WO2019121374A1 - Herbicidal pyrimidine compounds - Google Patents

Herbicidal pyrimidine compounds Download PDF

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WO2019121374A1
WO2019121374A1 PCT/EP2018/084901 EP2018084901W WO2019121374A1 WO 2019121374 A1 WO2019121374 A1 WO 2019121374A1 EP 2018084901 W EP2018084901 W EP 2018084901W WO 2019121374 A1 WO2019121374 A1 WO 2019121374A1
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crc
alkyl
alkoxy
formula
membered
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PCT/EP2018/084901
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French (fr)
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Florian Vogt
Tobias SEISER
Matthias Witschel
Gunther Zimmermann
Veronica LOPEZ CARRILLO
Thomas Seitz
Gerd Kraemer
Trevor William Newton
Doreen Schachtschabel
Klaus Kreuz
Peter Dombo
Klaus Reinhard
Eva HOLLENBACH
Ruth CAMPE
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/82—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
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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 describes 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 C r C 6 -alkyl, C r C 6 -haloalkyl, HO-CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -al- kynyl, C 3 -C 6 -haloalkynyl, CrC 6 -alkoxy-CrC 6 -alkyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C r C 6 -haloalkoxy, C 3 -C 6 -cycloal- koxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy,
  • R 2 is 5-membered heteroaryl selected from thiophenyl, furyl, which groups are substituted with one X, one Y and one W, or oxazolyl, 1-methylimidazolyl, which groups are substituted with one X and one Y, or 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl which groups are substituted with one Y;
  • X, W independently are H, halogen, CN, N0 2 , OH, C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 - alkoxy, C r C 6 -haloalkoxy, C r C 6 -alkylthio, C r C 6 -alkylsulfinyl, CrC 6 -alkylsulfonyl, which groups are unsubstituted or substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkyl, CrC 6 -haloalkyl, Ci-C 6 -alkoxy-(Ci-C4-alkoxy) n , C r C 6 -haloalkoxy, C r C 6 -al- kylthio, CrC 6 -alkylsulfinyl, or CrC 6 -alkylsulfonyl, which groups are substituted
  • R 20 is 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 -alkinylsulfinyl, aminosulfinyl, C r C 6 -alkylaminosulfinyl, di(CrC 6 -alkyl)aminosulfinyl, C 3 -C 6 -alkenylsulfonyl, C 3 -C 6 -alkinylsulfonyl, aminosulfonyl, CrC 6 -alkylaminosulfonyl, di(C r C 6 -alkyl)aminosulfonyl, C r C 6 -alkylcarbonylaminosulfonyl, C 3 -
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R a is OH, CN, C r C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 -haloalkoxy, C r C 6 - alkoxy-C r C 6 -alkoxy, NH 2 , C r C 6 -alkyl-amino, di(C r C 6 -alkyl)amino, SH, C r C 6 -alkylthio, C r C 6 -alkylsulfinyl, C r C 6 -alkylsulfonyl, CN, N0 2 , C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, hy droxycarbonyl, C r C 6 -alkoxycarbonyl, C r C 6 -haloalkoxycarbonyl, C 2 -C 6
  • R b is 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 -halocycloalkenyl, C r C 6 -alkoxycarbonyl-C r C 6 -alkyl, C r C 6 -alkylcarbonyl, C r C 6 -haloalkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, hy- droxycarbonyl-C r C 6 -alkyl, C r C 6 -alkyloxycarbonyl, C r C 6 -alkylthiocarbonyl, C r C 6
  • R c is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, OH, C r C 6 -alkoxy, C r C 6 -haloalkoxy,
  • R d is halogen, CN, N0 2 , OH, C r C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C r C 6 -haloalkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkinyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 - haloalkoxy, NH 2 , C r C 6 -alkyl-amino, di(C1-C6-alkyl)amino, SH, C r C 6 -alkylthio, C r C 6 -al- kylsulfinyl, C r C 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl,
  • R e is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkoxy, or C r C 6 -haloalkoxy;
  • R f is H, halogen, CN, OH, CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C r C 6 -haloalkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkinyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r 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, CrC 6 -alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkinyl, OH, NH 2 , C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 - alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkinylcarbonyl, CrC 6 -alkylsulfonyl, C r C 6 - haloalkylsulfonyl, C 3 -C 6 -alkenylsulfonyl, C 3 -C 6 -alkinylsulfonyl, C r C 6 -alkylsulfinyl, C 3 -C 6 - alkenylsulfinyl, C 3
  • 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 is H, halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 - C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C r C 6 -alkoxy, C r C 6 -haloalkoxy, C 3 -C 6 - alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, CrC 6 -alkoxy-C r C 6 -alkoxy, hydroxycarbonyl, C r C 6 -alkoxycarbonyl, C r C 6 -alkylthio, C
  • n 0, X 2, 3, or 4;
  • n is X 2, 3, 4, or 5;
  • the present invention also provides said pyrimidine compounds of formula (I), wherein when m is 2, 3 or 4, each R 3 in formula (I) is independently H, halogen, CN, N0 2 , C1-C6- alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3- C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbony
  • the present invention also provides the pyrimidine compounds of formula (I)
  • R 1 is C r C 6 -alkyl, C r C 6 -haloalkyl, HO-CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -al- kynyl, C 3 -C 6 -haloalkynyl, CrC 6 -alkoxy-C r C 6 -alkyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, CrC 6 -haloalkoxy, C 3 -C 6 -cycloal- koxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C
  • R 2 is 5-membered heteroaryl selected from thiophenyl, furyl, which groups are substituted with one X, one Y and one W, or oxazolyl, 1-methylimidazolyl, which groups are substituted with one X and one Y, or 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl which groups are substituted with one Y;
  • X, W independently are H, halogen, CN, N0 2 , OH, C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 - alkoxy, C r C 6 -haloalkoxy, C r C 6 -alkylthio, C r C 6 -alkylsulfinyl, C r C 6 -all ⁇ ylsulfonyl, which groups are unsubstituted or substituted with R a , or R 20 ;
  • Y is CrC 6 -alkyl, CrC 6 -haloalkyl, CrC 6 -alkoxy-(CrC4-alkoxy) n , C r C 6 -haloalkoxy, C r C 6 -al- kylthio, CrC 6 -alkylsulfinyl, or C r C 6 -alkylsulfonyl, which groups are substituted with R a , or
  • R 20 is 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,
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R a is OH, CN, C r C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, CrC 6 -haloalkoxy, C r C 6 - alkoxy-C r C 6 -alkoxy, NH 2 , C r C 6 -alkyl-amino, di(C r C 6 -alkyl)amino, SH, CrC 6 -alkylthio, C r C 6 -alkylsulfinyl, CrC 6 -alkylsulfonyl, CN, N0 2 , C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, hy- droxycarbonyl, C r C 6 -alkoxycarbonyl, CrC 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyloxy
  • R b is 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 -halocycloalkenyl, CrC 6 -alkoxycarbonyl-Cr C 6 -alkyl, C r C 6 -alkylcarbonyl, C r C 6 -haloalkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, hy- droxycarbonyl-C r C 6 -alkyl, C r C 6 -alkyloxycarbonyl, C r C 6 -alkylthiocarbonyl, C r C 6 -ami-
  • R c is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, OH, C r C 6 -alkoxy, C r C 6 -haloalkoxy,
  • R d is halogen, CN, N0 2 , OH, C r C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C r C 6 -haloalkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkinyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 - haloalkoxy, NH 2 , CrC 6 -alkyl-amino, di(C1-C6-alkyl)amino, SH, CrC 6 -alkylthio, C r C 6 -al- kylsulfinyl, CrC 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, C 4 -C 8
  • R e is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkoxy, or C r C 6 -haloalkoxy;
  • R f is H, halogen, CN, OH, CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C r C 6 -haloalkyl, C 3 -C 6 - haloalkenyl, C 3 -C 6 -haloalkinyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r 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, C2-C 6 -alkinyl, OH, NH 2 , C r C 6 -alkoxy, C 3 -C 6 -alkenyl
  • Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered fully unsaturated bicyclic ring containing 0, 1, 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
  • R 3 same or differently is H, halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C r C 6 -alkoxy, C r C 6 -halo- alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C r C 6 -alkoxy-C r C 6 -alkoxy, hydroxycarbonyl, C r C 6 -alkoxycarbonyl, C r C 6 -alky
  • n 1, 2, 3, 4, or 5;
  • the pyrimidine compounds of formula (I) is not N-[4-(2,5-Dimethyl-3-furyl)-5-(3- ethyl-4-pyridyl)-2-pyrimidinyl]-N-ethylamine, N-lsopropyl-5-(3-methylisoxazol-5-yl)-4-(5- methylthio-phen-2-yl)pyrimidin-2-amine, 3-Methyl-5-(2-(methylthio)-4-(5-methylthio- phen-2-yl)-pyrimidin-5-yl)isoxazole or 3-Methyl-5-(2-(methylsulfonyl)-4-(5-methylthio- phen-2-yl)pyrimidin-5-yl)isoxazole;
  • 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: Process A:
  • the pyrimidine compounds of formula (I) can be obtained by reacting respective aminoketones of formula (II) with base and amidine (III):
  • the reaction of the aminoketones (II) with amidines (III) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 20°C to the boiling point, particularly from 40°C to 120°C, in an inert organic solvent in the presence of a base.
  • reaction may in principle be carried out in substance. However, preference is given to re acting 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, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride (CCI 4 ) and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol, as well as dipolar aprotic solvents such as s
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCH 3 ), sodium ethoxide (NaOC 2 H 5 ), potassium ethoxide (KOC 2 H 5 ), potassium tert-butoxide (/BuOK), potassium tert-pent- oxide and dimethoxymagnesium
  • tertiary amines such as trimethyl- amine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy-hack amines.
  • TMA trimethyl- amine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • N-methylpiperidine pyri dine
  • substituted pyridines such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy-oul amines.
  • Particular preference is given to NaOCH 3 , NaOC 2 H 5 , KOC 2 H 5 , tBuOK and potassium tert-pentoxide.
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the amidine (XI), based on the aminoketone (X).
  • Amidines (XI) are known from literature or commercially available. In cases in which R 2 resem- Ibes a carbo- oder a heterocycle further, literature known, manipulations are possible: For exam ple oxazoles can selectively be halogenated following published procedures (e.g. Bioorganic & Medicinal Chemistry, 2010, 18, 4821).
  • the aminoketones (II) are prepared from the corresponding ketones (IV) with N,N-Dimethylfor- mamide dimethyl acetal (CAS 4637-24-5; DMFDMA).
  • the reaction is usually carried out at tem peratures from -100°C to the boiling point of the reaction mixture, preferably from 20°C to 160° C, particularly from 50°C to 130°C.
  • the reaction can optionally be catalyzed by an acid.
  • the reaction may be carried out in substance or in an organic solvent.
  • Suitable solvents are those capable of dissolving the ketones (IV) and DMFDMA (CAS 4637-24-5) at least partly, pref erably fully under reaction conditions.
  • solvents examples include aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole 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; preferably DMFDMA is used as solvent. It is also possible to use mixtures of the solvents mentioned.
  • aromatic hydrocarbons such as benzene, chlorobenzene, tol
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H 2 S0 4 ); organic acids p-tol- uenesulfonic 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 eguimolar 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, preferably 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, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, ani sole and THF, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and pro pionitrile, 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 solvent
  • the Grignard-reagents (V) are either commercially available or can be prepared from the corre sponding 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 (VI II) and the benzylhal ides (IX) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole 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 dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO, and NMP. It
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH 3 , NaOC 2 H 5 , KOC 2 H 5 , tBuOK, po tassium 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
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as col lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, LHMDS and LDA.
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the halide (IX), based on the morpholinonitrile (VIII).
  • Benzylhalides (IX) are commercially available.
  • Morpholinonitriles (VIII) are prepared from the corresponding aldehydes (X) as described in the literature (WO 2009/013462).
  • Aldehydes (X) are commercially available.
  • the pyrimidines of formula (XI) can be obtained from pyrimidines of formula (XII) by known methods e.g using PPh 3 and Iodine (analogous to Davies, James R. et ai Journal of Organic Chemistry, 70(15), 5840-5851, 2005 or Just-Baringo, Xavier et ai Angewandte Chemie, Interna tional Edition, 52(30), 7818-7821, 2013).
  • the pyrimidines of formula (XII) can be obtained from pyrimidines of formula (XIII) by reaction with the carboxylic acides (XIV), wherein R is alkyl, cycloalkyl, ha locycloa I kyl, haloalkyl, cycloal kenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
  • the reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, particularly from 0°C to 60°C, in an inert or ganic solvent.
  • Carboxylic acids RCOOH are commercially available. Carboxylic acids are activated using acti vating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethyla- mino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H- benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-hexafluorophosphate (HBTU), ethyl-3-(3-dimethyl- aminopropyl)carbodiimid (EDC).
  • acti vating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethyla- mino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H- benzotriazol-1-yl)
  • the carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chloride.
  • Carbonylimidazoles such as 1,T-Carbon- yldiimidazol (CDI) may also be used as activating reagent under neutral conditions.
  • Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered solvents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyridine, sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DI PEA.
  • TMA trimethylamine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • pyridine sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine
  • DBU Diazabicycloundecen
  • the bases are generally employed in excess amounts; however, they can also be employed in egual amounts as the pyrimidine.
  • the pyrimidines of formula (XIII) can be obtained from pyrimidines of formula (XV), wherein R is hydroxycarbonyl, alkoxycarbonyl, (H0) 2 (0)P, (alkoxy) 2 (0)P, alkyl sulfonyl or alkylcarbonyl, by reac tion with with an acid HA
  • the reaction of the pyrimidine (XV) is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, particularly from 0°C to 60°C, in an organic solvent using water as a cosolvent.
  • the starting materials are reacted with one another in eguimolar amounts or using an excess of one reagent. Preference is given to us ing an excess of acid HA.
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H 2 S0 4 ); organic acids p-tol- uenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; most preferably HCI.
  • Suitable solvents include dioxane and tetrahydrofuran (THF), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and N,N-di- methylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered solvents are alcohols. It is also possible to use mixtures of the solvents mentioned.
  • the pyrimidines of formula (XV) can be obtained by process C.
  • the pyrimidines of formula (XV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or a carboxylic ester, can be obtained by re acting respective pyrimidines of formula (XVI) with isocyanides (XVII):
  • the reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 78°C to 25°C, particularly from -78°C to 0°C, in an inert or ganic solvent using a base.
  • Suitable solvents are those capable of dissolving the pyrimidine (XVI) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, 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, tol uene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /?-BuLi.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH
  • alkali metal amides such as LHMDS and LDA
  • organometallic compounds in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /?-BuLi.
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the isocyanide (XVII) based on the pyrimidine (XVI).
  • the pyrimidines of formula (XVI) can be obtained by reacting respective pyrimidines of formula (XVIII) with boronic acids/esters of formula (XIX):
  • reaction of pyrimidines (XVIII) with boronic acids/esters (XIX) is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XVIII) with the boronic acids/esters (XIX) in an organic solvent with or without water as co-solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XVIII) and the boronic acids (XIX) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, 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, tol uene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • suitable metal-containing bases are inorganic compounds including metal-contain ing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li 2 0, Na 2 0, K 2 0, MgO, and CaO, Fe 2 0 3 , Ag 2 0; alkali metal and alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3 , and CaC0 3 , as well as alkali metal bicarbonates such as LiHC0 3 , NaHC0 3 , KHC0 3 ; alkali metal and alkaline earth metal phosphates such as K 3 P0 4 , Ca 3 (P0 4 ) 2 ; alkali metal and alkaline earth
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydrox ides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3 , and CaC0 3 and alkaline earth metal phosphates such as K 3 P0 4 ; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • alkali metal and alkaline earth metal hydrox ides such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3
  • Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkaline earth metal phosphates such as K 3 P0 4 .
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably at from 1 to 10 eguivalents based on the pyrimidine (XVIII), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XVIII), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XVIII).
  • a catalyst examples include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)pal- ladium(ll)chloride or (1,1,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl) 3 , triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1,T-binaphthyl).
  • palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 eguivalents) based on the py rimidine (XVIII).
  • halopyrimidines are known from the literature (e.g. WO 2011154327), are commer cially available or can be prepared by known procedures.
  • boronic acids/esters (XIX) reguired for the preparation of pyrimidines of formula (XVI) are commercially available, known from literature or can easily be prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
  • the pyrimidines of formula (XV) can also be obtained by reacting respective pyrimidine alde hydes (XX) with tosyl isocyanides (XXI), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, Oheteroaryl.
  • the reaction of the pyrimidine (XX) with the tosyl isocyanides (XXI) is usually carried out at temperatures of from - 100°C to the boil ing point of the reaction mixture, preferably from 0°C to the boiling point of the reaction mixture, particularly from 25°C to 65°C, in an inert organic solvent using a base.
  • Suitable solvents are those capable of dissolving the pyrimidine (XX) and the isocyanides (XXI) at least partly and pref erably fully under reaction conditions.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered solvents are methanol and ethanol.
  • Suitable bases are alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCH 3 ), sodium ethoxide (NaOC 2 H 5 ), potassium ethoxide (KOC 2 H 5 ), potassium tert-butoxide (/BuOK), potassium tert-pentoxide and dimethoxymagnesium.
  • metal carbonates such as caesium carbonate and potassium carbonate.
  • organic bases e.g.
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as col lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU).
  • DBU Diazabicycloundecen
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the tosyl isocyanide (XXI), based on the pyrimidine (XX).
  • the pyrimidines of formula (XX) can be obtained by oxidizing respective pyrimidine alcohols of formula (XXII).
  • the oxidation of pyrimidines (XXII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 100 °C, particularly at from 0 °C to 75 °C, in an inert organic solvent.
  • the reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XXII) in an organic solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XXII) at least partly and pref erably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH 2 CI 2 , CHCI 3 ,
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are halogenated hydrocarbons such as CH 2 CI 2 , CHCI 3 , CCH 2 CICH 2 CI or CCI 4 ,and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, N,N' -dimethyl- ⁇ propylene urea (DMPU), DMSO and NMP. More preferred solvents halogenated hydrocarbons such as CH 2 CI 2 , CMO S , CCH 2 CICH 2 CI or CCI 4 . It is also possible to use mixtures of the solvents mentioned.
  • oxidizing agents for the synthesis of pyrimidines 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 -com- plex.
  • methods like the Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyrimidines of formula (XX).
  • Preferred agents include Mn0 2 , KMn0 4 and PCC, more preferred Mn0 2 .
  • the oxidizing agent is used preferably from 1 to 50 eguivalents based on the pyrimidine (XXII), more preferably at from 1.0 to 20.0 eguivalents based on the pyrimidine (XXII), most preferably from 1.0 to 10.0 eguivalents based on the pyrimidine (XXII).
  • the pyrimidines of formula (XXII) can be obtained by reacting respective pyrimidines of formula (XVI) with a red
  • the reduction of pyrimidines (XVI) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 60 °C, particularly at from 0 °C °C to 25 °C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, 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 mix tures of the solvents mentioned.
  • Examples of reducing agents for pyrimidines include LAH, DIBALH, LiBH 4 or lithium tri- ethylborohydride.
  • Preferred agents include LAH and DIBALH.
  • the hydride-source is used preferably from 1 to 10 eguivalents based on the pyrimidine (XVI), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XVI), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XVI).
  • the pyrimidines of formula (XXIII) can be obtained from pyrimidines of formula (XXIV) by known methods e.g using actic acid anhydride/ concentrated sulfuric acid (e.g Godfrey, Alexander G. et al Journal of Organic Chemistry, 68(7), 2623-2632, 2003) or using burgess reagent (e.g. Brain, C.
  • the pyrimidines of formula (XXIV) can be obtained from carboxylic acids of formula (XXV) by reaction with amino ketones of formula (XXVI), wherein R substituents of the amino ketones are indenpendently of each alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
  • the reaction of the carboxylic acids (XXV) with amino ketones (XXVI, commercially available), is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, partic ularly from 0°C to 60°C, in an inert organic solvent.
  • Carboxylic acids are activated using activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-hex- afluorophosphate (HBTU), ethyl-3-(3-dimethylaminopropyl)carbodiimid (EDC).
  • activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-
  • the carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chlo ride.
  • Carbonylimidazoles such as 1,T-Carbonyldiimidazol (CDI) may also be used as activating re agent under neutral conditions.
  • Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
  • Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN).
  • Prefered solvents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyridine, sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DI PEA.
  • TMA trimethylamine
  • TEA triethylamine
  • DIPEA diisopropylethylamine
  • pyridine sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine
  • DBU Diazabicycloundecen
  • the bases are generally employed in excess amounts; however, they can also be employed ain egual amounts as the pyrimidine.
  • the reaction is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) in an organic solvent with or without water as co-solvent.
  • Suitable solvents are those capable of dissolving the pyrimidines (XXVII) and the boronic acids (XXVIII) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, 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, tol uene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • suitable metal-containing bases are inorganic compounds including metal-contain ing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li 2 0, Na 2 0, K 2 0, MgO, and CaO, Fe 2 0 3 , Ag 2 0; alkali metal and alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3 , and CaC0 3 , as well as alkali metal bicarbonates such as LiHC0 3 , NaHC0 3 , KHC0 3 ; alkali metal and alkaline earth metal phosphates such as K 3 P0 4 , Ca 3 (P0 4 ) 2 ; alkali metal and alkaline earth
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydrox ides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3 , and CaC0 3 and alkaline earth metal phosphates such as K 3 P0 4 ; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • alkali metal and alkaline earth metal hydrox ides such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkali metal or alkaline earth metal carbonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3
  • Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 and alkaline earth metal phosphates such as K 3 P0 4 .
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably at from 1 to 10 eguivalents based on the pyrimidine (XXVII), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XXVII), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XXVII).
  • a catalyst examples include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)pal- ladium(ll)chloride or (1,1,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl) 3 , triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1,T-binaphthyl).
  • palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 eguivalents) based on the py rimidine (XXVII).
  • boronic acids/esters (XXVIII) reguired for the preparation of pyrimidines of formula (XI) are commercially available, known from literature or can easily be prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
  • the reaction of the pyrimidine with the nucleohpile is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particu- larly from 20°C to 80°C, in an inert organic solvent using a base.
  • Suitable solvents are those ca pable of dissolving the pyrimidine (XXVII) and the nucleophile at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, 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, tol uene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH 3 , NaOC 2 H 5 , KOC 2 H 5 , tBuOK, po tassium tert-pentoxide and dimethoxymagnesium alkali metal and alkaline earth metal car bonates such as Li 2 C0 3 , Na 2 C0 3 , K 2 C0 3 , Cs 2 C0 3 , MgC0 3 , and CaC0 3 , as well as alkali metal bicar bonates such as LiHC0 3 , NaHC0 3 , KHC0 3 ; alkali metal and alkaline
  • tertiary amines such as TMA, TEA, DIPEA and N- methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethyla- minpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, LHMDS, LDA, NaOCH and K 2 C0 3 .
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the nucleophile based on the pyrimidine (XXVII).
  • the pyrimidines of formula (XI) with R' 1-hydroxy-alkyl, 1- hydroxy-aryl, 1-hydroxy-heteroaryl, 1-hydroxy-heterocyclyl, 1-hydroxy-cycloalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, al- kinylcarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carbocyclylcarbonyl and re lated compounds can also be obtained by reacting respective pyrimidines of formula (XV) with a base and an electrophile.
  • the reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 78°C to 25°C, particularly from -78°C to 0°C, in an inert or ganic solvent using a base.
  • Suitable solvents are those capable of dissolving the pyrimidine (XV) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, 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, tol uene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /7-BuLi.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH
  • alkali metal amides such as LHMDS and LDA
  • organometallic compounds in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /7-BuLi.
  • the bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
  • Suitable electrophiles are for example aldehydes and acid anhydrides, which are commercially available.
  • the starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the electrophile based on the pyrimidine (XV).
  • reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separa tion 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 ele vated 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.
  • pyrimidine compounds of formula (I) as described herein have one or more centres of chirality and, as a conseguence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according 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 cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C 4 -alkyl, HO-CrC 4 -alkyl, CrC 4 -alkoxy-Ci-C 4 -al- kyl, HO-CrC 4 -alkoxy-CrC 4 -alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae-
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C r C 4 -alka- noic 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-C r C 6 -alkyl- amides or arylamides, as esters, e.g.
  • allyl esters propargyl esters, Ci-C 0 -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl) methyl) esters and also as thioesters, e.g. as C r Ci 0 -alkylthio esters.
  • Preferred mono- and di-CrC 6 -alkylamides are the CH 3 and the dimethylamides.
  • Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, e.g., the me thyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylhep- tyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Preferred Ci-C 4 -alkoxy-Ci-C 4 -alkyl esters are the straight-chain or branched C r C 4 -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 members.
  • the term halogen denotes in each case F, Cl, Br, or I.
  • All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • CrC 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 ;
  • CrC 6- alkyl CrC 4- alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-di methyl propyl, 1,2- dimethylpropyl, 1- methyl pentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethyl- butyl, 1,2-di methyl butyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1-ethylbutyl, 2-ethyl butyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpro- pyl, or 1-ethyl-2-methylpropyl, preferably
  • Ci-C 4- haloalkyl CrC 4- alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, 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, 2-
  • CrC 6- haloalkyl CrC 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;
  • C 3- C 6- cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C 3- C 6- 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-
  • C 3- C 6- cycloalkenyl monocyclic partially unsaturated hydrocarbons having 3 to 6 ring members e.g. cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl.
  • C 3- C 6- haloalkenyl a C 3- C 6- alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3- chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2- en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibro- moprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl, or 2,3-dibromobut-2- en-1-yl;
  • C 3- C 6- alkynyl e.g. 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-
  • C 2- C 6- alkynyl C 3- C 6- alkynyl as mentioned above and also ethynyl;
  • C 3- C 6- haloalkynyl a C 3- C 6- 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- difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluo- rohex-4-yn-1-yl, or 6-iodohex-5-yn-1-yl;
  • CrC 4- alkoxy e.g. methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2- methylpropoxy, and 1,1-dimethylethoxy;
  • CrC 6- alkoxy CrC 4- alkoxy as mentioned above, and also, e.g., pentoxy, 1- methyl butoxy,
  • thyl propoxy 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.
  • CrC 4- haloalkoxy a CrC 4- alkoxy group as mentioned above which is partially or fully sub stituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroeth- oxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy
  • CrC 6- haloalkoxy a CrC 4- haloalkoxy as mentioned above, and also, e.g., 5-fluoropentoxy,
  • CrC 4- alkylthio e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1,1-dimethylethylthio;
  • CrC 6- alkylthio CrC 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- ethylbutylthio, 1,1,2-trimethylpropy
  • (CrC4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1,1-dimethylethylamino;
  • (CrC 6- alkyl)amino (C r C4-alkylamino) as mentioned above, and also, e.g., pentylamino, 1- methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethyl- propylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutyla- mino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamin
  • di(CrC 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- propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1- methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-
  • di(CrC 6- alkyl)amino di(CrC 4- alkyl)amino as mentioned above, and also, e.g., N-methyl- 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- dimethylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-N-(3-methyl
  • C r C 6 -alkylsulfonyl (CrC 6 -alkyl-S(0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1- methylethylsulfonyl, butylsu Ifonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-di- methylethylsulfonyl, pentylsu Ifonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfonyl, hexy
  • C 3 -C 6 -cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C 3 -C 6 -cycloalkenyl 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1- cyclopentenyl, 2-cyclopentenyl, 1,3-cyclopentadienyl, 1,4-cyclopentadienyl, 2,4-cyclopentadienyl, 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
  • bicyclic ring examples of such bicyclic ring are, 2,3-dihydrobenzothiophene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1,3-benzodioxole, 1,3-benzodithiole, 1,3- benzoxathiole, indole, indane, [1,3]dioxolo[4,5-c] pyridine, [1,3]dioxolo[4,5-b] pyridine, 2,3-dihydro- furo[2,3-c]pyridine, furo[2,3-c]pyridine, 2,3-dihydrofuro[2,3-b]pyridine, fu ro[2,
  • heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
  • 3- or 4-membered heterocycles like 2-oxiranyl, 2-aziridinyl, 2-thiiranyl, 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 1-azetinyl, or 2-azetinyl;
  • 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-thi- opyran-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, pyrazol-4- yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3-yl, iso- thiazol-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.
  • pyrimidin-2-yl pyrimidin-4-yl, py- rimidin-5-yl
  • pyrazin-2-yl pyrazin-2-yl
  • triazinyl e.g. 1,3,5-triazin-2-yl, or 1,2,4— triazin-3-yl, 1,2,4-triazin-5-yl
  • substituted if not specified otherwise refers to substituted with 1, 2 or maximum pos sible 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 mentioned other wise.
