EP1638962A2 - Substituierte oxyarene, and use thereof for controlling pests - Google Patents

Substituierte oxyarene, and use thereof for controlling pests

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Publication number
EP1638962A2
EP1638962A2 EP04729628A EP04729628A EP1638962A2 EP 1638962 A2 EP1638962 A2 EP 1638962A2 EP 04729628 A EP04729628 A EP 04729628A EP 04729628 A EP04729628 A EP 04729628A EP 1638962 A2 EP1638962 A2 EP 1638962A2
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EP
European Patent Office
Prior art keywords
cyano
alkyl
optionally
substituted
nitro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP04729628A
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German (de)
English (en)
French (fr)
Inventor
Peter Jeschke
Michael Müller
Iris Escher
Olga Malsam
Karl-Josef Haack
Ralf Braun
Christian Arnold
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP1638962A2 publication Critical patent/EP1638962A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to new substituted oxyarenes, ner processes for their preparation and their use as pesticides.
  • a 2 represents in each case straight-chain or branched alkanediyl or alkenediyl each having up to 8 carbon atoms, which optionally contains an oxygen atom, a sulfur atom or a group selected from SO, SO 2 , NH or N (CC 4 at the beginning, at the end or within the carbon chain -Alkyl) contains
  • R 1 for hydrogen, nitro, hydroxy, amino, cyano, halogen, for alkyl, alkoxy, alkylthio, alkylamino, each optionally substituted by cyano, halogen, C 1 -C 6 alkylsulfonyl, CC 6 alkylsulfonyl or C 1 -C 6 alkoxy, Dialkylamino, alkylcarbonylamino or alkoximinoalkyl, each with 1 to 10 carbon atoms in the alkyl groups, for C 1 -C 6 -
  • R, R ' represents straight-chain or branched alkanediyl having up to 8 carbon atoms, which may be selected from an oxygen atom, a sulfur atom or a group at the beginning, at the end or within the carbon chain SO, SO 2 , NH or N (-C 4 alkyl) contains,
  • R 2 for hydrogen, nitro, hydroxy, amino, cyano, cyanato, thiocyanato, formyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl, alkylamino, dialkylamino or alkylcarbonylamino, each optionally substituted by cyano, halogen or - -alkoxy 1 to 6 carbon atoms in the alkyl groups, C ⁇ -C 6 - alkyl-carbonyl, C ⁇ -C 6 -alkoxy-carbonyl, C ⁇ -C 6 -Alkoximinoforrnyl, C ⁇ -C 6 -Alkoximino- acetyl, or C 2 -C 6 -Alkenyl or C 2 -C 6 -alkynyl, R 3 stands for hydrogen, nitro, hydroxyl, amino, cyano, halogen, for alkyl,
  • R 4 stands for hydrogen, nitro, hydroxyl, amino, cyano, halogen, for alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino, each with 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or CC 6 alkoxy,
  • R 5 represents hydrogen, optionally by nitro, hydroxyl, amino, cyano, halogen, CC 6 - alkyl, C 1 -C 6 haloalkyl, - alkoxy, C 1 -C 6 haloalkoxy, CC 2 alkylene dioxy, -
  • Substituents can be selected:
  • a 3 represents a single bond or C 1 -C 6 -alkanediyl, which is optionally substituted by one to six identical or different substituents from the group C r C 3 haloalkyl, C 3 -C 8 cycloalkyl and C 3 -C 8 - Cycloalkyl -CC 6 alkyl is substituted,
  • R 7 together with R 6 represents in each case optionally mono- to tetrasubstituted by identical or different manner by C r C 6 alkyl, C 3 -C 8 cycloalkyl-C ⁇ -C 6 -alkyl, halo-C 6 alkyl, cyano or C ⁇ -C 6 alkylcarbonyl substituted C 4 -C 8 -AIkandiyl or C 4 -C 8 - alkylenediyl group, wherein optionally a CH 2 group may be replaced by O, S or NR 9, or
  • R 9 represents hydrogen, CC 6 -alkyl, CC 3 -haloalkyl, d-Qs-haloalkylcarbonyl, CC 6 -alkoxyalkyl, CC 6 -alkylcarbonyl or C 3 -C 8 -cycloalkyl, and
  • Substituents from the series nitro, hydroxyl, amino, cyano, halo, C ⁇ -C 6 - alkyl, C ⁇ -C 6 - haloalkyl, C ⁇ -C 6 -alkoxy, C 6 haloalkoxy, C ⁇ -C 6 - alkylthio, - C ⁇ -Haloalkyl-thio can be substituted.
