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EP1483248A1 - Derives d'esters et d'amides d'acide phenylacetique substitues par des benzenes halogenes et leur utilisation dans la lutte contre les organismes nuisibles - Google Patents

Derives d'esters et d'amides d'acide phenylacetique substitues par des benzenes halogenes et leur utilisation dans la lutte contre les organismes nuisibles

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Publication number
EP1483248A1
EP1483248A1 EP03706519A EP03706519A EP1483248A1 EP 1483248 A1 EP1483248 A1 EP 1483248A1 EP 03706519 A EP03706519 A EP 03706519A EP 03706519 A EP03706519 A EP 03706519A EP 1483248 A1 EP1483248 A1 EP 1483248A1
Authority
EP
European Patent Office
Prior art keywords
formula
optionally substituted
compounds
halogen
methyl
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.)
Withdrawn
Application number
EP03706519A
Other languages
German (de)
English (en)
Inventor
Fritz Maurer
Christiane Boie
Herbert Gayer
Ulrich Heinemann
Bernd-Wieland Krüger
Ulrike Wachendorff-Neumann
Astrid Mauler-Machnik
Peter Lösel
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1483248A1 publication Critical patent/EP1483248A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Definitions

  • the invention relates to new halogenobenzenes, several processes for their preparation and their use for controlling harmful organisms, and new ones
  • R 5 represents optionally substituted aryl
  • R 6 represents optionally substituted aryl
  • R 7 , R 8 , R 9 and R 10 are identical or different and independently of one another represent hydrogen, halogen, optionally substituted alkyl or optionally substituted alkoxy,
  • R 1 ! represents optionally substituted alkyl
  • R 12 represents in each case optionally substituted alkyl, alkoxy or aryl
  • R 13 represents in each case optionally substituted alkyl or aryl
  • R 14 represents optionally substituted aryl
  • R 15 and R 16 are identical or different and independently of one another represent hydrogen, halogen or alkyl
  • X represents hydrogen or halogen
  • R 2 , R 3 and R 4 are the same or different and are independently hydrogen or halogen, but at least one of the radicals R 2 , R 3 or R 4 is halogen and
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are also each straight-chain or in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino branched. Unless otherwise stated, hydrocarbon chains having 1 to 6 carbon atoms are preferred.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
  • R 2 , R 3 , R 4 and T have the meanings given above,
  • Y 1 represents halogen
  • R 14 , R 15 and R 16 has the meaning given above and
  • Y 2 represents alkysulfonyl or arylsulfonyl
  • R 2 , R 3 , R 4 , T and X have the meanings given above and Y 3 represents halogen
  • R 13 has the meaning given above
  • R 5 has the meaning given above and
  • Y 5 represents halogen
  • R 2 , R 3 , R 4 and T have the meanings given above and
  • Y 6 represents halogen
  • R 6 has the meaning given above
  • R 7 , R 8 , R 9 and R 10 have the meanings given above,
  • R 1 1 and R 12 have the meanings given above,
  • R 5 has the meaning given above
  • R 1 , R 2 , R 3 and R 4 have the meanings given above, with methylamine, optionally in the presence of a diluent, or if one
  • the compounds of the invention can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E- and Z- are present. Both the E and the Z isomers and any mixtures of these isomers are claimed.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 for each optionally substituted phenoxy or phenoxymethyl or for one of the groupings
  • R 5 represents optionally substituted phenyl
  • R 6 represents optionally substituted phenyl
  • R 7 , R 8 , R 9 and R 10 are identical or different and independently of one another represent hydrogen, optionally alkyl substituted by halogen or alkoxy optionally substituted by halogen, each having 1 to 4 carbon atoms, fluorine, chlorine, bromine or iodine,
  • R 1 1 represents alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen
  • R 12 represents in each case optionally substituted by halogen alkyl or alkoxy having 1 to 6 carbon atoms or optionally substituted phenyl
  • R 13 represents in each case optionally substituted by halogen alkyl having 1 to 6 carbon atoms or optionally substituted phenyl,
  • R 14 represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen
  • R 15 and R 16 are the same or different and independently of one another represent hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms,
  • X represents hydrogen, fluorine, chlorine, bromine or iodine
  • R 2 , R 3 and R 4 are the same or different and are independently hydrogen, fluorine, chlorine, bromine or iodine, but at least one of the radicals R 2 , R 3 or R 4 is fluorine, chlorine, bromine or iodine and
  • alkyl in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms;