  • 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 C r C 6 -alkyl, CrC 6 -haloalkyl, HO-C r C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 - C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C r C 6 -alkoxy-C r C 6 -alkyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C r C 6 -haloalkoxy, C 3 -C 6 -cycloalkoxy, C 3 - C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3
  • R 1 is C r C 6 -alkyl, C r C 6 -haloalkyl, HO- CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, CrC 6 -alkoxy-CrC 6 -alkyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6- haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C r C 6 -haloalkoxy, C 3 -C 6 -cycloalkoxy, C 3 - C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -cycl
  • R 1 is C r C 6 -alkyl, C r C 6 -alkoxy, C r C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloal- kenyloxy, C 3 -C 6 -alkynyloxy, C 4 -C 6 -haloalkynyloxy, C r C 6 -alkylthio, C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is C r C 6 -alkyl, C r C 6 -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 C 2 H 5 , i-C 3 H 7 , i-C 4 H 9 , OCH 3 , c-C 3 H 5 , or c-C 4 H 7 ;
  • R 1 is C 2 H 5 , OCH 3 , or c-C 3 H 5 ; most preferred R 1 is c-C 3 H 5 ;
  • R 2 is selected from R 2 -1 to R 2 -24 as shown below,
  • R 2 is R 2 -1, R 2 -2, R 2 -3, R 2 -4, R 2 -5, R 2 -6, R 2 -7, R 2 -8, R 2 -9, R 2 -10, R 2 -11, or R 2 -12;
  • R 2 is R 2 -1, R 2 -2, R 2 -3, R 2 -4, R 2 -5, or R 2 -6;
  • R 2 is R 2 -7, R 2 -8, R 2 -9, R 2 -10, R 2 -11, or R 2 -12;
  • R 2 is R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -19, R 2 -20, R 2 -21, R 2 -22, R 2 -23, or R 2 -24;
  • R 2 is R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, or R 2 -18;
  • R 2 is R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -23, or R 2 -24;
  • R 2 is R 2 -19, R 2 -20, R 2 -23, or R 2 -24;
  • R 2 is R 2 -23, or R 2 -24;
  • R 2 is R 2 -13, R 2 -14, R 2 -15, or R 2 -16;
  • R 2 is R 2 -17, or R 2 -18;
  • R 2 is R 2 -13, or R 2 -14;
  • R 2 is R 2 -15, or R 2 -16;
  • R 2 is R 2 -13;
  • R 2 is R 2 -14;
  • R 2 is R 2 -15;
  • R 2 is R 2 -16;
  • R 2 is R 2 -17;
  • R 2 is R 2 -18;
  • X is H, halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, CrC 6 -alkoxy, CrC 6 -haloalkoxy, C r C 6 -alkylthio, or R 20 ;
  • particularly preferred X is H, halogen, CN, C r C 6 -alkyl, OH, C r C 6 -alkoxy, C r C 6 -alkylthio, or R 20 ; also particularly preferred X is H, halogen, CN, C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkoxy, C r C 6 - haloalkoxy, or R 20 ;
  • especially preferred X is H, halogen, CN, Ci-C 4 -alkyl, OH, C r C 4 -alkoxy, C -C 4 -alkylthio, or R 20 ; also especially preferred X is H, C r C 4 -alkyl, or R 20 ;
  • X is C r C 4 -alkyl, or R 20 ; also especially preferred X is H or R 20 ;
  • X is H, CH 3 , C 2 H 5 , n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH 3 , SCH 3 , F, Cl, Br, I, or R 20 ;
  • X is H, CH 3 , C 2 H 5 , n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH 3 , SCH 3 , F, Cl, Br, or I;
  • X is H, CH 3 , C 2 H 5 , OH, OCH 3 , or R 20 ;
  • X is H, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • X is H, CH 3 , C 2 H 5 , SCH 3 , or R 20 ;
  • X is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • X is H, CH 3 , C 2 H 5 , F, Cl, Br, I, or R 20 ;
  • X is H, CH 3 , C 2 H 5 , F, Cl, Br, or I;
  • X is H, CH 3 , C 2 H 5 , or R 20 ;
  • X is H, CH 3 , or C 2 H 5 ;
  • X is H or R 20 ;
  • X is H
  • X is CH 3 or R 20 ;
  • X is CH 3 ;
  • X is C 2 H 5 or R 20 ;
  • X is C 2 H 5 ;
  • W is H, halogen, CN, C r C 6 -alkyl, C r C 6 -haloalkyl, OH, C r C 6 -alkoxy, C r C 6 -haloalkoxy, CrC 6 -alkylthio, or R 20 ;
  • W is H, halogen, CN, C r C 6 -alkyl, OH, C r C 6 -alkoxy, CrC 6 -alkylthio, or R 20 ; also particularly preferred W is H, halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, C r C 6 -alkoxy, C r C 6 - haloalkoxy, or R 20 ;
  • W is H, halogen, CN, C r C4-alkyl, OH, CrC palkoxy, CrC palkylthio, or R 20 ; also especially preferred W is H, CrC 4 -alkyl, or R 20 ;
  • W is CrC ralkyl, or R 20 ;
  • W is H or R 20 ;
  • W is R 20 ;
  • W is H, CH 3 , C 2 H 5 , n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH 3 , SCH 3 , F, Cl, Br, I, or R 20 ;
  • W is H, CH 3 , C 2 H 5 , n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH 3 , SCH 3 ,
  • W is H, CH 3 , C 2 H 5 , OH, OCH 3 , or R 20 ;
  • W is H, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • W is H, CH 3 , C 2 H 5 , SCH 3 , or R 20 ;
  • W is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • W is H, CH 3 , C 2 H 5 , F, Cl, Br, I, or R 20 ;
  • W is H, CH 3 , C 2 H 5 , F, Cl, Br, or I;
  • W is H, CH 3 , C 2 H 5 , or R 20 ;
  • W is H, CH 3 , or C 2 H 5 ;
  • W is H or R 20 ;
  • W is H
  • W is CH 3 or R 20 ; also most particularly preferred W is CH 3 ;
  • W is C 2 H 5 or R 20 ;
  • W is C 2 H 5 ;
  • Y is C r C 6 -alkyl, C r C 6 -haloalkyl, CrC 6 -alkoxy-(C r C 4 -alkoxy) n , C r C 6 -haloalkoxy, C r C 6 - alkylthio, CrC 6 -alkylsulfi nyl, or CrC 6 -alkylsulfonyl, which groups are substituted with R a ;
  • Y is R 20 ;
  • Y is C r C 6 -alkyl, C r C 6 -haloalkyl, CrC 6 -alkoxy-(CrC 4 -alkoxy) n , C r C 6 -haloalkoxy, which groups are substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkyl substituted with R a , or R 20 ;
  • Y is CrC 6 -haloalkyl substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkoxy-(Ci-C 4 -alkoxy) n substituted with R a , or R 20 ;
  • Y is Ci-C 6 -haloalkoxy substituted with R a , or R 20 ;
  • Y is C r C 6 -alkyl, C r C 6 -haloalkyl, CrC 6 -alkoxy-(CrC 4 -alkoxy) n , C r C 6 -haloal- koxy, which groups are substituted with R a ;
  • Y is C r C 6 -alkyl, preferably CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, isobutyl, which groups are substituted with R a ;
  • Y is CrC 6 -haloalkyl substituted with R a ;
  • Y is CrC 6 -alkoxy-(CrC 4 -alkoxy) n substituted with R a ;
  • Y is C r C 6 -haloalkoxy substituted with R a ;
  • Y is CrC 6 -alkylthio, C r C 6 -alkylsulfinyl, or CrC 6 -alkylsulfonyl, which groups are substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkylthio substituted with R a , or R 20 ;
  • Y is C r C 6 -alkylsulfinyl substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkylsulfonyl substituted with R a , or R 20 ;
  • Y is Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, or CrC 6 -alkylsulfonyl, which groups are substituted with R a ;
  • Y is Ci-C 6 -alkylthio substituted with R a ;
  • Y is Ci-C 6 -alkylsulfinyl substituted with R a ;
  • Y is CrC 6 -alkylsulfonyl substituted with R a ;
  • Y is C r C 6 -alkyl, C r C 6 -alkylthio, C r C 6 -alkylsulfinyl, or C r C 6 -alkylsulfonyl, which groups are substituted with R a , or R 20 ;
  • Y is C r C 6 -alkyl, C r C 6 -alkylthio, C r C 6 -alkylsulfinyl, or C r C 6 -alkylsulfonyl, which groups are substituted with R a ;
  • Y is CrC 6 -alkyl, or C r C 6 -alkylthio, which groups are substituted with R a , or R 20 ;
  • Y is CrC 6 -alkyl, or CrC 6 -alkylthio, which groups are substituted with R a ; also more preferred Y is C r C 6 -alkylthio, CrC 6 -alkoxy-(CrC 4 -alkoxy) n , or C r C 6 -alkylsulfinyl, which groups are substituted with R a , or R 20 ;
  • Y is C r C 6 -alkylthio, CrC 6 -alkoxy-(CrC 4 -alkoxy) n , or C r C 6 -alkylsulfinyl, which groups are substituted with R a ;
  • Y is C r C 4 -alkyl, C r C 2 -fluoroalkyl, C r C 4 -alkoxy, or C r C 4 -alkylthio, which groups are substituted with R a , or R 20 ;
  • Y is CrC 4 -alkyl, C r C 2 -fluoroalkyl, C r C 4 -alkoxy, or C r C 4 -alkylthio which groups are substituted with R a ; more especially Y is CH 3 , C 2 H 5 , n- propyl, iso-propyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH 3 , or SCH 3 , which groups are substituted with R a , or R 20 ;
  • Y is CH 3 , C 2 H 5 , n- propyl, iso-propyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH 3 , or SCH 3 , which groups are substituted with R a ;
  • Y is CH 3 , C 2 H 5 , n-propyl, iso-propyl, OCH 3 , or SCH 3 , which groups are substi tuted with R a , or R 20 ;
  • Y is CH 3 , C 2 H 5 , n-propyl, iso-propyl, OCH 3 , or SCH 3 , which groups are sub stituted with R a ;
  • R 20 is 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 r C 6 -alkylsulfi- nyl, CrC 6 -alkylsulfonyl, C 3 -C 6 -alkenylsulfinyl, C 3 -C 6 -alkinylsulfinyl, aminosulfinyl, C r C 6 -alkylamino- sulfinyl, di(CrC 6 -alkyl)aminosulfinyl, C 3 -C 6 -alkenylsulfonyl, hydroxysulfonyl, CrC 6 -alkoxysulfonyl, aminocarbonyl, C r C 6 -alkylcarbonyl, Ci-C 6 -alky
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R 20 is 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 r C 6 - alkylsulfinyl, CrC 6 -alkylsulfonyl, hydroxysulfonyl, C r C 6 -alkoxysulfonyl, aminocarbonyl, C r C 6 -alkyl- carbonyl, CrC 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, (HO) 2 (0)P, (C r C 6 - alkoxy) 2 (0)P, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R 20 is 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 r C 6 -alkylsulfinyl, CrC 6 -alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocy clyl;
  • cyclic groups of R 20 are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of R 20 are unsubstituted or substituted with R d ;
  • R a is OH, CN, C r C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 -haloalkoxy, C 3 - C 6 -cycloalkyl, hydroxycarbonyl, C r C 6 -alkoxycarbonyl, C r C 6 -haloalkoxycarbonyl, C r C 6 -alkyla- minocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, C r C 6 -alkylcarbonyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl;
  • R a is OH, CN, C r C 6 -alkoxy, C 3 -C 6 -cycloalkyl, hydroxycarbonyl, C r C 6 -alkyla- minocarbonyl, di(CrC 6 -alkyl)aminocarbonyl, C r C 6 -alkylcarbonyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl;
  • R a is OH, CN, C r C 6 -alkoxy, C 3 -C 6 -cycloalkyl, hydroxycarbonyl, C r C 6 -alkyla- minocarbonyl, di(C r C 6 -alkyl)aminocarbonyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6- membered heterocyclyl;
  • R b is C r C 6 -alkyl, C r C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C r C 6 -ami- nocarbonyl, phenyl-C r C 6 -alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het erocyclyl;
  • R b is C 3 -C 6 -cycloalkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-mem bered heterocyclyl;
  • R b is C 3 -C 6 -cycloalkyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het erocyclyl;
  • R c is halogen, CN, OH, C r C 6 -alkyl or C r C 6 -alkoxy, C r C 6 -haloalkoxy, or NH 2 ; more preferred R c is C r C 6 -alkyl or C r C 6 -alkoxy;
  • R c is C r C 6 -all ⁇ yl
  • R d is CN, OH, halogen, C r C 6 -alkyl, C 3 -C 6 -cycloalkyl, C r C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C r C 6 -haloalkoxy, NH 2 , phenyl-CrC 6 -alkyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl, or phenylthio;
  • R d is halogen, C r C 6 -alkoxy, or phenylthio
  • R d is halogen or C r C 6 -alkoxy
  • R e is halogen, OH, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy;
  • R e is halogen, CN, OH, C r C 6 -alkoxy or C r C 6 -alkyl;
  • R e is OH or C r C 6 -alkoxy
  • R f is H, halogen, CN, OH, C r C 6 -alkyl, or C r C 6 -alkoxy;
  • R f is OH, C r C 6 -alkyl, or C r C 6 -alkoxy
  • R f is OH or C r C 6 -alkoxy.
  • X, W independently are H, halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, OH, C r C 6 -alkoxy, hy- droxycarbonyl, C r C 6 -alkoxycarbonyl, C r C 6 -haloalkoxy or phenyl, preferably H or C r C 6 - alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 3 -C 6 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 3 -C 6 -alkenyloxy, C 3 - C 6 -alkinyloxy, CrC 6 -alkoxy-(CrC4-alkoxy) n , SH, NH 2 , C r C 6 -alkylamino, di(C r C 6 -al- kyl)amino, (C r C 6 -alkyl)(C r C 6 -alkoxy)amino, C r C 6 -alkylthio, CrC 6 -alkylthio-CrC 6 -alkyl, CrC 6 -alkylsulfinyl, C r C 6 -alkylsulfonyl, CrC 6 -alkoxy-C r
  • 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, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio.
  • X, W is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, CrC 6 -alkoxy, hydroxycarbonyl, C C 6 - alkoxycarbonyl, C r C 6 -haloalkoxy, or phenyl, preferably H or CrC 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, SH, C r C 6 -alkylamino, di(C r C 6 -alkyl)amino, C r C 6 -alkylthio, CrC 6 -alkylsulfinyl, C r C 6 -alkylsulfonyl, CrC 6 -alkoxy-CrC 6 -alkyl, hydroxycarbonyl, C r C 6 - alkoxycarbonyl, aminocarbonyl, CrC 6 -alkylaminocarbonyl, di(CrC 6 -alkyl)aminocarbonyl, C r C 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C r C 6 -alkylcarbonylamino, CrC 6 -alkylsulfonylamino, CrC 6 -haloalkyl
  • 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, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio.
  • X, W is H, CrC 6 -alkyl, hydroxycarbonyl, or phenyl, preferably H or C r C 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C4-alkoxy) n , NH 2 , C r C 6 -alkylthio-CrC 6 -alkyl, Ci-C 6 -alkoxy-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, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio.
  • R 4 and R 5 are independently from each other selected from hydrogen, OH, C r C 6 -al- kyl, NH 2 , C r C 6 -alkylcarbonyl, C r C 6 -alkylsulfonyl, C r C 6 -haloalkylsulfonyl, C r C 6 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-mem bered heterocyclyloxycarbonyl, C 3 -C 6 -cycloalkyloxycarbonyl, C 3 -C 6 -cycloalkenyloxycarbonyl, ami nocarbonyl, CrC 6 -
  • R 4 and R 5 are independently from each other selected from OH, C r C 6 -alkylcar- bonyl, C r C 6 -alkylsulfonyl, and C r C 6 -haloalkylsulfonyl.
  • R 3 is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkoxy, or C 3 -C 6 -cycloalkyl; also preferred R 3 is halogen, CN, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy;
  • R 3 is halogen, CN, C r C 6 -alkyl, or C r C 6 -alkoxy;
  • R 3 is halogen or CH 3 ;
  • R 3 is halogen
  • R 3 is Cl, Br, or 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,
  • Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered partially or fully unsaturated bicyclic ring containing 0, 1, 2, 3, 4 or 5 heteroatoms selected from O, N, and S; also preferred 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;
  • 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 pyrim idine 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 W1,
  • R 3 is as defined herein including its preferred embodiments
  • n 0, 1, or 2, prferrably 0 or 1;
  • # denotes the point of attachment to the pyrimidine ring
  • R 3 is halogen, CN, N0 2 , C r C 6 -alkyl, C r C 6 -haloalkyl, C r C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 - C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C r C 6 -alkoxy, C r C 6 -haloalkoxy, C 3 - C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C r C 6 - alkoxy-CrC 6 -alkoxy, hydroxycarbonyl, CrC 6 -alkoxycarbonyl, CrC 6 -alkylthio, C r C 6 -
  • R 3b and R 3c each independently is H, halogen, CN, N0 2 , Ci-C 6 -alkyl, CrC 6 -haloalkyl, C1-C6- a I kylca r bony I, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C r C 6 -alkoxy, CrC 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -
  • # 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, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
  • n 0 or 1
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C3-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 A1 to G1,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or CrC 6 -alkoxy;
  • R 3b is H, halogen, CHO, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, CrC 6 -alkyl, CrC 6 -haloalkyl, CrC 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 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 A1, B1, C1, and D1;
  • 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 E, F, and G;
  • Z[i.e. the group "Z-(R 3 ) m "] is selected from E1, F1, and G1;
  • 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,
  • Z is 9- or 10-membered partially or fully unsaturated bicyclic ring, wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 het eroatoms selected from O or N;
  • Z is 9- 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- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 heteroatoms selected from O or N;
  • Z is 9 membered bicyclic ring
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially 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 bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms; most particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the py rimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered car- bocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 heteroatoms se lected from O or N;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is 10 membered bicyclic ring
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 heteroatoms selected from O or N;
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z-(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 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or CrC 6 -alkoxy;
  • n 0, 1 or 2;
  • R 4 is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, or C r C 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, CrC 6 -alkyl, CrC 6 -haloalkyl, C r 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-(R 3 ) m "] is selected from groups H to V,
  • Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1, 2, or 3 het eroatoms selected from O, N, and S;
  • R 3 is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, or C r C 6 -alkoxy;
  • n 0, 1 or 2;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, CrC 6 -alkyl, CrC 6 -haloalkyl, C r 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 se lected from O, N, and S;
  • R 3 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or CrC 6 -alkoxy;
  • R 3b and R 3c each independently is H, halogen, CN, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy ;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, C r C 6 -alkyl, C r C 6 -haloalkyl, C r 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 H1, 11, K1, L1 and R1;
  • 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 comprising 1, or 2 heteroatoms selected from O, N, and S;
  • Y 1 is 5-membered partially unsaturated carbocycle comprising 0, 1, or 2 heteroa toms selected from O, N, and S, e.g. 1,3-dithiolane, 1,3-oxathiolane, 1,3-dioxolane, 2,3-dihydrofu- ran, 2,3-dihydrothiophene, or 2,3-dihydro-1H-pyrrole ; more preferably heteroatoms are selected from O and S, e.g. 1,3-oxathiolane, 1,3-dioxolane, 2,3-dihydrofuran, or 2,3-dihydrothiophene; most preferred heteroatom in Y 1 is O, e.g. 1,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y 1 is S, e.g. 2,3-dihydrothiophene;
  • Y 1 is 5-membered fully unsaturated carbocycle comprising 0, 1, or 2 het eroatoms selected from O, N, and S (furan, thiophene, 1H-pyrrole, 1,2-oxazole, 1,3-oxazole, 1,2- thiazole, 1,3-thiazole, imidazole, 1H-pyrazole); more preferably 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 at oms;
  • Y 1 is 6-membered partially or fully unsaturated carbocycle comprising 0, 1, or 2 heteroatoms selected from O, N, and S;
  • Y 1 is 6-membered partially unsaturated carbocycle comprising 0, 1, or 2 heteroa toms 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;
  • 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 S, T, U, or V.
  • Z i.e. the group "Z-(R 3 ) m "] is H1, 11, J1, K1, L1, M1, N1, 01, P1, Q1, or R1;
  • Z[i.e. the group "Z-(R 3 ) m "] is H1, L1, or M1;
  • Z[i.e. the group "Z-(R 3 ) m "] is H1;
  • 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 H1, 11, K1, L1 and R1;
  • n 0, 1, 2, or 3;
  • m is 0, 1, or 2; also most preferred m is 1;
  • n 0, 1, 2, or 3;
  • n 0, 1, or 2;
  • n 0;
  • n 1;
  • n 2
  • R 1 is CrC 6 -alkyl, CrC 6 -alkoxy, CrC 6 -alkylthio, or C 3 -C 6 -cycloalkyl, preferably unsubstituted C 3 - C 6 -cycloalkyl, more preferably unsubstituted cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -24, preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -19, R 2 -20, R 2 -21, R 2 -23, and R 2 -24, more preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 -15, or R 2 -16;
  • X, W is H, halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, C r C 6 -alkoxy, hydroxycarbonyl, C & - alkoxycarbonyl, C r C 6 -haloalkoxy or phenyl, preferably H or Ci-C 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 3 -C 6 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 3 -C 6 -alkenyloxy, C 3 - C 6 -alkinyloxy, CrC 6 -alkoxy-(CrC4-alkoxy) n , SH, NH 2 , C r C 6 -alkylamino, di(C r C 6 -al- kyl)amino, (CrC 6 -alkyl)(C r C 6 -alkoxy)amino, CrC 6 -alkylthio, CrC 6 -alkylthio-CrC 6 -alkyl, CrC 6 -alkylsulfinyl, CrC 6 -alkylsulfonyl, CrC 6 -alkoxy-C r C 6 -al
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, C r C 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or CrC 6 -alkylthio;
  • Z[i.e. the group "Z-(R 3 ) m "] is formula W1 wherein m is 0 or 1; and R 3 is halogen.
  • R 1 is C r C 6 -alkyl, C r C 6 -alkoxy, C r C 6 -alkylthio, or C 3 -C 6 -cycloalkyl, preferably unsubstituted C 3 - C 6 -cycloalkyl, more preferably unsubstituted cyclopropyl;
  • R 2 is selected from R 2 -1 to R 2 -24, preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -19, R 2 -20, R 2 -21, R 2 -23, and R 2 -24, more preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 -15, or R 2 -16;
  • X is H, halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, OH, C r C 6 -alkoxy, hydroxycarbonyl, C &- alkoxycarbonyl, C r C 6 -haloalkoxy or phenyl, preferably H or CrC 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, SH, C r C 6 -alkylamino, di(C r C 6 -alkyl)amino, C r C 6 -alkylthio, CrC 6 -alkylsulfinyl, C r C 6 -alkylsulfonyl, CrC 6 -alkoxy-CrC 6 -alkyl, hydroxycarbonyl, C r C 6 - alkoxycarbonyl, aminocarbonyl, C r C 6 -alkylaminocarbonyl, di(C r C 6 -alkyl)aminocarbonyl, C r C 6 -alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C r C 6 -alkylcarbonylamino, CrC 6 -alkylsulfonylamino, CrC 6 -halo
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio;
  • Z[i.e. the group "Z-(R 3 ) m "] is formula W1 wherein m is 0 or 1; and R 3 is halogen.
  • R 1 is unsubstituted cyclopropyl
  • R 2 is selected from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -19, R 2 -20, and R 2 -21, more prefer ably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 - 15, or R 2 -16;
  • X is H, CrC 6 -alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, C r C6-alkoxy-(CrC4-alkoxy) n , NH 2 , SH, CrC 6 -alkylthio-CrC 6 -alkyl, C r C 6 -alkoxy-C r C 6 -alkyl, C r C 6 -alkylcarbonyl, hydroxycar bonyl, C r C 6 -alkoxycarbonyl, aminocarbonyl, Ci-C 6 -alkylaminocarbonyl, di(C r C 6 -al- kyl)a mi nocarbonyl, NH 2 -aminocarbonyl, hydroxyaminocarbonyl, C 3 -C 6 -cycloalkyla- minocarbonyl, CrC 6 -alkylcarbonylamino, CrC 6
  • cyclic groups of X and Y are unsubstituted or substituted with R c ; and acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ; n is 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or CrC 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or Ci-C 6 -alkylthio;
  • Z[i.e. the group "Z-(R 3 ) m "] is formula W1 or H, wherein m is 0 or 1; and R 3 is halogen;
  • Y 1 is 5- or 6-membered partially unsaturated carbocycle comprising 0, 1,or 2 oxygen atoms.
  • R 1 is unsubstituted cyclopropyl
  • R 2 is selected from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -19, R 2 -20, and R 2 -21, more prefer ably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 - 15, or R 2 -16;
  • X is H, CrC 6 -alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC 6 -alkyl, more preferably H, CH 3 , C 2 H 5 , or n-propyl;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy) n , NH 2 , SH, CrC 6 -alkylthio-CrC 6 -alkyl, CrC 6 -alkoxy-CrC 6 -alkyl, CrC 6 -alkylcarbonyl, hydroxycar bonyl, C r C 6 -alkoxycarbonyl, aminocarbonyl, CrC 6 -alkylaminocarbonyl, di(CrC 6 -al- kyl)a mi nocarbonyl, NH 2 -aminocarbonyl, hydroxyaminocarbonyl, C 3 -C 6 -cycloalkyla- minocarbonyl, CrC 6 -alkylcarbonylamino, CrC 6 -alkylsulfony
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or CrC 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or CrC 6 -alkylthio;
  • Z[i.e. the group "Z-(R 3 ) m "] is formula W1, wherein m is 0 or 1; and R 3 is halogen.
  • R 1 is C3-C 6 -cycloalkyl, C3-C 6 -halocycloalkyl, CrC 6 -alkyl, or CrC 6 -haloalkyl, preferably cyclopro- pyl;
  • R 2 is selected from R 2 -1 to R 2 -24, preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -23, and R 2 -24, more preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 -15, or R 2 -16; Z[i.e. the group "Z-(R 3 ) m "] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 1 or 2;
  • R 3 each independently is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen.
  • R 1 is C3-C 6 -cycloalkyl, C3-C 6 -halocycloalkyl, CrC 6 -alkyl, or CrC 6 -haloalkyl, preferably cyclopro- pyl;
  • R 2 is selected from R 2 -1 to R 2 -24, preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, R 2 -18, R 2 -23, and R 2 -24, more preferably from R 2 -13, R 2 -14, R 2 -15, R 2 -16, R 2 -17, and R 2 -18, most preferably R 2 is R 2 -13, R 2 -14, R 2 -15, or R 2 -16;
  • R 3 is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen.
  • R 1 is C 3 -C 6 -cycloalkyl, CrC 6 -alkyl, or CrC 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is H, halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, CrC 6 -alkoxy, hydroxycarbonyl, CrC 6 - alkoxycarbonyl, CrC 6 -haloalkoxy or phenyl, preferably H, Ci-C 6 -alkyl, or CrC 6 -haloalkyl, more preferably H, CH 3 , C 2 H 5 , n-propyl, CF 3 , CH 2 CF 3 , CH 2 CHF 2 ;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy) n , NH 2 , C r C 6 -alkylthio-Ci-C 6 -alkyl, CrC 6 -alkoxy-CrC 6 -alkyl, CrC 6 -alkylcarbonyl, hydroxycarbonyl, CrC 6 -alkoxycarbonyl, aminocarbonyl, CrC 6 -alkylaminocarbonyl, di(CrC 6 -alkyl)ami- nocarbonyl, NH 2 -aminocarbonyl, hydroxyaminocarbonyl, C 3 -C 6 -cycloalkylaminocar- bonyl, CrC 6 -alkylcarbonylamino, CrC 6 -alkylsulfonylamino
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or CrC 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or CrC 6 -alkylthio;
  • R 3 each independently is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen.
  • R 1 is C3-C 6 -cycloalkyl, CrC 6 -alkyl, or CrC 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is H, halogen, Ci-C 6 -alkyl, CrC 6 -haloalkyl, OH, CrC 6 -alkoxy, hydroxycarbonyl, 0-C 6 - alkoxycarbonyl, CrC 6 -haloalkoxy or phenyl, preferably H, CrC 6 -alkyl, or CrC 6 -haloalkyl, more preferably H, CH 3 , C 2 H 5 , n-propyl, CF 3 , CH 2 CF 3 , CH 2 CHF 2 ;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy) n , NH 2 , C r C 6 -alkylthio-CrC 6 -alkyl, CrC 6 -alkoxy-CrC 6 -alkyl, CrC 6 -alkylcarbonyl, hydroxycarbonyl, CrC 6 -alkoxycarbonyl, aminocarbonyl, CrC 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)ami- nocarbonyl, NH 2 -aminocarbonyl, hydroxya mi nocarbonyl, C 3 -C 6 -cycloalkylaminocar- bonyl, CrC 6 -alkylcarbonylamino, CrC 6 -alkylsulfonylamino
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or CrC 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or CrC 6 -alkylthio;
  • R 3 each independently is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen.
  • R 2 is R 2 -11
  • Z[i.e. the group "Z-(R 3 ) m "] is formula W1, which corresponds to formula (I.D), and their use as herbicide, wherein R 1 is C3-C 6 -cycloalkyl, C r C 6 -alkyl, or C r C 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is H, halogen, C r C 6 -alkyl, CrC 6 -haloalkyl, OH, C r C 6 -alkoxy, hydroxycarbonyl, C & - alkoxycarbonyl, C r C 6 -haloalkoxy or phenyl, preferably H, C r C 6 -alkyl, or C r C 6 -haloalkyl, more preferably H, CH 3 , C 2 H 5 , n-propyl, CF 3 , CH 2 CF 3 , CH 2 CHF 2 ;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, Ci-C 6 -alkoxy-(Ci-C4-alkoxy) n , NH 2 , C r C 6 -alkylthio-CrC 6 -alkyl, Ci-C 6 -alkoxy-C-
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio;
  • R 3 each independently is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen.
  • R 1 is C 3 -C 6 -cycloalkyl, C r C 6 -alkyl, or C r C 6 -alkoxy, preferably cyclopropyl;
  • R 3 is halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is H, halogen, C r C 6 -alkyl, CrC 6 -haloalkyl, OH, C r C 6 -alkoxy, hydroxycarbonyl, C & - alkoxycarbonyl, C r C 6 -haloalkoxy or phenyl, preferably H, C r C 6 -alkyl, or C r C 6 -haloalkyl, more preferably H, CH 3 , C 2 H 5 , n-propyl, CF 3 , CH 2 CF 3 , CH 2 CHF 2 ;
  • Y is C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 4 -C 8 -cycloalkenyl, CrC 6 -alkoxy-(CrC 4 -alkoxy) n , NH 2 , C r C 6 -alkylthio-CrC 6 -alkyl, Ci-C 6 -alkoxy-C-
  • cyclic groups of X and Y are unsubstituted or substituted with R c ;
  • acyclic aliphatic groups of X and Y are unsubstituted or substituted with R d ;
  • n 1, 2 or 3;
  • R c is halogen, CN, CrC 6 -alkyl, CrC 6 -haloalkyl, OH, or C r C 6 -alkoxy;
  • R d is C 2 -C 6 -alkinyl, OH, phenyl, or C r C 6 -alkylthio;
  • R 3 each independently is halogen, CrC 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen.
  • R 1 is C 3 -C 6 -cycloalkyl, C r C 6 -alkyl, or C r 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 bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is 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,
  • CONH 2 CONHCH 3 , CON(CH 3 ) 2 , CH 2 CHCH 2 , or CH 2 CoCH;
  • Y is CHCH 2 , C(CH 3 )CH 2 , CH 2 CHCH 2 , CH 2 OCH 3 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), Co CH, CH 2 CHCH 2 , CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCHs, COOC 2 H s , CONH 2 , CONHCH 3 , or CON(CH 3 ) 2 ;
  • Z i.e. 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.
