WO2019141552A1 - Composés herbicides de triazine - Google Patents
Composés herbicides de triazine Download PDFInfo
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- WO2019141552A1 WO2019141552A1 PCT/EP2019/050376 EP2019050376W WO2019141552A1 WO 2019141552 A1 WO2019141552 A1 WO 2019141552A1 EP 2019050376 W EP2019050376 W EP 2019050376W WO 2019141552 A1 WO2019141552 A1 WO 2019141552A1
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- alkyl
- alkoxy
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- haloalkoxy
- carbonyl
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- 0 CC(C)(c1nc(C(*)=O)c(C2CCCC(C)(C)CCC2)nn1)F Chemical compound CC(C)(c1nc(C(*)=O)c(C2CCCC(C)(C)CCC2)nn1)F 0.000 description 5
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
Definitions
- the present invention relates to triazine 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.
- R 1 is C 2 -C 6 -alkyl, Ci-C 6 -haloalkyl, HO-Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 - C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -cyclo- alkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3
- R 1 is formula R 1A
- R x , R y independently of each other are selected from H, halogen, Ci-C6-alkyl, Ci-C6-haloal- kyl, HO-Ci-C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 - alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C6-haloalkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -halocyc- loalkoxy, C 3 -C 6
- 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-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxy- carbonyl-Ci-C 6 -alkyl, Ci-C 6 -haloalkylcarbonyl-Ci-C 6 -alkyl, Ci-C 6 -haloalkoxycarbonyl-Ci- C 6 -alkyl, Ci-C 6 -alkylcarbonyl-Ci-C 6 -haloalkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -haloalkyl, C1- C 6 -haloalkylcarbonyl-Ci-C 6 -haloalkyl, Ci-C 6 -haloalkoxycarbonyl-Ci-C 6 -haloalkyl, OH, C1- C 6 -alkoxy
- 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, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy or C1-C6- 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 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, NO2, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al- kynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycar- bonyl, C1-C6-alkoxycarbonyl, C1-
- the present invention provides the compounds of formula (I)
- R 1 is C2-C6-alkyl, Ci-C 6 -haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C 6 -alkynyl, C3-C6-haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyl- oxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloal- koxy, C3-C6-cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, Ci-C 6 -alkylthi
- R 1 is R 1A
- R x , R y independently of each other are selected from H, halogen, Ci-C 6 -alkyl, C 1 -C 6 - haloalkyl, HO-Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloal- kenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -Ce-cyc- loalkoxy, C 3 -C 6 -halocyclo
- 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-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl-Ci-C 6 -alkyl, C 1 -C 6 - alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -haloalkylcarbonyl-Ci-C 6 -alkyl, Ci-C 6 -haloalkoxy- carbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl-Ci-C 6 -haloalkyl, Ci-C 6 -alkoxycarbonyl-Ci- C 6 -haloalkyl, Ci-C 6 -haloalkylcarbonyl-Ci-C 6 -haloalkyl, Ci-C 6 -haloalkylcarbonyl-Ci-C 6 -haloalkyl, Ci-C 6 -haloalkylcarbon
- 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 Ci-C6-haloalkoxy;
- Z is phenyl, 5- or 6-membered heteroaryl, or 9- or 1 0-membered partially or fully un- saturated bicyclic ring containing 0, 1 , 2, 3, 4, or 5 heteroatoms selected from O, N, and S;
- R 3 is same or differently H, halogen, CN, NO 2 , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl- carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 - alkoxy, Ci-C6-haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycar- bonyl, Ci-C 6 -alkylthio, Ci-C 6 -halo
- R e is halogen, CN, NO2, 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 phenyl
- R 2 is NHCH(CH3)2
- Z-(R 3 ) m is not phenyl, 4-CIC6H4 or 4- N0 2 C 6 H 4 ;
- R 1 when R 1 is phenyl, R 2 is NH2, Z-(R 3 ) m is not phenyl, 4-CIC6H4 or 4-N02C6H4; and when R 1 is phenyl, R 2 is CH 3 , Z-(R 3 ) m is not phenyl.
- the present invention also provides use of the triazine compounds of formula (I) as described 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 triazine compounds of formula (I) as described 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 triazine compound of formula (I) in- cluding agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, or compositions thereof.
- the present invention also provides a method of controlling undesired vegetation, which corn- prises allowing a herbicidal active amount of at least one triazine compound of formula (I) in- cluding agriculturally acceptable salts or derivatives of compounds of formula (I), or composi- tions thereof.
- triazine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:
- O-triflate (OTf) (II) can be performed with a triflate transfering reagent like tri- flic anhydride.
- the reaction is usually carried out at from 0 °C to the boiling point of the reaction mixture, pref- erably at from 10 °C to 110 °C, particularly preferably at from 10 °C to 30 °C, in an inert organic solvent in the presence of a base.
- suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform, carbon tetrachloride and chloroben- zene, preferentially dichloromethane.
- Suitable bases are tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substi- tuted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to triethylamine and diisopropylethylamine.
- methyltriazines of formula (IV) can be obtained by reacting respective triazines of formula (II) with boronic acids of formula (III):
- the reaction of the triazine (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.
- the reaction may in principle be carried out in substance. However, preference is given to re- acting the triazines (II) with the boronic acids (III) in an organic solvent.
