Classifications

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  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
  • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
  • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
  • C07D249/14—Nitrogen atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/02—Acaricides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

• the present invention relates to new 5-amino-substituted pyrazoles and triazoles, processes for their preparation and their use for combating animal pests, especially arthropods and in particular insects, arachnids and nematodes.
• the object of the present invention was to provide compounds for use in combating animal pests, by means of which the spectrum of pesticides is supplemented under various aspects.
• the present invention therefore relates to new compounds of the formula (I) in which (configuration 1-1)
• Ar represents phenyl or a 5- or 6-membered heteroaromatic ring, in each case unsubstituted or substituted by 1 to 4 R ⁇ ; each stands
• R A independently for halogen, cyano, nitro, SFs, C (Q ') R a , C (0) 0R a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or CVCV-cycloalkyl, all of which can be unsubstituted or monosubstituted up to 13-fold with halogen and / or optionally with 1 to 3 R f could be; or for phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered heteroaromatic ring system, all in each case unsubstituted or substituted with 1 to 3 R g ;
• A is N or CR A ; it stands
• R A for H, Halogen, Cyano, Nitro, SF 5 , C (Q ') R a , C (0) 0R a , C (Q') NR b R c , NR d R e , OR a , S (0 ) n R a or S0 2 NR b R c ; or for CVCV-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C3-Cvcycloalkyl, all of which can be unsubstituted or monosubstituted up to 13 times by halogen and / or optionally by 1 to 3 R f ; or for phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered heterocyclic aromatic ring system, all in each case unsubstituted or substituted by 1 to 3 R g ;
• R n for H; or for CVCV-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or CVCV-cycloalkyl, all of which can be unsubstituted or mono- to five-fold substituted by halogen and / or optionally by 1 to 2 R h ; or for phenyl or for a 4- to 7-membered saturated, partially saturated or aromatic heterocycle with 1 to 3 heteroatoms, each unsubstituted or substituted by 1 to 5 R g ;
• R 12 for H; or for CVCV-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or CVCV-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R g ; or
• R 2 stands for the substructure of the general formula -XYZ. It stands for the
• X is phenyl or a 5- or 6-membered heteroaromatic ring, all unsubstituted or substituted by 1 to 3 R x ; each stands
• R x independently of one another for halogen, cyano, nitro, C (Q ') R a , C (0) OR a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -
• each R Y1 and R Y2 stands for H; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 7 -cycloalkyl, all unsubstituted or substituted by 1 to 7 R Yn ; each stands for H; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 7 -cycloalkyl, all unsubstituted or substituted by 1 to 7 R Yn ; each stands
• R Yn independently of one another for halogen, cyano, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;
• Q Y for O or S;
• R Z1 independently of one another for a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, in each case unsubstituted or substituted by 1 to 4 R zn ; each stands
• R zn independently represent halogen, cyano, nitro, SFs, C (Q ') R a , C (0) OR a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or CYCV-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R zla ; or for phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R zla ; or two adjacent R zn together form an unsubstituted or with 1 to 6 R zla substituted linear C3-Cs-alkylene group, independently of one another, the 1 CH 2 unit
• R zla for halogen, cyano, Ci-G t -alkyl, Ci-G t -alkoxy, Ci-G t -thioalkyl, Ci-C4-haloalkyl or Ci-C4-haloalkoxy;
• Rz 2 , R Z2a and R Z3 independently of one another represent H; or for C (0) R a , C (0) OR a , C (0) NR b R c , S (0) n R a ; or for CYCY-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C3-C7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R Z21 ; or for phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, all unsubstituted or substituted by 1 to 4 R Z21 ; each stands
• R Z21 independently of one another for halogen, cyano, nitro, SFs, C (Q ') R a , C (0) OR a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C3-C7-cycloalkyl; or
• R Z21 independently of one another for halogen, cyano, CVCY-alkyl, C3-C6-cycloalkyl, Ci- G, -haloalkyl, Ci-Ce-alkoxy, or CYCY-haloalkoxy; or
• R Z2a and a second R Z2a together with the NCN unit form a 5- to 7-membered ring;
• R Z41 , R Z42 and R Z43 independently of one another represent H, halogen or NR d R e ; or C i -CA, - alkyl, C2-C6-alkenyl, C2-C6-alkynyl, CVCVCycloalkyl, Ci-Ce-alkoxy, C2-C6-alkenyloxy, C2- C ö alkynyloxy, CV C 7 - C yc 1 a 1 kxy, Ci-Ce-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C3-C7-cycloalkylcarbonyloxy, all unsubstituted or substituted by 1 to 7 R f ; or one of the radicals R Z41 , R Z42 or R Z43 for oxo;
• R 244 for H; or for CVCV-alkyl, Ci-Ce-alkoxy, C2-C6-alkenyloxy, all unsubstituted or substituted by 1 to 5 R f ;
• R a independently of one another for CVCV-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, all of which can each be unsubstituted or mono- up to 13-fold substituted with halogen and / or optionally with 1 to 3 R f could be; or for phenyl, unsubstituted or substituted with 1 to 7 R g ;
• R b and R c independently of one another represent H; or for CVCV-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, all in each case unsubstituted or substituted by 1 to 7 R f ; or for phenyl, or for a 5- or 6-membered heteroaromatic ring, all unsubstituted or substituted by 1 to 4 R g ; or R b and R c together form a 3- to 7-membered ring;
• R d and R e independently of one another for H, C (Q ') R a , C (0) OR a ; or for CVCV-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted by 1 to 7 R f ; or for phenyl, unsubstituted or substituted with 1 to 7 R g ; or R d and R e together form a 3- to 7-membered ring;
• R f independently of one another for halogen, cyano, nitro, C3-C6-cycloalkyl, Ci-C4-alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4 -Haloalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci-C4-Alcarbonyl, Ci-C4-Alkoxy- carbonyl; or for phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 7 R g ;
• R g independently of one another for halogen, cyano, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4 -Haloalkylthio, C1-C4-Al- kylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C1-C4-Al- kylcarbonyl, Ci-C4-alkoxycarbonyl;
• R h independently of one another for halogen, cyano, nitro, hydroxy, C3-C6-cycloalkyl, Ci-C4-alkoxy, C3-C6-cycloalkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C3-C6-cycloalkylthio, Ci -C4-Haloal- kylthio, Ci-C4-Alkylsulfinyl, C3-C6-Cycloalkylsulfinyl, Ci-C4-Haloalkylsulfinyl, Ci-C4-Alkylsulfonyl, C3-C6-Cycloalkylsulfonyl, Ci-C4-Haloalkylsulfonyl, OS0 2 R a , S0 2 NR b R c , N (R b ) (R c ), C (Q ')
• Preferred (embodiment 2-1) are the compounds of the formula (I) in which
• Ar is phenyl, unsubstituted or substituted with 1 to 4 R ⁇ ; each stands
• R A independently of one another for halogen, cyano, nitro, SF 5 , C (Q ') R a , C (0) OR a , C (Q') NR b R c , NR d R e , OR a , S (0 ) n R a or S0 2 NR b R c ; or for Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C2-C6-alkynyl or C3-C7-cycloalkyl, all of which can each be unsubstituted, or simply up to 13-fold with halogen and / or optionally with 1 to 2 R f can be substituted; or for phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R g ;
• A is N or CR A ; it stands
• R A for H, halogen, cyano or SF 5 ; or for Ci-C4-alkyl, C2-C4-alkenyl or C3-C6-cycloalkyl, all of which can each be unsubstituted or mono- to sevenfold with halogen and / or optionally with an R f ;
• R n for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all of which can be unsubstituted, or simply to five times with halogen and / or optionally with 1 to 2 R h can be substituted; or for phenyl or for a heterocycle the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2, 5-thiadia
• R 12 for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or CVCV-cycloalkyl, all unsubstituted or substituted by 1 to 3 R g ; or
• R n and R 12 together with the nitrogen atom to which they are bonded represent a heterocycle from the series U1 to U-30
• R x independently of one another for halogen, cyano, nitro, C (Q ') R a , C (0) OR a ; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C6-alkynyl or C3-C4-cycloalkyl, all each unsubstituted or substituted by 1 to 3 R f ;
• R Y1 and R Y2 for H; or for C iG, -alkyl, C2-C6-alkenyl, C2-C6-alkynyl or CYCV-cycloalkyl, all unsubstituted or substituted by 1 to 5 R Yn ; each stands
• R Yn independently of one another for halogen, cyano, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;
• R ZI is phenyl, unsubstituted or substituted with 1 to 4 R zn ; each stands
• R zn independently of one another for halogen, cyano, nitro, SFs, C (Q ') R a , C (0) 0R a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-C 6 -alkyl, C 2 -C 6 - alkenyl, C2-C6-alkynyl or C3-C7-cycloalkyl, all unsubstituted or substituted by 1 to 5 R zla ; or for phenyl or a 5- or 6-membered one heteroaromatic ring, all unsubstituted or substituted by 1 to 3 R zla ; or two adjacent R zn together form an unsubstituted or with 1 to 4 R zla substituted linear Cs-Cs-alkylene group, independently of one another 1 CH2 unit by carbon
• R zla for halogen, cyano, Ci-C3-alkyl, Ci-C3-alkoxy, Ci-C3-thioalkyl, Ci-C3-haloalkyl or Ci-C3-haloalkoxy;
• R Z2 , R Z2a and R Z3 independently of one another represent H; or for C (0) R a , C (0) OR a , C (0) NR b R c , S (0) n R a ; or for CVCV-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 4 R Z21 ; or for phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, all unsubstituted or substituted by 1 to 3 R Z21 ; each stands
• R Z21 independently of one another for halogen, cyano, nitro, SFs, C (Q ') R a , C (0) OR a , C (Q') NR b R c , NR d R e , OR a , S (0) n R a or S0 2 NR b R c ; or for Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C7-cycloalkyl; or
• R Z21 independently of one another for halogen, cyano, CVCV-alkyl, C3-C6-cycloalkyl, Ci-CVHaloalkyl, CVCValkoxy, or CVCVHaloalkoxy; or
• R Z2a and a second R Z2a together with the NCN unit form a 5- to 7-membered ring;
• this R Z2 -R Z3 unit is unsubstituted or substituted by 1 to 4 R Z21 ;
• R Z41 , R Z42 and R Z43 independently of one another represent H, halogen or NR d R e ; or for C i -Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, CVCV-cycloalkyl
• R Z44 for H; or for CVCV-alkyl, Ci-Ce-alkoxy, C 2 -C 6 -alkenyloxy, all unsubstituted or substituted by 1 to 5 R f ;
• R a independently of one another for CVCV-alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, all of which can each be unsubstituted, or simply up to 13-fold with halogen and / or optionally with an R f ; or for phenyl, unsubstituted or substituted with 1 to 5 R g ;
• R b and R c independently of one another represent H; or for CVCV-alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, all in each case unsubstituted or substituted by 1 to 5 R f ; or for phenyl, or for a heteroaromatic ring from the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, pyridyl or pyrimidyl, all unsubstituted or substituted by 1 up to 5 R g ; or R b and R c together form a 3- to 7-membered ring;
• R d and R e independently of one another for H, C (Q ') R a , C (0) OR a ; or for Ci-Ce-alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, all unsubstituted or substituted by 1 to 5 R f ; or for phenyl, unsubstituted or substituted with 1 to 5 R g ; or R d and R e together form a 3- to 7-membered ring;
• R f independently of one another for halogen, cyano, nitro, C 3 -C 6 cycloalkyl, Ci-C 4 alkoxy, C 1 -C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Ci- C 4 -Alkylsulfinyl, Ci-C 4 -Haloalkylsulfinyl, Ci-C 4 -Alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, Ci-C 4 -Alcarbonyl, Ci-C 4 -Alkoxycar- bonyl; or for phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 5 R g ;
• R g independently of one another for halogen, cyano, nitro, Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci- C 4 -Alkylthio, Ci-C 4 -haloalkylthio, C 1 -C 4 -AI- kylsulfinyl, Ci-C 4 -haloalkylsulfinyl, Ci-C 4 -Alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, C 1 -C 4 -AI - kylcarbonyl, Ci-C 4 -alkoxycarbonyl;
• R h independently of one another for halogen, cyano, nitro, hydroxy, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C 3 -C 6 -cycloalkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, C 3 -C 6 -cycloalkylsulfinyl, Ci-C 4 -haloalkylsulfinyl, C 1 -C 4 - Alkylsulfonyl, C3-C6-cycloalkylsulfonyl, Ci-C4-haloalkylsulfonyl, 0S0 2 R a , S0 2 NR b R c , N (R b ) (R c
• Ar is phenyl, unsubstituted or substituted with 1 to 4 R Ar ; each stands
• R A independently of one another for halogen, SFs, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4-haloalkoxy.
