EP0851863A1 - Acides phenylacetiques, procedes permettant de les preparer et agents les contenant - Google Patents

Acides phenylacetiques, procedes permettant de les preparer et agents les contenant

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Publication number
EP0851863A1
EP0851863A1 EP96931781A EP96931781A EP0851863A1 EP 0851863 A1 EP0851863 A1 EP 0851863A1 EP 96931781 A EP96931781 A EP 96931781A EP 96931781 A EP96931781 A EP 96931781A EP 0851863 A1 EP0851863 A1 EP 0851863A1
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EP
European Patent Office
Prior art keywords
formula
compounds
alkyl
methyl
halogen
Prior art date
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Withdrawn
Application number
EP96931781A
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German (de)
English (en)
Inventor
Herbert Bayer
Ruth Müller
Hubert Sauter
Michael Rack
Albrecht Harreus
Eberhard Ammermann
Volker Harries
Gisela Lorenz
Siegfried Strathmann
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BASF SE
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BASF SE
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Publication of EP0851863A1 publication Critical patent/EP0851863A1/fr
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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    • 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
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    • 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
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
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    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
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    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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Definitions

  • Phenylacetic acids process for their preparation and compositions containing them Description
  • the present invention relates to phenylacetic acids of the formula I.
  • R is hydrogen and C 1 -C 4 alkyl
  • Z a possibly subst. a saturated or partially or completely unsaturated cyclic radical bonded via a nitrogen atom, which, in addition to the nitrogen atom via which it is bonded, can contain, in addition to carbon ring members, one to four heteroatoms from the group consisting of nitrogen, oxygen and sulfur;
  • R 1 is hydrogen and C 1 -C 4 alkyl; R 2 cyano, nitro, trif luormethyl, halogen, C 1 -C 4 alkyl and
  • R 3 is hydrogen, cyano, nitro, hydroxy, amino, cyclopropyl,
  • Halogen C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy,
  • R 4 is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 alkylcarbonyl, C 2 -C 10 alkenylcarbonyl, C 2 -C 10 alkynylcarbonyl or C 1 -C 10 alkylsulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups:
  • Halogen C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl,
  • Hetaryloxy and hetarylthio where the 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 ,
  • Halogen C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl,
  • A represents oxygen, sulfur and nitrogen and the nitrogen carries hydrogen or C 1 -C 6 alkyl; n represents 0 or 1, and
  • R a , R b each represent hydrogen or C 1 -C 6 alkyl, and their salts.
  • the invention 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 controlling animal pests and harmful fungi are known from the literature (EP-A 422 597, EP-A 463 488, EP-A 370 629, EP-A 460 575, EP-A 472 300, WO-A 90 / 07,493 , WO-A 92 / 13,830, WO-A 92 / 18,487).
  • the older German patent applications P 44 03 447.4 and P 44 03 448.2 describe phenylacetic acid derivatives with bis-oxime side chains with action against animal pests and harmful fungi.
  • the present invention was based on compounds with improved activity as an object.
  • L 1 in formula II stands for a nucleophilically interchangeable
  • Leaving group e.g. Halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate and triflate.
  • the reaction takes place in a manner known per se in an inert organic solvent in the presence of a base (for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine) in accordance with the methods described in Houben-Weyl, Vol. E 14b, p. 370f and Houben-Weyl, Vol. 10 / 1, p. 1189f described methods.
  • a base for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine
  • the required hydroxyimine III is obtained, for example, by reacting a corresponding purple dihydroxyimine with a nucleophilically substituted reagent V.
  • L 2 in formula V stands for a nucleophilically interchangeable
  • halogen or sulfonate groups preferably chlorine, bromine, iodine, mesylate, tosylate and triflate.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (for example potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine) in accordance with the methods described in Houben-Weyl, vol. E 14b, p. 307f, p. 370f and p . 385f; Houben-Weyl, Vol. 10/4, p. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f.
  • a base for example potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine
  • the compounds III can also be obtained by first converting the carbonylhydroxyimine IIIb with the sulfurization reagent into the corresponding thiocarbonylhydroxyimine IIIc and then IIIc either a) first with hydroxylamine or its salt and then with a compound of the formula V or
