EP0865432A1 - Derives d'acide phenylacetique, procede et intermediaires pour leur production, et leur utilisation en tant que pesticides et/ou fongicides - Google Patents

Derives d'acide phenylacetique, procede et intermediaires pour leur production, et leur utilisation en tant que pesticides et/ou fongicides

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Publication number
EP0865432A1
EP0865432A1 EP96941603A EP96941603A EP0865432A1 EP 0865432 A1 EP0865432 A1 EP 0865432A1 EP 96941603 A EP96941603 A EP 96941603A EP 96941603 A EP96941603 A EP 96941603A EP 0865432 A1 EP0865432 A1 EP 0865432A1
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EP
European Patent Office
Prior art keywords
formula
alkyl
compounds
hydrogen
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP96941603A
Other languages
German (de)
English (en)
Inventor
Ruth Müller
Herbert Bayer
Reinhard Kirstgen
Hubert Sauter
Michael Rack
Albrecht Harreus
Bernd Müller
Thomas Grote
Klaus Oberdorf
Wassilios Grammenos
Franz Röhl
Gisela Lorenz
Eberhard Ammermann
Volker Harries
Siegfried Strathmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
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BASF SE
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Publication date
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Publication of EP0865432A1 publication Critical patent/EP0865432A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon 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

Definitions

  • the present invention relates to phenylacetic acid derivatives of the formula I.
  • R a , R 1 are hydrogen and alkyl
  • R 2 cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
  • R 3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;
  • A is a 5- or 6-membered heteroaromatic ring
  • R 4 substituted aryl
  • R 5 hydrogen, optionally subst.
  • the invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi. Phenylacetic acid derivatives for pest control are known from the literature [WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A
  • the present invention was based on new compounds with improved activity as an object.
  • the compounds I are obtainable in various ways according to methods known per se in the literature.
  • L 1 in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.
  • a base e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.
  • the required hydroxyimine III is obtained, for example, by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
  • L 2 in formula VI represents a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
  • reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
  • a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
  • the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula v, where v is then converted to I with the nucleophilically substituted reagent VI.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,
  • a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,
  • Q ⁇ in formula IXb stands for the anion of an acid, in particular an inorganic acid, for example.
  • reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73f; Houben-Weyl, vol. E 14b, p. 369f and p. 385f.
  • the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VII into a corresponding benzyloxyimine of the formula VIII, VIII being subsequently converted to I with the hydroxylamine IXa or its salt IXb.
  • the reaction is carried out in a manner known per se in an inert organic solvent according to the in Houben-Weyl, vol. E 14b, p. 369f; Houben-Weyl, Vol. 10/1, pp. 1189f and Houben-Weyl, Vol. 10/4, pp. 73f or EP-A 513 580.
  • reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488, DE-Anm. No. 42 28 867.3 methods described.
  • the required carbonyl compound X is obtained, for example, by reacting a corresponding hydroxyiminocarbonyl compound VIa with a nucleophilically substituted reagent VI
  • the reactions are carried out in a manner known per se in an inert organic solvent in accordance with the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55f, p. 73f, p. 180f and p. 217f; Houben-Weyl, vol. E 14b, pp. 307f and 369f, Houben-Weyl, vol. E 5, pp. 780f. 1.5
  • the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyimino derivative VIa in the corresponding benzyloxyimino derivative of the formula V, V being subsequently converted to I with the nucleophilically substituted reagent VI as described above.
  • the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl derivative of the formula XI into the benzyloxyimino derivative of the formula VIII and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.
  • the corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII. 4.
  • Compounds I in which R 3 is bonded to the skeleton via an oxygen atom are in some cases also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, pp. 826f; Aust. J. Chem. 27, 1341-9 (1974)].
  • the corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII.
  • Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the ⁇ -keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)).
  • the corresponding carboxamides are obtained from the derivatives XV by amidation and are subsequently converted into the compounds I.
  • compounds XVI are obtained by converting an ortho-halogen compound after metalation with oxalyl chloride into the corresponding keto acid chloride, which is then converted into the corresponding amide XVI with an amine (cf. J. Org.
  • the compounds I in which Y denotes NR a are obtained , starting from the keto esters XV, by first derivatizing the keto function and converting the derivatives thus obtained to the amide using a corresponding amine (Houben-Weyl, Vol. E5, p. 941 f.)
  • the compounds II are known (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 585 751, EP-A 400 417, EP-A 251 082) or can be prepared by the methods described therein become.
  • Particularly preferred intermediates for the preparation of the compounds I are the compounds III '
  • U 2 is oxygen, NOH or NOR 5 , where the radicals A, R 3 , R 4 and R 5 in general and in particular have the meaning given above.