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (R b ) OR a , -N (R b ) -CN, -N (R n ) C (Q ') R b , -N (R n ) C (Q 1 ) NR b R c , -N (R n ) C (0) OR a , - N (R n ) C (0) C (0) (0) 0R a , -N (R n ) S0 2 R a , -N C (R b ) N (R b ) (R c ); it stands
• R n for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all of which can be unsubstituted or substituted one to five times with halogen and / or optionally with 1 to 2 R h could be; or for phenyl or for a heterocycle from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyrimidyl, oxetanyl, Oxolanyl, oxanyl, thiethanyl, all unsubstituted or substituted by 1 to 3 R g ;
• R 12 for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all unsubstituted or substituted by 1 to 3 R g ; or
• R n and R 12 together with the nitrogen atom to which they are bonded for a heterocycle from the series Ul to U-7; U-13, U-14 or U-22 to U-27 U-25, U-26, U-27
• U b independently of one another for halogen, cyano, nitro, Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, Ci- C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4- alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -haloalkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl; and wherein the ring N atoms in U-13, U-14, and U-25 are not substituted by halogen, nitro, cyano, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy; m for 0.1, or 2
• R 2 stands for the substructure of the general formula -XYZ. It stands for the
• X represents phenyl, pyridyl or thienyl, all unsubstituted or substituted by 1 to 3 R x ; it stands
• R x independently of one another represent halogen, cyano, nitro; or for Ci-C 4 -alkyl, each unsubstituted or substituted by 1 to 3 R f ;
• R Y1 and R Y2 for H; or for Ci-C 2 -alkyl or C 3 -C 6 -cycloalkyl, all unsubstituted or substituted by 1 to 3 R Yn ; each stands
• R Yn independently of one another for halogen, cyano, Ci-C 2 -alkyl, C 3 -C 6 -cyc- loalkyl, Ci-C 2 -haloalkyl, Ci-C 2 -alkoxy, or Ci-C 2 -haloalkoxy;
• R zi is phenyl substituted with 1 to 4 R , stands; each stands
• R zn independently of one another for halogen, cyano, OR a , SR a , or for Ci-G t -alkyl, C3-CS r cycloalkyl, all unsubstituted or substituted by 1 to 3 R zla ; or two adjacent R zn together form an unsubstituted or with 1 to 4 R zla substituted linear C3-Cs-alkylene group, independently of one another 1 CFF unit by carbonyl and 1 to 2 CFb units by O, S, NF1 or N (CFb) can be replaced; each stands
• R zla for flalogues, cyano, CiV-alkyl, Ci-C3-alkoxy, Ci-C3-thioalkyl, Ci-C3-flaloalkyl or Ci-C3-flaloalkoxy;
• R Z2 , R Z2a and R Z3 independently of one another for Fl; or for CYG, - alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 4 R Z 21; ( J ci - f jj t phenyl or benzyl, all unsubstituted or substituted with 1 to 3
• R Z21 independently of one another for flalogues, cyano, Ci-G t -alkyl, C3-C6-cycloalkyl, Ci-C4-flaloalkyl, Ci-C4-alkoxy, or Ci-G t -haloalkoxy; or
• R Z2 and R Z3 together with the TCN unit form a 5- to 7-membered ring; be the R Z2 -R Z3 ring members made of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; there is that
• R Z21 independently of one another for halogen, cyano, Ci-C 3 -alkyl, C 3 -C 6 -cycloalkyl, Ci- C 3 -haloalkyl, Ci-C 3 -alkoxy, or Ci-C 3 -haloalkoxy;
• R Z41 , R Z42 and R Z43 independently of one another represent Ci-C 4 -alkoxy, C 2 -C 4 -alkenyloxy;
• R Z44 for H or Ci-C 4 -alkyl
• R a independently of one another for Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, all of which can be unsubstituted, or simply up to 7 times with halogen and / or optionally can be substituted by an R f ;
• R b and R c independently of one another represent H; or for Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, all unsubstituted or substituted by 1 to 3 R f ;
• R f independently of one another for halogen, cyano, nitro, C 3 -C 6 cycloalkyl, Ci-C 4 alkoxy, C 1 -C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Ci- C 4 -Alkylsulfinyl, Ci-C 4 -Haloalkylsulfinyl, Ci-C 4 -Alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, Ci-C 4 -Alcarbonyl, Ci-C 4 -Alkoxycar- bonyl; or for phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R g ;
• R g independently of one another for halogen, cyano, nitro, Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci- C 4 -alkylthio, Ci-C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, Ci-C 4 -haloalkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, C 1 -C 4 -AI - kylcarbonyl, Ci-C 4 -alkoxycarbonyl;
• R h independently of one another for halogen, cyano, nitro, hydroxy, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C 3 -C 6 cycloalkylthio, Ci-C 4 alkylthio -Haloal-, Ci-C 4 alkylsulfinyl, C 3 -C 6 cycloalkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C 4 -Alkylsul- fonyl, C 3 -C 6 -cycloalkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, C (Q ') NR b R c , N (R b ) C (Q') R a
• Ar is phenyl, unsubstituted or substituted with 1 to 3 R ⁇ ; each stands
• R A independently of one another for halogen, SFs, CF3, OCF3, OCH2CF3 or OCF2CF3.
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (R b ) OR a , -N (R b ) -CN, -N (R n ) C (Q ') R b , -N (R 11 ) C (Q 1 ) NR b R c , -N (R n ) C (0) 0R a , - N (R n ) C (0) C (0) (0) 0R a , -N (R n ) S0 2 R a , -N C (R b ) N (R b ) (R c ); it stands
• R n for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all of which can be unsubstituted or substituted one to three times with halogen and / or optionally with 1 to 2 R h could be; or for a heterocycle from the series pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, oxanyl, thiethanyl, all unsubstituted or substituted by 1 to 3 R g ;
• R n and R 12 together with the nitrogen atom to which they are bonded for a heterocycle from the series (U-2), (U-3), (U-6), (U-22), (U-23 ), (U-24), (U-25), (U-26) or (U-27)
• X is phenyl, unsubstituted or substituted with 1 to 3 R x ; it stands
• R x independently of one another represent halogen, cyano, methyl
• each R Y1 and R Y2 here represents H, CH 3 or CH 2 CH 3 ;
• R zl is phenyl substituted with 1 to 4 R zn ; where 1 R zn is in the 2-position and each is standing
• RZ n independently of one another for F, CI, Br, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 , CH 2 CH 2 CH 2 CH3, cyclopropyl, OCH 3 , OCH 2 CH3, OCH 2 CH 2 CH 3 , OCH (CH 3 ) 2 , CH 2 OCH 3 , or CH (CH 3 ) OCH 3 ;
• R Z2 , R Z2a and R Z3 independently of one another represent H; or
• R Z21 independently of one another for halogen, cyano, Ci-C3-alkyl, C3-C6-cycloalkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, or Ci-C3-haloalkoxy;
• R a independently of one another for Ci-C4-alkyl or C3-C6-cycloalkyl, all of which can be unsubstituted or can be monosubstituted up to 7 times with halogen and / or with an R f ;
• R b and R c independently of one another represent H; or for Ci-C4-alkyl or C3-C4-cycloalkyl, in each case unsubstituted or substituted with 1 to 3 R f ;
• R f independently of one another for halogen, cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4-AI- kylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, Ci -C4-alkoxycarbonyl;
• R g independently of one another for halogen, cyano, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4 -Alkylsulfinyl, C1-C4-AI- kylsulfonyl;
• R h independently of one another for halogen, cyano, nitro, hydroxy, C3-C6-cycloalkyl, Ci-C4-alkoxy, C3-C6-cycloalkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, C3 -C6-Cycloalkylsulfinyl, Ci-C4-Alkylsulfonyl, C (Q ') NR b R c , N (R b ) C (Q') R a ; or for a heterocycle from the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,3-0-xadiazolyl, 1,2,4-oxadiazolyl, 1 , 3,4-oxadiazolyl, 1, 2,5-oxadia
• Ar is phenyl, unsubstituted or substituted with 1 to 3 R ⁇ ; each R A independently of one another stands for halogen, SFs, CF3, OCF3, OCH2CF3 or OCF2CF3.