  • each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
  • Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl and in each case doubly linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms;
  • a 1 represents hydrogen, hydroxy or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 for each optionally substituted phenoxy or phenoxymethyl or for one of the groupings
  • R 5 represents optionally substituted phenyl
  • R 6 represents optionally substituted phenyl
  • R 7 , R 8 , R 9 and R 10 are the same or different and independently of one another represent hydrogen, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, fluorine, chlorine, bromine or iodine,
  • R 1 ! represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R 12 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy or optionally substituted phenyl,
  • R 13 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl or optionally substituted phenyl,
  • R 14 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl which is optionally substituted by fluorine or chlorine
  • R 15 and R 16 are the same or different and independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl or ethyl
  • X represents hydrogen, fluorine, chlorine, bromine or iodine
  • R 2 , R 3 and R 4 are the same or different and are independently hydrogen, fluorine or chlorine, but at least one of the radicals R 2 , R 3 or R 4 is fluorine or chlorine and
  • a 2 "A 1 represents hydrogen, methyl or hydroxy and A 2 represents hydroxy, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl.
  • radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.
  • Formula (II) provides a general definition of the hydroxyhalophenyl derivatives required as starting materials for carrying out process a) according to the invention.
  • R 2 , R 3 , R 4 and T preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 2 , R 3 , R 4 and T were given.
  • the starting materials of formula (II) are new and also the subject of the present application.
  • R 2 , R 3 and R 4 have the meanings given above and
  • R 17 represents alkyl
  • R 18 represents hydrogen or alkyl or
  • R 17 and R 18 together with the atoms to which they are attached form a six-membered ring
  • R 2 , R 3 and R 4 have the meanings given above,
  • R 2 , R 3 and R 4 have the meanings given above,
  • Formula (XIII) provides a general definition of the keto esters required as starting materials for carrying out process g) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 and R 4 have been given.
  • R 17 represents alkyl, preferably methyl or ethyl.
  • R 18 represents hydrogen or alkyl, preferably hydrogen, methyl or ethyl.
  • R 17 and R 18 together with the atoms to which they are attached also represent a six-membered ring, preferably a tetrahydropyran ring.
  • keto esters of the formula (XIII) are new and also a subject of the present invention. They are obtained (process i) if a ketal of the general formula (XV),
  • R 2 , R 3 , R 17 and R 18 have the meanings given above,
  • dimethyl oxalate optionally in the presence of a diluent and optionally in the presence of a strong base.
  • Formula (XV) provides a general definition of the ketals required as starting materials for carrying out process i) according to the invention.
  • R 2 , R 3 , R 17 and R 18 preferably or in particular have those meanings which are preferred or particularly preferred in connection with the description of the compounds of the formulas (I) and (XIII) according to the invention were preferably given for R 2 , R 3 , R 17 and R 18 .
  • the compounds of the formula (XV) are known or can be prepared by known processes (see, for example, J.Amer.Chem.Soc. 119; 6; 1997; 1208-1216).
  • the dimethyl oxalate further required to carry out process i) according to the invention is a generally known laboratory chemical.
  • Formula (XIV) provides a general definition of the hydroxyphenylglyoxylic acid esters which are alternatively required as starting materials for carrying out process g) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 and R 4 have been given.
  • hydroxyphenylglyoxylic acid esters of the formula (XIV) are new and also the subject of the present application. They are obtained (process j) if fluorophenols of the general formula (XVI), in which
  • R 2 , R 3 and R 4 have the meanings given above,
  • Formula (XVI) provides a general definition of the fluorophenols required as starting materials for carrying out process j) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 and R 4 have been given.
  • the fluorophenols of the formula (XVI), and also the methyl oxalate chloride required to carry out process j) according to the invention, are commercially available laboratory chemicals.
  • hydroxylamine and its salts required to carry out process g) according to the invention and their salts are commercially available laboratory chemicals.