  • the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures are obtained in the synthesis, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (for example under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the ice isomers of the compounds I are generally preferred with regard to their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1 -Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl , 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2 E
  • Dialkylamino an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;
  • Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkylsulfonyl straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-SO 2 -);
  • Alkylaminocarbonyl alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Dialkylaminocarbonyl dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkylaminothiocarbonyl alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
  • Dialkylaminothiocarbonyl dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluor
  • Alkoxy straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via an oxygen atom (-O-), e.g.
  • C 1 -C 6 alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbuty
  • Halogenalkoxy straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, and where these groups are bonded to the skeleton via an oxygen atom;
  • Alkylthio straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g.
  • C 1 -C 6 alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2- Dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,
  • Alkenyloxy straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via an oxygen atom (-O-);
  • Alkenylthio straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via a sulfur atom (-S-);
  • Alkenylamino an amino group which carries a straight-chain or branched alkenyl group having 2 to 6 carbon atoms as mentioned above;
  • Alkenylcarbonyl straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propy
  • Alkynyloxy straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via an oxygen atom (-O-);
  • Alkynylthio straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a sulfur atom (-S-);
  • Alkynylamino an amino group which carries a straight-chain or branched alkynyl group having 2 to 6 carbon atoms as mentioned above;
  • Alkynylcarbonyl straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Cycloalkoxy monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-);
  • Cycloalkylthio monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-); Cycloalkylamino: an amino group bearing a monocyclic alkyl group having 3 to 6 carbon ring members as mentioned above;
  • Cycloalkenyl monocyclic alkenyl groups with 5 to 8 carbon ring members, e.g. Cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; Cycloalkenyloxy: monocyclic alkenyl groups with 5 to 8
  • Aryl or aryloxy, arylthio, arylamino, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon residues which directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (arylamino) via a nitrogen atom or (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-SO 2 -) are bound to the structure, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl - and sulfonyl residues;
  • Hetaryl or hetaryloxy, hetarylthio, hetarylamino, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-O-) or (hetarylthio) a sulfur atom (-S-), (hetarylamino) via a nitrogen atom or (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a Sulfonyl group (-SO 2 -) are bound to the skeleton, for example
  • 5-membered heteroaryl containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2- yl;
  • 5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl , 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadi azol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen - Or can contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1,4-diyl group;
  • 5-membered heteroaryl bound via nitrogen containing one to four nitrogen atoms.
  • benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one
  • Nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-the-n-1,4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1, 2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;
  • 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline, or the corresponding oxy, thio, amino, carbonyl or sulfonyl groups.
  • cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 - Alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C
  • substituted by conventional groups is intended to express that the radicals in question can be partially or completely halogenated and / or can carry one to three of the following substituents: cyano, nitro, hydroxy, amino, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, di-C 1 -C 4 - alkylamino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, phenyl, phenoxy, benzyl and benzyloxy, and / or a C 3 -C 5 alkylene, C 2 -C 4 alkyleneoxy bonded to two adjacent atoms , C 1 -C 4 -Oxyalkylenoxy, and / or a group C (
  • 5- or 6-membered heteroaromatic rings in the definition of A are to be understood in particular as the following groups A-1 to A-88.
  • the positions marked with # mark the bond to the rest of the molecule.
  • the nitrogen atoms the 5-ring heteroaromatics with free valences can carry hydrogen or C 1 -C 6 alkyl in this position.
  • X is NO 3 and Y is NR a and R a is hydrogen or methyl.
  • X is NO 3 and Y is NR a and R 1 is hydrogen or methyl.
  • X is NO 3 and Y is NR a and R a is hydrogen and R 1 is
  • CHCH 3 and Y means oxygen.
  • compounds of the formula I are preferred in which X is CHCH 2 CH 3 and Y is oxygen.
  • R 2 is halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, in particular fluorine, chlorine, methyl and methoxy.
  • R 3 represents one of the following substituents: hydrogen, hydroxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 - C 4 alkylthio and C 3 -C 6 cycloalkyl, in particular hydrogen, hydroxy, chlorine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, methylthio and cyclopropyl.
  • R 3 represents one of the following substituents: hydrogen, halogen,
