WO2022053453A1 - Azole carboxamide servant d'agents de lutte contre les nuisibles - Google Patents

Azole carboxamide servant d'agents de lutte contre les nuisibles Download PDF

Info

Publication number
WO2022053453A1
WO2022053453A1 PCT/EP2021/074562 EP2021074562W WO2022053453A1 WO 2022053453 A1 WO2022053453 A1 WO 2022053453A1 EP 2021074562 W EP2021074562 W EP 2021074562W WO 2022053453 A1 WO2022053453 A1 WO 2022053453A1
Authority
WO
WIPO (PCT)
Prior art keywords
unsubstituted
spp
substituted
halogen
cycloalkyl
Prior art date
Application number
PCT/EP2021/074562
Other languages
German (de)
English (en)
Inventor
Alexander Sudau
Markus Heil
Robert Velten
Philipp Winter
Tobias HARSCHNECK
Marc LINKA
Elke Hellwege
Peter Lösel
Andreas Turberg
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Publication of WO2022053453A1 publication Critical patent/WO2022053453A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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

Definitions

  • the present invention relates to new azolecarboxamides, processes for their preparation and their use for controlling animal pests, especially arthropods and in particular insects and arachnids.
  • new azolecarboxamides have advantages over the already known compounds, for example better biological or ecological properties, broader application methods, better insecticidal, acaricidal action and good compatibility with useful plants.
  • the new azolecarboxamides can be used in combination with other agents to improve the effectiveness, in particular against insects that are difficult to control.
  • the new compounds according to the invention have not been disclosed hitherto.
  • the present invention therefore relates to new compounds of the formula (I) wherein (embodiment 1-1)
  • A is N or CR A ; stands by
  • R A is H, halogen, cyano, nitro, SF5, NR d R e , OR a , S(O) n R a or SC>2NR b R c ; or for Ci-Ce-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl or CACACycloalkyl. each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R f ;
  • V is -C(Q 1 )NR V1 R V2 ; stands by
  • R V1 is Ci-Cg-alkyl, Cz-Cg-alkenyl, Cz-Cg-alkynyl, C 3 -C 7 -cycloalkyl, C 5 -C 7 -cycloalkenyl or saturated C 3 -C 7 -heterocyclyl, all of which are unsubstituted can be, or can optionally be substituted once to 13 times with halogen and/or with 1 to 2 Rh;
  • R V2 for H; or for Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -Cg-alkynyl, Ci-Cg-alkoxy, C 3 -C 7 -cycloalkyl or Cs-C 7 -cycloalkenyl, all unsubstituted or simple substituted up to 13 times with halogen and/or optionally with 1 to 2 R g ; or
  • R1 is H; or for Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -Cg-alkynyl, C 3 -C 7 -cycloalkyl, Ci-Cg-alkyl carbonyl, C 3 -C 7 -cycloalkylcarbonyl, Ci-Cg- Alkoxycarbonyl, C 3 -C 7 -cycloalkoxyylcarbonyl, Ci-Cg -alkylsulfonyl or C 3 -C 7 -cycloalkylsulfonyl, each of which can be unsubstituted, or mono- to 13-fold with halogen and/or optionally with 1 to 2 R h may be substituted;
  • R 2 represents the substructure of the general formula -XYZ; stands by X is phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted by 1 to 3 R x ; each is included
  • R x are independently halogen, cyano, nitro, C(Q 1 )R a , C(O)OR a , C(Q 1 )NR b R c , NR d R e , OR a , S(O) n R a or SO 2 NR b R c ; or for Ci-Cg-alkyl, C 2 -C6-alkenyl, C 2 - Cg-alkynyl or C3-C?-cycloalkyl, each unsubstituted or mono- to 13-substituted by halogen and/or optionally by 1 to 3 R f ;
  • R Y1 and R Y2 for H; or for Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -Cg-alkynyl or C3-C 2 -cycloalkyl, all unsubstituted or substituted by 1 to 7 RY11 ; each is included
  • R Y11 independently for halogen, cyano, Ci-C4-alkyl, C3-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;
  • Q Y is O or S
  • R Z1 independently represent a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, each unsubstituted or substituted by 1 to 4 R Z11 ; each is included
  • R Z11 independently represent halogen, cyano, nitro, S . C(Q 1 )R a , C(O)OR a , C(Q 1 )NR b R c , NR d Re , OR a , S(O) n R a or SO 2 NR b R c ; or for Ci-Cg-alkyl, C 2 -Cg- alkenyl, C 2 -Cg-alkynyl or C3-C?-cycloalkyl, all unsubstituted or substituted by 1 to 5 R zla ; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted by 1 to 3 R zla ; or two adjacent R Z11 together form an unsubstituted or 1 to 6 R zla substituted linear Cs-Cs-alkylene group, where independently from one another 1 CH 2 unit can be replaced by carbonyl and 1 to 2 CH 2 units
  • R zla for halogen, cyano, Ci-Ci-alkyl, Ci-C4-alkoxy, Ci-Ci-thioalkyl, Ci-C4-haloalkyl or Ci-C4-haloalkoxy;
  • R Z2 , R Z2a and R Z3 independently represent H; or for C(O)R a , C(O)OR a , C(O)NR b R c , S(O) n R a ; or for C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 7 -cycloalkyl, each unsubstituted or substituted by 1 to 5 R Z21 ; or phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted by 1 to 4 R Z21 ; each is included
  • R Z21 are independently halogen, cyano, nitro, SFs, C(Q')R a . C(O) ORa , CfQ1 ) NRb Rc . NR d R e , OR a , S(O) n R a or SO 2 NR b R c ; or for Ci-C 6 alkyl, Ci-C 6 haloalkyl, C 2 -Cg alkenyl, CS-Cg alkynyl or C 3 -C 7 cycloalkyl; or
  • R Z2 and R Z3 together with the TCN moiety form a 5- to 7-membered ring;
  • R Z21 independently of one another for halogen, hydroxy, cyano, Ci-Cg-alkyl, C 3 -Cg-cycloalkyl, Ci-Cg-haloalkyl, Ci-C4-alkenyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or for spirocyclically bonded heterocyclyl having 2 to 7 ring atoms, where 1 to 2 oxygen atoms are present as heteroatoms; or
  • R Z2a and a second R Z2a together with the NCN moiety form a 5- to 7-membered ring;
  • C2-Cg-alkenyl or C2-Cg-alkynyl all of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R f ; or phenyl unsubstituted or substituted by 1 to 5 R g ;
  • R b and R c independently represent H; or for Ci-Cg-alkyl, GG-cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R f ; or R b and R c together form a 3- to 7-membered ring;
  • R d and R e are independently H, C(Q')R a . C(O) ORa ; or for Ci-Cg-alkyl, GG-cycloalkyl.
  • R f are independently halogen, cyano, nitro, GG-cycloalkyl.
  • R g independently for halogen, cyano, nitro, Ci-C4-alkyl, GG-cycloalkyl.
  • R h are independently halogen, cyano, nitro, hydroxy, SF5, OSO2FV.
  • SO2NRb Rc N(Rd )(Re ), C (Q ' ) NRb Rc .
  • NCR ⁇ Q ⁇ R 3 , C(O)R a , OC(O)R a or Q 2 ; or for Ci-C4- alkyl , G-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, GG-cycloalkyl.
  • Q 1 independently represents O, S, N0R a or NCN;
  • Q 2 are independently O or N0R a ; n are independently 0, 1 or 2.
  • Preferred (embodiment 2-1) are the compounds of the formula (I) in which
  • A is N or CR A ; stands by
  • R A is H, halogen, cyano or SF5; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-Cg-alkynyl or CAG-cycloalkyl. each of which may be unsubstituted, or may be substituted one to seven times with halogen and/or optionally with an R f ;
  • V is -C(Q 1 )NR V1 R V2 ; stands by
  • R V2 for H; or for Ci-C 6 -alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Ci-Cg-alkoxy, C 3 -C 7 -cycloalkyl or Cs-C 7 -cycloalkenyl all unsubstituted or simple substituted up to five times with halogen and/or optionally with 1 to 2 R g ; or
  • R V1 and R V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06
  • U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 rows
  • R 1 for H stands for Ci-C4-alkyl, C2-C4-alkenyl, C2-Cg-alkynyl or C 3 -Cg -cycloalkyl, all of which may be unsubstituted in each case, or substituted one to five times by halogen and/or optionally by Ibis 2 Rh could be;
  • R 2 represents the substructure of the general formula -XYZ; stands by
  • X is phenyl, pyridyl, pyrimidyl, pyridazinyl or thienyl, each unsubstituted or substituted by 1 to 3 R x ; stands by R x are independently halogen, cyano, nitro, C(Q 1 )R a , C(O)OR a ; or for Ci-C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 alkoxy, C 2 -Cg alkynyl or C 3 -Cg cycloalkyl, all unsubstituted or substituted by 1 to 3 R f ;
  • R Y1 and R Y2 for H; or for Ci-C-ralkyl, C2-Cg-alkenyl, C2-C4-alkynyl or G-CS-cycloalkyl, all unsubstituted or substituted by 1 to 3 R Y11 ; each is included
  • R Y11 independently represent halogen, cyano, Ci-C-ralkyl, C 3 -Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy;
  • R Z1 is phenyl unsubstituted or substituted by 1 to 4 R Z11 ; each is included
  • R Z11 independently represent halogen, cyano, nitro, S .
  • R zla for halogen, cyano, C'i-C 3 -alkyl. Ci-C 3 alkoxy, C1-C3 thioalkyl, Ci C's haloalkyl or Ci-C 3 haloalkoxy;
  • R Z2 , R Z2a and R Z3 are independently H; or for C(O)R a , C(O)OR a , C(O)NR b R c , S(O) n R a ; or for Ci-Cg-alkyl, Cz-Cg-alkenyl, C -Cg-alkmyl or C 3 -C 6 -cycloalkyl, all unsubstituted or substituted by 1 to 4 R Z21 ; or for phenyl or benzyl all in each case unsubstituted or substituted by 1 to 3 R Z21 ; each is included R Z21 independently for halogen, cyano, nitro, SF5, C(Q')R a .
  • R Z2 and R Z3 together with the TCN moiety form a 5- to 7-membered ring;
  • R Z21 independently for halogen, hydroxy, cyano, Ci-Cg-alkyl, G-Cg-cycloalkyl, Ci-Cg-haloalkyl, Ci-C 4 -alkenyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or
  • R Z2a and a second R Z2a together with the NCN moiety form a 5- to 7-membered ring;
  • R a independently for Ci-Cg-alkyl, G-Cg-cycloalkyl. C -Cg -alkcnyl or C -Cg -alkynyl. each of which can be unsubstituted or substituted once to five times by halogen and/or optionally by an R f ; or phenyl unsubstituted or substituted by 1 to 3 R g ;
  • R b and R c are independently H; or for Ci-Cg-alkyl, G-Cg-cycloalkyl.
  • R d and R e are independently H, C (Q 1 )R a . C(O) ORa ; or for Ci-Cg-alkyl, G-Cg-cycloalkyl.
  • R f are independently halogen, cyano, nitro, G-Cg-cycloalkyl.
  • R g are independently halogen, cyano, nitro, Ci-C4-alkyl, Cs-Cg-cycloal
  • Q 1 independently represents O, S, N0R a or NCN;
  • Q 2 are independently O or N0R a ; and n is independently 0, 1 or 2.
  • A is N or CR A ; stands by
  • R A for H, halogen or Ci-C4-alkyl
  • V is -C(Q 1 )NR V1 R V2 ; stands by
  • R V2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or Cß-Cv-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R g ; or
  • R V1 and R V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06
  • U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 rows
  • R1 for H stands for C 1 -C 4 -alkyl or C 2 -C 4 -alkenyl , all of which can be unsubstituted or substituted once to five times with halogen and/or optionally with 1 to 2 Rh;
  • R 2 represents the substructure of the general formula -XYZ; stands by
  • X is phenyl or pyridyl, each unsubstituted or substituted by 1 to 3 R x ; stands by
  • R x independently of one another is halogen, cyano or C 1 -C 4 -alkyl, each unsubstituted or substituted by 1 to 2 R f ;
  • R Y11 independently for halogen, cyano, Ci-C2-alkyl or C1-C2-alkoxy
  • R Z1 is phenyl substituted with 1 to 3 R Z11 ; each is included
  • R Z11 independently for halogen, cyano, OR a SR a , or for Ci-Cralkyl, C3-Cg-cycloalkyl, all unsubstituted or substituted by 1 to 3 R zla ; each is included
  • R Z2 , R Z2a and R Z3 are independently H; or for C1-C4-alkyl, in each case unsubstituted or substituted by 1 to 3 R Z21 ; each is included
  • R Z21 independently of one another are halogen or C iG-alkoxy: or
  • R Z21 independently represent halogen, C' iG-alkyl. C1-C3 alkenyl, or C1-C3-
  • R a is independently Ci-Cg-alkyl, Cs-Cg-cycloalkyl, C2-Cg-alkenyl or C2-Cg-alkynyl, all of which may be unsubstituted in each case, or 1 to 5 times by halogen and/or optionally by a R f may be substituted; or phenyl unsubstituted or substituted by 1 to 3 R g ;
  • R f is independently halogen, cyano, nitro, CAG, -cycloalkyl.
  • R g independently for halogen, cyano, nitro, Ci-C4-alkyl, GG-cycloalkyl.
  • R h independently for halogen, cyano, nitro, hydroxy, SF5, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, C1-C4-alkylsulfonyl, GG-cycloalkyl. spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl with 3 to 7 ring atoms, C3-Cg-cycloalkylthio, GG-cycloalkoxy. GG-cycloalkylsilfmyl. GG-cycloalkylstilfonyl.
  • A is N or CR A ; stands by
  • V is -C(O)NR V1 R V2 ; stands by R V1 for C'i-Cfi-alkyl.
  • R V1 for C'i-Cfi-alkyl.
  • P-01 P-04 where these substituents and P-01 and P-04 may all each be unsubstituted, or optionally substituted once to five times with halogen and/or with 1 to 2 Rh;
  • R V2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or C3-C?-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R g ; or
  • R V1 and R V2 together with the nitrogen atom to which they are attached represent a heterocycle U-01;
  • U-01 where U-01 can in each case be unsubstituted or optionally substituted once to three times by halogen and/or optionally by 1 to 2 Rh ;
  • R 1 is Ci-C4-alkyl, each of which may be unsubstituted or mono- to tri-substituted by halogen and/or optionally by 1 to 2 Rh;
  • R 2 represents the substructure of the general formula -XYZ; stands by
  • X is phenyl unsubstituted or substituted with 1 to 3 R x ; stands by
  • R x are independently halogen, cyano or methyl
  • R Y1 and R Y2 for H; Q Y for O;
  • R Z1 is phenyl substituted with 1 to 3 R Z11 ; where 1 R Z11 is in 2-position and where each is standing
  • R Z11 is independently F, Cl, Br, CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, cyclopropyl, OCH3 , OCH2CH3, OCH2CH2CH3, OCH(CH3) 2 , CH2OCH3 or CH(CH3 ) OCH3 ;
  • R Z2 , R Z2a and R Z3 independently represent H;
  • R Z21 is independently methyl; each is included
  • R g independently of one another is halogen, cyano, Ci-C4-alkyl, Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, C1-C4-alkoxy or Ci-C4-haloalkoxy;
  • R h independently for halogen, cyano, nitro, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclic bonded C2-Cg-cycloalkyl, spirocyclic bonded heterocyclyl with 3 to 7 ring atoms, C -Cg- cycloalkylthio, C's-Cg-cycloalkoxy.
  • Cs-Cg-cycloalkylsulphinyl or Cs-Cg-cycloalkylsulphonyl all of which may be unsubstituted or substituted once to 5 times with halogen and/or optionally with 1 to 2 R g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of 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-thiadiazol
  • A is N;
  • V is -C(O)NR V1 R V2 ; stands by
  • R V2 is H or methyl
  • R 1 is methyl
  • R 2 represents the substructure of the general formula -XYZ; stands by
  • X is phenyl unsubstituted or substituted by 1 R x ; stands by
  • R x is chloro, fluoro, cyano or methyl
  • R Z11 independently represent methyl, methoxy or isopropyl.
  • a further preferred embodiment of the invention is represented by compounds of the formula (I) in which A is N and all the other structural elements in embodiment (1-1) or in embodiment (2-1) or in embodiment (3-1 ) or have the meanings given in embodiment (4-1).
  • Cs-Cg-cycloalkoxy, Cs-Cg-cycloalkylsulphinyl or C's-Cg-cycloalkylsilfonyl each of which can be unsubstituted or substituted once to 13 times by halogen and/or optionally by 1 to 2 R g and all other structural elements have the meanings given in embodiment (1-1).
  • a further preferred embodiment of the invention are compounds of the formula (I) in which R h independently represent halogen, cyano, nitro, hydroxy, SFs, OSCFR' 1 .
  • SO2NR b R c , N(R d )( Re ), C(Q 1 )NR b R c , N(R b )C(Q 1 )R a , C(O)R a , OC(O)R a or Q 2 ; or for Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, Ci-C 4 -alkylsulfmyl, Ci-C 4 -alkylsulfonyl, G-Cg-cycloalkyl.
  • a further preferred embodiment of the invention are compounds of the formula (I) in which R h independently represent halogen, cyano, nitro, hydroxy, SF5, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -Alkylthio, Ci-C 4 -alkylsulfmyl, Ci-C 4 -alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl having 3 to 7 ring atoms, -Cg-cycloalkylthio.
  • a further preferred embodiment of the invention are compounds of the formula (I) in which R h independently represent halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci- C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl with 3 to 7 ring atoms, CACg-cycloalkylthio.
  • a further preferred embodiment of the invention are compounds of the formula (I) in which R h is trifluoromethylcyclohexyl, 3,3,3-trifluoropropyl, isopropyl, cyclohexyl, 4,4,4-trifluorobutyl, 4,4- Difluorocyclohexyl, trifluoromethoxyethyl, tetrahydrothiopyran, (1-cyanocyclopropyl)methyl or 1,1,2,2-tetrafluorobutyl and all other structural elements (5-1) have the meanings given.
  • the invention relates to compounds of the general formula (Ia) in which the structural elements V, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or in aspect (3-1) or have the meanings given in aspect (4-1) or the meanings given in aspect (5-1).
  • the invention relates to compounds of the general formula (Ib) in which the structural elements V, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or in aspect (3-1) or have the meanings given in aspect (4-1) or the meanings given in aspect (5-1). (Ib)
  • the invention relates to compounds of the general formula (Ic) in which the structural elements V, R 1 , R Y1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or in Embodiment (3-1) or have the meanings given in embodiment (4-1) or in embodiment (5-1).
  • the invention relates to compounds of the general formula (Id) in which the structural elements V, R 1 , RY1 and R Z1 are in embodiment (1-1) or in embodiment (2-1) or in Embodiment (3-1) or have the meanings given in embodiment (4-1) or in embodiment (5-1).
  • the compounds of the formula (I) can optionally also be present as stereoisomers, i.e. as geometric and/or 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 in general only compounds of the formula (I) are mentioned here.
  • 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 both to the pure enantiomers and diastereomers and to mixtures thereof for controlling animal pests, which include arthropods and, in particular, insects.
  • the compounds of formula (I) can optionally exist in different polymorphic forms or as a mixture of different 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 on its own or in combination with other terms such as haloalkyl, is understood in the context of the present invention to mean a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched.
  • Examples of Ci-C 12 alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, see.
  • Ci-Cg-alkyl radicals are particularly preferred.
  • Ci-C4-alkyl radicals are particularly preferred.
  • alkenyl is a linear or branched C2-Cn-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.
  • preference is given to C2-C9-alkenyl radicals and particular preference is given to C2-C4-alkenyl radicals.
  • alkynyl refers to a linear or branched C2-Cn-alkynyl radical which has at least one triple bond, for example ethynyl, 1-propynyl, either on its own or in combination with other terms and propargyl, understood. Of these, preference is given to C-Cg-alkynylrcstc and particular preference is given to C3-C4-alkynyl radicals.
  • the alkynyl radical can also have at least one double bond.
  • cycloalkyl either on its own or in combination with other terms, is understood according to the invention as meaning a C -CV cycloalkyl group, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Preferred of these are Cs-Cg-cycloalkylrcstc.
  • aryl is understood according to the invention as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthrenyl, particularly preferably phenyl.
  • arylalkyl is understood to mean a combination of “aryl” and “alkyl” radicals defined according to the invention, with the radical generally being bonded via the alkyl group, examples of which are benzyl, phenylethyl or a- methylbenzyl, with benzyl being particularly preferred.
