WO2019121408A1 - Composés herbicides de pyrimidine - Google Patents

Composés herbicides de pyrimidine Download PDF

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WO2019121408A1
WO2019121408A1 PCT/EP2018/085006 EP2018085006W WO2019121408A1 WO 2019121408 A1 WO2019121408 A1 WO 2019121408A1 EP 2018085006 W EP2018085006 W EP 2018085006W WO 2019121408 A1 WO2019121408 A1 WO 2019121408A1
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alkyl
alkoxy
carbonyl
compositions
haloalkoxy
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PCT/EP2018/085006
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English (en)
Inventor
Veronica LOPEZ CARRILLO
Tobias SEISER
Gunther Zimmermann
Matthias Witschel
Florian Vogt
Thomas Seitz
Gerd Kraemer
Trevor William Newton
Peter Dombo
Klaus Reinhard
Klaus Kreuz
Doreen Schachtschabel
Eva HOLLENBACH
Ruth CAMPE
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

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.
  • WO2016/120355 discloses the use of phenylpyrimidines as herbicides.
  • R 1 is formula R 1 R 1
  • R x , R y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C1-C6- haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloalkoxy, C3-C6- cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycl
  • phenyl, heteroaryl and heterocyclyl rings of R 2 independently from one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or C 1 -C 6 - haloalkoxy;
  • 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, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C3- C 6 -alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6- alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C 6 -alkyl)
  • R e is halogen, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, or Ci-C 6 -haloalkoxy; m is 0, 1 , 2, 3, or 4;
  • the present invention also provides the pyrimidine compounds of formula (I) as above, wherein when m is 2, 3 or 4, each R 3 in formula (I) is independently H, halogen, CN, N02, C1 -C6-alkyl, C1 -C6-haloalkyl, C1 -C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-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, hy- droxycarbonyl, C1 -C6
  • the present invention also provides the pyrimidine compounds of formula (I)
  • R 1 is formula R 1
  • R x , R y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C1-C6- haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloalkoxy, C3-C6-cycloal- koxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-hal
  • R x and R y together with the carbon they are attached can form a 3-to 5-membered satu- rated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl-Ci-C6-alkyl, C 1 -C 6 - alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxy- carbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci- C6-haloalkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C6-alk
  • phenyl, heteroaryl and heterocyclyl rings of R 2 independently from one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy or C 1 - C 6 -haloalkoxy;
  • Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 10-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
  • R 3 is H, halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 - alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, C 1 -C 6 - haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloal- kynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, C 1 -C 6 - alkylthio, Ci-
  • R e is halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, or Ci-C 6 -haloal- koxy;
  • n 0, 1 , 2, 3, or 4;
  • R 1 is CF 3 and Z-(R 3 ) m is 2-CI-Phenyl, R 2 is not OH or OCH 3 .
  • the present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
  • the present invention also provides use of the pyrimidine compounds of formula (I) as de- scribed herein including agriculturally acceptable salts or derivatives of compounds of formula (I) as herbicide.
  • the present invention also provides a method of controlling undesired vegetation, which corn- prises allowing a herbicidal active amount of at least one pyrimidine compound of formula (I) in- cluding agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, or compositions thereof.
  • pyrimidine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:
  • the phenylpyrimidines of formula (I) can be obtained by reacting respective pyrimidines of for- mula (II) with boronic acids of formula (III):
  • the reaction of the pyridine (II) with boronic acids (III) is usually carried out at from 0 °C to the boiling point of the reaction mixture, preferably at from 15 °C to 1 10 °C, particularly preferably at from 20 °C to 60 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out without solvent. However, preference is given to reacting the pyrimidines (II) with the boronic acids (lll)in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyrimidines (II) and the boronic acids (III) at least partly and preferably fully under reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • TBME -butyl methylether
  • dioxane anisole and tetrahydrofuran
  • dipolar aprotic sol- vents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethyla- cetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrrolidinone (NMP).
  • Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF) and dipolar aprotic solvents such as sul- folane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3- dimethyl-2-imidazolidinone (DMI), N,N'-dimethyhpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrroli-dinone (NMP).
  • ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF) and dipolar aprotic solvents such as sul
  • More preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert.-butyl meth- ylether (TBME), dioxane, anisole and tetrahydrofuran (THF).
  • ethers such as diethyl ether, diisopropyl ether, tert.-butyl meth- ylether (TBME), dioxane, anisole and tetrahydrofuran (THF).
  • suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate magnesium carbonate, and calcium carbonate, as well as alkali metal hydrogen car- bonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, po- tassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potas- sium phosphate, calcium phosphate.
  • metal-con- taining bases such as alkali metal and alkaline
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hy- droxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, and calcium carbonate.
  • Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, po- tassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide.
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably at from 1 to 10 equivalents based on the pyrimidine (II), more preferably at from 1.0 to 5.0 equivalents based on the pyrimidine (II), most preferably from 1 .2 to 2.5 equivalents based on the pyrimidine (II).
  • the reaction of the pyridines (II) with the boronic acids (II) is carried out in the presence of a catalyst.
  • suitable catalysts include for example, palladium based catalysts like, for example, Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(tri- phenylphosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, for example, phosphines like, for example, P(o-tolyl)3, tr phenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,T-binaphthyl).
  • the amount of catalyst is usually 10 to 20 mol % (0.1 to 0.2 equivalents) based on the pyrimi- dine (II).
  • phenylpyrimidines (I), wherein R 2 has any one of the above mentioned meanings except OH can also be obtained by modifying phenylpyrimidines (I) wherein R 2 is OH by known methods (e.g.“oxy-substituents” exept“OH” analogous to Arnab, P. et. al. Angew. Chem. Int. Ed. 2010, 49, 1492-1495;“thio-substituents” analogous to Silvestri, M. A. et. al. J. Med. Chem. 2004, 47, 3149-3162;“amino-sustituents” analogous to Kuhn, B. et. al. J. Med. Chem. 2010, 53, 2601 -261 1 ).
  • known methods e.g.“oxy-substituents” exept“OH” analogous to Arnab, P. et. al. Angew. Chem. Int. Ed. 2010,
  • pyrimidines (II) wherein R 2 is OH are known from the literature (e.g. WO 06/004532) or are commercially available.
  • the pyrimidines (II) wherein R 2 is OH can easily be modified by known methods (e.g. “oxy-substituents” exept“OH” analogous to Arnab, P. et. al. Angew. Chem. Int. Ed. 2010, 49, 1492-1495;“thio-substituents” analogous to Silvestri, M. A. et. al. J. Med. Chem. 2004, 47, 3149-3162;“amino-sustituents” analogous to Kuhn, B. et. al. J. Med. Chem. 2010, 53, 2601 - 261 1 ).
  • known methods e.g. “oxy-substituents” exept“OH” analogous to Arnab, P. et. al. Angew. Chem. Int. Ed. 2010, 49, 1492-1495;“thio-substituents” analogous to Silvestri, M. A.
  • boronic acids (III) required for the preparation of phenylpyrimidines of formula (I) are known from the literature or are commercially available.
  • the pyrimidine compounds of formula (I) can be obtained by reacting respective methylpyrim- idines of formula (II) with an oxidant:
  • the reaction of the methyalpyrimidine (II) with an oxidant 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 preferably from 40 °C to 120 °C, in an inert organic solvent in the presence of a base.
  • the reaction may in principle be carried out without solvent. However, preference is given to reacting the methylpyrimidines (II) and the oxidant in water or an an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the aminoketones (III) with the amidine (IV) at least partly and preferably fully under the reaction conditions.
  • suitable solvents are water, aromatic hydrocarbons such as benzene, chloroben- zene, toluene, cresols, o-, m- and p-xylene, pyridine, halogenated hydrocarbons such as di- chloromethane, 1 ,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as benzene, chloroben- zene, toluene, cresols, o-, m- and p-xylene
  • pyridine halogenated hydrocarbons such as di- chloromethane, 1 ,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • TBME -butyl methylether
  • dioxane dioxane
  • anisole and tet- rahydrofuran esters such as ethyl acetate and butyl acetate
  • esters such as ethyl acetate and butyl acetate
  • nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethyl- propylene urea (DMPU) and 1 -methyl-2 pyrrolidinone (NMP).
