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WO2025026738A1 - Dérivés de 6-[5-(éthylsulfonyl)-1-méthyl-1h-imidazol-4-yl]-7-méthyl-3-(pentafluoroéthyl)-7h-imidazo [4,5-c]pyridazine en tant que pesticides - Google Patents

Dérivés de 6-[5-(éthylsulfonyl)-1-méthyl-1h-imidazol-4-yl]-7-méthyl-3-(pentafluoroéthyl)-7h-imidazo [4,5-c]pyridazine en tant que pesticides Download PDF

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Publication number
WO2025026738A1
WO2025026738A1 PCT/EP2024/070220 EP2024070220W WO2025026738A1 WO 2025026738 A1 WO2025026738 A1 WO 2025026738A1 EP 2024070220 W EP2024070220 W EP 2024070220W WO 2025026738 A1 WO2025026738 A1 WO 2025026738A1
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spp
methyl
cycloalkyl
cyano
compounds
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Inventor
Yolanda Cancho Grande
Rüdiger Fischer
Steffen Müller
Yeshua SEMPERE MOLINA
Matthieu WILLOT
Elke Hellwege
Kerstin Ilg
Marc LINKA
Peter Lösel
Manuel SOMMER
Olga Malsam
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents

Definitions

  • BCS233014 FC-Text Gam/lep 2024-05-29 - 1 - Heterocycle derivatives as pesticides
  • the present invention relates to heterocycle derivatives of the formula (I), to their use as acaricides and/or insecticides for controlling animal pests, particularly arthropods and especially insects and arachnids, and to methods and intermediates for their preparation.
  • Heterocycle derivatives having insecticidal properties are already described in the literature, for example in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/180193, WO 2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557, WO 2015/121136, WO 2015/133603, WO 2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO 2016/005263, WO 2016/039441, WO 2015/198817, WO 2016/041819, WO 2016/039441, WO 2016/039444, WO 2016/026848, WO 2016/023954, WO 2016/020286, WO 2016/046071, WO 2016/058928, WO 2016/059145, WO 2016/071214, WO 2016/091731
  • Novel heterocycle derivatives have now been found, these having advantages over the compounds already known, examples of which include better biological or environmental properties, a wider range of application methods, better insecticidal or acaricidal action, and good compatibility with crop plants.
  • the heterocycle derivatives can be used in combination with further compositions for improving efficacy, especially against insects that are difficult to control.
  • R 1 represents aryl or 5 to 6 membered hetaryl, each of which is optionally mono- or polysubstituted by identical or different substituents, where (in the case of hetaryl) at least one carbonyl group may optionally be present and where possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, SCN, SF5, tri(C1-C4)alkylsilyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3- C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, (C1-C4)haloalkyl-(C3-C6)cycloalkyl, halo(C3- C6)cycloalkyl, cyano(configuration 1-1)
  • R 1 represents aryl or 5 to 6 membered hetaryl, each of which is optionally mono- or polysubsti
  • the compounds of the formula (I) have very good efficacy as pesticides, preferably as insecticides and/or acaricides, and additionally generally have very good plant compatibility, in particular with respect to crop plants.
  • the compounds according to the invention are defined in general terms by the formula (I).
  • R 1 preferably represents phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, furanyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where (in the case of hetaryl) at least one carbonyl group may optionally be present and where possible substituents in each case are as follows: cyano, halogen, nitro, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3- C6)cycloalkyl, (C1-C4)
  • R 1 particularly preferably represents phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, pyrazolyl or thiazolyl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents, where possible substituents in each case are as follows: cyano, halogen, nitro, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C3-C6)cycloalkyl, (C1-C4)alkyl-(C3-C6)cycloalkyl, (C1-C4)haloalkyl-(C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, cyano(C3-C6)cycloalkyl, (C1- C4)alkyl, (C1-C4)haloalkyl, (C1-C4)cyanoalkyl,
  • R 1 very particularly preferably represents phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, pyrazolyl, thiazolyl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents – bridged via a carbon atom to the rest of the molecule – where possible substituents in each case are as follows: cyano, halogen, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkyl-(C 3 - C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, cyano(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C
  • R 1 with emphasis represents phenyl, pyridyl (pyridinyl), pyrimidyl (pyrimidinyl), pyridazinyl, pyrazinyl, thienyl, pyrazolyl, thiazolyl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents – bridged via a carbon atom to the rest of the molecule – where possible substituents in each case are as follows: cyano, fluorine, bromine, chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyclopropyl, 1-cyanocyclopropyl, 1- trifluoromethylcyclopropyl, 1-fluorocyclopropyl, 2-cyanopropan-2-yl, cyano(difluoro)methyl, methoxyimino, ethoxyimino, aminocarbonyl, chlorophenyl or chloropyridy
  • Configuration 5-2 R 1 with emphasis represents phenyl which is optionally mono-, di- or trisubstituted by identical or different substituents where possible substituents in each case are as follows: cyano, fluorine, bromine, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluorocyclopropyl, methoxyimino, ethoxyimino, aminocarbonyl or chlorophenyl, or pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, pyrazolyl, thiazolyl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents – bridged via a carbon BCS233014 FC-Text - 5 - atom to the rest of the molecule – where possible substituents in each case are as follows: cyano, fluorine, bromine, chlorine, methyl,
  • Configuration 6-1 R 1 especially represents phenyl, which is mono-, di- or trisubstituted identically or differently by fluorine, bromine, chlorine, cyano, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1- fluorocyclopropyl, aminocarbonyl, methoxyimino, ethoxyimino or chlorophenyl, or pyridin-2-yl which is optionally mono- or disubstituted identically or differently by fluorine, bromine, chlorine, cyano, trifluoromethyl, trifluoromethoxy or 1-cyanocyclopropyl, or pyridin-3-yl which is monosubstituted by fluorine, chlorine, cyano, cyano(difluoro)methyl (-CF 2 CN), methoxy, aminocarbonyl, 1-cyanocyclopropyl or chloropyridin-3-yl, or pyridin-4-yl which is monosub
  • FC-Text - 6 - R 1 especially represents phenyl, which is mono-, di- or trisubstituted identically or differently by fluorine, bromine, cyano, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1- fluorocyclopropyl, aminocarbonyl, methoxyimino, ethoxyimino or chlorophenyl, or pyridin-2-yl which is optionally mono- or disubstituted identically or differently by fluorine, bromine, chlorine, cyano, trifluoromethyl, trifluoromethoxy or 1-cyanocyclopropyl, or pyridin-3-yl which is monosubstituted by fluorine, chlorine, cyano, cyano(difluoro)methyl (-CF2CN), methoxy, aminocarbonyl, 1-cyanocyclopropyl or chloropyridin-3-yl, or pyr
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is optionally mono-, di- or trisubstituted identically or differently by fluorine, bromine, chlorine, cyano, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1- fluorocyclopropyl, aminocarbonyl, methoxyimino, ethoxyimino or chlorophenyl.
  • R 1 represents phenyl, which is optionally mono-, di- or trisubstituted identically or differently by fluorine, bromine, chlorine, cyano, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1- fluorocyclopropyl, aminocarbonyl, methoxyimino, ethoxyimino or chlorophenyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is optionally mono-, di- or trisubstituted identically or differently by fluorine, cyano, methyl, 1-cyanocyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluorocyclopropyl, aminocarbonyl, methoxyimino, ethoxyimino or chlorophenyl.
  • R 1 represents phenyl, which is optionally mono-, di- or trisubstituted identically or differently by fluorine, bromine or chlorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is mono-, di- or trisubstituted by fluorine. In a preferred embodiment, the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is monosubstituted by fluorine, bromine or chlorine. In a preferred embodiment, the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is disubstituted identically or differently by fluorine, bromine or chlorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is trisubstituted identically or differently by fluorine, bromine or chlorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is monosubstituted by fluorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is disubstituted by fluorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is trisubstituted by fluorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is monosubstituted by chlorine. In a preferred embodiment, the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is disubstituted by chlorine. In a preferred embodiment, the invention relates to compounds of the formula (I), in which R 1 represents phenyl, which is trisubstituted by chlorine.
  • the invention relates to compounds of the formula (I), in which BCS233014 FC-Text - 8 - R 1 represents pyridin-2-yl which is optionally mono- or disubstituted identically or differently by fluorine, bromine, chlorine, cyano, trifluoromethyl, trifluoromethoxy or 1-cyanocyclopropyl, or pyridin-3-yl which is monosubstituted by fluorine, chlorine, cyano, cyano(difluoro)methyl, methoxy, aminocarbonyl, 1-cyanocyclopropyl or chloropyridin-3-yl, or pyridin-4-yl which is monosubstituted by chlorine, 2-cyanopropan-2-yl (-C(CH3)2CN) or chloropyridin-4-yl, or pyridazin-3-yl which is monosubstituted by chlorine or cyano, or pyrimidin-2-yl which is mono- or
  • the invention relates to compounds of the formula (I), in which R 1 represents pyridin-2-yl which is optionally mono- or disubstituted identically or differently by fluorine, bromine, chlorine, cyano, trifluoromethyl, trifluoromethoxy or 1-cyanocyclopropyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents pyridin-3-yl which is monosubstituted by fluorine, chlorine, cyano, cyano(difluoro)methyl, methoxy, aminocarbonyl, 1-cyanocyclopropyl or chloropyridin-3-yl.
  • the invention relates to compounds of the formula (I), in which R 1 represents pyridin-4-yl which is monosubstituted by chlorine, 2-cyanopropan-2-yl (-C(CH 3 ) 2 CN) or chloropyridin-4-yl.
  • the invention relates to compounds of the formula (I), in which R 1 represents pyridazin-3-yl which is monosubstituted by chlorine or cyano.
  • the invention relates to compounds of the formula (I), in which R 1 represents pyrimidin-2-yl which is mono- or disubstituted identically or differently by fluorine, bromine, chlorine, cyano, trifluoromethyl or methoxy.
  • the invention relates to compounds of the formula (I), in which R 1 represents pyrazin-2-yl which is monosubstituted by chlorine.
  • the invention relates to compounds of the formula (I), in which R 1 represents 1H-pyrazol-4-yl which is monosubstituted by methyl, cyclopropyl or 1-cyanocyclopropyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents 1H-pyrazol-3-yl which is monosubstituted by methyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents 1H-pyrazol-1-yl which is optionally monosuhstituted by bromine, chlorine, iodine, cyano or trifluoromethyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents thien-2-yl which is monosubstituted by 1-cyanocyclopropyl.
