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WO2019121373A1 - Composés herbicides de pyrimidine - Google Patents

Composés herbicides de pyrimidine Download PDF

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Publication number
WO2019121373A1
WO2019121373A1 PCT/EP2018/084899 EP2018084899W WO2019121373A1 WO 2019121373 A1 WO2019121373 A1 WO 2019121373A1 EP 2018084899 W EP2018084899 W EP 2018084899W WO 2019121373 A1 WO2019121373 A1 WO 2019121373A1
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alkyl
alkoxy
formula
membered
cycloalkyl
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Inventor
Veronica LOPEZ CARRILLO
Matthias Witschel
Gunther Zimmermann
Tobias SEISER
Florian Vogt
Thomas Seitz
Gerd Kraemer
Peter Dombo
Klaus Reinhard
Eva HOLLENBACH
Ruth CAMPE
Klaus Kreuz
Doreen Schachtschabel
Trevor William Newton
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only 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
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—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 three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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.
  • WO2013/178585 describes the substituted pyridine compound and its use as herbicides compounds.
  • R 1 is Ci-C 6 -alkyl, Ci-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 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -cyclo- alkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C
  • R 2 is 5-membered heteroaryl selected from pyrrolyl, imidazolyl, isooxazolyl, pyrazolyl, thia- zolyl, isothiazolyl, thiadiazolyl, 1 ,2,3-oxadiazolyl, triazolyl, and tetrazolyl, wherein carbon atoms of R 2 independently are unsubstituted or substituted with X, Y or W and nitrogen atoms of R 2 independently are unsubstituted or substituted with Q, provided that R 2 is not 1 -methylimidazol-2-yl;
  • Q is H, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -dialkylamino- sulfonyl, or Ci-C 6 -alkylaminosulfonyl;
  • X , Y and W are independently H, halogen, CN, NO 2 , OH, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 1 -C 6 - alkoxy-(Ci-C 4 -alkoxy) n , Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkylsulfonyl, OR b , SH, SR b , C 2 -C 6 - 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
  • cyclic groups of X, Y and W are independently unsubstituted or substituted with R c ; and acyclic aliphatic groups of X, Y and W are independently 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-halocycloal- kenyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, Ci-C 6 -haloalkylcarbonyl, C3- C 6 -cycloalkylcarbonyl, hydroxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkyloxycarbonyl, Ci-C 6 -alkylthi- ocarbonyl, Ci-C 6 -a
  • 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, C1- C 6 -alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocar- bonyl, 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-C6- haloalkenyl, C3-C6-haloalkinyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C1-C6- haloalkoxy, NH2, Ci-C 6 -alkyl-amino, di(C1-C6-alkyl)amino, SH, Ci-C 6 -alkylthio, Ci-C 6 -al- kylsulfinyl, Ci-C 6 -alkylsulfonyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, hydroxycarbonyl, C1- C 6 -alkoxy
  • 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;
  • R 4 and R 5 are independently from each other selected from hydrogen, Ci-C 6 -alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkinyl, OH, NH 2 , Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C 1 -C 6 - alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C 6 -alkylsulfonyl, C 1 -C 6 - haloalkylsulfonyl, C 3 -C 6 -alkenylsulfonyl, C 3 -C 6 -alkinylsulfonyl, Ci-C 6 -alkylsulfinyl, C 3 -C 6 - alkenylsulfinyl, C
  • Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered partially or fully unsatu- rated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
  • R 3 same or differently are selected from 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 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -al- kynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, C 1 -C 6 - alkoxycarbonyl, Ci-C 6 -alkylthio,
  • n 0, 1 , 2, 3, or 4;
  • n 0, 1 , 2, 3, 4, or 5;
  • the present invention also provides the pyrimidine compounds of formula (I)
  • R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, HO-Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl, C 3 -C 6 -haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C 3 -C 6 -alkenyloxy, C 3 - C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -cyclo- alkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -halocycl
  • R 2 is 5-membered heteroaryl selected from pyrrolyl, imidazolyl, isooxazolyl, pyrazolyl, thia- zolyl, isothiazolyl, thiadiazolyl, 1 ,2,3-oxadiazolyl, triazolyl, and tetrazolyl, wherein carbon atoms of R 2 independently are unsubstituted or substituted with X, Y or W and nitrogen atoms of R 2 independently are unsubstituted or substituted with Q, provided that R 2 is not 1 -methylimidazol-2-yl;
  • Q is H, Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, Ci-C6-alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, Ci-C6-dialkylamino- sulfonyl, or Ci-C6-alkylaminosulfonyl;