  • Formula (II-a) generally defines the hydroxyhalophenyl derivatives required as starting materials for carrying out process h) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular those meanings which have already been given in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 2 , R 3 and R 4 .
  • hydroxyhalophenyl derivatives of the formula (ITa) are compounds according to the invention and can be prepared by process g).
  • the methylamine which is furthermore required as starting material for carrying out the process h) according to the invention is a commercially available laboratory chemical.
  • Formula (III) provides a general definition of the phenoxypyrimidines required as starting materials for carrying out process a) according to the invention.
  • R 13 and X preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for
  • Y 1 represents halogen, preferably fluorine or chlorine.
  • the starting materials of the formula (III) are known and / or can be prepared by known methods (compare, for example, WO 97-27189).
  • Formula (IV) provides a general definition of the alkoxypyrimidines which can alternatively be used as starting materials for carrying out process a) according to the invention.
  • R 14 , R 15 and R 16 preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 14 , R 15 and R 16 were specified.
  • Y 2 represents alkysulfonyl or arylsulfonyl, preferably methysulfonyl or tolylsulfonyl.
  • Formula (V) provides a general definition of the 4-phenoxypyrimidines required as starting materials for carrying out process b) according to the invention.
  • R 2 , R 3 , R 4 , T and X preferably or in particular have those meanings which have been preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention for R 2 , R 3 , R 4 , T and X were specified.
  • Y 3 represents halogen, preferably fluorine or chlorine.
  • Y7 represents halogen, with a hydroxyhalophenyl derivative of the formula (II)
  • Formula (XVII) provides a general definition of the halopyrimidines required as starting materials for carrying out process 1) according to the invention.
  • Y 3 and X preferably or in particular have those meanings which have already been given as preferred or as particularly preferred for Y 3 and X in connection with the description of the compounds of the formula (V) according to the invention.
  • Y7 represents halogen, preferably fluorine or chlorine.
  • the halopyrimidines of the formula (XVII) are known and can be prepared according to known ones
  • Processes are prepared (compare, for example, WO 97-27189 or WO 98-41513).
  • Formula (VI) provides a general definition of the phenols which are furthermore required as starting materials for carrying out process b) according to the invention.
  • R 13 preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R 13 in connection with the description of the compounds of the formula (I) according to the invention.
  • the phenols of the formula (VI) are generally known synthetic chemicals.
  • Formula (VII) provides a general definition of the diaryliodonium halides required as starting materials for carrying out process c) according to the invention.
  • R 5 preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R 5 in connection with the description of the compounds of the formula (I) according to the invention.
  • the diaryliodonium halides of the formula (VII) are known or can be prepared by known methods (compare, for example, Synthesis (1995), (8), 1027-3).
  • Formula (VIII) provides a general definition of the 2- (2-halomethylphenyl) -2-methoxyimino derivatives required as starting materials for carrying out process d) according to the invention.
  • R 2 , R 3 , R 4 and T preferably or in particular have those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention or as being particularly preferred for R 2 , R 3 , R 4 and T.
  • Y 6 represents halogen, preferably chlorine or bromine.
  • R 2 , R 3 , R 4 and T have the meanings given above,
  • Formula (XVIII) provides a general definition of the 2- (2-methylphenyl) -2-methoxyimino derivatives required as starting materials for carrying out process m) according to the invention.
  • R 2 , R 3 , R 4 and T preferably or in particular have those meanings which have already been in connection with the Description of the compounds of formula (I) according to the invention as being preferred or as being particularly preferred for R 2 , R 3 , R 4 and T.
  • R 2 , R 3 and R 4 have the meanings given above,
  • R 2 , R 3 and R 4 have the meanings given above,
  • Formula (XIX) provides a general definition of the O-tolylpyruvic acid esters required as starting materials for carrying out process n) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (XIX) according to the invention, are preferred or particularly preferred for R 2 , R 3 and R 4 were given.
  • O-tolylpyruvic acid esters of the formula (XIX) are new and also the subject of the present application. They are obtained (process p) if benzoyl cyanides of the formula (XX), in which
  • R 2 , R 3 and R have the meanings given above,
  • Formula (XX) provides a general definition of the benzoyl cyanides required as starting materials for carrying out process p) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 and R 4 have been given.