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (R b ) OR a , -N (R b ) -CN, -N (R n ) C (Q ') R b , -N (R n ) C (Q 1 ) NR b R c , -N (R n ) C (0) 0R a , - N (R n ) C (0) C (0) (0) 0R a , -N (R n ) S0 2 R a , -N C (R b ) N (R b ) (R c ); it stands
• R n for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all of which can be unsubstituted or substituted one to three times with halogen and / or optionally with 1 to 2 R h could be; or for a heterocycle from the series pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, oxanyl, thiethanyl, all unsubstituted or substituted by 1 to 3 R g ;
• R 12 for H; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, all unsubstituted or substituted by 1 to 3 R g ; or
• R n and R 12 together with the nitrogen atom to which they are bonded for a heterocycle from the series (U-2), (U-3), (U-6), (U-22), (U-23 ), (U-24), (U-25), (U-26) or (U-27)
• U b independently of one another for halogen, cyano, nitro, C1-C4-alkyl or Ci-C4-alkoxy; and wherein the ring N atoms in U-25 are not substituted by halogen, nitro, cyano, Ci-C4-alkoxy, Ci-C4-haloalkoxy; m for 0 or 1
• R 2 stands for the substructure of the general formula -XYZ. It stands for the
• X is phenyl or pyridyl, unsubstituted or substituted by 1 to 3 R x ; it stands
• R x independently of one another represent halogen, cyano, or methyl
• R Y1 and R Y2 represent H, CH 3 or CH 2 CH 3 ;
• R zl is phenyl substituted with 1 to 4 R zn ; where 1 R zn is in the 2-position and each is standing R zn independently represent F, CI, Br, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , cyclopropyl, OCH 3 , OCH 2 CH 3 , OCH 2 CH 2 CH 3 , OCH (CH 3 ) 2 , CH 2 OCH 3, or CH (CH 3 ) OCH 3 ;
• R Z2 , R Z2a and R Z3 independently of one another represent H; or
• R Z21 independently of one another for halogen, cyano, Ci-C 3 -alkyl, C 3 -C 6 -cycloalkyl, Ci- C 3 -haloalkyl, Ci-C 3 -alkoxy, or Ci-C 3 -haloalkoxy;
• R a independently of one another for Ci-C 4 -alkyl or C 3 -C 6 -cycloalkyl, all of which can each be unsubstituted or can be monosubstituted up to 7 times by halogen and / or by one R f ;
• R b and R c independently of one another represent H; or for Ci-C 4 -alkyl or C 3 -C 4 -cycloalkyl, each unsubstituted or substituted with 1 to 3 R f ;
• R f independently of one another for halogen, cyano, nitro, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C 1 -C 4 -AI- kylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci -C 4 -alkylcarbonyl, Ci-C 4 -alkoxycarbonyl;
• R g independently of one another for halogen, cyano, nitro, Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci- C 4 -alkylthio, Ci-C 4 -alkylsulfinyl, C 1 -C 4 -alkyl kylsulfonyl;
• R h independently of one another for halogen, cyano, nitro, hydroxy, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -alkylsulfinyl, C 3 -C 6 - Cycloalkylsulfinyl, Ci-G t -alkylsulfonyl, C (Q ') NR b R c , N (R b ) C (Q') R a ; or for a heterocycle from the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1 , 3,4-oxadiazol
• Ar is phenyl, unsubstituted or substituted with 1 to 2 R ⁇ ; each R A independently of one another represents fluorine, chlorine, SFs, CF 3 , OCF 3 or OCF 2 CF 3 ;
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (R b ) OR a , -N (R b ) -CN, -N (R n ) C (0) R b , -N (R n ) C (0) NR b R c , -N (R n ) C (0) 0R a , - N (R n ) C (0) C (0) 0R a , -N (R n ) S0 2 R a , -N C (R b ) N (R b ) (R c ); it stands
• R n for H; or for methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, ethenyl, or propenyl, all of which can be unsubstituted or simply up to can be substituted three times with halogen and / or optionally with 1 R h ; or for a heterocycle selected from the series oxolan-3-yl, thietan-3-yl, oxetan-3-yl, all unsubstituted or substituted by one R g ;
• R 12 for H or represents methyl or ethyl
• R n and R 12 together with the nitrogen atom to which they are bonded represent a heterocycle from the series (U-3), (U-6) or (U-23);
• U b independently of one another represent fluorine, chlorine, methyl, ethyl, methoxy or ethoxy;
• m for 0.1 R 2 stands for the substructure of the general formula -XYZ. It stands
• R Y1 represents H or CH 3 ;
• R zl is phenyl substituted with 1 to 4 R zn ; where 1 R zn is in the 2-position and each is standing
• R zn independently represents F, CI, Br, CFb, CH 2 CH 3 , CH 2 CH 2 CH 3 , CF 1 (CF [ 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , cyclopropyl, OCH 3 , OCH 2 CH 3 , OCH 2 CH 2 CH 3 , OCH (CH 3 ) 2 or CH 2 OCH 3 ;
• R a independently of one another represent methyl, ethyl, n-propyl, iso-propyl or cyclopropyl, all of which may be unsubstituted, mono- to five-fold with halogen and / or optionally with an R f ;
• R b and R c independently of one another represent H; or for methyl, ethyl, n-propyl, iso-propyl or cyclopropyl, all each unsubstituted or substituted by 1 to 3 R f ;
• R f independently of one another represents fluorine, chlorine, cyano, methoxy or ethoxy
• R g independently of one another represent fluorine, chlorine, cyano, methoxy or ethoxy;
• R h independently of one another represents fluorine, chlorine, cyano, methoxy, ethoxy, NHCOCH3, NHCOCH2CH3.
• Ar is phenyl, unsubstituted or substituted with 1 to 2 R Ar ; each R A independently of one another represents fluorine, chlorine, SF5, CF 3 , OCF 3 or OCF 2 CF 3 ;
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (R b ) OR a , -N (R b ) -CN, -N (R n ) C (0) R b , -N (R n ) C (0) NR b R c , -N (R n ) C (0) 0R a , - N (R n ) C (0) C (0) 0R a , -N (R n ) S0 2 R a , -N C (R b ) N (R b ) (R c ); it stands
• R n for H; or for methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, ethenyl, or propenyl, all of which can be unsubstituted or simply to three times may be substituted with halogen and / or optionally with 1 or 2 R h ; or for a heterocycle from the series oxan-4-yl, oxolan-3-yl, thietan-3-yl, oxetan-3-yl, all unsubstituted or substituted by one R g ;
• R 12 for H; or for methyl or ethyl; or
• R n and R 12 together with the nitrogen atom to which they are bonded represent a heterocycle from the series (U-3), (U-6) or (U-23); It stands
• U b independently of one another represent fluorine, chlorine, methyl, ethyl, methoxy or ethoxy;
• m stands for 0 or 1 R 2 for the substructure of the general formula -XYZ. It stands
• X is phenyl or pyridyl, unsubstituted or substituted with 1 to 2 R x ; it stands
• R x independently of one another represent halogen, cyano, or methyl
• each R Y1 here represents H or CH 3 ;
• R Z1 is phenyl substituted with 1 to 4 R zn ; where 1 R zn is in the 2-position and each is standing
• R zn independently of one another for F, CI, Br, CH3, CH2CH3, CH2CH2CH3, CH (CH3) 2, CH2CH2CH2CH3, cyclopropyl, OCH 3 , OCH2CH3, OCH 2 CH 2 CH 3 , OCH (CH 3 ) 2 or CH2OCH3;
• R Z45 for CH 3 or C 2 H 5 ;
• R a independently of one another represent methyl, ethyl, n-propyl, iso-propyl or cyclopropyl, all of which may be unsubstituted, mono- to five-fold with halogen and / or optionally with an R f ;
• R b and R c independently of one another represent H; or for methyl, ethyl, n-propyl, iso-propyl or cyclopropyl, all each unsubstituted or substituted by 1 to 3 R f ;
• R f independently of one another represents fluorine, chlorine, cyano, methoxy or ethoxy
• R g independently of one another represent fluorine, chlorine, cyano, methoxy or ethoxy;
• R h independently of one another represent fluorine, chlorine, cyano, hydroxy, methoxy, ethoxy, NHCOCH 3 , NHCOCH 2 CH 3 , -SO 2 CH 3 .
• Highlighted (embodiment 6-1) are the compounds of the formula (I) in which Ar represents phenyl which is substituted in the 4-position by OCF3 or OCF2CF3;
• A is N or CR A ; it stands
• R 1 for -NR n R 12 , -N (CH 3 ) OCH 3 , -NH-CN, -NHC (0) CH 3 , -NHC (0) CH 2 CH 3 , -NHC (0) -cyelopropyl, - NHC (0) CHF 2 , -NHC (0) NHCH 3 , -NHC (0) 0CH 2 CH 3 , -NHC (0) C (0) 0CH 2 CH 3 , -NHSO2CH3, -NHSO2CH2CH3, -NHS0 2 -cyelopropyl , -NHSO2CHF2 or -N CHN (CH 3) (CH 3); it stands R n for H; or for methyl, ethyl, iso-propyl, cyclopropyl, cyclobutyl, 2- (acetamide) ethyl, 2-ethoxyethyl, oxolan-3-yl, thietan
• R 12 for H or represents methyl or ethyl
• R n and R 12 together with the nitrogen atom to which they are attached represent (U-3-1) or (U-23-1);
• R 2 stands for the substructure of the general formula -XYZ. It stands for the
• R zl is phenyl substituted with 1 to 2 R zn ; where 1 R zn is in the 2-position and each is standing
• RZ n independently of one another represent CH3 or iso-propyl R Z45 for CH3 or C2H5.
• A is N or CR A ;
• R A stands for H;
• R 1 for -NR n R 12 , -N (CH 3 ) OCH 3 , -NH-CN, -NHC (0) CH 3 , -NHC (0) CH 2 CH 3 , -NHC (0) -cyelopropyl, - NHC (0) CHF 2 , -NHC (0) NHCH 3 , -NHC (0) 0CH 2 CH 3 , -NHC (0) C (0) 0CH 2 CH 3 , -NHSO2CH3, -NHSO2CH2CH3, -NHS0 2 -cyciopropyl , -NHSO2CHF2 or -N CHN (CH 3) (CH 3); where R n stands for H; or for methyl, ethyl, iso-propyl, cyclopropyl, cyclobutyl, 2- (acetamide) ethyl,
• R 12 for H; or for methyl or ethyl; or
• R n and R 12 together with the nitrogen atom to which they are attached represent (U-3-1) or (U-23-1);
• R 2 stands for the substructure of the general formula -XYZ.
• X stands for phenyl unsubstituted or substituted by 1 to 2 R x or for pyrid-2-yl; it stands
• R x independently of one another represent fluorine, chlorine, cyano, or methyl
• R Y1 for H or CH 3 ;
• R Y2 for H;
• R ZI is phenyl substituted with 1 to 2 R zn ; where 1 R zn is in the 2-position and each is standing
• R zn independently of one another represent OCH3, CH3 or iso-propyl
• R Z45 for CH 3 or C 2 H 5 .
• the invention relates to compounds of the general formula (1-1) in which the structural elements Ar, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or those in configuration (3-1) or those in configuration (4-1) or those in configuration (5-1) or those in configuration (6-1) or those in configuration (4-2) or those in configuration (5-2) or have the meanings given in embodiment (6-2).
• the invention relates to compounds of the general formula (1-2) in which the structural elements Ar, R 1 , R Y1 and R Z1 in embodiment (1-1) or in embodiment (2-1) or those in configuration (3-1) or those in configuration (4-1) or those in configuration (5-1) or those in configuration (6-1) or those in configuration (4-2) or those in configuration ( 5-2) or have the meanings given in embodiment (6-2).
• the invention relates to compounds of the general formula (1-3) in which the structural elements Ar, R 1 , R Y1 and R Z1 in embodiment (1-1) or in embodiment (2-1) or those in configuration (3-1) or those in configuration (4-1) or those in configuration (5-1) or those in configuration (6-1) or those in configuration (4-2) or those in configuration (5-2) or have the meanings given in embodiment (6-2).
• the invention relates to compounds of the general formula (1-4) in which the structural elements Ar, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or those in configuration (3-1) or those in configuration (4-1) or those in configuration (5-1) or those in configuration (6-1) or those in configuration (4-2) or those in configuration ( 5-2) or have the meanings given in embodiment (6-2).
• the invention relates to compounds of the general formula (1-5) in which the structural elements Ar, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or those in configuration (3-1) or those in configuration (4-1) or those in configuration (5-1) or those in configuration (6-1) or those in configuration (4-2) or those in configuration ( 5-2) or have the meanings given in embodiment (6-2).
• the invention relates to compounds of the general formula (1-6) in which the structural elements Ar, R 1 and R 245 are those in embodiment (1-1) or in embodiment (2-1) or in Design (3-1) or those in design (4-1) or those in design (5-1) or those in design (6-1) or those in design (4-2) or those in design (5-2 ) or have the meanings given in embodiment (6-2).
• the compounds of the formula (I) can optionally also be present as stereoisomers, i.e. as geometrical 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, even if only compounds of the formula (I) are mentioned here in general.
• the optically active, stereoisomeric forms of the compounds of the formula (I) and their salts are preferably used according to the invention.
• the invention therefore relates to both the pure enantiomers and diastereomers and their mixtures for combating animal pests, including arthropods and in particular insects.
• the compounds of the formula (I) can optionally exist in various polymorphic forms or as a mixture of various polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
• alkyl either alone or in combination with other terms, such as haloalkyl, in the context of the present invention is a residue of a saturated, aliphatic hydrocarbon group with 1 to 12 Koh understood lenstoffatomen, which can be branched or unbranched.
• Ci-Ci2-alkyl radicals are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl , 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.
• CVC alkyl radicals are particularly preferred.
• Ci-C4-alkyl radicals are particularly preferred.
• alkenyl is a linear or branched C2-Ci2-alkenyl radical which has at least one double bond, for example vinyl, allyl , 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1 -Hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl.
