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WO2019121352A1 - Herbicidal pyrimidine compounds - Google Patents

Herbicidal pyrimidine compounds Download PDF

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Publication number
WO2019121352A1
WO2019121352A1 PCT/EP2018/084863 EP2018084863W WO2019121352A1 WO 2019121352 A1 WO2019121352 A1 WO 2019121352A1 EP 2018084863 W EP2018084863 W EP 2018084863W WO 2019121352 A1 WO2019121352 A1 WO 2019121352A1
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Prior art keywords
alkyl
haloalkyl
alkoxy
formula
cycloalkyl
Prior art date
Application number
PCT/EP2018/084863
Other languages
French (fr)
Inventor
Veronica LOPEZ CARRILLO
Tobias SEISER
Gunther Zimmermann
Matthias Witschel
Thomas Seitz
Florian Vogt
Gerd Kraemer
Trevor William Newton
Peter Dombo
Klaus Reinhard
Klaus Kreuz
Doreen Schachtschabel
Eva HOLLENBACH
Ruth CAMPE
Original Assignee
Basf Se
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Publication of WO2019121352A1 publication Critical patent/WO2019121352A1/en

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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
    • C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to pyrimidine compounds of the general formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
  • WO 2000/073278 de-scribes such compounds being antagonists of the Neurokinin 1 receptor and thus having phar- maceutical properties.
  • WO2016/120355 discloses the use of phenylpyrimidines as herbicides.
  • R 1 is formula R 1
  • R x , R y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C1-C6- haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloal- kynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloalkoxy, C3-C6-cycloalkoxy, C3-C6-hal- ocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halo
  • R 2 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Ci-C 6 -alkoxy-C 2 -C 6 - alkenyl, Ci-C 6 -alkoxy-C 2 -C 6 -haloalkenyl, Ci-C 6 -haloalkoxy-C 2 -C 6 -alkenyl, Ci-C 6 -haloal- koxy-C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy-C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy-C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy-C 3 -C 6 -haloal
  • carbon atoms of cyclic groups of R 2 are unsubstituted or substituted independently of each other with 1 , 2, or 3 moieties R 20 ; and heteroatoms of cyclic groups of R 2 are un- substituted or substituted with Q;
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
  • Q is H, Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C6-alkylcarbonyl, C 2 -C 6 -alkenylcar- bonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6-al- kyl)aminosulfonyl, or Ci-C6-alkylaminosulfonyl;
  • R 20 is H, halogen, CN, NO 2 , OH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl, OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , C 3 -C 6 -alkenylsulfinyl, C 3 -C 6 -a I ki nyl s ulf i nyl , aminosulfinyl, C 1 - C6-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfinyl, C 3 -C
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R b is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6- haloalkinyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocyclo- alkenyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, Ci-C 6 -haloalkylcar- bonyl, C3-C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkyloxycarbonyl, Ci-C 6 -alkylthiocarbonyl, Ci-C 6 -amino
  • R c is halogen, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, NH2, Ci-C 6 -alkyl-amino, di(Ci-C 6 -alkyl)amino, SH, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, Ci-C 6 -alkyla- minocarbonyl, or di(Ci-C 6 -alkyl)aminocarbonyl;
  • R d is halogen, CN, NO2, OH, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C 6 -haloalkyl, C3- C 6 -haloalkenyl, C3-C6-haloalkinyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C 6 -haloalkoxy, NH2, Ci-C 6 -alkyl-amino, di(C1-C6-alkyl)amino, SH, Ci -C 6 -a I ky Ith i o , C1- C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, hydroxycar- bonyl, Ci-
  • R 4 and R 5 are independently from each other selected from hydrogen, Ci-C 6 -alkyl, C2-C6- alkenyl, C2-C6-alkinyl, OH, NH2, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C 6 -alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, Ci-C 6 -alkylsulfonyl, C1- C 6 -haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, Ci-C 6 -alkylsulfinyl, C3- C 6 -alkenylsulfinyl, C3-C6-alkinylsulfonyl, Ci-C 6 -alkyls
  • Z is phenyl, 5-, 6- or 9 membered heteroaryl, or 9- or 10-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
  • R 3 is H, halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alke- nyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloal- koxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkylthio, C 1 -
  • R e is halogen, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, or Ci-C 6 -haloalkoxy;
  • R f is H, halogen, CN, OH, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C 6 -haloalkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkinyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C 1 -C 6 - haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; m is 0, 1 , 2, 3, or 4;
  • n 1 , 2, 3, 4, or 5;
  • the present invention also provides the pyrimidine compounds of formula (I)
  • R 1 is formula R 1
  • R x , R y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C 1 -C 6 - haloalkyl, HO-Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloal- kenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -cycloal- koxy, C 3 -C 6 -halocyclo
  • R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom se- lected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Ci-C 6 -alkoxy-C 2 -C 6 - alkenyl, Ci-C 6 -alkoxy-C 2 -C 6 -haloalkenyl, Ci-C 6 -haloalkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 - haloalkoxy-C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy-C 2 -C 6 - alkynyl, Ci-C 6 -alkoxy-C 3 -C 6 -haloalkynyl, Ci-C 6 -haloalkoxy-C 2 -C 6
  • carbon atoms of cyclic groups of R 2 are unsubstituted or substituted independently of each other with 1 , 2, or 3 moieties R 20 ; and heteroatoms of cyclic groups of R 2 are unsubstituted or substituted with Q;
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
  • R b is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalky
  • R 20 is H, halogen, CN, NO2, OH, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(Ci-C 4 - alkoxy) n , Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkylsulfonyl, OR b , SH, SR b , C2-C6-alkenyl, C2-C6-alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , C3-C6-alkenylsulfinyl, C3-C6-a I ki nyl su If i ny I , aminosulfinyl, Ci-C 6 -alkylaminosulfinyl, di(Ci-C 6 -alkyl)aminosulfinyl, C3-C6-alken- ylsulfon
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R b is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3- C 6 -haloalkinyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6- halocycloalkenyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, C1-C6- haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C 6 -alkyl, C1-C6- alkyloxycarbonyl, Ci-C 6 -alkylthiocarbonyl, Ci-C 6 -aminocarbon
  • R c is halogen, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, C1-C6- haloalkoxy, NH2, Ci-C 6 -alkyl-amino, di(Ci-C 6 -alkyl)amino, SH, Ci-C 6 -alkylthio, C1- C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6- alkenyloxycarbonyl, alkinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, ami- nocarbonyl, Ci-C6-alkylaminocarbonyl, or di(Ci-C6-alkyl)aminocarbonyl;
  • R d is halogen, CN, NO 2 , OH, Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C6-haloal- kyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -haloalkinyl, Ci-C6-alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - alkinyloxy, Ci-C6-haloalkoxy, NH 2 , Ci-C6-alkyl-amino, di(C1-C6-alkyl)amino, SH, C 1 -C6-a I ky Ith i o , Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C 3 -C 6 -cycloalkyl, C 4 -C 8 - cyclo
  • R 4 and R 5 are independently from each other selected from hydrogen, Ci-C6-alkyl, C 2 - C6-alkenyl, C 2 -C 6 -alkinyl, OH, NH 2 , Ci-C6-alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -al- kinyloxy, Ci-C6-alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C 3 -C 6 -alkenylsulfonyl, C 3 -C 6 -alkinyl- sulfonyl, Ci-C6-alkylsulfinyl, C 3 -C 6 -alkenylsulfinyl, C 3 -C 6 -al
  • Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 1 0-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
  • R 3 is H, halogen, CN, NO 2 , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C 2 -C 6 - alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C6-alkoxy, C 1 -C 6 - haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloal- kynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, C 1 -C 6 - alkylthio, Ci-C6-haloalky
  • R f is H, halogen, CN, OH, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C 6 -haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, Ci-C 6 -haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-mem- bered heterocyclyl;
  • n 0, 1 , 2, 3, or 4;
  • n 1 , 2, 3, 4, or 5;
  • R 1 is CF 3 and Z-(R 3 ) m is Phenyl
  • R 2 is not CF 3
  • R 1 is CF 3 and Z-(R 3 ) m is 4-CN-Phenyl
  • R 2 is not Phenyl, Piperidyl, or N-substituted piperidinyl.
  • the present invention provides the pyrimidine compounds of said formula (I), wherein when m is 2, 3 or 4, each R 3 in formula (I) is independently H, halogen, CN, NO2, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al- kynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycar- bonyl, C1-C6-alkoxycarbonyl, C1
  • the present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
  • the present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) as herbicide.
  • pyrimidine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes or process described for preparation examples:
  • the pyrimidine compounds of formula (I) can be obtained by reacting respective amino- ketones of formula (II) with base and amidine (III):
  • the reaction of the aminoketones (II) with amidines (III) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 20°C to the boiling point, particularly from 40°C to 120°C, in an inert organic solvent in the presence of a base.
  • the reaction may in principle be carried out without solvent. However, preference is given to reacting the aminoketones (II) with the amidine (III) in an organic solvent. Suitable solvents are those capable of dissolving the aminoketones (II) with the amidine (III) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride (CCI 4 ) and chlorobenzene, ethers such as di- ethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofu- ran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propi- onitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-buta- nol, as well as dipolar aprotic
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCFh), sodium ethoxide (NaOC 2 H 5 ), potassium ethoxide (KOC 2 H 5 ), potassium tert-butoxide (/BuOK), potassium tert- pentoxide and dimethoxymagnesium,
  • tertiary amines such as tri- methylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperi- dine
  • TMA tri- methylamine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • N-methylpiperi- dine pyridine
  • substituted pyridines such as collidine, lutidine and 4-dimethylaminpyridine
  • bicyclic amines Particular preference is given to NaOCFh, NaOC2H 5 , KOC2H5, tBuOK and potassium tert-pentoxide.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the amidine (XI), based on the aminoketone (X).
  • Amidines (XI) are known from literature or commercially available. In cases in which R 2 resem- Ibes a carbo- Oder a heterocycle further, literature known, manipulations are possible: For ex- ample oxazoles can selectively be halogenated following published procedures (e.g. Bioorganic & Medicinal Chemistry, 2010, 18, 4821 ).
  • the aminoketones (II) are prepared from the corresponding ketones (IV) with N,N-Dimethylfor- mamide dimethyl acetal (CAS 4637-24-5; DMFDMA).
  • the reaction is usually carried out at tem- peratures from -100° C to the boiling point of the reaction mixture, preferably from 20°C to 160° C, particularly from 50°C to 130°C.
  • the reaction can optionally be catalyzed by an acid.
  • the reaction may be carried out in substance or in an organic solvent. Suitable solvents are those capable of dissolving the ketones (IV) and DMFDMA (CAS 4637-24-5) at least partly, preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, esters such as ethyl acetate and bu- tyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP; preferably DMFDMA is used as sol- vent. It is also possible to use mixtures of the solvents mentioned.
  • aromatic hydrocarbons such as benzene, chlorobenzen
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2SO4); organic acids p- toluenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI. Most preferred is no use of acid.
  • the acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • VI carbonyl-electrophile
  • the reaction is carried out at temperatures of from -100° C to the boiling point of the reaction mixture, prefera- bly from -80° C to 60° C, particularly from -80° C to 20° C, in an inert solvent.
  • Suitable solvents are those capable of dissolving the Grignard-reagent (V) and the carbonyl- electrophile (VI) at least partly and preferably fully under reaction conditions.
  • suita- ble solvents are aliphatic aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, an- isole and THF, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as tert-butyl methyl ether or THF. It is also possible to use mixtures of
  • the Grignard-reagents (V) are either commercially available or can be prepared from the cor- responding halides by known methods.
  • the carbonyl electrophiles (VI) are either commercially available or can be prepared from the corresponding carboxylic acid or carboxylic ester by known methods.
  • Ketones (IV) can as well be prepared from morpholinonitriles (VII) as described in the literature (European Journal of Organic Chemistry 2013, 36, 8083).
  • the morpholinonitriles (VII) are prepared from morpholinonitriles (VIII) and benzylhalides (IX) in the presence of a base.
  • the reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -80°C to 60°C, particularly from -50°C to 20°C, in an inert organic solvent in the presence of a base.
  • Suitable solvents are those capable of dissolving the morpholinonitriles (VIII) and the benzyl- halides (IX) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, esters such as ethyl acetate and bu- tyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO, and NMP
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCFh, NaOC2H 5 , KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alka
  • ter- tiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular pref- erence is given to NaH, LHMDS and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the halide (IX), based on the morpholinonitrile (VIII).
  • Morpholinonitriles (VIII) are prepared from the corresponding aldehydes (X) as described in the literature (WO 2009/013462). Aldehydes (X) are commercially available.
  • the pyrimidines of formula (XI) can be obtained from pyrimidines of formula (XII) by known methods e.g using PPhs and Iodine (analogous to Davies, James R. etai Journal of Organic Chemistry, 70(15), 5840-5851 , 2005 or Just-Baringo, Xavier etal. Angewandte Chemie, Inter- national Edition, 52(30), 7818-7821 , 2013).
  • the pyrimidines of formula (XII) can be obtained from pyrimidines of formula (XIII) by reaction with the carboxylic acides (XIV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloal- kenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
  • the reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an inert or- ganic solvent.
  • Carboxylic acids RCOOH are commercially available. Carboxylic acids are activated using ac- tivating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethyla- mino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1 H- benzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluronium-hexafluorophosphate (HBTU), ethyl-3-(3-dimethyl- aminopropyl)carbodiimid (EDC).
  • HATU 1-[Bis(dimethyla- mino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate
  • HBTU 2-(1 H- benzotriazol-1-yl)-1 ,1 ,3,3-t
  • the carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chloride.
  • Carbonylimidazoles such as 1 ,T-Carbon- yldiimidazol (CDI) may also be used as activating reagent under neutral conditions.
  • Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Suitable bases include inorganic and organic bases, e.g.
  • tertiary amines such as trimethyla- mine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy-hack amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DIPEA.
  • TMA trimethyla- mine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • N-methylpiperidine pyri dine
  • substituted pyridines such as collidine, lutidine and 4-dimethylaminpyridine
  • DBU Diazabicycloundecen
  • the bases are generally employed in excess amounts; however, they can also be employed in equal amounts as the pyrimidine.
  • the pyrimidines of formula (XIII) can be obtained from pyrimidines of formula (XV), wherein R is hydroxycarbonyl, alkoxycarbonyl, (HO) 2 (0)R, (alkoxy) 2 (0)P, alkyl sulfonyl or alkylcarbonyl, by reaction with with an acid HA
  • the reaction of the pyrimidine (XV) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an organic solvent using water as a cosolvent.
  • the starting materials are reacted with one another in equimolar amounts or using an excess of one reagent. Preference is given to us- ing an excess of acid HA.
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2SO4); organic acids p- toluenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; most preferably HCI.
  • Suitable solvents include dioxane and tetrahydrofuran (THF), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and N,N- dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered solvents are alcohols. It is also possi- ble to use mixtures of the solvents mentioned.
  • the pyrimidines of formula (XV) can be obtained by process C.
  • the pyrimidines of formula (XV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or a carboxylic ester, can be ob- tained by reacting respective pyrimidines of formula (XVI) with isocyanides (XVII):
  • the reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -78°C to 25°C, particularly from -78°C to 0°C, in an inert or- ganic solvent using a base.
  • Suitable solvents are those capable of dissolving the pyrimidine (XVI) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH
  • alkali metal amides such as LHMDS and LDA
  • organometallic compounds in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the isocyanide (XVII) based on the pyrimidine (XVI).
  • the pyrimidines of formula (XVI) can be obtained by reacting respective pyrimidines of formula (XVIII) with boronic acids/esters of formula (XIX):
  • reaction of pyrimidines (XVIII) with boronic acids/esters (XIX) is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XVIII) with the boronic acids/esters (XIX) in an organic solvent with or without water as co-solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XVIII) and the boronic acids (XIX) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as LhO, Na 2 0, K 2 O, MgO, and CaO, Fe 2 0 3 , Ag 2 0; alkali metal and alkaline earth metal carbonates such as U 2 CO 3 , Na 2 C0 3 , K 2 CO 3 , CS2CO3, MgC03, and CaC03, as well as alkali metal bicarbonates such as UHCO3, NaHCOs, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate,
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hy- droxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH)3 and alkali metal or alkaline earth metal carbonates such as L12CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03 and alkaline earth metal phosphates such as K3PO4; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • alkali metal and alkaline earth metal acetates such as sodium acetate.
  • Especially preferred bases are inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkaline earth metal phosphates such as K 3 PO 4 .
  • inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkaline earth metal phosphates such as K 3 PO 4 .
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably at from 1 to 10 equivalents based on the pyrimidine (XVIII), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (XVIII), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XVIII).
  • the reaction of the pyrimidines (XVIII) with the boronic acids/esters (XIX) is carried out in the presence of a catalyst.
  • suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphos- phine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphos- phine or BINAP (2,2'-Bis(diphenylphospino)-1 ,T-binaphthyl).
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyrimidine (XVIII).
  • halopyrimidines are known from the literature (e.g. WO 2011 154327), are commer- cially available or can be prepared by known procedures.
  • boronic acids/esters (XIX) required for the preparation of pyrimidines of formula (XVI) are commercially available, known from literature or can easily be prepared analogously to pub- lished procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
  • the pyrimidines of formula (XV) can also be obtained by reacting respective pyrimidine alde- hydes (XX) with tosyl isocyanides (XXI), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
  • the reaction of the pyrimidine (XX) with the tosyl isocyanides (XXI) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 0°C to the boiling point of the reaction mixture, particularly from 25°C to 65°C, in an inert organic solvent using a base.
  • Suitable sol- vents are those capable of dissolving the pyrimidine (XX) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), di- methylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered sol- vents are methanol and ethanol.
  • Suitable bases are alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCFh), sodium ethoxide (NaOC 2 H 5 ), potassium ethoxide (KOC 2 H 5 ), potassium tert-butoxide ( BuOK), potassium tert-pentoxide and dimethoxymagnesium.
  • metal carbonates such as caesium carbonate and potassium carbonate.
  • organic bases e.g.
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as col- lidine, lutidine and 4-dimethylaminpyridine
  • bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU).
  • DBU Diazabicycloundecen
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the tosyl isocyanide (XXI), based on the pyrimidine (XX).
  • the pyrimidines of formula (XX) can be obtained by oxidizing respective pyrimidine alcohols of formula (XXII).
  • the oxidation of pyrimidines (XXII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 100 °C, particularly at from 0 °C to 75 °C, in an in- ert organic solvent.
  • reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XXII) in an organic solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XXII) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH 2 CI 2 , CHCI 3 , CCH 2 CICH 2 CI or CCU, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as CH 2 CI 2 , CHCI 3 , CCH 2 CICH 2 CI or CCU
  • ethers such as diethyl ether, diisopropyl
  • Preferred solvents are halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCU, and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, N,N'-dimethyhpropyl- ene urea (DMPU), DMSO and NMP. More preferred solvents halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCU. It is also possible to use mixtures of the solvents men- tioned.
  • oxidizing agents for the synthesis of pyrimidines are metal oxides such as M h q2, KM h q4, Cr03 or PCC, and non-metal oxides such as NaCIO, Nal04 or pyridine/S03- complex.
  • methods like the Swern oxidation or the TEMPO oxidation known to a per- son skilled in the art can be used to obtain pyrimidines of formula (XX).
  • Preferred agents include M h q2, KM h q4 and PCC, more preferred Mn02.
  • the oxidizing agent is used preferably from 1 to 50 equivalents based on the pyrimidine (XXII), more preferably at from 1.0 to 20.0 equivalents based on the pyrimidine (XXII), most preferably from 1.0 to 10.0 equivalents based on the pyrimidine (XXII).
  • the pyrimidines of formula (XXII) can be obtained by reacting respective pyrimidines of for- mula (XVI) with a reducing agent such as LAH or DIBAIH.
  • the reduction of pyrimidines (XVI) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 60 °C, particularly at from 0 °C °C to 25 °C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, 0-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly diethyl ether, dioxane and THF. It is also possible to use mixtures of the solvents mentioned.
  • Examples of reducing agents for pyrimidines include LAH, DIBALH, LiBFU or lithium tri- ethylborohydride.
  • Preferred agents include LAH and DIBALH.
  • the hydride-source is used preferably from 1 to 10 equivalents based on the pyrimidine (XVI), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (XVI), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XVI).
  • the pyrimidines of formula (XXIII) can be obtained from pyrimidines of formula (XXIV) by known methods e.g using actic acid anhydride/ concentrated sulfuric acid (e.g Godfrey, Alexan- der G. etal. Journal of Organic Chemistry, 68(7), 2623-2632, 2003) or using burgess reagent (e.g. Brain, C. T etal. Synlett, 1642-1644, 1999).
  • actic acid anhydride/ concentrated sulfuric acid e.g Godfrey, Alexan- der G. etal. Journal of Organic Chemistry, 68(7), 2623-2632, 2003
  • burgess reagent e.g. Brain, C. T etal. Synlett, 1642-1644, 1999.
  • the pyrimidines of formula (XXIV) can be obtained from carboxylic acids of formula (XXV) by reaction with amino ketones of formula (XXVI), wherein R substituents of the amino ketones are indenpendently of each alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloal- kenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
  • reaction of the carbox- ylic acids (XXV) with amino ketones (XXVI, commercially available), is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an inert organic solvent.
  • Carboxylic acids are activated using activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1 H-benzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluronium-hex- afluorophosphate (HBTU), ethyl-3-(3-dimethylaminopropyl)carbodiimid (EDC).
  • activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1 H-benzotriazol-1-yl)-1 ,1 ,3,3-te
  • the carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chlo- ride.
  • Carbonylimidazoles such as 1 ,T-Carbonyldiimidazol (CDI) may also be used as activating reagent under neutral conditions.
  • Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), di- methylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Suitable bases include inorganic and organic bases, e.g.
  • tertiary amines such as trimethyla- mine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy-hack amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DIPEA.
  • TMA trimethyla- mine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • N-methylpiperidine pyri dine
  • substituted pyridines such as collidine, lutidine and 4-dimethylaminpyridine
  • DBU Diazabicycloundecen
  • the bases are generally employed in excess amounts; however, they can also be employed ain equal amounts as the pyrimidine.
  • the reaction is usually carried out at from 0 °C to the boil- ing point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) in an organic solvent with or without water as co-solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XXVII) and the boronic acids (XXVIII) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC,
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as LhO, Na 2 0, K 2 O, MgO, and CaO, Fe 2 0 3 , Ag 2 0; alkali metal and alkaline earth metal carbonates such as U 2 CO 3 , Na 2 C0 3 , K 2 CO 3 ,
  • alkali metal bicarbonates such as UHCO3, NaHCOs, KHCO3
  • alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2
  • alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hy- droxides, and other metal hydroxides, such as LiOH, NaOH, KOH , Mg(OH)2, Ca(OH)2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as U2CO 3 , Na 2 C0 3 , K2CO 3 , CS2CO3, MgC03, and CaC03 and alkaline earth metal phosphates such as K3PO4; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • metal hydroxides such as LiOH, NaOH, KOH , Mg(OH)2, Ca(OH)2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as U2CO 3 , Na 2 C0 3 , K2CO 3 , CS2CO3, MgC03, and CaC03 and alkaline earth metal phosphates such as K3PO4; alkali
  • Especially preferred bases are inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH)3 and alkaline earth metal phosphates such as K 3 PO 4 .
  • inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH)3 and alkaline earth metal phosphates such as K 3 PO 4 .
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably at from 1 to 10 equivalents based on the pyrimidine (XXVII), more preferably at from 1 .0 to 5.0 equivalents based on the pyrimidine (XXVII), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XXVII).
  • a catalyst examples include e.g., palladium based cata- lysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenyl- phosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphe- nylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,T-binaphthyl).
  • phosphines like, e.g., P(o-tolyl)3, triphe- nylphosphine or BINAP (2,2'-B
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyrimidine (XXVII).
  • boronic acids/esters (XXVIII) required for the preparation of pyrimidines of formula (XI) are commercially available, known from literature or can easily be prepared analogously to pub- lished procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
  • the reaction of the pyrimidine with the nucleohpile is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particu- larly from 20°C to 80°C, in an inert organic solvent using a base.
  • Suitable solvents are those ca- pable of dissolving the pyrimidine (XXVII) and the nucleophile at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH 3 , NaOC2H 5 , KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium alkali metal and alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03, as well as al- kali metal bicarbonates such as UHCO3, NaHC0 3 , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca 3 (P0 4 ) 2 ; al
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, LHMDS, LDA, NaOCH and K2CO3.
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the nucleophile based on the pyrimidine (XXVII).
  • the pyrimidines of formula (XI) with R’ 1 -hydroxy-alkyl, 1 -hydroxy-aryl, 1-hydroxy-het- eroaryl, 1-hydroxy-heterocyclyl, 1 -hydroxy-cycloalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcar- bonyl, alkinylcarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carbocyclylcar- bonyl and related compounds can also be obtained by reacting respective pyrimidines of for- mula (XV) with a base and an electrophile.
  • the reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -78°C to 25°C, particularly from -78°C to 0°C, in an inert or- ganic solvent using a base.
  • Suitable solvents are those capable of dissolving the pyrimidine (XV) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH
  • alkali metal amides such as LHMDS and LDA
  • organometallic compounds in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
  • Suitable electrophiles are for example aldehydes and acid anhydrides, which are commercially available.
  • the starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the electrophile based on the pyrimidine (XV).
  • reaction mixtures are worked up in a customary manner, e.g. by mixing with water, sepa- ration of the phases and, if appropriate, chromatographic purification of the crude product.
  • Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately el- evated temperature.
  • purification can also be carried out by recrystallization or digestion.
  • the present invention also provides agrochemical compositions comprising at least one pyrimidine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
  • the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyrimidine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat.
  • Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • pyrimidine compounds of formula (I) as described herein are capable of forming geomet- rical isomers, e.g. E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
  • the pyrimidine compounds of formula (I) as described herein have one or more centres of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions ac- cording to the invention.
  • the pyrimidine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, more preferably a carboxylic group or a sulphonic group, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cati ons and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C 4 -alkyl, HO-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 - alkyl, HO-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C 4 -al- kanoic acids, preferably formate, acetate, propionate and butyrate.
  • Pyrimidine compounds of formula (I) as described herein having an acidic functionality can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with the cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C 6 -al- kylamides or arylamides, as esters, e.g.
  • allyl esters propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, e.g. as Ci-Cio-alkylthio esters.
  • Preferred mono- and di-Ci-C 6 -alkylamides are the CH 3 and the dimethyl- amides.
  • Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
  • Preferred alkyl es- ters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Preferred Ci-C 4 -alkoxy- Ci-C 4 -alkyl esters are the straight-chain or branched Ci-C 4 -alkoxy ethyl esters, e.g.
  • the organic moieties mentioned in the definition of the variables of the compound of formula I are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case F, Cl, Br, or I.
  • All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denot- ing in each case the possible number of carbon atoms in the group.
  • Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C 6 -alkyl Ci-C 4 -alkyl as mentioned above, and also, e.g., n-pentyl, 1 -methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,
  • Ci-C 4 -haloalkyl Ci-C 4 -alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodi- fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di- chloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1 , 1 -diflu
  • Ci-C 6 -haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-io- dohexyl, and dodecafluorohexyl;
  • C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-halocycloalkyl C3-C6-cycloalkyl as mentioned above which is partially or fully sub- stituted with fluorine, chlorine, bromine and/or iodine, e.g., 1 -fluorocyclopropyl;
  • C3-C6-alkenyl e.g. 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-bu- tenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1 - pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl--
  • C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1 -yl, 3- chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1 -yl, 2,3,3-trichloro-2-en- 1 -yl, 2,3-dichlorobut-2-en-1 -yl, 2-bromoprop-2-en-1 -yl, 3-bromoprop-2-en-1 -yl, 2,3-dibromoprop- 2-en-1 -yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1 -yl, or 2,3-dibromobut-2-en-1 -yl
  • C3-C6-alkynyl e.g. 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl- 4-pent
  • C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
  • C3-C6-haloalkynyl a C3-C6-alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1 ,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bro- moprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1 , 1 -difluoro- but-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-
  • Ci-C 4 -alkoxy e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy,
  • Ci-C 6 -alkoxy Ci-C 4 -alkoxy as mentioned above, and also, e.g., pentoxy, 1 -methylbut- oxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trime- thylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy, and 1
  • Ci-C 4 -haloalkoxy a Ci-C 4 -alkoxy group as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluorometh- oxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chlor
  • Ci-C 6 -haloalkoxy a Ci-C 4 -haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
  • Ci -C 4 -a I ky Ith i o e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 - methylpropylthio, 2-methylpropylthio, and 1 , 1 -dimethylethylthio;
  • Ci-C 6 -alkylthio Ci-C 4 -alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hex- ylthio, 1 , 1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethy
  • (Ci-C4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1-dimethylethylamino;
  • (Ci-C 6 -alkyl)amino (Ci-C4-alkylamino) as mentioned above, and also, e.g., pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethyl- propylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethylpropylamino, 1-methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1-dimethylbutyla- mino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1-ethylbutyla
  • di(Ci-C4-alkyl)amino e.g. N,N-dimethylamino, N,N-diethylamino, N,N-di(1-meth- ylethyl)amino, N,N-dipropylamino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2- methylpropyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-prop- ylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpro- pyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,1
  • di(Ci-C 6 -alkyl)amino di(Ci-C4-alkyl)amino as mentioned above, and also, e.g., N-me- thyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-me- thyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1-dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylp
  • Ci-C 6 -alkylsulfonyl (Ci-C 6 -alkyl-S(0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1-di- methylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfonyl
  • C3-C6-cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-cycloalkenyl 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1- cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadi- enyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 2,5-cyclohexadienyl;
  • bicyclic ring a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and inde- pendent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole
  • heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
  • 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
  • heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an ox ygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
  • pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
  • thiazol-2-yl thiazol-4-yl, thiazol-5-yl
  • oxadia- zolyl e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl,
  • thiadiazolyl e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl
  • triazolyl e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl
  • 1 -tetrazolyl 6-membered aromatic rings like pyridyl (e.g.