  • Q- in the formula VIIIb means the anion of an inorganic acid (in particular a halide such as chloride).
  • IIIb to IIIc takes place in a manner known per se [cf. Bull Soc. Chim. Belg. 87, 293 (1978)] at temperatures from 10 ° C to 150 ° C, preferably 20 ° C to 120 ° C in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -Butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, particularly preferably dioxane, toluene and xylene. Mixtures of the solvents mentioned can also be used.
  • P 4 S 10 or the Lawesson reagent [2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-di-phosphetane-2,4-disulfide] are used as sulfurization reagents, for example.
  • the compounds I can also be obtained by first converting the benzyl derivative II with a dihydroxyimine IIIa into a corresponding benzyloxime IVa and then IVa with the nucleophilic substitution
  • Reagent V converts to I.
  • 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 methods described in Houben-Weyl, Vol. 10/1, p. 1189f;
  • a base e.g. potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine
  • the compounds I can also be obtained by first converting the benzyl derivative II with a carbonylhydroxyimine IIIb into the corresponding benzyloxyimine VIa, VIa then converting the thio compound VIb with a sulfurization reagent and VIb either a) initially with hydroxylamine or its salt and then with a compound of formula V or
  • the reaction of the benzyl derivative II with the carbonylhydroxyimine IIIb is carried out as described in general and in particular for the reaction of II with III.
  • the sulfurization reaction and the oximation to I take place in general and in particular under the conditions described above.
  • the compounds VIa can also be obtained, for example, by a carboxylic acid VIc in a manner known per se [HouibenWeyl, Vol. E5, p. 941f] with a nitrogen-containing heterocycle IX.
  • the reaction is usually carried out at temperatures from -20 ° C to 100 ° C, preferably -10 ° C to 50 ° C, in an inert organic solvent, preferably in the presence of an activation reagent (eg phosgene, thionyl chloride, oxalyl chloride, N, N- Carbonyldiimidazole and triphenylphosphine / CCl 4 ).
  • an activation reagent eg phosgene, thionyl chloride, oxalyl chloride, N, N- Carbonyldiimidazole and triphenylphosphine / CCl 4 .
  • reaction is carried out in a manner known per se in an inert organic solvent according to that in EP-A 463 488 and
  • the required carbonyl compounds Villa are obtained, for example, by reacting the corresponding hydroxyiminocarbonyl compounds VIIIb with a nucleophilically substituted reagent V.
  • the compounds VIIIb can be obtained by reacting a hydroxamic acid VIIId in a manner known per se [cf.
  • the compounds I can also be obtained by first converting the benzylhydroxylamine Ha with the hydroxyimino derivative VIIIb into the corresponding benzyloxyimino derivative of the formula IVa and then reacting IVa to I with the nucleophilically substituted reagent V as described above.
  • the compounds I can also be obtained by first converting the benzylhydroxylamine IIa with the hydroxamic acid chloride VIIId into the corresponding compound IVb and then IVb first with IX in IVa and IVa then in I.
  • a further possibility for the preparation of the compounds I consists in converting the benzylhydroxylamine IIa with an ⁇ -keto acid VIIIe into the corresponding oximino-carboxylic acid VIc, converting VIc into the corresponding hydroxamic acid IVc by reaction with Vlla or Vllb, IVc to the hydroxamic acid halide IVd halogenated and IVd reacted with IX to I.
  • Molecule-bound are also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. HoubenWeyl, Vol. E5, pp.826f; Aust. J. Chem. 27, 1341 (1974)].
  • the corresponding reactions to the alkoxy derivatives are preferably carried out at stages I and VIa.
  • corresponding ⁇ -ketocarboxamides XIIc can be obtained by reacting the ⁇ -ketocarboxylic acids XIIb or the esters XIIa [cf. Houben-Weyl, Vol. E5, p.
  • ⁇ -ketocarboxamides XIIc in which R is hydrogen, can also be obtained directly from the carboxylic acid halides XIb by reaction with isocyanides XIII (R 1 -NC) [cf. EP-A 547 825].
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the CH 3 , CH 2 CH 3 or OCH 3 group to form the COYR 1 group).
  • the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radicals R 3 in relation to the OCH 2 grouping).
  • the configuration of the C (Z) NOR 4 double bond generally has only an insignificant influence on the biological activity of the compounds I. In cases in which an influence can be determined, the cis isomers (configuration based on the residues OR 4 in relation to the Z grouping).
  • isomer mixtures are formed in the synthesis, the separation into the individual compounds is generally not absolutely necessary, since the individual isomers partially convert into one another during preparation for use or during use (for example under the action of light, acid or base) can. Corresponding conversions can also take place after use, for example in the treatment of plants, fungi and animal pests in the treated organism.
  • 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,
  • Dialkylamino an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 4 or 6 carbon atoms as mentioned above;
  • Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-); Alkvisulfonyl; 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 -); Alkyl sulfoxyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which have a sulfoxyl group
  • 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 4 or 6 carbon atoms, in which case the hydrogen atoms in these groups 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-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
  • 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,
  • Haloalkoxy straight-chain or branched alkyl groups with 1 to 4 or 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 skeleton 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,
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,
  • 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 skeleton via an oxygen atom (-O-);
  • 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- Pentinyl,
  • Heterocyclyl or heterocyclyloxy ; three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are directly or (heterocyclyloxy) bonded to the skeleton via an oxygen atom are, such as 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiaziazolidinyl, 4-isothiaziazolidinyl, 4 3-pyrazolidinyl,
  • Oxygen and sulfur can contain: three- to twelve-membered saturated or partially or completely unsaturated, mono- or polycyclic systems, which, in addition to the nitrogen atom via which they are attached, and in addition to carbon ring members, one to five further heteroatoms from a group consisting of nitrogen, oxygen and may contain sulfur, and in the event that the cycle contains more than one oxygen and / or sulfur ring member, these oxygen or sulfur atoms are not in an adjacent position to one another, for example
  • aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a Sulfonyl group (-SO 2 -) are bound to the skeleton, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals; Hetaryl or hetaryloxy. Hetarylthio, hetarylcarbonyl and
  • Hetarylsulfonyl aromatic mono- or polycyclic radicals which in addition to carbon ring members additionally one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or may contain an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four sticks atoms of matter or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or
  • 5-membered heteroaryl bound via nitrogen. containing one to four nitrogen atoms. or nitrogen-bonded condensed 5-membered heteroaryl. containing one to five 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 can be bridged to form an aromatic or heteroaromatic bi or polycycle, these rings being bridged one of the nitrogen ring members is bound to the frame: e.g.
  • 6-ring heteroaryl groups which, in addition to carbon atoms, contain one to three or one to four nitrogen may contain atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazine -2-yl, 1,2,4-triazin-3-yl and
  • C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylaminocarbonyl, Di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy or C ( NOR a ) -A n -R b ;
  • Hetaryl, hetaryloxy and hetarylthio where the 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 6 alkoxycarbonyl,
  • Oxy-C 1 -C 4 alkyleneoxy, the alkylene chains being partial or full can be constantly halogenated and / or one to three
  • C 1 -C 3 alkyl groups can carry.
  • 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, 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 haloalkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, phenyl, phenoxy, benzyl and benzyloxy, and / or a group C ( NOR a ) -A n -R b can carry.
  • R 1 is methyl.
  • R 3 is hydrogen, hydroxy, cyano, cyclopropyl, chlorine, methyl, ethyl,
  • compounds I are preferred in which R 3 is methoxy. In addition, compounds I are preferred in which R 3 is cyano.
  • R 3 represents chlorine.
  • R 3 represents methylthio.
  • R 4 is C 1 -C 6 alkyl.
  • R 4 represents methyl or ethyl.
  • R 4 represents aryloxyalkyl or hetaryloxyalkyl.
  • R 4 represents arylalkyl or heteroarylalkyl.
  • R 4 represents aryl or hetaryl.
  • R 4 is C 2 -C 6 alkenyl
  • 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 and Basidiomycetes. Some of them are systemically effective and can be used as foliar 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 vegetable plants such as cucumbers, beans and pumpkin family, as well as on the seeds of these plants.
  • crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetable plants 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 species on cereals, Rhizoctonia species and Rhizoctonia Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species
  • Cereals Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and various plants , Plasmopara viticola on vines, Alternaria species
  • 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.
  • auxiliary agents come there The following are essentially considered: 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 non-ionic 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 non-ionic 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. Depending on the type of effect desired, the application rates are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • 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 with fertilizers are Fungicides or with fertilizers.
