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WO2025201958A1 - Pyrimidyléthers à action herbicide - Google Patents

Pyrimidyléthers à action herbicide

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Publication number
WO2025201958A1
WO2025201958A1 PCT/EP2025/057295 EP2025057295W WO2025201958A1 WO 2025201958 A1 WO2025201958 A1 WO 2025201958A1 EP 2025057295 W EP2025057295 W EP 2025057295W WO 2025201958 A1 WO2025201958 A1 WO 2025201958A1
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WO
WIPO (PCT)
Prior art keywords
alkoxy
alkyl
halogen
compounds
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/057295
Other languages
English (en)
Inventor
Matthias Witschel
Juri Gerhard SKOTNITZKI
Thomas Seitz
Mihiret Tekeste SISAY
Trevor William Newton
Martin HARTMUELLER
Philipp Rudi Johnen
Peter Dombo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of WO2025201958A1 publication Critical patent/WO2025201958A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom

Definitions

  • the present invention relates to substituted pyrimidylethers as well as to compositions comprising the same.
  • the invention also relates to the use of said substituted pyrimidylethers or the compositions comprising the same for controlling undesired vegetation.
  • the invention relates to methods for controlling undesired vegetation by using substituted pyrimidylethers or the compositions comprising the same.
  • weeds Undesired vegetation
  • Weeds compete with crops for essential resources such as water, nutrients, and sunlight. Their rapid growth and aggressive nature can significantly reduce crop yields if not adequately controlled. Over time, weeds can develop resistance to herbicides, making them less susceptible to chemical control methods. This can render certain herbicides ineffective and limit the options available for weed management.
  • the compounds should also show a broad activity spectrum against a large number of different unwanted plants. Further, the compounds should provide weed control over an adequately long period, thus allowing flexible application.
  • X 1 is O or S
  • R 2 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl,
  • R 3 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkylcarbonyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloal- kynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyloxy, C2-Ce-haloalkenyloxy, C2-C6- alkynyloxy, C2-Ce-haloalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkoxy, hydroxycarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, NH2, Ci-Ce-alkylamino, di(
  • R 4 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloal- kynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyloxy, C2-Ce-haloalkenyloxy, C2-C6- alkynyloxy, C2-Ce-haloalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkoxy, hydroxycarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, NH2, Ci-Ce-alkylamino, di(
  • R 5 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkylcarbonyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloal- kynyl, Ci-Ce-
  • R 6 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkylcarbonyl, C2-Ce-alkenyl, C2-C6-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloal- kynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6- alkynyloxy, C2-C6-haloalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkoxy, hydroxycarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, NH 2 , Ci-Ce-alkylamino,
  • R a is halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, or Ci-Ce-haloalkoxy;
  • R 7 is selected from H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl; provided that at least one of R 2 , R 3 , R 4 , R 5 , R 6 is not H and provided that when R 1 is halogen, X 1 is O, X 2 is O and R 2 , R 3 , R 5 , R 6 are H, then R 4 is not halogen, preferably provided that when R 1 is halogen, X 1 is O, X 2 is O, then R 4 is not halogen. including their agriculturally acceptable salts and derivatives for controlling undesired vegetation.
  • the compounds of formula (I) [also referred to as compounds (I)] show a strong herbicidal activity, in particular even at low application rates, and/or a high compatibility with crop plants, in particular low phytotoxicity to the crops.
  • the compounds (I) also show a broad activity spectrum against a large number of different unwanted plants. Further, the compounds (I) provide weed control over an adequately long period, thus allowing flexible application. Moreover, compounds (I) increase crop productivity and/or have a sufficiently low toxicity for humans and animals.
  • the compounds of formula (I) may have one or more centers of chirality, in which case they may be present as mixtures of enantiomers or diastereomers but also in the form of the pure enantiomers or pure diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds of formula I or their mixtures.
  • Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) as a specific form of diastereomers and mixtures thereof.
  • Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety.
  • the term "stereoisomer(s)” encompasses both optical isomers, such as enantiomers or diastereomers existing due to more than one stereogenic center in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of formula (I) have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Compounds of formula (I) having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-C -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cw-alkylthio esters.
