[go: up one dir, main page]

AU2024260362A1 - Pyrimidine compounds for the control of invertebrate pests - Google Patents

Pyrimidine compounds for the control of invertebrate pests

Info

Publication number
AU2024260362A1
AU2024260362A1 AU2024260362A AU2024260362A AU2024260362A1 AU 2024260362 A1 AU2024260362 A1 AU 2024260362A1 AU 2024260362 A AU2024260362 A AU 2024260362A AU 2024260362 A AU2024260362 A AU 2024260362A AU 2024260362 A1 AU2024260362 A1 AU 2024260362A1
Authority
AU
Australia
Prior art keywords
alkyl
haloalkyl
cycloalkyl
substituted
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
AU2024260362A
Inventor
Julia Pedroni
Matthias Pohlman
Christoph Schissler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP23169385.4A external-priority patent/EP4455137A1/en
Application filed by BASF SE filed Critical BASF SE
Publication of AU2024260362A1 publication Critical patent/AU2024260362A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Insects & Arthropods (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catching Or Destruction (AREA)

Abstract

The invention relates to compounds of formula I wherein the variables have the meanings as defined in the specification, to compositions comprising them, to active compound combinations comprising them, and to their use for protecting growing plants and animals from attack or infestation by invertebrate pests, furthermore, to seed comprising such compounds.