  • R 3 represents hydrogen or C 1 -C 4 alkyl, in particular methyl.
  • R 4 represents substituted phenyl.
  • R 4 represents phenyl substituted by customary groups.
  • R 4 is phenyl which carries at least one of the following substituents: cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 - Alkoxy, especially fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy and ethoxy.
  • R 4 is phenyl which carries at least one trifluoromethyl group.
  • A represents one of the following radicals: A-2, A-6, A-10, A-11, A-12, A-17, A-18, A-20, A- 21, A-27, A-29, A-33, A-35, A-39, A-43, A-44, A-45, A-46, A-49, A-50, A-51, A-52, A-55, A-59, A-60, A-61, A-62, A-63, A-65, A-67, A-68, A-69, A-71, A- 72, A-76, A-78, A-79, A-80, A-81 and A-83.
  • A represents one of the following radicals: A-2, A-20, A-21, A-39, A-55, A-59, A-67, A-68, A- 69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-20.
  • A represents one of the following radicals: A-10, A-II, A-12, A-27, A-29, A-43, A-44, A-45, A- 46, A-63 and A-65, particularly preferably A-44.
  • A represents one of the following radicals: A-17, A-18, A-33, A-35, A-49, A-50, A-51, A-52, A- 60, A-61 and A-62, particularly preferably A-50.
  • compounds I are preferred in which A is A-2, A-20, A-21 and A-39, particularly preferably A-20.
  • compounds I are preferred in which A is A-10, A-II and A-12, particularly preferably A-10.
  • compounds I are preferred in which A is A-17 and A-18, particularly preferably A-18.
  • compounds I are preferred in which A is A-27, A-29, A-33 and A-35, particularly preferably A-33 and A-35.
  • compounds I are preferred in which A is A-43, A-44, A-45 and A-46, particularly preferably A-44 and A-46.
  • compounds I are preferred in which A is A-49, A-50, A-51 and A-52, particularly preferably A-50 and A-52.
  • compounds I are preferred in which A is A-55, A-59, A-60, A-61, A-62, A-63 and A-65, particularly preferably A-60, A-62 and A- 65, stands.
  • compounds I are preferred in which A is A-67, A-68, A-69, A-71 and A-72, particularly preferably A-67 and A-68.
  • compounds I are preferred in which A is A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-79.
  • R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, di- C 1 -C 4 alkylamino-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl.
  • R 5 represents one of the following substituents: hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, in particular hydrogen, methyl, ethyl, n-propyl, iso-propyl and methoxyethyl.
  • R 5 represents one of the following substituents: hydrogen and C 1 -C 4 -alkyl, in particular methyl, ethyl, n-propyl and isopropyl, particularly preferably methyl.
  • R 5 is C 3 -C 6 alkenyl and C 3 -C 6 haloalkenyl.
  • R 5 is C 3 -C 6 alkynyl and C 3 -C 6 haloalkynyl.
  • the compounds I are suitable as fungicides.
  • the compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides. They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans and pumpkin family, as well as on the seeds of these plants.
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia types on cereals, Rhizoctonia and rice species Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Cereospora arachidicola on peanuts, Pseudocrichosidesella on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viti
  • the compounds I are also suitable for combating
  • Harmful fungi in material protection e.g. wood, paper, fibers or fabric
  • material protection e.g. wood, paper, fibers or fabric
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
  • formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compounds according to the invention.
  • the formulations are prepared in a known manner for example, by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • amounts of active ingredient generally range from 0.001 to 0.1 g, preferably 0.01 to 0.05 g required per kilogram of seed.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates are in
  • Material protection for example 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
  • the agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
  • Sulfur, dithiocarbamates and their derivatives such as iron, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, Tetramethylthiuramdisulfide, ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), ammonia complex of Zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6
  • Strobilurins such as methyl-E-methoxyimino- [ ⁇ - (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino- [ ⁇ - (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [ ⁇ - (2,5-dimethylphenoxy) -o-tolyl] acetamide.
  • Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 -cyclopropyl-pyrimidin-2-yl) aniline.
  • Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile.
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide.
  • the compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, storage protection and veterinary sectors.
  • the harmful insects from the order of the butterflies include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobisturaumumone, Cheimatobisturaumumone Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,
  • Diptera From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropucitae, Cordylobia anthropucaga, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropacea, brassylaciaacropaceacita, brassylaciaacropia , Fannia canicularis, Gasterophilus intestinalis,
  • Tipula oleracea Tipula paludosa.
  • Thrips for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
  • From the order of the hymenoptera for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invieta.
  • Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leueopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensidata, Nezara pratensidata, Sol .
  • bugs Heteroptera
  • Acrosternum hilare Blissus leueopterus
  • Cyrtopeltis notatus Dysdercus cingulatus
  • Dysdercus intermedius Eurygaster integriceps
  • Euschistus impictiventris Leptoglossus phyllopus
  • Lygus lineolaris Lygus pratensidata
  • Nezara pratensidata Sol .
  • suckers for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui,