  • DMF N,N-dimethylformamide
  • DMAC N,N-dimethylacetamide
  • DI N,N'-dimethyl-2-imidazolidinone
  • Preferred solvents are pyridine and water.
  • Suitable oxidants are Se02, KMn04, Mn02, 02, Oxone, NaCI02, H202, preferably Se02 or KMn04.
  • the pyrimidine compounds of formula (II) can be obtained by reacting respective amino- ketones of formula (III) with base and amidine (XIV):
  • the reaction of the aminoketone (III) with the amidine (IV) is usually carried out at tempera- tures of from -100 °C to the boiling point of the reaction mixture, preferably from 20 °C to the boiling point, particularly preferably from 40 °C to 120 °C, in an inert organic solvent in the pres- ence of a base.
  • the reaction may in principle be carried out without solvent. However, preference is given to reacting the aminoketones (III) with the amidine (IV) in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the aminoketones (III) with the amidine (IV) at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • TBME -butyl methylether
  • dioxane dioxane
  • anisole and tetrahydrofuran esters
  • esters such as ethyl acetate and butyl acetate
  • nitriles such as acetonitrile and propi- onitrile
  • alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-buta- nol
  • dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylforma- mide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dime- thylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrrolidinone (NMP).
  • Preferred solvents are alcohols such as methanol and ethanol.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hy- dride, alkali metal azides, such as lithium hexamethyidisilazide, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, and also al- kali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, po- tassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyr
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the amidine (IV), based on the aminoketone (III).
  • the end of the reaction can easily be determined by the skilled worker by means of routine methods.
  • reaction mixtures are worked up in a customary manner, for example by mixing with wa- ter, separation of the phases and, if appropriate, chromatographic purification of the crude prod- uct.
  • Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately el- evated temperature.
  • purification can also be carried out by recrystallisation or digestion.
  • a Palladium contain- ing complex e.g. Pd(PPhi3)2Cl2 in an organic solvent, preferrably DMF.
  • a fluorinating agent preferrably diethylaminosulfurtrifluorid
  • the aminoketones (III) are prepared from the corresponding ketones (V) with N,N-Dimethylfor- mamide dimethyl acetal (CAS 4637-24-5).
  • the reaction is usually carried out at temperatures from -100 °C to the boiling point of the reaction mixture, preferably from 20 °C to 160 °C, partic- ularly preferably from 50 °C to 130 °C.
  • the reaction can optionally be catalyzed be an acid.
  • the reaction may be carried out without solvent or in an organic solvent. Suitable in principle are all solvents which are capable of dissolving the ketones (V) and N,N-Dimethylformamide di- methyl acetal (CAS 4637-24-5) at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • TBME -butyl methylether
  • dioxane dioxane
  • anisole and tetrahydrofuran esters
  • esters such as ethyl acetate and butyl acetate
  • nitriles such as acetonitrile and propi- onitrile, as well as dipolar aprotic solvents
  • dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylfor- mamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'- dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrrolidinone (NMP); preferably N,N-Dimethylformamide dimethyl acetal is used as solvent.
  • DMF N,N-dimethylfor- mamide
  • DMAC
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid; organic acids p-toluenesul- fonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methansulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI. Most preferred, no acid is used.
  • the acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the end of the reaction can easily be determined by the skilled worker by means of routine methods.
  • reaction mixtures are worked up in a customary manner, for example by mixing with wa- ter, separation of the phases and, if appropriate, chromatographic purification of the crude prod- uct.
  • Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately el- evated temperature.
  • purification can also be carried out by recrystallization or digestion.
  • the present invention also provides agrochemical compositions comprising at least one pyrimidine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
  • the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyrimidine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat.
  • Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • 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.
  • the pyrimidine compounds of formula (I) as described herein have one or more centres of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions ac- cording to the invention.
  • pyrimidine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, more preferably a carboxylic group or a sulphonic group, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cati ons and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C 4 -alkyl, HO-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 - alkyl, HO-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C 4 -al- kanoic acids, preferably formate, acetate, propionate and butyrate.
  • Pyrimidine compounds of formula (I) as described herein having an acidic functionality can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with the cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C 6 -al- kylamides or arylamides, as esters, e.g.
  • allyl esters propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, e.g. as Ci-Cio-alkylthio esters.
  • Preferred mono- and di-Ci-C 6 -alkylamides are the CH 3 and the dimethyl- amides.
  • Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
  • Preferred alkyl es- ters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Preferred Ci-C 4 -alkoxy- Ci-C 4 -alkyl esters are the straight-chain or branched Ci-C 4 -alkoxy ethyl esters, e.g.
  • Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C 6 -alkyl Ci-C 4 -alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1-dimethylpropyl, 1 ,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1 -ethylbutyl, 2-ethylbutyl, 1 , 1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1
  • Ci-C 4 -haloalkyl Ci-C 4 -alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodi- fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di- chloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1 , 1 -diflu
  • Ci-C 6 -haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-io- dohexyl, and dodecafluorohexyl;
  • 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 -halocycloalkyl C 3 -C 6 -cycloalkyl as mentioned above which is partially or fully sub- stituted with fluorine, chlorine, bromine and/or iodine, e.g., 1-fluorocyclopropyl;
  • 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-
  • C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1 -yl, 3- chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1 -yl, 2,3,3-trichloro-2-en-
  • C3-C6-alkynyl e.g. 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl- 4-pent
  • C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
  • C3-C6-haloalkynyl a C3-C6-alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1 ,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bro- moprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1 , 1 -difluoro- but-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn- 1 -yl, or 6-iodohex-5-yn-1 -y
  • Ci-C 4 -alkoxy e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy, and 1 ,1 -dimethylethoxy;
  • Ci-C 6 -alkoxy Ci-C 4 -alkoxy as mentioned above, and also, e.g., pentoxy, 1 -methylbut- oxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trime- thylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy, and 1
  • Ci-C 4 -haloalkoxy a Ci-C 4 -alkoxy group as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluorometh- oxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chlor
  • Ci-C 6 -haloalkoxy a Ci-C 4 -haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
  • Ci -C 4 -a I ky Ith i o e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1 , 1 -dimethylethylthio;
  • Ci-C 6 -alkylthio Ci-C 4 -alkylthio as mentioned above, and also, e.g., pentylthio, 1-methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1 , 1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-
  • (Ci-C4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1-dimethylethylamino;
  • (Ci-C 6 -alkyl)amino (Ci-C 4 -alkylamino) as mentioned above, and also, e.g., pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethyl- propylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethylpropylamino, 1-methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1-dimethylbutyla- mino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1-ethylbuty
  • di(Ci-C 4 -alkyl)amino e.g. N,N-dimethylamino, N,N-diethylamino, N,N-di(1-meth- ylethyl)amino, N,N-dipropylamino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2- methylpropyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-prop- ylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpro- pyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,
  • di(Ci-C 6 -alkyl)amino di(Ci-C 4 -alkyl)amino as mentioned above, and also, e.g., N-me- thyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-me- thyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1-dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methyl
  • Ci-C 6 -alkylsulfonyl (Ci-C 6 -alkyl-S(0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1-di- methylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfonyl
  • C3-C6-cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-cycloalkenyl 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1- cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadi- enyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 2,5-cyclohexadienyl;
  • bicyclic ring a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and inde- pendent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole
  • heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
  • 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
  • heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an ox ygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
  • pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
  • thiazol-2-yl thiazol-4-yl, thiazol-5-yl
  • oxadia- zolyl e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl,
  • thiadiazolyl e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl
  • triazolyl e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl
  • 1 -tetrazolyl 6-membered aromatic rings like pyridyl (e.g.
  • pyridine-2 -yl pyridine-3-yl, pyridine-4-yl
  • pyrazinyl e.g. pyridazin-3-yl, pyridazin-4-yl
  • pyrimidinyl e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl
  • pyrazin-2-yl triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl
  • substituted if not specified otherwise refers to substituted with 1 , 2, or up to maxi- mum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not men- tioned otherwise.