  • R 2 is R 2 -10, which corresponds to formula (I.G), and their use as herbicide, wherein R 1 is C3-C 6 -cycloalkyl, Ci-C 6 -alkyl, or CrC 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 bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is 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 , CH F 2 , CF 3 , CH 2 CF 3 , CH 2 CHF 2 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H s , CONH 2 , CONHCH 3 , CON(CH 3 ) 2 , CH 2 CHCH 2 , or CH 2 CoCH;
  • Y is CHCH 2 , C(CH 3 )CH 2 , CH 2 CHCH 2 , CH 2 OCH 3 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), C o CH, CH 2 CHCH 2 , CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H s , CONH 2 , CONHCH 3 , or CON(CH 3 ) 2;
  • Z i.e. 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.
  • R 1 is C 3 -C 6 -cycloalkyl, C r C 6 -alkyl, or C r 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 bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, C r C 6 -alkyl, C r C 6 -haloalkyl, or C r C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is 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 , CH F 2 , CF 3 , CH 2 CF 3 , CH 2 CHF 2 , OCHF 2 , OCF 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H s , CONH 2 , CONHCH 3 , CON(CH 3 ) 2 , CH 2 CHCH 2 , or CH 2 CoCH;
  • Y is CHCH 2 , C(CH 3 )CH 2 , CH 2 CHCH 2 , CH 2 OCH 3 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), C o CH, CH 2 CHCH 2 , CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H s , CONH 2 , CONHCH 3 , or CON(CH 3 ) 2 ;
  • Z i.e. 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.
  • R 1 is C 3 -C 6 -cycloalkyl, C r C 6 -alkyl, or C r 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 bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • CON H 2 CON HCHS, CON(CH 3 ) 2 , CH 2 CHCH 2 , or CH 2 CoCH;
  • Y is CHCH 2 , C(CH 3 )CH 2 , CH 2 CHCH 2 , CH 2 OCH 3 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), C o CH, CH 2 CHCH 2 , CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCHs, COOC 2 H s , CONH 2 , CONHCH 3 , or CON(CH 3 ) 2 ;
  • Z i.e. 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.
  • R 1 is C 3 -C 6 -cycloalkyl, CrC 6 -alkyl, or CrC 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 bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, CrC 6 -alkyl, CrC 6 -haloalkyl, or CrC 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • X is 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,
  • CONH 2 CONHCH 3 , CON(CH 3 ) 2 , CH 2 CHCH 2 , or CH 2 CoCH;
  • Y is CHCH 2 , C(CH 3 )CH 2 , CH 2 CHCH 2 , CH 2 OCH 3 , CHC(CH 3 ) 2 , C(CH 3 )C(CH 3 ) 2 , CHCH(CH 3 ), C o CH, CH 2 CHCH 2 , CH(CH 3 )CHCH 2 , CH 2 CoCH, CH(CH 3 )CoCH, SH, NHCH 3 , N(CH 3 ) 2 , COOH, COOCH 3 , COOC 2 H s , CONH 2 , CONHCH 3 , or CON(CH 3 ) 2 ;
  • Z i.e. 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 that are compiled in the Tables 1 to 96, wherein the meaning for the combination of variables X and Y of R 2 for each individual compound of tables 1 to 96 corresponds to each row of Table R2.
  • Compound 1.1.3 e.g. comprises the compound of formula 1.1 from Table 1 and row 3 from Table R2;
  • 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.
  • components for mixtures are, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,
  • pyrimidinediones pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazoli nones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, or ureas.
  • 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 com 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 com 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 com 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 com 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 com 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 com 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 com 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 com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I. I) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.J) (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
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase 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, difenzoguat, difenzoguat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluid- ide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, me thyl iod
  • the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bio synthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter-termed ACCase herbicides) or through a different mode of action (hereinafter termed non-ACCase herbicides).
  • ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
  • the compositions contain at least one ALS inhibitor (herbicide b2).
  • the herbicidal activity of these compounds is based on the inhibition of acetolac tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • the compositions contain at least one inhibitor of photosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the inhibition 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 inhibi tors, 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 inhi bition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), com pounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and com 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
  • compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • EPSP synthase inhibitor herebicide 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, com 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 in hibition 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.
  • the compositions contain at least one decoupler herb icide (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 affect the growth of the plants. These compounds belong to the group O of the HRAC classification 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 classification 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, propaguizafop, guizalofop, guizalof
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfa mu ron, 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, penoxsulam, pyrimisulfan and pyroxsulam,
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy] phenyl] methyl]amino] -benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01- 8),
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions comprising 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-pyra- zol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654057-
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide.
  • a preferred em bodiment of the invention relates to those compositions comprising at least one triazine herbi cide.
  • a preferred embodiment of the invention relates to those composi tions comprising at least one nitrile herbicide;
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopy- raniffluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluorogly- cofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiar- gyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, s
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5
  • 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, com 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, ipfencarba- zone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1, II.2, II.3, II.4, II.5,
  • isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;
  • chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b11) 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, aminocyclopyra- chlor 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 es ters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethy
  • 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:
  • 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, metaza- chlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the for mulae 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)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5- fluoro
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B that can be used in combination with the pyrimidine com pounds of the formula (I) according to the present invention are:
  • b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'- Chloro-4-cyclopropyl-2'-fluoro[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,T-biphenyl]-3-yl)-5-hydroxy-
  • ALS inhibitors from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaguin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sul- fosulfuron, thiencarbazon-methyl, tritosul
  • b3 from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraguat, paraguat-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, fentraza- mide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarba- zone and pyroxasulfone; likewise, preference is given to 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;
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B are the herbicides B as defined above; in particular, the herb icides 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. (guinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5- diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agricultural
  • Examples of preferred safeners C are benoxacor, cloguintocet, cyometrinil, cyprosulfamide, di- chlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxa- difen, 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-oxazoli- dine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).
  • Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlo- razole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, ox- abetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-tri- methyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
  • Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroacetyl)- 1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
  • safeners C which, as component C, are constituent of the composition ac cording 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 Company, 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 America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science 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 agricultur ally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally ac ceptable 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 dicamba-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-dimethylammo- nium.
  • 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 ester 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, prefer ably 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-so- dium.
  • 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 guinclorac is e.g. guinclorac-dimethylammonium.
  • a suitable salt of guinmerac is e.g. guinmerac-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 imazaguin is e.g. i mazaguin-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 herbi- cidal 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 herbicides 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), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
  • 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), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound

Abstract

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

Description

Herbicidal pyrimidine compounds
The present invention relates to pyrimidine compounds of the general formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
Description:
Compounds having a 5-phenyl pyrimidine moiety are known in the art. WO 2000/073278 de scribes such compounds being antagonists of the Neurokinin 1 receptor and thus having phar maceutical properties. WO2013/178585 describes the substituted pyridine compound and its use as herbicides compounds.
In agriculture, there is a constant demand to develop novel active ingredients, which comple ment or outperform present methods of treatment regarding activity, selectivity and envi ron mental safety.
These and further objects are achieved by pyrimidine compounds of formula (I), defined below, and by their agriculturally suitable salts.
Accordingly, the present invention provides the compounds of formula (I)
Figure imgf000002_0001
wherein
R1 is CrC6-alkyl, CrC6-haloalkyl, HO-CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al- kynyl, C3-C6-haloalkynyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-haloalkoxy, C3-C6-cycloal- koxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, CrC6-al- kylthio, CrC6-haloalkylthio, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, CrC6-alkylsulfinyl, Cr C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocyclo- alkenyl, [1-(CrC6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-al- kynyl)]-C3-C6-cycloalkyl, [1-(CrC6-haloalkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6- cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl-CrC6-alkyl, C3-C6-cyclo- alkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-CrC6-alkoxy, C3-C6-cycloalkyl-CrC6-haloalkoxy, phe nyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted with Re;
R2 is 5-membered heteroaryl selected from thiophenyl, furyl, which groups are substituted with one X, one Y and one W, or oxazolyl, 1-methylimidazolyl, which groups are substituted with one X and one Y, or 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl which groups are substituted with one Y;
X, W independently are H, halogen, CN, N02, OH, CrC6-alkyl, CrC6-haloalkyl, CrC6- alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, which groups are unsubstituted or substituted with Ra, or R20; Y is Ci-C6-alkyl, CrC6-haloalkyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, CrC6-haloalkoxy, CrC6-al- kylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra, or R20;
R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, aminosulfinyl, CrC6-alkylaminosulfinyl, di(CrC6-alkyl)aminosulfinyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, aminosulfonyl, CrC6-alkylaminosulfonyl, di(CrC6-alkyl)aminosulfonyl, CrC6-alkylcarbonylaminosulfonyl, C3-C6-cycloalkylcarbonyl- aminosulfonyl, hydroxysulfonyl, CrC6-alkoxysulfonyl, hydroxycarbonyl, aminocarbonyl, NH2-aminocarbonyl, CrC6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkinylcarbonyl, thiocarbonyl, CrC6-alkylcarbonylaminocarbonyl, C3-C6-cycloalkylcarbonylaminocarbonyl, CrC6-alkylsulfonylaminocarbonyl, C3-C6-cycloalkylsulfonylaminocarbonyl, di(CrC6-al- kyl)aminosulfonylaminocarbonyl, hydroxyaminocarbonyl, CrC6-alkoxyaminocarbonyl, [(CrC6-alkoxy)(CrC6-alkyl)amino]carbonyl, phenylcarbonyl, 5- or 6-membered het- eroarylcarbonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, (HO)2(0)P, (HO)(CrC6-alkoxy)(0)P, (CrC6-alkoxy)2(0)P, C3-C8-cycloalkyl, C4-C8-cycloal- kenyl, CrC8-alkylidenyl-cycloalkyl, CrC8-alkylidenyl-heterocyclyl, phenyl, 5- or 6-mem bered heteroaryl, or 3- to 6-membered heterocyclyl, phenylsulfinyl, 5- or 6-membered heteroa rylsu Ifi nyl, 3- to 6-membered heterocyclylsulfinyl, C3-C6-cycloalkylsulfinyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- to 6-membered heterocyclyl- sulfonyl, C3-C6-cycloalkylsulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Ra is OH, CN, CrC6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6-haloalkoxy, CrC6- alkoxy-CrC6-alkoxy, NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6-alkylthio, Cr C6-alkylsulfinyl, CrC6-alkylsulfonyl, CN, N02, C3-C6-cycloalkyl, C3-C8-cycloalkenyl, hy droxycarbonyl, CrC6-alkoxycarbonyl, CrC6-haloalkoxycarbonyl, C2-C6-alkenyloxycar- bonyl, C3-C6-alkinyloxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, phenyl, phenylthio, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rb is C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6-haloalkinyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocycloalkenyl, CrC6-alkoxycarbonyl-Cr C6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, hy- droxycarbonyl-CrC6-alkyl, CrC6-alkyloxycarbonyl, CrC6-alkylthiocarbonyl, CrC6-ami- nocarbonyl, CrC6-dialkylaminocarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, C3- C6-cycloalkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, phenyl-CrC6-alkyl, phenyl, 5- or 6-mem bered heteroaryl, or 3- to 6-membered heterocyclyl;
Rc is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, CrC6-haloalkoxy,
NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6-alkylthio, CrC6-alkylsulfinyl, Cr C6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, CrC6-alkylaminocar- bonyl, or di(CrC6-alkyl)aminocarbonyl;
Rd is halogen, CN, N02, OH, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-C6- haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- haloalkoxy, NH2, CrC6-alkyl-amino, di(C1-C6-alkyl)amino, SH, CrC6-alkylthio, CrC6-al- kylsulfinyl, CrC6-alkylsulfonyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, hydroxycarbonyl, Cr C6-alkoxycarbonyl, Ci-C6-alkenyloxycarbonyl, CrC6-alkinyloxycarbonyl, CrC6-alkoxycar- bonyl-CrC6-alkyl, hydroxycarbonyl-CrC6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcar- bonyl, C3-C6-cycloalkylcarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, CrC6-alkylthiocarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, CrC6-alkoxy- CrC6-alkyl, phenylthio, phenyl-CrC6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
Re is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, or CrC6-haloalkoxy;
Rf is H, halogen, CN, OH, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-C6- haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
R4 and R5 are independently from each other selected from hydrogen, CrC6-alkyl, C2-C6- alkenyl, C2-C6-alkinyl, OH, NH2, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, CrC6-alkylsulfonyl, CrC6- haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, CrC6-alkylsulfinyl, C3-C6- alkenylsulfinyl, C3-C6-alkinylsulfinyl, CrC6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3- C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-membered hetero cyclyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3- or 6-membered heterocyclyloxy, C3-C6- cycloalkyloxy, C3-C6-cycloalkenyloxy, phenylcarbonyl, 5- or 6-membered heteroarylcar- bonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloal- kenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl,
5- or 6-membered heteroa rylsu Ifi nyl, 3- or 6-membered hete rocycly Isu Ifi ny I, C3-C6-cy- cloalkylsulfinyl, C3-C6-cycloa I kenylsu Ifi nyl, phenyloxycarbonyl, 5- or 6-membered het- eroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6-cycloalkyloxycar- bonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Cr C6-alkyl)aminocarbonyl, aminosulfonyl, CrC6-alkylaminosulfonyl, di(CrC6-alkyl)amino- sulfonyl, aminosulfinyl, CrC6-alkylaminosulfinyl, and di(CrC6-alkyl)aminosulfinyl;
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;
R3 is H, halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy, CrC6-haloalkoxy, C3-C6- alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-alkoxy-Cr C6-alkoxy, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-alkylthio, CrC6-haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, (C-i-C 6-a I kyl)su Ifi nyl, (CrC6-alkyl)sulfonyl, C3-C6-cy- cloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re;
m is 0, X 2, 3, or 4;
n is X 2, 3, 4, or 5;
including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality.
Preferably, the present invention also provides said pyrimidine compounds of formula (I), wherein when m is 2, 3 or 4, each R3 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-alkynyl, C2- C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3- C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, NH2, (C1-C6-alkyl)amino, di(C1-C6-alkyl)- amino, (C1-C6-alkyl)sulfi nyl, (C1-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re.
Preferably, the present invention also provides the pyrimidine compounds of formula (I)
Figure imgf000005_0001
wherein
R1 is CrC6-alkyl, CrC6-haloalkyl, HO-CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al- kynyl, C3-C6-haloalkynyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-haloalkoxy, C3-C6-cycloal- koxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocydoalkenyloxy, CrC6-al- kylthio, CrC6-haloalkylthio, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, CrC6-alkylsulfinyl, Cr C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocyclo- alkenyl, [1-(CrC6-alkyl)]-C3-C6-cycloalkyl [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-al- kynyl)]-C3-C6-cycloalkyl, [1-(CrC6-haloalkyl)]-C3-C6-cycloalkyl [1-(C2-C6-haloalkenyl)]-C3-C6- cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl-CrC6-alkyl, C3-C6-cyclo- alkyl-CrC6-haloalkyl, C3-C6-cycloalkyl-CrC6-alkoxy, C3-C6-cycloalkyl-CrC6-haloalkoxy, phe nyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted with Re;
R2 is 5-membered heteroaryl selected from thiophenyl, furyl, which groups are substituted with one X, one Y and one W, or oxazolyl, 1-methylimidazolyl, which groups are substituted with one X and one Y, or 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl which groups are substituted with one Y;
X, W independently are H, halogen, CN, N02, OH, CrC6-alkyl, CrC6-haloalkyl, CrC6- alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, CrC6-alkylsulfinyl, CrC6-all<ylsulfonyl, which groups are unsubstituted or substituted with Ra, or R20;
Y is CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy-(CrC4-alkoxy)n, CrC6-haloalkoxy, CrC6-al- kylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra, or
R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfinyl,
C3-C6-alkinylsulfinyl, aminosulfinyl, CrC6-alkylaminosulfinyl, di(CrC6-alkyl)aminosulfinyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, aminosulfonyl, CrC6-alkylaminosulfonyl, di(CrC6-alkyl)aminosulfonyl, CrC6-alkylcarbonylaminosulfonyl, C3-C6-cycloalkylcarbonyl- aminosulfonyl, hydroxysulfonyl, CrC6-alkoxysulfonyl, hydroxycarbonyl, aminocarbonyl, NH2-aminocarbonyl, CrC6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkinylcarbonyl, thiocarbonyl, CrC6-alkylcarbonylaminocarbonyl, C3-C6-cycloalkylcarbonylaminocarbonyl, CrC6-alkylsulfonylaminocarbonyl, C3-C6-cycloalkylsulfonylaminocarbonyl, di(CrC6-al- kyl)aminosulfonylaminocarbonyl, hydroxya mi nocarbonyl, CrC6-alkoxyaminocarbonyl, [(CrC6-alkoxy)(CrC6-alkyl)amino]carbonyl, phenylcarbonyl, 5- or 6-membered het- eroarylcarbonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, (HO)2(0)P, (HO)(CrC6-alkoxy)(0)P, (CrC6-alkoxy)2(0)P, C3-C8-cycloalkyl, C4-C8-cycloal- kenyl, CrC8-alkylidenyl-cycloalkyl, CrC8-alkylidenyl-heterocyclyl, phenyl, 5- or 6-mem bered heteroaryl, or 3- to 6-membered heterocyclyl, phenylsulfinyl, 5- or 6-membered heteroa rylsu Ifi nyl, 3- to 6-membered heterocyclylsulfinyl, C3-C6-cycloalkylsulfinyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- to 6-membered heterocyclyl- sulfonyl, C3-C6-cycloalkylsulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Ra is OH, CN, CrC6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6-haloalkoxy, CrC6- alkoxy-CrC6-alkoxy, NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6-alkylthio, Cr C6-alkylsulfinyl, CrC6-alkylsulfonyl, CN, N02, C3-C6-cycloalkyl, C3-C8-cycloalkenyl, hy- droxycarbonyl, CrC6-alkoxycarbonyl, CrC6-haloalkoxycarbonyl, C2-C6-alkenyloxycar- bonyl, C3-C6-alkinyloxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, phenyl, phenylthio, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rb is C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6-haloalkinyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocycloalkenyl, CrC6-alkoxycarbonyl-Cr C6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, hy- droxycarbonyl-CrC6-alkyl, CrC6-alkyloxycarbonyl, CrC6-alkylthiocarbonyl, CrC6-ami- nocarbonyl, CrC6-dialkylaminocarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, C3- C6-cycloalkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, phenyl-CrC6-alkyl, phenyl, 5- or 6-mem bered heteroaryl, or 3- to 6-membered heterocyclyl;
Rc is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, CrC6-haloalkoxy,
NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6-alkylthio, CrC6-alkylsulfinyl, Cr C6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, al- kinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, CrC6-alkylaminocar- bonyl, or di(CrC6-alkyl)aminocarbonyl;
Rd is halogen, CN, N02, OH, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-C6- haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- haloalkoxy, NH2, CrC6-alkyl-amino, di(C1-C6-alkyl)amino, SH, CrC6-alkylthio, CrC6-al- kylsulfinyl, CrC6-alkylsulfonyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, hydroxycarbonyl, Cr C6-alkoxycarbonyl, CrC6-alkenyloxycarbonyl, CrC6-alkinyloxycarbonyl, CrC6-alkoxycar- bonyl-CrC6-alkyl, hydroxycarbonyl-CrC6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcar- bonyl, C3-C6-cycloalkylcarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, CrC6-alkylthiocarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, CrC6-alkoxy- CrC6-alkyl, phenylthio, phenyl-CrC6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
Re is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, or CrC6-haloalkoxy;
Rf is H, halogen, CN, OH, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-C6- haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; R4 and R5 are independently from each other selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkinyl, OH, NH2, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6- alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, CrC6-alkylsulfonyl, CrC6- haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, CrC6-alkylsulfinyl, C3-C6- alkenylsulfinyl, C3-C6-alkinylsulfinyl, CrC6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3- C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-membered hetero- cyclyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3- or 6-membered heterocyclyloxy, C3-C6- cycloalkyloxy, C3-C6-cycloalkenyloxy, phenylcarbonyl, 5- or 6-membered heteroarylcar- bonyl, 3- or 6-membered heterocyclylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloal- kenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl, 5- or 6-membered heteroa rylsu If i nyl, 3- or 6-membered hete rocycly Isu Ifi ny I, C3-C6-cy- cloalkylsulfinyl, C3-C6-cycloa I kenylsu Ifi nyl, phenyloxycarbonyl, 5- or 6-membered het- eroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6-cycloalkyloxycar- bonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Cr C6-alkyl)aminocarbonyl, aminosulfonyl, CrC6-alkylaminosulfonyl, di(CrC6-alkyl)amino- sulfonyl, aminosulfinyl, Ci-C6-alkylaminosulfinyl, and di(Ci-C6-alkyl)aminosulfinyl;
Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered fully unsaturated bicyclic ring containing 0, 1, 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
R3 same or differently is H, halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy, CrC6-halo- alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Cr C6-alkoxy-CrC6-alkoxy, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-alkylthio, CrC6- haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, (CrC6-alkyl)sulfinyl, (CrC6-al- kyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; m is 0, 1, 2, 3, or 4;
n is 1, 2, 3, 4, or 5;
provided that the pyrimidine compounds of formula (I) is not N-[4-(2,5-Dimethyl-3-furyl)-5-(3- ethyl-4-pyridyl)-2-pyrimidinyl]-N-ethylamine, N-lsopropyl-5-(3-methylisoxazol-5-yl)-4-(5- methylthio-phen-2-yl)pyrimidin-2-amine, 3-Methyl-5-(2-(methylthio)-4-(5-methylthio- phen-2-yl)-pyrimidin-5-yl)isoxazole or 3-Methyl-5-(2-(methylsulfonyl)-4-(5-methylthio- phen-2-yl)pyrimidin-5-yl)isoxazole;
including agriculturally acceptable salts or derivatives of compounds of formula (I).
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.
The pyrimidine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes: Process A:
The pyrimidine compounds of formula (I) can be obtained by reacting respective aminoketones of formula (II) with base and amidine (III):
Figure imgf000008_0001
The reaction of the aminoketones (II) with amidines (III) is usually carried out at temperatures of from -100°C to the boiling point of the reaction mixture, preferably from 20°C to the boiling point, particularly from 40°C to 120°C, in an inert organic solvent in the presence of a base.
The reaction may in principle be carried out in substance. However, preference is given to re acting the aminoketones (II) with the amidine (III) in an organic solvent.
Suitable solvents are those capable of dissolving the aminoketones (II) with the amidine (III) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride (CCI4) and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol, as well as dipolar aprotic solvents such as sulfolane, dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), DMSO, and 1-methyl-2 pyrrolidinone (NMP). Preferred solvents are alcohols such as methanol and etha nol. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCH3), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide (/BuOK), potassium tert-pent- oxide and dimethoxymagnesium, moreover organic bases, e.g. tertiary amines, such as trimethyl- amine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyri dine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicy- clic amines. Particular preference is given to NaOCH3, NaOC2H5, KOC2H5, tBuOK and potassium tert-pentoxide. The bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the amidine (XI), based on the aminoketone (X). Amidines (XI) are known from literature or commercially available. In cases in which R2 resem- Ibes a carbo- oder a heterocycle further, literature known, manipulations are possible: For exam ple oxazoles can selectively be halogenated following published procedures (e.g. Bioorganic & Medicinal Chemistry, 2010, 18, 4821).
Preparation of compounds (II):
Figure imgf000009_0001
The aminoketones (II) are prepared from the corresponding ketones (IV) with N,N-Dimethylfor- mamide dimethyl acetal (CAS 4637-24-5; DMFDMA). The reaction is usually carried out at tem peratures from -100°C to the boiling point of the reaction mixture, preferably from 20°C to 160° C, particularly from 50°C to 130°C. The reaction can optionally be catalyzed by an acid.
The reaction may be carried out in substance or in an organic solvent. Suitable solvents are those capable of dissolving the ketones (IV) and DMFDMA (CAS 4637-24-5) at least partly, pref erably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole 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; preferably DMFDMA is used as solvent. It is also possible to use mixtures of the solvents mentioned.
Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2S04); organic acids p-tol- uenesulfonic 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 eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
Figure imgf000009_0002
The ketones (IV) are prepared by reacting Grignard-reagent (V) with a carbonyl-electrophile (VI) (e.g. an acid halide (Z = F, Cl or Br) or a Weinreb-Amide (Z = N(Me)OMe)). The reaction is carried out at temperatures of from -100° C to the boiling point of the reaction mixture, preferably from -80° C to 60° C, particularly from -80° C to 20° C, in an inert solvent.
Suitable solvents are those capable of dissolving the Grignard-reagent (V) and the carbonyl- electrophile (VI) at least partly and preferably fully under reaction conditions. Examples of suita ble solvents are aliphatic aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, ani sole and THF, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and pro pionitrile, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. Preferred solvents are ethers such as tert-butyl methyl ether or THF. It is also possible to use mixtures of the solvents mentioned.
The Grignard-reagents (V) are either commercially available or can be prepared from the corre sponding halides by known methods.
The carbonyl electrophiles (VI) are either commercially available or can be prepared from the corresponding carboxylic acid or carboxylic ester by known methods.
Figure imgf000010_0001
Ketones (IV) can as well be prepared from morpholinonitriles (VII) as described in the literature (European Journal of Organic Chemistry 2013, 36, 8083).
Figure imgf000010_0002
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 (VI II) and the benzylhal ides (IX) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-di- chloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole 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 dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO, and NMP. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2H5, KOC2H5, tBuOK, po tassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as col lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, LHMDS and LDA.
The bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the halide (IX), based on the morpholinonitrile (VIII).
Benzylhalides (IX) are commercially available. Morpholinonitriles (VIII) are prepared from the corresponding aldehydes (X) as described in the literature (WO 2009/013462). Aldehydes (X) are commercially available.
Process B :
Figure imgf000011_0001
The pyrimidines of formula (XI) can be obtained from pyrimidines of formula (XII) by known methods e.g using PPh3 and Iodine (analogous to Davies, James R. et ai Journal of Organic Chemistry, 70(15), 5840-5851, 2005 or Just-Baringo, Xavier et ai Angewandte Chemie, Interna tional Edition, 52(30), 7818-7821, 2013).
Figure imgf000011_0002
The pyrimidines of formula (XII) can be obtained from pyrimidines of formula (XIII) by reaction with the carboxylic acides (XIV), wherein R is alkyl, cycloalkyl, ha locycloa I kyl, haloalkyl, cycloal kenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl.
The reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, particularly from 0°C to 60°C, in an inert or ganic solvent.
Carboxylic acids RCOOH are commercially available. Carboxylic acids are activated using acti vating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethyla- mino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H- benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-hexafluorophosphate (HBTU), ethyl-3-(3-dimethyl- aminopropyl)carbodiimid (EDC). The carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chloride. Carbonylimidazoles such as 1,T-Carbon- yldiimidazol (CDI) may also be used as activating reagent under neutral conditions. Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU.
Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered solvents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyridine, sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DI PEA.
The bases are generally employed in excess amounts; however, they can also be employed in egual amounts as the pyrimidine.
Figure imgf000012_0001
The pyrimidines of formula (XIII) can be obtained from pyrimidines of formula (XV), wherein R is hydroxycarbonyl, alkoxycarbonyl, (H0)2(0)P, (alkoxy)2(0)P, alkyl sulfonyl or alkylcarbonyl, by reac tion with with an acid HA
The reaction of the pyrimidine (XV) is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, particularly from 0°C to 60°C, in an organic solvent using water as a cosolvent. The starting materials are reacted with one another in eguimolar amounts or using an excess of one reagent. Preference is given to us ing an excess of acid HA.
Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid (H2S04); organic acids p-tol- uenesulfonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; most preferably HCI.
Suitable solvents include dioxane and tetrahydrofuran (THF), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and N,N-di- methylacetamide (DMAC), Acetonitrile (ACN). Prefered solvents are alcohols. It is also possible to use mixtures of the solvents mentioned.
The pyrimidines of formula (XV) can be obtained by process C.
Process C:
The pyrimidines of formula (XV), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or a carboxylic ester, can be obtained by re acting respective pyrimidines of formula (XVI) with isocyanides (XVII):
Figure imgf000012_0002
The reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 78°C to 25°C, particularly from -78°C to 0°C, in an inert or ganic solvent using a base. Suitable solvents are those capable of dissolving the pyrimidine (XVI) and the isocyanides (XXI) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /?-BuLi.
The bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the isocyanide (XVII) based on the pyrimidine (XVI).
The pyrimidines of formula (XVI) can be obtained by reacting respective pyrimidines of formula (XVIII) with boronic acids/esters of formula (XIX):
Figure imgf000013_0001
The reaction of pyrimidines (XVIII) with boronic acids/esters (XIX) is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
The reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XVIII) with the boronic acids/esters (XIX) in an organic solvent with or without water as co-solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XVIII) and the boronic acids (XIX) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-contain ing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li20, Na20, K20, MgO, and CaO, Fe203, Ag20; alkali metal and alkaline earth metal carbonates such as Li2C03, Na2C03, K2C03, Cs2C03, MgC03, and CaC03, as well as alkali metal bicarbonates such as LiHC03, NaHC03, KHC03; alkali metal and alkaline earth metal phosphates such as K3P04, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydrox ides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkali metal or alkaline earth metal carbonates such as Li2C03, Na2C03, K2C03, Cs2C03, MgC03, and CaC03 and alkaline earth metal phosphates such as K3P04; alkali metal and alkaline earth metal acetates such as sodium acetate. Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkaline earth metal phosphates such as K3P04.
The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
The bases are used preferably at from 1 to 10 eguivalents based on the pyrimidine (XVIII), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XVIII), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XVIII).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyrimidines (XVIII) with the boronic acids/esters (XIX) is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)pal- ladium(ll)chloride or (1,1,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1,T-binaphthyl).
The amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 eguivalents) based on the py rimidine (XVIII).
The halopyrimidines (XVIII) are known from the literature (e.g. WO 2011154327), are commer cially available or can be prepared by known procedures.
The boronic acids/esters (XIX) reguired for the preparation of pyrimidines of formula (XVI) are commercially available, known from literature or can easily be prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
Process
Figure imgf000014_0001
The pyrimidines of formula (XV) can also be obtained by reacting respective pyrimidine alde hydes (XX) with tosyl isocyanides (XXI), wherein R is alkyl, cycloalkyl, halocycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, Oheteroaryl. The reaction of the pyrimidine (XX) with the tosyl isocyanides (XXI) is usually carried out at temperatures of from - 100°C to the boil ing point of the reaction mixture, preferably from 0°C to the boiling point of the reaction mixture, particularly from 25°C to 65°C, in an inert organic solvent using a base. Suitable solvents are those capable of dissolving the pyrimidine (XX) and the isocyanides (XXI) at least partly and pref erably fully under reaction conditions.
Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered solvents are methanol and ethanol.