Description

Pyrimidine compounds for the control of invertebrate pests Description The invention relates to compounds of formula I I wherein R1 is H, OH, NR12R13, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C5-alkoxy, C1-C4- alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-halocycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, which groups are unsub- stituted, or partially or fully substituted with R11; or C(=N-R11)R12, C(O)R11a; R10 is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C4-cycloalkyl-C1-C2-alkyl, C3-C4-halocycloalkyl-C1-C2-alkyl, C(O)-C1-C4-alkyl, C(O)-C1-C4-haloalkyl, C(O)-C3-C4-cycloalkyl, C(O)- C3-C4-halocycloalkyl, SOm-C1-C4-alkyl, SOm-C1-C4-haloalkyl, SOm-C3-C6-cycloalkyl, or phenyl which is unsubstituted or partially or fully substituted with R3a; R11 is halogen, CN, NO2, NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR10, Si(CH3)3; C1-C6-alkyl; C1-C6- haloalkyl; C2-C6-alkenyl; C2-C6-haloalkenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl-C1-C2- alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, C1-C3- haloalkyl, and/or CN; R11a is NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR10, Si(CH3)3; C1-C6-haloalkyl; C2-C6-alkenyl; C2-C6- haloalkenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl-C1-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; R12, R13 are independently from each other H, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4- haloalkyl, C3-C6-cycloalkyl, C(O)-C1-C4-alkyl, C(O)-C1-C4-haloalkyl, C(O)-C3-C4-cycloalkyl, C(O)-C3-C4- halocycloalkyl, C(O)NH-C1-C4-alkyl, C(O)NH-C1-C4-haloalkyl, C(O)N(C1-C4-alkyl)-C1-C4-alkyl, C(O)N(C1-C4-haloalkyl)-C1-C4-alkyl, C(O)N(C1-C4-haloalkyl)-C1-C4-haloalkyl, C(O)NH-C1-C4-alkoxy, C(O)NH-C1-C4-haloalkoxy, C(O)NH-C1-C4-alkoxy-C1-C4-alkyl, C(O)NH-C1-C4-alkoxy-C1-C4-haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocyclyl or 5- or 6-membered hetaryl, C(O)NH-C1-C4- alkyl-phenyl, C(O)NH-C1-C4-alkyl-3-6-membered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; S(O)m-C1-C4-haloalkyl, S(O)m-C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloalkyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; or or R12 and R13 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially or fully unsaturated heterocycle, which heterocycle may additionally contain 1 or 2 heteroatoms or heteroatom-containing groups selected from N, O, S(O)m, and optionally one or two groups C(O) as ring members, and which heterocycle is unsubstituted or substituted with one or more R3a; m is 0, 1, or 2; R2 is H, CN, C1-C3-alkyl, C1-C3-haloalkyl, C2-C3-alkynyl; R3 halogen, CN, NO2; C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-alkenyl, C1-C6- alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C6-cycloalkyl, 3- to 6-membered heterocyclyl, which are unsubstituted or substituted with R3a; OR14, NR12R13, C(O)NR12R13, C(O)OR14, C(O)R15, S(O)m-R15; R14 is as defined for R10; R15 is H, C1-C4-alkyl, or C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, which carbon chains are unsubstituted or partially or fully substituted with R11; or 3- to 6-membered heterocyclyl, 5- or 6- membered hetaryl, or phenyl, which rings are unsubstituted or substituted with R3a; R3a is halogen, CN, NO2, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy, C3- C4-cycloalkyl, C3-C4-halocycloalkyl, S(O)m-C1-C4-alkyl, S(O)m-C1-C4-haloalkyl, S(O)m-C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloalkyl; n is 0, 1, 2, or 3; R4 is 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or partially or fully substituted with R3; or R4 is 3- to 7-membered saturated or unsaturated heterocyclyl containing at least one heteroatom or group selected from N, O, S(O)m, and optionally one or two groups C(O) as ring members, which rings are unsubstituted or partially or fully substituted with R3; if substituted to a ring C atom, or partially or fully substituted with R3b if substituted to a ring N atom: R3b C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3- C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C6-cycloalkyl which are unsubstituted or substituted with R3a; C(O)NR12R13, C(O)OR14, C(O)R15, S(O)m-R15; R5 is defined as for R3; X is N, CH, or CR3c; R3c is as defined for R3; and the N-oxides, stereoisomers, and agriculturally or veterinarily acceptable salts thereof. The invention also provides agricultural compositions comprising at least one compound of formula I, a stereoisomer thereof and/or an agriculturally acceptable salt thereof and at least one liquid and/or solid carrier, especially at least one inert liquid and/or solid agriculturally acceptable carrier. The invention also provides a veterinary composition comprising at least one compound of formula I, a stereoisomer thereof and/or a veterinarily acceptable salt thereof and at least one liquid and/or solid carrier, especially at least one inert veterinarily liquid and/or solid acceptable carrier. The invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein. The invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof. The invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of formula I or a veterinarily acceptable salt thereof. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal. WO2017/192385, WO2019/170626, WO2019/197468, WO2021/165195, WO2021/224323, WO2023/037249, and WO2023/058748 describe structurally closely related active compounds, wherein the 4-pyrimidine is generally substituted at the 6-position, usually with groups selected from CN, amides, CF3, and sulfoximines. These compounds are mentioned to be useful for combating invertebrate pests. Nevertheless, there remains a need for highly effective and versatile agents for combating invertebrate pests. It is therefore an object of the invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control pests, such as insects. It has been found that these objects can be achieved by compounds of formula I as depicted and defined below, and by their stereoisomers, salts, tautomers and N-oxides, in particular their agriculturally acceptable salts. Compounds I can be prepared by reaction of the corresponding precursor compounds I with R1=H with a suitable reagent R1-Y, in which Y is a nucleophilic leaving group, such as halogen, tosylate or mesylate, preferably Br or Cl. The reaction can be effected under conditions generally known. I This transformation is usually carried out at temperatures from -10°C to +110°C, preferably from 0°C to 25°C, in an inert solvent and in the presence of a base [cf. WO 2002100846]. The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of III, based on II, as described e.g. in WO2023/025617. Alternatively, compounds I can be prepared from intermediates IV and hydrazines V, as described in WO2021/224323: I Compounds IV are known from WO2017/192385 and WO2019/206799. Compounds V with R4 can be prepared in two steps from dihalopyrimidines Va, wherein X is halogen, preferably Cl, and reagents R4-X’, wherein X’ is halogen, e.g. I, Br, Cl, or F, preferably Br: The first step is a cross-coupling reaction, as known from e.g. WO2019/072143, and WO2015/008073. The obtained intermediates Vb can be converted to compounds V by reaction with hydrazine or its salt (cf. WO2021/224323). Alternatively, compounds I can be prepared by reaction of a carboxylic acid VI with an amine VII, as described in WO2023/025617: I Carboxylic acids VI are commercially available, or can be prepared by methods known from literature (e.g. WO2019/197468). Amines VII can be prepared from compounds IVa in two steps: Compounds IVa and their reaction with pyrimidinohydrazines, including the subsequent Boc-group cleavage, are known from WO2019/197468. The reaction of IVa with V via VIIa to yield VII can be run under the conditions described in WO2019/197468. The reaction mixtures are worked up in a customary manner, for example by mixing with water, extracting with an appropriate organic solvent, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colourless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds I cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds I. However, if the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the pest to be controlled. The organic moieties groups mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group. The term “partially or fully substituted” by a radical means that in general the group is substituted with same or different radicals. The term “halogen” denotes in each case fluorine, bromine, chlorine, or iodine, in particular fluorine, chlorine, or bromine. The term "alkyl" as used herein and in the alkyl moieties of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms. Examples of an alkyl group are methyl (Me), ethyl (Et), n-propyl (n-Pr), iso-propyl, n-butyl, 2-butyl, iso- butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 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-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. The term "haloalkyl" as used herein and in the haloalkyl moieties of haloalkylcarbonyl, haloalkoxycarbonyl, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy and haloalkoxyalkyl, denotes in each case a straight- chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C1-C4-haloalkyl, more preferably from C1-C3-haloalkyl or C1-C2-haloalkyl, in particular from C1-C2-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1- fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group which is bonded via an oxygen atom and has usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, and the like. The term "alkoxyalkyl" as used herein refers to alkyl usually comprising 1 to 10, frequently 1 to 4, preferably 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are CH2OCH3, CH2-OC2H5, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl. The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Preferred haloalkoxy moieties include C1-C4-haloalkoxy, in particular C1-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoro-ethoxy, 2,2dichloro-2-fluorethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and the like. The term "alkylthio "(alkylsulfanyl: S-alkyl)" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4-alkylthio), more preferably 1 to 3 carbon atoms, which is attached via a sulfur atom. The term "haloalkylthio" as used herein refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkylsulfinyl" (alkylsulfoxyl: S(=O)-alkyl), as used herein refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms bonded through the sulfur atom of the sulfinyl group at any position in the alkyl group. The term "haloalkylsulfinyl" as used herein refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkylsulfonyl" (S(=O)2-alkyl) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4-alkylsulfonyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfonyl group at any position in the alkyl group. The term "haloalkylsulfonyl" as used herein refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkylcarbonyl" refers to an alkyl group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule. The term "haloalkylcarbonyl" refers to an alkylcarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkoxycarbonyl" refers to an alkylcarbonyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule. The term "haloalkoxycarbonyl” refers to an alkoxycarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkenyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. vinyl, allyl (2-propen-1-yl), 1-propen-1-yl, 2-propen-2-yl, methallyl (2-methylprop-2-en-1-yl), 2-buten-1-yl, 3-buten-1-yl, 2-penten-1-yl, 3-penten-1-yl, 4-penten-1-yl, 1- methylbut-2-en-1-yl, 2-ethylprop-2-en-1-yl and the like. The term "haloalkenyl" as used herein refers to an alkenyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms. The term "alkynyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. ethynyl, propargyl (2-propyn-1-yl), 1-propyn-1-yl, 1- methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl, 4-pentyn-1-yl, 1-methylbut-2-yn-1-yl, 1- ethylprop-2-yn-1-yl and the like. The term "haloalkynyl" as used herein refers to an alkynyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms. The term "cycloalkyl" as used herein and in the cycloalkyl moieties of cycloalkoxy and cycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl (cC3H5), cyclobutyl (cC4H7), cyclopentyl (cC5H9), cyclohexyl (cC6H11), cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "halocycloalkyl" as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 C atoms or 3 to 6 C atoms, wherein at least one, e.g.1, 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2- trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5- difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like. The term “halocycloalkenyl” as used herein and in the halocycloalkenyl moieties of halocycloalkenyloxy and halocycloalkenylthio denotes in each case a monocyclic singly unsaturated non-aromatic radical having usually from 3 to 10, e.g.3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms, wherein at least one, e.g.1, 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 3,3- difluorocyclopropen-1-yl and 3,3-dichlorocyclopropen-1-yl. The term "cycloalkenylalkyl" refers to a cycloalkenyl group as defined above which is bonded via an alkyl group, such as a C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (= cycloalkenylmethyl), to the remainder of the molecule. The term “carbocycle” or “carbocyclyl” includes in general a 3- to 12-membered, preferably a 3- to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, non-aromatic ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms. Preferably, the term “carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above. The term “heterocycle” or "heterocyclyl" includes in general 3- to 12-membered, preferably 3- to 6-membered, in particular 6-membered monocyclic heterocyclic non-aromatic radicals. The heterocyclic non-aromatic radicals usually comprise 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms selected from N, O, and S, wherein S-atoms as ring members may be present as S, SO, or SO2, and optionally one or two groups C(O) as ring members. Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S.oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, S- oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl and the like. Examples for heterocyclic ring also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2- onyl, thiazolidin-2-onyl, and the like. The term "hetaryl" includes monocyclic 5- or 6-membered heteroaromatic radicals comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O, and S. Examples of 5- or 6-membered heteroaromatic radicals include pyridyl, i.e.2-, 3-, or 4-pyridyl, pyrimidinyl, i.e.2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e.3- or 4-pyridazinyl, thienyl, i.e.2- or 3-thienyl, furyl, i.e.2-or 3-furyl, pyrrolyl, i.e.2- or 3-pyrrolyl, oxazolyl, i.e.2-, 3- or 5-oxazolyl, isoxazolyl, i.e.3-, 4- or 5-isoxazolyl, thiazolyl, i.e.2-, 3- or 5-thiazolyl, isothiazolyl, i.e.3-, 4- or 5-isothiazolyl, pyrazolyl, i.e.1-, 3-, 4- or 5-pyrazolyl, i.e.1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g.2- or 5-[1,3,4]oxadiazolyl, 4- or 5- (1,2,3-oxadiazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, thiadiazolyl, e.g.2- or 5-(1,3,4-thiadiazol)yl, 4- or 5-(1,2,3-thiadiazol)yl, 3- or 5-(1,2,4-thiadiazol)yl, triazolyl, e.g.1H-, 2H- or 3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or 4H-1,2,4-triazolyl and tetrazolyl, i.e.1H- or 2H-tetrazolyl. The term "hetaryl" also includes bicyclic 8 to 10-membered heteroaromatic radicals comprising as ring members 1, 2 or 3 heteroatoms selected from N, O, and S, wherein a 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical. Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like. These fused hetaryl radicals may be bonded to the remainder of the molecule via any ring atom of 5- or 6-membered heteroaromatic ring or via a carbon atom of the fused phenyl moiety. The terms "heterocyclylalkyl" and "hetarylalkyl" refer to heterocyclyl or hetaryl, respectively, as defined above which are bonded via a C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (= heterocyclylmethyl or hetarylmethyl, respectively), to the remainder of the molecule. The term “arylalkyl” and "phenylalkyl" refer to aryl as defined above and phenyl, respectively, which are bonded via C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (= arylmethyl or phenylmethyl), to the remainder of the molecule, examples including benzyl, 1-phenylethyl, 2-phenylethyl, 2-phenoxyethyl etc. The terms “alkylene”, “cycloalkylene”, “heterocycloalkylene”, “alkenylene”, “cycloalkenylene”, “heterocycloalkenylene” and “alkynylene” refer to alkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl and alkynyl as defined above, respectively, which are bonded to the remainder of the molecule, via two atoms, preferably via two carbon atoms, of the respective group, so that they represent a linker between two moieties of the molecule. In a particular embodiment, the variables of the compounds of the formula I have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of the formula I. Embodiments and preferred compounds of the invention for use in pesticidal methods and for insecticidal application purposes are outlined in the following paragraphs. With respect to the variables, the particularly preferred embodiments of the intermediates correspond to those of the compounds of the formula I. In a preferred embodiment, the compounds I are present in form of a mixture of compounds I.S and I.R, wherein compound I.S with S-configuration of the carbon atom neighboring the nitrogen is present in an amount of more than 50% by weight, in particular of at least 70% by weight, more particularly of at least 85% by weight, specifically of at least 90% by weight, based on the total weight of compounds I.S and I.R. Compounds of formula I.S are a particularly preferred embodiment of the invention. In one particularly preferred embodiment of the invention, the method comprises the step of contacting the plant, parts of it, its propagation material, the pests, their food supply, habitat or breeding grounds with a pesticidally effective amount of a compound of formula I.S. R1 is preferably H, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkyl, more preferably H, CH3, C2H5, CH2cC3H5, CH2CH=CH2, or CH2C≡CH, particularly H or CH2cC3H5. R2 is preferably CH3. X is preferably CH or CR3, particularly CH. Such compounds correspond to Formula I.1 In another embodiment X is N. Such compounds correspond to formula I.2. R3 is preferably halogen, CN, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C4-cycloalkyl unsubstituted or substituted with one or more CN or halogen, C3-C4-halocycloalkyl, S(O)m-C1-C4-alkyl, S(O)m-C1-C4-haloalkyl, S(O)m-(substituted phenyl); particularly selected from F, Cl, Br, I, CN, CF3, CHF2, OCH3, OC2H5, OcC3H5, O(4-F-C6H4), OCF3, OCHF2, 1- CN-cC3H4, 1-F-cC3H4, 2,2-F2-cC3H3, SO2CH3, SO2CH(CH3)2, SO2CF3, SO2(4-F-C6H4), and C(CH3)2CN. In another embodiment R3 is halogen, CN, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C4-cycloalkyl unsubstituted or substituted with one or more CN or halogen, C3-C4-halocycloalkyl, O-S(O)m-halomethyl, O-S(O)m-C3-C4-cycloalkyl unsubstituted or substituted with one or more CN or halogen, S(O)m-C1-C4-alkyl, S(O)m-C1-C4-haloalkyl, S(O)m- (substituted phenyl); particularly selected from F, Cl, Br, I, CN, CF3, CHF2, OCH3, OC2H5, OcC3H5, O(4-F-C6H4), OCF3, OCHF2, 1-CN-cC3H4, 1-F-cC3H4, 2,2-F2-cC3H3, OSO2CF3, OSO2cC3H5, SO2CH3, SO2CH(CH3)2, SO2CF3, SO2(4-F-C6H4), and C(CH3)2CN. R3 is more preferred selected from Cl, Br, CF3, 1-CN-cC3H4, C(CH3)2CN, SO2CF3, SO2(4-F-C6H4), OCHF2. Particular preferred embodiments of (R3)n are 3,5-(CF3)2; 3-CF3,5-Cl; 3-CF3,5-Br; 3-(1-CN-cC3H4),5-Cl; 3- C(CH3)2CN,5-Cl; 3-SO2CF3,5-Cl; 3-SO2(4-F-C6H4),5-Cl; 3-OCHF2,5-Cl. R3 is more preferred selected from Br, Cl, CF3, SO2(4-F-C6H4), 1-CN-cC3H4. R3 bonded to a N-atom of a saturated or unsaturated heterocycle is preferably selected form R3b: C1-C4-alkyl, C3- C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-alkenyl, C1-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6- alkyl-C3-C6-cycloalkyl which are unsubstituted or substituted with R3a; C(O)NR12R13, C(O)OR14, C(O)R15, S(O)m-R15. In another preferred embodiment at least one R3 group in (R3)n is selected from R3d: C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C6-cycloalkyl which are unsubstituted or substituted with R3a; NR12R13, C(O)NR12R13, C(O)OR14, C(O)R15, and S(O)m-R15, wherein m is 1 or 2. Index m in R3 is preferably 2. Index n is preferably 2. In a particular embodiment one R3 group of the two is selected from R3d, the other is as defined or preferred above for R3. R3 groups in (R3)n stand preferably in positions 3 and 5. R4 is preferably selected from pyridine, pyrimidine, pyrazine, pyridazine, thiazole, oxazole, pyrazole, and triazole, particularly from 2-pyridine, and 3-pyridine. In another preferred embodiment R4 is heterocyclyl which is bonded via a ring C atom, the ring optionally substituted with R3. In another preferred embodiment R4 is heterocyclyl which is bonded via a ring N atom, the ring optionally substituted with R3. In another preferred embodiment R4 is selected from azetidine substituted with R3, oxetane, thietane, thietane-1- oxide, and thietane-1,1-dioxide, particularly from 3-azetidine N-substituted with R3d, thietane, thietane-1-oxide, and thietane-1,1-dioxide. R4 is more preferred selected from 2-pyridinyl, 3-pyridinyl, 2-thiazolyl, 1-pyrazolyl, 3-thietanyl, 3-(1-oxo-thietanyl), 3-(1,1-dioxo-thietanyl), and 3-(N-acetyl)azetidinyl. In another preferred embodiment R4 is selected from 2-imidazolyl, 3-(1,2,4-triazolyl), 3-pyrazolyl, 4-pyrazolyl, 4- (1,2,3-triazolyl), and 5-tetrazolyl. In another preferred embodiment R4 is 1-pyrazolyl. In another preferred embodiment R4 is 2-thiazolyl. In another preferred embodiment R4 is a 5-membered heteroaromatic ring substituted with R3 selected from C1-C6- haloalkyl, OR14, NR12R13, or C(O)NR12R13. In another preferred embodiment R4 is selected from phenyl or pyridyl, which rings are substituted with R3 selected from C1-C6-haloalkyl, OR14, NR12R13, or C(O)NR12R13. Another embodiment are compounds I wherein R4 is phenyl or hetaryl and at least one R3 group in (R3)n is selected from R3d. R5 is preferably H, halogen, C1-C4-alkyl, or C3-C6-cycloalkyl, more preferred H, F, Cl, CH3, or cC3H5. R5 being H or cC3H5 is more preferred. R5 being H is particularly preferred. In another embodiment R10 is selected from H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C4-cycloalkyl-C1-C2-alkyl, C3-C4-halocycloalkyl-C1-C2-alkyl, C(O)-C1-C4-alkyl, C(O)-C1-C4-haloalkyl, C(O)-C3-C4- cycloalkyl, C(O)-C3-C4-halocycloalkyl, or phenyl which is unsubstituted or partially or fully substituted with R3a. In particular with a view to their use, preference is given to the compounds of formula I com-piled in the tables below. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question. Table 1 : Compounds of formula I.1* in which R4 is 2-pyridinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 2 : Compounds of formula I.1* in which R4 is 3-pyridinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 3 : Compounds of formula I.1* in which R4 is 2-thiazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 4 : Compounds of formula I.1* in which R4 is N-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 5 : Compounds of formula I.1* in which R4 is 3-thietanyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 6 : Compounds of formula I.1* in which R4 is 3-(N-acetyl)azetidinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 7 Compounds of formula I.1* in which R4 is 2-imidazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 8 Compounds of formula I.1* in which R4 is 3-(1,2,4-triazolyl), and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 9 Compounds of formula I.1* in which R4 is 3-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 10 Compounds of formula I.1* in which R4 is 4-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 11 Compounds of formula I.1* in which R4 is 4-(1,2,3-triazolyl), and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 12 Compounds of formula I.1* in which R4 is 5-tetrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 13 : Compounds of formula I.2* in which R4 is 2-pyridinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 14 : Compounds of formula I.2* in which R4 is 3-pyridinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 15 : Compounds of formula I.2* in which R4 is 2-thiazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 16 : Compounds of formula I.2* in which R4 is N-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 17 : Compounds of formula I.2* in which R4 is 3-thietanyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 18 : Compounds of formula I.2* in which R4 is 3-(N-acetyl)azetidinyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 19 Compounds of formula I.2* in which R4 is 2-imidazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 20 Compounds of formula I.2* in which R4 is 3-(1,2,4-triazolyl), and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 21 Compounds of formula I.2* in which R4 is 3-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 22 Compounds of formula I.2* in which R4 is 4-pyrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 23 Compounds of formula I.2* in which R4 is 4-(1,2,3-triazolyl), and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table 24 Compounds of formula I.2* in which R4 is 5-tetrazolyl, and the combination of R1 and (R3)n for a compound corresponds in each case to one row of Table A Table A No. R1 (R3)n No. R1 (R3)n A-1 H 3,5-F2 A-31 H 3-Cl,5-SO2CH(CH3)2 A-2 H 3,5-Cl2 A-32 H 3-Cl,5-SO2cC3H5 A-3 H 3,5-Br2 A-33 H 3-Cl,5-OSO2CF3 A-4 H 3,5-I2 A-34 H 3-Cl,5-OSO2cC3H5 A-5 H 3,5-(CF3)2 A-35 H 3-Cl,5-[SO2(4-Cl-C6H4)] A-6 H 3-Cl,5-F A-36 H 3-Cl,5-[SO2(4-F-C6H4)] A-7 H 3-Cl,5-Br A-37 H 3-CF3,5-OCF3 A-8 H 3-Cl,5-I A-38 H 3-CF3,5-cC3H5 A-9 H 3-F,5-CN A-39 H 3-Cl,5-[(1-CN)cC3H4] A-10 H 3-Cl,5-CN A-40 H 3-CF3,5-[(1-CN)cC3H4] A-11 H 3-CF3,5-CN A-41 H 3-CF3,5-[(2,2-Cl2)-cC3H3] A-12 H 3-F,5-CF3 A-42 H 3-OCF3,5-cC3H5 A-13 H 3-Cl,5-CF3 A-43 H 3,5-SO2CH3 A-14 H 3-Br,5-CF3 A-44 H 3,5-SO2CF3 A-15 H 3-I,5-CF3 A-45 CH3 3,5-F2 A-16 H 3-Cl,5-SO2CH3 A-46 CH3 3,5-Cl2 A-17 H 3-Cl,5-SO2CF3 A-47 CH3 3,5-Br2 A-18 H 3-Cl,5-cC3H5 A-48 CH3 3,5-I2 A-19 H 3-Cl,5-[2,2-Cl2-cC3H3] A-49 CH3 3,5-(CF3)2 A-20 H 3-Cl,5-OCF3 A-50 CH3 3-Cl,5-F A-21 H 3-Br,5-OCF3 A-51 CH3 3-Cl,5-Br A-22 H 3-F,5-cC3H5 A-52 CH3 3-Cl,5-I A-23 H 3-Cl,5-CH2CN A-53 CH3 3-F,5-CN A-24 H 3-Cl,5-C(CH3)2CN A-54 CH3 3-Cl,5-CN A-25 H 3-CF3,5-CH2CN A-55 CH3 3-CF3,5-CN A-26 H 3-CF3,5-C(CH3)2CN A-56 CH3 3-F,5-CF3 A-27 H 3-CF3,5-SO2CH3 A-57 CH3 3-Cl,5-CF3 A-28 H 3-CF3,5-SO2CF3 A-58 CH3 3-Br,5-CF3 A-29 H 3-CF3,5-OSO2CF3 A-59 CH3 3-I,5-CF3 A-30 H 3-CF3,5-OSO2cC3H5 A-60 CH3 3-Cl,5-SO2CH3 No. R1 (R3)n No. R1 (R3)n A-61 CH3 3-Cl,5-SO2CF3 A-97 CH2-cC3H5 3-F,5-CN A-62 CH3 3-Cl,5-cC3H5 A-98 CH2-cC3H5 3-Cl,5-CN A-63 CH3 3-Cl,5-[2,2-Cl2-cC3H3] A-99 CH2-cC3H5 3-CF3,5-CN A-64 CH3 3-Cl,5-OCF3 A-100 CH2-cC3H5 3-F,5-CF3 A-65 CH3 3-Br,5-OCF3 A-101 CH2-cC3H5 3-Cl,5-CF3 A-66 CH3 3-F,5-cC3H5 A-102 CH2-cC3H5 3-Br,5-CF3 A-67 CH3 3-Cl,5-CH2CN A-103 CH2-cC3H5 3-I,5-CF3 A-68 CH3 3-Cl,5-C(CH3)2CN A-104 CH2-cC3H5 3-Cl,5-SO2CH3 A-69 CH3 3-CF3,5-CH2CN A-105 CH2-cC3H5 