  • the invention relates to compounds of the formula (I), in which R 1 represents 1,3-thiazol-2-yl which is monosubstituted by bromine, chlorine or cyano.
  • R 1 represents 1,3-thiazol-2-yl which is monosubstituted by bromine, chlorine or cyano.
  • halogen is selected from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of fluorine, chlorine and bromine.
  • Aryl (including as part of a larger unit, for example arylalkyl), unless defined differently elsewhere, is selected from the series phenyl, naphthyl, anthryl, phenanthrenyl, and is preferably in turn phenyl.
  • alkyl either on its own or else in combination with further terms, for example haloalkyl, is understood to mean a radical of a saturated, aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may be branched or unbranched.
  • C 1 -C 12 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1- ethylpropyl, 1,2-dimethylpropyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.
  • alkenyl either on its own or else in combination with further terms, is understood to mean a straight-chain or branched C2-C12-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.
  • alkynyl either on its own or else in combination with further terms, is understood to mean a straight-chain or branched C 2 -C 12 -alkynyl radical which has at least one triple bond, for example ethynyl, 1-propynyl and propargyl.
  • the alkynyl radical may also contain at least one double bond.
  • cycloalkyl either on its own or else in combination with further terms, is understood to mean a C 3 -C 8 -cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Among these, preference is given to C 3 -C 6 -cycloalkyl radicals.
  • alkoxy either on its own or else in combination with further terms, for example haloalkoxy, is understood in the present case to mean an O-alkyl radical, where the term "alkyl" is as defined above.
  • Halogen-substituted radicals for example haloalkyl, are mono- or polyhalogenated, up to the maximum number of possible substituents.
  • the halogen atoms may be identical or different.
  • Halogen here is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine.
  • optionally substituted radicals may be mono- or polysubstituted, where the substituents in the case of polysubstitutions may be the same or different.
  • the radical definitions or illustrations given above in general terms or listed within ranges of preference apply correspondingly to the end products and to the starting materials and intermediates. These radical definitions can be combined with one another as desired, i.e.
  • Preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. Particular preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred. BCS233014 FC-Text - 11 - Very particular preference according to the invention is given to using compounds of the formula (I) which contain a combination of the definitions listed above as being very particularly preferred. Emphasis according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being emphasized. Special emphasis according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being especially emphasized.
  • the compounds of the formula (I) may be in the form of geometric and/or optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Isotopic variants The present invention also encompasses all suitable isotopic variants of the compounds of the formula (I).
  • An isotopic variant of such a compound is understood to mean a compound of the formula (I) in which at least one atom is replaced by another atom of the same atomic number, but with a different atomic mass than the atomic mass usually or predominantly occurring in nature.
  • isotopes that can be incorporated into a compounds of the formula (I) are those of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, bromine and iodine, such as 2 H (deuterium), 3 H (tritium), 13 C, 14 C, 15 N, 17 O, 18 O, 32 P, 33 P, 33 S, 34 S, 35 S, 36 S, 18 F, 36 Cl, 82 Br, 123 I, 124 I, 129 I and 131 I.
  • isotopic variants of a compounds of the formula (I), such as in particular those in which one or more radioactive isotopes are incorporated, can be useful, for example, for investigating the mechanism of action or the active ingredient distribution, for example in the body of a pathogen; for this purpose, compounds labeled with 3 H or 14 C isotopes are particularly suitable, because their production and detection which is comparatively easy.
  • isotopes such as, for example, deuterium
  • Isotopic modifications of the compounds of the formula (I) can therefore also represent a preferred embodiment of the invention.
  • Isotopic variants of the compounds of the formula (I) can be prepared by methods known to the person skilled in the art, for example by the methods described below and the instructions given in the exemplary embodiments, by using appropriate isotopic modifications of the respective reagents and/or starting compounds (educts).
  • the inventive compounds of the formula (I) can be obtained by the processes shown in the following schemes: BCS233014 FC-Text - 12 - Process A
  • R 1 is preferably aryl, 6- membered hetaryl or C-connected 5-membered hetaryl (R 1 is bridged via a carbon atom to the rest of the molecule) is described below.
  • the radical R 1 has the meanings described above.
  • Step a) Compound of the formula (IV) can be prepared from starting materials (II) and (III) in the presence of a condensing agent.
  • Compound (II) is either commercially available or can be prepared by known methods, for example analogously to the methods described in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2015/000715, WO 2015/121136, WO 2016/039441, WO 2016/059145, WO 2016/071214, WO 2016/169882, WO 2016/169886 or WO 2016/124557.
  • Compound of the formula (III) can be prepared by known methods, for example analogously to the methods described in WO 2018/130437, WO 2018/130443, WO 2020/002082
  • the conversion to compound of the formula (IV) can be effected neat or in a solvent, preference being given to conducting the reaction in a solvent selected from customary solvents that are inert under the prevailing reaction conditions.
  • ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons, for example dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanol or isopropanol; nitriles, for example acetonitrile or propionitrile; aromatic hydrocarbons, for example toluene or xylene; aprotic polar solvents, for example N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, for example pyridine.
  • halogenated hydrocarbons for example dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene
  • alcohols such as methanol, ethanol or isopropan
  • suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride, or a mixture of triphenylphosphine and an azo diester, for example diethylazodicarboxylic acid.
  • the reaction can be conducted in the presence of a suitable catalyst, for example 1-hydroxybenzotriazole.
  • the reaction can be carried out in the presence of an acid or a base.
  • an acid which can be used in the reaction described are sulfonic acids such as methanesulfonic acid or para-toluenesulfonic acid; carboxylic acids such as acetic acid, or polyphosphoric acids.
  • suitable bases are nitrogenous heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8- diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N- diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • Step b) The compounds of the formulas (V) or (I) can be prepared by oxidation of the corresponding intermediates of the formula (IV) or (VI), for example analogously to the methods described in WO 2018/130437, WO 2018/130443 or WO 2020/002082.
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons, for example dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing compositions is hydrogen peroxide and meta-chloroperbenzoic acid.
  • Step c) Compounds of the formulas (IV) or (V) may be converted to compounds of the corresponding formula (VI) or (I), for example by transition metal-mediated cross-couplings [cf. Chem. Rev. 1995, 95, 2457- 2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed.,Wiley-VCH, Weinheim, 2004] or by nucleophilic aromatic substitution (cf. the processes described in Bioorganic and Medicinal Chemistry Letters 2007, 17, 5825-5830 or US 4125726).
  • transition metal-mediated cross-couplings cf. Chem. Rev. 1995, 95, 2457- 2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F.
  • compounds of the formula (IV) or (V) may be reacted with suitable boronic acids [R 1 - B(OH)2] or boronic esters according to known methods (cf. WO 2012/143599, US 2014/094474, US 2014/243316, US 2015/284358 or Journal of Organic Chemistry 2004, 69, 8829-8835) in the presence of suitable catalysts from the series of transition metal salts to give compounds of the formula (VI) or (I).
  • preferred coupling catalysts include palladium catalysts such as [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(triphenylphosphine)palladium(II) dichloride or tetrakis(triphenylphosphine)palladium.
  • Suitable basic reaction auxiliaries used to conduct the processes are preferably carbonates of sodium, potassium or caesium.
  • Some of the required boronic acid derivatives [R 1 -B(OH)2] or boronic ester derivatives are known and/or commercially available, or they can be prepared by generally known methods (cf.
  • the reaction is preferably conducted in a mixture of water and an organic solvent selected from customary solvents that are inert under the prevailing reaction conditions.
  • Ethers such as tetrahydrofuran, dioxane or 1,2-dimethoxyethane are frequently used.
  • stannane derivatives [R 1 -Sn(n-Bu) 3 ] as coupling partners (cf. US 2013/281433, WO 2004/099177 or WO 2016/071214).
  • R 1 - Sn(n-Bu) 3 Some of the required stannane derivatives [R 1 - Sn(n-Bu) 3 ] are known and/or commercially available, or they can be prepared by generally known methods (cf. WO 2016/071214 or WO 2007/148093).
  • Process B The general method for the preparation of compounds of the formula (I) in which R 1 is preferably aryl, 6- membered hetaryl or C-connected 5-membered hetaryl hetaryl (R 1 is bridged via a carbon atom to the rest of the molecule) is described below.
  • the radical R 1 has the meanings described above.
  • X is halogen, preferably iodine or bromine.
  • Step a) The conversion of compound of the formula (II) into compound of the formula (VII) is carried out in BCS233014 FC-Text - 15 - acetic acid or triethyl orthoformate at high temperatures, e.g. between 120 °C and 150 °C and eventually assisted by microwaves as described in US 2019/202829 or US 2020/146293.
  • Step b) The compound of the formula (VII) is coupled with compound of the formula (VIII) to give compound of the formula (IX) as described in WO 2020/074558.
  • the deprotonation of compound of the formula (VII) is generally carried out in tetrahydrofurane using 2,2,6,6-tetramethylpiperidinylzinc chloride lithium chloride as a base and the in-situ Negishi coupling is carried out using preferentially tetrakis(triphenylphosphine)palladium(0) or XPhos-G3-palladacycle as a catalyst and at temperatures between 60 °C and 80 °C.
  • the synthesis of compound of the formula (VIII) is described in US 2022/009930.
  • Step c) The compound of the formula (IX) is coupled with halogenated cycles of the formula R 1 -X to give compounds of the formula (VI) as described in WO 2020/074560.
  • the deprotonation of compounds of the formula (IX) is generally carried out in tetrahydrofurane using 2,2,6,6-tetramethylpiperidinylzinc chloride lithium chloride as a base and the in-situ Negishi coupling is carried out using preferentially tetrakis(triphenylphosphine)palladium(0) or XPhos-G3-palladacycle as a catalyst and at temperatures included between 60 °C and 80 °C.
  • the compounds of the formula (I) can be prepared by oxidation of compounds of the formula (VI), for example analogously to the methods described in WO 2018/130437, WO 2018/130443 or WO 2020/002082.
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons, for example dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing compositions is hydrogen peroxide and meta-chloroperbenzoic acid.