Suitable bases are alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCH3), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide (/BuOK), potassium tert-pentoxide and dimethoxymagnesium. Moreover metal carbonates such as caesium carbonate and potassium carbonate. Moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as col lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to potassium carbonate.
The bases are generally employed in eguimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the tosyl isocyanide (XXI), based on the pyrimidine (XX).
Figure imgf000015_0001
The pyrimidines of formula (XX) can be obtained by oxidizing respective pyrimidine alcohols of formula (XXII).
The oxidation of pyrimidines (XXII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 100 °C, particularly at from 0 °C to 75 °C, in an inert organic solvent.
The reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XXII) in an organic solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XXII) at least partly and pref erably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH2CI2, CHCI3,
CCH2CICH2CI or CCI4, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCI4,and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, N,N' -dimethyl-· propylene urea (DMPU), DMSO and NMP. More preferred solvents halogenated hydrocarbons such as CH2CI2, CMOS, CCH2CICH2CI or CCI4. It is also possible to use mixtures of the solvents mentioned.
Examples of oxidizing agents for the synthesis of pyrimidines (XX) are metal oxides such as Mn02, KMn04, Cr03 or PCC, and non-metal oxides such as NaCIO, Nal04 or pyridine/S03-com- plex. In addition, methods like the Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyrimidines of formula (XX).
Preferred agents include Mn02, KMn04 and PCC, more preferred Mn02.
The oxidizing agent is used preferably from 1 to 50 eguivalents based on the pyrimidine (XXII), more preferably at from 1.0 to 20.0 eguivalents based on the pyrimidine (XXII), most preferably from 1.0 to 10.0 eguivalents based on the pyrimidine (XXII).
The pyrimidines of formula (XXII) can be obtained by reacting respective pyrimidines of formula (XVI) with a red
Figure imgf000015_0002
The reduction of pyrimidines (XVI) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably at from -20 °C to 60 °C, particularly at from 0 °C °C to 25 °C, in an inert organic solvent.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, 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 mix tures of the solvents mentioned.
Examples of reducing agents for pyrimidines (XVI) include LAH, DIBALH, LiBH4 or lithium tri- ethylborohydride. Preferred agents include LAH and DIBALH.
The hydride-source is used preferably from 1 to 10 eguivalents based on the pyrimidine (XVI), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XVI), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XVI).
Process E:
Figure imgf000016_0001
The pyrimidines of formula (XXIII) can be obtained from pyrimidines of formula (XXIV) by known methods e.g using actic acid anhydride/ concentrated sulfuric acid (e.g Godfrey, Alexander G. et al Journal of Organic Chemistry, 68(7), 2623-2632, 2003) or using burgess reagent (e.g. Brain, C.
T et ai Synlett, 1642-1644, 1999).
Figure imgf000016_0002
The pyrimidines of formula (XXIV) can be obtained from carboxylic acids of formula (XXV) by reaction with amino ketones of formula (XXVI), wherein R substituents of the amino ketones are indenpendently of each alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl. The reaction of the carboxylic acids (XXV) with amino ketones (XXVI, commercially available), is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 20°C to 60°C, partic ularly from 0°C to 60°C, in an inert organic solvent.
Carboxylic acids (XXX) are activated using activating reagents commonly used in solid-phase peptides synthesis such as 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-hex- afluorophosphate (HBTU), ethyl-3-(3-dimethylaminopropyl)carbodiimid (EDC). The carboxylic acid can also be activated by formation of the acid chloride using oxalyl chloride or thionyl chlo ride. Carbonylimidazoles such as 1,T-Carbonyldiimidazol (CDI) may also be used as activating re agent under neutral conditions. Phosphoryl azides such as Diphenylphosphoryl azide (DPPA) may also be employed. Preference is given to HATU. Suitable solvents include dioxane, anisole and tetrahydrofuran (THF), dichloromethane (DCM), alcohols such methanol (MeOH) and Ethanol (EtOH) and also dimethyl sulfoxide (DMSO), dime- thylformamide (DMF) and N,N-dimethylacetamide (DMAC), Acetonitrile (ACN). Prefered solvents are acetontrile and DMF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases include inorganic and organic bases, e.g. tertiary amines, such as trimethylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperidine, pyridine, sub stituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines and annelated amidines such as Diazabicycloundecen (DBU). Particular preference is given to DI PEA.
The bases are generally employed in excess amounts; however, they can also be employed ain egual amounts as the pyrimidine.
Process
Figure imgf000017_0001
The pyrimidines of formula (XI) with R'= alkyl, alkenyl, cycloalkenyl, alkinyl, aryl or heteroaryl can be obtained by reacting respective pyrimidines of formula (XXVII) with X = Cl, Br with boronic ac ids/esters of formula (XXVIII). The reaction is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 110 °C, particularly at from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
The reaction may in principle be carried out in substance. However, preference is given to re acting the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) in an organic solvent with or without water as co-solvent.
Suitable solvents are those capable of dissolving the pyrimidines (XXVII) and the boronic acids (XXVIII) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and MP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-contain ing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li20, Na20, K20, MgO, and CaO, Fe203, Ag20; alkali metal and alkaline earth metal carbonates such as Li2C03, Na2C03, K2C03, Cs2C03, MgC03, and CaC03, as well as alkali metal bicarbonates such as LiHC03, NaHC03, KHC03; alkali metal and alkaline earth metal phosphates such as K3P04, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate. Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydrox ides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkali metal or alkaline earth metal carbonates such as Li2C03, Na2C03, K2C03, Cs2C03, MgC03, and CaC03 and alkaline earth metal phosphates such as K3P04; alkali metal and alkaline earth metal acetates such as sodium acetate. Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3 and alkaline earth metal phosphates such as K3P04.
The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
The bases are used preferably at from 1 to 10 eguivalents based on the pyrimidine (XXVII), more preferably at from 1.0 to 5.0 eguivalents based on the pyrimidine (XXVII), most preferably from 1.2 to 2.5 eguivalents based on the pyrimidine (XXVII).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyrimidines (XXVII) with the boronic acids/esters (XXVIII) is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)pal- ladium(ll)chloride or (1,1,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1,T-binaphthyl).
The amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 eguivalents) based on the py rimidine (XXVII).
The boronic acids/esters (XXVIII) reguired for the preparation of pyrimidines of formula (XI) are commercially available, known from literature or can easily be prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
Figure imgf000018_0001
The pyrimidines of formula (XXVII) with X = Cl, Br can be obtained from pyrimidines of formula (XV) by known methods e.g using hexachloroethane or dibromochloroethane (Bioorg. Med. Chem. 2010, 18, 4821-4829).
Process G:
Figure imgf000018_0002
The pyrimidines of formula (XI) with R'= OH, SH, ORb, SRb, NR4R5 can be obtained from pyrim idines of formula (XXVII) with X = Cl, Br by reaction with 0-, S- or N-nucleophiles.
The reaction of the pyrimidine with the nucleohpile is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particu- larly from 20°C to 80°C, in an inert organic solvent using a base. Suitable solvents are those ca pable of dissolving the pyrimidine (XXVII) and the nucleophile at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2H5, KOC2H5, tBuOK, po tassium tert-pentoxide and dimethoxymagnesium alkali metal and alkaline earth metal car bonates such as Li2C03, Na2C03, K2C03, Cs2C03, MgC03, and CaC03, as well as alkali metal bicar bonates such as LiHC03, NaHC03, KHC03; alkali metal and alkaline earth metal phosphates such as K3P04, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or po tassium acetate; moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N- methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethyla- minpyridine, and also bicyclic amines. Particular preference is given to NaH, LHMDS, LDA, NaOCH and K2C03.
The bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the nucleophile based on the pyrimidine (XXVII).
Process H:
Figure imgf000019_0001
The pyrimidines of formula (XI) with R' = 1-hydroxy-alkyl, 1- hydroxy-aryl, 1-hydroxy-heteroaryl, 1-hydroxy-heterocyclyl, 1-hydroxy-cycloalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, al- kinylcarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carbocyclylcarbonyl and re lated compounds can also be obtained by reacting respective pyrimidines of formula (XV) with a base and an electrophile.
The reaction is usually carried out at temperatures of from - 100°C to the boiling point of the reaction mixture, preferably from - 78°C to 25°C, particularly from -78°C to 0°C, in an inert or ganic solvent using a base. Suitable solvents are those capable of dissolving the pyrimidine (XV) at least partly and preferably fully under reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, tol uene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
Preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF and dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP. More preferred solvents are ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF. It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi. Particular preference is given to lithium hexamethyldisilazide, LDA and /7-BuLi.
The bases are generally employed in eguimolar amounts; however, they can also be employed in excess.
Suitable electrophiles are for example aldehydes and acid anhydrides, which are commercially available.
The starting materials are reacted with one another in eguimolar amounts. It may be advanta geous to employ an excess of base and/or the electrophile based on the pyrimidine (XV).
The end of the reactions can easily be determined by the skilled worker by means of routine methods.
The reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separa tion 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 ele vated temperature.
If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallization or digestion.
The present invention also provides agrochemical compositions comprising at least one pyrimidine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
The present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyrimidine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat. Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
If the pyrimidine compounds of formula (I) as described herein are capable of forming geomet rical isomers, e.g. E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
If the pyrimidine compounds of formula (I) as described herein have one or more centres of chirality and, as a conseguence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
If the pyrimidine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, more preferably a carboxylic group or a sulphonic group, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations 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-CrC4-alkyl, CrC4-alkoxy-Ci-C4-al- kyl, HO-CrC4-alkoxy-CrC4-alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae- thylamm-onium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxy- eth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-HO-ethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrime- thylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), fur thermore phosphon-ium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trime- thylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of CrC4-alka- noic acids, preferably formate, acetate, propionate and butyrate.
Pyrimidine compounds of formula (I) as described herein having an acidic functionality, prefera bly a carboxylic group or a sulphonic group, can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with the cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-CrC6-alkyl- amides or arylamides, as esters, e.g. as allyl esters, propargyl esters, Ci-C 0-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl) methyl) esters and also as thioesters, e.g. as CrCi0-alkylthio esters. Preferred mono- and di-CrC6-alkylamides are the CH3 and the dimethylamides. Preferred arylamides are, e.g., the anilides and the 2-chloroanilides. Preferred alkyl esters are, e.g., the me thyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylhep- tyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched CrC4-alkoxy ethyl esters, e.g. the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched Ci-Ci0-alkylthio ester is the ethylthio ester.
The organic moieties mentioned in the definition of the variables R1, R2, Z, R3, and R3A, are - like the term halogen - collective terms for individual enumerations of the individual group members. The term halogen denotes in each case F, Cl, Br, or I. All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix Cn-Cm denoting in each case the possible number of carbon atoms in the group.
Examples of such meanings are: CrC4-alkyl: e.g. CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2, and C(CH3)3;
CrC6-alkyl: CrC4-alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-di methyl propyl, 1,2- dimethylpropyl, 1- methyl pentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethyl- butyl, 1,2-di methyl butyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1-ethylbutyl, 2-ethyl butyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpro- pyl, or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1— di- methylethyl, n-pentyl, or n-hexyl;
Ci-C4-haloalkyl: CrC4-alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, 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, 2-fluoropropyl, 3-fluoropropyl, 2,2- difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromo- propyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoro-propyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromome- thyl)-2-bromo-ethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1, 1,2,2, -tetra- fluoroethyl, and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;
CrC6-haloalkyl: CrC4-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-
1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,
2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2- dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1- pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl- 4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-bu- tenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-bu- tenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-bu- tenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-pro- penyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl;
C3-C6-cycloalkenyl: monocyclic partially unsaturated hydrocarbons having 3 to 6 ring members e.g. cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl.
C3-C6-haloalkenyl: a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3- chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2- en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibro- moprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl, or 2,3-dibromobut-2- en-1-yl;
C3-C6-alkynyl: e.g. 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4- pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-bu- tynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,
1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl;
C2-C6-alkynyl: C3-C6-alkynyl as mentioned above and also ethynyl;
C3-C6-haloalkynyl: a C3-C6-alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bro- moprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1- difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluo- rohex-4-yn-1-yl, or 6-iodohex-5-yn-1-yl;
CrC4-alkoxy: e.g. methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2- methylpropoxy, and 1,1-dimethylethoxy;
CrC6-alkoxy: CrC4-alkoxy as mentioned above, and also, e.g., pentoxy, 1- methyl butoxy,
2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1 -ethyl propoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,
4- methyl pentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethyl butoxy, 2-ethyl butoxy, 1,1,2-trime
thyl propoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.
CrC4-haloalkoxy: a CrC4-alkoxy group as mentioned above which is partially or fully sub stituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroeth- oxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromo- propoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3- trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoeth- oxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, and nonafluorobutoxy;
CrC6-haloalkoxy: a CrC4-haloalkoxy as mentioned above, and also, e.g., 5-fluoropentoxy,
5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6- chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
CrC4-alkylthio: e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1,1-dimethylethylthio;
CrC6-alkylthio: CrC4-alkylthio as mentioned above, and also, e.g., pentylthio, 1-methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2- ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1- ethyl-2-methylpropylthio;
(CrC4-alkyl)amino: e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1,1-dimethylethylamino;
(CrC6-alkyl)amino: (CrC4-alkylamino) as mentioned above, and also, e.g., pentylamino, 1- methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethyl- propylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutyla- mino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropyl- amino, 1,2,2-trimethyl-propylamino, 1-ethyl-1-methylpropylamino, or 1-ethyl-2-methylpropyla- mino;
di(CrC4-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- propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1- methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1- methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N- (l-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N- (2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-meth- ylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpro- pyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N- butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2- methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino, or N-(1,1-dimethylethyl)-N- (2-methylpropyl)amino;
di(CrC6-alkyl)amino: di(CrC4-alkyl)amino as mentioned above, and also, e.g., N-methyl- 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- dimethylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1,1-dime- thylbutyl)amino, N-methyl-N-(1,2-dimethylbutyl)amino, N-methyl-N-(1,3-dimethylbutyl)amino, N- methyl-N-(2,2-dimethylbutyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3- dimethylbutyl)amino, N-methyl-N- (l-ethylbutyl)amino, N-methyl-N-(2-ethylbutyl)amino, N-me- thyl-N-(1,1,2-trimethylpropyl)amino, N-methyl-N- (1,2,2-trimethylpropyl)amino, N-methyl-N-(1- ethyl-1-methylpropyl)amino, N-methyl-N- (1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentyla- mino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methyl- butyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N- hexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino, N-ethyl-N-(1,2-dimethylpropyl)amino, N- ethyl-N-(1-methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpen- tyl)amino, N-ethyl-N-(4-methylpentyl)amino, N-ethyl-N-(1,1-dimethylbutyl)amino, N-ethyl-N-(1,2- dimethylbutyl)amino, N-ethyl-N-(1,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N-(2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethyl- butyl)amino, N-ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1,1,2-trimethylpropyl)amino, N-ethyl-N- (1,2,2-trimethylpropyl)amino, N-ethyl-N-(1-ethyl-1-methylpropyl)amino, N-ethyl-N-(1-ethyl-2- methylpropyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, N,N-dipentylamino, N- propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino, or N,N-dihexylamino;
CrC6-alkylsulfinyl (CrC6-Alkyl-S(=0)-): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1- methylethylsulfinyl, butylsulfinyl, 1 - methyl propyl su Ifi ny I, 2-methylpropylsulfinyl, 1,1-d imethylethyl- sulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3 - methyl butylsu Ifi ny I, 2,2-di methyl propylsulfinyl, 1 -ethyl propylsu Ifi nyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropyl-sulfinyl, hexylsulfinyl, 1-methylpentylsulfi nyl, 2-methylpentylsulfi nyl, 3 - methyl pentylsu Ifi nyl, 4-methylpen- tyl-sulfinyl, 1,1 -d i methyl butyl su Ifi nyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutyl-sulfinyl, 2,2-dime- thyl butylsu Ifi nyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutyl-sulfinyl, 1 -ethyl butylsu Ifi nyl, 2-ethyl- butylsulfinyl, 1,1,2-trimethyl propylsulfinyl, 1,2,2-trimethyl propylsulfinyl, 1-ethyl-1-methylpropyl-sul- finyl, and 1-ethyl-2-methylpropylsulfinyl;
CrC6-alkylsulfonyl (CrC6-alkyl-S(0)2-): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1- methylethylsulfonyl, butylsu Ifonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-di- methylethylsulfonyl, pentylsu Ifonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfonyl, hexylsu Ifonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpen- tylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dime- thyl butylsu Ifonyl, 2,2-dimethyl butylsu Ifonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutyl-sulfonyl,
1 -ethyl butylsu Ifo nyl, 2-ethylbutylsulfonyl, 1,1,2-trimethyl-pro pylsulfonyl, 1,2,2-trimethyl-propyl- sulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl;
C3-C6-cycloalkyl: a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
C3-C6-cycloalkenyl: 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1- cyclopentenyl, 2-cyclopentenyl, 1,3-cyclopentadienyl, 1,4-cyclopentadienyl, 2,4-cyclopentadienyl, 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-dihydrobenzothiophene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1,3-benzodioxole, 1,3-benzodithiole, 1,3- benzoxathiole, indole, indane, [1,3]dioxolo[4,5-c] pyridine, [1,3]dioxolo[4,5-b] pyridine, 2,3-dihydro- furo[2,3-c]pyridine, furo[2,3-c]pyridine, 2,3-dihydrofuro[2,3-b]pyridine, fu ro[2,3-b] pyridine, 2,3- dihydrofuro[3,2-c] pyridine, furo[3,2-c]pyridine, 2,3-dihydrofuro[3,2-b]pyridine, furo[3,2-b]pyri- dine, furo[3,2-d]pyrimidine, furo[2,3-d]pyrimidine, 6,7-dihydrofuro[3,2-d]pyrimidine, 5,6-dihydro- furo[2,3-d]pyrimidine, thieno[3,2-d] pyrimidine, thieno[2, 3-d] pyrimidine, 6,7-dihydrothieno[3,2- d]pyrimidine, 5,6-dihydrothieno[2,3-d]pyrimidine, 2, 3-dihydrothieno[2,3-c] pyridine, thieno[2,3- c]pyridine, 2,3-dihydrothieno[2,3-b]pyridine, thieno[2,3-b]pyridine, 2,3-dihydrothieno[3,2-c]pyri- dine, thieno[3,2-c]pyridine, 2,3-dihydrothieno[3,2-b]pyridine, thieno[3,2-b]pyridine, 1H-pyr- rolo[2,3-c] pyridine, 1H-pyrrolo[2,3-b] pyridine, 1 H-pyrrolo[3,2-c] pyridine, 1H-pyrrolo[3,2-b] pyri dine, 1H-imidazo[4,5-c]pyridine, 1H-imidazo[4,5-b]pyridine, 3H-imidazo[4,5-c]pyridine, 3H-imid- azo[4,5-b] pyridine, 1H-pyrazolo[3,4-b]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[4,3- b] pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-indazole, benzimidazole, 1,2-benzoxazole, 1,3-benzox- azole, 1,3-benzothiazole, 1,2-benzothiazole, naphthalene, quinolone, isoquinoline, quinazoline, 1,3-benzoxathiole, [1,3]oxathiolo[4,5-b] pyridine, [1,3]oxathiolo[4,5-c] pyridine, [1,3]oxathiolo[5,4- c] pyridine, [1,3]oxathiolo[5,4-b] pyridine, 2,3-dihydro-1,4-benzodioxine, 2, 3-d i hyd ro- [1,4] d iox- ino[2,3-b] pyridine, 2,3-dihyd ro-[1,4]dioxino[2,3-c] pyridine;
heterocyclyl: a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
3- or 4-membered heterocycles like 2-oxiranyl, 2-aziridinyl, 2-thiiranyl, 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 1-azetinyl, or 2-azetinyl;
5-membered saturated heterocycles like 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahy- drothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 2-isothiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothia- zolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazol- idinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazoli- dinyl, 4-imidazolidinyl, 3-oxazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 3-thiazoli- dinyl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,2,4-oxadiazolidin- 2-yl, 1,2,4-oxadiazolidin-4-yl, 1,3,4-oxadiazolidin-2-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazoli- din-4-yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl, or 1,3,4-triazolidin-2-yl;
5-membered partial unsaturated heterocycles like 2, 3 -d i hyd rofu r-2 -y I, 2, 3-d i hyd rofu r- 3 -yl, 2,4- dihydrofur-2-yl, 2,4-d i hyd rofu r- 3 -y I, dioxolan-2-yl, 1,3-dioxol-2-yl, 2,3-dihydrothien-2-yl, 2,3-di- hydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihyd rothien-3-yl, 4,5-dihyd ropyrrol-1-yl, 4,5-dihy- dropyrrol-2-yl, 4, 5 - d i hyd ro py r ro I - 3 -y I, 2,5-dihyd ropyrrol-1-yl, 2,5-dihyd ropyrrol-2-yl, 2,5-dihy- dropyrrol-3-yl, 2,3-dihydroisoxazol-1-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3- dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,
4.5-dihydroisoxazol-2-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol- 5-yl, 2,3-dihyd roisothiazol-1-yl, 2,3-dihyd roisothiazol-3-yl, 2,3-dihyd roisothiazol-4-yl, 2,3-dihy- droisothiazol-5-yl, 2,5-dihyd roisothiazol-3-yl, 2,5-dihyd roisothiazol-4-yl, 2,5-dihydroisothiazol-5- yl, 4,5-dihydroisothiazol-1-yl, 4,5-dihyd roisothiazol-3-yl, 4,5-dihyd roisothiazol-4-yl, 4,5-dihyd roi- sothiazol-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-di hyd ropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4- dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl,
4.5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihyd roimidazol-1-yl, 2,3-dihydroimidazol- 2-yl, 2,3-dihydroimidazol-3-yl ,2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihy- droimidazol-1-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,
2.5-dihyd roimidazol-1-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimid- azol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydroox- azol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-di hydroox- azol-5-yl, 2,3-dihyd rothiazol-2-yl, 2,3-dihyd rothiazol-3-yl, 2,3-dihyd rothiazol-4-yl, 2,3-dihydro- thiazol-5-yl, 3,4-dihyd rothiazol-2-yl, 3,4-dihyd rothiazol-3-yl, 3,4-dihyd rothiazol-4-yl, 3,4-dihy- drothiazol-5-yl, 3,4-d i hyd rothi azol -2-y I, 3,4-dihyd rothiazol-3-yl, or 3,4-dihydrothiazol-4-yl;
6-membered saturated heterocycles like 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-plperid inyl, 1,3-dioxan-5-yl, 1,4-dioxanyl, 1,3-d ithlan-5-yl, 1,3-d ithianyl, 1,3-oxathian-5-yl, 1,4-oxathianyl, 2- tetrahydropyranyl, 3-tetrahydopyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahy- drothiopyranyl,4-tetrahydrothiopyranyl, 1-hexahydropyridazinyl, 3-hexahydropyridazinyl, 4-hexa- hydropyridazinyl, 1-hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5- hexa hyd ropyri midi nyl, 1-piperazinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotri- azin-2-yl, 1,2,4-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-1-yl, tet- rahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl, 1-morpholinyl, or 2-morpholinyl, 3-mor- pholinyl;
6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thi- opyran-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, pyrazol-4- yl), isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3-yl, iso- thiazol-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), oxadiazolyl (e.g. 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4- oxadiazol-2-yl), thiadiazolyl (e.g. 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-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-triazol-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, pyrimidin-4-yl, py- rimidin-5-yl), pyrazin-2-yl, triazinyl (e.g. 1,3,5-triazin-2-yl, or 1,2,4— triazin-3-yl, 1,2,4-triazin-5-yl,
1.2.4-triazin-6-yl).
The term "substituted" if not specified otherwise refers to substituted with 1, 2 or maximum pos sible 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 mentioned other wise.
The term "acidic functionality" if not specified otherwise refers to a functionality capable of do nating a hydrogen (proton or hydrogen ion H+), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
The terms "compounds of formula (I)", "Pyrimidine compounds of formula (I)", "Compounds I" and "compounds of invention" are synonyms.
The term "cyclic groups" comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another.
In general, pyrimidine compounds of formula (I) are suitable as herbicides. According to a preferred embodiment of the invention preference is given pyrimidine com pounds of formula (I), and their use as herbicides, wherein the variables, either independently of one another or in combination with one another, have the following meanings:
preferred R1 is CrC6-alkyl, CrC6-haloalkyl, HO-CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-haloalkoxy, C3-C6-cycloalkoxy, C3- C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, CrC6-alkylthio, Cr &- haloalkylthio, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, C3- C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocycloalkenyl, [1-(CrC6-alkyl)]- C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1-(Cr C6-haloalkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3- C6-cycloalkyl, C3-C6-cycloalkyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-haloalkyl, C3-C6-cycloalkyl-Cr C6-alkoxy, C3-C6-cycloalkyl-CrC6-haloalkoxy, 5-membered heteroaryl, or 3- to 6-membered het- erocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted with Ra;
also preferred R1 is CrC6-alkyl, CrC6-haloalkyl, HO- CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-haloalkoxy, C3-C6-cycloalkoxy, C3- C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, CrC6-alkylthio, CrC6- haloalkylthio, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, C3- C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocycloalkenyl, [1-(CrC6-all<yl)]- C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1-(Cr C6-haloalkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3- C6-cycloalkyl, C3-C6-cycloalkyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-haloalkyl, C3-C6-cycloalkyl-Cr C6-alkoxy, or C3-C6-cycloalkyl-CrC6-haloalkoxy,
wherein the cyclic groups of R1 are unsubstituted or substituted with Ra;
also preferred R1 is CrC6-alkyl, CrC6-alkoxy, CrC6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C4-C6-haloalkynyloxy, CrC6-alkylthio, C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
particularly preferred R1 is CrC6-alkyl, CrC6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
especially preferred R1 is C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R1 is C2H5, i-C3H7, i-C4H9, OCH3, c-C3H5, or c-C4H7;
more preferred R1 is C2H5, OCH3, or c-C3H5; most preferred R1 is c-C3H5;
preferred R2 is selected from R2-1 to R2-24 as shown below,
Figure imgf000028_0001
wherein # denotes attachment to the pyrimidine ring,
preferred R2 is R2-1, R2-2, R2-3, R2-4, R2-5, R2-6, R2-7, R2-8, R2-9, R2-10, R2-11, or R2-12;
more preferred R2 is R2-1, R2-2, R2-3, R2-4, R2-5, or R2-6;
also more preferred R2 is R2-7, R2-8, R2-9, R2-10, R2-11, or R2-12;
also preferred R2 is R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, R2-21, R2-22, R2-23, or R2-24;
also more preferred R2 is R2-13, R2-14, R2-15, R2-16, R2-17, or R2-18;
also more preferred R2 is R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-23, or R2-24;
particularly preferred R2 is R2-19, R2-20, R2-23, or R2-24;
also particularly preferred R2 is R2-23, or R2-24;
also particularly preferred R2 is R2-13, R2-14, R2-15, or R2-16;
also particularly preferred R2 is R2-17, or R2-18;
also particularly preferred R2 is R2-13, or R2-14;
also particularly preferred R2 is R2-15, or R2-16;
most preferred R2 is R2-13;
also most preferred R2 is R2-14;
also most preferred R2 is R2-15;
also most preferred R2 is R2-16;
also most preferred R2 is R2-17;
also most preferred R2 is R2-18;
preferred X is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, or R20;
particularly preferred X is H, halogen, CN, CrC6-alkyl, OH, CrC6-alkoxy, CrC6-alkylthio, or R20; also particularly preferred X is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, CrC6- haloalkoxy, or R20;
especially preferred X is H, halogen, CN, Ci-C4-alkyl, OH, CrC4-alkoxy, C -C4-alkylthio, or R20; also especially preferred X is H, CrC4-alkyl, or R20;
also especially preferred X is CrC4-alkyl, or R20; also especially preferred X is H or R20;
also especially preferred X is R20;
more preferred X is H, CH3, C2H5, n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH3, SCH3, F, Cl, Br, I, or R20;
also more preferred X is H, CH3, C2H5, n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH3, SCH3, F, Cl, Br, or I;
most preferred X is H, CH3, C2H5, OH, OCH3, or R20;
most preferred X is H, CH3, C2H5, OH, or OCH3;
also most preferred X is H, CH3, C2H5, SCH3, or R20;
also most preferred X is H, CH3, C2H5, or SCH3;
also most preferred X is H, CH3, C2H5, F, Cl, Br, I, or R20;
also most preferred X is H, CH3, C2H5, F, Cl, Br, or I;
also most preferred X is H, CH3, C2H5, or R20;
also most preferred X is H, CH3, or C2H5;
most particularly preferred X is H or R20;
most particularly preferred X is H;
also most particularly preferred X is CH3 or R20;
also most particularly preferred X is CH3;
also most particularly preferred X is C2H5 or R20;
also most particularly preferred X is C2H5;
preferred W is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, or R20;
particularly preferred W is H, halogen, CN, CrC6-alkyl, OH, CrC6-alkoxy, CrC6-alkylthio, or R20; also particularly preferred W is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, CrC6- haloalkoxy, or R20;
especially preferred W is H, halogen, CN, CrC4-alkyl, OH, CrC palkoxy, CrC palkylthio, or R20; also especially preferred W is H, CrC4-alkyl, or R20;
also especially preferred W is CrC ralkyl, or R20;
also especially preferred W is H or R20;
also especially preferred W is R20;
more preferred W is H, CH3, C2H5, n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH3, SCH3, F, Cl, Br, I, or R20;
also more preferred W is H, CH3, C2H5, n-propyl, iso-propyl, isobutyl, n-butyl, OH, OCH3, SCH3,
F, Cl, Br, or I;
most preferred W is H, CH3, C2H5, OH, OCH3, or R20;
most preferred W is H, CH3, C2H5, OH, or OCH3;
also most preferred W is H, CH3, C2H5, SCH3, or R20;
also most preferred W is H, CH3, C2H5, or SCH3;
also most preferred W is H, CH3, C2H5, F, Cl, Br, I, or R20;
also most preferred W is H, CH3, C2H5, F, Cl, Br, or I;
also most preferred W is H, CH3, C2H5, or R20;
also most preferred W is H, CH3, or C2H5;
most particularly preferred W is H or R20;
most particularly preferred W is H;
also most particularly preferred W is CH3 or R20; also most particularly preferred W is CH3;
also most particularly preferred W is C2H5 or R20;
also most particularly preferred W is C2H5;
preferred Y is CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy-(CrC4-alkoxy)n, CrC6-haloalkoxy, CrC6- alkylthio, CrC6-alkylsulfi nyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra;
also preferred Y is R20;
more preferred Y is CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy-(CrC4-alkoxy)n, CrC6-haloalkoxy, which groups are substituted with Ra, or R20;
particularly preferred Y is Ci-C6-alkyl substituted with Ra, or R20;
also particularly preferred Y is CrC6-haloalkyl substituted with Ra, or R20;
also particularly preferred Y is Ci-C6-alkoxy-(Ci-C4-alkoxy)n substituted with Ra, or R20;
also particularly preferred Y is Ci-C6-haloalkoxy substituted with Ra, or R20;
also more preferred Y is CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy-(CrC4-alkoxy)n, CrC6-haloal- koxy, which groups are substituted with Ra;
particularly preferred Y is CrC6-alkyl, preferably CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, which groups are substituted with Ra;
also particularly preferred Y is CrC6-haloalkyl substituted with Ra;
also particularly preferred Y is CrC6-alkoxy-(CrC4-alkoxy)n substituted with Ra;
also particularly preferred Y is CrC6-haloalkoxy substituted with Ra;
also more preferred Y is CrC6-alkylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra, or R20;
particularly preferred Y is Ci-C6-alkylthio substituted with Ra, or R20;
also particularly preferred Y is CrC6-alkylsulfinyl substituted with Ra, or R20;
also particularly preferred Y is Ci-C6-alkylsulfonyl substituted with Ra, or R20;
also more preferred Y is Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra;
particularly preferred Y is Ci-C6-alkylthio substituted with Ra;
also particularly preferred Y is Ci-C6-alkylsulfinyl substituted with Ra;
also particularly preferred Y is CrC6-alkylsulfonyl substituted with Ra;
also more preferred Y is CrC6-alkyl, CrC6-alkylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra, or R20;
also more preferred Y is CrC6-alkyl, CrC6-alkylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra;
particularly preferred Y is CrC6-alkyl, or CrC6-alkylthio, which groups are substituted with Ra, or R20;
particularly preferred Y is CrC6-alkyl, or CrC6-alkylthio, which groups are substituted with Ra; also more preferred Y is CrC6-alkylthio, CrC6-alkoxy-(CrC4-alkoxy)n, or CrC6-alkylsulfinyl, which groups are substituted with Ra, or R20;
also more preferred Y is CrC6-alkylthio, CrC6-alkoxy-(CrC4-alkoxy)n, or CrC6-alkylsulfinyl, which groups are substituted with Ra;
especially preferred Y is CrC4-alkyl, CrC2-fluoroalkyl, CrC4-alkoxy, or CrC4-alkylthio, which groups are substituted with Ra, or R20;
also especially preferred Y is CrC4-alkyl, CrC2-fluoroalkyl, CrC4-alkoxy, or CrC4-alkylthio which groups are substituted with Ra; more especially Y is CH3, C2H5, n- propyl, iso-propyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH3, which groups are substituted with Ra, or R20;
also more especially Y is CH3, C2H5, n- propyl, iso-propyl, isobutyl, n-butyl, 2-butyl, t-butyl, OCH3, or SCH3, which groups are substituted with Ra;
most preferred Y is CH3, C2H5, n-propyl, iso-propyl, OCH3, or SCH3, which groups are substi tuted with Ra, or R20;
also most preferred Y is CH3, C2H5, n-propyl, iso-propyl, OCH3, or SCH3, which groups are sub stituted with Ra;
preferred R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, CrC6-alkylsulfi- nyl, CrC6-alkylsulfonyl, C3-C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, aminosulfinyl, CrC6-alkylamino- sulfinyl, di(CrC6-alkyl)aminosulfinyl, C3-C6-alkenylsulfonyl, hydroxysulfonyl, CrC6-alkoxysulfonyl, aminocarbonyl, CrC6-alkylcarbonyl, Ci-C6-alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, (HO)2(0)P, (HO)(CrC6-alkoxy)(0)P, (CrC6-alkoxy)2(0)P, C3-C8-cycloalkyl, phenyl, 5- or 6-mem- bered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein, cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
more preferred R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, CrC6- alkylsulfinyl, CrC6-alkylsulfonyl, hydroxysulfonyl, CrC6-alkoxysulfonyl, aminocarbonyl, CrC6-alkyl- carbonyl, CrC6-alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, (HO)2(0)P, (CrC6- alkoxy)2(0)P, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein, cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
particularly preferred R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, Cr C6-alkylsulfinyl, CrC6-alkylsulfonyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocy clyl;
wherein, cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
preferred Ra is OH, CN, CrC6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6-haloalkoxy, C3- C6-cycloalkyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-haloalkoxycarbonyl, CrC6-alkyla- minocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, CrC6-alkylcarbonyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl;
more preferred Ra is OH, CN, CrC6-alkoxy, C3-C6-cycloalkyl, hydroxycarbonyl, CrC6-alkyla- minocarbonyl, di(CrC6-alkyl)aminocarbonyl, CrC6-alkylcarbonyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl;
most preferred Ra is OH, CN, CrC6-alkoxy, C3-C6-cycloalkyl, hydroxycarbonyl, CrC6-alkyla- minocarbonyl, di(CrC6-alkyl)aminocarbonyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6- membered heterocyclyl;
preferred Rb is CrC6-alkyl, CrC6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, CrC6-ami- nocarbonyl, phenyl-CrC6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het erocyclyl;
more preferred Rb is C3-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-mem bered heterocyclyl;
most preferred Rb is C3-C6-cycloalkyl, 5- or 6-membered heteroaryl, or 3- to 6-membered het erocyclyl;
preferred Rc is halogen, CN, OH, CrC6-alkyl or CrC6-alkoxy, CrC6-haloalkoxy, or NH2; more preferred Rc is CrC6-alkyl or CrC6-alkoxy;
most preferred Rc is CrC6-all<yl;
preferred Rd is CN, OH, halogen, CrC6-alkyl, C3-C6-cycloalkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6-haloalkoxy, NH2, phenyl-CrC6-alkyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl, or phenylthio;
more preferred Rd is halogen, CrC6-alkoxy, or phenylthio;
most preferred Rd is halogen or CrC6-alkoxy;
preferred Re is halogen, OH, CN, N02, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
more preferred Re is halogen, CN, OH, CrC6-alkoxy or CrC6-alkyl;
most preferred Re is OH or CrC6-alkoxy;
preferred Rf is H, halogen, CN, OH, CrC6-alkyl, or CrC6-alkoxy;
more preferred Rf is OH, CrC6-alkyl, or CrC6-alkoxy;
most preferred Rf is OH or CrC6-alkoxy.