  • R 2 , R 3 and R 4 have the meanings given above,
  • Formula (XXI) provides a general definition of the benzoic acid derivatives required as starting materials for carrying out process r) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 and R 4 have been given.
  • the benzoic acid derivatives of the formula (XXI) are known or can be prepared by known methods (compare, for example, DE 3328494).
  • Formula (XVIII-a) provides a general definition of the 2- (2-methylphenyl) -2-methoxyimino derivative required as starting materials for carrying out process o) according to the invention.
  • R 2 , R 3 and R 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 2 , R 3 and R 4 were given.
  • the 2- (2-methyl-phenyl) -2-methoxyimino derivatives of the formula (XVIII-a) are compounds according to the invention and can be prepared by process n).
  • the methylamine which is furthermore required as starting material for carrying out the process o) according to the invention is a commercially available laboratory chemical.
  • the 2- (2-methylphenyl) -2-methoxyimino derivatives required as starting materials for carrying out the process q) according to the invention are generally defined by the formula (XVIII-a) and have already been described in the description of the process n) according to the invention.
  • the substances hydroxylamine, or its salts and dibromoethane, which are further required as starting materials for carrying out the process q) according to the invention, are commercially available laboratory chemicals.
  • Suitable halogenating agents for carrying out process m) according to the invention are preferably all customary chlorination, bromination and iodination agents. Examples include: chlorine, bromine, iodine, chlorosuccinimide, bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin or iodosuccinimide.
  • halogenating agents mentioned are all common laboratory chemicals.
  • Formula (IX) provides a general definition of the oximes required as starting materials for carrying out process d) according to the invention. In this
  • R 6 has preferably or in particular has that meaning which preferred as being preferred or particularly in connection with the description of the compounds of formula (I) according to the invention was specified for R. 6
  • the oximes of the formula (IX) are known synthetic chemicals or can be prepared from ketones and hydroxylamine by generally customary methods.
  • Formula (X) provides a general definition of the benzofuranone oximes additionally required as starting materials for carrying out process d) according to the invention.
  • R 7 , R 8 , R 9 and R 10 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 7 , R 8 , R 9 and R 10 were given.
  • benzofuranone oximes of the formula (X) are known or can be prepared by known methods (compare, for example, WO 9621640).
  • Formula (XI) provides a general definition of the bisoximes additionally required as starting materials for carrying out process d) according to the invention.
  • R 1 1 and R 12 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R 1 ! and R 12 were given.
  • the bisoximes of the formula (XI) are known or can be prepared by known methods (compare, for example: WO 97-24317).
  • Formula (XII) provides a general definition of the phenols which are alternatively required as starting materials for carrying out process d) according to the invention.
  • R 5 preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R 5 in connection with the description of the compounds of the formula (I) according to the invention.
  • the phenols of the formula (XII) are generally known synthetic chemicals.
  • Formula (I-a) provides a general definition of the halogenobenzenes required as starting materials for carrying out process e) according to the invention.
  • halobenzenes of the formula (I-a) are substances according to the invention and can be prepared by processes a), b), c) or d) according to the invention.
  • the methylamine which is furthermore required as a starting material for carrying out process e) according to the invention is a commercially available laboratory chemical.
  • Formula (Ia) provides a general definition of the halogenobenzenes required as starting materials for carrying out process f) according to the invention.
  • the halobenzenes of the formula (Ia) are substances according to the invention and can be prepared by processes a), b), c) or d) according to the invention.
  • the substances hydroxylamine, or its salts and dibromoethane, which are further required as starting materials for carrying out the process f) according to the invention, are commercially available laboratory chemicals.
  • Suitable diluents for carrying out processes a), b) and 1) are all inert organic solvents. These preferably include ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides such as dimethyl sulfoxide; or sulfones, such as sulfolane.
  • ethers such as diethyl ether, diisopropyl
  • Processes a), b) and 1) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, alcoholates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate ,
  • reaction temperatures can be carried out when carrying out the inventive reaction temperatures.
  • Processes a), b) and 1) can be varied over a wide range. In general, temperatures from 10 ° C to 80 ° C, preferably at temperatures from 20 ° C to 50 ° C.