  • acidic functionality if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
  • cyclic groups comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
  • pyrimidine compounds of formula (I) are suitable as herbicides.
  • R 1 is not fluoromethyl, difluoromethyl, tri- fluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, 1 ,1 ,2,2,-tetrafluoroethyl, 1-trifluoromethyl-1 ,2,2,2-tetrafluoro- ethyl and undecafluoropentyl;
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocycloalkenyl;
  • R x is Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocy- cloalkenyl;
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocy- cloalkyl;
  • R x is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C 3 -C 6 -cycloalkyl;
  • R x is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R x is H, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl
  • R x is H, halogen, Ci-C 6 -alkyl
  • R x is H, or Ci-C 6 -alkyl
  • R x is H or halogen
  • R x is H
  • R x is Ci-C6-alkyl e.g. CH3, C2H5, i-C3H 7 , n-C4H9, and i-C ⁇ g;
  • R x is C 3 -C 6 -cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C 3 H 5 , C-C 4 H 7 , and C-C 5 H 9 ;
  • R x is halogen
  • R x is Ci-C6-haloalkyl e.g. CHF 2 , CHF 2 , and CF 3 ;
  • R x is C 3 -C 6 -halocycloalkyl
  • R x is H, CH3, C2H5, F, 1-C3H7 , CHF2, CHF2, or c-C3H 5 ;
  • R ⁇ is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocycloalkenyl;
  • R ⁇ is H, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halo- cycloalkenyl; also preferred R y is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocy- cloalkyl;
  • R y is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C3-C6-cycloalkyl;
  • R y is H, halogen, Ci-C 6 -alkyl, or C3-C6-cycloalkyl;
  • R y is H, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl
  • R y is H, halogen, Ci-C 6 -alkyl
  • R y is H, or Ci-C 6 -alkyl
  • R y is H or halogen
  • R y is H
  • R y is Ci-C6-alkyl e.g. CH 3 , C 2 H 5 , i-C3H 7 , n-C4Hg, and 1-C 4 H 9 ;
  • R y is C 3 -C 6 -cycloalkyl, preferably Cs-Cs-cycloalkyl e.g. C-C 3 H 5 , C-C 4 H 7 , and C-C 5 H 9 ;
  • R y is halogen
  • R y is Ci-C 6 -haloalkyl e.g. CHF2, CHF2, and CF3;
  • R y is C3-C6-halocycloalkyl
  • R y is H, CH3, C2H5, F, 1-C3H7 , CHF2, CHF2, or c-C3H 5 ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 R e ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, R e ; also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered saturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- membered saturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, or N, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, R e ;
  • R 1 wherein R x and R y together with the carbon they are attached form a 3- to 5-membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 also preffered is the R 1 wherein R x and R y together with the carbon they are attached form a 3- membered partially unsaturated carbocyclic ring, wherein the ring is unsubstituted;
  • R 1 is CF2CH3, 1-F-isopropyl or 1-F-cyclopropyl;
  • R e is halogen, OH, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R e is halogen, CN, OH, Ci-C 6 -alkoxy or Ci-C 6 -alkyl;
  • R e is OH or Ci-C 6 -alkoxy
  • Ci-C 6 -alkoxy particularly preferred OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 -alkynyloxy, Ci-C 6 -alkylthio, phenyloxy or phenyl-Ci-C 6 -alkoxy,
  • Ci-C6-alkoxy also particularly preferred OH, Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy, or Ci-C6-haloalkoxy;
  • Ci-C6-alkoxy especially preferred Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy, or Ci-C6-haloalkoxy;
  • Ci-C 6 -alkoxy also especially preferred OH, Ci-C 6 -alkoxy, or Ci-C 6 -haloalkoxy;
  • Ci-C 6 -alkoxy also most preferred Ci-C 6 -alkoxy.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C 3 -C 6 -cycloalkyl;
  • R 2 is OH, Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy or Ci-C6-haloalkoxy;
  • R 2 is Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy or Ci-C6-haloalkoxy
  • R 2 is OH or Ci-C 6 -alkoxy
  • R 2 is OH
  • R 2 is Ci-C 6 -alkoxy.
  • R x , R y together with the carbon they are attached form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring containing 0 or 1 heteroatom selected from O, N, or S, wherein the ring is substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is OH, Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy or Ci-C6-haloalkoxy;
  • R 2 is Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy, or Ci-C6-haloalkoxy
  • R 2 is OH or Ci-C 6 -alkoxy
  • R 2 is OH
  • R 2 is Ci-C 6 -alkoxy.
  • R 3 are selected from halogen, CN, NO 2 , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, and C 3 -C 6 -cycloalkyl;
  • R 3 are selected from halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci-C 6 -alkoxy; particularly preferred R 3 are selected from halogen, Ci-C 6 -alkyl, and Ci-C 6 -haloalkyl;
  • R 3 are selected from halogen, and Ci-C 6 -alkyl
  • R 3 is halogen, CH 3 , or CF 3 ;
  • R 3 is halogen
  • R 3 are selected from Cl, Br, and F; most preferred R 3 is Br or I;
  • R 3 is Br or Cl
  • R 3 is Br
  • R 3 is Cl
  • R 3 is F.
  • Preferred Z is phenyl or 5- or 6-membered heteroaryl ring
  • Z is phenyl or 9- or 10-membered partially or fully unsaturated bicyclic ring con- taining 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
  • Z is 5- or 6-membered heteroaryl ring or 9- or 10-membered partially or fully unsaturated bicyclic ring containing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; more preferred Z is phenyl substituted independently of their position with 0, 1 , 2, 3, or 4 R 3 ; most preferred Z is phenyl which is substituted at ortho position to the bond attached to pyrimi- dine ring with at least one R 3 , and which phenyl ring is further substituted with 0, 1 , 2, or 3 R 3 ; particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 ,
  • R 3 same or different are as defined herein including their preferred definition; m is 0, 1 , or 2, preferrably 0 or 1 ; and
  • # denotes the point of attachment to the pyrimidine ring
  • R 3 same or different are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and
  • # denotes the point of attachment to the pyrimidine ring
  • R 3 same or different are as defined herein including their preferred definition; m is 0, 1 , or 2, prferrably 0 or 1 ; and # denotes the point of attachment to the pyrimidine ring;
  • Z i.e. the group“Z-(R 3 ) m ”
  • R 3 is halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C 1 - C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkylthio, C 1 - C 6 -hal
  • # denotes the point of attachment to the pyrimidine ring; also more preferred Z is 5- or 6-membered heteroaryl ring;
  • Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine; particularly preferred Z is pyrimidine or pyridine;
  • especially preferred Z is pyridine.
  • Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole;
  • Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thio phene, furan, or pyrrole;
  • Z is thiophene, furan, or pyrrole
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups A to G,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • n 0 or 1 ;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups A1 to G1 ,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R 3b is H, halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from A, B, C, and D;
  • Z[i.e. the group“Z-(R 3 ) m ”] is A or C;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from E, F, and G; also most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is E or G;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from A1 , B1 , C1 , and D1 ; most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is A1 or C1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from E1 , F1 , and G1 ; also most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is E1 or G1 ;
  • Z is 9- or 10-membered partially or fully unsaturated bicyclic ring contain- ing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S; 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;
  • Z is 9 membered bicyclic ring
  • Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsatu- rated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N; also more particularly preferred Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the py- rimidine ring is a phenyl ring which is fused with another partially unsaturated 5-membered car- bocycle comprising 1 or 2 oxygen atoms;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 5- or 6- mem- bered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 heteroatoms se- lected from O or N;
  • Z is a 9-membered bicyclic ring wherein the ring attached to the pyrimidine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is 10 membered bicyclic ring
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered partially unsaturated 5- or 6- membered carbocycle comprising 1 , 2 or 3 heteroatoms selected from O or N;
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z is a 10-membered bicyclic ring wherein the ring attached to the pyrimidine ring is phenyl ring which is fused with another 6-membered partially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups H to V,
  • Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
  • R 3 same or differently are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci- C 6 -alkoxy;
  • n 0, 1 or 2;
  • R 4 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, 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 groups H to V,
  • Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
  • R 3 same or differently are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci- C 6 -alkoxy;
  • n 0, 1 or 2;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, or C 3 -C 6 -cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups H1 to V1 ,
  • Y 1 is 5- or 6-membered fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • R 3 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • R 3b and R 3c each independently is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or C1-C6- alkoxy ;
  • X 1 is O, S, or NR 3A ;
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyrimidine ring
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from H1 , 11 , K1 , L1 and R1.