In a preferred embodiment of compounds of formula (I), and their use as herbicide,
X, W independently are H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hy- droxycarbonyl, CrC6-alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H or CrC6- alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3- C6-alkinyloxy, CrC6-alkoxy-(CrC4-alkoxy)n, SH, NH2, CrC6-alkylamino, di(CrC6-al- kyl)amino, (CrC6-alkyl)(CrC6-alkoxy)amino, CrC6-alkylthio, CrC6-alkylthio-CrC6-alkyl, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hy- droxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Cr C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, C1-C6-alkylcarbonylaminocarbonyl, CrC6- haloalkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, CrC6-alkylcarbonylamino, C3-C6-cycloalkylcarbonylamino, CrC6-alkylsulfonylamino, Cr C6-alkylsulfonylaminocarbonyl, di(CrC6-alkylsulfonyl)aminocarbonyl CrC6-haloalkyl- sulfonylamino, CrC6-alkylcarbonyl(CrC6-alkyl)amino, CrC6-alkylaminocarbonylamino, CrC6-dialkylaminocarbonylamino, CrC6-alkoxycarbonylamino, hydroxycarbonyl-CrC6- alkyl, hydroxcarbonyl-CrC6-haloalkyl, CrC6-alkylaminocarbonyl-CrC6-alkyl, CrC6-all<yla- minocarbonyl-CrC6-haloalkyl, CrC6-dialkylaminocarbonyl-CrC6-alkyl, CrC6-dialkyla- minocarbonyl-CrC6-haloalkyl, hydroxyCrC6-alkyl, CrC6-alkylcarbonylalkyl, cyano-CrC6- alkyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl-CrC6-alkyl, 3- to 6-membered heterocyclyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocy clyl, 3- to 6-membered heterocyclylcarbonyl,C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, 3- to 6-membered heterocyclyloxy, hydroxysulfonyl, CrC6-alkoxysulfonyl, (HO)2(0)P, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X, W, and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X, W, and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio.
In another preferred embodiment of compounds of formula (I), and their use as herbicide, X, W is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, C C6- alkoxycarbonyl, CrC6-haloalkoxy, or phenyl, preferably H or CrC6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, SH, CrC6-alkylamino, di(CrC6-alkyl)amino, CrC6-alkylthio, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, hydroxycarbonyl, CrC6- alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-alkyl)aminocarbonyl, CrC6-alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylamino, CrC6-haloalkylsulfonylamino, C-|-C6-alkylcarbonyl(Ci-C6-al- kyl)amino, hydroxcarbonyl-CrC6-alkyl, CrC6-alkylaminocarbonyl-CrC6-alkyl, CrC6-dial- kylaminocarbonyl-CrC6-alkyl, hydroxyCrC6-alkyl, cyano-CrC6-alkyl, phenyl-CrC6-alkyl, 5- or 6-membered heteroaryl-Ci-C6-alkyl, 3- to 6-membered heterocyclyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocy- clyl, C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, or 3- to 6-membered hetero- cyclyloxy;
wherein
cyclic groups of X, W, and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X, W, and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio.
In another preferred embodiment of compounds of formula (I), and their use as herbicide,
X, W is H, CrC6-alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Cr C6-alkylthio-CrC6-alkyl, Ci-C6-alkoxy-C-|-C6-alkyl, CrC6-alkylcarbonyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-alkyl)ami- nocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocar- bonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-alkyl- sulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X, W, and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X, W, and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio.
Preferred R4 and R5 are independently from each other selected from hydrogen, OH, CrC6-al- kyl, NH2, CrC6-alkylcarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, CrC6-alkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, 5- or 6-membered heteroaryloxycarbonyl, 3- or 6-mem bered heterocyclyloxycarbonyl, C3-C6-cycloalkyloxycarbonyl, C3-C6-cycloalkenyloxycarbonyl, ami nocarbonyl, CrC6-alkylaminocarbonyl, and di(CrC6-alkyl)aminocarbonyl; more preferred R4 and R5 are independently from each other selected from hydrogen, OH, Cr C6-alkyl, NH2, CrC6-alkylcarbonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, CrC6-alkoxycar- bonyl, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, CrC6-alkylaminocarbonyl, and di(CrC6-al- kyl)aminocarbonyl;
most preferred R4 and R5 are independently from each other selected from OH, CrC6-alkylcar- bonyl, CrC6-alkylsulfonyl, and CrC6-haloalkylsulfonyl.
Preferred R3 is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, or C3-C6-cycloalkyl; also preferred R3 is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
particularly preferred R3 is halogen, CN, CrC6-alkyl, or CrC6-alkoxy;
especially preferred R3 is halogen or CH3;
also especially preferred R3 is halogen;
more preferred R3 is Cl, Br, or I;
most preferred R3 is Br or I;
also most preferred R3 is Br or Cl;
preferred Z is phenyl or 5- or 6-membered heteroaryl ring;
also preferred Z is phenyl or 9- or 10-membered partially or fully unsaturated bicyclic ring con taining 0, 1, 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
also preferred Z is 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 preferred Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered partially or fully unsaturated bicyclic ring containing 0, 1, 2, 3, 4 or 5 heteroatoms selected from O, N, and S; also preferred 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;
also preferred Z is phenyl substituted independently of their position with 0, 1, 2, 3, or 4 R3; most preferred Z is phenyl which is substituted at ortho position to the bond attached to pyrim idine ring with at least one R3, and which phenyl ring is further substituted with 0, 1, 2, or 3 R3; particularly preferred Z [i.e. the group "Z-(R3)m"] is formula W1,
Figure imgf000035_0001
wherein R3 is as defined herein including its preferred embodiments;
m is 0, 1, or 2, prferrably 0 or 1; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z [i.e. the group "Z-(R3)m"] is formula W1a
Figure imgf000035_0002
wherein
R3 is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy, CrC6-haloalkoxy, C3- C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6- alkoxy-CrC6-alkoxy, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-alkylthio, CrC6- haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, (CrC6-alkyl)sulfinyl, (Cr C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; R3b and R3c each independently is H, halogen, CN, N02, Ci-C6-alkyl, CrC6-haloalkyl, C1-C6- a I kylca r bony I, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cr C6-alkoxy, CrC6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, CrC6-alkoxycar- bonyl, CrC6-alkylthio, CrC6-haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)- amino, (Ci-C6-alkyl)sulfi nyl, (CrC6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3b and R3c are unsubstituted or substituted with substitu ents Re;
and
# denotes the point of attachment to the pyrimidine ring;
also more preferred Z is 5- or 6-membered heteroaryl ring;
most preferred Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine; particularly preferred Z is pyrimidine or pyridine;
especially preferred Z is pyridine;
most preferred Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole;
particularly preferred Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thio phene, furan, or pyrrole;
especially preferred Z is thiophene, furan, or pyrrole;
particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from below groups A to G,
Figure imgf000036_0001
wherein
R3 is halogen, CHO, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
m is 0 or 1;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-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;
particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from below groups A1 to G1,
Figure imgf000037_0001
wherein
R3 is halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy;
R3b is H, halogen, CHO, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from A, B, C, and D;
most particularly preferred Z[i.e. the group "Z-(R3)m"] is A or C;
more particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from A1, B1, C1, and D1;
most particularly preferred Z[i.e. the group "Z-(R3)m"] is A1 or C1;
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from E, F, and G;
also most particularly preferred Z[i.e. the group "Z-(R3)m"] is E or G;
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is selected from E1, F1, and G1;
also most particularly preferred Z[i.e. the group "Z-(R3)m"] is E1 or G1;
also more preferred Z is 9- or 10-membered partially or fully unsaturated bicyclic ring contain ing 0, 1, 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
also more preferred Z is 9- or 10-membered 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 partially or fully unsaturated bicyclic ring, wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 het eroatoms selected from O or N;
also more preferred 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- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 heteroatoms selected from O or N;
particularly preferred Z is 9 membered bicyclic ring;
more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the 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 bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms; most particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the py rimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered car- bocycle comprising 1 or 2 oxygen atoms;
also more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 heteroatoms se lected from O or N;
also most particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
particularly preferred Z is 10 membered bicyclic ring;
more particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1, 2 or 3 heteroatoms selected from O or N;
also more particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
most particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
more preferred Z[i.e. the group "Z-(R3)m"] is selected from below groups H to V,
Figure imgf000038_0001
wherein Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1, 2, or 3 het eroatoms selected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy;
m is 0, 1 or 2;
R4 is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3- C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z[i.e. the group "Z-(R3)m"] is selected from groups H to V,
wherein
Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1, 2, or 3 het eroatoms selected from O, N, and S;
R3 is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
m is 0, 1 or 2;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3- C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyrimidine ring;
more preferred Z[i.e. the group "Z-(R3)m"] is selected from below groups H1 to V1,
Figure imgf000039_0001
wherein Y1 is 5- or 6-membered fully unsaturated carbocycle comprising 0, 1, 2, or 3 heteroatoms se lected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy;
R3b and R3c each independently is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy ;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-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;
most preferably Z[i.e. the group "Z-(R3)m"] is selected from H1, 11, K1, L1 and R1;
preferred Y1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1, 2, or 3 heteroatoms selected from O, N, and S;
particularly preferred Y1 is phenyl;
also particularly preferred Y1 is 5-membered partially or fully unsaturated carbocycle comprising 1, or 2 heteroatoms selected from O, N, and S;
more preferred Y1 is 5-membered partially unsaturated carbocycle comprising 0, 1, or 2 heteroa toms selected from O, N, and S, e.g. 1,3-dithiolane, 1,3-oxathiolane, 1,3-dioxolane, 2,3-dihydrofu- ran, 2,3-dihydrothiophene, or 2,3-dihydro-1H-pyrrole ; more preferably heteroatoms are selected from O and S, e.g. 1,3-oxathiolane, 1,3-dioxolane, 2,3-dihydrofuran, or 2,3-dihydrothiophene; most preferred heteroatom in Y1 is O, e.g. 1,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y1 is S, e.g. 2,3-dihydrothiophene;
also more preferred Y1 is 5-membered fully unsaturated carbocycle comprising 0, 1, or 2 het eroatoms selected from O, N, and S (furan, thiophene, 1H-pyrrole, 1,2-oxazole, 1,3-oxazole, 1,2- thiazole, 1,3-thiazole, imidazole, 1H-pyrazole); more preferably heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
most preferred Y1 is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen at oms;
also particularly preferred Y1 is 6-membered partially or fully unsaturated carbocycle comprising 0, 1, or 2 heteroatoms selected from O, N, and S;
more preferred Y1 is 6-membered partially unsaturated carbocycle comprising 0, 1, or 2 heteroa toms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O;
also more preferred Y1 is 6-membered fully unsaturated carbocycle comprising 0, 1, or 2 het eroatoms N;
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is H, I, J, K, L, M, N, O, P, Q, or R; most particularly preferred Z[i.e. the group "Z-(R3)m"] is H, L, or M;
most particularly preferred Z[i.e. the group "Z-(R3)m"] is H;
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is S, T, U, or V.
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is H1, 11, J1, K1, L1, M1, N1, 01, P1, Q1, or R1;
most particularly preferred Z[i.e. the group "Z-(R3)m"] is H1, L1, or M1;
most particularly preferred Z[i.e. the group "Z-(R3)m"] is H1;
also more particularly preferred Z[i.e. the group "Z-(R3)m"] is S1, T1, U1, or V1.
most preferred Z[i.e. the group "Z-(R3)m"] is H1, 11, K1, L1 and R1;
preferred m is 0, 1, 2, or 3;
more preferred m is 0, 1, or 2; also most preferred m is 1;
also most preferred m is 2;
preferred n is 0, 1, 2, or 3;
more preferred n is 0, 1, or 2;
most preferred n is 0;
also most preferred n is 1;
also most preferred n is 2.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
R1 is CrC6-alkyl, CrC6-alkoxy, CrC6-alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3- C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
R2 is selected from R2-1 to R2-24, preferably from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, R2-21, R2-23, and R2-24, more preferably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2-15, or R2-16;
wherein
X, W is H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, C &- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H or Ci-C6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C3-C6-cycloalkyl, C4-C8-cycloalkenyl, C3-C6-alkenyloxy, C3- C6-alkinyloxy, CrC6-alkoxy-(CrC4-alkoxy)n, SH, NH2, CrC6-alkylamino, di(CrC6-al- kyl)amino, (CrC6-alkyl)(CrC6-alkoxy)amino, CrC6-alkylthio, CrC6-alkylthio-CrC6-alkyl, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hy droxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Cr C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, C1-C6-alkylcarbonylaminocarbonyl, CrC6- haloalkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, CrC6-alkylcarbonylamino, C3-C6-cycloalkylcarbonylamino, CrC6-alkylsulfonylamino, Cr C6-alkylsulfonylaminocarbonyl, di(CrC6-alkylsulfonyl)aminocarbonyl CrC6-haloalkyl- sulfonylamino, CrC6-alkylcarbonyl(CrC6-alkyl)amino, CrC6-alkylaminocarbonylamino, CrC6-dialkylaminocarbonylamino, CrC6-alkoxycarbonylamino, hydroxycarbonyl-CrC6- alkyl, hydroxcarbonyl-CrC6-haloalkyl, CrC6-alkylaminocarbonyl-CrC6-alkyl, CrC6-alkyla- minocarbonyl-CrC6-haloalkyl, CrC6-dialkylaminocarbonyl-CrC6-alkyl, CrC6-dialkyla- minocarbonyl-CrC6-haloalkyl, hydroxyCrCe-alkyl, CrC6-alkylcarbonylalkyl, cyano-CrC6- alkyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl-CrC6-alkyl, 3- to 6-membered heterocyclyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocy- clyl, 3- to 6-membered heterocyclylcarbonyl,C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, 3- to 6-membered heterocyclyloxy, hydroxysulfonyl, CrC6-alkoxysulfonyl, (HO)2(0)P, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
Z[i.e. the group "Z-(R3)m"] is formula W1 wherein m is 0 or 1; and R3 is halogen.
Also preferred are compounds of formula (I), and their use as herbicide, wherein R1 is CrC6-alkyl, CrC6-alkoxy, CrC6-alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3- C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
R2 is selected from R2-1 to R2-24, preferably from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, R2-21, R2-23, and R2-24, more preferably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2-15, or R2-16;
wherein
X is H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, C &- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H or CrC6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, SH, CrC6-alkylamino, di(CrC6-alkyl)amino, CrC6-alkylthio, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, hydroxycarbonyl, CrC6- alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-alkyl)aminocarbonyl, CrC6-alkylcarbonylaminocarbonyl, hydroxyaminocarbonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylamino, CrC6-haloalkylsulfonylamino, CrC6-alkylcarbonyl(CrC6-al- kyl)amino, hydroxcarbonyl-CrC6-alkyl, CrC6-alkylaminocarbonyl-CrC6-alkyl, CrC6-dial- kylaminocarbonyl-CrC6-alkyl, hydroxyCrC6-alkyl, cyano-CrC6-alkyl, phenyl-CrC6-alkyl, 5- or 6-membered heteroaryl-CrC6-alkyl, 3- to 6-membered heterocyclyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocy- clyl, C3-C6-cycloalkyloxy, 5- or 6-membered heteroaryloxy, or 3- to 6-membered hetero- cyclyloxy;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
Z[i.e. the group "Z-(R3)m"] is formula W1 wherein m is 0 or 1; and R3 is halogen.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
R1 is unsubstituted cyclopropyl;
R2 is selected from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, and R2-21, more prefer ably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2- 15, or R2-16;
wherein
X is H, CrC6-alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, SH, CrC6-alkylthio-CrC6-alkyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hydroxycar bonyl, CrC6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkyla- minocarbonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-al- kylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd; n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or Ci-C6-alkylthio;
Z[i.e. the group "Z-(R3)m"] is formula W1 or H, wherein m is 0 or 1; and R3 is halogen;
Y1 is 5- or 6-membered partially unsaturated carbocycle comprising 0, 1,or 2 oxygen atoms.
Also preferred are compounds of formula (I), and their use as herbicide, wherein
R1 is unsubstituted cyclopropyl;
R2 is selected from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, and R2-21, more prefer ably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2- 15, or R2-16;
wherein
X is H, CrC6-alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC6-alkyl, more preferably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, SH, CrC6-alkylthio-CrC6-alkyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hydroxycar bonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-al- kyl)a mi nocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkyla- minocarbonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-al- kylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
Z[i.e. the group "Z-(R3)m"] is formula W1, wherein m is 0 or 1; and R3 is halogen.
Also preferred are compounds of formula (I), which correspond to formula (1.1), and their use as herbicide,
Figure imgf000043_0001
wherein
R1 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl, CrC6-alkyl, or CrC6-haloalkyl, preferably cyclopro- pyl;
R2 is selected from R2-1 to R2-24, preferably from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-23, and R2-24, more preferably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2-15, or R2-16; Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 1 or 2;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein Z[i.e. the group "Z-(R3)m"] is formula W1, which correspond to formula (I.A), and their use as herbicide,
Figure imgf000044_0001
wherein
R1 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl, CrC6-alkyl, or CrC6-haloalkyl, preferably cyclopro- pyl;
R2 is selected from R2-1 to R2-24, preferably from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-23, and R2-24, more preferably from R2-13, R2-14, R2-15, R2-16, R2-17, and R2-18, most preferably R2 is R2-13, R2-14, R2-15, or R2-16;
R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-9, Z[i.e. the group "Z-(R3)m"] is for mula W1, which corresponds to formula (I.B), and their use as herbicide,
Figure imgf000044_0002
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
R3 is halogen, Ci-C6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, CrC6- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H, Ci-C6-alkyl, or CrC6-haloalkyl, more preferably H, CH3, C2H5, n-propyl, CF3, CH2CF3, CH2CHF2;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, Cr C6-alkylthio-Ci-C6-alkyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-alkyl)ami- nocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloalkylaminocar- bonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(Ci-C6-alkyl- sulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P; preferably Y is CH2CHCH2, CH2OCH3, CHCH2, or CºCH;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-10, Z[i.e. the group "Z-(R3)m"] is formula W1, which corresponds to formula (I.C), and their use as herbicide,
Figure imgf000045_0001
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, halogen, Ci-C6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, 0-C6- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H, CrC6-alkyl, or CrC6-haloalkyl, more preferably H, CH3, C2H5, n-propyl, CF3, CH2CF3, CH2CHF2;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, Cr C6-alkylthio-CrC6-alkyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Ci-C6-alkyl)ami- nocarbonyl, NH2-aminocarbonyl, hydroxya mi nocarbonyl, C3-C6-cycloalkylaminocar- bonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-alkyl- sulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P; preferably Y is CH2CHCH2, CH2OCH3, CHCH2, or C ºCH;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-11, Z[i.e. the group "Z-(R3)m"] is formula W1, which corresponds to formula (I.D), and their use as herbicide, wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, C &- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H, CrC6-alkyl, or CrC6-haloalkyl, more preferably H, CH3, C2H5, n-propyl, CF3, CH2CF3, CH2CHF2;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, Ci-C6-alkoxy-(Ci-C4-alkoxy)n, NH2, Cr C6-alkylthio-CrC6-alkyl, Ci-C6-alkoxy-C-|-C6-alkyl, CrC6-alkylcarbonyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(CrC6-alkyl)ami- nocarbonyl, NH2-aminocarbonyl, hydroxya mi nocarbonyl, C3-C6-cycloalkylaminocar- bonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-alkyl- sulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P; preferably Y is CH2CHCH2, CH2OCH3, CHCH2, or CºCH;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-17, Z[i.e. the group "Z-(R3)m"] is W1, which corresponds to formula (I.E), and their use as herbicide,
Figure imgf000046_0001
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, halogen, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, hydroxycarbonyl, C &- alkoxycarbonyl, CrC6-haloalkoxy or phenyl, preferably H, CrC6-alkyl, or CrC6-haloalkyl, more preferably H, CH3, C2H5, n-propyl, CF3, CH2CF3, CH2CHF2;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, Cr C6-alkylthio-CrC6-alkyl, Ci-C6-alkoxy-C-|-C6-alkyl, CrC6-alkylcarbonyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6-alkyl)ami- nocarbonyl, NH2-aminocarbonyl, hydroxya mi nocarbonyl, C3-C6-cycloalkylaminocar- bonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(CrC6-alkyl- sulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6-alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclyl- carbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P; preferably Y is CH2CHCH2, CH2OCH3, CHCH2, or CCH;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
more preferably, when m is 2, R3 each independently is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen.
Also preferred are compounds of formula (I) wherein R2 is R2-9, which corresponds to formula (I.F), and their use as herbicide,
Figure imgf000047_0001
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein; R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH,
SCH3, CH F2, CF3, CH2CF3, CH2CHF2, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2H
CONH2, CONHCH3, CON(CH3)2, CH2CHCH2, or CH2CºCH;
Y is CHCH2, C(CH3)CH2, CH2CHCH2, CH2OCH3, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), Cº CH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)CºCH, SH, NHCH3, N(CH3)2, COOH, COOCHs, COOC2Hs, CONH2, CONHCH3, or CON(CH3)2;
more preferably, Z [i.e. the group "Z-(R3)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.
Also preferred are compounds of formula (I) wherein R2 is R2-10, which corresponds to formula (I.G), and their use as herbicide, wherein R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein; R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CH F2, CF3, CH2CF3, CH2CHF2, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2Hs, CONH2, CONHCH3, CON(CH3)2, CH2CHCH2, or CH2CºCH;
Y is CHCH2, C(CH3)CH2, CH2CHCH2, CH2OCH3, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), C º CH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)CºCH, SH, NHCH3, N(CH3)2, COOH, COOCH3, COOC2Hs, CONH2, CONHCH3, or CON(CH3)2;
more preferably, Z [i.e. the group "Z-(R3)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.
Also preferred are compounds of formula (I) wherein R2 is R2-11, which corresponds to formula (I.H), and their use as herbicide,
Figure imgf000048_0001
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein; R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CH F2, CF3, CH2CF3, CH2CHF2, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2Hs, CONH2, CONHCH3, CON(CH3)2, CH2CHCH2, or CH2CºCH;
Y is CHCH2, C(CH3)CH2, CH2CHCH2, CH2OCH3, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), C º CH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)CºCH, SH, NHCH3, N(CH3)2, COOH, COOCH3, COOC2Hs, CONH2, CONHCH3, or CON(CH3)2;
more preferably, Z [i.e. the group "Z-(R3)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.
Also preferred are compounds of formula (I) wherein R2 is R2-12, which corresponds to formula (I. I), and their use as herbicide,
Figure imgf000048_0002
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl; Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein; R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
is H, Cl, Br, CN, CH3, C2Hs, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH, SCH3, CH F2, CF3, CH2CF3, CH2CHF2, OCHF2, OCF3, N(CH3)2, COOH, COOCH3, COOC2Hs,
CON H2, CON HCHS, CON(CH3)2, CH2CHCH2, or CH2CºCH;
Y is CHCH2, C(CH3)CH2, CH2CHCH2, CH2OCH3, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), C º CH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)CºCH, SH, NHCH3, N(CH3)2, COOH, COOCHs, COOC2Hs, CONH2, CONHCH3, or CON(CH3)2;
more preferably, Z [i.e. the group "Z-(R3)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.
Also preferred are compounds of formula (I) wherein R2 is R2-17, which corresponds to formula (I.J), and their use as herbicide,
Figure imgf000049_0001
wherein R1 is C3-C6-cycloalkyl, CrC6-alkyl, or CrC6-alkoxy, preferably cyclopropyl;
Z[i.e. the group "Z-(R3)m"] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein; R3 is halogen, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy, preferably halogen;
m is 0, 1 or 2;
X is H, Cl, Br, CN, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, isobutyl, C(CH3)3, OH, OCH3, SH,
SC H3, CH F2, CF3, CH2CF3, C H2CH F2, OC H F2, OCF3, N(C H3)2, COOH, COOCH3, COOC2Hs,
CONH2, CONHCH3, CON(CH3)2, CH2CHCH2, or CH2CºCH;
Y is CHCH2, C(CH3)CH2, CH2CHCH2, CH2OCH3, CHC(CH3)2, C(CH3)C(CH3)2, CHCH(CH3), C º CH, CH2CHCH2, CH(CH3)CHCH2, CH2CºCH, CH(CH3)CºCH, SH, NHCH3, N(CH3)2, COOH, COOCH3, COOC2Hs, CONH2, CONHCH3, or CON(CH3)2;
more preferably, Z [i.e. the group "Z-(R3)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.