  • pyridine-2 -yl pyridine-3-yl, pyridine-4-yl
  • pyrazinyl e.g. pyridazin-3-yl, pyridazin-4-yl
  • pyrimidinyl e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl
  • pyrazin-2-yl triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl
  • substituted if not specified otherwise refers to substituted with 1 , 2, or up to maxi- mum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not men- tioned otherwise.
  • acidic functionality if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
  • cyclic groups comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
  • pyrimidine compounds of formula (I) are suitable as herbicides.
  • R 1 is not fluoromethyl, difluoromethyl, tri- fluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, 1 ,1 ,2,2,-tetrafluoroethyl, 1 -trifluoromethyl-1 ,2,2,2-tetrafluoro- ethyl and undecafluoropentyl;
  • R 1 is not 1 ,1 ,2,2,-tetrafluoroethyl
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocycloalkenyl;
  • R x is Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocy- cloalkenyl;
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocy- cloalkyl;
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C 3 -C 6 -cycloalkyl;
  • R x is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R x is H, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl
  • R x is H, halogen, Ci-C 6 -alkyl
  • R x is H, or Ci-C 6 -alkyl
  • R x is H or halogen
  • R x is H
  • R x is Ci-C6-alkyl e.g. CH 3 , C 2 H 5 , i-C 3 H 7 , n-C 4 H 9 , and 1-C 4 H 9 ;
  • R x is C 3 -C 6 -cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C 3 H 5 , C-C 4 H 7 , and C-C 5 H 9 ;
  • R x is halogen
  • R x is Ci-C6-haloalkyl e.g. CHF 2 , CHF 2 , and CF 3 ;
  • R x is C 3 -C 6 -halocycloalkyl
  • R x is H, CH3, C2H5, F, i-C3H 7 , CHF2, CHF2, or c-C3H 5 ;
  • R ⁇ is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocycloalkenyl;
  • R ⁇ is H, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halo- cycloalkenyl;
  • R ⁇ is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocy- cloalkyl;
  • R ⁇ is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C 3 -C 6 -cycloalkyl;
  • R ⁇ is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R ⁇ is H, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl
  • R ⁇ is H, halogen, Ci-C 6 -alkyl
  • R ⁇ is H, or Ci-C 6 -alkyl
  • R y is H or halogen
  • R y is H
  • R ⁇ is Ci-C 6 -alkyl e.g. CH 3 , C 2 H 5 , i-C 3 H 7 , n-C 4 Hg, and 1-C 4 H 9 ; also more preferred R y is C 3 -C 6 -cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C 3 H 5 , C-C 4 H 7 , and C-C 5 H 9 ;
  • R y is halogen
  • R y is Ci-C 6 -haloalkyl e.g. CHF2, CHF2, and CF3;
  • R y is C3-C6-halocycloalkyl
  • R y is H, CH3, C2H5, F, 1-C3H7 , CHF2, CHF2, or c-C3H 5 ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 R e ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, R e ; also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- membered saturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 is CF2CH 3 , 1-F-isopropyl or 1-F-cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -43 as shown below, wherein W, X, and Y denotes R 20 which independently of each other are identical or different;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C 6 -alkylcarbonyl, C2-C6-alkenylcar- bonyl, C2-C6-alkinylcarbonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl, di(Ci-C 6 -alkyl)amino- sulfonyl, or Ci-C 6 -alkylaminosulfonyl;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 , or R 2 -22; also preferred R 2 is R 2 -5, R 2 -6, or R 2 -7;
  • R 2 is R 2 -20, R 2 -21 , or R 2 -22;
  • R 2 is R 2 -5, R 2 -7 or R 2 -20;
  • R 2 is R 2 -5;
  • R 2 is R 2 -6;
  • R 2 is R 2 -7;
  • R 2 is R 2 -20; preferred X is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkylsulfinyl, Ci-C 6 - alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (HO) 2 (0)P, (Ci-C 6 -alkoxy
  • cyclic groups of X are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X are unsubstituted or substituted with R d ;
  • X is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci- C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkyl- sulfinyl, Ci-C 6 -alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of X are unsubstituted or substituted with R c ; and
  • acyclic aliphatic groups of X are unsubstituted or substituted with R d ;
  • X is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with R c ;
  • X is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy- (Ci-C 4 -alkoxy) n , OR b , SH, or SR b , wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with R d ;
  • X is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(Ci-C 4 - alkoxy)n, Ci-C6-haloalkoxy;
  • X is H
  • X is halogen
  • Ci-C 6 -alkyl is Ci-C 6 -alkyl
  • Ci-C 6 -haloalkyl is Ci-C 6 -haloalkyl
  • Ci-C 6 -haloalkoxy is Ci-C 6 -haloalkoxy
  • Ci-C 6 -alkyl preferably CH 3 , C 2 H 5 , n-propyl, CH(CHs) 2 , n-butyl, isobutyl;
  • X is H, Ci-C4-alkyl, Ci-C 2 -fluoroalkyl, Ci-C4-alkoxy, or Ci-C4-alkylthio;
  • especially preferred X is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH 3 , or SCH 3 ;
  • X is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, OCH 3 , or SCH 3 ;
  • X is H, halogen, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • X is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • X is H, CH 3 , C 2 H 5 , F, Cl, Br, or I;
  • X is H, CH 3 , or C 2 H 5 ;
  • X is H
  • X is CH 3 ;
  • X is C 2 H 5 ;
  • Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkylsulfinyl, Ci-C 6 - alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (HO) 2 (0)P, (Ci-C 6 -alkoxy) 2 (0)P, phenyl,
  • cyclic groups of Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of Y are unsubstituted or substituted with R d ; particularly preferred Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci- C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkyl- sulfinyl, Ci-C 6 -alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of Y are unsubstituted or substituted with R c ; and
  • acyclic aliphatic groups of Y are unsubstituted or substituted with R d ;
  • Y is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with R c ;
  • Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy- (Ci-C 4 -alkoxy) n , OR b , SH, or SR b , wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with R d ;
  • Y is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(C-i-C 4 - alkoxy)n, Ci-C6-haloalkoxy;
  • Y is H
  • Y is halogen
  • Y is Ci-C 6 -alkyl
  • Y is Ci-C 6 -haloalkyl
  • Y is Ci-C 6 -haloalkoxy
  • Y is Ci-C 6 -alkyl, preferably CH 3 , C 2 H 5 , n-propyl, CH(CHs) 2 , n-butyl, isobutyl;
  • Y is H, Ci-C 4 -alkyl, Ci-C 2 -fluoroalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -alkylthio;
  • Y is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH 3 , or SCH 3 ;
  • Y is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, OCH 3 , or SCH 3 ;
  • Y is H, halogen, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • Y is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • Y is H, CH 3 , C 2 H 5 , F, Cl, Br, or I;
  • Y is H, CH 3 , or C 2 H 5 ;
  • Y is H
  • Y is CH 3 ;
  • Y is C 2 H 5 ;
  • W is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkylsulfinyl, Ci-C 6 - alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (H0) 2 (0)P, (Ci-C 6 -alkoxy) 2 (0)P, phenyl,
  • cyclic groups of X are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X are unsubstituted or substituted with R d ;
  • W is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(Ci- C 4 -alkoxy) n , OR b , SH, SR b , C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, NR 4 R 5 , CONR 4 R 5 , COR f , Ci-C 6 -alkyl- sulfinyl, Ci-C 6 -alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of X are unsubstituted or substituted with R c ; and
  • acyclic aliphatic groups of X are unsubstituted or substituted with R d ;
  • W is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with R c ; also particularly preferred W is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy- (Ci-C4-alkoxy) n , OR b , SH, or SR b , wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with R d ;
  • W is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(C-i-C 4 - alkoxy)n, Ci-C6-haloalkoxy;
  • W is H
  • W is halogen
  • W is Ci-C 6 -alkyl
  • W is Ci-C 6 -haloalkyl
  • W is Ci-C 6 -haloalkoxy
  • W is Ci-C6-alkyl, preferably CH 3 , C 2 H 5 , n-propyl, CH(CHs) 2 , n-butyl, isobutyl;
  • W is H, Ci-C 4 -alkyl, Ci-C2-fluoroalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -alkylthio;
  • W is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH 3 ;
  • W is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, OCH 3 , or SCH 3 ;
  • W is H, halogen, CH 3 , C 2 H 5 , OH, or OCHs;
  • W is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • W is H, CH 3 , C 2 H 5 , F, Cl, Br, or I;
  • W is H, CH 3 , or C 2 H 5 ;
  • W is H
  • W is CH 3 ;
  • W is C 2 H 5 ;
  • Q is H, Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C6-alkylcarbonyl, C 2 -C 6 -alkenyl- carbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, or Ci-C6-alkylaminosulfonyl;
  • Q is H, Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, or Ci-C6-alkylcarbonyl;
  • Q is H, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6- alkyl, or Ci-C6-alkylaminosulfonyl;
  • Q is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, or t-butyl;
  • R b is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C6-ami- nocarbonyl, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl;
  • R b is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
  • R b is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkyl, 5- or 6-membered het- eroaryl, or 3- to 6-membered heterocyclyl;
  • R c is halogen, CN, OH, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, or NH 2 ;
  • R c is Ci-C 6 -alkyl or Ci-C 6 -alkoxy
  • R c is Ci-C 6 -alkyl
  • R d is CN, OH, halogen, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, Ci-C 6 -haloalkoxy, NH 2 , phenyl-Ci-C 6 -alkyl, phenyl, 5- or 6-membered het- eroaryl, or 3- to 6-membered heterocyclyl, or phenylthio;
  • R d is halogen, Ci-C 6 -alkoxy, or phenylthio; most preffered R d is halogen or Ci-C 6 -alkoxy;
  • R e is halogen, OH, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R e is halogen, CN, OH, Ci-C 6 -alkoxy or Ci-C 6 -alkyl;
  • R e is OH or Ci-C 6 -alkoxy
  • R f is H, halogen, CN, OH, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy;
  • R f is OH, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy
  • R f is OH or Ci-C 6 -alkoxy.
  • R 2 is selected from formulae R 2 -1 to R 2 -43;
  • Q is H, Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, or Ci-C 6 -alkylaminosul- fonyl;
  • X , Y and W independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hy- droxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C3- C 6 -cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy, Ci-C 6 -alkoxy-(Ci-C 4 - alkoxy)n, SH, NH2, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)(Ci-C6- alkoxy)amino, Ci-C 6 -alkylthio, Ci-
  • cyclic groups of X, Y, and W are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, Y, and W are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, Ci-C 6 -haloalkoxy or phenyl, preferably H or Ci-C 6 -alkyl, more prefera- bly H, CH3, C2H5, or n-propyl;
  • Y is H, C2-C6-alkenyl, C2-C6-alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6- alkenyloxy, C3-C6-alkinyloxy, Ci-C6-alkoxy-(Ci-C4-alkoxy) n , SH, NH2, Ci-C6-alkylamino, di(Ci-C 6 -alkyl)amino, (Ci-C 6 -alkyl)(Ci-C 6 -alkoxy)amino, Ci-C 6 -alkylthio, Ci-C 6 -alkylthio- Ci-C 6 -alkyl, Ci-C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -al-
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X is H, Ci-C 6 -alkyl, hydroxycarbonyl, or phenyl, preferably H or Ci-C 6 -alkyl, more prefera- bly H, CH3, C2H5, or n-propyl;
  • Y is H, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n ,
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio.
  • Preffered R 4 and R 5 are independently from each other selected from hydrogen, OH, OI-O Q - alkyl, NH 2 , Ci-C 6 -alkylcarbonyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -haloalkylsulfonyl, Ci-C 6 -alkoxycar- bonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroaryl- sulfonyl, 3- or 6-membered heterocyclylsulfonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6-cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycar- bonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl
  • R 4 and R 5 are independently from each other selected from hydrogen, OH, Ci- C 6 -alkyl, NH 2 , Ci-C 6 -alkylcarbonyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -haloalkylsulfonyl, Ci-C 6 -alkoxycar- bonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, Ci-C 6 -alkylaminocarbonyl, and di(Ci-C 6 -al- kyl)aminocarbonyl;
  • R 4 and R 5 are independently from each other selected from OH, Ci-C 6 -alkylcar- bonyl, Ci-C 6 -alkylsulfonyl, and Ci-C 6 -haloalkylsulfonyl.
  • R 3 are selected from halogen, CN, N0 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, and C3-C6-cycloalkyl;
  • R 3 are selected from halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci-C 6 -alkoxy; particularly preferred R 3 are selected from halogen, Ci-C 6 -alkyl, and Ci-C 6 -haloalkyl;
  • R 3 are selected from halogen, and Ci-C 6 -alkyl
  • R 3 is halogen, CH3, or CF3;
  • R 3 is halogen
  • R 3 are selected from Cl, Br, and F;
  • R 3 is Br or I
  • R 3 is Br or Cl
  • R 3 is Br
  • R 3 is Cl
  • R 3 is F.
  • Preferred Z is phenyl or 5- or 6-membered heteroaryl ring
  • Z is phenyl or 9- or 10-membered partially or fully unsaturated bicyclic ring con- taining 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
  • Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered partially or fully unsaturated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; more preferred Z is phenyl substituted independently of their position with 0, 1 , 2, 3, or 4 R 3 ; most preferred Z is phenyl which is substituted at ortho position to the bond attached to pyrimi- dine ring with at least one R 3 , and which phenyl ring is further substituted with 0, 1 , 2, or 3 R 3 ; particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 ,
  • R 3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, preferrably 0 or 1 ; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 -A,
  • R 3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 -B,
  • R 3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and
  • # denotes the point of attachment to the pyrimidine ring
  • R 3 is halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C 1 - C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkylthio, C 1 - C 6 -hal
  • R 3b and R 3c each independently is H, halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloal- kynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 - C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbon
  • # denotes the point of attachment to the pyrimidine ring
  • Z is 5- or 6-membered heteroaryl ring
  • Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine; particularly preferred Z is pyrimidine or pyridine;
  • especially preferred Z is pyridine
  • Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole; particularly preferred Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thio phene, furan, or pyrrole;
  • Z is thiophene, furan, or pyrrole
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups A to G,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • n 0 or 1 ;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups A1 to G1 ,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R 3b is H, halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from A, B, C, and D;
  • Z[i.e. the group“Z-(R 3 ) m ”] is A or C;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from E, F, and G;
  • Z i.e. the group“Z-(R 3 ) m ”] is E or G;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from A1 , B1 , C1 , and D1 ; most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is A1 or C1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from E1 , F 1 , and G1 ; also most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is E1 or G1 ;
  • Z is 9- or 10-membered partially or fully unsaturated bicyclic ring contain- ing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
  • Z is 9- or 10-membered partially or fully unsaturated bicyclic ring, wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 het- eroatoms selected from O or N;
  • Z is 9 membered bicyclic ring
  • Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsatu- rated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N; also more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered car- bocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 heteroatoms se- lected from O or N;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is 10 membered bicyclic ring
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N;
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms; most particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups H to V,
  • Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
  • R 3 same or differently are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci- C 6 -alkoxy;
  • n 0, 1 or 2;
  • R 4 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from groups H to V,
  • Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
  • R 3 same or differently are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci- C 6 -alkoxy;
  • n 0, 1 or 2;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups H1 to V1 ,
  • Y 1 is 5- or 6-membered fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • R 3 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R 3b and R 3c each independently is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C1-C6- alkoxy ;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Preferred Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • Y 1 is phenyl
  • Y 1 is 5-membered partially or fully unsaturated carbocycle compris- ing 1 , or 2 heteroatoms selected from O, N, and S; more preferred Y 1 is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3-di- hydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole ; more preferably heteroatoms are selected from O and S, e.g.
  • Y 1 is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole,
  • heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
  • Y 1 is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms
  • Y 1 is 6-membered partially or fully unsaturated carbocycle compris- ing 0, 1 , or 2 heteroatoms selected from O, N, and S;
  • more preferred Y 1 is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y 1 is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms N;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H, I, J, K, L, M, N, O, P, Q, or R; most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is H, L, or M;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H or W 1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is S, T, U, or V;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 , 11 , J1 , K1 , L1 , M1 , N1 , 01 ,
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 , L1 , or M1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H 1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 or W1 a;
  • Z[i.e. the group“Z-(R 3 ) m ”] is S1 , T1 , U1 , or V1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H 1 , 11 , K1 , L1 and R1 ;
  • m 0, 1 , 2, or 3;
  • m is 0, 1 , or 2;
  • m 0;
  • m 1 ;
  • n 0, 1 , 2, or 3;
  • n 0, 1 , or 2;
  • n 0;
  • n 1 ;
  • n 2
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl , or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci- C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2- C 6 -alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C6-alkoxy-(Ci-C4-alkoxy)n, SH, NH2, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, (O-I-OQ- alkyl)(Ci-C 6 -alkoxy)amino, Ci-C 6 -alkylthio, Ci-C 6 -alky
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, O-I-OQ- alkyl, or Ci-C 6 -haloalkyl.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, SH, Ci-C 6 -alkylamino, di(Ci-C 6 -alkyl)amino, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, O C 6 -alkylsulfonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, ami- nocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)amino
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, O-I-OQ- alkyl, or Ci-C 6 -haloalkyl.
  • R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, O-I-OQ- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, SH, Ci-C 6 -alkylamino, di(Ci-C 6 -alkyl)amino, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, Ci- C 6 -alkylsulfonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, ami- nocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)a
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, C1-C6- alkyl, or Ci-C 6 -haloalkyl.
  • R 1 is 1-F-cyclopropyl
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X and Y independently are selected from H, Ci-C 6 -alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, NH2- aminocarbonyl, hydroxya mi nocarbonyl, C3-C6-cycloalkylaminocarbonyl, C1-C6- alkylcarbonylamino,
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, O-I-OQ- alkyl, or Ci-C 6 -haloalkyl.
  • R 1 is 1 -F-isopropyl
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • X and Y independently are selected from H, Ci-C 6 -alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci- C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, O-I-OQ- alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C 3 -C 6 -cycloalkylaminocarbonyl, C1-C6- alkylcarbon
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, C1-C6- alkyl, or Ci-C 6 -haloalkyl.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • Z i.e. the group“Z-(R 3 ) m ”
  • Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • Z i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci- C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycar- bonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2, or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci- C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycar- bonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2, or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • Z i.e. the group“Z-(R 3 ) m ”
  • Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H or Ci-C 6 -alkyl, preferably CH 3 or C 2 H 5 ;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci- C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycar- bonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 2 is Z[i.e. the group“Z-(R 3 ) m ”] is W 1 , which corresponds to formula (I.C.1 ), and their use as herbicide,
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 or R 2 -22, R 2 is more preferably R 2 -5, R 2 -7, or R 2 -20;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, O-I-OQ- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)a
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or Ci-C6-alkylthio;
  • R 3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H or Ci-C 6 -alkyl, preferably CH 3 or C 2 H 5 ;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C 3 -C 6 -cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C 1 -C 6 - alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 - alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH 2 , Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(C
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )C oCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CON
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)amin
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 Co CH, CH(CH 3 )CoCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH 2
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci- C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycar- bonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2 or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )C oCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H 5
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)amin
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2, or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio; more preferably, when m is 2, R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )C oCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H 5
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)amin
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2, or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )C oCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CON
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)amin
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 0, 1 , 2, or 3;
  • R c is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, or Ci-C 6 -alkoxy;
  • R d is C2-C6-alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, C(CH 3 ) 3 , OH, OCH 3 , SH, SCH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CONH2, CONHCH3, CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), CoCH, CH2CHCH2, CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )C oCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCH3, COOC 2 H 5 , CON
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is CF 2 CH 3 , 1-F-isopropyl, or 1-F-cyclopropyl;
  • R 2 is R 2 -5, R 2 -6, R 2 -7, R 2 -20, R 2 -21 , or R 2 -22; wherein X and Y independently are selected from H, CH3, and C2H5;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from 2-CI-C6H4, 2-Br-C6H4, 2-CH3-C6H4, 2-CI-4-F-C6H3, 2-CI-5-CF3-C6H3, 2-CI-5-F-C 6 H 3 , 3-CI-2-naphthyl, and 3-CH 3 -2-naphthyl.
  • compounds of the invention are the compounds of the formulae I that are compiled in the Tables 1 to 144, wherein the meaning for the combination of variables X and Y of R 2 for each individual compound of tables 1 to 144 corresponds to each row of Table A.
  • Table 60 Compounds of formula , wherein R 1 is 1 -F-isopropyl, R 2 is R 2 -6, Z is 2-CI-4-F-C 6 H 3 (compounds of formula 1 .60); Table 61 . Compounds of formula , wherein R 1 is 1 -F-isopropyl, R 2 is R 2 -6, Z is 2-CI-5-CF3- C 6 H 3 (compounds of formula 1 .61 );
  • Table 82 Compounds of formula , wherein R 1 is 1 -F-isopropyl, R 2 is R 2 -21 , Z is 2-Br-C 6 H 4 (compounds of formula 1 .82); Table 83. Compounds of formula I, wherein R 1 is 1 -F-isopropyl, R 2 is R 2 -21 , Z is 2-CH3-C6H4 (compounds of formula 1 .83);
  • Table 104 Compounds of formula I, wherein R 1 is 1 -F-cyclopropyl, R 2 is R 2 -5, Z is 3-CH 3 -2- naphthyl (compounds of formula 1.104); Table 105. Compounds of formula I, wherein R 1 is 1-F-cyclopropyl, R 2 is R 2 -6, Z is 2-CI-C 6 H 4 (compounds of formula 1.105);
  • Table 126 Compounds of formula I, wherein R 1 is 1-F-cyclopropyl, R 2 is R 2 -20, Z is 2-CI-5-F- C 6 H 3 (compounds of formula 1.126); Table 127. Compounds of formula I, wherein R 1 is 1 -F-cyclopropyl, R 2 is R 2 -20, Z is 3-CI-2- naphthyl (compounds of formula 1 .127);
  • Compound 1.1.3 e.g. comprises the compound of formula 1.1 from Table 1 and row 3 from Ta- ble A;
  • the pyrimidine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly.
  • Suitable components for mixtures are, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxypro- pionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbama- tes, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthal- imides, oxadiazoles, oxazolidinediones, oxyacetamides
  • pyrimidine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • other crop protection agents e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • compositions according to the present inven- tion comprise at least one pyrimidine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyrimidine compound of formula (I.
  • A) cor- responds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.B) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.C) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.D) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.E) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.F) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.G) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.H) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I. I) (corresponds to pyrimidine compound of formula (I)), as defined herein.
  • Preferred compounds of the formula (I) which, as component A, are constituent of the compo- sition according to the invention are the compounds I.A to 1.1, as defined above.
  • compositions according to the present in- vention comprise at least one pyrimidine compound of formula (I) and at least one further active compound B (herbicide B).
  • the further herbicidal compound B (component B) is preferably selected from the herbicides of class b1 ) to b15):
  • compositions can be selected from below herbicides B as defined below:
  • ALS inhibitors acetolactate synthase inhibitors
  • PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors

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Abstract

The present invention relates to the pyrimidine compounds of formula (I), or their agriculturally acceptable salts or derivatives as herbicides, wherein the variables are defined according to the description, use of pyrimidine compounds of formula (I) as herbicide, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one pyrimidine compounds of the formula (I) to act on plants, their seed and/or their habitat.

Description

Herbicidal pyrimidine compounds
The present invention relates to pyrimidine compounds of the general formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
Description:
Compounds having a 5-phenyl pyrimidine moiety are known in the art. WO 2000/073278 de- scribes such compounds being antagonists of the Neurokinin 1 receptor and thus having phar- maceutical properties. WO2016/120355 discloses the use of phenylpyrimidines as herbicides.
In agriculture, there is a constant demand to develop novel active ingredients, which comple- ment or outperform present methods of treatment regarding activity, selectivity and environmen- tal safety.
These and further objects are achieved by pyrimidine compounds of formula (I), defined below, and by their agriculturally suitable salts. Compared with the compounds described in WO2016/120355, the compounds of formula (I) provided in the present invention show lower leaching risk.
