WO2014033244A2 - Composés imines mésoioniques substitués pour lutter contre des nuisibles d'animaux - Google Patents

Composés imines mésoioniques substitués pour lutter contre des nuisibles d'animaux Download PDF

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WO2014033244A2
WO2014033244A2 PCT/EP2013/067962 EP2013067962W WO2014033244A2 WO 2014033244 A2 WO2014033244 A2 WO 2014033244A2 EP 2013067962 W EP2013067962 W EP 2013067962W WO 2014033244 A2 WO2014033244 A2 WO 2014033244A2
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alkyl
independently
formula
compounds
substituted
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WO2014033244A3 (fr
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Arun Narine
Joachim Dickhaut
Florian Kaiser
Nina Gertrud Bandur
Karsten KÖRBER
Wolfgang Von Deyn
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00

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  • the invention relates to substituted mesoionic compounds and salts thereof, to methods for preparing these compounds and to compositions comprising such compounds.
  • the invention also relates to the use of the substituted mesoionic compounds, of their salts or of compositions comprising them for combating animal pests. Furthermore the invention relates to methods of applying such compounds.
  • Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.
  • WO 2012/0921 15 and WO 2012/106495 disclose pesticides having a mesoionic pyrimidine structure.
  • the known compounds are not completely satisfactory in many cases, in terms, for example, of application rate, spectrum of activity, duration of activity, tendency to form resistance or economic aspects of the preparation process.
  • R 1 , R 2 is independently hydrogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals are unsubstituted or substituted with one or more R b ; or R 1 and R 2 together with the nitrogen and carbon atom to which they are bonded, form the following substituted heterocyclic ring system:
  • k 0, 1 , 2, 3 or 4;
  • R 3 is (CR 30 R 31 )aQ 1 , Ci-C6-alkyl unsubstituted or substituted with one or more halogen or C3-C6-cycloalkyl unsubstituted or substituted with 1 to 4 substituents selected from the group consisting of halogen, Ci-C2-alkyl, 1 cyclopropyl and 1 CF3;
  • a is O or l ;
  • R A is hydrogen, Ci-C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 4 -C 8 - cycloalkenyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • R A is OR A0 or N(R A1 ) 2 ;
  • R B is hydrogen, CrC 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are un
  • R B is N(R 9 ) 2 ;
  • each R a is independently halogen, cyano, azido, nitro, SCN, SF 5 , Ci-C 8 -alkyl, C2-C 8 - alkenyl, C2-C 8 -alkynyl, C3-C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • each R c is independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl,
  • each R d is independently Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, or phenyl which is unsubstituted or substituted with one or more substituents selected independently from halogen, cyano, NO2, CiC6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy;
  • each R e is independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl,
  • each R9 is independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxyalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl or C1-C6- haloalkoxyalkyl;
  • each Q 3 is independently phenyl, unsubstituted or substituted with at least one
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from oxygen, nitrogen, sulfur, NO, SO and SO2 unsubstituted or substituted with up to four substituents selected independently from halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; each b is independently 0 or 1 ;
  • each c is independently 0, 1 or 2;
  • substituted mesoionic compounds of formula (I), their N-oxides and their agriculturally or veterinarily acceptable salts are highly active against animal pests, especially harmful arthro- podes and nematodes, in particular against harmful insects and acaridae.
  • the invention provides substituted mesoionic compounds of formula (I), N-oxides and agriculturally or veterinarily useful salts thereof.
  • the invention provides and includes the following embodiments:
  • compositions comprising at least one compound of formula (I), N-oxide or salt thereof;
  • a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (I), N-oxide or salt thereof;
  • a method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of at least one compound of the formula (I), N-oxide or salt thereof;
  • a method for protecting seeds from soil insects and seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermina- tion with at least one compound of formula (I), N-oxide or salt thereof;
  • a method for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of at least one compound of formula (I), N-oxide or veterinarily acceptable salt thereof;