  • Formula (II) generally 1 to 5 moles, preferably 1 to 2 moles of phenoxypyrimidine in the formula (III).
  • Formula (II) generally 1 to 5 mol, preferably 1 to 2 mol of alkoxypyrimidine of the formula (IV).
  • Formula (II) generally 1 to 15 moles, preferably 2 to 8 moles of halopyrimidine in the formula (XVII).
  • Suitable diluents for carrying out process c) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, but
  • Process c) is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, potassium tert.
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N- Methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out process c) according to the invention. In general, temperatures from 0 ° C to 100 ° C, preferably at temperatures from 20 ° C to 80 ° C.
  • Formula (II) generally 1 to 2 mol, preferably 1 to 1.5 mol of diaryliodonium halide of the formula (VII).
  • Suitable diluents for carrying out process d) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone,
  • Process d) according to the invention is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or
  • Alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Sodium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary
  • Amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out process d) according to the invention. In general, temperatures from 0 ° C to 100 ° C, preferably at temperatures from 20 ° C to 80 ° C.
  • Suitable diluents for carrying out processes e), h) and o) according to the invention are all inert organic solvents.
  • aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as
  • reaction temperatures can be varied within a substantial range when carrying out processes e), h) and o) according to the invention. In general, temperatures from 0 ° C to 100 ° C, preferably at temperatures from 0 ° C to 60 ° C.
  • Suitable diluents for carrying out processes f) and q) according to the invention are polar solvents. These preferably include alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propan-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, their mixtures with water or pure
  • alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propan-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, their mixtures with water or pure
  • reaction temperatures can be varied within a substantial range when carrying out processes f) and q) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • Suitable diluents for carrying out processes g) and n) according to the invention are polar solvents. These preferably include alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethane diol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethane diol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • reaction temperatures can be carried out when carrying out the inventive reaction temperatures.
  • Processes g) and n) can be varied over a wide range. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • Inert organic solvents are suitable as diluents for carrying out process i) according to the invention.
  • These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or
  • Process i) according to the invention is optionally carried out in the presence of a strong base.
  • a strong base preferably include n-, s-, t-butylitium or lithium diisopropyamide.
  • the reaction temperatures can be varied within a substantial range when carrying out process i) according to the invention. In general, temperatures from -150 ° C to 0 ° C, preferably at temperatures from -100 ° C to -40 ° C.
  • Inert organic solvents are suitable as diluents for carrying out process j) according to the invention.
  • These preferably include aliphatic or alicyclic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • aliphatic or alicyclic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin
  • Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trich
  • Process j) according to the invention is optionally carried out in the presence of a Lewis acid.
  • a Lewis acid include, for example, boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, titanium tetrachloride, tetrabutyl orthotitanate, zinc chloride, iron III chloride or antimony pentachloride.
  • reaction temperatures can be varied within a substantial range when carrying out process j) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol,
  • Process k) according to the invention is optionally carried out in the presence of an acid.
  • All inorganic and organic protonic and Lewis acids, as well as all polymeric acids, are suitable as such. These include, for example, hydrogen chloride, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulphonic acid, trifluoromethanesulphonic acid, toluenesulphonic acid, boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, titanium tetrachloride, tetrabutyl chloride, iron-III-pentahloridotitanate, acidic ion exchangers, acidic clays and acidic silica gel.
  • reaction temperatures can be varied within a substantial range when carrying out process k) according to the invention. In general, temperatures from 0 ° C to 120 ° C, preferably at temperatures from 0 ° C to 50 ° C.
  • Inert organic solvents are suitable as diluents for carrying out process m) according to the invention.
  • halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • reaction temperatures can be varied within a substantial range when carrying out process m) according to the invention. Generally works one at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 100 ° C.
  • Suitable diluents for carrying out process p) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole.
  • reaction temperatures can be varied within a substantial range when carrying out process p) according to the invention. In general, temperatures from -20 ° C to 80 ° C, preferably at temperatures from 0 ° C to 50 ° C.