  • the compounds of the formula can optionally also be present as stereoisomers, ie as geometric and / or as optical isomers or isomer mixtures in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, too if in general only the compounds of the formula (I) are mentioned here.
  • the invention also relates to the salt-like derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds.
  • a 2 preferably represents in each case straight-chain or branched alkanediyl or alkenediyl each having up to 4 carbon atoms, which optionally contains an oxygen atom, a sulfur atom or a group selected from SO, SO 2 , NH or N (CC) at the beginning, at the end or within the carbon chain 3 alkyl) contains.
  • R 1 preferably represents hydrogen, nitro, hydroxyl, amino, cyano, halogen, in each case optionally by cyano, halogen, Cr -alkylsulfmyl, -C-C 3 -alkylsulfonyl or -C-C 5 -
  • Grouping selected from SO, SO 2 , NH or N (CC 3 alkyl) contains.
  • R 2 preferably represents hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, halogen, each alkyl optionally substituted by cyano, halogen or C 1 -C 5 -alkoxy,
  • R 3 preferably represents hydrogen, nitro, halogen, in each case alkyl, alkoxy, alkylthio or alkylamino, each of which is optionally substituted by cyano, halogen or C 1 -C 5 -alkoxy, each having 1 to 5 carbon atoms in the alkyl groups.
  • R 4 preferably represents hydrogen, nitro, halogen, alkyl, alkoxy, alkylthio or alkylamino, each optionally substituted by cyano, halogen or C] -C 5 -alkoxy, each having 1 to 5 carbon atoms in the alkyl groups.
  • R 5 preferably represents hydrogen, optionally by nitro, hydroxy, amino, cyano, halogen, -Cs-alkyl, CC 5 -haloalkyl, -C-C 3 -alkoxy, CC 5 -haloalkoxy, CC 2 -
  • Substituents can be selected:
  • a 3 preferably represents a single bond or CC 6 -alkanediyl, which is optionally substituted by one to six identical or different substituents from the group -C-C 3 - haloalkyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl- -C-C 6 alkyl is substituted.
  • R 7 preferably represents hydrogen, cyano, C 1 -C 5 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-
  • Haloalkyl C ⁇ -C 5 -alkoxy, C 5 haloalkoxy, hydroxy, cyano or nitro-substituted phenyl or benzyl.
  • R 7 is also preferably taken together with R 6 represents in each case optionally mono- to tetrasubstituted by identical or different substituents from C ⁇ -C 5 alkyl, C 3 -C 6 cycloalkyl-C ⁇ -C 5 alkyl, C 1 -C 5 - haloalkyl, Cyano or C 1 -C 5 alkylcarbonyl substituted C 4 -C 6 alkanediyl or C -C 6 -
  • Alkylenediyl where a CH 2 group can optionally be replaced by O, S or NR 9 .
  • CH 2 group can be replaced by O, S or NR 9 , or
  • R 8 preferably represents C r C 5 alkyl, C r C 5 haloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 haloalkenyl, C 2 -C 5 alkynyl, Q-Cs-alkoxy , -C-C 5 haloalkoxy, C 2 -C 5 alkenyloxy, C 2 -C 5 -
  • Haloalkenyloxy, C 2 -C 5 alkynyloxy, C 3 -C 5 cycloalkyl represents in each case optionally mono- to trisubstituted in the aryl moiety by identical or different halogen, cyano, nitro, QC 5 - alkyl, C ⁇ -C 5 haloalkyl, CC 5 -Alkylcarbonyl, C 2 -C 5 -alkenyl, C 2 -C 5 -halogenalkenyl, C 2 -C 5 -alkynyl, CC 5 -alkoxy, C ⁇ -C 5 -halogenalkoxy, C ⁇ -C 5 -alkoxycarbonyl, CC 3 - Halogenalkoxycarbonyl or C 2 -C 5 haloalkenyloxy substituted phenyl or benzyl.
  • R 9 preferably represents are hydrogen, C 5 -alkyl, C 3 haloalkyl, halo-dC 3 alkylcarbonyl, C] -C 5 alkoxyalkyl, CC 5 alkylcarbonyl or C 3 -C 6 cycloalkyl.
  • R 9 preferably represents a heterocyclic group linked to the neighboring groups at two different positions selected from the following list (the exocyclic dashes in each case indicate the links to the neighboring groups according to the arrangement in formula (I)),
  • heterocyclic groups are each optionally substituted by one or two substituents from the series nitro, hydroxy, amino, cyano, halogen, C 1 -C 5 -alkyl, C 1 -C 5 - haloalkyl, CC 5 -alkoxy, Ci-Cs-haloalkoxy, C ⁇ -C 5 -Alkylthio, -C-C 5 -Halogenalkyl- thio may be substituted.
