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US-20260125360-A1 - HERBICIDAL IMIDAZOLE COMPOUNDS

US20260125360A1US 20260125360 A1US20260125360 A1US 20260125360A1US-20260125360-A1

Abstract

The present invention relates to compounds of Formula (I), (I) or an agronomically acceptable salt of said compounds wherein Q, R 2 , R 3 and U are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.

Inventors

  • Suzanna DALE
  • PHILIP MICHAEL ELVES
  • James Alan Morris
  • Vikas Sikervar
  • Samuel Vaughan WATKIN

Assignees

  • SYNGENTA CROP PROTECTION AG

Dates

Publication Date
20260507
Application Date
20230929
Priority Date
20221006

Claims (15)

  1. 1 . A compound of Formula (I): or an agronomically acceptable salt thereof, wherein Q is phenyl or a C-linked 6-membered heteroaryl wherein said phenyl or 6-membered heteroaryl is optionally substituted by one or more independent R 1 ; U is a 5-membered heteroaryl optionally substituted by one or more independent R 7 ; R 1 is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxyC 1 -C 3 alkyl-, C 1 -C 4 alkoxyC 1 -C 3 alkoxy-, C 1 -C 4 alkoxyC 1 -C 3 alkoxyC 1 -C 3 alkyl-, —CN, NO 2 , C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, —S(O) p C 1 -C 4 alkyl, —S(O) p C 1 -C 4 haloalkyl, —C(O)OC 1 -C 4 alkyl and —C(O)NR 4 R 5 ; R 2 is selected from the group consisting of halogen, —CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, —C(O)C 1 -C 4 alkyl, —C(O)OC 1 -C 4 alkyl, C 1 -C 4 haloalkoxy, —S(O) p C 1 -C 4 alkyl, —C(R 6 )═NOR 8 and C 3 -C 6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, —CN, NO 2 , C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, —S(O) p C 1 -C 4 alkyl, —S(O) p C 1 -C 4 haloalkyl, —C(O)OC 1 -C 4 alkyl and —C(O)NR 4 R 5 ; R 4 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 5 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 6 is hydrogen or C 1 -C 2 alkyl; R 7 is independently of halogen, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxyC 1 -C 3 alkyl-, C 1 -C 4 alkoxyC 1 -C 3 alkoxy-, —CN, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, —S(O) p C 1 -C 4 alkyl, —S(O) p C 1 -C 4 haloalkyl, —C(O)OC 1 -C 4 alkyl, —C(O)NR 9 R 10 , —NR 11 COR 12 and —S(O) p NR 13 R 14 , R 8 is hydrogen or C 1 -C 2 alkyl; R 9 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 10 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 11 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 12 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 13 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 14 is selected from the group consisting of hydrogen, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; and p=0, 1 or 2.
  2. 2 . A compound of Formula (I) according to claim 1 , wherein U is selected from the group consisting of U1 to U46: wherein R 7 is as defined in claim 1 ; R 7a is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 3 -C 4 cycloalkyl; and n=0, 1 or 2.
  3. 3 . A compound according to claim 2 , wherein U is selected from the group consisting of U13, U23, U25, U27 and U28.
  4. 4 . A compound according to claim 1 , wherein Q is selected from the group consisting of Q 1 to Q-11: wherein R 1 is as defined in claim 1 ; and m is 0, 1 or 2.
  5. 5 . A compound according to claim 4 , wherein Q is selected from the group consisting of Q-1, Q-3 and Q-7.
  6. 6 . A compound according to claim 7 , wherein Q is Q-1.
  7. 7 . A compound according to claim 5 , wherein m is 1.
  8. 8 . A compound according to claim 1 , wherein R 2 is halogen or C 1 -C 4 haloalkyl.
  9. 9 . A compound according to claim 8 , wherein R 2 is —CF 3 or —CF 2 H.
  10. 10 . A compound according to claim 1 , wherein R 3 is hydrogen or halogen.
  11. 11 . A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
  12. 12 . A herbicidal composition according to claim 11 , further comprising at least one additional pesticide.
  13. 13 . A herbicidal composition according to claim 12 , wherein the additional pesticide is a herbicide or herbicide safener.
  14. 14 . A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 11 .
  15. 15 . Use of a compound of Formula (I) as defined in claim 1 as a herbicide.