- Suitable in principle are all solvents which are capable of dissolving the triazines (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'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrrolidinone (NMP).
- ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF) and dipolar aprotic solvents such as sul- folane
- 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 aluminium 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, caesium 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
- 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 aluminium hydroxide and alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, caesium carbonate, magnesium carbonate, and calcium carbonate.
- metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminium hydroxide
- alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, caesium 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 aluminium hydroxide.
- 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 aluminium 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 triazines (II), more preferably at from 1.0 to 5.0 equivalents based on the triazines (II), most preferably from 1.2 to 2.5 equivalents based on the triazines (II).
- the reaction of the triazines (II) with the boronic acids (III) 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 triazine
- the triazine compounds of formula (I) can be obtained by reacting respective methyltriazines (IV) with an oxidant:
- the reaction of the methyltriazine (IV) 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.
- 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 SeC>2, KMn0 4 , MnC>2, O2, Oxone, NaCI02, H2O2, preferably SeC>2 or KMn0 2 .
- 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 tria- zine 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 triazine 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.
- triazine compounds of formula (I) as described herein are capable of forming geometrical 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.
- triazine compounds of formula (I) as described herein have one or more centres of chi rality 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 according to the invention.
- triazine 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 gen- eral, the salts of those cations and the acid addition salts of those acids whose cations and ani- ons, respectively, have no adverse effect on the activity of the active compounds.
- Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C4-alkyl, HO-Ci-C4-alkyl, Ci-C 4 -alkoxy-Ci-C 4 - alkyl, HO-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, hep- tylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylamm
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic acids, preferably formate, acetate, propionate and butyrate.
- Triazine compounds of formula (I) as described herein having an acidic functionality, prefera- bly a carboxylic group or a sulphonic group, can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with the cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C6-al- kylamides or arylamides, as esters, e.g.
- allyl esters propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, e.g. as Ci-Cio-alkylthio esters.
- Preferred mono- and di-Ci-C6-alkylamides are the CH3 and the dimethyl- amides.
- Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
- Preferred alkyl es- ters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
- Preferred Ci-C4-alkoxy- Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g.
- the organic moieties mentioned in the definition of the variables R 1 , R 2 , Z, R 3 , and R 3A are - like the term halogen - collective terms for individual enumerations of the individual group mem- bers.
- the term halogen denotes in each case F, Cl, Br, or I.
- All hydrocarbon chains, e.g. all al- kyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
- Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
- Ci-C 6 -alkyl Ci-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1 -methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -
- Ci-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, 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-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, 1 ,1 -difluor
- Ci-C 6 -haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-io- dohexyl, and dodecafluorohexyl;
- C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
- C3-C6-halocycloalkyl C3-C6-cycloalkyl as mentioned above which is partially or fully substi- tuted with fluorine, chlorine, bromine and/or iodine, e.g., 1 -fluorocyclopropyl; 1 -fluorocyclobutyl, 1 -fluorocyclopentyl
- C3-C6-alkenyl e.g. 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-bu- tenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1 - pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl--
- C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1 -yl, 3- chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1 -yl, 2,3,3-trichloro-2-en-
- C3-C6-alkynyl e.g. 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl- 4-pent
- C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
- C3-C6-haloalkynyl a C3-C6-alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1 ,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bro- moprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1 , 1 -difluoro- but-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-
- 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 -methylbutoxy,
- Ci-C 4 -haloalkoxy a Ci-C 4 -alkoxy group as mentioned above which is partially or fully sub- stituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,
- 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 -alkylthio e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 - methylpropylthio, 2-methylpropylthio, and 1 , 1 -dimethylethylthio;
- Ci-C 6 -alkylthio Ci-C 4 -alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hex- ylthio, 1 , 1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethy
- (Ci-C 4 -alkyl)amino e.g. methylamino, ethylamino, propylamino, 1 -methylethylamino, bu- tylamino, 1 -methylpropylamino, 2-methylpropylamino, or 1 ,1 -dimethylethylamino;
- (Ci-C 6 -alkyl)amino (Ci-C 4 -alkylamino) as mentioned above, and also, e.g., pentylamino, 1 -methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1 -ethyl- propylamino, hexylamino, 1 ,1 -dimethylpropylamino, 1 ,2-dimethylpropylamino, 1 -methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1 -dimethylbutyla- mino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino
- di(Ci-C 6 -alkyl)amino di(Ci-C4-alkyl)amino as mentioned above, and also, e.g., N-methyl- N-pentylamino, N-methyl-N-(l-methylbutyl) amino, N-methyl-N-(2-methylbutyl)amino, N-methyl- N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1-dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-
- Ci-C 6 -alkylsulfonyl (Ci-C 6 -alkyl-S(0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1 -di- methylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1 - ethy
- C3-C6-cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
- C3-C6-cycloalkenyl 1 -cyclopropenyl, 2-cyclopropenyl, 1 -cyclobutenyl, 2-cyclobutenyl, 1 - cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadi- enyl, 1 -cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 2,5-cyclohexadienyl;
- bicyclic ring a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and inde- pendent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole
- heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
- 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
- heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an ox ygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
- pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
- thiazol-2-yl thiazol-4-yl, thiazol-5-yl
- oxadia- zolyl e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl,
- thiadiazolyl e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl
- triazolyl e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl
- 1-tetrazolyl 6-membered aromatic rings like pyridyl (e.g.