  • Sulfur, dithiocarbamates and their derivatives such as iron, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate min, 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-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-iso-propyl carbonate, 5-nitro -iso-phthalic acid di-iso-propyl ester; heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate,
  • Strobilurins such as methyl-E-methoximino- [ ⁇ - (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl ⁇ - 3-methoxyacrylate, methyl-E-methoximino- [ ⁇ - (2-phenoxyphenyl)] acetamide, methyl-E-methoximino- [ ⁇ - (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 acid morpholide. (2RS, 3SR) -1- [3- (2-chlorophenyl) -2- [4-fluorophenyl] oxiran-2-ylmethyl] -1H-1,2,4-triazole.
  • the compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. You can in crop protection as well as on the
  • Hygiene storage protection and veterinary sector are used as pesticides.
  • 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,
  • Galleria mellonella Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria,
  • brasiliensis Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,
  • Leptinotarsa decemlineata Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae,
  • 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,
  • Muscina stabulans Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa. From the order of the thrips (Thysanoptera) for example
  • Hoplocampa minuta Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
  • Bugs Heteroptera
  • Acrosternum hilare Blissus leucopterus
  • Cyrtopeltis notatus From the order of the bugs (Heteroptera), for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps,
  • suckers for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypy, Dreianafiaisolumiaia, Dreianafusiaolaia, Dreianafusiaolaia, Dreyfusiaolaia Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida
  • Arachnoid for example, arachnids
  • Acarina such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyinommobusuncus, Iinoblus, I megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychuschusus, Tetranychuschuschusch.
  • Carina such as Amblyomma americanum, Am
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita
  • active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or
  • Dispersions emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Preparations can be varied in larger areas.
  • 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.
  • UUV ultra-low-volume process
  • 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.
  • emulsions, pastes or old dispersions mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • Solvents e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.
  • Aqueous application forms can be made from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions)
  • Water can be added.
  • the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared 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).
  • Castor oil consists (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 milled in a hammer mill (active ingredient content 80% by weight).
  • VIII.20 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and in one
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour,
  • Mineral soils such as silica gel, silicas, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers
  • 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 7 Preparation of (Z, E, E) -2-methoxyimino-2- ⁇ 2 '- [(1 "-methyl, 1" - (1 "' - (1" "- piperidinyl), 1" '- methoxyiminomethyl)) - iminooxymethyl] phenyl ⁇ - methyl acetate (Example 1.002)
  • Dimethylformamide was first mixed with 2.0 g (5 mmol) of the compound from Example 4 and then with 4.3 g (50 mmol) of piperidine. After 60 h at room temperature (approx. 25 ° C), the reaction mixture was poured onto cooled, dilute hydrochloric acid. The product was tert with from the mixture thus obtained. -Butyl methyl ether extracted. After washing with water, drying and removing the solvent, 0.8 g (40%) of the title compound was obtained as a colorless oil from the ether phase.
  • 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.
  • Tritici wheat flour dew
  • Leaves of wheat seedlings ("early gold” variety) were first treated with the aqueous preparation of the active ingredients (application rate: 63 ppm). After about 24 hours, the plants were dusted with spores of powdery mildew (Erysiphe graminis var. Tritici). The plants treated in this way were then incubated for 7 days at 20-22 ° C. and a relative atmospheric humidity of 75-80%. The extent of fungal development was then determined.
  • the no. 1,007, 1,011, 1,012, 1,014 and 1,016 treated plants had an infection of 15% and less, while the plants treated with the known active ingredients A. and B were 40% infected. The untreated (control) plants were 70% infected.
  • % Emulphor® EL Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with acetone in the case of a) or with water in the case of b) according to the desired concentration. After the end of the tests, the lowest concentration was determined at which the compounds still caused 80-100% inhibition or mortality compared to control tests (without treatment) (threshold of action or minimum concentration).