  • a process for the preparation of a composition for treating or protecting animals against infestation or infection by parasites which comprises mixing a parasiticidally effective amount of at least one compound of formula (I), N-oxide or a veterinarily acceptable salt thereof with at least one veterinarily acceptable carrier;
  • the invention also provides plant propagation materials, in particular seeds, comprising at least one compound of formula (I), N-oxide or agriculturally acceptable salt thereof.
  • At least one compound of formula (I), N-oxide or salt thereof means at least one compound selected from the group consisting of compounds of formula (I), N-oxides of the compounds of formula (I), salts of the compounds of formula (I) and salts of the N-oxides of the compounds of formula (I).
  • a compound of the invention means a compound of formula (I), an N-oxide of a compound of formula (I), a salt of a compound of formula (I) or a salt of an N-oxide of a compound of formula (I).
  • the compounds of formula (I) encompass every possible stereoisomer of the compounds of formula (I), e.g. single enantiomers or diastereomers, as well as mixtures thereof.
  • the compounds of formula (I) may be amorphous or may exist in one or more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability, or show different biological properties such as activity against certain pests.
  • the invention encompasses both amorphous and crystalline compounds of formula (I), mixtures of different crystalline states or modifications of the respective compound (I), as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of formula (I) are preferably agriculturally and/or veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question, if the compound of formula (I) has a basic functionality, or by reacting an acidic compound of formula (I) with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4- alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of formula (I) with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.
  • Halogen means fluoro, chloro, bromo and iodo.
  • partially or fully halogenated means that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • C n -C m -alkyl refers to a branched or unbranched saturated hydrocarbon group having n to m, carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2- methylpentyl, 3-methyl
  • Ci-C4-alkyl means for example me- thyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl and 1 ,1 -dimethylethyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, dichlorome- thyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro- fluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2- difluor
  • Ci-Cio-haloalkyl in particular comprises Ci-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted with fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoro- methyl.
  • C n -C m -alkoxy and “C n -C m -alkylthio” refer to straight-chain or branched alkyl groups having n to m carbon atoms, (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group.
  • Examples include Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, futher Ci- C4-alkylthio such as methylthio, ethylthio, propylthio, isopropylthio and n-butylthio.
  • C n -C m -haloalkoxy and "C n -C m -haloalkylthio” refer to straight-chain or branched alkyl groups having n to m carbon atoms, (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloro- methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluo- romethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2- fluoroethoxy, 2,2-difluoro
  • Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bonded to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.
  • C2-C m -alkenyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g.
  • C2-C m -alkynyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, e.g. like the specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group.
  • C3-C m -cycloalkyl refers to a monocyclic 3- to m-membered saturated cycloaliphatic radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.
  • aryl refers to an aromatic hydrocarbon radical such as naph- thyl or in particular phenyl.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
  • heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members
  • ring members refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl include:
  • oxiranyl aziridinyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4
  • Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-
  • 3-, 4-, 5-, 6- or 7-membered aromatic heterocyclyl is 5- or 6-membered aromatic heterocyclyl (hetaryl).
  • Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5- thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • C2-C7-alkylene is divalent branched or preferably unbranched saturated aliphatic chain having 2 to 7 carbon atoms, for example CH 2 CH 2 , -CH(CH 3 )-, CH2CH2CH2, CH(CH 3 )CH 2 , CH 2 CH(CH 3 ), CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2, and