  • reaction can be carried out under an inert gas atmosphere by catalysis with copper(I) salts, copper(I) iodide for example, in the presence of a suitable ligand, e.g. trans-N,N'- dimethylcyclohexane-1,2-diamine or R-(+)-proline, and a suitable base, e.g. potassium carbonate or potassium phosphate, in a suitable solvent such as 1,4-dioxane or toluene (cf., for example WO 2016/109559).
  • a suitable ligand e.g. trans-N,N'- dimethylcyclohexane-1,2-diamine or R-(+)-proline
  • a suitable base e.g. potassium carbonate or potassium phosphate
  • a suitable solvent such as 1,4-dioxane or toluene (cf., for example WO 2016/109559).
  • Step b) The compounds of the formula (I) can be prepared by oxidation of compounds of the formula (VI), for example analogously to the methods described in WO 2018/130437, WO 2018/130443 or WO 2020/002082.
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons, for example dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing compositions is hydrogen peroxide and meta-chloroperbenzoic acid.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and/or their habitat.
  • the control of the animal pests is preferably conducted in agriculture and forestry, and in material protection.
  • Preferably excluded herefrom are methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods carried out on the human or animal body.
  • the invention furthermore relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
  • the term "pesticide” in each case also always comprises the term "crop protection agent".
  • the compounds of the formula (I) having good plant tolerance, favourable homeotherm toxicity and good environmental compatibility, are suitable for protecting plants and plant organs against biotic and abiotic stressors, for increasing harvest yields, for improving the quality of the harvested material and for controlling animal pests, especially insects, arachnids, helminths, in particular nematodes, and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in aquatic cultures, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector.
  • the term “hygiene” is understood to mean any and all measures, procedures and practices which aim to prevent disease, in particular infectious disease, and which serve to protect the health of humans and animals and/or to protect the environment, and/or which maintain cleanliness.
  • this especially includes measures for cleaning, disinfection and sterilisation of, for example, textiles or hard surfaces, especially surfaces of glass, wood, concrete, porcelain, ceramics, plastic or also of metal(s), and for ensuring that these are kept free of hygiene pests and/or their excretions.
  • surgical or therapeutic treatment procedures applicable to the human body or to the bodies of animals and diagnostic procedures which are carried out on the human body or on the bodies of animals.
  • honeygiene sector thus covers all areas, technical fields and industrial applications in which these hygiene measures, procedures and practices are important, in relation for example to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandries, etc.
  • the term “hygiene pest” is therefore understood to mean one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons. It is therefore a primary objective to avoid or minimize the presence of hygiene pests, and/or exposure to them, in the hygiene sector. This can be achieved in particular through the application of a pesticide that can be used both to prevent infestation and to tackle an infestation which is already present. Preparations which avoid or reduce exposure to pests can also be used.
  • Hygiene pests include, for example, the organisms mentioned below.
  • the term “hygiene protection” thus covers all actions to maintain and/or improve these hygiene measures, procedures and practices.
  • 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 stages of development.
  • pests from the phylum of the Arthropoda in particular from the class of the Arachnida, for example Acarus spp., for example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculus fockeui, Aculus Mattendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., for example Brevipalpus phoenicis, Bryobia graminum, Bryobia BCS233014 FC-Text - 18 - praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacent
  • phytoparasitic nematodes in particular Aglenchus spp., for example Aglenchus agricola, Anguina spp., for example Anguina tritici, Aphelenchoides spp., for example Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., for example Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., for example Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella
  • the compounds of the formula (I) can optionally, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
  • Formulations/Use forms The present invention further relates to formulations, in particular formulations for controlling unwanted controlling animal pests. The formulation may be applied to the animal pest and/or in their habitat.
  • the formulation of the invention may be provided to the end user as “ready-for-use” use form, i.e. the formulations may be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device.
  • the formulations may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.
  • the wording “formulation” therefore means such concentrate
  • the wording “use form” means the end user as “ready-for-use” solution, i.e. usually such diluted formulation.
  • the formulation of the invention can be prepared in conventional manners, for example by mixing the compound of the invention with one or more suitable auxiliaries, such as disclosed herein.
  • the formulation comprises at least one compound of the invention and at least one agriculturally suitable auxiliary, e.g. carrier(s) 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 instance, to plants, plants parts or seeds.
  • suitable solid carriers include, but are not limited to, ammonium salts, in particular ammonium sulfates, ammonium phosphates and ammonium nitrates, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel and synthetic rock flours, such as finely divided silica, alumina and silicates.
  • ammonium salts in particular ammonium sulfates, ammonium phosphates and ammonium nitrates
  • natural rock flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth
  • silica gel and synthetic rock flours such as finely divided silica, alumina and silicates.
  • typically useful 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 material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.
  • suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as ethanol, propanol, butanol, benzylalcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted
  • the carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • a liquefied gaseous extender i.e. liquid which is gaseous at standard temperature and under standard pressure
  • aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • Preferred solid carriers are selected from clays, talc and silica.
  • Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and nonaromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly)ethers.
  • the amount of carrier typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the formulation.
  • Liquid carriers are typically present in a range of from 20 to 90%, for example 30 to 80% by weight of the formulation.
  • Solid carriers are typically present in a range of from 0 to 50%, preferably 5 to 45%, for example 10 to 30% by weight of the formulation. If the formulation comprises two or more carriers, the outlined ranges refer to the total amount of carriers.
  • the surfactant can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s), penetration enhancer(s) and any mixtures thereof.
  • surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated polya(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 sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols (such a fatty acid esters of g
  • any reference to salts in this paragraph refers preferably to the respective alkali, alkaline earth and ammonium salts.
  • Preferred surfactants are selected from ethoxylated polya(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 surfactants typically ranges from 5 to 40%, for example 10 to 20%, by weight of the formulation.
  • auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids BCS233014 FC-Text - 27 - 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.
  • binders adheresive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids BCS233014 FC-Text
  • stabilizers e.g. cold stabilizers, preservatives (e.g. dichlorophene, benzyl alcohol hemiformal, 1,2-Benzisothiazolin-3-on, 2- methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, in particular UV stabilizers, or other agents which improve chemical and/or physical stability
  • dyes or pigments such as inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g.
  • auxiliaries mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.
  • the choice of the auxiliaries depends on the intended mode of application of the compound of the invention and/or on the physical properties of the compound(s).
  • the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the formulations or use forms prepared therefrom. The choice of auxiliaries may allow customizing the formulations to specific needs.
  • the formulation comprises an insecticidal/acaricidal/nematicidal effective amount of the compound(s) of the invention.
  • effective amount denotes an amount, which is sufficient for controlling harmful insects/mites/nematodes on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the insect/mite/nematode species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of the invention used.
  • the formulation according to the invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferred from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of the invention. It is possible that a formulation comprises two or more compounds of the invention. In such case the outlined ranges refer to the total amount of compounds of the present invention.
  • the formulation of the invention may be in any customary formulation type, 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, granules for broadcasting suspoemulsion concentrates, natural or synthetic products impregnated with the compound of the invention, fertilizers and also microencapsulations in polymeric substances.
  • the compound of the invention may be present in a suspended, emulsified or dissolved form.
  • suitable formulation types are solutions, watersoluble concentrates (e.g. SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (e.g. SC, OD, OF, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME, SE), capsules (e.g.
  • the formulation of the invention is in form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, more preferred EC, SC, OD, WG, CS. Further details about examples of formulation types and their preparation are given below. If two or more compounds of the invention are present, the outlined amount of compound of the invention refers to the total amount of compounds of the present invention. This applies mutatis mutandis for any further component of the formulation, if two or more representatives of such component, e.g. wetting agent, binder, are present.
  • Water-soluble concentrates (SL, LS) 10-60 % by weight of at least one compound of the invention and 5-15 % by weight surfactant (e.g. polycondensates of ethylene oxide and/or propylene oxide with alcohols) are dissolved in such amount of water and/or water-soluble solvent (e.g. alcohols such as propylene glycol or carbonates such as propylene carbonate) to result in a total amount of 100 % by weight. Before application the concentrate is diluted with water.
  • Dispersible concentrates (DC) 5-25 % by weight of at least one compound of the invention and 1-10 % by weight surfactant and/or binder (e.g.
  • Emulsifiable concentrates EC 15-70 % by weight of at least one compound of the invention and 5-10 % by weight 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 needed additional water-soluble solvent to result in a total amount of 100 % by weight.
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • Emulsions EW, EO, ES 5-40 % by weight of at least one compound of the invention and 1-10 % by weight surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and/or propylene oxide with or without alcohols) are dissolved in 20-40 % by weight water- BCS233014 FC-Text - 29 - insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is added to such amount of water by means of an emulsifying machine to result in a total amount of 100 % by weight.
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and/or propylene oxide with or without alcohols
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and cast
  • the resulting formulation is a homogeneous emulsion. Before application the emulsion may be further diluted with water.
  • SC, FS Water-based
  • 20-60 % by weight of at least one compound of the invention are comminuted with addition of 2-10 % by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 % by weight thickener (e.g. xanthan gum) and water to give a fine active substance suspension.
  • surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
  • thickener e.g. xanthan gum
  • Dilution with water gives a stable suspension of the active substance.
  • binder e.g. polyvinylalcohol
  • a suitable grinding equipment e.g. an agitated ball mill
  • 20-60 % by weight of at least one compound of the invention are comminuted with addition of 2-10 % by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 % by weight thickener (e.g. modified clay, in particular Bentone, or silica) and an organic carrier to give a fine active substance oil suspension.
  • surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
  • thickener e.g. modified clay, in particular Bentone, or silica
  • the organic carrier is added in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion of the active substance.
  • Water-dispersible granules and water-soluble granules (WG, SG) 1-90 % by weight, preferably 20-80%, most preferably 50-80 % by weight of at least one compound of the invention are ground finely with addition of surfactant (e.g. sodium lignosulfonate and sodium alkylnaphthylsulfonates) and potentially carrier material and converted to water-dispersible or water- soluble granules by means of typical technical appliances like e.g. extrusion, spray drying, fluidized bed granulation.