  • hetaryl means a mono-, bi- or tricyclic heterocyclic group composed of carbon atoms and at least one heteroatom, where at least one cycle is aromatic.
  • the hetaryl group preferably contains 3, 4, 5 or 6 carbon atoms selected from the group consisting of 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,
  • heterocyclyl means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring made up of C 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 and 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 one or more times up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different.
  • Halogen stands for fluorine, chlorine, bromine or iodine, preferably for fluorine or chlorine.
  • alkoxy either on its own or in combination with other terms such as, for example, haloalkoxy, is understood here to mean an O-alkyl radical, the term “alkyl” having the meaning given above.
  • MciAI. toluene or THF 40°C to 80°C
  • EtOH, reflux a) EtOH, NaOAc, reflux;
  • the methyl ester E-1 is converted to the corresponding amide.
  • the required amine is pre-stirred with MesAl at room temperature for between 5 and 30 minutes, then the ester is added and the mixture is heated to 40 to 100 °C for a period of between 4 and 16 h.
  • Toluene, THF or dichloromethane are suitable as solvents.
  • Such a prescription can be found, for example, in A. Basha, M. Lipton and SM Weinreb, Tetrahedron Lett., 1977, 18, 4171-4172.
  • the intermediates E-2 can be converted to the intermediates E-3 by means of palladium catalysis.
  • Either the NH-triazole El a can be alkylated directly or the symmetrical NH-triazole El-b is first alkylated and then converted to the methyl ester El by means of a Pd-catalyzed carbonylation.
  • the starting material is stirred with a base, for example Na 2 CO3, K2CO3 or CS2CO3 in DMF at temperatures between 40°C and 100°C and then isolated using standard methods known to a person skilled in the art.
  • the radical R 1 can be introduced via a Michael addition, for which the starting material El a is dissolved in a suitable solvent such as toluene, acetonitrile or DMF and a suitable base such as triethylamine or N,N-diisopropylethylamine at temperatures between 40° C. and 80 ° C is stirred with the appropriate electrophile.
  • a suitable solvent such as toluene, acetonitrile or DMF
  • a suitable base such as triethylamine or N,N-diisopropylethylamine at temperatures between 40° C. and 80 ° C is stirred with the appropriate electrophile.
  • the symmetrical NH-triazole El-b can be converted under conditions analogous to a) to give the intermediate E-lc. This is then converted to the desired starting material El.
  • El-c is dissolved in methanol, sodium acetate and a suitable catalyst are added.
  • Pd(dppf)Cl 2 or Pd(OAc) 2 with ligands such as PPI13 or dppe are suitable here.
  • the mixture is then stirred at temperatures between 40° C. and 100° C. under a carbon monoxide pressure of 1 to 10 bar.
  • the starting materials E1 can be represented in this way.
  • the compounds of the formula (I) can be present as geometric and/or as optically active isomers or corresponding isomer mixtures in various compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus encompasses both pure stereoisomers and any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which the compounds of formula (I) are allowed to act on animal pests and/or their habitat. Preference is given to combating animal pests in agriculture and forestry and in the protection of materials. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.
  • the invention also relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
  • pesticide always also includes the term plant protection agent.
  • 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 crop and for controlling animal pests, in particular insects, Arachnids, helminths and molluscs found in agriculture, horticulture, animal husbandry, aquaculture, forests, gardens and leisure facilities, in the protection of stored products and materials and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, regulations and procedures which aim to prevent diseases, in particular infectious diseases, and which serve to protect human health and animals and/or protect the environment and/or maintain cleanliness. According to the invention, 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, ceramics, plastic or metal(s) to ensure that they are free of Hygiene pests and/or their excrements.
  • surgical or therapeutic regimens of treatment to be applied to the human or animal bodies and diagnostic regimens to be performed on the human or animal bodies.
  • honeygiene sector thus covers all areas, technical fields and industrial applications where 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 husbandry, etc.
  • sanitary pest should therefore be understood to mean one or more animal pests whose presence in the sanitary sector is problematic, particularly for health reasons. It is therefore a major objective to avoid or minimize the presence and/or exposure to hygiene pests in the hygiene sector. In particular, this can be achieved by using a pesticide that can be used both to prevent an infestation and to manage an infestation that is already present. One can also use preparations that prevent or reduce exposure to pests.
  • Sanitary pests include, for example, the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as pesticides. They are active against normally sensitive and resistant species and against all or some developmental stages.
  • the pests mentioned above include:
  • Pests from the phylum Arthropoda in particular from the class Arachnida z.
  • B. Acarus spp. e.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculus Schlechtedali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g. B.
  • Eriophyes pyri Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g.
  • B. Hemitarsonemus latus ( Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., e.g.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., e.g. 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 z.
  • Anoplophora glabripennis Anthonomus spp., e.g. 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, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g . 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 comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., e.g. B.
  • Hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., e.g. B.
  • Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus ( Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., e.g. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., e.g. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., e.g. B.
  • 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.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulema oryzae, Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga Helleri, Phyllotreta spp., e.g. B.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., e.g.
  • 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.
  • Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., e.g. B.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena 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.
  • Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striate Uns, Lecanium spp., e.g. B. Lecanium comi ( Parthenolecanium comi), Lepidosaphes spp., e.g. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum 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., e.g.
  • Myzus ascalonicus Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.
  • 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. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., e.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Pianococcus spp., e.g. B.
  • Pianococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., e.g. B.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., e.g. B.
  • Trioza spp. e.g. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; from the suborder of theHeteropteraz.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops fiircatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., e.g. B.
  • Nezara spp. e.g. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus 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 z.
  • 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 Wasmannia auropunctata, Xeris spp.; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera z. B. Coptotermes spp., e.g. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g. B.
  • Reticulitermes flavipes Reticulitermes hesperus; from the order of the Lepidoptera z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., e.g. B. Dioryctria tremani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., e.g.
  • Grapholita molesta Grapholita prunivora
  • Hedylepta spp. Helicoverpa 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. 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. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., e.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp.,
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera z.
  • Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., e.g. B.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., e.g. B. Scutigerella immaculata;
  • Pests from the Mollusca tribe 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., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;
  • the compounds of the formula (I) can optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant traits, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or used as an anti-MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) agent. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active substances.
  • the present invention further relates to formulations, in particular formulations for controlling unwanted animal pests.
  • the formulation can be applied to the animal pest and/or its habitat.
  • the formulation according to the invention can be provided to the end user as a ready-to-use “application form”, ie the formulations can be applied directly to the plants or seeds using a suitable device such as a spray or dust device.
  • the formulations may be provided to the end user in the form of concentrates to be diluted, preferably with water, prior to use.
  • the term “formulation” refers to such a concentrate
  • the term “use form” refers to a solution ready for use by the end user, ie usually such a diluted formulation.
  • the formulation according to the invention may 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 of the invention and at least one agriculturally useful adjuvant, e.g., carrier and/or surfactant(s).
  • agriculturally 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, plant parts or seeds.
  • suitable solid supports include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates and ammonium nitrates, ground natural rocks 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 preparing granules include, but are not limited to, crushed 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, alkylnaphthalene, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethyl - ene 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), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), Esters (including fats and oils) and (poly)ethers, unsubstitute
  • the carrier can also be a liquified gaseous diluent, i.e. a liquid which is gaseous at normal temperature and pressure, for example aerosol propellants such as halocarbons, butane, propane, nitrogen and carbon dioxide.
  • a liquified gaseous diluent i.e. a liquid which is gaseous at normal temperature and pressure
  • aerosol propellants such as halocarbons, 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, (poly)ethers.
  • the amount of carrier typically ranges from 1% to 99.99% by weight, preferably from 5% to 99.9% by weight, more preferably from 10% to 99.5% by weight and most preferably from 20% to 99% by weight. -% of formulation.
  • Liquid carriers are typically present in the range 20% to 90%, for example 30% to 80% by weight of the formulation.
  • Solid carriers are typically present in the range 0% to 50%, preferably 5% to 45%, for example 10% to 30% by weight of the formulation.
  • the outlined ranges refer to the total amount of carrier.
  • the surfactant can be ionic (cationic or anionic), amphoteric or nonionic such as ionic or nonionic emulsifiers, foaming agents, dispersing agents, wetting agents, penetrants and any mixtures thereof.
  • suitable surfactants include, without limitation, salts of polyacrylic acid, ethoxylated poly(alpha-substituted)acrylate derivatives, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and/or propylene oxide with or without alcohols, fatty acids or fatty amines (for example polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfos
  • 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, alkylbenzene sulfonates, sulfonated polymers of naphthalene/formaldehyde, polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.
  • the amount of surfactant is typically in the range 5 to 40%, for example 10 to 20% by weight of the formulation.
  • suitable excipients 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 latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays e.g.
  • stabilizers e.g. cold stabilizers, preservatives (e.g. dichlorophone, benzyl alcohol hemiformal, l, 2-benzisothiazolin-3-one, 2-methyl -4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV stabilizers, and other agents that improve chemical and/or physical stability
  • dyes or pigments e.g inorganic cal pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g.
  • silicone antifoams and magnesium stearate silicone antifoams and magnesium stearate
  • antifreeze adhesives
  • gibberellins and processing aids mineral and vegetable oils
  • fragrances waxes
  • nutrients including trace nutrients such as salts of iron, manganese , boron, copper, cobalt, molybdenum and zinc
  • protective colloids including protective colloids, thixotropic substances, penetrants, sequestrants and complexing agents.
  • excipients 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 selected in such a way that they impart certain properties (technical, physical and/or biological properties) to the formulations or the use forms produced from them. Through the choice of excipients, it may be possible to tailor the formulations to specific needs.
  • the formulation comprises an insecticidally/acaricidally/nematicidally effective amount of the compound(s) of the invention.
  • effective amount means an amount sufficient to control insect/mite pests on cultivated plants or for the protection of materials and which does not cause significant damage to the plants treated. Such an amount can vary within a wide range and depends on various factors such as the insect/mite 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 of the invention. It is possible that a formulation comprises two or more compounds according to the invention. In such case, the outlined ranges refer to the total amount of the compounds of the present invention.
  • the formulation of the present invention may be in any conventional type of formulation such as solutions (e.g. aqueous solutions), emulsions, water and oil based suspensions, Powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, scattered granules), suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers and also microencapsulations in polymeric substances.
  • the compound of the invention may be in a suspended, emulsified or dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g.
  • SL, LS 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), granules (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.
  • the outlined amount of compound of the present invention refers to the total amount of the compounds of the present invention. Conversely, this also applies to all other components of the formulation if two or more representatives of such a component, e.g. a wetting agent or binder, are present.
  • a wetting agent or binder e.g. a wetting agent or binder
  • Emulsifiable Concentrates 15-70% by weight of at least one compound of the invention and 5-10% by weight of surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in such amount of water-insoluble organic solvent (e.g. aromatic hydrocarbon or fatty acid amide) and, if necessary, additional water-soluble solvent, so that the total amount is 100% by weight.
  • water-insoluble organic solvent e.g. aromatic hydrocarbon or fatty acid amide
  • a suitable grinder e.g. B. a ball mill
  • 20-60 wt .-% of at least one inventive compound with the addition of 2-10 wt .-% surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 wt .-% thickener (e.g. xanthan gum ) and water to a fine active ingredient suspension.
  • the water is added in such an amount that the total amount is 100% by weight.
  • a stable suspension of the active substance is obtained by dilution with water.
  • binder e.g. polyvinyl alcohol
  • a suitable grinding device for example a ball mill
  • 20-60% by weight of at least one compound according to the invention are ground with the addition of 2-10% by weight of surfactant (for example sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight.
  • Thickeners e.g. modified clay, in particular Bentone, or silicon dioxide
  • an organic vehicle are crushed into a fine suspension of active ingredient and oil.
  • the organic carrier is added in such an amount that the total amount is 100% by weight.
  • a stable dispersion of the active substance is obtained by dilution with water.
  • 5-25% by weight of at least one compound according to the invention are mixed with the addition of 3-10% by weight of surfactant (e.g. sodium lignosulfonate), 1-5% by weight of binder (e.g. carboxymethylcellulose) and an amount of water that you come to a total of 100 wt .-% crushed.
  • surfactant e.g. sodium lignosulfonate
  • binder e.g. carboxymethylcellulose
  • 5-20% by weight of at least one compound according to the invention are added to 5-30% by weight organic solvent mixture (e.g. fatty acid dimethylamide and cyclohexanone), 10-25% by weight surfactant mixture (e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and such an amount of water that you come to a total amount of 100 wt .-%, given. This mixture is stirred for 1 hour, whereby a thermodynamically stable microemulsion forms spontaneously.
  • organic solvent mixture e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant mixture e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate
  • 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 (e.g. aromatic hydrocarbon), 2-15% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic acid and a di - or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol).
  • a protective colloid eg polyvinyl alcohol
  • a free-radical polymerization initiated with a free-radical initiator leads to the formation of poly(methy)acrylate microcapsules.
  • an oil phase comprising 5-50% by weight of at least one compound of the invention, 0-40% by weight of water-insoluble organic solvent e.g.
  • an isocyanate monomer e.g. diphenylmethene-4,4'-diisocyanate
  • a protective colloid eg polyvinyl alcohol
  • you can also add 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 associated with such an amount of solid support (e.g. silicate) that the total amount is 100% by weight.
  • solid support e.g. silicate
  • Formulation types i) to xiii) can contain further auxiliaries such as 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoams, 0.1-1% by weight of dyes and/or pigments and 5- 10% by weight of antifreeze.
