WO2024170484A1 - Composés amides à activité pesticide - Google Patents

Composés amides à activité pesticide Download PDF

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Publication number
WO2024170484A1
WO2024170484A1 PCT/EP2024/053453 EP2024053453W WO2024170484A1 WO 2024170484 A1 WO2024170484 A1 WO 2024170484A1 EP 2024053453 W EP2024053453 W EP 2024053453W WO 2024170484 A1 WO2024170484 A1 WO 2024170484A1
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optionally substituted
alkyl
compound
methyl
cycloalkyl
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PCT/EP2024/053453
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English (en)
Inventor
Victor CEBAN
Thomas A. CLOHESSY
Stephania CHRISTOU
Thomas G.R. SELLERS
Simon Dieterich
Victoria Elizabeth JACKSON
Lorna BINKS
Peter Maienfisch
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Globachem Nv
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Publication of WO2024170484A1 publication Critical patent/WO2024170484A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/0827—Syntheses with formation of a Si-C bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/083—Syntheses without formation of a Si-C bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the present invention relates to novel pesticidally active amide compounds and in particular heteroaromatic amide compounds, to compositions comprising those compounds, and to their use in agriculture, for example in controlling insect pests and/or pests of the order Acarina damaging crops.
  • the present invention relates to a method for controlling insect pests and/or pests of the order Acarina damaging crops in which the compounds or the compositions of the present invention are applied.
  • the present invention therefore aims the provision of pesticidally active compounds and to compositions thereof which are useful in agriculture.
  • the present invention aims to provide novel compounds which are active against insect pests and/or pests of the order Acarina damaging crops, and which therefore can be used as agricultural agent and in methods of controlling these animal pests.
  • the present invention is based on the finding that the above object can be solved by novel compounds having a specific structure that includes an amide and a (hetero)aromatic moiety.
  • the present invention provides a compound of formula I:
  • Y is O or S;
  • R 1 is hydrogen, OH, OBenzyl or is selected from Ci-Ce alkyl, Ci-Ce cyanoalkyl, aminocarbonyl Ci-Ce alkyl, hydroxycarbonyl Ci-Ce alkyl, Ci-Ce nitroalkyl, trimethylsilyl Ci-Ce alkyl, C1-C3 alkoxy Ci-Ce alkyl, C1-C3 alkoxy Ci-Ce acyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C4 cycloalkyl C1-C2 alkyl-, oxetan-3-yl-CH2-, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl and
  • R 2 is selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, C1- C3 haloalkoxy, halogen, NO2, SF5, CN, C(O)NH2, C(O)OH, C(S)NH2, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2-one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1-yl that is optionally substituted, C3-C6
  • R 3 is hydrogen, C1-C3 alkyl or C1-C3 haloalkyl
  • a 1 is selected from N, CH and CR P , with R p being selected from hydrogen, C1-C3 alkyl, C1- C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, CN and cyclopropyl;
  • a 2 is selected from N, CH, CR q , with R q being selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, NO2, SF5, CN, C(O)NH2, C(O)OH, C(S)NH2, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2- one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrroli
  • Q is selected from pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, each of which is substituted with one or more R 4 and further optionally substituted with one or more R 6 ;
  • X is selected from (i) N and (ii) C which forms part of a 6-membered carbocyclic or heterocyclic ring fused to the 5-membered heterocycle to which Q is attached;
  • R 4 is Si(R’)3, wherein each R’ is independently selected from Ci-Ce alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-Ce alkynyl; optionally substituted phenyl; and Ci-Ce alkyl aryl;
  • R 5 is selected from hydrogen, halogen, CN, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, amino, C1-C3 alkyl amino, di(Ci-Cs alkyl) amino, Ci-Ce alkyloxycarbonyl amino, C(O)O C1-C3 alkyl, C(O)N(H) C1-C3 alkyl, N(H)C(O)O Ci-Ce alkyl, N(Ci- C3 alkyl)C(O)O Ci-Ce alkyl, N(H)SC>2 C1-3 alkyl, aryl and heteroaryl;
  • R 6 is selected from hydrogen, C1-C3 alkyl, Ci-Cs haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, C1- C3 haloalkoxy, halogen, NO2, SF5, CN, C(O)NH2, C(O)OH, C(S)NH2, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2-one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1-yl that is optionally substituted, C3-C6
  • the present invention provides a composition
  • a composition comprising a compound of formula I as defined in the first aspect, one or more auxiliaries and/or adjuvants, and optionally one or more other active ingredients.
  • the present invention provides a use of the compound according to the first aspect or a composition according to the second aspect in controlling insect pests and/or pests of the order Acarina damaging crops.
  • the present invention provides a method of controlling insect pests and/or pests of the order Acarina damaging crops which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an effective amount of a compound as defined in the first aspect of the invention, or a composition as defined in the second aspect of the invention.
  • the present invention provides compounds which may be useful intermediates in the preparation of the compounds according to the first aspect, as well as the use of any of these compounds in the preparation of a compound according to the first aspect, and a process for preparing a compound according to the first aspect that involves any of these compounds.
  • the present invention may provide compounds with improved human and environmental profiles compared to other products used to control insect pests and/or pests of the order Acarina in certain crops.
  • the present invention provides a method for the protection of plant propagation material from the attack by insects and/or the order Acarina damaging crops, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect of the present invention.
  • the present invention provides a plant propagation material, such as a seed, comprising, or treated with or adhered thereto, a compound of formula I as defined in the first aspect or a composition as defined in the second aspect of the present invention.