  • amides such as mono- and di-Ci-Ce-alkylamides or arylamides
  • esters for example as allyl esters, propargyl esters, Ci-C -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cio-al kylthio ester is the ethylthio ester. If the compounds of formula (I) can form tautomers due to intramolecular proton transfer, these tautomers are also encompassed by the definition and comprised by the scope of general formula (I) according to the invention.
  • partially or fully halogenated means that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given chemical group have been replaced by halogen atoms.
  • partially or fully halogenated alkyl is also called haloalkyl.
  • alkyl denotes a straight-chain or branched saturated hydrocarbon group having usually 1 to 6 carbon atoms (Ci-Ce-alkyl), more frequently 1 to 4 carbon atoms (Ci-C4-alkyl), especially 1 to 3 carbon atoms (Ci-Cs-alkyl) or 1 or 2 carbon atoms (Ci-C2-alkyl).
  • haloalkyl denotes an alkyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.
  • Ci-Ce-haloalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluo- roethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1 -chloroethyl, 2-chloroethyl, 2, 2, -dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2
  • cyanoalkyl denotes an alkyl group as defined above, wherein the hydrogen atoms are partially replaced by cyano groups.
  • Examples of Ci-Ce-cyanoalkyl are cyanomethyl, 1-cy- anoethyl, 2-cyanoethyl, 1 -cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, and the like.
  • alkenyl denotes an unsaturated straight-chain or branched hydrocarbon group having usually 2 to 6 carbon atoms (C2-Ce-alkenyl), more frequently 2 to 4 carbon atoms (C2-C4- alkenyl) or 2 to 3 carbon atoms (C2-C3-alkenyl), and a double bond in any position.
  • haloalkenyl denotes an alkenyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms, for example chlorovinyl, chloroallyl and the like.
  • alkynyl denotes an unsaturated straight-chain or branched hydrocarbon groups having usually 2 to 6 carbon atoms (C2-Ce-alkynyl), more frequently 2 to 4 carbon atoms (C2-C4-al- kynyl) or 2 to 3 carbon atoms (C2-C3-alkynyl) and a triple bond in any position.
  • haloalkynyl denotes an alkynyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.
  • haloalkoxy denotes an alkoxy group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.
  • Ci-Ce-haloalkoxy are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2, 2, 2-tri chloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-di
  • haloalkenyloxy denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • alkynyloxy denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • haloalkynyloxy denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • cycloalkoxy (O-cycloalkyl) denotes a cycloalkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • Examples of Cs-Ce-cycloalkoxy are cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy.
  • Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1 -methoxyethoxy, 1 -ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 2- meth oxy ethoxy, 2-ethoxy- ethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1 -methoxypropoxy, 1-ethoxypropoxy, 1 -propoxypropoxy, 1 -isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-iso- propoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypro- poxy, and the like.
  • alkylthio denotes an alkyl group as defined above, attached via a sulfur atom to the remainder of the molecule.
  • Examples of Ci-Ce-alkylthio are methylthio, ethylthio, n- propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2- methylpropylthio (isobutylthio), 1 , 1-dimethylethylthio (tert-butylthio), pentylthio, 1-methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1
  • alkylamino denotes an amino group in which one hydrogen is replaced by an alkyl group as defined above.
  • Examples of (Ci-Ce-alkyl)amino are methylamino, ethylamino, propylamino, 1 -methylethylamino, butylamino, 1 -methylpropylamino, 2-methylpropylamino, or 1 ,1-di- methylethylamino, pentylamino, 1 -methylbutylamino, 2-methylbutylamino, 3-methylbutylamino,
  • Ci-Ce- alkylsulfonyl examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropyl- sulfony
  • alkylsulfonylamino [NHS(O) 2 -alkyl] denotes an amino group in which one hydrogen is replaced by an alkylsulfonyl group, as defined above.
  • phenoxy denotes a phenyl ring (Ph) attached via an O atom to the remainder of the molecule.