  • Preferred Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • Y 1 is phenyl
  • Y 1 is 5-membered partially or fully unsaturated carbocycle compris- ing 1 , or 2 heteroatoms selected from O, N, and S;
  • Y 1 is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3-di- hydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole ; more preferably heteroatoms are selected from O and S, e.g.
  • Y 1 is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole,
  • heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
  • Y 1 is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms
  • Y 1 is 6-membered partially or fully unsaturated carbocycle compris- ing 0, 1 , or 2 heteroatoms selected from O, N, and S;
  • more preferred Y 1 is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y 1 is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms N;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H, I, J, K, L, M, N, O, P, Q, or R; most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is H, L, or M;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H or W 1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is S, T, U, or V;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 , 11 , J1 , K1 , L1 , M1 , N1 , 01 ,
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 , L1 , or M1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H 1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H1 or W1 a;
  • Z[i.e. the group“Z-(R 3 ) m ”] is S1 , T1 , U1 , or V1 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is H 1 , 11 , K1 , L1 and R1 ;
  • m 0, 1 , 2, or 3;
  • m is 0, 1 , or 2;
  • m 0;
  • m 1 ;
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl , or R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy;
  • Z is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl;
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cycloalkyl;
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy;
  • Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl.
  • R x and R y together with the carbon they are attached can form a 3-to 5-membered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy;
  • Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, C1-C6- alkyl, or Ci-C 6 -haloalkyl.
  • R 1 is 1 -F-cyclopropyl
  • R 2 is is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy;
  • Z is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl;
  • R 1 is 1 -F-isopropyl
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy;
  • R 2 is Ci-C 6 -alkoxy, C2-C6-alkynyloxy or Ci-C 6 -haloalkoxy
  • R 2 is OH or Ci-C 6 -alkoxy
  • R 2 is OH
  • R 2 is Ci-C 6 -alkoxy
  • Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 or H wherein m is 0 or 1 ; and R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 1 or 2;
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2.
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2.
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2;
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2.
  • compounds of formula (I) which corresponds to formula (I.E), and their use as herbicide,
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2.
  • R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2.
  • Z[i.e. the group“Z-(R 3 ) m ”] is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
  • R 3 is halogen, Ci-C 6 -alkyl, or Ci-C 6 -haloalkyl, preferably halogen;
  • n 0, 1 or 2.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2; more preferably, when m is 2, R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cyclo- alkyl, or R x and R y together with the carbon they are attached can form a 3-to 5-mem- bered saturated or partially unsaturated carbocyclic ring substituted with 0,1 , 2, 3, or 4 R e ;
  • R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen;
  • n 0, 1 or 2;
  • R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloal- kyl, or Ci-C 6 -alkoxy, preferably halogen.
  • R 1 is CF2CH 3 , 1 -F-isopropyl, or 1 -F-cyclopropyl;
  • R 2 is OH, OCH 3 , or OC 2 H 5 ;
  • Z[i.e. the group“Z-(R 3 ) m ”] is selected from 2-CI-C6H 4 , 2-Br-C6H 4 , 2-OH3-OQH 4 , 2-CI-4-F-C6H3, 2-CI-5-CF 3 -C 6 H 3 , 2-CI-5-F-C 6 H 3 , 3-CI-2-naphthyl, and 3-CH 3 -2-naphthyl;
  • compounds of the invention are the compounds of the formulae I that are compiled in the Tables A.
  • Compound 1 is compound 1 from Table A;
  • the pyrimidine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly.
  • Suitable components for mixtures are, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxypro- pionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbama- tes, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthal- imides, oxadiazoles, oxazolidinediones, oxyacetamides
  • pyrimidine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • other crop protection agents e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • compositions according to the present inven- tion comprise at least one pyrimidine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyrimidine compound of formula (I.
  • A) cor- responds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.B) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.C) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.D) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.E) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.F) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.G) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.H) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I. I) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- 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;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.K) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • the composition comprises as active corn- pound A or component A at least one, preferably exactly one, pyrimidine compound of for- mula (I.L) (corresponds to pyrimidine compound of formula (I)), as defined herein;
  • Preferred compounds of the formula (I) which, as component A, are constituent of the compo- sition according to the invention are the compounds I.A to I.L, 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 very long chain fatty acids
  • b11 cellulose biosynthesis inhibitors
  • herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dym- ron, methyl iodide,
  • the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bi- osynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-AC- Case herbicides).
  • ACCase herbicides belong to the group A of the HRAC classification sys- tem whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
  • compositions contain at least one ALS inhibitor (herbicide b2).
  • the herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • the compositions contain at least one inhibitor of pho- tosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the in- hibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI in- hibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSII inhibitors are preferred.
  • compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4).
  • the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
  • These inhibitors belong to the group E of the HRAC classification system.
  • the compositions contain at least one bleacher-herbi- cide (herbicide b5).
  • the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
  • These include compounds which inhibit carotenoid biosynthesis by in- hibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and corn- pounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - un- known target, group F3 of HRAC classification).
  • PDS inhibitors group F1 of HRAC classification
  • HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
  • DOXsynthase group F4 of HRAC class
  • corn- pounds which inhibit carotenoid
  • the compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid bio- synthesis in plants.
  • These inhibitors belong to the group G of the HRAC classification system.
  • compositions contain at least one glutamine syn- thetase inhibitor (herbicide b7).
  • the herbicidal activity of these compounds is based on the inhi- bition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants.
  • These inhibitors belong to the group H of the HRAC classification system.
  • compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • DHP synthase inhibitor herebicide b8
  • the herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase.
  • These inhibitors belong to the group I of the HRAC classification system.
  • the compositions contain at least one mitosis inhibitor (herbicide b9).
  • the herbicidal activity of these compounds is based on the disturbance or inhibi- tion of microtubule formation or organization, and thus on the inhibition of mitosis.
  • These inhibi- tors belong to the groups K1 and K2 of the HRAC classification system. Among these, corn- pounds of the group K1 , in particular dinitroanilines, are preferred.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • VLCFA inhibitor herebicide b10
  • the herbicidal activity of these compounds is based on the inhibition of the syn- thesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants.
  • These inhibitors belong to the group K3 of the HRAC classification system.
  • the compositions contain at least one cellulose bio- synthesis inhibitor (herbicide b11 ).
  • the herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants.
  • These inhibitors belong to the group L of the HRAC classification system.
  • compositions contain at least one decoupler herbi- cide (herbicide b12).
  • the herbicidal activity of these compounds is based on the disruption of the cell membrane.
  • These inhibitors belong to the group M of the HRAC classification system.
  • the compositions contain at least one auxinic herbi- cide (herbicide b13).
  • auxinic herbi- cide include compounds that mimic auxins, i.e. plant hormones, and af- fect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor hereinicide b14
  • the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
  • These compounds belong to the group P of the HRAC classifica- tion system.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
  • herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
  • herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
  • pyhmidinylbenzoates such as bispyribac, bispyhbac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-40- 5), N-(4-bromophenyl)-2-[
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions compris- ing at least one imidazolinone herbicide
  • inhibitors of the photosystem II e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one
  • a preferred embodiment of the invention relates to those composi- tions comprising at least one aryl urea herbicide.
  • a preferred embodi- ment of the invention relates to those compositions comprising at least one triazine herbicide.