Accordingly, the present invention provides the compounds of formula (I)
Figure imgf000002_0001
wherein R1 is formula R1
Figure imgf000002_0002
Rx, Ry independently of each other are selected from H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, HO-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloal- kynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6-cycloalkoxy, C3-C6-hal- ocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, Ci-C6-alkylsulfinyl, Ci-C6-alkyl- sulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocycloal- kenyl, [1 -(Ci-C6-alkyl)]-C3-C6-cycloalkyl, [1 -(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1 -(C2-C6- alkynyl)]-C3-C6-cycloalkyl, [1 -(Ci-C6-haloalkyl)]-C3-C6-cycloalkyl, [1 -(C2-C6-haloalkenyl)]- C3-C6-cycloalkyl, [1 -(C3-C6-haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl-Ci-C6- haloalkoxy, phenyl, 5- or 6-membered heteroaryl, and 3- to 6-membered heterocyclyl; wherein the cyclic groups of Rx and Ry independently of each other are unsubstituted or substituted with Re; or Rx and R y together with the carbon they are attached can form a 3-to 5-membered satu- rated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 Re;
R2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6- alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, Ci-C6-haloal- koxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy-C2-C6-alkynyl, Ci-C6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C2-C6-alkynyl, Ci-C6-haloalkoxy-C3- C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocy- cloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-halocy- cl oa I kyl-Ci -C6-a I ky I , C3-C6-halocycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkenyl-Ci-C6-haloalkyl, C3-C6-halocycloalkenyl-Ci-C6-alkyl, C3-C6-halocyclo- alkenyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl, C3-C6-cycloalkyl-C2-C6-haloal- kenyl, C3-C6-halocycloalkyl-C2-C6-alkenyl, C3-C6-halocycloalkyl-C2-C6-haloalkenyl, C3-C6- cycloalkenyl-C2-C6-alkenyl, C3-C6-cycloalkenyl-C2-C6-haloalkenyl, C3-C6-halocycloal- kenyl-C2-C6-alkenyl, C3-C6-halocycloalkenyl-C2-C6-haloalkenyl, C3-C6-cycloalkyl-C2-C6- alkynyl, C3-C6-cycloalkyl-C3-C6-haloalkynyl, C3-C6-halocycloalkyl-C2-C6-alkynyl, C3-C6- halocycloalkyl-C3-C6-haloalkynyl, C3-C6-cycloalkenyl-C2-C6-alkynyl, C3-C6-cycloalkenyl- C3-C6-haloalkynyl, C3-C6-halocycloalkenyl-C2-C6-alkynyl, C3-C6-halocycloalkenyl-C3-C6- haloalkynyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkyl-C2-C6-haloalkylidenyl, C3-C6-halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkyl-C2-C6-haloalkylidenyl, C3- C6-cycloalkenyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-C2-C6-haloalkylidenyl, C3-C6-halo- cycloalkenyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkenyl-C2-C6-haloalkylidenyl, heterocy- clyl-Ci-C6-alkylidenyl, heterocyclyl-C2-C6-haloalkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6- alkyl, C3-C6-hydroxycycloalkyl-Ci-C6-haloalkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-alkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-haloalkyl, Ci-C6-hydroxyalkyl, C2-C6-hydroxyhaloalkyl, C3-C6-hydroxyalkenyl, C3-C6-hydroxyhaloalkenyl, C3-C6-hydroxyalkynyl, C4-C6-hydroxy- haloalkynyl, C3-C6-hydroxycycloalkyl, C3-C6-hydroxyhalocycloalkyl, C3-C6-hydroxycyclo- alkenyl, C3-C6-hydroxyhalocycloalkenyl, C3-C6-cycloalkyl-Ci-C6-hydroxyalkyl, C3-Ce-cy- cloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkyl-Ci-C6-hydroxyalkyl, C3-C6-halocy- cloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloalkenyl-Ci-C6-hydroxyalkyl, C3-C6-cycloal- kenyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkenyl-Ci-C6-hydroxyalkyl, C3-C6-halocy- cloalkenyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloalkyl-C3-C6-hydroxyalkenyl, C3-C6-cycloal- kyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocycloalkyl-C3-C6-hydroxyalkenyl, C3-C6-halocy- cloalkyl-C3-C6-hydroxyhaloalkenyl, C3-C6-cycloalkenyl-C3-C6-hydroxyalkenyl, C3-Ce-cy- cloalkenyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydroxyalkenyl, C3- C6-halocycloalkenyl-C3-C6-hydroxyhaloalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyalkynyl, C3-C6-halocycloalkyl-C3-C6-hydroxyalkynyl, C3-C6-cycloalkenyl-C3-C6-hydroxyalkynyl, C3- C6-halocycloalkenyl-C3-C6-hydroxyalkynyl, C3-C6-cycloalkyl-C2-C6-hydroxyalkylidenyl, C3- C6-halocycloalkyl-C2-C6-hydroxyalkylidenyl, C3-C6-cycloalkenyl-C2-C6-hydroxyalkylidenyl, C3-C6-halocycloalkyl-C2-C6-hydroxyalkylidenyl, heterocyclyl-C2-C6-hydroxyalkylidenyl, hy- droxycarbonyl-Ci-C6-hydroxyalkyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci-C6- haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-hydroxyalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-hy- droxyalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6- haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, C3- C6-hydroxycycloalkyl-Ci-C6-hydroxyalkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-hydroxyalkyl, C3-C6-hyd roxycycloa I kyl-C3-C6-hyd roxyal kenyl , C3-C6-hyd roxycycloal kenyl-C3-C6-hyd rox- ya I kenyl , C3-C6-hyd roxycycloa I kyl-C3-C6-hyd roxya Ikynyl , C3-C6-hyd roxycycloa I kenyl-C3- C6-hyd roxyal kenyl, C2-C6-dihydroxyalkyl, C3-C6-dihydroxyhaloalkyl, C4-C6-di hydroxy- alkenyl, C4-C6-dihydroxyhaloalkenyl, C4-C6-di hyd roxya I kynyl, Cs-Ce-dihydroxyhaloal- kynyl, C4-C6-dihydroxycycloalkyl, C4-C6-dihydroxyhalocycloalkyl, C4-C6-dihyd roxycycloa I- kenyl, C4-C6-dihydroxyhalocycloalkenyl, C3-C6-cycloalkyl-C2-C6-dihydroxyalkyl, C3-C6- halocycloalkyl-C2-C6-dihydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-dihydroxyalkyl, C3-C6-hal- ocycl oa I kenyl-C2-C6-d i hyd roxya I kyl , C3-C6-cycloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-ha lo- cycloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-cycloa I kenyl-C3-C6-d i hyd roxya I kenyl , C3-C6-ha I- ocycl oa I kenyl-C3-C6-d i hyd roxya I kenyl , C3-C6-cycloa I kyl-C4-C6-d i hyd roxya I kynyl , C3-C6- halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkenyl-C4-C6-dihydroxyalkynyl, C3-C6- halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkyl-C3-C6-dihydroxyalkylidenyl, C3- C6-halocycloalkyl-C3-C6-dihydroxyalkylidenyl, heterocyclyl-C3-C6-dihydroxyalkylidenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, hydroxycarbonyl-C3-C6-dihydroxyhaloalkyl, C1-C6- alkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloalkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloalkoxycarbonyl-C3-C6-dihydroxyhaloalkyl, C3-C6-dihydroxycycloalkyl- C1-C6- alkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-haloalkylC3-C6-dihydroxycycloalkyl- C2-C6- alkenyl, C3-C6-dihydroxycycloalkyl- C2-C6-haloalkenyl, C3-C6-dihydroxycycloalkyl- C2-C6- alkynyl, C3-C6-dihydroxycycloalkyl- C3-C6-haloal kynyl, Ci-C6-alkylcarbonyl-Ci-C6-alkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-haloal- kylcarbonyl-Ci-C6-haloalkyl, hydroxycarbonyl-C2-C6-alkenyl, hydroxycarbonyl-C2-C6- haloalkenyl, Ci-C6-alkoxycarbonyl-C2-C6-alkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6- alkenyl, Ci-C6-alkoxycarbonyl-C2-C6-haloalkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6-haloal- kenyl, hydroxycarbonyl-C2-C6-alkynyl, hydroxycarbonyl-C3-C6-haloalkynyl, Ci-C6-alkoxy- carbonyl-C2-C6-alkynyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkynyl, Ci-C6-alkoxycarbonyl- C3-C6-haloalkynyl, Ci-C6-haloalkoxycarbonyl-C3-C6-haloalkynyl, Ci-C6-cyanoalkyl, C2-C6- cyanohaloalkyl, Ci-C6-dicyanoalkyl, C2-C6-dicyanohaloalkyl, di(hydroxycarbonyl)-C-i-C6- alkyl, di(hydroxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-alkyl, di(Ci- C6-haloalkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6- haloalkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxyl)phosphoryl-Ci-C6-alkyl, di(Ci-C6- haloalkoxyl)phosphoryl-Ci-C6-alkyl, di(Ci-C6-alkoxyl)phosphoryl-Ci-C6-haloalkyl, di(Ci- C6-haloalkoxyl)phosphoryl-Ci-C6-haloalkyl, phosphoryl-Ci-C6-alkyl , phosphoryl-Ci-C6- haloalkyl , di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-haloalkoxyl)phos- phoryl-)]Ci-C6-alkyl, di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-haloalkyl, di[di(Ci-C6-haloal- koxyl)phosphoryl-)]Ci-C6-haloalkyl, diphosphoryl-Ci-C6-alkyl , diphosphoryl-Ci-C6-haloal- kyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-haloalkylthio-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6- haloalkyl, Ci-C6-haloalkylthio-Ci-C6-haloalkyl, Ci-C6-alkylsulfinly-Ci-C6-alkyl, C1-C6- haloalkylsulfinly-Ci-C6-alkyl, Ci-C6-alkylsulfinly-Ci-C6-haloalkyl, Ci-C6-haloalkylsulfinly- Ci-C6-haloalkyl, Ci-C6-alkylsulfonyl-Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6-alkyl, C1- C6-haloalkylsulfonyl-Ci-C6-haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6- membered heterocyclyl, (Ci-C6-alkyl)carbonylaminocarbonyl, (C3-C6-alkenyl)carbonyla- minocarbonyl, (C3-C6-alkynyl)carbonylaminocarbonyl, (Ci-C6-haloalkyl)carbonyla- minocarbonyl, alkynylphenylcarbonylaminocarbonyl, (C3-C6-cycloalkyl)carbonyla- minocarbonyl, [di(Ci-C6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonyla- minocarbonyl, heteroarylcarbonylaminocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkyl)ami- nocarbonyl, [(Ci-C6-haloalkyl)carbonyl](Ci-C6-alkyl)aminocarbonyl, [(C3-C6-cycloal- kyl)carbonyl](Ci-C6-alkyl)aminocarbonyl, (phenylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (heterocyclylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkyl)ami- nocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(Ci-C6-haloalkyl)car- bonyl](Ci-C6-alkoxy)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](Ci-C6-alkyloxy)ami- nocarbonyl, (phenylcarbonyl)(Ci-C6-alkoxy)aminocarbonyl, (heterocyclylcarbonyl)(Ci-C6- alkoxy)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkoxy)aminocarbonyl, [(Ci-C6-al- kyl)carbonyl](C3-C6-alkenyl)aminocarbonyl, [(Ci-C6-haloalkyl)carbonyl](C2-C6- alkenyl)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkenyl)aminocarbonyl, (phe- nylcarbonyl)(C3-C6-alkenyl)aminocarbonyl, (heterocyclylcarbonyl)(C3-C6-alkenyl)ami- nocarbonyl, (heteroarylcarbonyl)(C3-C6-alkenyl)aminocarbonyl, [(Ci-C6-alkyl)car- bonyl](C3-C6-alkynyl)aminocarbonyl, [(Ci-C6-haloalkyl)carbonyl](C3-C6-alkynyl)aminocar- bonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkynyl)aminocarbonyl, (phenylcarbonyl)(C3-C6- alkynyl)aminocarbonyl, (heterocyclylcarbonyl)(C3-C6-alkynyl)aminocarbonyl, (heteroaryl- carbonyl)(C3-C6-alkynyl)aminocarbonyl, [(C2-C6-alkenyl)carbonyl]aminocarbonyl, [(C2-C6- alkenyl)carbonyl](Ci-C6-alkyl)aminocarbonyl, [(C2-C6-alkenyl)carbonyl](Ci-C6-alkoxy)ami- nocarbonyl, [(C3-C6-alkynyl)carbonyl]aminocarbonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-al- kyl)aminocarbonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [di(Ci-C6-al- kyl)amino]carbonylaminocarbonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkyl)aminocar- bonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkoxy)aminocarbonyl;
wherein OH groups of R2 are unsubstituted or substituted by Rb;
carbon atoms of cyclic groups of R2 are unsubstituted or substituted independently of each other with 1 , 2, or 3 moieties R20; and heteroatoms of cyclic groups of R2 are un- substituted or substituted with Q;
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenylcar- bonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6-al- kyl)aminosulfonyl, or Ci-C6-alkylaminosulfonyl;
R20 is H, halogen, CN, NO2, OH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfinyl, C3-C6-a I ki nyl s ulf i nyl , aminosulfinyl, C1- C6-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfinyl, C3-C6-alkenylsulfonyl, C3-C6-alkinyl- sulfonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, C1-C6- alkylcarbonylaminosulfonyl, C3-C6-cycloalkylcarbonylaminosulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, hydroxycarbonyl, aminocarbonyl, NH2-aminocarbonyl, Ci-C6-al- kylcarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkinylcarbonyl, thiocarbonyl, Ci-C6-alkylcar- bonylaminocarbonyl, C3-C6-cycloalkylcarbonylaminocarbonyl, Ci-C6-alkylsulfonyla- minocarbonyl, C3-C6-cycloalkylsulfonylaminocarbonyl, di(Ci-C6-alkyl)aminosulfonyla- minocarbonyl, hydroxyaminocarbonyl, Ci-C6-alkoxyaminocarbonyl, [(Ci-C6-alkoxy)(Ci- C6-alkyl)amino]carbonyl, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6- membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, (H0)2(0)P, (HO)(OI-OQ- alkoxy)(0)P, (Ci-C6-alkoxy)2(0)P, Cs-Cs-cycloalkyl, C4-C8-cycloalkenyl, C-i-Cs-alkyli- denyl-cycloalkyl, C-i-Cs-alkylidenyl-heterocyclyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, phenylsulfinyl, 5- or 6-membered heteroarylsulfinyl, 3- to 6-membered heterocyclylsulfinyl, C3-C6-cycloalkylsulfinyl, phenylsulfonyl, 5- or 6- membered heteroarylsulfonyl, 3- to 6-membered heterocyclylsulfonyl, C3-C6-cycloalkyl- sulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6- haloalkinyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocyclo- alkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcar- bonyl, C3-C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C6-alkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-aminocarbonyl, Ci-C6-dialkylaminocarbonyl, Ci-C6-alkyl- sulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered hetero- cyclyl;
Rc is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, NH2, Ci-C6-alkyl-amino, di(Ci-C6-alkyl)amino, SH, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, Ci-C6-alkyla- minocarbonyl, or di(Ci-C6-alkyl)aminocarbonyl;
Rd is halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloalkyl, C3- C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C6-haloalkoxy, NH2, Ci-C6-alkyl-amino, di(C1-C6-alkyl)amino, SH, Ci -C6-a I ky Ith i o , C1- C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, hydroxycar- bonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkenyloxycarbonyl, Ci-C6-alkinyloxycarbonyl, C1- C6-alkoxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, C1- C6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, aminocarbonyl, Ci-C6-alkylaminocar- bonyl, di(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, Ci-C6-alkoxy- Ci-C6-alkyl, phenylthio, phe- nyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocy- clyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
R4 and R5 are independently from each other selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkinyl, OH, NH2, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkylsulfonyl, C1- C6-haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, Ci-C6-alkylsulfinyl, C3- C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, Ci-C6-alkoxycarbonyl, C3-C6-alkenyloxycar- bonyl, C3-C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-mem- bered heterocyclyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3- or 6-membered heterocy- clyloxy, C3-C6-cycloalkyloxy, C3-C6-cycloalkenyloxy, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl, 5- or 6-membered heteroarylsulfinyl, 3- or 6-membered heterocyclylsulfi- nyl, C3-C6-cycloalkylsulfinyl, C3-C6-cycloalkenylsulfinyl, phenyloxycarbonyl, 5- or 6- membered heteroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6- cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, Ci-C6-alkyla- minocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, aminosulfinyl, Ci-C6-alkylaminosulfinyl, and di(Ci-C6-al- kyl)aminosulfinyl;
Z is phenyl, 5-, 6- or 9 membered heteroaryl, or 9- or 10-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
R3 is H, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alke- nyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1- C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re;
Re is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
Rf is H, halogen, CN, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloalkyl, C3-C6- haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1-C6- haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; m is 0, 1 , 2, 3, or 4;
n is 1 , 2, 3, 4, or 5;
including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality.
Preferably, the present invention also provides the pyrimidine compounds of formula (I)
Figure imgf000007_0001
wherein R1 is formula R1
Figure imgf000007_0002
Rx, Ry independently of each other are selected from H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, HO-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6-cycloal- koxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, C1- C6-alkylthio, Ci-C6-haloalkylthio, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, Ci-C6-al- kylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocyclo- alkyl, C3-C6-halocycloalkenyl, [1-(Ci-C6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]- C3-C6-cycloalkyl, [1 -(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1 -(Ci-C6-haloalkyl)]-C3-C6-cy- cloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6-cy- cloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cyclo- alkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl-Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, and 3- to 6-membered heterocyclyl;
wherein the cyclic groups of Rx and Ry independently of each other are unsubsti- tuted or substituted with Re;
or Rx and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom se- lected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 Re;
R2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6- alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, C1-C6- haloalkoxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy-C2-C6- alkynyl, Ci-C6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C2-C6-alkynyl, C1-C6- haloalkoxy-C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloal- kenyl, C3-C6-halocycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6- haloalkyl, C3-C6-halocycloalkyl-Ci-C6-alkyl, C3-C6-halocycloalkyl-Ci-C6-haloalkyl, C3- C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkenyl-Ci-C6-haloalkyl, C3-C6-halocycloal- kenyl-Ci-C6-alkyl, C3-C6-halocycloalkenyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6- alkenyl, C3-C6-cycloalkyl-C2-C6-haloalkenyl, C3-C6-halocycloalkyl-C2-C6-alkenyl, C3- C6-halocycloalkyl-C2-C6-haloalkenyl, C3-C6-cycloalkenyl-C2-C6-alkenyl, C3-C6-cyclo- alkenyl-C2-C6-haloalkenyl, C3-C6-halocycloalkenyl-C2-C6-alkenyl, C3-C6-halocycloal- kenyl-C2-C6-haloalkenyl, C3-C6-cycloalkyl-C2-C6-alkynyl, C3-C6-cycloalkyl-C3-C6- haloalkynyl, C3-C6-halocycloalkyl-C2-C6-alkynyl, C3-C6-halocycloalkyl-C3-C6-haloal- kynyl, C3-C6-cycloalkenyl-C2-C6-alkynyl, C3-C6-cycloalkenyl-C3-C6-haloalkynyl, C3- C6-halocycloalkenyl-C2-C6-alkynyl, C3-C6-halocycloalkenyl-C3-C6-haloalkynyl, C3-C6- cycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkyl-C2-C6-haloalkylidenyl, C3-C6-halocyclo- alkyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkyl-C2-C6-haloalkylidenyl, C3-C6-cycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-C2-C6-haloalkylidenyl, C3-C6-halocycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkenyl-C2-C6-haloalkylidenyl, heterocyclyl- Ci-C6-alkylidenyl, heterocyclyl-C2-C6-haloalkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6- alkyl, C3-C6-hydroxycycloalkyl-Ci-C6-haloalkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-al- kyl, C3-C6-hydroxycycloalkenyl-Ci-C6-haloalkyl, Ci-C6-hydroxyalkyl, C2-C6-hydroxy- haloalkyl, C3-C6-hydroxyalkenyl, C3-C6-hydroxyhaloalkenyl, C3-C6-hydroxyalkynyl, C4-C6-hydroxyhaloalkynyl, C3-C6-hydroxycycloalkyl, C3-C6-hydroxyhalocycloalkyl, C3-C6-hydroxycycloalkenyl, C3-C6-hydroxyhalocycloalkenyl, C3-C6-cycloalkyl-Ci-C6- hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkyl-Ci-C6- hydroxyalkyl, C3-C6-halocycloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloalkenyl-Ci- C6-hydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkenyl- Ci-C6-hydroxyalkyl, C3-C6-halocycloalkenyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloal- kyl-C3-C6-hydroxyalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocy- cloalkyl-C3-C6-hydroxyalkenyl, C3-C6-halocycloalkyl-C3-C6-hydroxyhaloalkenyl, C3- C6-cycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-cycloalkenyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydrox- yhaloalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyalkynyl, C3-C6-halocycloalkyl-C3-C6-hy- droxyalkynyl, C3-C6-cycloalkenyl-C3-C6-hydroxyalkynyl, C3-C6-halocycloalkenyl-C3- C6-hydroxyalkynyl, C3-C6-cycloalkyl-C2-C6-hydroxyalkylidenyl, C3-C6-halocycloalkyl- C2-C6-hydroxyalkylidenyl, C3-C6-cycloalkenyl-C2-C6-hydroxyalkylidenyl, C3-C6-halo- cycloalkyl-C2-C6-hydroxyalkylidenyl, heterocyclyl-C2-C6-hydroxyalkylidenyl, hy- droxycarbonyl-Ci-C6-hydroxyalkyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl- Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-hydroxyalkyl, Ci-C6-haloalkoxycar- bonyl-Ci-C6-hydroxyalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloal- koxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloal- koxyca rbonyl-Ci -C6-a I kyl , C3-C6-hyd roxycycloa I kyl-Ci -C6-hyd roxyal kyl , C3-C6-hy- d roxycycl oa I kenyl-Ci -C6-hyd roxya I kyl , C3-C6-hyd roxycycloa I kyl-C3-C6-hyd roxy- a I kenyl , C3-C6-hyd roxycycloal kenyl-C3-C6-hyd roxya I kenyl , C3-C6-hyd roxycycloa I kyl- C3-C6-hyd roxya I kynyl , C3-C6-hyd roxycycloal kenyl-C3-C6-hyd roxyal kenyl , C2-C6-d ihy- droxyalkyl, C3-C6-dihydroxyhaloalkyl, C4-C6-dihyd roxya I kenyl, C4-C6-dihydroxy- haloalkenyl, C4-C6-d ihyd roxya I kynyl, Cs-Ce-dihydroxyhaloalkynyl, C4-C6-dihydroxycy- cloalkyl, C4-C6-dihydroxyhalocycloalkyl, C4-C6-dihydroxycycloalkenyl, C4-C6-dihy- droxyhalocycloalkenyl, C3-C6-cycloalkyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloalkyl- C2-C6-dihydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloal- kenyl-C2-C6-d i hyd roxya I kyl , C3-C6-cycloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-hal ocy- cloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-cycloa I kenyl-C3-C6-d i hyd roxya I kenyl , C3-C6- halocycloalkenyl-C3-C6-dihydroxyalkenyl, C3-C6-cycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-halocycloal kyl-C4-C6-d ihyd roxyal kynyl , C3-C6-cycloal kenyl-C4-C6-d ihyd roxy- alkynyl, C3-C6-halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkyl-C3-C6-dihy- droxyalkylidenyl, C3-C6-halocycloalkyl-C3-C6-dihydroxyalkylidenyl, heterocyclyl-C3- C6-d ihyd roxyal kyl idenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, hydroxycarbonyl-C3- C6-dihydroxyhaloalkyl, Ci-C6-alkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloal- koxycarbonyl-C2-C6-d ihyd roxya I kyl, Ci-C6-haloalkoxycarbonyl-C3-C6-dihydroxy- haloalkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-alkyl, C3-C6-dihydroxycycloalkyl- C1-C6- haloalkylC3-C6-dihydroxycycloalkyl- C2-C6-alkenyl, C3-C6-dihydroxycycloalkyl- C2-C6- haloalkenyl, C3-C6-dihydroxycycloalkyl- C2-C6-alkynyl, C3-C6-dihydroxycycloalkyl- C3-C6-haloalkynyl, Ci-C6-alkylcarbonyl-Ci-C6-alkyl, Ci-C6-haloalkylcarbonyl-Ci-C6- alkyl, Ci-C6-alkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-haloalkyl, hydroxycarbonyl-C2-C6-alkenyl, hydroxycarbonyl-C2-C6-haloalkenyl, Ci-C6-alkoxy- carbonyl-C2-C6-alkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkenyl, Ci-C6-alkoxycar- bonyl-C2-C6-haloalkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6-haloalkenyl, hydroxycar- bonyl-C2-C6-alkynyl, hydroxycarbonyl-C3-C6-haloalkynyl, Ci-C6-alkoxycarbonyl-C2- C6-alkynyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkynyl, Ci-C6-alkoxycarbonyl-C3-C6- haloalkynyl, Ci-C6-haloalkoxycarbonyl-C3-C6-haloalkynyl, Ci-C6-cyanoalkyl, C2-C6- cyanohaloalkyl, Ci-C6-dicyanoalkyl, C2-C6-dicyanohaloalkyl, di(hydroxycarbonyl)-Ci- C6-alkyl, di(hydroxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-haloalkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-haloalkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxyl)phosphoryl-Ci-C6- alkyl, di(Ci-C6-haloalkoxyl)phosphoryl-Ci-C6-alkyl, di(Ci-C6-alkoxyl)phosphoryl-Ci- C6-haloalkyl, di(Ci-C6-haloalkoxyl)phosphoryl-Ci-C6-haloalkyl, phosphoryl-Ci-C6-al- kyl , phosphoryl-Ci-C6-haloalkyl , di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-haloalkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci- C6-haloalkyl, di[di(Ci-C6-haloalkoxyl)phosphoryl-)]Ci-C6-haloalkyl, diphosphoryl-C-i- C6-alkyl , diphosphoryl-Ci-C6-haloalkyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-haloal- kylthio-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6-haloalkyl, Ci-C6-haloalkylthio-Ci-C6-haloal- kyl, Ci-C6-alkylsulfinly-Ci-C6-alkyl, Ci-C6-haloalkylsulfinly-Ci-C6-alkyl, Ci-C6-alkyl- sulfinly-Ci-C6-haloalkyl, Ci-C6-haloalkylsulfinly-Ci-C6-haloalkyl, Ci-C6-alkylsulfonyl- Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6- haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (Ci-C6-alkyl)carbonylaminocarbonyl, (C3-C6-alkenyl)carbonylaminocarbonyl, (C3-C6- alkynyl)carbonylaminocarbonyl, (Ci-C6-haloalkyl)carbonylaminocarbonyl, al- kynylphenylcarbonylaminocarbonyl, (C3-C6-cycloalkyl)carbonylaminocarbonyl,
[di(Ci-C6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkyl)aminocar- bonyl, [(Ci-C6-haloalkyl)carbonyl](Ci-C6-alkyl)aminocarbonyl, [(C3-C6-cycloalkyl)car- bonyl](Ci-C6-alkyl)aminocarbonyl, (phenylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (het- erocyclylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkyl)ami- nocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(Ci-C6-haloal- kyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](Ci-C6-al- kyloxy)aminocarbonyl, (phenylcarbonyl)(Ci-C6-alkoxy)aminocarbonyl, (heterocyclyl- carbonyl)(Ci-C6-alkoxy)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkoxy)aminocar- bonyl, [(Ci-C6-alkyl)carbonyl](C3-C6-alkenyl)aminocarbonyl, [(Ci-C6-haloalkyl)car- bonyl](C2-C6- alkenyl)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkenyl)ami- nocarbonyl, (phenylcarbonyl)(C3-C6-alkenyl)aminocarbonyl, (heterocyclylcar- bonyl)(C3-C6-alkenyl)aminocarbonyl, (heteroarylcarbonyl)(C3-C6-alkenyl)aminocar- bonyl, [(Ci-C6-alkyl)carbonyl](C3-C6-alkynyl)aminocarbonyl, [(Ci-C6-haloalkyl)car- bonyl](C3-C6-alkynyl)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkynyl)ami- nocarbonyl, (phenylcarbonyl)(C3-C6-alkynyl)aminocarbonyl, (heterocyclylcar- bonyl)(C3-C6-alkynyl)aminocarbonyl, (heteroarylcarbonyl)(C3-C6-alkynyl)aminocar- bonyl, [(C2-C6-alkenyl)carbonyl]aminocarbonyl, [(C2-C6-alkenyl)carbonyl](Ci-C6-al- kyl)aminocarbonyl, [(C2-C6-alkenyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(C3-C6- alkynyl)carbonyl]aminocarbonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-alkyl)aminocar- bonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [di(Ci-C6-al- kyl)amino]carbonylaminocarbonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkyl)ami- nocarbonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkoxy)aminocarbonyl;
wherein OH groups of R2 are unsubstituted or substituted by Rb;
carbon atoms of cyclic groups of R2 are unsubstituted or substituted independently of each other with 1 , 2, or 3 moieties R20; and heteroatoms of cyclic groups of R2 are unsubstituted or substituted with Q;
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenylcar- bonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6- alkyl)aminosulfonyl, or Ci-C6-alkylaminosulfonyl; Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3- C6-halocycloalkenyl, Ci-C6-alkoxycarbonyl-C-i-C6-alkyl, Ci-C6-haloalkoxycarbonyl- Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-haloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, hydroxycarbonyl-Ci- C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-haloal- kyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-haloalkylthiocarbonyl, Ci-C6-alkyl- aminocarbonyl, Ci-C6-haloalkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, C1- C6-dihaloalkylaminocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C1-C6- alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-haloalkyl, Ci-C6-haloalkoxy-Ci-C6-haloalkyl, phenyl-Ci-C6-alkyl, or phenyl-Ci-C6-haloalkyl;
R20 is H, halogen, CN, NO2, OH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(Ci-C4- alkoxy)n, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfinyl, C3-C6-a I ki nyl su If i ny I , aminosulfinyl, Ci-C6-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfinyl, C3-C6-alken- ylsulfonyl, C3-C6-alkinylsulfonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci- C6-alkyl)aminosulfonyl, Ci-C6-alkylcarbonylaminosulfonyl, C3-C6-cycloalkylcar- bonylaminosulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, hydroxycarbonyl, ami- nocarbonyl, NH2-aminocarbonyl, Ci-C6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3- C6-alkinylcarbonyl, thiocarbonyl, Ci-C6-alkylcarbonylaminocarbonyl, C3-C6-cyclo- alkylcarbonylaminocarbonyl, Ci-C6-alkylsulfonylaminocarbonyl, C3-C6-cycloalkyl- sulfonylaminocarbonyl, di(Ci-C6-alkyl)aminosulfonylaminocarbonyl, hydroxy- aminocarbonyl, Ci-C6-alkoxyaminocarbonyl, [(Ci-C6-alkoxy)(Ci-C6-al- kyl)amino]carbonyl, phenylcarbonyl, 5 or 6-membered heteroarylcarbonyl, 3 or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, (HO)2(0)P,
(HO)(Ci-C6-alkoxy)(0)P, (Ci-C6-alkoxy)2(0)P, Cs-Cs-cycloalkyl, C4-C8-cycloal- kenyl, C-i-Cs-alkylidenyl-cycloalkyl, C-i-Cs-alkylidenyl-heterocyclyl, phenyl, 5 or 6- membered heteroaryl, or 3 to 6-membered heterocyclyl, phenylsulfinyl, 5 or 6- membered heteroarylsulfinyl, 3 to 6-membered heterocyclylsulfinyl, C3-C6-cyclo- alkylsulfinyl, phenylsulfonyl, 5 or 6-membered heteroarylsulfonyl, 3 to 6-mem- bered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3- C6-haloalkinyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6- halocycloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C6-alkyl, C1-C6- alkyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-aminocarbonyl, Ci-C6-dialkyla- minocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl- sulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rc is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, C1-C6- haloalkoxy, NH2, Ci-C6-alkyl-amino, di(Ci-C6-alkyl)amino, SH, Ci-C6-alkylthio, C1- C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6- alkenyloxycarbonyl, alkinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, ami- nocarbonyl, Ci-C6-alkylaminocarbonyl, or di(Ci-C6-alkyl)aminocarbonyl;
Rd is halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloal- kyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6- alkinyloxy, Ci-C6-haloalkoxy, NH2, Ci-C6-alkyl-amino, di(C1-C6-alkyl)amino, SH, C1 -C6-a I ky Ith i o , Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C4-C8- cycloalkenyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkenyloxycarbonyl, Ci-C6-alkinyloxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci- C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl- sulfonyl, Ci-C6-alkoxy- Ci-C6-alkyl, phenylthio, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
R4 and R5 are independently from each other selected from hydrogen, Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkinyl, OH, NH2, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, Ci-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinyl- sulfonyl, Ci-C6-alkylsulfinyl, C3-C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, C1-C6- alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-membered heterocyclyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, 3- or 6-membered heterocyclyloxy, C3-C6-cycloalkyloxy, C3-Ce-cy- cloalkenyloxy, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6- membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkenylcar- bonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl, 5- or 6-membered heteroarylsulfinyl, 3- or 6-membered heterocy- clylsulfinyl, C3-C6-cycloalkylsulfinyl, C3-C6-cycloalkenylsulfinyl, phenyloxycar- bonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-membered heterocy- clyloxycarbonyl, C3-C6-cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, amino- sulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, aminosulfinyl, Ci-C6-alkylaminosulfinyl, and di(Ci-C6-alkyl)aminosulfinyl;
Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 1 0-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
R3 is H, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloal- kynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, C1-C6- alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (C1-C6- alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl; wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; Re is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloal- koxy;
Rf is H, halogen, CN, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-mem- bered heterocyclyl;
m is 0, 1 , 2, 3, or 4;
n is 1 , 2, 3, 4, or 5;
including agriculturally acceptable salts or derivatives of compounds of formula (I);
provided that when R1 is CF3 and Z-(R3)m is Phenyl, R2 is not CF3 ; and when R1 is CF3 and Z-(R3)m is 4-CN-Phenyl, R2 is not Phenyl, Piperidyl, or N-substituted piperidinyl.
More preferably, the present invention provides the pyrimidine compounds of said formula (I), wherein when m is 2, 3 or 4, each R3 in formula (I) is independently H, halogen, CN, NO2, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al- kynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycar- bonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, NH2, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, (C1-C6-alkyl)sulfinyl, (C1-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6- cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re.
The present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
The present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) as herbicide.