  • heterocyclyl denotes a saturated or partially or fully unsaturated cyclic group having four to six ring members which comprises apart from carbon atoms 1 , 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO 2 , N or NR 7 as ring members.
  • Partially unsaturated heterocycles contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size. Examples for four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic heterocycles are:
  • X 1 is O. According to another embodiment X 1 is S.
  • X 1 is O and X 2 is S.
  • X 1 is S and X 2 is O.
  • R 1 is CH3.
  • R 1 is CN.
  • R 2 is preferably selected from H, halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2- Ce-alkenyloxy, C2-Ce-haloalkenyloxy, C2-Ce-alkynyloxy, or C2-Ce-haloalkynyloxy; more preferably R 2 is selected from H, halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, or C2- Ce-alkynyl; even more preferably R 2 is selected from H, halogen, CN, or Ci-C4-alkyl; most preferably R 2 is selected from H, F, Br, Cl, CN, or CH3; in particular R 2
  • R 4 is preferably selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cy- anoalkyl, Ci-Ce-alkylcarbonyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-C6- haloalkynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyloxy, C2-Ce-haloalkenyloxy, C2- Ce-alkynyloxy, C2-Ce-haloalkynyloxy, Ci-Ce-alkylsulfinyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-al- kylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfonyl, phenyllsul
  • R 5 is preferably selected from H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-C6- haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-C6- alkenyloxy, C2-Ce-haloalkenyloxy, C2-Ce-alkynyloxy, or C2-Ce-haloalkynyloxy; more preferably R 5 is selected from H, halogen, Ci-Ce-alkyl, C2-Ce-alkenyl, or C2-C6- alkynyl; even more preferably R 5 is selected from H, halogen, or Ci-C4-alkyl; most preferably R 5 is selected from H, F, Br, Cl, or CH 3 ; in particular R 5 is H.
  • the cyclic groups of R 2 , R 3 , R 4 , R 5 , R 6 can be unsubstituted or substituted by 1 , 2 or 3 residues R a , preferably by 1 or 2 residues R a . According to one embodiment, the cyclic groups of R 2 , R 3 , R 4 , R 5 , R 6 are unsubstituted. According to another embodiment, the cyclic groups of R 2 , R 3 , R 4 , R 5 , R 6 are substituted by 1 residue R a . According to another embodiment, the cyclic groups of R 2 , R 3 , R 4 , R 5 , R 6 are substituted by 2 residues R a . According to another embodiment, the cyclic groups of R 2 , R 3 , R 4 , R 5 , R 6 are substituted by 3 residues R a .
  • X 1 is O;
  • X 2 is O;
  • R 1 is halogen, preferably F, Br or Cl;
  • X 1 is O;
  • X 2 is O;
  • R 1 is CN;
  • R n the residues R 2 , R 3 , R 4 , R 5 or R 6 have the meanings as defined anywhere in this application, provided that:
  • R n -2 R 3 or R 5 is not H; R n -4: at least two of R 2 , R 3 , R 4 , R 5 or R 6 are not H;
  • XR 1 -1/ R n -1 to XR 1 -6/ R n -4 the combination of X 1 , X 2 and R 1 in each case corresponds to the respective embodiment XR 1 (i.e. XR 1 - 1 to XR 1 -6); and the combination of R 2 , R 3 , R 4 , R 5 and R 6 in each case corresponds to the respective embodiment R n (i.e. R n -1 to R n -41).
  • R 1 is selected from halogen, CH 3 or CN; preferably from halogen or CH 3 ;
  • R 2 is selected from H, halogen, or Ci-Ce-alkyl
  • R 3 is selected from H, halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl,
  • Ci-Ce-alkylcarbonyl C2-Ce-alkenyl, C2-C6-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloal- kynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6- alkynyloxy, C2-C6-haloalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkoxy, hydroxycarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, NH 2 , Ci-Ce-alkylamino, di(Ci-Ce- alkyl)amino, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-
  • R 6 is H
  • R 5 is selected from H, halogen, and Ci-Ce-alkyl
  • R a is selected from halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, or Ci-Ce-haloalkoxy;
  • R 7 is selected from H or Ci-C4-alkyl; provided that at least one of R 2 , R 3 , R 4 , R 5 , R 6 is not H and provided that when R 1 is halogen, X 1 is O, X 2 is O and R 2 , R 3 , R 5 , R 6 are H, then R 4 is not halogen, preferably provided that when R 1 is halogen, X 1 is O, X 2 is O, then R 4 is not halogen.