3-Cl,5-SO2CF3 A-70 CH3 3-CF3,5-C(CH3)2CN A-106 CH2-cC3H5 3-Cl,5-cC3H5 A-71 CH3 3-CF3,5-SO2CH3 A-107 CH2-cC3H5 3-Cl,5-[2,2-Cl2-cC3H3] A-72 CH3 3-CF3,5-SO2CF3 A-108 CH2-cC3H5 3-Cl,5-OCF3 A-73 CH3 3-CF3,5-OSO2CF3 A-109 CH2-cC3H5 3-Br,5-OCF3 A-74 CH3 3-CF3,5-OSO2cC3H5 A-110 CH2-cC3H5 3-F,5-cC3H5 A-75 CH3 3-Cl,5-SO2CH(CH3)2 A-111 CH2-cC3H5 3-Cl,5-CH2CN A-76 CH3 3-Cl,5-SO2cC3H5 A-112 CH2-cC3H5 3-Cl,5-C(CH3)2CN A-77 CH3 3-Cl,5-OSO2CF3 A-113 CH2-cC3H5 3-CF3,5-CH2CN A-78 CH3 3-Cl,5-OSO2cC3H5 A-114 CH2-cC3H5 3-CF3,5-C(CH3)2CN A-79 CH3 3-Cl,5-[SO2(4-Cl-C6H4)] A-115 CH2-cC3H5 3-CF3,5-SO2CH3 A-80 CH3 3-Cl,5-[SO2(4-F-C6H4)] A-116 CH2-cC3H5 3-CF3,5-SO2CF3 A-81 CH3 3-CF3,5-OCF3 A-117 CH2-cC3H5 3-CF3,5-OSO2CF3 A-82 CH3 3-CF3,5-cC3H5 A-118 CH2-cC3H5 3-CF3,5-OSO2cC3H5 A-83 CH3 3-Cl,5-[(1-CN)cC3H4] A-119 CH2-cC3H5 3-Cl,5-SO2CH(CH3)2 A-84 CH3 3-CF3,5-[(1-CN)cC3H4] A-120 CH2-cC3H5 3-Cl,5-SO2cC3H5 A-85 CH3 3-CF3,5-[(2,2-Cl2)-cC3H3] A-121 CH2-cC3H5 3-Cl,5-OSO2CF3 A-86 CH3 3-OCF3,5-cC3H5 A-122 CH2-cC3H5 3-Cl,5-OSO2cC3H5 A-87 CH3 3,5-(SO2CH3)2 A-123 CH2-cC3H5 3-Cl,5-[SO2(4-Cl-C6H4)] A-88 CH3 3,5-(SO2CF3)2 A-124 CH2-cC3H5 3-Cl,5-[SO2(4-F-C6H4)] A-89 CH2-cC3H5 3,5-F2 A-125 CH2-cC3H5 3-CF3,5-OCF3 A-90 CH2-cC3H5 3,5-Cl2 A-126 CH2-cC3H5 3-CF3,5-cC3H5 A-91 CH2-cC3H5 3,5-Br2 A-127 CH2-cC3H5 3-Cl,5-[(1-CN)cC3H4] A-92 CH2-cC3H5 3,5-I2 A-128 CH2-cC3H5 3-CF3,5-[(1-CN)cC3H4] A-93 CH2-cC3H5 3,5-(CF3)2 A-129 CH2-cC3H5 3-CF3,5-[(2,2-Cl2)-cC3H3] A-94 CH2-cC3H5 3-Cl,5-F A-130 CH2-cC3H5 3-OCF3,5-cC3H5 A-95 CH2-cC3H5 3-Cl,5-Br A-131 CH2-cC3H5 3,5-(SO2CH3)2 A-96 CH2-cC3H5 3-Cl,5-I A-132 CH2-cC3H5 3,5-(SO2CF3)2 Table B: Particularly preferred compounds of formula I No. R1 R2 X (R3)n R4 R5 B1 H CH3 CH 3,5-(CF3)2 2-pyridinyl H B2 H CH3 CH 3-Cl,5-SO2-(4-F-C6H4) 2-pyridinyl H B3 H CH3 CH 3-Br,5-[(1-CN)cC3H4] 2-pyridinyl H B4 H CH3 N 3-Cl,5-[(1-CN)cC3H4] 2-pyridinyl H B5 H CH3 CH 3,5-(CF3)2 3-pyridinyl H B6 CH2-cC3H5 CH3 CH 3,5-(CF3)2 2-pyridinyl H B7 H CH3 CH 3,5-(CF3)2 2-pyridinyl cC3H5 B8 H CH3 CH 3,5-(CF3)2 N-pyrazolyl H B9 H CH3 CH 3-Cl,5-SO2-(4-F-C6H4) N-pyrazolyl H B10 H CH3 CH 3-Br,5-[(1-CN)cC3H4] N-pyrazolyl H B11 H CH3 N 3-Cl,5-[(1-CN)cC3H4] N-pyrazolyl H B12 H CH3 CH 3,5-(CF3)2 N-pyrazolyl H B13 CH2-cC3H5 CH3 CH 3,5-(CF3)2 N-pyrazolyl H B14 H CH3 CH 3,5-(CF3)2 N-pyrazolyl cC3H5 The term “compound(s) of the invention” refers to compound(s) of formula I, or “compound(s) I”, and includes their salts, tautomers, stereoisomers, and N-oxides. The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I. An agrochemical composition comprises a pesticidally effective amount of a compound I. The compounds I can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials e.g. seeds (e.g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No.2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders. Suitable solvents and liquid carriers are water and organic solvents. Suitable solid carriers or fillers are mineral earths. Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetra- tion enhancer, protective colloid, or adjuvant. Surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Deter- gents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International or North American Ed.). Suitable anionic sur- factants are alkali, alkaline earth, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates. Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants. Suitable cationic surfactants are qua-ternary surfactants. The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a pu- rity of from 90% to 100%, preferably from 95% to 100%. Various types of oils, wetters, adjuvants, or fertilizer may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be ad- mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1. The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agro-chemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the ag- rochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. The compounds I are suitable for use in protecting 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 re- lates 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 I. The compounds I are also suitable for use in combating or controlling animal pests. Therefore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habi- tat, breeding ground, or food supply, or the crops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound I. The compounds I are effective through both contact and ingestion to any and all developmental stages, such as egg, larva, pupa, and adult. The compounds I can be applied as such or in form of compositions comprising them. The application can be carried out both before and after the infestation of the crops, plants, plant propagation mate- rials by the pests. The term "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant) and indirect contact (applying the compounds/compositions to the locus). The term “animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / 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. rape- seed (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; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grape-fruits or mandarins; vegetables, e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cu- curbits or sweet peppers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material plants, e.g. corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, , shrubs, broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, bar- ley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamen- tals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes. The term “seed” embraces seeds and plant propagules including true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots, and means preferably true seeds. "Pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise dimin- ishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary ac- cording to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application. For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this inven- tion may be in the range of 0.0001g to 4000g per hectare, e.g. from 1g to 2kg per hectare or from 1g to 750g per hectare, desirably from 1g to 100g per hectare. The compounds I are also suitable for use against non-crop insect pests. For use against said non-crop pests, com- pounds I can be used as bait composition, gel, general insect spray, aero-sol, as ultra-low volume application and bed net (impregnated or surface applied). The term “non-crop insect pest” refers to pests, which are particularly relevant for non-crop targets, e.g. ants, ter- mites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches, such as: Aedes aegypti, Musca domestica, Tribolium spp.; termites such as Reticulitermes flavipes, Coptotermes formosanus; roaches such as Blatella german- ica, Periplaneta Americana; ants such as Solenopsis invicta, Linepithema humile, and Camponotus pennsylvanicus. The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). For use in bait compositions, the typical con- tent of active ingredient is from 0.001wt% to 15wt%, desirably from 0.001wt% to 5wt% of active compound. The compounds I and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants, termites and/or wood or textile destroying beetles, and for controlling ants and termites from doing harm to crops or human beings (e.g. when the pests invade into houses and public fa- cilities or nest in yards, orchards or parks). Customary application rates in the protection of materials are, e.g., from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2. Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 wt%, preferably from 0.1 to 45 wt%, and more preferably from 1 to 25 wt% of at least one repellent and/or insecticide. The compounds of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, and nematodes including: insects from the sub-order of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citri; Lepidoptera, e.g. Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseu- doplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medi- alis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens; True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus; Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettii; Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schizaphis graminum, Megoura viciae; Whiteflies, e.g. Trialeurodes vaporariorum, Bemisia spp.; Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria 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, e.g. Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans. The compounds I are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention re- lates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a com- pound I. The invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting ani- mals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound I. The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or controlling parasites in and on animals, which com- prises contacting the parasites with a parasitically effective amount of a compound I. The invention also relates to the non-therapeutic use of compounds I for controlling or combating parasites. Moreo- ver, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises apply- ing to a locus a parasiticidally effective amount of a compound I. The compounds I can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds I can be applied to any and all developmental stages. The compounds I can be applied as such or in form of compositions comprising them. The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a para- site is growing or may grow outside of the animal. As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments of the invention, en- doparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas. The compounds of the invention are especially useful for combating the following parasites: Cimex lectularius, Rhip- icephalus sanguineus, and Ctenocephalides felis. As used herein, the term “animal” includes warm-blooded animals (including humans) and fish. Preferred are mam- mals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in furbearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particu- larly preferred are domestic animals, such as dogs or cats. The compounds I may be applied in total amounts of 0.5mg/kg to 100mg/kg per day, preferably 1mg/kg to 50mg/kg per day. For oral administration to warm-blooded animals, the compounds I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and cap- sules. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds I, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day. Alternatively, the compounds I may be administered to animals parenterally, e.g., by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds I may be dispersed or dissolved in a physiologically accepta- ble carrier for subcutaneous injection. Alternatively, the compounds I may be formulated into an implant for subcuta- neous administration. In addition the compounds I may be transdermally administered to animals. For parenteral ad- ministration, the dosage form chosen should provide the animal with 0.01mg/kg to 100mg/kg of animal body weight per day of the compounds I. The compounds I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medal- lions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5ppm to 5,000ppm and preferably 1ppm to 3,000ppm of the compounds I. In addition, the compounds I may be formulated as ear tags for animals, particularly quadrupeds e.g. cattle and sheep. Oral solutions are administered directly. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Gels are applied to or spread on the skin or introduced into body cavities. Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active com- pound in suitable skin-compatible solvents or solvent mixtures. Emulsions can be administered orally, dermally or as injections. Suspensions can be administered orally or topically/dermally. Semi-solid preparations can be administered orally or topically/dermally. For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the com- pound I. Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentra- tions of 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight, more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight. Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight. Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2% by weight, preferably of 0.05 to 0.9% by weight, very particularly preferably of 0.005 to 0.25% by weight. Solid formulations which release compounds of the invention may be applied in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks. A. Preparation examples The compounds were characterized by melting point determination, by NMR spectroscopy or by the mass-to- charge ratio ([m/z]) and retention time (RT; [min]), as determined by mass spectrometry (MS) coupled with HPLC analysis (HPLC-MS = high performance liquid chromatography-coupled mass spectrometry) or LC analysis (LC-MS = liquid chromatography-coupled mass spectrometry). Method A: Shimadzu Nexera UHPLC + Shimadzu LCMS-2020, ESI; Column: Kinetex 1.7µ XB-C18100A, 2.1x50mm; Mobile phase: A: water + 0.1% TFA; B: ACN; Temperature: 60°C; Gradient: 5% B to 100% B in 1.5min; 100% B 0.25min; Flow: 0.8 mL/min to 1.0 mL/min in 1.5min; MS: ESI positive; Mass range (m/z): 100–700. Example 1: Synthesis of [N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)ben- zamide] (I-1) Step 1: Synthesis of [[6-(2-pyridyl)pyrimidin-4-yl]amino]ammonium chloride: To a solution of 4-chloro-6-(2- pyridyl)pyrimidine (400 mg, 2.09 mmol, 1.00 eq) in EtOH (8 mL), hydrazine hydrate (0.12 mL, 125 mg, 2.51 mmol, 1.2eq) was added at 0 °C. The reaction mixture was stirred for 18 h while warming up to 20-25°C. Additional hydra- zine hydrate (0.03 mL, 31.3 mg, 0.63 mmol, 0.3 eq) was added and the reaction mixture was stirred for another 3 days at 20-25°C. The precipitate was filtered to deliver [[6-(2-pyridyl)pyrimidin-4-yl]amino]ammonium chloride (330 mg, 1.48 mmol, 71%) as a white solid. LCMS: Desired Mass: m/z = 188,1; Observed Mass: m/z = 188.0. Step 2: Synthesis of N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide: To a solution N-[2-[dimethylaminomethyleneamino]-1-methyl-2-oxo-ethyl]-3,5-bis(trifluoromethyl)benzamide (300 mg, 783 µmol, 1 eq) in AcOH (5 mL), [[6-(2-pyridyl)pyrimidin-4-yl]amino]ammonium chloride (158 mg, 704 µmol, 0.9 eq) was added at 20-25°C. The reaction mixture was stirred for 4 h at 70 °C and for 17 h at 20-25°C. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc (40 mL), washed with aq. sat. NaHCO3 solu- tion (3×30 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The resulting resi- due was dried purified by flash chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford N-[1-[2-[6- (2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (100 mg, 177 µmol, 23%) as a white solid. LCMS: Desired Mass: m/z = 508.1; Observed Mass: m/z = 508.0. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.80 (d, J=6.8 Hz, 1H), 9.32 (d, J=1.1 Hz, 1H), 8.82 (d, J=1.1 Hz, 2H), 8.51 – 8.47 (m, 3H), 8.35 – 8.30 (m, 2H), 8.09 (td, J=7.8, 1.8 Hz, 1H), 7.66 (ddd, J=7.6, 4.8, 1.1 Hz, 1H), 6.36 – 6.27 (m, 1H), 1.70 (d, J=7.0 Hz, 3H). Example 2: Synthesis of [3-(1-cyanocyclopropyl)-5-(difluoromethoxy)-N-[(1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)- 1,2,4-triazol-3-yl]ethyl]benzamide] (I-2) Step 1: Synthesis of methyl 3-hydroxy-5-methyl-benzoate: To a stirred solution of 3-hydroxy-5-methyl-benzoic acid (110g, 723mmol, 1eq) in MeOH (3 L), SOCl2 (173g, 1.45mol, 2eq) was added dropwise. The mixture was stirred at 60°C overnight and concentrated to afford methyl 3-hydroxy-5-methyl-benzoate (118g), which was used in the next step without further purification. Step 2: Synthesis of methyl 3-(difluoromethoxy)-5-methyl-benzoate: To a stirred solution of methyl 3-hydroxy-5- methyl-benzoate (118g, 710mmol, 1eq) in DMF (3.5L), sodium 2-chloro-2,2-difluoroacetate (325g, 2.13mol, 3eq) and cesium carbonate (463g, 1.42mol, 3eq) were added under inert atmosphere. The mixture was stirred at 100°C over- night. After cooling to 20-25°C, the solvent was evaporated and the residue was dissolved in water (6L) and ex- tracted with EtOAc (5×500mL). The organic layer was dried over sodium sulfate and concentrated to afford the crude product, which was purified by column chromatography to deliver methyl 3-(difluoromethoxy)-5-methyl-benzoate (71.6g, 46% yield). Step 3: Synthesis of methyl 3-(bromomethyl)-5-(difluoromethoxy)benzoate: To a stirred solution of methyl 3-(difluo- romethoxy)-5-methyl-benzoate (71.6g, 0.33mol, 1eq) in dichloroethane (1L), NBS (64.1g, 0.36mol, 1.1eq) was added in one portion. The mixture was refluxed overnight, cooled to 20-25°C, filtered through a pad of SiO2 and concen- trated to afford methyl 3-(bromomethyl)-5-(difluoromethoxy)benzoate (85.2g, 79% yield). Step 4: Synthesis of methyl 3-(cyanomethyl)-5-(difluoromethoxy)benzoate: To a stirred solution of methyl 3-(bromo- methyl)-5-(difluoromethoxy)benzoate (85.2g, 0.26mol, 1eq) in EtOH (1.7L) and H2O (425mL), KCN (33.9g, 520mmol, 2eq) was added in one portion. The mixture was stirred at 85 °C for 2 h, cooled to 20-25°C and sodium carbonate (excess) was added. The mixture was extracted with EtOAc (3×200mL). The organic layer was washed with water (2×300 mL), dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography to afford methyl 3-cyanomethyl-5-(difluoromethoxy)benzoate (16.8g, 27% yield). Step 5: Synthesis of methyl 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)benzoate: To a stirred solution of methyl 3- cyanomethyl-5-(difluoromethoxy)benzoate (16.8 g, 70 mmol, 1eq) in DMF (200 mL), Cs2CO3 (45.6g, 0.14mol, 2eq) was added followed by BrCH2CH2Br (39.4 g, 210mmol, 3 eq). The mixture was stirred at 120°C overnight, cooled to 20-25°C and concentrated, partitioned between EtOAc (200mL) and aq. conc. HCl (400mL). The organic phase was separated, dried over Na2SO4, and concentrated to afford crude methyl 3-(1-cyanocyclopropyl)-5-(difluorometh- oxy)benzoate (17 g, 86% yield), which was used in the next step without further purification. Step 6: Synthesis of 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)benzoic acid: To a stirred solution of methyl 3-(1- cyanocyclopropyl)-5-(difluoromethoxy)benzoate (17g, 60 mmol, 1eq) in THF (200 mL)/water (50 mL), NaOH (2.39g, 60 mmol, 1eq) was added at 0°C. The reaction mixture was stirred at 20-25°C overnight and partitioned between EtOAc (200 mL) and aq. HCl (400 mL). Organic phase was separated, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (CHCl3/AcNACN/AcOH) to afford 3-(1-cyanocyclopropyl)-5-(difluoro- methoxy)benzoic acid (10g, 66% yield) 1H-NMR (400MHz, DMSO-d6) δ [ppm] =13.51 (bs, 1H), 7.85–7.81 (m, 1H), 7.62–7.58 (m, 1H), 7.37 (t, 2JFH=73.3 Hz, 1H), 7.30–7.27 (m, 1H), 1.89–1.77 (m, 2H), 1.70–1.57 (m, 2H). LCMS: Desired Mass: m/z = 253.2; Observed Mass: m/z = 253.06 Step 7: Synthesis of (6-pyrazol-1-ylpyrimidin-4-yl)hydrazine: A solution of 4-chloro-6-pyrazol-1-yl-pyrimidine (1.01g, 5.59 mmol, 1eq) and hydrazine hydrate (1.12g, 22.4mmol, 4eq) in MeOH (35 mL) was stirred for 4 h at 65 °C until LCMS showed full conversion. The reaction mixture was diluted with H2O and the volatiles were removed under re- duced pressure. The remaining solution was adjusted to pH8 using aq. HCl and aq. K2CO3. The resulting precipitate was filtered, washed with H2O, and dried to obtain (6-pyrazol-1-ylpyrimidin-4-yl)hydrazine (920 mg, 5.22 mmol, 93%). 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 8.62 (bs, 1H), 8.55 (d, J=2.6 Hz, 1H), 8.28 (bs, 1H), 7.83 (d, J=1.6 Hz, 1H), 7.22 (bs, 1H), 6.55 (dd, J=2.6, 1.6 Hz, 1H), 4.5 (bs, 2H). Step 8: Synthesis of tert-butyl N-[(1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]carbamate: To a solution of (6-pyrazol-1-ylpyrimidin-4-yl)hydrazine (2.54 g, 10.4 mmol, 2 eq) in acetic acid (14 mL), tert-butyl N-[(1S)- 2-[dimethylaminomethyleneamino]-1-methyl-2-oxo-ethyl]carbamate (920 mg, 5.22 mmol, 1eq) was added dropwise at 20-25°C. The reaction mixture was stirred at 20-25°C for 19 h until LCMS showed full conversion. The solvent was removed under reduced pressure and the resulting solid was washed with MTBE. The residue was purified by flash chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford N-[(1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)- 1,2,4-triazol-3-yl]ethyl]carbamate (1.00g, 2.81 mmol, 54%) as a colorless wax. Step 9: Synthesis of: (1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-triazol-3-yl]ethanamine: To a solution of tert-butyl N-[(1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]carbamate (1.00 g, 2.81 mmol, 1 eq) in 1,4-dioxane (30 mL), HCl (4N in 1,4-dioxane, 7 mL, 28eq ) was added. The reaction mixture was stirred at 50°C for 5 h and 1 h at 60°C. The solvent was removed under reduced pressure to afford (1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-tria- zol-3-yl]ethanamine (842 mg) as colorless solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.14 (d, J=1.1 Hz, 1H), 8.90 (bs, 2 to 3H), 8.77 (d, J=2.8 Hz, 1H), 8.50 (s, 1H), 8.27 (d, J=1.1,1H), 8.07–8.03 (m, 1H), 6.74 (dd, J=2.8 Hz, 1.6 Hz, 1H), 5.57–5.47 (m, 1H), 1.68 (d, J=6.7 Hz, 3H). Step 10: Synthesis of 3-(difluoromethoxy)-5-methyl-N-[(1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-triazol-3- yl]ethyl]benzamide: A solution of 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)benzoic acid (148 mg, 585 µmol, 1eq), (1S)-1-[2-(6-pyrazol-1-ylpyrimidin-4-yl)-1,2,4-triazol-3-yl]ethanamine (150 mg, 585 µmol, 1eq), 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (289 mg, 761 µmol, 1.3 eq) and N,N-diisopropylethylamine (0.25 mL, 189 mg, 1.46 mmol, 2.5 eq) was stirred at 20-25°C for 18 h. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc (10 mL), washed with H2O (2×5 mL), dried over Na2SO4, filtered and concentrated. The crude product was further purified by flash chromatog- raphy on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford 3-(difluoromethoxy)-5-methyl-N-[(1S)-1-[2-(6-pyrazol- 1-ylpyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]benzamide (233 mg, 450 µmol, 77%) as a beige wax. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.29 (d, J=7.0 Hz, 1H), 9.10 (d, J=1.1 Hz, 1H), 8.76 (d, J=2.6 Hz, 1H), 8.31 (s, 1H), 8.26 (d, J=1.0,1H), 8.03 (d, J=1.6 Hz, 1H), 7.68–7.64 (m, 1H), 7.59–7.56 (m, 1H), 7.31 (t, 2JFH=73.5 Hz, 1H), 7.28–7.26 (m, 1H), 6.73 (dd, J=2.8, 1.6 Hz, 1H), 6.31–6.23 (m, 1H), 1.82–1.77 (m, 2H), 1.66 (d, J=7.0 Hz, 3H), 1.63– 1.58 (m, 2H). LCMS: Desired Mass: m/z = 492.2; Observed Mass: m/z = 492.1. Example 3: Synthesis of 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)-N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-tria- zol-3-yl]ethyl]benzamide (I-12) Step 1: Synthesis of 4-chloro-6-hydrazineylpyrimidine: To a mixture of 4,6-dichloropyrimidine (10.0g, 67.1mmol, 1 eq) in EtOH (50mL) was added dropwise hydrazinium hydroxide (4.11 g, 80.5mmol, 98% purity, 1.2 eq) at 0 °C. The reaction mixture was stirred at 0°C for 2h, then filtered. The filter cake was washed with EtOH (20mL) and water (20 mL), and was dried to afford 4-chloro-6-hydrazineylpyrimidine (4.2g, 50% yield) as a white solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 8.81 (s, 1H), 8.17 (s, 1H), 6.75 (bs, 1H), 4.50 (bs, 2H). Step 2: Synthesis of tert-butyl (1-(1-(6-chloropyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamat: To a mixture of 4- chloro-6-hydrazineylpyrimidine (3.7g, 25.6mmol, 1eq) and tert-butyl N-[2-[dimethylaminomethyleneamino]-1-methyl- 2-oxo-ethyl]carbamate (12.5g, 51.2mmol, 2eq) in 1,4-dioxane (50 mL) was added dropwise HCl (2M in EtOAc, 20mL). The reaction mixture was stirred at 25°C for 16h. AcOH (20mL) was added and the reaction mixture was stirred at 50°C for 2h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography on silica gel (DCM/MeOH = 30/1) to afford tert-butyl (1-(1-(6-chloropyrimidin-4-yl)-1H-1,2,4-triazol-5- yl)ethyl)carbamate (3.17 g, 38% yield) as a white solid. LC-MS (ES) m/z (M+H)+ = 325.3. Step 3: Synthesis of tert-butyl (1-(1-(6-(pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate: A mixture of tert-butyl (1-(1-(6-chloropyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (2.87g, 8.8mmol, 1eq), 2-(tribu- tylstannyl)pyridine (3.24g, 8.8mmol, 1eq), Pd(PPh3)4 (1.02g, 0.88 mmol, 0.1eq) and CuI (0.17g, 0.88mmol, 0.1eq) in toluene (60 mL) was stirred at 110 °C for 2h under N2. The reaction mixture was diluted with water (100 mL) and ex- tracted with EtOAc (2×100mL). The combined organic phase was concentrated. The residue was purified by column chromatography on silica gel (DCM/MeOH = 19/1) to afford the crude product, which was triturated with MeOH (20 mL) to afford tert-butyl (1-(1-(6-(pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (1.4 g, 43% yield) as a white solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.31 (s, 1H), 8.83–8.80 (m, 2H), 8.52 (d, J=8.0 Hz, 1H), 8.28 (s, 1H), 8.11– 8.06 (m, 1H), 7.67–7.63 (m, 1H), 7.57 (d, J=7.6 Hz, 1H), 5.86–5.79 (m, 1H), 1.48 (d, J=6.8 Hz, 3H), 1.32 (s, 9H). Step 4: Synthesis of 1-(1-(6-(pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethan-1-amine hydrochloride: To a mixture of tert-butyl (1-(1-(6-(pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (1.1 g, 3.0 mmol, 1 eq) in EtOAc (10 mL) was added HCl (2M in EtOAc, 10mL) at 30°C, and the resulting mixture was stirred at 30°C for 2h. The mixture was filtered and the filter cake was washed with EtOAc (10mL) and dried under vacuum to afford 1-(1-(6- (pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethan-1-amine hydrochloride (830mg, 90% yield) as a white solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.36 (s, 1H), 8.91 (bs, 3H), 8.84–8.83 (m, 2H), 8.54–8.52 (m, 1H), 8.50 (s, 1H), 8.13–8.08 (m, 1H), 7.69–7.66 (m, 1H), 5.58–5.52 (m, 1H), 1.70 (d, J=6.8 Hz, 3H). LC-MS (ES) m/z (M+H-HCl)+ = 268.0. Step 5: Synthesis of 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)-N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3- yl]ethyl]benzamide: A solution of 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)benzoic acid (71.0 mg, 281 µmol, 1eq), 1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethanamine (75 mg, 281 µmol, 1eq), 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (139 mg, 365 µmol, 1.3 eq) and N,N-diisopropylethylamine (0.12 mL, 91.0 mg, 0.70 mmol, 2.5 eq) was stirred at 20-25°C for 5d. Afterwards the solvent was removed under reduced pressure, the residue redissolved in EtOAc (10 mL), washed with H2O (2×5 mL) dried over Na2SO4 filtered and concentrated. The crude product was further purified by two consecutive flash chromatography purification steps. The first flash chromatography purification step was conducted on silica gel (c-hexane:EtOAc = 100:0 to 0:100), the second flash chromatography purification step was conducted on RP-18-column (H2O:CH3CN = 100:0 to 0:100) to afford 3-(1-cyanocyclopropyl)-5-(difluoromethoxy)-N-[1-[2-[6-(2- pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]benzamide (35 mg, 70 µmol, 25%) as a colorless solid. 