  • surfactant e.g. sodium lignosulfonate and sodium alkylnaphthylsulfonates
  • the surfactant and carrier material are used in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 % by weight of at least one compound of the invention are ground in a rotor-stator mill with addition of 1-20 % by weight surfactant (e.g. sodium lignosulfonate, sodium alkylnaphthylsulfonates) and such amount of solid carrier, e.g. silica gel, to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • surfactant e.g. sodium lignosulfonate, sodium alkylnaphthylsulfonates
  • solid carrier e.g. silica gel
  • Microcapsules An oil phase comprising 5-50 % by weight of at least one compound of the invention, 0-40 % by weight water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 % by weight acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol
  • Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 % by weight of at least one compound of the invention, 0-40 % by weight water-insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g.
  • xii) Granules (GR, FG) 0.5-30 % by weight of at least one compound of the invention are ground finely and associated with such amount of solid carrier (e.g. silicate) to result in a total amount of 100 % by weight.
  • solid carrier e.g. silicate
  • Ultra-low volume liquids (UL) 1-50 % by weight of at least one compound of the invention are dissolved in such amount of organic solvent, e.g. aromatic hydrocarbon, to result in a total amount of 100 % by weight.
  • the formulations types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 % by weight preservatives, 0.1-1 % by weight antifoams, 0.1-1 % by weight dyes and/or pigments, and 5-10% by weight antifreezes.
  • the compounds of the formula (I) may also be employed as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial species, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and/or plant growth regulators, in order thus, for example, to broaden the spectrum of action, to prolong the duration of action, to increase the rate of action, to prevent repulsion or prevent evolution of resistance.
  • active compound combinations may improve plant growth and/or tolerance to abiotic factors, for example high or low temperatures, to drought or to elevated water content or soil salinity.
  • the compounds of the formula (I) can be present in a mixture with other active compounds or semiochemicals such as attractants and/or bird repellants and/or plant activators and/or growth regulators and/or fertilizers.
  • the compounds of the formula (I) can be used to improve plant properties such as, for example, growth, yield and quality of the harvested material.
  • the compounds of the formula (I) are present in formulations or the use forms prepared from these formulations in a mixture with further compounds, preferably those as described below. If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included even if not explicitly mentioned in each case. Further, all named mixing partners can, if their functional groups enable this, optionally form salts with suitable bases or acids. Insecticides/acaricides/nematicides
  • the active compounds identified here by their common names are known and are described, for example, in the pesticide handbook (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be found on the Internet (e.g. http://www.alanwood.net/pesticides).
  • Acetylcholinesterase (AChE) inhibitors preferably carbamates selected from alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, BCS233014 FC-Text - 32 - propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos
  • GABA-gated chloride channel blockers preferably cyclodiene-organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiproles) 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,
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolids selected from flupyradifurone, or mesoionics selected from triflumezopyrim, or pyridylidenes selected from Flupyrimin.
  • nAChR Nicotinic acetylcholine receptor
  • Nicotinic acetylcholine receptor (nAChR) allosteric modulators site I
  • nAChR Nicotinic acetylcholine receptor
  • site I preferably spinosyns selected from spinetoram and spinosad.
  • Glutamate-gated chloride channel (GluCl) allosteric modulators preferably avermectins/milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimics preferably juvenile hormone analogues selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
  • Miscellaneous non-specific (multi-site) inhibitors preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet and metam.
  • Mite growth inhibitors affecting CHS1 selected from clofentezine, hexythiazox, diflovidazin and etoxazole.
  • Microbial disruptors of the insect gut membranes selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and B.t.
  • 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.
  • Uncouplers of oxidative phosphorylation via disruption of the proton gradient selected from chlorfenapyr, DNOC and sulfluramid.
  • Nicotinic acetylcholine receptor channel blockers selected from bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.
  • Moulting disruptors in particular for Diptera, i.e. dipterans selected from cyromazine.
  • Ecdysone receptor agonists preferably diacylhydrazines selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists selected from amitraz.
  • Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.
  • Mitochondrial complex I electron transport inhibitors preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).
  • METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).
  • Voltage-dependent sodium channel blockers 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, spiropidion and spirotetramat.
  • Mitochondrial complex IV electron transport inhibitors preferably phosphides selected from aluminium phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.
  • Mitochondrial complex II electron transport inhibitors preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.
  • Ryanodine receptor modulators preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.
  • Chordotonal organ Modulators (with undefined target site) selected from flonicamid.
  • GABA-gated chlorid channel allosteric modulators 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 Anticarsia gemmatalis MNPV, Flucypyriprole and Helicoverpa armigera NPV.
  • GVs Granuloviruses
  • NPVs Nucleopolyhedroviruses
  • Nicotinic acetylcholine receptor allosteric modulators site II
  • Site II selected from GS-omega/kappa HXTX-Hv1a peptide.
  • Calcium-activated potassium channel KCa2 modulators selected from acynonapyr.
  • Mitochondrial complex III electron transfer inhibitors (non-Qo site), selected from flometoquin.
  • UN Compounds of unknown or uncertain MoA (Target protein responsible for biological activity is unknown, or uncharacterized), selected from azadirachtin, benzoximate, bromopropylate, chinomethionat, dicofol, lime sulfur, mancozeb, pyridalyl, and sulfur.
  • UNB Bacterial agents (non-Bt) of unknown or uncertain MoA (Target protein responsible for biological activity is unknown or uncharacterized), selected from Burkholderia spp., and Wolbachia pipientis (Zap).
  • UNE Botanical essence including synthetic, extracts and unrefined oils with unknown or uncertain MoA (Target protein responsible for biological activity is unknown, or uncharacterized), selected from Chenopodium ambrosioides near ambrosioides extract and fatty acid monoesters with glycerol or propanediol neem oil.
  • Non-specific mechanical and physical disruptors (Target protein responsible for biological activity is unknown, or uncharacterized), selected from Diatomaceous earth, and mineral oil. Further active compounds selected from Afoxolaner, Benbenzaramine, Benzpyrimoxan, Chloroprallethrin, Cryolite, Cyclobutrifluram, Cycloxaprid, Cyetpyrafen, Cyhalodiamide, Cyproflanilide (CAS 2375110-88-4), Dicloromezotiaz, Dimpropyridaz, epsilon-Metofluthrin, epsilon-Momfluthrin, Fenmezoditiaz, Fluazaindolizine, Fluchlordiniliprole, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fufenozide, Flupentiofenox,
  • Nematicides The active compounds identified here by their common names are known and are described, for example, in the pesticide handbook (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be found on the Internet (e.g. http://www.alanwood.net/pesticides). The classification is based on the current Nematicide IRAC Mode of Action Classification Groups at the time of filing of this patent application.
  • Acetylcholinesterase (AChE) inhibitors preferably (N-1A) carbamates selected from aldicarb, benfuracarb, carbofuran, carbosulfan and thiodicarb, or (N-1B) organophosphates selected from cadusafos, ethoprofos, fenamiphos, fosthiazate, imicyafos, phorate and terbufos.
  • Group N-2 Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably avermectins selected from abamectin and emamectin benzoate.
  • Group N-UNX Compounds of unknown or uncertain mode of action: Presumed multi-site inhibitors, preferably volatile sulphur generators selected from carbon disulphide and dimethyl disulphide (DMDS), or carbon disulphide liberators selected from sodium tetrathiocarbonate, or alkyl halides selected from methyl bromide and methyl iodide (iodomethane), or halogenated hydrocarbons selected from 1,2- dibromo-3-chloropropane (DBCP) and 1,3-dichloropropene, or chloropicrin, or methyl isothiocyanate generators selected from allyl isothiocyanate, diazomet, metam potassium and metam sodium.
  • DMDS carbon disulphide and dimethyl disulphide
  • iodomethane alkyl halides selected from methyl bromide and methyl iodide (iodomethane)
  • DBCP 1,2- dibromo-3-chloropropane
  • Bacterial agents (non-Bt) of unknown or uncertain mode of action, preferably bacterium or bacterium-derived, selected from Burkholderia spp., e.g. rinojensis A396, Bacillus spp., e.g. firmus, licheniformis, amyloliquefaciens or subtilis, Pasteuria spp., e.g. penetrans or nishizawae, Pseudomonas spp., e.g. chlororaphis or fluorescens, and Streptomyces spp., e.g. lydicus, dicklowii or albogriseolus.
  • Burkholderia spp. e.g. rinojensis A396, Bacillus spp., e.g. firmus, licheniformis, amyloliquefaciens or subtilis, Pasteuria spp
  • BCS233014 FC-Text - 38 - (Group N-UNF) Fungal agents of unknown or uncertain mode of action, preferably fungus or fungus- derived, selected from Actinomyces spp., e.g. streptococcus, Arthrobotrys spp., e.g. oligospora, Aspergillus spp., e.g. niger, Muscodor spp., e.g. albus, Myrothecium spp., e.g. verrucaria, Paecilomyces spp., e.g.
  • Botanical or animal derived agents including synthetic extracts and unrefined oils, with unknown or uncertain mode of action, preferably botanical or animal derived agents selected from azadirachtin, camellia seed cake, essential oils, garlic extract, pongamia oil, terpenes, e.g.
  • Inhibitors of the ergosterol biosynthesis for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) Fluoxytioconazole, (1.010) fluquinconazole, (1.011) flutriafol, (1.012) hexaconazole, (1.013) imazalil, (1.014) imazalil sulfate, (1.015) ipconazole, (1.016) ipfentrifluconazole, (1.017) mefentrifluconazole, (1.018) metconazole, (1.019) myclobutanil, (1.020) paclobutrazol, (1.021) penconazole, (1.022) prochloraz,
  • Inhibitors of the respiratory chain at complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) flubeneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) furametpyr, (2.012) inpyrfluxam, (2.013) Isofetamid, (2.014) isoflucypram, (2.015) isopyrazam, (2.016) penflufen, (2.017) penthiopyrad, (2.018) pydiflumetofen, (2.019) pyrapropoyne, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) Thifluzamide (aka trifluzamide), (2.023) 5,8-difluoro-N-[
  • Inhibitors of the respiratory chain at complex III for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florylpicoxamid, (3.013) flufenoxystrobin, (3.014) fluoxastrobin, (3.015) kresoxim-methyl, (3.016) mandestrobin, (3.017) metarylpicoxamid, (3.018) metominostrobin, (3.019) metyltetraprole, (3.020) orysastrobin, (3.021) picoxystrobin, (3.022) pyraclostrobin, (3.021) pic
  • Inhibitors of the mitosis and cell division for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridachlometyl, (4.009) pyriofenone (chlazafenone), (4.010) thiabendazole, (4.011) thiophanate-methyl, (4.012) zoxamide, (4.013) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6- methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)
  • BCS233014 FC-Text - 42 - 5 Compounds capable to have a multisite action, for example (5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine- copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro
  • Compounds capable to induce a host defence for example (6.001) acibenzolar-S-methyl, (6.002) fosetyl-aluminium, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.007) probenazole, (6.008) tiadinil.