  • a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide; b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufen
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NOS NOS NOS NOS NOS NOS
  • HPPD inhibitors benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophen
  • bilanaphos biases
  • bilanaphos biases
  • bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, corn- pounds of group K1 , in particular dinitroanilines are preferred; b10) from the group of the VLCFA inhibitors:
  • chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3,
  • isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
  • chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pentafluorphenyloxy-1 4 - [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
  • 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl
  • auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
  • Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
  • 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
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
  • glufosinate glufosinate-P, glufosinate-ammonium
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • 2,4-D and its salts and esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and es- ters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chlor
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B that can be used in combination with the pyrimidine corn- pounds of the formula (I) according to the present invention are:
  • b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro- 4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-flu
  • ALS inhibitors from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon
  • b3 from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1 );
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • auxinic herbicides 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
  • herbicides B could also be B.203 which is cyclopyranil.
  • compositions according to the present in- vention comprise at least one pyrimidine compound of formula (I) and at least one safener C.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the pre- sent compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant.
  • the safeners and the pyrimidine compounds of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-d i hyd ro-5-a I kyl- 1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-
  • Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxa- zolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).
  • Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy- dride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3),
  • Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroace- tyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroace- tyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
  • safeners C which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
  • the active compounds B of groups b1 ) to b15) and the active compounds C are known herbi- cides and safeners, see, e.g., The Compendium of Pesticide Common Names (http://www.alan- wood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Com- pany, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of Amer- ica, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Sci- ence Society of America, 1998.
  • the assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this sub- stance was only assigned to one mechanism of action.
  • Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agricul- turally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • suitable ester are dicamba-methyl and dicam ba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammoni- um, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and 2,4-D- N,N,N-trimethylethanolammonium (2,
  • esters of 2,4-D are 2,4- D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D- ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D- octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • Suitable salts of 2,4-DB are e.g. 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethyl- ammonium.
  • Suitable esters of 2,4-DB are e.g. 2,4-DB-butyl and 2,4-DB-isoctyl.
  • Suitable salts of dichlorprop are e.g. dichlorprop-sodium, dichlorprop-potassium and dichlor- prop-dimethylammonium.
  • suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable es- ter of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are e.g. triclopyr-ethyl and triclopyr-butotyl.
  • Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diola- mine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
  • Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6- TBA-potassium and 2,3,6-TBA-sodium.
  • Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dime- thylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are e.g. glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref- erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sul- fosate).
  • a suitable salt of glufosinate is e.g. glufosinate-ammonium.
  • a suitable salt of glufosinate-P is e.g. glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are e.g. bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • Suitable salts and esters of ioxonil are e.g. ioxonil-octanoate, ioxonil-potassium and ioxonil- sodium.
  • Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammo- nium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
  • Suitable salts of mecoprop-P are e.g. mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-so- dium.
  • a suitable salt of diflufenzopyr is e.g. diflufenzopyr-sodium.
  • a suitable salt of naptalam is e.g. naptalam-sodium.
  • Suitable salts and esters of aminocyclopyrachlor are e.g. aminocyclopyrachlor-dimethylammo- nium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclo- pyrachlor-sodium and aminocyclopyrachlor-potassium.
  • a suitable salt of quinclorac is e.g. quinclorac-dimethylammonium.
  • a suitable salt of quinmerac is e.g. quinmerac-dimethylammonium.
  • a suitable salt of imazamox is e.g. imazamox-ammonium.
  • Suitable salts of imazapic are e.g. imazapic-ammonium and imazapic-isopropylammonium.
  • Suitable salts of imazapyr are e.g. imazapyr-ammonium and imazapyr-isopropylammonium.
  • a suitable salt of imazaquin is e.g. imazaquin-ammonium.
  • Suitable salts of imazethapyr are e.g. imazethapyr-ammonium and imazethapyr-isoprop- ylammonium.
  • a suitable salt of topramezone is e.g. topramezone-sodium.
  • the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
  • the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
  • the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbi- cides B different from each other.
  • the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
  • the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, and as 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 selected from compound 1 to 72 from the table A, and at least two, preferably exactly two, herbi- cides B different from each other.
  • component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, and at least two, preferably exactly two, herbi- cides B different from each other.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, and at least three, preferably exactly three, herbicides B different from each other.
  • the composition comprises as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, 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 selected from compound 1 to 72 from the table A, as component B at least one, preferably ex- actly one, herbicide B, and as component C at least one, preferably exactly one safener C.
  • the composition comprises as component A at least one, preferably exactly pyrimidine compound of formula (I), preferably se- lected from compound 1 to 72 from the table A, 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 as component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, at least three, preferably exactly three herbi- cides B different from each other, and as component C at least one, preferably exactly one, saf- ener C.
  • component A at least one, preferably exactly one pyrimidine compound of formula (I), preferably selected from compound 1 to 72 from the table A, at least three, preferably exactly three herbi- cides B different from each other, and as component C at least one, preferably exactly one, saf- ener C.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b1 ), in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P- ethyl, metamifop, pinoxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb and triallate.
  • an active compound from the group consisting of compound 1 to 72 from the table A at least one and especially exactly one herbi- cidally active compound from group b1
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b2), in particular selected from the group consisting of ben- sulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosul- famuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammo- nium, imazapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, imazaquin, imazaquin- am
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting compound 1 to 72 from the table A, at least one and especially exactly one herbicid- ally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bro- moxynil-potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, paraquat-dichloride, propanil, simazin, terbutryn and terbuthylazine.
  • ametryn atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bro- moxynil-potassium, di
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin , ethyl [3-[2-chloro-4- fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyri- dyl
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), pico- linafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, topramezone-sodium and 2-chloro-3-methylsulfanyl-N-(1 -methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0) .
  • an active compound from the group consisting of compound 1 to 72 from the table A in
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium , glyphosate-isoprop- ylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate-P and glufosinate-P-ammonium.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone.
  • a pyrimidine compounds of formula (I) especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentraz
  • compositions comprising in addition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, 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, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
  • a pyrimidine compounds of formula (I) especially an active compound from the group consisting of compound 1 to 72 from the table A, 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, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b1 1), in particular indaziflam, isoxaben and triaziflam.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally 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, aminocy- clopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, ami- nopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammo- nium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicam ba-butotyl, dicamba-di- glycol
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
  • a pyrimidine compounds of formula (I) especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one herbi- cidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
  • the composition comprises, in ad- dition to a pyrimidine compounds of formula (I), especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31-4).
  • a pyrimidine compounds of formula (I) especially an active compound from the group consisting of compound 1 to 72 from the table A, at least one and especially exactly one safener C, in particular selected from the
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , prefera- bly in the range of from 1 :500 to 500:1 , in particular in the range of from
  • weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
  • compositions mentioned below comprising the pyrimidine corn- pounds of formula I as defined and the substance(s) as defined in the respective row of table T; especially preferred comprising as only herbicidal active compounds the pyrimidine corn- pounds of formula I as defined and the substance(s) as defined in the respective row of table T; most preferably comprising as only active compounds the pyrimidine compounds of formula I as defined and the substance(s) as defined in the respective row of table T.
  • compositions 1.1 to 1.3653 comprising the compound 1 from table A and the substance(s) as defined in the respective row of table T:
  • compositions 1.3654 to 1.3671 comprising the compound (1.49.15), and the substance(s) as defined in the respective row of table W:
  • Composition 1.203 e.g. comprises the compound 1 from table A, clethodim (B.1 ) and be- noxacor (C.I ) (see table B, entry B.1 and table C, entry C.1 ).
  • compositions 2.1 to 2.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound 2 from table A, in place of the compound 1.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • compositions 10.1 to 10.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.51 as further herbicide B.
  • compositions 1 1.1 to 1 1.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.55 as further herbicide B.
  • compositions 12.1 to 12.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.56 as further herbicide B.
  • compositions 13.1 to 13.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.64 as further herbicide B.
  • compositions 14.1 to 14.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.66 as further herbicide B.
  • compositions 15.1 to 15.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.67 as further herbicide B.
  • compositions 16.1 to 16.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.68 as further herbicide B.
