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EA-053294-B1 - HERBICIDAL IMIDAZOLE COMPOUNDS

EA053294B1EA 053294 B1EA053294 B1EA 053294B1EA-053294-B1

Abstract

The present invention relates to compounds of formula (I) or an agronomically acceptable salt of said compounds, wherein A, Q, R1, R2, R3 and m are as defined in this invention. The present invention further relates to herbicidal compositions that contain a compound of formula (I) and to the use of compounds of formula (I) for the control of weeds, in particular in agricultural crops of useful plants.

Inventors

  • Аспиналл Мэри Бернадетт
  • Бриггс Эмма
  • ДЕЙЛ Сюзанна Джейн
  • Эльвз Филипп Майкл
  • Кингстон Чарльз Уильям Фредерик
  • Моррис Джеймс Алан
  • СИКЕРВАР Викас
  • Уоткин Сэмюэл Воган

Assignees

  • СИНГЕНТА КРОП ПРОТЕКШН АГ

Dates

Publication Date
20260504
Application Date
20230707
Priority Date
20220715

Claims (15)

  1. 1. Compound of formula (I): or its agronomically acceptable salt, where A represents CR 11 or N; Q is selected from the group consisting of C2- C8 alkyl, C2- C8 alkenyl, C2-C8 alkynyl, C1 - C3 haloalkyl, C2 - C8 haloalkenyl, C2 - C8 haloalkynyl, C1-C4 alkoxy- C1 - C3 alkyl-, C1 - C4 haloalkoxy-C1- C3 alkyl-, C1 -C4 alkoxy- C1 - C3 haloalkyl-, C1- C8 cyanoalkyl-, C3 - C6 cycloalkyl (optionally substituted with CN, fluorine or chlorine), -S(O) p R 4 and -(CH 2 ) n R 10 ; R 1 is independently selected from the group consisting of halogen, -CN, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 2 alkoxy- and C 1 -C 2 haloalkoxy-; R 2 is selected from the group consisting of halogen, -CN, NO2, C1-C4 haloalkyl, C1-C4 alkoxy, -C(O)C1-C4 alkyl, -C(O)OC1-C4 alkyl, C1-C4 haloalkoxy, -S(O)pC1-C4 alkyl, -C(R 6 )=NOR7 and C3-C 6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halogen, C1-C 4 alkyl, C 1 -C 4 haloalkyl, C1-C 4 alkoxy, C1-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 8 R 9 ; R 4 is selected from the group consisting of C1-C 4 alkyl, C1-C 4 haloalkyl and C 3 -C 6 cycloalkyl; R 5 is selected from the group consisting of hydrogen, methyl, ethyl, -(CH 2 )-cyclopropyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl and cyclopropyl; R 6 is selected from the group consisting of hydrogen, methyl and ethyl; R 7 represents methyl or ethyl; R 8 is hydrogen or C 1 -C 4 alkyl; R 9 is hydrogen or C 1 -C 4 alkyl; R 10 is selected from the group consisting of -OH, -C(H)O, -C(O)R 4 , -S(O)pR 4 , -C(H)(OH)-CH2OH, -C(R 6 )=NOR 5 , -NR 12 R 13 , C 3 -C 6 cycloalkyl (optionally substituted with CN, fluorine or hydroxy), - 54 053294 saturated C3 - C6 heterocycle containing one or more oxygen atoms and a 5-membered heteroaryl which contains from 1 to 3 heteroatoms, each of which is independently selected from the group consisting of oxygen, nitrogen and sulfur, wherein said heteroaryl is optionally substituted with one or two substituents independently selected from the group consisting of halogen, cyano, C1 - C2 alkyl, C1 - C2 haloalkyl, C3 - C4 cycloalkyl, C1 - C2 alkoxy and C1 - C4 haloalkoxy; R 11 is selected from the group consisting of hydrogen, fluorine, chlorine and CN; R 12 and R 13 are independently selected from the group consisting of C 1-C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl-S(O) p -, C 3 -C 4 cycloalkyl-S(O) p -, C 1 -C 4 alkyl-C(O)- and C 3 -C 4 cycloalkyl-C(O)-; m is equal to 1 or 2; n is 1, 2, or 3; and p is 0, 1, or 2.
  2. 2. A compound of formula (I) according to claim 1, which is represented by formula (Ia): Q (la) where Q, R 1 , R 2 and R 3 are as defined in paragraph 1 above.
  3. 3. A compound according to any one of the preceding claims, wherein R 1 is chlorine.
  4. 4. A compound according to any one of the preceding claims, wherein R 2 is halogen or C 4 haloalkyl.
  5. 5. A compound according to any one of the preceding claims, wherein R 3 is hydrogen or halogen.