1H-NMR (400MHz, Acetone-d6) δ [ppm] = 9.29 (d, J=1.2 Hz, 1H), 8.98 (d, J=1.3 Hz, 1H,) 8.84–8.80 (m, 1H), 8.60 (dt, J=7.9, 1.1 Hz, 1H), 8.55 (d, J=7.6 Hz, 1H), 8.14 (s, 1H), 8.07 (td, J=7.8, 1.8 Hz, 1H), 7.74 (t, J=1.6 Hz, 1H), 7.67– 7.60 (m, 2H), 7.33–7.30 (m, 1H), 7.09 (t, 2JFH=73.7 Hz, 1H), 6.51–6.43 (m, 1H), 1.81–1.77 (m, 2H), 1.73 (d, J=7.0 Hz, 3H), 1.63–1.58 (m, 2H). LCMS: Desired Mass: m/z = 503.5; Observed Mass: m/z = 503.1. Example 4: Synthesis of N-(cyclopropylmethyl)-N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5- bis(trifluoromethyl)benzamide (I-14) Step 1: Synthesis of N-(cyclopropylmethyl)-1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethanamine (I-14): A solution of 1-(1-(6-(pyridin-2-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethan-1-amine hydrochloride (90 mg, 337 µmol, 1 eq), cyclopropanecarbaldehyde (26.0 mg, 370 µmol, 1.1 eq), sodium cyanoborohydride (42.3 mg, 673 µmol, 2eq) and AcOH (5.06 mg, 84 µmol, 0.25 eq) in MeOH (2 mL) was stirred at 20-25°C for 18 h. Additional cyanoborohydride (42.3 mg, 0.673 mmol, 2eq) was added and stirred for 7 h. Subsequently, sodium borohydride (25.5 mg, 370 µmol, 1.1eq), 3 Å molecular sieves (1 g) and cyclopropanecarbaldehyde (26.0 mg, 370 µmol, 1.1eq) were added and the mixture was further stirred for 21 h. Sodium cyanoborohydride was added (42.3 mg, 673 µmol, 2 eq) and the mixture was stirred for 16 h. The reaction was quenched with H2O (10 mL) and extracted with EtOAc (2×5 mL). The organic layer was washed with H2O (2×5 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pres- sure. The crude product was purified by flash chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to af- ford N-(cyclopropylmethyl)-1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethanamine (20 mg, 62 µmol, 18%). LCMS: Desired Mass: m/z = 322.2; Observed Mass: m/z = 321.9. Step 2: Synthesis of N-(cyclopropylmethyl)-N-[1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(tri- fluoromethyl)benzamide: A solution of N-(cyclopropylmethyl)-1-[2-[6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]eth- anamine (18 mg, 56 µmol, 1 eq), 3,5-bis(trifluoromethyl)benzoic acid (14.5 mg, 56 µmol, 1eq), 1-[bis(dimethyla- mino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (27.7 mg, 73 µmol, 1.3 eq) and N,N-diisopropylethylamine (0.024 mL, 18.1 mg, 140 µmol, 2.5 eq) in DMF (3 mL) was stirred at 20-25°C for 16 h. Subsequently the solvent was removed under reduced pressure, the residue was dissolved in EtOAc (10 mL), washed with H2O (2×5 mL), dried over Na2SO4, filtered, and the solvent was removed. The crude product was puri- fied by flash chromatography on silica gel (c-hexane:EtOAc = 100:0 to 40:60) to afford N-(cyclopropylmethyl)-N-[1-[2- [6-(2-pyridyl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (18 mg, 32 µmol, 57%). 1H-NMR (400MHz, Acetone-d6) δ [ppm] = 9.46–8.90 (m, 1H), 8.92 (bs, 1H), 8.81 (ddd, J=4.8, 1.8, 0.9 Hz, 1H), 8.57 (d, J=8.0 Hz, 1H), 8.23 (s, 1H), 8.06 (td, J=7.7, 1.8 Hz, 2H), 7.62 (d, J=1.7 Hz, 2H), 7.62 (ddd, J=7.6, 4.7, 1.2 Hz, 1H), 6.90–6.39 (m, 1H), 4.69–3.80 (m, 1H), 3.68–2.94 (m, 2H), 1.88 (d, J=7.0 Hz, 3H), 1.02–0.53 (m, 2H), 0.50–0.15 (m, 2H). LCMS: Desired Mass: m/z (M+H)+ = 562.2; Observed Mass: m/z = 562.1. Example 5: N-[1-[2-[6-(1-acetylazetidin-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)ben- zamide (I-16) Step 1: Synthesis of tert-butyl (1-(1-(6-(1-acetylazetidin-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate: A mixture of tert-butyl N-[1-[2-(6-chloropyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]carbamate (15.0g, 46.2 mmol, 1eq), 1- acetylazetidine-3-carboxylic acid (9.9g, 69.3mmol, 1.5eq), 2,2′-bipyridine4,4′-bis(1,1-dimethylethyl) (1.86g, 6.9mmol, 0.1eq), dichloro(1,2-dimethoxyethane)nickel (1.02 g, 4.6 mmol, 0.05 eq), Cs2CO3 (22.58g, 69.3mmol, 1.5eq) and [Ir{dF(CF3)ppy}2(dtbpy)]PF6 (1.55g, 1.4mmol, 0.03eq) in DMAC (10 mL) was stirred under nitrogen and irradiation at 450 nm (LED) at 20-25°C overnight. The reaction mixture was diluted with water (50mL), extracted with ethyl ether (3×50mL). The organic phase was washed with brine (50mL), dried over anhydrous Na2SO4, filtered, and concen- trated. The residue was purified by flash chromatography on silica gel (DCM/MeOH = 20/1) to afford tert-butyl (1-(1- (6-(1-acetylazetidin-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (0.9g, 5%) as yellow oil. 1H-NMR (300MHz, DMSO-d6) δ [ppm]= 9.25 (s, 1H), 8.27 (s, 1H), 7.97 (s, 1H), 7.57 (d, J=6.9 Hz, 1H), 5.81–5.75 (m, 1H), 4.55–4.50 (m, 1H), 4.38-4.34 (m, 1H), 4.27–4.15 (m, 2H), 4.07–4.03 (m, 1H), 1.83 (s, 3H), 1.48 (d, J=6.9 Hz, 3H), 1.35 (s, 9H). Step 2: Synthesis of 1-[3-[6-[5-(1-aminoethyl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-1-yl]ethanone TFA salt: To a solution of tert-butyl (1-(1-(6-(1-acetylazetidin-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (600 mg, 1.54 mmol, 1 eq) in DCM (5 mL) was added TFA (1 mL) at 20-25°C and stirred for 5 h. The mixture was concentrated to afford 1-[3-[6-[5-(1-aminoethyl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-1-yl]ethanone TFA salt (280 mg, 63%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ [ppm] = 9.25 (s, 1H), 8.69 (bs, 2H), 8.48 (s, 1H), 8.00 (s, 1H), 5.54 – 5.50 (m, 1H), 4.53 – 4.49 (m, 1H), 4.34 – 4.30 (m, 1H), 4.25 – 4.16 (m, 2H), 4.02 – 3.99 (m, 1H), 1.80 (s, 3H), 1.64 (d, J = 6.8 Hz, 3H). LC-MS (ES) m/z = 288.1 (M+H-TFA)+. Step 3: Synthesis of N-[1-[2-[6-(1-acetylazetidin-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5- bis(trifluoromethyl)benzamide: A solution of 1-[3-[6-[5-(1-aminoethyl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-1- yl]ethanone TFA salt (50 mg, 0.125 µmol, 1 eq), 3,5-bis(trifluoromethyl)benzoic acid (45 mg, 0.174 mmol, 1.39 eq), 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (86.0 mg, 226 µmol, 1.81 eq) and N-ethyl-N-isopropyl-propan-2-amine (0.07 mL, 56.2 mg, 435 µmol, 3.48 eq) in DMF (3 mL) was stirred at 20-25°C for 20 h. The solvent was removed under reduced pressure and the residue wasdissolved in CH2Cl2 (40 mL), washed with H2O (15 mL), dried over MgSO4, and filtered. The solvent was removed under reduced pres- sure and the crude product was purified by column chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford N-[1-[2-[6-(1-acetylazetidin-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (39 mg, 74 µmol, 59%). 1H NMR (400 MHz, CDCl3) δ [ppm] = 9.21 – 9.17 (m, 1H), 8.31 – 8.27 (m, 2H), 8.02 – 7.96 (m, 3H), 7.88 (dd, J=7.6, 0.8 Hz, 1H), 6.57 – 6.49 (m, 1H), 4.57 – 4.46 (m, 2H), 4.45 – 4.39 (m, 1H), 4.28 – 4.22 (m, 1H), 4.05 – 3.95 (m, 1H), 1.96 – 1.91 (m, 3H), 1.77 – 1.72 (m, 3H). LCMS: Desired Mass: m/z (M+H)+ = 528.2; Observed Mass: m/z = 528.0. Example 6: 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]-N-[1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4-tria- zol-3-yl]ethyl]benzamide (I-17) Step 1: Synthesis of methyl 3-chloro-5-[N'-hydroxycarbamimidoyl]benzoate: To a solution of methyl 3-chloro-5-cy- ano-benzoate (5 g, 25.6 mmol, 1 eq) and hydroxyl ammonium chloride (2.6 g, 38.3mmol, 1.5 eq) in EtOH (50 mL) wase added triethylamine (3.9 g, 38.3mmol, 1.5 eq) at 25°C. The resulting mixture was stirred for 3h, at which time completion was determined by TLC (PE: EtOAc= 5: 1). The reaction mixture was quenched with water (50 mL), ex- tracted with EtOAc (3×30 mL), washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (PE in EtOAc= 0~30%) to afford methyl 3-chloro-5-[N'-hydroxycar- bamimidoyl]benzoate (5.23 g, 90%) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ [ppm] = 9.95 (s, 1H) 8.24 - 8.27 (m, 1H) 7.98 (t, J=1.69 Hz, 1H) 7.91 (t, J=1.63 Hz, 1H) 6.05 (bs, 2H) 3.89 (s, 3H). Step 2: Synthesis of methyl 3-chloro-5-[N'-methoxycarbamimidoyl]benzoate: To a solution of methyl 3-chloro-5-[N'- hydroxycarbamimidoyl]benzoate (8.2 g, 36 mmol, 1 eq) in DMSO/dioxane (20 mL/ 100 mL) was added dimethyl sul- fate (6.8 g, 54 mmol, 1.5 eq) at 0 °C. A solution of LiOH ×H2O (2.3 g, 54 mmol, 1.5 eq) in H2O ( 9.8 mL) was added dropwise to the reaction mixture at 0°C and allowed to warm up to 20-25°C under stirring over 5h, at which time completion was determined by. TLC (PE: EtOAc=5: 1). The reaction mixture was poured in water (400 mL) and ex- tracted with EtOAc (3×200 mL). The organic layers were washed with brine (500 mL), dried over Na2SO4 and con- centrated. The residue was purified by column chromatography on silica gel (PE in EtOAc= 0~25%) to deliver methyl 3-chloro-5-[N'-methoxycarbamimidoyl]benzoate (4.5 g, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ [ppm] = 8.22 (t, J=1.44 Hz, 1H) 7.98 (t, J=1.75 Hz, 1H) 7.93 (t, J=1.69 Hz, 1H) 6.31 (bs, 2H) 3.89 (s, 3H) 3.77 (s, 3H). Step 3: Synthesis of methyl 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoate: The reaction was con- ducted in two parallel batches. To a solution of methyl 3-chloro-5-[N'-methoxycarbamimidoyl]benzoate (2 g, 8.23 mmol, 1 eq) and (HCHO)3 (7.4 g, 82.3 mmol, 10 eq) in DCE (20 mL) was added TFA (4.9 g, 41.1 mmol, 5 eq) and the mixture stirred at 80°C for 2h. Then Et3SiH (2.9 g, 24.7 mmol, 3 eq) was added dropwise at 80°C and the mixture was stirred for 16h, at which time completion was determined by TLC (PE: EtOAc=10: 1). The two batches were combined. The reaction mixture was poured in water (150 mL), extracted with DCM (50 mL×3), washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE in EtOAc= 0~25%) to afford methyl 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoate (2 g, 45%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.06 (t, J=1.75 Hz, 1H) 7.88 (t, J=1.44 Hz, 1H) 7.46 - 7.53 (m, 1 H) 3.94 (s, 3H) 3.68 (s, 3H) 2.74 (s, 6H). Step 4: Synthesis of 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoic acid: To a solution of methyl 3- chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoate (2.2 g, 8.15 mmol, 1 eq) in THF/H2O (20 mL/4 mL) was added LiOH × H2O (684 mg, 16.29 mmol, 2 eq) at 0°C. The mixture was allowed to warm up to 20-25°C under stir- ring over 4h, at which time completion was determined by TLC (PE: EtOAc=10: 1). The reaction mixture was poured in water (50 mL) and extracted with EtOAc (20 mL). The aqueous layer was adjusted to pH 3 and extracted with EtOAc (3×20 mL ). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated to deliver 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoic acid (1.45 g, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ [ppm] = 7.93 (s, 1H) 7.68 (s, 1H) 7.57 (s, 1H) 3.53 (s, 3H) 2.61 (s, 6H). LCMS: Desired Mass: m/z (M–H)– = 255,1; Observed Mass: m/z = 255.0. Step 5: Synthesis of tert-butyl (1-(1-(6-(oxetan-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate: A mixture of tert-butyl N-[1-[2-(6-chloropyrimidin-4-yl)-1,2,4-triazol-3-yl]ethyl]carbamate (10.0g, 30.8mmol, 1eq), oxetane-3-car- boxylic acid (4.72 g, 46.2 mmol, 1.5 eq), 2,2′-bipyridine4,4′-bis(1,1-dimethylethyl) (1.24g, 4.6mmol, 0.15eq), di- chloro(1,2-dimethoxyethane)nickel (0.68g, 3.1 mmol, 0.1eq), Cs2CO3 (15.05g, 46.2mmol, 1.5eq) and [Ir{dF(CF3)ppy}2(dtbpy)]PF6 (1.04g, 0.9mmol, 0.03eq) in DMAC (10mL) was stirred under nitrogen and irradiation at 450 nm (LED) at 20-25°C overnight. The reaction mixture was diluted with water (50 mL), extracted with Et2O (3×350mL). The organic phase was washed with brine (50mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (DCM/MeOH = 20/1) to afford tert-butyl (1-(1-(6-(oxetan-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (1.1 g, 7%) as a yellow oil. 1H-NMR (300MHz, DMSO-d6) δ 9.25 (s, 1H), 8.26 (s, 1H), 7.92 (s, 1H), 7.58 (d, J=7.5 Hz, 1H), 5.81-5.76 (m, 1H), 4.98-4.93 (m, 2H), 4.86-4.82 (m, 2H), 4.62-4.60 (m, 1H), 1.47 (d, J=6.9 Hz, 3H), 1.34 (s, 9H). Step 6: Synthesis of 1-(1-(6-(oxetan-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethan-1-ammonium trifluoroacetate: To a solution of tert-butyl (1-(1-(6-(oxetan-3-yl)pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)carbamate (550mg, 1.60mmol, 1 eq) in DCM (6mL) was added TFA (2mL) at 20-25°C and the resulting mixture was stirred at 20-25°C for 5h. The volatiles were removed under reduced pressure to afford 1-(1-(6-(oxetan-3-yl)pyrimidin-4-yl)-1H-1,2,4- triazol-5-yl)ethan-1-ammonium trifluoroacetate (270 mg, 69%) as a yellow solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm]= 9.26 (d, J=0.8Hz, 1H), 8.60 (bs, 2H), 8.48 (s, 1H), 7.96 (d, J=0.8Hz, 1H), 5.54–5.49 (m, 1H), 4.96–4.93 (m, 2H), 4.82–4.79 (m, 2H), 4.64–4.56 (m, 1H), 1.64 (d, J=6.8 Hz, 3H). LC-MS (ES) m/z = 247.1 (M+H-TFA)+. Step 7: Synthesis of 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]-N-[1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]- 1,2,4-triazol-3-yl]ethyl]benzamide: A solution of 1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethylammonium trifluoroacetate (50 mg, 139 µmol, 1 eq), 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]benzoic acid (35.6 mg, 139 µmol, 1eq), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (68.6 mg, 180 µmol, 1.3eq) and diisopropylethylamine (59 µL, 44.8 mg, 347 µmol, 2.5 eq) in DMF (2 mL) was stirred at 20-25°C for 20 h. the volatiles were removed under reduced pressure and the residue was dissolved in CH2Cl2 (40 mL). The solution was washed with H2O (15 mL), dried over MgSO4, and filtered. The solvent was removed un- der reduced pressure and the residue was purified by column chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford 3-chloro-5-[N'-methoxy-N,N-dimethyl-carbamimidoyl]-N-[1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4- triazol-3-yl]ethyl]benzamide (55 mg, 0.113 mmol, 82%). 1H-NMR (400MHz, CDCl3) δ [ppm] = 9.21 (d, J=1.2 Hz, 1H), 8.00 (s, 1H), 7.91 (d, J=1.2 Hz, 1H), 7.83 (t, J=1.9 Hz, 1H), 7.62 (t, J=1.5 Hz, 1H), 7.49–7.44 (m, 1H), 7.42 (d, J=8.2 Hz, 1H), 6.55–6.42 (m, 1H), 5.10 (dd, J=8.4, 6.0 Hz, 2H), 4.98 (td, J=6.3, 2.3 Hz, 2H), 4.44 (ddd, J=14.8, 8.4, 6.5 Hz, 1H), 3.66 (s, 3H), 2.68 (s, 6H), 1.71 (d, J=6.7 Hz, 3H). LCMS: Desired Mass: m/z (M+H)+ = 485,2; Observed Mass: m/z = 485.0. Example 7: 3-chloro-N-[1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-5-(4-pyridylsulfonyl)benzamide (I-18) Step 1: Synthesis of 3-chloro-5-(4-pyridylsulfanyl)benzonitrile: To a solution of 3-chloro-5-fluorobenzonitrile (4g, 25.6mmol, 1eq) in DMF (60mL) was added pyridine-4-thiol (3.13g, 28.2 mmol, 1.1 eq) and Cs2CO3 (12.5g, 38.5mmol, 1.5 eq) at 25 °C,. The mixture was stirred at 80°C for 2h, at which time completion was determined by TLC (PE: EtOAc = 5:1). The reaction mixture was poured into H2O (100 mL), extracted with EtOAc (2×100mL), washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (EtOAc in PE = 0% - 20%) to afford 3-chloro-5-(4-pyridylsulfanyl)benzonitrile (3.3 g, 52%) as a yellow solid. 