  • a 2 particularly preferably represents one of the alkanediyl groups listed below,
  • R 1 particularly preferably represents hydrogen, nitro, hydroxyl, amino, cyano, fluorine, chlorine, bromine, iodine, in each case optionally by cyano, fluorine, chlorine, methylsulfinyl, methylsulfonyl, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio , Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t
  • R 2 particularly preferably represents hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, fluorine, chlorine, bromine, iodine, and in each case methyl, ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n - or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-buty
  • R 3 particularly preferably represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy
  • R 4 particularly preferably represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy
  • R 5 particularly preferably represents hydrogen, optionally by nitro, hydroxyl, amino, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • Pentinyl CC 2 -alkylenedioxy, Cj-C 2 -fluoroalkylenedioxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoximinomethyl, ethoximinomethyl, ethoximinomethyl Methoximinoethyl or Ethoximinoethyl and the grouping
  • a 3 particularly preferably represents a single bond or one of the groups -CH 2 -, -CH 2 CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -CH 2 -, -CH (CH 3 ) -, -CH (CH 3 ) CH 2 -CH 2 -, -CH (C 2 H 5 ) -, -C (CH 3 ) 2 -, -CH (CH 3 ) CH 2 -, -CH (CH 3 ) CH (CH 3 ) - and -CH 2 C (CH 3 ) 2 -CH 2 -, which optionally with one to four identical or different substituents from the group difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroe
  • R 6 particularly preferably represents hydrogen, cyano, hydroxy, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo- propylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoromethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichlorooxy, n-i-methyl, n-i-trichloro-oxy, n-methoxy, n-me
  • R 7 particularly preferably represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, Cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl, difluoromethyl, trifluoromethyl,
  • R 7 is also particularly preferably together with R 6 each optionally single to quadruple, identical or different by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • -CH 2 -CH CH-CH 2 -
  • -CH (CH 3 ) CH CH-
  • a CH 2 group can optionally be replaced by O, S or NR 9 .
  • R 8 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichloroethyl, ethenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, fluoroethenyl, difluoroethenyl, trifluoroethenyl, chloroethenyl, dichloroethenyl, trichloroethenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-but
  • Trichloroethyl methylcarbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s- or t-butylcarbonyl, ethenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2- Pentenyl, 3-pentenyl, fluoroethenyl, difluoroethenyl, trifluoroethenyl, chloroethenyl, dichloroethenyl, trichloroethenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3- Pentinyl, methoxy, ethoxy, n- or i-propoxy, n-,
  • R 9 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichloroethyl, Methoxymethyl, methoxyethyl,
  • Y particularly preferably stands for a heterocyclic group linked to the neighboring groups at two different positions selected from the following list (the exocyclic dashes in each case indicate the links to the neighboring groups according to the arrangement in formula (I)),
  • these heterocyclic groupings each optionally having one or two substituents from the series nitro, hydroxy, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichloroethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, Chlorodifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, chloroeth
  • a 2 very particularly preferably represents one of the groupings listed below:
  • R 1 very particularly preferably represents hydrogen, nitro, hydroxyl, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, for each optionally by nitro, hydroxy, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i -, s- or t-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl,
  • R 2 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
  • R 3 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
  • R 4 very particularly preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
  • R 5 very particularly preferably represents hydrogen, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichloroethyl , Methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, chloroethoxy or dichloroethoxy, C ⁇ -C 2 -alkylenedioxy, C ⁇ -C 2 -fluorio-nthio-alkylenedioxy, methyl or i-propylthio,
  • radicals A 3 , R 6 and R 7 have one of the meanings given above.
  • Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio can be substituted.
  • R 1 most preferably represents hydrogen, nitro, hydroxy, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino or dimethylamino.
  • R 2 most preferably represents hydrogen, fluorine, chlorine or bromine.
  • R 5 most preferably represents hydrogen or optionally fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, chloroethyl, dichloroethyl, trichloroethyl, methoxy, ethoxy , n- or i-Propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, chloroethoxy or dichloroethoxy substituted pyridinyl.
  • Y most preferably represents one of the heterocyclic groups below
  • R is C r C 4 alkyl and preferably methyl.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • hydrocarbon radicals such as alkyl - in each case straight-chain or branched - as far as possible - also in connection with heteroatoms such as in alkoxy.