According to a particularly preferred embodiment of the compounds of formula I and their use as herbicide, compounds of the invention are the compounds of the formula I that are compiled in the Tables 1 to 96, wherein the meaning for the combination of variables X and Y of R2 for each individual compound of tables 1 to 96 corresponds to each row of Table R2.
Each of the groups mentioned for a substituent in the tables is furthermore per se, inde pendently of the combination in which it is mentioned, a particularly preferred aspect of the sub stituent in guestion.
Table 1. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-13, Z is 2"-CI-C6H4 (com pounds of formula 1.1); Table 2. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-Br-C6H4 (com- pounds of formula 1.2).
Table 3. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-CI-3"-F-C6H3
(compounds of formula 1.3).
Table 4. Compounds of formula , wherein R1 is 0C3H5, R2 is R2-13, Z s 2"-CI-4"-F-C6H3
(compounds of formula 1.4).
Table 5. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-CI-5"-F-C6H3
(compounds of formula 1.5).
Table 6. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-CI-6"-F-C6H3
(compounds of formula 1.6).
Table 7. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-Br-3"-F-C6H3
(compounds of formula 1.7).
Table 8. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-Br-4"-F-C6H3
(compounds of formula 1.8).
Table 9. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-Br-5"-F-C6H3
(compounds of formula 1.9).
Table 10. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 2"-CI-4"-F-5"-F-
C6H2 (compounds of formula 1.10).
Table 11. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-13, Z s 3"- CH3-2"-naphthyl
(compounds of formula 1.11).
Table 12. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-CI-C6H4 (com- pounds of formula 1.12)
Table 13. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-Br-C6H4 (com pounds of formula 1.13).
Table 14. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-CI-3"-F-C6H3
(compounds of formula 1.14).
Table 15. Compounds of formula , wherein R1 is c-C3Hs, R2 is R2-14, Z s 2"-CI-4"-F-C6H3
(compounds of formula 1.15).
Table 16. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-CI-5"-F-C6H3
(compounds of formula 1.16).
Table 17. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-CI-6"-F-C6H3
(compounds of formula 1.17).
Table 18. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-Br-3"-F-C6H3
(compounds of formula 1.18).
Table 19. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-Br-4"-F-C6H3
(compounds of formula 1.19).
Table 20. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-Br-5"-F-C6H3
(compounds of formula 1.20).
Table 21. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 2"-CI-4"-F-5"-F-
C6H2 (compounds of formula 1.21).
Table 22. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-14, Z s 3"- CH3-2"-naphthyl
(compounds of formula 1.22).
Table 23. Compounds of formula , wherein R1 is c-C3H5, R2 is R2-15, Z s 2"-CI-C6H4 (com pounds of formula 1.23) Table 24. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-Br-C6H4 (com- pounds of formula 1.24).
Table 25. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.25).
Table 26. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.26).
Table 27. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.27).
Table 28. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.28).
Table 29. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.29).
Table 30. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.30).
Table 31. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.31).
Table 32. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.32).
Table 33. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 3"- CH3-2"-naphthyl (compounds of formula 1.33).
Table 34. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-C6H4 (com- pounds of formula 1.34)
Table 35. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-Br-C6H (com- pounds of formula 1.35).
Table 36. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.36).
Table 37. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.37).
Table 38. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.38).
Table 39. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.39).
Table 40. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.40).
Table 41. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.41).
Table 42. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.42).
Table 43. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.43).
Table 44. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 3"- CH3-2"-naphthyl (compounds of formula 1.44).
Table 45. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-17, Z is 2"-CI-C6H4 (com- pounds of formula 1.45). Table 46. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-Br-C6H4 (com- pounds of formula 1.46)
Table 47. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.47).
Table 48. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.48).
Table 49. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.49).
Table 50. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.50).
Table 51. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.51).
Table 52. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.52).
Table 53. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.53).
Table 54. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.54).
Table 55. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-17, Z is 3"- CH3-2"-naphthyl (compounds of formula 1.55).
Table 56. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-C6H (com- pounds of formula 1.56).
Table 57. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-Br-C6H (com- pounds of formula 1.57)
Table 58. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.58).
Table 59. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.59).
Table 60. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.60).
Table 61. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.61).
Table 62. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.62).
Table 63. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.63).
Table 64. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.64).
Table 65. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.65).
Table 66. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-18, Z is 3"- CH3-2"-naphthyl (compounds of formula 1.66).
Table 67. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-CI-C6H4 (com- pounds of formula 1.67). Table 68. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-Br-C6H4 (com pounds of formula 1.68)
Table 69. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.69).
Table 70. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.70).
Table 71. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.71).
Table 72. Compounds of formula I, wherein R1 is c-C3H5 R2 is R2-23, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.72).
Table 73. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.73).
Table 74. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.74).
Table 75. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.75).
Table 76. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.76).
Table 77. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-23, Z is 3"- CH3-2"- naphthyl (compounds of formula 1.77).
Table 78. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-C6H4 (com pounds of formula 1.78).
Table 79. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-Br-C6H4 (com pounds of formula 1.79)
Table 80. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-3"-F-C6H3 (compounds of formula 1.80).
Table 81. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-4"-F-C6H3 (compounds of formula 1.81).
Table 82. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-5"-F-C6H3 (compounds of formula 1.82).
Table 83. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-6"-F-C6H3 (compounds of formula 1.83).
Table 84. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-Br-3"-F-C6H3 (compounds of formula 1.84).
Table 85. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-Br-4"-F-C6H3 (compounds of formula 1.85).
Table 86. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-Br-5"-F-C6H3 (compounds of formula 1.86).
Table 87. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 2"-CI-4"-F-5"-F- C6H2 (compounds of formula 1.87).
Table 88. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-24, Z is 3"- CH3-2"- naphthyl (compounds of formula 1.88).
Table 89. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-13, Z is 3"-CI-2"-naphthyl (compounds of formula 1.89).
Table 90. Compounds of formula I, wherein R1 is c-C3H5, R2 is R2-14, Z is 3"-CI-2"-naphthyl (compounds of formula 1.90).
Table 91. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-15, Z is 3"-CI-2"-naphthyl (compounds of formula 1.91).
Table 92. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-16, Z is 3"-CI-2"-naphthyl (compounds of formula 1.92).
Table 93. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-17, Z is 3"-CI-2"-naphthyl (compounds of formula 1.93).
Table 94. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-18, Z is 3"-CI-2"-naphthyl (compounds of formula 1.94).
Table 95. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-23, Z is 3"-CI-2"-naphthyl (compounds of formula 1.95).
Table 96. Compounds of formula I, wherein R1 is C-C3H5, R2 is R2-24, Z is 3"-CI-2"-naphthyl (compounds of formula 1.96).
Table R2
The specific number for each single compound is deductible as follows:
Compound 1.1.3 e.g. comprises the compound of formula 1.1 from Table 1 and row 3 from Table R2;
To widen the spectrum of action and to achieve synergistic effects, the pyrimidine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly. Suitable
components for mixtures are, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,
isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides,
pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazoli nones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, or ureas.
It may furthermore be beneficial to apply the pyrimidine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
In one embodiment of the present invention the compositions according to the present inven tion comprise at least one pyrimidine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1) to b15), and safeners C (compound C).
In a preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyrimidine compound of formula (I.A) (cor responds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.B) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.C) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.D) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.E) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.F) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.G) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.H) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I. I) (corresponds to pyrimidine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyrimidine compound of for mula (I.J) (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;
In another embodiment of the present invention the compositions according to the present in vention comprise at least one pyrimidine compound of formula (I) and at least one further active compound B (herbicide B).
The further herbicidal compound B (component B) is preferably selected from the herbicides of class b1) to b15):
Mixing partners for the composition can be selected from below herbicides B as defined below:
B) herbicides of class b1) to b15):
b1) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors);
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b11) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoguat, difenzoguat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluid- ide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, me thyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, guinoclamine, tria- ziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223- 49-3) and its salts and esters;
including their agriculturally acceptable salts or derivatives;
In one embodiment of the invention, the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bio synthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter-termed ACCase herbicides) or through a different mode of action (hereinafter termed non-ACCase herb icides). The ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
In another embodiment of the invention, the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system. In another embodiment of the invention, the compositions contain at least one inhibitor of photosynthesis (herbicide b3). The herbicidal activity of these compounds is based either on the inhibition 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 inhibi tors, group D of HRAC classification) and thus on an inhibition of photosynthesis. Amongst these, PSII inhibitors are preferred.
In another embodiment of the invention, the compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4). The herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase. These inhibitors belong to the group E of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one bleacher-herbi cide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhi bition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), com pounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and com pounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - un known target, group F3 of HRAC classification).
In another embodiment of the invention, the compositions contain at least one EPSP synthase inhibitor (herbicide b6). The herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid bio synthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one glutamine syn thetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhi bition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants. These inhibitors belong to the group H of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one DHP synthase inhibitor (herbicide b8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to the group I of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one mitosis inhibitor (herbicide b9). The herbicidal activity of these compounds is based on the disturbance or inhibi tion of microtubule formation or organization, and thus on the inhibition of mitosis. These inhibi tors belong to the groups K1 and K2 of the HRAC classification system. Among these, com pounds of the group K1, in particular dinitroanilines, are preferred.
In another embodiment of the invention, the compositions contain at least one VLCFA inhibitor (herbicide b10). The herbicidal activity of these compounds is based on the inhibition of the syn thesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one cellulose bio synthesis inhibitor (herbicide b11). The herbicidal activity of these compounds is based on the in hibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants. These inhibitors belong to the group L of the HRAC classification system. In another embodiment of the invention, the compositions contain at least one decoupler herb icide (herbicide b12). The herbicidal activity of these compounds is based on the disruption of the cell membrane. These inhibitors belong to the group M of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one auxinic herbi cide (herbicide b13). These include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one auxin transport inhibitor (herbicide b14). The herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants. These compounds belong to the group P of the HRAC classification system.
As to the given mechanisms of action and classification of the active substances, see e.g.
"HRAC, Classification of Herbicides According to Mode of Action", http://www. plant protec tion. org/hrac/MOA.html).
Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1, b2, b3, b4, b5, b6, b9, b10, b13, and b14.
Specific preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1, b2, b4, b5, b9, b10, b13, and b14.
Particular preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1, b2, b4, b5, b9, b10, and b13
Examples of herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
b1) from the group of the lipid biosynthesis inhibitors:
ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaguizafop, guizalofop, guizalofop-ethyl, guizalofop-tefuryl, guizalo- fop-P, guizalofop-P-ethyl, guizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,
4-(4'-Chloro-4-cyclopropyl-2 -fluoro[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,T-biphenyl]-3-yl)-5-hy- droxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-flu- oro[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1,T-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,T-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4- cyclopropyl- [1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)- 4-(4'-chloro-4-ethyl-2 -fluoro[1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3- one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,T-biphenyl]-3-yl)-3,6-dihydro- 2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1,T-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'- fluoro[1,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1,T-biphenyl]-3-yl)-5,6-dihydro- 2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, espro- carb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thioben- carb, tiocarbazil, triallate and vernolate;
b2) from the group of the ALS inhibitors:
sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfa mu ron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfa mu ron, oxasulfuron, primi- sulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron- ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl and tritosulfuron,
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, penoxsulam, pyrimisulfan and pyroxsulam,
pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy] phenyl] methyl]amino] -benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01- 8),
sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
among these, a preferred embodiment of the invention relates to those compositions compris ing at least one imidazolinone herbicide;
b3) from the group of the photosynthesis inhibitors:
amicarbazone, inhibitors of the photosystem II, e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4- chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyra- zol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hy- droxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-
78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-
79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin- 2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazoli- din-2-one (CAS 1844836-64-1), triazine herbicides, including of chlorotriazine, triazinones, triazin- diones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, met- amitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phen- medipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and para- quat-dimetilsulfate. Among these, a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred em bodiment of the invention relates to those compositions comprising at least one triazine herbi cide. Among these, likewise a preferred embodiment of the invention relates to those composi tions comprising at least one nitrile herbicide;
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopy- raniffluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluorogly- cofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiar- gyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1- methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]ace- tate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1/A pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1/Y-pyrazole-1- carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H- benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2- (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro- isoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4- prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (7)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1/7-methyl-pyrazol-3-yl]-4-fluoro-phe- noxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluorome- thyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754- 02-4); b5) from the group of the bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl- 3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- dinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium, glyposate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors:
compounds of group K1: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, 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, com pounds of group K1, in particular dinitroanilines are preferred;
b10) from the group of the VLCFA inhibitors:
chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarba- zone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1, II.2, II.3, II.4, II.5,
the isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;
among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3- ylamine (CAS 175899-01-1);
b12) from the group of the decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyra- chlor 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 es ters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, guinclorac, guinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5- fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3 and its salts and esters, dalapon, dazomet, difenzoguat, difenzoguat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, inda- nofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, me thyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, guinoclamine and tridiphane.
Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
b1) from the group of the lipid biosynthesis inhibitors:
clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P- ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaguizafop, guizalofop-P-ethyl, guizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4- cyclopropyl-2'-fluoro[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1,T-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1,T-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5- (Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2 -fluoro[1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetrame- thyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1,T-bi- phenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4- ethyl-2'-fluoro[1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tet- ramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,T-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1,T-biphenyl]-3-yl)-5,6-dihydro-2,2, 6,6-tet- ramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,T-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors:
amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlor- sulfuron, cloransulam-methyl, cyclosulfa mu ron, diclosulam, ethametsulfuron-methyl, ethoxysulfu- ron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, ima- zapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-so- dium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metosulam, metsulfu- ron-methyl, nicosulfuron, orthosulfa mu ron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, py- rimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenu- ron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors:
ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluome- turon, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyri- date, simazine, terbutryn, terbuthylazine, thidiazuron, 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4- chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyra- zol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hy- droxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-
78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-
79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin- 2-one (CAS 2023785-80-8) and 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imid- azolidin-2-one (CAS 1844836-64-1);
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, cyclopyranil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-me- thyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1/Y-py- razole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1- carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H- benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2- (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro- isoindole-1, 3-dione (CAS 1300118-96-0);1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4- prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)- 1H-pyrimidine-2,4-dione (CAS 212754-02-4);
b5) from the group of the bleacher herbicides:
aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoro- methylphenyOpyrimidine (CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0, 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl- 3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- dinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors:
glufosinate, glufosinate-P, glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors:
benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop- M-isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metaza- chlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the for mulae 11.1, II.2, II.3, 11.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
b11) from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);
b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5- fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, cyclopy- rimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoguat, difenzoguat- metilsulfate, DSMA, dymron (= daimuron), indanofan, metam, methylbromide, MSMA, oxazi- clomefone, pyributicarb and tridiphane.
Particularly preferred herbicides B that can be used in combination with the pyrimidine com pounds of the formula (I) according to the present invention are:
b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'- Chloro-4-cyclopropyl-2'-fluoro[1,T-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,T-biphenyl]-3-yl)-5-hydroxy-
2.2.6.6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1,T- biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'- Dichloro-4-ethyl[1,T-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,T-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4- cyclopropyl- [1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)- 4-(4'-chloro-4-ethyl-2 -fluoro[1,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3- one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,T-biphenyl]-3-yl)-3,6-dihydro-
2.2.6.6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1,T-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'- fluoro[1,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1,T-biphenyl]-3-yl)-5,6-dihydro-
2.2.6.6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); espro- carb, prosulfocarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaguin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sul- fosulfuron, thiencarbazon-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraguat, paraguat-dichloride, propanil, terbutryn, terbuthylazine, 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1);
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: cyclopyranil, flumioxazin, oxyfluorfen, pyraflufen, pyraflufen -ethyl, saflufenacil, sulfentrazone, trifludimoxazin, ethyl [3-[2- chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phe- noxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100, 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-di- hydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484- 50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tet- rahydro-isoindole-1,3-dione (CAS 1300118-96-0), and 1-methyl-6-trifluoromethyl-3-(2,2,7-tri- fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0);
b5) from the group of the bleacher herbicides: amitrole, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21- 3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 2-chloro-3-me- thylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); and 2-(2,5-dichloro- phenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
b9) from the group of the mitosis inhibitors: pendimethalin and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentraza- mide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarba- zone and pyroxasulfone; likewise, preference is given to 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;
b11) from the group of the cellulose biosynthesis inhibitors: indaziflam, isoxaben and triaziflam; b13) from the group of the auxinic herbicides: 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr-mep- tyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) from the group of the other herbicides: cinmethylin, dymon (= daimuron), indanofan, oxa- ziclomefone.
Particularly preferred herbicides B are the herbicides B as defined above; in particular, the herb icides B.1 - B.202 listed below in table B:
Table B Particularly preferred herbicides B could also be B.203 which is cyclopyranil.
In another embodiment of the present invention the compositions according to the present in vention comprise at least one pyrimidine compound of formula (I) and at least one safener C. Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the pre sent compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. The safeners and the pyrimidine compounds of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
Suitable safeners are e.g. (guinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5- diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
Examples of preferred safeners C are benoxacor, cloguintocet, cyometrinil, cyprosulfamide, di- chlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxa- difen, 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-oxazoli- dine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4). Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlo- razole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, ox- abetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-tri- methyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroacetyl)- 1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C, which, as component C, are constituent of the composition ac cording to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
Table C:
Figure imgf000079_0001
Figure imgf000079_0002
The active compounds B of groups b1) to b15) and the active compounds C are known herbi cides and safeners, see, e.g., The Compendium of Pesticide Common Names (http://www.alan- wood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 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 America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also re ferred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.
The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this sub stance was only assigned to one mechanism of action.
Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agricultur ally acceptable derivative in the compositions according to the invention.
In the case of dicamba, suitable salts include those, where the counterion is an agriculturally ac ceptable cation. E.g., suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammoni- um, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and 2,4-D- N,N,N-trimethylethanolammonium (2,4-D choline). Examples of suitable esters of 2,4-D are 2,4- D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D- ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D- octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
Suitable salts of 2,4-DB are e.g. 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammo- nium. Suitable esters of 2,4-DB are e.g. 2,4-DB-butyl and 2,4-DB-isoctyl.
Suitable salts of dichlorprop are e.g. dichlorprop-sodium, dichlorprop-potassium and dichlor- prop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.
Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.
Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester 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, prefer ably 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-so- dium.
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 guinclorac is e.g. guinclorac-dimethylammonium.
A suitable salt of guinmerac is e.g. guinmerac-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 imazaguin is e.g. i mazaguin-ammonium.
Suitable salts of imazethapyr are e.g. imazethapyr-ammonium and imazethapyr-isoprop- ylammonium.
A suitable salt of topramezone is e.g. topramezone-sodium.
According to a preferred embodiment of the invention, the composition comprises as herbi- cidal active compound B or component B at least one, preferably exactly one herbicide B.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
(1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621),
(1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631),
(1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26),
(1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
(1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621),
(1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631),
(1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26),
(1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
(1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621),
(1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631),
(1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26),
(1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
(1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621),
(1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631),
(1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26),
(1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.1), (1.2), (1.4), (1.11), (1.12), (1.15), (1.89), or (1.90), especially preferred the compound
(1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26),
(1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46),
(1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566),
(1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686),
(1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), or (1.90.686), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41),
(1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46), (1.94.566), (1.94.621), (1.94.631), or (1.94.686), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), or (1.94.686), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), or (1.94.686), and at least three, preferably exactly three, herbi cides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46), (1.94.566), (1.94.621), (1.94.631), or (1.94.686), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41),
(1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46),
(1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), or (1.94.686), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41), (1.91.41),
(1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46),
(1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566),
(1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46), (1.48.566),
(1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566),
(1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46), (1.56.566), (1.56.621), (1.56.631),
(1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46), (1.59.566), (1.59.621), (1.59.631),
(1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46), (1.66.566), (1.66.621), (1.66.631),
(1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46), (1.94.566), (1.94.621), (1.94.631), or
(1.94.686), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably of formula (1.23), (1.26), (1.33), (1.91), (1.34), (1.35), (1.37), (1.44), (1.92), (1.45), (1.48), (1.55), (1.93), (1.56), (1.59), (1.66), or (1.94), especially preferred the compound (1.23.41), (1.26.41), (1.33.41),
(1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46),
(1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46),
(1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46),
(1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46),
(1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46),
(1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46), (1.94.566), (1.94.621), (1.94.631), or (1.94.686), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxa prop-ethyl, fenoxaprop-P-ethyl, met- amifop, pinoxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb and triallate.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfu- ron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammonium, ima- zapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, imazaguin, imazaguin-ammo- nium, imazethapyr, imazethapyr-ammonium, imazethapyr-isopropylammonium, imazosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, met- azosulfuron, metsulfuron-methyl, metosulam, nicosulfuron, penoxsulam, propoxycarbazon-so- dium, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyroxsulam, propyrisulfuron, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, thifensulfuron-methyl, tribenuron-methyl, tritosulfuron and triafamone.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686),
(1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-po- tassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, para- guat-dichloride, propanil, simazin, terbutryn and terbuthylazine.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin , ethyl [3-[2-chloro-4-fluoro-5-(1-me- thyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100).
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenguintrone, fluometuron, flurochlo- ridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), picolinafen, sulcotri- one, tefuryltrione, tembotrione, tolpyralate, topramezone, topramezone-sodium and 2-chloro-3- methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0) .
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium , glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate-P and glufosinate-P-ammonium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20),
(1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26),
(1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendime- thalin and trifluralin.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686),
(1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566),
(1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631),
(1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20),
(1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26),
(1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone. Likewise, prefer ence is given to compositions comprising in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41),
(1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566),
(1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21), (1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631),
(1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41), (1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686),
(1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46), (1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20),
(1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21),
(1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26),
(1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41),
(1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41), (1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46),
(1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566),
(1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21), (1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566),
(1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41), (1.93.46), (1.93.566), (1.93.621),
(1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46), (1.56.566), (1.56.621), (1.56.631),
(1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46), (1.59.566), (1.59.621), (1.59.631),
(1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46), (1.66.566), (1.66.621), (1.66.631),
(1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46), (1.94.566), (1.94.621), (1.94.631), and
(1.94.686), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae 11.1,
II.2, II.3, 11.4, II.5, II.6, II.7, I I.8 and II.9, as defined above.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566),
(1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621),
(1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631),
(1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b11), in particular indaziflam, isoxaben and triaziflam.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46), (1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D, 2,4- D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopy- rachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyra- lid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butotyl, dicamba-diglycola- mine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopro- pyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, ha- lauxifen, halauxifen-methyl, MCPA, MCPA-2-ethylhexyl, MCPA-dimethylammonium, guinclorac, guinclorac-dimethylammonium, guinmerac, guinmerac-dimethylammonium, florpyrauxifen , florpyrauxifen-benzyl (CAS 1390661-72-9), and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol- 6-yl)picolinic acid (CAS 1629965-65-6) .
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufen- zopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of cinme- thylin, dymron (= daimuron), indanofan and oxaziclomefone.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of (1.1.20), (1.1.21), (1.1.26), (1.1.41), (1.1.46), (1.1.566), (1.1.621), (1.1.631), (1.1.686), (1.2.20), (1.2.21), (1.2.26), (1.2.41), (1.2.46), (1.2.566), (1.2.621), (1.2.631), (1.2.686), (1.4.20), (1.4.21),
(1.4.26), (1.4.41), (1.4.46), (1.4.566), (1.4.621), (1.4.631), (1.4.686), (1.11.20), (1.11.21), (1.11.26), (1.11.41),
(1.11.46), (1.11.566), (1.11.621), (1.11.631), (1.11.686), (1.12.20), (1.12.21), (1.12.26), (1.12.41), (1.12.46),
(1.12.566), (1.12.621), (1.12.631), (1.12.686), (1.15.20), (1.15.21), (1.15.26), (1.15.41), (1.15.46), (1.15.566), (1.15.621), (1.15.631), (1.15.686), (1.89.20), (1.89.21), (1.89.26), (1.89.41), (1.89.46), (1.89.566), (1.89.621), (1.89.631), (1.89.686), (1.90.20), (1.90.21), (1.90.26), (1.90.41), (1.90.46), (1.90.566), (1.90.621), (1.90.631), (1.90.686), (1.23.41), (1.26.41), (1.33.41), (1.91.41), (1.34.41), (1.35.41), (1.37.41), (1.44.41), (1.92.41),
(1.23.46), (1.26.46), (1.33.46), (1.91.46), (1.34.46), (1.35.46), (1.37.46), (1.44.46), (1.92.46), (1.45.20), (1.45.21), (1.45.26), (1.45.41), (1.45.46), (1.45.566), (1.45.621), (1.45.631), (1.45.686), (1.48.20), (1.48.21),
(1.48.26), (1.48.41), (1.48.46), (1.48.566), (1.48.621), (1.48.631), (1.48.686), (1.55.20), (1.55.21), (1.55.26), (1.55.41), (1.55.46), (1.55.566), (1.55.621), (1.55.631), (1.55.686), (1.93.20), (1.93.21), (1.93.26), (1.93.41),
(1.93.46), (1.93.566), (1.93.621), (1.93.631), (1.93.686), (1.56.20), (1.56.21), (1.56.26), (1.56.41), (1.56.46),
(1.56.566), (1.56.621), (1.56.631), (1.56.686), (1.59.20), (1.59.21), (1.59.26), (1.59.41), (1.59.46),
(1.59.566), (1.59.621), (1.59.631), (1.59.686), (1.66.20), (1.66.21), (1.66.26), (1.66.41), (1.66.46),
(1.66.566), (1.66.621), (1.66.631), (1.66.686), (1.94.20), (1.94.21), (1.94.26), (1.94.41), (1.94.46),
(1.94.566), (1.94.621), (1.94.631), and (1.94.686), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloguintocet, cyprosulfamide, di- chlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxa- zolidine (R-29148, CAS 52836-31-4).
Here and below, the term "binary compositions" includes compositions comprising one or more, e.g. 1, 2 or 3, active compounds of the formula (I) and either one or more, e.g. 1, 2 or 3, herbicides B or one or more safeners C.
Correspondingly, the term "ternary compositions" includes compositions comprising one or more, e.g. 1, 2 or 3, active compounds of the formula (I), one or more, e.g. 1, 2 or 3, herbicides B and one or more, e.g. 1, 2 or 3, safeners C.
I n binary compositions comprising at least one pyrimidine of formula (I) as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. In binary compositions comprising at least one pyrimidine of formula (I) as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
In ternary compositions comprising at least one pyrimidine of formula (I) as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the com ponents A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1, the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1, and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. The weight ratio of components A + B to component C is preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
Particularly preferred are the compositions mentioned below comprising the pyrimidine com pounds of formula I as defined and the substance(s) as defined in the respective row of table T; especially preferred comprising as only herbicidal active compounds the pyrimidine compounds of formula I as defined and the substance(s) as defined in the respective row of table T;
most preferably comprising as only active compounds the pyrimidine compounds of formula I as defined and the substance(s) as defined in the respective row of table T.
Particularly preferred are compositions 1.1 to 1.3653, comprising the compound (1.1.20), and the substance(s) as defined in the respective row of table T:
Table T (compositions 1.1 to 1.3653):
WO 2019/121374 PCT/EP2018/084901
Figure imgf000124_0001
Also particularly preferred are compositions 1.3654 to 1.3671, comprising the compound (1.1.20), and the substance(s) as defined in the respective row of table W:
Table W (compositions 1.3654 to 1.3671):
Figure imgf000125_0001
Figure imgf000125_0002
The specific number for each single composition is deductible as follows:
Composition 1.203 e.g. comprises the compound (1.1.20), clethodim (B.1) and benoxacor (C.1) (see table B, entry B.1 and table C, entry C.1).
Also especially preferred are compositions 2.1 to 2.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.21) in place of the com pound (1.1.20).
Also especially preferred are compositions 3.1 to 3.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.2 as further herbicide B.
Also especially preferred are compositions 4.1 to 4.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 5.1 to 5.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.30 as further herbicide B.
Also especially preferred are compositions 6.1 to 6.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 7.1 to 7.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.35 as further herbicide B.
Also especially preferred are compositions 8.1 to 8.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.38 as further herbicide B.
Also especially preferred are compositions 9.1 to 9.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 10.1 to 10.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 11.1 to 11.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.1 to 12.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 13.1 to 13.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.1 to 14.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.1 to 15.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.67 as further herbicide B. Also especially preferred are compositions 16.1 to 16.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.68 as further herbicide B. Also especially preferred are compositions 17.1 to 17.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.69 as further herbicide B. Also especially preferred are compositions 18.1 to 18.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.73 as further herbicide B. Also especially preferred are compositions 19.1 to 19.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.76 as further herbicide B. Also especially preferred are compositions 20.1 to 20.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.81 as further herbicide B. Also especially preferred are compositions 21.1 to 21.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.82 as further herbicide B. Also especially preferred are compositions 22.1 to 22.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.85 as further herbicide B. Also especially preferred are compositions 23.1 to 23.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.88 as further herbicide B. Also especially preferred are compositions 24.1 to 24.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.89 as further herbicide B. Also especially preferred are compositions 25.1 to 25.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.94 as further herbicide B. Also especially preferred are compositions 26.1 to 26.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.95 as further herbicide B. Also especially preferred are compositions 27.1 to 27.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.98 as further herbicide B. Also especially preferred are compositions 28.1 to 28.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.100 as further herbicide B. Also especially preferred are compositions 29.1 to 29.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.103 as further herbicide B. Also especially preferred are compositions 30.1 to 30.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.67 as further herbi- cides B.
Also especially preferred are compositions 31.1 to 31.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.76 as further herbi- cides B.
Also especially preferred are compositions 32.1 to 32.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.82 as further herbi- cides B.
Also especially preferred are compositions 33.1 to 33.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.104 as further herbicide B. Also especially preferred are compositions 34.1 to 34.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.67 as further herbi- cides B.
Also especially preferred are compositions 35.1 to 35.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.76 as further herbi- cides B.
Also especially preferred are compositions 36.1 to 36.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.82 as further herbi- cides B.
Also especially preferred are compositions 37.1 to 37.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 38.1 to 38.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.107 as further herbicide B.
Also especially preferred are compositions 39.1 to 39.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.67 as further herbi- cides B.
Also especially preferred are compositions 40.1 to 40.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.76 as further herbi- cides B.