• C2-C6-alkenyl radicals are preferred and C2-C4-alkenyl radicals are particularly preferred.
• alkynyl is a linear or branched C2-Ci2-alkynyl radical which has at least one triple bond, for example ethynyl, 1 -Propinyl and propargyl, understood.
• CVCV-alkynyl groups are preferred, and C3-C4-alkynyl groups are particularly preferred.
• the alkynyl radical can also have at least one double bond.
• cycloalkyl either alone or in combination with other terms, according to the invention is a C3-Cs-cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and Cyclooctyl understood. Of these, C3-C6 cycloalkyl radicals are preferred.
• aryl is understood according to the invention to mean an aromatic radical with 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthenyl, particularly preferably phenyl.
• arylalkyl is understood to mean a combination of radicals “aryl” and “alkyl” defined according to the invention, the radical generally being bonded via the alkyl group, examples of which are benzyl, phenylethyl or a- Methylbenzyl, benzyl being particularly preferred.
• hetaryl means a mono-, bi- or tricyclic heterocyclic group composed of carbon atoms and at least one heteroatom, at least one cycle being aromatic.
• the hetaryl group preferably contains 3, 4, 5 or 6 carbon atoms selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4- Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5- Triazinyl, benzofuranyl, benzisofuryl, benzothi
• heterocyclyl means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring made up of carbon atoms and at least one heteroatom in the ring.
• the heterocyclyl group preferably contains 3, 4, 5 or 6 carbon atoms and 1 or 2 heteroatoms from the group consisting of oxygen, sulfur or nitrogen.
• Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl.
• radicals substituted by halogen are understood to mean radicals halogenated once or several times up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be identical or different.
• Halogen here stands for fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
• alkoxy either on its own or in combination with other terms, such as haloalkoxy, is understood here to mean an O-alkyl radical, the term “alkyl” having the meaning given above.
• R 1 , A, R 2 , X, R Y1 , T and R Z1 have the meanings described above.
• a suitable solvent such as, for example, ethanol or methanol
• R 1 , A, X, R Y1 , R Z3 and R Z1 have the meanings described above.
• T stands for S.
• a base such as potassium carbonate or triethylamine
• a suitable solvent such as acetone or dichloromethane
• Compounds of general formula (Ie) can be prepared according to Figure 5 from isocyanates of general formula (V) and alcohols of general formula (V) in a suitable solvent, such as tetrahydrofuran, and at a suitable temperature, such as in a range of 40 ° C to 80 ° C.
• a suitable solvent such as tetrahydrofuran
• a suitable temperature such as in a range of 40 ° C to 80 ° C.
• Compounds of general formula (If) can be prepared from amines of general formula (VII) and 4-nitrophenylcarbamates of general formula (VIII) in the presence of a base such as cesium carbonate in a suitable solvent such as acetonitrile, and with a suitable temperature, such as in a range from 0 ° C to 40 ° C.
• a base such as cesium carbonate
• a suitable solvent such as acetonitrile
• Compounds of the general formula (If) can be prepared according to Figure 7 by first reacting amines of the general formula (VII) with 4-nitrophenoxyformic acid chloride in a suitable solvent such as tetrahydrofuran to give 4-nitrophenyl carbamates of the general formula (IX).
• Compounds of the general formula (IX) can then in a suitable solvent, such as, for example, acetonitrile, and at a suitable temperature, such as, for example, in a range from 0 ° C. to 40 ° C., with imines of the general formula (X) to give compounds of the general formula (If) are implemented.
• a suitable solvent such as, for example, acetonitrile
• a suitable temperature such as, for example, in a range from 0 ° C. to 40 ° C.
• a base such as pyridine
• suitable solvent such as chloroform
• a strong base such as sodium hydride
• Amines of the general formula (VIIb) can be prepared according to Figure 10.
• chlorotriazoles of the general formula (XII, A N) with amines of the general formula (XIII), optionally in the presence of a base such as pyridine, in a suitable solvent such as ethanol and at a suitable temperature, such as in a range implemented from 20 ° C to 60 ° C to compounds of the general formula (XIVb).
• a suitable reducing agent such as tin chloride in a suitable solvent such as ethanol at a suitable temperature such as in a range from 60 ° C. to 80 ° C. gives amines of the general formula (VIIb).
• L 1 and L 2 each represent Fl or together represent C (CFl3) 2-C (CF [3) 2
• Compounds of general formula (II) can be prepared according to Figure 11 by a Suzuki coupling between a bromine compound of general formula (XVI) and a boronic acid derivative of general formula (XVIIa) in the presence of a Pd catalyst, such as tetrakis (triphenylphosphine ) palladium and a base, such as sodium carbonate, in a suitable solvent, such as an ethanol-toluene mixture, 1,2-dimethoxyethane or dioxane, and at a suitable temperature, such as in a range from 60 ° C to 150 ° C , getting produced.
• a Pd catalyst such as tetrakis (triphenylphosphine ) palladium
• a base such as sodium carbonate
• a suitable solvent such as an ethanol-toluene mixture, 1,2-dimethoxyethane or dioxane
• a suitable temperature such as in a range from 60 ° C to 150 ° C
• Ar, A, R yl , X, R a and R b have the meanings described above.
• a base such as pyridine
• suitable solvent such as chloroform
• Ar, A, R yl , X, R a and R b have the meanings described above.
• Compounds of the general formula (IIf) can be prepared from compounds of the general formula (IIb 1 ) and carbonyl derivatives of the formula (XXVII) in a suitable solvent, such as ethanol or toluene, and at a suitable temperature, such as in a range of 50 ° C to 120 ° C.
• Ar, X and R b have the meanings described above.
• Pyrazoles of the general formula (Hg) can be prepared according to Figure 15 by first adding Flydrazines of the general formula (XXIX) with cyanoketones of the general formula (XXXIV) in a suitable solvent, such as, for example, methanol, and at a suitable reaction temperature, such as, for example, at 0 ° to 60 ° C., to give pyrazoles of the general formula (XXXV).
• a suitable solvent such as, for example, methanol
• a suitable reaction temperature such as, for example, at 0 ° to 60 ° C.
• Bromotriazoles of the general formula (XVIa) can, according to Figure 16, by nucleophilic substitution starting from the dibromotriazoles of the general formula (XVIII) and an amino compound such as ammonia, a primary or secondary aliphatic amine or a Fleterocycle with free NF1 such as pyrazole, if appropriate by adding a base such as potassium carbonate in a suitable solvent such as ethanol and at a suitable temperature such as in a range from 20 ° C to 100 ° C.
• a base such as potassium carbonate
• a suitable solvent such as ethanol
• Bromotriazoles of the general formula (XVIb) can, according to Figure 17, starting from dibromotriazoles of the general formula (XXI) and a compound of the general formula (XXVI) in the presence of a palladium catalyst, such as, for example, tris (dibenzylidenactone) dipalladium in a suitable solvent such as dioxane, and at a suitable temperature, such as in a range from 50 ° C to 120 ° C.
• a palladium catalyst such as, for example, tris (dibenzylidenactone) dipalladium in a suitable solvent such as dioxane
• Ar and R 1 have the meanings described above.
• Bromotriazoles of the general formula (XVIc) can be prepared according to Figure 18 by reacting dibromotriazoles of the general formula (XXI) and a sulfonamide of the general formula (XXV) in the presence of a base such as potassium carbonate in a suitable solvent such as dimethyl formamide, and with suitable temperature, such as in a range of 60 ° C to 120 ° C, can be prepared.
• a base such as potassium carbonate
• suitable solvent such as dimethyl formamide
• Ar, A, R b and R c have the meanings described above.
• Heteroaryl bromides of the general formula (XVId) can be prepared according to Figure 19 by reacting compounds of the general formula (XVIa), where R a and R b are hydrogen and an acetal of the general formula (XXVI) in a suitable solvent such as toluene and at a suitable temperature, such as in a range from 0 ° C to 120 ° C.
• Dibromotriazoles of the general formula (XXI) can according to Figure 20 in analogy to WO 2011/006903 from dibromotriazole and an arylboronic acid of the general formula (XXVIII) in the presence of a copper catalyst, such as copper (II) acetate and a base, such as Pyridine, in a suitable solvent, such as toluene, and at a suitable temperature, such as in a range from 20 ° C to 120 ° C.
• a copper catalyst such as copper (II) acetate and a base, such as Pyridine
• a suitable solvent such as toluene
• Chlorotriazoles of the general formula (XII) can be prepared according to Figure 21 by first adding hydrazines of the general formula (XXIX) with carboxylic acids of the general formula (XXX) in a suitable solvent, such as, for example, water to give hydrazones of the general formula (XXXI) are implemented.
• Iminothiazolidinones of the general formula (X) are known from the literature or can be obtained in analogy to methods known from the literature (cf. e.g. US 2014/0274688 or WO 2016/033025)
• the compounds of the formula (I) can exist as geometrical and / or optically active isomers or corresponding isomer mixtures in different compositions.
• These stereoisomers are, for example, enantiomers, diastereomers, atropiso mers or geometric isomers.
• the invention thus comprises both pure stereoisomers and any mixtures of these isomers.
• the invention also relates to methods for combating animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat.
• the control of animal pests is preferably carried out in agriculture and forestry and in material protection. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are carried out on the human or animal body.
• the invention also relates to the use of the compounds of the formula (I) as pest control agents, in particular crop protection agents.
• pesticides always also includes the term pesticides.
• the compounds of the formula (I) are suitable for protecting plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the harvested material and for controlling animal pests, especially insects, if they are well tolerated by plants, have a favorable warm-blooded toxicity and are environmentally friendly , Arachnids, helminths, in particular nematodes, and mollusks, which occur in agriculture, horticulture, animal breeding, aquaculture, forests, gardens and leisure facilities, in the protection of stocks and materials and in the hygiene sector.
• the term “hygiene” is to be understood to mean that any and all measures, regulations and procedures are meant, the aim of which is to prevent diseases, in particular infectious diseases, and which serve to improve the health of To protect people and animals and / or to protect the environment and / or to maintain cleanliness.
• this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that they are free from hygiene pests and / or their excretions.
• Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, on the human body or Treatment regulations to be applied to the bodies of animals and diagnostic regulations that are carried out on the human body or the bodies of animals.
• honeygiene sector thus covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, Hotels, hospitals, stables, animal facilities, etc.
• Hygiene pest should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons. It is therefore a primary objective to avoid or minimize the presence of and / or exposure to hygiene pests in the hygiene sector. This can be achieved in particular through the use of a pesticide that can be used both to prevent an infestation and to cope with an existing infestation. Preparations can also be used that prevent or reduce exposure to pests.
• Hygiene pests include, for example, the organisms mentioned below.
• the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
• the pests mentioned above include:
• Pests from the Arthropoda tribe in particular from the Arachnida class, e.g. B. Acarus spp "e.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp “Aculus spp” z.
• Panonychus citri Metatetranychus citri
• Panonychus ulmi Metatetranychus ulmi
• Phyllocoptruta oleivora Platytetranychus multidigituli
• Polyphagotarsonemus latus Psoroptes spp.
• Rhipicephalus spp. Rhipicephalus spp.
• Rhhipicephalus spp. Rhhipicephalus spp.
• Rhhipicephalus spp. Rhhipicephalus m .
• Steneotarsonemus spinki Tarsonemus spp.
• E.g. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp. E.g.
• B. Blaniulus guttulatus from the class of the Insecta, e.g. B. from the order of the Blattodea z.
• B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera, e.g. B.
• Anoplophora glabripennis Anthonomus spp., E.g. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., E.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. B. Bruchus pisorum, Bruchus rufimanus, Casida spp., Cerotoma trifurcata, Ceutorrhynchus spp., E.g.
• Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spnap., Dicladispa armi gerus sp., Dicladispa armi gerus sp .
• B. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. B.
• Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hete ronyx spp., Hyperlia, Hop argentea, Hylamorpha elegica, Hylamorpha. Hypomeces squa musus, Hypothenemus spp., E.g. B.
• hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Z. B.
• Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus ( Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., Z.
• Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g. B.
• Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Oti orhynchus sulcatus, Oulema spp., E.g. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. B.
• Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. B. Zabrus tenebrioides; from the order of the Dermaptera z.
• Aedes spp. E.g. B.
• Bactrocera cucurbitae Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya.
• Delia antiqua Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Droso phila spp., E.g. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hippobosca spp., Liriomyza spp., E.g. B.
• Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonosca spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., E.g. B.
• Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Z. B.
• Myzus ascalonicus Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., E.g. B.
• Nephotettix cincticeps Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B.
• Pemphigus bursarius Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
• Planococcus citri Pro- sopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z.
• Pseudococcus calceolariae Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Z. B.
• Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., Z. B.
• Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Z. B.
• Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., Z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezo dorus spp., E.g. B.
• Piezodorus guildinii Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera, for. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., E.g. B.
• Diprion similis, Hoplocampa spp. E.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. B.
• Vespa crabro Wasman- nia auropunctata, Xeris spp. ; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera e.g. B. Coptotermes spp., E.g. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontermes spp., Porotermes spp., Reticulitermes spp., E.g. B.
• Reticulitermes flavipes Reticulitermes hespe rus; from the order of the Lepidoptera, for.
• Euproctis chrysorrhoea Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., E.g. B. Heliothis virescens, Hepialus spp., E.g. B.
• Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., Z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., E.g. B.
• Scirpophaga spp. E.g. B. Scirpophaga innotata, Ontario segetum, Sesamia spp., E.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. B.
• Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of the Orthoptera or Saltatoria z.
• B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., E.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. B. Locusta migratoria, Melanoplus spp., E.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B.
• Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera, for.
• Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., E.g. B.
• Ctenolepisma spp. Fepisma saccharina, Fepismodes inquilinus, Thermobia domestica; from the class of the Symphyla z.
• B. Scutigerella spp. E.g. B. Scutigerella immaculata;
• Pests from the trunk of the Mollusca e.g. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., E.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. B. Deroceras laeve, Galba spp., Fymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
• Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. B. Cacopaurus pestis, Criconemella spp., E.g. B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. B.
• Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. B.
• the compounds of the formula (I) can optionally also be used in certain concentrations or application quantities as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids ) or as a remedy against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
• the present invention further relates to formulations, in particular formulations for controlling undesired animal pests.
• the formulation can be applied to the animal pest and / or in its habitat.
• the formulation according to the invention can be provided to the end user as a ready-to-use "application form", i.e. the formulations can be applied directly to the plants or seeds by means of a suitable device such as a spray or dust device.
• the formulations can be provided to the end user in the form of concentrates to be diluted, preferably with water, before use.
• formulation denotes such a concentrate
• application form denotes a ready-to-use solution for the end user, i.e. usually such a diluted formulation.
• the formulation of the invention can be prepared in a conventional manner, for example by mixing the compound of the invention with one or more suitable excipients such as those disclosed herein.
• the formulation comprises at least one compound according to the invention and at least one economically useful adjuvant, e.g. carrier and / or surfactant (s).
• at least one economically useful adjuvant e.g. carrier and / or surfactant (s).
• a carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert.
• the carrier generally improves the application of the compounds, for example to plants, parts of plants or seeds.
• suitable solid supports include, but are not limited to, ammonium salts, in particular ammonium sulfates, ammonium phosphates and ammonium nitrates, ground natural rock such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel, and ground synthetic Rocks such as finely divided silica, alumina and silicates.
• suitable solid carriers for the production of granules include, but are not limited to, cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours, and granules of organic materials such as paper , Sawdust, coconut shells, corn on the cob and tobacco stalks.
• suitable liquid carriers include, but are not limited to, water, organic solvents and Combinations thereof.
• suitable solvents include polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, Chlorethylene or methylene chloride), alcohols and polyols (which can also be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ke tone (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), Esters (including fats and oils) and (poly) ethers, unsubstituted and substituted
• the carrier can also be a liquefied gaseous extender, ie a liquid which is gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
• a liquefied gaseous extender ie a liquid which is gaseous at normal temperature and under normal pressure
• aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
• Preferred solid supports are selected from clays, talc and silica.
• Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones and (poly) ethers.
• the amount of carrier is typically in the range of 1 to 99.99% by weight, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight and most preferably 20 to 99% by weight. -% of the formulation.
• Liquid carriers are typically present in a range of 20 to 90%, for example 30 to 80% by weight of the formulation.
• Solid carriers are typically present in a range of 0 to 50%, preferably 5 to 45%, for example 10 to 30% by weight of the formulation.
• the areas outlined relate to the total amount of carrier.
• the surfactant can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant such as ionic or nonionic emulsifiers, foaming agents, dispersants, wetting agents, penetration promoters and any mixtures thereof.
• surfactants close, although this is not limiting, salts of polyacrylic acid, ethoxylated poly (alpha- substituted) acrylate derivatives, salts of lignosulphonic acid (such as sodium lignosulphonate), salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols, fatty acids or fatty amines (for example polyoxyethylene fatty acid esters, for example polyoxyethylene fatty acid esters, for example ricinus oiloxyethoxylate, polyglycol ethers, e.g.
• substituted phenols preferably alkylphenols or arylphenols
• fatty acid esters of polyols such as fatty acid esters of glycerol, sorbitol or sucrose
• sulfates such as alkyl sulfates
• alkyl ether sulfates Sulfonates (for example alkyl sulfonates, aryl sulfonates and alkylbenzenesulfonates), sulfonated polymers of naphthalene / formaldehyde, phosphate esters, protein hydrolyzates, fignosulfite waste liquors and methyl cellulose.
• salts in the present paragraph this preferably refers to the alkali, alkaline earth and ammonium salts concerned
• Preferred surfactants are selected from ethoxylated poly (alpha-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde, polyoxyethylene fatty acid esters such as ricinus oil ethoxylate, sodium lignosulfonate, sodium lignosulfonate.
• the amount of surfactant is typically in the range of 5 to 40%, for example 10 to 20% by weight of the formulation.
• auxiliaries include water-repellent substances, drying agents, binders (adhesives, adhesives, fixing agents such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or fatices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and fecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, e.g. the products available under the name Bentone, and finely divided silicon dioxide), stabilizers (e.g.
• cold stabilizers preservatives (e.g. dichlorophemonic, benzyl alcohol , l, 2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light protection agents, especially UV protection agents, and other agents that improve the chemical and / or physical stability), dyes or Pigments (such as a organic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoam agents (e.g.
• silicone antifoam and magnesium stearate silicone antifoam and magnesium stearate
• antifreeze adhesives
• gibberellins and processing aids mineral and vegetable oils
• fragrances waxes
• nutrients including trace nutrients such as iron salts, Manganese, boron, copper, cobalt, molybdenum and zinc
• protective colloids including protective colloids, thixotropic substances, penetrants, sequestering agents and complexing agents.
• auxiliaries depends on the intended use of the compound according to the invention and / or on the physical properties of the compound (s). Furthermore, auxiliaries can be chosen so that they match the formulations or the use forms produced therefrom give certain properties (technical, physical and / or biological properties). The selection of auxiliaries may make it possible to adapt the formulations to specific needs.
• the formulation comprises an insecticidally / acaricidally / nematicidically effective amount of the compound (s) according to the invention.
• effective amount denotes an amount which is sufficient to control harmful insects / mites / nematodes on cultivated plants or for material protection and which does not significantly damage the treated plants. Such an amount can vary within a wide range and depends on various factors such as the insect / mite / nematode species to be controlled, the cultivated plant or material treated, the climatic conditions and the particular compound according to the invention used.
• the formulation according to the invention usually contains 0.01 to 99% by weight, preferably 0.05 to 98% by weight, particularly preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight %, most preferably 1 to 80% by weight of the compound according to the invention. It is possible for a formulation to comprise two or more compounds according to the invention. In such a case, the areas outlined relate to the total of the compounds of the present invention.
• the formulation according to the invention can be in any conventional formulation type, such as solutions (e.g. aqueous solutions), emulsions, suspensions based on water and oil, powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, granules) ), Suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers and also microencapsulations in polymeric substances.
• the compound according to the invention can be in suspended, emulsified or dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g.
• SF, FS dispersion concentrates
• DC suspensions and suspension concentrates
• emulsion concentrates e.g. EC
• emulsions e.g. EW, EO, ES, ME, SE
• capsules e.g. CS, ZC
• pastes lozenges, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressed parts (e.g. BR, TB, DT), granulates (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g.
• the formulation according to the invention is preferably in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.
• surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate
• organic solvent e.g. aromatic hydrocarbon or fatty acid amide
• dissolved additional water-soluble solvent so that one comes to a total amount of 100 wt .-%.
• An emulsion is obtained by diluting with water. iv) emulsions (EW, EO, ES)
• wt .-% of at least one compound according to the invention and 1-10 wt .-% surfactant for example a Mi mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols
• surfactant for example a Mi mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols
• water-insoluble organic solvent e.g. aromatic hydrocarbon
• a suitable grinding device e.g. B. a ball mill
• 20-60 wt .-% of at least one inventive compound with the addition of 2-10 wt .-% surfactant (eg sodium lignosulfonate and Polyoxyethylene fatty alcohol ether), 0.1-2 wt .-% thickener (eg xanthan) and water comminuted to a fine active ingredient suspension.
• the water is added in such an amount that a total amount of 100% by weight is obtained.
• a stable suspension of the active ingredient is obtained by diluting with water.
• binders eg polyvinyl alcohol
• a suitable milling device for example a ball mill, 20-60% by weight of at least one compound according to the invention with the addition of 2-10% by weight of surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight Thickening agent (for example modified clay, especially bentone, or silicon dioxide) and an organic carrier comminuted to a fine active ingredient-oil suspension.
• surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
• Thickening agent for example modified clay, especially bentone, or silicon dioxide
• organic carrier for example modified clay, especially bentone, or silicon dioxide
• ком ⁇ онент 1-90% by weight, preferably 20-80% by weight, most preferably 50-80% by weight, of at least one compound according to the invention are finely ground with the addition of a surfactant (eg sodium lignosulfonate and sodium alkylnaphthylsulfonate) and optionally carrier material and converted into water-dispersible or water-soluble granules by means of typical technical applications such as extrusion, spray drying, fluidized bed granulation.
• surfactant and carrier material are used in such an amount that a total amount of 100% by weight is obtained.
• a stable dispersion or solution of the active ingredient is obtained by diluting with water.
• Water-dispersible powders and water-soluble powders WP, SP, WS
• a rotor-stator mill with 1-20% by weight of surfactant (e.g. sodium lignosulphonate, sodium alkylnaphthylsulphonate) and an amount of solid support, e.g. silica gel, such that a total of 100% by weight is obtained, ground.
• surfactant e.g. sodium lignosulphonate, sodium alkylnaphthylsulphonate
• solid support e.g. silica gel
• 5-25% by weight of at least one compound according to the invention with the addition of 3-10% by weight surfactant (eg sodium lignosulfonate), 1-5% by weight binder (eg carboxymethyl cellulose) and such an amount of water so that a total amount of 100% by weight is comminuted.
• surfactant eg sodium lignosulfonate
• binder eg carboxymethyl cellulose
• microemulsion (ME) 5-20% by weight of at least one compound according to the invention becomes 5-30% by weight of organic solvent mixture (e.g. fatty acid dimethylamide and cyclohexanone), 10-25% by weight of surfactant mixture (e.g.