The pyrimidine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes or process described for preparation examples:
Process A:
The pyrimidine compounds of formula (I) can be obtained by reacting respective amino- ketones of formula (II) with base and amidine (III):
Figure imgf000013_0001
The reaction of the aminoketones (II) with amidines (III) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 20°C to the boiling point, particularly from 40°C to 120°C, in an inert organic solvent in the presence of a base.
The reaction may in principle be carried out without solvent. However, preference is given to reacting the aminoketones (II) with the amidine (III) in an organic solvent. Suitable solvents are those capable of dissolving the aminoketones (II) with the amidine (III) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride (CCI4) and chlorobenzene, ethers such as di- ethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofu- ran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propi- onitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-buta- nol, as well as dipolar aprotic solvents such as sulfolane, dimethylformamide (DMF), N,N-dime- thylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), DMSO, and 1 -methyl-2 pyrrolidinone (NMP). Preferred solvents are alcohols such as methanol and ethanol. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCFh), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide (/BuOK), potassium tert- pentoxide and dimethoxymagnesium, moreover organic bases, e.g. tertiary amines, such as tri- methylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperi- dine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaOCFh, NaOC2H5, KOC2H5, tBuOK and potassium tert-pentoxide. The bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the amidine (XI), based on the aminoketone (X).
Amidines (XI) are known from literature or commercially available. In cases in which R2 resem- Ibes a carbo- Oder a heterocycle further, literature known, manipulations are possible: For ex- ample oxazoles can selectively be halogenated following published procedures (e.g. Bioorganic & Medicinal Chemistry, 2010, 18, 4821 ).
Preparation of compounds (II):
(R 3)m
Figure imgf000014_0001
The aminoketones (II) are prepared from the corresponding ketones (IV) with N,N-Dimethylfor- mamide dimethyl acetal (CAS 4637-24-5; DMFDMA). The reaction is usually carried out at tem- peratures from -100° C to the boiling point of the reaction mixture, preferably from 20°C to 160° C, particularly from 50°C to 130°C. The reaction can optionally be catalyzed by an acid. The reaction may be carried out in substance or in an organic solvent. Suitable solvents are those capable of dissolving the ketones (IV) and DMFDMA (CAS 4637-24-5) at least partly, preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, esters such as ethyl acetate and bu- tyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP; preferably DMFDMA is used as sol- vent. It is also possible to use mixtures of the solvents mentioned.
Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2SO4); organic acids p- toluenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI. Most preferred is no use of acid.
The acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
Figure imgf000015_0001
The ketones (IV) are prepared by reacting Grignard-reagent (V) with a carbonyl-electrophile (VI) (e.g. an acid halide (Z = F, Cl or Br) or a Weinreb-Amide (Z = N(Me)OMe)). The reaction is carried out at temperatures of from -100° C to the boiling point of the reaction mixture, prefera- bly from -80° C to 60° C, particularly from -80° C to 20° C, in an inert solvent.
Suitable solvents are those capable of dissolving the Grignard-reagent (V) and the carbonyl- electrophile (VI) at least partly and preferably fully under reaction conditions. Examples of suita- ble solvents are aliphatic aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, an- isole and THF, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. Preferred solvents are ethers such as tert-butyl methyl ether or THF. It is also possible to use mixtures of the solvents mentioned.
The Grignard-reagents (V) are either commercially available or can be prepared from the cor- responding halides by known methods.
The carbonyl electrophiles (VI) are either commercially available or can be prepared from the corresponding carboxylic acid or carboxylic ester by known methods.
Figure imgf000015_0002
Ketones (IV) can as well be prepared from morpholinonitriles (VII) as described in the literature (European Journal of Organic Chemistry 2013, 36, 8083).
Figure imgf000016_0001
The morpholinonitriles (VII) are prepared from morpholinonitriles (VIII) and benzylhalides (IX) in the presence of a base. The reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -80°C to 60°C, particularly from -50°C to 20°C, in an inert organic solvent in the presence of a base.
Suitable solvents are those capable of dissolving the morpholinonitriles (VIII) and the benzyl- halides (IX) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, esters such as ethyl acetate and bu- tyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. Preferred solvents are dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO, and NMP. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCFh, NaOC2H5, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g. ter- tiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular pref- erence is given to NaH, LHMDS and LDA.
The bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the halide (IX), based on the morpholinonitrile (VIII).
Benzylhalides (IX) are commercially available.
Figure imgf000016_0002
Morpholinonitriles (VIII) are prepared from the corresponding aldehydes (X) as described in the literature (WO 2009/013462). Aldehydes (X) are commercially available.
Process B :
Figure imgf000016_0003
The pyrimidines of formula (XI) can be obtained from pyrimidines of formula (XII) by known methods e.g using PPhs and Iodine (analogous to Davies, James R. etai Journal of Organic Chemistry, 70(15), 5840-5851 , 2005 or Just-Baringo, Xavier etal. Angewandte Chemie, Inter- national Edition, 52(30), 7818-7821 , 2013).
Figure imgf000017_0001
The pyrimidines of formula (XII) can be obtained from pyrimidines of formula (XIII) by reaction with the carboxylic acides (XIV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloal- kenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
The reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an inert or- ganic solvent.
Carboxylic acids RCOOH are commercially available. Carboxylic acids are activated using ac- tivating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethyla- mino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1 H- benzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluronium-hexafluorophosphate (HBTU), ethyl-3-(3-dimethyl- aminopropyl)carbodiimid (EDC). The carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chloride. Carbonylimidazoles such as 1 ,T-Carbon- yldiimidazol (CDI) may also be used as activating reagent under neutral conditions. Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered sol- vents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned. Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethyla- mine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy- clic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DIPEA.
The bases are generally employed in excess amounts; however, they can also be employed in equal amounts as the pyrimidine.
Figure imgf000017_0002
The pyrimidines of formula (XIII) can be obtained from pyrimidines of formula (XV), wherein R is hydroxycarbonyl, alkoxycarbonyl, (HO)2(0)R, (alkoxy)2(0)P, alkyl sulfonyl or alkylcarbonyl, by reaction with with an acid HA The reaction of the pyrimidine (XV) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an organic solvent using water as a cosolvent. The starting materials are reacted with one another in equimolar amounts or using an excess of one reagent. Preference is given to us- ing an excess of acid HA.
Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2SO4); organic acids p- toluenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; most preferably HCI.
Suitable solvents include dioxane and tetrahydrofuran (THF), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and N,N- dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered solvents are alcohols. It is also possi- ble to use mixtures of the solvents mentioned.
The pyrimidines of formula (XV) can be obtained by process C.
Process C:
The pyrimidines of formula (XV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or a carboxylic ester, can be ob- tained by reacting respective pyrimidines of formula (XVI) with isocyanides (XVII):
Figure imgf000018_0001
The reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -78°C to 25°C, particularly from -78°C to 0°C, in an inert or- ganic solvent using a base. Suitable solvents are those capable of dissolving the pyrimidine (XVI) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
The bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the isocyanide (XVII) based on the pyrimidine (XVI).
The pyrimidines of formula (XVI) can be obtained by reacting respective pyrimidines of formula (XVIII) with boronic acids/esters of formula (XIX):
Figure imgf000019_0001
The reaction of pyrimidines (XVIII) with boronic acids/esters (XIX) is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
The reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XVIII) with the boronic acids/esters (XIX) in an organic solvent with or without water as co-solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XVIII) and the boronic acids (XIX) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as LhO, Na20, K2O, MgO, and CaO, Fe203, Ag20; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03, as well as alkali metal bicarbonates such as UHCO3, NaHCOs, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hy- droxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkali metal or alkaline earth metal carbonates such as L12CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03 and alkaline earth metal phosphates such as K3PO4; alkali metal and alkaline earth metal acetates such as sodium acetate. Especially preferred bases are inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkaline earth metal phosphates such as K3PO4.
The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
The bases are used preferably at from 1 to 10 equivalents based on the pyrimidine (XVIII), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (XVIII), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XVIII).
It may be advantageous to add the base offset over a period of time. The reaction of the pyrimidines (XVIII) with the boronic acids/esters (XIX) is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphos- phine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphos- phine or BINAP (2,2'-Bis(diphenylphospino)-1 ,T-binaphthyl).
The amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyrimidine (XVIII).
The halopyrimidines (XVIII) are known from the literature (e.g. WO 2011 154327), are commer- cially available or can be prepared by known procedures.
The boronic acids/esters (XIX) required for the preparation of pyrimidines of formula (XVI) are commercially available, known from literature or can easily be prepared analogously to pub- lished procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
Process
Figure imgf000020_0001
The pyrimidines of formula (XV) can also be obtained by reacting respective pyrimidine alde- hydes (XX) with tosyl isocyanides (XXI), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl. The reaction of the pyrimidine (XX) with the tosyl isocyanides (XXI) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 0°C to the boiling point of the reaction mixture, particularly from 25°C to 65°C, in an inert organic solvent using a base. Suitable sol- vents are those capable of dissolving the pyrimidine (XX) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), di- methylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered sol- vents are methanol and ethanol.
Suitable bases are alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCFh), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide ( BuOK), potassium tert-pentoxide and dimethoxymagnesium. Moreover metal carbonates such as caesium carbonate and potassium carbonate. Moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as col- lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to potassium carbonate.
The bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the tosyl isocyanide (XXI), based on the pyrimidine (XX).
Figure imgf000021_0001
The pyrimidines of formula (XX) can be obtained by oxidizing respective pyrimidine alcohols of formula (XXII).
The oxidation of pyrimidines (XXII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 100 °C, particularly at from 0 °C to 75 °C, in an in- ert organic solvent.
The reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XXII) in an organic solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XXII) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCU, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCU, and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, N,N'-dimethyhpropyl- ene urea (DMPU), DMSO and NMP. More preferred solvents halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCU. It is also possible to use mixtures of the solvents men- tioned.
Examples of oxidizing agents for the synthesis of pyrimidines (XX) are metal oxides such as Mhq2, KMhq4, Cr03 or PCC, and non-metal oxides such as NaCIO, Nal04 or pyridine/S03- complex. In addition, methods like the Swern oxidation or the TEMPO oxidation known to a per- son skilled in the art can be used to obtain pyrimidines of formula (XX).
Preferred agents include Mhq2, KMhq4 and PCC, more preferred Mn02.
The oxidizing agent is used preferably from 1 to 50 equivalents based on the pyrimidine (XXII), more preferably at from 1.0 to 20.0 equivalents based on the pyrimidine (XXII), most preferably from 1.0 to 10.0 equivalents based on the pyrimidine (XXII).
The pyrimidines of formula (XXII) can be obtained by reacting respective pyrimidines of for- mula (XVI) with a reducing agent such as LAH or DIBAIH.
Figure imgf000021_0002
The reduction of pyrimidines (XVI) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 60 °C, particularly at from 0 °C °C to 25 °C, in an inert organic solvent.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, 0-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly diethyl ether, dioxane and THF. It is also possible to use mixtures of the solvents mentioned.
Examples of reducing agents for pyrimidines (XVI) include LAH, DIBALH, LiBFU or lithium tri- ethylborohydride. Preferred agents include LAH and DIBALH.
The hydride-source is used preferably from 1 to 10 equivalents based on the pyrimidine (XVI), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (XVI), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XVI).
Process E:
Figure imgf000022_0001
The pyrimidines of formula (XXIII) can be obtained from pyrimidines of formula (XXIV) by known methods e.g using actic acid anhydride/ concentrated sulfuric acid (e.g Godfrey, Alexan- der G. etal. Journal of Organic Chemistry, 68(7), 2623-2632, 2003) or using burgess reagent (e.g. Brain, C. T etal. Synlett, 1642-1644, 1999).
Figure imgf000022_0002
The pyrimidines of formula (XXIV) can be obtained from carboxylic acids of formula (XXV) by reaction with amino ketones of formula (XXVI), wherein R substituents of the amino ketones are indenpendently of each alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloal- kenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl. The reaction of the carbox- ylic acids (XXV) with amino ketones (XXVI, commercially available), is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 60°C, in an inert organic solvent.
Carboxylic acids (XXX) are activated using activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1 H-benzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluronium-hex- afluorophosphate (HBTU), ethyl-3-(3-dimethylaminopropyl)carbodiimid (EDC). The carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chlo- ride. Carbonylimidazoles such as 1 ,T-Carbonyldiimidazol (CDI) may also be used as activating reagent under neutral conditions. Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), di- methylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered sol- vents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned. Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethyla- mine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy- clic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DIPEA.
The bases are generally employed in excess amounts; however, they can also be employed ain equal amounts as the pyrimidine.
Process
Figure imgf000023_0001
The pyrimidines of formula (XI) with R’= alkyl, alkenyl, cycloalkenyl, alkinyl, aryl or heteroaryl can be obtained by reacting respective pyrimidines of formula (XXVII) with X = Cl, Br with bo- ronic acids/esters of formula (XXVIII). The reaction is usually carried out at from 0 °C to the boil- ing point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
The reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) in an organic solvent with or without water as co-solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XXVII) and the boronic acids (XXVIII) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC,
DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as LhO, Na20, K2O, MgO, and CaO, Fe203, Ag20; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3,
CS2CO3, MgC03, and CaC03, as well as alkali metal bicarbonates such as UHCO3, NaHCOs, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hy- droxides, and other metal hydroxides, such as LiOH, NaOH, KOH , Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkali metal or alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03 and alkaline earth metal phosphates such as K3PO4; alkali metal and alkaline earth metal acetates such as sodium acetate. Especially preferred bases are inor- ganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hy- droxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkaline earth metal phosphates such as K3PO4.
The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
The bases are used preferably at from 1 to 10 equivalents based on the pyrimidine (XXVII), more preferably at from 1 .0 to 5.0 equivalents based on the pyrimidine (XXVII), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XXVII).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based cata- lysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenyl- phosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphe- nylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,T-binaphthyl).
The amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyrimidine (XXVII).
The boronic acids/esters (XXVIII) required for the preparation of pyrimidines of formula (XI) are commercially available, known from literature or can easily be prepared analogously to pub- lished procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
Figure imgf000024_0001
The pyrimidines of formula (XXVII) with X = Cl, Br can be obtained from pyrimidines of formula (XV) by known methods e.g using hexachloroethane or dibromochloroethane (Bioorg. Med. Chem. 2010, 18, 4821-4829).
Process G:
Figure imgf000024_0002
The pyrimidines of formula (XI) with R’= OH, SH, ORb, SRb, NR4R5 can be obtained from pyrim- idines of formula (XXVII) with X = Cl, Br by reaction with O-, S- or N-nucleophiles.
The reaction of the pyrimidine with the nucleohpile is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particu- larly from 20°C to 80°C, in an inert organic solvent using a base. Suitable solvents are those ca- pable of dissolving the pyrimidine (XXVII) and the nucleophile at least partly and preferably fully under reaction conditions. Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2H5, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium alkali metal and alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03, as well as al- kali metal bicarbonates such as UHCO3, NaHC03, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate; moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, LHMDS, LDA, NaOCH and K2CO3.
The bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the nucleophile based on the pyrimidine (XXVII).
Process H:
Figure imgf000025_0001
The pyrimidines of formula (XI) with R’ = 1 -hydroxy-alkyl, 1 -hydroxy-aryl, 1-hydroxy-het- eroaryl, 1-hydroxy-heterocyclyl, 1 -hydroxy-cycloalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcar- bonyl, alkinylcarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carbocyclylcar- bonyl and related compounds can also be obtained by reacting respective pyrimidines of for- mula (XV) with a base and an electrophile.
The reaction is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from -78°C to 25°C, particularly from -78°C to 0°C, in an inert or- ganic solvent using a base. Suitable solvents are those capable of dissolving the pyrimidine (XV) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /T-BuLi.
The bases are generally employed in equimolar amounts; however, they can also be em- ployed in excess.
Suitable electrophiles are for example aldehydes and acid anhydrides, which are commercially available.
The starting materials are reacted with one another in equimolar amounts. It may be advanta- geous to employ an excess of base and/or the electrophile based on the pyrimidine (XV).
The end of the reactions can easily be determined by the skilled worker by means of routine methods.
The reaction mixtures are worked up in a customary manner, e.g. by mixing with water, sepa- ration of the phases and, if appropriate, chromatographic purification of the crude product.
Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately el- evated temperature.
If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallization or digestion.
The present invention also provides agrochemical compositions comprising at least one pyrimidine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
The present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyrimidine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat. Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
If the pyrimidine compounds of formula (I) as described herein are capable of forming geomet- rical isomers, e.g. E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
If the pyrimidine compounds of formula (I) as described herein have one or more centres of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions ac- cording to the invention. If the pyrimidine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, more preferably a carboxylic group or a sulphonic group, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cati ons and anions, respectively, have no adverse effect on the activity of the active compounds.
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C4-alkyl, HO-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkyl, HO-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylamm- onium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1- oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-HO-ethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrime- thylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), fur- thermore phosphon-ium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trime- thylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic acids, preferably formate, acetate, propionate and butyrate.
Pyrimidine compounds of formula (I) as described herein having an acidic functionality, prefer- ably a carboxylic group or a sulphonic group, can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with the cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C6-al- kylamides or arylamides, as esters, e.g. as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, e.g. as Ci-Cio-alkylthio esters. Preferred mono- and di-Ci-C6-alkylamides are the CH3 and the dimethyl- amides. Preferred arylamides are, e.g., the anilides and the 2-chloroanilides. Preferred alkyl es- ters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy- Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g. the 2-meth- oxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An ex- ample of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
The organic moieties mentioned in the definition of the variables of the compound of formula I, are - like the term halogen - collective terms for individual enumerations of the individual group members. The term halogen denotes in each case F, Cl, Br, or I. All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix Cn-Cm denot- ing in each case the possible number of carbon atoms in the group.
Examples of such meanings are:
- Ci-C4-alkyl: e.g. CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2, and C(CH3)3; Ci-C6-alkyl: Ci-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1 -methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1 -ethylbutyl, 2-ethylbutyl, 1 , 1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpro- pyl, or 1 -ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 ,1— dimethylethyl, n-pentyl, or n-hexyl;
Ci-C4-haloalkyl: Ci-C4-alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodi- fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di- chloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1 , 1 -difluoroethyl, 2-fluoropropyl, 1 -fluoroisopropyl, 3- fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 3,3-difluoropropyl, 2-chloropropyl, 3-chloro- propyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloro- propyl, 2,2,3,3,3-pentafluoropropyl, 1 -(fluoromethyl)-2-fluoroethyl, 1 -(chloromethyl)-2-chloro- ethyl, 1 -(bromomethyl)-2-bromo-ethyl, 4-fluorobutyl, 4-chlorobutyl, and 4-bromobutyl;
Ci-C6-haloalkyl: Ci-C4-haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-io- dohexyl, and dodecafluorohexyl;
C3-C6-cycloalkyl: monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
C3-C6-halocycloalkyl: C3-C6-cycloalkyl as mentioned above which is partially or fully sub- stituted with fluorine, chlorine, bromine and/or iodine, e.g., 1 -fluorocyclopropyl;
C3-C6-alkenyl: e.g. 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-bu- tenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1 - pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-
1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-3-butenyl,
2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-1 -propenyl, 1 ,2- dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1 - pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl- 4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1 -dimethyl-2-bu- tenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-bu- tenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-bu- tenyl, 2, 3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -bu- tenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 -ethyl-3-butenyl, 2-ethyl-1 - butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-pro- penyl, 1 -ethyl-2-methyl-1 -propenyl, and 1 -ethyl-2-methyl-2-propenyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1 -yl, 3- chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1 -yl, 2,3,3-trichloro-2-en- 1 -yl, 2,3-dichlorobut-2-en-1 -yl, 2-bromoprop-2-en-1 -yl, 3-bromoprop-2-en-1 -yl, 2,3-dibromoprop- 2-en-1 -yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1 -yl, or 2,3-dibromobut-2-en-1 -yl;
C3-C6-alkynyl: e.g. 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4-pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl-2-butynyl, 1 ,1 -dimethyl-3-butynyl, 1 ,2- dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 -butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3- butynyl, 2-ethyl-3-butynyl, and 1 -ethyl-1 -methyl-2-propynyl;
C2-C6-alkynyl: C3-C6-alkynyl as mentioned above and also ethynyl;
C3-C6-haloalkynyl: a C3-C6-alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1 ,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bro- moprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1 , 1 -difluoro- but-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-
1 -yl, or 6-iodohex-5-yn-1 -yl;
Ci-C4-alkoxy: e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy,
2-methylpropoxy, and 1 ,1 -dimethylethoxy;
Ci-C6-alkoxy: Ci-C4-alkoxy as mentioned above, and also, e.g., pentoxy, 1 -methylbut- oxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trime- thylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy, and 1 -ethyl-2-methylpropoxy.
Ci-C4-haloalkoxy: a Ci-C4-alkoxy group as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluorometh- oxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromo- propoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3- trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1 - (fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromomethyl)-2-bromoeth- oxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, and nonafluorobutoxy;
Ci-C6-haloalkoxy: a Ci-C4-haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
Ci -C4-a I ky Ith i o : e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 - methylpropylthio, 2-methylpropylthio, and 1 , 1 -dimethylethylthio;
Ci-C6-alkylthio: Ci-C4-alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hex- ylthio, 1 , 1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2- ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1 -ethyl-1 -methylpropylthio, and 1- ethyl-2-methylpropylthio;
(Ci-C4-alkyl)amino: e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1-dimethylethylamino;
(Ci-C6-alkyl)amino: (Ci-C4-alkylamino) as mentioned above, and also, e.g., pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethyl- propylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethylpropylamino, 1-methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1-dimethylbutyla- mino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1 ,1 ,2-trimethylpropyl- amino, 1 ,2,2-trimethyl-propylamino, 1 -ethyl-1 -methylpropylamino, or 1-ethyl-2-methylpropyla- mino;
di(Ci-C4-alkyl)amino: e.g. N,N-dimethylamino, N,N-diethylamino, N,N-di(1-meth- ylethyl)amino, N,N-dipropylamino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2- methylpropyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-prop- ylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpro- pyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,1-dimethylethyl)-N-methylamino, N-ethyl-N- propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpro- pyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1 ,1-dimethylethyl)amino, N-(1-meth- ylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2- methylpropyl)-N-propylamino, N-(1 ,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-meth- ylethyl)amino, N-(1 -methylethyl)-N-(1 -methylpropyl)amino, N-(1 -methylethyl)-N-(2-methylpro- pyl)amino, N-(1 ,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N- butyl-N-(2-methylpropyl)amino, N-butyl-N-(1 ,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2- methylpropyl)amino, N-(1 ,1-dimethylethyl)-N-(1-methylpropyl)amino, or N-(1 ,1-dimethylethyl)-N- (2-methylpropyl)amino;
di(Ci-C6-alkyl)amino: di(Ci-C4-alkyl)amino as mentioned above, and also, e.g., N-me- thyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-me- thyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1-dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N- methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1 ,1-dimethyl- butyl)amino, N-methyl-N-(1 ,2-dimethylbutyl)amino, N-methyl-N-(1 ,3-dimethylbutyl)amino, N-me- thyl-N-(2,2-dimethylbutyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dime- thylbutyl)amino, N-methyl-N- (l-ethylbutyl)amino, N-methyl-N-(2-ethylbutyl)amino, N-methyl-N- (1 ,1 ,2-trimethylpropyl)amino, N-methyl-N- (1 ,2,2-trimethylpropyl)amino, N-methyl-N-(1 -ethyl-1 - methylpropyl)amino, N-methyl-N- (1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentylamino, N- ethyl-N-(1 -methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N-hexylamino, N- ethyl-N-(1 , 1 -dimethylpropyl)amino, N-ethyl-N-(1 ,2-dimethylpropyl)amino, N-ethyl-N-(1 - methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl)amino, N- ethyl-N-(4-methylpentyl)amino, N-ethyl-N-(1 ,1-dimethylbutyl)amino, N-ethyl-N-(1 ,2-dimethyl- butyl)amino, N-ethyl-N-(1 ,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N- (2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1 -ethylbutyl)amino, N- ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1 ,1 ,2-trimethylpropyl)amino, N-ethyl-N-(1 ,2,2-trime- thylpropyl)amino, N-ethyl-N-(1 -ethyl-1 -methylpropyl)amino, N-ethyl-N-(1 -ethyl-2-methylpro- pyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, N,N-dipentylamino, N-propyl-N-hex- ylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino, or N,N-dihexylamino;
Ci-C6-alkylsulfinyl (Ci-C6-Alkyl-S(=0)-): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1- methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 ,1-di- methylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfi- nyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1 , 1 -dimethylpropylsulfinyl, 1 ,2-dimethylpro- pyl-sulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4- methylpentyl-sulfinyl, 1 , 1 -dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1 ,3-dimethylbutyl-sulfi- nyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutyl-sulfinyl, 1-ethylbutyl- sulfinyl, 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl, 1 ,2,2-trimethylpropylsulfinyl, 1 -ethyl-1 - methyl propyl-sulfinyl, and 1-ethyl-2-methylpropylsulfinyl;
Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1-di- methylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpen- tylsulfonyl, 4-methylpentylsulfonyl, 1 ,1-dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-di- methylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutyl-sul- fonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 ,1 ,2-trimethyl-propylsulfonyl, 1 ,2,2-trimethyl- propylsulfonyl, 1 -ethyl-1 -methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl;
C3-C6-cycloalkyl: a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
C3-C6-cycloalkenyl: 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1- cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadi- enyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 2,5-cyclohexadienyl;
bicyclic ring: a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and inde- pendent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole, 1 ,3-benzoxathiole, indole, indane, [1 ,3]dioxolo[4,5-c]pyridine, [1 ,3]dioxolo[4,5-b]pyridine, 2,3-dihydrofuro[2,3-c]pyridine, furo[2,3-c]pyridine, 2,3-dihydrofuro[2,3-b]pyridine, furo[2,3-b]pyri- dine, 2,3-dihydrofuro[3,2-c]pyridine, furo[3,2-c]pyridine, 2,3-dihydrofuro[3,2-b]pyridine, furo[3,2- b]pyridine, furo[3,2-d]pyrimidine, furo[2,3-d]pyrimidine, 6,7-dihydrofuro[3,2-d]pyrimidine, 5,6-di- hydrofuro[2,3-d]pyrimidine, thieno[3,2-d]pyrimidine, thieno[2,3-d]pyrimidine, 6,7-dihy- drothieno[3,2-d]pyrimidine, 5,6-dihydrothieno[2,3-d]pyrimidine, 2,3-dihydrothieno[2,3-c]pyridine, thieno[2,3-c]pyridine, 2,3-dihydrothieno[2,3-b]pyridine, thieno[2,3-b]pyridine, 2,3-dihy- drothieno[3,2-c]pyridine, thieno[3,2-c]pyridine, 2,3-dihydrothieno[3,2-b]pyridine, thieno[3,2-b]pyr- idine, 1 H-pyrrolo[2,3-c]pyridine, 1 H-pyrrolo[2,3-b]pyridine, 1 H-pyrrolo[3,2-c]pyridine, 1 H-pyr- rolo[3,2-b]pyridine, 1 H-imidazo[4,5-c]pyridine, 1 H-imidazo[4,5-b]pyridine, 3H-imidazo[4,5-c]pyri- dine, 3H-imidazo[4,5-b]pyridine, 1 H-pyrazolo[3,4-b]pyridine, 1 H-pyrazolo[3,4-c]pyridine, 1 H-py- razolo[4,3-b]pyridine, 1 H-pyrazolo[4,3-c]pyridine, 1 H-indazole, benzimidazole, 1 ,2-benzoxazole,
1 .3-benzoxazole, 1 ,3-benzothiazole, 1 ,2-benzothiazole, naphthalene, quinolone, isoquinoline, quinazoline, 1 ,3-benzoxathiole, [1 ,3]oxathiolo[4,5-b]pyridine, [1 ,3]oxathiolo[4,5-c]pyridine,
[1 ,3]oxathiolo[5,4-c]pyridine, [1 ,3]oxathiolo[5,4-b]pyridine, 2,3-dihydro-1 ,4-benzodioxine, 2,3-di- hydro-[1 ,4]dioxino[2,3-b]pyridine, 2,3-dihydro-[1 ,4]dioxino[2,3-c]pyridine;
heterocyclyl: a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
3- or 4-membered heterocycles like 2-oxiranyl, 2-aziridinyl, 2-thiiranyl, 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1 -azetidinyl, 2-azetidinyl, 1-azetinyl, or 2-azetinyl;
5-membered saturated heterocycles like2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahy- drothienyl, 3-tetrahydrothienyl, 1 -pyrrolidinyl,2-pyrrolidinyl, 3-pyrrol i d i nyl , 3-isoxazolidinyl, 4-isox- azolidinyl, 5-isoxazolidinyl, 2-isothiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 1 -pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazoli- dinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1 -imidazolidinyl, 2-imidazoli- dinyl, 4-imidazolidinyl, 3-oxazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 3-thiazol- idinyl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,2,4-oxadiazolidin- 2-yl, 1 ,2,4-oxadiazolidin-4-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,2,4-thiadiazolidin-2-yl, 1 ,2,4-thiadiazoli- din-4-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,2,4-triazolidin-1 -yl, or 1 ,3,4-triazolidin-2-yl;
5-membered partial unsaturated heterocycles like 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4- dihydrofur-2-yl, 2,4-dihydrofur-3-yl, dioxolan-2-yl, 1 ,3-dioxol-2-yl, 2,3-dihydrothien-2-yl, 2,3-dihy- drothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 4,5-dihyd ropyrrol-1 -yl, 4,5-dihydro- pyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-1 -yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydro- pyrrol-3-yl, 2,3-dihydroisoxazol-1 -yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihy- droisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,
4.5-dihydroisoxazol-2-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol- 5-yl, 2,3-dihyd roisothiazol-1 -yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihy- droisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5- yl, 4,5-dihydroisothiazol-1 -yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihyd roi- sothiazol-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihy- dropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4- dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihyd ropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl,
4.5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-1 -yl, 2,3-dihydroimidazol-2- yl, 2,3-dihydroimidazol-3-yl ,2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimid- azol-1 -yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihy- droimidazol-1 -yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,
2.3-d i hyd rooxazol-2-yl , 2 , 3-d i hyd rooxazol-3-yl , 2 , 3-d i hyd rooxazol-4-yl , 2 , 3-d i hyd rooxazol-5-yl ,
3.4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2.3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,
3.4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydrothiazol-5-yl,
3.4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, or 3,4-dihydrothiazol-4-yl;
6-membered saturated heterocycles like 1 -piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,
1 ,3— dioxan— 5— yl, 1 ,4-dioxanyl, 1 ,3-dithian-5-yl, 1 ,3-dithianyl, 1 ,3-oxathian-5-yl, 1 ,4-oxathianyl, 2-tetrahydropyranyl, 3-tetrahydopyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetra- hydrothiopyranyl,4-tetrahydrothiopyranyl, 1 -hexahydropyridazinyl, 3-hexahydropyridazinyl, 4- hexahydropyridazinyl, 1 -hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 1 -piperazinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-1 -yl, 1 ,3,5-hexahy- drotriazin-2-yl, 1 ,2,4-hexahydrotriazin-1 -yl, 1 ,2,4-hexahydrotriazin-3-yl, tetrahydro-1 ,3-oxazin-1 - yl, tetrahydro-1 ,3-oxazin-2-yl, tetrahydro-1 ,3-oxazin-6-yl, 1 -morpholinyl, or 2-morpholinyl, 3-mor- pholinyl;
6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
heteroaryl: a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an ox ygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g. pyrazol-3-yl, pyra- zol-4-yl), isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g. thiazol-2-yl, thiazol-4-yl, thiazol-5-yl), oxadia- zolyl (e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl,
1 .3.4-oxadiazol-2-yl), thiadiazolyl (e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl), triazolyl (e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl); 1 -tetrazolyl; 6-membered aromatic rings like pyridyl (e.g. pyridine-2 -yl, pyridine-3-yl, pyridine-4-yl), pyrazinyl (e.g. pyridazin-3-yl, pyridazin-4-yl), pyrimidinyl (e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl), pyrazin-2-yl, triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl,
1 .2.4-triazi n-5-yl , 1 ,2,4-triazin-6-yl).