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Abstract

L'invention concerne des acides phénylacétiques de la formule (I) dans laquelle les substituants et l'indice ont la notation suivante: X désigne NOCH3, CHOCH3, CHCH3 et CHCH2CH3; Y désigne O et NR (R = hydrogène et alkyle); Z désigne un hétérocyclyle ou hétéroaryle lié par un atome d'azote évent. subst.; R<1> désigne hydrogène et alkyle; R<2> désigne cyano, nitro, trifluorométhyle, halogène, alkyle et alcoxy; m vaut 0, 1 ou 2; R<3> désigne hydrogène, cyano, nitro, hydroxy, amino, cyclopropyle, halogène, alkyle, halogénure d'alkyle, alcoxy, halogénure d'alcoxy, alkylthio, alkylamino et dialkylamino; R<4> désigne hydrogène, alkyle évent. subst., alcényle, alcynyle, alkylcarbonyle, alcénylcarbonyle, alcynylcarbonyle, alkylsulfonyle, cycloalkyle, aryle, arylcarbonyle, arylsulfonyle, hétaryle, hétarylcarbonyle et hétarylsulfonyle. L'invention concerne également leurs sels, des procédés permettant de les préparer et des agents les contenant.
EP96931781A 1995-09-18 1996-09-09 Acides phenylacetiques, procedes permettant de les preparer et agents les contenant Withdrawn EP0851863A1 (fr)

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Application Number Priority Date Filing Date Title
DE19534492 1995-09-18
DE19534492 1995-09-18
PCT/EP1996/003937 WO1997011065A1 (fr) 1995-09-18 1996-09-09 Acides phenylacetiques, procedes permettant de les preparer et agents les contenant

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EP0851863A1 true EP0851863A1 (fr) 1998-07-08

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EP96931781A Withdrawn EP0851863A1 (fr) 1995-09-18 1996-09-09 Acides phenylacetiques, procedes permettant de les preparer et agents les contenant

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EP (1) EP0851863A1 (fr)
JP (1) JPH11512446A (fr)
KR (1) KR19990045731A (fr)
CN (1) CN1200117A (fr)
AR (1) AR004684A1 (fr)
AU (1) AU706982B2 (fr)
BR (1) BR9610592A (fr)
CA (1) CA2230106A1 (fr)
CZ (1) CZ64598A3 (fr)
EA (1) EA199800308A1 (fr)
HU (1) HUP9900772A2 (fr)
IL (1) IL123421A0 (fr)
NZ (1) NZ318771A (fr)
PL (1) PL325551A1 (fr)
WO (1) WO1997011065A1 (fr)
ZA (1) ZA967817B (fr)

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WO2011161945A1 (fr) * 2010-06-24 2011-12-29 クミアイ化学工業株式会社 Dérivé alcoxyimino et agent antiparasitaire
US9745253B2 (en) 2015-03-13 2017-08-29 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
JP2023525047A (ja) 2020-05-06 2023-06-14 エイジャックス セラピューティクス， インコーポレイテッド Ｊａｋ２阻害薬としての６－ヘテロアリールオキシベンゾイミダゾール及びアザベンゾイミダゾール
CA3234638A1 (fr) 2021-11-09 2023-05-19 Ajax Therapeutics, Inc. 6-hetero-aryloxy-benzimidazoles et azabenzimidazoles en tant qu'inhibiteurs de jak2

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CZ293803B6 (cs) * 1994-02-04 2004-08-18 Basfáaktiengesellschaft Deriváty fenyloctové kyselinyŹ způsob jejich přípravyŹ prostředekŹ způsob potírání zvířecích škůdců nebo škodlivých hub
US5889059A (en) * 1994-02-04 1999-03-30 Basf Aktiengesellschaft Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them

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Title
See references of WO9711065A1 *

Also Published As

Publication number Publication date
WO1997011065A1 (fr) 1997-03-27
CA2230106A1 (fr) 1997-03-27
AR004684A1 (es) 1999-03-10
EA199800308A1 (ru) 1998-10-29
BR9610592A (pt) 1999-07-06
AU706982B2 (en) 1999-07-01
ZA967817B (en) 1998-03-17
KR19990045731A (ko) 1999-06-25
PL325551A1 (en) 1998-08-03
NZ318771A (en) 1999-07-29
IL123421A0 (en) 1998-09-24
AU7084496A (en) 1997-04-09
JPH11512446A (ja) 1999-10-26
CZ64598A3 (cs) 1998-08-12
HUP9900772A2 (hu) 1999-06-28
CN1200117A (zh) 1998-11-25

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