  • X , Y and W are independently H, halogen, CN, NO 2 , OH, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 1 -C 6 - alkoxy-(Ci-C 4 -alkoxy) n , Ci-C 6 -alkylsulfinyl, or Ci-C 6 -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 su If i ny I , aminosulfinyl, Ci-C 6 -alkylaminosulfinyl, di(Ci-C 6 -alkyl)aminosul
  • cyclic groups of X, Y and W are independently unsubstituted or substituted with R c ; and acyclic aliphatic groups of X, Y and W are independently unsubstituted or substituted with R d ;
  • R b is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkinyl, C 3 -C 6 - haloalkinyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloal- kenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, C 3 - C6-cycloalkylcarbonyl, hydroxycarbonyl-Ci-C6-alkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-alkylthi- ocarbonyl,
  • R c is halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, NH 2 , Ci-C 6 -alkyl-amino, di(Ci-C 6 -alkyl)amino, SH, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, C 1 - C 6 -alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C 2 -C 6 -alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocar- bonyl, or di(Ci-C 6 -alkyl)aminocarbonyl;
  • R d is halogen, CN, NO 2 , 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, NH 2 , Ci-C 6 -alkyl-amino, di(C1-C6-alkyl)amino, SH, Ci-C 6 -alkylthio, Ci-C 6 -al- kylsulfinyl, Ci-C 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, C 4 -C 8
  • R e is halogen, CN, NO 2 , 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;
  • R 4 and R 5 are independently from each other selected from hydrogen, Ci-C 6 -alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkinyl, OH, NH 2 , Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C 1 -C 6 - alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, Ci-C 6 -alkylsulfonyl, C 1 -C 6 - haloalkylsulfonyl, C 3 -C 6 -alkenylsulfonyl, C 3 -C 6 -alkinylsulfonyl, Ci-C 6 -alkylsulfinyl, C 3 -C 6 - alkenylsulfinyl, C
  • Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered partially or fully unsatu- rated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
  • R 3 same or differently are selected from 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 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-al- kynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, Ci-C 6 -alkylthio, Ci-C 6 -haloalky
  • n 0, 1 , 2, 3, 4, or 5;
  • 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, N02, 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, C
  • 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 described 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:
  • the pyrimidine compounds of formula (I) can be obtained by reacting respective aminoketones of formula (II) with
  • 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, TBME, dioxane, anisole and THF, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, alcohols such as methanol, etha- nol, n-propanol, isopropanol, n-butanol
  • -butanol as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and 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 LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS or 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, 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 or LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and al
  • 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 NaOCH 3 , NaOC2H 5 , KOC2H5, tBuOK and potassium tert-pentoxide.
  • the ba- ses are generally employed in equimolar amounts; however, they can also be employed in cata- lytic 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 (III), based on the aminoketone (II).
  • Amidines (III) are known from literature or commercially available.
  • 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 without solvent 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.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o
  • 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 synthesis of pyrimidines (XIII) 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 (XI) in an organic solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XI) at least partly and prefer- ably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH2CI2, CHC , CCH2CICH2CI or CCU, ethers such as diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP as well as alcohols such as methanol, ethanol, isopropanol, butanol.
  • Preferred solvents are methanol and ethanol . It is also possible to use mixtures of the solvents mentioned.
  • the oxidation of pyrimidines (XIV) 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 (XIV) in an organic solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XIV) at least partly and pref- erably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, 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, 0-, 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,
  • Preferred solvents are halogenated hydrocarbons such as CH2CI2, CHCU, 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, CHCU, CCH2CICH2CI or CCU. It is also possible to use mixtures of the solvents men- tioned.
  • oxidizing agents for the synthesis of pyrimidines (XI) are metal oxides such as Mn0 2 , KMn0 4 , Cr0 3 or PCC, and non-metal oxides such as NaCIO, Nal0 4 or pyridine/S0 3 - complex.
