# US 2010/0167929 A1 · Pyrido-pyrazine derivatives useful as herbicidal compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0167929 A1 - Document ID: US20100167929A1 - Status: Published application - Kind: A1 - Application number: 12/518,923 - Filed: 2007-12-06 - Published: 2010-07-01 - Earliest claimed: 2006-12-12 - Assignees: Syngenta Crop Protection AG - Inventors: Neil Brian Carter; Matthew Robert Cordingley; Patrick Jelf Crowley; Michael Drysdale Turnbull - Web page: https://patentgrep.com/patent/US20100167929A1 ## CPC - C07D 471/04: Ortho-condensed systems - A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - 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 ## Abstract The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4 and R5 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to methods of controlling plants and compositions comprising compounds of formula (I). ## Claims ### Claim 1 A compound of formula (I) wherein R1 and R2 are independently hydrogen, C1-C4alkyl, C1-C4haloalkyl, halo, cyano, hydroxy, C1-C4alkoxy, C1-C4alkylthio, aryl or aryl substituted by one to five R6, which may be the same or different, or heteroaryl or heteroaryl substituted by one to five R6, which may be the same or different; R3 is C1-C4haloalkyl, C2-C4haloalkenyl or C2-C4haloalkynyl; R4 is aryl or aryl substituted by one to five R8, which may be the same or different, or heteroaryl or heteroaryl substituted by one to four R8, which may be the same or different; R5 is hydroxy or a group which can be metabolised to the hydroxy group; each R6 and R8 is independently halo, cyano, nitro, C1-C10alkyl, C1-C4haloalkyl, C2-C10alkenyl, C2-C10alkynyl, hydroxy, C1-C10alkoxy, C1-C4haloalkoxy, C1-C10alkoxy-C1-C4alkyl-, C3-C7cycloalkyl, C3-C7cycloalkoxy, C3-C7cycloalkyl-C1-C4alkyl-, C3-C7cycloalkyl-C1-C4alkoxy-, C1-C6alkylcarbonyl-, formyl, C1-C4alkoxycarbonyl-, C1-C4alkylcarbonyloxy-, C1-C10alkylthio-, C1-C4haloalkylthio-, C1-C10alkylsulfinyl-, C1-C4haloalkylsulfinyl-, C1-C10alkylsulfonyl-, C1-C4haloalkylsulfonyl-, amino, C1-C10alkylamino-, di-C1-C10alkylamino-, C1-C10alkylcarbonylamino-, aryl or aryl substituted by one to three R13, which may be the same or different, heteroaryl or heteroaryl substituted by one to three R13, which may be the same or different, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to three R13, which may be the same or different, heteroaryl-C1-C4alkyl- or heteroaryl-C1-C4alkyl- wherein the heteroaryl moiety is substituted by one to three R13, which may be the same or different, aryloxy- or aryloxy- substituted by one to three R13, which may be the same or different, heteroaryloxy- or heteroaryloxy- substituted by one to three R13, which may be the same or different, arylthio- or arylthio- substituted by one to three R13, which may be the same or different, or heteroarylthio- or heteroarylthio- substituted by one to three R13, which may be the same or different; and each R13 is independently halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy; or a salt or N-oxide thereof. ### Claim 2 (depends on 1) A compound according to claim 1 wherein R1 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, halo, cyano, hydroxy or C1-C4alkoxy. ### Claim 3 (depends on 1, 2) A compound according to claim 1 or claim 2 wherein R2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, halo, cyano, hydroxy or C1-C4alkoxy. ### Claim 4 (depends on 1, 2, 3) A compound according to any one of claims 1 to 3 wherein R3 is C1-C4haloalkyl or C2-C4haloalkenyl. ### Claim 5 (depends on 1, 2, 3, 4) A compound according to any one of claims 1 to 4 wherein R3 is 2,2-difluoro-ethyl. ### Claim 6 (depends on 1, 2, 3, 4, 5) A compound according to any one of claims 1 to 5 wherein R4 is aryl or aryl substituted by one to five R8, which may be the same or different. ### Claim 7 (depends on 1, 2, 3, 4, 5, 6) A compound according to any one of claims 1 to 6 wherein R5 is hydroxy, R9-oxy-, R10-carbonyloxy-, tri-R10-silyloxy- or R12-sulfonyloxy-, wherein R9 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy; R10 is C1-C10alkyl, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C10alkyl-, C1-C10haloalkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C4alkoxy-C1-C10alkyl-, C1-C4alkylthio-C1-C4alkyl-, C1-C10alkoxy, C2-C10alkenyloxy, C2-C10alkynyloxy, C1-C10alkylthio-, N—C1-C4alkyl-amino-, N,N-di-(C1-C4alkyl)-amino-, aryl or aryl substituted by one to three