  • the compounds of formula (I) can also be used in a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial insects, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and/or plant growth regulators become, e.g. B. to broaden the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent repellency or to prevent the development of resistance.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial insects, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and/or plant growth regulators become, e.g. B. to broaden the spectrum of action, to extend the duration of action, to increase the speed of action, to
  • the compounds of formula (I) in a mixture with other active ingredients or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or Growth regulators and/or fertilizers are present.
  • the compounds of the formula (I) can be used to improve the plant traits such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the use forms prepared from these formulations as a mixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) Inhibitors preferably carbamates selected from Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, O- xamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl
  • GAB A-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, cyphenothrin [(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-isomer], es
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximine selected from sulfoxaflor, or butenolide selected from flupyradifuron , or mesoionics selected from triflumezopyrim.
  • Allosteric modulators of the nicotinic acetylcholine receptor preferably spinosyns 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 analogues selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
  • Non-specific (multi-site) inhibitors preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin, or sulfuryl fluoride, or borax, or tartar emetic, or methyl isocyanate generators 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.
  • Insect intestinal membrane microbial disruptors selected from Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenehrionis and B./. plant proteins selected from CrylAb, CrylAc, CrylFa, Cry 1A. 105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Abl/35Abl.
  • Inhibitors of mitochondrial ATP synthase preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifon.
  • Oxidative phosphorylation decouplers by perturbation of the proton gradient selected from chlorfenapyr, DNOC and sulfluramide.
  • Blockers of the nicotinic acetylcholine receptor channel selected from Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
  • CHS1-related chitin biosynthesis inhibitors preferably benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • Moult disruptor particularly in Diptera, i.e., fly flies 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 hydramethylnon, acequinocyl, fluacrypyrim and bifenazate.
  • Mitochondrial complex I electron transport inhibitors preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).
  • Blockers of the voltage-gated sodium channel preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumizone.
  • Inhibitors of acetyl-CoA carboxylase preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidione 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 pyflubumid.
  • Ryanodine receptor modulators preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.
  • Modulators of chordotonal organs selected from flonicamid.
  • Allosteric modulators of the GABA -dependent chloride channel preferably meta-diamides selected from broflanilide or isoxazoles selected from fluxametamide.
  • Baculoviruses preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedroviruses (NPVs) selected from Anticar sia gemmatalis MNPV and Helicoverpa armigera NPV.
  • GVs granuloviruses
  • NPVs nucleopolyhedroviruses
  • All of the mixing partners mentioned in classes (1) to (15) can optionally form salts with suitable bases or acids if they are able to do so because of their functional groups. All of the fungicidal mixing 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) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1009) flutriafol, (1010) imazalil, (1011) imazalil sulfate, (1012) ipconazole, (1013) metconazole, (1014) myclobutanil, (1015) paclobutrazol, (1016) prochloraz, (1017) propiconazole, ( 1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.0
  • Respiratory chain inhibitors 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) ametoctradine, (3.002) amisulbromine, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamide, (3.007) dimoxystrobin, (3.008) enoxastrobin , (3.009) famoxadone, (3.010) fenamidone, (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-[( ⁇ [(lE)-l-(3-)
  • Inhibitors of mitosis and cell division for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl )-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2- bromo-4-fluorophenyl)-N-(2,6-difluorophenyl
  • Inhibitors of amino acid and/or protein biosynthesis for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.
  • 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) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (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)-l-(morpholin-4-yl)prop-2-en-l-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).
  • 13) Inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (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) cyflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon (15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiin,
  • the compounds of formula (I) can be combined with biological pest control agents.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pest control agents include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.
  • 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 subsp. israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular 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.
  • B. thuringiensis subsp. israelensis serotype H-14
  • strain AM65-52 Accession No. ATCC 1276
  • B. thuringiensis subsp. aizawai in particular strain ABTS-1857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-1 or B. thuringiensis
  • fungi and yeasts that are used 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 anisoplicie, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isarici fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that are or can be used as biological pest control agents are:
  • bacteria and fungi that are added to plants or plant parts or plant organs as 'inoculants' and promote plant growth and plant health through their special properties. Examples are:
  • plant extracts and such products formed by microorganisms, including proteins and secondary metabolites, which are or can be used as biological pest control agents are:
  • the compounds of formula (I) can be combined with safeners, such as benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormide, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenime, furilazole, isoxadifen (-ethyl ), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 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-o-xazolidine (CAS 52836-3
  • Plants are understood to mean all plants and parts of plants, such as desired and undesired wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes , peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (e.g. cabbage) and other types of vegetables, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soybeans
  • potatoes sugar beets
  • sugar cane tomatoes , peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans
  • Brassica oleracea e.g. cabbage
  • Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant varieties that can or cannot be protected by plant variety rights. Plants should be understood to mean all stages of development such as seeds, cuttings, young (immature) plants through to mature plants. Plant parts are to be understood as meaning all above-ground and subterranean parts and organs of plants such as shoots, leaves, flowers and roots, with leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes being listed as examples. 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 space according to the usual treatment methods, e.g. B. by dipping, spraying, vaporizing, nebulizing, sprinkling, brushing, injecting and in the case of propagation material, especially seeds, also by one or more layers of encasing.
  • plants and parts thereof 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, and parts thereof are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • Plants of the plant varieties that are commercially available or in use are particularly preferably treated according to the invention.
  • Plant varieties are plants with new properties (“traits”) that have been obtained through conventional breeding, through mutagenesis or through recombinant DNA techniques. This can be varieties, breeds, organic and genotypes.
  • the compounds of the formula (I) can advantageously be used for treating transgenic plants, plant cultivars or plant parts which have received genetic material which imparts advantageous and/or useful properties (traits) to these plants, plant cultivars or plant parts. It is therefore contemplated to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof.
  • a transgenic event results from the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome.
  • the insertion creates a new DNA sequence, termed an "event", which is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to the inserted DNA/flanking the inserted DNA at both ends.
  • traits or transgenic events include, without limitation, resistance to pests, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, hybrid seed production and herbicide tolerance, the trait in relation to a plant of such a trait or a such a transgenic event is absent, is measured.
  • Such advantageous and/or useful properties are better plant growth, vitality, stress tolerance, standing ability, 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 salinity, increased flowering, easier harvesting, accelerated ripening, 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 to animal and microbial pests such as against insects, arachnids, mites and snails.
  • Bt Cry or VIP proteins which include CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof , and also hybrids or combinations thereof, in particular the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA-CrylF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the Cry 1 Ac protein or hybrids derived from the Cry 1 Ac protein (e.g.
  • hybrid CrylAb-CrylAc proteins or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the Cry 1A. 105 protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as in Estruch et al. (1996), Proc Natl Acad Sei US A.
  • herbicides for example imidazolinones, sulphonylureas, glyphosate or phospinothricin.
  • bar or PAT gene or the Streptomyces coelicolor gene which is described in WO2009/152359 and which tolerance to Glufonsin herbicides confers a gene encoding an appropriate EPSPS (5-enolpyruvylshikimate-3-phosphate synthase) that confers tolerance to EPSPS-targeted herbicides, particularly herbicides such as glyphosate and its salts, a for glyphosate N-acetyltransferase gene encoding or a gene encoding glyphosate oxoreductase may be mentioned.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. WO2007/024782), a mutant Arabidopsis ALS/AHAS gene (e.g. US Patent 6,855,533), genes encoding 2,4-D monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid) and genes encoding dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).
  • ALS acetolactate synthase
  • a mutant Arabidopsis ALS/AHAS gene e.g. US Patent 6,855,533
  • genes encoding 2,4-D monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid) genes encoding dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).
  • Such properties are an increased resistance to phytopathogenic fungi, bacteria and/or viruses, which, for example, goes back to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and the correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • systemin phytoalexins
  • elicitors also resistance genes and the correspondingly expressed proteins and toxins.
  • Particularly useful transgenic events in transgenic plants or plant cultivars 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 deposited, 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 3006-210-23 (Cotton,
  • Event BLR1 Rapeseed, restoration of male sterility, deposited as NCIMB 41193, described in WO2005/074671
  • 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, 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, insect control, not deposited, not deposited, described in US-A 2007-
  • PTA-11041) optionally stacked with Event EE-GM1/LL27 or Event EE-GM2 /LL55 (WO2011/063413 A2), Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA-10442, WO2011/066360A1), Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA-10442, WO2011/066384A1), Event DP-040416-8 (corn, insect control, ATCC Accession No. PTA-11508, WO2011/075593 A1), Event DP-043A47-3 (corn, insect control, ATCC Accession No.
  • Event DP-11509, WO2011/075595A1 Event DP-004114-3 (corn, insect control, ATCC Accession No. PTA-11506, WO2011/084621A1), Event DP-032316-8 (Ma is, Insect Control, ATCC accession no. PTA-11507, WO2011/084632A1), Event MON-88302-9 (rapeseed, herbicide tolerance, ATCC Accession No. PTA-10955, WO2011/153186A1), Event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession no.
  • transgenic plants can also be present in the transgenic plants in combination with one another.
  • transgenic plants that can be 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, rapeseed and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed.
  • Traits that are particularly emphasized are the plants' increased resistance to insects, arachnids and snails, and the plants' increased resistance to one or more herbicides.
  • the treatment of the plants and parts of plants with the compounds of formula (I) is carried out directly or by affecting their environment, habitat or storage space according to the usual treatment methods, e.g. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenching), drip irrigation and with propagating material, especially seeds, also by dry dressing, wet dressing, slurry dressing, encrusting , single or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) by the ultra-low volume method or to inject the use form or the compound of formula (I) itself into the soil.
  • a preferred direct treatment of plants is foliar application, i. H. the compounds of the formula (I) are applied to the foliage, with the frequency of treatment and the application rate being 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 formula (I) on the habitat of the plant. This can be done, for example, by drenching, mixing into the soil or the nutrient solution, i. H. the locus of the plant (e.g. soil or hydroponic systems) is drenched with a liquid form of the compounds of formula (I), or by soil application, d. H.
  • the compounds of the formula (I) according to the invention are introduced into the site of the plants in solid form (eg in the form of granules) or by drip application (often also referred to as "chemigation"), ie the compounds of the formula according to the invention (I) are introduced at defined locations near the plants by means of surface or underground drip tubes over specified periods of time together with varying amounts of water. In the case of paddy rice cultures, this can also be done by metering the compound of the formula (I) in a solid application form (eg as granules) into a flooded paddy 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 arable farming, precision arable farming or precision farming.
  • models support site-specific management of agricultural assets with data from various sources such as soil, 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 optimize agronomic decisions, guide the precision of pesticide applications, and record the work performed.
  • one can apply the compounds of the invention to a crop according to an appropriate application protocol when 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 of the invention to the crop.
  • the compounds of the invention can also be used in combination with smart spray equipment such as spot spray equipment or precision spray equipment attached to a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone - or housed, are used.
  • a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone - or housed
  • UAV unmanned aerial vehicle
  • Such equipment usually comprises input sensors (such as a camera) and a processing unit responsible for analyzing the input data and providing a decision, based on the analysis of the input data, to apply the compound of the invention to the crop ( or the weeds) is configured in a specific and precise way.
  • Deploying such smart sprayers usually requires positioning systems (e.g., GPS receivers) to locate the recorded data and control farm vehicles, geographic information systems (GIS) to present the information on understandable maps, and appropriate farm vehicles to operate the required agricultural measure such as spraying.
  • positioning systems e.g., GPS receiver
  • pests can be detected from images captured by a camera.
  • the pests can be identified and/or classified based on these images.
  • image processing algorithms can use machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. 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 seed and germinating plants from infestation by pests by treating the seed with one of the compounds of the formula (I).
  • the method according to the invention for protecting seed and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It further also includes a method in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of formula (I) for the treatment of seed to protect the seed and the plant resulting therefrom from animal pests.
  • the invention also 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 seed which has been treated at the same time with a compound of formula (I) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component.
  • the individual substances can be present in different layers on the seed.
  • the layers which contain a compound of the formula (I) and mixture components can optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • the invention also 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.
  • a further advantage can be seen in the fact that treating the seed with a compound of the formula (I) can promote germination and emergence of the treated seed. It is also to be regarded as advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
  • Compounds of formula (I) can also be used in combination with compositions or compounds of signaling technology, resulting in better colonization with symbionts, such as rhizobia, mycorrhiza and/or endophytic bacteria or fungi, and/or optimized nitrogen fixation .
  • symbionts such as rhizobia, mycorrhiza and/or endophytic bacteria or fungi, and/or optimized nitrogen fixation .
  • the compounds of the formula (I) are suitable for protecting seed of any plant variety used in agriculture, in greenhouses, in forests or in horticulture.
  • these are seeds from cereals (e.g. wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beet (e.g Sugar beet and fodder beet), peanut, vegetables (e.g. tomato, cucumber, bean, cabbage, onion and lettuce), fruit plants, turf and ornamental plants.
  • cereals e.g. wheat, barley, rye and oats
  • corn, soybeans, cotton, canola, oilseed rape, vegetables and rice are examples of seed from cereals (e.g. wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beet (e.g Sugar beet