  • R 5 has the meanings given in the list below:
  • R 5 has the meanings given above in Grappe 1.
  • R 5 has the meanings given above in Group 1.
  • R 5 has the meanings given above in Grappe 1.
  • R 5 has the meanings given above in Group 1: Group 6
  • R 5 has the meanings given above in Grappe 1.
  • R 5 has the meanings given above in Grappe 1.
  • R 5 has the meanings given above in Grappe 1.
  • the new substituted oxyarenes of the general formula (I) have interesting biological properties. They are characterized in particular by strong arthropodicides (insecticidal and acaricidal) and nematicidal activity and can be used in agriculture, in the forest, in the protection of stocks and materials, and in the hygiene sector.
  • X 1 represents halogen
  • a 2 and R 5 have the meaning given above and
  • the carbon atoms of the olefinic double bond are optionally substituted as indicated above for Y, if appropriate in the presence of one or more diluents and if appropriate in the presence of one or more reaction auxiliaries,
  • R, R, R, R, A and A have the meanings given above;
  • a 2 and R 5 have the meaning given above,
  • R 1 , R 2 , R 3 , R 4 , R 5 , A 1 and A 2 have the meanings given above, or
  • a suitable thionating agent for example diphosphorus pentasulfide (P 2 S 5 ) or Lawesson's reagent (cf. review of Lawesson's reagent: RA Cherkasov et al., Tetrahedron 41, 1985, p. 2567)
  • the cyclization sequence is known to involve incorporation of Sulfur (see also JM Sprague, AM Land; Heterocyclic Compounds, RC Elderfield, Vol. 5, New York, J. Wiley & Sons 1957, p. 484; RH Wiley, DC England, LC Behr, Org. Reactions 6 (1951 ) 367), or
  • R 1 , R 2 , R 3 , R 4 , R 5 , A 1 and A 2 have the meanings given above.
  • substituted benzaldoximes to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (D) are generally defined by the formula (II).
  • a 1 , R 1 , R 2 , R 3 and R have 4 preferably those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) as preferred or as particularly, very particularly or most preferably for A 1 , R 1 , R 2 , R 3 and R 4 have been specified.
  • a 1 , R 1 , R 2 , R 3 and R 4 have the meaning given above,
  • hydroxylamine hydrochloride optionally in the presence of a diluent, e.g. Acetonitrile or N, N-dimethylformamide, and optionally in the presence of a reaction auxiliary such as e.g. Potassium carbonate or triethylamine, at temperatures between 0 ° C and 100 ° C (see Houben-Weyl, Methods of Organic Chemistry, Vol. X / 4, 4th ed., 1968, G. Thieme Verlag, Stuttgart New York, p 55; Vol. 14 b, 4th ed. 1990, G. Thieme Verlag, Stuttgart New York, p. 287; JP Freemann Chem. Rev. 73 (1973), p. 283.
  • a diluent e.g. Acetonitrile or N, N-dimethylformamide
  • a reaction auxiliary such as e.g. Potassium carbonate or triethylamine
  • the halogenation to give compounds of the general formula (in) is carried out by initially placing compounds of the general formula (H) in a diluent and adding the corresponding halogenating agent, which is optionally dissolved in a diluent (see also Houben-Weyl, Methoder der Organischen Chemie, 4th ed., 1952, G. Thieme Verlag, Stuttgart New York, p. 691; Vol. X / 3, 4th ed. 1965, G. Thieme Verlag, Stuttgart-New York, p. 847, Preparation Examples).
  • the benzaldoximes of the general formula (II) and the compounds of the general formula (HI) can of course be used both in the form of their E or Z isomers and in the form of their mixtures of these stereoisomers.
  • the substituted benzaldehydes of the formula (VHT) are obtained in a manner known per se (cf. Houben-Weyl, Methods of Organic Chemistry, Volume E3, pages 3-608, G. Thieme Verlag, Stuttgart New York), for example by reacting appropriate ones Hydroxybenzoic acid esters of the general formula (IX) with halogen compounds of the general formula (X), subsequent hydrolysis of the esters of the general formula (XI), reduction of the carboxylic acids of the general formula (XII) thus formed to the benzyl alcohols of the general formula (Xi ⁇ ) and Oxidation of these compounds, as can be represented, for example, by the following reaction scheme:
  • a 1 , R 1 , R 2 , R 3 and R 4 have the meanings given above;
  • X 1 represents halogen, especially chlorine, bromine or iodine.