  • the substituted mesoionic compound of formula (I) is a compound of formula (1-1 ):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-2):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-3);
  • the substituted mesoionic compound of formula (I) is a com- pound of formula (1 -4):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-5):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-6):
  • the substitutet mesoionic compound of formula (i) is a compound of formula (1 -7):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-8):
  • the substituted mesoionic compound of formula (I) is a compound of formula (I-9):
  • each A 1 , A 2 , A 3 , A 4 ist independently N or C-R a' ,
  • each R a' is independently H or R a .
  • X is preferably O or S.
  • Y is preferably O or S.
  • A, A 0 is preferably independently phenyl, naphthyl or a 5- or 6-membered heteroaromatic ring system, or a 8-10-membered heteroaromatic bicyclic ring system, each unsubstituted or substituted with up to 6 substituents R a .
  • R 1 , R 2 is preferably independently hydrogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl,
  • R 1 and R 2 together with the nitrogen and carbon atom to which they are bonded, form the fol- lowing substituted heterocyclic ring system:
  • k is preferably 0, 1 or 2.
  • R 3 is preferably (CR 30 R 31 ) a Q 1 .
  • a is preferably 1 .
  • Each R 30 and R 31 is preferably independently hydrogen or halogen, and one of R 30 , R 31 is hydrogen, halogen, cyano, or methyl.
  • Q 1 is preferably a heterocyclic ring system:
  • R A is preferably hydrogen, Ci-C3-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl,
  • R A is OR A0 or N(R A ) 2 .
  • R B is preferably hydrogen, CrC 3 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • Each R a is preferably independently halogen, cyano, Ci-C3-alkyl, C2-C4-alkenyl, C2-C4- alkynyl, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals are unsubstituted or substituted with one or more R b .
  • Each R b is preferably independently halogen, cyano, nitro, Ci-C3-alkoxy, C1-C3- haloalkoxy, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl, C1-C3- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl or C2-C4-haloalkynyl.
  • Each R c is preferably independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxyalkyl, Ci-C6-haloalkoxyalkyl or phenyl which is unsubstituted or substituted with one or more substituents selected independently from halo- gen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • Each R d is preferably independently Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, or phenyl which is unsubstituted or substituted with one or more substituents selected independently from halogen, cyano, NO2, CiC6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy.
  • Each R e is preferably independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, Ci-C6-alkoxyalkyl, Ci-C6-haloalkoxyalkyl or phenyl which is unsubstituted or substituted with one or more substituents selected independently from halo- gen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • Each R f is preferably independently hydrogen, halogen, cyano, nitro, OH , SH , SCN , SF 5 , Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, Ci-
  • Each R9 is preferably independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxyalkyl or Ci- C6-haloalkoxyalkyl.
  • Each Q 3 is preferably independently phenyl, unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from oxygen, nitrogen, sulfur, NO, SO and SO2 unsubstituted or substituted with up to four substituents selected independently from halogen, cyano, NO2, Ci-C6-alkyl,
  • Ci-C6-haloalkyl Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • Each b is preferably independently 0 or 1 .
  • Each c is preferably independently 0, 1 or 2.
  • each of the symbols in formula (I) has the preferred meanings.
  • X is more preferred O.
  • Y is more preferred O.
  • A is more preferred phenyl with up to 3 substituents R a .
  • a 0 is more preferred phenyl with up to 3 substituents R a or pyridyl, with up to 2 substituents R a .
  • R 1 , R 2 is more preferred independently hydrogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals are unsubstituted or substituted with one or more R b ; or
  • R 1 and R 2 together with the nitrogen and carbon atom to which they are bonded, more preferred form the following substituted heterocyclic ring system:
  • k is more preferred 0, 1 or 2.
  • R 3 is more preferred (CR 30 R 31 ) a Q 1 .
  • a is more preferred 1 .
  • Each R 30 and R 31 is more preferred hydrogen and one of R 30 , R 31 , hydrogen or methyl.
  • Q 1 is more preferred a heterocyclic ring system:
  • R A is more preferred Ci-C3-alkyl, C3-C6-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • R A is OR A0 or N(R A ) 2
  • R B is more preferred hydrogen, Ci-C3-alkyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • R B is N(R 9 ) 2 .