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • This is the seed of plants which generally contain at least one heterologous gene which controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties.
  • the heterologous genes in transgenic seed can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for treating transgenic seed containing at least one heterologous gene derived from Bacillus sp. originates. It is particularly preferably a heterologous gene which originates from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state in which it is sufficiently stable that no damage occurs during the treatment.
  • seed treatment can be done at any time between harvest and sowing.
  • seeds are used which have been separated from the plant and freed from cobs, husks, stems, husks, wool or pulp.
  • seed can be used that has been harvested, cleaned and dried to a storable moisture content.
  • seeds can also be used which, after drying, e.g. B. treated with water and then dried again, for example priming.
  • care when treating the seed, care must be taken to ensure that the amount of the compound of the formula (I) and/or other additives applied to the seed is chosen so that the germination of the seed is not impaired or the resulting plant is not damaged. This is particularly important for active ingredients that can have phytotoxic effects when applied in certain quantities.
  • 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 seed, and also ULV 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, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • customary additives such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which can be present 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 here. Examples which may be mentioned are those designated Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which can be present in the seed-dressing formulations which can be used according to the invention are all substances which promote wetting and which are customary for the formulation of agrochemical active ingredients.
  • Alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates, can preferably be used.
  • Suitable dispersants and/or emulsifiers which can be present 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 anionic dispersants can preferably be used.
  • Particularly suitable nonionic dispersants are 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, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates.
  • All foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be present as defoamers in the seed-dressing formulations which can be used according to the invention. Silicone defoamers and magnesium stearate can preferably be used. 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 thickeners which can be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical agents. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silicic acid are preferred.
  • Suitable adhesives which can be present in the dressing formulations which can be used according to the invention are all the usual binders which can be used in dressings. Mention may preferably be made of polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • the gibberellins are known (cf. R. Wegler "Chemie der convinced für Schweizer- und Swdlingskampfmitel", 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 the treatment of a very wide variety of seeds.
  • the concentrates or the preparations obtainable therefrom by diluting with water can be used for dressing grain seeds, such as wheat, barley, rye, oats and triticale, and also corn, rice, rapeseed, peas, beans and cotton seeds , sunflowers, soybeans and turnips or also from vegetable seeds of the most diverse nature.
  • the seed dressing formulations which can be used according to the invention or their diluted application forms can also be used for seed dressing of transgenic plants.
  • the treatment is carried out in such a way that the seed is placed in a mixer in discontinuous or continuous operation, the desired amount of dressing formulations is added either as such or after prior dilution with water and until the formulation is evenly distributed mixed with the seed. If necessary, a drying process follows.
  • the application rate of the seed dressing formulations that 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 seed.
  • 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. animal health
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, particularly insects or acarids.
  • the compounds of formula (I) which have a favorable toxicity to warm-blooded animals, are useful for controlling parasites occurring in livestock, farm animals, zoo animals, laboratory animals, experimental animals and domestic animals in animal breeding and animal husbandry. They are effective against all or individual developmental stages of the parasites.
  • farm animals include 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 aquaculture, or possibly insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and in particular dogs, cats, house birds; Reptiles, amphibians or aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of formula (I) are administered to birds, namely pet birds or in particular poultry.
  • the use of the compounds of formula (I) for combating animal parasites is said to reduce or prevent disease, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey and the like) so that animal husbandry is more economical and simpler and a better welfare of the animals can be achieved.
  • control or “control” as used herein means that the compounds of formula (I) are effective in preventing the occurrence of the relevant parasite in an animal infected with such parasite to a harmless level , is reduced. More specifically, “combat” in the present context means that the compounds of formula (I) kill, prevent the growth of or prevent the proliferation of the parasite in question.
  • Arthropods include, 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., Trimenopon spp., Trinoton spp., Wemeckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia
  • 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.; and nuisance and hygiene pests from the
  • the following Akari are exemplary, without being limited to them:
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae such as Argas spp., Omithodorus 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., Omithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp ., Hyalomma spp., Ixodes spp., Rhipicephal
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as:
  • Metamonada from the order Vaccinonadida, for example Giardia spp., Spironucleus spp.
  • Parabasala from the order Trichomonadida, for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
  • Euglenozoa from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, e.g. Entamoeba spp., Centramoebidae, e.g. 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 z. B. Hepatozoon spp., Klosiella spp.; from the order Haemosporida z. B.
  • Leucocytozoon spp. Plasmodium spp.; from the order Piroplasmida z.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and also e.g. B. Myxozoa spp.
  • Helminths pathogenic to humans or animals include, for example, Acanthocephala, Pentastoma and Platyhelminths (e.g. Monogenea, Cestodes and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea e.g. B.: 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 spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma sp.
  • 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., Fasciolopsis spp., Fischoederius spp ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp
  • Acanthocephala from the order Oligacanthorhynchida e.g. Macracanthorhynchus spp., Prosthenorchis spp.; from the order Moniliformida for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida, for example Linguatula spp.
  • the compounds of formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration can be prophylactic; be metaphylactic or therapeutic.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as medicaments.
  • a further aspect relates to the compounds of the formula (I) for use as an anti-endoparasitic.
  • a further special aspect relates to the compounds of the formula (I) for use as an anthelmintic, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.
  • a further special aspect relates to the compounds of the formula (I) for use as an antiprotozoal.
  • a further aspect relates to the compounds of formula (I) for use as an antiectoparasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. solid or liquid diluents), a pharmaceutically acceptable adjuvant (e.g. surfactants), especially one a pharmaceutically acceptable excipient conventionally used in veterinary formulations and/or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient e.g. solid or liquid diluents
  • a pharmaceutically acceptable adjuvant e.g. surfactants
  • a related aspect of the invention is a method of preparing a veterinary formulation as described herein, comprising the step of admixing at least one compound of Formula (I) with pharmaceutically acceptable excipients and/or auxiliaries, in particular with pharmaceutically acceptable excipients and/or auxiliaries conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and accaricidal formulations, according to the aspects mentioned, and methods for their production.
  • Another aspect relates to a method of treating a parasitic infection, particularly an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, by applying an effective amount of a compound of formula (I) to an animal, particularly a non-human animal in need of it.
  • Another aspect relates to a method of treating a parasitic infection, particularly an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, particularly a non-human animal, which requirement.
  • Another aspect relates to the use of the compounds of formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, 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 hereby provided for the veterinary field.
  • mixture not only means that two (or more) different active ingredients are formulated in a common formulation and thus applied together, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, when more than two active ingredients are to be employed, all of the active ingredients can be formulated in a common formulation, or all of the 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 permit separate or sequential application 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.alan-wood.net/pesticides).
  • Exemplary active ingredients from the group of ectoparasiticides as mixing partners include, without this being intended to constitute a restriction, the insecticides and acaricides listed in detail above.
  • Other useful active ingredients are listed below according to the above classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GAB A-gated 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-gated chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonal organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disrupt
  • Drugs with unknown or non-specific mechanisms of action e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazon, gossyplur, flutenzin, bromopropylate, cryolite;
  • organochlorine compounds e.g. B. camphechlor, lindane, heptachlor; or phenylpyrazoles, e.g. B. acetoprol, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. B. sarolaner, afoxolaner, lotilaner, fluralaner; pyrethroids, e.g. B.
  • neonicotinoids e.g. B. Nithiazine
  • dicloromezotiaz triflumezopyrim macrocyclic lactones e.g. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime
  • Bios, hormones or pheromones for example natural products, e.g. thuringiensin, codlemon or neem components
  • dinitrophenols e.g. B. Dinocap, Dinobuton, Binapacryl;
  • benzoylureas e.g. e.g. fluazuron, penfluron,
  • amidine derivatives e.g. chlormebuform, cymiazole, demiditraz
  • Beehive varroa acaricides for example organic acids, e.g., formic acid, oxalic acid.
  • Exemplary endoparasiticidal active ingredients include, but are not limited to, anthelmintic active ingredients and antiprotozoal active ingredients.
  • Anthelmintic agents include, but are not limited to, the following nematicidal, trematicidal and/or cestocidal agents: from the macrocyclic lactone class, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubend
  • Antiprotozoal agents including but not limited to the following agents: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the polylether ionophore class, for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones, for example: enrofloxacin, pradofloxacin; from the class of quinines, for example: chloroquine; from the class of pyrimidines, for example: pyrimethamine; from the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozine; from the class of thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin; from the
  • a vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, which is capable of pathogens such as. B. viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to transfer to a host.
  • pathogens can be transmitted to a host either mechanically (e.g. trachoma by non-stinging flies) or after injection (e.g. malaria parasites by mosquitoes) into a host.
  • Anopheles malaria, filariasis
  • Flies sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;
  • Ticks Lyme disease such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesia (Babesia canis canis), Ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example aphids, flies, leafhoppers or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice and beetles.
  • 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, Lutzomyia, lice, fleas, flies, mites and ticks that 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, Lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and/or humans.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and/or pathogens which are transmitted by vectors.
  • a further aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, in horticulture, in gardens and leisure facilities as well as in the protection of stored products and materials.
  • the compounds of formula (I) are suitable for protecting technical materials against infestation or destruction by insects, e.g. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • non-living materials such as preferably plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints.
  • Application of the invention to the protection of 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 formula (I) are present as a ready-to-use pest control agent, ie they can be applied to the appropriate material is applied.
  • insecticides or fungicides those mentioned above are particularly suitable.
  • the compounds of the formula (I) can be used to protect objects, in particular ship hulls, sieves, nets, structures, quays and signaling systems, which come into contact with seawater or brackish water, from fouling.
  • the compounds of the formula (I) can be used alone or in combination with other active ingredients as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and stored product protection, especially for combating insects, arachnids, ticks and mites that occur in closed rooms such as apartments, factory buildings, 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 insecticide products.
  • the compounds of 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 application takes place, for example, in aerosols, non-pressurized sprays, e.g. B. pump and atomizer sprays, smoke machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energyless or passive vaporization systems, moth paper, moth bags and moth gels, as granules or dust, in scatter baits or bait stations.
  • the measurements of the 1 H-NMR spectra were carried out with a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI probe head with tetramethylsilane as standard (0.00 ppm) and the measurements were recorded usually from solutions in the solvents CD3CN, CDCL or dg-DMSO.
  • a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements.
  • the measurements were carried out at a probe head temperature of 298 K. If other measurement temperatures were used, this will be noted separately.
  • the 'H NMR data of selected examples are reported in the form of 'H NMR packages. For each signal peak, first the 5 value in ppm and then the signal intensity is listed in round brackets. The 5-value signal intensity number pairs from different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form:
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra measured in DMSO.
  • the tetramethylsilane peak can therefore appear in NMR peak lists, but it does not have to.
  • 1 H NMR Pcaks are equivalent to the classical 1 HN MR printouts and thus usually contain all peaks that are also listed in a classical NMR interpretation.
  • they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and/or peaks from impurities.
  • the peaks of stereoisomers of the target compounds and/or peaks of impurities usually have on average a lower intensity than the peaks of the compounds according to the invention (for example with a purity of >90%).
  • Such stereoisomers and/or impurities can be typical of the particular production process. Their peaks can thus help to identify the reproduction of our manufacturing process using 'by-product fingerprints'.
  • An expert who calculates the peaks of the target compounds using known methods can isolate the peaks of the target compounds as required, with additional intensity filters being used if necessary. This isolation would be similar to the peak picking involved in classical 1 H NMR interpretation.
  • the solvent used can be read from the JCAMP file with the parameter "solvent”, the measuring frequency of the spectrometer with “observe frequency” and the spectrometer model with “spectrometer/data system”.
  • test tubes To coat the test tubes, first 9 mg of active substance are dissolved in 1 ml of acetone AR and then diluted to the desired concentration with acetone AR. 250 ⁇ l of the solution are distributed homogeneously on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h rocking rotation at 30 rpm). With a 900 ppm active ingredient solution and an internal surface area of 44.7 cm 2 , a dose per unit area of 5 pg/cm 2 is achieved with homogeneous distribution.
  • the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying down at room temperature and ambient humidity. After 48 hours, the effectiveness is determined in comparison to the untreated control. To do this, the jars are placed upright and the fleas are knocked on the bottom of the jar. Fleas that remain motionless on the ground or move in an uncoordinated manner are considered dead or battered.
  • 100% effectiveness means that all fleas were infected or dead.
  • 0% effectiveness means no fleas were harmed.
  • the destruction in % is determined in comparison to the untreated control. 100% means that all fleas have been killed; 0% means none of the fleas have been killed.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
  • Preswollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water for one day (5 seeds per well). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Each cavity is then infected with 10-20 Diabrotica balteata beetle larvae.
  • Emulsifier alkylaryl polyglycol ether
  • Barley plants (Hordeum vulgare) are sprayed with a preparation of active compound of the desired concentration and infected with larvae of the green rice bug (Nezara viridula).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.
  • Corn leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with caterpillars of the armyworm (Spodoptera frugiperda). After 7 days, the effect is determined in %. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