- pyridine-2 -yl pyridine-3-yl, pyridine-4-yl
- pyrazinyl e.g. pyridazin-3-yl, pyridazin-4-yl
- pyrimidinyl e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl
- pyrazin-2-yl triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl
- substituted if not specified otherwise refers to substituted with 1 , 2, or up to maxi- mum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not men- tioned otherwise.
- acidic functionality if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
- cyclic groups comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
- triazine compounds of formula (I) are suitable as herbicides.
- triazine compounds of formula (I) and their use as herbicides, wherein the variables, either independently of one another or in combination with one another, have the following meanings:
- R 1 is C2-C6-alkyl, Ci-C 6 -haloalkyl, HO-Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C3-C6-alkenyloxy, C3- C 6 -haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C 6 -haloalkoxy, C3-C6-cycloalk- oxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C 6 -alkylthio, Ci
- R 1 is C 2 -C 6 -alkyl, Ci-C 6 -haloalkyl, HO- Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloal- kenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyl- oxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -haloalkoxy, C 3 -Ce-cy- cloalkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkenyl
- R 1 is C 2 -C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -halo- alkenyloxy, C 3 -C 6 -alkynyloxy, C 4 -C 6 -haloalkynyloxy, Ci-C 6 -alkylthio, C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
- R 1 is C 2 -C 6 -alkyl, Ci-C6-alkoxy, or C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
- R 1 is C 3 -C 6 -cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R 1 is C2H5, 1-C3H7, 1-C4H9, OCH3, C-C3H5, or C-C4H7;
- R 1 is C2H5, OCH3, or C-C3H5; most preferred R 1 is C-C3H5;
- R 1 is formula R 1A
- R x 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 x is Ci-C6-haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, or C 3 -C 6 -halocy- cloalkenyl;
- R x is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocy- cloalkyl;
- R x is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or C 3 -C 6 -cycloalkyl;
- R x is H, halogen, Ci-C6-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-C 6 -alkyl e.g. CH 3 , C2H 5 , 1-C 3 H 7 , n-C 4 Hg, and 1-C4H 9 ; also more preferred 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-C 6 -haloalkyl e.g. CHF2, CHF2, and CF3;
- R x is C3-C6-halocycloalkyl
- R x is H, CH3, C2H5, F, i-C3H 7 , CHF2, CHF2, or c-C3H 5 ;
- R y is H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halocycloalkenyl;
- R y is H, Ci-C 6 -haloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, or C3-C6-halo- cycloalkenyl;
- 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. CH3, C2H5, 1-C3H7, n-C 4 H9, and 1-C4H9;
- 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-C3H5;
- R 1 is the formula R 1A wherein R x and R y together with the carbon they are at- tached 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 ; also preferred R 1 is the formula R 1A wherein R x and R y together with the carbon they are at- tached form a 3-to 5-membered saturated carbocyclic ring containing 0 or 1 heteroatom se- lected from O, or N, wherein the ring is substituted with 0,1 , or 2, R e ;
- R 1 is the formula R 1A wherein R x and R y together with the carbon they are at- tached form a 3-to 5-membered saturated carbocyclic ring, wherein the ring is substituted with 0,1 , or 2, R e ;
- R 1 is the formula R 1A wherein R x and R y together with the carbon they are at- tached form a 3-to 5-membered saturated carbocyclic ring, wherein the ring is unsubstituted; also preferred R 1 is the formula R 1A wherein R x and R y together with the carbon they are at- tached form a 3- membered saturated carbocyclic ring, wherein the ring is unsubstituted;
- R 1 is the R 1A 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 ; also preferred R 1 is the R 1A 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 is the R 1A 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; also preferred R 1 is the R 1A 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
- R e is halogen
- R 2 is OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-al- kynyloxy, C2-C6-haloalkynyloxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, (C1-C6- alkoxy)carbonyl-Ci-C 6 -alkylthio, NH2, (Ci-C 6 -alkyl)amino, (Ci-C 6 -alkyl)sulfonylamino, [di(Ci-C 6 - alkyl)amino]sulfonylamino, phenyloxy, phenyl-Ci-C 6 -alkoxy or phenyl-Ci-C 6 -alkylthio
- R 2 is OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C2-C6-alkynyloxy, (Ci-C 6 -alkoxy)carbonyl- Ci-C 6 -alkoxy, Ci -C 6 -a I ky Ith i o , (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkylthio, NH2, (Ci-C 6 -alkyl)amino, (Ci-C 6 -alkyl)sulfonylamino, [di(Ci-C 6 -alkyl)amino]sulfonylamino, phenyloxy, phenyl-Ci-C 6 -alkoxy or phenyl-Ci-C 6 -alkylthio,
- R 2 is OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C2-C6-alkynyloxy, Ci-C 6 -al- kylthio, phenyloxy or phenyl-Ci-C 6 -alkoxy,
- R 2 is OH, Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy, or Ci-C6-haloalkoxy; especially preferred R 2 is Ci-C6-alkoxy, C 2 -C 6 -alkynyloxy, or Ci-C6-haloalkoxy;
- R 2 is OH, Ci-C 6 -alkoxy, or Ci-C 6 -haloalkoxy
- R 2 is OH, or Ci-C 6 -alkoxy
- R 2 is OH
- R 2 is Ci-C 6 -alkox
- R x , R y independently are H, halogen, Ci-C6-alkyl, Ci-C6-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 1 is R 1A 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-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
- R 3 are selected from halogen, CN, NO2, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, and C3-C6-cycloalkyl;
- R 3 are selected from halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, and Ci-C 6 -haloalkoxy;
- 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;
- 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 un- saturated 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 tria- zine ring with at least one R 3 , and which phenyl ring is further substituted with 0, 1 , 2, or 3 R 3 ; particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is formula W 1 ,
- R 3 same or differently are as defined herein including their preferred defini- tion;
- n 0, 1 , or 2, preferably 0 or 1 ;
- # denotes the point of attachment to the triazine ring
- R 3 same or differently are as defined herein including their preferred defini- tion;
- n 0, 1 , or 2, preferably 0 or 1 ;
- # denotes the point of attachment to the triazine ring