  • T1-1/T2-1/T3-1 to T1-16/T2-30/T3-429 wherein the combination of X 1 , X 2 and R 1 in each case corresponds to a respective line of Table T 1 (i.e. lines T1-1 to T1-16); the combination of R 2 , R 5 and R 6 in each case corresponds to a respective line of Table T2 (i.e. lines T2-1 to T2-30); and the combination of R 3 and R 4 in each case corresponds to a respective line of Table T3 (i.e. lines T3-1 to T3- 429), except compounds:
  • R 2 is F
  • R 5 is F
  • R 6 is Cl (line T2-15 of Table T2)
  • R 3 is COOCH3
  • R 4 is OCF 3 (line T3-264 of Table T3). This numbering convention allowes that sometimes one and the same compound of formula (I) has two different numbers. For example, the compound can be enumerated as:
  • X 1 is O
  • X 2 is O
  • R 1 is F (line T1-1 of Table T1)
  • the ether or thioether bond can be formed by nucleophilic substitution of an (het)aryl halide, preferably a chloride or bromide, or alkylsulfonyl, preferably methylsulfonyl, by a thiophenol or phenol in the presence of a base, preferably sodium hydride, sodium carbonate, pyridine or triethylamine, optionally in presence of 0.001-1 equivalents of a transition metal salt, preferably copper, nickel or palladium, and optionally in presence of a ligand, like ethylenediamine or triphenylphosphine.
  • Protic or aprotic solvents can be used, preferably THF, toluene or methylene chloride, at temperatures from 0 °C to the boiling point of the solvent.
  • the (thio)ether bond can be formed by substitution of an (het)aryl boronic acid derivative, preferably the free boronic acid, by a thiophenol or phenol in presence of a base, preferably sodium carbonate, pyridine or triethylamine, optionally in presence of 0.001-1 equivalents of a transition metal salt, preferably copper, nickel or palladium, and optionally in presence of a ligand, like ethylenediamine or triphenylphosphine.
  • Protic or aprotic solvents can be used, preferably THF, toluene or methylene chloride, at temperatures from 0 °C to the boiling point of the solvent.
  • an oxidant can be present, preferably atmospheric oxygen.
  • the starting phenols, thiophenols, pyrimidine halides and arylboronic acids are known or can be prepared by standard laboratory methods.
  • the compounds of formula (I) may be applied in combination with other herbicides (B).
  • the present invention additionally provides compositions comprising a compound of formula (I) (component A) and a further herbicidal compound B (component B).