  • compositions 17.1 to 17.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.69 as further herbicide B.
  • compositions 18.1 to 18.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.73 as further herbicide B.
  • compositions 19.1 to 19.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.76 as further herbicide B.
  • compositions 20.1 to 20.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.81 as further herbicide B.
  • compositions 21.1 to 21.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.82 as further herbicide B.
  • compositions 22.1 to 22.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.85 as further herbicide B.
  • compositions 23.1 to 23.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.88 as further herbicide B.
  • compositions 24.1 to 24.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.89 as further herbicide B.
  • compositions 25.1 to 25.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.94 as further herbicide B.
  • compositions 26.1 to 26.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.95 as further herbicide B.
  • compositions 27.1 to 27.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.98 as further herbicide B.
  • compositions 28.1 to 28.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.100 as further herbicide B.
  • compositions 29.1 to 29.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 as further herbicide B.
  • compositions 30.1 to 30.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.67 as further herbicides B.
  • compositions 31.1 to 31.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.76 as further herbicides B.
  • compositions 32.1 to 32.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.103 and B.82 as further herbicides B.
  • compositions 33.1 to 33.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 as further herbicide B.
  • compositions 34.1 to 34.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.67 as further herbicides B.
  • compositions 35.1 to 35.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.76 as further herbicides B.
  • compositions 36.1 to 36.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.104 and B.82 as further herbicides B.
  • compositions 37.1 to 37.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.106 as further herbicide B.
  • compositions 38.1 to 38.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.107 as further herbicide B.
  • compositions 39.1 to 39.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
  • compositions 40.1 to 40.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
  • compositions 41.1 to 41.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
  • compositions 42.1 to 42.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.109 as further herbicide B.
  • compositions 43.1 to 43.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 as further herbicide B.
  • compositions 44.1 to 44.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 11 and B.67 as further herbicides B.
  • compositions 45.1 to 45.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 and B.76 as further herbicides B.
  • compositions 46.1 to 46.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.11 1 and B.82 as further herbicides B.
  • compositions 47.1 to 47.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B. 1 16 as further herbicide B.
  • compositions 48.1 to 48.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.67 as further herbicides B.
  • compositions 49.1 to 49.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.116 and B.94 as further herbicides B.
  • compositions 50.1 to 50.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.103 as fur- ther herbicides B.
  • compositions 51.1 to 51.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.128 as fur- ther herbicides B.
  • compositions 52.1 to 52.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.104 as fur- ther herbicides B.
  • compositions 53.1 to 53.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.107 as fur- ther herbicides B.
  • compositions 54.1 to 54.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.1 16 and B.11 1 as fur- ther herbicides B.
  • compositions 55.1 to 55.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.122 as further herbicide B.
  • compositions 56.1 to 56.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.126 as further herbicide B.
  • compositions 57.1 to 57.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.128 as further herbicide B.
  • compositions 58.1 to 58.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.131 as further herbicide B.
  • compositions 59.1 to 59.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.132 as further herbicide B.
  • compositions 60.1 to 60.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.133 as further herbicide B.
  • compositions 61.1 to 61.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.135 as further herbicide B.
  • compositions 62.1 to 62.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.137 as further herbicide B.
  • compositions 63.1 to 63.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.138 as further herbicide B.
  • compositions 64.1 to 64.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.140 as further herbicide B.
  • compositions 65.1 to 65.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.145 as further herbicide B.
  • compositions 66.1 to 66.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.153 as further herbicide B.
  • compositions 67.1 to 67.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.156 as further herbicide B.
  • compositions 68.1 to 68.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.171 as further herbicide B.
  • compositions 69.1 to 69.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they additionally comprise B.174 as further herbicide B.
  • compositions 70.1 to 70.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 3 from table A, in place of the compound 1.
  • compositions 71.1 to 71.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 4 from table A, in place of the compound 1.
  • compositions 72.1 to 72.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 5 from table A, in place of the compound 1.
  • compositions 73.1 to 73.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 6 from table A, in place of the compound 1.
  • compositions 74.1 to 74.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 7 from table A, in place of the compound 1.
  • compositions 75.1 to 75.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 8 from table A, in place of the compound 1.
  • compositions 76.1 to 76.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 9 from table A, in place of the compound 1.
  • compositions 77.1 to 77.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 10 from table A, in place of the compound 1.
  • compositions 78.1 to 78.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 1 1 from table A, in place of the compound 1.
  • compositions 79.1 to 79.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 12 from table A, in place of the compound 1.
  • compositions 80.1 to 80.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 13 from table A, in place of the compound 1 .
  • compositions 81.1 to 81.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 14 from table A, in place of the compound 1 .
  • compositions 82.1 to 82.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they comprise the compound 15 from table A, in place of the compound 1 .
  • compositions 83.1 to 83.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 16 from table A, in place of the compound 1 .
  • compositions 84.1 to 84.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 17 from table A, in place of the compound 1 .
  • compositions 85.1 to 85.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 18 from table A, in place of the compound 1 .
  • compositions 86.1 to 86.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 19 from table A, in place of the compound 1 .
  • compositions 87.1 to 87.3653 which differ from the correspond- ing compositions 1 .1 to 1.3653 only in that they comprise the compound 20 from table A, in place of the compound 1 .
  • compositions 88.1 to 88.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 21 from table A, in place of the compound 1.
  • compositions 89.1 to 89.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 22 from table A, in place of the compound 1 .
  • compositions 90.1 to 90.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 23 from table A, in place of the compound 1 .
  • compositions 91.1 to 91.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 24 from table A, in place of the compound 1 .
  • compositions 92.1 to 92.3653 which differ from the correspond- ing compositions 1 .1 to 1.3653 only in that they comprise the compound 25 from table A, in place of the compound 1 .
  • compositions 93.1 to 93.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 26 from table A, in place of the compound 1 .
  • compositions 94.1 to 94.3653 which differ from the correspond- ing compositions 1 .1 to 1 .3653 only in that they comprise the compound 27 from table A, in place of the compound 1 .
  • compositions 95.1 to 95.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 28 from table A, in place of the compound 1.
  • compositions 96.1 to 96.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 29 from table A, in place of the compound 1.
  • compositions 97.1 to 97.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 30 from table A, in place of the compound 1.
  • compositions 98.1 to 98.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 31 from table A, in place of the compound 1.
  • compositions 99.1 to 99.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound 32 from table A, in place of the compound 1.
  • compositions 100.1 to 100.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 33 from table A, in place of the compound 1.
  • compositions 101.1 to 101.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 34 from table A, in place of the compound 1.
  • compositions 102.1 to 102.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 35 from table A, in place of the compound 1.
  • compositions 103.1 to 103.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 36 from table A, in place of the compound 1.
  • compositions 104.1 to 104.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 37 from table A, in place of the compound 1.
  • compositions 105.1 to 105.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 38 from table A, in place of the compound 1.
  • compositions 106.1 to 106.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound 39 from table A, in place of the compound 1.
  • compositions 107.1 to 107.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 40 from table A, in place of the compound 1.
  • compositions 108.1 to 108.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 41 from table A, in place of the compound 1.
  • compositions 109.1 to 109.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 42 from table A, in place of the compound 1.
  • compositions 1 10.1 to 110.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 43 from table A, in place of the compound 1.
  • compositions 11 1.1 to 1 11.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 44 from table A, in place of the compound 1.
  • compositions 1 12.1 to 112.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 45 from table A, in place of the compound 1.
  • compositions 1 13.1 to 113.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 46 from table A, in place of the compound 1.
  • compositions 1 14.1 to 114.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 47 from table A, in place of the compound 1.
  • compositions 1 15.1 to 115.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 48 from table A, in place of the compound 1.
  • compositions 1 16.1 to 116.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 49 from table A, in place of the compound 1.
  • compositions 117.1 to 1 17.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 50 from table A, in place of the compound 1.
  • compositions 118.1 to 1 18.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 51 from table A, in place of the compound 1.
  • compositions 1 19.1 to 119.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 52 from table A, in place of the compound 1.