Description

The present invention relates to herbicidal compounds, to herbicidal compositions which comprise the compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth. WO2023/066783 discloses herbicidal imidazole compounds which feature a pyrimidinyl group corresponding to the U position identified in Formula (I) below. The compounds of the present invention are differentiated in that they contain a 5-membered heteroaryl at this position. Thus, according to the present invention there is provided a compound of Formula (I): or an agronomically acceptable salt thereof,whereinQ is phenyl or a C-linked 6-membered heteroaryl wherein said phenyl or 6-membered heteroaryl is optionally substituted by one or more independent R1;U is a 5-membered heteroaryl optionally substituted by one or more independent R7;R1 is selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6cycloalkyl, C1-C4alkoxyC1-C3alkyl-, C1-C4alkoxyC1-C3alkoxy-, C1-C4alkoxyC1-C4alkoxyC1-C3alkyl-, —CN, NO2, C2-C4alkenyl, C2-C4alkynyl, —S(O)pC1-C4alkyl, —S(O)pC1-C4haloalkyl, —C(O)OC1-C4alkyl and —C(O)NR4R5;R2 is selected from the group consisting of halogen, —CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, —C(O)C1-C4alkyl, —C(O)OC1-C4alkyl, C1-C4haloalkoxy, —S(O)pC1-C4alkyl, —C(R6)═NOR8 and C3-C6cycloalkyl;R3 is selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, —CN, NO2, C2-C4alkenyl, C2-C4alkynyl, —S(O)pC1-C4alkyl, —S(O)pC1-C4haloalkyl, —C(O)OC1-C4alkyl and —C(O)NR4R5;R4 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R5 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R6 is hydrogen or C1-C2 alkyl;R7 is independently of halogen, C1-C4 alkyl, C3-C4cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4alkoxyC1-C3alkyl-, C1-C4alkoxyC1-C3alkoxy-, —CN, C2-C4alkenyl, C2-C4alkynyl, —S(O)pC1-C4alkyl, —S(O)pC1-C4haloalkyl, —C(O)OC1-C4alkyl, —C(O)NR9R10, —NR11COR12 and —S(O)pNR13R14;R8 is hydrogen or C1-C2 alkyl;R9 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R10 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R11 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R12 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R13 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl;R14 is selected from the group consisting of hydrogen, C3-C4cycloalkyl, C1-C4alkyl and C1-C4haloalkyl; andp=0, 1 or 2.C1-C4alkyl- and C1-C6alkyl-includes, for example, methyl (Me, CH3), ethyl (Et, C2H5), n-propyl (n-Pr), isopropyl (i-Pr), n-butyl (n-Bu), isobutyl (i-Bu), sec-butyl and tert-butyl (t-Bu). C1-C2alkyl is methyl (Me, CH3) or ethyl (Et, C2H5).C2-C4alkenyl- includes, for example, —CH═CH2 (vinyl) and —CH2—CH═CH2 (allyl).C2-C4alkynyl- refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to four carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C2-C4alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl), and but-1-ynyl. Halogen (or halo) includes, for example, fluorine, chlorine, bromine or iodine. The same correspondingly applies to halogen in the context of other definitions, such as haloalkyl. C1-C4haloalkyl-includes, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoropropyl and 2,2,2-trichloroethyl and heptafluoro-n-propyl. C1-C2haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, or 1,1-difluoro-2,2,2-trichloroethyl. C1-C6alkoxy includes methoxy and ethoxy. C1-C4haloalkoxy- includes, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy or 2,2,2-trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy. C1-C4alkoxyC1-C3alkyl- includes, for example, methoxymethyl-. C1-C4alkoxyC1-C3alkoxy- includes, for example, methoxyethoxy-. C1-C4alkoxyC1-C3alkoxyC1-C3alkyl- includes, for example, meth-oxyethoxymethyl-. C3-C6cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl. C1-C4alkyl-S— (alkylthio) includes, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, prefer