  • PPO Protoporphyrinogen Oxidase
  • Diphenyl ethers such as acifluorfen, bifenox, chlomethoxyfen, chlornitrofen, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, lactofen, nitrofen, and oxyfluorfen;
  • N-Phenyl-imides such as butafenacil, chlorphthalim, epyrifenacil, flufenoximacil, flumiclorac, flumioxazin, flumipropyn, fluthiacet, isoxafenacil, pentoxazone, saflufenacil, tiafenacil, and trifludimoxazin;
  • N-Phenyl- oxadiazolones such as oxadiargyl and oxadiazon;
  • N-Phenyl-triazoli nones such as azafenidin, carfentrazone, and s
  • B7 Glutamine Synthase inhibitors comprising Phosphinic acids such as glufosinate, and glufosinate-P;
  • DHPS Dihydropteroate Synthase inhibitors, comprising Carbamates such as asulam;
  • Microtubule Assembly inhibitors comprising: Benzamides such as propyzamide (prona- mide); Benzoic acids such as chlorthal; Dinitroanilines such as benfluralin (benefin), butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin; Phosphoramidates such as butamiphos; Pyridines such as dithiopyr; and Isoxazolines such as icafolin; B9.2) Microtubule Organization inhibitors, comprising: Carbamates such as carbetamide, chlorbufam, chlorpropham, propham and swep;
  • VLCFA Very Long-Chain Fatty Acid Synthesis
  • Azolyl-carboxamides such as cafenstrole, fentrazamide and ipfencarbazone; Benzofuranes such as benfuresate and ethofumesate; a-Chloroacetamides such as acetochlor, alachlor, bu- tachlor, butenachlor, delachlor, diethatyl-ethyl, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propisochlor, prynachlor and thenylchlor; Isoxazolines such as fenoxasulfone and pyroxasulfone; Oxiranes such as inda- nofan; a-Oxyacetamides_suc as flufenacet and mefenacet; a-Thioacetamides such as anilofo
  • B11 Cellulose synthesis inhibitors comprising: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, / ⁇ / 2 -(3-Chloro-5,6-difluoro-2- methoxyphenyl)-6-(1-fluoro-1-methylethyl)-1 ,3,5-triazine-2,4-diamine (CAS 2813322-23-3), N 2 - (3-Bromo-5,6-difluoro-2-methoxyphenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine (CAS 2813322-22-2) and /V 2 -(3-Chloro-4,5,6-trifluoro-2-methoxyphenyl)-6-(1-fluoro-1-meth- ylethyl)-1,3,5-triazine-2,4-diamine
  • B12 Uncouplers comprising dinosam, dinoterb, etinofen, and medinoterb;
  • 6-Arylpicolinates such as florpyrauxifen, halauxifen, fluchloraminopyr and indolauxipyr; 6-Chlo- ropicolinates such as aminopyralid, clopyralid, and picloram; Benzoates such as dicamba, and TBA (2,3,6); Phenoxy-carboxylates such as 2,4-D, clacyfos, 2,4-DB, clomeprop, dichlorprop, di- chlorprop-P, fenoprop, MCPA, MCPB, mecoprop, mecoprop-P; Phenyl carboxylates such as chlorfenac (fenac), and chlorfenprop; Pyridyloxy-carboxylates such as fluroxypyr and triclopyr; Pyrimidine-carboxylates such as aminocyclopyrachlor; Quinoline-carboxylates such as quin- clorac and quinmerac; and others such as benazolin;
  • Aryl pyrrolidinone anilides such as tetflupyrolimet and others such as 3-ethyl-2-[3-(trifluorome- thyl)phenoxy]-6-[3-(trifluoromethyl)-1 H-1 ,2 ,4-triazol- 1 -yl]pyridi ne (CAS 3052252-60-2);
  • Fatty Acid Thioesterase (FAT) inhibitors comprising
  • Benzyl ethers such as cinmethylin, cinflubrolin and methiozolin; Benzamides such as bromobu- tide, cumyluron, oxaziclomefone, and tebutam;
  • HST Homogentisate Solanesyltransferase inhibitors, comprising Phenoxypyridazines such as cyclopyrimorate;
  • B19 other herbicides selected from the group consisting of amitrole, bensulide, dazomet, dym- ron (daimuron), etobenzanid, flamprop, flamprop-M, flurprimidol, maleic hydrazide, metam, napropamide, napropamide-M, oleic acid, pelargonic acid, perfluidone, pyributicarb, quinocla- mine, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510- 21-5) including their agriculturally acceptable salts or derivatives.
  • compositions comprising a compound of formula (I) (component A), a herbicide B (component B) and a safener C (component C).
  • the compound (I) and component B) and/or component C) are applied jointly or separately. In the case of separate application, it is of minor importance, in which order the application takes place. It is only necessary, that the compound (I) and component B) and/or component C) are applied in an effective amount and in a time frame that allows simultaneous action of the Components on the plants, preferably within a timeframe of at most 14 days, in particular at most 7 days, very particular at most 1 day.
  • the compounds B and C described herein may have one or more centers of chirality, in which case they may exist in form of enathiomeric or diastereomeric mixtures and also in form of the pure enantiomers or pure diastereomers.