Abstract

L'invention concerne de nouveaux composés de formule (I), dans laquelle A, V, R1 et R2 ont la signification mentionnée ci-dessus, et leur utilisation pour lutter contre les animaux nuisibles, en particulier les arthropodes et en particulier les insectes et les arachnides.
PCT/EP2021/074562 2020-09-09 2021-09-07 Azole carboxamide servant d'agents de lutte contre les nuisibles WO2022053453A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20195314 2020-09-09
EP20195314.8 2020-09-09

Publications (1)

Publication Number Publication Date
WO2022053453A1 true WO2022053453A1 (fr) 2022-03-17

Family

ID=72470187

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2021/074562 WO2022053453A1 (fr) 2020-09-09 2021-09-07 Azole carboxamide servant d'agents de lutte contre les nuisibles

Country Status (2)

Country Link
AR (1) AR123476A1 (fr)
WO (1) WO2022053453A1 (fr)

Citations (132)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2009A (en) 1841-03-18 Improvement in machines for boring war-rockets
US137395A (en) 1873-04-01 Improvement in nuts
WO1997017432A1 (fr) 1995-11-06 1997-05-15 Wisconsin Alumni Research Foundation Toxines proteiques insecticides provenant de photorhabdus
WO1998008932A1 (fr) 1996-08-29 1998-03-05 Dow Agrosciences Llc TOXINES PROTEINIQUES INSECTICIDES ISOLEES A PARTIR DE $i(PHOTORHABDUS)
WO1998044140A1 (fr) 1997-04-03 1998-10-08 Dekalb Genetics Corporation Lignees de mais resistantes aux glyphosates
WO1998050427A1 (fr) 1997-05-05 1998-11-12 Dow Agrosciences Llc TOXINES PROTEIQUES INSECTICIDES ISSUES DE $i(XENORHABDUS)
WO2000026345A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N.V. Riz tolerant au glufosinate
WO2000026356A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N. V. Riz tolerant au glufosinate
WO2001031042A2 (fr) 1999-10-29 2001-05-03 Aventis Cropscience N.V. Plantes brassica male sterile et procedes de production de ces plantes
WO2001041558A1 (fr) 1999-12-08 2001-06-14 Aventis Cropscience N.V. Colza oleagineux d'hiver hybrides et son procede de production
WO2001047952A2 (fr) 1999-12-28 2001-07-05 Bayer Cropscience N.V. Proteines insecticides provenant de bacillus thuringiensis
WO2001051654A2 (fr) 2000-01-11 2001-07-19 Bayer Cropscience N.V. Procedes et assortiments de materiel permettant d'identifier l'evenement elite gat-zm1 dans les echantillons biologiques
WO2002027004A2 (fr) 2000-09-29 2002-04-04 Monsanto Technology Llc Plante de ble 33391 resistante au glyphosate et compositions et procedes de detection de celle-ci
WO2002034946A2 (fr) 2000-10-25 2002-05-02 Monsanto Technology Llc Mecanisme biochimique de plant de coton pv-ghgt07(1445), compositions et techniques de detection de celui-ci
WO2002036831A2 (fr) 2000-10-30 2002-05-10 Monsanto Technology Llc Colza canola pv-bngt(rt73), compositions et procedes de detection correspondants
WO2002040677A2 (fr) 2000-11-20 2002-05-23 Monsanto Technology Llc Evenement du coton pv-ghbk04 (531) et compositions et procedes permettant de detecter la presence de ce dernier
WO2002044407A2 (fr) 2000-11-30 2002-06-06 Ses Europe N.V. Séquence des flancs de t227-1
US20020102582A1 (en) 2000-09-13 2002-08-01 Levine Elaine B. Corn event MON810 and compositions and methods for detection thereof
WO2002100163A2 (fr) 2001-06-11 2002-12-19 Monsanto Technology Llc Evenement mon15985 du coton et compositions et procedes servant a sa detection
WO2003013224A2 (fr) 2001-08-06 2003-02-20 Bayer Bioscience N.V. Cotonniers avec tolerance aux herbicides et procedes de production et d'identification de ces cotonniers
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US20030126634A1 (en) 1990-08-09 2003-07-03 Dekalb Genetics Corporation Methods and compositions for the increase of yield in plants
WO2004011601A2 (fr) 2002-07-29 2004-02-05 Monsanto Technology, Llc Mais pv-zmir13 designe mon863, composition et procedes de detection
WO2004039986A1 (fr) 2002-10-29 2004-05-13 Syngenta Participations Ag Coton insecticide cot102
WO2004053062A2 (fr) 2002-12-05 2004-06-24 Monsanto Technology Llc Evenement associe a l'agrostide asr-368 et compositions et procedes de detection de la presence de celle-ci
WO2004072235A2 (fr) 2003-02-12 2004-08-26 Monsanto Technology Llc Evenement mon 88913 de plant de coton et procedes de detection correspondants
US20040172669A1 (en) 2003-02-28 2004-09-02 Josef Kraus Glyphosate tolerant sugar beet
WO2004074492A1 (fr) 2003-02-20 2004-09-02 Kws Saat Ag Betteraves sucrieres tolerant le glyphosate
WO2004099447A2 (fr) 2003-05-02 2004-11-18 Dow Agrosciences Llc Mais tc1507 et procedes de detection de celui-ci
US6855533B2 (en) 1995-04-20 2005-02-15 Basf Corporation Structure-based designed herbicide resistant products
WO2005054480A2 (fr) 2003-12-01 2005-06-16 Syngenta Participations Ag Plants de coton resistant aux insectes et procedes de detection de ces derniers
WO2005054479A1 (fr) 2003-12-01 2005-06-16 Syngenta Participations Ag Cotonnier resistant aux insectes et procedes pour detecter celui-ci
WO2005059103A2 (fr) 2003-12-15 2005-06-30 Monsanto Technology Llc Plant de mais mon88017, compositions et procedes de detection associes
WO2005061720A2 (fr) 2003-12-11 2005-07-07 Monsanto Technology Llc Compositions de mais a haute teneur en lysine et methodes de detection correspondantes
WO2005074671A1 (fr) 2004-01-30 2005-08-18 Syngenta Participations Ag Restauration amelioree de la fertilite pour le systeme ogura d'androsterilite cytoplasmique du brassica, et procede correspondant
US20050216969A1 (en) 2004-03-26 2005-09-29 Dow Agrosciences Llc Cry1F and Cry1AC transgenic cotton lines and event-specific identification thereof
WO2005103301A2 (fr) 2004-03-25 2005-11-03 Syngenta Participations Ag Mais mir604
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
US20060070139A1 (en) 2004-09-29 2006-03-30 Pioneer Hi-Bred International, Inc. Corn event DAS-59122-7 and methods for detection thereof
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
WO2006098952A2 (fr) 2005-03-16 2006-09-21 Syngenta Participations Ag Mais 3272 et procedes pour le detecter
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2006128571A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce44-69d
WO2006128568A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide t342-142
WO2006128572A1 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce46-02a
WO2006128570A1 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide 1143-51b
WO2006128573A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce43-67b
WO2006128569A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide 1143-14a
WO2007017186A1 (fr) 2005-08-08 2007-02-15 Bayer Bioscience N.V. Cotonniers tolerants aux herbicides et leurs procedes d'identification
WO2007024782A2 (fr) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions assurant une tolerance a de multiples herbicides et methodes d'utilisation
WO2007040282A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Compose d'amine cyclique et agent pesticide
WO2007091277A2 (fr) 2006-02-10 2007-08-16 Maharashtra Hybrid Seeds Company Limited (Mahyco) Aubergine transgenique (solanum melongena) comprenant un evenement ee-i
WO2007140256A1 (fr) 2006-05-26 2007-12-06 Monsanto Technology, Llc Plant et semence de maïs correspondant au produit transgénique mon89034, procédés de détection et utilisation associés
WO2007142840A2 (fr) 2006-06-03 2007-12-13 Syngenta Participations Ag Événement de transformation de maïs mir162
US20070292854A1 (en) 2000-06-22 2007-12-20 Behr Carl F Corn event PV-ZMGT32(nk603) and compositions and methods for detection thereof
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
US20080064032A1 (en) 2006-09-13 2008-03-13 Syngenta Participations Ag Polynucleotides and uses thereof
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2008112019A2 (fr) 2006-10-30 2008-09-18 Pioneer Hi-Bred International, Inc. Evènement dp-098140-6 du maïs et compositions et procédés pour son identification et/ou sa détection
WO2008114282A2 (fr) 2007-03-19 2008-09-25 Maharashtra Hybrid Seeds Company Limited Riz transgénique (oryza sativa) comprenant l'événement pe-7 et son procédé de détection
WO2008122406A1 (fr) 2007-04-05 2008-10-16 Bayer Bioscience N.V. Plants de coton résistant aux insectes et leurs procédés d'identification
US20080289060A1 (en) 2006-08-24 2008-11-20 Bayer Bioscience N.V. Herbicide tolerant rice plants and methods for identifying same
WO2008151780A1 (fr) 2007-06-11 2008-12-18 Bayer Bioscience N.V. Cotonniers résistant aux insectes comprenant un événement élite ee-gh6 et leurs procédés d'identification
CN101337940A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具杀虫活性的含氮杂环二氯烯丙醚类化合物
CN101337937A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具有杀虫活性的n-苯基-3-取代氨基吡唑类化合物
US20090130071A1 (en) 2007-11-15 2009-05-21 Ai-Guo Gao Soybean Plant And Seed Corresponding To Transgenic Event MON87701 And Methods For Detection Thereof
WO2009100188A2 (fr) 2008-02-08 2009-08-13 Dow Agrosciences Llc Procédés de détection de l’événement de maïs das-59132
WO2009103049A2 (fr) 2008-02-14 2009-08-20 Pioneer Hi-Bred International, Inc. Evénement spt flanquant l'adn génomique végétal et procédés d'identification de l'événement spt
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
WO2009111263A1 (fr) 2008-02-29 2009-09-11 Monsanto Technology Llc Plant de maïs correspondant au produit transgénique mon87460 et compositions et procédés de détection associés
WO2009152359A2 (fr) 2008-06-11 2009-12-17 Dow Agrosciences Llc Produits de recombinaison pour l’expression de gènes de tolérance aux herbicides, plantes associées, et combinaisons de caractères associées
JP2010018586A (ja) 2008-07-14 2010-01-28 Meiji Seika Kaisha Ltd Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
WO2010024976A1 (fr) 2008-08-29 2010-03-04 Monsanto Technology Llc Plante et semences de soja correspondant à l’événement transgénique mon87754 et procédés pour détection de celui-ci
WO2010037016A1 (fr) 2008-09-29 2010-04-01 Monsanto Technology Llc Événement transgénique de soja t mon87705 et procédés pour la détection de celui-ci
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2010052161A2 (fr) 2008-11-06 2010-05-14 Syngenta Participations Ag Compositions herbicides
CN101715774A (zh) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 一个具有杀虫活性化合物制备及用途
WO2010062559A1 (fr) 2008-10-28 2010-06-03 Schering Corporation Pyrazoloquinoléines substituées et leurs dérivés
WO2010066780A1 (fr) 2008-12-12 2010-06-17 Syngenta Participations Ag N-oxypipéridines spirohétérocycliques utilisées comme pesticides
WO2010077816A1 (fr) 2008-12-16 2010-07-08 Syngenta Participations Ag Evénement transgénique du maïs 5307
WO2010076212A1 (fr) 2008-12-19 2010-07-08 Syngenta Participations Ag Événement de betterave sucrière transgénique gm rz13
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2010117735A1 (fr) 2009-03-30 2010-10-14 Monsanto Technology Llc Évènement 17314 de riz transgénique et ses procédés d'utilisation
WO2010117737A1 (fr) 2009-03-30 2010-10-14 Monsanto Technology Llc Evénement de riz transgénique 17053 et ses procédés d'utilisation
WO2011022469A2 (fr) 2009-08-19 2011-02-24 Dow Agrosciences Llc Événement das-40278-9 d'aad-1, lignées transgéniques de maïs connexes et identification spécifique d'événement de celui-ci
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011062904A1 (fr) 2009-11-23 2011-05-26 Monsanto Technology Llc Événement du maïs transgénique mon 87427 et échelle de développement relative
WO2011063413A2 (fr) 2009-11-23 2011-05-26 Bayer Bioscience N.V. Plantes de soja tolérant un herbicide et leurs procédés d'identification
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011066360A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Détection de l'événement 416 du soja aad-12
WO2011075595A1 (fr) 2009-12-17 2011-06-23 Pioneer Hi-Bred International, Inc. Maïs dp-043a47-3 et procédés de détection associés
WO2011075593A1 (fr) 2009-12-17 2011-06-23 Pioneer Hi-Bred International, Inc. Maïs dp-040416-8 et procédés de détection associés
WO2011084632A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de maïs dp-032316-8 et ses procédés de détection
WO2011084621A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de transformation dp-004114-3 du maïs et son procédé de détection
WO2011085575A1 (fr) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 Composés de formanilide hétérocyclique, leurs procédés de synthèse et leur utilisation
WO2011151146A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Procédé d'amélioration du rendement d'un produit cultivé
WO2011153186A1 (fr) 2010-06-04 2011-12-08 Monsanto Technology Llc Evénement mon 88032 d'une plante transgénique du genre brassica et ses procédés d'utilisation
WO2012033794A2 (fr) 2010-09-08 2012-03-15 Dow Agrosciences Llc Événement 1606 d'aad-12 et lignées de soja transgénique associées
WO2012034403A1 (fr) 2010-09-14 2012-03-22 中化蓝天集团有限公司 Composés de fluorométhoxypyrazole et d'anthranilamide, leurs procédés de synthèse et leurs utilisations
CN102391261A (zh) 2011-10-14 2012-03-28 上海交通大学 一种n-取代噁二嗪类化合物及其制备方法和应用
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
US20120131692A1 (en) 2010-11-24 2012-05-24 Pioneer Hi-Bred International, Inc. Brassica gat event dp-073496-4 and compositions and methods for the identification and/or detection thereof
WO2012071039A1 (fr) 2010-11-24 2012-05-31 Pioner Hi-Bred International, Inc. Événement dp-061061-7 de brassica gat et compositions et procédés pour l'identifier et/ou le détecter
WO2012075426A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8264.44.06.1 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012075429A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8291.45.36.2 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012134808A1 (fr) 2011-03-30 2012-10-04 Monsanto Technology Llc Événement transgénique mon 88701 du coton et ses procédés d'utilisation
WO2013003558A1 (fr) 2011-06-30 2013-01-03 Monsanto Technology Llc Plante et graine de luzerne correspondant à l'événement transgénique kk 179-2 et procédés pour la détection de celui-ci
WO2013010094A1 (fr) 2011-07-13 2013-01-17 Dow Agrosciences Llc Événement 8264.42.32.1 « empilé » de tolérance aux herbicides, lignées de soja transgénique associées et détection dudit événément
WO2013012775A1 (fr) 2011-07-15 2013-01-24 Syngenta Participations Ag Événement mzdt09y dans le maïs
WO2013050317A1 (fr) 2011-10-03 2013-04-11 Syngenta Limited Formes polymorphes d'un dérivé d'isoxazoline
CN103109816A (zh) 2013-01-25 2013-05-22 青岛科技大学 硫代苯甲酰胺类化合物及其应用
CN103232431A (zh) 2013-01-25 2013-08-07 青岛科技大学 一种二卤代吡唑酰胺类化合物及其应用
WO2013116053A1 (fr) 2012-02-02 2013-08-08 Dow Agrosciences Llc Compositions pesticides et procédés associés
WO2013116052A1 (fr) 2012-02-02 2013-08-08 Dow Agrosciences Llc Compositions pesticides et procédés associés
CN103265527A (zh) 2013-06-07 2013-08-28 江苏省农用激素工程技术研究中心有限公司 邻氨基苯甲酰胺化合物及其制备方法和应用
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2013162716A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
CN103524422A (zh) 2013-10-11 2014-01-22 中国农业科学院植物保护研究所 苯并咪唑衍生物及其制备方法和用途
WO2014053450A1 (fr) 2012-10-02 2014-04-10 Bayer Cropscience Ag Composés hétérocycliques utilisés comme pesticides
US20140213448A1 (en) 2012-04-27 2014-07-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US20140275503A1 (en) 2013-03-13 2014-09-18 Dow Agrosciences Llc Process for the preparation of certain triaryl rhamnose carbamates
WO2014187846A1 (fr) 2013-05-23 2014-11-27 Syngenta Participations Ag Formulations de mélange en cuve
WO2018177781A1 (fr) 2017-03-28 2018-10-04 Basf Se Composés pesticides
WO2018177970A1 (fr) 2017-03-31 2018-10-04 Basf Se Procédé de préparation de composés chiraux 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium
WO2019059412A1 (fr) 2017-09-20 2019-03-28 Mitsui Chemicals Agro, Inc. Agent de lutte prolongée contre les ectoparasites pour un animal
WO2019121159A1 (fr) 2017-12-21 2019-06-27 Basf Se Composés pesticides
WO2019236274A1 (fr) 2018-06-08 2019-12-12 Dow Agrosciences Llc Molécules à utilité pesticide, compositions et procédés associés
WO2020083733A1 (fr) 2018-10-24 2020-04-30 Basf Se Composés pesticides