  6. 6. A compound according to any one of the preceding claims, wherein Q is selected from the group consisting of C2 -C8 alkyl, C2 -C8 alkenyl, C1 - C8 haloalkyl, C1 - C4 alkoxy- C1 - C3 alkyl-, C1-C4 haloalkoxy- C1 - C3 alkyl-, -S(O) pR4 and -(CH2) nR10 .
  7. 7. The compound of claim 6, wherein Q is -(CH 2 ) n R 10 , n is 1, 2, or 3, and R 10 is selected from the group consisting of -OH, -C(H)(OH)-CH 2 OH, and -C(H)=NOR 5 .
  8. 8. The compound according to claim 6, wherein Q is C 2 -C 8 alkyl.
  9. 9. The compound according to claim 6, wherein Q is C1- C8 haloalkyl.
  10. 10. The compound according to claim 6, wherein Q is C 1 -C 4 haloalkoxy-C 1 -C 3 alkyl-.
  11. 11. A herbicidal composition comprising a compound according to any one of the preceding claims and an agriculturally acceptable excipient.
  12. 12. The herbicidal composition according to claim 11, further comprising at least one additional pesticide.
  13. 13. The herbicidal composition according to claim 11, further comprising an additional herbicide or herbicide antidote.
  14. 14. A method for controlling weeds in a growing area, comprising treating the growing area with an amount of a composition according to any one of paragraphs 11-13 sufficient to control the weeds.
  15. 15. Use of a compound of formula (I): Q (I) or its agronomically acceptable salt, where A represents CR 11 or N; Q is selected from the group consisting of C2-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1 - C8 haloalkyl, C2 - C8 haloalkenyl, C2 -C8 haloalkynyl, C1- C4 alkoxy- C1 - C3 alkyl-, C1 - C4 haloalkoxy- C1 - C3 alkyl-, C 1 -C 4 alkoxy-C 1 -C 3 haloalkyl-, C 1 -C 8 cyanoalkyl-, C 3 -C 6 cycloalkyl (optionally substituted with CN, fluorine or chlorine), -S(O) p R 4 and -(CH 2 ) n R 10 ; R 1 is independently selected from the group consisting of halogen, -CN, C1-C 2 alkyl, C1-C 2 haloalkyl, C 3 -C 6 cycloalkyl, C1-C 2 alkoxy- and C1-C 2 haloalkoxy-; R 2 is selected from the group consisting of halogen, -CN, NO 2 , C 1 - C 4 alkyl, C 1 - C 4 haloalkyl, C1-C 4 alkoxy, -C(O)C1-C 4 alkyl, -C(O)OC 1 -C 4 alkyl, C1-C 4 haloalkoxy, -S(O) p C 1 -C 4 alkyl, -C(R 6 )=NOR 7 and C 3 -C 6 cycloalkyl; - 55 053294 R 3 is selected from the group consisting of hydrogen, halogen, CpCdalkyl, C1 - C4 haloalkyl, C1- C4 alkoxy, C4 haloalkoxy, -CN, NO 2 , C2 - C4 alkenyl, C2 - C4 alkynyl, -S(O) p C1 - C4 alkyl, -S(O) p C1 - C4 haloalkyl, -C(O)OC1- C4 alkyl and -C(O)NR 8 R 9 ; R 4 is selected from the group consisting of C1-C 4 alkyl, C1-C 4 haloalkyl and C 3 -C 6 cycloalkyl; R 5 is selected from the group consisting of hydrogen, methyl, ethyl, -(CH 2 )-cyclopropyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl and cyclopropyl; R 6 is selected from the group consisting of hydrogen, methyl and ethyl; R 7 represents methyl or ethyl; R 8 is hydrogen or C1-C 4 alkyl; R 9 is hydrogen or C1-C 4 alkyl; R 10 is selected from the group consisting of -OH, -C(H)O, -C(O)R 4 , -S(O)pR 4 , -C(H)(OH)-CH2OH, -C(R 6 )=NOR 5 , -NR 12 R 13 , C 3 -C 6 cycloalkyl (optionally substituted with CN, fluorine, or hydroxy), a saturated C 3 -C 6 heterocycle containing one or more oxygen atoms, and a 5-membered heteroaryl that contains from 1 to 3 heteroatoms, each of which is independently selected from the group consisting of oxygen, nitrogen, and sulfur, wherein said heteroaryl is optionally substituted with one or two substituents independently selected from the group consisting of halogen, cyano, C1-C 2 alkyl, C1-C 2 haloalkyl, C 3 -C 4 cycloalkyl, C1-C 2 alkoxy and C1-C 4 haloalkoxy; R 11 is selected from the group consisting of hydrogen, fluorine, chlorine and CN; R 12 and R 13 are independently selected from the group consisting of C1-C 4 alkyl, C 3 -C 4 cycloalkyl, C1-C 4 alkyl-S(O) p -, C 3 -C 4 cycloalkyl-S(O) p -, C1-C 4 alkyl-C(O)- and C 3 -C 4 cycloalkyl-C(O)-; m is equal to 1 or 2; n is 1, 2, or 3; and p is 0, 1, or 2; as a herbicide.