  • compositions described herein it is possible to use the compounds B and C in any of the beforementioned forms.
  • Compounds B and C having double bonds, such as alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety can be used in form of all possible geometrical stereoisomers (cis/trans isomers) as a specific form of diastereomers and mixtures thereof
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba-potas- sium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • a suitable ester are dicamba-methyl and dicamba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammo- nium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and 2,4-D- N,N,N-trimethylethanolammonium
  • esters of 2,4-D are 2,4- D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D- ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D- octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable ester of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.
  • Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
  • a suitable salt of glufosinate is for example glufosinate-ammonium.
  • a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
  • the agrochemical formulations may also comprise auxiliaries which are customary in agrochemical formulations.
  • auxiliaries depend on the particular application form.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. toluene, paraffin, tetrahydronaphthalene, and alkylated n
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. /V-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (Int. Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and of alkyl naphthalenes, sulfosuccinates, or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids, of oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, /V-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Examples of /V-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters, or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters, or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides may be added to the compositions described herein as premix, or, not until immediately prior to use (tank mix).
  • pesticides e.g. fungicides, growth regulators, herbicides, insecticides, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
  • the invention further relates to the use of a compound of formula (I) or of compositions comprising a compound of formula (I) for controlling undesired vegetation.
  • the undesired vegetation can be controlled in a non-crop area or in the cultivation area of a crop, where weeds grow or may grow.
  • non-crop area refers to any area of land that is not used for the cultivation of crops or agricultural production.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) can be used to control weeds and undesired plant growth in turf, lawns, parks, and gardens. They can also be used to maintain vegetation- free areas around roads, railways, sidewalks, and other infrastructure.
  • an effective amount refers to the quantity or application rate of the herbicidally active compound(s) that is necessary to achieve the desired effect or result. Hence, this is the amount of the herbicidally active compound(s) that is sufficient to effectively control or eliminate the target weeds or plants, while minimizing any adverse effects on non-target organisms or the environment.
  • the specific effective amount may vary depending on factors such as target plant species, application method, environmental conditions, and the desired level of control.
  • the required application rate of the compounds of formula (I) or compositions comprising compounds of formula (I) depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the compounds (I) are used and on the application method.
  • the application rate of compounds (I) is usually from 0.1 to 1000 g/ha, or from 0.1 to 750 g/ha, or from 1 to 500 g/ha, or from 1 to 475 g/ha, or from 1 to 450 g/ha, or from 1 to 425 g/ha, or from 1 to 400 g/ha, or from 1 to 375 g/ha, or from 1 to 350 g/ha, or from 1 to 325 g/ha, or from 1 to 300 g/ha, or from 1 to 275 g/ha, or from 1 to 250 g/ha, or from 1 to 225 g/ha, or from 1 to 200 g/ha, or from 1 to 175 g/ha or from 1 to 150 g/ha, or from 1 to 125 g/ha or from 1 to 100 g/ha, or from 1 to 75 g/ha or from 1 to 50 g/ha, or from 1 to 25 g/ha, or from 1 to 15 g/ha, of the active substance
  • the compounds of formula (I) or compositions comprising compounds of formula (I) can generally be applied for pre-plant burn-down, as pre- or post-emergence treatment of the crop, or together with the seed of a crop plant, preferably as post-emergence treatment.
  • pre-plant burndown refers to the practice of applying a herbicide to a field or area before planting crops.
  • the purpose of pre-plant burndown is to control or eliminate existing weeds or vegetation to create a weed-free environment for the crops.
  • Pre-plant burndown can also help to prevent the development of herbicide-resistant weeds, as it reduces the overall weed seed bank in the soil.
  • pre-emergence refers to an herbicide treatment that is applied to an area before the crop has emerged from the ground or growing medium.
  • post-emergence refers to an herbicide treatment that is applied to an area after the crop has germinated and emerged from the ground or growing medium.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are applied to an area by spraying, in particular foliar spraying of an aqueous dilution of the active ingredient of the composition.
  • Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 to 2000 l/ha or 50 to 1000 l/ha, for example from 100 to 500 l/ha.