1H-NMR (400MHz, CDCl3) δ [ppm] = 8.51 (d, J=6.00 Hz, 2H) 7.63–7.73 (m, 3H) 7.06–7.14 (m, 2H). Step 2: Synthesis of 3-chloro-5-(4-pyridylsulfonyl)benzonitrile: To a solution of 3-chloro-5-(4-pyridylsulfanyl)benzo- nitrile (3.2g, 13.0mmol, 1eq) in EtOH (80mL) was added (NH4)6Mo7O24 . 4H2O (7.56g, 6.5mmol, 0.5eq) and H2O2 (30%, 2.95g, 26.0mmol, 2eq) at 25°C and stirred for 16h, at which time completion was determined by TLC (PE: EtOAc = 1:1). The reaction mixture was poured into H2O (200mL), extracted with EtOAc (2×100 mL), washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on sil- ica gel (EtOAc in PE = 0% ~ 50%) to deliver 3-chloro-5-(4-pyridylsulfonyl)benzonitrile (1.7g, 47%) as a white solid. 1H-NMR (400MHz, CDCl3) δ [ppm] = 8.91–8.97 (m, 2H) 8.14 (dt, J=12.1, 1.63 Hz, 2H) 7.85–7.90 (m, 1H) 7.76-7.83 (m, 2H). Step 3: Synthesis of 3-chloro-5-(4-pyridylsulfonyl)benzoic acid: The reaction was run in two parallel batches. A so- lution of 3-chloro-5-(4-pyridylsulfonyl)benzonitrile (1.35g, 4.85mmol, 1eq) in 75% H2SO4 (15mL) was stirred at 100°C for 12h, at which time completion was determined by TLC (PE: EtOAc = 1:1). The two batches were combined and quenched with cold water (150 mL). After adjusting the pH to 4~5 with aq 2N HCl, the mixture was extracted with EtOAc (3×100 mL), washed with brine (100 mL), dried over Na2SO4, filtered, concentrated to deliver 3-chloro-5-(4- pyridylsulfonyl)benzoic acid (total 2.65 g, 92%) as a white solid. 1H-NMR (400MHz, DMSO-d6) δ [ppm] = 8.89 – 8.93 (m, 2H) 8.40 (t, J=1.88 Hz, 1H) 8.35 (t, J=1.50 Hz, 1H) 8.20 - 8.23 (m, 1H) 8.02 - 8.05 (m, 2H). LCMS: Desired Mass: m/z (M–H)– = 296.0; Observed Mass: m/z = 296.0 Step 4: Synthesis of 3-chloro-N-[1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethyl]-5-(4-pyridylsulfonyl)ben- zamide: A solution of 1-[2-[6-(oxetan-3-yl)pyrimidin-4-yl]-1,2,4-triazol-3-yl]ethylammonium trifluoroacetate (50 mg, 139 µmol, 1 eq), 3-chloro-5-(4-pyridylsulfonyl)benzoic acid (41.3 mg, 139 µmol, 1 eq), 1-[bis(dimethylamino)meth- ylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (68.6 mg, 180 µmol, 1.3 eq) and diisopro- pylethylamine (59 µL, 44.8 mg, 347 µmol, 2.5 eq) in DMF (2 mL) was stirred at 20-25°C for 20 h. The solvent was removed under reduced pressure and the residue was dissolved in CH2Cl2 (40 mL), washed with H2O (15 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by col- umn chromatography on silica gel (c-hexane:EtOAc = 100:0 to 0:100) to afford 3-chloro-N-[1-[2-[6-(oxetan-3-yl)pyrim- idin-4-yl]-1,2,4-triazol-3-yl]ethyl]-5-(4-pyridylsulfonyl)benzamide (60 mg, 114 µmol, 82%). 1H-NMR (400MHz, CDCl3) δ [ppm]= 9.22 (d, J=1.2 Hz, 1H), 8.90 – 8.85 (m, 2H), 8.26 (t, J=1.6 Hz, 1H), 8.04 (d, J=1.7 Hz, 2H), 8.00 (s, 1H), 7.92 (d, J=1.2 Hz, 1H), 7.80 – 7.76 (m, 2H), 7.61 (d, J=7.6 Hz, 1H), 6.54–6.44 (m, 1H), 5.11 (dd, J=8.4, 6.1 Hz, 2H), 4.98 (td, J=6.3, 2.2 Hz, 2H), 4.50 – 4.38 (m, 1H), 1.72 (d, J=6.8 Hz, 3H). LCMS: Desired Mass: m/z (M+H)+ = 485.2; Observed Mass: m/z = 485.0. s r e mo it n S S c a c a r a r n e * H ] z/ 8 5. 3 6 M m [ 0 5 2 9 4 5 5 3 0 5 1 5 at a d T . R ] s n y C i 1 8 9 2 7 1 5 4 2 5 3 3 0 2 7 0 9 7 6 0 2 5 9 h L p P m [ 2. 1 1. 1 2. 2 1 . 1 . 1 2. 1 2. 1 1. 2 1 . 1 2. 1 3. 1 1 . 1 2. 1 H d o ht e A A A A A A A A A A A A A M I 5 R H H H H H H H H H H H H H * l 4 y l y d l l i R r o yl l yl l y z o y l y l y l yl l yl l yl l yl l y l y p a z o r a z a di r di r di r o z o a z o a z o a z a di r di r 2 y r y r y y - - - p y y r r r r y y - p p p - p 2 - p 2 - 2 y p y - p y - p y p p- p- 1 1 1 1 1 - 1 - 1 2 2 X H C H C H C H C H C H C H C H C H C H C H C H C H C F2 H ) ) F 2 C H4 H4 )4 )2 )3 H )3 O - C 6 3 3 6 H - F F 3 3 H C H 3 C- C 3 H F C 3 O - C 3 ) 2 5 F C 2 C 2 F F c - C ( C 2 c- 5 c 3 F 3 , R C ) - O O C - N N O l 2 , ) -l 2 (- H4 4 ( 2 S S - 5 4 ( 2 C C S C 4 C 5, 3 C 3 O - - c - S- 5 , , 5 , l C O - S 1(- C - - 5 - , 2 H ( 3 - - C 2(- N 5 l C , l C l - C - - 3 - 5 , 5 5 l , r , r r 5 c B B- , l - N 5 , l I - 3 3 1 C- C- B - - 3 3 C - C - C-al (- 3 3 3 3 1 ( 3 u 3 - 3 m r o f f o s d n u o 1 p R H H H H H H H H H H H H H m o C : I el b a . 1 2 3 0 1 2 3 T o N - I - I - I 4- I 5- I 6- I 7- I 8- I 9- I 1- I 1- I 1- I 1- I s r e mo it c n a c a c a c c c c c c c a c c a S S S S S S S a r r r a r a r a r a r a r a r r a r r n e * H ] 1 9 9 1 8 1 9 + z/ . M m 2 [ 6 7 5 8 8 5 . 4 2 5 8 4 5 . 2 0 . 5 5 2 . 4 4 2 . 5 6 3 5 2 4 5 8 . 0 9. 3 9. 9. 1. 7 7 5 5 3 5 3 5 5 9 4 6 4 3 7 3 4 7 8 4 4 5 9 4 9 4 at a d T . R ] s n 7 8 5 3 8 9 3 2 5 5 9 3 2 6 3 8 9 7 4 6 8 6 7 8 y C i 3. 1. 0. 8. 9. 9. 4 0. 2 1. 5 0. 3 0. 9 0. 0 9. 7 2 5 2 8 1 5 2 1 4 5 2 7 3 h L p P m [ 1 1 1 0 0 0 1 1 1 1 1 0 . 1 . 1 . 1 . 1 . 1 . 1 . 1 H d o ht e A A A A A A A A A A A A A A A A A A A M H5 5 R H H H H H H H H H H H H H H H H C 3 H H c )l y )l )l )l )l )l ni y l l y d n i i y t d n i i y d n i i y d n i i y d n i i di e l y l y l y t e l y t e t e t t l y l yl l l l l yl l yl 4 y di n R r a y t z a n - at n at n at z a n - at z a z e z e z l - a- a- a - o z o z y p a di y r di y r di r o z o a z a - e 2 x l o- yt e 3 e x e c o x e - o x l - o- yt e e x l o- yt l e yt l e yt l e yt a i e h r t - y y y y r r p p- p- p - y p y p a- 3 3 3 c a - 3 c a c c c - a- a a 2 - 1 2 2 2 - 1 - 1 1( - 1 ( - 1 ( 1 - ( 1 - ( 1 ( 3 3 - 3 - 3 - 3 - 3 X H C H C H C H C H C N N H C H C H C H C H C H C H C H C H C H C H C H C H 3 C 4 F 2 H3 ) 2 O -l )4 H C H4 )3 5 5 5 F N y n H3 C 3 O 6 H3 H H H3 C ) 2 ) 2 ) 2 = ] i 2 d ir C O c - 5 F C N = ) C - 3 3 F C c C c F F 3 C 3 c F 3 ) 2 C c = ) )5 3 F 3 R C F 3 (- C F 3 ) 3 y - ( C H p- 2 N , C ) O 2 5 - H4 S 5 - H3 4 ( - 2 l C 2 - - O 2 C O- C - ) C 5 O ( - 5 F 3 C O ( H3 C C , - ( 3 5, - 3 5 C , ( 3 N O - [ S 1( 3 - C C - c 5 , C O 2 S r c( S- (- - 5 5 , l , l C C - - 5 , l ( C - 5 - c , 5 ( , C- - 5 5 5 , , -N B - C- 5 5 , , l C- 3 3 , l - 3 3 F 3 5 , l l C l C C - - C - 3 5 , l , l C l C- C- C 3 - 3 C- , l C - 3 3 1 ( - 3 - C 3 - 3 3 3 3 - 3 H 5 C 3 1 R c- H H H H H H H H H H H H H H H H H H H2 C . o N 4 1 5 6 7 8 9 0 1 2 3 4 5 6 7 - I 1- I 1- I 1- I 1- I 1- I 2- I 2- I 2- I 2- I 2- I 2- I 2- I 2 8 - I 2 9 - I 2 0 - I 3 1 - I 3 2 - I 3- I s r e mo it n S S c a c c S c c S c c a c c a c c c a a r a r a r a r a r a r r a r r a r a r r n e * H ] 9 + z/ . 3 1. 9. 9. 9. M m [ 1 3 5 4 5 5 2 3 6 6 3 5 6 1 9 5 6 . 4 3 3. 5 8 5 8 2 5 6 7 5 1 0 9 5 3 . 5 2 0 5 9 5 3 . 5 8 9. 1 7 4 5 0 5 4 5 at a d T . R ] n 9 0 9 5 1 0 2 1 8 2 1 6 1 0 8 2 1 4 6 4 1 4 6 6 5 s y C h L i p P m [ 3. 1 2. 1 3. 1 2. 1 2. 1 3. 1 3. 1 3. 1 4. 4 1 2. 9 1 9. 8 0 2. 3 1 1. 0 1 . 8 1 0. 3 1 9. 0 H d o ht e A A A A A A A A A A A A A A A A M H5 H5 5 R H C 3 H H H H H H 3 H H H H H H H c C c )l y )l n y )l y l a n )l y n y l t a t n a t l l y l y l l yl l l l l y ei l y ei a t l y ei 4 o z di r di y r di y r di r o z y di y r di y r di n r a h t t - n ht o at - ei h n h t at t- R a i ht y - p y 2 - p y y a 2 - p 2 - p 2 - r 2 y y p- p y y - p- p- e i ht x o 1 2 2 2 - 3 i e i d h o - t x - oi - d o e x i h o t x oi 1, 3 - o- - 3 d- 1 1, 1 1, ( - 1 ( (- 3 1 ( 3 - 3 - 3 X H C H C H C H C H C H C H C H C H C N H C H C H C H C H C H C 4 2 )4 ) ) 2 4 H4 H F C 3 H C H H4 H4 H 3 H3 O C 3 c- ) 2 - 5 C 6 -r C 6 - C 6 C = F 3 F F -F )5 C2 C C 2 c- c- ) 2 ) ) N ) N ) 2 ) 2 ) 2 C- ) 2 5 H 3 3 F 3 , R C ) B - - - H3 O OS F 3 N C C- F 3 F 3 3 , C ( (- H4 4 ( 2 2 ( 2 3 ( 2 C S O C -1 1 ( C C F C F 3 N 5, 3 C 3 c O O O c - S S ( O- -5 (- (- - - S- C- 5 , 5, 5 5 ( , - ( 5, - ( 5, -5, C ) ) O O ( N - 5 5 , , 5 , 5 l 3 C F 3 , 3 F 2 3 3 3 ( S C- C- , l 1 ( C l C l , l - C - C- C 3 - F 3 C H C - 3 1(- - - 3 3 3 3 - 3 O- 3 O - 5 3 , l C- 3 1 3 R H H H H H H H H H C H H H H H H H . o N 3 3 4 5 6 7 8 9 0 1 2 3 - I 3- I 3- I 3- I 3- I 3- I 3- I 4- I 4- I 4- I 4 4 - I 4 5 - I 4 6 - I 4 7 - I 4 8 - I 4- I B. Biological examples If not otherwise specified, the test solutions are prepared as follow: The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water : acetone. The test solution is prepared on the day of use. The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the fol- lowing biological tests. B.1 Tobacco budworm (Heliothis virescens) For evaluating control of tobacco budworm (Heliothis virescens) the test unit consists of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds are formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concen- trations of formulated compounds are sprayed onto the insect diet at 10µl, using a custom-built micro atomizer, at two replications. After application, microtiter plates are incubated at about 28 + 1°C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality is then visually assessed. In this test, compounds I-1, I-2, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-14, I-15, I-16, I-20, I-21, I-23, I-24, I-26, I-27, I- 29, I-30, I-32, I-34, I-39, I-40, I-41, I-42, I-44, resp., at 2500 ppm showed at least 75% mortality in comparison with untreated controls. B.2 Boll weevil (Anthonomus grandis) For evaluating control of boll weevil (Anthonomus grandis) the test unit consists of 96-well-microtiter plates contain- ing an insect diet and 5-10 A. grandis eggs. The compounds are formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concen- trations of formulated compounds are sprayed onto the insect diet at 5µl, using a custom-built micro atomizer, at two replications. After application, microtiter plates are incubated at about 25 + 1°C and about 75 + 5 % relative humidity for 5 days. Egg and larval mortality is then visually assessed. In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-19, I-20, I-21, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31, I-32, I-34, I-35, I-37, I-38, I-39, I-40, I-41, I-42, I-43, I-44, resp., at 2500 ppm showed at least 75% mortality in comparison with untreated controls. B.3 Southern armyworm (Spodoptera eridania), 2nd instar larvae The active compounds are formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution is serially diluted in 100% cyclohexanone to make interim solutions. These serves as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20ml glass vials. A nonionic surfactant (Kinetic®) is included in the solution at a volume of 0.01% (v/v). The vials are then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects. Lima bean plants (variety Sieva) are grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions are sprayed onto the foliage by an auto-mated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants are dried in the sprayer fume hood and then removed from the sprayer. Each pot is placed into perforated plastic bags with a zip closure. Ten to 11 armyworm larvae are placed into the bag and the bags zipped closed. Test plants are maintained in a growth room at about 25ºC and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (14:10 light:dark photoperiod) to prevent trapping of heat in- side the bags. Mortality and reduced feeding are assessed 4 days after treatment, compared to untreated control plants. In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-14, I-15, I-16, resp., at 300 ppm showed at least 75% mortality in comparison with untreated controls. B.4 Yellow fever mosquito (Aedes aegypti) For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consists of 96-well-microtiter plates containing 200µl of tap water per well and 5-15 freshly hatched A. aegypti larvae. The active compounds are formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures are sprayed onto the insect diet at 2.5µl, using a custom-built micro atomizer, at two replications. After application, microtiter plates are incubated at 28±1°C, 80±5 % RH for 2 days. Larval mortality is then visually assessed. In this test, compounds I-1, I-2, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-14, I-15, I-16, I-19, I-20, I-21, I-23, I-26, I- 27, I-28, I-29, I-30, I-31, I-32, I-34, I-35, I-37, I-38, I-39, I-40, I-41, I-42, I-43, I-44, resp., at 2500 ppm showed at least 75% mortality in comparison with untreated controls. B.5 Green peach aphid (Myzus persicae) For evaluating control of green peach aphid (Myzus persicae) through systemic means, the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concen- trations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications. After application, 5-8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 ± 1°C and about 50 ± 5% rela- tive humidity for 3 days. Aphid mortality and fecundity was then visually assessed. In this test, compounds I-1, I-2, I-4, I-6, I-7, I-8, I-9, I-11, I-12, I-14, I-15, I-16, I-17, I-19, I-20, I-21, I-22, I-23, I-24, I- 25, I-26, I-29, I-31, I-34, I-35, I-38, I-43, I-44, resp., at 2500 ppm showed at least 75% mortality in comparison with untreated controls. Comparison of activity with prior art The beneficial activity of the compounds according to the invention containing a 6-substituted 4-pyrimidinyl ring over structurally close compounds known from prior art differing in the 6-membered hetaryl moiety linked to the 1,2,4- triazoles, was demonstrated by the following comparative experiments: The tables show % mortality in comparison to untreated controls. B.4 B.2 Structure Example 90 ppm 10 ppm I-27 100% 75% WO2019/206799 0% 0% I-159