  • Ci-C n alkyl refers to a saturated straight-chain or branched hydrocarbon radical attached via any of the carbon atoms having 1 to n carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1 ,1 -dimethylpropyl, 1,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethylbutyl, 2-
  • Ci-C n haloalkyl refers to a straight-chain or branched saturated alkyl radical attached via any of the carbon atoms having 1 to n carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of chloro methyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2- iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroe
  • Ci-C2fluoroalkyl would refer to a Ci-C2alkyl radical which carries 1, 2, 3, 4, or 5 fluorine atoms, for example, any one of difluoromethyl, trifluoromethyl, 1- fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1 ,2,2-tetrafluoroethyl or pentafluoroethyl.
  • Ci-C n alkoxy refers to a straight-chain or branched saturated alkyl radical having 1 to n carbon atoms (as mentioned above) which is attached via an oxygen atom, i.e., for example, any one of the radicals methoxy, ethoxy, n-propoxy, 1 -methylethoxy, n-butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1,1 -dimethylethoxy.
  • haloCi-C n alkoxy refers to a Ci-C n alkoxy radical where one or more hydrogen atoms on the alkyl radical is replaced by the same or different halo atom(s) - examples include trifluoromethoxy, 2- fluoroethoxy, 3-fluoropropoxy, 3,3,3-trifluoropropoxy, 4-chlorobutoxy.
  • Ci-C n cyanoalkyl refers to a straight chain or branched saturated Ci- C n alkyl radical having 1 to n carbon atoms (as mentioned above), where one of the hydrogen atoms in these radicals is be replaced by a cyano group: for example, cyanomethyl, 2- cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-(cyanomethyl)-2-ethyl, 1-(methyl)-2-cyanoethyl, 4- cyanobutyl, and the like.
  • Cs-Cncycloalkyl refers to 3 to n membered cycloalkyl groups such as cyclopropane, cyclobutane, cyclopentane and cyclohexane.
  • C3-C4cycloalkyl-Ci-C2alkyl refers to 3 or 4 membered cycloalkyl group with either a methylene or ethylene group, which methylene or ethylene group is connected to the rest of the molecule. In the instance, the C3-C4cycloalkyl-Ci-C2alkyl- group is substituted, the substituent(s) can be on the cycloalkyl group and/or on the alkyl group.
  • C3-C6cycloalkylCi-C4haloalkoxy refers to a 3 to 6 membered cycloalkyl group connected to a 1 to 4 membered haloalkoxy, which haloalkoxy group is connected to the rest of the molecule.
  • aminocarbonylCi-C n alkyl refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by CONH2 group.
  • hydroxycarbonylCi-C n alkyl refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by COOH group.
  • Ci-C n alkylsulfanyl refers to a Ci-C n alkyl moiety linked through a sulfur atom.
  • Ci-C n haloalkylthio or “Ci-C n haloalkylsulfanyl” as used herein refers to a Ci-C n haloalkyl moiety linked through a sulfur atom.
  • C3- Cncycloalkylsulfanyl refers to 3 to n membered cycloalkyl moiety linked through a sulfur atom.
  • trimethylsilaneCi-C n alkyl refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by a -Si(CH3)3 group.
  • C2-C n alkenyl refers to a straight or branched alkenyl chain having from two to n carbon atoms and one or two double bonds, for example, ethenyl, prop-1 -enyl, but-2-enyl.
  • C2-C n haloalkenyl refers to a C2-C n alkenyl moiety substituted with one or more halo atoms which may be the same or different.
  • C2-C n alkynyl refers to a straight or branched alkynyl chain having from two to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl, but-3-ynyl.
  • C2-C n haloalkynyl refers to a C2-C n alkynyl moiety substituted with one or more halo atoms which may be the same or different.
  • Halogen or “halo” is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl.
  • aryl refers to a carbocyclic ring system comprising 6 to 10 carbon atoms and at least one aromatic ring.
  • the aryl group is a monocyclic or bicyclic ring system.
  • Aryl groups include, but are not limited to, aryl residues derived from benzene or naphthalene (i.e. , phenyl or naphthyl). Unless stated otherwise specifically in the specification, the term “aryl” or the prefix “ar “ (such as in “aralkyl”) is meant to include aryl groups that are optionally substituted.
  • heteroaryl refers to a 5- or 6-membered aromatic monocyclic ring having one or more heteroatoms independently selected from, for example, N, O and S.
  • heteroaryls J-1 to J-35 with their respective bonding site indicated as an arrow are shown below but are not limited thereto.
  • heteroaryl or the prefix “hetar” is meant to include aryl groups that are optionally substituted.
  • C3-C4cycloalkyl is optionally substituted with 1 or 2 halo atoms
  • C3-C4cycloalkyl is optionally substituted with 1 or 2 halo atoms
  • optional substitution means that the group referenced is either unsubstituted or is substituted by one or more, preferably 1 , 2, 3, 4 or 5, non-hydrogen substituents selected from R 1 , R 2 , R 3 , R 4 , R’, R 5 and R 6 as defined hereinabove.