  • Application by the low-volume and the ultra-low-volume method is possible, as is application in the form of microgranules.
  • compositions comprising compounds of formula (I) are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal composition is sprayed, with the aid of the spray apparatus, in such a way that they come into as little contact, if any, as possible with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil (post-directed, lay-by).
  • the compounds of formula (I) or compositions comprising compounds of formula (I) can be also applied by treating seed.
  • the treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting).
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the crop plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) may also be applied in combination with, or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition, or smart agricultural site management programs.
  • smart agricultural technologies typically include models, e.g. computer programs, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environmental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures.
  • Information input for these models include but is not limited to soil data (e.g. pH, organic matter content, moisture level, nutrient content such as nitrogen, potassium, phosphorous and micronutrient content); information on the plants that are currently growing or that may grow at the area of interest including crop plants and/or weeds (e.g. type of plant, chlorophyl levels, biomass, growth stage, plant health, plant water status, plant growth models, genetic traits, biotic damage by infestation or infection with pests, abiotic damage as caused by drought or nutrient stress etc.); weather information (e.g. information on past and present, and forecast of future temperature, humidity, and /or precipitation); information on the location of the area and directly derivable information thereof (e.g.
  • soil data e.g. pH, organic matter content, moisture level, nutrient content such as nitrogen, potassium, phosphorous and micronutrient content
  • information on the plants that are currently growing or that may grow at the area of interest including crop plants and/or weeds (e.g. type of plant, chlor
  • terrain features like altitude, slope, water bodies, sun exposure and hours of sunshine per day, vegetation period, etc.
  • information on pest pressure e.g. information of the past or present occurrence of unwanted vegetation, fungal diseases and invertebrate pests at the area of interest, at neighboring areas, the region, or the vegetation zone
  • information on beneficial organisms e.g. information of the past or present occurrence of beneficial organisms at the area of interest, at neighboring areas, the region, or the vegetation zone
  • I or historic information of any of the aforementioned e.g. information on previous seasons, or of an earlier point in time of the same season.
  • the information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data.
  • Data sources typically include proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones, or satellites.
  • Imaging technologies includes poly- and multispectral imagery in the LIV-VIS, NIR and UV spectrum.
  • Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and/or cloud applications.
  • the information is typically taken into account by at least one processing unit and used to provide recommendations, generate control signals (e.g.
  • the recommendations, control signals and (digital) maps may relate to or be used for controlling the application of water, nutrients, agrochemical products, or plant propagation material to the field of interest, or for taking other management measures like tilling, physical or laser-induced weeding.
  • Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, and model generation, cloud computing, and machine-to-machine communication.
  • self-steering robots such as tractors, harvesters, drones
  • artificial intelligence e.g. machine learning
  • imaging technologies e.g. image segmentation technologies
  • big data analysis e.g. image segmentation technologies
  • cloud computing e.g. image segmentation technologies
  • Precision agriculture such as precision farming is characterized by spatially and/or temporally resolved, targeted application of active ingredients like pesticides, preferably the compositions according to the present invention, plant-growth-regulators, fertilizers, and/or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and/or temporally resolved, targeted planting or seeding of desired plant propagation material to a agronomic site.
  • Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geo-positioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.
  • the compounds of formula (I) and compositions comprising compounds of formula (I) have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are used to control monocotyledonous weeds, such as weeds from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..
  • monocotyledonous weeds such as weeds from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp
  • Preferred examples of monocotyledonous weeds on which compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.
  • Especially preferred examples of monocotyledonous weeds on which compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are used to control dicotyledonous weeds, such as weeds selected from the genera Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., llrtica spp., Sida weeds, such
  • Preferred examples of dicotyledonous weeds on which the compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra
  • dicotyledonous weeds on which the compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are suitable for application in any variety of crops as outlined herein.
  • all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and/or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc.
  • corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn.
  • all maize or corn subspecies and/or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var.
  • indentata flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).
  • soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856).
  • the indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins.