Claims

Claims 1. Compounds of formula I I wherein R1 is H, OH, NR12R13, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C5-alkoxy, C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-halocycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, which groups are unsubstituted, or partially or fully substituted with R11; or C(=N-R11)R12, C(O)R11a; R10 is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C4-cycloalkyl-C1-C2- alkyl, C3-C4-halocycloalkyl-C1-C2-alkyl, C(O)-C1-C4-alkyl, C(O)-C1-C4-haloalkyl, C(O)-C3-C4- cycloalkyl, C(O)-C3-C4-halocycloalkyl, SOm-C1-C4-alkyl, SOm-C1-C4-haloalkyl, SOm-C3-C6- cycloalkyl, or phenyl which is unsubstituted or partially or fully substituted with R3a; R11 is halogen, CN, NO2, NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR10, Si(CH3)3; C1-C6-alkyl; C1-C6- haloalkyl; C2-C6-alkenyl; C2-C6-haloalkenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl- C1-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; R11a is NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR10, Si(CH3)3; C1-C6-haloalkyl; C2-C6-alkenyl; C2-C6- haloalkenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl-C1-C2-alkyl, which ring is unsub- stituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, which rings are un- substituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; R12, R13 are independently from each other H, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1- C4-haloalkyl, C3-C6-cycloalkyl, C(O)-C1-C4-alkyl, C(O)-C1-C4-haloalkyl, C(O)-C3-C4-cycloalkyl, C(O)-C3-C4-halocycloalkyl, C(O)NH-C1-C4-alkyl, C(O)NH-C1-C4-haloalkyl, C(O)N(C1-C4-alkyl)- C1-C4-alkyl, C(O)N(C1-C4-haloalkyl)-C1-C4-alkyl, C(O)N(C1-C4-haloalkyl)-C1-C4-haloalkyl, C(O)NH-C1-C4-alkoxy, C(O)NH-C1-C4-haloalkoxy, C(O)NH-C1-C4-alkoxy-C1-C4-alkyl, C(O)NH- C1-C4-alkoxy-C1-C4-haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocyclyl or 5- or 6- membered hetaryl, C(O)NH-C1-C4-alkyl-phenyl, C(O)NH-C1-C4-alkyl-3-6-membered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, C1-C3- haloalkyl, and/or CN; S(O)m-C1-C4-haloalkyl, S(O)m-C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloal- kyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsub- stituted or substituted with halogen, C1-C3-haloalkyl, and/or CN; or R12 and R13 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-mem- bered saturated, partially or fully unsaturated heterocycle, which heterocycle may additionally contain 1 or 2 heteroatoms or heteroatom-containing groups selected from N, O, S(O)m, and optionally one or two groups C(O) as ring members, and which heterocycle is unsubstituted or substituted with one or more R3a; m is 0, 1, or 2; R2 is H, CN, C1-C3-alkyl, C1-C3-haloalkyl, C2-C3-alkynyl; R3 halogen, CN, NO2; C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-halocycloalkyl, C1-C6-alkenyl, C1-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C6-cycloalkyl which are unsubstituted or substituted with R3a; OR14, NR12R13, C(O)NR12R13, C(O)OR14, C(O)R15, S(O)m-R15; R14 is as defined for R10; R15 is H, C1-C4-alkyl, or C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C6-halocycloalkyl, which carbon chains are unsubstituted or partially or fully substituted with R11; or 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with R3a; R3a is halogen, CN, NO2, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloal- koxy, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, S(O)m-C1-C4-alkyl, S(O)m-C1-C4-haloalkyl, S(O)m- C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloalkyl; n is 0, 1, 2, or 3; R4 is 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or partially or fully substituted with R3; or R4 is 3- to 7-membered saturated or unsaturated heterocyclyl containing at least one heteroatom or group selected from N, O, S(O)m, and optionally one or two groups C(O) as ring members, which heterocyclyl are unsubstituted or partially or fully substituted with R3; if substituted at a ring C atom, or partially or fully substituted with R3b if substituted at a ring N atom, R3b C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-halocycloalkyl, C1-C6-alkenyl, C1-C6-al- kynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C6-cycloalkyl which are unsubstituted or sub- stituted with R3a; C(O)NR12R13, C(O)OR14, C(O)R15, S(O)m-R15; R5 is defined as for R3; X is N, CH, or CR3c; R3c is as defined for R3; and the N-oxides, stereoisomers, and agriculturally or veterinarily acceptable salts thereof.
2. Compounds of formula I according to claim 1, wherein R1 is H or CH2-cC3H5.
3. Compounds of formula I according to claim 1 or 2, wherein R2 is CH3.
4. Compounds of formula I according to any of claim 1 to 3, wherein R3 is halogen, CN, C1-C4-haloalkyl, C1-C4- haloalkoxy, C3-C4-cycloalkyl unsubstituted or substituted with one or more CN or halogen, C3-C4-halocycloal- kyl, S(O)m-C1-C4-alkyl, S(O)m-C1-C4-haloalkyl, S(O)m-(phenyl partially substituted with R11).
5. Compounds of formula I according to any of claim 1 to 4, wherein n is 2 and R3 is in positions 3 and 5.
6. Compounds of formula I according to any one of claims 1 to 5, wherein X is CH.
7. Compounds of formula I according to any one of claims 1 to 6, wherein R4 is 2-pyridinyl, 3-pyridinyl, 2-thia- zolyl, 1-pyrazolyl, 3-thietanyl, 3-(1-oxo-thietanyl), 3-(1,1-dioxo-thietanyl), or 3-azetidinyl substituted with R3.
8. Compounds of formula I according to any one of the preceding claims wherein R4 is phenyl or hetaryl and at least one R3 group in (R3)n is selected from R3d, R3d C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1- C6-alkyl-C3-C6-cycloalkyl which are unsubstituted or substituted with R3a; NR12R13, C(O)NR12R13, C(O)OR14, C(O)R15, and S(O)m-R15 wherein m is 1 or 2.
9. Compounds of formula I according to any one of the preceding claims, wherein R5 is H or cC3H5.
10. Compounds of formula I according to any one of the preceding claims, which consist mainly of the isomer I.S.
11. An agricultural or veterinary composition comprising at least one compound according to any one of claims 1 to 10 and/or at least one agriculturally or veterinarily acceptable salt thereof, and at least one inert liquid and/or solid agriculturally or veterinarily acceptable carrier.
12. An agricultural composition for combating animal pests comprising at least one compound as defined in any of claims 1 to 10 and at least one inert liquid and/or solid acceptable carrier and, if desired, at least one surfac- tant.
13. A method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound as de- fined in any one of claims 1 to 10.
14. A method for protecting growing plants from attack or infestation by invertebrate pests, which method com- prises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound as defined in any of claims 1 to 10.
15. Seed comprising a compound as defined in any of claims 1 to 10, or the enantiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
16. A method for treating or protecting an animal from infestation or infection by invertebrate pests which com- prises bringing the animal in contact with a pesticidally effective amount of at least one compound of the for- mula I as defined in any of claims 1 to 10, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.
AU2024260362A 2023-04-24 2024-04-17 Pyrimidine compounds for the control of invertebrate pests Pending AU2024260362A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP23169386.2 2023-04-24
EP23169385.4A EP4455137A1 (en) 2023-04-24 2023-04-24 Pyrimidine compounds for the control of invertebrate pests
EP23169386 2023-04-24
EP23169385.4 2023-04-24
EP23216860.9 2023-12-14
EP23216860 2023-12-14
PCT/EP2024/060340 WO2024223373A1 (en) 2023-04-24 2024-04-17 Pyrimidine compounds for the control of invertebrate pests

Publications (1)

Publication Number Publication Date
AU2024260362A1 true AU2024260362A1 (en) 2025-11-06

Family

ID=90720455

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2024260362A Pending AU2024260362A1 (en) 2023-04-24 2024-04-17 Pyrimidine compounds for the control of invertebrate pests

Country Status (5)

Country Link
CN (1) CN121039120A (en)
AU (1) AU2024260362A1 (en)
IL (1) IL324056A (en)
MX (1) MX2025012595A (en)
WO (1) WO2024223373A1 (en)

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1395571A1 (en) 2001-06-11 2004-03-10 Shire Biochem Inc. Compounds and methods for the treatment or prevention of flavivirus infections
GB201312800D0 (en) 2013-07-17 2013-08-28 Heptares Therapeutics Ltd mGlu5 modulators
TWI696615B (en) 2016-05-05 2020-06-21 瑞士商伊蘭科動物健康公司 Heteroaryl-1,2,4-triazole and heteroaryl-tetrazole compounds
CN109651358B (en) 2017-10-11 2023-04-07 上海迪诺医药科技有限公司 4-aminopyridine derivative, pharmaceutical composition, preparation method and application thereof
CN111818801A (en) 2018-03-08 2020-10-23 拜耳公司 Use of heteroaryl-triazoles and heteroaryl-tetrazole compounds as pesticides in plant protection
ES2941857T3 (en) 2018-04-12 2023-05-26 Bayer Ag N-(Cyclopropylmethyl)-5-(methylsulfonyl)-n-{1-[1-(pyrimidin-2-yl)-1h-1,2,4-triazol-5-yl]ethyl}benzamide derivatives and the corresponding pyridine-carboxamide derivatives as pesticides
MY202639A (en) 2018-04-25 2024-05-13 Bayer Ag Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
EP4107151A1 (en) 2020-02-18 2022-12-28 Bayer Aktiengesellschaft Heteroaryl-triazole compounds as pesticides
TWI891782B (en) 2020-05-06 2025-08-01 德商拜耳廠股份有限公司 Novel heteroaryl-triazole compounds as pesticides
AU2022335656A1 (en) 2021-08-27 2024-03-07 Basf Se Pyrazine compounds for the control of invertebrate pests
TW202328089A (en) 2021-09-08 2023-07-16 印度商皮埃企業有限公司 Sulfoximines/sulfilimine containing aromatic caboxamide compounds and their use therof
MX2024002709A (en) 2021-10-08 2024-03-20 Nihon Nohyaku Co Ltd PYRIMIDINYL TRIAZOLE COMPOUND OR SALT THEREOF, PEST CONTROL AGENT CONTAINING SUCH COMPOUND AS AN ACTIVE INGREDIENT AND METHOD OF PEST CONTROL.

Also Published As

Publication number Publication date
IL324056A (en) 2025-12-01
MX2025012595A (en) 2025-11-03
WO2024223373A1 (en) 2024-10-31
CN121039120A (en) 2025-11-28

Similar Documents

Publication Publication Date Title
KR20240052751A (en) Pyrazine compounds for control of invertebrate pests
WO2023041422A1 (en) Heterocyclic compounds for the control of invertebrate pests
WO2023285175A1 (en) Triazole compounds for the control of invertebrate pests
EP4291551B1 (en) Substituted isoxazoline derivatives
EP4392408A1 (en) Pyrazine compounds for the control of invertebrate pests
US20250026757A1 (en) Bicyclic Compounds for the Control of Invertebrate Pests
WO2024061665A1 (en) N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides
WO2023110473A1 (en) Heterocyclic compounds for the control of invertebrate pests
US20230180754A1 (en) Heterocyclic compounds for the control of invertebrate pests
WO2023104564A1 (en) Pyrazine compounds for the control of invertebrate pests
WO2024223373A1 (en) Pyrimidine compounds for the control of invertebrate pests
KR20250174920A (en) Pyrimidine compounds for control of invertebrate pests
US20250163037A1 (en) Substituted isoxazoline derivatives
WO2025008247A1 (en) Triazole compounds for the control of invertebrate pests
KR20250127064A (en) Heteroaryl compounds for controlling invertebrate pests
WO2025008250A1 (en) Triazole compounds for the control of invertebrate pests
WO2025008249A1 (en) Triazole compounds for the control of invertebrate pests
CN117957221A (en) Heterocyclic compounds for combating invertebrate pests
CN118355017A (en) Bicyclic compounds for controlling invertebrate pests
CN118871437A (en) Substituted isoxazoline derivatives
WO2025131957A1 (en) Diazinone compounds for the control of invertebrate pests
CN117642390A (en) Triazole compounds for controlling invertebrate pests
CN117980299A (en) Pyrazine compounds for controlling invertebrate pests
CN117836279A (en) Pyrazine compounds for controlling invertebrate pests