  • substituted means any of the above groups ⁇ e.g., alkyl, alkylene, alkylcycloalkyl, alkoxy, alkylphosphoryl, alkylphosphorylaminyl, amidinylalkyloxy, guanidinylalkyloxy, alkylcarbonylaminylalkyloxy, heterocyclylalkyloxy, heteroarylalkyloxy, aminylalkyloxy, alkoxyalkyl, alkoxycarbonyl, haloalkylaminyl, hydroxylalkylaminyl, amidinylalkylaminyl, guanidinylalkylaminyl, aminylalkyl, aminylalkylaminyl, aminylalkoxy, alkylaminylalkoxy aryloxy, alkylaminyl, alkylcarbonylaminyl, alkylaminylalkyl, am
  • “Substituted” also means any of the above groups in which one or more hydrogen atoms are replaced by a higher-order bond (e.g., a double- or triple-bond) to a heteroatom such as oxygen in oxo, carbonyl, carboxyl, and ester groups; and nitrogen in groups such as imines, oximes, hydrazones, and nitriles.
  • “substituted” includes any of the above groups in which one or more hydrogen atoms are replaced with -SChNRgRh.
  • R g and Rh are the same or different and independently hydrogen, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, /V-heterocyclyl, heterocyclylalkyl, heteroaryl, /V-heteroaryl and/or heteroarylalkyl.
  • “Substituted” further means any of the above groups in which one or more hydrogen atoms are replaced by a bond to an aminyl, cyano, hydroxyl, imino, nitro, oxo, thioxo, halo, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, /V- heterocyclyl, heterocyclylalkyl, heteroaryl, /V-heteroaryl and/or heteroarylalkyl group.
  • each of the foregoing substituents may also be optionally substituted with one or more of the above substituents.
  • controlling refers to reducing the number of pests, eliminating pests and/or preventing further pest damage such that damage to a plant or to a plant derived product is reduced.
  • pest refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain and timber); and those pests associated with the damage of man-made structures.
  • the term pest encompasses all stages in the life cycle of the pest.
  • the term "effective amount” refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.
  • an effective amount is readily determined by the skilled person in the art, by the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to: the type of plant or derived product to be applied; the pest to be controlled & its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.
  • Embodiments according to the invention are provided as set out below.
  • the disclosure in the present application makes available each and every combination of these embodiments disclosed in the following.
  • the compound according to the first aspect of the invention is characterized by having in combination an amide moiety and a (hetero)aromatic moiety.
  • the compound according to the first aspect of the invention corresponds to the following formula I, or an agrochemically acceptable salt thereof, a stereoisomer thereof, an enantiomer thereof, a tautomer thereof or an /V-oxide thereof:
  • Y is O or S; preferably O.
  • R 1 is hydrogen, OH, OBenzyl or is selected from Ci-Ce alkyl, Ci-Ce cyanoalkyl, aminocarbonyl Ci-Ce alkyl, hydroxycarbonyl Ci-Ce alkyl, Ci-Ce nitroalkyl, trimethylsilayl Ci-Ce alkyl, C1-C3 alkoxy Ci-Ce alkyl, C1-C3 alkoxy Ci-Ce acyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-Ce haloalkynyl, C3-C4 cycloalkyl C1-C2 alkyl-, oxetan-3-yl-CH2-, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl and benzyl, each of which
  • R 1 is selected from hydrogen, OH, OBenzyl or is selected from Ci-Ce alkyl, Ci-Ce cyanoalkyl, C1-C3 alkoxy Ci-Ce alkyl, C1-C3 alkoxy Ci-Ce acyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C3- C4 cycloalkyl C1-C2 alkyl, Ci-Ce alkylcarbonyl and Ci-Ce alkoxycarbonyl, each of which is optionally substituted; more preferably hydrogen, OH, methyl, ethyl, acetyl, 2-methoxyacetyl, cyclopropylmethyl, prop- 2-yn-1-yl, 2-difluoroethyl, cyanomethyl or allyl; most preferably methyl.
  • R 2 is selected from hydrogen, C1-C3 alkyl, Ci-Cs haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, Ci- C3 haloalkoxy, halogen, NO2, SF5, ON, C(O)NH2, C(O)OH, C(S)NH2, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2-one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1-yl that is optionally substituted, C3-C6 cyclo
  • R 2 is C1-C3 haloalkyl; more preferably CF3.
  • R 3 is hydrogen, C1-C3 alkyl or C1-C3 haloalkyl.
  • R 3 is hydrogen or Ci-Cs alkyl; more preferably methyl.
  • a 1 is selected from N, CH and CR P , with R p being selected from hydrogen, C1-C3 alkyl, C1- C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, CN and cyclopropyl.
  • a 1 is CR P ; more preferably CH.
  • a 2 is selected from N, CH, CR q , with R q being selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, NO2, SFs, CN, C(O)NH2, C(O)OH, C(S)NH2, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2- one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrol
  • a 2 is CR P ; more preferably CR P with R p being C1-C3 haloalkyl.
  • Q is selected from pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, each of which is substituted with one or more R 4 and further optionally substituted with one or more R 6 .
  • Q is pyridinyl; more preferably, Q is selected from 2-pyridinyl, 3-pyridinyl and 4-pyridinyl; most preferably, Q is 2-pyridinyl.
  • Q is preferably substituted with one R 4 only.
  • X is selected from (i) N, and (ii) C which forms part of a 6-membered carbocyclic or heterocyclic ring fused to the 5-membered heterocycle to which Q is attached; preferably X is N.
  • R 4 is Si(R’)3, wherein each R’ is independently selected from Ci-Ce alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-Ce alkynyl, aryl, and Ci-Ce alkyl aryl.
  • each R’ in any R 4 is independently selected from Ci-Ce alkyl, C2-C6 alkenyl, phenyl and benzyl; more preferably, each R’ is independently selected from methyl, ethyl, /so-propyl, terf-butyl, allyl, phenyl and benzyl.
  • at least one C2-C6 alkenyl, aryl, or Ci-Ce alkyl aryl is vinyl or optionally substituted phenyl.