  • compositions 120.1 to 120.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 53 from table A, in place of the compound 1.
  • compositions 121.1 to 121.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 54 from table A, in place of the compound 1.
  • compositions 122.1 to 122.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 55 from table A, in place of the compound 1.
  • compositions 123.1 to 123.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 56 from table A, in place of the compound 1.
  • compositions 124.1 to 124.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 57 from table A, in place of the compound 1.
  • compositions 125.1 to 125.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 58 from table A, in place of the compound 1.
  • compositions 126.1 to 126.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 59 from table A, in place of the compound 1.
  • compositions 127.1 to 127.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 60 from table A, in place of the compound 1.
  • compositions 128.1 to 128.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 61 from table A, in place of the compound 1.
  • compositions 129.1 to 129.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 62 from table A, in place of the compound 1.
  • compositions 130.1 to 130.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 63 from table A, in place of the compound 1.
  • compositions 131.1 to 131.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 64 from table A, in place of the compound 1.
  • compositions 132.1 to 132.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 65 from table A, in place of the compound 1.
  • compositions 133.1 to 133.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 66 from table A, in place of the compound 1.
  • compositions 134.1 to 134.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 67 from table A, in place of the compound 1.
  • compositions 135.1 to 135.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 68 from table A, in place of the compound 1.
  • compositions 136.1 to 136.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 69 from table A, in place of the compound 1.
  • compositions 137.1 to 137.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 70 from table A, in place of the compound 1.
  • compositions 138.1 to 138.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 71 from table A, in place of the compound 1.
  • compositions 139.1 to 139.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 72 from table A, in place of the compound 1.
  • 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 2 from table A, in place of the compound 1.
  • compositions 3.3654 to 3.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.2 as further herbi- cide B.
  • compositions 4.3654 to 4.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.8 as further herbi- cide B.
  • compositions 5.3654 to 5.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.30 as further herbi- cide B.
  • compositions 6.3654 to 6.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.32 as further herbi- cide B.
  • compositions 7.3654 to 7.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.35 as further herbi- cide B.
  • compositions 8.3654 to 8.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.38 as further herbi- cide B.
  • compositions 9.3654 to 9.3671 which differ from the correspond- ing compositions 1.3654 to 1.3671 only in that they additionally comprise B.40 as further herbi- cide B.
  • compositions 10.3654 to 10.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.51 as further herbicide B.
  • compositions 11.3654 to 1 1.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.55 as further herbicide B.
  • compositions 12.3654 to 12.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.56 as further herbicide B.
  • compositions 13.3654 to 13.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.64 as further herbicide B.
  • compositions 14.3654 to 14.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.66 as further herbicide B.
  • compositions 15.3654 to 15.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.67 as further herbicide B.
  • compositions 16.3654 to 16.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.68 as further herbicide B.
  • compositions 17.3654 to 17.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.69 as further herbicide B.
  • compositions 18.3654 to 18.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.73 as further herbicide B.
  • compositions 19.3654 to 19.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.76 as further herbicide B.
  • 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.
  • compositions 21.3654 to 21.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.82 as further herbicide B.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 herbi-cides B.
  • compositions 31.3654 to 31.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.103 and B.76 as further herbi-cides B.
  • 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 herbi-cides B.
  • 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.
  • 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 herbi-cides B.
  • 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 herbi-cides B.
  • 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 herbi-cides B.
  • 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.
  • 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.
  • 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 herbi-cides B.
  • 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 herbi-cides B.
  • compositions 41.3654 to 41.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B. 107 and B.82 as further herbi-cides B.
  • 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.
  • 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.11 1 as further herbicide B.
  • 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.1 11 and B.67 as further herbi-cides B.
  • compositions 45.3654 to 45.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.11 1 and B.76 as further herbi-cides B.
  • 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.11 1 and B.82 as further herbi-cides B.
  • 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. 1 16 as fur- ther herbicide B.
  • 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 herbi-cides B.
  • 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.1 16 and B.94 as further herbi-cides B.
  • compositions 50.3654 to 50.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.103 as further herbi-cides B.
  • compositions 51.3654 to 51.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.1 16 and B.128 as further herbi-cides B.
  • 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.1 16 and B.104 as further herbi-cides B.
  • 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.1 16 and B.107 as further herbi-cides B.
  • 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.1 16 and B.1 1 1 as further herbi-cides B.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • compositions 61.3654 to 61.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.135 as further herbicide B.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 3 from table A, in place of the compound 1.
  • compositions 71.3654 to 71.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 4 from table A, in place of the compound 1.
  • 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 5 from table A, in place of the compound 1.
  • 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 6 from table A, in place of the compound 1.
  • 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 7 from table A, in place of the compound 1.
  • 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 8 from table A, in place of the compound 1.
  • 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 9 from table A, in place of the compound 1.
  • 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 10 from table A, in place of the compound 1.
  • 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 1 from table A, in place of the compound 1.
  • 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 12 from table A, in place of the compound 1.
  • 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 13 from table A, in place of the compound 1.
  • compositions 81.3654 to 81.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 14 from table A, in place of the compound 1.
  • 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 15 from table A, in place of the compound 1.
  • 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 16 from table A, in place of the compound 1.
  • 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 17 from table A, in place of the compound 1.
  • 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 18 from table A, in place of the compound 1.
  • 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 19 from table A, in place of the compound 1.
  • 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 20 from table A, in place of the compound 1.
  • 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 21 from table A, in place of the compound 1.
  • 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 22 from table A, in place of the compound 1.
  • 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 23 from table A, in place of the compound 1.
  • compositions 91.3654 to 91.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 24 from table A, in place of the compound 1.
  • 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 25 from table A, in place of the compound 1.
  • 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 26 from table A, in place of the compound 1.
  • 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 27 from table A, in place of the compound 1.
  • 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 28 from table A, in place of the compound 1.
  • 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 29 from table A, in place of the compound 1.
  • 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 30 from table A, in place of the compound 1.
  • 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 31 from table A, in place of the compound 1.
  • 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 32 from table A, in place of the compound 1.
  • compositions 100.3654 to 100.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 33 from table A, in place of the compound 1.
  • compositions 101.3654 to 101.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 34 from table A, in place of the compound 1.
  • 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 35 from table A, in place of the compound 1.
  • 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 36 from table A, in place of the compound 1.
  • 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 37 from table A, in place of the compound 1.
  • 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 38 from table A, in place of the compound 1.
  • 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 39 from table A, in place of the compound 1.
  • 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 40 from table A, in place of the compound 1.
  • 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 41 from table A, in place of the compound 1.
  • 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 42 from table A, in place of the compound 1.
  • 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 43 from table A, in place of the compound 1.
  • compositions 11 1.3654 to 11 1.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 44 from table A, in place of the compound 1.
  • 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 45 from table A, in place of the compound 1.
  • compositions 1 13.3654 to 113.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 46 from table A, in place of the compound 1.
  • compositions 114.3654 to 114.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 47 from table A, in place of the compound 1.
  • compositions 115.3654 to 115.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 48 from table A, in place of the compound 1.
  • compositions 116.3654 to 116.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 49 from table A, in place of the compound 1.
  • compositions 117.3654 to 117.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 50 from table A, in place of the compound 1.
  • compositions 118.3654 to 118.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 51 from table A, in place of the compound 1.
  • compositions 119.3654 to 119.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 52 from table A, in place of the compound 1.
  • 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 53 from table A, in place of the compound 1.
  • 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 54 from table A, in place of the compound 1.
  • 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 55 from table A, in place of the compound 1.
  • 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 56 from table A, in place of the compound 1.
  • 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 57 from table A, in place of the compound 1.
  • 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 58 from table A, in place of the compound 1.
  • 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 59 from table A, in place of the compound 1.
  • 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 60 from table A, in place of the compound 1.
  • 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 61 from table A, in place of the compound 1.
  • compositions 129.3654 to 129.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 62 from table A, in place of the compound 1.
  • compositions 130.3654 to 130.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 63 from table A, in place of the compound 1.
  • compositions 131.3654 to 131.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they comprise the compound 64 from table A, in place of the compound 1.