  • all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are generally suitable for controlling weeds in the following crops:
  • Theobroma cacao (cacao plants), Trifolium pratense (red clover), Triticum aestivum (wheat), Triticale (triticale), Triticum durum (durum wheat), Triticum turgidum (hard wheat), Triticum spelta (Spelt), Vicia faba (tick beans), Vitis vinifera (grapes), and Zea mays (Indian corn, sweet corn, maize).
  • the compounds of formula (I) or compositions comprising compounds of formula (I) are particularly suitable for controlling weeds in the following crops:
  • the undesirable vegetation is controlled in cereals.
  • the cereals are selected from the group comprising wheat, barley, rye, oat, and triticale.
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.
  • Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
  • Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
  • Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
  • detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WG2017/011288.
  • ISAAA International Service for the Acquisition of Agri-biotech Applications
  • CERA Center for Environmental Risk Assessment
  • effects which are specific to a crop comprising a certain gene or event may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate.
  • the seeds of the test plants were sown separately for each species.
  • test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • test plants were kept at 10 - 25°C or 20 - 35°C, respectively.
  • test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.
  • test plants used in the greenhouse experiments were of the following species:
  • Table CU1 Herbicidal activity of the compound (CE-1) disclosed in US 4,427,437

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne les composés de formule (I), dans laquelle les variables sont telles que définies dans la description et les revendications. L'invention concerne en outre des procédés d'utilisation de ceux-ci et des compositions.
PCT/EP2025/057295 2024-03-27 2025-03-18 Pyrimidyléthers à action herbicide Pending WO2025201958A1 (fr)

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Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
US4427437A (en) 1977-09-13 1984-01-24 Ici Australia Limited Use of 2-phenoxypyrimidines as herbicides
EP0307103A2 (fr) * 1987-09-09 1989-03-15 Zeneca Limited Fongicides
WO1991013546A1 (fr) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Granules pesticides dispersibles ou solubles dans l'eau, obtenus a partir de liants thermo-actives
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0707445A1 (fr) 1993-07-03 1996-04-24 Basf Ag Formulation aqueuse polyphasee et stable prete a l'emploi pour produits phytosanitaires et procede de preparation
EP3028573A1 (fr) 2014-12-05 2016-06-08 Basf Se Utilisation d'un triazole fongicide sur des plantes transgéniques
WO2017011288A1 (fr) 2015-07-13 2017-01-19 E I Du Pont De Nemours And Company Éthers d'aryloxypyrimidinyle employés comme herbicides

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
US4427437A (en) 1977-09-13 1984-01-24 Ici Australia Limited Use of 2-phenoxypyrimidines as herbicides
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
EP0307103A2 (fr) * 1987-09-09 1989-03-15 Zeneca Limited Fongicides
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
WO1991013546A1 (fr) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Granules pesticides dispersibles ou solubles dans l'eau, obtenus a partir de liants thermo-actives
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0707445A1 (fr) 1993-07-03 1996-04-24 Basf Ag Formulation aqueuse polyphasee et stable prete a l'emploi pour produits phytosanitaires et procede de preparation
EP3028573A1 (fr) 2014-12-05 2016-06-08 Basf Se Utilisation d'un triazole fongicide sur des plantes transgéniques
WO2017011288A1 (fr) 2015-07-13 2017-01-19 E I Du Pont De Nemours And Company Éthers d'aryloxypyrimidinyle employés comme herbicides

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"Klingman: Weed Control as a Science", 1961, J. WILEY & SONS
"Perry's Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57
B. HOCKC. FEDTKER. R. SCHMIDT: "Herbizide [Herbicides", 1995, GEORG THIEME VERLAG
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC
K. K. HATZIOS: "Herbicide Handbook", 1998, WEED SCIENCE SOCIETY OF AMERICA
MCCUTCHEON'S: "Emulsifiers & Detergents, McCutcheon's Directories", vol. 1, 2008, INT. ED. OR NORTH AMERICAN
MOLLET, H.GRUBEMANN, A.: "Formulation technology", 2001, WILEY VCH VERLAG
no. 73222-52-3
PNAS, vol. 107, no. 19, 2010, pages 8563 - 856
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