  • Si(R’)3 in any R 4 is selected from SiMea, Si Eta, Si/Pr 3 , SiMeaPh, SiMeat-Bu, Sif- BuPha, SiMeaBn, SiMeaCy, SiMeaallyl, SiMeapropargyl and SiMeavinyl; more preferably, selected from SiMea, SiEts SiMeavinyl and SiMeaPh; most preferably SiMea.
  • R 5 is selected from hydrogen, halogen, CN, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, amino, C1-C3 alkyl amino, di(Ci-Ca alkyl) amino, Ci-Ce alkyloxycarbonyl amino, C(O)O C1-C3 alkyl, C(O)N(H) C1-C3 alkyl, N(H)C(O)O Ci-Ce alkyl, N(Ci- C3 alkyl)C(O)O Ci-Ce alkyl, N(H)SOa C1-3 alkyl, aryl and heteroaryl.
  • R 5 is hydrogen, halogen, C1-C3 alkyl, C3-C4 cycloalkyl, amino, Ci-Ce alkyloxycarbonyl amino, C(O)O C1-C3 alkyl, C(O)N(H) C1-C3 alkyl, N(H)C(O)O Ci-C 6 alkyl, N(CI-C 3 alkyl)C(O)O Ci-Ce alkyl, N(H)SC>2 C1-3 alkyl or heteroaryl; more preferably, hydrogen, chlorine, bromine, cyclopropyl, methyl, isopropyl, tert-butyl, amino, tert-butyloxycarbonyl amino, C(O)OCH3, or pyridnyl; most preferably, hydrogen, methyl, amino, cyclopropyl, N(H)CH3, N(CH3)a, N(CH3)Boc, N(H)SO 2 )CH 3 , N(
  • R 6 is selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, Ci-Cs haloalkylthio, C1-C3 alkoxy, C1- C3 haloalkoxy, halogen, NO2, SFs, CN, C(O)NHa, C(O)OH, C(S)NHa, C3-C6 cycloalkyl that is optionally substituted, C3-C6 cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR S with R s being phenyl, benzyl, heteroaryl or C3-C6 cycloalkyl each of which is optionally substituted, piperidin-2-one-1-yl, pyridin-2-one-1-yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1-yl that is optionally substituted, C3
  • R 6 is H.
  • Y is O
  • R 1 is hydrogen
  • R 2 is CF3
  • a 1 is CR P with R p being hydrogen
  • a 2 is R q with R q being trifluoromethyl
  • R 2 is trifluoromethyl
  • R 3 is methyl
  • Q is represented by the following structure wherein R 4 is SiMea; preferably Q is represented by wherein R 4 is SiMea.
  • the compound of formula I corresponds to a compound of formula II:
  • X is C which forms part of a 6-membered carbocyclic or heterocyclic ring fused to the 5-membered heterocycle to which Q is attached.
  • the compound may be selected from any of the following formulae llla-llle: more preferably the compound corresponds to formula lllb; and Y, R 1 -R 6 , A 1 , A 2 and Q are defined as above.
  • the invention corresponds to the following formula Ila, or an agrochemically acceptable salt thereof, a stereoisomer thereof, an enantiomer thereof, a tautomer thereof or an /V-oxide thereof, wherein all groups are as defined hereinabove:
  • the invention corresponds to any of the following formulae lib to Hz or llaa, or an agrochemically acceptable salt thereof, a stereoisomer thereof, an enantiomer thereof, a tautomer thereof or an /V-oxide thereof, wherein Y is O or S, preferably O, and the remaining groups are defined as follows:
  • the compound of the invention corresponds to a compound of formula III or an agrochemically acceptable salt thereof, a stereoisomer thereof, an enantiomer thereof, a tautomer thereof or an /V-oxide thereof, wherein X is C which forms part of a 6- membered carbocyclic or heterocyclic ring fused to the 5-membered heterocycle to which
  • the compound may be selected from any of the following formulae llla-llle:
  • Y is O or S, more preferably O. Even more preferably, the compound corresponds to formula 11 lb and the remaining groups are defined as follows:
  • Sensitive functional groups may need to be protected and deprotected during synthesis of a compound of the invention. This may be achieved by conventional methods using protecting groups (sometimes abbreviated as “PG” hereinafter), for example as described in “Protective Groups in Organic Synthesis” by TW Greene and PGM Wuts, John Wiley & Sons Inc. (1999), and references therein.
  • protecting groups sometimes abbreviated as “PG” hereinafter
  • the silyl moiety is added in the last step on the appropriate silylated material using the conditions mentioned in schemes 1 , 2 and 7-13.
  • the silyl moiety may be also added in a different position using the conditions mentioned in schemes 1-18.
  • the compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • the present invention also relates to novel compounds which are intermediates in the preparation of the compound according to formula I.
  • the invention therefore provides compounds having the following structures:
  • compositions comprising a compound of formula I
  • compositions comprising a compound of formula I as defined in any of the above embodiments relating to the first aspect of the invention, one or more auxiliary and/or adjuvant, and optionally one or more other active ingredients.
  • compositions can be in various physical forms, e.g., in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g., from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010).
  • Such compositions can either be used directly or diluted prior to use.
  • the dilutions can be made, for example, with water, liquid fertilisers, micronutrients
  • compositions according to the second aspect of the invention are prepared in a known manner, by mixing the compounds of the formula I with the one or more adjuvants, and optionally one or more other active ingredients.
