en) 2007-02-22 2012-10-09 Bayer Cropscience Ag Fungicide N-(3-phenylpropyl) carboxamide derivatives
WO2008101976A1 (fr) 2007-02-22 2008-08-28 Bayer Cropscience Sa Dérivés fongicides de n-(3-phénylpropyl)carboxamide
US8455499B2 (en) 2008-12-11 2013-06-04 Amira Pharmaceuticals, Inc. Alkyne antagonists of lysophosphatidic acid receptors
US8048902B2 (en) 2008-12-15 2011-11-01 Amira Pharmaceuticals, Inc. Antagonists of lysophosphatidic acid receptors
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