  • the substituents of the compounds of the formula (VIH), such as, for example, the substituent R 1 can also be modified in further reaction steps.
  • R 1 is halogen, in particular fluorine
  • a nucleophilic exchange with suitable nucleophiles can be carried out in the presence of basic reaction auxiliaries mentioned below as part of the definition of substituents for R 1 (cf. for example the method from: Bioorg. Med. Chem. 9 (2001) for the N, N-dimethylamino radical, pp. 677-694; J. Med. Chem. 45, 25 (2002) p. 5417, for the isopropylthio radical).
  • Suitable nucleophiles in the exchange reaction are mercapto compounds, hydroxy compounds or amino compounds.
  • the aldehydes of the general formula (VET) can also be prepared by first generating an aldehyde of the general formula (VITIb) using generally known methods and then introducing the radical A 1 using generally known methods:
  • compounds of the general formula (VIUc) which have a suitable protective group (SG) can also be used as a precursor for the preparation of the compounds of the general formula (VIlb).
  • suitable protective groups (SG) known for hydroxygroups, substituted methyl ethers and ethers, substituted ethyl ethers, substituted benzyl ethers, silyl ethers, esters, carbonates or sulfonates (see Greene TW, Wuts PGW in Protective Groups in Organic Synthesis; John Wiley & Sons, Inc. 1999).
  • Possible reaction paths can be outlined as follows:
  • R preferably represents methyl, ethyl or benzyl
  • SG 1 preferably represents benzyl (Bn), Si (Pr) 3 (TIBS) or SiMe 2 -fßu (TBDMS).
  • R represents the same radicals as indicated above for R 1 .
  • R ' is hydrogen, methoxy or phenyl.
  • alkenes to be used further as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (V).
  • a 2 and R 5 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention as preferred or as particularly, very particularly or most preferably for A 2 and R 5 have been given.
  • the starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. preparation examples).
  • Suitable halogenating agents are all halogen compounds which are suitable for converting benzaldehyde oximes into corresponding benzhydroxamic acid halides. Examples include N-bromo called succinimide and N-chloro-succinimide.
  • the process according to the invention for the preparation of the compounds of the general formula (T) is preferably carried out using one or more acid binders or reaction auxiliaries. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention.
  • alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium, cesium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine,
  • the process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using one or more diluents.
  • Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the compounds of the general formula (I) according to the invention can form salts.
  • suitable suitable salts of the compounds of the general formula (I) are customary non-toxic salts, i.e. Salts with bases and salts (“adducts”) with acids.
  • Salts are formed according to standard salt manufacturing processes.
  • the compounds according to the invention are reacted with appropriate acids to form acid addition salts.
  • Representative acid addition salts are salts which are formed, for example, by reaction with inorganic acids, such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, succinic acid, lactic acid, formic acid, maleic acid, camphoric acid, phthalic acid, phthalic acid, Form glutaric acid, stearic acid, salicylic acid, sorbic acid, cinnamic acid, picric acid, benzoic acid or organic sulfonic acids such as methanesulfonic acid and para-toluenesulfonic acid.
  • inorganic acids such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids such as acetic acid,
  • the active compounds according to the invention are suitable, with good plant tolerance, favorable warm-blood toxicity and good environmental compatibility, for protecting plants and plant organs, for increasing crop yields, improving the quality of the crop and for Control of animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in gardens and leisure facilities, in the protection of supplies and materials as well as in the hygiene sector.
  • animal pests in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in gardens and leisure facilities, in the protection of supplies and materials as well as in the hygiene sector.
  • insects in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in gardens and leisure facilities, in the protection of supplies and materials as well as 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 for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda for example, Blaniulus guttulatus.
  • Chilopoda for example Geophilus carpophagus
  • Scutigera spp From the order of the Symphyla, for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus.
  • Orthoptera for example Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • the Blattaria for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
  • the Dermaptera for example, Forficula auricularia.
  • From the order of the Isoptera for example Reticulitermes spp.
  • Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi , Frankliniella accidentalis.
  • Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Aleurodes brassicae Bemisia tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigeram, Hyalopteras arandinis, Phylloxera vastatrix, Pemphigusums spp.
  • Sitophilus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agribiole spp., Tenebrio molitor.
  • Conoderas spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp ..
  • From the class of the Arachnida for example Scorpio maurus, Latrodectus mactans, Acaras siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora.
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsppv., Hemitarspp ..
  • 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., Bursaph.
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • 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, Bulbs and rhizomes are listed.
  • 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, injecting and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and 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, as solid carriers for granules are possible: e.g.