  • the composition may comprise further additives that are conventional in this technical field, including but not limited to colorants, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • the compositions can be prepared e.g., by mixing a compound according the first aspect of the present invention as the active ingredient with the adjuvant(s) in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g., slow-release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95% by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • the adjuvants that are suitable for the preparation of the compositions according to the second aspect of the present invention are known in this technical field.
  • liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, /V,/V-dimethylformamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
  • a large number of surface-active substances can be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.
  • Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes.
  • Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty
  • Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
  • compositions according to the second aspect of the present invention can further include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • the amount of oil additive in the composition according to the invention is generally from 0.01 to 10%, based on the mixture to be applied.
  • the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared.
  • Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively).
  • Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.
  • inventive compositions generally comprise from 0.1 to 99% by weight, especially from 0.1 to 95% by weight, of compounds of the present invention and from 1 to 99.9% by weight of a formulation adjuvant which preferably includes from 0 to 25% by weight of a surface-active substance.
  • Formulation types for the composition of the invention include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EG), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (Sil), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.
  • the rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • Preferred formulations can have the following compositions (% refers to weight % unless otherwise indicated), wherein “active ingredient” refers to the compounds of the present invention:
  • Emulsifiable concentrates active ingredient: 1 to 95%, preferably 20 to 80% surface-active agent: 1 to 30%, preferably 5 to 20% liquid carrier: 1 to 80%, preferably 1 to 35%
  • Dusts active ingredient: 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99%
  • Suspension concentrates active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably 88 to 30% surface-active agent: 1 to 40%, preferably 2 to 30%
  • Wettable powders active ingredient: 0.5 to 90%, preferably 1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 95%, preferably 15 to 90%
  • Granules active ingredient: 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%.
  • compositions according to the second aspect of the present invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients.
  • the mixtures of the compounds of formula I with other insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use. Therefore, the composition according to the second aspect of the present invention may further contain one or more other active ingredients.
  • Suitable other active ingredients are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.
  • compositions according to the second aspect of the invention are preferred: substances consisting of petroleum oils (628); an insect control active substance selected from Abamectin, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, Acynonapyr, Afidopyropen, Afoxolaner, Alanycarb, Allethrin, Alpha- Cypermethrin, Alphamethrin, Amidoflumet, Aminocarb, Azocyclotin, Bensultap, Benzoximate, Benzpyrimoxan, Betacyfluthrin, Beta- cy permethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin S)-cyclopentylisomer, Bioresmethrin, Bistrifluron, Broflanilide, Brofluthrinate, Brom
  • Bacillus pumilus (NRRL Accession No B-30087), Bacillus pumilus AQ717 (NRRL Accession No. B-21662), Bacillus sp. AQ178 (ATCC Accession No. 53522), Bacillus sp. AQ175 (ATCC Accession No. 55608), Bacillus sp. AQ177 (ATCC Accession No. 55609), Bacillus subtilis unspecified, Bacillus subtilis AQ153 (ATCC Accession No. 55614), Bacillus subtilis AQ30002 (NRRL Accession No. B-50421), Bacillus subtilis AQ30004 (NRRL Accession No.
  • Bacillus subtilis AQ713 (NRRL Accession No. B-21661), Bacillus subtilis AQ743 (NRRL Accession No. B-21665), Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619), Bacillus thuringiensis BD#32 (NRRL Accession No B-21530), Bacillus thuringiensis subspec.
  • israeltaki BMP 123 Beauveria bassiana, D-limonene, Granulovirus, Harpin, Helicoverpa armigera Nucleopolyhedrovirus, Helicoverpa zea Nucleopolyhedrovirus, Heliothis virescens Nucleopolyhedrovirus, Heliothis punctigera Nucleopolyhedrovirus, Metarhizium spp., Muscodor albus 620 (NRRL Accession No. 30547), Muscodor roseus A3-5 (NRRL Accession No.
  • Neem tree based products Paecilomyces fumosoroseus, Paecilomyces lilacinus, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, P- cymene, Plutella xylostella Granulosis virus, Plutella xylostella Nucleopolyhedrovirus, Polyhedrosis virus, pyrethrum, QRD 420 (a terpenoid blend), QRD 452 (a terpenoid blend), QRD 460 (a terpenoid blend), Quillaja saponaria, Rhodococcus globerulus AQ719 (NRRL Accession No B-21663), Spodoptera frugiperda Nucleopolyhedrovirus, Streptomyces galbus (NRRL Accession No.
  • an algicide selected from the group of substances consisting of bethoxazin [CON], copper dioctanoate (170), copper sulfate (172), cybutryne [CON], dichlone (1052), dichlorophen (232), endothal (295), fentin (347), hydrated lime [CON], nabam (566), quinoclamine (714), quinonamid (1379), simazine (730), triphenyltin acetate (347) and triphenyltin hydroxide (347); an anthelmintic selected from the group of substances consisting of abamectin (1), crufomate (1011), Cyclobutrifluram, doramectin [CCN], emamectin (291), emamectin benzoate (291), eprinomect
  • Anagrapha falcifera NPV 28
  • Anagrus atomus 29
  • Aphelinus abdominalis 33
  • Aphidius colemani 34
  • Aphidoletes aphidimyza 35
  • Autographa californica NPV 38
  • Bacillus firmus 48
  • Bacillus sphaericus Neide 49
  • Bacillus thuringiensis 49
  • Bacillus thuringiensis 49
  • Bacillus thuringiensis Berliner 51
  • Bacillus thuringiensis subsp. aizawai 51
  • Bacillus thuringiensis subsp. israelensis 51
  • Bacillus thuringiensis subsp. japonensis 51
  • Bacillus thuringiensis subsp. kurstaki 51
  • Bacillus thuringiensis subsp. tenebrionis 51
  • Beauveria bassiana 53
  • Beauveria brongniartii 54
  • Chrysoperla carnea 151
  • Cryptolaemus montrouzieri 178
  • Cydia pomonella GV (191)
  • Dacnusa sibirica 212
  • Diglyphus isaea 254
  • Encarsia formosa 293
  • Eretmocerus eremicus 300
  • Helicoverpa zea NPV 431
  • Heterorhabditis bacteriophora and H.