The term“substituted” if not specified otherwise refers to substituted with 1 , 2, or up to maxi- mum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not men- tioned otherwise.
The term“acidic functionality” if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H+), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
The terms“compounds of formula (I)”,“Pyrimidine compounds of formula (I)”,“Compounds I” ‘compounds of formula I” and“compounds of invention” are synonyms.
The term“cyclic groups” comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another.
In general, pyrimidine compounds of formula (I) are suitable as herbicides. According to a preferred embodiment of the invention preference is given pyrimidine corn- pounds of formula (I), and their use as herbicides, wherein the variables, either independently of one another or in combination with one another, have the following meanings:
in one embodiment of the compound of formula (I), R1 is not fluoromethyl, difluoromethyl, tri- fluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, 1 ,1 ,2,2,-tetrafluoroethyl, 1 -trifluoromethyl-1 ,2,2,2-tetrafluoro- ethyl and undecafluoropentyl;
in another embodiment of the compound of formula I, R1 is not 1 ,1 ,2,2,-tetrafluoroethyl;
preferred Rx is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halocycloalkenyl;
wherein the cyclic groups of Rx are unsubstituted or substituted with Re;
also preferred Rx is Ci-C6-haloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halocy- cloalkenyl;
also preferred Rx is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocy- cloalkyl;
also preferred Rx is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or C3-C6-cycloalkyl;
also preferred Rx is H, halogen, Ci-C6-alkyl, or C3-C6-cycloalkyl;
also preferred Rx is H, Ci-C6-alkyl, or Ci-C6-haloalkyl;
also preferred Rx is H, halogen, Ci-C6-alkyl;
also preferred Rx is H, or Ci-C6-alkyl;
also preferred Rx is H or halogen;
more preferred Rx is H;
also more preferred Rx is Ci-C6-alkyl e.g. CH3, C2H5, i-C3H7, n-C4H9, and 1-C4H9;
also more preferred Rx is C3-C6-cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C3H5, C-C4H7, and C-C5H9;
also more preferred Rx is halogen;
also more preferred Rx is Ci-C6-haloalkyl e.g. CHF2, CHF2, and CF3;
also more preferred Rx is C3-C6-halocycloalkyl;
also more preferred Rx is H, CH3, C2H5, F, i-C3H7 , CHF2, CHF2, or c-C3H5;
preferred R^ is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halocycloalkenyl;
wherein the cyclic groups of R y are unsubstituted or substituted with Re;
also preferred R^ is H, Ci-C6-haloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halo- cycloalkenyl;
also preferred R^ is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocy- cloalkyl;
also preferred R^ is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or C3-C6-cycloalkyl;
also preferred R^ is H, halogen, Ci-C6-alkyl, or C3-C6-cycloalkyl;
also preferred R^ is H, Ci-C6-alkyl, or Ci-C6-haloalkyl;
also preferred R^ is H, halogen, Ci-C6-alkyl;
also preferred R^ is H, or Ci-C6-alkyl;
also preferred R y is H or halogen;
more preferred Ry is H;
also more preferred R^ is Ci-C6-alkyl e.g. CH3, C2H5, i-C3H7, n-C4Hg, and 1-C4H9; also more preferred Ry is C3-C6-cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C3H5, C-C4H7, and C-C5H9;
also more preferred Ry is halogen;
also more preferred Ry is Ci-C6-haloalkyl e.g. CHF2, CHF2, and CF3;
also more preferred Ry is C3-C6-halocycloalkyl;
also more preferred Ry is H, CH3, C2H5, F, 1-C3H7 , CHF2, CHF2, or c-C3H5;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 Re;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, Re;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, Re; also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is unsubstituted;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- membered saturated carbocyclic ring, wherein the ring is unsubstituted;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, Re;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, Re;
also preffered is the R1 wherein Rx and Ry together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
also preffered is the R1 wherein Rx and R y together with the carbon they are attached form a 3- membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
more preffered R1 is CF2CH3, 1-F-isopropyl or 1-F-cyclopropyl;
preferred R2 is selected from R2-1 to R2-43 as shown below, wherein W, X, and Y denotes R20 which independently of each other are identical or different;
Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenylcar- bonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6-alkyl)amino- sulfonyl, or Ci-C6-alkylaminosulfonyl;
Figure imgf000035_0001
Figure imgf000036_0001
preferred R2 is R2-5, R2-6, R2-7, R2-20, R2-21 , or R2-22; also preferred R2 is R2-5, R2-6, or R2-7;
also preferred R2 is R2-20, R2-21 , or R2-22;
more preferred R2 is R2-5, R2-7 or R2-20;
most preferred R2 is R2-5;
also most preferred R2 is R2-6;
also most preferred R2 is R2-7;
also most preferred R2 is R2-20; preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkylsulfinyl, Ci-C6- alkylsulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, aminocarbonyl, Ci-C6-alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (HO)2(0)P, (Ci-C6-alkoxy)2(0)P, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein, cyclic groups of X are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X are unsubstituted or substituted with Rd;
particularly preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci- C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkyl- sulfinyl, Ci-C6-alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of X are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X are unsubstituted or substituted with Rd;
also particularly preferred X is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with Rc;
also particularly preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy- (Ci-C4-alkoxy)n, ORb, SH, or SRb, wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with Rd;
also more preferred X is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(Ci-C4- alkoxy)n, Ci-C6-haloalkoxy;
more particularly preferred X is H;
also more particularly preferred X is halogen;
also more particularly preferred X is Ci-C6-alkyl;
also more particularly preferred X is Ci-C6-haloalkyl;
also more particularly preferred X is Ci-C6-haloalkoxy;
most particularly preferred X is Ci-C6-alkyl, preferably CH3, C2H5, n-propyl, CH(CHs)2, n-butyl, isobutyl;
also preferred X is H, Ci-C4-alkyl, Ci-C2-fluoroalkyl, Ci-C4-alkoxy, or Ci-C4-alkylthio;
especially preferred X is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH3;
most especially preferred X is H, CH3, C2H5, n-propyl, isopropyl, OCH3, or SCH3;
most preferred X is H, halogen, CH3, C2H5, OH, or OCH3;
also most preferred X is H, CH3, C2H5, or SCH3;
also most preferred X is H, CH3, C2H5, F, Cl, Br, or I;
also most preferred X is H, CH3, or C2H5;
most particularly preferred X is H;
also most particularly preferred X is CH3;
also most particularly preferred X is C2H5;
preferred Y is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkylsulfinyl, Ci-C6- alkylsulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, aminocarbonyl, Ci-C6-alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (HO)2(0)P, (Ci-C6-alkoxy)2(0)P, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein, cyclic groups of Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of Y are unsubstituted or substituted with Rd; particularly preferred Y is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci- C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkyl- sulfinyl, Ci-C6-alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of Y are unsubstituted or substituted with Rd;
also particularly preferred Y is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with Rc;
also particularly preferred Y is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy- (Ci-C4-alkoxy)n, ORb, SH, or SRb, wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with Rd;
also more preferred Y is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(C-i-C4- alkoxy)n, Ci-C6-haloalkoxy;
more particularly preferred Y is H;
also more particularly preferred Y is halogen;
also more particularly preferred Y is Ci-C6-alkyl;
also more particularly preferred Y is Ci-C6-haloalkyl;
also more particularly preferred Y is Ci-C6-haloalkoxy;
most particularly preferred Y is Ci-C6-alkyl, preferably CH3, C2H5, n-propyl, CH(CHs)2, n-butyl, isobutyl;
also preferred Y is H, Ci-C4-alkyl, Ci-C2-fluoroalkyl, Ci-C4-alkoxy, or Ci-C4-alkylthio;
especially preferred Y is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH3;
most especially preferred Y is H, CH3, C2H5, n-propyl, isopropyl, OCH3, or SCH3;
most preferred Y is H, halogen, CH3, C2H5, OH, or OCH3;
also most preferred Y is H, CH3, C2H5, or SCH3;
also most preferred Y is H, CH3, C2H5, F, Cl, Br, or I;
also most preferred Y is H, CH3, or C2H5;
most particularly preferred Y is H;
also most particularly preferred Y is CH3;
also most particularly preferred Y is C2H5;
preferred W is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkylsulfinyl, Ci-C6- alkylsulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, aminocarbonyl, Ci-C6-alkylcarbonyl, C1-C6- alkylcarbonylaminocarbonyl, hydroxya mi nocarbonyl, (H0)2(0)P, (Ci-C6-alkoxy)2(0)P, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein, cyclic groups of X are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X are unsubstituted or substituted with Rd;
particularly preferred W is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy-(Ci- C4-alkoxy)n, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Ci-C6-alkyl- sulfinyl, Ci-C6-alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein, cyclic groups of X are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X are unsubstituted or substituted with Rd;
also particularly preferred W is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl which are unsubstituted or substituted with Rc; also particularly preferred W is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy- (Ci-C4-alkoxy)n, ORb, SH, or SRb, wherein alkyl or alkoxy groups of X are unsubstituted or sub- stituted with Rd;
also more preferred W is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(C-i-C4- alkoxy)n, Ci-C6-haloalkoxy;
more particularly preferred W is H;
also more particularly preferred W is halogen;
also more particularly preferred W is Ci-C6-alkyl;
also more particularly preferred W is Ci-C6-haloalkyl;
also more particularly preferred W is Ci-C6-haloalkoxy;
most particularly preferred W is Ci-C6-alkyl, preferably CH3, C2H5, n-propyl, CH(CHs)2, n-butyl, isobutyl;
also preferred W is H, Ci-C4-alkyl, Ci-C2-fluoroalkyl, Ci-C4-alkoxy, or Ci-C4-alkylthio;
especially preferred W is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH3;
most especially preferred W is H, CH3, C2H5, n-propyl, isopropyl, OCH3, or SCH3;
most preferred W is H, halogen, CH3, C2H5, OH, or OCHs;
also most preferred W is H, CH3, C2H5, or SCH3;
also most preferred W is H, CH3, C2H5, F, Cl, Br, or I;
also most preferred W is H, CH3, or C2H5;
most particularly preferred W is H;
also most particularly preferred W is CH3;
also most particularly preferred W is C2H5;
preferred Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl- carbonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, or Ci-C6-alkylaminosulfonyl;
more preferred Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C6-alkylcarbonyl;
also more preferred Q is H, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6- alkyl, or Ci-C6-alkylaminosulfonyl;
most preferred Q is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, or t-butyl;
particularly preferred Q is H;
preferred Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-ami- nocarbonyl, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het- erocyclyl;
more preferred Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
most preferred Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, 5- or 6-membered het- eroaryl, or 3- to 6-membered heterocyclyl;
preffered Rc is halogen, CN, OH, Ci-C6-alkyl or Ci-C6-alkoxy, Ci-C6-haloalkoxy, or NH2;
preffered Rc is Ci-C6-alkyl or Ci-C6-alkoxy;
more preffered Rc is Ci-C6-alkyl;
preffered Rd is CN, OH, halogen, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, Ci-C6-haloalkoxy, NH2, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered het- eroaryl, or 3- to 6-membered heterocyclyl, or phenylthio;
more preffered Rd is halogen, Ci-C6-alkoxy, or phenylthio; most preffered Rd is halogen or Ci-C6-alkoxy;
preffered Re is halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
more preffered Re is halogen, CN, OH, Ci-C6-alkoxy or Ci-C6-alkyl;
most preffered Re is OH or Ci-C6-alkoxy;
most preffered Re is halogen;
preffered Rf is H, halogen, CN, OH, Ci-C6-alkyl, or Ci-C6-alkoxy;
more preffered Rf is OH, Ci-C6-alkyl, or Ci-C6-alkoxy;
most preffered Rf is OH or Ci-C6-alkoxy.
In a preferred embodiment of compounds of formula (I), and their use as herbicide, wherein R2 is selected from formulae R2-1 to R2-43;
Q is H, Ci-C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, or Ci-C6-alkylaminosul- fonyl;
X , Y and W independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hy- droxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C3- C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy, Ci-C6-alkoxy-(Ci-C4- alkoxy)n, SH, NH2, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)(Ci-C6- alkoxy)amino, Ci-C6-alkylthio, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkylsulfinyl, Ci-C6-alkyl- sulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-ami- nocarbonyl, C1-C6-alkylcarbonylaminocarbonyl, Ci-C6-haloalkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, C3-C6- cycloalkylcarbonylamino, Ci-C6-alkylsulfonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcar- bonyl(Ci-C6-alkyl)amino, Ci-C6-alkylaminocarbonylamino, Ci-C6-dialkylaminocarbonyla- mino, Ci-C6-alkoxycarbonylamino, hydroxycarbonyl-Ci-C6-alkyl, hydroxcarbonyl-Ci-C6- haloalkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-haloal- kyl, Ci-C6-dialkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-dialkylaminocarbonyl-Ci-C6-haloalkyl, hydroxyCi-C6-alkyl, Ci-C6-alkylcarbonylalkyl, cyano-Ci-C6-alkyl, phenyl, phenoxy, phenyl- Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl- Ci-C6-alkyl, 3- to 6-membered heterocyclyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl- carbonyl,C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, 3- to 6-membered hetero- cyclyloxy, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, (HO)2(0)P, (HO)(Ci-C6-alkoxy)(0)P, or (Ci-C6-alkoxy)2(0)P;
wherein
cyclic groups of X, Y, and W are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X, Y, and W are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio.
In a preferred embodiment of compounds of formula (I), and their use as herbicide, wherein Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; X is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, Ci-C6-haloalkoxy or phenyl, preferably H or Ci-C6-alkyl, more prefera- bly H, CH3, C2H5, or n-propyl;
Y is H, C2-C6-alkenyl, C2-C6-alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6- alkenyloxy, C3-C6-alkinyloxy, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, SH, NH2, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)(Ci-C6-alkoxy)amino, Ci-C6-alkylthio, Ci-C6-alkylthio- Ci-C6-alkyl, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-al- kylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkyla- minocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, C1-C6-alkylcarbonyl- aminocarbonyl, Ci-C6-haloalkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, C3-C6-cycloalkylcarbonylamino, Ci-C6-alkylsulfonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)ami- nocarbonyl Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonyl(Ci-C6-alkyl)amino, C1- C6-alkylaminocarbonylamino, Ci-C6-dialkylaminocarbonylamino, Ci-C6-alkoxycarbonyl- amino, hydroxycarbonyl-Ci-C6-alkyl, hydroxcarbonyl-Ci-C6-haloalkyl, Ci-C6-alkyla- minocarbonyl-Ci-C6-alkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-haloalkyl, Ci-C6-dialkyla- minocarbonyl-Ci-C6-alkyl, Ci-C6-dialkylaminocarbonyl-Ci-C6-haloalkyl, hydroxyCi-C6- alkyl, Ci-C6-alkylcarbonylalkyl, cyano-Ci-C6-alkyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl-Ci-C6-al- kyl, 3- to 6-membered heterocyclyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, 5- or 6- membered heteroaryl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl- carbonyl,C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, 3- to 6-membered het- erocyclyloxy, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, (HO)2(0)P, (HO)(OI-OQ- alkoxy)(0)P or (Ci-C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio.
In another preferred embodiment of compounds of formula (I), and their use as herbicide, wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20;
X is H, Ci-C6-alkyl, hydroxycarbonyl, or phenyl, preferably H or Ci-C6-alkyl, more prefera- bly H, CH3, C2H5, or n-propyl;
Y is H, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n,
NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hy- droxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci- C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkyla- minocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6- alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-al- kylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered hetero- cyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (Ci-C6-alkoxy)2(0)P; wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio.
Preffered R4 and R5 are independently from each other selected from hydrogen, OH, OI-OQ- alkyl, NH2, Ci-C6-alkylcarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkoxycar- bonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroaryl- sulfonyl, 3- or 6-membered heterocyclylsulfonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6-cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, and di(Ci-C6-alkyl)aminocarbonyl;
more preffered R4 and R5 are independently from each other selected from hydrogen, OH, Ci- C6-alkyl, NH2, Ci-C6-alkylcarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkoxycar- bonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, Ci-C6-alkylaminocarbonyl, and di(Ci-C6-al- kyl)aminocarbonyl;
most preffered R4 and R5 are independently from each other selected from OH, Ci-C6-alkylcar- bonyl, Ci-C6-alkylsulfonyl, and Ci-C6-haloalkylsulfonyl.
Preferred R3 are selected from halogen, CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, and C3-C6-cycloalkyl;
also preferred R3 are selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, and Ci-C6-alkoxy; particularly preferred R3 are selected from halogen, Ci-C6-alkyl, and Ci-C6-haloalkyl;
also particularly preferred R3 are selected from halogen, and Ci-C6-alkyl;
especially preferred R3 is halogen, CH3, or CF3;
also especially preferred R3 is halogen;
more preferred R3 are selected from Cl, Br, and F;
most preferred R3 is Br or I;
also more preferred R3 is Br or Cl;
also most preferred R3 is Br;
also most preferred R3 is Cl;
also most preferred R3 is F.
Preferred Z is phenyl or 5- or 6-membered heteroaryl ring;
also preferred Z is phenyl or 9- or 10-membered partially or fully unsaturated bicyclic ring con- taining 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
also preferred Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered partially or fully unsaturated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; more preferred Z is phenyl substituted independently of their position with 0, 1 , 2, 3, or 4 R3; most preferred Z is phenyl which is substituted at ortho position to the bond attached to pyrimi- dine ring with at least one R3, and which phenyl ring is further substituted with 0, 1 , 2, or 3 R3; particularly preferred Z[i.e. the group“Z-(R3)m”] is formula W1,
Figure imgf000042_0001
wherein R3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, preferrably 0 or 1 ; and
# denotes the point of attachment to the pyrimidine ring;
also particularly preferred Z[i.e. the group“Z-(R3)m”] is formula W1-A,
Figure imgf000043_0001
wherein R3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and
# denotes the point of attachment to the pyrimidine ring;
also particularly preferred Z[i.e. the group“Z-(R3)m”] is formula W1-B,
Figure imgf000043_0002
wherein R3 same or differently are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z [i.e. the group“Z-(R3)m”] is formula W1a
Figure imgf000043_0003
wherein
R3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1- C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1- C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; R3b and R3c each independently is H, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloal- kynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3- C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R3b and R3c are independently unsubstituted or substituted with substituents Re; and
# denotes the point of attachment to the pyrimidine ring;
also more preferred Z is 5- or 6-membered heteroaryl ring;
most preferred Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine; particularly preferred Z is pyrimidine or pyridine;
especially preferred Z is pyridine;
most preferred Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole; particularly preferred Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thio phene, furan, or pyrrole;
especially preferred Z is thiophene, furan, or pyrrole;
particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from below groups A to G,
Figure imgf000044_0001
wherein
R3 is halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0 or 1 ;
X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from below groups A1 to G1 ,
Figure imgf000044_0002
wherein
R3 is halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
R3b is H, halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy; X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from A, B, C, and D;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is A or C;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from E, F, and G;
also most particularly preferred Z[i.e. the group“Z-(R3)m”] is E or G;
more particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from A1 , B1 , C1 , and D1 ; most particularly preferred Z[i.e. the group“Z-(R3)m”] is A1 or C1 ;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is selected from E1 , F 1 , and G1 ; also most particularly preferred Z[i.e. the group“Z-(R3)m”] is E1 or G1 ;
also more preferred Z is 9- or 10-membered partially or fully unsaturated bicyclic ring contain- ing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
also more preferred Z is 9- or 10-membered partially or fully unsaturated bicyclic ring, wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 het- eroatoms selected from O or N;
particularly preferred Z is 9 membered bicyclic ring;
more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsatu- rated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N; also more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
most particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered car- bocycle comprising 1 or 2 oxygen atoms;
also more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 heteroatoms se- lected from O or N;
also most particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
particularly preferred Z is 10 membered bicyclic ring;
more particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N;
also more particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms; most particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
more preferred Z[i.e. the group“Z-(R3)m”] is selected from below groups H to V,
Figure imgf000046_0001
wherein
Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
R3 same or differently are selected from halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, and Ci- C6-alkoxy;
m is 0, 1 or 2;
R4 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z[i.e. the group“Z-(R3)m”] is selected from groups H to V,
wherein
Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
R3 same or differently are selected from halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, and Ci- C6-alkoxy;
m is 0, 1 or 2;
X1 is O, S, or NR3A; R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z[i.e. the group“Z-(R3)m”] is selected from below groups H1 to V1 ,
Figure imgf000047_0001
wherein
Y1 is 5- or 6-membered fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
R3b and R3c each independently is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or C1-C6- alkoxy ;
X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
Preferred Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
particularly preferred Y1 is phenyl;
also particularly preferred Y1 is 5-membered partially or fully unsaturated carbocycle compris- ing 1 , or 2 heteroatoms selected from O, N, and S; more preferred Y1 is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3-di- hydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole ; more preferably heteroatoms are selected from O and S, e.g. 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3-dihydrofuran, or 2,3-dihydrothio- phene; most preferred heteroatom in Y1 is O, e.g. 1 ,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y1 is S, e.g. 2,3-dihydrothiophene;
also more preferred Y1 is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole,
1 ,2-thiazole, 1 ,3-thiazole, imidazole, 1 H-pyrazole); more preferably heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
most preferred Y1 is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
also particularly preferred Y1 is 6-membered partially or fully unsaturated carbocycle compris- ing 0, 1 , or 2 heteroatoms selected from O, N, and S;
more preferred Y1 is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y1 is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms N;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is H, I, J, K, L, M, N, O, P, Q, or R; most particularly preferred Z[i.e. the group“Z-(R3)m”] is H, L, or M;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is H;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is H or W1;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is S, T, U, or V;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is H1 , 11 , J1 , K1 , L1 , M1 , N1 , 01 ,
P1 , Q1 , or R1 ;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is H1 , L1 , or M1 ;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is H 1 ;
most particularly preferred Z[i.e. the group“Z-(R3)m”] is H1 or W1 a;
also more particularly preferred Z[i.e. the group“Z-(R3)m”] is S1 , T1 , U1 , or V1 ;
most preferred Z[i.e. the group“Z-(R3)m”] is H 1 , 11 , K1 , L1 and R1 ;
preferred m is 0, 1 , 2, or 3;
more preferred m is 0, 1 , or 2;
most preferred m is 0;
also most preferred m is 1 ;
also most preferred m is 2;
preferred n is 0, 1 , 2, or 3;
more preferred n is 0, 1 , or 2;
most preferred n is 0;
also most preferred n is 1 ;
also most preferred n is 2.
Also preferred are compounds of formula (I), and their use as herbicide, wherein Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl , or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; wherein
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci- C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2- C6-alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1- C6-alkoxy-(Ci-C4-alkoxy)n, SH, NH2, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, (O-I-OQ- alkyl)(Ci-C6-alkoxy)amino, Ci-C6-alkylthio, Ci-C6-alkylthio-Ci-C6-alkyl, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, C1-C6-alkylcarbonylaminocarbonyl, Ci-C6-haloalkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, C3-C6-cycloalkylcarbonylamino, Ci-C6-alkylsulfonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6- alkylsulfonyl)aminocarbonyl Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonyl(Ci-C6- alkyl)amino, Ci-C6-alkylaminocarbonylamino, Ci-C6-dialkylaminocarbonylamino, C1-C6- alkoxycarbonylamino, hydroxycarbonyl-Ci-C6-alkyl, hydroxcarbonyl-Ci-C6-haloalkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-haloalkyl, C1- C6-dialkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-dialkylaminocarbonyl-Ci-C6-haloalkyl, hydroxyCi-C6-alkyl, Ci-C6-alkylcarbonylalkyl, cyano-Ci-C6-alkyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl-Ci-C6-alkyl, 3- to 6-membered heterocyclyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci- C6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl, 3- to 6- membered heterocyclylcarbonyl,C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, 3- to 6-membered heterocyclyloxy, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, (HO)2(0)P, (HO)(Ci-C6-alkoxy)(0)P or (Ci-C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z [i.e. the group“Z-(R3)m”] is formula W1 or H wherein m is 0 or 1 ; and R3 is halogen, O-I-OQ- alkyl, or Ci-C6-haloalkyl.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; wherein
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, SH, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, O C6-alkylsulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, ami- nocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkylcarbonyl- aminocarbonyl, hydroxya mi nocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonyla- mino, Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonyl(Ci-C6-alkyl)amino, hydroxcar- bonyl-Ci-C6-alkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-dialkylaminocarbonyl-Ci- C6-alkyl, hydroxyCi-C6-alkyl, cyano-Ci-C6-alkyl, phenyl-Ci-C6-alkyl, 5- or 6-membered het- eroaryl-Ci-C6-alkyl, 3- to 6-membered heterocyclyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-al- kyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl, C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, or 3- to 6-membered heterocyclyloxy;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z [i.e. the group“Z-(R3)m”] is formula W1 or H wherein m is 0 or 1 ; and R3 is halogen, O-I-OQ- alkyl, or Ci-C6-haloalkyl.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; wherein
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, O-I-OQ- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, SH, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, ami- nocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkylcarbonyl- aminocarbonyl, hydroxya mi nocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonyla- mino, Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonyl(Ci-C6-alkyl)amino, hydroxcar- bonyl-Ci-C6-alkyl, Ci-C6-alkylaminocarbonyl-Ci-C6-alkyl, Ci-C6-dialkylaminocarbonyl-Ci- C6-alkyl, hydroxyCi-C6-alkyl, cyano-Ci-C6-alkyl, phenyl-Ci-C6-alkyl, 5- or 6-membered het- eroaryl-Ci-C6-alkyl, 3- to 6-membered heterocyclyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-al- kyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl, C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, or 3- to 6-membered heterocyclyloxy;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z [i.e. the group“Z-(R3)m”] is formula W1 or H wherein m is 0 or 1 ; and R3 is halogen, C1-C6- alkyl, or Ci-C6-haloalkyl.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
R1 is 1-F-cyclopropyl; R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; wherein
X and Y independently are selected from H, Ci-C6-alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2- aminocarbonyl, hydroxya mi nocarbonyl, C3-C6-cycloalkylaminocarbonyl, C1-C6- alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6- alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered
heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (Ci-C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z [i.e. the group“Z-(R3)m”] is formula W1 or H wherein m is 0 or 1 ; and R3 is halogen, O-I-OQ- alkyl, or Ci-C6-haloalkyl.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
R1 is 1 -F-isopropyl;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; wherein
X and Y independently are selected from H, Ci-C6-alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci- C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, O-I-OQ- alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C1-C6- alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6- alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered
heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (Ci-C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z [i.e. the group“Z-(R3)m”] is formula W1 or H wherein m is 0 or 1 ; and R3 is halogen, C1-C6- alkyl, or Ci-C6-haloalkyl.