• An oil phase with 5-50% by weight of at least one compound according to the invention, 0-40% by weight of water-insoluble organic solvent (eg aromatic hydrocarbon), 2-15% by weight of acrylic monomers (eg methyl methacrylate, methacrylic acid and a Di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol).
• a radical polymerisation initiated with a radical initiator leads to the formation of poly (methy) acrylate microcapsules.
• a 5-50% by weight of at least one compound according to the invention, 0-40% by weight of water-insoluble organic solvent (for example aromatic hydrocarbon) and an isocyanate monomer (for example diphenylmethene-4,4'-diisocyanate) is used in an aqueous oil phase Solution of a protective colloid (e.g. polyvinyl alcohol) dispersed, this leads to the formation of polyurea microcapsules.
• a protective colloid e.g. polyvinyl alcohol
• a polyamine e.g. hexamethylenediamine
• the monomers make up 1-10% by weight of the total CS formulation.
• At least one compound according to the invention is finely ground and intimately mixed with such an amount of solid carrier, e.g. finely divided kaolin, that a total amount of 100% by weight is obtained.
• solid carrier e.g. finely divided kaolin
• Formulation types i) to xiii) can contain further auxiliaries such as 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoam agents, 0.1-1% by weight of dyes and / or pigments and 5- 10 wt .-% include antifreeze.
• the compounds of the formula (I) can also be used as a mixture with one or more suitable Fungi cides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, flerbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or the Plant growth regulators can be used so as to B. to broaden the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent repellence or to prevent the development of resistance. Furthermore, such active ingredient combinations can promote plant growth and / or tolerance to abiotic factors such. B. high or low tempe temperatures, against drought or against increased water or soil salt content.
• the flowering and fruiting behavior can also be improved, germination and rooting can be optimized, harvesting easier and yield increased, ripening can be influenced, the quality and / or nutritional value of the harvested products can be increased, the shelf life can be extended and / or the workability of the harvested products can be improved .
• the compounds of the formula (I) can be present as a mixture with further active ingredients or semi-chemicals, such as attractants and / or bird repellants and / or plant activators and / or growth regulators and / or fertilizers.
• the compounds of the formula (I) can also be used to improve the plant properties such as, for example, growth, yield and quality of the harvested material.
• the compounds of the formula (I) are in the formulations or in the use forms prepared from these formulations as a mixture with further compounds, preferably those as described below.
• the active ingredients named here with their “Common Name” are known and described, for example, in the pesticide manual (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be researched on the Internet (e.g. http: //www.alanwood .net / pesticides).
• the classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.
• Acetylcholinesterase (AChE) inhibitors preferably carbamates selected from alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfane, ethiofencarb, fenobucarb, meta-foncarb, isocyanate carbide, isopathiocarbomide Oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorpyrumephosphos, chlorpyrumephosphos, chlorpyrifaphosphos, chlormephaphos-methyl phos, Demet
• GABA-controlled chloride channel blockers preferably cyclodiene organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiprole) selected from ethiprole and fipronil.
• Sodium channel modulators preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin , beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cy- phenothrin [(lR) -trans-isomer], deltamethrin Empenthrin [(EZ) - (lR) -isomer
• nAChR nicotinic acetylcholine receptor
• neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine
• sulfoximines selected from sulfupoxafloride, or sulfoximines , or mesoionics selected from triflumezopyrim.
• Allosteric modulators of the nicotinic acetylcholine receptor preferably Spinosynes selected from Spinetoram and Spinosad.
• Allosteric modulators of the glutamate-dependent chloride channel preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.
• Juvenile hormone mimetics preferably juvenile hormone analogs selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
• Various non-specific (multi-site) inhibitors preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin or sulfuryl fluoride or borax or tartrate or methyl isocyanate producers selected from diazomet and metam.
• TRPV channel modulators of chordotonal organs preferably pyridinazomethanes, selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene.
• CHS1-related mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole.
• Microbial disruptors of the insect intestinal membrane selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. -Plant proteins selected from CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab 1/35 Abi.
• Inhibitors of mitochondrial ATP synthase preferably ATP disruptors selected from di-afenthiuron, or organotin compounds selected from azocyclotine, cyhexatin and fenbutatin oxide, or propargite or tetradifon.
• Blocker of the nicotinic acetylcholine receptor channel selected from bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium.
• CHS1-related inhibitors of chitin biosynthesis preferably benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, fufenuron, novaluron, noviflumuron, teflubenzuron and triflubenzuron.
• Inhibitors of chitin biosynthesis type 1 selected from buprofezin.
• molting disruptor especially in diptera, i.e. bifurcated selected from cyromazine.
• Ecdysone receptor agonists preferably diacylhydrazines, selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
• Octopamine receptor agonists selected from amitraz.
• Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.
• Mitochondrial complex I electron transport inhibitors preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad and tolfenpyrad, or Rotenone (Derris).
• Blockers of the voltage-dependent sodium channel preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumiz.on.
• Inhibitors of acetyl-CoA carboxylase preferably tetronic and tetramic acid derivatives, selected from Spirodiclofen, Spiromesifen, Spiropidion and Spirotetramat.
• Inhibitors of mitochondrial complex IV electron transport preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.
• Inhibitors of mitochondrial complex II electron transport preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.
• Ryanodine receptor modulators preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.
• Allosteric modulators of the GABA-dependent chloride channel preferably meta-diamide selected from broflanilide or isoxazole selected from fhixametamide.
• Baculoviruses preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedro viruses (NPVs) selected from Anticar sia gemmatalis MNPV and Helicoverpa armigera NPV.
• GVs granuloviruses
• NPVs nucleopolyhedro viruses
• All of the above-mentioned mixing partners of classes (1) to (15) can, if they are capable of doing so on the basis of their functional groups, form salts with suitable bases or acids. All of the fungicidal mixture partners mentioned in classes (1) to (15) can optionally include tautomeric forms.
• Inhibitors of ergosterol biosynthesis for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamide, (1.005) fenpropidine, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, ( 1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triad
• Inhibitors of the respiratory chain at complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008 ) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS , 4SR, 9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R
• Inhibitors of the respiratory chain at complex III for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008 , (3.009) famoxadon, (3.010) fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018 ) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(1E) -l- (3- ⁇ [(
• inhibitors of mitosis and cell division for example (4.001) carbendazim, (4.002) diethofencarb,
• Inhibitors of ATP production for example (8.001) Silthiofam.
• Inhibitors of cell wall synthesis for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalat, (9.008) (2E) - 3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3 - (4-tert-Butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one.
• Inhibitors of lipid and membrane synthesis for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.
• Inhibitors of melanin biosynthesis for example (11.001) tricyclazole, (11.002) ⁇ 3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamic acid 2,2,2-trifluoroethyl ester.
• Inhibitors of nucleic acid synthesis for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
• Inhibitors of signal transmission for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) procinazid, (13.005) quinoxyfen, (13.006) vinclozoline.
• fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamid, (15.011) flutianil, (15.012) fosetyl-aluminum, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline,
• 1,4-benzoxazepine (15,055) ⁇ 6 - [( ⁇ [(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino ⁇ oxy) methyl] pyridin-2-yl ⁇ but-3-yn-1-yl carbamic acid, (15.056) (2Z) -3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.057) phenazine-1-carboxylic acid, (15.058) 3,4,5- Propyl trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinoline-8-olsulfate (2: 1), (15.061) ⁇ 6 - [( ⁇ [(1-methyl-1H-tetrazol-5-yl) (phe - nyl) methylen] amino ⁇ oxy) methyl] pyridin-2-yl ⁇ carbamic acid tert-butyl ester
• the compounds of formula (I) can be combined with biological pesticides.
• Bio pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products that were formed by microorganisms, including proteins and secondary metabolic products.
• Biological pest control agents include bacteria such as spore-forming bacteria, root-settling bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides. Examples of such bacteria that are or can be used as biological pesticides are:
• Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No.
• NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thurin giensis subsp. aizawai, especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
• fungi and yeasts that are or can be used as biological pest control agents are:
• Beauveria bassiana especially strain ATCC 74040, Coniothyrium minitans, especially strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., Especially strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii) , in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowiafructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
• Paecilomyces lilacinus especially P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, especially strain VI 17b, Trichoderma atroviride, especially strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
• viruses that are or can be used as biological pest control agents are:
• Adoxophyes orana (apple peel moth) granulosic virus (GV), Cydia pomonella (codling moth) granulosic virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (sugar beet owl) mNPerwurm (HeVerda frug) Spodoptera littoralis (African cotton worm) NPV.
• Bacteria and fungi are also included, which are added to plants or plant parts or plant organs as "inoculants” and which, through their special properties, promote plant growth and plant health. Examples are: Agrobacterium spp. , Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monospora, Laccobacpillus, Lacci spp., Glomus spp.
• Agrobacterium spp. Azorhizobium caulinodans
• Azospirillum spp. Azotobacter spp.
• Bradyrhizobium spp. Bradyrhizobium spp.
• Paraglomus spp. Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp ..
• plant extracts and such products that were formed by microorganisms including proteins and secondary metabolic products that are or can be used as biological pesticides are:
• the compounds of the formula (I) can be combined with safeners, such as, for example, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamid, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Fluorazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), Mefenpyr (diethyl), naphthalic anhydride, oxab- etrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) - l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (
• Plants are understood here as meaning all plants and parts of plants, such as desired and undesired wild plants or cultivated plants (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soy, potato, sugar beet, sugar cane , Tomatoes, peppers, cucumber, melon, carrots, watermelon, onions, lettuce, spinach, leeks, beans, Brassica oleracea (e.g. cabbage) and other vegetables, cotton, tobacco, rape, and fruit plants (with the fruits apples , Pears, citrus fruits and grapes).
• Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those which can or cannot be protected by plant variety rights Plant varieties.
• Plants should be understood to mean all stages of development such as seeds, cuttings, young (immature) plants up to mature plants.
• Plant parts are to be understood as meaning all above-ground and subterranean parts and organs of plants such as shoot, leaf, flower and root, with leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes being listed as examples will.
• the plant parts also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.
• the treatment according to the invention of the plants and parts of plants with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the living space or the storage room by the customary treatment methods, e.g. B. by immersion, spraying, evaporation, misting Ver, scattering, brushing on, injecting and with propagation material, especially in seeds, further through single or multilayer wrapping.
• customary treatment methods e.g. B. by immersion, spraying, evaporation, misting Ver, scattering, brushing on, injecting and with propagation material, especially in seeds, further through single or multilayer wrapping.
• plants and their parts can be treated according to the invention.
• plant species and plant cultivars occurring in the wild or obtained by conventional biological breeding methods such as crossing or protoplast fusion, as well as their parts are treated.
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
• the term “parts” or “parts of plants” or “plant parts” has been explained above. Particular preference is given to treating the plants according to the invention of the plant varieties which are commercially available or in use.
• Plant cultivars are understood to be plants with new properties (“traits”) that have been obtained through conventional breeding, mutagenesis or recombinant DNA techniques. These can be varieties, races, bio and genotypes.
• the compounds of formula (I) can advantageously be used for treating transgenic plants, plant cultivars or plant parts which have received genetic material which gives these plants, plant cultivars or plant parts advantageous and / or useful properties (traits). It is therefore contemplated to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof.
• insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome results in a transgenic event.
• the insertion creates a new DNA sequence, which is referred to as an "event" and which is identified by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to the inserted DNA / the inserted DNA flanking at both ends .
• traits or transgenic events include, although this is not limiting, resistance to pests, water utilization efficiency, yield performance, drought tolerance, Seed quality, improved nutrient quality, hybrid seed production and herbicide tolerance, the trait being measured in relation to a plant lacking such a trait or transgenic event.