  • a soil sterilant selected from the group of substances consisting of iodomethane (542) and methyl bromide (537); a chemosterilant selected from the group of substances consisting of apholate [CCN], bisazir [CCN], busulfan [CCN], diflubenzuron (250), dimatif [CCN], hemel [CCN], hempa [CCN], metepa [CCN], methiotepa [CCN], methyl apholate [CCN], morzid [CCN], penfluron [CCN], tepa [CCN], thiohempa [CCN], thiotepa [CCN], tretamine [CCN] and uredepa [CCN]; an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with
  • lecontei NPV, Orius spp. Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis , Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en-1-yl a
  • the compounds in this paragraph may be prepared from the methods described in WO2017/055473, WO2017/055469, WO2017/093348 and WO2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1 - yl)propan-2-ol (this compound may be prepared from the methods described in WO2017/055473, WO2017/055469, WO2017/093348 and WO2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1 - yl)propan-2-ol (this compound may be prepared from the methods described in
  • microbials including: Acinetobacter Iwoffii, Acremonium alternatum, Acremonium cephalosporium, Acremonium diospyri, Acremonium obclavatum, Adoxophyes orana granulovirus (AdoxGV) (Capex®), Agrobacterium radiobacter strain K84 (Galltrol-A®), Alternaria alternate, Alternaria cassia, Alternaria destruens (Smolder®), Ampelomyces quisqualis (AQ10®), Aspergillus flavus AF36 (AF36®), Aspergillus flavus NRRL 21882 (Aflaguard®), Aspergillus spp., Aureobasidium pullulans, Azospirillum, (MicroAZ®, TAZO B®), Azotobacter, Azotobacter chroocuccum (Azotomeal®), Azotobacter cysts (Bionatural Blooming Blo
  • amyloliquefaciens strain FZB24 (Taegro®, Rhizopro®), Bacillus thuringiensis Cry 2Ae, Bacillus thuringiensis CrylAb, Bacillus thuringiensis aizawai GC 91 (Agree®), Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®), Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP ®, Astuto®, Dipel WP®, Biobit®, Foray®), Bacillus thuringiensis kurstaki BMP 123 (Baritone®), Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®), Bacillus thuringiensis strain BD#32, Bacillus thuringiensis strain AQ52, Bacillus
  • aizawai XenTari®, DiPei®
  • bacteria spp. GROWMEND®, GROWSWEET®, Shootup®
  • bacteriophage of Clavipacter michiganensis AgriPhage®
  • Bakflor® Beauveria bassiana
  • Beauveria bassiana GHA Mycotrol ES®, Mycotrol O®, BotaniGuard®
  • Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®
  • Beauveria spp. Botrytis cineria, Bradyrhizobium japonicum (TerraMax®), Brevibacillus brevis, Bacillus thuringiensis tenebrionis (Novodor®), BtBooster, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®), Burkholderia gladii, Burkholderia glad
  • SoilGard® Gliocladium virens (Soilgard®), Granulovirus (Granupom®), Halobacillus halophilus, Halobacillus litoralis, Halobacillus trueperi, Halomonas spp., Halomonas subglaciescola, Halovibrio variabilis, Hanseniaspora uvarum, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®), Helicoverpa zea nuclear polyhedrosis virus (Gemstar®), Isoflavone - formononetin (Myconate®), Kloeckera apiculata, Kloeckera spp., Lagenidium giganteum (Laginex®), Lecanicillium longisporum (Vertiblast®), Lecanicillium muscarium (Vertikil®), Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®), Marinococcus
  • LC 52 (Sentinel®), Trichoderma lignorum, Trichoderma longibrachiatum, Trichoderma polysporum (Binab T®), Trichoderma taxi, Trichoderma virens, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®), Trichoderma viride, Trichoderma viride strain ICC 080 (Remedier®), Trichosporon pullulans, Trichosporon spp., Trichothecium spp., Trichothecium roseum, Typhula phacorrhiza strain 94670, Typhula phacorrhiza strain 94671, Ulocladium atrum, Ulocladium oudemansii (Botry-Zen®), Ustilago maydis, various bacteria and supplementary micronutrients (Natural II®), various fungi (Millennium Microbes®), Verticillium chlamydosporium, Vertic
  • Plant extracts including: pine oil (Retenol®), azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, Botanical IGR (Neemazad®, Neemix®), canola oil (Lilly Miller Vegol®), Chenopodium ambrosioides near ambrosioides (Requiem®), Chrysanthemum extract (Crisant®), extract of neem oil (Trilogy®), essentials oils of Labiatae (Botania®), extracts of clove rosemary peppermint and thyme oil (Garden insect killer®), Glycinebetaine (Greenstim®), garlic, lemongrass oil (Green Match®), neem oil, Nepeta cataria (Catnip oil), Nepeta catarina, nicotine, oregano oil (MossBuster®), Pedaliaceae oil (Nematon®), pyrethrum, Quillaja
  • Anagyrus fusciventris Anagyrus kamali, Anagyrus loecki, Anagyrus pseudococci (Citripar®), Anicetus remedies, Anisopteromalus calandrae, Anthocoris nemoralis (Anthocoris-System®), Aphelinus abdominalis (Apheline®, Aphiline®), Aphelinus asychis, Aphidius colemani (Aphipar®), Aphidius ervi (Ervipar®), Aphidius gifuensis, Aphidius matricariae (Aphipar-M®), Aphidoletes aphidimyza (Aphidend®), Aphidoletes aphidimyza (Aphidoline®), Aphytis lingnanensis, Aphytis melinus, Aprostocetus hagenowii, Atheta coriaria (Staphyline®), Bombus spp., Bomb
  • the one or more other active ingredients that may optionally present in the compositions of the invention are selected from Alpha-Cypermethrin, Bifenthrin, Broflanilide, Chlorantraniliprole, Clothianidin, Cyantraniliprole, Cypermethrin, Deltamethrin, Dicloromezotiaz, dimpropyridaz, Emamectin (or Emamectin Benzoate), Fluazaindolizine, Flubendiamide, Fluopyram, Imidacloprid, Indoxacarb, Isocycloseram, Lambda-Cyhalothrin, Permethrin, Spinetoram, Spinosad, Spiropidion, Spirotetramat, Sulfoxaflor, Tetraniliprole, Thiamethoxam, Tioxazafen, Bacillus thuringiensis, Helicoverpa armigera Nucleopolyhedr
  • the active ingredient mixture of the compounds of formula I with active ingredients described above comprises preferably in a mixing ratio by weight of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1 :3, or 1:2, or 1:600, or 1 :300, or 1:150, or 1:35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 4:
  • the compounds according to the first aspect of the invention and the compositions according to the second aspect of the invention as described above may be used in agriculture, in particular in controlling insect pests and/or pests of the order Acarina damaging crops. Therefore, the present invention provides in a third aspect of the present invention the use of the compound according to the first aspect of the invention or the composition according to the second aspect of the invention in agriculture.
  • a method for controlling insect pests and/or pests of the order Acarina damaging crops comprising applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of the compound according to the first aspect of the present invention or a composition according to the second aspect of the present invention.
  • insects from the sub-order of Auchenorrhyncha e.g., Amrasca biguttula, Empoasca spp., Ne- photettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citrr, Lepidoptera, e.g., Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplu- sia ni, Tuvaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavaszavas
  • Whiteflies e.g., Thaleurodes vaporariorum, Bemisia spp.; Coleoptera, e.g., Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimline- ata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaha linearia, Agriotes spp., Epilachna spp.; Flies, e.g., Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.; Coccoidea, e.g., Aonidiella aurantia, Ferrisia virgate; Anthropods of class Arachnida (Mites), e.g., Penthaleus major, Tetranychus spp.; Nematodes,
  • the compounds and/or compositions of the invention may also be suitable for use in treating or protecting animals against infestation or infection by parasites, such as animals on pets like fleas.
  • the compounds according to the first aspect of the invention and/or the compositions according to the second aspect of the invention are especially suitable for efficiently combating pests from the order Acarina, for example, Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp., Eotetranychus spp., Eriophyes spp., Hemitarsonemus spp.
  • Acarina for example, Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomm
  • a composition according to the second aspect of the invention as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds according to the first aspect of the present invention and further other active ingredients as described above, if present, is not essential.
  • the application methods for the compounds and compositions that is the methods of controlling the indicated pests, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compounds and compositions for controlling pests of the abovementioned type are subjects of the invention.
  • Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient.
  • the rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.
  • a preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question.
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.
  • the compounds according to the first aspect of the invention and compositions thereof according to the second aspect of the invention are also suitable for the protection of crops, plants, plant propagation materials, e.g., seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g., seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound according to the first aspect of the invention or a composition according to the second aspect of the invention.
  • a plant protection method which comprises contacting crops, plants, plant propagation materials, e.g., seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound according to the first aspect of the invention or a composition according to the second aspect of the invention.
  • plant includes cereals, e.g., durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize I sweet and field corn); beet, e.g., sugar beet, or fodder beet; fruits, e.g., pomes, stone fruits, or soft fruits, e.g., apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, e.g., beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g., rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g., squashes, pumpkins, cucumber or melons
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g., cucumbers, tomatoes, beans or squashes.
  • compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling.
  • These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention.
  • Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • the present invention also comprises seeds coated or treated with or containing a compound of formula I.
  • coated or treated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application.
  • the present invention makes available a plant propagation material adhered thereto with a compound of formula I.
  • a composition comprising a plant propagation material treated with a compound of formula I.
  • Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the seed treatment application of the compound according to the first aspect of the invention or the composition according to the second aspect of the invention can be carried out by any known methods, such as spraying or by dusting the seeds before.
  • Flash chromatography was carried out using a Biotage Isolera 4, with Biotage® SNAP KP-Sil cartridges, packed with 50 pm silica particles with a surface area of 500 m 2 /g, or alternative cartridges ⁇ e.g., Puriflash, produced by Interchim) where stated, or using silica gel (40 - 63 pm particles).
  • Visualisation was carried out with UV light (254 nm) and by staining with either potassium permanganate, phosphomolybdic acid (PMA) or ninhydrin solutions.
  • Preparative HPLC was carried out using Teledyne ISCO ACCQ HP125 instrument using methods E (low pH) or F (high pH).
  • LogD was measured using the shake flask methodology.