  • methods like the Swern oxidation or the TEMPO oxidation known to a per- son skilled in the art can be used to obtain pyridines of formula (XI).
  • Preferred agents include Mhq2, KMn0 4 and PCC, more preferred Mn0 2 .
  • the pyrimidines of formula (XIV) can be obtained by reacting respective pyrimidines of formula (XV) with a reducing agent such
  • the reduction of pyrimidines (XV) 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.
  • reducing agents for pyrimidines include LAH, DIBALH, LiBH 4 or lithium triethyl- borohydride.
  • Preferred agents include LAH and DIBALH.
  • the hydride-source is used preferably from 1 to 10 equivalents based on the pyrimidine (XV), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (XV), most preferably from 1.2 to 2.5 equivalents based on the pyrimidine (XV).
  • the reaction is usually carried out at temperatures from -100° C to the boiling point of the reaction mixture, preferably from -20°C to 60°C, particularly from 0°C to 25° C.
  • the reaction may be carried out without solvent or in an organic solvent.
  • Suitable solvents are those capable of dissolving the alkynes X(IV) and 2-chloro-2-(iminohydroxy)-acetates (XVII) 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 THF is used as solvent. It is also possible to use mixtures of the solvents mentioned.
  • aromatic hydrocarbons such as benzene, chlorobenzene, tol
  • Suitable bases are, in general, organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dime- thylaminpyridine, and also bicyclic amines. Particular preference is given to TEA and DIPEA.
  • the pyrimidines of formula (XIX) can be obtained from pyrimidines of formula (XXX) by known methods e.g using CBr 4 / PPh 3 / base (e.g. Corey E.J. etai I Tetrahedron Letters, 1972, 3769- 3772) or using the Bestmann-Ohira reagent (e.g. Ohira S. Syn. Comm. 1989,19:561 ).
  • 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.
  • 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-C 4 -alkoxy-Ci-C 4 - 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
  • 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 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.
  • 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 organic moieties mentioned in the definition of the variables R 1 , R 2 , Z, R 3 , and R 3A are - like the term halogen - collective terms for individual enumerations of the individual group mem- bers.
  • the term halogen denotes in each case F, Cl, Br, or I.
  • All hydrocarbon chains, e.g. all al- kyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting 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-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 -
  • 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, pentafluoroethyl,
  • Ci-C 6 -haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, and dodecafluorohexyl;
  • C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • 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-
  • 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- 1 -yl, or 6-iodohex-5-yn-1 -y
  • Ci-C 4 -alkoxy e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy, and 1 ,1-dimethylethoxy;
  • 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-ethyl-2-methylpropoxy.
  • 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-ethylbutylthio, 2-
  • (Ci-C 4 -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-C 4 -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-ethylbuty
  • di(Ci-C 4 -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 ,
  • 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 -alkylthio (Ci-C 6 -alkyl-S-): e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1 ,1-dimethylethylthio, pentylthio, 1-methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, 1 ,1-di- methylpropylthio, 1 ,2-dimethylpropyl-thio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentyl-thio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio,
  • 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 - ethy
  • 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 Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3- C 6 -haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloalkoxy, C3-C6-cycloalk- oxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C 6 -alkylthio,
  • R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, HO- Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloal- kenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C 3 -C 6 -alkenyl- oxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C6-haloalkoxy, C 3 -Ce-cy- cloalkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -halo- alkenyloxy, C 3 -C 6 -alkynyloxy, C 4 -C 6 -haloalkynyloxy, Ci-C6-alkylthio, C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R 1 is C2H5, 1-C3H7, 1-C4H9, OCH3, C-C3H5, or C-C4H7;