  • Each R a is more preferred independently halogen, cyano, OCH3, CF3, OCF3, SCF3 or
  • Each R b is more preferred independently halogen, cyano, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl or Ci-C3-haloalkylthio.
  • Each R c is more preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each R d is more preferred independently Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6-alkenyl, C 2 -C6- haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl or Cs-Cs-halocycloalkyl.
  • Each R e is more preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each R9 is more preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxyalkyl or C1-C6- haloalkoxyalkyl.
  • Each Q 3 is more preferred independently phenyl, unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from oxygen, nitrogen, sulfur, NO, SO and SO2 unsubstituted or substituted with up to four substituents selected independently from halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy.
  • Each b is more preferred independently 0 or 1 .
  • Each c is more preferred independently 0, 1 or 2.
  • each of the symbols in formula (I) has the more preferred meanings.
  • X is especially preferred O.
  • Y is especially preferred O.
  • A is especially preferred phenyl with up to 3 substituents R a .
  • a 0 is especially preferred phenyl with up to 3 substituents R a or pyridyl, with up to 2 substituents R a .
  • R 1 and R 2 together with the nitrogen and carbon atom to which they are bonded, form especially preferred the following substituted heterocyclic ring system:
  • k is especially preferred 0, 1 or 2.
  • R 3 is especially preferred CH 2 Q 1 or CH(CH 3 )Q 1 .
  • Q 1 is especially preferred a heterocyclic ring system:
  • R A is especially preferred Ci-C3-alkyl, C3-C6-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • R A is OR A0 or N(R A ) 2 .
  • R B is especially preferred hydrogen, Ci-C3-alkyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R b ,
  • R B is N(R 9 ) 2 .
  • Each R c is especially preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each R d is especially preferred independently Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6-alkenyl, C 2 - C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl or Cs-Cs-halocycloalkyl.
  • Each R e is especially preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each Rs is especially preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Ci-C6-alkoxyalkyl or C1-C6- haloalkoxyalkyl.
  • Each Q 3 is especially preferred independently phenyl, unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy, a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from oxygen, nitrogen, sulfur, NO, SO and SO2 unsubstituted or substituted with up to four substituents selected independently from halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy.
  • Each b is especially preferred independently 0 or 1 .
  • Each c is especially preferred independently 0, 1 or 2.
  • X is particularly preferred O.
  • Y is particularly preferred O.
  • A, A 0 is particularly preferred independently phenyl, unsubstituted or substituted with up to
  • R 1 and R 2 together with the nitrogen and carbon atom to which they are bonded, particularly preferred form the following substituted heterocyclic ring system:
  • CH2Q 1 is particularly preferred.
  • R A is particularly preferred Ci-C3-alkyl, C3-C6-cycloalkyl, Ci-C3-haloalkyl or C3-C6- halocycloalkyl;
  • R A is OR A0 or N(R A ) 2 .
  • R B is particularly preferred hydrogen, Ci-C3-alkyl, Ci-C3-haloalkyl or C3-C6-halocycloalkyl.
  • Each R c is particularly preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each R d is particularly preferred independently Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl.
  • Each R e is particularly preferred independently hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxyalkyl or Ci-C6-haloalkoxyalkyl.
  • Each R f is particularly preferred independently hydrogen, halogen, cyano, nitro, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylthio, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals are unsubstituted, partially or fully halogenated.
  • Each Q 3 is particularly preferred independently phenyl, unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from oxygen, nitrogen, sulfur, NO, SO and SO2 unsubstituted or substituted with up to four substituents selected independently from halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy.
  • Each b is particularly preferred independently 0 or 1 .
  • Each c is particularly preferred independently 0, 1 or 2.
  • each of the symbols in formula (I) has the particularly preferred meanings.
  • R a' , R a" each independently are hydrogen or R a , and
  • R a' , R 30 , Q 1 , R A , R B have the meanings given in formula (I)
  • Me is CHs
  • Et is C 2 H 5
  • i-Pr isCH(CH 3 ) 2
  • c-Pr is cyclopropyl.