  • emulsifying and / or foam-generating agents are possible: for example non- ionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • emulsifying and / or foam-generating agents are possible: for example non- ionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • dispersants for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and 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% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • 2-phenylphenol 8-hydroxyquinoline sulfates; AcibenzoIar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
  • bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
  • Buthiobate butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim;
  • carboxin carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;
  • diclocymet Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines;
  • Fenbuconazole fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph;
  • fluoromides fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;
  • flutriafol flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
  • Imibenconazole hninoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; Iramamycin; isoprothiolane; Isovaledione; kasugamycin;
  • Metalaxyl-M metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
  • phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
  • procymidone propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
  • prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur;
  • trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin;
  • Preparations such as Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; mancopper; Oxine-copper.
  • bactericides Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
  • the active compounds according to the invention can also be used 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 compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues ,
  • 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 substance When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • all plants and their parts can be treated.
  • wild plant species and plant varieties and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, are increased Tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storage life and / or workability of the harvested products possible that go beyond the expected effects.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important crop plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, with corn, soybeans , Potato, cotton, tobacco and rapeseed are highlighted.
  • the traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryUA, CrylUA, CryIUB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example hnidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Bt plants are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YEELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (Potato) are distributed.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Anoplurida for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtiras spp., Solenopotes spp.
  • Mallophagida and the subordinates Amblycerina and Ischnocerina for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
  • Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
  • Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • the Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • the Blattarida for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. From the subclass of the Acari (Acarina) and the orders of the Meta and Mesostigmata, e.g.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods By fighting these arthropods, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the aid of shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holsters, marking line devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation: Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicolles, Lyctus pubisxis, Lyctus pubisoleis, Lyctus pubisoleis, Lyctus pubxis syllable, Lyctus pubxis, Tryptodendron spec.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably cc-monochloronaphthalene, are used.
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • hydroxyl and / or ester and / or Aliphatic organic chemical solvents containing ether groups such as, for example, glycol ethers, esters or the like, are used.
  • organic-chemical binders Acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.
  • a vinyl resin e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol ether and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl stearate or amyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Especially preferred mixing partners which may insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide, triflumuron, clothianidin, spinosad, tefluthrin and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanide, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-n-
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as in bis (trialkyltin) sulfides, tri- n-butyltin laurate, tri-ra-butyltin chloride, copper (I) oxide, triethyltin chloride, tri- / z-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine ) -wismutchlorid, tri-w-butylzinnfluorid, carbamate Manganethylenbisthio-, zinc dimethyldithiocarbamate, Zinkethylenbisthiocarbamat, zinc and copper salts of 2-pyridinethiol-1-oxide, Bisdimethyldithiocarbamoylzinkethylenbisthiocarbamat,
  • the ready-to-use antifouling paints can optionally contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn; Fungicides such as benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynylbutylcarbamate, tolylfluanid and azoles such as azaconazole, cyconconazole, epoxyconazole, hexaconazole, metazazole, metconazole, metconazole, metconazole, metconazole, Molluscicides such as fentin acetate, metaldehyde, methio
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, ParkRidge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt as well as epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, theological properties modifiers and other conventional ingredients. The compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Scorpionidea for example Buthus occitanus.
  • acarina for example Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus for Dermatophagoides for Dermatophagoides.
  • Araneae for example Aviculariidae, Araneidae.
  • Opiliones for example Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Isopoda for example Oniscus asellus, Porcellio scaber.
  • Diplopoda for example, Blaniulus guttulatus, Polydesmus spp.
  • Chilopoda for example Geophilus spp.
  • Zygentoma for example Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Psocoptera for example Lepinatus spp., Liposcelis spp.
  • Coleoptera for example Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila domppis, Phanncaotpp , Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • From the order of the Lepidoptera for example Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • From the order of the Siphonaptera for example Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • From the order of the Hymenoptera for example Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Pediculus humanus capitis for example Pediculus humanus capitis, Pediculus humanus corporis, Phthiras pubis.
  • Heteroptera for example Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • reaction solution 16 hours at RT and then for a further 24 hours at 70 ° C.
  • reaction solution is mixed with about 20 ml of water and extracted three times with 50 ml of dichloromethane. After the organic phase has been evaporated to dryness, the remaining residue is purified by means of preparative HPLC.