Patent Citations (173)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US137395A (en) 1873-04-01 Improvement in nuts
US2009A (en) 1841-03-18 Improvement in machines for boring war-rockets
US20030126634A1 (en) 1990-08-09 2003-07-03 Dekalb Genetics Corporation Methods and compositions for the increase of yield in plants
US6855533B2 (en) 1995-04-20 2005-02-15 Basf Corporation Structure-based designed herbicide resistant products
WO1997017432A1 (fr) 1995-11-06 1997-05-15 Wisconsin Alumni Research Foundation Toxines proteiques insecticides provenant de photorhabdus
WO1998008932A1 (fr) 1996-08-29 1998-03-05 Dow Agrosciences Llc TOXINES PROTEINIQUES INSECTICIDES ISOLEES A PARTIR DE $i(PHOTORHABDUS)
US20050086719A1 (en) 1997-04-03 2005-04-21 Michael Spencer Glyphosate resistant maize lines
US20050188434A1 (en) 1997-04-03 2005-08-25 Michael Spencer Method for plant breeding
US20060059581A1 (en) 1997-04-03 2006-03-16 Dekalb Genetics Corporation Method of breeding glyphosate resistant plants
WO1998044140A1 (fr) 1997-04-03 1998-10-08 Dekalb Genetics Corporation Lignees de mais resistantes aux glyphosates
WO1998050427A1 (fr) 1997-05-05 1998-11-12 Dow Agrosciences Llc TOXINES PROTEIQUES INSECTICIDES ISSUES DE $i(XENORHABDUS)
WO2000026356A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N. V. Riz tolerant au glufosinate
US6468747B1 (en) 1998-11-03 2002-10-22 Plant Genetic System, N.V. Glufosinate tolerant rice
WO2000026345A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N.V. Riz tolerant au glufosinate
WO2001031042A2 (fr) 1999-10-29 2001-05-03 Aventis Cropscience N.V. Plantes brassica male sterile et procedes de production de ces plantes
WO2001041558A1 (fr) 1999-12-08 2001-06-14 Aventis Cropscience N.V. Colza oleagineux d'hiver hybrides et son procede de production
US20030188347A1 (en) 1999-12-08 2003-10-02 Both Greta De Hybrid winter oilseed rape and methods for producing same
WO2001047952A2 (fr) 1999-12-28 2001-07-05 Bayer Cropscience N.V. Proteines insecticides provenant de bacillus thuringiensis
WO2001051654A2 (fr) 2000-01-11 2001-07-19 Bayer Cropscience N.V. Procedes et assortiments de materiel permettant d'identifier l'evenement elite gat-zm1 dans les echantillons biologiques
US20010029014A1 (en) 2000-01-11 2001-10-11 Beuckeleer Marc De Methods and kits for identifying elite event GAT-ZM1 in biological samples
US20070292854A1 (en) 2000-06-22 2007-12-20 Behr Carl F Corn event PV-ZMGT32(nk603) and compositions and methods for detection thereof
US20020102582A1 (en) 2000-09-13 2002-08-01 Levine Elaine B. Corn event MON810 and compositions and methods for detection thereof
WO2002027004A2 (fr) 2000-09-29 2002-04-04 Monsanto Technology Llc Plante de ble 33391 resistante au glyphosate et compositions et procedes de detection de celle-ci
US20020120964A1 (en) 2000-10-25 2002-08-29 Rangwala Tasneem S. Cotton event PV-GHGT07(1445) and compositions and methods for detection thereof
WO2002034946A2 (fr) 2000-10-25 2002-05-02 Monsanto Technology Llc Mecanisme biochimique de plant de coton pv-ghgt07(1445), compositions et techniques de detection de celui-ci
WO2002036831A2 (fr) 2000-10-30 2002-05-10 Monsanto Technology Llc Colza canola pv-bngt(rt73), compositions et procedes de detection correspondants
US20080070260A1 (en) 2000-10-30 2008-03-20 Rachel Krieb Canola event PV-BNGT04(RT73) and compositions and methods for detection thereof
WO2002040677A2 (fr) 2000-11-20 2002-05-23 Monsanto Technology Llc Evenement du coton pv-ghbk04 (531) et compositions et procedes permettant de detecter la presence de ce dernier
WO2002044407A2 (fr) 2000-11-30 2002-06-06 Ses Europe N.V. Séquence des flancs de t227-1
US20090265817A1 (en) 2000-11-30 2009-10-22 Ses Europe N.V./S.A. T227-1 flanking sequence
WO2002100163A2 (fr) 2001-06-11 2002-12-19 Monsanto Technology Llc Evenement mon15985 du coton et compositions et procedes servant a sa detection
US20040250317A1 (en) 2001-06-11 2004-12-09 Huber Scott A Cotton event moni5985 and compositions and methods for detection thereof
US20030097687A1 (en) 2001-08-06 2003-05-22 Linda Trolinder Herbicide tolerant cotton plants and methods for producing and identifying same
WO2003013224A2 (fr) 2001-08-06 2003-02-20 Bayer Bioscience N.V. Cotonniers avec tolerance aux herbicides et procedes de production et d'identification de ces cotonniers
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2004011601A2 (fr) 2002-07-29 2004-02-05 Monsanto Technology, Llc Mais pv-zmir13 designe mon863, composition et procedes de detection
US20060095986A1 (en) 2002-07-29 2006-05-04 Cavato Tracey A Corn event pv-zmir13 (mon863) plants and compositions and methods for detection thereof
WO2004039986A1 (fr) 2002-10-29 2004-05-13 Syngenta Participations Ag Coton insecticide cot102
US20060130175A1 (en) 2002-10-29 2006-06-15 Ellis Daniel M Cot102 insecticidal cotton
WO2004053062A2 (fr) 2002-12-05 2004-06-24 Monsanto Technology Llc Evenement associe a l'agrostide asr-368 et compositions et procedes de detection de la presence de celle-ci
US20060162007A1 (en) 2002-12-05 2006-07-20 Monsanto Technology Llc Bentgrass event asr-368 and compositions and methods for detection thereof
US20060059590A1 (en) 2003-02-12 2006-03-16 Monsanto Technology Llc Cotton event mon 88913 and compositions and methods for detection thereof
WO2004072235A2 (fr) 2003-02-12 2004-08-26 Monsanto Technology Llc Evenement mon 88913 de plant de coton et procedes de detection correspondants
WO2004074492A1 (fr) 2003-02-20 2004-09-02 Kws Saat Ag Betteraves sucrieres tolerant le glyphosate
US20040172669A1 (en) 2003-02-28 2004-09-02 Josef Kraus Glyphosate tolerant sugar beet
WO2004099447A2 (fr) 2003-05-02 2004-11-18 Dow Agrosciences Llc Mais tc1507 et procedes de detection de celui-ci
US20050039226A1 (en) 2003-05-02 2005-02-17 Dow Agrosciences Llc Corn event TC1507 and methods for detection thereof
WO2005054479A1 (fr) 2003-12-01 2005-06-16 Syngenta Participations Ag Cotonnier resistant aux insectes et procedes pour detecter celui-ci
US20070067868A1 (en) 2003-12-01 2007-03-22 Negrotto David V Insect resistant cotton plants and methods of detecting the same
WO2005054480A2 (fr) 2003-12-01 2005-06-16 Syngenta Participations Ag Plants de coton resistant aux insectes et procedes de detection de ces derniers
US20070028322A1 (en) 2003-12-11 2007-02-01 Dizigan Mark A High lysine maize compositions and methods for detection thereof
WO2005061720A2 (fr) 2003-12-11 2005-07-07 Monsanto Technology Llc Compositions de mais a haute teneur en lysine et methodes de detection correspondantes
WO2005059103A2 (fr) 2003-12-15 2005-06-30 Monsanto Technology Llc Plant de mais mon88017, compositions et procedes de detection associes
US20080028482A1 (en) 2003-12-15 2008-01-31 Beazley Kim A Corn Plant Mon88017 and Compositions and Methods for Detection Thereof
WO2005074671A1 (fr) 2004-01-30 2005-08-18 Syngenta Participations Ag Restauration amelioree de la fertilite pour le systeme ogura d'androsterilite cytoplasmique du brassica, et procede correspondant
WO2005103301A2 (fr) 2004-03-25 2005-11-03 Syngenta Participations Ag Mais mir604
US20080167456A1 (en) 2004-03-25 2008-07-10 Syngenta Participations Ag Corn Event MIR604
WO2005103266A1 (fr) 2004-03-26 2005-11-03 Dow Agrosciences Llc Lignees de coton transgeniques cry1f et cry1ac et leur identification specifique a l'evenement
US20070143876A1 (en) 2004-03-26 2007-06-21 Dow Agrosciences Llc Cry1F and Cry1Ac transgenic cotton lines and event-specific identification thereof
US20050216969A1 (en) 2004-03-26 2005-09-29 Dow Agrosciences Llc Cry1F and Cry1AC transgenic cotton lines and event-specific identification thereof
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
US20060070139A1 (en) 2004-09-29 2006-03-30 Pioneer Hi-Bred International, Inc. Corn event DAS-59122-7 and methods for detection thereof
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
WO2006098952A2 (fr) 2005-03-16 2006-09-21 Syngenta Participations Ag Mais 3272 et procedes pour le detecter
US20060230473A1 (en) 2005-03-16 2006-10-12 Syngenta Participations Ag Corn event 3272 and methods for detection thereof
US20080320616A1 (en) 2005-04-08 2008-12-25 Bayer Bioscience N.V. Elite Event A2407-12 and Methods and Kits for Identifying Such Event in Biological Samples
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
US20080196127A1 (en) 2005-04-11 2008-08-14 Bayer Bioscience N.V. Elite Event A5547-127 and Methods and Kits For Identifying Such Event in Biological Samples
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
US20060282915A1 (en) 2005-05-27 2006-12-14 Monsanto Technology Llc Soybean event MON89788 and methods for detection thereof
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2006128572A1 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce46-02a
US20100024077A1 (en) 2005-06-02 2010-01-28 Syngenta Participations Ag Ce44-69d insecticidal cotton
WO2006128571A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce44-69d
WO2006128568A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide t342-142
WO2006128570A1 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide 1143-51b
WO2006128569A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide 1143-14a
WO2006128573A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce43-67b
US20090217423A1 (en) 2005-06-02 2009-08-27 Cayley Patricia J Ce43-67b insecticidal cotton
WO2007017186A1 (fr) 2005-08-08 2007-02-15 Bayer Bioscience N.V. Cotonniers tolerants aux herbicides et leurs procedes d'identification
US20100050282A1 (en) 2005-08-08 2010-02-25 Bayer Bioscience N.V. Herbicide Tolerant Cotton Plants and Methods for Identifying the Same
WO2007024782A2 (fr) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions assurant une tolerance a de multiples herbicides et methodes d'utilisation
WO2007040282A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Compose d'amine cyclique et agent pesticide
WO2007040280A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
WO2007091277A2 (fr) 2006-02-10 2007-08-16 Maharashtra Hybrid Seeds Company Limited (Mahyco) Aubergine transgenique (solanum melongena) comprenant un evenement ee-i
WO2007140256A1 (fr) 2006-05-26 2007-12-06 Monsanto Technology, Llc Plant et semence de maïs correspondant au produit transgénique mon89034, procédés de détection et utilisation associés