Description

The present invention relates to herbicidal compounds, methods for their preparation, herbicidal compositions that contain these compounds, and their use for controlling weeds, in particular in agricultural crops of useful plants, or for suppressing plant growth. Some imidazole compounds are disclosed in the prior art, such as CN 106317072 and WO 2022/015975. However, the potential use of such imidazole compounds as herbicides has never been reported. Thus, according to the present invention, there is provided a compound of formula (I): Q (I) or an agronomically acceptable salt thereof, where A represents CR 11 or N; Q is selected from the group consisting of C2 - C8 alkyl, C2 - C8 alkenyl, C2 - C8 alkynyl, C1- C8 haloalkyl, C2 - C8 haloalkenyl, C2 - C8 haloalkynyl, C1 - C4 alkoxy- C1 - C3 alkyl-, C1 - C4 haloalkoxy- C1 - C3 alkyl-, C1 - C4 alkoxy- C1 - C3 haloalkyl-, C1- C8 cyanoalkyl- (e.g., -CH2CH2CN ), C3 - C6 cycloalkyl (optionally substituted with CN, fluorine or chlorine ), -S(O) pR4 and -( CH2 ) nR10 ; R 1 is independently selected from the group consisting of halogen, -CN, C1-C 2 alkyl, C1-C 2 haloalkyl, C 3 -C 6 cycloalkyl, C1-C 2 alkoxy- and C1-C 2 haloalkoxy-; R 2 is selected from the group consisting of halogen, -CN, NO 2 , C1-C 4 alkyl, C1-C 4 haloalkyl, C1-C 4 alkoxy, -C(O)C1-C 4 alkyl, -C(O)OC1-C 4 alkyl, C1-C 4 haloalkoxy, -S(O) p C 1 -C 4 alkyl, -C(R 6 )=NOR 7 and C3-C6 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 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 8 R 9 ; R 4 is selected from the group consisting of C1-C 4 alkyl, C1-C 4 haloalkyl and C 3 -C 6 cycloalkyl; R 5 is selected from the group consisting of hydrogen, methyl, ethyl, -(CH 2 )-cyclopropyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl and cyclopropyl; R 6 is selected from the group consisting of hydrogen, methyl and ethyl; R 7 represents methyl or ethyl; R 8 is hydrogen or C1-C 4 alkyl; R 9 is hydrogen or C1-C 4 alkyl; R 10 is selected from the group consisting of -OH, -C(H)O, -C(O)R 4 , -S(O)pR 4 , -C(H)(OH)- CH2OH, -C(R 6 )=NOR 5 , -NR 12 R 13 , C 3 -C 6 cycloalkyl (optionally substituted with CN, fluorine, or hydroxy), a saturated C 3 -C 6 heterocycle containing one or more oxygen atoms (e.g., tetrahydropyran and tetrahydrofuran), and a 5-membered heteroaryl (e.g., pyrazolyl) that contains from 1 to 3 heteroatoms each independently selected from the group consisting of oxygen, nitrogen, and sulfur, wherein said heteroaryl is optionally substituted with one or two substituents independently selected from the group consisting of halogen, cyano, C1-C 2 alkyl, C1-C 2 haloalkyl, C 3 -C 4 cycloalkyl, C1-C 2 alkoxy and C1-C 4 haloalkoxy; R 11 is selected from the group consisting of hydrogen, fluorine, chlorine and CN; R 12 and R 13 are independently selected from the group consisting of C1-C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 4 alkyl-S(O) p -, C 3 -C 4 cycloalkyl-S(O) p -, C1-C 4 alkyl-C(O)- and C 3 -C 4 cycloalkyl-C(O)-; m is equal to 1 or 2; n is 1, 2, or 3; and p is 0, 1, or 2. C1- C4 alkyl and C1-C6 alkyl include, 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- C2 alkyl is methyl (Me, CH3) or ethyl (Et, C2H5). Halogen (or halo) includes, for example, fluorine, chlorine, bromine, or iodine. The same applies to halogen in the context of other definitions, such as haloalkyl. C 1 -C 8 haloalkyl includes, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro2,2,2-trichloroethyl, 2,2,3,3-tetrafluoropropyl and 2,2,2-trichloroethyl, heptafluoro-n-propyl and perfluoro-n-hexyl. C 1 -C 4 haloalkyl and C 1 -C 2 haloalkyl include, for example, fluoromethyl, difluoromethyl, - 1 053294 trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl or 1,1-difluoro-2,2,2-trichloroethyl. C 1 -C 4 alkoxy and C 1 -C 3 alkoxy include, for example, methoxy and ethoxy. C1 - C8 haloalkoxy- and C1- C8 haloalkoxy- include, 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. C 2 -C 8 alkenyl includes, for example, -CH=CH 2 (vinyl) and -CH 2 -CH=CH 2 (allyl). C 2 -C 8 alkynyl- refers to a group that is a straight or branched chain hydrocarbon radical consisting solely of carbon and hydrogen atoms, containing at least one triple bond containing from two to four carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C 2 -C 4 alkyny