  • Inhibitors of the 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 8) Inhibitors of the ATP production, for example (8.001) silthiofam.
  • Inhibitors of the cell wall synthesis for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) 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)-1-(morpholin-4-yl)prop-2-en-1-one.
  • Inhibitors of the lipid synthesis or transport, or membrane synthesis for example (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) 1-(4- ⁇ 4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl ⁇ piperidin-1-yl)-2-[5- methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.009) 1-(4- ⁇ 4-[(5S)-5-(2,6-difluorophenyl)- 4,5-dihydro-1,2-oxazol-3-yl]-1
  • Inhibitors of the melanin biosynthesis for example (11.001) tolprocarb, (11.002) tricyclazole.
  • Inhibitors of the nucleic acid synthesis for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • 13) Inhibitors of the signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.
  • Bio pesticides as mixing components
  • the compounds of the formula (I) can be combined with biological pesticides.
  • Biological pesticides comprise in particular bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides comprise bacteria such as spore-forming bacteria, root-colonising bacteria and bacteria which act as biological insecticides, fungicides or nematicides. Examples of such bacteria which are employed or can be used as biological pesticides are: Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B.
  • thuringiensis subspecies 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), Methylorubrum extorquens TS201, Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which are employed or can be used as biological pesticides are: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain BCS233014 FC-Text - 47 - CON/M/91-8 (Accession No.
  • Lecanicillium spp. in particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P.
  • viruses which are employed or can be used as biological pesticides are: Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, Spodoptera littoralis (African cotton leafworm) NPV.
  • Adoxophyes orana sumr fruit tortrix granulosis virus
  • GV Cydia pomonella (codling moth) granulosis virus
  • NPV Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus
  • Spodoptera exigua beet armyworm
  • Spodoptera frugiperda fall armyworm
  • bacteria and fungi which are added as 'inoculant' to plants or plant parts or plant organs and which, by virtue of their particular properties, promote plant growth and plant health.
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp.
  • plant extracts and products formed by microorganisms including proteins and secondary metabolites which are employed or can be used as biological pesticides are: Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM Insecticide", rotenone, ryania/ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album
  • BCS233014 FC-Text - 48 - Safener as mixing components The compounds of the formula (I) can be combined with safeners such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-( ⁇ 4-[(methylcarbamoyl)amino]phenyl ⁇ sulphonyl)benzamide (CAS 129531- 12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacet
  • plants and plant parts can be treated in accordance with the invention.
  • plants are to be understood to mean all plants and plant parts such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soya bean, potato, sugar beet, sugar cane, tomatoes, pepper, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage) and other vegetable species, cotton, tobacco, oilseed rape, and also fruit plants (with the fruits apples, pears, citrus fruits and grapevines).
  • cereals wheat, rice, triticale, barley, rye, oats
  • soya bean potato
  • sugar beet sugar cane
  • tomatoes pepper, cucumber, melon, carrot
  • watermelon onion
  • lettuce spinach
  • leek beans
  • Brassica oleracea e.g. cabbage
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights.
  • Plants should be understood to mean all developmental stages, such as seeds, seedlings, young (immature) plants up to mature plants.
  • Plant parts should be understood to mean all parts and organs of the plants above and below ground, such as shoot, leaf, flower and root, examples given being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also tubers, roots and rhizomes.
  • Parts of plants also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
  • Treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by allowing the compounds to act on the surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • wild plant species and plant cultivars or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • the invention is used with particular preference to treat plants of the respective commercially customary BCS233014 FC-Text - 49 - cultivars or those that are in use. Plant cultivars are to be understood as meaning plants having new properties ("traits”) and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • the compounds of formula (I) can be advantageously used to treat transgenic plants, plant cultivars or plant parts that received genetic material which imparts advantageous and/or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention may be combined with one or more recombinant traits or transgenic event(s) or a combination thereof.
  • a transgenic event is created by the insertion of a specific recombinant DNA molecule into a specific position (locus) within the chromosome of the plant genome.
  • the insertion creates a novel DNA sequence referred to as an “event” and is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to/flanking both ends of the inserted DNA.
  • trait(s) or transgenic event(s) include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, in which the trait is measured with respect to a plant lacking such trait or transgenic event.
  • Such advantageous and/or useful properties are better plant growth, vigor, stress tolerance, standability, lodging resistance, nutrient uptake, plant nutrition, and/or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processability of the harvested products, and increased resistance or tolerance against animal and microbial pests, such as against insects, arachnids, nematodes, mites, slugs and snails.
  • animal and microbial pests such as against insects, arachnids, nematodes, mites, slugs and snails.
  • Bt Cry or VIP proteins which include the CrylA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof and also hybrids or combinations thereof, especially 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 CrylAc protein or hybrids derived from the CrylAc 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 CrylA.105 protein or a toxic fragment thereof, the VIP3Aa19 protein, the VIP3Aa20 protein, the VIP3A proteins produced in the COT202 or COT203 cotton events, the BCS233014 FC-Text - 50 - VIP3Aa protein or a toxic fragment thereof as described in Estruch et al.
  • any variants or mutants of any one of these proteins differing in some amino acids (1-10, preferably 1-5) from any of the above named sequences, particularly the sequence of their toxic fragment, or which are fused to a transit peptide, such as a plastid transit peptide, or another protein or peptide, is included herein.
  • a transit peptide such as a plastid transit peptide, or another protein or peptide
  • Another and particularly emphasized example of such properties is conferred tolerance to one or more herbicides, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin.
  • DNA sequences encoding proteins which confer properties of tolerance to certain herbicides on the transformed plant cells and plants mention will be particularly be made to the bar or PAT gene or the Streptomyces coelicolor gene described in WO2009/152359 which confers tolerance to glufosinate herbicides, a gene encoding a suitable EPSPS (5-enolpyruvylshikimat-3-phosphat-synthase) which confers tolerance to herbicides having EPSPS as a target, especially herbicides such as glyphosate and its salts, a gene encoding glyphosate-n-acetyltransferase, or a gene encoding glyphosate oxidoreductase.
  • EPSPS 5-enolpyruvylshikimat-3-phosphat-synthase
  • herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. WO2007/024782), a mutated Arabidopsis ALS/AHAS gene (e.g. U.S. Patent 6,855,533), genes encoding 2,4-D- monooxygenases conferring tolerance to 2,4-D (2,4- dichlorophenoxyacetic acid) and genes encoding Dicamba monooxygenases conferring tolerance to dicamba (3,6-dichloro-2- methoxybenzoic acid).
  • ALS acetolactate synthase
  • a mutated Arabidopsis ALS/AHAS gene e.g. U.S. Patent 6,855,533
  • Such properties are increased resistance against phytopathogenic fungi, bacteria and/or viruses owing, for example, to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • systemin phytoalexins
  • elicitors resistance genes and correspondingly expressed proteins and toxins.
  • Particularly useful transgenic events in transgenic plants or plant cultivars which can be treated with preference in accordance with the invention include Event 531/ PV-GHBK04 (cotton, insect control, described in WO2002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006/128570); Event 1445 (cotton, herbicide tolerance, not 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, insect control - herb
  • Event BLRl (oilseed rape, 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, described, described in US-A 2007-067868 or
  • transgenic event(s) is provided by the United States Department of Agriculture’s (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website at https://www.aphis.usda.gov/. For this application, the status of such list as it is/was on the filing date of this application, is relevant.
  • the genes/events which impart the desired traits in question may also be present in combinations with one another in the transgenic plants.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetable, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis being given to maize, soya beans, wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and slugs and snails, as well as the increased resistance of the plants to one or more herbicides.
  • Crop protection – types of treatment The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seed, furthermore as a powder for dry seed treatment, a solution for liquid seed treatment, a water-soluble powder for slurry treatment, by incrusting, by coating with one or more coats, etc.
  • customary treatment methods for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seed, furthermore as a powder for
  • the compounds of the formula (I) by the ultra-low volume method or to inject the application form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i.e. the compounds of the formula (I) are applied to the foliage, where treatment frequency and the application rate should be adjusted according to the level of infestation with the pest in question.
  • the compounds of the formula (I) also access the plants via the root system.
  • the plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant. This may be done, for example, by drenching, or by mixing into the soil or the nutrient solution, i.e.
  • the locus of the plant e.g. soil or hydroponic systems
  • a liquid form of the compounds of the formula (I) or by soil application, i.e. the compounds of the formula (I) according to the invention are introduced in solid form (e.g. in the form of granules) into the locus of the plants, or by drip application (often also referred to as "chemigation"), i.e. the liquid application of the compounds of the formula (I) according to the invention from surface or sub-surface driplines over a certain period of time together with varying amounts of water at defined locations in the vicinity of the plants.
  • chemigation i.e. the liquid application of the compounds of the formula (I) according to the invention from surface or sub-surface driplines over a certain period of time together with varying amounts of water at defined locations in the vicinity of the plants.
  • the compounds of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture.
  • models support the site specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield etc. with the purpose to optimize profitability, sustainability and protection of the environment.
  • the compounds of the invention can be applied to a crop plant according to an appropriate dose regime if a model models the development of a pest and calculates that a threshold has been reached for which it is recommendable to apply the compound of the invention to the crop plant.
  • Commercially available systems which include agronomic models are e.g. FieldScriptsTM from The climate Corporation, XarvioTM from BASF, AGLogicTM from John Deere, etc.
  • the compounds of the invention can also be used in combination with smart spraying equipment such as e.g.
  • Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • input sensors such as e.g. a camera
  • processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • the use of such smart spraying equipment usually also requires positions systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the spraying.
  • GPS geographic information systems
  • pests can be detected from imagery acquired by a camera.
  • the pests can be identified and/or classified based on that imagery.
  • image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed.
  • Treatment of seed The control of animal pests by treating the seed of plants has been known for a long time and is the subject of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner.
  • the present invention therefore in particular also relates to a method for the protection of seed and germinating plants, from attack 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 against attack by pests furthermore comprises a method where the seed is treated simultaneously in one operation or sequentially with a compound of the formula (I) and a mixing component. It also comprises a method where the seed is treated at different times with a compound of the formula (I) and a mixing component.