- R 3 same or differently are as defined herein including their preferred defini- tion;
- n 0, 1 , or 2, preferably 0 or 1 ;
- # denotes the point of attachment to the triazine 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
- R 3b and R 3c each independently is H, halogen, CN, NO 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 1 - C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 3 -C 6 -al- kynyloxy, C 3 -C 6 -haloalkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, hydroxycarbonyl, C 1 -C 6 - alkoxycarbonyl, Ci-C 6 -alky
- # denotes the point of attachment to the triazine ring
- Z is 5- or 6-membered heteroaryl ring
- Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine; particularly preferred Z is pyrimidine or pyridine;
- especially preferred Z is pyridine
- Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole; particularly preferred Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thio phene, furan, or pyrrole;
- Z is thiophene, furan, or pyrrole
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from below groups A to G,
- R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy or Ci-C 6 -haloalkoxy; m is 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-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
- # denotes the point of attachment to the triazine 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 triazine ring
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from A, B, C, and D;
- Z[i.e. the group“Z-(R 3 ) m ”] is A or C;
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from E, F, and G;
- Z i.e. the group“Z-(R 3 ) m ”] is E or G;
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from A1 , B1 , C1 , and D1 ; most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is A1 or C1 ;
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from E1 , F1 , and G1 ; also most particularly preferred Z[i.e. the group“Z-(R 3 ) m ”] is E1 or G1 ;
- Z is 9- or 10-membered partially or fully unsaturated bicyclic ring contain- ing 0, 1 , 2, 3, 4 or 5 heteroatoms selected from O, N, and S;
- Z is 9- or 10-membered partially or fully unsaturated bicyclic ring, wherein the ring attached to the triazine 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 heteroa- toms selected from O or N;
- Z is 9 membered bicyclic ring
- Z is a 9-membered bicyclic ring wherein the ring attached to the tri azine 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 triazine ring is phenyl or pyridine ring which is fused with another 5-membered partially un- saturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
- Z is a 9-membered bicyclic ring wherein the ring attached to the tri azine ring is a phenyl ring which is fused with another partially unsaturated 5-membered carbo- cycle comprising 1 or 2 oxygen atoms;
- Z is a 9-membered bicyclic ring wherein the ring attached to the triazine 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 triazine ring is thiophene, furan or pyrrole ring which is fused with another 6-membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms;
- Z is 10 membered bicyclic ring
- Z is a 10-membered bicyclic ring wherein the ring attached to the triazine 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 triazine ring is phenyl or pyridine ring which is fused with another 5- or 6- membered par- tially unsaturated 5- or 6- membered carbocycle comprising 1 or 2 oxygen atoms; most particularly preferred Z is a 10-membered bicyclic ring wherein the ring attached to the triazine 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 different are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and C1-C6- alkoxy;
- n 0, 1 or 2;
- R 4 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
- X 1 is O, S, or NR 3A ;
- R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
- Z[i.e. the group“Z-(R 3 ) m ”] is selected from groups H to V,
- Y 1 is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 het- eroatoms selected from O, N, and S;
- R 3 same or differently are selected from halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, and Ci- C 6 -alkoxy;
- n 0, 1 or 2;
- X 1 is O, S, or NR 3A ;
- R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
- # denotes the point of attachment to the triazine 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 triazine ring
- 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 , J 1 , K1 , L1 , M1 , N1 , 01 ,
- Z[i.e. the group“Z-(R 3 ) m ”] is H1 , L1 , or M1 ;
- Z[i.e. the group“Z-(R 3 ) m ”] is H 1 ;
- Z[i.e. the group“Z-(R 3 ) m ”] is H1 or W1a;
- 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 1 is the R 1A 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 1 is C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 2 is 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. Also preferred are compounds of formula (I), and their use as herbicide, wherein 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 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 the R 1A , 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 1 is 1-F-cyclopropyl
- 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 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 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 unsubstituted cyclopropyl
- 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 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; also preferred are compounds of formula (I), and their use as herbicide,
- R 1 is cyclopropyl or the R 1A wherein
- 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 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 -haloalkoxy, preferably halogen;
- n 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R x , R y independently are H, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalky, or C3-C6-cy- cloalkyl, 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, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably halogen;
- n 0, 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R 2 is 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 -haloalkoxy, preferably halogen;
- n 0, 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R 2 is OH, Ci-C 6 -alkoxy, C2-C6-alkynyloxy, or Ci-C 6 -haloalkoxy;
- Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, 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. Also preferred are compounds of formula (I) wherein Z is W 1 , which corresponds to formula (I.C), and their use as herbicide,
- 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 -haloalkoxy, 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.
- Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, 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.
- Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, 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. Also preferred are 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 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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.
- Z is phenyl, or 5- or 6-membered heteroaryl group selected from A to G as defined herein, or 9- to 10-membered bicyclic ring selected from H to V as defined herein;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, 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-cy- cloalkyl, 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal ogen;
- 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 C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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-cy- cloalkyl, 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal ogen;
- m is 0, 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R 1 is C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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-cy- cloalkyl, 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal ogen;
- n 0, 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R 1 is C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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-cy- cloalkyl, 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal ogen;
- 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 C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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-cy- cloalkyl, 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 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal ogen;
- n 0, 1 or 2;
- R 3 each independently is halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy, preferably halogen.
- R 1 is C2-C6-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, or C3-C6-cycloalkyl, preferably unsubstituted C3-C6-cycloalkyl, more preferably unsubstituted cyclopropyl;
- R 3 is halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, or Ci-C 6 -haloalkoxy, preferably hal- ogen;
- 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, cyclopropyl, or 1-F-cyclopropyl;
- R 2 is OH, OCH 3 , or OC 2 H 5 ;
- Z is selected from 2-CI-C 6 H 4 , 2-Br-C 6 H 4 , 2-CH 3 -C 6 H 4 , 2-CI-4-F-C 6 H 3 , 2-CI-5-CF 3 -C 6 H3, 2-CI-5- F-C6H3, 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 triazine 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
- triazine 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 triazine compound of formula (I) (compound A) and at least one fur- ther 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, triazine compound of formula (I. A) (corre- sponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active compound A or component A at least one, preferably exactly one, triazine compound of formula (I.A2) (corre- sponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.B) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.C) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.D) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.D2) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.E) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.F) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.G) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.H) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.H2) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I. I) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (1.12) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.J) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.J2) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.K) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.K2) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of formula (I.L) (corresponds to triazine compound of formula (I)), as defined herein.
- the composition comprises as active corn- pound A or component A at least one, preferably exactly one, triazine compound of for- mula (I.L2) (corresponds to triazine 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 selected from I .A to I.L, I.A2, or I.H2 to I.L2 , as defined above.
- compositions according to the present in- vention comprise at least one triazine compound of formula (I) and at least one further active compound B (herbicide B).
- the further herbicidal compound B (component B) is preferably se- lected from the herbicides of class b1) to b15):
- compositions can be selected from below herbicides B as defined below:
- ALS inhibitors acetolactate synthase inhibitors
- PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
- EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
- DHP inhibitors 7,8-dihydropteroate synthase inhibitors
- VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
- herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, 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.
- the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
- the compositions contain at least one inhibitor of 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 inhibitors, 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).
- the herbicidal activity of these compounds is based on the inhibition of the syn- thesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
- the compositions contain at least one cellulose bio- synthesis inhibitor (herbicide b11 ). The herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants. These inhibitors belong to the group L of the HRAC classification system.
- compositions contain at least one decoupler herbi- cide (herbicide b12).
- the herbicidal activity of these compounds is based on the disruption of the cell membrane.
- These inhibitors belong to the group M of the HRAC classification system.
- the compositions contain at least one auxinic herbi- cide (herbicide b13).
- auxinic herbi- cide include compounds that mimic auxins, i.e. plant hormones, and af- fect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
- compositions contain at least one auxin transport inhibitor (herbicide b14).
- auxin transport inhibitor hereinicide b14
- the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
- These compounds belong to the group P of the HRAC classifica- tion system.
- compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
- compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
- compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13.
- herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
- ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-
- sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
- imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
- pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6
- sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
- compositions compris- ing at least one imidazolinone herbicide
- inhibitors of the photosystem II e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one
- a preferred embodiment of the invention relates to those composi- tions comprising at least one aryl urea herbicide.
- a preferred embodi- ment of the invention relates to those compositions comprising at least one triazine herbicide.
- a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
- acifluorfen 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, pyr
- PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5
- bilanaphos biases
- bilanaphos biases
- bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
- compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, corn- pounds of group K1 , in particular dinitroanilines are preferred;
- chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone
- chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b11 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-1 4 - [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1 );
- 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, 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 es- ters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thio
- auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
- Preferred herbicides B that can be used in combination with the triazine compounds of the for- mula (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 triazine 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 );
- glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
- VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
- auxinic herbicides 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
- auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
- herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
- herbicides B could also be B.203 which is cyclopyranil.
- compositions according to the present in- vention comprise at least one triazine 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 triazine 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 (sulfosate).
- 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 triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compound of formula (I), preferably selected from compound 1 to 96 from the table A, and at least two, preferably exactly two, herb- icides B different from each other.