Also especially preferred are compositions 41.1 to 41.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.82 as further herbi- cides B.
Also especially preferred are compositions 42.1 to 42.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 43.1 to 43.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.111 as further herbicide B.
Also especially preferred are compositions 44.1 to 44.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.111 and B.67 as further herbi- cides B.
Also especially preferred are compositions 45.1 to 45.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.111 and B.76 as further herbi- cides B.
Also especially preferred are compositions 46.1 to 46.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.111 and B.82 as further herbi- cides B.
Also especially preferred are compositions 47.1 to 47.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B. 116 as further herbicide B.
Also especially preferred are compositions 48.1 to 48.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.67 as further herbi- cides B.
Also especially preferred are compositions 49.1 to 49.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.94 as further herbi- cides B.
Also especially preferred are compositions 50.1 to 50.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.103 as further herbi- cides B.
Also especially preferred are compositions 51.1 to 51.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.128 as further herbi- cides B. Also especially preferred are compositions 52.1 to 52.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.104 as further herbi- cides B.
Also especially preferred are compositions 53.1 to 53.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.107 as further herbi- cides B.
Also especially preferred are compositions 54.1 to 54.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.111 as further herbi- cides B.
Also especially preferred are compositions 55.1 to 55.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.122 as further herbicide B. Also especially preferred are compositions 56.1 to 56.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.126 as further herbicide B. Also especially preferred are compositions 57.1 to 57.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.128 as further herbicide B. Also especially preferred are compositions 58.1 to 58.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.131 as further herbicide B. Also especially preferred are compositions 59.1 to 59.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.132 as further herbicide B. Also especially preferred are compositions 60.1 to 60.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.133 as further herbicide B. Also especially preferred are compositions 61.1 to 61.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.135 as further herbicide B. Also especially preferred are compositions 62.1 to 62.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.137 as further herbicide B. Also especially preferred are compositions 63.1 to 63.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.138 as further herbicide B. Also especially preferred are compositions 64.1 to 64.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.140 as further herbicide B. Also especially preferred are compositions 65.1 to 65.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.145 as further herbicide B. Also especially preferred are compositions 66.1 to 66.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.153 as further herbicide B. Also especially preferred are compositions 67.1 to 67.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.156 as further herbicide B. Also especially preferred are compositions 68.1 to 68.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.171 as further herbicide B. Also especially preferred are compositions 69.1 to 69.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.174 as further herbicide B. Also especially preferred are compositions 70.1 to 70.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.26) in place of the com pound (1.1.20).
Also especially preferred are compositions 71.1 to 71.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.41) in place of the com- pound (1.1.20). Also especially preferred are compositions 72.1 to 72.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.46) in place of the com pound (1.1.20).
Also especially preferred are compositions 73.1 to 73.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.566) in place of the com pound (1.1.20).
Also especially preferred are compositions 74.1 to 74.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.621) in place of the com pound (1.1.20).
Also especially preferred are compositions 75.1 to 75.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.631) in place of the com pound (1.1.20).
Also especially preferred are compositions 76.1 to 76.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.1.686) in place of the com pound (1.1.20).
Also especially preferred are compositions 77.1 to 77.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.20) in place of the com pound (1.1.20).
Also especially preferred are compositions 78.1 to 78.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.21) in place of the com pound (1.1.20).
Also especially preferred are compositions 79.1 to 79.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.26) in place of the com pound (1.1.20).
Also especially preferred are compositions 80.1 to 80.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.41) in place of the com pound (1.1.20).
Also especially preferred are compositions 81.1 to 81.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.46) in place of the com pound (1.1.20).
Also especially preferred are compositions 82.1 to 82.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.566) in place of the compound (1.1.20).
Also especially preferred are compositions 83.1 to 83.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.621) in place of the com pound (1.1.20).
Also especially preferred are compositions 84.1 to 84.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.631) in place of the com pound (1.1.20).
Also especially preferred are compositions 85.1 to 85.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.2.686) in place of the compound (1.1.20).
Also especially preferred are compositions 86.1 to 86.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.20) in place of the com- pound (1.1.20). Also especially preferred are compositions 87.1 to 87.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.21) in place of the com pound (1.1.20).
Also especially preferred are compositions 88.1 to 88.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.26)) in place of the com pound (1.1.20).
Also especially preferred are compositions 89.1 to 89.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.41) in place of the com pound (1.1.20).
Also especially preferred are compositions 90.1 to 90.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.46) in place of the com pound (1.1.20).
Also especially preferred are compositions 91.1 to 91.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.566) in place of the compound (1.1.20).
Also especially preferred are compositions 92.1 to 92.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.621) in place of the com pound (1.1.20).
Also especially preferred are compositions 93.1 to 93.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.631) in place of the com pound (1.1.20).
Also especially preferred are compositions 94.1 to 94.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.4.686) in place of the compound (1.1.20).
Also especially preferred are compositions 95.1 to 95.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.20) in place of the com pound (1.1.20).
Also especially preferred are compositions 96.1 to 96.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.21) in place of the com pound (1.1.20).
Also especially preferred are compositions 97.1 to 97.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.26) in place of the com pound (1.1.20).
Also especially preferred are compositions 98.1 to 98.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.41) in place of the com pound (1.1.20).
Also especially preferred are compositions 99.1 to 99.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.46) in place of the com pound (1.1.20).
Also especially preferred are compositions 100.1 to 100.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.566) in place of the compound (1.1.20).
Also especially preferred are compositions 101.1 to 101.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.621) in place of the compound (1.1.20). Also especially preferred are compositions 102.1 to 102.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.631) in place of the compound (1.1.20).
Also especially preferred are compositions 103.1 to 103.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.11.686) in place of the compound (1.1.20).
Also especially preferred are compositions 104.1 to 104.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.20) in place of the compound (1.1.20).
Also especially preferred are compositions 105.1 to 105.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.21) in place of the compound (1.1.20).
Also especially preferred are compositions 106.1 to 106.3653 which differ from the
corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.26) in place of the compound (1.1.20).
Also especially preferred are compositions 107.1 to 107.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.41) in place of the compound (1.1.20).
Also especially preferred are compositions 108.1 to 108.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.46) in place of the compound (1.1.20).
Also especially preferred are compositions 109.1 to 109.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.566) in place of the compound (1.1.20).
Also especially preferred are compositions 110.1 to 110.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.621) in place of the compound (1.1.20).
Also especially preferred are compositions 111.1 to 111.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.631) in place of the compound (1.1.20).
Also especially preferred are compositions 112.1 to 112.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.12.686) in place of the compound (1.1.20).
Also especially preferred are compositions 113.1 to 113.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.20) in place of the com pound (1.1.20).
Also especially preferred are compositions 114.1 to 114.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.21) in place of the com pound (1.1.20).
Also especially preferred are compositions 115.1 to 115.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.26) in place of the com pound (1.1.20).
Also especially preferred are compositions 116.1 to 116.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.41) in place of the com pound (1.1.20). Also especially preferred are compositions 117.1 to 117.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.46) in place of the com pound (1.1.20).
Also especially preferred are compositions 118.1 to 118.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.566) in place of the compound (1.1.20).
Also especially preferred are compositions 119.1 to 119.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.621) in place of the compound (1.1.20).
Also especially preferred are compositions 120.1 to 120.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.631) in place of the compound (1.1.20).
Also especially preferred are compositions 121.1 to 121.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.686) in place of the compound (1.1.20).
Also especially preferred are compositions 122.1 to 122.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.20) in place of the compound (1.1.20).
Also especially preferred are compositions 123.1 to 123.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.21) in place of the compound (1.1.20).
Also especially preferred are compositions 124.1 to 124.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.26) in place of the compound (1.1.20).
Also especially preferred are compositions 125.1 to 125.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.41) in place of the compound (1.1.20).
Also especially preferred are compositions 126.1 to 126.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.46) in place of the compound (1.1.20).
Also especially preferred are compositions 127.1 to 127.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.566) in place of the compound (1.1.20).
Also especially preferred are compositions 128.1 to 128.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.621) in place of the compound (1.1.20).
Also especially preferred are compositions 129.1 to 129.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.631) in place of the compound (1.1.20).
Also especially preferred are compositions 130.1 to 130.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.89.686) in place of the compound (1.1.20).
Also especially preferred are compositions 131.1 to 131.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.20) in place of the compound (1.1.20). Also especially preferred are compositions 132.1 to 132.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.21) in place of the compound (1.1.20).
Also especially preferred are compositions 133.1 to 133.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.26) in place of the compound (1.1.20).
Also especially preferred are compositions 134.1 to 134.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.41) in place of the compound (1.1.20).
Also especially preferred are compositions 135.1 to 135.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.46) in place of the compound (1.1.20).
Also especially preferred are compositions 136.1 to 136.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.566) in place of the compound (1.1.20).
Also especially preferred are compositions 137.1 to 137.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.621) in place of the compound (1.1.20).
Also especially preferred are compositions 138.1 to 138.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.631) in place of the compound (1.1.20).
Also especially preferred are compositions 139.1 to 139.3653 which differ from the correspond ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.90.686) in place of the compound (1.1.20).
Also especially preferred are compositions 2.3654 to 2.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.21) in place of the corn-pound (1.1.20).
Also especially preferred are compositions 3.3654 to 3.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.2 as further herbicide B.
Also especially preferred are compositions 4.3654 to 4.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 5.3654 to 5.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.30 as further herbicide B.
Also especially preferred are compositions 6.3654 to 6.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 7.3654 to 7.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.35 as further herbicide B.
Also especially preferred are compositions 8.3654 to 8.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.38 as further herbicide B. Also especially preferred are compositions 9.3654 to 9.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 10.3654 to 10.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 11.3654 to 11.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.3654 to 12.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 13.3654 to 13.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.3654 to 14.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.3654 to 15.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 16.3654 to 16.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 17.3654 to 17.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 18.3654 to 18.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 19.3654 to 19.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 20.3654 to 20.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 21.3654 to 21.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 22.3654 to 22.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 23.3654 to 23.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.88 as further herbicide B. Also especially preferred are compositions 24.3654 to 24.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 25.3654 to 25.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 26.3654 to 26.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 27.3654 to 27.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 28.3654 to 28.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.100 as further herbicide B.
Also especially preferred are compositions 29.3654 to 29.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 as further herbicide B.
Also especially preferred are compositions 30.3654 to 30.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.67 as further herb-icides B.
Also especially preferred are compositions 31.3654 to 31.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.76 as fur ther herb-icides B.
Also especially preferred are compositions 32.3654 to 32.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.82 as further herb-icides B.
Also especially preferred are compositions 33.3654 to 33.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 as further herbicide B.
Also especially preferred are compositions 34.3654 to 34.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.67 as further herbicides B.
Also especially preferred are compositions 35.3654 to 35.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.76 as further herbicides B.
Also especially preferred are compositions 36.3654 to 36.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.104 and B.82 as further herbicides B.
Also especially preferred are compositions 37.3654 to 37.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 38.3654 to 38.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.107 as further herbicide B. Also especially preferred are compositions 39.3654 to 39.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
Also especially preferred are compositions 40.3654 to 40.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
Also especially preferred are compositions 41.3654 to 41.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.82 as fur ther herbicides B.
Also especially preferred are compositions 42.3654 to 42.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 43.3654 to 43.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.111 as further herbicide B.
Also especially preferred are compositions 44.3654 to 44.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.111 and B.67 as further herbicides B.
Also especially preferred are compositions 45.3654to 45.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.111 and B.76 as further herbicides B.
Also especially preferred are compositions 46.3654 to 46.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.111 and B.82 as further herbicides B.
Also especially preferred are compositions 47.3654 to 47.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B. 116 as further herbicide B.
Also especially preferred are compositions 48.3654 to 48.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.67 as further herbicides B.
Also especially preferred are compositions 49.3654 to 49.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.94 as further herbicides B.
Also especially preferred are compositions 50.3654 to 50.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.103 as further herbicides B.
Also especially preferred are compositions 51.3654 to 51.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.128 as fur ther herbicides B.
Also especially preferred are compositions 52.3654 to 52.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.104 as further herbicides B.
Also especially preferred are compositions 53.3654 to 53.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.107 as further herbicides B. Also especially preferred are compositions 54.3654 to 54.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.116 and B.111 as further herbicides B.
Also especially preferred are compositions 55.3654 to 55.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.122 as further herbicide B.
Also especially preferred are compositions 56.3654 to 56.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.126 as further herbicide B.
Also especially preferred are compositions 57.3654 to 57.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.128 as further herbicide B.
Also especially preferred are compositions 58.3654 to 58.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.131 as further herbicide B.
Also especially preferred are compositions 59.3654 to 59.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.132 as further herbicide B.
Also especially preferred are compositions 60.3654 to 60.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.133 as further herbicide B.
Also especially preferred are compositions 61.3654 to 61.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.135 as further herbi cide B.
Also especially preferred are compositions 62.3654 to 62.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.137 as further herbicide B.
Also especially preferred are compositions 63.3654 to 63.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.138 as further herbicide B.
Also especially preferred are compositions 64.3654 to 64.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.140 as further herbicide B.
Also especially preferred are compositions 65.3654 to 65.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.145 as further herbicide B.
Also especially preferred are compositions 66.3654 to 66.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.153 as further herbicide B.
Also especially preferred are compositions 67.3654 to 67.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.156 as further herbicide B.
Also especially preferred are compositions 68.3654 to 68.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.171 as further herbicide B. Also especially preferred are compositions 69.3654 to 69.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.174 as further herbicide B.
Also especially preferred are compositions 70.3654 to 70.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.26) in place of the compound (1.1.20).
Also especially preferred are compositions 71.3654 to 71.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.41) in place of the compound (1.1.20).
Also especially preferred are compositions 72.3654 to 72.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.46) in place of the compound (1.1.20).
Also especially preferred are compositions 73.3654 to 73.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.566) in place of the compound (1.1.20).
Also especially preferred are compositions 74.3654 to 74.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.621) in place of the compound (1.1.20).
Also especially preferred are compositions 75.3654 to 75.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.631) in place of the compound (1.1.20).
Also especially preferred are compositions 76.3654 to 76.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.1.686) in place of the compound (1.1.20).
Also especially preferred are compositions 77.3654 to 77.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.20) in place of the compound (1.1.20).
Also especially preferred are compositions 78.3654 to 78.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.21) in place of the compound (1.1.20).
Also especially preferred are compositions 79.3654 to 79.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.26) in place of the compound (1.1.20).
Also especially preferred are compositions 80.3654 to 80.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.41) in place of the compound (1.1.20).
Also especially preferred are compositions 81.3654 to 81.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.46) in place of the compound (1.1.20).
Also especially preferred are compositions 82.3654 to 82.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.566) in place of the compound (1.1.20).
Also especially preferred are compositions 83.3654 to 83.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.621) in place of the compound (1.1.20). Also especially preferred are compositions 84.3654 to 84.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.631) in place of the compound (1.1.20).
Also especially preferred are compositions 85.3654 to 85.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.2.686) in place of the compound (1.1.20).
Also especially preferred are compositions 86.3654 to 86.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.20) in place of the compound (1.1.20).
Also especially preferred are compositions 87.3654 to 87.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.21) in place of the compound (1.1.20).
Also especially preferred are compositions 88.3654 to 88.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.26)) in place of the compound (1.1.20).
Also especially preferred are compositions 89.3654 to 89.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.41) in place of the corn-pound (1.1.20).
Also especially preferred are compositions 90.3654 to 90.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.46) in place of the compound (1.1.20).
Also especially preferred are compositions 91.3654 to 91.3671 which differ from the correspond ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.566) in place of the compound (1.1.20).
Also especially preferred are compositions 92.3654 to 92.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.621) in place of the compound (1.1.20).
Also especially preferred are compositions 93.3654 to 93.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.631) in place of the compound (1.1.20).
Also especially preferred are compositions 94.3654 to 94.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.4.686) in place of the compound (1.1.20).
Also especially preferred are compositions 95.3654 to 95.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.20) in place of the compound (1.1.20).
Also especially preferred are compositions 96.3654 to 96.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.21) in place of the compound (1.1.20).
Also especially preferred are compositions 97.3654 to 97.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.26) in place of the compound (1.1.20).
Also especially preferred are compositions 98.3654 to 98.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.41) in place of the compound (1.1.20). Also especially preferred are compositions 99.3654 to 99.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.46) in place of the compound (1.1.20).
Also especially preferred are compositions 100.3654 to 100.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.566) in place of the compound (1.1.20).
Also especially preferred are compositions 101.3654 to 101.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.621) in place of the compound (1.1.20).
Also especially preferred are compositions 102.3654 to 102.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.631) in place of the compound (1.1.20).
Also especially preferred are compositions 103.3654 to 103.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.11.686) in place of the compound (1.1.20).
Also especially preferred are compositions 104.3654 to 104.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.20) in place of the compound (1.1.20).
Also especially preferred are compositions 105.3654 to 105.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.21) in place of the compound (1.1.20).
Also especially preferred are compositions 106.3654 to 106.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.26) in place of the compound (1.1.20).
Also especially preferred are compositions 107.3654 to 107.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.41) in place of the compound (1.1.20).
Also especially preferred are compositions 108.3654 to 108.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.46) in place of the compound (1.1.20).
Also especially preferred are compositions 109.3654 to 109.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.566) in place of the compound (1.1.20).
Also especially preferred are compositions 110.3654 to 110.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.621) in place of the compound (1.1.20).
Also especially preferred are compositions 111.3654 to 111.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.631) in place of the compound (1.1.20).
Also especially preferred are compositions 112.3654 to 112.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.12.686) in place of the compound (1.1.20).
Also especially preferred are compositions 113.3654 to 113.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.20) in place of the compound (1.1.20). Also especially preferred are compositions 114.3654 to 114.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.21) in place of the compound (1.1.20).
Also especially preferred are compositions 115.3654 to 115.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.26) in place of the compound (1.1.20).
Also especially preferred are compositions 116.3654 to 116.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.41) in place of the compound (1.1.20).
Also especially preferred are compositions 117.3654 to 117.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.46) in place of the compound (1.1.20).
Also especially preferred are compositions 118.3654 to 118.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.566) in place of the compound (1.1.20).
Also especially preferred are compositions 119.3654 to 119.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.621) in place of the compound (1.1.20).
Also especially preferred are compositions 120.3654 to 120.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.631) in place of the compound (1.1.20).
Also especially preferred are compositions 121.3654 to 121.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.15.686) in place of the compound (1.1.20).
Also especially preferred are compositions 122.3654 to 122.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.20) in place of the compound (1.1.20).
Also especially preferred are compositions 123.3654 to 123.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.21) in place of the compound (1.1.20).
Also especially preferred are compositions 124.3654 to 124.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.26) in place of the compound (1.1.20).
Also especially preferred are compositions 125.3654 to 125.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.41) in place of the compound (1.1.20).
Also especially preferred are compositions 126.3654 to 126.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.46) in place of the compound (1.1.20).
Also especially preferred are compositions 127.3654 to 127.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.566) in place of the compound (1.1.20).
Also especially preferred are compositions 128.3654 to 128.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.621) in place of the compound (1.1.20). Also especially preferred are compositions 129.3654 to 129.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.631) in place of the compound (1.1.20).
Also especially preferred are compositions 130.3654 to 130.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.89.686) in place of the compound (1.1.20).
Also especially preferred are compositions 131.3654 to 131.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.20) in place of the compound (1.1.20).
Also especially preferred are compositions 132.3654 to 132.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.21) in place of the compound (1.1.20).
Also especially preferred are compositions 133.3654 to 133.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.26) in place of the compound (1.1.20).
Also especially preferred are compositions 134.3654 to 134.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.41) in place of the compound (1.1.20).
Also especially preferred are compositions 135.3654 to 135.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.46) in place of the compound (1.1.20).
Also especially preferred are compositions 136.3654 to 136.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.566) in place of the compound (1.1.20).
Also especially preferred are compositions 137.3654 to 137.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.621) in place of the compound (1.1.20).
Also especially preferred are compositions 138.3654 to 138.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.631) in place of the compound (1.1.20).
Also especially preferred are compositions 139.3654 to 139.3671 which differ from the corre sponding compositions 1.3654 to 1.3671 only in that they comprise the compound (1.90.686) in place of the compound (1.1.20).
The invention also relates to agrochemical compositions comprising at least an auxiliary and at least one pyrimidine compound of formula (I) according to the invention.
An agrochemical composition comprises a pesticidal effective amount of a pyrimidine com pound of formula (I). The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling unwanted plants, especially for controlling un wanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic condi tions and the specific pyrimidine compound of formula (I) used.
The pyrimidine compounds of formula (I), their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agro chemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propaga tion materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Tech nical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New devel opments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liguid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bacte ricides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liguid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; ali phatic, cyclic, and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkyl ated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma- butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaCºCHarides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. ce real meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, non-ionic, and am photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of con densed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl car boxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, es ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkox ylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or pro pylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N- substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfac tants are sorbitans, ethoxylated sorbitans, sucrose, and glucose esters, or alkylpoly-glucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelec trolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the pyrimidine compounds of for mula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants, and additives, Agrow Reports DS256, T&F In forma UK, 2006, chapter 5.
Suitable thickeners are polysaCºCHarides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacya noferrate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinyl pyrrolidons, polyvinylacetates, polyvinyl alcohols, pol yacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for agrochemical composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a pyrimidine compound of formula (I) according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a pyrimidine compound of formula (I) according to the invention and 1-10 wt% dis persant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a pyrimidine compound of formula (I) according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in wa ter-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES) 5-40 wt% of a pyrimidine compound of formula (I) according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20- 40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a pyrimidine compound of formula (I) according to the in vention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a pyrimidine compound of formula (I) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a pyrimidine compound of formula (I) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wet ting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with wa ter gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a pyrimidine compound of formula (I) according to the in vention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
iv) Microemulsion (ME)
5-20 wt% of a pyrimidine compound of formula (I) according to the invention are added to 5- 30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% sur factant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mix ture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid, and a di- or triacrylate) are dispersed into an agueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initi ated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alterna tively, an oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an iso cyanate monomer (e.g. diphenylmethene-4,4'-diisocyanate) are dispersed into an agueous solu tion of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition. ix) Dustable powders (DP, DS)
1-10 wt% of a pyrimidine compound of formula (I) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
x) Granules (GR, FG)
0.5-30 wt% of a pyrimidine compound of formula (I) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xi) Ultra-low volume liguids (UL)
1-50 wt% of a pyrimidine compound of formula (I) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
The agrochemical compositions comprising generally comprise between 0.01 and 95%, prefera bly between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the pyrimidine compound of formula (I). The pyrimidine compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The agrochemical com positions in guestion give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
Methods for applying pyrimidine compounds of formula (I) and agrochemical compositions thereof, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, py rimidine compounds of formula (I) and agrochemical compositions thereof, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the pyrimidine compounds of formula (I) and the agrochemical compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the agrochemical compositions according to the invention in a weight ratio of 1:100 to 100:1, prefera bly 1:10 to 10:1.
The user applies the pyrimidine compound of formula (I) according to the invention and the agrochemical compositions comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composi tion is made up with water, butter, and/or further auxiliaries to the desired application concentra tion and the ready-to-use spray liguor or the agrochemical composition according to the inven tion is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liguor are applied per hectare of agricultural useful area.
According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising py rimidine compounds of formula (I) may be mixed by the user in a spray tank and further auxilia ries and additives may be added, if appropriate.
In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition ac cording to the invention or partially premixed components, e. g components comprising pyrimi dine compounds of formula (I) can be applied jointly (e.g. after tank mix) or consecutively.
The pyrimidine compounds of formula (I), are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising the pyrimidine compounds of formula (I), control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya, and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, e.g., water as carrier by customary spraying technigues using spray liguor amounts of from about 100 to 1000 l/ha (e.g. from 300 to 400 l/ha). The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, may also be applied by the low-volume or the ultra-low-volume method, or in the form of micro granules.
Application of the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can be done before, during, and/or after, preferably during and/or after, the emergence of the undesirable plants.
The pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the pyrimidine compounds of formula (I), or the agrochemical composi tions comprising them, by applying seed, pretreated with the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application technigues may be used in which the herbicidal compositions are sprayed, with the aid of the spraying eguipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can be applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the pyrimidine compounds of formula (I), or the agrochemical compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.
The term "seed" comprises seed of all types, such as, e.g., corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
When employed in plant protection, the amounts of active substances applied, i.e. the pyrimi dine compounds of formula (I) without formulation auxiliaries, are, depending on the kind of ef fect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
In another embodiment of the invention, the application rate of the pyrimidine compounds of formula (I) is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
In another preferred embodiment of the invention, the rates of application of the pyrimidine compounds of formula (I) according to the present invention (total amount of pyrimidine compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
In another preferred embodiment of the invention, the application rates of the pyrimidine com pounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
In another preferred embodiment of the invention, the application rate of the pyrimidine com pounds of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drench ing seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, and most preferably from 5 to 100 g, per 100 kilogram of plant propa gation material (preferably seeds) are generally reguired.
In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. the pyrimidine compounds of formula (I) are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Depending on the application method in guestion, the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec altissima, Beta vulgaris spec rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),
Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis,
SaCºCHarum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Preferred crops are Arachis hypogaea, Beta vulgaris spec altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, SaCºCHarum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or permanent crops.
The pyrimidine compounds of formula (I) according to the invention, or the agrochemical com positions comprising them, can also be used in the treatment of genetically modified plants. The term "genetically modified plants" is to be understood as plants whose genetic material has been modified by the use of recombinant DNA technigues to include an inserted seguence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technigue. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g., by inclusion therein of amino acid muta- tion(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl shikimate 3-phosphate synthase (EPSP) in hibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protopor- phyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (AC- Case) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional meth ods of breeding or genetic engineering; furthermore, plants have been made resistant to multi ple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are, e.g., described in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and references guoted therein. Several cultivated plants have been rendered tolerant to herbicides by mutagen esis and conventional methods of breeding, e. g., Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g., imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, toler ant to herbicides such as glyphosate, imidazolinones, and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany), and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
Furthermore, plants also include those are by the use of recombinant DNA technigues capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photo- rhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Strep- tomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribo some-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3 -hydroxy- steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the con text of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such tox ins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810, and WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publica tions mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to syn thesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars produc ing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g., Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars pro ducing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Bel gium (corn cultivars producing the Cry1F toxin and PAT enzyme).
Furthermore, plants also include those are by the use of recombinant DNA technigues capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bac terial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-re lated proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
Furthermore, plants also include those are by the use of recombinant DNA technigues capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral patho gens of those plants.
Furthermore, plants also include those contain by the use of recombinant DNA technigues a modified amount of ingredients or new ingredients, specifically to improve human or animal nu trition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsatu rated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
Furthermore, plants also include those that contain by the use of recombinant DNA technigues a modified amount of ingredients or new ingredients, specifically to improve raw material pro duction, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
The preparation of the pyrimidine compounds of formula (I) is illustrated by the following examples.
A Preparation examples
With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the table Ex that follows, together with physical data.
5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-(3-furyl)-4-methyl-oxazole
(Ex.35)
To a solution of 4-methyloxazole-5-carboxylic acid (9.50 g, cas 2510-32-9) in dichloromethane (150 mL) is added at 0°C N,O-dimethylhydroxylamine hydrochloride (8.31 g, cas 6638-79-5), tri- ethylamine (8.62 g, cas 121-44-8) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydro chloride (16.3 g, cas 25952-53-8). The reaction is warmed to room temperature over 16 hours. Water and dichloromethane is added, the phases are separated and the agueous phase is washed with dichloromethane (2x). The combined organic phases are dried over magnesium sul fate, filtered and concentrated to yield N-methoxy-N,4-dimethyl-oxazole-5-carboxamide (12.0 g). m/z: 171.0 [M + H+]; To a solution of N-methoxy-N,4-dimethyl-oxazole-5-carboxamide (12.0 g) in dry tetrahydrofu- rane (100 mL) under Argon is added at -60°C to -70°C a solution of 2-Chlorbenzylmagnesium- chloride (170 mL, 0.5 M in 2-Methyltetrahydrofurane). After stirring for 1 hour at -78°C the reac tion is warmed to room temperature and stirred for 16 hours. Agueous Sodium Bicarbonate solu tion is added and the mixture is extracted with ethyl acetate (3x). The combined organic phases are dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatog raphy using a gradient (cyclohexane/ethyl acetate) yielded 2-(2-chlorophenyl)-1-(4-methyloxa- zol-5-yl)ethenone (5.27 g).
m/z: 236.0 [M + H+]
To a solution of 2-(2-chlorophenyl)-1-(4-methyloxazol-5-yl)ethenone (5.27 g) in toluene (20 mL) is added N,N-Dimethylformamide-dimethylacetal (29.6 mL, cas 4637-24-5) and the reaction is stirred for 65 hours at 60°C. The reaction mixture is concentrated and purified by flash chroma tography using a gradient (cyclohexane/ethyl acetate) yielding 2-(2-chlorophenyl)-3-(dimethyla- mino)-1-(4-methyloxazol-5-yl)prop-2-en-1-one (5.94 g,).
m/z: 291.0 [M + H +]
To a solution of 2-(2-chlorophenyl)-3-(dimethylamino)-1-(4-methyloxazol-5-yl)prop-2-en-1-one (5.94 g) and cyclopropanecarboxamidine hydrochloride (2.96 g, cas 57297-29-7) in ethanol (60 mL) is added drop-wise a 20% solution of sodium ethanolate in ethanol (9.13 mL, cas 141-52-6). The reaction mixture is stirred at reflux over night. The reaction mixture is concentrated and taken up in water / dichloromethane, the phases are separated and the organic phase is concen trated to yield 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole (5.97 g). m/z: 312.0 [M + H +]
To a solution of 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole (3.30 g) in dry THF (10 mL) under Argon is added drop-wise at -78°C Lithium bis(trimethylsilyl)amide (15.9 mL, 1 M in THF, cas 4039-32-1). After stirring for 30 min. 1,2-Dibromotetrachloroethane (7.11 g, cas 630-25-1) is added drop-wise at -78°C. The reaction is slowly warmed to room temperature over night. Agueous Sodium Bicarbonate solution is added and the mixture is extracted with ethyl acetate (3x). The combined organic phases are dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography using a gradient (cyclohexane/ethyl acetate) yielded 2-bromo-5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole (3.18 g). m/z: 391.9 [M + H+];
To a mixture of 3-furylboronic acid (160 mg, cas 55552-70-0), potassium phosphate (685 mg) and [1,T-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (98.3 mg, cas 95464-05-4) in Di- oxane (7.5 mL) under Argon is added a solution of 2-bromo-5-[5-(2-chlorophenyl)-2-cyclopro- pyl-pyrimidin-4-yl]-4-methyl-oxazole (350 mg) in Dioxane (7.5 mL) at room temperature. The re action mixture is stirred for 3 hours at 90 °C and over night at room temperature. Water and ethyl acetate is added and the agueous phase is extracted with ethyl acetate (3x). The combined organic phases are washed with water, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography using a gradient (cyclohexane/ethyl acetate) yielded 5-[5- (2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-(3-furyl)-4-methyl-oxazole (139 mg).