Also preferred are compounds of formula (I), which correspond to formula (1.1 ), and their use as herbicide,
Figure imgf000052_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20;
Z [i.e. the group“Z-(R3)m”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 1 or 2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein Z [i.e. the group“Z-(R3)m”] is formula W1, which correspond to formula (I.A), and their use as herbicide,
Figure imgf000052_0003
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 0, 1 or 2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) which corresponds to formula (I.B), and their use as herbicide,
Figure imgf000052_0002
wherein
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; Z [i.e. the group“Z-(R3)m”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci- C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-ami- nocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonyla- mino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-mem- bered heteroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1- C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2, or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein Z is W1, which corresponds to formula (I.B.1 ), and their use as herbicide,
Figure imgf000053_0001
wherein
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci- C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-ami- nocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonyla- mino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-mem- bered heteroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1- C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2, or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) which corresponds to formula (I.B.2), and their use as herbicide,
Figure imgf000054_0001
wherein
Z [i.e. the group“Z-(R3)m”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H or Ci-C6-alkyl, preferably CH3 or C2H5;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) which corresponds to formula (I.C), and their use as herbicide,
Figure imgf000054_0002
wherein
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20; Z[i.e. the group“Z-(R3)m”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2; X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci- C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-ami- nocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonyla- mino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-mem- bered heteroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1- C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.C.1 ), and their use as herbicide,
Figure imgf000055_0001
wherein
R2 is R2-5, R2-6, R2-7, R2-20, R2-21 or R2-22, R2 is more preferably R2-5, R2-7, or R2-20;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, O-I-OQ- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy; Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) which corresponds to formula (I.C.2), and their use as herbicide,
Figure imgf000056_0002
wherein
Z[i.e. the group“Z-(R3)m”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H or Ci-C6-alkyl, preferably CH3 or C2H5;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-5, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.D), and their use as herbicide,
Figure imgf000056_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloal- kyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-5, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.D.1 ), and their use as herbicide,
Figure imgf000057_0002
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)C ºCH, SH, NHCHs, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or
CON(CH3)2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-20, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.E), and their use as herbicide,
Figure imgf000057_0001
wherein Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-20, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.E.1 ), and their use as herbicide,
Figure imgf000058_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2Cº CH, CH(CH3)CºCH, SH, NHCHs, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or CON(CH3)2; more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-7, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.F), and their use as herbicide,
Figure imgf000059_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci- C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-ami- nocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonyla- mino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-mem- bered heteroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1- C6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2 or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-7, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.F.1 ), and their use as herbicide,
Figure imgf000059_0002
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)C ºCH, SH, NHCH3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or
CON(CH3)2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-22, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.G), and their use as herbicide,
Figure imgf000060_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2, or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio; more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-22, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.G.1 ), and their use as herbicide,
Figure imgf000061_0002
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)C ºCH, SH, NHCH3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or
CON(CH3)2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-21 , Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.H), and their use as herbicide,
Figure imgf000061_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2, or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-21 , Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I.H.1 ), and their use as herbicide,
Figure imgf000062_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)C ºCH, SH, NHCHs, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or
CON(CH3)2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-6, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (I. I), and their use as herbicide,
Figure imgf000062_0002
wherein Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, C1-C6- alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2-aminocar- bonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, Ci-C6-alkylcarbonylamino, Ci-C6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-Ci-C6-alkyl, phenyl-Ci-C6-alkylthio, phenylthio-Ci-C6-alkyl, 5- or 6-membered het- eroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(Ci-C6-alkoxy)(0)P or (C1-C6- alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 0, 1 , 2, or 3;
Rc is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, or Ci-C6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-6, Z[i.e. the group“Z-(R3)m”] is W1, which corresponds to formula (1.1.1 ), and their use as herbicide,
Figure imgf000063_0001
wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X and Y independently are selected from H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CHF2, CF3, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, CON(CH3)2, CHCH2, C(CH3)CH2, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), CºCH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)C ºCH, SH, NHCHs, N(CH3)2, COOH, COOCH3, COOC2H5, CONH2, CONHCH3, or
CON(CH3)2;
more preferably, when m is 2, R3 each independently is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein,
R1 is CF2CH3, 1-F-isopropyl, or 1-F-cyclopropyl; R2 is R2-5, R2-6, R2-7, R2-20, R2-21 , or R2-22; wherein X and Y independently are selected from H, CH3, and C2H5;
Z[i.e. the group“Z-(R3)m”] is selected from 2-CI-C6H4, 2-Br-C6H4, 2-CH3-C6H4, 2-CI-4-F-C6H3, 2-CI-5-CF3-C6H3, 2-CI-5-F-C6H3, 3-CI-2-naphthyl, and 3-CH3-2-naphthyl.
According to a particularly preferred embodiment of the compounds of formula I and their use as herbicide, compounds of the invention are the compounds of the formulae I that are compiled in the Tables 1 to 144, wherein the meaning for the combination of variables X and Y of R2 for each individual compound of tables 1 to 144 corresponds to each row of Table A.
Each of the groups mentioned for a substituent in the tables is furthermore per se, inde- pendently of the combination in which it is mentioned, a particularly preferred aspect of the sub- stituent in question.
Table 1 . Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-CI-C6H4 (com- pounds of formula 1 .1 );
Table 2. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-Br-CeH4 (com- pounds of formula 1 .2);
Table 3. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-CH3-C6H4 (com- pounds of formula 1 .3);
Table 4. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-CI-4-F-C6H3 (com- pounds of formula 1 .4);
Table 5. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-CI-5-CF3-C6H3
(compounds of formula 1 .5);
Table 6. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 2-CI-5-F-C6H3 (com- pounds of formula 1 .6);
Table 7. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 3-CI-2-naphthyl (com- pounds of formula 1 .7);
Table 8. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-5, Z is 3-CH3-2-naphthyl
(compounds of formula 1 .8);
Table 9. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-CI-C6H4 (com- pounds of formula 1 .9);
Table 10. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-Br-CeH4 (corn- pounds of formula 1 .10);
Table 1 1 . Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-CH3-C6H4 (corn- pounds of formula 1 .1 1 );
Table 12. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-CI-4-F-C6H3 (corn- pounds of formula 1 .12);
Table 13. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-CI-5-CF3-C6H3 (compounds of formula 1 .13);
Table 14. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 2-CI-5-F-C6H3 (corn- pounds of formula 1 .14);
Table 15. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 3-CI-2-naphthyl (compounds of formula 1 .15);
Table 16. Compounds of formula I, wherein R1 is CF2CH3, R2 is R2-6, Z is 3-CH3-2-naphthyl (compounds of formula 1 .16); Table 17. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-CI-C6H4 (com- pounds of formula 1 .17);
Table 18. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-Br-C6H4 (com- pounds of formula 1 .18);
Table 19. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-CH3-C6H4 (com- pounds of formula 1 .19);
Table 20. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-CI-4-F-C6H3 (com- pounds of formula 1 .20);
Table 21 . Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-CI-5-CF3-C6H3 (compounds of formula 1 .21 );
Table 22. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 2-CI-5-F-C6H3 (com- pounds of formula 1 .22);
Table 23. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 3-CI-2-naphthyl (compounds of formula 1 .23);
Table 24. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-7, Z is 3-CH3-2-naphthyl (compounds of formula 1 .24);
Table 25. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-CI-C6H4 (com- pounds of formula 1 .25);
Table 26. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-Br-C6H4 (com- pounds of formula 1 .26);
Table 27. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-CH3-C6H4 (com- pounds of formula 1 .27);
Table 28. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .28);
Table 29. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-CI-5-CF3-C6H3 (compounds of formula 1 .29);
Table 30. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .30);
Table 31 . Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 3-CI-2-naphthyl (compounds of formula 1 .31 );
Table 32. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-20, Z is 3-CH3-2-naphthyl (compounds of formula 1 .32);
Table 33. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-CI-C6H4 (com- pounds of formula 1 .33);
Table 34. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-Br-C6H4 (com- pounds of formula 1 .34);
Table 35. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-CH3-C6H4 (com- pounds of formula 1 .35);
Table 36. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-CI-4-F-C6H3 (compounds of formula 1 .36);
Table 37. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-CI-5-CF3-C6H3 (compounds of formula 1 .37);
Table 38. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 2-CI-5-F-C6H3 (compounds of formula 1 .38); Table 39. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 3-CI-2-naphthyl (compounds of formula 1 .39);
Table 40. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-21 , Z is 3-CH3-2-naphthyl (compounds of formula 1 .40);
Table 41 . Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-CI-C6H4 (com- pounds of formula 1 .41 );
Table 42. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-Br-CeH4 (com- pounds of formula 1 .42);
Table 43. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-CH3-C6FU (com- pounds of formula 1 .43);
Table 44. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .44);
Table 45. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-CI-5-CF3-C6H3 (compounds of formula 1 .45);
Table 46. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .46);
Table 47. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 3-CI-2-naphthyl (compounds of formula 1 .47);
Table 48. Compounds of formula , wherein R1 is CF2CH3, R2 is R2-22, Z is 3-CH3-2-naphthyl (compounds of formula 1 .48);
Table 49. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-CI-C6FU (compounds of formula 1 .49);
Table 50. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-Br-CeH4 (compounds of formula 1 .50);
Table 51 . Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-CH3-C6FU (compounds of formula 1 .51 );
Table 52. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .52);
Table 53. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .53)
Table 54. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .54);
Table 55. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 3-CI-2-naphthyl (compounds of formula 1 .55);
Table 56. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-5, Z is 3-CH3-2-naph- thyl (compounds of formula 1 .56);
Table 57. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-CI-C6FU (compounds of formula 1 .57);
Table 58. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-Br-CeH4 (compounds of formula 1 .58);
Table 59. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-CH3-C6FU (compounds of formula 1 .59);
Table 60. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .60); Table 61 . Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .61 );
Table 62. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .62);
Table 63. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 3-CI-2-naphthyl (compounds of formula 1 .63);
Table 64. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-6, Z is 3-CH3-2-naph- thyl (compounds of formula 1.64);
Table 65. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-CI-C6H4 (compounds of formula 1 .65);
Table 66. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-Br-C6H4 (compounds of formula 1 .66);
Table 67. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-CH3-C6H4 (compounds of formula 1 .67);
Table 68. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .68);
Table 69. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .69);
Table 70. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .70);
Table 71 . Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 3-CI-2-naphthyl (compounds of formula 1 .71 );
Table 72. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-7, Z is 3-CH3-2-naph- thyl (compounds of formula 1.72);
Table 73. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-CI-C6H4 (compounds of formula 1 .73);
Table 74. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-Br-C6H4 (compounds of formula 1 .74);
Table 75. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-CH3-C6H4 (compounds of formula 1 .75);
Table 76. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .76);
Table 77. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .77);
Table 78. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .78);
Table 79. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 3-CI-2-naph- thyl compounds of formula 1.79);
Table 80. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-20, Z is 3-CH3-2- naphthyl (compounds of formula 1.80);
Table 81 . Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-CI-C6H4 (compounds of formula 1 .81 );
Table 82. Compounds of formula , wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-Br-C6H4 (compounds of formula 1 .82); Table 83. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-CH3-C6H4 (compounds of formula 1 .83);
Table 84. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-CI-4-F-C6H3 (compounds of formula 1 .84);
Table 85. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .85);
Table 86. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 2-CI-5-F-C6H3 (compounds of formula 1 .86);
Table 87. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 3-CI-2-naph- thyl (compounds of formula 1.87);
Table 88. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-21 , Z is 3-CH3-2- naphthyl (compounds of formula 1.88);
Table 89. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-CI-C6H4 (compounds of formula 1 .89);
Table 90. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-Br-C6H4 (compounds of formula 1 .90);
Table 91 . Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-CH3-C6H4 (compounds of formula 1 .91 );
Table 92. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-CI-4-F-C6H3 (compounds of formula 1 .92);
Table 93. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .93);
Table 94. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 2-CI-5-F-C6H3 (compounds of formula 1 .94);
Table 95. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 3-CI-2-naph- thyl (compounds of formula 1.95);
Table 96. Compounds of formula I, wherein R1 is 1 -F-isopropyl, R2 is R2-22, Z is 3-CH3-2- naphthyl (compounds of formula 1.96);
Table 97. Compounds of formula I , wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-CI-C6H4 (compounds of formula 1 .97);
Table 98. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-Br-C6H4 (compounds of formula 1 .98);
Table 99. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-CH3-C6H4 (compounds of formula 1 .99);
Table 100. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-CI-4-F- C6H3 (compounds of formula 1 .100);
Table 101 . Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1 .101 );
Table 102. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 2-CI-5-F- C6H3 (compounds of formula 1 .102);
Table 103. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 3-CI-2- naphthyl (compounds of formula 1 .103);
Table 104. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-5, Z is 3-CH3-2- naphthyl (compounds of formula 1.104); Table 105. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-CI-C6H4 (compounds of formula 1.105);
Table 106. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-Br-C6H4 (compounds of formula 1.106);
Table 107. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-CH3-C6H4 (compounds of formula 1.107);
Table 108. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-CI-4-F- C6H3 (compounds of formula 1.108);
Table 109. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1.109);
Table 110. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 2-CI-5-F- C6H3 (compounds of formula 1.110);
Table 111. Compounds of formula I , wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 3-CI-2- naphthyl (compounds of formula 1.111);
Table 112. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-6, Z is 3-CH3-2- naphthyl (compounds of formula 1.112);
Table 113. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-CI-C6H4 (compounds of formula 1.113);
Table 114. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-Br-CeH4 (compounds of formula 1.114);
Table 115. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-CH3-C6H4 (compounds of formula 1.115);
Table 116. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-CI-4-F- C6H3 (compounds of formula 1.116);
Table 117. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-CI-5-CF3- C6H3 (compounds of formula 1.117);
Table 118. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 2-CI-5-F- C6H3 (compounds of formula 1.118);
Table 119. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 3-CI-2- naphthyl (compounds of formula 1.119);
Table 120. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-7, Z is 3-CH3-2- naphthyl (compounds of formula 1.120);
Table 121. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-CI-C6H4 (compounds of formula 1.121);
Table 122. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-Br-C6H4 (compounds of formula 1.122);
Table 123. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-CH3- C6H4 (compounds of formula 1.123);
Table 124. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-CI-4-F- C6H3 (compounds of formula 1.124);
Table 125. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-CI-5- CF3-C6H3 (compounds of formula 1.125);
Table 126. Compounds of formula I, wherein R1 is 1-F-cyclopropyl, R2 is R2-20, Z is 2-CI-5-F- C6H3 (compounds of formula 1.126); Table 127. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-20, Z is 3-CI-2- naphthyl (compounds of formula 1 .127);
Table 128. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-20, Z is 3-CH3-2- naphthyl (compounds of formula 1.128);
Table 129. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-CI-C6H4 (compounds of formula 1 .129);
Table 130. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-Br-C6H4 (compounds of formula 1 .130);
Table 131 . Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-CH3- C6H4 (compounds of formula 1 .131 );
Table 132. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-CI-4-F- C6H3 (compounds of formula 1 .132);
Table 133. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-CI-5- CF3-C6H3 (compounds of formula 1 .133);
Table 134. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 2-CI-5-F- C6H3 (compounds of formula 1 .134);
Table 135. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 3-CI-2- naphthyl (compounds of formula 1.135);
Table 136. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-21 , Z is 3-CH3-2- naphthyl (compounds of formula 1.136);
Table 137. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-CI-C6H4 (compounds of formula 1 .137);
Table 138. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-Br-C6H4 (compounds of formula 1 .138);
Table 139. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-CH3- C6H4 (compounds of formula 1 .139);
Table 140. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-CI-4-F- C6H3 (compounds of formula 1.140);
Table 141 . Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-CI-5- CF3-C6H3 (compounds of formula 1 .141 );
Table 142. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 2-CI-5-F- C6H3 (compounds of formula 1 .142);
Table 143. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 3-CI-2- naphthyl (compounds of formula 1.143);
Table 144. Compounds of formula I, wherein R1 is 1 -F-cyclopropyl, R2 is R2-22, Z is 3-CH3-2- naphthyl (compounds of formula 1.144);
Table A:
Figure imgf000070_0001
Figure imgf000070_0002
Figure imgf000071_0001
Figure imgf000071_0002
Figure imgf000072_0001
Figure imgf000072_0002
Figure imgf000073_0002
Figure imgf000073_0001
The specific number for each single compound is deductible as follows:
Compound 1.1.3 e.g. comprises the compound of formula 1.1 from Table 1 and row 3 from Ta- ble A;
To widen the spectrum of action and to achieve synergistic effects, the pyrimidine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly. Suitable components for mixtures are, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxypro- pionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbama- tes, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthal- imides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarba- mates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoro- amidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecar- boxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecar- boxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazoli- nones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolo- carboxamides, triazolopyrimidines, triketones, uracils, or ureas.
It may furthermore be beneficial to apply the pyrimidine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
In one embodiment of the present invention the compositions according to the present inven- tion comprise at least one pyrimidine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
In a preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyrimidine compound of formula (I. A) (cor- responds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.B) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.C) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.D) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.E) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.F) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.G) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.H) (corresponds to pyrimidine compound of formula (I)), as defined herein.
In another preferred embodiment of the invention, the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I. I) (corresponds to pyrimidine compound of formula (I)), as defined herein.
Preferred compounds of the formula (I) which, as component A, are constituent of the compo- sition according to the invention are the compounds I.A to 1.1, as defined above.
In another embodiment of the present invention the compositions according to the present in- vention comprise at least one pyrimidine compound of formula (I) and at least one further active compound B (herbicide B).
The further herbicidal compound B (component B) is preferably selected from the herbicides of class b1 ) to b15):
Mixing partners for the composition can be selected from below herbicides B as defined below:
B) herbicides of class b1) to b15):
b1 ) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors);
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitosis inhibitors; b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); b11 ) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dym- ron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinocla- mine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;
including their agriculturally acceptable salts or derivatives;
In one embodiment of the invention, the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bi- osynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-AC- Case herbicides). The ACCase herbicides belong to the group A of the HRAC classification sys- tem whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
In another embodiment of the invention, the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one inhibitor of pho- tosynthesis (herbicide b3). The herbicidal activity of these compounds is based either on the in- hibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI in- hibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis. Amongst these, PSII inhibitors are preferred.
In another embodiment of the invention, the compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4). The herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase. These inhibitors belong to the group E of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one bleacher-herbi- cide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by in- hibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and corn- pounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - un- known target, group F3 of HRAC classification). In another embodiment of the invention, the compositions contain at least one EPSP synthase inhibitor (herbicide b6). The herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid bio- synthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one glutamine syn- thetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhi- bition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants. These inhibitors belong to the group H of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one DHP synthase inhibitor (herbicide b8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to the group I of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one mitosis inhibitor (herbicide b9). The herbicidal activity of these compounds is based on the disturbance or inhibi- tion of microtubule formation or organization, and thus on the inhibition of mitosis. These inhibi- tors belong to the groups K1 and K2 of the HRAC classification system. Among these, corn- pounds of the group K1 , in particular dinitroanilines, are preferred.
In another embodiment of the invention, the compositions contain at least one VLCFA inhibitor (herbicide b10). The herbicidal activity of these compounds is based on the inhibition of the syn- thesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one cellulose bio- synthesis inhibitor (herbicide b11 ). The herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants. These inhibitors belong to the group L of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one decoupler herbi- cide (herbicide b12). The herbicidal activity of these compounds is based on the disruption of the cell membrane. These inhibitors belong to the group M of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one auxinic herbi- cide (herbicide b13). These include compounds that mimic auxins, i.e. plant hormones, and af- fect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
In another embodiment of the invention, the compositions contain at least one auxin transport inhibitor (herbicide b14). The herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants. These compounds belong to the group P of the HRAC classifica- tion system.
As to the given mechanisms of action and classification of the active substances, see e.g. "HRAC, Classification of Herbicides According to Mode of Action", http://www.plantprotec- tion.org/hrac/MOA.html).
Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14. Specific preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
Particular preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
Examples of herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop- P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,
4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1 '-biphenyl]-3-yl)-5-hy- droxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-flu- oro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-di- chloro-4-cyclopropyl- [1 ,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5- (Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one (CAS 1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid me- thyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1'-biphenyl]-3-yl)-5,6-dihydro- 2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-flu- oro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid me- thyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tio- carbazil, triallate and vernolate;
b2) from the group of the ALS inhibitors:
sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primi- sulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron- ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu ron, triflusulfu- ron-methyl and tritosulfuron,
imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, thazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
pyhmidinylbenzoates such as bispyribac, bispyhbac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS
420138-01-8),
sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
among these, a preferred embodiment of the invention relates to those compositions compris- ing at least one imidazolinone herbicide;
b3) from the group of the photosynthesis inhibitors:
amicarbazone, inhibitors of the photosystem II, e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-me- thoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hy- droxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1 ), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, des- metryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, sim- etryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlo- rotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metam- itron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthi- uron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and es- ters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and benta- zon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat- dimetilsulfate. Among these, a preferred embodiment of the invention relates to those composi- tions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodi- ment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1- methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]ace- tate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl- 1 A pyrazole-l -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l-car- boxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxa- zin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3- oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (£)- 4-[2- chloro-5-[4-chloro-5-(difluoromethoxy)-1 methyl-pyrazol-S-ylH-fluoro-phenoxyl-S-methoxy- but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol- 4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);
b5) from the group of the bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS
180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxa- zolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium, glyposate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors:
compounds of group K1 : dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyhdines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, corn- pounds of group K1 , in particular dinitroanilines are preferred;
b10) from the group of the VLCFA inhibitors:
chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3,
Figure imgf000080_0001
the isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
2006/037945, WO 2007/071900 and WO 2007/096576;
among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pentafluorphenyloxy-14- [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
b12) from the group of the decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino- 3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, inda- nofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, me- thyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.
Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P- ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4- cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetra- methyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 - biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4- ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS
1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2, 2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2, 2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2, 2,6, 6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors:
amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlor- sulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysul- furon, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfu- ron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metosulam, met- sulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, py- rimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenu- ron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors:
ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluome- turon, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyri- date, simazine, terbutryn, terbuthylazine, thidiazuron, 1 -(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1 -(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro-
2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butyl-1 -methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1 -(5-tert-butyl-1 -methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1 - methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4- hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8) and 1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1 );
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, cyclopyranil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -me- thyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 TT-py- razole-1 -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 TT-pyrazole-l -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 TT-pyrazole-l -carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 TT-pyrazole-l -car- boxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxa- zin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-
3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-di- one (CAS 13001 18-96-0);1 -methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4- dihydro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), and 3-[7- chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimi- dine-2,4-dione (CAS 212754-02-4);
b5) from the group of the bleacher herbicides:
aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)- pyrimidine (CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoro- methyl)benzamide (CAS 1361 139-71-0, 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- done (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors:
glufosinate, glufosinate-P, glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors:
benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M- isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
b11 ) from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1 );
b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and es- ters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, cyclopy- rimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat- metilsulfate, DSMA, dymron (= daimuron), indanofan, metam, methylbromide, MSMA, oxazi- clomefone, pyributicarb and tridiphane.
Particularly preferred herbicides B that can be used in combination with the pyrimidine corn- pounds of the formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-
4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3);
5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 , 1 '-biphenyl]-3-yl)-3,6-dihyd ro-2,2,6,6-tetra- methyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 - biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2l-l-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4- ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS
1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2, 2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2, 2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2, 2,6, 6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); esprocarb, prosul- focarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1 );
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: cyclopyranil, flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, ethyl [3-[2- chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phe- noxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100, 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS
451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)- 4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0), and 1-methyl-6-trifluoromethyl-3- (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4- dione (CAS 1304113-05-0);
b5) from the group of the bleacher herbicides: amitrole, bicyclopyrone, clomazone, diflufeni- can, fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 2- chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139- 71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); and 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
b9) from the group of the mitosis inhibitors: pendimethalin and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
b11 ) from the group of the cellulose biosynthesis inhibitors: indaziflam, isoxaben and tria- ziflam;
b13) from the group of the auxinic herbicides: 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) from the group of the other herbicides: cinmethylin, dymon (= daimuron), indanofan, oxa- ziclomefone.
Particularly preferred herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
Table B
Figure imgf000085_0001
Figure imgf000085_0002
Figure imgf000086_0001
Figure imgf000086_0002
Figure imgf000087_0001
Figure imgf000087_0002
Figure imgf000088_0001
Figure imgf000088_0002
Particularly preferred herbicides B could also be B.203 which is cyclopyranil.
In another embodiment of the present invention the compositions according to the present in- vention comprise at least one pyrimidine compound of formula (I) and at least one safener C.
Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the pre- sent compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. The safeners and the pyrimidine compounds of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-d i hyd ro-5-a I kyl- 1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-
5.5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxa- zolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).
Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy- dride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3),
2.2.5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroace- tyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroace- tyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C, which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
Table C:
Figure imgf000088_0003
Figure imgf000089_0001
Figure imgf000089_0002
The active compounds B of groups b1 ) to b15) and the active compounds C are known herbi- cides and safeners, see, e.g., The Compendium of Pesticide Common Names (http://www.alan- wood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Com- pany, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of Amer- ica, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Sci- ence Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.
The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this sub- stance was only assigned to one mechanism of action.
Active compounds B and C 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 agricul- turally acceptable derivative in the compositions according to the invention.
In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. E.g., suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicam ba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammoni- um, 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 (2,4-D choline). Examples of suitable 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.
Suitable salts of 2,4-DB are e.g. 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethyl- ammonium. Suitable esters of 2,4-DB are e.g. 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are e.g. dichlorprop-sodium, dichlorprop-potassium and dichlor- prop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
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.
Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable es- ter of picloram is picloram-isoctyl.
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are e.g. triclopyr-ethyl and triclopyr-butotyl.
Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diola- mine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6- TBA-potassium and 2,3,6-TBA-sodium.
Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dime- thylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
Suitable salts of glyphosate are e.g. glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref- erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sul- fosate).
A suitable salt of glufosinate is e.g. glufosinate-ammonium.
A suitable salt of glufosinate-P is e.g. glufosinate-P-ammonium.
Suitable salts and esters of bromoxynil are e.g. bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
Suitable salts and esters of ioxonil are e.g. ioxonil-octanoate, ioxonil-potassium and ioxonil- sodium.
Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammo- nium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
Suitable salts of mecoprop-P are e.g. mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-so- dium.
A suitable salt of diflufenzopyr is e.g. diflufenzopyr-sodium.
A suitable salt of naptalam is e.g. naptalam-sodium. Suitable salts and esters of aminocyclopyrachlor are e.g. aminocyclopyrachlor-dimethylammo- nium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclo- pyrachlor-sodium and aminocyclopyrachlor-potassium.
A suitable salt of quinclorac is e.g. quinclorac-dimethylammonium.
A suitable salt of quinmerac is e.g. quinmerac-dimethylammonium.
A suitable salt of imazamox is e.g. imazamox-ammonium.
Suitable salts of imazapic are e.g. imazapic-ammonium and imazapic-isopropylammonium.
Suitable salts of imazapyr are e.g. imazapyr-ammonium and imazapyr-isopropylammonium.
A suitable salt of imazaquin is e.g. imazaquin-ammonium.
Suitable salts of imazethapyr are e.g. imazethapyr-ammonium and imazethapyr-isoprop- ylammonium.
A suitable salt of topramezone is e.g. topramezone-sodium.
According to a preferred embodiment of the invention, the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbi- cides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29),
(1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29),
(1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably ex- actly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least two, prefer- ably exactly two herbicides B different from each other, and as component C at least one, pref- erably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I) from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15),
(1.56.15), (1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29),
(1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29),
(1.74.29), (1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least three, pref- erably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pinoxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb and triallate.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clori- muron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-iso- propylammonium, imazapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, ima- zaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazethapyr-isoprop- ylammonium, imazosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, metosulam, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyroxsulam, pro- pyrisulfuron, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, thifensulfuron-methyl, tribenuron- methyl, tritosulfuron and triafamone.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-hep- tanoate, bromoxynil-potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metam- itron, metribuzin, paraquat-dichloride, propanil, simazin, terbutryn and terbuthylazine.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin , ethyl [3-[2- chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phe- noxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100). According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617- 21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, toprame- zone-sodium and 2-chloro-3-methylsulfanyl-N-(1 -methyltetrazol-5-yl)-4-(trifluoromethyl)ben- zamide (CAS 1361139-71-0) .
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium , glyphosate- isopropylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate-P and glufosinate-P-ammonium.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyrox- asulfone. Likewise, preference is given to compositions comprising in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15),
(1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15), (1.49.29), (1.50.29),
(1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15),
(1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29), (1.75.29), (1.76.29),
(1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicid- ally active compound from group b10), in particular selected from the group consisting of isoxa- zoline compounds of the formulae 11.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15),
(1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b11 ), in particular indaziflam, isoxaben and triaziflam.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethano- lammonium, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-me- thyl, aminopyralid, aminopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba- butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-iso- propylammonium, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis- (3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, MCPA, MCPA-2-ethylhexyl, MCPA-dimethylammonium, quinclorac, quinclorac-dimethylammonium, quinmerac, quinmerac-dimethylammonium, florpyrauxifen , florpyrauxifen-benzyl (CAS 1390661-72-9), and 4-amino-3-chloro-5-fluoro-6-(7- fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6) .
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium. According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of cinmethylin, dymron (= daimuron), indanofan and oxaziclomefone.
According to another preferred embodiment of the invention, the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.49.15), (1.50.15), (1.51.15), (1.52.15), (1.53.15), (1.54.15), (1.55.15), (1.56.15),
(1.49.29), (1.50.29), (1.51.29), (1.52.29), (1.53.29), (1.54.29), (1.55.29), (1.56.29), (1.73.15), (1.74.15), (1.75.15), (1.76.15), (1.77.15), (1.78.15), (1.79.15), (1.80.15), (1.73.29), (1.74.29),
(1.75.29), (1.76.29), (1.77.29), (1.78.29), (1.79.29), and (1.80.29), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, clo- quintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trime- thyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4).