  • the invention likewise relates to the use of the compounds of the formula (I) for the treatment of seed for protecting the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated with a compound of the formula (I) according to the invention so as to afford protection from animal pests.
  • the invention also relates to seed which has been treated simultaneously with a compound of the formula (I) and a mixing component.
  • the invention furthermore relates to seed which has been treated at different times with a compound of the formula (I) and a mixing component.
  • the individual substances may be present on the seed in different layers.
  • the layers comprising a compound of the formula (I) and mixing components may optionally be separated by an intermediate layer.
  • the invention also relates to seed where a compound of the formula (I) and a mixing component have been applied as component of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after the treatment with a compound of the formula (I), is subjected to a film-coating process to prevent dust abrasion on the seed.
  • One of the advantages encountered with a systemically acting compound of the formula (I) is the fact that, by treating the seed, not only the seed itself but also the plants resulting therefrom are, after emergence, protected against animal pests. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • this takes the form of seed of cereals (for example wheat, barley, rye, millet and oats), corn, cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola, oilseed rape, beets (for example sugarbeets and fodder beets), peanuts, vegetables (for example tomatoes, cucumbers, bean, cruciferous vegetables, onions and lettuce), fruit plants, lawns and ornamental plants.
  • cereals for example wheat, barley, rye and oats
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • 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 suitable for the treatment of transgenic seed which comprises at least one heterologous gene originating from Bacillus sp.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state in which it is stable enough to avoid damage during treatment.
  • the seed may be treated at any point in time between harvest and sowing.
  • the seed usually used has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content which allows storage.
  • seed which, after drying, has been treated BCS233014 FC-Text - 58 - with, for example, water and then dried again, for example priming In the case of rice seed, it is also possible to use seed which has been soaked, for example in water to a certain stage of the rice embryo (‘pigeon breast stage’), stimulating the germination and a more uniform emergence.
  • care must generally be taken that the amount of the compound of the formula (I) applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged.
  • the compounds of the formula (I) are applied to the seed in a suitable formulation. Suitable formulations and processes for seed treatment are known to the person skilled in the art.
  • the compounds of the formula (I) can be converted to the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
  • These formulations are prepared in a known manner, by mixing the compounds of the formula (I) with customary additives such as, for example, customary extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Colorants which may be present in the seed-dressing formulations which can be used in accordance with the invention are all colorants which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.
  • Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting, and which are conventionally used for the formulation of agrochemically active compounds. Preference is given to using alkylnaphthalenesulphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates.
  • Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Suitable nonionic dispersants include in particular ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers, and the phosphated or sulphated derivatives thereof.
  • Suitable anionic dispersants are in particular lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
  • BCS233014 FC-Text - 59 - Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Preference is given to using silicone antifoams and magnesium stearate.
  • the gibberellins are known (cf. R. Wegler "Chemie der convinced für Schweizer- and Schdlingsbelampfungsstoff", vol.2, Springer Verlag, 1970, pp.401-412).
  • the seed dressing formulations usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also the seed of maize, rice, oilseed rape, peas, beans, cotton, sunflowers, soya beans and beets, or else a wide variety of different vegetable seed.
  • the seed dressing formulations usable in accordance with the invention, or the dilute use forms thereof can also be used to dress seed of transgenic plants.
  • all mixing units usable customarily for the seed dressing are useful.
  • the procedure in the seed dressing is to place the seed into a mixer, operated batch- wise or continously, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying operation.
  • the application rate of the seed dressing formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the compounds of the formula (I) in the formulations and by the seed.
  • the application rates of the compound of the formula (I) are BCS233014 FC-Text - 60 - generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoae, such as coccidia.
  • Ectoparasites are typically and preferably arthropods, in particular insects or acarids.
  • the compounds of the formula (I) are suitable, with favourable toxicity in warm blooded animals, for controlling parasites which occur in animal breeding and animal husbandry in livestock, breeding, zoo, laboratory, experimental and domestic animals. They are active against all or specific stages of development of the parasites.
  • Agricultural livestock include, for example, mammals, such as, sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeers, fallow deers, and in particular cattle and pigs; or poultry, such as turkeys, ducks, geese, and in particular chickens; or fish or crustaceans, e.g. in aquaculture; or, as the case may be, insects such as bees.
  • domestic animals include, for example, mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets or in particular dogs, cats; cage birds; reptiles; amphibians or aquarium fish.
  • the compounds of the formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely cage birds or in particular poultry.
  • the compounds of the formula (I) By using the compounds of the formula (I) to control animal parasites, it is intended to reduce or prevent illness, cases of deaths and performance reductions (in the case of meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible and better animal well-being is achievable.
  • control or "controlling”, as used herein with regard to the animal health field, means that the compounds of the formula (I) are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels.
  • controlling means that the compounds of the formula (I) are effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation.
  • arthropods include, without any limitation from the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; BCS233014 FC-Text - 61 - from the order of the 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., Werneckiella spp.; from the order of the Diptera and the suborders Nemato
  • Siphonapta for example Ceratophyllus spp.; Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; from the order of the Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; as well as nuisance and hygiene pests from the order of the Blattarida.
  • acari may be mentioned by way of example, without any limitation: from the subclass of the Acari (Acarina) and the order of the Metastigmata, for example, from the family of argasidae like Argas spp., Ornithodorus spp., Otobius spp., from the family of Ixodidae like Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp , Rhipicephalus spp.
  • Exemplary parasitic protozoa include, without any limitation: Mastigophora (Flagellata) 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 BCS233014 FC-Text - 62 - Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example, Entamoeba spp., Centramoebidae, for example, Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveolata such as Apicomplexa (Sporozoa): e.g.
  • Cryptosporidium spp. from the order Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; from the order Adeleida e.g. Hepatozoon spp., Klossiella spp.; from the order Haemosporida e.g. Leucocytozoon spp., Plasmodium spp.; from the order Piroplasmida e.g.
  • helminths include, without any limitation: Monogenea: e.g.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglocephalus spp. Cestodes: from the order of the 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 spp.
  • Trematodes from the class of the 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., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Or
  • Nematodes from the order of the Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. BCS233014 FC-Text - 63 - from the order of the Tylenchida, for example: Micronema spp., Parastrongyloides spp., Strongyloides spp.
  • Aelurostrongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus s
  • Spirurida from the order of the Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp
  • Acantocephala from the order of the Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp.; from the order of the Moniliformida, for example: Moniliformis spp. from the order of the Polymorphida, for example: Filicollis spp.; from the order of the Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. Pentastoma: from the order of the Porocephalida, for example: Linguatula spp.
  • Fish parasites include crustaceans which in turn include the family Caligidae with representative genus Dissonus, Caligus (i.e. C. curtus, C. elongatus, C. clemensi, C.rogercresseyii), and Lepeophtheirus (i.e. L.
  • the administration of the compounds of the formula (I) is carried out by methods generally known in the art, such as enterally, parenterally, dermally or nasally, in the form of suitable preparations. Administration can be carried out prophylactically, methaphylactically or therapeutically.
  • one embodiment of the present invention refers to the compounds of the formula (I) for use as a medicament.
  • Another aspect refers to the compounds of the formula (I) for use as an antiendoparasitical agent.
  • Another particular aspect refers to the compounds of the formula (I) for use as a anthelmintic agent, more particular for use as a nematicidal agent, a platyhelminthicidal agent, an acanthocephalicidal agent, or a pentastomicidal agent.
  • Another particular aspect refers to the compounds of the formula (I) for use as an antiprotozoal agent.
  • Another aspect refers to the compounds of the formula (I) for use as an antiectoparasitical agent, in particular an arthropodicidal agent, more particular an insecticidal agent or acaricidal agent.
  • veterinary formulations comprising an effective amount of at least one compound of the formula (I) and at least one of the following: pharmaceutically acceptable excipient (e.g. solid or liquid diluents), pharmaceutically acceptable auxiliary (e.g. surfactants), in particular a pharmaceutically acceptable excipient and/or pharmaceutically acceptable auxiliary which is normally used in veterinary formulations.
  • pharmaceutically acceptable excipient e.g. solid or liquid diluents
  • pharmaceutically acceptable auxiliary e.g. surfactants
  • a related aspect of the invention is a method for preparing a veterinary formulation as described herein, comprising the step of mixing at least one compound of the formula (I) with pharmaceutically acceptable excipients and/or auxiliaries, in particular with pharmaceutically acceptable excipients and/or auxiliaries which are normally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, more particular selected from the group of anthelmintic, antiprotozoal, and arthropodicidal formulations, even more particular selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal, and acaricidal formulations, in accordance with the mentioned aspects, as well as their methods for preparation.
  • Another aspect refers to a method for treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human animal, in need thereof.
  • Another aspect refers to a method for treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, in need thereof.
  • Another aspect refers to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic or therapeutical treatment.
  • mixtures of at least one compound of the formula (I) with other active ingredients, particularly with endo- and ectoparasiticides, for the veterinary field are provided herewith.
  • mixture not only means that two (or more) different active ingredients are formulated in a joint formulation and are accordingly applied together but also refers to products which comprise separate formulations for each active compound. Accordingly, if more than two active compounds are to be applied, all active compounds may be formulated in a joint formulation or all active compounds may be formulated in separate formulations; also feasible are mixed forms where some of the active compounds are formulated jointly and some of the active compounds are formulated separately. Separate formulations allow the separate or successive application of the active compounds in question.
  • the active compounds specified herein by their common names are known and described, for example, in the Pesticide Manual (see above) or can be searched in the internet (e.g. http://www.alanwood.net/pesticides).
  • active ingredients from the group of ectoparasiticides, as mixing partners include, without limitation insecticides and acaricides listed in detail above. Further active ingredients which may be used are listed below following the aforementioned classification which is based on the current IRAC Mode of Action Classification Scheme: (1) Acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) Sodium channel modulators; (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) Glutamate-gated chloride channel (GluCl) allosteric modulators; (7) Juvenile hormone mimics; (8) Miscellaneous non-specific (multi-site) inhibitors; (9) Modulators of chordotonal organs; (10) Mite growth inhibitors; (12) Inhibitors of mitochondrial ATP synthase, such as, ATP disruptors; (13)
  • Active compounds with unknown or non-specific mode of action e.g., fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplure, flutenzin, bromopropylate, cryolite; Compounds from other classes: butacarb, dimetilan, cloethocarb, phosphocarb, pirimiphos (-ethyl), parathion (-ethyl), methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos, sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methyls
  • camphechlor lindane, heptachlor
  • phenylpyrazoles e.g. acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil
  • isoxazolines e.g. afoxolaner, esafoxolaner, fluralaner, lotilaner, mivorilaner, modoflaner, sarolaner, umifoxolaner
  • pyrazolyl-arylamides e.g. nicofluprole, tigolaner
  • pyrethroids e.g.