  • 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 65 from table A, in place of the compound 1.
  • 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 66 from table A, in place of the compound 1.
  • 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 67 from table A, in place of the compound 1.
  • 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 68 from table A, in place of the compound 1.
  • 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 69 from table A, in place of the compound 1.
  • 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 70 from table A, in place of the compound 1.
  • 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 71 from table A, in place of the compound 1.
  • 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 72 from table A, in place of the compound I .
  • the invention also relates to agrochemical compositions compris- ing at least an auxiliary and at least one pyrimidine compound of formula (I) according to the in- vention.
  • An agrochemical composition comprises a pesticidal effective amount of a pyrimidine corn- pound of formula (I).
  • 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.
  • 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.
  • agrochemical 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 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
  • gel formulations for the treat- ment of plant propagation materials such as seeds (e.g. GF).
  • 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.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, disper- sants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibil- izers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil frac- tions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic, and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydr
  • 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.
  • 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.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, non-ionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty ac- ids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sul- fonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates
  • Examples of sul- fates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Exam- pies of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters, or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose, and glucose esters, or al- kylpoly-glucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium corn- pounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable am- photeric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block poly- mers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the pyrimidine compounds of for- mula (I) on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants, and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaCoCHarides (e.g. xanthan gum, carboxymethylcellulose), inor- ganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • a pyrimidine compound of formula (I) according to the invention 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.
  • a pyrimidine compound of formula (I) according to the invention 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.
  • dis persant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • 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).
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a pyrimidine compound of formula (I) in an agitated ball mill, 20-60 wt% of a pyrimidine compound of formula (I) according to the in- vention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspen- sion of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 01-2 wt% thickener e.g. xanthan gum
  • water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspen- sion of the active substance.
  • binder e.g. polyvinylalco- hol
  • a pyrimidine compound of formula (I) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethox- ylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a sta- ble dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethox- ylate
  • a pyrimidine compound of formula (I) 50-80 wt% of a pyrimidine compound of formula (I) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wet- ting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-3 wt% wet- ting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a pyrimidine compound of formula (I) 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.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. carboxymethylcellulose
  • 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.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • sur- factant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the in- vention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid, and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initi- ated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol
  • an oil phase comprising 5-50 wt% of a pyrimidine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an iso- cyanate monomer (e.g. diphenylmethene-4,4’-diisocyanate) are dispersed into an aqueous so- lution of a protective colloid (e.g. polyvinyl alcohol).
  • a polyamine e.g. hexameth- ylenediamine
  • the monomers amount to 1- 10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 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%.
  • solid carrier e.g. finely divided kaolin
  • a pyrimidine compound of formula (I) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • solid carrier e.g. silicate
  • Granulation is achieved by extru- sion, spray-drying or the fluidized bed.
  • a pyrimidine compound of formula (I) according to the invention 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%.
  • organic solvent e.g. aromatic hydrocarbon
  • 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.
  • auxiliaries such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
  • the agrochemical compositions comprising generally comprise between 0.01 and 95%, prefer- ably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the pyrimidine compound of formula (I).
  • the pyrimidine compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the agrochemi- cal compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use prepa- rations. Application can be carried out before or during sowing.
  • Methods for applying pyrimidine compounds of formula (I) and agrochemical compositions thereof, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • 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.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the py- rimidine compounds of formula (I) and the agrochemical compositions comprising them as pre- mix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the agrochemical compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the pyrimidine compound of formula (I) according to the invention and the ag- rochemical compositions comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical compo- sition is made up with water, buffer, and/or further auxiliaries to the desired application concen- tration and the ready-to-use spray liquor or the agrochemical composition according to the in- vention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to- use spray liquor are applied per hectare of agricultural useful area.
  • 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.
  • 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.
  • 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 them are applied to the plants mainly by spraying the leaves.
  • the application can be carried out using, e.g., water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (e.g. from 300 to 400 l/ha).
  • the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them may also be applied by the low-volume or the ultra-low-volume method, or in the form of micro granules.
  • pyrimidine compounds of formula (I), or the agrochemical compositions corn- prising them can be done before, during, and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the pyrimidine compounds of formula (I), or the agrochemical composi- tions comprising them, by applying seed, pretreated with the pyrimidine compounds of formula (I), or the agrochemical compositions comprising them, of a crop plant.
  • application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • 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
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, e.g., corns, seeds, fruits, tubers, seedlings and similar forms.
  • 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.
  • the amounts of active substances applied 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.
  • 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.).
  • the rates of application of the pyrimidine compounds of formula (I) according to the present invention 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.
  • the application rates of the pyrimidine corn- pounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
  • the application rate of the pyrimidine corn- pounds of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, and most preferably from 5 to 100 g, per 100 kilogram of plant prop- agation material (preferably seeds) are generally required.
  • 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.
  • 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.
  • 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.
  • suitable crops are the following:
  • 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 sativ
  • Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or permanent crops.
  • the pyrimidine compounds of formula (I) according to the invention, or the agrochemical corn- positions comprising them, can also be used in the treatment of genetically modified plants.
  • the term“genetically modified plants” is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species’ genome or to exhibit a deletion of DNA that was na- tive to that species’ genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone.
  • a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique.
  • one or more genes have been inte- grated into the genetic material of a genetically modified plant in order to improve certain prop- erties of the plant.
  • Such genetic modifications also include but are not limited to targeted post- translational modification of protein(s), oligo- or polypeptides e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
  • e. bromoxynil or ioxynil herbicides as a result of con- ventional methods of breeding or genetic engineering; furthermore, plants have been made re- sistant to multiple classes of herbicides through multiple genetic modifications, such as re- sistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • herbicide resistance technologies are, e.g., described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Sci- ence 316, 2007, 1185; and references quoted therein.
  • Several cultivated plants have been ren- dered tolerant to herbicides by mutagenesis and conventional methods of breeding, e. g., Clear- field® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.
  • plants also include those are by the use of recombinant DNA techniques 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, Cryl 11 B(b1 ) or Cry9c; vegetative insecticidal pro- teins (VIP), e. g., VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of bacteria colonizing nema- todes, e. g., Photorhabdus spp.
  • delta-endotoxins e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, Cryl 11 B(b1 ) or Cry9c
  • VIP
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins pro- prised by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; ag- glutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cys- tatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxy-steroid oxidase, ec- dysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-re- ductase
  • i fungi
  • RIP proteinas
  • these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combina- tion of protein domains, (see, e. g., WO 02/015701 ).
  • Further examples of such toxins or genet- ically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810, and WO
  • insecticidal proteins contained in the genetically modified plants impart to the plants pro- ducing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, espe- cially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecti- cidal proteins are, e.
  • YieldGard® (com cultivars producing the CrylAb toxin), Yield- Gard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars pro- ducing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars produc- ing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeat® (potato cultivars producing the Cry3A toxin); Bt-Xtra
  • 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 producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants also include those are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called“pathogenesis- related proteins” (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Er- winia amylovora).
  • PR proteins so-called“pathogenesis- related proteins”
  • 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
  • plants also include those are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral patho- gens of those plants.
  • productivity e.g., bio-mass production, grain yield, starch content, oil content or protein content
  • tolerance to drought e.g., salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral patho- gens of those plants.
  • plants also include those contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nu- trition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsatu- rated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
  • 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).

Abstract

La présente invention concerne des composés de pyrimidine de formule (I), ou leurs sels ou dérivés acceptables sur le plan agricole, en tant qu'herbicides, les variables étant définies selon la description, l'utilisation de composés de pyrimidine de formule (I) en tant qu'herbicide, des compositions les comprenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nuisibles, l'invention concerne également un procédé pour lutter contre la végétation indésirable qui consiste à laisser agir une quantité herbicide efficace d'au moins un des composés de pyrimidine de formule (I) sur les plantes, leurs graines et/ou leur habitat.
PCT/EP2018/085006 2017-12-20 2018-12-14 Composés herbicides de pyrimidine WO2019121408A1 (fr)

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