  • R 1 is C2H5, OCH3, or C-C3H5; most preferred R 1 is C-C3H5;
  • R 2 is selected from R 2 -1 to R 2 -32 as shown below,
  • R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9, or R 2 -31 ;
  • R 2 is R 2 -4, R 2 -5, or R 2 -6;
  • R 2 is R 2 -10, R 2 -1 1 , R 2 -12, R 2 -13, R 2 -15, R 2 -16, R 2 -17, or R 2 -18;
  • R 2 is R 2 -19, R 2 -20, R 2 -21 , R 2 -22, R 2 -23, R 2 -24, R 2 -25, R 2 -26, R 2 -27, R 2 -28, R 2 - 29, R 2 -30, R 2 -31 , or R 2 -32;
  • R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • R 2 is R 2 -1 , R 2 -2, or R 2 -3;
  • R 2 is R 2 -1 ;
  • R 2 is R 2 -2;
  • R 2 is R 2 -3;
  • R 2 is R 2 -7, R 2 -8, or R 2 -9;
  • R 2 is R 2 -7;
  • R 2 is R 2 -8;
  • R 2 is R 2 -9;
  • 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, 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-alkenylsul
  • cyclic groups of X are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X are unsubstituted or substituted with R d ; more preferred X is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(C-i-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 -alkylsulfi- nyl, Ci-C 6 -alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcar- bonyl, Ci-C 6 -alkylcarbonylaminocarbonyl, hydroxya
  • 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-C6-alkoxy-(Ci-C 4 -alkoxy) n is Ci-C6-alkoxy-(Ci-C 4 -alkoxy) n ;
  • 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 Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkylsulfonyl;
  • Ci-C 6 -alkylthio is Ci-C 6 -alkylthio
  • X is Ci-C 6 -alkylsulfinyl
  • Ci-C 6 -alkylsulfonyl is also more particularly preferred X is Ci-C 6 -alkylsulfonyl
  • X is H, Ci-C 6 -alkyl, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkyl- sulfonyl;
  • X is H, Ci-C 6 -alkyl, or Ci-C 6 -alkylthio;
  • X is H, Ci-C 6 -alkylthio, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , or Ci-C 6 -alkylsulfinyl; also especially preferred X is H, Ci-C 4 -alkyl, Ci-C 2 -fluoroalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -alkylthio; more especially preferred X is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t- butyl, OCH3, or SCH3;
  • 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 ;
  • most particularly preferred X is H; also most particularly preferred X is CH3;
  • 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, 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-alkenylsulf
  • cyclic groups of Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of Y are unsubstituted or substituted with R d ;
  • Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy-(C-i-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 -alkylsulfi- nyl, Ci-C 6 -alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcar- bonyl, Ci-C 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, (HO) 2 (0)P, (C1-C6- alkoxy) 2 (0)P
  • cyclic groups of Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of Y are unsubstituted or substituted with R d ;
  • 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 Y are unsubstituted or sub- stituted with R d ;
  • Y is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(Ci-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-C6-alkoxy-(Ci-C 4 -alkoxy) n ;
  • Y is Ci-C 6 -haloalkoxy
  • Y is Ci-C 6 -alkyl, preferably CH 3 , C 2 H 5 , n-propyl, CH(CH3) 2 , n-butyl, isobutyl;
  • Y is Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkylsulfonyl;
  • Y is Ci-C 6 -alkylthio
  • Y is Ci-C 6 -alkylsulfinyl
  • Y is Ci-C 6 -alkylsulfonyl
  • Y is H, Ci-C 6 -alkyl, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, or Ci-C 6 -alkyl- sulfonyl; particularly preferred Y is H, Ci-C 6 -alkyl, or Ci-C 6 -alkylthio;
  • Y is H, Ci-C 6 -alkylthio, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , or Ci-C 6 -alkylsulfinyl; also especially preferred Y is H, Ci-C 4 -alkyl, Ci-C2-fluoroalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -alkylthio; more especially preferred Y is H, CH3, C2H5, n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t- butyl, OCH3, or SCH3;
  • Y is H, CH 3 , C2H 5 , n-propyl, isopropyl, OCH 3 , or SCH 3 ;
  • Y is H, halogen, CH 3 , C2H 5 , OH, or OCH 3 ;
  • Y is H, CH 3 , C2H 5 , or SCH 3 ;
  • Y is H, CH 3 , C2H 5 , F, Cl, Br, or I;
  • Y is H, CH 3 , or C2H 5 ;
  • Y is H
  • Y is CH 3 ;
  • Y is C2H 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, 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-alkenylsulfon