US20080260932A1 (en) 2006-05-26 2008-10-23 Anderson Heather M Corn Plant and Seed Corresponding to Transgenic Event MON89034 and Methods For Detection and Use Thereof
WO2007142840A2 (fr) 2006-06-03 2007-12-13 Syngenta Participations Ag Événement de transformation de maïs mir162
US20090300784A1 (en) 2006-06-03 2009-12-03 Syngenta Participations Ag Corn event mir162
US20100184079A1 (en) 2006-06-28 2010-07-22 Pioneer Hi-Bred International, Inc. Soybean event 3560.4.3.5 and compositions and methods for the identification and detection thereof
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
US20080289060A1 (en) 2006-08-24 2008-11-20 Bayer Bioscience N.V. Herbicide tolerant rice plants and methods for identifying same
US20080064032A1 (en) 2006-09-13 2008-03-13 Syngenta Participations Ag Polynucleotides and uses thereof
WO2008112019A2 (fr) 2006-10-30 2008-09-18 Pioneer Hi-Bred International, Inc. Evènement dp-098140-6 du maïs et compositions et procédés pour son identification et/ou sa détection
US20080312082A1 (en) 2006-10-31 2008-12-18 Kinney Anthony J Soybean event dp-305423-1 and compositions and methods for the identification and/or detection thereof
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2008114282A2 (fr) 2007-03-19 2008-09-25 Maharashtra Hybrid Seeds Company Limited Riz transgénique (oryza sativa) comprenant l'événement pe-7 et son procédé de détection
US20100077501A1 (en) 2007-04-05 2010-03-25 Bayer Bioscience N.V. Insect resistant cotton plants and methods for identifying same
WO2008122406A1 (fr) 2007-04-05 2008-10-16 Bayer Bioscience N.V. Plants de coton résistant aux insectes et leurs procédés d'identification
WO2008151780A1 (fr) 2007-06-11 2008-12-18 Bayer Bioscience N.V. Cotonniers résistant aux insectes comprenant un événement élite ee-gh6 et leurs procédés d'identification
WO2009064652A1 (fr) 2007-11-15 2009-05-22 Monsanto Technology Llc Plante et graine de soja correspondant à l'événement transgénique mon87701 et procédés pour les détecter
US20090130071A1 (en) 2007-11-15 2009-05-21 Ai-Guo Gao Soybean Plant And Seed Corresponding To Transgenic Event MON87701 And Methods For Detection Thereof
WO2009100188A2 (fr) 2008-02-08 2009-08-13 Dow Agrosciences Llc Procédés de détection de l’événement de maïs das-59132
WO2009103049A2 (fr) 2008-02-14 2009-08-20 Pioneer Hi-Bred International, Inc. Evénement spt flanquant l'adn génomique végétal et procédés d'identification de l'événement spt
US20090210970A1 (en) 2008-02-14 2009-08-20 Pioneer Hi-Bred International, Inc. Plant Genomic DNA Flanking SPT Event and Methods for Identifying SPT Event
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
US20110067141A1 (en) 2008-02-15 2011-03-17 Byron Froman Soybean plant and seed corresponding to transgenic event mon87769 and methods for detection thereof
WO2009111263A1 (fr) 2008-02-29 2009-09-11 Monsanto Technology Llc Plant de maïs correspondant au produit transgénique mon87460 et compositions et procédés de détection associés
US20110138504A1 (en) 2008-02-29 2011-06-09 Monsanto Technology Llc Corn plant event mon87460 and compositions and methods for detection thereof
WO2009152359A2 (fr) 2008-06-11 2009-12-17 Dow Agrosciences Llc Produits de recombinaison pour l’expression de gènes de tolérance aux herbicides, plantes associées, et combinaisons de caractères associées
JP2010018586A (ja) 2008-07-14 2010-01-28 Meiji Seika Kaisha Ltd Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
CN101337937A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具有杀虫活性的n-苯基-3-取代氨基吡唑类化合物
CN101337940A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具杀虫活性的含氮杂环二氯烯丙醚类化合物
WO2010024976A1 (fr) 2008-08-29 2010-03-04 Monsanto Technology Llc Plante et semences de soja correspondant à l’événement transgénique mon87754 et procédés pour détection de celui-ci
WO2010037016A1 (fr) 2008-09-29 2010-04-01 Monsanto Technology Llc Événement transgénique de soja t mon87705 et procédés pour la détection de celui-ci
US20100080887A1 (en) 2008-09-29 2010-04-01 Monsanto Technology Llc Soybean Transgenic Event MON87705 and Methods for Detection Thereof
CN101715774A (zh) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 一个具有杀虫活性化合物制备及用途
WO2010062559A1 (fr) 2008-10-28 2010-06-03 Schering Corporation Pyrazoloquinoléines substituées et leurs dérivés
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2010052161A2 (fr) 2008-11-06 2010-05-14 Syngenta Participations Ag Compositions herbicides
WO2010066780A1 (fr) 2008-12-12 2010-06-17 Syngenta Participations Ag N-oxypipéridines spirohétérocycliques utilisées comme pesticides
WO2010077816A1 (fr) 2008-12-16 2010-07-08 Syngenta Participations Ag Evénement transgénique du maïs 5307
WO2010076212A1 (fr) 2008-12-19 2010-07-08 Syngenta Participations Ag Événement de betterave sucrière transgénique gm rz13
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2010117737A1 (fr) 2009-03-30 2010-10-14 Monsanto Technology Llc Evénement de riz transgénique 17053 et ses procédés d'utilisation
WO2010117735A1 (fr) 2009-03-30 2010-10-14 Monsanto Technology Llc Évènement 17314 de riz transgénique et ses procédés d'utilisation
WO2011022469A2 (fr) 2009-08-19 2011-02-24 Dow Agrosciences Llc Événement das-40278-9 d'aad-1, lignées transgéniques de maïs connexes et identification spécifique d'événement de celui-ci
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011062904A1 (fr) 2009-11-23 2011-05-26 Monsanto Technology Llc Événement du maïs transgénique mon 87427 et échelle de développement relative
WO2011063413A2 (fr) 2009-11-23 2011-05-26 Bayer Bioscience N.V. Plantes de soja tolérant un herbicide et leurs procédés d'identification
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011066360A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Détection de l'événement 416 du soja aad-12
WO2011084621A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de transformation dp-004114-3 du maïs et son procédé de détection
WO2011084632A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de maïs dp-032316-8 et ses procédés de détection
WO2011075595A1 (fr) 2009-12-17 2011-06-23 Pioneer Hi-Bred International, Inc. Maïs dp-043a47-3 et procédés de détection associés
WO2011075593A1 (fr) 2009-12-17 2011-06-23 Pioneer Hi-Bred International, Inc. Maïs dp-040416-8 et procédés de détection associés
WO2011085575A1 (fr) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 Composés de formanilide hétérocyclique, leurs procédés de synthèse et leur utilisation
WO2011151146A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Procédé d'amélioration du rendement d'un produit cultivé
WO2011153186A1 (fr) 2010-06-04 2011-12-08 Monsanto Technology Llc Evénement mon 88032 d'une plante transgénique du genre brassica et ses procédés d'utilisation
WO2012033794A2 (fr) 2010-09-08 2012-03-15 Dow Agrosciences Llc Événement 1606 d'aad-12 et lignées de soja transgénique associées
WO2012034403A1 (fr) 2010-09-14 2012-03-22 中化蓝天集团有限公司 Composés de fluorométhoxypyrazole et d'anthranilamide, leurs procédés de synthèse et leurs utilisations
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
WO2012071039A1 (fr) 2010-11-24 2012-05-31 Pioner Hi-Bred International, Inc. Événement dp-061061-7 de brassica gat et compositions et procédés pour l'identifier et/ou le détecter
US20120131692A1 (en) 2010-11-24 2012-05-24 Pioneer Hi-Bred International, Inc. Brassica gat event dp-073496-4 and compositions and methods for the identification and/or detection thereof
WO2012075426A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8264.44.06.1 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012075429A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8291.45.36.2 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012134808A1 (fr) 2011-03-30 2012-10-04 Monsanto Technology Llc Événement transgénique mon 88701 du coton et ses procédés d'utilisation
WO2013003558A1 (fr) 2011-06-30 2013-01-03 Monsanto Technology Llc Plante et graine de luzerne correspondant à l'événement transgénique kk 179-2 et procédés pour la détection de celui-ci
WO2013010094A1 (fr) 2011-07-13 2013-01-17 Dow Agrosciences Llc Événement 8264.42.32.1 « empilé » de tolérance aux herbicides, lignées de soja transgénique associées et détection dudit événément
WO2013012775A1 (fr) 2011-07-15 2013-01-24 Syngenta Participations Ag Événement mzdt09y dans le maïs
WO2013050317A1 (fr) 2011-10-03 2013-04-11 Syngenta Limited Formes polymorphes d'un dérivé d'isoxazoline
CN102391261A (zh) 2011-10-14 2012-03-28 上海交通大学 一种n-取代噁二嗪类化合物及其制备方法和应用
WO2013116053A1 (fr) 2012-02-02 2013-08-08 Dow Agrosciences Llc Compositions pesticides et procédés associés
WO2013116052A1 (fr) 2012-02-02 2013-08-08 Dow Agrosciences Llc Compositions pesticides et procédés associés
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2013162716A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
US20140213448A1 (en) 2012-04-27 2014-07-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
WO2013162715A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
WO2014053450A1 (fr) 2012-10-02 2014-04-10 Bayer Cropscience Ag Composés hétérocycliques utilisés comme pesticides
CN103232431A (zh) 2013-01-25 2013-08-07 青岛科技大学 一种二卤代吡唑酰胺类化合物及其应用
CN103109816A (zh) 2013-01-25 2013-05-22 青岛科技大学 硫代苯甲酰胺类化合物及其应用
US20140275503A1 (en) 2013-03-13 2014-09-18 Dow Agrosciences Llc Process for the preparation of certain triaryl rhamnose carbamates
WO2014187846A1 (fr) 2013-05-23 2014-11-27 Syngenta Participations Ag Formulations de mélange en cuve
CN103265527A (zh) 2013-06-07 2013-08-28 江苏省农用激素工程技术研究中心有限公司 邻氨基苯甲酰胺化合物及其制备方法和应用
CN103524422A (zh) 2013-10-11 2014-01-22 中国农业科学院植物保护研究所 苯并咪唑衍生物及其制备方法和用途
WO2018177781A1 (fr) 2017-03-28 2018-10-04 Basf Se Composés pesticides
WO2018177970A1 (fr) 2017-03-31 2018-10-04 Basf Se Procédé de préparation de composés chiraux 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium
WO2019059412A1 (fr) 2017-09-20 2019-03-28 Mitsui Chemicals Agro, Inc. Agent de lutte prolongée contre les ectoparasites pour un animal
WO2019121159A1 (fr) 2017-12-21 2019-06-27 Basf Se Composés pesticides
WO2019236274A1 (fr) 2018-06-08 2019-12-12 Dow Agrosciences Llc Molécules à utilité pesticide, compositions et procédés associés
WO2020083733A1 (fr) 2018-10-24 2020-04-30 Basf Se Composés pesticides