  • Suitable diluents for carrying out the first step of process r) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclo- hexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclo- hexane, benzene, toluene, xylene or decalin
  • halogenated hydrocarbons such as chlorobenzene
  • Process r are all customary chlorinating agents that can be used for the production of acid chlorides, such as. B. thionyl chloride, phosphorus trichloride or phosphorus pentachloride.
  • Process r) according to the invention is optionally carried out in the presence of a catalyst, such as, for example, dimethylformamide or dimethylacetamide.
  • a catalyst such as, for example, dimethylformamide or dimethylacetamide.
  • reaction temperatures can be varied within a substantial range when carrying out both the first and the second stage of process r) according to the invention.
  • the first stage is carried out at temperatures from 20 ° C. to 150 ° C., preferably at temperatures from 20 ° C. to 100 ° C. and for the second stage at 100 to 250 ° C., preferably at 100 to 200 ° C.
  • (XXI) generally 1 to 15 mol, preferably 1 to 8 mol of halogenating agent and 1 to 5 mol, preferably 1 to 2 mol of trimethylsilyl cyanide.
  • All of the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phoropalisumum , Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes sppus, spp., Trog.
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,
  • Trichodorus spp. Bursaphelenchus spp. They can be used with particularly good success to control insects which damage plants, such as, for example, against the larvae of the green peach aphid (Myzus persicae) and the caterpillars of the green army worm (Spodoptera frugiperda).
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Altemaria species such as, for example, Altemaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to protect plants against attack by the named pathogens within a certain period of time after the treatment.
  • the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • the active compounds according to the invention can be used with particularly good success in combating cereal diseases, such as, for example, against Erysiphe or Leptosphaeria species, and diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia, Sphaerotheca, Podosphaera- and Phytophtora- Types, use.
  • cereal diseases such as, for example, against Erysiphe or Leptosphaeria species
  • diseases in wine, fruit and vegetable cultivation such as, for example, against Venturia, Sphaerotheca, Podosphaera- and Phytophtora- Types, use.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth, and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention adhesives, glues, paper and cardboard, textiles, leather, wood, paints and
  • Plastic items, coolants and other materials may be those of Microorganisms can be attacked or decomposed.
  • parts of production plants for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • the preferred technical materials are adhesives, glues, papers and cartons, leather,
  • Wood, paints, cooling lubricants and heat transfer liquids called, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and, for example, are microorganisms which can cause degradation or a change in the technical materials
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic
  • Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as Dimethylformamide and dimethyl sulfoxide, as well as water.
  • Liquefied gaseous extenders or carriers mean such liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • emulsifiers and / or foaming agents come in
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be mixed with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, for example to spread the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononine
  • Fenpiclonil fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimidol,
  • Flusilazole Flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fosetyl Sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Iprovalicarb, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Cyanophos Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flcythrinate, Fluftoxinhrininate, Fufonoxhrhrininate, Fumetoxinhrininate, Fumetoxin , Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these mushrooms is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to
  • the application rates can be varied within a substantial range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars and their parts which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are treated.
  • transgenic plants are Zen and plant varieties, which were obtained by genetic engineering methods, if necessary in combination with conventional methods (Genetic Modified Organisms) and their parts treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects. For example, reduced application rates and / or extensions of the
  • Nutritional value of the harvested products higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvest products, higher storability and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi,
  • transgenic plants Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans , Potato, cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus Thuringenisis (eg by the genes Cry ⁇ A (a), Cry ⁇ A (b ), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) in the
  • Plants are created (hereinafter “Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • the traits are also particularly emphasized by the plants' increased tolerance to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the "PAT” gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” are maize varieties,
  • YIELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf ® NewLeaf ®
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example corn, Cotton, soy), Liberty Link® (tolerance against phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • Dimethylformamide is added dropwise to 1.12 g (0.01 mol) of o-cresol. The mixture is stirred for 3 hours at room temperature, then a solution of 4.5 g (0.01 mol) of (2-bromomethyl-6-fluorophenyl) methoxyiminoacetic acid methyl ester in 20 ml of dimethylformamide is added and the mixture is stirred Mix overnight at room temperature. Then the reaction mixture is poured into water and extracted twice with
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)
  • the double bond of the methoxyimino-N-methylacetamide group or the methoxyiminoacetic acid methyl ester group is in the E configuration, if not marked differently.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Sphaerotheca fuliginea inoculated The plants are then placed in the greenhouse at about 23 ° C. and a relative atmospheric humidity of about 70%.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Apple scab pathogen Venturia inaequalis and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity.