  • cyclic groups of W are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of W 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 -alkylsulfi- nyl, Ci-C 6 -alkylsulfonyl, hydroxysulfonyl, Ci-C 6 -alkoxysulfonyl, aminocarbonyl, Ci-C 6 -alkylcar- bonyl, Ci-C 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, (HO) 2 (0)P, (C1-C6- alkoxy) 2 (0)P, HO
  • cyclic groups of W are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of W 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 W are unsubstituted or substituted with R c ; and
  • acyclic aliphatic groups of W 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 ;
  • 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, or SR b , wherein alkyl or alkoxy groups of W are unsubstituted or sub- stituted with R d ;
  • W is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-(Ci-C 4 - alkoxy) n , Ci-C6-haloalkoxy;
  • W is H
  • W is halogen
  • W is Ci-C 6 -alkyl; also more particularly preferred W is Ci-C6-haloalkyl;
  • W is Ci-C6-alkoxy-(Ci-C4-alkoxy) n ;
  • W is Ci-C6-haloalkoxy
  • W is Ci-C6-alkyl, preferably CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl;
  • W is Ci-C6-alkylthio, C 1 -C6-a I ky I s u If i ny I , or Ci-C6-alkylsulfonyl;
  • W is Ci-C6-alkylthio
  • W is Ci-C6-alkylsulfinyl
  • W is Ci-C6-alkylsulfonyl
  • W is H, Ci-C6-alkyl, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkyl- sulfonyl;
  • W is H, Ci-C6-alkyl, or Ci-C6-alkylthio
  • W is H, Ci-C6-alkylthio, Ci-C6-alkoxy-(Ci-C4-alkoxy) n , or Ci-C6-alkylsulfi- nyl;
  • W is H, Ci-C 4 -alkyl, Ci-C 2 -fluoroalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -al- kylthio;
  • W is H, CH 3 , C 2 H 5 , n-propyl, isopropyl, isobutyl, n-butyl, 2-butyl, t- butyl, OCH3, or SCH3;
  • 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 CH3;
  • 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; perticularly preferred Q is H;
  • 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-C6-alkyl or Ci-C6-alkoxy, Ci-C6-haloalkoxy, or NH 2 ;
  • R c is Ci-C6-alkyl or Ci-C6-alkoxy
  • R c is Ci-C6-alkyl
  • preffered R d is CN, OH, halogen, Ci-C 6 -alkyl, C3-C6-cycloalkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, Ci-C 6 -haloalkoxy, NH2, 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
  • 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.
  • 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 2 is selected from R 2 -1 to R 2 -32; preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 - 31 , R 2 is more preferably R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W independently of each other are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, O I -O Q - alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy or phenyl, preferably H or Ci-C 6 -alkyl, more preferably 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-
  • acyclic aliphatic groups of W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl.
  • R 2 is selected from R 2 -1 to R 2 -32; preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 - 31 , R 2 is more preferably R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W independently of each other are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, O-I-OQ- alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -haloalkoxy, or phenyl, preferably H or Ci-C 6 -alkyl, more preferably H, CH3, C2H5, or n-propyl;
  • Y is H, C2-C6-alkenyl, C2-C6-alkinyl, SH, Ci-C 6 -alkylamino, di(Ci-C 6 -alkyl)amino, C1-C6- alkylthio, Ci-C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, hydroxycar- bonyl, Ci-C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -al- kyl)aminocarbonyl, Ci-C 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C1-C6- alkylcarbonylamino, Ci-C 6 -alkylsulfonylamino, Ci-C 6 -haloalky
  • cyclic groups of X, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl.
  • R 2 is selected from R 2 -1 to R 2 -31 ; preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 - 31 , R 2 is more preferably R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W independently of each other are H, Ci-C 6 -alkyl, hydroxycarbonyl, or phenyl, preferably H or Ci-C 6 -alkyl, more preferably 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, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl.
  • Preffered R 4 and R 5 are independently from each other selected from hydrogen, OH, C1-C6- alkyl, NH2, 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, and di
  • 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, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, and C3-C6-cycloalkyl;
  • R 3 are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and C1-C6- alkoxy;
  • R 3 are selected from halogen, CN, Ci-C 6 -alkyl, and Ci-C 6 -alkoxy;
  • R 3 is halogen or CH 3 ;
  • R 3 is halogen
  • R 3 are selected from Cl, Br, and I;
  • R 3 is Br or I
  • R 3 is Br or Cl.