  • Termes natalensis From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinataus, Melanopladusana, Melanopladipana Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
  • Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexican
  • arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata Otobius megnini, Paratetranyehus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sar
  • Amblyomma americanum such as Amblyomma
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g.
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied.
  • the application forms depend entirely on the purposes; she should ensure the finest possible distribution of the active compounds according to the invention in any case.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
  • active ingredients are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • the application rate of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent, by means of wetting agents,
  • Adhesives, dispersants or emulsifiers are homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • Parts of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil are present (active ingredient content 9% by weight).
  • V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenalphasulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and in grind in a hammer mill (active ingredient content 80% by weight).
  • Spray liquor containing 0.1% by weight of the active ingredient.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • Example 1 Synthesis of (E, E, E) -2 - [[[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] - ⁇ - (methoxyimino) phenylacetic acid methyl ester
  • the active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight.
  • % Emulphor® EL Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration.
  • Emulsifier was prepared, sprayed and dusted with spores of powdery mildew (Erysiphe graminis var. Tritici) 24 hours after the spray coating had dried on.
  • the test plants were then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area. In this test, those with 250 ppm of compounds no.
  • Leaves of potted vines of the "Müller-Thurgau" variety were sprayed with an aqueous spray mixture which had been prepared with a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier.
  • the plants were divided in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
  • the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C.
  • the active ingredients were:
  • b. as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) processed and with the desired concentration with acetone in the case of a. or with water in the case of b. diluted.
  • Nekanil® LN Litensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Emulphor® EL Emulphor® EL
  • Potted bush beans with a fully developed pair of leaves were sprayed to runoff point in the spray booth with the aqueous active ingredient solution.
  • the plants were guided over a running rail to the turntable of the spray booth and sprayed on all sides with 3 differently oriented nozzles when 30 cm 3 of active ingredient solution was applied.
  • the spraying process took about 20 seconds.
  • the plants were heavily infested with mites and abundant oviposition. The effect was assessed after 5 days using a binocular. It was determined whether all stages were recorded evenly. The plants were under normal greenhouse conditions during this time. In this experiment, substance 1.17 from the table showed an activity threshold of 200 ppm.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne des dérivés d'acide phénylacétique de formule (I), dans laquelle les substituants et l'indice ont la signification suivante: X représente NOCH3, CHOCH3, CHCH3 et CHCH2CH3; Y représente NRa et O; Ra, R1 représentent hydrogène et alkyle; R2 représente cyano, nitro, halogène, alkyle, halogénure d'alkyle et alcoxy, m vaut 0, 1, ou 2; R3 représente hydrogène, hydroxy, amino, cyano, halogène, alkyle, halogénure d'alkyle, cycloalkyle, alcoxy, alkylthio, alkylamino et dialkylamino; A représente un noyau hétéroaromatique à 5 ou 6 chaînons; R4 représente aryle substitué; R5 représente hydrogène, l'un des groupes suivants éventuellement substitués: alkyle, alcényle, alcynyle, cycloalkyle, cycloalcényle, hétérocyclyle, aryle et hétaryle. L'invention concerne également les sels desdits dérivés d'acide phénylacétique, un procédé et des intermédiaires pour leur production et leur utilisation.
EP96941603A 1995-12-04 1996-11-28 Derives d'acide phenylacetique, procede et intermediaires pour leur production, et leur utilisation en tant que pesticides et/ou fongicides Withdrawn EP0865432A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1995145094 DE19545094A1 (de) 1995-12-04 1995-12-04 Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
DE19545094 1995-12-04
PCT/EP1996/005247 WO1997020816A1 (fr) 1995-12-04 1996-11-28 Derives d'acide phenylacetique, procede et intermediaires pour leur production, et leur utilisation en tant que pesticides et/ou fongicides

Publications (1)

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EP0865432A1 true EP0865432A1 (fr) 1998-09-23

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EP (1) EP0865432A1 (fr)
JP (1) JP2000505058A (fr)
AU (1) AU1094097A (fr)
DE (1) DE19545094A1 (fr)
WO (1) WO1997020816A1 (fr)
ZA (1) ZA9610127B (fr)

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JP5923038B2 (ja) * 2010-06-24 2016-05-24 クミアイ化学工業株式会社 アルコキシイミノ誘導体及び節足動物防除剤

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WO1992013830A1 (fr) * 1991-01-30 1992-08-20 Zeneca Limited Fongicides
AU690190B2 (en) * 1994-01-05 1998-04-23 Bayer Aktiengesellschaft Pesticides
HUT75534A (en) * 1994-02-04 1997-05-28 Basf Ag Phenyl acetic acid derivatives, process and intermediate products for their production and agents containing them

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WO1997020816A1 (fr) 1997-06-12
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DE19545094A1 (de) 1997-06-05
JP2000505058A (ja) 2000-04-25

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