  • the plants are then placed in a greenhouse at approx. 21 ° C and a relative humidity of approx. 90%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example F the substances according to the invention listed in Examples (1, 3, 4, 8, 10, 12, 14, 40, 41, 42, 43, 44, 50, 51) show an efficiency at an application rate of 500 g / ha of 98% or more.
  • Example F the substances according to the invention listed in Examples (1, 3, 4, 8, 10, 12, 14, 40, 41, 42, 43, 44, 50, 51) show an efficiency at an application rate of 500 g / ha of 98% or more.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of 80%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example G the substances according to the invention listed in Examples (2, 16, 22, 31, 45, 46, 47, 48, 57) show an efficiency of 98% or more at an application rate of 500 g / ha.
  • Example G the substances according to the invention listed in Examples (2, 16, 22, 31, 45, 46, 47, 48, 57) show an efficiency of 98% or more at an application rate of 500 g / ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and stated emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Seedlings of the field bean (Vicia faba minor), which are infested with the green peach aphid (Myzus persicae), are immersed in an active ingredient preparation of the desired concentration and placed in a plastic can.
  • the kill is determined in percent. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • the compound of preparation example (56) at an exemplary active ingredient concentration of 100 ppm causes a kill of 100% after 6 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.
  • a specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed.
  • one larva (L3) of the Herrwurm (Spodoptera frugiperda) is placed on the feed.
  • the mortality is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Example (1) shows a degree of destruction of 98% or more at an active substance concentration of 500 ppm.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Pyrane Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de formule (I), plusieurs procédés de production desdits composés et leur utilisation dans la lutte contre les organismes nuisibles ainsi que des produits intermédiaires. Dans cette formule (I), R1 désigne un groupement parmi R5-O-#, R5-O-CH2-#, (a), (b), (c), (d) ou (e) et T désigne un groupement (f), (g) ou (h).
EP03706519A 2002-03-01 2003-02-17 Derives d'esters et d'amides d'acide phenylacetique substitues par des benzenes halogenes et leur utilisation dans la lutte contre les organismes nuisibles Withdrawn EP1483248A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10209145A DE10209145A1 (de) 2002-03-01 2002-03-01 Halogenbenzole
DE10209145 2002-03-01
PCT/EP2003/001565 WO2003074496A1 (fr) 2002-03-01 2003-02-17 Derives d'esters et d'amides d'acide phenylacetique substitues par des benzenes halogenes et leur utilisation dans la lutte contre les organismes nuisibles

Publications (1)

Publication Number Publication Date
EP1483248A1 true EP1483248A1 (fr) 2004-12-08

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Country Status (6)

Country Link
US (1) US20050124498A1 (fr)
EP (1) EP1483248A1 (fr)
JP (1) JP2005526746A (fr)
AU (1) AU2003208863A1 (fr)
DE (1) DE10209145A1 (fr)
WO (1) WO2003074496A1 (fr)

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CN100443463C (zh) * 2005-06-28 2008-12-17 沈阳化工研究院 取代的对三氟甲基苯醚类化合物及其制备与应用
JP2023025308A (ja) * 2020-01-31 2023-02-22 住友化学株式会社 ＱｏＩ殺菌剤に対して耐性を有するダイズさび病菌の防除方法
BR112022021753A2 (pt) * 2020-04-28 2022-12-06 Basf Se Uso de compostos de fórmula i, métodos para combater fungos fitopatogênicos, compostos e composições agroquímicas
WO2022008303A1 (fr) * 2020-07-08 2022-01-13 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine du cytochrome b mitochondrial conférant une résistance à des inhibiteurs de qo vi

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Publication number Publication date
AU2003208863A1 (en) 2003-09-16
JP2005526746A (ja) 2005-09-08
WO2003074496A1 (fr) 2003-09-12
DE10209145A1 (de) 2003-09-04
WO2003074496A8 (fr) 2005-05-12
US20050124498A1 (en) 2005-06-09

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