  • 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 phenyl or 9- or 10-membered fully unsaturated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; also referred Z is 5- or 6-membered het- eroaryl 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;
  • Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered 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, 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 -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
  • # 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;
  • 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, C 3 -C 6 -alkenyl, C 3 -C 6 -haloal- kenyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, or C 3 -C 6 -cycloalkyl; and
  • 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, C 3 -C 6 -alkenyl, C 3 -C 6 -haloal- kenyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, or C 3 -C 6 -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; also most particularly preferred 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 , F1 , 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 fully unsaturated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; also more preferred Z is 9- or 10-membered par- tially 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 heteroatoms selected from O or N;
  • Z is 9- or 10-membered fully unsaturated bicyclic ring, wherein the ring at- tached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms se- lected from O or N;
  • Z is 9 membered bicyclic ring
  • Z is a 9-membered bycyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially un- saturated 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 bycyclic 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 bycyclic ring wherein the ring attached to the pyrimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bycyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrol 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 bycyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrol ring which is fused with another 6-membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is 10 membered bicyclic ring
  • Z is a 10-membered bycyclic 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 bycyclic 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;
  • Z is a 10-membered bycyclic 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, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, or C 3 -C 6 -cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from 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, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, or C 3 -C 6 -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;
  • 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 S, T, U, or V;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 , 11 , J 1 , 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 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 1 is Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -32, preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 -31 , more preferably R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W, and Y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C1-C6- haloalkyl, OH, Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -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
  • cyclic groups of X, W and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • Z [i.e. the group“Z-(R 3 ) m ”] is formula W 1 wherein m is 0 or 1 ; and R 3 is halogen.
  • R 1 is Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -32, preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 -31 , more preferably R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W, and Y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C1-C6- haloalkyl, OH, Ci-C 6 -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, C1-C6- alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alky
  • cyclic groups of X, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • Z [i.e. the group“Z-(R 3 ) m ”] is formula W 1 wherein m is 0 or 1 ; and R 3 is halogen.
  • R 1 is unsubstituted cyclopropyl
  • R 2 is selected from R 2 -1 to R 2 -32, preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 -31 , more preferably R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W, and Y independently of each other are selected from H, Ci-C 6 -alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6-alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , Nhh, 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, Ci-C
  • cyclic groups of X, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • Z [i.e. the group“Z-(R 3 ) m ”] is formula W 1 wherein m is 0 or 1 ; and R 3 is halogen.
  • R 1 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably cyclo- propyl;
  • R 2 is selected from R 2 -1 to R 2 -32, preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9 or R 2 -31 , more preferably R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W, and Y independently of each other are selected from H, Ci-C 6 -alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6-alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, C1- 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, Ci-C
  • cyclic groups of X, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • 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 bycyclic ring selected from H to V as de- fined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -32, preferably R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9, or R 2 - 31 , more preferably R 2 is R 2 -1 , R 2 -7, or R 2 -31 ;
  • X, W, and Y independently of each other are selected from H, Ci-C 6 -alkyl, hydroxycarbonyl, C2-C6-alkenyl, C2-C6-alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n , NH2, C1- 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, Ci-C
  • cyclic groups of X, W, and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X, W, 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;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, 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 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • Q is H, C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • 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 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen. Also preferred are compounds of formula (I) wherein R 2 is R 2 -2, Z [i.e. the group“Z-(R 3 ) m ”] is
  • W 1 which corresponds to formula (I.C), and their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • 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 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • Q is H, Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or Ci-C 6 -alkylcarbonyl;
  • 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 , Nhh, 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 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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; more preferably, when m is 2, R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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, C1-C6- haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • W 1 which corresponds to formula (I.G), and their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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 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 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is C 3 -C 6 -cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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 bycyclic 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;
  • n 0, 1 or 2;
  • Q is H, C 2 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, or Ci-C 6 -alkylcarbonyl;
  • 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, COOCHs, COOC 2 H 5 , CONH 2 , CON HCH S , CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH 3 ) 2
  • Z i.e. the group“Z-(R 3 ) m ”
  • Z is phenyl, or 5- or 6-membered heteroaryl group selected from A1 to G1 as defined herein, or 9- to 10-membered bicyclic ring selected from H1 to V1 as defined herein.
