# US 2022/0030864 A1 · Methods of controlling or preventing infestation of cereal plants by phytopathogenic microorganisms fusarium pseudograminearum > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0030864 A1 - Document ID: US20220030864A1 - Status: Published application - Kind: A1 - Application number: 17/277,522 - Filed: 2019-09-16 - Published: 2022-02-03 - Earliest claimed: 2018-09-19 - Assignees: Syngenta Participations AG - Applicants: Syngenta Participations AG - Inventors: Kenneth MCKEE - Web page: https://patentgrep.com/patent/US20220030864A1 ## CPC - A01N 43/40: six-membered rings - C07D 213/81: Amides; Imides - A01P 3/00: Fungicides - C07D 213/54: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals - C07D 213/82: in position 3 - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS ## Abstract The present invention relates to methods for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum, comprising applying to a crop of plants, the locus thereof, or seed thereof, a compound according to formula (I) wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein. ## Claims ### Claim 1 A method for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum comprising applying to a crop of plants, the locus thereof, or seed thereof, a compound according to formula (I) wherein Y is O, C═O, or CR12R13; A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6; R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, R5 is hydrogen, methoxy or hydroxyl, B is phenyl substituted by one or more R8, R8 is, independently of each other, halogen, cyano or a group -L-R9, where each L is independently of each other a bond, —O—, —OC(O)—, —NR7-, —NR7CO—, —NR7S(O)n-, —S(O)n-, —S(O)nNR7-, —COO— or CONR7-, n is 0, 1 or 2, R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl is unsubstituted or substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, R9 is, independently of each other, C1-C6-alkyl, which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by one or more R10, C6-C14-bicycloalkyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl, which is unsubstituted or substituted by one or more R10, phenyl, which is unsubstituted or substituted by R10, or heteroaryl, which is unsubstituted or substituted by one or more R10, R10 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy; or a salt or N-oxide thereof; wherein B and A-CO—NR5 are cis to each other on the four-membered ring, or a tautomer or stereoisomer of these compounds. ### Claim 2 (depends on 1) The method according to claim 1, wherein Y is O or CH2; A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6; R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-haloalkoxy; R1, R2, R3, R4, and R5 are each hydrogen; B is phenyl substituted by one or more R8; R8 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl. ### Claim 3 (depends on 1) The method according to claim 1, wherein A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, or a phenyl ring having 1 or 3 substitutents selected from R6. ### Claim 4 (depends on 1) The method according to claim 1, wherein wherein B is a phenyl substituted by 1 to 3 substitutents R8. ### Claim 5 (depends on 1) The method according to claim 1, wherein Y is CH2; B is a mono or di-halogen substituted phenyl; A is selected from phenyl, pyrazinyl and pyridyl, each of which is mono or di-substituted by substituents independently selected from halogen and C1-C4-haloalkyl; R1, R2, R3, R4 and R5 are each hydrogen. ### Claim 6 (depends on 1) The method according to claim 1, wherein the compound is a compound of formula (Ic) wherein R11 and R12 are independently selected from halogen; A is pyridyl which is substituted by one or two substituents independently selected from halogen and C1-C4-haloalkyl. ### Claim 7 (depends on 1) The method according to claim 1, wherein A is selected from R13 is C1-C4-haloalkyl. ### Claim 8 (depends on 1) The method according to claim 1, wherein the compound is selected from any one of compounds 1 to 7 of formula (Ic) wherein R11, R12 and A are as defined in the following table: Compound A R11 R12 1 2-trifluoromethyl-pyrid-3-yl Cl Cl 2 3-trifluoromethyl-pyrid-2-yl Cl Cl 3 3-trifluoromethyl-pyrid-2-yl F F 4 3-trifluoromethyl-pyrid-2-yl Cl F 5 3-chloro-pyrid-2-yl Cl Cl 6 2-methyl-pyrid-3-yl Cl Cl 7 2-trifluoromethyl-pyrid-3-yl Cl F ### Claim 9 (depends on 8) The method according to claim 8, wherein the compound is of formula (Ic) wherein R11, R12 and A are as defined in the following table: Compound A R11 R12 1 2-trifluoromethyl-pyrid-3-yl Cl Cl ### Claim 10 (depends on 1) The method according to claim 1, wherein the compound is applied to a seed. ### Claim 11 (depends on 10) The method according to claim 10, wherein the rate of application to the seed is in the range of 0.002 and 0.03 mg AI per seed. ### Claim 12 (depends on 1) Use of a compound as defined in claim 1, for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum. ### Claim 13 (depends on 1) A method for growing cereal plants comprising applying or treating a seed thereof with a compound as defined in claim 1. ### Claim 14 (depends on 13) The method according to claim 13, wherein the rate of application is in the range of 0.002 and 0.03 mg AI per seed.