• Such advantageous and / or useful properties are better plant growth, vitality, stress tolerance, stability, resistance to storage, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased flowering capacity, easier harvest, acceleration of ripeness, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products and increased resistance or tolerance towards animals and microbial pests such as against insects, arachnids, nematodes, mites and snails.
• microbial pests such as against insects, arachnids, nematodes, mites and snails.
• Bt-Cry or VIP proteins which include CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof, and also hybrids or combinations thereof, in particular the CrylF protein or hybrids derived from a CrylF protein (for example hybrid Cryl A-CrylF proteins or toxic fragments thereof), the proteins of the CrylA type or toxic fragments thereof, preferably the CrylAc Protein or hybrids derived from the CrylAc protein (e.g.
• cry proteins as described in WO2001 / 47952, the insecticidal proteins from Xenorhabdus (as described in WO98 / 50427), Serratia (in particular from S. entomophila) or strands of the Photorhabdus species, such as Tc proteins from Photorhabdus, as described in WO98 / 08932.
• Serratia in particular from S. entomophila
• Tc proteins from Photorhabdus
• This also includes all variants or mutants of one of these proteins which differ in some amino acids (1-10, preferably 1-5) from any of the above-mentioned sequences, in particular the sequence of their toxic fragment, or which are linked to a transit peptide such as a plastid transit peptide or other protein or peptide are fused.
• herbicides for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin.
• DNA sequences coding for proteins that give the transformed plant toes and plants tolerance properties to certain herbicides in particular the bar or PAT gene or the Streptomyces coelicolor gene, which is shown in WO2009 / 152359 and which confers tolerance to glufonsin herbicides, a gene which codes for a suitable EPSPS (5-enolpyruvylshikimate-3-phosphate synthase), tolerance to herbicides with EPSPS as a target, in particular herbicides such as glyphosate and its salts , ver lent, a gene coding for glyphosate N-acetyltransferase or a gene coding for glyphosate oxoreductase can be mentioned.
• EPSPS 5-enolpyruvylshikimate-3-phosphate syntha
• herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. W02007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g. US Pat. No. 6,855,533), genes coding for 2,4-D-monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and genes coding for dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).
• ALS acetolactate synthase
• W02007 / 024782 e.g. W02007 / 024782
• a mutated Arabidopsis ALS / AHAS gene e.g. US Pat. No. 6,855,533
• Particularly useful transgenic events in transgenic plants or plant cultivars that can preferably be treated according to the invention include Event 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); Event 1445 (cotton, herbicide tolerance, not backed up, described in US-A 2002-120964 or WO2002 / 034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010 / 117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005 / 103266 or US-A 2005-216969); Event 300
• Event BLR1 rape, restoration of male sterility, deposited as NCIMB 41193, described in W02005 / 074671
• Event CE43-67B cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006 / 128573
• Event CE44-69D cotton, insect control, not deposited, be described in US-A 2010- 0024077
• Event CE44-69D cotton, insect control, not deposited, described in WO2006 / 128571
• Event CE46-02A cotton, insect control, not deposited, described in WO2006 / 128572
• Event COT102 cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986
• Event COT202 cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479
• Event COT203 cotton,
• PTA-11041) optionally stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55 (WO2011 / 063413A2), Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA-10442, W02011 / 066360A1), event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA- 10442, WO2011 / 066384A1), Event DP-040416-8 (maize, insect control, ATCC accession no. PTA-11508, WO2011 / 075593A1), Event DP-043A47-3 (maize, insect control, ATCC accession no.
• transgenic events are also provided by the United States Department of Agriculture’s (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov. The status of this list as it was on the filing date of the present application is relevant for the present application.
• USDA United States Department of Agriculture
• APIHS Animal and Plant Health Inspection Service
• transgenic plants which confer the desired characteristics in question can also be present in combinations with one another in the transgenic plants.
• transgenic plants that are mentioned are important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed being particularly emphasized.
• Traits that are particularly emphasized are the increased resistance of plants to insects, arachnids, nematodes and snails as well as the increased resistance of plants to one or more herbicides.
• plants, plant parts or plant seeds which can preferably be treated according to the invention, include commercially available products such as plant seeds, which are under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2 YIELD®-, YIELDGARD®-, ROUNDUP READY® 2 XTEN D TM -, INTACTA RR2 PRO®-, VISTIVE GOLD®- and / or XTENDFLEX TM trade names are sold or distributed.
• plant seeds which are under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2
• the treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their surroundings, habitat or storage room by the customary treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, watering (drenching), drip irrigation and in the case of propagation material, especially in the case of seeds, also by dry dressing, wet dressing, slurry dressing, Encrusting, single-layer or multilayer coating, etc. It is also possible to apply the compounds of the formula (I) by the ultra-low-volume process or to apply the application form or the compound of the formula (I) to the soil itself inject.
• a preferred direct treatment of the plants is foliar application; H. the compounds of formula (I) are applied to the foliage, the frequency of treatment and the amount applied should be tailored to the infestation pressure of the pest in question.
• the compounds of the formula (I) also get into the plants via the root system.
• the plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (e.g.
• the compounds of the formula (I) according to the invention are introduced into the site of the plants in solid form (for example in the form of granules) or by drop application (often also referred to as "chemigation"), ie the compounds of the formula according to the invention (I) are introduced by means of surface or underground drip pipes over certain periods of time together with varying amounts of water at defined points near the plants. This can also be done with water rice crops by metering the compound of the formula (I) in a solid use form (for example as granules) into a flooded rice field.
• the compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite farming, precision farming or precision farming.
• models support the site-specific management of agricultural facilities with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, Satellite data, yield, etc., with the aim of optimizing profitability, sustainability and environmental protection.
• such models can help to optimize agronomic decisions, control the precision of pesticide applications and record the work carried out.
• the compounds according to the invention can be applied to a crop plant according to an appropriate application protocol if the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound according to the invention to the crop plant.
• the compounds according to the invention can also be used in combination with a smart sprayer, such as a device for spot spraying or precision spraying, on a farm vehicle such as a tractor, a robot, a helicopter, an aircraft, an unmanned aerial vehicle (UAV) such as a drone is attached or housed.
• a smart sprayer such as a device for spot spraying or precision spraying, on a farm vehicle such as a tractor, a robot, a helicopter, an aircraft, an unmanned aerial vehicle (UAV) such as a drone is attached or housed.
• a smart sprayer usually comprises input sensors (such as a camera) and a processing unit which is responsible for the analysis of the input data and the provision of a decision, which is based on the analysis of the input data, regarding the application of the compound according to the invention to the crops ( or the weeds) is configured in a specific and precise manner.
• the use of such smart sprayers usually requires position systems (e.g. GPS receivers) with which the recorded data can be localized and farm
• pests can be detected from images captured by a camera.
• the pests can be identified and / or classified based on these images.
• algorithms for image processing can be algorithms for machine remote control such as artificial neural networks, decision trees, and artificial intelligence algorithms use. In this way it is possible to use the connections described here only where they are needed.
• the present invention therefore also relates in particular to a method for protecting seeds and germinating plants from attack by pests by treating the seeds with one of the compounds of the formula (I).
• the method according to the invention for protecting seeds and germinating plants from attack by pests further comprises a method in which the seed is treated simultaneously in one process or sequentially with a compound of the formula (I) and a mixture component. It also includes a method in which the seed is treated at different times with a compound of the formula (I) and a mixture component.
• the invention also relates to the use of the compounds of the formula (I) for treating seeds to protect the seeds and the resulting plants from animal pests.
• the invention further relates to seed which has been treated with a compound of the formula (I) according to the invention for protection against animal pests.
• the invention also relates to seeds which have been treated at the same time with a compound of the formula (I) and a mixture component.
• the invention further relates to seeds which have been treated at different times with a compound of the formula (I) and a mixture component.
• the individual substances may well be present in different layers on the seed.
• the layers which contain a compound of the formula (I) and mixing components can optionally be separated by an intermediate layer.
• the invention relates to also on seeds in which a compound of the formula (I) and a mixture component are applied as a constituent of a coating or as a further layer or layers in addition to a coating.
• the invention further relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
• Compounds of the formula (I) can also be used in combination with compositions or compounds of signal technology, as a result of which there is better colonization with symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, and / or there is an optimized nitrogen fixation .
• symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi
• the compounds of the formula (I) are suitable for protecting seeds of any type of plant which is used in agriculture, in the greenhouse, in forests or in horticulture.
• these are grains (e.g. wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g. Sugar beet and fodder beet), peanuts, vegetables (e.g. tomatoes, cucumbers, beans, cabbage plants, onions and lettuce), fruit plants, lawns and ornamentals.
• the treatment of the seeds of cereals (such as wheat, barley, rye and oats), maize, soy, cotton, canola, rapeseed, vegetables and rice is of particular importance.
• transgenic seeds with a compound of the formula (I) are also of particular importance.
• the heterologous genes in transgenic seeds can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
• the present invention is particularly suitable for the treatment of transgenic seeds which contain at least one heterologous gene derived from Bacillus sp. originates.
• the compound of the formula (I) is applied to the seed.
• the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
• the seed can be treated at any point in time between harvest and sowing.
• seeds are used that have been separated from the plant and freed from cobs, peels, stems, coats, wool or pulp.
• seeds can be used that have been harvested, cleaned and dried to a storable moisture content.
• seeds can also be used that, after drying, for. B. treated with water and then dried again, for example priming.
• the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
• suitable formulations and methods for seed treatment are known to those skilled in the art.
• the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seeds, and also UFV formulations.
• formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and also water.
• customary additives such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and also water.
• Suitable dyes which can be contained in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments which are sparingly soluble in water and dyes which are soluble in water can be used. Examples are those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
• Suitable wetting agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which are customary for the formulation of agrochemical active ingredients and which promote wetting.
• Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
• Suitable dispersants and / or emulsifiers which can be contained in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active ingredients. Nonionic or anionic dispersants or mixtures of nonionic or ionic dispersants can preferably be used.
• Suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
• Suitable anionic dispersants are in particular Eigninsulfonate, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
• the seed dressing formulations which can be used according to the invention can contain all foam-inhibiting substances customary for the formulation of agrochemical active ingredients as defoamers. Silicone defoamers and magnesium stearate can be used with preference.
• All substances which can be used for such purposes in agrochemical agents can be present as preservatives in the seed dressing formulations which can be used according to the invention.
• Examples include dichlorophene and benzyl alcohol hemiformal.
• Secondary thickening agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which can be used in agrochemical agents for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silicic acid are preferred.
• Suitable adhesives which can be contained in the seed dressing formulations which can be used according to the invention are all conventional binders which can be used in seed dressings.
• Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned as preferred.
• the gibberellins are known (see R. Wegler “Chemistry of Plant Protection and Pest Control Agents”, Vol. 2, Springer Verlag, 1970, pp. 401-412).
• the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for treating seeds of the most varied of types.
• the concentrates or the preparations that can be obtained by diluting them with water can be used to dress the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of maize, rice, rape, peas, beans, Cotton, sunflowers, soybeans and beets or vegetable seeds of the most varied nature.
• the seed dressing formulations which can be used according to the invention or their diluted application forms can also be used for dressing seeds of transgenic plants.
• the procedure for dressing is to put the seed in a mixer in batch or continuous mode, add the desired amount of dressing formulations either as such or after prior dilution with water and until the formulation is evenly distributed mixes the seeds. If necessary, this is followed by a drying process.
• the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seeds.
• the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
• the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
• animal parasites in particular ectoparasites or endoparasites.
• endoparasit particularly includes helminths and protozoa such as coccidia.