  • the preparation is carried out analogously to the procedure according to Example (II), with stirring after addition of NCS for 18 hours at RT and after addition of triethylamine for 18 hours at 80 ° C. with 370 mg (1.25 mmol) of 3-benzyloxy 5-trifluoromethyl-benzaldehyde oxime, 579 mg (2.51 mmol) 2-pent-4-enyloxy-5-trifluoromethyl-pyridine, 184 mg (1.38 mmol) NCS, 101 mg (1.38 mmol) triethylamine, 15 ml DMF.
  • the 4- (2,4-dichloro-phenoxy) -butyric acid chloride prepared beforehand is added and the mixture is stirred at 90 ° C. for about 24 hours under a gentle stream of nitrogen in an open flask. After cooling, water is added and brought to pH ⁇ 7 with dilute HC1. It is extracted several times with ethyl acetate, the combined organic phases are dried over Na 2 SO 4 , filtered and evaporated to dryness.
  • the acid chloride is added and the mixture is stirred at 90 ° C. for about 24 h in an open flask under a gentle stream of nitrogen.
  • the mixture is allowed to cool, about 10 ml of water are added, the pH is brought to ⁇ 6 using dilute HCl and the mixture is extracted several times with ethyl acetate. Combined organic phases are dried over Na 2 SO 4 , filtered and concentrated.
  • the crude product is chromatographed on silica gel (hexane: ethyl acetate 4: 1).
  • the silylation is carried out analogously to the instructions for example (II-5a) with 7.6 g (40.7 mmol) of 1- (3-chloro-2,5-dihydroxyphenyl) ethanone, 9.4 g (48.9 mmol) triisopropylsilyl chloride, 5.35 g (52.9 mmol) triethylamine, 150 ml dichloromethane.
  • the methylation is carried out analogously to the instructions for example (1-63) with a reaction time of
  • the allylation is carried out analogously to the procedure according to Example (1-63) with 90 mg (purity 50%; 0.1 mmol) of 3-chloro-4-methoxy-5- ⁇ 2- [2- (5-trifluoromethyl-pyridine-2 -yloxy) -ethyl] -thiazol-4-yl ⁇ - phenol, 48 mg (0.25 mmol) 3-bromo-l, l-dichlorotropene, 58 mg (0.42 mmol) potassium carbonate and 15 ml acetone.
  • N-chlorosuccinimide N-chlorosuccinimide
  • the mixture is poured onto 200 ml of water in a separating funnel and extracted with a mixture of 200 ml of heptane and 200 ml of ethyl acetate.
  • the organic phase is washed again with approx. 100-200 mL water and then the solvent is stripped off (increase the bath temperature on the rotary evaporator to approx. 70 ° C / 15 mbar in order to remove residual DMF).
  • a brown solid (approx.
  • the mixture is allowed to cool to room temperature and then poured to about 50 mL conc. Hydrochloric acid in the separating funnel, mixes the phases and adds about 100 mL water. After the organic phase has been separated off, the aqueous phase is extracted twice more with about 200 ml of toluene and the combined organic phases are evaporated to dryness. Finally, the 3-bromo-l, l-dichloropropene formed in the reaction also passes over and has a somewhat pungent and irritating smell.
  • the formation of the oxi takes place analogously to the procedure from example (II-2) with a reaction time of 18 hours with: 350 mg (1.25 mmol)) 3-benzyloxy-5-trifluoromethyl-benzaldehyde, 130 mg (1.87 mmol ) Hydroxylamine hydrochloride, 378 mg (3.75 mmol) triethylamine, 20 ml acetonitrile. After concentrating the organic phase to dryness, 370 mg (purity 86%, 86% of theory) of 3-benzyloxy-5-trifluoromethyl-benzaldehyde oxime are obtained. MS (ES +): 296.
  • the oxidation is carried out analogously to the procedure according to Example (II-1) with: 12.7 g (30 mmol) (2-benzyloxy-3-chloro-5-triisopropylsilyloxy-phenyl) -methanol, 10.8 g (50 mmol) pyridine chlorochromate , 300 ml dichloromethane.
  • the oxime is formed analogously to the procedure from Example (II-2) with a reaction time of one hour with: 500 mg (1.19 mmol) 2-benzyloxy-3-chloro-5-triisopropylsilyloxy-benzaldehyde, 124 mg ( 1.79 mmol) hydroxylamine hydrochloride, 361 mg (3.58 mmol) triethylamine, 20 ml acetonitrile.
  • 2-Pent-4-enyloxy-5-trifluoromethyl-pyridine is prepared in accordance with Example (III-1) using 4.75 g of penten-5-ol (55.1 mmol), 1.21 g of sodium hydride (60%) (30.3 mmol) and 2-chloro-5-trifluoromethyl-pyridine (27.5 mmol).