  • R 1 is C 3 -C 6 -cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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 bycyclic 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;
  • 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, COOCHs, COOC 2 H 5 , CONH 2 , CON HCH S , CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 ,
  • CHC(CH S ) 2 C(CH 3 )C(CH S ) 2 , CHCH(CH S ), CoCH, CH 2 CHCH 2 , CH(CH S )CHCH 2 , CH 2 Co CH, CH(CHs)CoCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCHs, COOC 2 H 5 , CONH 2 , CONHCHs, or CON(CH 3 ) 2 ;
  • Z i.e. the group“Z-(R 3 ) m ”
  • Z is phenyl, or 5- or 6-membered heteroaryl group selected from A1 to G1 as defined herein, or 9- to 10-membered bicyclic ring selected from H1 to V1 as defined herein.
  • R 1 is C 3 -C 6 -cycloalkyl, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, preferably cyclopropyl;
  • 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 bycyclic 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;
  • n 0, 1 or 2;
  • W, 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, COOCHs, COOC 2 H 5 , CONH 2 , CON HCH S , CON(CH 3 ) 2 , CHCH 2 , C(CH 3 )CH 2 , CHC(CH S ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH S ), CoCH, CH 2 CHCH 2 , CH(CH S )CHCH 2 , CH 2 Co CH, CH(CHs)CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCHs,
  • the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A1 to G1 as defined herein, or 9- to 10-membered bicyclic ring selected from H1 to V1 as defined herein.
  • compounds of the invention are the compounds of the formula I,
  • R 1 is C-C 3 H 5 ;
  • R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -7, R 2 -8, R 2 -9, or R 2 -10;
  • Z is 2”-CI-C 6 H 4 , 2”-Br-C 6 H 4 , 2”-CI-4”-F-C 6 H 3 , 2”-CI-5”-F-C 6 H 3 , 2”-CI-6”-F-C 6 H 3 , 3”-CH 3 -2”- naphthyl, or 2”-CI-4”-F-5”-F-C 6 H 2 ;
  • Q is H or C2H 5 ;
  • X and Y independently are selected from H, Cl, Br, CN, CH 3 , C2H5, 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, COOCHs, COOC 2 H 5 , CONH2, CONHCHs, 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 )CoCH, SH, NHCHs, N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H 5 , CONH 2
  • compounds of the invention are the compounds of the formula I that are compiled in the Tables 1 to 70, wherein the meaning for the combination of variables X and Y of R 2 for each individual compound of tables 1 to 70 corresponds to each row of Table A.
  • 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 (l.l) (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 (l.l) (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 I.J, 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
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • 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,
  • 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).
  • 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.
  • 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.
  • 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.
  • PSII inhibitors are preferred.
  • 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.
  • 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).
  • PDS inhibitors group F1 of HRAC classification
  • HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
  • DOXsynthase group F4 of HRAC class
  • corn- pounds which inhibit carotenoid
  • 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.
  • 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.
  • compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • DHP synthase inhibitor herebicide 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.
  • 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.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • VLCFA inhibitor herebicide 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.
  • 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.
  • 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.
  • the compositions contain at least one auxinic herbi- cide (herbicide b13).
  • auxinic herbi- cide 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.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor hereinicide 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.
  • 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.
  • 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.
  • 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
  • herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
  • 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-
  • 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, met-
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine 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 420138-40- 5), N-(4-bromophenyl)-2-[
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions compris- ing at least one imidazolinone herbicide
  • 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
  • a preferred embodiment of the invention relates to those composi- tions comprising at least one aryl urea herbicide.
  • a preferred embodi- ment of the invention relates to those compositions comprising at least one triazine herbicide.