  • nithiazine dicloromezotiaz, triflumezopyrim
  • macrocyclic lactones e.g. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate, milbemycin oxime; triprene, epofenonane, diofenolan; biologicals, hormones or pheromones, for example natural products, e.g. thuringiensin, codlemone or neem components; dinitrophenols, e.g.
  • Anthelmintically active compounds including, without limitation, the following nematicidally, trematicidally and/or cestocidally active compounds: from the class of macrocyclic lactones, 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, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole-sulphoxide, albendazole, flu
  • Antiprotozoal active compounds including, without limitation, the following active compounds: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class of polylether ionophore, 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, sulfaclozin; from the class of thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin
  • a vector is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as, for example, viruses, worms, single-cell organisms and bacteria from a reservoir (plant, animal, human, etc.) to a host.
  • pathogens can be transmitted either mechanically (for example trachoma by non-stinging flies) to a host, or by injection (for example malaria parasites by mosquitoes) into a host.
  • vectors and the diseases or pathogens they transmit are: 1) Mosquitoes - Anopheles: malaria, filariasis; - Culex: Japanese encephalitis, other viral diseases, filariasis, transmission of other worms; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis; - Simuliidae: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis 2) Lice: skin infections, epidemic typhus; 3) Fleas: plague, endemic typhus, cestodes; 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases; 5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean–Congo haemorrhagic fever, borreliosis;
  • vectors in the sense of the present invention are insects, for example aphids, flies, leafhoppers or thrips, which are capable of transmitting plant viruses to plants.
  • Other vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.
  • Further examples of vectors in the sense of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.
  • a further aspect of the present invention is the use of compounds of the formula (I) for vector control, for example in agriculture, in horticulture, in gardens and in leisure facilities, and also in the protection of materials and stored products.
  • the compounds of the formula (I) are suitable for protecting industrial materials against attack or destruction by insects, for example from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • Industrial materials in the present context are understood to mean inanimate materials, such as preferably plastics, adhesives, sizes, papers and cards, leather, wood, processed wood products and coating compositions. The use of the invention for protecting wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and/or at least one fungicide.
  • the compounds of the formula (I) are present as a ready-to-use pesticide, i.e.
  • the compounds of the formula (I) can be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
  • the compounds of the formula (I) alone or in combinations with other active compounds, can be used as antifouling agents. Control of animal pests in the hygiene sector
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be applied in the domestic sector, in the hygiene sector and in the protection of stored products, especially for controlling insects, arachnids, ticks and mites encountered in enclosed spaces such as dwellings, factory halls, offices, vehicle cabins, animal husbandries.
  • the compounds of the formula (I) are used alone or in combination with other active compounds and/or auxiliaries. They are preferably used in domestic insecticide products.
  • the compounds of the formula (I) are effective against sensitive and resistant species, and against all developmental stages.
  • 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.
  • BCS233014 FC-Text - 71 - They are used, for example, in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.
  • Analytical methods The analytical methods described below refer to all information in the entire document, unless the procedure of the respective analytical determination is described separately at the respective passage.
  • LC-MS6 and LC-MS7 Agilent 1290 LC, Agilent MSD, HTS PAL autosampler. Linear gradient 0.0 to 1.80 minutes from 10 % acetonitrile to 95 % acetonitrile, from 1.80 to 2.50 minutes constant 95 % acetonitrile, flow 1.0 ml/min.
  • LC-MS8 Waters IClass Acquity with QDA mass spectrometer and FTN autosampler (column Waters Acquity 1.7 ⁇ m 50 mm * 2.1 mm, oven temperature 45°C). Linear gradient 0.0 to 2.10 minutes from 10 % acetonitrile to 95 % acetonitrile, from 2.10 to 3.00 minutes constant 95 % acetonitrile, flow 0.7 ml/min.
  • BCS233014 FC-Text - 72 - Retention time indices were calculated in all cases according to a homologue series of straight chain alkan-2-ones with 3 to 16 carbons where the index of the first alkanone was set to 300, the last to 1600, the ones between correspondingly and using linear interpolation between successive alkanones.
  • the determination of 1 H-NMR data was done with a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI probehead, with tetramethylsilane as reference (0.00 ppm) and the measurements were recorded usually from solutions in the solvents CD3CN, CDCl3 or d6-DMSO.
  • a Bruker Avance III 600 MHz instrument equipped with a 5 mm CPNMP probehead or a Bruker Avance NEO 600 MHz instrument equipped with a 5 mm TCI probehead were used for the measurements. Usually, the measurements were carried out with a probehead temperature of 298 K. Other measurement temperatures are explicitly noticed.
  • NMR peak lists procedure 1 H-NMR data of selected examples are written in form of 1 H-NMR peak lists. ⁇ -Values in ppm and the signal intensity in round brackets are listed to each signal peak. Semicolons are depicted as delimiters between the ⁇ -value – signal intensity pairs.
  • the peak list of an example has the form: ⁇ 1 (intensity1); ⁇ 2 (intensity2);........; ⁇ i (intensityi); hence; ⁇ n (intensityn)
  • the intensity of sharp signals correlates with the height of the signals in a printed view of a 1 H-NMR spectrum in cm and shows the real relations of signal intensities.
  • Several peaks from broad signals or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown. Tetramethylsilane or the chemical shift of the solvent in cases where the sample does not contain tetramethylsilane is used for a calibration of the chemical shift for 1 H spectra.
  • the tetramethylsilane peak can occur in 1 H-NMR peak lists, but not necessarily.
  • 1 H-NMR peak lists are equivalent to classical 1 H-NMR prints and contain usually all peaks, which are also listed at classical 1 H-NMR-interpretations. In addition, they can show signals of solvents, stereoisomers of the compounds which are optionally object of the invention, and/or peaks of impurities, like classical 1 H-NMR prints.
  • 1 H-NMR solvent signals, the tetramethylsilane signal and the water signal in the corresponding solvent are excluded from the relative intensity calibration as they have very high intensity values.
  • the peaks of stereoisomers of the compounds according to the invention and/or peaks of impurities have usually a lower intensity than the peaks of compounds according to the invention (for example with a purity >90%).
  • Such stereoisomers and/or impurities can be typical for the specific preparation process.
  • the corresponding peaks can help to recognize the reproduction of the preparation process via “side-products- fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods (MestreC, ACD- simulation, but also with empirically evaluated expectation values), can assign the peaks of the target compounds as needed, optionally using additional intensity filters. This assignment would be similar to the usual peak picking at classical 1 H-NMR interpretations.
  • the used solvent can be extracted from the JCAMP file with the parameter “solvent”, the spectrometer frequency with “observe frequency” and the spectrometer type with “spectrometer/data system”.
  • 13 C-NMR data are displayed analogous to 1 H-NMR data as peak lists from broadband decoupled 13 C- NMR spectra.
  • 13 C-NMR solvent signals and tetramethylsilane are excluded from the relative intensity calibration as these signals can have very high intensities. Further details of NMR-data description with peak lists are disclosed in the publication “Citation of NMR Peaklist Data within Patent Applications” of the Research Disclosure Database Number 564025.
  • logP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). Calibration was done with straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values between successive alkanones are determined by linear regression.
  • Step 2 6-[5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5- c]pyridazine (INT-04/compound of the formula (IX)) This reaction was carried out under argon atmosphere using a Schlenk tube.
  • Step 4 1-(6- ⁇ 5-(ethylsulfanyl)-1-methyl-4-[7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5-c]pyridazin-6- yl]-1H-imidazol-2-yl ⁇ pyridin-3-yl)cyclopropanecarbonitrile (INT-06) This reaction was carried out under argon atmosphere using a Schlenk tube.
  • Step 5 18 ⁇ L (0.468 mmol) of formic acid and an aqueous solution (35%) of hydrogen peroxide (0.113 mL, 1.31 mmol) were added dropwise to a solution of 50 mg (0.094 mmol) of 1-(6- ⁇ 5-(ethylsulfanyl)-1-methyl-4- [7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]-1H-imidazol-2-yl ⁇ pyridin-3- yl)cyclopropanecarbonitrile (INT-06) in dichloromethane (2.0 mL) and the resulting solution was stirred at RT overnight.
  • INT-06 1-(6- ⁇ 5-(ethylsulfanyl)-1-methyl-4- [7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]-1
  • the resulting solution was cooled down to 0 °C, diluted with water and a saturated aqueous solution of NaHSO3.
  • the organic layer was washed with a saturated aqueous NaCl solution and a 20% aqueous NaHCO3 solution, dried with Na2SO4, filtered and concentrated under reduced pressure.
  • Step 2 1-(5-iodo-2-thienyl)cyclopropanecarbonitrile (INT-08)
  • a solution (2.5 M) of n-butyl lithium in hexanes (0.84 mL, 2.1 mmol) was added dropwise to a solution of 300 mg (2.01 mmol) of 1-(2-thienyl)cyclopropanecarbonitrile (INT-07) in tetrahydrofurane (12 mL) and the reaction mixture was stirred at -78 °C for 5 minutes.
  • Step 4 54.5 ⁇ L (1.32 mmol) of formic acid and an aqueous solution (35%) of hydrogen peroxide (0.318 mL, 3.71 mmol) were added dropwise to a solution of 143 mg (0.265 mmol) of 1-(5- ⁇ 5-(ethylsulfanyl)-1-methyl- 4-[7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5-c]pyridazin-6-yl]-1H-imidazol-2-yl ⁇ -2- thienyl)cyclopropanecarbonitrile (INT-09) in dichloromethane (5.7 mL) and the resulting solution was stirred at RT overnight.
  • the resulting solution was cooled down to 0 °C, diluted with water and a saturated aqueous solution of NaHSO3.