- component A at least one, preferably exactly one triazine compound of formula (I), preferably selected from compound 1 to 96 from the table A, and at least two, preferably exactly two, herb- icides B different from each other.
- the composition comprises as component A at least one, preferably exactly one triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compound of formula (I), preferably se- lected from compound 1 to 96 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 triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compound of formula (I), preferably selected from compound 1 to 96 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 triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally 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.
- group b1 in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycl
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b2), in particular selected from the group consisting of bensul- furon-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosulfamu- ron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imaza- mox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammonium, imazapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, imazaquin, imazaquin, imazaquin, im
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting compound 1 to 96 from the table A, at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-po- tassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, para- quat-dichloride, propanil, simazin, terbutryn and terbuthylazine.
- ametryn atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-po-
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally 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-
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flu- rochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, topramezone-sodium and 2- chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139- 71-0) .
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b6), in particular selected from the group consisting of glypho- sate, glyphosate-ammonium, glyphosate-dimethylammonium , glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally 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 triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b9), in particular selected from the group consisting of pendi- methalin and trifluralin.
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b10), in particular selected from the group consisting of aceto- chlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metaza- chlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone.
- a triazine compounds of formula (I) especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b10), in particular selected from the group consisting of aceto- chlor, butachlor, cafenstrole, dimethenamid-P,
- compositions comprising in addition to a triazine 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 par- ticular selected from the group consisting of isoxazoline compounds of the formulae 11.1 , II.2,
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally active compound from group b1 1), in particular indaziflam, isoxaben and triaziflam.
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally 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
- the composition comprises, in ad- dition to a triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one herbicid- ally 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 triazine compounds of formula (I), especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, di- chlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31-4).
- a triazine compounds of formula (I) especially an active compound from the group con- sisting of compound 1 to 96 from the table A, at least one and especially exactly one safener
- 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 compo- nents 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
- 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 triazine 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 triazine 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.1 ) (see table B, entry B.1 and table C, entry C.1 ).
- AIso especially preferred are corn- positions 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. Also especially preferred are compositions 5.1 to 5.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they additionally comprise B.30 as further herbicide B.
- 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.1 11 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.1 11 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.1 11 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.1 16 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.116 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 116.1 to 1 16.3653 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 1 18.1 to 118.3653 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 119.1 to 1 19.3653 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 140.1 to 140.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 73 from table A, in place of the compound 1.
- compositions 141.1 to 141.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 74 from table A, in place of the compound 1.
- compositions 142.1 to 142.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 75 from table A, in place of the compound 1.
- compositions 143.1 to 143.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 76 from table A, in place of the compound 1.
- compositions 144.1 to 144.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 77 from table A, in place of the compound 1.
- compositions 145.1 to 145.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 78 from table A, in place of the compound 1.
- compositions 146.1 to 146.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 79 from table A, in place of the compound 1.
- compositions 147.1 to 147.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 80 from table A, in place of the compound 1.
- compositions 148.1 to 148.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 81 from table A, in place of the compound 1.
- compositions 149.1 to 149.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 82 from table A, in place of the compound 1.
- compositions 150.1 to 150.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 83 from table A, in place of the compound 1.
- compositions 151.1 to 151.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 84 from table A, in place of the compound 1.
- compositions 152.1 to 152.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 85 from table A, in place of the compound 1.
- compositions 153.1 to 153.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 86 from table A, in place of the compound 1.
- compositions 154.1 to 154.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 87 from table A, in place of the compound 1.
- compositions 155.1 to 155.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 88 from table A, in place of the compound 1.
- compositions 156.1 to 156.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 89 from table A, in place of the compound 1.
- compositions 157.1 to 157.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 90 from table A, in place of the compound 1.
- compositions 158.1 to 158.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 91 from table A, in place of the compound 1.
- compositions 159.1 to 159.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 92 from table A, in place of the compound 1.
- compositions 160.1 to 160.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 93 from table A, in place of the compound 1.
- compositions 161.1 to 161.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 94 from table A, in place of the compound 1.
- compositions 162.1 to 162.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 95 from table A, in place of the compound 1.
- compositions 163.1 to 163.3653 which differ from the corre- sponding compositions 1.1 to 1.3653 only in that they comprise the compound 96 from table A, in place of the compound 1.
- compositions 2.3654 to 2.3671 which differ from the corresponding 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 corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.2 as further herbicide B.
- compositions 4.3654 to 4.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.8 as further herbicide B.
- compositions 5.3654 to 5.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.30 as further herbicide B.
- compositions 6.3654 to 6.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.32 as further herbicide B.
- compositions 7.3654 to 7.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.35 as further herbicide B.
- compositions 8.3654 to 8.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.38 as further herbicide B.
- compositions 9.3654 to 9.3671 which differ from the corresponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.40 as further herbicide 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 herb-icides 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 herb-icides 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 herb-icides 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 herb-icides 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 herb-icides 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 herb-icides 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 herbicides 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 herbicides 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 herbicides 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.1 11 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.11 1 and B.67 as further herb-icides 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 herb-icides 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 herb-icides 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.1 16 and B.67 as further herb-icides 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.116 and B.94 as further herb-icides 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 herbicides 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 herbicides 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 herbicides 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 herbicides 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 herbicides 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. Also especially preferred are compositions 62.3654 to 62.3671 which differ from the corre- sponding compositions 1.3654 to 1.3671 only in that they additionally comprise B.137 as further herbicide B.