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"The Pesticide Manual", 2012, BRITISH CROP PROTECTION COUNCIL
A. BASHAM. LIPTONS. M. WEINREB, TETRAHEDRON LETT., vol. 18, 1977, pages 4171 - 4172
CAS , no. 1207977-87-4
CAS, no. 1440516-42-6
ESTRUCH ET AL., PROC NATL ACAD SCI US A. 28, vol. 93, no. 11, 1996, pages 5389 - 94
R. WEGLER: "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", 1970, SPRINGER VERLAG, pages: 401 - 412

Also Published As

Publication number Publication date
AR123476A1 (es) 2022-12-07

Similar Documents

Publication Publication Date Title
AU2020318590A1 (en) Novel heteroaryl-triazole compounds as pesticides
EP4107151A1 (fr) Composés hétéroaryle-triazole utilisés comme pesticides
WO2018095953A1 (fr) Dérivés de 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridine et composés similaires utilisés comme pesticides
WO2018141954A1 (fr) Dérivés d&#39;imidazopyridine substitués par un aryle ou hétéroaryle et leur utilisation comme pesticides
EP4041721B1 (fr) Nouveaux composés d&#39;hétéroaryl-triazole en tant que pesticides
EP3619212B1 (fr) Dérivés d&#39;hétérocycles condensés 2-(het)aryl-substitués en tant que pesticides
AU2017217919A1 (en) Substituted -oxyimidazolyl-carboxamides as pest control agents
EP4139304A1 (fr) Dérivés hétérocycliques condensés à substitution 2- (het) aryle utilisés comme agents de lutte contre les organismes nuisibles
WO2018202494A1 (fr) Dérivés d&#39;hétérocycles condensés à substitution 2-(hét)aryle utilisés comme pesticides
WO2022033991A1 (fr) Triazoles à substitution 5-amino utilisés en tant qu&#39;agents de lutte contre les nuisibles
EP3974414A1 (fr) Pyrazoles et triazoles substitués par un 5-amino en tant que pesticides
AU2017256505A1 (en) Substituted 2-alkylimidazolyl-carboxamides as pest control agents
EP4003966A1 (fr) Triazoles et pyrazoles à substitution 5-amino utilisés comme pesticides
WO2021089673A1 (fr) Sulfonyl amides substitués pour lutter contre des animaux nuisibles
WO2022053453A1 (fr) Azole carboxamide servant d&#39;agents de lutte contre les nuisibles
EP3615540B1 (fr) Dérivés d&#39;hétérocyclène bicycliques condensés en tant que pesticides
EP4144739A1 (fr) Pyrazoles annelés en tant que produit pesticide
EP4036083A1 (fr) Hétéréocycles substitués de 5-oxy en tant que pesticides
WO2022238391A1 (fr) Dérivés hétérocycliques condensés à substitution 2-(het)aryle utilisés comme agents de lutte antiparasitaire
EP4175961A1 (fr) Dérivés d&#39;hétérocyclène utiles en tant qu&#39;agents de lutte contre les nuisibles
AU2022335669A1 (en) Novel pyrazinyl-triazole compounds as pesticides
BR112019006985B1 (pt) Derivados de heterocíclicos fundidos bicíclicos substituídos por 2- (het)arila, seu uso, formulação agroquímica, e método para controle de pragas animais

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21773362

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21773362

Country of ref document: EP

Kind code of ref document: A1