  • the organic layer was washed with a saturated aqueous NaCl solution and a 20% aqueous NaHCO3 solution, dried with Na2SO4, filtered and concentrated under reduced pressure.
  • Step 2 33 ⁇ L (0.89 mmol) of formic acid and an aqueous solution (35%) of hydrogen peroxide (0.106 mL, 1.24 mmol) were added dropwise to a solution of 98.2 mg (0.177 mmol) of 6-[2-(4-bromo-1,3-thiazol-2-yl)-5- (ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5-c]pyridazine (INT-10) in dichloromethane (4.4 mL) and the resulting solution was stirred at RT overnight.
  • the resulting solution was cooled down to 0 °C, diluted with water and a saturated aqueous solution of NaHSO 3 .
  • the organic layer was washed with a saturated aqueous NaCl solution and a 20% aqueous NaHCO 3 solution, BCS233014 FC-Text - 84 - dried with Na2SO4, filtered and concentrated under reduced pressure.
  • Step 2 19 ⁇ L (0.503 mmol) of formic acid and an aqueous solution (35%) of hydrogen peroxide (0.121 mL, 1.41 mmol) were added dropwise to a solution of 54.1 mg (0.101 mmol) of 6-[2-(3-bromo-1H-pyrazol-1-yl)- 5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7H-imidazo[4,5- c]pyridazine (INT-11) in dichloromethane (4.3 mL) and the resulting solution was stirred at RT overnight.
  • the resulting solution was cooled down to 0 °C, diluted with water and a saturated aqueous solution of NaHSO 3 .
  • the organic layer was washed with a saturated aqueous NaCl solution and a 20% aqueous NaHCO 3 solution, dried with Na 2 SO 4 , filtered and concentrated under reduced pressure.
  • test concentrations are prepared by dilution with emulsifier containing water. Soaked wheat seeds (Triticum aestivum) are placed in a multiple well plate filled with agar and some water and are incubated for 1 day to germinate (5 seeds per well). The germinated wheat seeds are sprayed with a test solution containing the desired concentration of the active ingredient. Afterwards each unit is infected with 10-20 larvae of the banded cucumber beetle (Diabrotica balteata). After 7 days efficacy in % is determined. 100 % means all the seedlings have grown up like in the untreated, uninfected control; 0 % means none of the seedlings have grown.
  • Common bean (Phaseolus vulgaris) leaf disks are sprayed with a preparation of the active ingredient of the desired concentration and infected with all instars of the western flower thrips (Frankliniella occidentalis) afterwards. After 7 days leaf protection efficacy is determined in %.100 % means no visible leaf damage (very good protection) and 0 % means a complete damaged leaf disk (no protection). In this test, for example, the following compounds from the preparation examples showed a very good leaf protection of 90 % at an application rate of 500 g/ha: I-13, I-84.
  • the plates are sealed with parafilm through which a mixed population of the green peach aphid (Myzus persicae) can suck on the compound preparation.
  • a mixed population of the green peach aphid Myzus persicae
  • mortality in % is determined.100 % means all aphids have been killed and 0 % means none of the aphids have been killed.
  • test concentrations are prepared by dilution with emulsifier containing water.
  • Chinese cabbage (Brassica pekinensis) leaf disks infected with all instars of the green peach aphid (Myzus persicae) are sprayed with a preparation of the active ingredient of the desired concentration. After 5 days mortality in % is determined.100 % means all aphids have been killed and 0 % means none of the aphids have been killed.
  • the following compounds from the preparation examples showed good activity of 100 % at an application rate of 100 g/ha: I-6, I-9, I-10, I-53, I-57, I-79, I-95, I-96, I-98, I-103.
  • the following compounds from the preparation examples showed good activity of 95 % at an application rate of 100 g/ha: I-84.
  • the following compounds from the preparation examples showed good activity of 90 % at an application rate of 100 g/ha: I-8, I-11, I-20, I-22, I-23, I-24, I-26, I-28, I-30, I-38, I-45, I-48, I-49, I-50, I-51, I-55, I-59, I-62, I-63, I-69, I-71, I-72, I-76, I-80, I-92, I-93, I-97, I-99, I-101, I-104, I-106.
  • the following compounds from the preparation examples showed good activity of 85 % at an application rate of 100 g/ha: I-14, I-89.
  • the following compounds from the preparation examples showed good activity of 80 % at an application rate of 100 g/ha: I-83.
  • the following compounds from the preparation examples showed good activity of 70 % at an application rate of 100 g/ha: I-4, I-27, I-37, I-40, I-54, I-58, I-61, I-70, I-78, I-94, I-102.
  • Nezara viridula – spray test Solvent 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide
  • Emulsifier alkylarylpolyglycol ether
  • To produce a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water. Barley plants (Hordeum vulgare) are sprayed with a test solution containing the desired concentration of the active ingredient and are infested with larvae of the southern green stink bug (Nezara viridula). After 4 days mortality in % is determined.
  • Rice plants (Oryza sativa) are sprayed with a preparation of the active ingredient of the desired concentration and the plants are infested with the brown planthopper (Nilaparvata lugens). After 4 days mortality in % is determined.100 % means all planthoppers have been killed and 0 % means none of the planthoppers have been killed. In this test, for example, the following compounds from the preparation examples showed good activity of 100 % at an application rate of 500 g/ha: I-10, I-27, I-28, I-30, I-36, I-40, I-41, I-48, I-49, I-51, I-70, I- 72, I-73, I-74, I-76.
  • BCS233014 FC-Text - 110 - Chinese cabbage (Brassica pekinensis) leaf disks are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf disks are infested with mustard beetle larvae (Phaedon cochleariae). After 7 days mortality in % is determined.100 % means all beetle larvae have been killed and 0 % means none of the beetle larvae have been killed. In this test, for example, the following compounds from the preparation examples showed good activity of 100 % at an application rate of 100 g/ha: I-53.
  • Spodoptera frugiperda – spray test Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide
  • Emulsifier alkylarylpolyglycol ether
  • To produce a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
  • Maize (Zea mays) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda). After 7 days mortality in % is determined.
  • Nezara viridula – spray test Solvent: 52.5 parts by weight of acetone 7 parts by weight of dimethylformamide
  • Emulsifier alkylaryl polyglycolether BCS233014 FC-Text - 111 -
  • To produce a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Ammonium salt and/or penetration enhancer in a dosage of 1000 ppm are added to the desired concentration if necessary.
  • Barley plants (Hordeum vulgare) are sprayed with a test solution containing the desired concentration of the active ingredient and are infested with larvae of the southern green stink bug (Nezara viridula). After 4 days mortality in % is determined. 100 % means all the stink bugs have been killed; 0 % means none of the stink bugs have been killed.
  • the following compounds from the preparation examples showed good activity of 100 % at an application rate of 100 g/ha: I-1, I-2, I-3, I-6, I-7, I-17, I-19, I-20, I-23, I-24, I-53, I-54, I- 55, I-57, I-58, I-62, I-63, I-78, I-79, I-92, I-93, I-94, I-95, I-97, I-98, I-99, I-100, I-101, I-102, I-103, I- 104, I-105, I-106.
  • test concentrations are prepared by dilution with emulsifier containing water.
  • Ammonium salt and/or penetration enhancer in a dosage of 1000 ppm are added to the desired concentration if necessary.
  • Rice plants (Oryza sativa) are treated by being sprayed with the desired concentration of the active compound and are infested with larvae of the brown planthopper (Nilaparvata lugens). After 4 days mortality in % is determined.100 % means all planthoppers have been killed and 0 % means none of the planthoppers have been killed.
  • the following compounds from the preparation examples showed good activity of 100 % at an application rate of 100 g/ha: I-1, I-4, I-6, I-7, I-19, I-22, I-24, I-53, I-54, I-55, I-57, I-58, I- BCS233014 FC-Text - 112 - 59, I-61, I-62, I-63, I-71, I-78, I-79, I-92, I-93, I-94, I-95, I-96, I-97, I-98, I-99, I-100, I-101, I-102, I-103, I-104, I-106.
  • Chinese cabbage (Brassica pekinensis) leaf disks are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf disks are infested with mustard beetle larvae (Phaedon cochleariae). After the specified period of time mortality in % is determined. 100 % means all beetle larvae have been killed and 0 % means none of the beetle larvae have been killed.
  • Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds.
  • the lettuce seeds germinate and the seedlings grow. Galls develop in the roots. After 14 days the nematicidal effect in percent is determined by the formation of galls.100 % means no galls were found and 0 % means the number of galls found on the roots of the treated plants was equal to that in untreated control plants.
  • Cabbage leaves (Brassica oleracea) are treated by being sprayed with the preparation of the active compound of the desired concentration and are infested with larvae of the diamondback moth (Plutella xylostella). After the specified period of time mortality in % is determined.100 % means all the caterpillars have been killed and 0 % means none of the caterpillars have been killed.
  • Ammonium salt and/or penetration enhancer in a dosage of 1000 ppm are added to the desired concentration.
  • Cotton plants (Gossypium hirsutum), which are heavily infested with the cotton aphid (Aphis gossypii), are treated by being sprayed with the preparation of the active compound of the desired concentration. After the specicifed period of time mortality in % is determined. 100 % means all the aphids have been killed and 0 % means none of the aphids have been killed.
  • Corn plant leaves (Zea mays) in pots filled with soil, are treated by being drenched with the preparation of the active compound of the desired concentration and are infested with caterpillars of the fall army worm (Spodoptera frugiperda). After the specicifed period of time mortality in % is determined. 100 % means all the caterpillars have been killed and 0 % means none of the caterpillars have been killed. In this test, for example, the following compound from the preparation examples shows a superior level of activity compared to the prior state of the art: see table BCS233014 FC-Text - 115 - Table: Substance Structure Object Concentration % Efficacy dat* Example No. I-063 o ,0_ , . .

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Abstract

L'invention concerne de nouveaux composés de formule (I), les composés de formule (I) destinés à être utilisés en tant qu'acaricides et/ou insecticides pour lutter contre des parasites d'animaux, ainsi que des procédés et des intermédiaires pour leur préparation.
PCT/EP2024/070220 2023-07-31 2024-07-17 Dérivés de 6-[5-(éthylsulfonyl)-1-méthyl-1h-imidazol-4-yl]-7-méthyl-3-(pentafluoroéthyl)-7h-imidazo [4,5-c]pyridazine en tant que pesticides Pending WO2025026738A1 (fr)

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