  • a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
  • 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, saflufen
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NOS NOS NOS NOS NOS NOS
  • 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-dichlorophen
  • bilanaphos biases
  • bilanaphos biases
  • bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
  • 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, pyridines 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;
  • 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,
  • isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
  • chloroacetamides and oxyacetamides 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-1 4 - [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
  • 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
  • auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
  • Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
  • 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, iofens
  • 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
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
  • glufosinate glufosinate-P, glufosinate-ammonium
  • VLCFA inhibitors 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, 11.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • 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-chlor
  • herbicides B that can be used in combination with the pyrimidine corn- pounds of the formula (I) according to the present invention are:
  • lipid biosynthesis inhibitors from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-
  • ALS inhibitors 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
  • 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 );
  • glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
  • VLCFA inhibitors 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;
  • 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);
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
  • herbicides B could also be B.203 which is cyclopyranil.
  • 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-
  • 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),
  • 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:
  • 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.
  • 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.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • 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.
  • 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,
  • 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.
  • 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.
  • the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
  • the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
  • the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbi- cides B different from each other.
  • the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
  • 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.
  • 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.
  • 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.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1 ), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730), (1.16.755), (1.17.730), (1.17.755), (1.19.730), (1.19.755), (1.29.730), (1.29.755), (1.30.730),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1 ), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1 ), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • component B at least one, preferably exactly one, herbicide B
  • component C at least one, preferably exactly one safener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1 ), (1.2), (1.15), (1.16), (1.17), (1.19), (1.29), (1.30), or (1.31 ), especially preferred the compound (1.1.730), (1.1.755), (1.2.730), (1.2.755), (1.15.730), (1.15.755), (1.16.730),
  • At least three, preferably exactly three herbicides B differ- ent from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • component B at least one, pref- erably exactly one, herbicide B, and as component C at least one, preferably exactly one saf- ener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230), (1.43.729),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.43), especially preferred the compound (1.43.34), (1.43.35), (1.43.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • component B at least one, pref- erably exactly one, herbicide B, and as component C at least one, preferably exactly one saf- ener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230), (1.45.729),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.45), especially preferred the compound (1.45.34), (1.45.35), (1.45.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • component B at least one, pref- erably exactly one, herbicide B, and as component C at least one, preferably exactly one saf- ener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230), (1.48.729),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.48), especially preferred the compound (1.48.34), (1.48.35), (1.48.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • component B at least one, pref- erably exactly one, herbicide B, and as component C at least one, preferably exactly one saf- ener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230), (1.49.729),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.49), especially preferred the compound (1.49.34), (1.49.35), (1.49.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230), (1.50.729),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.50), especially preferred the compound (1.50.34), (1.50.35), (1.50.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.52), especially preferred the compound (1.52.34), (1.52.35), (1.52.230),
  • component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.52), especially preferred the compound (1.52.34), (1.52.35), (1.52.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.52), especially preferred the compound (1.52.34), (1.52.35), (1.52.230),
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.52), especially preferred the compound (1.52.34), (1.52.35), (1.52.230),

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  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne des composés de pyrimidine de formule (I), ou leurs sels ou dérivés acceptables sur le plan agricole, en tant qu'herbicides, les variables étant telles que définies dans la description, l'invention concerne également l'utilisation de composés de pyrimidine de formule (I) en tant qu'herbicide, des compositions les comprenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nuisibles, l'invention concerne en outre un procédé de lutter contre la végétation indésirable consistant à laisser agir une quantité herbicide efficace d'au moins un des composés de pyrimidine de formule (I) sur les plantes, leurs graines et/ou leur habitat.
PCT/EP2018/084899 2017-12-20 2018-12-14 Composés herbicides de pyrimidine Ceased WO2019121373A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11033547B2 (en) * 2019-03-07 2021-06-15 Merck Patent Gmbh Carboxamide-pyrimidine derivatives as SHP2 antagonists
US12331027B2 (en) 2017-11-23 2025-06-17 Basf Se Herbicidal pyridylethers

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12331027B2 (en) 2017-11-23 2025-06-17 Basf Se Herbicidal pyridylethers
US11033547B2 (en) * 2019-03-07 2021-06-15 Merck Patent Gmbh Carboxamide-pyrimidine derivatives as SHP2 antagonists
CN113795483A (zh) * 2019-03-07 2021-12-14 默克专利有限公司 作为shp2拮抗剂的甲酰胺-嘧啶衍生物
CN113795483B (zh) * 2019-03-07 2024-12-31 默克专利有限公司 作为shp2拮抗剂的甲酰胺-嘧啶衍生物

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