Abstract

L'invention concerne un composé mésoionique substitué de formule (I) où les symboles ont les significations données dans la description, qui est approprié pour la lutte contre des nuisibles.
PCT/EP2013/067962 2012-09-03 2013-08-30 Composés imines mésoioniques substitués pour lutter contre des nuisibles d'animaux WO2014033244A2 (fr)

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WO2017093214A1 (fr) * 2015-12-03 2017-06-08 Bayer Cropscience Aktiengesellschaft Dérivés mésoioniques halogénés de 3-(acétyl)-1-[(1,3-thiazol-5-yl)méthyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate et composés associés en tant qu'insecticides
WO2018062082A1 (fr) * 2016-09-28 2018-04-05 日本化薬株式会社 Nouveau composé insecticide mésoionique
WO2018108730A1 (fr) * 2016-12-16 2018-06-21 Bayer Aktiengesellschaft Imidazopyridines mésoioniques utilisées comme insecticides
WO2018189077A1 (fr) * 2017-04-12 2018-10-18 Bayer Aktiengesellschaft Imidazopyridines mésoioniques utilisées comme insecticides
WO2019086474A1 (fr) 2017-10-31 2019-05-09 Syngenta Participations Ag Composés hétérocycliques mésoioniques à activité pesticide
WO2019115404A1 (fr) 2017-12-13 2019-06-20 Syngenta Participations Ag Composés hétérocycliques mésoioniques à activité pesticide
US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides

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WO2011017342A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2011017334A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2012106495A1 (fr) * 2011-02-03 2012-08-09 E. I. Du Pont De Nemours And Company Pesticides méso-ioniques

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Publication number Priority date Publication date Assignee Title
WO2011017342A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2011017334A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2012106495A1 (fr) * 2011-02-03 2012-08-09 E. I. Du Pont De Nemours And Company Pesticides méso-ioniques

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US10986840B2 (en) 2015-08-07 2021-04-27 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
WO2017093214A1 (fr) * 2015-12-03 2017-06-08 Bayer Cropscience Aktiengesellschaft Dérivés mésoioniques halogénés de 3-(acétyl)-1-[(1,3-thiazol-5-yl)méthyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate et composés associés en tant qu'insecticides
CN108602819A (zh) * 2015-12-03 2018-09-28 拜耳作物科学股份公司 作为杀虫剂的介离子卤化的3-(乙酰基)-1-[(1，3-噻唑-5-基)甲基]-1H-咪唑并[1，2-a]吡啶-4-鎓-2-醇盐衍生物和相关化合物
WO2018062082A1 (fr) * 2016-09-28 2018-04-05 日本化薬株式会社 Nouveau composé insecticide mésoionique
JPWO2018062082A1 (ja) * 2016-09-28 2019-07-11 日本化薬株式会社 新規メソイオン性殺虫化合物
WO2018108730A1 (fr) * 2016-12-16 2018-06-21 Bayer Aktiengesellschaft Imidazopyridines mésoioniques utilisées comme insecticides
JP2020502110A (ja) * 2016-12-16 2020-01-23 バイエル・アクチエンゲゼルシヤフト 殺虫剤として使用するためのメソイオン性イミダゾピリジン類
CN110225915A (zh) * 2016-12-16 2019-09-10 拜耳公司 用作杀虫剂的介离子咪唑并吡啶
CN110691781A (zh) * 2017-04-12 2020-01-14 拜耳公司 用作杀虫剂的介离子咪唑并吡啶
WO2018189077A1 (fr) * 2017-04-12 2018-10-18 Bayer Aktiengesellschaft Imidazopyridines mésoioniques utilisées comme insecticides
WO2019086474A1 (fr) 2017-10-31 2019-05-09 Syngenta Participations Ag Composés hétérocycliques mésoioniques à activité pesticide
WO2019115404A1 (fr) 2017-12-13 2019-06-20 Syngenta Participations Ag Composés hétérocycliques mésoioniques à activité pesticide

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