  • the aqueous phase used is a 10 mM solution of sodium phosphate buffer adjusted to pH 7.4 and Octanol is used as the organic solvent. Quantitation of test compound in both phases is via LC-MS/MS.
  • DIPEA - N,N-diisopropylethylamine also referred to as “Hunig's base”.
  • Example 2 The following Examples were prepared using the general method described in Example 1-2 from the appropriate intermediates or commercial materials.
  • Example l-2a The following Examples were prepared using the general method described in Example l-2a from the appropriate intermediates or commercial materials.
  • Example P-1 (S)-3,5-bis(trifluoromethyl)-A/-(1-(1 -(5-(trimethylsilyl)pyridin-2-yl)-1 /7-1 ,2,4-triazol- 5-yl)ethyl)benzamide
  • Example 1-11 were prepared using the general method described in Example 1-11 from the appropriate intermediates or commercial materials.
  • Example P-2 (S)-/V-(1-(3-methyl-1-(5-(trimethylsilyl)pyridin-2-yl)-1/7-1 ,2,4-triazol-5-yl)ethyl)-3,5- bis(trifluoromethyl)benzamide
  • 1 ,1-dimethoxy-/V,/ ⁇ /-dimethylethanamine 41 mg
  • 2- methyltetrahydrofuran 1 .9 mL
  • stir the reaction mixture at 70 °C for 2 hours then concentrate.
  • 2-methyltetrahydrofuran (1.9 mL) followed by l-2a (55 mg) and acetic acid (1 mL).
  • Example P-3 (S)-/V-(1-(3-cyclopropyl-1-(5-(trimethylsilyl)pyridin-2-yl)-1/7-1 ,2,4-triazol-5-yl)ethyl)-
  • Example P-4 tert-Butyl (S)-(5-(1-(3,5-bis(trifluoromethyl)benzamido)ethyl)-1-(5- (tri methy Isi ly I) py rid i n-2-y I)- 1 /7-1 ,2,4-triazol-3-yl)carbamate
  • Example P-21 tert-butyl (S)-(5-(1-(3,5-bis(trifluoromethyl)benzamido)ethyl)-1-(5-
  • Example P-22 (S)-/V-(1-(3-(methylamino)-1-(5-(trimethylsilyl)pyridin-2-yl)-1/7-1 ,2,4-triazol-5- yl)ethyl)-3,5-bis(trifluoromethyl)benzamide
  • Example P-4 The following Examples were prepared using the general method described in Example P-4 from the appropriate intermediates or commercial materials.
  • Example P-24 methyl (S)-(5-(1-(3,5-bis(trifluoromethyl)benzamido)ethyl)-1-(5-
  • Example P-6 A/-hydroxy-3,5-bis(trifluoromethyl)-A/-(1-(1 -(5-(trimethylsilyl)pyridin-2-yl)-1 /7-1 ,2,4- triazol-5-yl)ethyl)benzamide
  • Example P-8 (S)-/V-(2-methoxyacetyl)-3,5-bis(trifluoromethyl)-/ ⁇ /-(1-(1-(5-(trimethylsilyl)pyridin- 2-y I)- 1 /7-1 ,2,4-triazol-5-yl)ethyl)benzamide
  • Example P-9 (S)-/V-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)-/ ⁇ /-(1-(1-(5-(trimethylsilyl)pyridin- 2-y I)- 1 /7-1 ,2,4-triazol-5-yl)ethyl)benzamide
  • TEA 56 pL
  • 3,5-bis(trifluoromethyl)benzoyl chloride 24 pL
  • a solution of 1-10 42 mg
  • chloroform 1 mL
  • Example P-1 The following Examples were prepared using the general method described in Example P-1 from the appropriate intermediates or commercial materials.
  • Example P-19 methyl (S)- 5-(1-(3,5-bis(trifluoromethyl)benzamido)ethyl)-1-(5- (tri methy Isi ly I) py rid i n-2-y I)- 1 /7-1 ,2,4-triazole-3-carboxylate
  • Example P-28 (S)-3,5-bis(trifluoromethyl)-A/-(1-(3-(5-(trimethylsilyl)pyridin-2-yl)-3/7-imidazo[4,5- b]pyridin-2-yl)ethyl)benzamide
  • Test compounds were diluted in an IF-50 water/tween solution. Cabbage leaf discs were immersed in the test solutions and dried. The dried leaves were placed in petri dishes containing a moistened piece of filter paper and infested with 5 second-instar diamondback moth larvae. The dishes were placed in a growth chamber for 4 days and percent mortality of the larvae recorded.
  • the following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 40 ppm: P-1 , P-2, P-3, P-4, P- 5, P-6, P-7, P-8, P-9, P-10, P-11 , P-12, P-13, P-14, P-15, P-16, P-17, P-18, P-19, , P-20, P-21 , P-22, P-23, P-24, P-25, P-26, P-27, P-28.

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  • Pest Control & Pesticides (AREA)
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  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

La présente invention concerne de nouveaux composés amides à activité pesticide et en particulier des composés amides hétéroaromatiques, des compositions comprenant ces composés, et leur utilisation en agriculture, par exemple dans la lutte contre les insectes nuisibles et/ou les nuisibles de l'ordre des Acariens endommageant les cultures. De plus, la présente invention concerne un procédé de lutte contre les insectes nuisibles et/ou les nuisibles de l'ordre des Acariens endommageant les cultures dans lesquelles les composés ou les compositions de la présente invention sont appliqués.
PCT/EP2024/053453 2023-02-13 2024-02-12 Composés amides à activité pesticide WO2024170484A1 (fr)

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