- 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 11 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- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 33 from ta- ble A, in place of the compound 1.
- compositions 101.3654 to 101.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 34 from ta- ble A, in place of the compound 1.
- compositions 102.3654 to 102.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 35 from ta- ble A, in place of the compound 1.
- compositions 103.3654 to 103.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 36 from ta- ble A, in place of the compound 1.
- compositions 104.3654 to 104.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 37 from ta- ble A, in place of the compound 1.
- compositions 105.3654 to 105.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 38 from ta- ble 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- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 40 from ta- ble A, in place of the compound 1.
- compositions 108.3654 to 108.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 41 from ta- ble A, in place of the compound 1.
- compositions 109.3654 to 109.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 42 from ta- ble A, in place of the compound 1.
- compositions 110.3654 to 110.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 43 from ta- ble A, in place of the compound 1.
- compositions 11 1.3654 to 11 1.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 44 from ta- ble A, in place of the compound 1.
- compositions 112.3654 to 112.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 45 from ta- ble A, in place of the compound 1.
- compositions 1 13.3654 to 1 13.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 46 from ta- ble A, in place of the compound 1.
- compositions 1 14.3654 to 1 14.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 47 from ta- ble A, in place of the compound 1.
- compositions 115.3654 to 115.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 48 from ta- ble A, in place of the compound 1.
- compositions 116.3654 to 116.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 49 from ta- ble A, in place of the compound 1.
- compositions 117.3654 to 117.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 50 from ta- ble A, in place of the compound 1.
- compositions 118.3654 to 118.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 51 from ta- ble A, in place of the compound 1.
- compositions 1 19.3654 to 1 19.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 52 from ta- ble A, in place of the compound 1.
- compositions 120.3654 to 120.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 53 from ta- ble A, in place of the compound 1.
- compositions 121.3654 to 121.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 54 from ta- ble A, in place of the compound 1.
- compositions 122.3654 to 122.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 55 from ta- ble A, in place of the compound 1.
- compositions 123.3654 to 123.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 56 from ta- ble A, in place of the compound 1.
- compositions 124.3654 to 124.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 57 from ta- ble A, in place of the compound 1.
- compositions 125.3654 to 125.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 58 from ta- ble A, in place of the compound 1.
- compositions 126.3654 to 126.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 59 from ta- ble A, in place of the compound 1.
- compositions 127.3654 to 127.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 60 from ta- ble A, in place of the compound 1.
- compositions 128.3654 to 128.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 61 from ta- ble A, in place of the compound 1.
- compositions 129.3654 to 129.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 62 from ta- ble A, in place of the compound 1.
- compositions 130.3654 to 130.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 63 from ta- ble A, in place of the compound 1.
- compositions 131.3654 to 131.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 64 from ta- ble A, in place of the compound 1.
- compositions 132.3654 to 132.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 65 from ta- ble A, in place of the compound 1.
- compositions 133.3654 to 133.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 66 from ta- ble A, in place of the compound 1.
- compositions 134.3654 to 134.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 67 from ta- ble A, in place of the compound 1.
- compositions 135.3654 to 135.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 68 from ta- ble A, in place of the compound 1.
- compositions 136.3654 to 136.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 69 from ta- ble A, in place of the compound 1.
- compositions 137.3654 to 137.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 70 from ta- ble A, in place of the compound 1.
- compositions 138.3654 to 138.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 71 from ta- ble A, in place of the compound 1.
- compositions 139.3654 to 139.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 72 from ta- ble A, in place of the compound 1.
- compositions 140.3654 to 140.3671 which differ from the corre- spond-ing compositions 1.3654 to 1.3671 only in that they comprise the compound 73 from ta- ble A, in place of the compound 1.