Here and below, the term“binary compositions” includes compositions comprising one or more, e.g. 1 , 2 or 3, active compounds of the formula (I) and either one or more, e.g. 1 , 2 or 3, herbicides B or one or more safeners C.
Correspondingly, the term“ternary compositions” includes compositions comprising one or more, e.g. 1 , 2 or 3, active compounds of the formula (I), one or more, e.g. 1 , 2 or 3, herbicides B and one or more, e.g. 1 , 2 or 3, safeners C.
In binary compositions comprising at least one pyrimidine of formula (I) as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
In binary compositions comprising at least one pyrimidine of formula (I) as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
In ternary compositions comprising at least one pyrimidine of formula (I) as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the com- ponents A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , and the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , prefera- bly in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and par- ticularly preferably in the range of from 1 :75 to 75:1. The weight ratio of components A + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1. The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
Particularly preferred are the compositions mentioned below comprising the pyrimidine corn- pounds of formula I as defined and the substance(s) as defined in the respective row of table T; especially preferred comprising as only herbicidal active compounds the pyrimidine corn- pounds of formula I as defined and the substance(s) as defined in the respective row of table T; most preferably comprising as only active compounds the pyrimidine compounds of formula I as defined and the substance(s) as defined in the respective row of table T.
Particularly preferred are compositions 1 .1 to 1 .3653, comprising the compound (1 .49.15) and the substance(s) as defined in the respective row of table T:
Figure imgf000097_0001
Figure imgf000097_0002
Figure imgf000097_0003
Figure imgf000098_0001
Figure imgf000098_0002
Figure imgf000098_0003
Figure imgf000099_0001
Figure imgf000099_0002
Figure imgf000099_0003
Figure imgf000100_0001
Figure imgf000100_0002
Figure imgf000100_0003
Figure imgf000101_0001
Figure imgf000101_0002
Figure imgf000101_0003
Figure imgf000102_0001
Figure imgf000102_0002
Figure imgf000102_0003
Figure imgf000103_0001
Figure imgf000103_0002
Figure imgf000103_0003
Figure imgf000104_0001
Figure imgf000104_0002
Figure imgf000104_0003
Figure imgf000105_0001
Figure imgf000105_0002
Figure imgf000105_0003
Figure imgf000106_0001
Figure imgf000106_0002
Figure imgf000106_0003
Figure imgf000107_0001
Figure imgf000107_0002
Figure imgf000107_0003
Figure imgf000108_0001
Figure imgf000108_0002
Figure imgf000108_0003
Figure imgf000109_0001
Figure imgf000109_0002
Figure imgf000109_0003
Figure imgf000110_0001
Figure imgf000110_0002
Figure imgf000110_0003
Figure imgf000111_0001
Figure imgf000111_0002
Figure imgf000111_0003
Figure imgf000112_0001
Figure imgf000112_0002
Figure imgf000112_0003
Figure imgf000113_0001
Figure imgf000113_0002
Figure imgf000113_0003
Figure imgf000114_0001
Figure imgf000114_0002
Figure imgf000114_0003
Figure imgf000115_0001
Figure imgf000115_0002
Figure imgf000115_0003
Figure imgf000116_0001
Figure imgf000116_0002
Figure imgf000116_0003
Figure imgf000117_0001
Figure imgf000117_0002
Figure imgf000117_0003
Figure imgf000118_0001
Figure imgf000118_0002
Figure imgf000118_0003
Figure imgf000119_0001
Figure imgf000119_0002
Figure imgf000119_0003
Figure imgf000120_0001
Figure imgf000120_0002
Figure imgf000120_0003
Figure imgf000121_0001
Figure imgf000121_0002
Figure imgf000121_0003
Figure imgf000122_0001
Figure imgf000122_0002
Figure imgf000122_0003
Figure imgf000123_0001
Figure imgf000123_0002
Figure imgf000123_0003
Figure imgf000124_0001
Figure imgf000124_0002
Figure imgf000124_0003
Figure imgf000125_0001
Figure imgf000125_0002
Figure imgf000125_0003
Figure imgf000126_0003
Figure imgf000126_0001
Figure imgf000126_0002
Also particularly preferred are compositions 1.3654 to 1.3671 , comprising the compound (1.49.15), and the substance(s) as defined in the respective row of table W:
Table W (compositions 1.3654 to 1.3671):
Figure imgf000127_0001
Figure imgf000127_0002
15
The specific number for each single composition is deductible as follows:
Composition 1.203 e.g. comprises the compound (1.49.15), clethodim (B.1 ) and benoxacor (C.1 ) (see table B, entry B.1 and table C, entry C.1 ).
Also especially preferred are compositions 2.1 to 2.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.50.15) in place of the compound (1.49.15).
Also especially preferred are compositions 3.1 to 3.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.2 as further herbicide B.
Also especially preferred are compositions 4.1 to 4.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 5.1 to 5.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.30 as further herbicide B.
Also especially preferred are compositions 6.1 to 6.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 7.1 to 7.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.35 as further herbicide B.
Also especially preferred are compositions 8.1 to 8.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.38 as further herbicide B.
Also especially preferred are compositions 9.1 to 9.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 10.1 to 10.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 11.1 to 11.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.1 to 12.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.56 as further herbicide B. Also especially preferred are compositions 13.1 to 13.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.1 to 14.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.1 to 15.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 16.1 to 16.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 17.1 to 17.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 18.1 to 18.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 19.1 to 19.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 20.1 to 20.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 21.1 to 21.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 22.1 to 22.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 23.1 to 23.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.88 as further herbicide B.
Also especially preferred are compositions 24.1 to 24.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 25.1 to 25.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 26.1 to 26.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 27.1 to 27.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 28.1 to 28.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.100 as further herbicide B.
Also especially preferred are compositions 29.1 to 29.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 as further herbicide B.
Also especially preferred are compositions 30.1 to 30.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.67 as further herbicides B.
Also especially preferred are compositions 31.1 to 31.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.76 as further herbicides B.
Also especially preferred are compositions 32.1 to 32.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.82 as further herbicides B.
Also especially preferred are compositions 33.1 to 33.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 as further herbicide B.
Also especially preferred are compositions 34.1 to 34.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.67 as further herbicides B.
Also especially preferred are compositions 35.1 to 35.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.76 as further herbicides B.
Also especially preferred are compositions 36.1 to 36.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.82 as further herbicides B.
Also especially preferred are compositions 37.1 to 37.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 38.1 to 38.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.107 as further herbicide B.
Also especially preferred are compositions 39.1 to 39.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
Also especially preferred are compositions 40.1 to 40.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
Also especially preferred are compositions 41.1 to 41.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.82 as further herbicides B. Also especially preferred are compositions 42.1 to 42.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 43.1 to 43.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 as further herbicide B.
Also especially preferred are compositions 44.1 to 44.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 11 and B.67 as further herbicides B.
Also especially preferred are compositions 45.1 to 45.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 and B.76 as further herbicides B.
Also especially preferred are compositions 46.1 to 46.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 and B.82 as further herbicides B.
Also especially preferred are compositions 47.1 to 47.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 1 16 as further herbicide B.
Also especially preferred are compositions 48.1 to 48.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.67 as further herbicides B.
Also especially preferred are compositions 49.1 to 49.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.94 as further herbicides B.
Also especially preferred are compositions 50.1 to 50.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.103 as fur- ther herbicides B.
Also especially preferred are compositions 51.1 to 51.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.128 as fur- ther herbicides B.
Also especially preferred are compositions 52.1 to 52.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.104 as fur- ther herbicides B.
Also especially preferred are compositions 53.1 to 53.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.107 as fur- ther herbicides B.
Also especially preferred are compositions 54.1 to 54.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.11 1 as fur- ther herbicides B.
Also especially preferred are compositions 55.1 to 55.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.122 as further herbicide B.
Also especially preferred are compositions 56.1 to 56.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.126 as further herbicide B.
Also especially preferred are compositions 57.1 to 57.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.128 as further herbicide B.
Also especially preferred are compositions 58.1 to 58.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.131 as further herbicide B.
Also especially preferred are compositions 59.1 to 59.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.132 as further herbicide B.
Also especially preferred are compositions 60.1 to 60.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.133 as further herbicide B.
Also especially preferred are compositions 61.1 to 61.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.135 as further herbicide B.
Also especially preferred are compositions 62.1 to 62.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.137 as further herbicide B.
Also especially preferred are compositions 63.1 to 63.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.138 as further herbicide B.
Also especially preferred are compositions 64.1 to 64.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.140 as further herbicide B.
Also especially preferred are compositions 65.1 to 65.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.145 as further herbicide B.
Also especially preferred are compositions 66.1 to 66.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.153 as further herbicide B.
Also especially preferred are compositions 67.1 to 67.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.156 as further herbicide B.
Also especially preferred are compositions 68.1 to 68.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.171 as further herbicide B.
Also especially preferred are compositions 69.1 to 69.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.174 as further herbicide B.
Also especially preferred are compositions 70.1 to 70.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.51.15) in place of the compound (1.49.15). Also especially preferred are compositions 71.1 to 71.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.52.15) in place of the compound (1.49.15).
Also especially preferred are compositions 72.1 to 72.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.53.15) in place of the compound (1.49.15).
Also especially preferred are compositions 73.1 to 73.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.54.15) in place of the compound (1.49.15).
Also especially preferred are compositions 74.1 to 74.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.55.15) in place of the compound (1.49.15).
Also especially preferred are compositions 75.1 to 75.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.56.15) in place of the compound (1.49.15).
Also especially preferred are compositions 76.1 to 76.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.49.29) in place of the compound (1.49.15).
Also especially preferred are compositions 77.1 to 77.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.50.29) in place of the compound (1.49.15).
Also especially preferred are compositions 78.1 to 78.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.51.29) in place of the compound (1.49.15).
Also especially preferred are compositions 79.1 to 79.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.52.29) in place of the compound (1.49.15).
Also especially preferred are compositions 80.1 to 80.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.53.29) in place of the compound (1.49.15).
Also especially preferred are compositions 81.1 to 81.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.54.29) in place of the compound (1.49.15).
Also especially preferred are compositions 82.1 to 82.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.55.29) in place of the compound (1.49.15).
Also especially preferred are compositions 83.1 to 83.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.56.29) in place of the compound (1.49.15).
Also especially preferred are compositions 84.1 to 84.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.73.15) in place of the compound (1.49.15).
Also especially preferred are compositions 85.1 to 85.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.74.15) in place of the compound (1.49.15).
Also especially preferred are compositions 86.1 to 86.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.75.15) in place of the compound (1.49.15).
Also especially preferred are compositions 87.1 to 87.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.76.15) in place of the compound (1.49.15).
Also especially preferred are compositions 88.1 to 88.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.77.15) in place of the compound (1.49.15).
Also especially preferred are compositions 89.1 to 89.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.78.15) in place of the compound (1.49.15).
Also especially preferred are compositions 90.1 to 90.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.79.15) in place of the compound (1.49.15).
Also especially preferred are compositions 91.1 to 91.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.80.15) in place of the compound (1.49.15).
Also especially preferred are compositions 92.1 to 92.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.73.29) in place of the compound (1.49.15).
Also especially preferred are compositions 93.1 to 93.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.74.29) in place of the compound (1.49.15).
Also especially preferred are compositions 94.1 to 94.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.75.29) in place of the compound (1.49.15).
Also especially preferred are compositions 95.1 to 95.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.76.29) in place of the compound (1.49.15).
Also especially preferred are compositions 96.1 to 96.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.77.29) in place of the compound (1.49.15).
Also especially preferred are compositions 97.1 to 97.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.78.29) in place of the compound (1.49.15).
Also especially preferred are compositions 98.1 to 98.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.79.29) in place of the compound (1.49.15).
Also especially preferred are compositions 99.1 to 99.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.80.29) in place of the compound (1.49.15). Also especially preferred are compositions 2.3654 to 2.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.50.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 3.3654 to 3.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.2 as further herbi- cide B.
Also especially preferred are compositions 4.3654 to 4.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.8 as further herbi- cide B.
Also especially preferred are compositions 5.3654 to 5.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.30 as further herbi- cide B.
Also especially preferred are compositions 6.3654 to 6.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.32 as further herbi- cide B.
Also especially preferred are compositions 7.3654 to 7.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.35 as further herbi- cide B.
Also especially preferred are compositions 8.3654 to 8.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.38 as further herbi- cide B.
Also especially preferred are compositions 9.3654 to 9.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.40 as further herbi- cide B.
Also especially preferred are compositions 10.3654 to 10.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 11.3654 to 1 1.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.3654 to 12.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 13.3654 to 13.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.3654 to 14.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.3654 to 15.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 16.3654 to 16.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 17.3654 to 17.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 18.3654 to 18.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 19.3654 to 19.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 20.3654 to 20.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 21.3654 to 21.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 22.3654 to 22.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 23.3654 to 23.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.88 as further herbicide B.
Also especially preferred are compositions 24.3654 to 24.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 25.3654 to 25.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 26.3654 to 26.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 27.3654 to 27.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 28.3654 to 28.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.100 as fur- ther herbi-cide B.
Also especially preferred are compositions 29.3654 to 29.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 as fur- ther herbi-cide B.
Also especially preferred are compositions 30.3654 to 30.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.67 as fur-ther herb-icides B. Also especially preferred are compositions 31.3654 to 31.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.76 as fur-ther herb-icides B.
Also especially preferred are compositions 32.3654 to 32.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.82 as fur-ther herb-icides B.
Also especially preferred are compositions 33.3654 to 33.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 as fur- ther herbi-cide B.
Also especially preferred are compositions 34.3654 to 34.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.67 as fur-ther herb-icides B.
Also especially preferred are compositions 35.3654 to 35.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.76 as fur-ther herb-icides B.
Also especially preferred are compositions 36.3654 to 36.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.82 as fur-ther herb-icides B.
Also especially preferred are compositions 37.3654 to 37.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.106 as fur- ther herbi-cide B.
Also especially preferred are compositions 38.3654 to 38.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.107 as fur- ther herbi-cide B.
Also especially preferred are compositions 39.3654 to 39.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.67 as fur-ther herbicides B.
Also especially preferred are compositions 40.3654 to 40.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.76 as fur-ther herbicides B.
Also especially preferred are compositions 41.3654 to 41.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.82 as fur-ther herbicides B.
Also especially preferred are compositions 42.3654 to 42.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.109 as fur- ther herbi-cide B.
Also especially preferred are compositions 43.3654 to 43.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 11 as fur- ther herbi-cide B.
Also especially preferred are compositions 44.3654 to 44.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 11 and B.67 as fur-ther herb-icides B.
Also especially preferred are compositions 45.3654to 45.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 11 and B.76 as fur-ther herb-icides B.
Also especially preferred are compositions 46.3654 to 46.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 11 and B.82 as fur-ther herb-icides B.
Also especially preferred are compositions 47.3654 to 47.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B. 1 16 as fur- ther herbi-cide B.
Also especially preferred are compositions 48.3654 to 48.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.67 as fur-ther herb-icides B.
Also especially preferred are compositions 49.3654 to 49.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.94 as fur-ther herb-icides B.
Also especially preferred are compositions 50.3654 to 50.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.103 as further herbicides B.
Also especially preferred are compositions 51.3654 to 51.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.128 as further herbicides B.
Also especially preferred are compositions 52.3654 to 52.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.104 as further herbicides B.
Also especially preferred are compositions 53.3654 to 53.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.107 as further herbicides B.
Also especially preferred are compositions 54.3654 to 54.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.1 11 as further herbicides B.
Also especially preferred are compositions 55.3654 to 55.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.122 as fur- ther herbi-cide B.
Also especially preferred are compositions 56.3654 to 56.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.126 as fur- ther herbi-cide B.
Also especially preferred are compositions 57.3654 to 57.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.128 as fur- ther herbi-cide B.
Also especially preferred are compositions 58.3654 to 58.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.131 as fur- ther herbi-cide B.
Also especially preferred are compositions 59.3654 to 59.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.132 as fur- ther herbi-cide B. Also especially preferred are compositions 60.3654 to 60.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.133 as fur- ther herbi-cide B.
Also especially preferred are compositions 61.3654 to 61.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.135 as fur- ther herbi-cide B.
Also especially preferred are compositions 62.3654 to 62.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.137 as fur- ther herbi-cide B.
Also especially preferred are compositions 63.3654 to 63.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.138 as fur- ther herbi-cide B.
Also especially preferred are compositions 64.3654 to 64.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.140 as fur- ther herbi-cide B.
Also especially preferred are compositions 65.3654 to 65.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.145 as fur- ther herbi-cide B.
Also especially preferred are compositions 66.3654 to 66.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.153 as fur- ther herbi-cide B.
Also especially preferred are compositions 67.3654 to 67.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.156 as fur- ther herbi-cide B.
Also especially preferred are compositions 68.3654 to 68.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.171 as fur- ther herbi-cide B.
Also especially preferred are compositions 69.3654 to 69.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.174 as fur- ther herbi-cide B.
Also especially preferred are compositions 70.3654 to 70.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.51.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 71.3654 to 71.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.52.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 72.3654 to 72.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.53.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 73.3654 to 73.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.54.15) in place of the compound (1.49.15).
Also especially preferred are compositions 74.3654 to 74.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.55.15) in place of the compound (1.49.15).
Also especially preferred are compositions 75.3654 to 75.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.56.15) in place of the compound (1.49.15).
Also especially preferred are compositions 76.3654 to 76.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.49.29) in place of the compound (1.49.15).
Also especially preferred are compositions 77.3654 to 77.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.50.29) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 78.3654 to 78.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.51.29) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 79.3654 to 79.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.52.29) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 80.3654 to 80.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.53.29) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 81.3654 to 81.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.54.29) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 82.3654 to 82.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.55.29) in place of the compound (1.49.15).
Also especially preferred are compositions 83.3654 to 83.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.56.29) in place of the compound (1.49.15).
Also especially preferred are compositions 84.3654 to 84.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.73.15) in place of the compound (1.49.15).
Also especially preferred are compositions 85.3654 to 85.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.74.15) in place of the compound (1.49.15).
Also especially preferred are compositions 86.3654 to 86.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.75.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 87.3654 to 87.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.76.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 88.3654 to 88.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.77.15)) in place of the compound (1.49.15). Also especially preferred are compositions 89.3654 to 89.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.78.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 90.3654 to 90.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.79.15) in place of the corn-pound (1.49.15).
Also especially preferred are compositions 91.3654 to 91.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.80.15) in place of the compound (1.49.15).
Also especially preferred are compositions 92.3654 to 92.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.73.29) in place of the compound (1.49.15).
Also especially preferred are compositions 93.3654 to 93.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.74.29) in place of the compound (1.49.15).
Also especially preferred are compositions 94.3654 to 94.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.75.29) in place of the compound (1.49.15).
Also especially preferred are compositions 95.3654 to 95.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.76.29) in place of the compound (1.49.15).
Also especially preferred are compositions 96.3654 to 96.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.77.29) in place of the compound (1.49.15).
Also especially preferred are compositions 97.3654 to 97.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.78.29) in place of the compound (1.49.15).
Also especially preferred are compositions 98.3654 to 98.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.79.29) in place of the compound (1.49.15).
Also especially preferred are compositions 99.3654 to 99.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.80.29) in place of the compound (1.49.15).
The invention also relates to agrochemical compositions comprising at least an auxiliary and at least one pyrimidine compound of formula (I) according to the invention.
An agrochemical composition comprises a pesticidal effective amount of a pyrimidine corn- pound of formula (I). The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling unwanted plants, especially for controlling un- wanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic condi- tions and the specific pyrimidine compound of formula (I) used.
The pyrimidine compounds of formula (I), their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for ag- rochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treat- ment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the“Catalogue of pesticide formulation types and interna- tional coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New devel- opments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, disper- sants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibil- izers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions 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, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaCºCHarides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. ce- real meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, non-ionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty ac- ids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sul- fonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sul- fates are sulfates of fatty acids and 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, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of 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. Exam- pies of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Ex- amples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose, and glucose esters, or al- kylpoly-glucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium corn- pounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable am- photeric surfactants are alkylbetains and imidazolines. Suitable block polymers are block poly- mers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the pyrimidine compounds of for- mula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants, and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaCºCHarides (e.g. xanthan gum, carboxymethylcellulose), inor- ganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for agrochemical composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a pyrimidine compound of formula (I) according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a pyrimidine compound of formula (I) according to the invention and 1-10 wt% dis persant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC) 15-70 wt% of a pyrimidine compound of formula (I) according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a pyrimidine compound of formula (I) according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is intro- duced into water ad 100 wt% by means of an emulsifying machine and made into a homogene- ous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a pyrimidine compound of formula (I) according to the in- vention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspen- sion of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalco- hol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a pyrimidine compound of formula (I) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethox- ylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a sta- ble dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a pyrimidine compound of formula (I) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wet- ting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a pyrimidine compound of formula (I) according to the in- vention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. iv) Microemulsion (ME)
5-20 wt% of a pyrimidine compound of formula (I) according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% sur- factant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mix- ture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the in- vention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid, and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initi- ated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alterna- tively, an oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an iso- cyanate monomer (e.g. diphenylmethene-4,4’-diisocyanate) are dispersed into an aqueous so- lution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1- 10 wt%. The wt% relate to the total CS composition.
ix) Dustable powders (DP, DS)
1-10 wt% of a pyrimidine compound of formula (I) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
x) Granules (GR, FG)
0.5-30 wt% of a pyrimidine compound of formula (I) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extru- sion, spray-drying or the fluidized bed.
xi) Ultra-low volume liquids (UL)
1-50 wt% of a pyrimidine compound of formula (I) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
The agrochemical compositions comprising generally comprise between 0.01 and 95%, prefer- ably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the pyrimidine compound of formula (I). The pyrimidine compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The agrochemi- cal compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use prepa- rations. Application can be carried out before or during sowing.
Methods for applying pyrimidine compounds of formula (I) and agrochemical compositions thereof, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, py- rimidine compounds of formula (I) and agrochemical compositions thereof, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the py- rimidine compounds of formula (I) and the agrochemical compositions comprising them as pre- mix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the agrochemical compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1. The user applies the pyrimidine compound of formula (I) according to the invention and the ag- rochemical compositions comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical compo- sition is made up with water, buffer, and/or further auxiliaries to the desired application concen- tration and the ready-to-use spray liquor or the agrochemical composition according to the in- vention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to- use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising py- rimidine compounds of formula (I) may be mixed by the user in a spray tank and further auxilia- ries and additives may be added, if appropriate.
In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition ac- cording to the invention or partially premixed components, e. g components comprising pyrimi- dine compounds of formula (I) can be applied jointly (e.g. after tank mix) or consecutively.
The pyrimidine compounds of formula (I), are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising the pyrimidine compounds of formula (I), control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya, and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, e.g., water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (e.g. from 300 to 400 l/ha). The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, may also be applied by the low-volume or the ultra-low-volume method, or in the form of micro granules.
Application of the pyrimidine compounds of formula (I), or the agrochemical compositions corn- prising them, can be done before, during, and/or after, preferably during and/or after, the emergence of the undesirable plants.
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the pyrimidine compounds of formula (I), or the agrochemical composi- tions comprising them, by applying seed, pretreated with the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can be 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) based on the pyrimidine compounds of formula (I), or the agrochemical compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.
The term“seed” comprises seed of all types, such as, e.g., corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
When employed in plant protection, the amounts of active substances applied, i.e. the pyrimi- dine compounds of formula (I) without formulation auxiliaries, are, depending on the kind of ef- fect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
In another embodiment of the invention, the application rate of the pyrimidine compounds of formula (I) is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
In another preferred embodiment of the invention, the rates of application of the pyrimidine compounds of formula (I) according to the present invention (total amount of pyrimidine compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
In another preferred embodiment of the invention, the application rates of the pyrimidine corn- pounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
In another preferred embodiment of the invention, the application rate of the pyrimidine corn- pounds of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drench- ing seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, and most preferably from 5 to 100 g, per 100 kilogram of plant prop- agation material (preferably seeds) are generally required.
In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. the pyrimidine compounds of formula (I) are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Depending on the application method in question, the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec altissima, Beta vulgaris spec rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,
Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, SaCºCHarum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Preferred crops are Arachis hypogaea, Beta vulgaris spec altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, SaCºCHarum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or permanent crops.
The pyrimidine compounds of formula (I) according to the invention, or the agrochemical corn- positions comprising them, can also be used in the treatment of genetically modified plants. The term“genetically modified plants” is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species’ genome or to exhibit a deletion of DNA that was na- tive to that species’ genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique. Typically, one or more genes have been inte- grated into the genetic material of a genetically modified plant in order to improve certain prop- erties of the plant. Such genetic modifications also include but are not limited to targeted post- translational modification of protein(s), oligo- or polypeptides e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbi- cides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) in- hibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA car- boxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of con- ventional methods of breeding or genetic engineering; furthermore, plants have been made re- sistant to multiple classes of herbicides through multiple genetic modifications, such as re- sistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are, e.g., described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Sci- ence 316, 2007, 1185; and references quoted therein. Several cultivated plants have been ren- dered tolerant to herbicides by mutagenesis and conventional methods of breeding, e. g., Clear- field® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g., ima- zamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribe- nuron. Genetic engineering methods have been used to render cultivated plants such as soy- bean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones, and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany), and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
Furthermore, plants also include those are by the use of recombinant DNA techniques capa- ble to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal pro- teins (VIP), e. g., VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of bacteria colonizing nema- todes, e. g., Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins pro- duced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; ag- glutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cys- tatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy-steroid oxidase, ec- dysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-re- ductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hor- mone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combina- tion of protein domains, (see, e. g., WO 02/015701). Further examples of such toxins or genet- ically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810, and WO
03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above.
These insecticidal proteins contained in the genetically modified plants impart to the plants pro- ducing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, espe- cially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecti- cidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1 Ab toxin), Yield- Gard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars pro- ducing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars produc- ing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syn- genta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), I PC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants also include those are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called“pathogenesis- related proteins” (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Er- winia amylovora). The methods for producing such genetically modi-fied plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
Furthermore, plants also include those are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral patho- gens of those plants.
Furthermore, plants also include those contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nu- trition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsatu- rated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
Furthermore, plants also include those contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material produc- tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
The preparation of the pyrimidine compounds of formula (I) is illustrated by the following examples. A Preparation examples
The preparation of the Phenyllpyrimidine compounds of formula (I) is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given.
The products shown below were characterized by the mass ([m/z]) or retention time (RT; [min.]) determined by HPLC-MS spectrometry.
HPLC-MS = high performance liquid chromatography-coupled mass spectrometry; HPLC col- umn: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile + 0.1 % trifluoroacetic acid (TFA)/water + 0.1 % TFA using a gradient from 5:95 to 100:0 over 5 minutes at 40°C, flow rate 1.8 ml/min.
MS: quadrupole electrospray ionization, 80 V (positive mode).
The following abbreviations are used:
DCM: Dichloromethane
EtOAc: Acetic acid ethyl ester
THF: Tetrahydrofuran
CH: Cyclohexane
HCI: hydrogen chloride
NaOH: Sodium hydroxyde
DMF: N,N-Dimethylformamide
HPLC: High pressure chromatography
LC: Liquid chromatography
MS: Mass spectrometry
KOAc: potassium acetate
Dppf: 1 ,T-bis(diphenylphosphino)-ferrocene
MeOH: Methanol
MTBE: Methyl-tert-butylether
PE: Petrolether
TFA: Trifluoroaceticacid
DIEA: Diispropylethylamine
DAST : Diethylaminosulfurtrifluorid
MeCN: Acetonitrile
Example 1 : 5-(2-chlorophenyl)-2-(1 ,1-difluoroethyl)-4-methyl-pyrimidine (Ex.1 ):
Step1 :3-(2-chlorophenyl)-4-(dimethylamino)but-3-en-2-one:
To a solution 1-(2-chlorophenyl)propan-2-one (100 g) in DMF-dimethylacetal (200 mL) was stirred for 2 h at 125 °C. The mixture was concentrated to give 3-(2-chlorophenyl)-4-(dimethyla- mino)but-3-en-2-one (134 g, crude) as a yellow oil, used directly.
1H NMR: (400 MHz, CDCI3) d 7.70 (s, 1 H) 7.43 - 7.48 (m, 1 H) 7.28 - 7.31 (m, 3 H) 2.63 - 2.88 (m, 5 H) 1.95 (s, 3 H)
Step2:5-(2-chlorophenyl)-4-methyl-pyrimidin-2-ol:
To a solution of 3-(2-chlorophenyl)-4-(dimethylamino)but-3-en-2-one (50 g) in EtOH (1 L) was added urea (85.8 g), t-BuOK (160 g) at 20 °C, then the mixture was stirred for 48 h at 95 °C un- der N2. The mixture was filtered, the filtrate was concentrated, poured into ice HCI (6N, 90 mL), adjusted pH ~ 4, extracted with EtOAc, dried over Na2S04, filtered and concentrated to give the crude product. The crude product was triturated with MTBE, and filtered, then the filteration was purified by column (PE:EtOAc = 10:1 DCM:MeOH = 10:1 ) to give the 5-(2-chlorophenyl)-4- methyl-pyrimidin-2-ol (16 g) as a yellow solid.