• Ectoparasites are typically and preferably arthropods, especially insects or acarids.
• the compounds of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for combating parasites that occur in livestock breeding and keeping in farm animals, breeding animals, zoo animals, laboratory animals, test animals and domestic animals. th. They are effective against all or individual stages of development of the parasites.
• the farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and in particular cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aqua culture, or possibly insects such as bees.
• mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and in particular cattle and pigs
• poultry such as turkeys, ducks, geese and especially chickens
• fish or crustaceans e.g. B. in aqua culture, or possibly insects such as bees.
• Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chin chillas, ferrets and in particular dogs, cats, housebirds; Reptiles, amphibians or aquarium fish.
• the compounds of the formula (I) are administered to mammals.
• the compounds of the formula (I) are administered to birds, namely house birds or, in particular, poultry.
• birds namely house birds or, in particular, poultry.
• the compounds of the formula (I) for combating animal parasites, disease, deaths and reduced performance (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and simpler one Animal husbandry is made possible and better animal welfare can be achieved.
• control or “control” in the present context means that the compounds of the formula (I) effectively prevent the occurrence of the respective parasite in an animal which is infected with such parasites to a harmless extent , is reduced. More precisely, “combating” in the present context means that the compounds of the formula (I) kill the respective parasite, prevent its growth or prevent its reproduction.
• the arthropods include, for example, but are not limited to, from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Tri- menopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chr
• Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp. ; as well as pests
• Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp ., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
• Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
• Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp ., Hyalomma spp., Ixodes spp.,
• parasitic protozoa examples include, but are not limited to:
• Mastigophora such as:
• Metamonada from the order Vaccinia spp., Spironucleus spp.
• Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetrichomonas spp., Trichomonas spp., Tritrichomonas spp.
• Euglenozoa from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.
• Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. B. Hartmanella sp.
• Alveolata such as Apicomplexa (Sporozoa): e.g. B. Cryptosporidium spp .; from the order Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida e.g. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida e.g. B.
• Leucocytozoon spp. Plasmodium spp .; from the order Piroplasmida e.g. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida e.g. B. Balantidium spp., Buxtonella spp.
• Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
• the helminths pathogenic for humans or animals include, for example, Acanthocephala, Nematodes, Pentastoma and Platyhelminths (e.g. Monogenea, Cestodes and Trematodes).
• Exemplary helminths include, but are not limited to:
• Monogenea e.g. For example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
• Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
• Cyclophyllida for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Me- socestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
• Trematodes from the class Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolides spp ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium s
• Nematodes from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
• Aelurostrongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides sppum., Crenosoma spp spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus sppphalus., Filaroides spp., Globocephaluscephalus spp., Haemonchus spp., Heligmosomoides spp.,
• Oesophagodontus spp. Oesophagostomum spp., Ollulanus spp .
• Ornithostrongylus spp. Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriaulostomum sppyl., Protostrongylus sppyl ., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
• Spirurida for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria
• Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,
• Pentastoma from the order Porocephalida, for example Linguatula spp.
• the compounds of the formula (I) are administered by methods generally known in the art, such as enteral, parenteral, dermal or nasal, in the form of suitable preparations. Administration can be prophylactic; metaphylactically or therapeutically.
• one embodiment of the present invention relates to the compounds of the formula (I) for use as medicaments.
• Another aspect relates to the compounds of the formula (I) for use as an anti-endoparic drug.
• Another special aspect relates to the compounds of the formula (I) for use as an antihelminthicide, in particular for use as a nematicide, platymelminticide, acanthocephalicide or penastomicide.
• Another special aspect relates to the compounds of the formula (I) for use as an antiprotozoal.
• Another aspect relates to the compounds of the formula (I) for use as an anti-parasitic agent, in particular an arthropodicide, very particularly an insecticide or an acaricide.
• veterinary formulations which comprise an effective amount of at least one compound of the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. solid or liquid diluent), a pharmaceutically acceptable auxiliary (e.g. surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary medical formulations and / or a pharmaceutically acceptable auxiliary agent conventionally used in veterinary medical formulations.
• a pharmaceutically acceptable excipient e.g. solid or liquid diluent
• auxiliary e.g. surfactants
• a related aspect of the invention is a method of making a veterinary medicinal formulation as described herein, which comprises the step of mixing at least one compound of the Formula (I) with pharmaceutically acceptable excipients and / or auxiliaries, in particular with pharmaceutically acceptable excipients and / or auxiliaries conventionally used in veterinary formulations.
• Another special aspect of the invention is veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozolic and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, insecticidal and pentastomicidal formulations according to the aspects mentioned, as well as processes for their preparation.
• Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular one non-human animal in need of it.
• Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined here in an animal, in particular a non-human animal, which that needs.
• Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasite infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
• treatment includes prophylactic, metaphylactic and therapeutic treatment.
• mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endo- and ectoparasiticides, are provided for the veterinary field.
• “mixture” not only means that two (or more) different active ingredients are formulated in a common formulation and are used together accordingly, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated in separate formulations; Mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow separate or successive use of the active ingredients in question.
• the active ingredients specified here with their “Common Name” are known and are described, for example, in the “Pesticide Manual” (see above) or can be researched on the Internet (eg http: //www.alanwood.net/pesticides).
• active ingredients from the group of ectoparasiticides as mixing partners include, without this being intended to represent a restriction, the insecticides and acaricides listed in detail above.
• Further active ingredients which can be used are listed below according to the above-mentioned classification, which is based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-directed chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) owners; (9) modulators of chordotonal organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase,
• Active ingredients with unknown or non-specific mechanisms of action e.g. B. Fentrifanil, Fenoxacrim, Cycloprene, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quinomethionat, Triarathen, Clothiazoben, Tetrasul, Potassium Oleate, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Crypropylat;
• Organochlorine compounds e.g. B. camphechlor, Eindan, heptachlor; or phenylpyrazoles, e.g. B. acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. B. Sarolaner, Afoxolaner, Lotilaner, fluoralaner; Pyrethroids, e.g. B.
• Neonicotinoids e.g. B. nithiazine
• Dicloromezotiaz, triflumezopyrim macrocyclic lactones e.g. B. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime
• Bios, flormones or pheromones for example natural products, e.g. thuringiensine, codlemon or neem components
• Dinitrophenols e.g. B. Dinocap, Dinobuton, Binapacryl;
• Benzoylureas e.g. B. Fluazuron, Penfluron,
• Amidine derivatives e.g. B. Chlormebuform, Cymiazol, Demiditraz
• Beehive varroa acaricides for example organic acids, e.g. formic acid, oxalic acid.
• Exemplary active ingredients from the group of endoparasiticides, as mixing partners, include, without being limited thereto, anthelmintic active ingredients and antiprotozoal active ingredients.
• the anthelmintic active ingredients include, without being limited thereto, the following nematicidal, trematicidal and / or cestocidal active ingredients: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latemidectin, Ivermectin, emamectin, milemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, from the class of the
• Antiprotozoal active ingredients including, but not limited to, the following active ingredients: from the class of the triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyletherionophore, for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of the macrocyclic lactones, for example: milbemycin, erythromycin; from the class of the quinolones, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the class of the pyrimidines, for example: pyrimethamine; from the class of the sulfonamides, for example: sulfachinoxaline, trimethoprim, sulfaclozine; from the class of the thiamines, for example: Amprolium; from the class of the lincosamides, for example:
• a vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, which is able to remove pathogens such.
• the pathogens can either be transmitted mechanically (e.g. trachoma by non-stinging flies) to a host or after injection (e.g. malaria parasites by mosquitoes) into a host.
• Anopheles malaria, filariasis
• flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
• Ticks Borelliosis such as Borrelia bungdorferi sensu lato., Borrelia duttoni, early summer meningoencephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), Ehrlichiosis.
• vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit viruses to plants from plants.
• Other vectors that can transmit plant viruses are spider mites, fice, beetles and nematodes.
• vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Futzomyia, fice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
• insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Futzomyia, fice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
• Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens that are transmitted by vectors.
• another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in fan management, in horticulture, in gardens and leisure facilities as well as in the protection of stocks and materials.
• the compounds of the formula (I) are suitable for protecting industrial materials against attack or destruction by insects, e.g. B. from the orders Coleoptera, Hymenoptera, Isoptera, Fepidoptera, Psocoptera and Zygentoma.
• non-living materials such as preferably plastics, adhesives, Feime, paper and cardboard, feather, wood, wood processing products and paints.
• the use of the invention to protect wood is particularly preferred.
• the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
• the compounds of the formula (I) are in the form of a ready-to-use pesticide, ie they can be applied to the pesticide without further changes appropriate material are applied.
• insecticides or fungicides those mentioned above are particularly suitable.
• the compounds of the formula (I) can be used to protect against growth on objects, in particular ship hulls, screens, nets, structures, quays and signal systems which come into contact with sea or brackish water.
• the compounds of the formula (I) can also be used as antifouling agents alone or in combination with other active ingredients.
• the compounds of the formula (I) are suitable for combating animal pests in the hygiene sector.
• the invention can be used in household, hygiene and stored goods protection, especially to combat insects, arachnids, ticks and mites that occur in closed spaces, such as apartments, factory halls, offices, vehicle cabins, animal breeding facilities.
• the compounds of the formula (I) are used alone or in combination with other active ingredients and / or auxiliaries. They are preferably used in household insecticidal products.
• the compounds of the formula (I) are active against sensitive and resistant species and against all stages of development.
• pests from the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
• the reaction mixture was poured into water, acidified with 10% hydrochloric acid and the precipitated precipitate was filtered off with suction and dried.
• the crude product was purified by chromatography on silica gel (gradient: cyclohexane / ethyl acetate). 261 mg of N- [5-bromo-2- [4- (trifluoromethoxy) phenyl] -1, 2,4-triazol-3-yl] methanesulfonamide were obtained.
• reaction mixture was diluted with ethyl acetate, mixed with 10% citric acid solution, extracted several times with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the crude product was purified by chromatography on silica gel (gradient: cyclohexane / ethyl acetate). 229 mg of 4- [5-amino-1- [4- (trifluoromethoxy) phenyl] -l, 2,4-triazol-3-yl] benzaldehyde were obtained.
• reaction mixture was poured into water and filtered through a Chromabond TM PTS separation column.
• the crude product was purified by chromatography on silica gel (gradient: cyclohexane / ethyl acetate). 100 mg of N- [5- (4-formylphenyl) -2- [4- (trifluoromethoxy) phenyl] -1, 2,4-triazol-3-yl] methanesulfonamide were obtained.
• reaction mixture was poured into water and filtered through a Chromabond TM PTS separation column.
• the crude product was purified by chromatography on silica gel (gradient: cyclohexane / ethyl acetate). 144 mg of 5- (4-aminophenyl) -N-methyl-2- [4- (trifluoromethoxy) phenyl] -l, 2,4-triazol-3-amine were obtained.
• Step 1
• step 1 N- [5- (4-nitrophenyl) -2- [4- (trifluoromethoxy) phenyl] -1, 2,4-triazol-3-yl] acetamide (step 1) (305 mg, 0.75 mmol) in methanol (10 ml) were first added copper chloride (74 mg, 0.75 mmol) and then sodium borohydride (285 mg, 7.5 mmol). The reaction mixture was stirred at room temperature for 0.5 h and concentrated under reduced pressure. Then saturated sodium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was distilled off under reduced pressure.
• the raw product was purified by chromatography on silica gel (gradient: cyclohexane / ethyl acetate) whereby 260 mg of N- [5- (4-aminophenyl) -2- [4- (trifluoromethoxy) phenyl] -l, 2,4-triazol-3-yl] acetamide was obtained.

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