1H NMR (400 MHz, Chloroform-d) d 8.42 (s, 1H), 7.56 - 7.28 (m, 6H), 6.39 (s, 1H), 2.70 (s, 3H), 2.43 - 2.33 (m, 1H), 1.31 - 1.23 (m, 2H), 1.22 - 1.11 (m, 2H); m/z: 378.1 [M + H+]
ethyl 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-phenyl-oxazole-4-carboxylate (Ex. 40): To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylic acid (5.0 g, synthesis as described in WO 2016120355) in THF ( 100 mL) was added 1,T Carbonyldiimidazole (CDI, 3.5 g) at room temperature. The reaction mixture was heated to 40°C. After 0.5 h CDI ( 0.4 g) was added. The reaction mixture was stirred for a further 15 min at 40°C. After cooling to 0°C DBU (3.3 g) and ethyl isocyanoacetate (2.3 mL) were added. The reaction mixture was allowed to warm to room temperature and stirred for an additional 16 h at room temperature. To the reac tion mixture was added sat. NH4CI solution (200 mL), the resulting reaction mixture was ex tracted twice with ethyl acetate (2 x 150 mL). The combined organic layers were dried over so dium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography using a gradient (cyclohexane/ethyl acetate) yielded ethyl 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrim- idin-4-yl]oxazole-4-carboxylate as a colorless oil (6.5 g).
1H NMR (500 MHz, Chloroform-d) d 8.65 (s, 1H), 7.82 (s, 1H), 7.40 - 7.34 (m, 1H), 7.33 - 7.22 (m, 2H), 7.23 - 7.16 (m, 1H), 4.21 (g, J = 7.1 Hz, 2H), 2.45 - 2.32 (m, 1H), 1.34 - 1.10 (m, 7H). HPLC/MS Rt: 1.176 min; m/z: 369.9 [M + H+]
To a solution of ethyl 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]oxazole-4-carboxylate (1.5 g) in ethanol (75 mL) was added 37% HCI in water (12 mL). The reaction mixture was stirred at room temperature for 16 h. Evaporation of the solvents yielded the crude product as an HC I salt which was triturated with ethylacetate (10 mL) to obtain ethyl 2-amino-3-[5-(2-chlorophenyl)-2- cyclopropyl-pyrimidin-4-yl]-3-oxo-propanoate. (0.33 g). HPLC/MS Rt: 0.867 min; m/z: 360.1 [M + H+].
To ethyl 2-amino-3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-3-oxo-propanoate (330 mg) in DMF (10 mL) was added HATU (380 mg), benzoic acid (134 mg) and DIPEA (0.5 mL). The reaction mixture stirred at RT for 16 h. To the reaction mixture was added sat. NaHC03 (10 mL), and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the ethyl 2-benzamido-3- [5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-3-oxo-propanoate (400 mg). HPLC/MS Rt: 1.302 min; m/z: 464.0 [M + H+]
To triphenylphosphin (452 mg), Iodine (437 mg), and triethylamine (350 mg) in DCM ( 5 mL) was added ethyl 2-benzamido-3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-3-oxo- propanoate (400 mg). The reaction mixture stirred at RT for 16 h. To the reaction mixture was added 5 mL sat. sodium thiosulfate solution, followed by water (5 mL) and DCM (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated in vacuo. Column
chromatography using an cyclohexane/ethyl acetate gradient afforded ethyl 5-[5-(2- chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-phenyl-oxazole-4-carboxylate (142 mg). HPLC/MS Rt: 1.432 min; m/z: 446.0 [M + H+]
2-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-5-phenyl-oxazole (Ex.49):
To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylic acid (1.0 g, synthesis as described in WO 2016120355) in DMF (5 mL) was added HATU (1.5 g), DIPEA (2.0 mL), and 1- amino-1-phenylpropan-1-on (HCI salt, 0.77 g) at room temperature. The reaction mixture was stirred for 16 h at room temperature and sat. NaHC03 (25 mL) was added. The reaction mixture was extracted with ethyl acetate (3x 10 mL). The combined organic layers were dried (sodium sul fate), filtered and concentrated in vacuo. Flash column chromatography using an cyclohex ane/ethyl acetate gradient afforded the 5-(2-chlorophenyl)-2-cyclopropyl-N-(1-methyl-2-oxo-2- phenyl-ethyl)pyrimidine-4-carboxamide. (127 mg). HPLC/MS Rt: 1.371 min; m/z: 406.0 [M + H+] To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-N-(1-methyl-2-oxo-2-phenyl-ethyl)pyrimi- dine-4-carboxamide (241 mg) in acetic anhydride (5 mL) is added slowly sulfuric acid (5 mL). The reaction mixture is stirred at room temperature for 1 h, then poured onto a mixture (1:1) of ice water and sat. NaHC03 (100 mL). The mixture is extracted with ethyl acetate (3x 50 mL), the com bined organic layers were dried (sodium sulfate), filtered and concentrated in vacuo. The residue was triturated with 20 mL diisopropylether to afford the product ( 140 mg).
1H NMR (400 MHz, Chloroform-d) d 8.55 (s, 1H), 7.56 - 7.27 (m, 7H), 7.11 - 7.02 (m, 2H), 2.61 - 2.46 (m, 1H), 2.50 (s, 3H), 1.33 - 1.25 (m, 2H), 1.20 - 1.13 (m, 2H). HPLC/MS Rt: 1.369 min; m/z:
388.1 [M + H+]
teAi-butyl 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole-2-carboxylate (Ex.117):
To a solution of 5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole (380 mg) in dry tetrahydrofurane (10 mL) under Argon is added Lithium bis(trimethylsilyl)amide (1.46 mL, 1 M in THF, cas 4039-32-1). After stirring for 30 minutes at -78°C di-te/T-butyl-dicarbonate (329 mg, cas 24424-99-5) is added and the reaction is warmed over 16 hours to room tempera ture. Water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated. Flash column chro matography using an cyclohexane/ethyl acetate gradient afforded tert-butyl 5-[5-(2-chloro- phenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole-2-carboxylate (215 mg).
1H NMR (500 MHz, Chloroform-d) d 8.49 (s, 1H), 7.47 - 7.44 (m, 1H), 7.40 - 7.32 (m, 2H), 7.25 - 7.21 (m, 1H), 2.59 (s, 3H), 2.39 - 2.37 (m, 1H), 1.47 (s, 9H), 1.28 - 1.23 (m, 2H), 1.19 - 1.14 (m, 2H); m/z: 412.0 [M + H+]
5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-2-phenoxy-oxazole (Ex. 122):
To a solution of phenol (145 mg, cas 108-95-2) in dimethylformamide (2.00 mL) is added so dium hydride (61.5 mg, 60%) and the mixture is stirred for 10 min at 0°C. 2-bromo-5-[5-(2-chlo- rophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-oxazole (300 mg) is added and the reaction is stirred over night at room temperature. After addition of water and te/T-butyl-methyl-ether the phases are separated. The agueous phase is extracted twice with fevt-butyl-methyl-ether and the combined organic phases are washed with water as well as with a 10 % ag. lithium chloride solu tion and brine. The combined organic phases are dried over sodium sulfate, filtered and concen trated. Flash column chromatography using an cyclohexane/ethyl acetate gradient afforded 5-[5- (2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-methyl-2-phenoxy-oxazole (222 mg).
1H NMR (500 MHz, Chloroform-d) d 8.37 (s, 1H), 7.35 - 6.81 (m, 9H), 2.53 (s, 3H), 2.36 - 2.26 (m, 1H), 1.30 - 1.18 (m, 2H), 1.18 - 1.07 (m, 2H); m/z: 404.0 [M + H+]
5-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-4-ethyl-oxazole:
To a mixture of 1-(1-lsocyanopropanesulfonyl)-4-methylbenzene (10 g) and potassium car bonate (6.1 g) in dry methanol (120 mL) was added 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine- 4-carbaldehyd (11.6 g, synthesis as described in WO 2016120355) at room temperature. The reac tion mixture was heated to 60°C and stirred at that temperature for 16 h. The reaction mixture was concentrated in vacuo and sat. sodium hydrogen carbonate (100 mL) was added. The result ing mixture was extracted with DCM ( 3x 150 mL), the combined organic layers were dried (so dium sulfate), filtered and concentrated in vacuo. Flash column chromatography using an cyclo hexane/ethyl acetate gradient afforded the product (11.3 g). 1H NMR (500 MHz, Chloroform-d) d 8.45 (s, 1H), 7.54 (s, 1H), 7.48 - 7.39 (m, 1H), 7.39 - 7.30 (m, 2H), 7.24 - 7.19 (m, 1H), 3.01 (q, J = 7.5 Hz, 2H), 2.39 - 2.30 (m, 1H), 1.29 - 1.11 (m, 7H). HPLC/MS Rt: 1.252 min; m/z: 326.0 [M + H+]
With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the table that follows, together with physical data.
The products shown below were characterized by melting point determination, by the masses ([m/z]) or retention time (RT; [min.]) determined by HPLC-MS or HPLC spectrometry.
HPLC-MS = high performance liquid chromatography-coupled mass spectrometry; HPLC meth ods:
Method: Column: Phenomenex Kinetex 1.7 pm XB-C18 100A; 50 x 2.1 mm; mobile phase: A: wa ter + 0.1% trifluoroacetic acid (TFA); B: acetonitrile + 0.1% TFA; gradient: 5-100% B in 1.50 minutes; 100% B 0.25 min; flow: 0.8-1.0ml/min in 1.51 minutes at 60°C.MS: quadrupole elec trospray ionization, 80 V (positive mode).
Figure imgf000155_0001
Table Ex:
Figure imgf000166_0001
B Use examples
The herbicidal activity of the pyrimidine compounds of formula (I) was demonstrated by the following greenhouse experiments:
The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subseguently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
Depending on the species, the plants were kept at 10 - 25°C or 20 - 35°C, respectively.
The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
The plants used in the greenhouse experiments were of the following species:
Figure imgf000174_0001
Figure imgf000174_0002
15
At an application rate of 500 g/ha, Ex.1 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and POLCO, and applied by the pre-emergence method showed very good herbicidal activity against ALOMY, APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.2 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.3 applied by the post-emergence method showed very good herbicidal activity against ALOMY and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.4 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.5 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.6 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and good herbicidal activity against AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.7 applied by the post-emergence method showed good herbicidal activity against ALOMY. At an application rate of 2000 g/ha, Ex.10 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
At an application rate of 2000 g/ha, Ex.11 applied by the post-emergence method showed very good herbicidal activity against POAAN, and applied by the pre-emergence method showed very good herbicidal activity against POAAN.
At an application rate of 2000 g/ha, Ex.16 applied by the post-emergence method showed good herbicidal activity against ALOMY.
At an application rate of 2000 g/ha, Ex.18 applied by the post-emergence method showed good herbicidal activity against ALOMY, and very good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.19 applied by the post-emergence method showed good herbicidal activity against AVEFA, and very good herbicidal activity against and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.21 applied by the post-emergence method showed very good herbicidal activity against ALOMY, SETVI and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.22 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV, SETFA and ECHCG.
At an application rate of 1000 g/ha, Ex.23 applied by the post-emergence method showed good herbicidal activity against AVEFA and ECHCG, and very good herbicidal activity against and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.24 applied by the post-emergence method showed very good herbicidal activity against ABUTH, and good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.25 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 500 g/ha, Ex.26 applied by the post-emergence method showed good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.27 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG.
At an application rate of 2000 g/ha, Ex.28 applied by the post-emergence method showed very good herbicidal activity against AMARE.
At an application rate of 1000 g/ha, Ex.29 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.31 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.32 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG. At an application rate of 1000 g/ha, Ex.33 applied by the post-emergence method showed very good herbicidal activity against ABUTH and good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.34 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.35 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.36 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.37 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.38 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.39 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.40 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.41 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.42 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.43 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and good herbicidal activity against AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
At an application rate of 2000 g/ha, Ex.44 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.45 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA, and applied by the pre-emergence method showed good herbicidal activity against APESV.
At an application rate of 1000 g/ha, Ex.46 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV. At an application rate of 2000 g/ha, Ex.47 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.48 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.49 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.50 applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.51 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 2000 g/ha, Ex.52 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG, and good herbicidal activity against AMARE.
At an application rate of 2000 g/ha, Ex.53 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.54 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.55 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.56 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.57 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.58 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against ECHCG.
At an application rate of 2000 g/ha, Ex.59 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against AMARE, APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.60 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against SETFA, APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.61 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG. At an application rate of 2000 g/ha, Ex.62 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.63 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against SETFA, APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.64 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against SETVI.
At an application rate of 1000 g/ha, Ex.65 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.66 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.67 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
At an application rate of 1000 g/ha, Ex.68 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and good herbicidal activity against SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.69 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.70 applied by the post-emergence method showed good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.71 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and applied by the pre-emergence method showed good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.72 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and good herbicidal activity against AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.73 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.74 applied by the post-emergence method showed good herbicidal activity against ECHCG, and applied by the pre-emergence method showed good herbicidal activity against ECHCG.
At an application rate of 500 g/ha, Ex.75 applied by the post-emergence method showed good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.76 applied by the post-emergence method showed good herbicidal activity against ALOMY and ECHCG At an application rate of 1000 g/ha, Ex.77 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ECHCG
At an application rate of 500 g/ha, Ex.78 applied by the post-emergence method showed very good herbicidal activity against AVEFA and POLCO, and good herbicidal activity against LOLMU, and applied by the pre-emergence method showed good herbicidal activity against APESV.
At an application rate of 1000 g/ha, Ex.79 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against ECHCG.
At an application rate of 1000 g/ha, Ex.80 applied by the post-emergence method showed very good herbicidal activity against ALOMY, SETVI and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.81 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and good herbicidal activity against AVEFA, and applied by the pre-emergence method showed good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.82 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG
At an application rate of 1000 g/ha, Ex.83 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.84 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.85 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.86 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and good herbicidal activity against AVEFA, and applied by the pre-emergence method showed good herbicidal activity against APESV and very good herbicidal activity against ECHCG.
At an application rate of 2000 g/ha, Ex.87 applied by the post-emergence method showed very good herbicidal activity against ALOMY, SETVI and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.88 applied by the post-emergence method showed very good herbicidal activity against ALOMY, SETVI and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 2000 g/ha, Ex.89 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
At an application rate of 1000 g/ha, Ex.90 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.

Claims

Claims
1. A pyrimidine compound of formula (I),
Figure imgf000180_0001
including agriculturally acceptable salts or derivatives of the pyrimidine compounds of for mula (I),
wherein
R1 is CrC6-alkyl, CrC6-haloalkyl, HO-CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6-haloalkoxy, C3- C6-cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloal- kenyloxy, CrC6-alkylthio, CrC6-haloalkylthio, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-hal- ocycloalkyl, C3-C6-halocycloalkenyl, [1-(CrC6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6- alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1-(CrC6-haloalkyl)]-C3- C6-cycloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6- cycloalkyl, C3-C6-cycloalkyl-CrC6-alkyl, C3-C6-cycloalkyl-CrC6-haloalkyl, C3-C6-cyclo- alkyl-CrC6-alkoxy, C3-C6-cycloalkyl-CrC6-haloalkoxy, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted with Re;
R2 is 5-membered heteroaryl selected from thiophenyl, furyl, which groups are substi tuted with one X, one Y and one W, or oxazolyl or 1-methylimidazolyl, which groups are substituted with one X and one Y, or 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5- oxadiazolyl which groups are substituted with one Y;
X, W independently are H, halogen, CN, N02, OH, CrC6-alkyl, CrC6-haloalkyl, CrC6- alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, Ci-C6-alkylsulfinyl, CrC6-alkylsulfonyl, which groups are unsubstituted or substituted with Ra, or R20;
Y is CrC6-alkyl, CrC6-haloalkyl, Ci-C6-alkoxy-(CrC4-alkoxy)n, CrC6-haloalkoxy, CrC6- alkylthio, CrC6-alkylsulfinyl, or CrC6-alkylsulfonyl, which groups are substituted with Ra, or R20;
R20 is ORb, SH, SRb, C2-C6-alkenyl, C2-C6-alkinyl, NR4R5, CONR4R5, CORf, C3-C6-alkenylsulfi- nyl, C3-C6-alkinylsulfinyl, aminosulfinyl, CrC6-alkylaminosulfinyl, di(CrC6-alkyl)amino- sulfinyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, aminosulfonyl, CrC6-alkylamino- sulfonyl, di(CrC6-alkyl)aminosulfonyl, CrC6-alkylcarbonylaminosulfonyl, C3-C6-cyclo- alkylcarbonylaminosulfonyl, hydroxysulfonyl, CrC6-alkoxysulfonyl, hydroxycarbonyl, aminocarbonyl, NH2-aminocarbonyl, CrC6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3- C6-alkinylcarbonyl, thiocarbonyl, CrC6-alkylcarbonylaminocarbonyl, C3-C6-cycloalkyl- carbonylaminocarbonyl, CrC6-alkylsulfonylaminocarbonyl, C3-C6-cycloalkylsulfonyla- minocarbonyl, di(CrC6-alkyl)aminosulfonylaminocarbonyl, hydroxyaminocarbonyl, Cr C6-alkoxyaminocarbonyl, [(CrC6-alkoxy)(CrC6-alkyl)amino]carbonyl, phenylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6-membered heterocyclylcarbonyl, C3- C6-cycloalkylcarbonyl, (H0)2(0)P, (HO)(CrC6-alkoxy)(0)P, (CrC6-alkoxy)2(0)P, C3-C8- cycloalkyl, C4-C8-cycloalkenyl, CrC8-alkylidenyl-cycloalkyl, CrC8-alkylidenyl-heterocy- clyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl, phenylsu Ifi nyl, 5- or 6-membered heteroa ryl su Ifi ny I, 3- to 6-membered heterocyclyl- sulfinyl, C3-C6-cycloalkylsulfinyl, phenylsulfonyl, 5- or 6-membered heteroa rylsulfonyl, 3- to 6-membered heterocyclylsulfonyl, C3-C6-cycloalkylsulfonyl;
cyclic groups of R20 are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of R20 are unsubstituted or substituted with Rd;
Ra is OH, CN, CrC6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkinyloxy, CrC6-haloalkoxy, Cr C6-alkoxy-Ci-C6-alkoxy, NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6- alkylthio, CrC6-alkylsulfi nyl, CrC6-alkylsulfonyl, CN, N02, C3-C6-cycloalkyl, C3-C8- cycloalkenyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-haloalkoxycarbonyl, C2-C6-alkenyloxycarbonyl, C3-C6-alkinyloxycarbonyl, aminocarbonyl, CrC6-alkyla- minocarbonyl, di(CrC6-alkyl)aminocarbonyl, CrC6-alkylcarbonyl, CrC6-haloalkyl- carbonyl, phenyl, phenylthio, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rb is C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6-haloalkinyl, C3-C6-cycloal- kyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocycloalkenyl, CrC6- alkoxycarbonyl-CrC6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, C3-C6-cy- cloalkylcarbonyl, hydroxycarbonyl-CrC6-alkyl, CrC6-alkyloxycarbonyl, CrC6-al- kylthiocarbonyl, CrC6-aminocarbonyl, CrC6-dialkylaminocarbonyl, Ci-C6-alkyl- sulfonyl, CrC6-haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, CrC6-alkoxy-CrC6-alkyl, phenyl-CrC6-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
Rc is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, OH, CrC6-alkoxy, CrC6-haloal- koxy, NH2, CrC6-alkyl-amino, di(CrC6-alkyl)amino, SH, CrC6-alkylthio, CrC6-alkyl- sulfinyl, CrC6-alkylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, C2-C6-alkenyloxycar- bonyl, alkinyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, CrC6- alkylaminocarbonyl, or di(Ci-C6-alkyl)aminocarbonyl;
Rd is halogen, CN, N02, OH, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-C6-haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, CrC6-haloalkoxy, NH2, CrC6-alkyl-amino, di(C1-C6-alkyl)amino, SH, Cr C6-alkylthio, CrC6-alkylsulfinyl, CrC6-alkylsulfonyl, C3-C6-cycloalkyl, C -C8-cycloal- kenyl, hydroxycarbonyl, CrC6-alkoxycarbonyl, Ci-C6-alkenyloxycarbonyl, CrC6-al- kinyloxycarbonyl, CrC6-alkoxycarbonyl-CrC6-alkyl, hydroxycarbonyl-CrC6-alkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, C3-C6-cycloalkylcarbonyl, aminocar bonyl, CrC6-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, CrC6-alkylthiocar- bonyl, CrC6-alkylsulfonyl, CrC6-haloalkylsulfonyl, C3-C6-cycloalkylsulfonyl, CrC6- alkoxy- CrC6-alkyl, phenylthio, phenyl-Ci-C6-alkyl, phenyl, 5- or 6-membered het eroaryl, or 3- to 6-membered heterocyclyl, C3-C6-cycloalkyl, or C4-C6-cycloalkenyl;
Re is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkoxy, or CrC6-haloalkoxy;
Rf is H, halogen, CN, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, CrC6-haloalkyl, C3-
C6-haloalkenyl, C3-C6-haloalkinyl, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
R4 and R5 are independently from each other selected from hydrogen, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, OH, NH2, CrC6-alkoxy, C3-C6-alkenyloxy, C3-C6-al- kinyloxy, CrC6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkinylcarbonyl, CrC6- alkylsulfonyl, CrC6-haloalkylsulfonyl, C3-C6-alkenylsulfonyl, C3-C6-alkinylsulfonyl, CrC6-alkylsulfinyl, C3-C6-alkenylsulfinyl, C3-C6-alkinylsulfinyl, CrC6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkinyloxycarbonyl, phenyl, 5- or 6-membered heteroaryl, 3- or 6-membered heterocyclyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3- or 6-membered heterocyclyloxy, C3-C6-cycloalkyloxy, C3-C6-cycloalkenyloxy, phe- nylcarbonyl, 5- or 6-membered heteroarylcarbonyl, 3- or 6-membered heterocy- clylcarbonyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroarylsulfonyl, 3- or 6-membered heterocyclylsulfonyl, C3- C6-cycloa Ikylsu Ifonyl, C3-C6-cycloalkenylsulfonyl, phenylsulfinyl, 5- or 6-membered heteroa rylsu Ifinyl, 3- or 6-membered hete rocycly Isu Ifi ny I, C3-C6-cycloalkylsulfinyl, C3-C6-cycloal kenylsu Ifi nyl, phenyloxycarbonyl, 5- or 6-membered het- eroaryloxycarbonyl, 3- or 6-membered heterocyclyloxycarbonyl, C3-C6-cycloalky- loxycarbonyl, C3-C6-cycloalkenyloxycarbonyl, aminocarbonyl, Ci-C6-alkylaminocar- bonyl, di(CrC6-alkyl)aminocarbonyl, aminosulfonyl, CrC6-alkylaminosulfonyl, di(CrC6-alkyl)aminosulfonyl, aminosulfinyl, CrC6-alkylaminosulfinyl, and di(CrC6- a I kyl)a mi nosu Ifi nyl;
Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered fully unsaturated bi- cyclic ring containing 0, 1, 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
R3 same or differently is H, halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcar- bonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy, CrC6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6- haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, CrC6-alkoxycarbonyl, Cr C6-alkylthio, CrC6-haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, (CrC6- alkyl)sulfinyl, (CrC6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; m is 0, 1, 2, 3, or 4;
n is 1, 2, 3, 4, or 5;
provided that the compound of formula (I) is not N-[4-(2,5-Dimethyl-3-furyl)-5-(3-ethyl-4- pyridyl)-2-pyrimidinyl]-N-ethylamine, N-lsopropyl-5-(3-methylisoxazol-5-yl)-4-(5- methylthio-phen-2-yl)pyrimidin-2-amine, 3-Methyl-5-(2-(methylthio)-4-(5-methylthi- ophen-2-yl)-pyrimidin-5-yl)isoxazole or 3-Methyl-5-(2-(methylsulfonyl)-4-(5-methyl- thiophen-2-yl)pyrimidin-5-yl)isoxazole.
2. The compound of formula I according to claim 1, wherein
R1 is CrC6-alkyl, CrC6-alkoxy, CrC6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C4-C6-haloalkynyloxy, CrC6-alkylthio, or C3-C6-cycloalkyl wherein cycloalkyl is unsubstituted.
3. The compound of formula I according to claim 1 or 2, wherein Z-(R3)m is formula W1, wherein
R3 is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6-alkylcarbonyl, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy, CrC6-haloalkoxy, C3- C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, CrC6- alkoxy-CrC6-alkoxy, hydroxycarbonyl, CrC6-alkoxycarbonyl, CrC6-alkylthio, C1-C6- haloalkylthio, NH2, (CrC6-alkyl)amino, di(CrC6-alkyl)amino, (CrC6-alkyl)sulfinyl, (Cr C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted with substituents Re; R3b and R3c each independently is H, halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, CrC6- a I kylca r bony I, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cr C6-alkoxy, CrC6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, CrC6-alkoxycar- bonyl, Ci-C6-alkylthio, CrC6-haloalkylthio, NH2, (CrC6-alkyl)amino, di(Ci-C6-alkyl)- amino, (C-|-C 6-a I kyl)su Ifi ny I, (CrC6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cyclic groups of R3b and R3c are unsubstituted or substituted with substitu ents Re;
and
# denotes the point of attachment to the pyrimidine ring.
4. The compound of formula I according to claim 1 or 2, wherein Z-(R3)m is selected from
groups A to G,
Figure imgf000183_0001
wherein
R3 is halogen, CHO, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or CrC6-alkoxy;
R3b is H, halogen, CHO, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-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.
5. The compound of formula I according to claim 1 or 2, wherein Z-(R3)m is selected from groups H to V,
Figure imgf000184_0001
wherein
Y1 is 5- or 6-membered fully unsaturated carbocycle comprising 0, 1, 2, or 3 heteroatoms selected from O, N, and S;
R3 is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or CrC6-alkoxy;
R3b and R3c each independently is H, halogen, CN, CrC6-alkyl, CrC6-haloalkyl, or C C6- alkoxy ;
X1 is O, S, or NR3A;
R3A is H, CrC6-alkyl, CrC6-haloalkyl, CrC6-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.
6. The compound of formula I according to any of preceeding claims, wherein R2 is selected from R2-1 to R2-24,
Figure imgf000184_0002
7. The compound of formula I according to any of the preceding claim, wherein
R1 is unsubstituted cyclopropyl;
R2 is selected from R2-13, R2-14, R2-15, R2-16, R2-17, R2-18, R2-19, R2-20, and R2-21;
wherein
X is H, CrC6-alkyl, hydroxycarbonyl, or phenyl, preferably H or CrC6-alkyl, more prefer ably H, CH3, C2H5, or n-propyl;
Y is C2-C6-alkenyl, C2-C6-alkinyl, C4-C8-cycloalkenyl, CrC6-alkoxy-(CrC4-alkoxy)n, NH2, SH, CrC6-alkylthio-CrC6-alkyl, CrC6-alkoxy-CrC6-alkyl, CrC6-alkylcarbonyl, hy droxycarbonyl, CrC6-alkoxycarbonyl, aminocarbonyl, CrC6-alkylaminocarbonyl, di(Cr C6-alkyl)aminocarbonyl, NH2-aminocarbonyl, hydroxyaminocarbonyl, C3-C6-cycloal- kylaminocarbonyl, CrC6-alkylcarbonylamino, CrC6-alkylsulfonylaminocarbonyl, di(Cr C6-alkylsulfonyl)aminocarbonyl, phenyl, phenoxy, phenyl-CrC6-alkyl, phenyl-CrC6- alkylthio, phenylthio-CrC6-alkyl, 5- or 6-membered heteroaryl, 3- to 6-membered heterocyclylcarbonyl, (HO)(CrC6-alkoxy)(0)P or (CrC6-alkoxy)2(0)P;
wherein
cyclic groups of X and Y are unsubstituted or substituted with Rc; and
acyclic aliphatic groups of X and Y are unsubstituted or substituted with Rd;
n is 1, 2 or 3;
Rc is halogen, CN, CrC6-alkyl, CrC6-haloalkyl, OH, or CrC6-alkoxy;
Rd is C2-C6-alkinyl, OH, phenyl, or CrC6-alkylthio;
Z is formula W1, wherein m is 0 or 1; and R3 is halogen.
8. The compound of formula I according to claim 6 or 7, wherein R2 is selected from R2-13, R2- 14, R2-15, R2-16, R2-17, and R2-18.
9. A use of pyrimidine compounds of formula (I), including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, according to any of claims 1 to 8, as herbicide.
10. A herbicidal composition comprising:
A) at least one pyrimidine compound of formula I, including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, ac cording to any of claims 1 to 8;
and
B) herbicides of class b1) to b15):
b1) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); b11) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, daz- omet, difenzoguat, difenzoguat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl io dide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, guinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6- methylphenoxy)-4-pyridazinol, and its salts and esters;
including their agriculturally acceptable salts or derivatives.
11. A herbicidal composition comprising the herbicidal composition according to claim 10, and safeners.
12. The herbicidal composition according to any of claim 10 to 11, wherein the weight ratio of component A to component B is in the range of from 1:500 to 500:1.
13. A herbicidal composition comprising a herbicidal active amount of at least one pyrimidine compound of formula (I) including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, according to any of claims 1 to 8, and at least one inert liguid and/or solid carrier and, if appropriate, at least one surface- active substance.
14. A herbicidal composition comprising a herbicidal composition according to any of claims 10 to 12, and at least one inert liguid and/or solid carrier and, if appropriate, at least one surface-active substance.
15. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of at least one pyrimidine compound of formula (I) including agriculturally ac- ceptable salts or derivatives of compounds of formula (I) having an acidic functionality, ac cording to any of claims 1 to 8 or a composition according to any of claims 10 to 13 to act on plants, their environment or on seed.
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EP4198033A1 (en) 2021-12-14 2023-06-21 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2023110473A1 (en) 2021-12-14 2023-06-22 Basf Se Heterocyclic compounds for the control of invertebrate pests

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