R14, which may be the same or different, heteroaryl or heteroaryl substituted by one to three R14, which may be the same or different, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to three R14, which may be the same or different, heteroaryl-C1-C4alkyl- or heteroaryl-C1-C4alkyl- wherein the heteroaryl moiety is substituted by one to three R14, which may be the same or different, aryloxy- or aryloxy- substituted by one to three R14, which may be the same or different, heteroaryloxy- or heteroaryloxy-substituted by one to three R14, which may be the same or different, arylthio- or arylthio-substituted by one to three R14, which may be the same or different; or heteroarylthio- or heteroarylthio- substituted by one to three R14, which may be the same or different; each R11 is independently C1-C10alkyl or phenyl or phenyl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy; R12 is C1-C10alkyl, C1-C10haloalkyl, or phenyl or phenyl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy; and each R14 is independently halo, cyano, nitro, C1-C10alkyl, C1-C4haloalkyl, C1-C10alkoxy, C1-C4alkoxycarbonyl-, C1-C4haloalkoxy, C1-C10alkylthio-, C1-C4haloalkylthio-, C1-C4haloalkylsulfinyl-, C1-C10alkylsulfonyl-, C1-C4haloalkylsulfonyl-, aryl or aryl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy, or heteroaryl or heteroaryl substituted by one to four substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy. ### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7) A compound according to any one of claims 1 to 7 wherein each R6 is independently halo, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy. ### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8) A compound according to any one of claims 1 to 8 wherein each R8 is independently halo, cyano, nitro, C1-C10alkyl, C1-C4haloalkyl, C1-C10alkoxy, C1-C4alkoxycarbonyl-, C1-C4haloalkoxy, C1-C10alkylthio-, C1-C4haloalkylthio-, C1-C1-C4haloalkylsulfinyl-, C1-C10alkylsulfonyl- or C1-C4haloalkyl-sulfonyl-. ### Claim 10 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9) A compound according to any one of claims 1 to 9 wherein R9 is C2-C10alkenyl, C2-C10alkynyl, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to three R13, which may be the same or different. ### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10) A compound according to any one of claims 1 to 10 wherein R10 is C1-C10alkyl, C3-C10cycloalkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C4alkoxy-C1-C10alkyl-, C1-C4alkylthio-C1-C4alkyl-, C1-C10alkoxy, C1-C10alkylthio-, N—C1-C4alkyl-amino-, N,N-di-(C1-C4alkyl)-amino-, phenyl or phenyl substituted by one to three R14, which may be the same or different, benzyl or benzyl wherein the phenyl moiety is substituted by one to three R14, which may be the same or different, thienyl or thienyl substituted by one to three R14, which may be the same or different, pyridyl or pyridyl substituted by one to three R14, which may be the same or different, phenoxy or phenoxy substituted by one to three R14, which may be the same or different, or phenylthio or phenylthio substituted by one to three R14, which may be the same or different. ### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) A compound according to any one of claims 1 to 11 wherein each R11 is independently C1-C4alkyl. ### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) A compound according to any one of claims 1 to 12 wherein R12 is C1-C4alkyl or C1-C4haloalkyl. ### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13) A compound according to any one of claims 1 to 13 wherein each R13 is independently halo, nitro, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy. ### Claim 15 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14) A compound according to any one of claims 1 to 14 wherein each R14 is independently halo, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy. ### Claim 16 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15) A method of controlling plants which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 15. ### Claim 17 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15) A herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 15 in addition to formulation adjuvants. ### Claim 18 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15) A herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 15, optionally one or more further herbicides, and optionally one or more safeners.