  • the brown suspension obtained in the reaction is mixed with about 50 ml of water and extracted with ethyl acetate / heptane.
  • the compound is prepared analogously to the procedure according to Example (VI) with: 267 mg (75%; 8.3 mmol) sodium hydride, 653 mg (7.6 mmol) 3-methyl-3-buten-l-ol, 1.5 g (8.3 mmol) 2-chloro-5-trifluoromethylpyridine, 12 ml THF.
  • the organic phase is then separated off and washed first with saturated NaHCO 3 solution and then with 2M NaOH solution.
  • the inorganic phases are combined with conc. Acidified hydrochloric acid and extracted with dichloromethane.
  • 2-N, N-dimethylamino-3-chloro-5-methoxy-benzaldehyde 450 mg (2.5 mmol) 2-N, N-dimethylamino-5-methoxy-benzaldehyde (preparation: see P. Damhaut et al, Tetrahedron, 53 (16), 5785-5796, 1997) 435.8 mg (3.2 mmol) of N-chlorosuccinimide are added in portions in 20 ml of N, N-dimethylformamide and while cooling with ice (0-10 ° C.) and then stirred for a further 18 hours at room temperature. The entire reaction mixture is then poured into water and extracted with dichloromethane.
  • 2-N, N-dimethylamino-3-chloro-5-methoxy-benzaldehyde oxime is prepared analogously to example (II-2) with 130 mg (0.6 mmol) of 2-N, N-dimethylamino-3-chlorine -5-methoxy-benzaldehyde, 60 mg (0.91 mmol) hydroxylamine hydrochloride, 180 mg (1.81 mmol) triethylamine, 10 ml acetonitrile.
  • reaction mixture is then shaken out with dichloromethane / water and the separated aqueous phase is extracted again with dichloromethane.
  • Emulsifier 2 parts 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 to the desired concentration with water containing emulsifier.
  • Soybean shoots (Glycine max) are treated by immersing them in the active ingredient preparation of the desired concentration and filling them with Heliothis armigera-R pen while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • the compound according to preparation example II shows an active ingredient concentration of 100 ppm after 7 days and kills 100%.
  • Emulsifier 2 parts 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.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne / »cogw / to-egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Emulsifier 2 parts 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 to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleraceä) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the cockroach ⁇ Flutella xylostell ⁇ ) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts 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 to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigu ⁇ ) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 0.5 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 to the desired concentration with water containing emulsifier.
  • Corn leaf disks (Zea mays) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with caterpillars of the army worm (Spodoptera frugiperda).
  • the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • Emulsifier 0.5 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 to the desired concentration with water containing emulsifier.
  • Bean leaf slices Phaseolus vulgaris
  • Triticae Tricholine dexase
  • Bean leaf slices Phaseolus vulgaris
  • which are affected by all stages of the common spider mite Tetranychus urticae
  • an active ingredient preparation of the desired concentration is sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
EP04729628A 2003-05-09 2004-04-27 Substituierte oxyarene, and use thereof for controlling pests Withdrawn EP1638962A2 (de)

Applications Claiming Priority (2)

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DE10320782A DE10320782A1 (de) 2003-05-09 2003-05-09 Substituierte Oxyarene
PCT/EP2004/004415 WO2004099197A2 (de) 2003-05-09 2004-04-27 Substituierte oxyarene und deren verwendung zur bekämpfung von schädlingen

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JP2009515855A (ja) * 2005-11-14 2009-04-16 ビーエーエスエフ ソシエタス・ヨーロピア レゾルシン誘導体およびその殺虫剤としての使用
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MX2009013469A (es) 2007-06-13 2010-01-20 Du Pont Insecticidas de isoxazolina.
TWI430995B (zh) 2007-06-26 2014-03-21 Du Pont 萘異唑啉無脊椎有害動物控制劑
MX368680B (es) 2007-06-27 2019-10-11 Du Pont Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga.
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TWI455919B (zh) 2008-04-09 2014-10-11 Du Pont 製備３－三氟甲基查耳酮（ｃｈａｌｃｏｎｅ）之方法
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JP2006525964A (ja) 2006-11-16
AU2004235909A1 (en) 2004-11-18
MXPA05011962A (es) 2006-02-02
DE10320782A1 (de) 2004-11-25
BRPI0410236A (pt) 2006-05-09
WO2004099197A2 (de) 2004-11-18
KR20060009892A (ko) 2006-02-01
WO2004099197A3 (de) 2005-01-27

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