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BR-112021016426-B1 - Herbicidal compounds, their use, herbicidal composition and method for controlling weeds.

BR112021016426B1BR 112021016426 B1BR112021016426 B1BR 112021016426B1BR-112021016426-B1

Abstract

HERBICIDAL COMPOUNDS. The present invention relates to compounds of Formula (I), wherein R1, R2, R3, R4 and G are as defined herein. The invention further relates to herbicidal compositions comprising a compound of Formula (I), to their use for controlling weeds, particularly in useful plant crops.

Inventors

  • ALAN JOSEPH HENNESSY
  • ELIZABETH PEARL JONES
  • Suzanna DALE
  • ALEXANDER WILLIAM GREGORY
  • IAN THOMAS TINMOUTH HOULSBY
  • Yunas Bhonoah
  • Julia COMAS-BARCELO

Assignees

  • SYNGENTA CROP PROTECTION AG

Dates

Publication Date
20260310
Application Date
20200219
Priority Date
20190222

Claims (10)

  1. 1. Compound characterized by having Formula (I) wherein R1 is 1-propynyl; R2 is methyl; R3 is methyl; R4 is -C(O)C(R5)=NO-R6 or -C(O)C(R5)=N-NR7R8; R5 is C1-C6 alkyl; R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy-C1-C3 alkyl, -CH2CN and pyridyl; R7 is hydrogen or C1-C6 alkyl; R8 is hydrogen or C1-C6 alkyl; G is hydrogen; or an agriculturally acceptable salt thereof.
  2. 2. Compound according to claim 1, characterized in that R5 is methyl.
  3. 3. Compound, according to claim 1 or 2, characterized in that R4 is -C(O)C(R5)=N-O-R6.
  4. 4. Compound, according to any one of claims 1 to 3, characterized in that R6 is methyl.
  5. 5. Compound, according to any one of claims 1 to 4, characterized in that G is hydrogen.
  6. 6. Herbicidal composition, characterized by comprising a compound of Formula (I), as defined in any one of claims 1 to 5, and an agriculturally acceptable formulation adjuvant.
  7. 7. Herbicidal composition, according to claim 6, characterized by further comprising at least one additional pesticide.
  8. 8. Herbicidal composition, according to claim 7, characterized in that the additional pesticide is a herbicide or herbicidal plant protection agent.
  9. 9. A method for controlling weeds in a location, characterized by comprising applying to the location an amount of weed control of a composition, as defined in any one of claims 6 to 8.
  10. 10. Use of a compound of Formula (I), as defined in claim 1, characterized in that it is a herbicide.

Description

[0001] The present invention relates to new herbicidal compounds, to processes for their preparation, to herbicidal compositions comprising the new compounds and to their use for weed control. [0002] Herbicidal compounds of cyclic diones substituted by a phenyl group having an alkynyl-containing substituent are disclosed, for example, in WO2014/096289 and WO2015/197468. The present invention relates to novel cyclohexanedione herbicide derivatives with improved properties. [0003] Thus, according to the present invention, a compound of Formula (I) is provided. wherein R1 is selected from the group consisting of methyl, ethinyl, 1-propynyl, phenyl and a 5- or 6-membered heteroaryl comprising one or two nitrogen heteroatoms, said phenyl and heteroaryl being optionally substituted by one or two substituents R9; R2 is selected from the group consisting of methyl, ethyl, methoxy and chlorine; R3 is selected from the group consisting of methyl, ethyl, methoxy and chlorine; R4 is -C(O)C(R5)=NO-R6 or -C(O)C(R5)=N-NR7R8; R5 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C3 alkyl, C3-C6 cycloalkyl, -CH2CN, tetrahydropyranyl, phenyl and pyridyl, wherein the phenyl and pyridyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro; R7 is hydrogen or C1-C6 alkyl; R8 is hydrogen or C1-C6 alkyl; R9 is independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, cyano and halogen; G is selected from the group consisting of hydrogen, -(CH2)n-Ra, -C(O)-Ra, -C(O)-(CRcRd)nO-Rb, -C(O)-(CRcRd)nS-Rb, -C(O)NRaRa, -S(O)2-Ra and C1-C8 alkoxy-C1-C3 alkyl; Ra is independently selected from the group consisting of hydrogen, C1-C8 alkyl, C1-C3 haloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, heterocyclyl and phenyl, wherein said heterocyclyl and phenyl groups are optionally substituted by a, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro; Rb is selected from the group consisting of C1-C8 alkyl, C1-C3 haloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, heterocyclyl and phenyl, wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro; Rc is hydrogen or C1-C3 alkyl; Rd is hydrogen or alkyl C1-C3; en is independently, 0, 1 or 2; or an agriculturally acceptable salt thereof. [0004] Alkyl groups (e.g. 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 (s-Bu) and tert-butyl (t-Bu). [0005] Alkenyl and alkynyl units may be in the form of linear or branched chains, and alkenyl units, when appropriate, may be in either (E) or (Z) configuration. Examples are vinyl, allyl, and propargyl. Alkenyl and alkynyl units may contain one or more double and/or triple bonds in any combination. [0006] Halogen (or halo) includes fluorine, chlorine, bromine, or iodine. The same applies correspondingly to halogen in the context of other definitions, such as haloalkyl. [0007] Haloalkyl groups (e.g. C1-C6 haloalkyl) are, 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-tetrafluoroethyl and 2,2,2-trichloroethyl, heptafluoro-n-propyl and perfluoro-n-hexyl. [0008] Alkoxy groups (e.g., C1-C4 alkoxy) are, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, or tert-butoxy, preferably methoxy and ethoxy. [0009] Alkoxyalkyl groups (e.g., C1-C8-alkyl C1-C3- alkoxy) include, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl, or isopropoxyethyl. [0010] Cycloalkyl groups (e.g. C3-C6-cycloalkyl) include, for example, cyclopropyl (c-propyl, c-Pr), cyclobutyl (c-butyl, c-Bu), cyclopentyl (c-pentyl) and cyclohexyl (c-hexyl), and may be substituted or unsubstituted as indicated. [0011] The invention also relates to agriculturally acceptable salts of the compounds of Formula (I). Such salts include those capable of forming with amines, alkali metal and alkaline earth metal bases, or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides as salt formers, special mention should be made of lithium, sodium, potassium, magnesium, and calcium hydroxides, but especially sodium and potassium hydroxides. The compounds of Formula