1H NMR: (400 MHz, CDCI3) d 8.19 (br s, 1 H), 7.52 - 7.51 (m, 1 H), 7.53 (d, J= 2.2 Hz, 1 H), 7.42
- 7.34 (m, 2H), 7.27 - 7.23 (m, 1 H), 2.31 (s, 3H)
Step3: 2-chloro-5-(2-chlorophenyl)-4-methyl-pyrimidine:
To a solution of 5-(2-chlorophenyl)-4-methyl-pyrimidin-2-ol (16 g) in 98 ml. POCI3, was added 4 drops DMF, then the mixture was stirred for 17 h at 100 °C. The mixture was concentrated, purified by column (PE:EtOAc = 1 :0~5: 1 ) to give the 2-chloro-5-(2-chlorophenyl)-4-methyl-py- rimidine (10 g) as a yellow oil.
1H NMR: (400 MHz, CDCI3) d 8.33 - 8.54 (m, 2 H) 7.55 (br d, J= 7.53 Hz, 1 H) 7.42 (dt, ^=13.93, 6.96 Hz, 2 H) 7.18 - 7.29 (m, 1 H) 2.41 (s, 3 H)
Step4: 5-(2-chlorophenyl)-2-(1 -ethoxyvinyl)-4-methyl-pyrimidine:
To the solution of 2-chloro-5-(2-chlorophenyl)-4-methyl-pyrimidine (1 .6 g) and 1 -ethoxyvinyl- tributylstannane (2.9 g) in DMF (32 ml.) was added Pd(PPh3)2Cl2 (160 mg). Then the mixture was stirred at 90 °C for 16 h under N2. The reaction solution was quenched by the addition of H2O (120 ml.) and extracted with EtOAc. The separated organic layer was dried over anhydrous Na2S04, filtered and concentrated to give 5-(2-chlorophenyl)-2-(1 -ethoxyvinyl)-4-methyl-pyrimi- dine (4.4 g, crude) as a black oil.
Step5: 1 -[5-(2-chlorophenyl)-4-methyl-pyrimidin-2-yl]ethenone:
To the solution of 5-(2-chlorophenyl)-2-(1 -ethoxyvinyl)-4-methyl-pyrimidine (4.4 g) in 1 ,4-diox- ane (40 ml.) was added HCI (1 N, 15 ml_). Then the mixture was stirred at 25 °C for 1 h under N2. The reaction solution was quenched by the addition of H20 (100 ml.) and extracted with EtOAc. The separated organic layer was dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by column (PE:EtOAc = 1 :0~3:1 ) to give 1 -[5-(2-chlorophenyl)-4-me- thyl-pyrimidin-2-yl]ethanone (0.8 g) as a yellow oil.
1H NMR: CDCI3 400MHz d 8.64 (s, 1 H), 7.56 (dd, J=2. >, 7.3 Hz, 1 H), 7.48 - 7.37 (m, 3H), 7.27
- 7.23 (m, 1 H), 2.84 (s, 3H), 2.49 (s, 3H)
Step6:5-(2-chlorophenyl)-2-(1 ,1 -difluoroethyl)-4-methyl-pyrimidine:
To the solution 1 -[5-(2-chlorophenyl)-4-methyl-pyrimidin-2-yl]ethanone (0.96 g) in DCM (10 ml.) was added DAST (7.2 ml.) dropwise at 0 °C. Then the mixture was stirred at 25 °C for 16 h under N2. The reaction solution was added dropwise to NaHCOs (aq, sat, 50 ml.) at 0 °C and ex- tracted with EtOAc. The separated organic layer was dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by the column (PE:EtOAc = 1 :1 ~DCM:MeOH = 10:1 ) to give 5-(2-chlorophenyl)-2-(1 ,1 -difluoroethyl)-4-methyl-pyrimidine
(0.864 g) as a yellow oil.
1H NMR: CDCI3 400MHz d 8.57 (s, 1 H), 7.58 - 7.54 (m, 1 H), 7.47 - 7.38 (m, 2H), 7.25 (dd,
J= 2.2, 7.1 Hz, 1 H), 2.46 (s, 3H), 2.13 (t, =18.5 Hz, 4H).
Example 2: 5-[5-(2-chlorophenyl)-2-(1 -fluorocyclopropyl)pyrimidin-4-yl]-2,4-dimethyl-oxazole:
Step 1 : 2-(2-chlorophenyl)-1 -(2,4-dimethyloxazol-5-yl)ethanone:
To a solution of N-methoxy-N,2,4-trimethyl-oxazole-5-carboxamide (CAS2060594-87-6,
1 .50g) in THF at -78°C was added 0.5M 2-chlorobenzyl magnesium chloride solution in 2-Me- THF (20ml), stirred for 1 h at -78°C, warmed to RT overnight and quenched with saturated Na- HC03-solution. The mixture was extracted with ethylacetate, the organic pases dried and evap- orated. The residue was chromatographed with ethylacetate/hexane, resulting in 2-(2-chloro- phenyl)-1-(2,4-dimethyloxazol-5-yl)ethanone (487mg) as colourless oil.
1H NMR: (400 MHz, CDCI3) d 7.40 (m, 1 H), 7.25 (m, 3H); 4.28 (s, 2H), 2.55 (s, 3H); 2.45 (s, 3H)
Step2: 2-(2-chlorophenyl)-3-(dimethylamino)-1 -(2,4-dimethyloxazol-5-yl)prop-2-en-1 -one:
To a solution 2-(2-chlorophenyl)-1-(2,4-dimethyloxazol-5-yl)ethanone (487mg) in toluol (50ml) was added DMF-dimethylacetal (2.58ml_) and the solution was stirred for 14 h at 80 °C. The mixture was concentrated to give 2-(2-chlorophenyl)-3-(dimethylamino)-1-(2,4-dimethyloxazol-5- yl)prop-2-en-1-one (522mg, crude) as a yellow oil, used directly.
1H NMR: (400 MHz, CDCI3) d 7.70 (s, 1 H); 7.40 (m, 1 H); 7.20 (m, 3H); 2.80 (br, 6H); 2.40 (s, 3H); 2.25 (s, 3H)
Step3: 5-[5-(2-chlorophenyl)-2-(1-fluorocyclopropyl)pyrimidin-4-yl]-2,4-dimethyl-oxazole:
2-(2-chlorophenyl)-3-(dimethylamino)-1 -(2,4-dimethyloxazol-5-yl)prop-2-en-1 -one (522mg, crude) and 1-fluorocyclopropanecarboxamidine hydrochloride (285mg) were dissloved in etha- nol (20ml). Sodium ethanolate in ethanol (20%, 0.766ml) was added slowly and heated under reflux for 14h. the solvents were evaporated, in water/DCM dissolved , the organic phase sepa- rated and evaporated. The residue was chromatographed with ethylacetate/hexane, resulting in 5-[5-(2-chlorophenyl)-2-(1 -fluorocyclopropyl)pyrimidin-4-yl]-2,4-dimethyl-oxazole (184mg) as colourless oil.
1H NMR: (400 MHz, CDCI3) d 8.55 (s, 1 H); 7.50 (m, 1 H); 7.35 (m, 3H); 2.60 (s, 3H); 2.10 (s, 3H), 1.65 (m, 4H).
With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the table Ex that follows, together with physical data.
Table Ex:
Figure imgf000152_0001
Figure imgf000153_0001
B Use examples
The herbicidal activity of the pyrimidine compounds of formula (I) was demonstrated by the following greenhouse experiments:
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.
For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
For the post-emergence treatment, the 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. For this purpose, 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.
Depending on the species, the plants were kept at 10 - 25°C or 20 - 35°C, respectively.
The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
The plants used in the greenhouse experiments were of the following species:
Figure imgf000154_0002
Figure imgf000154_0001
5
At an application rate of 2000 g/ha, Ex.2 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE, and AVEFA and applied by the pre-emer- gence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.3 applied by the pre-emergence method showed very good herbicidal activity against ALOMY, AMARE, and AVEFA and applied by the post-emer- gence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 500 g/ha, Ex.4 applied by the post-emergence method showed good herbicidal activity against ALOMY and AVEFA and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 500 g/ha, Ex.5 applied by the post-emergence method showed good herbicidal activity against ALOMY and AVEFA.
At an application rate of 500 g/ha, Ex.6 applied by the post-emergence method showed very good herbicidal activity against AMARE and applied by the pre-emergence method showed good herbicidal activity against SETFA.
At an application rate of 500 g/ha, Ex.7 applied by the post-emergence method showed very good herbicidal activity against AMARE and showed good herbicidal activity against AVEFA.

Claims

Claims
1. A pyrimidine compound of formula (I),
Figure imgf000155_0001
wherein R1 is formula R1
Figure imgf000155_0002
Rx, Ry independently of each other are selected from H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, HO-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6-cycloal- koxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, C1- C6-alkylthio, Ci-C6-haloalkylthio, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, Ci-C6-al- kylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocyclo- alkyl, C3-C6-halocycloalkenyl, [1-(Ci-C6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]- C3-C6-cycloalkyl, [1 -(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1 -(Ci-C6-haloalkyl)]-C3-C6-cy- cloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6-cy- cloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cyclo- alkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl-Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, and 3- to 6-membered heterocyclyl;
wherein the cyclic groups of Rx and Ry independently of each other are unsubstituted or substituted with Re;
or Rx and Ry together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 Re;
R2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6- alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, C1-C6- haloalkoxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy-C2-C6- alkynyl, Ci-C6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C2-C6-alkynyl, C1-C6- haloalkoxy-C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloal- kenyl, C3-C6-halocycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6- haloalkyl, C3-C6-halocycloalkyl-Ci-C6-alkyl, C3-C6-halocycloalkyl-Ci-C6-haloalkyl, C3- C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkenyl-Ci-C6-haloalkyl, C3-C6-halocycloal- kenyl-Ci-C6-alkyl, C3-C6-halocycloalkenyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6- alkenyl, C3-C6-cycloalkyl-C2-C6-haloalkenyl, C3-C6-halocycloalkyl-C2-C6-alkenyl, C3- C6-halocycloalkyl-C2-C6-haloalkenyl, C3-C6-cycloalkenyl-C2-C6-alkenyl, C3-C6-cyclo- alkenyl-C2-C6-haloalkenyl, C3-C6-halocycloalkenyl-C2-C6-alkenyl, C3-C6-halocycloal- kenyl-C2-C6-haloalkenyl, C3-C6-cycloalkyl-C2-C6-alkynyl, C3-C6-cycloalkyl-C3-C6- haloalkynyl, C3-C6-halocycloalkyl-C2-C6-alkynyl, C3-C6-halocycloalkyl-C3-C6-haloal- kynyl, C3-C6-cycloalkenyl-C2-C6-alkynyl, C3-C6-cycloalkenyl-C3-C6-haloalkynyl, C3- C6-halocycloalkenyl-C2-C6-alkynyl, C3-C6-halocycloalkenyl-C3-C6-haloalkynyl, C3-C6- cycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkyl-C2-C6-haloalkylidenyl, C3-C6-halocyclo- alkyl-C-i-C6-alkylidenyl, C3-C6-halocycloalkyl-C2-C6-haloalkylidenyl, C3-C6-cycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-C2-C6-haloalkylidenyl, C3-C6-halocycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkenyl-C2-C6-haloalkylidenyl, heterocyclyl- Ci-C6-alkylidenyl, heterocyclyl-C2-C6-haloalkylidenyl, C3-C6-hydroxycycloalkyl-C-i-C6- alkyl, C3-C6-hydroxycycloalkyl-Ci-C6-haloalkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-al- kyl, C3-C6-hydroxycycloalkenyl-Ci-C6-haloalkyl, Ci-C6-hydroxyalkyl, C2-C6-hydroxy- haloalkyl, C3-C6-hydroxyalkenyl, C3-C6-hydroxyhaloalkenyl, C3-C6-hydroxyalkynyl, C4-C6-hydroxyhaloalkynyl, C3-C6-hydroxycycloalkyl, C3-C6-hydroxyhalocycloalkyl, C3-C6-hydroxycycloalkenyl, C3-C6-hydroxyhalocycloalkenyl, C3-C6-cycloalkyl-Ci-C6- hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkyl-Ci-C6- hydroxyalkyl, C3-C6-halocycloalkyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloalkenyl-Ci- C6-hydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-hydroxyhaloalkyl, C3-C6-halocycloalkenyl- Ci-C6-hydroxyalkyl, C3-C6-halocycloalkenyl-C2-C6-hydroxyhaloalkyl, C3-C6-cycloal- kyl-C3-C6-hydroxyalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocy- cloalkyl-C3-C6-hydroxyalkenyl, C3-C6-halocycloalkyl-C3-C6-hydroxyhaloalkenyl, C3- C6-cycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-cycloalkenyl-C3-C6-hydroxyhaloalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydrox- yhaloalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyalkynyl, C3-C6-halocycloalkyl-C3-C6-hy- droxyalkynyl, C3-C6-cycloalkenyl-C3-C6-hydroxyalkynyl, C3-C6-halocycloalkenyl-C3- C6-hydroxyalkynyl, C3-C6-cycloalkyl-C2-C6-hydroxyalkylidenyl, C3-C6-halocycloalkyl- C2-C6-hydroxyalkylidenyl, C3-C6-cycloalkenyl-C2-C6-hydroxyalkylidenyl, C3-C6-halo- cycloalkyl-C2-C6-hydroxyalkylidenyl, heterocyclyl-C2-C6-hydroxyalkylidenyl, hy- droxycarbonyl-Ci-C6-hydroxyalkyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl- Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-hydroxyalkyl, Ci-C6-haloalkoxycar- bonyl-Ci-C6-hydroxyalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloal- koxycarbonyl-C-i-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloal- koxyca rbonyl-Ci -C6-a I kyl , C3-C6-hyd roxycycloa I kyl-Ci -C6-hyd roxyal kyl , C3-C6-hy- d roxycycl oa I kenyl-Ci -C6-hyd roxya I kyl , C3-C6-hyd roxycycloa I kyl-C3-C6-hyd roxy- a I kenyl , C3-C6-hyd roxycycloal kenyl-C3-C6-hyd roxya I kenyl , C3-C6-hyd roxycycloa I kyl- C3-C6-hyd roxya I kynyl , C3-C6-hyd roxycycloal kenyl-C3-C6-hyd roxyal kenyl , C2-C6-d ihy- droxyalkyl, C3-C6-dihydroxyhaloalkyl, C4-C6-dihyd roxya I kenyl, C4-C6-dihydroxy- haloalkenyl, C4-C6-dihyd roxya I kynyl, Cs-Ce-dihydroxyhaloalkynyl, C4-C6-dihydroxycy- cloalkyl, C4-C6-dihydroxyhalocycloalkyl, C4-C6-dihydroxycycloalkenyl, C4-C6-dihy- droxyhalocycloalkenyl, C3-C6-cycloalkyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloalkyl- C2-C6-dihydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloal- kenyl-C2-C6-d i hyd roxya I kyl , C3-C6-cycloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-hal ocy- cloa I kyl-C3-C6-d i hyd roxya I kenyl , C3-C6-cycloa I kenyl-C3-C6-d i hyd roxya I kenyl , C3-C6- halocycloalkenyl-C3-C6-dihydroxyalkenyl, C3-C6-cycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-halocycloal kyl-C4-C6-d ihyd roxyal kynyl , C3-C6-cycloal kenyl-C4-C6-d ihyd roxy- alkynyl, C3-C6-halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkyl-C3-C6-dihy- droxyalkylidenyl, C3-C6-halocycloalkyl-C3-C6-dihydroxyalkylidenyl, heterocyclyl-C3- C6-dihydroxyalkylidenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, hydroxycarbonyl-C3- C6-dihydroxyhaloalkyl, Ci-C6-alkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloal- koxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloalkoxycarbonyl-C3-C6-dihydroxy- haloalkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-alkyl, C3-C6-dihydroxycycloalkyl- C1-C6- haloalkylC3-C6-dihydroxycycloalkyl- C2-C6-alkenyl, C3-C6-dihydroxycycloalkyl- C2-C6- haloalkenyl, C3-C6-dihydroxycycloalkyl- C2-C6-alkynyl, C3-C6-dihydroxycycloalkyl- C3-C6-haloalkynyl, Ci-C6-alkylcarbonyl-C-i-C6-alkyl, Ci-C6-haloalkylcarbonyl-C-i-C6- alkyl, Ci-C6-alkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-haloalkyl, hydroxycarbonyl-C2-C6-alkenyl, hydroxycarbonyl-C2-C6-haloalkenyl, Ci-C6-alkoxy- carbonyl-C2-C6-alkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkenyl, Ci-C6-alkoxycar- bonyl-C2-C6-haloalkenyl, Ci-C6-haloalkoxycarbonyl-C2-C6-haloalkenyl, hydroxycar- bonyl-C2-C6-alkynyl, hydroxycarbonyl-C3-C6-haloalkynyl, Ci-C6-alkoxycarbonyl-C2- C6-alkynyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkynyl, C-i-C6-alkoxycarbonyl-C3-C6- haloalkynyl, Ci-C6-haloalkoxycarbonyl-C3-C6-haloalkynyl, Ci-C6-cyanoalkyl, C2-C6- cyanohaloalkyl, Ci-C6-dicyanoalkyl, C2-C6-dicyanohaloalkyl, di(hydroxycarbonyl)-Ci- C6-alkyl, di(hydroxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxycarbonyl)-C-i-C6-alkyl, di(Ci-C6-haloalkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-haloalkoxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxyl)phosphoryl-C-i-C6- alkyl, di(Ci-C6-haloalkoxyl)phosphoryl-Ci-C6-alkyl, di(Ci-C6-alkoxyl)phosphoryl-C-i- C6-haloalkyl, di(Ci-C6-haloalkoxyl)phosphoryl-Ci-C6-haloalkyl, phosphoryl-C-i-C6-al- kyl , phosphoryl-Ci-C6-haloalkyl , di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-haloalkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-alkoxyl)phosphoryl-)]C-i- C6-haloalkyl, di[di(Ci-C6-haloalkoxyl)phosphoryl-)]Ci-C6-haloalkyl, diphosphoryl-Ci- C6-alkyl , diphosphoryl-Ci-C6-haloalkyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-haloal- kylthio-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6-haloalkyl, Ci-C6-haloalkylthio-Ci-C6-haloal- kyl, Ci-C6-alkylsulfinly-Ci-C6-alkyl, Ci-C6-haloalkylsulfinly-Ci-C6-alkyl, Ci-C6-alkyl- sulfinly-Ci-C6-haloalkyl, Ci-C6-haloalkylsulfinly-Ci-C6-haloalkyl, Ci-C6-alkylsulfonyl- Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6- haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (Ci-C6-alkyl)carbonylaminocarbonyl, (C3-C6-alkenyl)carbonylaminocarbonyl, (C3-C6- alkynyl)carbonylaminocarbonyl, (Ci-C6-haloalkyl)carbonylaminocarbonyl, al- kynylphenylcarbonylaminocarbonyl, (C3-C6-cycloalkyl)carbonylaminocarbonyl,
[di(Ci-C6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkyl)aminocar- bonyl, [(Ci-C6-haloalkyl)carbonyl](Ci-C6-alkyl)aminocarbonyl, [(C3-C6-cycloalkyl)car- bonyl](Ci-C6-alkyl)aminocarbonyl, (phenylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (het- erocyclylcarbonyl)(Ci-C6-alkyl)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkyl)ami- nocarbonyl, [(Ci-C6-alkyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(Ci-C6-haloal- kyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](Ci-C6-al- kyloxy)aminocarbonyl, (phenylcarbonyl)(Ci-C6-alkoxy)aminocarbonyl, (heterocyclyl- carbonyl)(Ci-C6-alkoxy)aminocarbonyl, (heteroarylcarbonyl)(Ci-C6-alkoxy)aminocar- bonyl, [(Ci-C6-alkyl)carbonyl](C3-C6-alkenyl)aminocarbonyl, [(Ci-C6-haloalkyl)car- bonyl](C2-C6- alkenyl)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkenyl)ami- nocarbonyl, (phenylcarbonyl)(C3-C6-alkenyl)aminocarbonyl, (heterocyclylcar- bonyl)(C3-C6-alkenyl)aminocarbonyl, (heteroarylcarbonyl)(C3-C6-alkenyl)aminocar- bonyl, [(Ci-C6-alkyl)carbonyl](C3-C6-alkynyl)aminocarbonyl, [(Ci-C6-haloalkyl)car- bonyl](C3-C6-alkynyl)aminocarbonyl, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkynyl)ami- nocarbonyl, (phenylcarbonyl)(C3-C6-alkynyl)aminocarbonyl, (heterocyclylcar- bonyl)(C3-C6-alkynyl)aminocarbonyl, (heteroarylcarbonyl)(C3-C6-alkynyl)aminocar- bonyl, [(C2-C6-alkenyl)carbonyl]aminocarbonyl, [(C2-C6-alkenyl)carbonyl](Ci-C6-al- kyl)aminocarbonyl, [(C2-C6-alkenyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [(C3-C6- alkynyl)carbonyl]aminocarbonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-alkyl)aminocar- bonyl, [(C3-C6-alkynyl)carbonyl](Ci-C6-alkoxy)aminocarbonyl, [di(Ci-C6-al- kyl)amino]carbonylaminocarbonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkyl)ami- nocarbonyl, [di(Ci-C6-alkyl)aminocarbonyl](Ci-C6-alkoxy)aminocarbonyl;
wherein OH groups of R2 are unsubstituted or substituted by Rb;
carbon atoms of cyclic groups of R2 are unsubstituted or substituted independently of each other with 1 , 2, or 3 moieties R20; and heteroatoms of cyclic groups of R2 are unsubstituted or substituted with Q;
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl- carbonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6-alkyl)aminosulfonyl, or Ci-C6-alkylaminosulfonyl;
Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3- C6-halocycloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl- Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-haloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, hydroxycarbonyl-Ci- C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-haloal- kyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-haloalkylthiocarbonyl, Ci-C6-alkyl- aminocarbonyl, Ci-C6-haloalkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, C1- C6-dihaloalkylaminocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C1-C6- alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-haloalkyl, Ci-C6-haloalkoxy-Ci-C6-haloalkyl, phenyl-Ci-C6-alkyl, or phenyl-Ci-C6-haloalkyl; R20 is H, halogen, CN, NO2, OH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-(Ci-C4- alkoxy)n, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl, ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfinyl, C3-C6-a I ki nyl su If i ny I , aminosulfinyl, Ci-C6-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfinyl, C3-C6-alken- ylsulfonyl, C3-C6-alkinylsulfonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci- C6-alkyl)aminosulfonyl, Ci-C6-alkylcarbonylaminosulfonyl, C3-C6-cycloalkylcar- bonylaminosulfonyl, hydroxysulfonyl, Ci-C6-alkoxysulfonyl, hydroxycarbonyl, ami- nocarbonyl, NH2-aminocarbonyl, Ci-C6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3- C6-alkinylcarbonyl, thiocarbonyl, Ci-C6-alkylcarbonylaminocarbonyl, C3-C6-cyclo- alkylcarbonylaminocarbonyl, Ci-C6-alkylsulfonylaminocarbonyl, C3-C6-cycloalkyl- sulfonylaminocarbonyl, di(Ci-C6-alkyl)aminosulfonylaminocarbonyl, hydroxy- aminocarbonyl, Ci-C6-alkoxyaminocarbonyl, [(Ci-C6-alkoxy)(Ci-C6-al- kyl)amino]carbonyl, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, (HO)2(0)P,
(HO)(Ci-C6-alkoxy)(0)P, (Ci-C6-alkoxy)2(0)P, Cs-Cs-cycloalkyl, C4-C8-cycloal- kenyl, C-i-Cs-alkylidenyl-cycloalkyl, C-i-Cs-alkylidenyl-heterocyclyl, phenyl, 5- or 6- membered heteroaryl, or 3- to 6-membered heterocyclyl, phenylsulfinyl, 5- or 6- membered heteroarylsulfinyl, 3- to 6-membered heterocyclylsulfinyl, C3-C6-cyclo- alkylsulfinyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- to 6-mem- bered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Rb is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3- C6-haloalkinyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6- halocycloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C6-alkyl, C1-C6- alkyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-aminocarbonyl, Ci-C6-dialkyla- minocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl- sulfonyl, Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rc is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, C1-C6- haloalkoxy, NH2, Ci-C6-alkyl-amino, di(Ci-C6-alkyl)amino, SH, Ci-C6-alkylthio, C1- C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6- alkenyloxycarbonyl, alkinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, ami- nocarbonyl, Ci-C6-alkylaminocarbonyl, or di(Ci-C6-alkyl)aminocarbonyl;
Rd is halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloal- kyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6- alkinyloxy, Ci-C6-haloalkoxy, NH2, Ci-C6-alkyl-amino, di(C1-C6-alkyl)amino, SH, Ci -C6-a I ky Ith i o , Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C4-C8- cycloalkenyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkenyloxycarbonyl, Ci-C6-alkinyloxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci- C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl- sulfonyl, Ci-C6-alkoxy- Ci-C6-alkyl, phenylthio, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
R4 and R5 are independently from each other selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, OH, NH2, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, Ci-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, C1- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinyl- sulfonyl, Ci-C6-alkylsulfinyl, C3-C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, C1-C6- alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-membered heterocyclyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, 3- or 6-membered heterocyclyloxy, C3-C6-cycloalkyloxy, C3-C6-cy- cloalkenyloxy, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6- membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkenylcar- bonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl, 5- or 6-membered heteroarylsulfinyl, 3- or 6-membered heterocy- clylsulfinyl, C3-C6-cycloalkylsulfinyl, C3-C6-cycloalkenylsulfinyl, phenyloxycar- bonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-membered heterocy- clyloxycarbonyl, C3-C6-cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, amino- sulfonyl, Ci-C6-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, aminosulfinyl, Ci-C6-alkylaminosulfinyl, and di(Ci-C6-alkyl)aminosulfinyl;
Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
R3 same or differently is H, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl- carbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloal- kyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; Re is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloal- koxy;
Rf is H, halogen, CN, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-mem- bered heterocyclyl;
m is 0, 1 , 2, 3, or 4;
n is 1 , 2, 3, 4, or 5;
including agriculturally acceptable salts or derivatives of compounds of formula (I);
provided that when R1 is CF3 and Z-(R3)m is Phenyl, R2 is not CF3;
and when R1 is CF3 and Z-(R3)m is 4-CN-Phenyl, R2 is not Phenyl, Piperidyl or N-substi- tuted piperidinyl.
2. The compound of formula I according to claim 1 , wherein Z-(R3)m is formula W1,
Figure imgf000160_0001
wherein R3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1- C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1- C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; R3b and R3c each independently is H, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1- C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-al- kynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Cr C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6- cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3b and R3c are each independently unsubstituted or substi- tuted with substituents Re; and
# denotes the point of attachment to the pyrimidine ring.
3. The compound of formula I according to claim 1 or 2, wherein Z-(R3)m is selected from groups A to G,
Figure imgf000161_0001
wherein
R3 is halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, and Ci-C6-alkoxy;
R3b is H, halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring.
4. The compound of formula I according to claim 1 or 2, wherein Z-(R3)m is selected from groups H to V,
Figure imgf000162_0001
wherein
Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
R3 same or differently are selected from halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, and Ci-C6-alkoxy;
R3b and R3c each independently is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or C1-C6- alkoxy;
X1 is O, S, or NR3A;
R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring.
5. The compound of formula I according to any of the preceeding claims, wherein R2 is se- lected from R2-1 to R2-43,
Figure imgf000162_0002
Figure imgf000163_0001
wherein W, X, and Y denotes R20 which independently of each other are identical or differ ent; Q is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ci-C6-alkylcarbonyl, C2-C6-alkenylcar- bonyl, C2-C6-alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, di(Ci-C6- alkyl)aminosulfonyl, or Ci-C6-alkylaminosulfonyl.
6. The compound of formula I according to claim 5, wherein R2 is R2-5, R2-6, R2-7, R2-20, R2- 21 , or R2-22.
7. The compound of formula I according to any of preceding claims, wherein
Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cycloalkyl,
Or Rx and R y together with the carbon they are attached can form a 3-to 5-membered sat- urated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl.
8. The compound of formula I according to any of preceding claims is the compound of for- mula 1.1 ,
Figure imgf000164_0001
wherein Rx, Ry independently are H, halogen, Ci-C6-alkyl, Ci-C6-haloalky, or C3-C6-cyclo- alkyl, or Rx and Ry together with the carbon they are attached can form a 3-to 5- membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 Re;
R2 is R2-5, R2-7, or R2-20;
Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G, or 9- to 10- membered bicyclic ring selected from H to V;
R3 is halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl;
m is 1 or 2.
9. A use of pyrimidine compounds of formula (I), including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, according to any of claims 1 to 8, as herbicide.
10. A herbicidal composition comprising:
A) at least one pyrimidine compound of formula I, including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, ac- cording to any of claims 1 to 8;
and
B) herbicides of class b1) to b15):
b1 ) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibi- tors);
b11 ) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, daz- omet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indazi- flam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640- 27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphe- noxy)-4-pyridazinol, and its salts and esters;
including their agriculturally acceptable salts or derivatives.
1 1. A herbicidal composition comprising the herbicidal composition according to claim 10, and safeners.
12. The herbicidal composition according to any of claim 10 to 1 1 , wherein the weight ratio of component A to component B is in the range of from 1 :500 to 500:1.
13. A herbicidal composition comprising a herbicidal active amount of at least one pyrimidine compound of formula (I) including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, according to any of claims 1 to 8, and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface- active substance.
14. A herbicidal composition comprising a herbicidal composition according to any of claims 10 to 12, and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
15. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of at least one pyrimidine compound of formula (I) including agriculturally accepta- ble salts or derivatives of compounds of formula (I) having an acidic functionality, accord- ing to any of claims 1 to 8 or a composition according to any of claims 10 to 13 to act on plants, their environment or on seed.
PCT/EP2018/084863 2017-12-20 2018-12-14 Herbicidal pyrimidine compounds WO2019121352A1 (en)

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