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- Chemical & Material Sciences (AREA)
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
La présente invention concerne des composés triazine de formule (I), ou leurs sels ou dérivés acceptables sur le plan agricole, en tant qu'herbicides, les variables étant telles que définies dans la description, l'invention concerne également l'utilisation des composés triazine de formule (I) en tant qu'herbicide, des compositions les comprenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nuisibles, l'invention concerne en outre un procédé de lutte contre la végétation indésirable consistant à laisser agir une quantité herbicide efficace d'au moins un des composés triazine de formule (I) sur les plantes, leurs graines et/ou leur habitat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18152319 | 2018-01-18 | ||
| EP18152319.2 | 2018-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2019141552A1 true WO2019141552A1 (fr) | 2019-07-25 |
Family
ID=61007521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2019/050376 Ceased WO2019141552A1 (fr) | 2018-01-18 | 2019-01-09 | Composés herbicides de triazine |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2019141552A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024097598A1 (fr) * | 2022-11-02 | 2024-05-10 | Merck Sharp & Dohme Llc | Triazines utiles comme inhibiteurs de la protéine réceptrice de type nod 3 |
| US12331027B2 (en) | 2017-11-23 | 2025-06-17 | Basf Se | Herbicidal pyridylethers |
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|---|---|---|---|---|
| EP0374753A2 (fr) | 1988-12-19 | 1990-06-27 | American Cyanamid Company | Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines |
| EP0392225A2 (fr) | 1989-03-24 | 1990-10-17 | Ciba-Geigy Ag | Plantes transgéniques résistantes aux maladies |
| EP0427529A1 (fr) | 1989-11-07 | 1991-05-15 | Pioneer Hi-Bred International, Inc. | Lectines larvicides, et résistance induite des plantes aux insectes |
| EP0451878A1 (fr) | 1985-01-18 | 1991-10-16 | Plant Genetic Systems, N.V. | Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes |
| WO1993007278A1 (fr) | 1991-10-04 | 1993-04-15 | Ciba-Geigy Ag | Sequence d'adn synthetique ayant une action insecticide accrue dans le mais |
| WO1995034656A1 (fr) | 1994-06-10 | 1995-12-21 | Ciba-Geigy Ag | Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres |
| WO2002015701A2 (fr) | 2000-08-25 | 2002-02-28 | Syngenta Participations Ag | Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis) |
| WO2003018810A2 (fr) | 2001-08-31 | 2003-03-06 | Syngenta Participations Ag | Toxines cry3a modifiees et sequences d'acides nucleiques les codant |
| WO2003052073A2 (fr) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Nouvel evenement du mais |
| WO2013092244A1 (fr) * | 2011-12-20 | 2013-06-27 | Basf Se | Triazines herbicides |
| WO2016120355A2 (fr) | 2015-01-30 | 2016-08-04 | Basf Se | Phénylpyrimidines herbicides |
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2019
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|---|---|---|---|---|
| EP0451878A1 (fr) | 1985-01-18 | 1991-10-16 | Plant Genetic Systems, N.V. | Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes |
| EP0374753A2 (fr) | 1988-12-19 | 1990-06-27 | American Cyanamid Company | Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines |
| EP0392225A2 (fr) | 1989-03-24 | 1990-10-17 | Ciba-Geigy Ag | Plantes transgéniques résistantes aux maladies |
| EP0427529A1 (fr) | 1989-11-07 | 1991-05-15 | Pioneer Hi-Bred International, Inc. | Lectines larvicides, et résistance induite des plantes aux insectes |
| WO1993007278A1 (fr) | 1991-10-04 | 1993-04-15 | Ciba-Geigy Ag | Sequence d'adn synthetique ayant une action insecticide accrue dans le mais |
| WO1995034656A1 (fr) | 1994-06-10 | 1995-12-21 | Ciba-Geigy Ag | Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres |
| WO2002015701A2 (fr) | 2000-08-25 | 2002-02-28 | Syngenta Participations Ag | Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis) |
| WO2003018810A2 (fr) | 2001-08-31 | 2003-03-06 | Syngenta Participations Ag | Toxines cry3a modifiees et sequences d'acides nucleiques les codant |
| WO2003052073A2 (fr) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Nouvel evenement du mais |
| WO2013092244A1 (fr) * | 2011-12-20 | 2013-06-27 | Basf Se | Triazines herbicides |
| WO2016120355A2 (fr) | 2015-01-30 | 2016-08-04 | Basf Se | Phénylpyrimidines herbicides |
Non-Patent Citations (15)
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| "Farm Chemicals Handbook", vol. 86, 2000, MEISTER PUBLISHING COMPANY |
| B. HOCK; C. FEDTKE; R. R. SCHMIDT: "Herbizide [Herbicides", 1995, GEORG THIEME VERLAG |
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1361139-71-0 |
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1486617-21-3 |
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 19112-35-7 |
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 52836-31-4 |
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 71526-07-3 |
| K. K. HATZIOS: "Herbicide Handbook", 1998, WEED SCIENCE SOCIETY OF AMERICA |
| KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation" |
| KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants, and additives" |
| KOZHEVNIKOV ET AL: "The Ritter reaction in the 5-cyano-1,2,4-triazine series", MENDELEEV COMMUNICATIONS, INSTITUTE OF PHYSICS PUBLISHING, BRISTOL, GB, vol. 10, no. 3, 1 January 2000 (2000-01-01), pages 117 - 118, XP022529556, ISSN: 0959-9436, DOI: 10.1070/MC2000V010N03ABEH001255 * |
| MCCUTCHEON'S: "Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES |
| MOLLET; GRUBEMANN: "Formulation technology", 2001, WILEY VCH |
| SHOETSU KONNO ET AL: "Studies on as-triazine derivatives. V. Synthesis and Hydration of Alkynyl-1,2,4-triazines", HETEROCYCLES, JAPAN INSTITUTE OF HETEROCYCLIC CHEMISTRY, vol. 22, no. 10, 1 January 1984 (1984-01-01), pages 2245 - 2248, XP009506542, ISSN: 1881-0942, DOI: 10.3987/R-1984-10-2245 * |
| W. H. AHRENS: "Herbicide Handbook", 1994, WEED SCIENCE SOCIETY OF AMERICA |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12331027B2 (en) | 2017-11-23 | 2025-06-17 | Basf Se | Herbicidal pyridylethers |
| WO2024097598A1 (fr) * | 2022-11-02 | 2024-05-10 | Merck Sharp & Dohme Llc | Triazines utiles comme inhibiteurs de la protéine réceptrice de type nod 3 |
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